Bootstrapped Web

We're back!

Bootstrapped Web — Sat, 21 Feb 2026 11:58:07 -0400

Jordan and I are back on the mics together! But it's not Bootstrapped Web.

Jordan is joining Justin Jackson and me as the 3rd permanent co-host of The Panel Podcast.

Be sure to subscribe to The Panel Podcast feed to receive future episodes.

Subscribe to The Panel Podcast in your podcast player.

Subscribe to The Panel Podcast on YouTube

Follow Brian: Twitter / Bluesky
Follow Jordan: Twitter / Bluesky
Follow Justin: Twitter / Bluesky

2025 recap & 2026 outlook

Bootstrapped Web — Wed, 17 Dec 2025 15:07:16 -0400

Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook.

What Jordan's up to:

What Brian's up to:

2025 Mid-Year Update

Bootstrapped Web — Thu, 21 Aug 2025 16:29:28 -0300

We're back for a mid-year update!

The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year?

What we're working on:

Jordan's in rocket ship mode on Rosie.
Brian's building Builder Methods and YouTubing.

Don't be a stranger!

Jordan on X: @jordangal
Brian on X: @casjam

We're still podcasting here:

Jordan's: Offsite
Brian's: The Panel

...

Keep your Bootstrapped Web feed! We'll pop back in here again soon(ish).

Our final episode (for now)

Bootstrapped Web — Thu, 09 Jan 2025 13:05:18 -0400

It's true. We're calling this a final episode—for now—but don't unsubscribe! We promise to pop into the feed every few months to catch up :)

But for now, we're taking a breather and staying focused on executing our businesses in 2025: Jordan's crankin on Rosie, Brian's building Instrumental Products.

Don't be a stranger!

Connect with Jordan:

Follow Jordan on Bluesky / Twitter
Rosie

Connect with Brian:

Follow Brian on Bluesky / Twitter
Instrumental Products
Instrumental.dev - Components for Rails
Clarityflow

Subscribe to Brian's new podcast with Justin Jackson: The Panel

Year-end takeaways & goals

Bootstrapped Web — Fri, 13 Dec 2024 17:37:29 -0400

2024 look-back and takeaways. 2025 goals. Let's go!

Connect with Brian:

Follow Brian on Bluesky / Twitter
Brian's products:
- Building! Instrumental.dev
- Instrumental Products
- Clarityflow

Connect with Jordan:

- Follow Jordan on Bluesky / Twitter
- Jordan's company, Rosie

Bluesky.

Bootstrapped Web — Fri, 06 Dec 2024 13:38:37 -0400

Bluesky takes. Activation funnels. Retention. Delegating. Demo videos. Video marketing. Sick vacations.

Connect with Jordan:

Follow Jordan on Bluesky / Twitter
Jordan's company, Rosie

Connect with Brian:

Follow Brian on Bluesky / Twitter
Brian's products:
- Building! Instrumental.dev
- "One Month MVP" service
- Clarityflow

Building out of a job

Bootstrapped Web — Fri, 08 Nov 2024 14:30:17 -0400

Putting in more hours to put in less. Building systems for delivering software. Deploying demo video(s). Listening to customers. Using a business to deepen your craft. News detox.

Connect with Brian:

Follow Brian on Bluesky / Twitter
Brian's products:
- Building! Instrumental.dev
- "One Month MVP" service
- Clarityflow

Connect with Jordan:

- Follow Jordan on Bluesky / Twitter
- Jordan's company, Rosie

"Thank you for solving my problem."

Bootstrapped Web — Fri, 01 Nov 2024 13:35:34 -0300

Bluesky is having a moment. Halloween. Customers telling us their problems are solved. Essential onboarding. Calm before the (hiring) storm. Projects are waiting. The podcasting election.

Bluesky starter packs to follow:

Connect with Jordan:

- Follow Jordan on Twitter
- Jordan's company, Rosie

Connect with Brian:

- Follow Brian on Bluesky / Twitter
- Brian's products:
  - Building! Instrumental.dev
  - "One Month MVP" service
  - Clarityflow

Probably fine

Bootstrapped Web — Fri, 25 Oct 2024 16:06:42 -0300

Join us in the (free) Bootstrapped Web community on Ripple.fm

Today:

Political noise. Removing features. Positioning. Products for developers. Idea wireframes (as a service). Hiring a video editor. Retainer-based hiring. Frequent flyer miles. Apple picking.

Brian's stuff:

Brian's products:
- New! Instrumental.dev
- "One Month MVP" service
- Clarityflow
Brian on Twitter: @casjam

Jordan's stuff:

Jordan's product, Rosie
Jordan on Twitter: @jordangal

Funnels & Moonshots

Bootstrapped Web — Fri, 18 Oct 2024 13:49:52 -0300

Hey we didn't talk about WordPress this week! But we did talk about Elon... Also: Brian's working on a components product (instrumental.dev), Jordan's figuring out onboarding (heyrosie.com), and Brian's starting to scale consulting (onemonth.app).

Join our free community for Bootstrapped Web listeners

Connect with Jordan:

- Jordan's company, Rosie
- Jordan on Twitter: @jordangal

Connect with Brian:

Brian's products:
- New! Instrumental.dev
- "One Month MVP" service
- Clarityflow
Brian on Twitter: @casjam

Products For Builders

Bootstrapped Web — Fri, 11 Oct 2024 13:14:05 -0300

Join us in the (free) Bootstrapped Web community on Ripple.fm

Today:

Brian's new product (Instrumental.dev). Comparing the open-source leadership styles of Matt, DHH, and Taylor. Building products for builders. Components. Tightening the team. Scaling consulting from 1 to...? Let's Go Mets.

Brian's stuff:

Brian's products:
- New! Instrumental.dev
- "One Month MVP" service
- Clarityflow
Brian on Twitter: @casjam

Jordan's stuff:

Jordan's product, Rosie
Jordan on Twitter: @jordangal

Pressing Questions

Bootstrapped Web — Fri, 27 Sep 2024 13:15:28 -0300

Brian and Jordan's expert (lol) takes on WordPress-land. Car shopping. Netflix rec's. Funnel tracking. Customer observations. Over-building.

Join our free community for Bootstrapped Web listeners

If you're wondering "what's happening in WordPress?", our friend Matt Medieros published this excellent "just the facts" timeline.

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's MVP serice OneMonth.app
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Onboarding Funnels

Bootstrapped Web — Fri, 20 Sep 2024 13:58:17 -0300

Join us in the (free) Bootstrapped Web community on Ripple.fm

Today:

Optimizing our onboarding funnels. Calls to action. Lead ads. ARPU. API plans. Pearl Jam. Sleep (or lack thereof).

Brian's stuff:

Brian's "One Month MVP" service
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Jordan's stuff:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

What Customers Want

Bootstrapped Web — Fri, 13 Sep 2024 13:54:00 -0300

Q4 energy. Signup funnels. Self-serve vs. not. Building assets vs. building cashflow. Membership business models.

Join our free community for Bootstrapped Web listeners

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's MVP serice OneMonth.app
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Why is SaaS hard?

Bootstrapped Web — Fri, 30 Aug 2024 13:26:41 -0300

Join us in the (free) Bootstrapped Web community on Ripple.fm

Today:

Why makes SaaS more difficult than other business models? Rosie first customers! Brian's pricing experiment update. Training businesses. AI waves. Profitability at $1-2m. College Football. US Open Tennis.

Brian's stuff:

Brian's "One Month MVP" service
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Jordan's stuff:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

If we bootstrapped

Bootstrapped Web — Thu, 22 Aug 2024 14:33:16 -0300

Today on Bootstrapped Web:

What if we bootstrapped? Funnel projects. Pricing experiments. Software speed. Tech-enabled services. Listener conversations on Ripple.

Join our free community for Bootstrapped Web listeners

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's MVP serice OneMonth.app
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Funnels & Websites

Bootstrapped Web — Fri, 16 Aug 2024 13:04:34 -0300

Connect with Brian, Jordan and fellow listeners in the Bootstrapped Web community on Ripple.fm

Today:

Asking the hard-hitting questions like...

Coconut pastries... for or against? Is anyone actually able to log into the black hole that is Meta ads? Publishing a 1-page HTML landing page shouldn't be difficult. Should it?

Brian's stuff:

Brian's "One Month MVP" service
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Jordan's stuff:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Networks & Audiences

Bootstrapped Web — Fri, 09 Aug 2024 14:43:15 -0300

Ripple.fm is live and open. Rosie is live for self serve signups. Niche social networking. Advertising using video. Cold outreach playbooks. And a special guest joins the show

Join our free community for Bootstrapped Web listeners

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's Consulting services: OneMonth.app & Tailor-Made UI
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Pricing Experiments

Bootstrapped Web — Fri, 02 Aug 2024 15:33:29 -0300

Brian launches built and launched something new. 2 things actually. Jordan changes pricing strategy for Rosie. Brian also changes pricing strategy for Clarityflow. And all find our AI hardware "friend".

Connect with Brian, Jordan and fellow listeners in the Bootstrapped Web community on Ripple.fm

Brian's stuff:

Brian launched Ripple.fm
Brian's new "One Month MVP" service
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Jordan's stuff:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Era of Trying Stuff

Bootstrapped Web — Thu, 18 Jul 2024 17:21:35 -0300

Yet another new product announcement from Brian. Jordan launches to first customers. The era of hacking on new ideas. Summer speed ups. Professional standards. Vacations. Special guest joins us to tell us it's time to stop.

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's newest thing: Ripple.fm
Brian's Service: Tailor-Made UI
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

What's Next?

Bootstrapped Web — Fri, 12 Jul 2024 14:46:51 -0300

Brian's next product announcement. Marketing first. Small bets. Private podcasting. AI product development speed. Summer vacations.

Connect with Brian:

Brian's next product landing page
Brian's Service: Tailor-Made UI
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

The Morning After

Bootstrapped Web — Fri, 28 Jun 2024 13:43:50 -0300

US Presidential debate analysis. America. Launch week. First customers. Perfect storm for a new product idea. Questioning assumptions. Seeking feedback.

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Tailor-Made UI
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Dialing In

Bootstrapped Web — Fri, 21 Jun 2024 15:13:00 -0300

Tailor-Made UI. Knowing your customer. Launch-week learnings. Sales calls. Cold outreach. Margin & space. Date night hangovers. Summer camp.

Connect with Brian:

Brian's Service: Tailor-Made UI
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Hey, Rosie

Bootstrapped Web — Fri, 14 Jun 2024 13:28:11 -0300

Launching heyrosie.com. First demos. Twitter feeds. Productized consulting. Homepage rewrite. Summer camp. Concerts.

Connect with Jordan:

Jordan's company, Rosie
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Prompt Engineering

Bootstrapped Web — Fri, 07 Jun 2024 13:31:49 -0300

Launch week. AI demos. Prompt engineering. Help docs. Product marketing. New feature prep. B2B vs. B2C strategies. Coastal living. Mainstream AI.

Connect with Brian:

Brian's Product Consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Build in public

Bootstrapped Web — Fri, 31 May 2024 13:36:20 -0300

Troubleshooting back pain. "Early access" vs. "Sign up". Build (or brag) in public. Bootstrapping via consulting. Starter app templates. The AI voice space. No-BS marketing. Working outside.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Launch and learn

Bootstrapped Web — Fri, 24 May 2024 13:28:14 -0300

Shady domain brokers. Cooling off on product ideas. Pricing questions. High vs. low volume funnels. Launch and learn. Conflicting realities. Deadlifts. Summer travel.

Connect with Brian:

Brian's Product Consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

AI Products

Bootstrapped Web — Fri, 17 May 2024 17:24:37 -0300

GPT-4o. Sleepless nights. Product idea excitement. Self-serve funnels. Keeping calm before the storm. Selling to small business. Knicks in 6?

The David Park Tweet that Jordan referenced.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Product Hunting

Bootstrapped Web — Fri, 10 May 2024 16:55:49 -0300

No, we're not talking about Product Hunt (the website) today. This one's about:

Hunting for new product ideas. Categories in AI. Finding a partner. Divesting in audience. Hobbies. Attention diets. Mothers day.

Connect with Brian:

Brian's Product Consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Startup Names

Bootstrapped Web — Fri, 03 May 2024 16:52:35 -0300

Choosing a name. YouTube experiments. SEO. Reaching a foreign industry. Branding exercise. The New York Knicks.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's YouTube channel: @briancasel
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Entrepreneurial Seasons

Bootstrapped Web — Fri, 26 Apr 2024 16:53:52 -0300

Protyping with AI. Burnout aftermath. Validation theories that need retiring. Go-to-market. MVP speed. SaaS UI components as a service. Kitchen Reno. Passover. Knicks Games.

Connect with Brian:

Brian's Product Studio: Instrumental Products
Brian's YouTube channel: @briancasel
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Not Selling to SaaS

Bootstrapped Web — Fri, 19 Apr 2024 16:34:29 -0300

Email for SaaS. Selling to Main Street. AI in the real world. Offloading customer support. UI/UX consultancy pricing. YouTube experimentation. Vacation guilt. Kitchen renovations.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Sell to SaaS?

Bootstrapped Web — Thu, 11 Apr 2024 17:03:38 -0300

Exploring products that sell to SaaS. Flights. Credit card points. Passover. Elections. Twitter. Validation. No-kids vacations.

Connect with Brian:

Brian's Product Studio: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Make it Rough

Bootstrapped Web — Fri, 05 Apr 2024 17:16:06 -0300

Idea hunting. Competitors. Levels. Portfolios. Rough products. Customer success. Weekly pricing. Productized services. Earthquakes. Supplements.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Creating Content & New Product Ideas

Bootstrapped Web — Fri, 29 Mar 2024 16:50:58 -0300

Brian's first LinkedIn post. YouTube. Texas. Northeast. Inbound vs. outbound. New product ideas. AI. Ecommerce. Customer Success. Tapping demand.

Connect with Brian:

Brian's Product Studio: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Ideas & Tech Stacks

Bootstrapped Web — Fri, 15 Mar 2024 16:59:49 -0300

Exploring new ideas via conferences. Building in Laravel vs. Rails. Training customer success. Leveraging audience as an employee vs. founder. Travel energy.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's new consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

The internet is a confusing place

Bootstrapped Web — Fri, 08 Mar 2024 15:20:40 -0400

SaaS trends. Product studio. Pivots. Personal energy. Business energy. Ecommerce Space. Bootstrapping. First principles. Product idea mining. Platform risk. Elementary school talent shows.

Connect with Brian:

Brian's Product Studio: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Charging for Onboarding

Bootstrapped Web — Fri, 23 Feb 2024 17:10:16 -0400

Launching a consultancy. Generating pipeline. Breaking limiting mindsets. Outsource vs. in-house SDRs. Paid customer onboarding. Daddy-daughter dancing.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's new consultancy: Instrumental Products
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

New Directions

Bootstrapped Web — Fri, 16 Feb 2024 16:43:55 -0400

AI everywhere. Zuck's shots fired. Committing to the new direction. Customer success. "Starter for hire" consultancy concept. Skiing. Birthdays.

Connect with Brian:

Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

2024 Calculus

Bootstrapped Web — Fri, 02 Feb 2024 17:12:15 -0400

Homepage experiments. Marketing is too expensive. Product-led growth. VC game. Bootstrapper game. Cold outreach. Over-correcting. Shingles. Vienna. Snowboarding.

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's new content: fullstackfounder.co
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Enough Time

Bootstrapped Web — Fri, 19 Jan 2024 16:44:09 -0400

Customer Success. Offers product. Consulting aint so bad. Hiring a video editor. Redefining success. Not enough time. Ski trips with kids. Ski trips with adults. Selling before launching. Alarms.

Connect with Brian:

Brian's new business: fullstackfounder.co
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Pipeline Energy

Bootstrapped Web — Fri, 12 Jan 2024 16:15:29 -0400

Energizing the pipeline, energizing customer success, shipping a marketing site, unrealistic time estimations, getting snowed in, too much coffee (or not enough?)...

Connect with Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Connect with Brian:

Brian's new business: fullstackfounder.co
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Blank Canvas

Bootstrapped Web — Fri, 05 Jan 2024 17:05:06 -0400

New Year, new start, a blank canvas... Working more (or less). Clarityflow Commerce. New brand name. YouTube. Growing pipeline. Selling a product two ways. Runway pressure. Just another year :)

Connect with Brian and Jordan:

Brian's building: fullstackfounder.co (site is coming a few days after this episode publishes!)
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

What would a young Jordan and Brian say?

Bootstrapped Web — Fri, 15 Dec 2023 18:22:45 -0400

In our final show of 2023, we're going deep... What would our younger selves think? What were our biggest milestones to date? Hardest challenges? What's our favorite "cheat code"?

Connect with Brian and Jordan:

Brian's building: InstrumentalProducts.com
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Winning Partnerships

Bootstrapped Web — Fri, 08 Dec 2023 17:12:55 -0400

Creator businesses. Self-serve demos. Partnership Gold. Stair-stepping. Sales process. Economy and SaaS. YouTube. Marketing in 2024. Audience. What else? We'll see...

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's new thing: InstrumentalProducts.com
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Operating a Media Company

Bootstrapped Web — Fri, 01 Dec 2023 17:46:45 -0400

Black Friday fun. Cold email. Sales teams. Product market fit. Website redesign. Media company operations. Audience funnels.

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's new thing: InstrumentalProducts.com
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

News Diets & Work Balance

Bootstrapped Web — Fri, 17 Nov 2023 16:51:54 -0400

On today's episode:

Our news diets and managing stress with world events
New onboarding flows & outreach wins
Board meeting dynamics
SaaS viability in 2024

Connect with Brian and Jordan:

Brian's new thing: InstrumentalProducts.com
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

FOMO, Focus, and AI

Bootstrapped Web — Fri, 10 Nov 2023 17:42:21 -0400

On today's episode:

Brian goes public with his new thing for 2024...
Jordan onboards & optimizes the new sales team
Discovery channels vs. relationship channels
Spicy takes on AI startup land...

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's new thing: InstrumentalProducts.com
Brian's SaaS, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Compensation, Content, & Speed

Bootstrapped Web — Fri, 03 Nov 2023 16:40:23 -0300

On today's episode:

Sharing our real time stories publicly & transparently
Compensation for sales teams vs. product teams
Developing the content muscle
Self-serve & async demos and onboarding
Exploring a coaching offer around product strategy

Connect with Brian and Jordan:

Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Staring Reality In The Face

Bootstrapped Web — Fri, 27 Oct 2023 17:27:36 -0300

On today's episode:

A few words on world events
Brian's runway and strategic planning for 2024
Jordan's reallocating of resources and investment
Brian's firing himself from sales
Jordan's hiring for sales

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Product Growth Levers

Bootstrapped Web — Fri, 15 Sep 2023 17:28:43 -0300

On today's episode:

When does shipping product lead to growth?
Muddy Metrics
Sports, exercise, health, eating, and drinking habits

Connect with Brian and Jordan:

Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Getting Outside Help

Bootstrapped Web — Fri, 08 Sep 2023 17:26:22 -0300

On today's episode:

How we work with coaches & consultants to guide strategy & implementation
UX hangover on shipped features
Selling software "once"

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

Context Switching

Bootstrapped Web — Fri, 25 Aug 2023 17:03:18 -0300

On today's episode:

How we onboard and activate after a sales call
Strategic pricing and show vs. don't show
How to think about hiring a sales person
Context switching between product work and marketing work as a solo founder.

Connect with Brian and Jordan:

Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel
Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal

Learning to do business (over and over)

Bootstrapped Web — Fri, 11 Aug 2023 17:20:30 -0300

On today's episode:

Building in public. Why and how?
Learning sales. Process, strategy, tactics.
How we learn and implement.
A solo founder's dillemma

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Jordan on Threads: @jordangal
Brian's company, Clarityflow
Brian on Twitter: @casjam
Brian on Threads: @brian.casel

An appropriate level of mud slinging

Bootstrapped Web — Fri, 21 Jul 2023 18:23:20 -0300

On today's episode:

How do we think about runway and profitability?
What's an appropriate level of mud throwing?
Should founders spend time on personal brand?

Connect with Brian and Jordan:

Brian's company, Clarityflow
Brian on Threads: @brian.casel
Brian on Twitter: @casjam
Jordan's company, Rally
Jordan on Threads: @jordangal
Jordan on Twitter: @jordangal

Launching mobile apps, sales cadence, and summer work-life.

Bootstrapped Web — Fri, 07 Jul 2023 17:37:06 -0300

On today's episode:

Brian's back from Asia (did he stop working?)
Launching the Clarityflow app on iOS and Android (check the video)
Jordan's shifting the sales process & sequence
What it takes to close larger deals

Connect with Brian and Jordan:

Jordan's company, Rally
Jordan on Twitter: @jordangal
Brian's company, Clarityflow
Brian on Twitter: @casjam

Yo! We're on Threads too!

Sales Breakthroughs & In-Person Growth Strategy

Bootstrapped Web — Fri, 09 Jun 2023 17:10:57 -0300

On today's episode:

The value of in-person relationship building
The murky side of MRR growth
Transparency with our teams
PGA & LIV, Apple Vision Pro and other sidetracks!

Connect with Brian and Jordan:

Brian's company, Clarityflow
Jordan's company, Rally
Brian on Twitter: @casjam
Jordan on Twitter: @jordangal

High status vs. low status customers

Bootstrapped Web — Fri, 02 Jun 2023 17:18:01 -0300

What (and when) is a SaaS "feature complete"?
How do we sell and negotiate mid-market contracts?
How to please customers (and which ones are worth pleasing)?

...And other tricky questions we're thinking about this week.

Connect with Brian and Jordan:

Brian's company, Clarityflow
Jordan's company, Rally
Brian on Twitter: @casjam
Jordan on Twitter: @jordangal

Founder Shadowing

Bootstrapped Web — Fri, 19 May 2023 16:31:05 -0300

Founder shadowing (make it a thing?)
chatGPT vs. hiring a writer
Go to market strategy
Dialing in ICP
What is marketing, really?

Follow Brian and Jordan:

Jordan's company, Rally
Brian's company, Clarityflow
Jordan on Twitter
Brian on Twitter

Starting Up Sooner vs. Later

Bootstrapped Web — Fri, 12 May 2023 16:24:35 -0300

Brian and Jordan give their takes on the question of whether to start up your first business earlier vs. later in life.

Plus: Board meeting takeaways, MRR growth, sales demos, enterprise vs. mid-market, and BBQ smokers.

Brian's business: Clarityflow (formerly ZipMessage )

Jordan's business: Rally

Knowing what we know now...

Bootstrapped Web — Fri, 05 May 2023 17:41:00 -0300

What would we have done differently if we started Rally or Clarityflow over again? We get into that and other questions from Twitter. Keep em coming!

Brian's business: Clarityflow (formerly ZipMessage)
Jordan's business: Rally

Hangovers & Chaos

Bootstrapped Web — Fri, 28 Apr 2023 17:49:37 -0300

Brian's taming the chaos of inbound customer growth mixed with urgency to ship. Jordan's experimenting with 2 go-to-market strategies, one for enterprise, one with partners.

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage)

Raising Funding (& Pricing)

Bootstrapped Web — Fri, 21 Apr 2023 16:07:10 -0300

Jordan announces Rally's Series A and we unpack the whirlwind road that it took to get there.

Brian launched a pricing increase, which coincided with a competitor's unexpected shut down.

It's been a wild few weeks while we've been off, but we're back!

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage )

Artificial Intelligent Business

Bootstrapped Web — Wed, 29 Mar 2023 09:24:25 -0300

Random thoughts on what's happening in AI and startups. Jordan and co move to self-signups. Brian and co work on marketing projects.

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage)

Websites & Taxes

Bootstrapped Web — Wed, 22 Mar 2023 10:18:07 -0300

Both Jordan and Brian are in the thick of redesigning their SaaS websites. Plus some tax talk.

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage)

Learn about Section 174 tax issue for software businesses and join in the effort to repeal at ssballiance.org

ZipMessage has a new name...

Bootstrapped Web — Tue, 14 Mar 2023 19:45:13 -0300

Brian shares the news rebranding ZipMessage to a new name and the transition roadmap ahead... And the new name is...

Jordan and team step away to a conference while go-to-market heats up.

Oh yeah, and recorded on the day the Silicon Valley Bank saga unfolded in realtime... So that was a (and scary) discussion.

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage)

Putting in the hours

Bootstrapped Web — Wed, 08 Mar 2023 13:30:09 -0400

Jordan and Brian both feel overworked this week. Putting in more hours than usual, and more importantly, strategizing on which priorities get those hours.

Jordan's business, Rally

Brian's business, Clarityflow (formerly ZipMessage)

All the Things

Bootstrapped Web — Thu, 23 Feb 2023 09:58:30 -0400

Another week in the chaos that is startup land for Brian and Jordan. Topics include:

Starting and finishing our day
Managing focus through daily distractions
Delegating strategy and teeing up for results
And other rants… You know the drill

Hit us on Twitter @casjam @jordangal with feedback on what we should talk about next week!

As always, thanks for tuning in. Head here to leave a review on iTunes.

Projections… What Are They Good For?

Bootstrapped Web — Mon, 06 Feb 2023 18:49:47 -0400

The episode streak continues! Brian’s product design process, Jordan’s annual budget meeting (and takeaways), outbound vs. inbound marketing, and an interesting discussion around the usefulness of projections.

As always, thanks for tuning in. Head here to leave a review on iTunes.

Communicating What's Next

Bootstrapped Web — Tue, 31 Jan 2023 18:11:53 -0400

This week, Brian and Jordan yap about:

– Strategic partnerships

– Pricing on transactions

– Communicating company direction (internally)

– Developer-focused content

– …Creatine pills?

We’re running out of ideas! Hit us up on Twitter (@casjam, @jordangal) and tell us what we should talk about.

As always, thanks for tuning in. Head here to leave a review on iTunes.

Product in Market (Is How We Learn)

Bootstrapped Web — Tue, 24 Jan 2023 15:24:52 -0400

Back for our weekly founder therapy session, err… podcast episode

Here’s what’s up this week:

– Brian (finally) ships sub-threads in ZipMessage

– Jordan’s hiring an SDR

– Learning from strategic decisions that went wrong

– Product insights with vs without a product in market

As always, thanks for tuning in. Head here to leave a review on iTunes.

Building in public… More.

Bootstrapped Web — Tue, 17 Jan 2023 20:25:34 -0400

We kick off 2023 with a grab bag of topics:

– Jordan’s building in public more

– Brian’s building solo with contractors

– Headless ecom becoming “a thing”

– ChatGPT is firmly in Brian’s coding workflow

As always, thanks for tuning in. Head here to leave a review on iTunes.

Another Year

Bootstrapped Web — Tue, 03 Jan 2023 17:22:15 -0400

We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on…

Thanks for listening and for sticking with us another year on Bootstrapped Web.

“Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This PluginTweet This

Talking Points:

Viruses, holiday cards, and coming back from vacation
2022 for ZipMessage and Rally
Lack of product-market fit
Tim Ferriss’ Fear Setting
The Ten-Year Business
Staying “based” and staying true to your vision
Themes and goals for 2023
Building features specifically for specific markets

“The first year [for Zipmessage] was a dream and the second year was more bumpy and challenging.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Hey ChatGPT, what should we talk about?

Bootstrapped Web — Tue, 13 Dec 2022 16:11:56 -0400

We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“What can this do? How does this change our product? Does this change things significantly enough that we should come off our roadmap?” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The future of AI and creators
Q4 spreadsheets and budgeting
Updates in Rally and ZipMessage
- SEO content
- Marketing and sales
- Product-led content

“If we’re not working on those growth graphs, I don’t feel comfortable. But, at the same time, I need to work more on the product” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Twitter Takes (and Some Business Talk)

Bootstrapped Web — Wed, 09 Nov 2022 17:44:46 -0400

Our obligatory take on Twitter in the Elon era. Also: SEO, board meetings, and growth targets.

What are your thoughts on Twitter in the time of Elon? How do you run your board meetings? When it comes to growth targets, where do you focus your energy?

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“The more Twitter is in everyone’s everyday lives, the more leverage Twitter and Elon have to start taking marketshare in these parts of life.” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The conclusion of Jordan’s moving saga
The new era of Twitter
- Verification
- Twitter as a product
- Building in public
Team retreats and all-hands meetings
ZipMessage updates
SEO: quantity, speed, and AI tools
Board meetings and keeping records
Growth Targets

“I would love to build a culture where anyone in the company can say, ‘I think we’re focusing on this thing when we shouldn’t’ or ‘I think we’re missing this entirely.’” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Q4 Energy

Bootstrapped Web — Mon, 17 Oct 2022 19:31:11 -0300

Jordan talks defining their category and stepping back into the sales demo seat. Brian launched a community strategy while big product plans are underway in Q4.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“The single, most important element was… record your demos.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

NoSnowTinyConf Recap
Residual issues that arise after raising funds
Rally updates
Launch of Coach Club and Coach Club Digest
Treating marketing as a product
Team updates, accountability, and weekly stand-ups

“[I love] approaching marketing like its a product in itself.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Tools & People

Bootstrapped Web — Wed, 28 Sep 2022 15:45:29 -0300

What tools do you use for sales and support? Which tools work best for project management? How do you know who to hire first if you’re a bootstrapped company?

Brian and Jordan asked for your questions and Twitter delivered. Today, they are answering Twitter’s questions about what tools they use, and who to hire, and when.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“It’s interesting the way we think of tools and how we sell tools to other companies.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation Points:

NoSnow TinyConf
Tools that we use:
- Techstack (Laravel, Angular, React, Ruby on Rails, PHP, Tailwind)
- Project Management (Github, Notion, MixPanel, Confluence, Jira)
  - Marketing Changelog
- Sales, Marketing, and Support (Pipedrive, Asana, Hubspot, Salesforce, Intercom, Customer.io, HelpSpace, HelpScout)
- Metrics and Internal Tracking (Grafana, Profitwell, ChartMogul, MixPanel, Amplitude, Google Analytics, Fathom Analytics, Plausible Analytics)
- Communication (Slack)
Hiring when you’re bootstrapped, versus when you’re funded
- Who to hire first
- Who they are hiring now

“If you can market and get your tool into their hands sometime during that first year of the company, you have such a higher likelihood of getting in. Some of these tools are so sticky.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

What We'd Build (If Not This)

Bootstrapped Web — Tue, 20 Sep 2022 19:05:54 -0300

Brian and Jordan are back behind the mic and are powered by the chilly fall weather and some pretty strong cold brew. Are you ready for the most random Bootstrapped Web episode yet?

How do you navigate the Catch-22 that is operations versus growth? If you were to jump into a completely different niche or industry right now, what business would you start? Brian and Jordan are answering some of your questions and topics submitted through Twitter.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“Every business that I’ve ever had, has been a reaction to the previous business.” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation Points:

Operations versus growth
- In SaaS versus as a freelancer
- What you need to do in order to not interrupt the forward momentum
- Invite-only feature launch with ZipMessage
- Does funding really help extend your roadmap?
- The Catch-22 of growth and operations
New and different niches and industries
- Time away for research
- AI-driven tech
- Media businesses in the modern web
  - YouTube, TikTok, OnlyFans, etc.
  - Different use cases for almost anything
- Separating passion from a career?
The formatting of new podcasts
Types of tweets and content on Twitter

“Having millions of dollars in the bank doesn’t help.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Work-Life (Hour-by-Hour), Explained

Bootstrapped Web — Thu, 08 Sep 2022 15:27:59 -0300

What are the rocks in your life right now? How do you balance work and life? What are some good compartmentalizing tactics, so you can leave work at work? What are routines and habits that work for your schedule and team?

Today, Brian and Jordan are talking about their daily routines and how they plan their days around work, their personal life, exercise, and with team members that are scattered all around the globe. They share different time-saving tricks, apps that help hold them accountable to staying healthy, and their opinions on morning productivity and pulling all-nighters.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“I have some real issues with the morning. I’m not very productive in the morning.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation Points:

Rocks, pebbles, and boulders (and hair and sand)
Daily routines and how to optimize your day
- Personal life
- Professional life
Morning productivity versus night owl hours
The ultimate productivity app: a notepad and a pen
Productivity hours when your team members live in different time zones
Separating professional and personal life

“I”m very much a morning person. I like waking up relatively early but these people with the 5AM and 4AM wake-ups seem just a little bit extreme to me.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Research, Roadmaps, People, and Product

Bootstrapped Web — Wed, 31 Aug 2022 19:41:24 -0300

How do you figure out the next iteration of your business? What keeps you unemployable? Does your environment change your outlook on personal and professional goals?

After a short but busy couple of weeks, Brian and Jordan are back to talk about updates in their businesses and their lives. Jordan is starting to settle into Chicago and has come up with some interesting revelations. Meanwhile, Brian has also come up with some interesting revelations after listening to and analyzing customer feedback. This has all resulted in a surprising new waypoint on their roadmap.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“That’s the thing that keeps me unemployable, really, is that I own my own business and what I’m building here is an asset that will result in a much bigger win down the road.” – Brian Powered By the Tweet This PluginTweet This

Talking Points:

Jordan’s big move to Chicago
Happiness in comparison to other people and the struggles of finding your own path
The next iteration of ZipMessage
- Coaching
- Building more features and adapting what we have
Hiring, resignations, building up teams and the organization
NoCode consultants and solutions businesses

“The environment has a big impact on the conversation that I’m having in my head about ambition, money, business, and that soup.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Company as a Product

Bootstrapped Web — Wed, 10 Aug 2022 15:46:37 -0300

How do you get rid of post-illness brain fog? How do you build company culture when you’re absent? What are your steps to shipping out features?

There have been plenty of changes with Brian and Jordan since the last episode: moving and changing environments, changing energies, and changing up routines. Today, Brian and Jordan are talking about what they do to stay productive, how their teams are forming and evolving, and what sales in 2022 looks like.

What else should we talk about? What are you hearing (or not hearing from us) that you’d like to know about? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“The economy is going to do what it’s going to do. There’s not much we can do about that except work on the things we can control.” – Brian Powered By the Tweet This PluginTweet This

Talking Points:

Productivity during tumultuous/chaotic personal lives
Treating your company like a product
Updates with ZipMessage
- Creating a culture for a team
- Replacing SEO
- Asynchronous updates
- Building our own community
- Announcing features
Rally updates
- Building company culture when you feel too absent
- SaaS sales in 2022
- Building teams and laying out playbooks

“The market shifted but it didn’t implode. It’s not like everything is over. Everything feels a little more serious right now.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Product vs. Pipeline

Bootstrapped Web — Mon, 11 Jul 2022 14:54:19 -0300

What has happened in the venture funding world in the past couple of months? How do you handle repositioning? Can you lean too heavily on your product, features, and roadmaps? What do you do when one of your features falls flat?

It’s the middle of the summer edition of Bootstrapped Web. Brian and Jordan are back behind the mic after surviving family vacations, COVID, and cancelled flights. Today, Brian dives deep into repositioning and how ZipMessage has refocused in the past couple weeks. Meanwhile, Jordan talks about the biggest mistake he has made with Rally so far.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“It went from, everyone’s growing and there’s plenty of money to fund what you want to do to, all of a sudden, the water went back out and it turns out a lot of people don’t have pants on.” – Jordan Powered By the Tweet This PluginTweet This

Talking Points:

ZipMessage and Rally updates
The changes in the venture funding and the bootstrapped entrepreneur world
Repositioning and refocusing at ZipMessage
- Different pipelines: influencers, coaches, consultants, etc.
- Building CRMs (Airtable, Pipedrive)
Learning from mistakes
- Being led by product
How Jordan built a stronger working relationship with his team
- Learning from an existential crisis
The truth behind SaaS companies

“It doesn’t make sense to focus on product unless we have a daily pipeline that is ready to present that product too.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Talking to Customers

Bootstrapped Web — Tue, 07 Jun 2022 19:26:32 -0300

How do you avoid consistent churn with new products? What tools do you use to learn about your market? What influences the changes in your products?

It has been a while but Brian and Jordan are back, and they’ve brought updates with Rally and ZipMessage. Jordan talks about his fundraising efforts. Brian talks about his customer research project and what he has learned through that process.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“It went from, ‘This is going to be a piece of cake’ to… ‘That’s not what’s going on in the market.’” – Jordan Powered By the Tweet This PluginTweet This

Talking Points:

Trends in the industry and the economy
Can you avoid consistent churn numbers in new products?
Jordan’s fundraising efforts
- Investor behaviors
- Are people driven by FOMO
- The various stages in the funnel
Brian’s research project
- The lessons that Brian learned
- What motivates customers and what makes them think?
Shifting product features based on the market
- Learning from other competitors and their customers

“When you actually talk to [a customer], you not only learn a ton, it also helps me emotionally and mentally” – Brian Powered By the Tweet This PluginTweet This

Resources:

Brian’s Twitter thread documenting his customer research project

As always, thanks for tuning in. Head here to leave a review on iTunes.

Marketing in 2022

Bootstrapped Web — Thu, 28 Apr 2022 07:22:54 -0300

Brian and Jordan are both in flux between school, stressing over work, selling houses, and MicroConf. They summarize their chaotic couple of weeks and then do a deep dive on what content marketing will look like in 2022. Recently Aaron Francis (Tuple’s first marketer) talked about their $200,000 loan from Stripe and how he plans on publicly talking about how they will be spending that money. Brian and Jordan give their take on Aaron’s content marketing technique.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“You can make it happen, but not really. Your customers make it happen.” – Jordan Powered By the Tweet This PluginTweet This

Talking Points:

The timeline for Jordan’s big move
- What’s it like to sell and buy a house in this market
ZipMessage updates
- Changes on the website
- Surveys after signing up
- Coining “ZM”
- Perfect uses for ZipMessage
- Hiring strategists for SEO research
Traction with Rally
- Conversations with investors
- The importance of honesty and “when” to be honest
- Looking for marketers
Tuple’s marketing campaign
- Aaron Francis as Tuple’s first marketer
- Aaron’s tweet about their $200,000 loan from Stripe

“When a customer explains the whole value prop, it gives me so much more energy.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Traction... Then what?

Bootstrapped Web — Fri, 08 Apr 2022 11:33:57 -0300

How do you decide what features you should work on now? How do you stay unplugged during a vacation? What are the milestones and progress markers that tell you if you are on the right path?

As Brian comes back from a vacation and conference (and before Jordan leaves for his own), we’re catching up on the latest updates on ZipMessage and Rally. We’re also talking about how to best judge our own traction, and how to decide which feature to work on first.

“All the best paying customers are usually pretty quiet. ” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Staying unplugged during a vacation
Recognizing milestones and gauging progress
Updates on ZipMessage and Rally
- Dealing with big competitors head-on
- Future plans
Being a SaaS business owner and a SaaS customer
Integration partnerships: the approaches, the benefits, and the selection process
Deciding how to move forward: short term decisions versus long term/strategic decisions

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“I highly recommend working with a lawyer that you both trust and like, because there’s some moments out there…” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Everything Must Go

Bootstrapped Web — Fri, 08 Apr 2022 10:39:03 -0300

We have some big news to share before we go on a (much needed) two-week hiatus.

Brian talks about his sale of Productize, in addition to nearly every other business he has owned. Jordan talks about his latest tweet thread, responding to Moiz Ali’s criticisms of Shopify. We also talk about the power of audio, networking through podcasting, and marketing.

“The relationship built through audio is so much more powerful. It’s really hard to do that with copywriting, with a website, with ads. It’s just much harder to do.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Taking a break and staying away from the computer while on vacation
Moiz Ali’s tweet about Shopify’s problems
- The problems that they need to solve
Marketing and speaking your mind
The sale of the Productize brand (and everything else)
Networking through podcasting
- Connecting with people through audio
Competitors and marketing

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“I would focus on one thing at a time, but (in my experience) it’s not the end of the world to have a few different things going and learn and hone different types of chops and skillsets and meet different people.” – Brian Powered By the Tweet This PluginTweet This

Resources:

Jordan’s response to Moiz’ Shopify Tweet

As always, thanks for tuning in. Head here to leave a review on iTunes.

CartHook Acquired!

Bootstrapped Web — Wed, 06 Apr 2022 15:55:33 -0300

What do you get out of conferences? Do you mute competitors on Twitter? How to you utilize Twitter as a budding SaaS entrepreneur?

After a brief hiatus, Brian and Jordan are back with some big news: Carthook was officially acquired! Jordan shares what details he can about the acquisition as well as the process and journey of the company.

They also talk about the upcoming MicroConf and what conferences can do for you. After all, they’re not just about networking, there are a lot of things gained when meeting with colleagues, competitors …and podcast listeners.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“The thing that I want out of a conference is a huge boost of confidence.” – Jordan Powered By the Tweet This PluginTweet This

Talking Points:

Carthook officially acquired
- Shutting down and selling the supported Shopify app
- A mixture of emotions after a crazy journey
Unwinding after the stress of a trip
What conferences can do to your mindset
- The energizing effect of conferences
- Meeting podcast listeners
How it feels to be an anonymous company in a space with huge companies
Competitors on Twitter: To Mute or Not To Mute
How many people do you need for a startup?
Access the gratitude

“Since Day 1, we’ve had a fundamental difference of what ZipMessage is and that’s the intake ability.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Tokenizing

Bootstrapped Web — Tue, 22 Feb 2022 15:43:03 -0400

How are you and your company changing with the times? Are you considering tokenizing your software company? Have you begun adopting web3 technology?

Today, we’re talking about marketing, hiring developers and writers during “The Great Resignation,” and tokenizing. Token-based economics is the future of SaaS. Web3 tech isn’t just in the future, it’s happening right now.

“I would aim for zero commercial partnership: no rev share either way. Those are the best partnerships.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Dealing with bad days, finding additional sources of joy
Big Snow Tiny Conf (East)
Marketing: calming down after product launch and initial promotion
- Integrations and examples of
- Writing and promotion
Fundraising and tokenizing
- Adopting web3 technology
Transitioning between developers during “The Great Resignation”

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“I’m so excited to be a part of this podcast now. I feel like I get a front row seat and I’m slowly starting to see how Web3 actually starts to change things.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

So Meta

Bootstrapped Web — Tue, 08 Feb 2022 23:49:33 -0400

Brian and Jordan are having a great time as they ride good days, give great updates, and look forward to some exciting things in the near and far future.

In today’s unscripted and random episode, Brian and Jordan give us some great news in terms of business updates. They also talk about one of the bigger customer issues when it comes to running a SaaS company. Not to mention, a deep dive into the metaverse: what does the future look like with Web3?

“What shoe will need to drop in order for Web3 solutions or applications or products or services or platforms to spill over into the wider market?” – Brian Casel Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

That wonderful feeling when things are starting, building, and rolling
How to keep the momentum going
SaaS issues: the discomfort of having most of your market be anonymous to you
Foreshadowing of why we should take the metaverse seriously
- Will Web3 be corporate-owned or user-owned?
- Monetization through advertising and other types of models
TinyConf, Disney, and other events in the near future

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“No one is going to get to zero. But you do need to remain underneath the line of ‘too frustrating.’ And that line has not been determined yet.” – Jordan Gal Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Wheels Are Turning

Bootstrapped Web — Tue, 18 Jan 2022 15:26:43 -0400

Brian has sold ProcessKit! He explains the surprisingly stress-free and smooth process. Jordan talks about his upcoming move to Chicago. Meanwhile, they also give updates on Rally’s marking and sales funnels, and prioritization at ZipMessage.

Today’s episode is filled with business updates, optimism, and great outlooks for 2022. Don’t forget to check out ZipMessage on ProductHunt!

“I prioritize [the reliability of recording and playback] over shipping a brand new feature.” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The sale of ProcessKit
Chicago, look out for Jordan
ZipMessage on Product Hunt
Is Rally ready to go to market?
- Marketing funnels and sales funnels
Prioritization at ZipMessage
ZIpMessage conversion emails

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“What helps me is knowing what the journey looks like.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

2021/2022 New Year reflections

Bootstrapped Web — Tue, 18 Jan 2022 15:19:40 -0400

Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th

The Chaos

Bootstrapped Web — Mon, 10 Jan 2022 13:37:17 -0400

Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootstrapped Web.

Jordan talks about his hangups and why his need for idea exploration is causing difficulties with his leadership team. Meanwhile, Brian is continuing to navigate the challenges of starting a new business with a niche target market. Is podcasting the answer? They also go over some interesting tools for searching for the perfect podcast, marketing to specific groups, as well as their excitement for Andrew Chen’s newest book, “The Cold Start Problem.”

“I’m very much a middle sibling when it comes to management at the leadership level. It’s very collaborative.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

A new ZipMessage website
Hiring generalists or specialists
Challenging leadership team conversations
Marketing and and outreach for the podcasting community
- Influencer outreach
- SEO plays and search demands
Andrew Chen’s newest book release

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“I’m getting these things dialed in. It’s difficult but I think it’s finally starting to come together.” – Brian Powered By the Tweet This PluginTweet This

Resources:

SparkToro

Podseeker

“The Cold Start Problem: How to Start and Scale Network Effects” by Andrew Chen

As always, thanks for tuning in. Head here to leave a review on iTunes.

Define Traction

Bootstrapped Web — Mon, 10 Jan 2022 12:38:37 -0400

What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer milestone.

Today’s episode is all about the different ways you can build traction but also the different ways you can define traction.

“If you can work directly with your audience to monetize the people who are crazy about you, you can make more money in a different model, and everyone is the most happy.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Marketing site changes at Rally
- Getting credit for speed and momentum
- NFT Projects for marketing
ZipMessage website updates
- Personalization for customers
- Creating a WordPress plugin
- Premium enrollment/Private or public conversations
Phases of Product/market Fit
- What does traction feel like?
- Are customers willing to adapt for your product?

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“We did things a certain way and, if they didn’t like that, either they didn’t become a customer or they adapted. And we had plenty of customers who adapted.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Chicken or Egg Development

Bootstrapped Web — Wed, 08 Dec 2021 14:40:35 -0400

When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities?

Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free plans, website redesigns, and preparing themselves for an influx of activity, there is a lot going on behind the scenes. Exciting things are happening but with excitement come daunting tasks, important decisions, and possible mistakes.

“What we’re about to do is, we’re about to scramble people’s priorities in a challenging way.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

New activity with ZipMessage
Onboarding first merchants with Rally
- Remembering the excitement and joy that comes from sales demos
Experimenting with a free plan on ZipMessage
- The differences between the free and paid plan
Rally’s all-hands to mentally prepare for a different challenge: new priorities
ZipMessage’s website redesign
The daunting task of revamping landing pages

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“Nothing like having real customers to really drive what’s really important.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Go to Market vs. Marketing

Bootstrapped Web — Tue, 09 Nov 2021 18:02:40 -0400

What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and ZipMessage.

Jordan talks about Rally’s methodical blog posts, which will be released slowly over the next few months. Brian shares some of the new features on ZipMessage and his plans for ‘going to market.’ They also talk about how uncomfortable and rewarding the process can be. ‘Going to market’ is humbling and requires authenticity after all.

“There’s a lot going on inside the company and inside the product. And ‘go to market’ is one element of that but you can’t just focus on that because there’s a lot of other things going on that we have to get right.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The difference between going to market and marketing
What is involved when you go to market
Marketing techniques and content creators
Different versions of networking

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“It’s this idea (especially in the first year) where you’ve got to be doing activities that are introducing the product to more and more new people.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

How to Fund a Startup

Bootstrapped Web — Tue, 09 Nov 2021 17:38:59 -0400

Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to lead a round?

Meanwhile, Brian gives updates on ZipMessage including marketing projects (comparison/competitor pages), hiring designers for website redesigns, and falling behind on content.

“What we did was, we only worked with seed funds, because I wanted everyone to be focused on success at the seed stage.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Rally funding announcements
Planning for funding and growth for Rally
Strategic funding approaches and plans
Comparison/competitor pages
Website redesigns
SEO content opportunities for ZipMessage
How to get the right response and the right person for the job

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“In this early stage, there is an element of creativity and strategy. I have to bring that knowledge to the project. I can’t just hand that off to someone else.” – Brian Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Should We Rename the Podcast?

Bootstrapped Web — Tue, 26 Oct 2021 23:12:55 -0300

Bootstrapped Web is no longer bootstrapped, on either side!

Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market.

Brian takes funding from Calm Fund (formerly Earnest Capital), which has been a month in the making. He talks about the different decisions and considerations to be made when exiting Audience Ops and taking funding for ZipMessage.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“I love this [angel funding] ecosystem and how it’s been evolving.” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Jordan’s “coming out” strategy for Rally
Brian takes funding from Calm Fund (formerly Earnest Capital)

“I have been sitting on so many secrets, it’s not healthy. It’s not healthy to be quiet and fearful. It’s not my natural state.” – Jordan Powered By the Tweet This PluginTweet This

Resources

Rally Blog

“Your Startup is a Movement” by David Sacks

As always, thanks for tuning in. Head here to leave a review on iTunes.

Audience Ops Changes Hands

Bootstrapped Web — Thu, 23 Sep 2021 03:00:00 -0300

Some news! Brian has sold his business, Audience Ops, to JD Graffam! And what better way to announce this transition than to bring JD on the show!

Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now underway.

If you’re thinking about pursuing an exit from your business or thinking about acquiring one, we hope you’ll find some of our real-world experience from this deal helpful.

You can read Brian’s blog post that dives deeper into the deal and thought processes that led up to the exit.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

Mentioned on today’s episode:

Audience Ops

JD Graffam on Twitter

JD’s article, Fourteen Things That Will Keep Me from Buying Your App

As always, thanks for tuning in. Head here to leave a review on iTunes.

Marketing ideas

Bootstrapped Web — Thu, 19 Aug 2021 03:00:00 -0300

Introduction:

Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, their very professional podcasting process, Rally’s current markers and goals, and Brian’s exciting marketing ideas.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“Something didn’t sit right. It wasn’t ambitious enough. We need to challenge ourselves more.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Forming a new corporation with ZipMessage
- The need for full-service accounting/admin
Our “professional” podcasting process
- Listening back on episodes to help sharpen your gut
Rally’s current markers
- Do we have what we need to raise money?
- Working backwards from and mapping out the goal and markers
- How to project numbers at this stage
- Creating a safe space to make mistakes, changing your mind, and getting appropriate push-back
Marketing ideas and promotion
- The Shipped Podcast (using ZipMessage)
- Testing audiences and different marketing platforms
- Podcast sponsorships: targeting small podcasts
- YouTube advertising
- Alternative free trial program

“Let’s not think of the worst case scenario but the realistic scenario.” – Brian Powered By the Tweet This PluginTweet This

Mentioned on today’s episode:

Office Engine

Gusto

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes.

Back and Running

Bootstrapped Web — Thu, 05 Aug 2021 03:00:00 -0300

After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“Growth as headcount as an acceptable growth metric. And the reason for that is if you’re not shooting for
profitability and you’re shooting for milestones.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The relationship between founder and VC
- Headcount versus profitability as growth
- Hiring a recruiter
ZipMessage goals
- Prioritizing requests
- Setting up new features
- Opening it up to the public
- The Shipped podcast
- Brian’s new technical marketer
Introduction of technology to others
- Niche tools
- Summit, whiteboards that do math. The easiest way to create, test, and present your logic.
Taming the chaos

“If profitability isn’t the goal on this path (which makes sense), what are the metrics that you’re looking at for the next 12 months or 18 months?” – Brian Powered By the Tweet This PluginTweet This

Mentioned on today’s episode:

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes.

Metrics & Hiring Funnels

Bootstrapped Web — Thu, 24 Jun 2021 03:00:00 -0300

Brian and Jordan are back to back-to-back weeks before vacation and travel plans kick in because… It’s summertime! While Jordan deals with a minor lacrosse injury, they both gush over Matt Medeiros, and give updates on their latest business endeavors. They talk about the progress on the search for a media creator for both Rally and ZipMessage, hiring funnels and hiring hurdles, getting feedback, and ways to get out of a funk.

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here.

“I saw a ZipMessage pop up in my Slack the other day. I love seeing it organically used because that’s the tool that fits.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Matt Medeiros and the media creator role
The technical side of ZipMessage
Reading stats and getting feedback
Getting out of a funk
Completing tasks, self-induced stress, and forgiveness
Figuring out the right workflow and the right people
Hiring funnels, hurdles, testimonials, and role-specific adjustments

“People get value from it and they don’t tell you they’re getting value from it. It’s just happening and you don’t see it right in front of you. You have to see the stats.” – Brian Powered By the Tweet This PluginTweet This

Mentioned on today’s episode:

Matt Medeiros’ Twitter Thread on the media creator role

ChartMogul

DynamiteJobs

Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace

Brian’s 2 positions open for applications:

Media Creator

Technical Marketer

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes.

Hiring Media Creators

Bootstrapped Web — Thu, 17 Jun 2021 03:00:00 -0300

Brian and Jordan are back with updates about diving headfirst into team sports with an “old man lacrosse leagues,” to celebrating 10-year wedding anniversaries, job postings, and creating messages that resonate with customers. They’re covering a little bit of everything today.

Brian shares a couple of interesting job openings based on ZipMessage: a media creator and a technical marketer. Check out the job opening for media creator if you love to create content, are comfortable telling stories, and coming up with creative new ideas. He is also looking for a technical marketer who will work on distribution and optimizing channels and SaaS funnels. If you are interested in either job position, use the links below to apply.

Media Creator

Technical Marketer

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message here

“You want the authentic version of the media and the audience and value, and then allowing for a bridge from there, over to the product.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

ZipMessage Updates:
- Growth and skepticism
- Job openings:
  - Media creator
  - Technical marketer
Creating a community
The Bloomberg Model
Axios
Conversations and conveying the Rally message
- What to lead with
- How to make your message resonate
Shopify opinions
Brian is hiring for 2 roles:

Media Creator

Technical Marketer

“If you want an engaged community where they interact with each other, the audience has to come first.” – Brian Powered By the Tweet This PluginTweet This

Mentioned on today’s episode:

Leave us a message here

As always, thanks for tuning in. Head here to leave a review on iTunes.

Raising The Bar

Bootstrapped Web — Thu, 03 Jun 2021 03:00:00 -0300

Brian and Jordan are back with no excuses and plenty of updates for both Rally and ZipMessage. Today’s topics are all about roadmaps, leading tech teams, and ecommerce marketing. While ecommerce has been around for a while, SaaS is evolving in the way it is marketed and sold. What are your thoughts on SaaS marketing strategies? Do you prefer leading a large tech team or would you rather keep your team small and easily manageable? What are your thoughts on the importance of communication for teams who work remotely?

If you have any questions, comments, or topic ideas for Brian or Jordan, leave a message here.

“When you start to talk about a bunch of people, all in coordination, all in different time zones, all on different things, that stuff is just magic to me.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The next step for Rally
The many uses for ZipMessage
- Combining live Zoom calls with asynchronous follow-ups
- Direct Slack integrations
- The ZipMessage roadmap
Leading a tech team
- Requirements for leadership
- The importance of communication
Different strategies for marketing

“The way that I think about integrations generally is, it’s more about, ‘Does it solve a customer problem and customer conversion?’” – Brian Powered By the Tweet This PluginTweet This

Mentioned on today’s episode:

Patrick Campbell’s tweet about building a media brand, monetizing with software

Unthinkable podcast by Jay Acunzo

Our stuff:

Leave us a message here

Rally On

Bootstrapped Web — Thu, 20 May 2021 03:00:00 -0300

It’s a big day here at Bootstrapped Web now that Jordan can talk more openly about his newest endeavor: Rally. Brian and Jordan talk about what Rally is, breakdown Rally’s elevator pitch, as well as the steps Jordan has taken up to this point. They also get into a few updates with ZipMessage. Brian talks about the possibility of building a small team and the stigma around hiring a team full of contractors.

Are you a freelancer looking for a little work? Are you a marketing specialist? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here

“I’m in the middle of that thing that happens if you post a Twitter thread just at the right time. It’s fun. You have to remember to enjoy the fun days. This is one of those fun days.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Rally and RallyOn.com
- What does Rally do for customers?
- What does it mean to go headless?
- Definition of “Modern brands”
- What makes Rally different?
Enjoying and being in the moment
The importance of elevator pitches and headlines
Multiple fits and building relationships
The next step and roadmap for Rally
ZipMessage updates
- Doing everything yourself vs. building a small team
- Contractors and freelancers vs. employees
- The stigma behind hiring overseas
Creating your perfect company culture
Brian’s marketing talent wishlist:
- Technical marketer (Google analytics, SEO, etc.)
- Media producer (podcasting, interviews, etc.)

“I’m already all in in terms of hours. But to really go all in, I need a team with me.” – Brian Powered By the Tweet This PluginTweet This

Resources:

Leave us a message here

Rally On

Josh Pigford’s Maybe company compensation model

Sahil Lavingia on Gumroad’s team model

As always, thanks for tuning in. Head here to leave a review on iTunes.

Bugs vs. Customers

Bootstrapped Web — Thu, 06 May 2021 03:00:00 -0300

Brian and Jordan are back behind the mic for the second week in a row. Today they’re focusing on bugs over customers, or should it be the other way around? After some project and business updates, they talk about the early stages of development and launch for a new product. How do you decide if this new project is worth it? How do you find people who are as excited about it as you are?

If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb.

“I’m slowed down by the product and the bug-fixes.” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Project and business updates: marketing, development, and not moving fast enough
Talking with partners and agencies versus potential customers
Taking a position and what that means for a business
How to decide whether a project or a product is worth the time?
The Catch-22 of starting and growing a new business
How to evaluate a “head-of-growth” expert
Pivotal moments in ZipMessage and secret projects
Growth hacks for ZipMessage

“My favorite thing (the thing that I’m good at) is articulating that future vision clearly.” – Jordan Powered By the Tweet This PluginTweet This

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Staying positive

Bootstrapped Web — Thu, 29 Apr 2021 03:00:00 -0300

Brian and Jordan are back with big news about both of their newest projects. Today they’re doing a deep dive into some of the mental struggles when you start something new. Some touchy-feely topics, some logistics, and back to touchy-feely topics: a typical Bootstrapped Web episode. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave a message for Brian and Jordan on their ZipMessage account at https://zipmessage.com/bootstrappedweb.

“We need to complement each other more. Because everyone asks for feedback, nobody asks for compliments.” – Jordan Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

Updates on Jordan’s secret product
Feeling down and (surprising) external motivators
What founders do and the meaning of being a founder
The importance of compliments and empathy
Updates, changes, and uses for ZipMessage
Framework and patterns in successful niche SaaS products
- Three-phase process: enter, lean-in, all-in

“For founders, literally all we do is solve problems. What’s the next problem to solve? What’s the next thing that’s not working? Every single day.” – Brian Powered By the Tweet This PluginTweet This

Resources

ZipMessage

New! zipmessage.com/bootstrappedweb

As always, thanks for tuning in. Head here to leave a review on iTunes.

Never Fast Enough

Bootstrapped Web — Thu, 15 Apr 2021 03:00:00 -0300

Brian and Jordan are back before Brian leaves to scratch his travel itch. Today, they are talking about the things they can control (launching ZipMessage and Jordan’s new company), while also touching on a couple things they can’t control (vaccines and concerts). They also spend a little time talking about Josh Pigford’s amazing public journey, from exiting Baremetrics to starting his own company for modern financial planning & wealth management. How do you handle your professional persona? Are you an open book on your social media accounts? Are you strategic about what you post? Brian and Jordan discuss Josh’s strategic and surprisingly open discussions on Twitter and how they differ in their social media personas.

“I did want to step in and reiterate some of my larger goals and priorities to the team on Audience Ops, about what makes Audience Ops great. Kat really did that well, but I want to make sure that the team really knows, ‘This is why things work so well here. Let’s keep this going.’” – Brian Powered By the Tweet This PluginTweet This

Here are today’s conversation points:

The roller coaster of ZipMessage onboarding
Finalizing copy and launching landing pages
Audience Ops team changes and transitions
The vision at Audience Ops
Expectations, emotions, and performative reactions during Monday morning calls
The importance of understanding the “Why”
Josh Pigford’s exit from Baremetrics and his professional trajectory…in public
Angel investing and asking for money

“If you have an audience and you want to start a company, at this point, you can just ask for money. You can legally, publicly ask for money.” – Jordan Powered By the Tweet This PluginTweet This

Resources

Maybe.co

Josh Pigford’s Twitter

As always, thanks for tuning in. Head here to leave a review on iTunes.

Let’s Be Less Wrong in 2021

Bootstrapped Web — Thu, 24 Dec 2020 02:00:00 -0400

Brian and Jordan are rounding out 2020 by looking back and looking into the future. Brian talks about taking a break for the next couple weeks, ProcessKit updates, and looking back to see what he was wrong about when thinking about 2020. Jordan talks about a couple podcasts he was a part of, fun holiday parties, and minimizing risks of wasting hours. They also go over some final thoughts about the holidays, and what they plan on doing on their vacation.

[tweetthis]“What were all the things that I was wrong about? In the last year?” - Brian [/tweetthis]

Here are today’s conversation points:

Taking a break and the importance of stepping away
- What is burnout?
- Macro versus micro expectations for ourselves
Podcasts that Jordan has been a part of lately (Greylock, Better Done Than Perfect)
Looking back on 2020
What happens in ‘21?
ProcessKit updates: onboarding flow, new home pages, etc.
Holiday parties (and possibly monthly happy hours) using GatherTown
The process for validating products

[tweetthis]“I don’t do that many hours of intense work and writing and that sort of thing, but it is the constant thinking and worrying.” - Jordan [/tweetthis]

Resources:

Greylock (Greymatter): “Mike Duboe | The Rise of Headless Commerce”

Better Done Than Perfect: Radical Onboarding Experiments with Jordan Gal

Better Done Than Perfect: Launch Lessons & Product Surveys with Rand Fishkin

As always, thanks for tuning in. Head here to leave a review on iTunes.

All the Things

Bootstrapped Web — Thu, 10 Dec 2020 02:00:00 -0400

Vote for us on the SaaS Podcast Awards!

Jordan and Brian are back with new podcasting gear and set-ups. Today’s topics cover a little bit of everything: from making quality content, to morale boosting Zoom meeting activities. They are also talking about Jordan’s experience working with Shopify, Brian’s 2021 goals for consistency, as well as a surprise nomination, onboarding and conversion, marketing and tracking, and niche podcasting.

[tweetthis]“If you keep hammering on a topic that resonates with people, stuff still sits on the internet and attracts people.” - Brian [/tweetthis]

Here are today’s conversation points:

Making quality content
Friday snapshots, Spotify Wrapped Year in Review
Black Friday and Cyber Monday wrap-up
Shopify checkouts, quirks, and limitations
Nomination for bootstrapper podcasts
ProcessKit onboarding and the core of the product
How to change from conversion to paid?
Marketing
- Marketing and tracking from two different sources
- Paypal, what?!
- Focusing your marketing efforts; niching down
Goals for 2021: consistency
Podcasting in a niche versus having a wide audience

[tweetthis]“When you’re selling in an app store but you have your own website, there is a big disconnect on tracking.” - Jordan [/tweetthis]

Resources:

Microconf: SaaS Podcast Awards

As always, thanks for tuning in. Head here to leave a review on iTunes.

Satisfying Customers

Bootstrapped Web — Thu, 12 Nov 2020 02:00:00 -0400

On this episode of Bootstrapped Web (dubbed the “anything but election talk” episode), Jordan and Brian go over Carthook’s exciting launch in the Shopify App Store and ProcessKit’s visual upgrade. Brian also has a couple of aces up his sleeve when it comes to high level changes as well as day-to-day uses for ProcessKit. Today the focus is all about what it means to satisfy customers: new and existing customers. How do you convert trial customers? How fast should you handle feature requests? How do you deal with the pressures put onto you by customers? How to show your constant level of progress but how do you filter customer feedback/expectations?

[tweetthis]“Anytime you’re talking about visual user updates, especially if it affects the entire app (which this did) you get nervous. People don’t like change, even if it’s better change.” - Brian [/tweetthis]

Here are today’s conversation points:

The Carthook logo is in the Shopify App Store!
- Team morale
- Departments that need Jordan’s focus
- Updates, expectations, and reviews
The limitations of being both the designer and founder of a product
ProcessKit upgrades:
- To dashboard or not to dashboard?
- Email templates with liquid tags to increase the dynamic changes for these templates
The pressure of “What’s next?” and prioritization
The current competitive climate in SaaS
- Pipe
- MainStreet
- Visualize Value

[tweetthis]“I think we’ve spoken before about how I look at the company as like, ‘Where is the fire burning...the hottest?’ At any point in time it’s not like everything’s on fire or everything requires attention. There’s usually one part of your company where there’s more going on.” - Jordan [/tweetthis]

Resources:

Jason Lemkin’s post about Dashboards

As always, thanks for tuning in. Head here to leave a review on iTunes.

Calm Before the Storm

Bootstrapped Web — Thu, 05 Nov 2020 02:00:00 -0400

Jordan and Brian are back after a few weeks. It is election week; that means a lot of stress and a lot of chaos. But before that stuff hits the fan, Jordan is launching a new Carthook product inside the Shopify app store and Brian has been redesigning the ProcessKit app to fix little frustrations. They’re also talking about structure, spreadsheets, and the importance of app store reviews

[tweetthis]“As we started to add more and more features, the overall structure and experience (and I’m talking about very detailed things) hasn’t kept up and so I wanted to solve for all of these little frustrations in the app that have accumulated.” - Brian [/tweetthis]

Here are today’s conversation points:

New Carthook products inside the Shopify App Store
- Preparations and anticipating the launch
- Spreadsheets and scenarios
- The Prisoner’s Dilemma
- Dynamic pricing and price points
ProcessKit App redesign
- Progress in SaaS products
- Community-based promotions
- Marketing and funneling
Being able to separate yourself from your business
The importance of customer experience and app store reviews
Jordan’s new obsession: Cohere

[tweetthis]“It is a prisoner’s dilemma. You’re stuck, you don’t have all the information. What you do has a big impact on them, what they do has a big impact on you. But you’re not colluding.” - Jordan [/tweetthis]

Resources:

How to Price Your SaaS Product by Patrick Campbell

As always, thanks for tuning in. Head here to leave a review on iTunes.

Good morning

Bootstrapped Web — Thu, 15 Oct 2020 03:00:00 -0300

Today Brian and Jordan are talking about deadlines, Black Friday, and a little bit of introspection. They go over their love/hate relationship with mornings. They also take a deep dive into hopes, dreams, dedication, and hiring true believers.

[tweetthis]“I still really believe in dedicating time to writing tests and for us that really means integration tests and feature tests.” - Brian [/tweetthis]

Here are today’s conversation points:

The Carthook deadline
How the new ProcessKit developer stepped up
Testing features, web integration expectations
Different ways of coping with stress
The importance of mornings:
- Brian’s morning routine
- Jordan’s morning routine
- Can you change whether or not you can be a morning person?
Hopes, dreams, and dedication
- “What is the worst case scenario here?”
When it is okay to forgo delegating and doing things yourself?
- Freelancing versus Full-Time Employee
- Marketing projects
- Hiring a true believer

[tweetthis]“When you make a decision, go harder at it.” - Jordan [/tweetthis]

As always, thanks for tuning in. Head here to leave a review on iTunes.

Talkin shop with Ian Landsman

Bootstrapped Web — Thu, 08 Oct 2020 02:10:00 -0300

On today’s episode of Bootstrapped Web, Brian and Jordan are joined by Ian Landsman from HelpSpot. Ian has made product after product over the years, from UserScape to HelpSpot to LaravelJobs and Thermostatio. You can find him on Twitter or you can learn more about him on his website.

Brian, Jordan, and Ian are talking all about podcasts, business models, and privacy on the internet. They also go over the lessons they’ve all learned from previous products and projects they have been involved in.

[tweetthis]“How many years, how many decades, can you keep pushing project management software when that space just gets so big and so competitive?” - Brian [/tweetthis]

Here are today’s conversation points:

Ian’s potential new podcast: structure or no structure?
Hey, Clubhouse, and other email services
The hidden cost of privacy and complacency in a product
Previous products, projects, and the lessons learned
How involved Ian, after being 15 years into HelpSpot
What does feature development look like for Ian?
Optimizing websites as supplementary platforms
Business models: per user, paying per clients
Are demos worth it?
Affiliate programs and consulting hang ups for ProcessKit
- Third party hosting and consulting companies
Real-time brainstorming about onboarding consultants

[tweetthis]“Clubhouse jumped the shark from being exclusive to just being ‘annoyed that you couldn’t get in and now you’re resentful.’ And then, of course, I got an invite and a DM a minute later. [laughs]” - Jordan [/tweetthis]

As always, thanks for tuning in. Head here to leave a review on iTunes.

Company Design

Bootstrapped Web — Thu, 01 Oct 2020 02:34:00 -0300

We’re in a great mood on today here atf Bootstrapped Web. We’re talking about drive-in movies, apple picking, AirBnB’s, Twitter, and business updates. This episode is a bit of a topic potpourri is as we cover new features, hiring and interview processes, big picture visions, and building communities.

[tweetthis]“Aside from the obvious goal of marketing (which is to grow traffic and leads and sales), I think the bigger goal should be to build community.” - Brian [/tweetthis]

Here are today’s conversation points:

ProcessKit fields and features
- Web developer updates
Carthook’s newest app for Shopify
- Their new full-time, in-house product designer
Switching ProcessKit marketing site to a static site to Wordpress
- Static vs Dynamic
The hiring and interviewing process
- The importance of culture fit and temperament
Looking at the big picture and company design
- “What kind of company do I want to build?”
Building an ideal community, and longevity
- Building relationships
Snap Friday and current hobbies

[tweetthis]“Our culture fit is a nice, optimistic, happy person. And that might sound really thin but it really matters. If you’re naturally optimistic and curious, it leads to happiness, even in times of stress.” - Jordan [/tweetthis]

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Should You Audience?

Bootstrapped Web — Thu, 17 Sep 2020 02:00:00 -0300

Brian and Jordan are back behind the (brand new) mics. They’re reminiscing about the beginning of the podcast, the fires in the west coast, and catching up on the latest news in the industry as well as their businesses.

[tweetthis]“From a design standpoint, in the first year of an app, so many things change, like, in terms of the feature set and the scope.” - Brian [/tweetthis]

Here are today’s conversation points:

The tail end of the hiring process
- Using the Silo strategy
5 years in the business of podcasting and with our products
Personnel shake-up in ProcessKit
Finance topic: the launch of Long Term Stock Exchange
Making progress in different stages of products
New feature: Dynamic roles
Competition
Audiences Building
- Getting enjoyment from personal and professional endeavors...or not
- “You are not a product.”
- The Billion Dollar Blog
- How important is audience building?

[tweetthis]“So much is determined by that initial burst of energy and that initial first year or two that sets you up on this trajectory.” - Jordan [/tweetthis]

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

The Next Chapter in the Product

Bootstrapped Web — Thu, 10 Sep 2020 03:00:00 -0300

It’s been a little while but Brian and Jordan are back behind the mics. On today’s episode, they’re talking about vacations, a long first week back, marketing, big news with Carthook, cold emails, and guest features.

[tweetthis]“I wanted to get things moving and basically get things up and running, so I hired a marketer” - Brian [/tweetthis]

Here are today’s conversation points:

Carthook, Shopify, and working together
How Shopify works
What cold emailers get wrong
Conversion rates and automation
Initial onboarding systems and portals
Guest features
Questioning ourselves
Benedict Deicke’s Tweet

[tweetthis]“The wins don’t last very long. They just whiz by and then it’s just like, ‘Onto the next challenge, onto the next challenge, onto the next thing.” - Jordan [/tweetthis]

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Chicken or Egg or Fundraise

Bootstrapped Web — Thu, 20 Aug 2020 02:00:00 -0300

We’re back with “Boo-strapped Web”. We’re behind the mic talking about stress, marketing, executing decisions, and guilt over new hire experiences. Lastly, we’re going over the latest news in startup financing, which could blow everything out of the water: rolling funds.

[tweetthis]“Saas is an ongoing chicken or egg problem and it happens more in the product side and maybe even more so on the marketing side.” - Brian [/tweetthis]

Here are today’s conversation points:

New Hire Experiences
- New employee Slack introductions
- PoweredBySearch’s great online course/training for new hires
SaaS = Chicken or Egg Problem
Marketing
- Zapier
Rolling funds
- Sahil Lavingia (Gumroad)
- Exemption 506-B, 506-B, and Solicitation
- Funding per quarter
- Better access to capital, on better terms
- Transparency will be key

[tweetthis]“Audience is now a new form of power, it’s investing power. So if you have an audience and you take a stance and people believe in what you believe in, you can just raise your hand and now you’re a VC, yourself. If a fund can raise money this way, why can’t a startup?” - Jordan [/tweetthis]

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Hello Competitors

Bootstrapped Web — Thu, 06 Aug 2020 03:00:00 -0300

Today we’re talking about camping ratios, COVID and Black Friday, the eCommerce boom due to COVID, emotions versus moods, Twitter, and competitors. We go over some bold and unique marketing strategies with ProcessKit, how we’ve won Jordan over in the “Working-from-home” battle, and about hiring contractors and coaches.

[tweetthis]“He found the reviews where they’re complaining about the competitors and we’re, like, featuring those. Not to just poke at them but to show, ‘If [the customers] complain about this, here’s how ProcessKit solves that.” - Brian [/tweetthis]

Here are today’s conversation points:

COVID trends and looking into the near future
Competitor hype and making a dent in the market
“Aggressive” marketing in ProcessKit
People management and coaches
Hiring contractors for marketing strategies
Embracing the working from home life

[tweetthis]“Identify the difference between an emotion and a mood. A tweet from a competitor, that creates an emotion. But my mood is dictated by, like, my family and my wife and my amazing kids and our health. But how to separate those two out and not let an emotion ruin the mood, feels like a new skill.” - Jordan [/tweetthis]

Resources:

As always, thanks for tuning in. Head here to leave a review on iTunes.

What does VC really mean? And marketing.

Bootstrapped Web — Thu, 23 Jul 2020 03:00:00 -0300

We’re back after a two-week break. More specifically, a camping and Niagra Falls break. Today we go over two kinds of VC: vacations and venture capital. Not to mention, we go over ProcessKit’s newest marketing news, Ali Mese’s article on Medium, and our thoughts on positioning.

[tweetthis]“I’m trying to understand the type of person who discovers a SaaS product and starts emailing their support every single day for fourteen days straight, with multiple paragraphs.” - Brian [/tweetthis]

Here are today’s conversation points:

How do you know when you need a vacation?
Brian’s new purchase
How often do you contact support?
Marketing
- Positioning and building for additional platform integrations
- Ali Mese’s article on Medium
- Keyword research and other marketing ideas for ProcessKit
- Know who your best ideal customers are
Jordan’s lessons in venture capital

[tweetthis]“I always have in my mind that I have to be having the right dream. So if you win, make sure you want that outcome.” - Jordan [/tweetthis]

Resources:

“To Build a Business Empire, Own an Opinion, Not a Marketing Budget” by Ali Mese (published on Medium)

As always, thanks for tuning in. Head here to leave a review on iTunes.

What Should We Talk About?

Bootstrapped Web — Thu, 02 Jul 2020 03:00:00 -0300

We’re back in the studio with a very special agenda… in that we don’t have an agenda today. So we turned to Twitter to ask listeners and followers what topics they would be interested in hearing about. If you have a question or a comment you’d like us to cover in a future episode, feel free to tweet it to us! Today we cover everything from product management to marketing to hobbies.

[tweetthis]“To me the most important part of [product management] is the customer feedback.” - Brian [/tweetthis]

Here are today’s conversation points:

Product Management with ProcessKit and Carthook
Hiring and delegating in the early days of a product or business
Marketing these days is a puzzle
Twitter addictions
Managing product requests from users
Marlo, the special guest
How much time and money do you spend on hobbies?
COVID budgeting
Family and school plans for the future
Twitter conversations:
- Financing and Funding
Day-to-day tasks: A Day in the Life of Jordan Gal
How we feel about our businesses and progress

[tweetthis]“It’s a muscle; that ability to trust other people with very very critical things. It’s not an easy thing to get over.” - Jordan, on delegating important tasks to someone else[/tweetthis]

Resources:

The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It, by Michael E. Gerber

@PoweredBySearch Twitter

Twitter: @JordanGal

Twitter: @CasJam

As always, thanks for tuning in. Head here to leave a review on iTunes.

Heyyy + People-ing, Building & Marketing

Bootstrapped Web — Thu, 25 Jun 2020 03:00:24 -0300

We’re back and we have so much to talk about. First off, we’d like to dedicate this episode to Ian Landsman and his twitter account. “Hey” seems to have taken Twitter by storm. We’ll talk about how we feel about that, and, of course, we’ll update you on what’s going on in our businesses as well.

[tweetthis]"For an everyday email app, I need it to be as clean and simple as possible. But the experience and the functionality and the UI makes a lot of sense, I think." - Brian, on Hey from Basecamp [/tweetthis]

Here are today’s conversation points:

Hey (from Basecamp): the pros & cons, and the controversy with the Apple Store
Hiring at Carthook
- Recruiters
- People Ops person
- Culture and training
Onboarding updates at ProcessKit
To build or to market, that is the question
- Forms features
- Marketing tasks on my to-do list

[tweetthis]“Now we have 8 completely new people we’ve never met, we probably won’t be able to see for, like, a year. How do we give them a good experience? How do we make sure they don’t feel isolated?” - Jordan, on hiring new team members during COVID [/tweetthis]

Resources/Links:

HEY - Email at its best, new from Basecamp

Help Scout - Simple Customer Service Software and Education

As always, thanks for tuning in. Head here to leave a review on iTunes.

SaaS Onboarding & Recruiting at Scale

Bootstrapped Web — Thu, 18 Jun 2020 03:00:00 -0300

We’re back behind the mic today after a one-week hiatus. We had originally recorded an episode last week (which addressed current events) but decided not to publish it. Our hearts do go out to everyone in this time of chaos and uncertainty.

This week, we’re back, talking about business, bad habits, and kindergarten graduation parades. We’re talking about ProcessKit’s onboarding updates and one of their newest customers. We’re also talking about Jordan’s big problem and his recruiting and hiring issues.

[tweetthis]"He turned the tables on me and we bartered. So he’s a paying customer of ProcessKit and I gave him a pretty big ProcessKit plan in exchange for him writing three of these pages for ProcessKit." - Brian [/tweetthis]

Here are today’s conversation points:

Jordan’s big problem: putting off strategic tasks, but then having no energy
Brian’s early morning exercise schedule
Brian’s ProcessKit’s onboarding updates
1. The various levels of customers
2. Tools, widgets, checklists, and onboarding courses
3. What each customer needs in order to be successful
Jordan’s recruiting and hiring process
1. Their first (in a long time) fully remote hire
Brian’s newest customer experience
What to do with B2B SaaS these days?
1. E-commerce platform issues

[tweetthis]"The mistakes in hiring are more costly than any monetary mistake. Like, buying the wrong thing, using the wrong software, hiring the wrong consultant. I see those as monetary mistakes. When you making a hiring mistake, it hurts so much more.” - Jordan [/tweetthis]

Resources/Links:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Navigating Stress & Distractions

Bootstrapped Web — Thu, 04 Jun 2020 03:00:00 -0300

The world is in chaos but we’re still here. Today we’re talking about some of the trends and the future of podcasting after some big news with The Joe Rogan Experience. We’re also going over some updates with Carthook, ProcessKit, and Audience Ops.

[tweetthis]"It does seem like there’s still that massive gap between the seed rounds and the Series A. Right? When you’ve grown to a certain level and you still need more firepower to grow." - Brian [/tweetthis]

Here are today’s conversation points:

The big debate over Joe Rogan’s Spotify deal
Jordan’s (who is not soliciting for investments, SCC) fears over investors
ProcessKit’s onboarding course, not quite ready
Funding: social media ads, marketing partnerships (affiliates and referrals)
Jordan’s biggest deal ever...and he didn’t even talk to the prospect
Difficult clients in Audience Ops

[tweetthis]"You’ve been working on something for over five years. This is all you care about. You love it. You love the job, the company, the people. There’s so much involved in that. How are you supposed to find investors that are going to respect that?” - Jordan [/tweetthis]

Resources/Links:

As always, thanks for tuning in. Head here to leave a review on iTunes.

What if we take some off the table?

Bootstrapped Web — Thu, 28 May 2020 03:00:00 -0300

In today’s episode we’re talking about socializing with family friends and work during the pandemic, as well as the latest news and questions on our minds about the current status of tech and the world. PokerStars, weekly stand-ups, Facebook, and what reopening might look like. The big question on everyone’s mind is: “How long is this going to last?” In business news, we’re talking about Brian’s new ProcessKit course, and Jordan’s views on hiring.

[tweetthis]"You’re taking money off the table but you’re also taking off the table, the desire to sell when the first semi-big offer comes along and instead go super-big." - Brian [/tweetthis]

Here are today’s conversation points:

Facebook news
Jordan’s most popular tweet ever
- Taking on more money and the possibility of hitting zero
- What is Clubhouse and why is it so big right now?
Serendipitous audio conversations versus Twitter versus podcasting
- Private podcasts
Interesting new platforms: Substack
Updates on Brian’s new course about ProcessKit
Jordan’s views on hiring
Brian’s work on the sales demos

[tweetthis]"People watch how you treat people and then they put themselves in those shoes.” - Jordan [/tweetthis]

Resources/Links:

Managing Customers & Managing Teams

Bootstrapped Web — Thu, 21 May 2020 03:00:00 -0300

Welcome back! Brian and Jordan are back behind the mic. We’re talking about ProcessKit’s best month, and Brian’s excitement about moving forward and making progress. We’re also talking about Jordan’s experience with Carthook’s people coach and accidental faux pas with his leadership team.

[tweetthis]"I am acting fast on a lot of the smaller requests. I only do it when I’ve heard it two or three times from different customers. Usually and hopefully I’m shipping something fast and notifying multiple customers that, ‘Hey, we just shipped that thing." - Brian [/tweetthis]

Here are today’s conversation points:

ProcessKit’s best month with conversions
Jordan’s focus on hiring and salaries
Brian’s focus for ProcessKit: onboarding
Brian’s old blog posts
Setting up SEO
Jordan’s humbling experience with the people coach
Accidentally taking away authority
Brian’s support requests on ProcessKit

[tweetthis]"What am I really doing though? I’m taking authority away from their manager. I’m not allowing that manager to be that person, resource, and that trust and that bond and… I’m messing with that and it’s not helpful." - Jordan [/tweetthis]

Resources/Links:

As always, thanks for tuning in. Head here to leave a review on iTunes.

Value of a Coach / Hiring Spree / Launching in Public

Bootstrapped Web — Thu, 26 Apr 2018 03:00:05 -0300

Value of a Coach / Hiring Spree / Launching in Public

Bootstrapped Web — Thu, 26 Apr 2018 03:00:05 -0300

On today’s episode, we discuss the real value of a business coach. Jordan has announced that he would like to try his hand at it and Brian shares his own experience with it. We compare the pros and cons of being a coach for other founders and we explore why it is a good revenue source. We also continue our Armchair Quarterbacking Sessions with Derrick Reimer’s project Level. Derrick has noticed some productivity issues with the platform, Slack. He is out to recreate an alternative that can be customized for the tech world, where distractions are project killers. We offer our impressions of the idea and analyze how Derrick is approaching his product development. [tweetthis]There are so many really talented, really smart, really motivated people, they just want to work remotely. - Brian[/tweetthis] Here are today’s conversation points:

Getting ready for MicroConf.
Brian’s update on the podcasting service.
The only stumbling block Brian has encountered.
Jordan’s plans to start coaching.
Why he is interested in exploring coaching.
Who would benefit from Jordan’s coaching?
The value of a good business coach.
The pros and cons of being a coach.
Armchair Quarterbacking Session: Level.
Building an alternative to Slack, and is it possible?
Are there any benefits to being transparent?
Jordan’s advice to Derrick.
Brian’s impressions of Derrick’s idea.

[tweetthis]If you are going to provide value, it's not just talking, it's work. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Derrick Reimer’s Twitter Jordangal.com Jordan’s email Jordan’s Twitter Level Level on Twitter MicroConf Productize Slack As always, thanks for tuning in. Head here to leave a review on iTunes.

What If We Ran Your Business (For the Fun of It)?

Bootstrapped Web — Thu, 19 Apr 2018 03:00:51 -0300

What If We Ran Your Business (For the Fun of It)?

Bootstrapped Web — Thu, 19 Apr 2018 03:00:51 -0300

Things are getting back to normal in our respective business worlds. Brian has launched his podcasting service and Jordan is back to business as usual after a visit from Ben and Rok. Today we kick off our “armchair quarterbacking” sessions, and we are starting with Andrew Culver’s SaaS product, Bullet Train. We also give general updates on what is going with Carthook and Audience Ops. So tune in to hear about Brian’s new service and Jordan’s newfound ambition after having a rare full team meetup. [tweetthis]We [founders] think in a certain way and maybe we don't remember what it is like to be an employee. - Jordan[/tweetthis] Here are today’s conversation points:

How having Rok and Ben around has energized Carthook’s team.
The presentations and social activities that helped Jordan’s team get better in step with each other.
Adjusting back to regular business after Rok and Ben left.
Brian’s new podcasting service.
The hiring process Brian is using to build his podcast service.
An update on the Productize Course and Brian’s closed cart approach.
Jordan’s upcoming conference projects.
The struggle of working during business travel.
The benefit of doing one-on-one discussions with your employees.
The first armchair quarterbacking session: Bullet Train.
Why agencies would be the best fit for Bullet Train.

[tweetthis]Nobody is going to get as fired up and keep pushing than the founder. - Brian[/tweetthis]

Resources Mentioned Today:

Audience Ops Bullet Train Carthook MicroConf. Productize Shopify Unite As always, thanks for tuning in. Head here to leave a review on iTunes.

The Carthook Team Talks Product Development Process

Bootstrapped Web — Thu, 12 Apr 2018 03:00:05 -0300

We welcome Team Carthook to the podcast today! Jordan has brought two of his senior team members to discuss the evolution and future evolution of Carthook’s service. Ben Fisher is the co-founder of Carthook and head of product. Rok Knez is Carthook’s lead developer. He usually manages the company office over in Slovenia. Both Ben and Rok were a part of the company since the very beginning. The guys share how they met and how the business has gone from 3 guys hanging out to the large-scale team that is today’s Carthook. We discuss the technical issues that have reared their ugly head the last few months and Ben explains how they coped with this inevitable part of the business. Today the hood is being lifted on Carthook and we will learn about how Jordan and his team interact with each other and their clients. Buckle up for a very technical episode! [tweetthis]For bootstrapping new software startups, choose a more mature framework, rather than the trendiest stuff. - Brian[/tweetthis] Here are today’s conversation points:

Introducing Ben and Rok.
How Ben and Rok met Jordan and got involved in Carthook.
How Rok hired the engineering team.
Who helps with product design?
The new style guide the team has recently adopted.
How Carthook’s tech stack has evolved.
The importance of not cutting corners.
The benefits of using Angular.
Carthook’s road-mapping process.
When do frameworks and processes matter?
The 3 questions the team ask themselves when making decisions.
How Hiten Shah has influenced Carthook’s process.
How Jordan and the original team have coped with working with a larger team.
What Jordan and his team have learned about their product.
The importance of choosing the right colleagues.

[tweetthis]Spend whatever we need to spend, and eventually they [Ben & Rok] took that advice and now I regret it a bit. - Jordan[/tweetthis]

Resources Mentioned Today:

Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

The Carthook Team Talks Product Development Process

Bootstrapped Web — Thu, 12 Apr 2018 03:00:05 -0300

Launching a Podcasting Service / Learning to Code / Partner Webinars

Bootstrapped Web — Thu, 05 Apr 2018 03:00:55 -0300

MicroConf is right around the corner and Jordan is gearing up for his talk for the event. He bounces some topic ideas off Brian and reveals how his topic choices are reflecting what is happening in Carthook. The version 2 upgrade is finally working properly and Jordan and his team are seeing some major cultural shifts in the business. Brian has found himself with some downtime, so now he is thinking about new avenues for Audience Ops. Brian outlines his idea for a new service offered through Audience Ops. An done-for-you podcasting service. He gets Jordan’s feedback and really explores why he thinks podcasts are the next logical step for the business. He also drops a big announcement… Brian wants to learn to code. We have some interesting conversation about alternative content on this episode and some really useful reflections on the founder’s role within his company. [tweetthis]If somebody asked the most valuable thing you’ve learned the past months it would be related to our process. - Jordan[/tweetthis] Here are today’s conversation points:

Get ready for MicroConf.
Brian’s new service launch.
Considerations for future podcast topics.
Jordan’s March recap.
Why Brian wants to launch a new service.
The all-done-for-you podcast service breakdown.
Brian’s small beta group for the new service and the results.
The benefits of podcasting content.
The second version of Carthook update.
Jordan’s webinar experiment.
The benefits of webinars.
How to create pitch-hitter scenarios.
How Carthook uses paid ads.
The ad strategy Jordan used for the webinar.
Brian’s results from his Productize webinar.
Why Brian wants to learn to code.
How to be a full stack product person.
Jordan’s adjustment to a larger work team and changing the dynamic.

[tweetthis]If you are a designer of web applications, you should have a full stack skillset. - Brian[/tweetthis]

Resources Mentioned Today:

Audience Ops Podcasting Service Bullet Train CodeMentor.io Carthook Castos MicroConf Ops Calendar Productize As always, thanks for tuning in. Head here to leave a review on iTunes.

Launching a Podcasting Service / Learning to Code / Partner Webinars

Bootstrapped Web — Thu, 05 Apr 2018 03:00:55 -0300

Charging For Attention / Elusive Product-Market-Fit

Bootstrapped Web — Thu, 15 Mar 2018 03:00:54 -0300

Conference Strategy, Webinar Funnels, & Lead Developers

Bootstrapped Web — Thu, 01 Mar 2018 02:00:33 -0400

Sherry Walling Helps Us Keep Our Sh*t Together

Bootstrapped Web — Thu, 08 Feb 2018 02:00:08 -0400

Holiday Hustle vs. Rest And Community Marketing

Bootstrapped Web — Thu, 11 Jan 2018 02:00:01 -0400

Our 2017 Review & 2018 Preview

Bootstrapped Web — Thu, 21 Dec 2017 02:00:32 -0400

Our 2017 Review & 2018 Preview

Bootstrapped Web — Thu, 21 Dec 2017 02:00:32 -0400

2017 is coming to a close and Jordan and Brian are looking back on this explosive year. They also share their plans for 2018. Audience Ops and Carthook both saw tremendous amounts of growth this year. That growth has caused the guys to reflect on 2017 and the lessons they have taken away from the experience. Brian has seen an uptake in sign-ups and Audience Ops has ridden a roller coaster this year. Brian shares what he learned from the sudden stop and go growth of the business. 2018 looks to be a major year for Audience Ops, Ops Calendar, and Productize. Jordan has had a monster of a year. He is recuperating from a breakneck year with a well deserved slow down period. Jordan shares what this year taught him about team building and how he plans to fix some of the issues he noticed during Carthook’s major growth spurt. [tweetthis]Growth is great, but it will mask problems. - Jordan[/tweetthis] Here are today’s conversation points:

The problems Jordan discovered when onboarding new team members.
Brian’s surge in service sign-ups.
Carthook’s Drip campaign disaster.
Setting new goals and themes for 2018.
The downside of sudden growth.
Coping with wild growth and rapid plunge of business.
Jordan’s tech issue in 2017 and how he plans to fix them.
Productize’s new course launch in January.
Jordan’s general observations about 2017 and 2018.
Brian’s general observations about 2017 and 2018.

[tweetthis]I actually have a lot of firepower to play with going into 2018 now. - Brian[/tweetthis]

Resources Mentioned:

Audience Ops CasJam Carthook Ops Calendar Productize As always, thanks for tuning in. Head here to leave a review on iTunes.

Running a Black Friday Sale / Development Process

Bootstrapped Web — Thu, 07 Dec 2017 01:15:36 -0400

2017 has been a phenomenal year for Jordan and Brian. On today’s episode, they give the audience an update on the businesses and offer a glimpse into their plans for 2018. Brian is going to shift focus to Productize and relaunch a bigger and better product later. This means he will be closing enrollment in the course and beginning the maintenance phase of this upgrade. He shares how he reached this decision and why he is excited by the new possibilities it can bring. Jordan is adjusting to a growing business and finding ways to restructure his processes to make Carthook more efficient. He uses his previous experience over the last year to prepare Brian for his up-coming wild ride. The guys also share some new tools and resources that have found to make this new stage in their businesses a little easier. [tweetthis]This has been the biggest spike in revenue for Productize and way beyond expectations. - Brian [/tweetthis] Here are today’s conversation points:

Brian’s shift to working on Productize during the month of December.
Jordan’s look back over his year, from an investor’s point of view.
Coping with a larger team and the issues that arise.
Brian’s awesome Black Friday!
Brian’s plans for relaunching Productize.
Jordan’s new team members and the importance of good content writing.
How Jordan is restructuring his processes.
The trade-offs a team has to make for the sake of speed.
How to build a great product without slowing down the project.

[tweetthis]It's still a mindset and a process, if everything is a trade-off, where are you putting the emphasis? - Jordan [/tweetthis]

Resources Mentioned Today:

Appcues Audience Ops Beacon Carthook Drift Seeking Wisdom Podcast GoVideo Productize Course Ops Calendar Soapbox As always, thanks for tuning in. Head here to leave a review on iTunes.

Running a Black Friday Sale / Development Process

Bootstrapped Web — Thu, 07 Dec 2017 01:15:36 -0400

"Fattening" Your Company and... Freemium?

Bootstrapped Web — Thu, 16 Nov 2017 02:00:38 -0400

"Fattening" Your Company and... Freemium?

Bootstrapped Web — Thu, 16 Nov 2017 02:00:38 -0400

Welcome back to Bootstrapped Web! Today we share progress reports about our respective businesses and ask the question, “Should you go freemium or not?” Jordan has begun the process of “fattening” up Carthook’s systems to add value to the company and move the business to the next stage. Carthook is also growing their team and there have been some growing pains in the communication process. There have been some hard lessons in the process that Jordan hints at that could help business owners build their systems more effectively. Brian has been putting a lot of energy and time into Ops Calendar. He is getting a lot of interest in the service and the product. This new interest has given him a reason to ask the question if freemium is a viable option for Audience Ops. There is some really useful and thoughtful discussion in today’s episode, so tune in to join the conversation. [tweetthis]I feel freemium is one of these things that a lot of bootstrappers have not given a fair shake as a strategy. - Brian[/tweetthis] Here are today’s conversation points:

The “fattening up” process of Carthook.
The struggles of building an effective team.
Audience Ops and Ops Calendar progress reports.
Ops Calendar’s features and fixing the unexpected bugs.
The usefulness of Slack.
The benefits of letting people “win.”
Working with freelancers and building a positive business culture around them.
Jordan’s marketing experiments and the results.
The pros and cons of freemium.

[tweetthis]I admire people who are super product focused because I think it's fun. It's so creative and interesting. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Calendar Carthook As always, thanks for tuning in. Head here to leave a review on iTunes.

First Customer Demos, Paid Marketing Funnels, Team Communication

Bootstrapped Web — Thu, 05 Oct 2017 07:00:15 -0300

We have both reached a turning point in our marketing campaigns. Jordan has launched a new marketing funnel for Carthook’s Shopify tool. Brian has been running a new marketing campaign for Ops Calendar. We share how the campaigns are working for us and offer each other advice on how to improve our strategies. We also discuss how we keep our team culture positive when we ourselves are super busy and can’t give our undivided attention to individual projects. Our teams are growing and changing and we explore how we are coping with these mostly positive developments. It’s a good time for both Ops Calendar and Carthook! [tweetthis]These calls are dripping in, inbound, organically...these just feel like good signs to me. - Brian [/tweetthis] Here are today’s conversation points:

Carthook’s new paid marketing campaign.
Ops Calendar is finding a new audience and why Brian is excited by this.
How Brian uses and makes sense of Audience Ops’ analytics and metrics.
How Jordan set up his marketing campaign.
Jordan’s 3 blog post marketing strategy.
Other insights into email and ad marketing.
How we differ in our methods of team building and encouraging positive company culture.

[tweetthis]I tell people on my team think like an owner, think what do I need to fix this - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.

First Customer Demos, Paid Marketing Funnels, Team Communication

Bootstrapped Web — Thu, 05 Oct 2017 07:00:15 -0300

Pricing Page Teardown, Employee Onboarding, Company Transparency

Bootstrapped Web — Thu, 21 Sep 2017 07:00:44 -0300

Pricing Page Teardown, Employee Onboarding, Company Transparency

Bootstrapped Web — Thu, 21 Sep 2017 07:00:44 -0300

Today on Bootstrapped Web Jordan and Brian discuss what’s going on in their individual businesses. Brian is setting up Ops Calendar and takes today’s episode as a chance to get Jordan’s feedback from the customer’s point of view. Listeners who are interested in Ops Calendar can get excited because Brian gives a detailed description of what his service offers. Jordan has had some problems with retaining new team members. He shares what he has learned about the hiring process and how he keeps company morale high. He also shares a new service he has found for businesses who hire team members in different states and he is psyched by his results. [tweetthis]All your employees, there is a level of trust... it's better for everyone to be honest. - Jordan[/tweetthis] Here are today’s conversation points:

The benefits of providing hardware and tools to your remote team members.
The role trust plays in working with a remote team.
Ops Calendar is going live!
Jordan’s advice to Brian regarding Ops Calendar’s structure.
What Ops Calendar can do for each tier.
Why a business should always be recruiting.
The importance of staying positive when business isn’t going as expected.
How much transparency is too much?
Why the service Officeengine is awesome!

[tweetthis]Having full-time employees, especially in different states, adds a massive layer of complexity. - Brian [/tweetthis]

Resources Mentioned Today:

Carthook Ops Calendar Officeengine As always, thanks for tuning in. Head here to leave a review in iTunes.

SaaS Momentum, Servicing Demand, & Why Amazon Bought WholeFoods

Bootstrapped Web — Thu, 27 Jul 2017 07:00:00 -0300

We cover a lot in this episode of Bootstrapped Web. We give our listeners an update on both companies’ progress and we discuss some exciting news in the startup world. Brian shares some of the goals he has for Audience Ops in the near future. Jordan has an awesome story to share about his new VIP client. We compare our business needs and consider the unexpected problems that come with growth. We also discuss two really insightful articles that just came out, Amazon’s New Customer, by Ben Thompson and Why I Bought Your Software by Justin Jackson. Both articles are great reads and we have some good takeaways from them. [tweetthis]If it's not 100% core to what we do, first option will be to integrate with the big player in the field. - Jordan[/tweetthis] Here are today’s conversation points:

Jordan's new VIP customer.
Ben Thompson’s latest article.
The Amazon and Whole Foods merger.
Why the merger is a good thing.
Lessons Jordan has learned from his new hire.
The benefits of mastermind groups.
The biggest expense for any growing company.
How do you know when you’ve reached “feature completeness?”
Brian’s Ops Calendar update.
Justin Jackson’s latest article.
Seeking Wisdom with David Cancel.

[tweetthis]I feel like, if you're not in such a cut-throat, competitive space, you can get by with a slower road map. - Brian[/tweetthis]

Resources Mentioned Today:

Amazon’s New Customer, by Ben Thompson Audience Ops Carthook Drift Front App Intercom Ops Calendar Seeking Wisdom Why I Bought Your Software, by Justin Jackson As always, thanks for tuning in. Head here to leave a review in iTunes.

A Formula for Individual Success Metrics + Building a Hiring Engine

Bootstrapped Web — Thu, 06 Jul 2017 07:00:06 -0300

Happily, our client loads are increasing, but our staffs are starting to feel the increased workload. So, we need to hire more people to keep up. It’s a good problem to have. On today’s episode, we compare our staffing needs and discuss how we are trying to build a process that frees us both up for “CEO tasks.” As our businesses grow, our roles change. Brian shares his plans to cope with a couple of team members exiting the company. While Jordan recently spent some time away with his family. He shares how that trip changed how he looks at his team and responsibilities to the company. [tweetthis]I have to perform better as a CEO...the interference portion of my equation is just preposterous. - Jordan[/tweetthis] Here are today’s conversation points:

The uptake in business for Audience Ops.
Brian’s plan to cope with the increased workload.
Filling team positions for growth at Audience Ops.
The ups and downs of working with a remote team.
Jordan’s recent trip to New York.
The “performance equation:” performance= potential - interference.
How the performance equation has helped Jordan look at Carthook’s growth differently.
How difficult it can be to transition into the “CEO role.”

[tweetthis]Forget limiting the headcount, let’s get more than enough people on board and spread the work around. - Brian [/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Productize As always, thanks for tuning in. Head here to leave a review in iTunes.

KPI Dashboards, Hiring Sales vs. Customer Success, & Solo Founders

Bootstrapped Web — Thu, 22 Jun 2017 07:00:38 -0300

Today Brian and Jordan discuss growth. In Jordan’s case he is dealing with sudden growth, and in Brian’s case, he is planning for growth. Both share how they are handling this wonderful problem. Jordan has been focused on getting Carthook’s marketing up and running again, but it has become clear that his team needs him to focus on improving the customer support. It has been a struggle to really pinpoint what the team needs. Jordan calls it “customer success,” but Brian isn’t so sure that’s the best title for the position. Brian is working on his KPI (Key Performance Indicators.) While making the dashboard for these KPI, he learned that sometimes you need to just hire someone. Brian is also planning to do some hiring, he needs two project managers and a writer. He caps off today’s topics with an article from the website Baremetrics. [tweetthis]I'm now in this mindset with this business, it is all about growth. - Brian[/tweetthis] Here are the conversation points:

Brian’s four major categories for his KPI.
When to know you need to hire someone.
Jordan’s ever-growing stress.
Jordan’s undefinable job description.
What does “customer success” mean?
What Jordan needs for this new position.
The importance of taking care of “home base.”
Brian’s hiring needs.
Josh Pigford’s blog post.

[tweetthis]What we need to do is work harder and smarter on making sure existing customers are satisfied and happy. - Jordan[/tweetthis]

Resources Mentioned Today:

Being a Solo Founder: Pros, Cons, Tips, and Tricks, by Josh Pigford Audience Ops Carthook Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.

Customer Overwhelm, Hiring & Firing Teammates

Bootstrapped Web — Thu, 08 Jun 2017 07:00:46 -0300

We are both hitting some major growth right now in our businesses, and that means a lot of excitement and a lot of restructuring. We talk about project managing, hiring the right people, and the efforts we are putting into our marketing and lead generation. Jordan recently went to Europe and met up with his team. He tells us how the trip went and the exciting milestone he saw while working with the Carthook team in Europe. Jordan has also had some people leave the company. He explains why they had to go and how he plans to bounce back. Carthook’s marketing has stalled because of a sudden flux of customers, Jordan discusses his concerns and how he plans to fix the problem. Brian has really sunk into his Facebook ad campaign. He is working to generate leads for Audience Ops and filter people into a funnel that will lead potential clients to a consultation. He explains the 3 step ad campaign and shares how it is working for him. Brian is also hiring some new people and offers some advice for Jordan regarding his marketing problems. [tweetthis]We only have a certain number of bullets to fire, in terms of people we can have inside the company. - Jordan[/tweetthis] Here are our conversation points:

Jordan’s trip to Europe.
Brian’s Facebook ad campaign.
Brian’s current hiring needs.
How to create evergreen content for lead generation.
Jordan’s concern about customer support quality.
The “2 worlds” of Carthook.
Why Trello isn’t working for Jordan and his team.
How to discern what is urgent in your business.
What are the expectations of a Project Manager?
The difficulties of firing team members.
Brian’s podcast relaunch.
The 3 phases of online software.
How to build a brand online.

[tweetthis]My whole goal right now, is to drive more leads into Audience Ops. - Brian[/tweetthis]

Resources Mentioned Today:

Appointment Audience Ops Calendly Carthook CasJam Expert Secrets by: Russell Brunson Facebook Help Scout Intercom Seeking Wisdom Trello War of Art by: Steven Pressfield Weworkremotely.com Zendesk As always, thanks for tuning in. Head here to leave a review in iTunes.

YouTube Content, Creating Webinars, Team Retreats

Bootstrapped Web — Thu, 25 May 2017 07:00:14 -0300

We are back discussing our businesses and the progress that we have been making. On the personal front Jordan is heading off to Europe and Slovenia to work and hit the beach. Brian has been getting healthier with the BulletProof diet. Brian has been recording new episodes for his Productized podcast. He is hiring one person to take care of the editing, shownotes, social stuff, and posting. He is also trying to make two videos a week. He is also launching the Sell to Strangers webinar for his funnel. Jordan plans to get a lot of work done in Slovenia including writing a script for a webinar. He also wants to finish up the documentation for product including video. Jordan feels that he needs to go a little harder on his marketing and create more desire. [tweetthis]If you want to grow your business, you have to sell to strangers. - Brian[/tweetthis] Here are today’s conversation points:

Brians Productized podcast and his video progress.
Jordans list of things he wants to do for his business while in Slovenia.
Writing scripts for webinars.
Making a public calendar or roadmap to help hold yourself accountable.
Education for products has two parts - how to use the product, and how to get the most out of using it.
Using webinars for funnel content.
How Click Funnels grew off the back of one webinar Steal My $17,000 a Day Funnel.
Case studies and client interviews and the wins possible.
Marketing to marketers for Jordan’s business.
The project manager side of Audience Ops.
Breaking down processes and putting the right people in the right positions.

[tweetthis]We need to create interest and get people excited with our marketing. - Jordan[/tweetthis]

Resources Mentioned Today:

Carthook Audience Ops Ops Calendar Calendly Productize Podcast Baremetrics As always, thanks for tuning in. Head here to leave a review in iTunes.

Back from MicroConf! More Signups! Facebook Ads Funnels!

Bootstrapped Web — Thu, 11 May 2017 07:00:00 -0300

We are back from MicroConf and on this episode we share our takeaways and also update the important things going on in our businesses. Jordan shares how Russ Henneberry’s MicroConf talk encouraged him to look at his business differently. After this episode you may not look at funnels the same way again. Brian explains how MicroConf often helps him refocus his priorities. He has plans to reconnect with his personal brand and create some new engaging content. We discuss how he can do that. MicroConf has been an educational experience for both of us and we have some really good take aways that we discuss today. We also have some general updates about our businesses. Surprisingly, we both are having issues with our marketing. We compare situations and see if we have something that could be helpful to the other person. [tweetthis]It’s been very helpful for the team to see me very freely admit shortcomings. - Jordan[/tweetthis] Here are today’s conversation points:

How MicroConf changed Jordan’s approach to funnels.
Content marketing updates.
Why you should know why your customers use your product.
Brian’s update about Audience Ops and Casjam.
Jordan’s new hires.
The importance of improving SOPs.
The natural progress toward corporate structuring. Why it is inevitable.
Our marketing successes and woes.

[tweetthis]It's more about really understanding the underlying 'why' of that problem in your customers' minds. - Brian[/tweetthis]

Resources Mentioned Today:

Audience Ops Ops Calendar Carthook CasJam MicroConf As always, thanks for tuning in. Head here to leave a review in iTunes.

Onboarding First SaaS Customers

Bootstrapped Web — Thu, 30 Mar 2017 07:00:30 -0300

Today we discuss how our respective businesses have begun on-boarding customers to our new products. The Shopify checkout app is growing and Jordan and his team are learning what makes the app successful. Brian has begun on-boarding clients on to the Audience Ops Calendar. We discuss what we’re learning from these processes and how that will change how we move forward. Microconf Vegas is just around the corner. Jordan will be giving a talk to the event. He shares what has inspired his talk. [tweetthis]Even if I know what I'm focused on this quarter, things tend to change when I leave MicroConf. - Brian[/tweetthis] Some of the other things we discussed in today’s episode are:

Lessons Jordan’s team has learned from Hiten Shah’s course.
Should a customer support employee be full time?
Why SaaS is so competitive.
Why you can’t please everybody.
The upcoming Microconf Vegas.
Why Brian shut down Audience Ops Express.

[tweetthis]You need like a north star of what your product does or it's easy to get pulled in different directions. - Jordan[/tweetthis]

Resources Mentioned Today:

Carthook - Shopify Checkout App Audience Ops Calendar BootstrapTour Microconf As always, thanks for tuning in. Head here to leave a review in iTunes.

Launching a New Service in 5 Days & Hitting Your Product Stride

Bootstrapped Web — Thu, 09 Mar 2017 06:00:11 -0400

We have some big news coming up the following weeks. Brian discussed his recent experience with Facebook ads and the pros and cons of marketing on the platform. Jordan shares his found his new found security in his business. We are really excited about the new rewrites and product launches and we talk about it all! [tweetthis]Marketing needs to make that promise and then the product needs to deliver on that promise. - Jordan [/tweetthis] Here are today’s conversation points:

Brian’s Facebook ads and the results.
Jordan’s new confidence in Carthook.
Tweaking the Calendar app for beta testers.
Brian’s new service Audience Ops Express.
The reasons people leave Audience Ops.
How Audience Ops Express would change those reasons.
Carthook’s new release.
How to move into a self serve business model.
Audience Op’s Calendar gets a new name.
Gearing up for Microconf. Las Vegas.

[tweetthis]We'll do all the extra leg work to get it proofread, polished… whatever needs to happen. - Brian[/tweetthis]

Resources Mentioned Today:

Carthook Audience Ops Ops Calendar MicroConf. Las Vegas As always, thanks for tuning in. Head here to leave a review in iTunes.

Updates Facebook Ads, Public Speaking, & Entrepreneurial Parenting

Bootstrapped Web — Thu, 23 Feb 2017 06:00:33 -0400

Welcome back to Bootstrapped Web. On today’s episode we cover a lot of subjects that are both business and personal nature. We update you on Brian’s Calendar product and Jordan tells us about a talk he gave to his accelerator group. We also discuss Brian’s experience with Facebook ads and how Facebook is helping him get the word out about Audience Ops. He shares some tools he has found useful while creating these ads. If you are looking for some easy to use tools for your ads you might find this episode interesting. [tweetthis]For now the goal is to drive more leads through a funnel for the content service and keep that engine turning.- Brian[/tweetthis] Here are our conversation points:

Jordan’s talk with Portland’s Starve Ups.
How Brian uses Facebook ads to promote Audience Ops.
What is a Facebook lead ad?
Creating ad campaigns with Facebook.
Jordan’s problems with Facebook Pixel.
Our discussion about public school and it’s lack of individuality.
Brian’s update on the calendar project.
Why working with people in person is useful.

[tweetthis]We have become the default recovery app for subscription businesses. We own that market. - Jordan [/tweetthis]

Resources Mentioned Today:

Starve Ups Animoto Beacon.by Audience Ops Carthook Facebook As always, thanks for tuning in. Head here to leave a review in iTunes.

Get-to-Launch Roadmap, Hiring (more) Developers, When to Work on Marketing

Bootstrapped Web — Thu, 16 Feb 2017 06:00:45 -0400

We talk about Big Snow Tiny Conf and team growth today. Brian had a great time up at Vermont’s Big Snow Tiny Conf and has some awesome take-a-ways to share. Jordan is growing his team and is getting ready for a big marketing push. We both have some useful insights into team management and creating a successful product funnel. This is a good episode to see what goes into a product launch and how a project has several launches. [tweetthis]It’s amazing that something that you hate and weighs on you, just get it done and everything feels better. - Jordan[/tweetthis] Here are today’s conversation points:

Big Snow Tiny Conf
Kara Swisher on Tim Ferriss’ podcast.
Tax season for Startups.
Jordan’s new developer.
Ways to structure team management.
Josh Pigford’s latest blog post.
Why we stopped consuming business advice.
When we consume new business advice.
Brian’s new developer.
The benefits of hiring new team members.
Brian’s advice for marketing to Jordan.
Jordan’s Stave Ups talk.

[tweetthis]Frankly, I don’t think there are enough podcasts that are using the model we’re using here. - Brian [/tweetthis]

Resources Mentioned Today:

Audience Ops Calendar Audience Ops Training Program Carthook Starve Ups Big Snow Tiny Conf Tim Ferriss Podcast The Startup Echo Chamber is Making You Deaf, by: Josh Pigford As always, thanks for tuning in. Head here to leave a review in iTunes.

2016 Recap & 2017 Goals

Bootstrapped Web — Thu, 22 Dec 2016 05:00:30 -0400

Well, 2016 is coming to an end. Today we’ll compare our goal lists from last year and reflect back on what went wrong and what went right. Carthook and Audience Ops have both grown and changed so let’s sit down and take a look at our 2016 results. We will also discuss our goals for 2017 and how we plan to make them happen. This will be our last episode for 2016, and we’ll pick up next year. [tweetthis]I think another way to think bigger is to think long term and not short term. - Brian[/tweetthis] Here’s today’s conversation points:

Why Jordan wasn’t able to bring Carthook into profitability.
Brian’s goal for Audience Ops and finding organic leads.
How to think bigger.
The problems Jordan had pivoting away from cart abandonment.
Audience Ops is diversifying its product line.
Beta users will be getting the Audience Ops Calendar.
Wanting 2017 to be a breakout year.
Why Brian went back to sales.
When to raise prices?
Working with kids in the house.
Working with teams during the holidays.
Jordan’s 2017 goals.
Brian’s 2017 goals.
When to give yourself a raise.

Have a Happy Holidays everybody and we’ll see you next year! [tweetthis]My goal is to have a more balanced 2017. - Jordan[/tweetthis]

Resources Mentioned Today:

Carthook Audience Ops Audience Ops Calendar ProfitWell As always, thanks for tuning in. Head here to leave a review in iTunes.

Updates: Redesign, Marketing Multiple Products, & Selling Services

Bootstrapped Web — Thu, 15 Dec 2016 05:00:48 -0400

Today’s Bootstrapped Web is going to be an up-date episode. We both have a lot to talk about with what we’re working at the moment. Audience Ops and Carthook have new products and we discuss what is working for our sales respectively. We talk about transparency and some resources that will help you improve your sales game. So tune in for the latest developments in Carthook and Audience Ops and what you can expect in the coming months. [tweetthis]Force the demo and you will get fewer sign-ups, but you will get into a lot of conversations. - Jordan[/tweetthis] Here are today’s conversation points:

Why we don’t see the point to total transparency.
When to ask for the credit card during a sign-up.
Brian’s plans to redesign the Audience Ops website.
Getting ideas from Ruben Gamez from Bidsketch.
Jordan’s lessons from demos.
Tweaking Audience Ops for a Resource Hub pivot.
Brian’s plan for launching Calendar for beta testers.

[tweetthis]I feel like I can't launch anything else, until I have the new site up and running. - Brian[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Securing the Five Figure Sale, by: Ian Landsman Product Demos that Sell: How to Deliver Winning SAAS Demos, by: Steli Efti Audience Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.

Family & Entrepreneurship

Bootstrapped Web — Thu, 08 Dec 2016 05:00:22 -0400

Hey we’ve got a party episode with Rob and Sherry Walling from the podcast ZenFounder. We are going to discuss how to balance life with kids and entrepreneurship. We explore the common problems with living with kids and keeping a business going. We also discuss how entrepreneurship affects marriage. Rob and Sherry share how they are able to keep their communication open. We also discuss how we ourselves cope with the struggles of keeping family and entrepreneurship in a fair balance. [tweetthis]Working for a boss was not even a possibility when you see that & you know entrepreneurship as the default. - Jordan[/tweetthis] Here are today’s conversation points:

The issues we have the public school systems.
How to encourage entrepreneurship with your kids.
How entrepreneurship affects marriage.
How to leave work behind at the end of the day.
Why spouses aren’t necessarily the best person to vent to or use as a soundboard.
How kids change your goals and motivations.
How to deal with burnout.
How to make the shift from work time to family time.
How to plan your week beforehand.
The importance of giving your spouse non-kid time.

[tweetthis]I find a lot more value in having Mastermind groups and friends and advisors to talk about real issues. - Brian[/tweetthis]

Resources Mentioned Today:

Rob Walling on Twitter Sherry Walling on Twitter ZenFounder MicroConf Vegas As always, thanks for tuning in. Head here to leave a review in iTunes.

Launching 2nd Products w/ Ruben Gamez

Bootstrapped Web — Thu, 24 Nov 2016 05:00:18 -0400

Welcome back to Bootstrapped Web. Our guest today is Ruben Gamez, the founder of Bidsketch.com. We are talking to Ruben today because Bidsketch is getting ready to launch a new product. Since we both are launching new products we thought it would be good to compare notes. Bidsketch’s main product has been a proposal tool. Now they want to add a signature app to their brand. Today we discuss how to research for a new product and how to handle expanding when there are competitors. We compare notes about our own product lines and how to get the customers to notice. [tweetthis]I think there are plenty, well established competing companies who just have feature bloat. - Brian[/tweetthis] Here are today’s topics:

How to find positioning and distribution for a new product.
Why begin a separate product line.
Finding the “why” when people don’t use your product.
How to focus on two product lines.
Creating a good elevator pitch.
Finding your hook.
Asking the right questions of new customers.
How to reach people outside of your network.
Ruben’s timeline.
How to find the gaps in your competitor’s products.
Why you shouldn’t copy just to copy a competitor.

If you are interested in Bidsketch and their new product, you can go to bidsketch.com or find Ruben on Twitter. [tweetthis]There is all this lead up that goes into it [switching apps] that you don't see it beneath the surf. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Calendar Bidsketch Carthook Ruben Gamez’s Twitter As always, thanks for tuning in. Head here to leave a review in iTunes.

Updates: Validating a Consulting Offer / Self-Funding a New SaaS

Bootstrapped Web — Thu, 17 Nov 2016 05:00:42 -0400

Today’s episode is an update episode. Jordan tells us about finding his customer base for the funnel tool. Brian discusses how he is working with his developers on a new training product he is planning. We discuss when to allow custom jobs and when to say no. We also discuss what challenges a young bootstrapped company needs to expect. Building your company is so much harder, than it sounds. If you are just starting out as a bootstrapped business, then maybe this episode will help you get an idea of what you’re getting into and the other challenges. [tweetthis]We need to shift into a more diversified product line with software and training. - Brian[/tweetthis] Here are today’s conversation points:

Our reactions to the Presidential election.
Jordan’s new custom job, and how he’s preparing for it.
How to fill gaps in your business.
Brian’s new training program.
Building a good foundation ladder.
The challenges of bootstrapping.
Jordan’s time at Tanner Larson’s Mastermind.
Brian’s planning discussions with his developers.
Advice about pricing and how to decide it.

[tweetthis]We are not giving up on short-term stuff but it is nice to start thinking in terms of the next few weeks. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook’s Ecommerce Checkout Funnel As always, thanks for tuning in. Head here to leave a review in iTunes.

Taking a Big Shot vs. Lots of Little Shots

Bootstrapped Web — Thu, 10 Nov 2016 05:00:54 -0400

On today’s episode, we welcome Craig Hewitt and Justin Jackson to the podcast. Jordan is having some time away. On today’s episode Craig, Justin, and Brian all discuss how to build and keep a company on track. We discuss what drives us and what we’re working on at the moment. If you want to know how to plan a product or just try to set a trajectory for your business, this is the episode for you! Craig is the CEO of Podcast Motor, a podcast editing and production service. Justin is the host of his own podcast Mega Maker 3000 and a teacher of marketing for developers. We all have great insights to growing a company and how we’ve been able to stay on track. [tweetthis]I just really want to have a comfortable lifestyle, but also build valuable assets. - Brian[/tweetthis] Here are today’s conversation points:

Justin relaunch of Marketing for Developers.
Brian’s update on Audience Ops.
Craig’s update on Podcast Motor.
The lessons we’ve learned from starting and maintaining our businesses.
Our long term goals.
The disadvantages of working solo.
Why businesses choose to keep their companies small.
Justin belief in doing something uncomfortable for growth.
How you can over-plan.
Why you need to look at the bigger picture.
The importance of visibility and building relationships.
How to use evergreen content.
How we use automation in our businesses.
What keeps our ambition going?

[tweetthis]You can never retreat too much in working because you have to maintain a certain amount of visibility. - Justin[/tweetthis]

Resources Mentioned Today:

Market for Developers Podcast Motor Audience Ops Carthook Rogue Startups Podcast Justin’s website As always, thanks for tuning in. Head here to leave a review in iTunes.

Pricing Questions / SaaS vs. Service

Bootstrapped Web — Thu, 27 Oct 2016 06:00:24 -0300

We’ve got a party episode today. We welcome Rob Williams of Workshop and Folyo. Allan Branch joins us later on in the episode when we discuss his time with Less Accounting. [tweetthis]There are pros and cons to both the service and the software side of things. - Brian[/tweetthis] Today’s topic was primarily pricing. How to price effectively, why to price at a certain level, and what pricing can do for your business. This episode was a great discussion on how value to the customer is reflected in the pricing of a service or product. We had some great insights today and maybe we’ll help you decide how to price your own service or product. Here are today’s topics:

Rob’s service Workshop. What is it?
Why Rob has recently changed the pricing of the service.
The art of pricing.
How pricing attracts the “right” clientele.
What is Folyo?
To do or not to do a Free Trial.
What is Audience Ops Calendar?
How to offer value to a customer.
Catching up with Allan Branch.
Why you are always beholden to somebody.
Why Allan and his team sold Less Accounting.

[tweetthis]If you want to tie pricing to value isn't that [revenue] the ultimate value? But no one does it! - Jordan[/tweetthis]

Resources Mentioned Today:

Foylo Workshop Less Everything Carthook Audience Ops Calendar As always, thanks for tuning in. Head here to leave a review in iTunes.

Adding Service to Software / Marketing Pre-MVP

Bootstrapped Web — Thu, 13 Oct 2016 06:00:59 -0300

Today’s episode is basically a therapy session for us both. We lay out our current issues and talk each other though the options. Jordan is dealing with customers and their personal expectations for the products. Brian is looking for balance in his development stage on the calendar product. We try our best to see our situations from all angles and possibilities. [tweetthis]The first step is deciding which things are the right things to pursue. - Jordan[/tweetthis] So join us for our conversation today, you might learn some things about the futures of Carthook and Audience Ops. Here are today’s topics:

Carthook’s customer response to the checkout product.
Dealing with customer requests.
When it is time to expand a company.
Approaching service based business models.
Approaching product based business models.
The alternative answer to consulting services.
How to standardize operations.
The 2 approaches to launches.
Finding the balance of life and product development.
An Audience Ops podcast.
Audience Ops webinars.

[tweetthis]What's the higher level goal for the company? And that's not just revenue and profit. - Brian[/tweetthis]

Resources Mentioned Today:

CartHook Audience Ops Calendar

Sponsor

Indeed Prime – Get a $5,000 bonus when you get hired through Indeed Prime using Bootstrapped Web’s link. As always, thanks for tuning in. Head here to leave a review in iTunes.

Updates: Dev Process, MRR Milestones, Remote vs. Office

Bootstrapped Web — Thu, 06 Oct 2016 07:00:01 -0300

Today is a basic update episode, but we have a special guest as well. Justin McGill is the co-founder of LeadFuze and co-host of the podcast Zero to Scale. He joins us on the update train today and gives us an idea of what the future holds for LeadFuze. Jordan tells us how his team meetup is going and Brian fills us in on what is going on with Audience Ops. [tweetthis]Finding talent is so hard & to limit to just my zipcode is... I don't see how that would have worked. - Brian Casel[/tweetthis] We cover a lot of topics today. Our main discussion boils down to the pros and cons of remote teams. A lot of founders find remote works well for them, but today we discuss the virtues of a brick and mortar office space. Here are today's topics:

Jordan’s meetup progress.
The pressures of being the boss and having a life.
Jordan’s product development troubles.
Jordan’s new website and onboarding process for the check-out product.
Brian’s 50k milestone.
Brian’s search for a good writer.
Brian’s return to sale calls.
Justin’s LeadFuze issues.
The stress of going from remote team to office space.
The importance of office culture to a business.
How to decompress while working at home.
Slack vs. e-Mail
What’s going on with Audience Ops’ software.

[tweetthis]There is a point in time where you just say 'Screw it, I'm going to start marketing.' - Jordan Gal[/tweetthis]

Resources Mentioned Today:

Zero to Scale LeadFuze CartHook Audience Ops Calendar

Sponsor

Indeed Prime - Get a $5,000 bonus when you get hired through Indeed Prime using Bootstrapped Web's link.

As always, thanks for tuning in. Head here to leave a review in iTunes.

Going Global: Team Travel, Tiny Confs, & Remote Lifestyle

Bootstrapped Web — Thu, 29 Sep 2016 07:00:42 -0300

Going Global: Team Travel, Tiny Confs, & Remote Lifestyle

Bootstrapped Web — Thu, 29 Sep 2016 07:00:42 -0300

Going Global: Team Travel, Tiny Confs, & Remote Lifestyle

Bootstrapped Web — Thu, 29 Sep 2016 07:00:42 -0300

We’re are having a “party” episode with some special guests today. We’ve got Dave Rodenbaugh, Craig Hewitt, and later on Brad Touesnard joining us. We are all involved with Big Snow Tiny Conf. Brian is head of the Vermont event, Dave is head of the West event (Colorado.) Craig is taking care of our European event in France. Today we talk about the conference and why we love it. [tweetthis]It's [Big Snow Tiny Conf] half retreat, half mastermind. - Dave Rodenbaugh[/tweetthis] We also discuss living abroad and working remote and with remote teams. The startup world is going global and we want Big Snow Tiny Conf to reflect that. Here are today’s topics:

What is Big Snow Tiny Conf
Big Snow Tiny Conf East
Big Snow Tiny Conf West
Big Snow Tiny Conf Europe
Why the events are awesome!
Jordan’s meetup with his team
Why traveling is a perk to the Bootstrapped lifestyle

If you have an interest in Big Snow Tiny Conf tickets go on sale Oct. 10th. Remember these events are meant to be small so space is limited. Big Snow Tiny Confs East and West (Vermont and Colorado) are scheduled for Feb. 6-9. Big Snow Tiny Conf Europe (France) is scheduled for Jan. 16-19. [tweetthis]I think travel specifically is one of the big drivers of why I do this for a living. - Brian Casel[/tweetthis]

Resources Mentioned Today:

Big Snow Tiny Conf Bootstrapped Web

Sponsor

Indeed Prime - Get a $5,000 bonus when you get hired through Indeed Prime using Bootstrapped Web's link.

As always, thanks for tuning in. Head here to leave a review in iTunes.

Pre-selling and Planning to Build 'Audience Ops Calendar'

Bootstrapped Web — Thu, 22 Sep 2016 07:00:32 -0300

Pre-selling and Planning to Build 'Audience Ops Calendar'

Bootstrapped Web — Thu, 22 Sep 2016 07:00:32 -0300

Today on Bootstrapped Web we talk about a new product from Audience Ops. Brian has developed a software product called Audience Ops Calendar. He has offered it to 12 clients and based his approach on a pre-sale model. During today’s episode Brian tell us how he has developed the product. He answers why he chose to develop a calendar, how to use his software, and how he plans to market it. If you’ve ever been curious about a SAAS development this episode will tell you the right way to go about it. [tweetthis]Getting people into your software product to pay a monthly fee is not the only way to sell your software product. - Jordan[/tweetthis] Here are today’s conversation points:

Why Brian decided to launch this idea.
The problems the project has had.
The 3 ideal customers for Brian’s product.
The features of the product.
Brian’s process to develop the product.
Why having a beta group is a good idea.
Brian’s team building process.

[tweetthis]Reach certain milestones that you are able to invite 5 paying customers. Then another 5, then another 5. - Brian[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Audience Ops Calendar WP Simple Pay Pro As always, thanks for tuning in. Head here to leave a review in iTunes.

Cofounders - w/ Rob Walling and Ben Fisher

Bootstrapped Web — Thu, 01 Sep 2016 06:00:11 -0300

Cofounders - w/ Rob Walling and Ben Fisher

Bootstrapped Web — Thu, 01 Sep 2016 06:00:11 -0300

We welcome Rob Walling and Ben Fisher to the podcast today. We are going to discuss the topic of co-founders. Rob is the original founder of Drip, but has found a co-founder named Derek. Ben is Jordan’s co-founder in Carthook. Brian however is the solo founder prospective in today’s conversation. Brian has had co-founders, but Audience Ops is all him. On today’s episode Jordan and Ben talk about how they began their partnership and Rob discusses his partnership with Derek. In recent news Rob’s company Drip has been acquired by Leadpages. He tells us about that change and how it has affected his partnership. [tweetthis]In the early stage it's easy to overlook how difficult will it be to make it [SAAS] a viable business. - Brian[/tweetthis] The topics we covered are:

How Leadpages’ acquisition has changed Drip.
Why you are always reinvesting into your business.
Jordan’s original intentions for Carthook.
Why Jordan needed to work with Ben.
The issues for a solo founder.
How Ben found Jordan.
How Rob found his business partner.
The 2 factors of finding the right business partner.
How to divide up decision making.
The pros and cons of partnerships.
How to respect your partner.
Agreeing to a shared goal with your business partner.

[tweetthis]Is there a such thing as a final decision or is everything a collaboration? - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Drip Leadpages Lean Startup Machine ZenFounder As always, thanks for tuning in. Head here to leave a review in iTunes.

New Products First Steps & Next Steps

Bootstrapped Web — Thu, 25 Aug 2016 07:00:25 -0300

New Products First Steps & Next Steps

Bootstrapped Web — Thu, 25 Aug 2016 07:00:25 -0300

New Products First Steps & Next Steps

Bootstrapped Web — Thu, 25 Aug 2016 07:00:25 -0300

Well the launch for our new products are getting nearer. Today we give a general update on things and we talk about where we are on the new products. Brian is in the beginning of this process and Jordan is coming to the end of the process. Planning a new product is stressful. We discuss that stress and how we have personally dealt with it. There are tons of decisions that have to be made and there is the danger of getting caught up in the “what-ifs.” During today’s episode we talk about these roadblocks and how we plan to get pass them. [tweetthis]There is the factor that I am self-funding this and the need to budget. I need to do things in a smart way. - Brian[/tweetthis] The points we covered today:

Jordan’s upcoming vacation plans.
Brian’s mini- vacation.
When it is time to let go of the service side of your business to a team.
How a mind shift can help a project’s issues.
How an outsider’s perspective can help project disputes.
The importance of getting feedback from potential customers.
Brian’s new product process.
The benefits of having an “inner circle” of customers.
The stress of project decision making.
When to ask for a credit card.
How to on-board new customers the right way.
Why you should “launch ugly” instead of “ready.”

[tweetthis]I didn't know how to push a tech team, nor have the experience & the knowledge. I'm not a product manager. - Jordan[/tweetthis]

Resources Mentioned Today:

Audience Ops Carthook Productize As always, thanks for tuning in. Head here to leave a review in iTunes.

Pricing

Bootstrapped Web — Thu, 11 Aug 2016 07:00:29 -0300

Planning vs. Execution

Bootstrapped Web — Thu, 04 Aug 2016 07:00:24 -0300

Tools

Bootstrapped Web — Thu, 28 Jul 2016 07:00:21 -0300

The Bootstrapper's Search For Meaning

Bootstrapped Web — Thu, 21 Jul 2016 07:00:47 -0300

Playing the Long Game

Bootstrapped Web — Thu, 14 Jul 2016 07:00:17 -0300

Growing The Product Line & Shifting Priorities

Bootstrapped Web — Thu, 07 Jul 2016 07:00:21 -0300

Growing The Product Line & Shifting Priorities

Bootstrapped Web — Thu, 07 Jul 2016 07:00:21 -0300

Questions on Pricing, Charging a Percentage, and Why Podcast?

Bootstrapped Web — Thu, 30 Jun 2016 07:00:53 -0300

[112] Do Entrepreneurs Get to Have Hobbies? And Other Updates...

Bootstrapped Web — Thu, 23 Jun 2016 07:00:30 -0300

[111] How to Audit Your Design, UI & UX w/ Jane Portman

Bootstrapped Web — Thu, 16 Jun 2016 07:00:08 -0300

[110] Learning to Manage a Team / Launching a New Sales Strategy

Bootstrapped Web — Thu, 09 Jun 2016 07:00:28 -0300

[109] Behind Jordan's Rollercoaster New Product Launch

Bootstrapped Web — Thu, 02 Jun 2016 07:00:41 -0300

[108] Growing Families And Growing Businesses

Bootstrapped Web — Sun, 29 May 2016 07:04:55 -0300

[107] Our Recap of MicroConf 2016

Bootstrapped Web — Thu, 28 Apr 2016 07:00:44 -0300

[106] Launch Updates, Goals for a New Hire & Optimal Work Environments

Bootstrapped Web — Thu, 24 Mar 2016 07:00:48 -0300

[105] Crafting Your Sales Process w/ Damian Thompson

Bootstrapped Web — Thu, 17 Mar 2016 07:00:23 -0300

[104] Updates: A Stealth Launch, A Public Launch, & Hiring for a New Role

Bootstrapped Web — Thu, 10 Mar 2016 06:00:05 -0400

[103] The E-Commerce Episode

Bootstrapped Web — Fri, 04 Mar 2016 07:38:17 -0400

[102] Updates: Remote Company Culture & Bandwidth for Big Customers

Bootstrapped Web — Fri, 26 Feb 2016 08:16:07 -0400

[101] Evolving Your Sales Systems

Bootstrapped Web — Thu, 18 Feb 2016 06:00:17 -0400

[100] Updates: Repeatable Marketing Ideas, Outsourcing Sales, & "Secret" SaaS Tiers

Bootstrapped Web — Thu, 11 Feb 2016 06:00:31 -0400

[99] Updates De-Bottlenecking, Productize Relaunch, & Firing a Client

Bootstrapped Web — Thu, 21 Jan 2016 06:00:15 -0400

[98] Website Teardowns! a Form Builder, Invoicing, and WordPress products

Bootstrapped Web — Thu, 14 Jan 2016 02:00:13 -0400

[97] Problems to Solve in 2016

Bootstrapped Web — Thu, 07 Jan 2016 02:00:32 -0400

[96] Our 2015 Recap and 2016 Goals

Bootstrapped Web — Thu, 31 Dec 2015 02:00:15 -0400

[95] Rollercoaster Entrepreneurial Emotions, Working with Partners & Hiring Fast Enough

Bootstrapped Web — Thu, 24 Dec 2015 02:00:46 -0400

[94] From "Accidental Solution" to $50K Launch of a Productized Service, with Dan Schwartz

Bootstrapped Web — Thu, 17 Dec 2015 02:00:40 -0400

[93] 80/20 Hacks That Move the Needle for Us

Bootstrapped Web — Thu, 10 Dec 2015 02:00:45 -0400

[92] Updates! Plugin Launch Results, High Value Customer Triggers, & Seasonality

Bootstrapped Web — Thu, 03 Dec 2015 02:00:56 -0400

[91] Figuring Out Who Your Target Customer Is (And Why)

Bootstrapped Web — Thu, 26 Nov 2015 02:00:52 -0400

[90] Staying Accountable With Teammates and Launching a Plugin Product

Bootstrapped Web — Thu, 19 Nov 2015 02:00:46 -0400

[89] Making the Most of Outbound Sales Tools

Bootstrapped Web — Thu, 12 Nov 2015 02:00:39 -0400

[88] Staying Focused and Getting Things Prioritized

Bootstrapped Web — Thu, 05 Nov 2015 02:00:29 -0400

[87] Productized Services with Craig Hewitt of Podcast Motor

Bootstrapped Web — Thu, 29 Oct 2015 04:00:21 -0300

[86] Masterminds, Content Production, and Getting Things Done

Bootstrapped Web — Thu, 08 Oct 2015 03:00:10 -0300

[85] Refocusing and Getting Things Done in Less Time

Bootstrapped Web — Thu, 01 Oct 2015 03:00:48 -0300

[84] MicroConf Europe 2015 Recap Show

Bootstrapped Web — Thu, 10 Sep 2015 03:00:55 -0300

[83] Thomas Smale on Selling Your Online Business

Bootstrapped Web — Thu, 27 Aug 2015 03:00:27 -0300

[82] Growing Our Teams, New Initiatives, and Your Questions

Bootstrapped Web — Thu, 13 Aug 2015 03:00:27 -0300

[81] Scaling Our Businesses Through Process, Team and Procedures

Bootstrapped Web — Thu, 30 Jul 2015 03:00:16 -0300

[80] Brecht Palombo on Longterm Travel as an Entrepreneur

Bootstrapped Web — Thu, 23 Jul 2015 09:06:48 -0300

[79] Building Awesome Online Courses with Keith Perhac of Summit Evergreen

Bootstrapped Web — Mon, 20 Jul 2015 03:00:05 -0300

[78] Changing the Course of Our Businesses

Bootstrapped Web — Mon, 13 Jul 2015 03:00:45 -0300

[77] Justin McGill on the Importance of Visibility as a Founder

Bootstrapped Web — Thu, 25 Jun 2015 03:00:06 -0300

[76] Tim Conley on Entrepreneur Coaching

Bootstrapped Web — Fri, 12 Jun 2015 03:00:48 -0300

[75] Pricing Strategy, Marketing Focus, and Launch Updates

Bootstrapped Web — Mon, 08 Jun 2015 03:00:35 -0300

[74] Effective Positioning with Philip Morgan

Bootstrapped Web — Thu, 28 May 2015 03:00:18 -0300

[73] Taylor Pearson on The End of Jobs

Bootstrapped Web — Thu, 21 May 2015 03:00:08 -0300

[72] Updates on AudienceOps and Carthook

Bootstrapped Web — Thu, 14 May 2015 03:00:00 -0300

[71] The Reveal: Brian's New Business

Bootstrapped Web — Thu, 07 May 2015 03:00:10 -0300

[70] The MicroConf 2015 Recap Show

Bootstrapped Web — Thu, 30 Apr 2015 03:00:55 -0300

[69] Liam Martin on Building a Distributed Team and Lessons Learned Scaling

Bootstrapped Web — Thu, 16 Apr 2015 03:00:21 -0300

[68] Mike Taber on Life as a Single Founder

Bootstrapped Web — Thu, 09 Apr 2015 03:00:39 -0300

[67] What Our Past Failures Taught Us

Bootstrapped Web — Thu, 02 Apr 2015 03:00:21 -0300

[66] Decision Making to Move Your Startup Forward

Bootstrapped Web — Thu, 26 Mar 2015 03:00:14 -0300

[65] Rob Walling on Drip, Microconf, and the Future of Bootstrapped Startups

Bootstrapped Web — Thu, 19 Mar 2015 03:00:12 -0300

[64] Giving Customers What They (Really) Want w/ Robert Williams of Workshop

Bootstrapped Web — Thu, 12 Mar 2015 04:00:27 -0300

[63] Content Consumption to Fuel Our Work

Bootstrapped Web — Mon, 09 Mar 2015 07:08:09 -0300

[62] Transitioning From One Business to the Next

Bootstrapped Web — Fri, 27 Feb 2015 14:58:50 -0400

[61] What Makes a Podcast Irresistible? w/ Adam Clark

Bootstrapped Web — Fri, 20 Feb 2015 05:39:16 -0400

[60] From Leads to Trials to Customers

Bootstrapped Web — Thu, 12 Feb 2015 03:00:25 -0400

[59] The Dark Art of Product Validation

Bootstrapped Web — Fri, 06 Feb 2015 14:41:42 -0400

[58] Product vs. Marketing. Which to Focus on Right Now?

Bootstrapped Web — Thu, 29 Jan 2015 03:00:32 -0400

[57] Is $99 The New $19 in SaaS?

Bootstrapped Web — Thu, 22 Jan 2015 03:00:39 -0400

[56] How to Hire for Customer Support

Bootstrapped Web — Thu, 15 Jan 2015 14:01:07 -0400

[55] Leveraging Other People as a Solo Founder

Bootstrapped Web — Thu, 08 Jan 2015 03:00:25 -0400

[54] Our 2014 Recap & 2015 Goals

Bootstrapped Web — Thu, 01 Jan 2015 03:00:21 -0400

[53] Get More Leads with Brennan Dunn

Bootstrapped Web — Thu, 18 Dec 2014 11:56:08 -0400

[52] Exactly How to Build a Sales Funnel From Scratch, and Why

Bootstrapped Web — Thu, 11 Dec 2014 03:00:31 -0400

[51] Crush Every Goal You Set with Clint Warren

Bootstrapped Web — Thu, 04 Dec 2014 03:00:12 -0400

[50] Getting First Customers For a SaaS, Pricing Your Product, & Other Listener Questions

Bootstrapped Web — Thu, 27 Nov 2014 03:00:44 -0400

[49] Allan Branch Joins us to Talk Less, Life, Focus & SaaS

Bootstrapped Web — Thu, 20 Nov 2014 03:00:07 -0400

[48] Launch Sequence & a Case Study of Brian's Productize Course Launch

Bootstrapped Web — Thu, 13 Nov 2014 03:00:30 -0400

[47] Business Models for Bootstrappers

Bootstrapped Web — Thu, 06 Nov 2014 03:00:25 -0400

[46] Family Business

Bootstrapped Web — Thu, 30 Oct 2014 04:00:34 -0300

[45] To Build An Audience Or...

Bootstrapped Web — Fri, 24 Oct 2014 06:54:21 -0300

[44] How to Build a Productized Service Business w/ Nick Disabato (Draft Revise)

Bootstrapped Web — Thu, 16 Oct 2014 15:01:28 -0300

[43] How to Raise Prices, Outsourcing, and Other Listener Questions

Bootstrapped Web — Thu, 09 Oct 2014 04:00:51 -0300

[42] Using Webinars as a Bootstrapper

Bootstrapped Web — Thu, 02 Oct 2014 04:00:14 -0300

[41] Outsourcing: When, Why & How?

Bootstrapped Web — Thu, 25 Sep 2014 04:06:39 -0300

[40] Doing Customer Research

Bootstrapped Web — Thu, 18 Sep 2014 03:55:12 -0300

[39] Doing Things Manually

Bootstrapped Web — Thu, 11 Sep 2014 04:00:51 -0300

[38] Building an Audience-Based Business with Justin Jackson

Bootstrapped Web — Thu, 04 Sep 2014 04:00:35 -0300

[37] Thinking BIG

Bootstrapped Web — Thu, 28 Aug 2014 04:10:09 -0300

[36] Building a Business From Your Passion w/ Sean McCabe (seanwes)

Bootstrapped Web — Thu, 21 Aug 2014 04:00:48 -0300

[35] Why Do an Info Product?

Bootstrapped Web — Thu, 14 Aug 2014 03:00:22 -0300

[34] Hacking Productivity by Leveraging Pressure

Bootstrapped Web — Thu, 07 Aug 2014 03:24:33 -0300

[33] Launch Your Product Business... By Getting a Job?

Bootstrapped Web — Thu, 31 Jul 2014 04:00:34 -0300

[32] From The Verge to Niche Startups: Dann Berg talks Audience Focus

Bootstrapped Web — Thu, 24 Jul 2014 03:15:27 -0300

[31] Mastermind Groups. What, Who, How, and Why?

Bootstrapped Web — Thu, 17 Jul 2014 04:40:29 -0300

[30] Learn How to Systematize Like The Big Boys

Bootstrapped Web — Thu, 10 Jul 2014 04:56:38 -0300

[27] Let’s Dissect This Email Marketing Automation Sequence with Daniel Faggella (Science of Skill)

Bootstrapped Web — Thu, 05 Jun 2014 04:11:42 -0300

[19] Selling a Web Agency to Focus on Products w/ Brent Weaver (UGurus)

Bootstrapped Web — Thu, 03 Apr 2014 03:45:32 -0300

[14] Consulting vs. Products (or both?) with Brad Touesnard

Bootstrapped Web — Thu, 05 Dec 2013 03:01:10 -0400

[13] Case Study: Sacha Greif on His Redesign of Folyo.me

Bootstrapped Web — Thu, 24 Oct 2013 03:21:56 -0300

[12] Can a Consultancy Be Systemized? Let's Ask The Expert, Kelly Azevedo (She's Got Systems)

Bootstrapped Web — Fri, 13 Sep 2013 12:38:02 -0300

[11] From Idea to 10 Paying Customers in Less Than a Week - w/ Dan Norris (WP Curve)

Bootstrapped Web — Mon, 02 Sep 2013 03:29:41 -0300

[10] Rob Walling Shares His Approach to Scaling a Portfolio of Startups

Bootstrapped Web — Mon, 12 Aug 2013 03:35:20 -0300

[9] Becoming a 5-Tool Blogger

Bootstrapped Web — Mon, 29 Jul 2013 03:43:57 -0300

[8] Adii Pienaar (WooThemes & PublicBeta) on Starting Again From The Ground Up

Bootstrapped Web — Mon, 22 Jul 2013 03:00:26 -0300

[7] Nathan Barry Explains How His Very 1st Book Sold $12k on Day One... And more

Bootstrapped Web — Mon, 15 Jul 2013 03:00:46 -0300

[6] 10 First-Year Mistakes & Lessons Learned Bootstrapping a Startup - [Free Report]

Bootstrapped Web — Mon, 08 Jul 2013 02:45:52 -0300

[5] How I Transitioned From Consulting to Products, Full-Time

Bootstrapped Web — Mon, 01 Jul 2013 02:45:09 -0300

[4] 2 Years, 77+ Different Products?! An Inside Look at Pippin Williamson's WordPress Plugins Business

Bootstrapped Web — Mon, 24 Jun 2013 03:00:41 -0300

[3] How Brennan Dunn Leverages His Best Marketing Asset: His List

Bootstrapped Web — Mon, 17 Jun 2013 03:00:13 -0300

[2] How Choosing The Right Feedback Leads To Greater Product Focus - w/ Dan Norris of Inform.ly

Bootstrapped Web — Mon, 10 Jun 2013 02:16:03 -0300

[1] The Bootstrapper's Mindset — How Bootstrappers Learn by Doing

Bootstrapped Web — Fri, 31 May 2013 20:12:35 -0300