Personal goals for 2026

• Rick 
  • Getting back to basics
  • Going from reactive to proactive (and surviving to thriving)
  • Shifting from a strategy of playing it safe and reducing risk to taking smart risk and being ok looking a little foolish
• Tyler 
  • Handle the transition back to full-time work (as it impacts parenting)
  • Find clarity on what level of wealth we’re comfortable exposing our daughter to.
  • Help Shelly find more ways to go out at night while I take care of Syd
  • Finalize will+trust
  • Stretch goal: Start vibe coding personal apps

Professional goals for 2026

• Rick (hopes to achieve at least two of these goals) 
  • Outsource, delegate, or automate recurring tasks that I no longer value doing and/or others don’t value me doing
  • Try to grow LegUp Health by 50%, but do it in a way that we are all excited about
  • Rebuild personal website + read 10 really, really good nonfiction books and publish notes on them
  • Experiment with AI to generate 1 additional revenue stream
• Tyler 
  • Spend almost all IC time on design, product management, and coding. Fewer distractions!
  • Management: Get the team up to speed on AI, and make it self-sustaining
  • Product management/design: Figure out how to keep up with the devs (especially if AI allows them to move even faster)
  • Product 
    • Ship Mobile and Kanban
    • Reduce support by making things more self-serve
    • Main theme: The first 30 minutes 
      • Onboarding improvements
      • Rebuild the importing flow
      • Simplification 
        • Separate contacts and companies
        • Open contacts in page dialog
        • Statuses on the contact record
        • Table view of contacts

Here's the AI tool Rick mentioned for recording your screen (we'll talk about that in a future episode)

Here's the AI report Rick mentioned

Here's the blog post about First Team Principles Rick mentioned.

Takeaways

• Tyler prefers soda over coffee for his morning routine.
• Rick has re-engaged with podcasts, discovering new content.
• Leg Up Health achieved a record revenue month, nearing their goal.
• Setting realistic revenue goals can provide relief and stability.
• AI integration is becoming crucial for business operations.
• Internal tools can significantly improve team efficiency.
• Customer feedback is essential for product development.
• Pricing strategies need careful consideration for new offerings.
• Exploring new product opportunities can enhance revenue per user.
• Authenticity in customer outreach is vital for engagement.

Chapters
00:00 Parenting and Sleep Challenges
03:29 Reading Habits and Fantasy Literature
06:32 Business Growth and Revenue Updates
09:21 Form Metrics and Marketing Strategies
12:17 Internal Use Cases and New Features
15:23 Exploring Industry-Specific CRM Opportunities
21:22 Future of CRM and Industry Integration
28:57 Navigating Software Integration Challenges
32:34 The AI Dilemma: To Adopt or Not?
37:13 AI Readiness: Preparing for the Future
39:38 Revenue Metrics and AI Efficiency
50:28 Exploring AI Opportunities in Customer Experience

Takeaways

Fatherhood brings unexpected challenges and joys.
Work-life balance is crucial for new parents.
Fundraising milestones can be a time for reflection.
Vibe coding allows for rapid development with AI assistance.
AI can enhance productivity but may lead to fragility in code.
Clear communication is key in demonstrating value to clients.
Packaging benefits effectively can unlock new opportunities.
Understanding the market is essential for product success.
AI tools can streamline content creation processes.
The future of work may require new skills and adaptability.

Chapters

00:00 The Journey of Fatherhood
03:16 Navigating Work-Life Balance
06:21 Milestones in Professional Growth
09:09 The Dynamics of Startups
12:11 Innovations in Health Tech
15:20 Vibe Coding and AI in Development
18:19 The Future of Software Development
21:11 Content Creation with AI
25:43 Navigating the AI Landscape
32:56 The Future of Learning in an AI World
37:26 Innovating Benefit Programs
49:06 Packaging Value in Health Benefits

Personal goals for 2025:

• Rick: Primary theme: Buy back time
  • Take 1 personal day every 1-2 months
  • Get time back for things I love (skiing, basketball, be present on vacations, reading/writing, local networking)
  • Have a familiy vacation on the calendar to look forward to at all times
• Tyler
  • Baby stuff
    • Remain flexible and do whatever needs to be done
    • Create space for Shelly to have a life outside of just parenting
    • Take advantage of the calm life I've built
  • Don't hold myself to all my pre-baby health goals, but don't totally give them up either

Professional goals for 2025:

• Rick
  • Legup Health: I don't know yet, but most likely...
    • 2x revenue (maybe less)
    • Make sure JD's role is sustainable
    • Make sure the business is properly financed
  • Windfall: Scale myself. Level up, and make sure the team levels up with me
• Tyler
  • Don't worry about growth. Focus on input, not output.
  • Product
    • Tie off the big 2024 projects
    • Definitely ship kanban and a mobile app
    • Stretch goal: Ship one other big thing (sending email, automations, or reports)
  • Reduce the set of things I'm responsible for so I can focus on the things I'm best at

*Clickbait warning: We don't actually spend much time on this topic, I just wanted a catchy title for the episode. Did it work? Did you listen because of my misleading title? Let me know in the comments**

**There are no comments. This is a podcast.

Personal updates from 2023

• Tyler
  • Goals from last year
    • 🆗 Take more vacation and make up with with extra work off-hours work
    • 🆗 Renovate the house
  • Other updates
    • Found a band I like: Caligula's Horse
    • First time as an adult I feel good about my exercise routine
• Rick
  • Goals from last year
    • ❌ Get weight below 200lbs
    • ❌ Write a newsletter most Sundays (27 total)
  • Other updates
    • Built a new house and moved in
    • Had another baby (daughter)

Personal goals for 2024

• Tyler
  • Maintain exercise routine: 9k steps/day + 2 rucks/week + 200 pushups/week
  • Finish house remodel
• Rick
  • Rebuild daily exercise and writing habit
  • Be more present with family when I’m with them
  • Regular dates with Sable (2 per month minimum)
  • 4 vacations, with at least the next one scheduled at all times to look forward to

Professional updates from 2023

• Themes of the podcast
  • You can't optimize nothing (mostly applies to Rick)
  • Back to the basics (mostly applies to Tyler)
• Tyler
  • Goals from last year
    • ❌ Get back to decent growth: $36k ARR/ $3k MRR per month
    • ✅ Sense of urgency on the dev team. No more 2-week projects that end up taking six months.
    • 🆗 End the year with three major product wins
  • Other updates
    •  Announced the price increase for legacy customers 
    •  ~3 new devs sort of. Dev team is feeling way better than ever before.
    •  Improved money management 
    • Coded a lot
    • Joined LegUp Health as a side project
• Rick
  • Goals from last year
    • ✅ Retain JD full-time for another year
    • 🆗 Double the client base again (~200 clients) - 160 clients
    • ❌ Build V1 of LegUp Benefits and generate $1K per month in MRR from it (3-4 customers)
  • Other updates
    • Tyler joined LegUp Health as a partner
    •  Expanded services to group health insurance, and started figuring that out
    •  Made it to $100K annual revenue run rate + profitability in December

Professional goals for 2024

• Tyler
  • Don't worry about growth unless something unexpected happens
  • Focus on customer delight: If you ask a typical customer whether LACRM improved in 2024, their answer should be "hell yeah"
  • Maintain stability related to the team, culture, etc.
  • Protect coding time. Should be averaging >1 full day of coding per week
• Rick
  • Get LegUp Health to $200K ARR
  • Apply Profit First Framework / Pay partner distributions, even if small
  • Get JD to his target compensation
  • Prioritize better at Windfall / leverage over optimization

Biggest worry

• Tyler: Our execution on the product side won't be enough to close the gap with competitors
• Rick:  I won’t figure out how to prioritize and manage my personal health as I build a family 

What we want to learn

• Tyler: How to code like it's 2024. Should be able to do everything the other LACRM devs can do with no blind spots
• Rick: Nothing specific. 2024 is about execution

Full topic list:

• LegUp Health has a new website.
• Rick thinks he's feeling an inflection point.
• We daydream about the future of LegUp Health a bit.
• Things are calm at LACRM, and the employees are all increasingly experienced.
• Tyler is coding again.
• There's a new buzzword at LACRM.
• We complain about X/Twitter.

Here's the full topic list:

• Rick is finally in his new house, and a major stress has been removed.
• Rick gives updates on LegUp Health, including a major unlock to getting employers onboard.
• Rick talks about progress towards hitting annual sales goals.
• Tyler talks about other ways he's been able to simplify LACRM's operations.
• Tyler has a coughing fit and we give up early.

Here are all the topics:

• LACRM has started migrating to Paddle.
• LegUp Benefits has its first official customer!
• We discuss how LACRM's free trial pipeline isn't as correlated with paying user growth as you'd expect.
• We dive deep into the history of LACRM's product strategy, and what comes next.
• Rick has a major milestone to share.

Here are all the topics:

• Rick updates us on LegUp Health's progress. He talks about working on the sales pitch, building momentum, staying focused, and more.
• Tyler is merging two teams at LACRM. We discuss what the impact of that change might be.
• We spend a while discussing different growth ideas, especially related to sales and outbound marketing.

• Tyler is trying to focus everyone at LACRM on the top priorities including:
  • Having the devOps team do a bit more normal software engineering work.
  • Offering customer service people a chance to work on marketing and sales.
  • He himself is starting to code again.
• Rick explains how LegUp Health is focused on execution and it seems to be working.
• Rick/JD hired a sales coach.
• Rick talks about what he learned from the book Amp It Up.
• Tyler poorly explains why LACRM is going to work on a feature that isn't the top priority.
• We talk a bit about how to optimize a support team
• Rick is starting to think about how he can contribute to marketing.

Full topic list:

• Rick gives an update on how he and JD are getting out of a sales rut.
• Rick is busy and has absolutely zero free time.
• Tyler talks about how he's considering web forms and automations as possible features for LACRM.
• We discuss an alternative approach to freemium.
• We brainstorm how to use the "engineering as marketing" approach for LegUp Health, but don't really get anywhere.

Here's the full topic list:

• Rick is back from parental leave, and he has things to say about what it's like to take care of two kids at once.
• We discuss what our perfect days look like.
• Tyler talks about how LACRM had a bit of crunch mode, and how they stayed calm.
• Rick talks about a sales slump, and what he's doing about it.
• We talk about how LegUp Health migrated from no-code to full-code.
• Tyler gives an update on LACRM's growth the first half of the year.
• We talk about switching from Google Analytics to Fathom.
• LACRM is considering how to price a feature that has some extra infrastructure costs.
• Tyler is reconsidering a feature he's been talking about for years. Literally. Years.

Here are all the topics:

• Tyler has officially signed the partnership agreement with Rick and LegUp Health!
• Rick is wrapping up a position/brand/story project
• LegUp Health has updated their mission and core values
• Things are a bit hectic at LACRM
• Tyler is considering merging his personal blog back into the LACRM blog
• LACRM is probably switching from Stripe to Paddle
• Rick shares what he's learned servicing the early LegUp Health group insurance clients
• We talk a bit about ChatGPT and how it can be useful for no-code/low-code apps
• Tyler rants about how we talk about priorities

Here's the full topic list:

• Tyler takes a look back at LACRM's growth history, and explains their new approach to growth.
• Tyler explains how the recent Product Hunt launch went.
• Rick has cleared a lot off his LegUp Health plate and is starting to focus on new types of work.
• LegUp Health had its first partner meeting.
• April was a record month for LegUp Health.
• LACRM has their designer back with more hours than ever.
• Rick is looking to target CPAs as customers.
• The LACRM coding fellows have started.
• We discuss how to deal with the low points of being an entrepreneur.

Topics in this episode:

• Tyler is back from his sabbatical
• LACRM is getting ready to launch a major redesign
• Rick gives updates on how the LegUp Health/Benefits plan has changed
• Because of the changes, we renegotiated Tyler's compensation and involvement in the company
• Tyler talks about the difference building a product that customers don't expect to use regularly vs and every-day productivity tool.
• Rick gives an update on working with a marketing coach
• We talk about Seeyafuture.me

Topics:

• Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other more instead of having everything flow through Rick.
• Tyler gives some reflections on leaving LACRM for 6 weeks, and the early days of his sabbatical.
• Tyler describes a new positioning idea at LACRM.
• We discuss the early work on LegUp Benefits including customer validation and learning a new tech stack.
• Rick gives an update on his new group insurance efforts.
• We talk about Silicon Valley Bank even though we don't have anything to say that hasn't already been said.

Full topic list:

• We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to work for Rick on LegUp Benefits!
• Rick had his first annual offsite and shares a ton of great learnings.
• LACRM had a great month in February. There was absolutely nothing to learn from it.
• LACRM's major redesign is getting closer.
• Rick has streamlined bookkeeping and other financial tasks to save time.
• Tyler is thinking through when it makes sense to do custom work for a large client.
• We tackle a listener question: How do bootstrapped companies compete with funded competitors.

Full topic list:

• Rick already has a new group insurance client after deciding to give that a shot in the last episode.
• JD is visiting Rick in Utah next weekend.
• Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands...
• ...and Tyler is having to re-learn what to do with unstructured time.
• LegUp Health got hit with a bunch of spam contact forms.
• Tyler is planning the new office layout for LACRM.
• Apparently design debt is a thing.
• Tyler is having trouble getting started on the LegUp Benefits project. Side projects are hard.
• Rick brings up Youtube Premium, Quora, and NotionAI
• Big topic: We discuss the compensation proposal that Rick just sent Tyler.

Topics in this episode:

• Tyler shares his experience at Big Snow Tiny Conf
• Tyler is getting ready for a sabbatical which means delegating a lot of work to other people
• Rick talks about gather customer profiles at LegUp Health
• Rick explains what "aged leads" are
• We discuss whether or not it makes sense for Rick to go after group health insurance clients
• Tyler talks about an LACRM company tradition
• LACRM launched their Zapier integration!
• Tyler is preparing to do more design work
• We have some rants and shoutouts
• We talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire 

• Tyler is going to work with Rick to build the new LegUp Benefits SaaS product
• Rick has officially transitioned LegUp to 2023
• Rick talks about how Airtable Interfaces are useful
• Rick talks about an annual retreat with JD, and we discuss rituals and traditions
• Tyler is going to Big Snow Tiny Conf
• LACRM launched their new API, and are almost ready to launch Zapier integration
• We talk about the value of podcasting

• Tyler
  • Goals from last year
    • ✅ Plan for travel as part of relationship 
    • ❌ Build more schedule flexibility 
  • Other updates
    • Figured out personal finance plan with Shelly
• Rick
  • Goals from last year
    • ✅ Reprioritize daily personal health habits 
    • ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands) 
    • ❌Writing goals

Professional updates from 2022

• Tyler
  • Goals from last year
    • ❓ Spend more time working, but on my own terms 
    • ❓ Make space to do more individual contributor design work 
    • ❌ Release redesign of LACRM
    • ❓ Two blog post-worthy updates per quarter
    • ✅ Shift product priorities to be more focused on growth/strategy and less on low-impact customer requests.
    • ✅ Run the coding fellowship
  • Other updates
    • More of a CEO, less of a manager
    • Growth was bad, but not as bad as expected
    • Product team got more focused
• Rick
  • Goals from last year
    • ✅ Structure a partnership and financial plan that enables JD to go full-time
    • ❌ Grow the business to 400 clients 
    • ❓Fully automate the new user onboarding experience
    • ✅ Help scale Windfall the right way  

2023 personal themes/goals

• Tyler
  •  Take more vacation and make up for it with extra work days
  •  Start working towards my rich life: Renovate the house
• Rick
  • Get weight below 200lbs 
  • Write a newsletter most Sundays (at least 27 Newsletters)

2023 professional themes/goals

• Tyler
  • Reap the rewards we sowed in 2022 (marketing projects and product team productivity)
  • Get back to decent growth: +$36k ARR per month
  • More of a sense of urgency on the dev team
  • Three major product wins
    • Redesign
    • Finish all "first round" growth projects (Zapier, API platform, event invites)
    • Close the gap between us as other CRMs (email logging and/or kanban view)
  • If there's a recession, minimize impact on customers and employees
• Rick
  • Retain JD for another year
  • Double the client base again (~200 clients)
  • Build v1 of LegUp Benefits and get to $1k MRR

Biggest worry

• Tyler: Product relevance - Have we lost ground in the CRM market
• Rick: Personal and family health

What do we want to learn?

• Tyler
  • How to communicate how decisions are made better
  • How to simplify policies so they are easier to understand
• Rick
  • How to build a SaaS via contractors and self-taught coding (i.e. without giving up equity)
  • Further expertise in digital advertising and data
  • Best practices for effective leadership (in the home, neighborhood, and workplace)

Predictions

• Tyler
  • Generative AI will advance, but not break through in 2023 (it will still seem more like the future than the present at the end of the year)
  • Binance and/or Tether will collapse, and Bitcoin will end the year down
  • The recession will get worse
    • S&P500 will be down over the first half of the year
    • There will be more tech layoffs in 2023 than there were in 2022
• Rick
  •  Big swing back to co-location as a working requirement 
  •  AI gets embedded into workflows for millennials 

•  LACRM is having a good December
• Rick is feeling lots of momentum
• Rick gives an update on LegUp Health's growth
• Rick is reading the Warren Buffet bio: The Snowball
• Tyler explains LACRM's new approach to bug triage
• Rick is thinking about how hard to push for in-person
• Tyler describes a new shorthand: Following daylight
• Rick realizes he's learning a lot about digital marketing
• We discuss how it's good for businesses to be boring and complex
• Ricks suggests having "certifications" for new hires
• We discuss Webflow Logic
• Rick is going on a date!
• Tyler is trying to decide how to prioritize big bets vs. small bets at LACRM.

• Rick gives an update on open enrollment
• Tyler talks about some upcoming product launches including the new Zapier integration
• Rick is refining his Adwords approach
• Rick is starting to think about 2023
• Tyler talks about project management
• LACRM had a CRM Coach culture refresh
• We talk about the recent wave of AI innovation

• I mean, Twitter, obviously
• Rick gives an update on open enrollment including...
  • Sales so far
  • His misadventures with Google advertising
  • Website positioning and design
• Tyler gives an update on LACRM's integration project
• LACRM just went through a process that happens every six months
• We talk fruitlessly about the potential recession and tech layoffs

• Rick gives a big update on how LegUp Health is prepping for open enrollment
  • His goal is to be long-term patient, but have short-term urgency
  • He doesn't have enough traffic for retargeting
  • Outreach will be their main lever
  • This weekend is his chance to get everything ready for November 1st
• Tyler talks about his time at Founder Summit
• LACRM is thinking about brand marketing instead of just performance marketing
• Tyler recounts a churn cohort analysis they did at LACRM
• Rick shares some advice he got from a friend
• Tyler gives an update on LACRM's integration partners
• We discuss "Courses as marketing"
• We talk about the value of sharing what you're working on with other people

• Tyler is getting ready for Founder Summit
• Rick is learning about digital advertising, and we discuss whether tracking people on the internet is a net good or bad thing
• Tyler gives an update on his NPS saga
• Tyler talks about a joint webinar he did with ZipMessage
• Rick describes his chamber of commerce webinar strategy
• Windfall is opening a Utah office
• Rick is getting ready to do outreach, but needs to reduce friction first
• Tyler is making some changes to how he approaches project management and prioritization
• We discuss a possible niche audience
• Rick explains how a major hole in the health insurance laws has been fixed
• Tyler started listening to the ShipSaaSFaster podcast

• Figma got acquired by Adobe AND I DONT WANT TO TALK ABOUT IT I'M NOT CRYING YOU'RE CRYING SHUT UP YOU'RE NOT MY REAL DAD
• Rick spent a week in Cancun and soaked up some sweet business wisdom
• Tyler is experiencing a period of calm at work and has done some coding for the first time in a long time
• LACRM decided not to hire interns next summer
• Rick and JD planned their marketing blitz
• Tyler gives an update on his work to make LACRM into a platform for API integrations
• We discuss how a company should decide what they're willing to spend on customer acquisition
• Tyler heard a new take on what "product-led growth" means from this podcast episode

• LACRM had a great growth month in August, mostly because of expansion revenue.
• JD, Rick's business partner, is doing a great job.
• Rick is oscillating between investing in more resources and staying focused.
• Rick gives an update on his recent local marketing blitz.
• Tyler is rethinking the customer onboarding flow.
• LACRM is shifting around their marketing priorities.
• Rick shares some wisdom from Jason Lempkin.
• Rick is learning how it's hard to not have authority.
• Tyler talks about hollow abstraction by mostly just parroting what's said in this video.
• We talk about "Zucking" (please don't look it up on Urban Dictionary, we're not talking about that kind of Zucking).

• Summer is ending at LACRM and things are going back to normal.
• Rick attended a company offsite last week, and now he's behind.
• LegUp Health is planning a local marketing blitz.
• Tyler gives an update on pay transparency at LACRM.
• Tyler has been doing some cold outreach to try to find API partners.
• There's a new VP at Lucid.
• Tyler talks about how this episode of Default Alive has an interesting take on no-code.
• Tyler and Rick talk about how it seems like it's getting harder to build a SaaS business, largely inspired by this episode of Out of Beta.

• LACRM got DDoSed *again*
• Rick went to some networking events
• Tyler is ending his newsletter
• Rick gives a chamber of commerce update
• LegUp Health is seeing early success with an incentive offer
• We discuss handling an employee who leaves for an extended period and whether the goal should be to have no single points of failure
• Rick talks about how intentional assumptions can combat fear
• Tyler gives an LACRM product-led growth update

• Less Annoying CRM hit $3.5 million ARR.
• Rick and LegUp Health have signed up for several in-person networking events as well as a number of chambers of commerce.
• LACRM had a new CRM Coach start.
• Tyler reflects on why his updates haven't been interesting recently, and what that might mean about how he'd feel running a bigger company.
• Rick got a new client who followed the ideal customer journey. Feels good.
• Rick is considering working with an SEO contractor.
• We discuss how to pick a digital marketing agency, and whether it even makes sense to do so.
  • In this episode, we discuss DemandMaven and JH Scherck.

• Tyler thinks he's finally fixed his audio setup.
• Rick and Tyler are both having good sales months. Rick actually knows why!
• We discuss what indicators a SaaS company might look at to tell whether a recession is impacting their business.
• Rick is getting weekly updates from JD in a new format that is working well.
• Rick went to a fancy-pants senator's house to schmooze with the big wigs and now he wants to meet more powerful people so that they can laugh at us common folk.
• Tyler talks about the possibility of LACRM expanding into services.
• Rick is building a list of people he might want to hire/work with one day.
• Rick's CPA ghosted him. CPAs are the worst.
• We discuss health urgency.

• Rick has learned more about how to be a good business partner.
• Rick is prioritizing effectiveness over efficiency.
• Tyler asks about how best to track marketing ROI.
• Tyler has an idea for a platform play at LACRM.
• Another company in LegUp Health's space has been aquired.
• Tyler gives an argument against delegation.
• Rick revisits the importance of buffer.
• Tyler recommends listening to this episode of the IndieHackers podcast.

• Rick is working on updating and simplify LegUp Health's messaging.
• LegUp Health is testing out purchasing leads.
• Rick talks about the next step of his SEO work.
• Tyler has been listening to customer interviews and learned some things about pricing and features with LACRM.
• Tyler isn't listening to as many business podcasts.
• We discuss the blog post: We Need A Middle Class For Startups

• The possibility of a recession and how it might impact businesses like ours.
• LegUp Health just had a competitor acquired.
• Less Annoying CRM was DDoSed again.
• Tyler discusses some traction channels he's been considering.
• Rick asks about virtuous vs. vicious cycles.
• We discuss the merits of a multi-product business vs a single-product business.

• Tyler bought tickets to attend Founder Summit.
• Tyler is rethinking his investment strategy.
• A competitor of LegUp Health is going out of business.
• Tyler is working on renewing LACRM's office lease.
• LegUp Health is struggling to scale their outreach, so they're going back to basics.
• LACRM's new design is coming along.
• LACRM is making pay more transparent internally.
• Rick wants LegUp to be in the discussion when people talk about health insurance in Utah.
• We discuss how to provide mentorship to employees if no one at your company has expertise in the area they need help with.
• We discuss what future marketing channels might be similar to what SEO was in the early 2000's.

• A new employee started at LACRM
• Tyler is getting ready for lots of interns
• Rick has been struggling to form healthy habits
• Rick gives an update on his business partner's work/life balance
• Tyler finished his cycle of meeting/presentation/1:1s that he does every six months
• Tyler asks Rick about how to define mission, vision, and values
• Rick describes a new marketing funnel he found
• LegUp Health's vision is supported by a recent regulation change

• Tyler has been extremely busy with meetings, interviews, etc.
• LACRM hired two new CRM Coaches.
• Rick took some time off to ski with his family, watched a Duke basketball game, and celebrated his son's 1st birthday.
• LegUp Health has mixed results sending cookies to try to delight customers.
• Tyler gives some updates on product-led growth brainstorming from last episode.
• LegUp Health added some new tools to their workflow to start making things more efficient.
• Rick warns us about the dangers of thinking that tools solve problems.
• Tyler is in discussions with DemandMaven.
• Tyler isn't sure what the future of his blog/newsletter should be.
• We talk about how to be real without being rude.

• Tyler explains how bug bounties work.
• Rick discusses the power of incentives.
• LegUp Health is adding new clients every week, and we discuss how prospecting is working.
• Rick brags about his new X1 credit card (I swear this isn't sponsored, we don't have nearly enough listeners for anyone to bother paying us for product placement)
• We discuss how Rick can thank people who help his business.
• No-work Sunday is a success for Rick.
• We discuss Jason Cohen's blog post: The Elephant in the room: The myth of exponential hypergrowth
• Rick helps Tyler think through his new growth plan.

• Tyler is reading The Great CEO Within.
• Rick shares some early sales wins.
• LegUp Health is learning about their ICP (Ideal Customer Profile).
• Tyler has been experiencing ups and downs when it comes to design, but overall has learned a lot the last two weeks.
• Rick is making Sunday a "no work" day.
• Less Annoying CRM is hiring, and Tyler thinks there needs to be more of a sense of urgency.
• Rick has set a quarterly goal, but it's about learning rather than hitting certain metrics.
• Rick has additional responsibilities at Windfall.
• Tyler shouts out a few products from Elgato, especially the low-profile mic arm.
• We compare starting a business when you're younger vs when you're older.
• Update from last episode: This is the compensation agreement Rick finalized with his first employee.

• Rick is close to finalizing a partnership agreement with his first team member.
• Tyler is excited that LACRM has been shipping a lot of product improvements lately.
• Tyler has a new productivity hack he's trying.
• LegUp Health is doing some cold outreach and so far it's working.
• LegUp Health joined a new business association.
• Tyler is nervous about some marketing trends even though they haven't become a problem yet.
• NFTs. What are they? Why aren't we able to understand them? Why do we keep talking about them despite not understanding them? Because we're podcasters so we're obviously very comfortable acting like experts on topics we know nothing about.
• We respond to a listener question about how Rick balances his full-time job with running LegUp Health.

• Tyler is considering going to Founder Summit in Ashville this fall.
• LegUp Health signed a partnership deal with Pando Labs.
• LACRM is on a hiring spree.
• LACRM has a new thriving wage.
• We discuss whether video testimonials are a good idea.
• Tyler heard a podcast which made fun of LACRM's design, and this resulted in him getting some design coaching.
• We discuss how Rick can structure a partnership agreement with his first hire.

Personal updates from 2021

• Tyler
  • Goal from last year: ✅Spend more time with family and friends once vaccinated
  • Other updates
    • Started exercising
    • Froze embryos
• Rick
  • Goals from last year
    • ✅ Get sleep under control
    • ✅ Adjust to being a dad
  • Other updates
    • Wasn't good about exercising
    • Has only been on one date with Sable

Professional updates from 2021

• Tyler
  • Goals from last year
    • ✅ Get marketing to a point where if can be delegated
    • ❓ Design a new appointment scheduler product
    • ✅ Biggest worry: Growth leveling off
    • ❓ Want to learn: Re-learn how to iterate and move fast
  • Biggest disappointment: Losing a developer right when the product team was building momentum
  • Biggest learning: Wants to be a product designer
  • Other updates:
    • Fewer management responsibilities
    • Signed biggest client to-date
    • Full-funded the treasury
• Rick
  • Goals from last year
    • ❌ Get to $10k MRR. 
    • ✅ Automate/delegate so service can be scalable. 
    • ✅ Biggest worry: Being able to scale service. 
    • ✅ Want to learn: Learn more coding, especially working with API data and generating dynamic emails.
  • Biggest disappointment:  Not being able to work on LegUp Health full time
  • Biggest learning:  Sharing the journey at LegUp Health is better than going solo 
  • Other updates:
    •  Tried bringing on another friend as a Marketing contractor, but he decided to take a full-time job before he ramped up 

2022 Personal themes/goals

• Tyler
  • Plan for travel as part of relationship
  • Build more schedule flexibility so things can be done without needing willpower (e.g. exercise mid-day)
• Rick
  • Reprioritize daily personal health habits (write/exercise before family wakes up, daily calorie tracking)
  • Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)

2022 Professional themes/goals

• Tyler
  • Theme: Spend more time working, but on my own terms
  • Make space to do more individual contributor design work
  • Other things
    • Release 3.9 design
    • Two blog post-worthy releases per quarter
    • By end of year, have an equal balance of tech debt, core CRM, strategy, and product-led growth work on the dev team
    • Run the coding fellowship
• Rick
  • Support the growth of LeUp Health
    • Structure a partnership and financial plan that enables JD to go full-time
    • Grow the business to 400 clients
    • Fully automate the new user onboarding experience
  • Help scale Windfall the right way 
    • Prioritize both performance and people
    • Be a team player
    • Deliver on my responsibilities

Biggest worry

• Tyler: Growth slowed in 2021. Will it come back?
• Rick: Retaining JD for the long term

What do we want to learn?

• Tyler: More professional visual design
• Rick: First principles of leading others (e.g. influence, motivation, habits, trust, negotiation, communication, and decision-making)

Predictions

• Last year
  • Tyler: ❌ San Francisco will become a good place for early-stage startups again
  • Rick: ❓ Asynchronous video will become big in professional settings
• Next year
  • Tyler: The world will be less interested in speculative bubbles (NFTs, meme stocks, etc.)
  • Rick: VR headset use is going to become as common as playing a Wii

Topics in this episode:

• Rick accepted a new job. What does that mean for LegUp Health?
• Rick finished migrating his help site to Webflow.
• Rick notified his free users that the free service is shutting down.
• Tyler talks about compounding and what it means for thinking about the future.
• We discuss how it might be harder to start a company these days because there are so many success stories that are hard to live up to.
• We discuss Datafetcher.com as a nice no-code tool.
• We discuss the build vs. buy tradeoffs.

• Rick is canceling his CRM subscription.
• Tyler is considering where his newsletter fits into his overall plan.
• Based on our conversation last week, Rick has new clarity around the future of LegUp Health.
• Tyler explains how LACRM came up with their long-term product roadmap.
• Rick is going through continuing education.
• We discuss some touchy feely things related to the passage of time.

• Less Annoying CRM is back to remote-first because of the new wave of the virus.
• LACRM had a new developer start this week.
• Rick is thinking about how to simplify his business. Specifically, what can he cut?
• We discuss what it means to be a calm company. Or is that even the goal?

• Tyler hit 2,000 Twitter followers, and we discuss how Twitter is a hits-based business which doesn't suit Tyler's strengths.
• Rick gives an update on his personal website and newsletter optimization efforts.
• Rick reached the first page on an important search term.
• Less Annoying CRM is tweaking the format of help articles to appeal more the the easily distractible internet user.
• Rick has finished his javascript course.
• Tyler discusses the LACRM product roadmap.

• Tyler had fun with a once-per-year football bet, and Rick had to put in a full day of dad duty.
• Tyler is considering taking the ShiftNudge design course to get better at design. He also purchased a license to Tailwind UI so he can copy from better designers.
• LACRM is tweaking it's policy that everyone at the company must do an hour or support each week.
• Rick reflects on the value he gets from both writing and reading personal newsletters.
• LACRM is tweaking it's policy around employee conversation, partially based on a conversation we had on this podcast a couple weeks ago.
• Tyler's Mixergy interview is live.
• Now that Rick has a sense of what is and isn't working at his business, he wants to simplify which will mean cutting some current complexity away.

• Rick launched LegUpBenefits.com.
• We discuss Rick's new no-code tool: Outseta.
• Less Annoying CRM has a new developer starting next month.
• Tyler has refined his approach to writing internal documentation, and Rick makes a fantastic analogy.
• Tyler's co-founder/brother will be in town next week.
• Rick wants to keep practicing coding so his skills don't deteriorate.
• Rick is taking a break from podcasts.
• Tyler wants Rick's help to teach the coding fellows about no-code use cases.
• We discuss Rick's notes on Anything You Want which leads to a conversation about whether startup utopias are real.

• Rick took some time off, but is wondering if he earned it.
• Tyler wrote five blog posts in one day, and wonders if this should be the new approach to blogging.
• Rick decided to wait for Memberstack updates before taking on a coding project he was planning.
• Rick is using Outseta for his next technical project to diversify away from Memberstack. He plans to have the done in the next week.
• Rick is still waiting to decide how to handle the API vendor that closed down his account.
• Tyler is diving into design and is interested in improving his skills.
• Tyler has found a couple promising use cases for his new iPad which he mostly hates.
• The big topic for this week: What are ways a company can fairly share profits with employees? Specifically, is it better to pay current employees more, or hire more people to spread the wealth around.

• Tyler was interviewed to be on Mixergy, but didn't think he did a great job.
• Rick is adjusting his routine now that he has a kid to take care of.
• Rick enrolled in a new javascript course to hone his skills.
• Tyler's previous positive results converting website visitors to his newsletter have turned to failure. No one is signing up.
• Tyler attended Less Annoying CRM's first leadership team meeting.
• Tyler had his first person finish building a website based on his online course.
• Tyler (geez, enough with updates from Tyler, right?) is thinking through putting a limitation on LACRM.
• Tyler (seriously, stop) took a day to help his dad with a new project.
• Rick had a big coding win and finished two projects...
• ...just in time for one of his API vendors to close down his account, so the projects don't really work anymore. We discuss how Rick should respond.

• Tyler has a new iPad and doesn't know what it's good for.
• Rick has added a client through word of mouth, and we discuss how churn and word of mouth are constantly battling with one another.
• Rick has resolved a major issue one of his clients had with their dental insurance. Crisis averted.
• Tyler has been working on the wrong things, and is trying to correct that.
• We discuss Less Annoying CRM's new leadership team.
• Rick is applying his new javascript skills to his Airtable data.
• Tyler is writing blog posts in a new way: First write the tweet storm, then write the blog post.
• We discuss Earnest Capital's rebranding to Calm Company Fund.

• We selfishly discuss larger themes we've covered on the podcast which might make for good topics on the Indie Hackers podcast.
• Tyler's newsletter signups have increased since changing the call-to-action.
• Rick lost another LegUp Health client due to unavoidable churn.
• Tyler has a content idea centered around CRM pricing.
• Tyler wants to do engineering as marketing but doesn't have any good ideas.
• Rick is almost done learning javascript.
• Rick has his first coding projects lined up.
• We discuss the new Stripe payment links.
• We revisit last week's topic because a listener called in with a new thought on the topic.

• Tyler asks Rick how he configured the call-to-action for his newsletter on his blog.
• Tyler is adding a curated list of links to his newsletter.
• Tyler overcame writers block and wrote his first support-focused blog post.
• Rick is curious what a highly-compensated support rep might look like at LegUp Health.
• Rick started paying for Notion.
• Tyler gives a shout-out to SavvyCal.
• We take a listener question about how to reach customers who don't have online communities.

• Apparently online courses have a very low completion rate, but maybe that's ok?
• Rick is learning more about javascript and has a few questions.
• Rick is taking a vacation where he'll fully unplug.
• Tyler gives some learnings from the recent enterprise deal that LACRM closed.
• Tyler has the interview process figured out for LACRM's next hire.

• Rick crossed 200 subscribers for his personal newsletter.
• Rick gives an update on some recent milestones related to this podcast.
• Rick has been doing Wes Bos's beginner javascript course and is learning a lot.
• Tyler is on vacation, and is mostly just taking it easy.
• We discuss Notion's new API.
• Rick seriously sprained his ankle.
• Rick is dealing with a customer who is disappointed.

• We're using a tool called ZipMessage to collect listener questions. If there's something you'd like us to discuss on the podcast, leave us an audio recording of your question at zipmessage.com/tyler
• Less Annoying CRM had a good April.
• LACRM's average account size is going up slightly, but it's having a significant impact on revenue.
• We discuss the theory of constraints, and how Rick can apply it to his next project.
• We talk about interviewing software engineers, especially when people with different experience levels will be applying for the same position.
• Rick finished a book on taking notes, and he gets it now.
• Rick is enjoying the "two co-founders chatting" style podcasts (like this one)
• Rick set up Coinbase and Robinhood accounts for fun.
• We talk a bit more about the basecamp drama now that more news has come out.

• An effective, but maybe sleazy tactic for cold emails.
• LegUp Benefits got its second paying customer.
• Rick is done with SEO for now, and wrote 35 new pieces of content in April (holy shit!)
• Rick is focusing on LegUp Benefits for the next six weeks.
• Less Annoying CRM has finally closed a big enterprise deal they've been working on.
• Tyler is about to start trying to hire a developer.
• Less Annoying CRM's office setup is changing, and we discuss the importance of communicating changes carefully.
• We discuss how to write content when you hit a wall.
• Rick is dealing with unavoidable churn.
• We talk for way too long about Basecamp's recent drama. We reach no conclusions. You can have a full refund for the amount you paid for this podcast if you're disappointed by that.

• Tyler gave an internal presentation at Less Annoying CRM and announced a few new things...
• The office is being reopened in May.
• There will be a new remote work policy in place.
• A deep dive into how DEI (diversity, equity, and inclusion) fits into Less Annoying CRM's structure.
• A new leadership team.
• Rick is working on content and had a big SEO win.
• We discuss Roam Research as a possible note-taking tool for Rick.
• Rick recommends Readwise.io for converting Kindle notes into text.
• We discuss schema markup as an SEO strategy.
• Rick has made some improvements to ricklindquist.com.
• Tyler might have more free time soon and needs to figure out what to work on.

• Tyler is reading a book called Killing Marketing.
• Rick is trying some time management hacks.
• Tyler has a potential job candidate using his new approach to recruiting.
• Less Annoying CRM had their "day of rest" where developers take over customer service for a day.
• Rick is working on content and SEO for LegUp Health.
• Rick has filed his taxes.
• Rick gives a shoutout to a listener that makes software that verifies financial transactions who helped him with a question from last week.
• We discuss Webflow's product roadmap.

• Rick has a baby!
• Rick broke $2k MRR in March.
• Tyler gives an update on his content marketing site.
• Tyler is about to start recruiting a developer.
• We talk about all the speculative bullshit going on right now (NFTs, GME, bitclout, etc.).
• Rick feels pressure to narrow his focus now that he's a father.
• We discuss how to implement an internal tool with no-code.

• Rick is feeling burnt out. We discuss how he noticed, and what he's doing to fix it.
• Rick's baby is expected this next week, so the next two weeks of the podcast will be pre-recorded episodes.
• Tyler is drowning in meetings.
• Tyler gives an update on his new content site.
• We talk a bit about SEO.
• Rick is looking for two plugins to help with his Webflow site.
• We have both received our first vaccine shots, and we discuss what it would look like to re-open an office.
• Rick has realized how personal the information he needs from customers is, and how that impacts trust building.

• Rick breaks down how the new stimulus bill will impact health insurance and entrepreneurs.
• Rick is putting his big project on hold until after paternity leave.
• Tyler gives an update on Less Annoying Business.
• We discuss enterprise sales, and how it's more about project management than convincing someone to buy.
• We talk about Zapier's acquisition of Makerpad.

• Indie.vc is shutting down
• Rick gives a revenue and churn update.
• Rick is preparing for the birth of his first child, but has one more big project to finish first.
• Tyler recaps the first week of results after launching Less Annoying Business last week.
• We discuss whether it makes sense to build an audience.
• Tyler is trying to get help with Elasticsearch from his online community.
• We discuss the long, slow SaaS ramp of death.

• Rick finished his goal for February of automating the monthly emails at Legup Health.
• Tyler gives an update on his new small business advice website. How do you like that link building I just did?
• Tyler remembers how fast a project can move when you don't have legacy code slowing you down.
• We discuss a variety of tools used to build a content site, especially Webflow and ConvertKit.
• Tyler used Fiverr for the first time to hire a designer.
• We discuss multitasking for motivation.
• We both prefer creating content from our own personal voice rather than on behalf of the company.
• We brainstorm what's next for Less Annoying Business/

• Rick is learning more powerful no-code tricks with Zapier, and advancing his PHP knowledge.
• We discuss the best way to learn how to write secure code.
• Tyler is wrapping up a big project which involves setting deadlines. We discuss healthy vs. unhealthy deadlines.
• Tyler is brainstorming content marketing approaches which is tough because he's not an expert on the topics his customers are most interested in.
• We discuss Rick's learnings from Peter Drucker.
• We talk about the idea of running an online competition

• We discuss the state of independent SaaS and what it means to have a very low payback period.
• Rick has installed a development environment and is learning to code again.
• Tyler is almost done getting ready to switch the LACRM marketing site to Webflow.
• Tyler is considering trying out Mixpanel.
• Salesforce is going more remote. What does that mean for San Francisco.
• We discuss Tyler's tweet thread about his internal dashboards.
• We talk about the Trends.vc report on competitor risk.

• Rick officially launched a "give back" program
• Rick decided not to post internship openings until post-parental leave.
• Rick wants to start a group focused on reaching local consumers.
• Tyler is planning an at-home retreat.
• Morale is a bit low as covid drags on.
• We discuss a specific UI decision LACRM is facing.
• We discuss aligning what you want to have happen with what will actually happen.

• How Robinhood's recent controversy applies to Rick's business model.
• Rick received his first cancelation.
• Twitter acquired Revue.
• Rick is working on a low-code solution to an automation issue.
• Tyler is close to closing a deal with an enterprise client.
• We discuss how to handle security audits (e.g. SOC 2 compliance) with enterprise customers.

• Less Annoying CRM hit $3 million ARR, and the tweet about it got a lot of engagement.
• Rick paid out referral rewards to his clients.
• Rick explains his buyer journey exercise.
• Rick reflects on the value of customer appreciation.
• Tyler has been a guest on several other podcasts.
• We discuss how to react when a competitor launches.
• We discuss the idea of building buffer into everything we do, and how it relates to the startup to last philosophy.

• Tyler reviews what he learned from last week's DDoS attack.
• Rick has planned out the year and feels good about his ability to get it done.
• Rick is allocating 50% of his time to promotion and 50% to automating his product.
• Tyler is about to start teaching a design course.
• LACRM is close to finishing a migration to Webflow.
• We discuss Clubhouse.
• Tyler is getting a Peloton.
• Rick is experiencing anti-depressant withdrawal syndrome.

• Trump and his group of domestic terrorists are trying to overthrow the government and it sucks.
• What a Democrat-controlled government means for healthcare
• Rick's business is extremely seasonal.
• We give financial updates from 2020.
• Rick is working on some tooling changes: Twilio, Front, and knowledge bases.
• Don't be envious of other people.

Note, many of the goals mentioned here were set in our 2019 recap episode.

• Personal accomplishments 
  • Rick 
    • 2019 Goal: Get to a point where he and his wife feel comfortable having kids - ✅ Not only are they ready, Rick's wife is pregnant 🎉
    • 2019 Goal: Increase level of play - ✅ He's been playing basketball, skiing, playing water sports, etc.
    • Had success writing his newsletter almost every week.
  • Tyler 
    • 2019 Goal: Get a dog - ✅ His name is jolo and he's an idiot.
    • 2019 Goal: Exercise three times per week - ❌ Things were looking good until covid hit.
    • Got married and bought a house.
• Business accomplishments 
  • Rick 
    • 2019 Goal: Grow to $10k MRR - ❌ But did even better by focusing on one business and investing in the long term.
    • LegUp Health makes more money than it spends.
    • Built the LegUp Health product with no-code and low-code.
    • Shut down his old business, Group Current, while maintaining a strong relationship with his co-founder.
  • Tyler 
    • 2019 Goal: Continue product team's momentum - ✅ LACRM put out meaningful product improvements regularly throughout the year.
    • 2019 Goal: Write code once per week - ❌ Didn't even come close.
    • 2019 Goal: Average 50 paying users/month from the referral channel - ❌ Had the right input, but didn't get the results.
    • Launched a major redesign.
    • Made it through the pandemic despite a couple terrible months.
    • Raised prices.
    • Hired two new people.
• Biggest disappointment 
  • Rick - Not spending enough time with customers, friends, and family.
  • Tyler - Had to fire an employee.
• Biggest learning 
  • Rick - The difference between earning 10% of a business vs 100%.
  • Tyler - The role of an entrepreneur vs. the role of a CEO.

Discussing big picture goals

• Why are we entrepreneurs? What drives us? 
  • Rick - He's good at it, he likes it. It's the best pathway to freedom.
  • Tyler - Trust, building things, creating a great place to work.
• What do we want to accomplish over 10+ years 
  • Rick - $10mm ARR, 20% profit. Become the one-stop shop for consumers finding healthcare. Build a full benefits platform for employers.
  • Tyler - Turn the one successful product into a suite of products for small businesses. Be more than a CRM.
• What do we our roles to be long-term? 
  • Rick - Build a management team. Stay involved in product marketing.
  • Tyler - Manage the product team and innovate on the product as an individual contributor. Be CEO, but mostly have non-product things delegated to a management team.

Expectations for 2021

• Personal themes/goals 
  • Rick - Get sleep under control. Adjust to being a dad.
  • Tyler - Spend more time with friends and family once the pandemic is under control (knock on wood)
• Professional themes/goals 
  • Rick 
    • Get to $10k MRR.
    • Automate/delegate so service can be scalable.
  • Tyler 
    • Get marketing to the point that it can be delegated.
    • Design the new appointment scheduler product.
• Biggest worry 
  • Rick - Being able to scale service.
  • Tyler - Growth leveling off after the benefit of the price increase wears off.
• What do we want to learn? 
  • Rick - Learn more coding, especially working with API data and generating dynamic emails.
  • Tyler - Re-learn how to iterate and move fast.

Predictions

• Our predictions from last year 
  • Rick - An all-in-one solution will emerge in the no-code space ❌
  • Tyler - Startups raising money from non-VCs will become more mainstream (sort of happened, but still in progress)
• Next year 
  • Rick - Asynchronous video will become big in professional settings.
  • Tyler - San Francisco will start a new era of opportunity for early-stage startups.

• Tyler realized he might have more revenue growth next year than he originally thought.
• Rick is learning that things don't die down immediately after open enrollment, and that's making it hard to do end-of-year planning.
• Tyler has been thinking about what the approach might be when LACRM re-opens the office.
• Rick is meeting his intern for the first time in-person.
• Rick switched to Notion and is loving it.
• Tyler has a marketing approach that he wants feedback on.
• We discuss whether companies should donate money to charities.

• Rick is finished with open enrollment and walks through some metrics.
• Rick is expecting his first churn from customers who signed up earlier this year.
• Rick realizes that word of mouth happens at specific moments in time, such as when someone leaves their job, gets married, or has some other life event.
• Tyler is learning more about his strengths and weaknesses.
• Tyler is overwhelmed with interviews.
• Tyler is preparing a presentation on recruiting and diversity.

I would like to apologize for my lack of creativity in the sentence structure above. It's the middle of December and it's pitch black outside even though it's not even 6pm, so it just seems like writing up interesting show notes is not a great use of my time when I could instead be eating fast food and watching Netflix. Thanks for understanding.

• Advent of code
• The Less Annoying CRM design fellowship is finalized.
• Rick has a few different channels that are showing traction including Instagram DMs and getting referrals from other insurance agents.

• Slack was acquired by Salesforce for a bunch of money. Like, a whole lot.
• Stripe launched a new "Treasury" product.
• Tyler finished his end-of-year planning.
• Rick has been bouncing between projects.
• Google Search Console has been broken for Rick.
• My first million is a good podcast.

• The trend of SaaS companies bundling multiple products into a single subscription.
• Rick's marketing plan for the next few weeks.

• Rick has been reading two new books that teach about avoiding distraction and staying focused.
• Tyler had a product strategy breakthrough after giving himself time to think through a bunch of bad ideas first.
• Rick reflects on his failed startup from last year and we discuss the merits of having a portfolio of products vs a single product to focus on.
• Rick has been marketing LegUp Health, including making an appearance on tv.
• Tyler reports on the results of some help site changes Less Annoying CRM made a while back..
• Tyler is planning a design fellowship.

• Tyler has another lesson to share from the book he's reading.
• Rick stopped marketing and he's struggling to get momentum back.
• Tyler is trying to design team permissions for Less Annoying CRM and it's proving to be difficult.
• We give a shoutout to Jetboost.
• Rick is frustrated that no-code tools aren't more transparent about their product priorities.

• Tyler is switching Less Annoying CRM to Notion.
• Rick is finished with outreach to existing customers to prepare for open enrollment. Next up is marketing/sales.
• Rick's employee Lena is doing a great job executing their content strategy.
• Tyler gives an update on Less Annoying CRM's financial results in October.

• Rick is getting ready for open enrollment, and he explains the history behind why health insurance is sold all at the same time in the U.S.
• Tyler has been talking to customers a lot recently.
• Tyler is using "revenue per employee" as a simple guide for whether or not LACRM can afford to hire employees.
• Wildbit shows what it means to "startup to last" after celebrating their 20-year anniversary.
• Rick is interested in grain.co.
• Instagram/Facebook are a cancer upon humanity and they should be destroyed. Or they should let Rick log into his account. Either way.
• We discuss how Less Annoying CRM could package and position their product in a future where they have multiple sub-products all within the same app.

• Rick separated his marketing site from his app and launched a site for his b2b product: www.legupbenefits.com
• Less Annoying CRM launched a new help site and in-app help center.
• We discuss what interns can do to get the most out of a remote internship.
• Rick's ridiculous shoes arrived and they're meh. The lesson is: Don't buy shoes because a company put their logo on them.
  • Rick will yell at me if I don't point out that he didn't get the ones with Slack's logo, he got the same type of shoe without the logo.
• We give a few shoutouts:
  • Demodesk is a great tool for giving demos to customers.
  • Turn the ship around is a helpful book on leadership.
  • This episode on health insurance for startup founders is interesting and started a conversation about premium tax credits.

• Tyler has to decide between keeping his design consistent vs. optimizing each page's design for the content on that page.
• Rick has moved into a new house
• Tyler had his first meeting with the new mastermind group.
• Tyler gives updates on his ongoing Webflow project.
• We discuss the upsides and downsides of building a startup on tech platforms (e.g. no-code tools) as well as distribution platforms (e.g. the Shopify app store)
• We talk about how Covid might impact things for the rest of the year.

• Tyler gives an update on the 1:1 meetings he's had with his whole team over the last week.
• Rick launched a digital health tool marketplace
• Rick is wrapping up his projects from earlier in the year and is ready to focus on a few important things going forward.
• Less Annoying CRM is close to close two new accounts, each of which are significantly larger than any customer they've had before.
• Rick complains about his CRM adding data automatically.
• We give a shoutout to Rick's wife who helped launch Lucidspark.
• We give a shoutout to Dru Riley and Trends.vc.
• We give a shoutout (how many shoutouts are there?) to Courtland Allen who's starting a podcast network which we're joining.
• Tyler complains about restaurants that aren't trying to compete.
• Rick likes some extremely stupid shoes that Cole Haan made in partnership with Slack.

• The difference between work and hobbies when hobbies involve work topics.
• Rick is focusing more on outreach.
• Tyler gave a 6-month presentation to his employees.
• Rick is about to build his employer-facing product using Glide.
• Should startups with multiple products put them all under a single brand umbrella, or run separate marketing sites for each one?
• Rick is switching from Google Meet to Zoom.
• Should startups ask for a credit card when signing up for a trial, or after the trial has ended?

• Rick was on an entrepreneurship panel at his former high school.
• Rick has automated most of the onboarding process at LegUp health.
• Tyler gives an update on his price increase.
• Rick closed his first employer client and has lots of other opportunities coming up soon.
• Rick gives shout-outs to The Infinite Game and INTRO (we also discuss Trailhead).
• We commiserate about Webflow limitations.
• We talk about smart home devices (what does this have to do with startups? Nothing).

• Rick is on a roll with his website build-out. Check it out at leguphealth.com and let him know what you think.
• We talk about mistakes you can make when handing off ownership to employees.
• Tyler is reconsidering the benefits philosophy at LACRM.
• Rick is thinking about how to build out an employer-facing app.

• Tyler is preparing for vacation.
• Rick has his new CRM set up.
• Rick is working on his website and isn't sure the right approach to take.
• Less Annoying CRM hired a new developer.
• Less Annoying CRM has a bunch of new features getting launched.
• Tyler is considering how to get the rest of the team more involved in product prioritization.
• Rick has been adding some new customers based on outreach he did months ago.
• Deep dive: How should Rick build and price and MVP of a new b2b service?

• Rick is taking a vacation which has him considering if his business should be remote-first so he can spend more time outside of Utah.
• Tyler was on support last weekend and started testing out ways to limit wasteful uses of customer service time.
• Tyler is prepping a presentation for his employees which he does every six months.
• Tyler is formalizing the org chart at LACRM a bit.
• We discuss how to network without annoying people.
• Rick has people reaching out looking for opportunities to work at LegUp Health and wants to figure out how to respond.

• University leadership handling covid this fall.
• Rick is using Copper CRM.
• Rick is done with positioning and moving on to making a website.
• Tyler has pricing and growth updates.
• Tyler has been learning about co-ops and thinking about succession plans.
• We discuss whether ARR or MRR is the right metric to communicate to the team.
• We discuss whether or not it's healthy/smart/necessary to work more than 40 hours per week as a founder.

• Tyler bought a house.
• Tyler is starting to do some startup mentorship.
• Rick's interns are gone.
• Rick has made progress on his positioning work.

• LACRM shipped a handful of small improvements the interns had been working on.
• Tyler gives an update on the price increase.
• Rick is applying the positioning framework we applied last week which involved competitor analysis.
• Tyler officially decided to go with Sococo as a virtual office for the team while everyone is remote.
• Rick decided what to do with this Slack community.
• Rick's internship are wrapping up and he has a virtual get-together with all the interns next week.
• Tyler is getting close to deploying the first stage of his Webflow project.
• Rick wants to know how to maximize his experience with his first paid hire this fall.

• Now that Rick is fully committed to Legup Health, he's getting used to giving something his all again.
• Tyler is considering tweaking the plan for the coding fellowship.
• Tyler is evaluating Sococo to help with remote team culture.

• Tyler's price increase went into effect, but it's too early to draw any conclusions.
• Rick has gotten great feedback from sharing his slide deck.
• Tyler has been tweaking how his team communicates remotely.
• Rick has heard from his early customers that he's asking them for too much info, but it's necessary for him to provide them with service.
• Tyler has reached a decision on what his mid-term product strategy will be.
• Rick is reconsidering his ambitions to run a Slack community.

• Tyler's growth is still going strong.
• Rick is going to write content to build trust with his early leads.
• Rick created a slide deck to explain his business. Check it out here and let him know what you think.
• Tyler is making long-term product decisions.
• Tyler is thinking about making no-code a core part of the coding fellowship next year.
• Rick recorded an interview with Memberstack which will be featured on their site.
• Tyler is going to invest in Earnest Capital.
• Rick had to give advice about how to come up with an idea.

• Less Annoying CRM was named the #1 CRM by U.S. News and World Report.
• Tyler restarted employee raises after temporarily freezing them when the pandemic started.
• Rick now has fully self-serve onboarding.
• We discuss how to write a terms of service and privacy policy.
• Rick is making trade offs between sales and product time.
• Rick wants to retain some of his interns after the summer.
• Rick has validated that real estate is a good customer segment and is planning next steps.

• All of Rick's interns are onboarding, and things are going well
• Rick is building up a bit of sales momentum
• We discuss whether or not it makes sense to create artificial scarcity by requiring a referral before signing up.

• Tyler talks about the reaction he got when telling his customers about an upcoming price increase.
• Rick launched his referral program.
• Tyler is working on a new API for LACRM.
• Rick has finalized the interns he'll bring on this summer.
• Rick wasted a bunch of time talking to the IRS about a notification that was sent in error.
• We discuss HEY, the new email program from Basecamp.

• Rick's interns are acting as a forcing function to keep him more productive.
• Tyler has decided on a plan for LACRM pricing changes.
• Tyler has refined how he talks about project priorities with his team.
• Akshay from UserBit (a boostrapped company that makes software for UX teams) wrote in to ask about how we should handle inbound enterprise leads.

• Tyler and Rick both have interns and need to figure out what projects they should be working on.
• Rick has been working on a client referral program.
• Tyler is wondering if there's anything for him to do to partner with customers who love LACRM.
• Rick was considering an intrapreneurship opportunity (working as an entrepreneur within a larger company) and decided against it.
• Tyler is struggling to prioritize product improvements.
• Less Annoying CRM will need to raise prices at some point. Tyler is wondering if now is the right time.

• Tyler's interns started and they're keeping him busy.
• Rick took a vacation over Memorial day weekend and feels refreshed.
• Tyler has been brainstorming his product strategy more since last week.
• Tyler gives an update on how May has been for Less Annoying CRM financially.
• Rick has added his first non "beta" client.
• Tyler used GDPR to get a company to delete some data.
• Rick has a new professional opportunity that would come at the expense of LegUp Health.
• We discuss the merits of masterminds and talk about the Microconf community.

• Rick made his first revenue with LegUp Health
• Tyler pimped out his home office with a new chair
• Rick is using Heap for product analytics
• Less Annoying CRM had a "CRM Coach day of rest" where developers handled support for the day
• Rick's intern has started and is already paying off
• Tyler has a new framework for thinking about product improvements
• We discuss how several tech companies are moving to a more permanent remote work model

• Tyler got a new standing desk.
• Rick hit a wall with his product.
• Both Rick and Tyler have interns starting soon. There's a lot of work to do to prepare.
• Less Annoying CRM had a breakthrough with their demo call workflow.
• Rick learned from the wisdom of Charlie Munger.
• Tyler is thinking about analytics because of a fan suggestion.
• LegUp Health got their first user referral.

• Rick finished a project for a consulting client that probably won't get used. He talked about how deflating that feels, and how managers should be careful when doing this to employees.
• Less Annoying CRM just received money through the PPP and we discuss what should be done with the extra cash that frees up.
• Rick is dissolving one of his businesses as of July.
• Tyler reached a better understanding of when optimizations are good (i.e. everyone benefits) vs. when they're bad (i.e. the company makes money but the customer experience becomes worse)
• Rick's business taxes are done and we discussed the value of having an accountant who understands your unique needs.
• Tyler is thinking about moving Less Annoying CRM's marketing site to Webflow. We discussed the merits of building web sites in-house vs. using a third-party platform.
• Rick is looking into analytics tools to help understand user behavior.
• College students have been reaching out to Rick asking about internships for Startup to Last.

• It's important to separate marketing tactics from strategy. It's possible that specific tactics make sense, but you need to understand why you're doing those things? What's the goal?
• It's important to focus on a segment or niche, but not all niches are created equal. The goal is to find a niche where the people within it share with each other so that your work can have a multiplicative effect.

• Rick isn't at a point where he needs to figure this out right now. He thought he might need to know this so he could start courting potential employees for the future, but he can do that without knowing the details of compensation.
• Compensation is a combination of salary, benefits, equity, and other perks. One way or another, you need to put a package together that is competitive. One reason a lot of startups give stock options is because they can't afford to pay a high salary.
• Companies that aren't planning on exiting might not want to give equity because it's not worth much without an exit.
• If you want to share upside with employees without giving equity, you can offer a profit share. There are different models, and you can structure yours to align with the goals and incentives you want to provide to employees.

• Ideally, a healthy remote culture won't just mimic an in-person culture, it will actually take advantage of the unique characteristics remote has to offer.
• After companies start going back to in-person work, we shouldn't just go back to business as usual. We should try to maintain the things that are better about remote.
• There are a number of subtle elements of in-person conversations that break down over video chat because of the lag and worse audio quality. This makes it difficult to have more than 5-6 people in the same conversation remotely.
  • One solution to this is to break into smaller groups.
  • Another solution is to add structure to the conversation (e.g. everyone goes in a circle taking turns at doing something) so that people know who's turn it is to talk.
• Many relationship-building moments are based around sharing experiences. Consider what experiences can be shared online (playing games, watching the same video, etc.)
• There's not currently a tool for high-fidelity, asynchronous communication at a business. This is an opportunity to explore.

• There are two common reasons for a manager to feel impatient: someone isn't motivated to work hard, or they're working hard but not getting enough done.
  • The first type is best to avoid entirely by hiring people who are intrinsically motivated. If you can trust that they aren't intentionally slacking off, it takes a lot of pressure off your plate as a manager.
  • The second type is frustrating, but it's not the employee's fault. If they're working hard but not getting the results you want, either your expectations are off, or you're not putting them in a position to succeed.
• Deadlines can be a major cause of impatience and can cause stress for the manager and the employee. Avoid deadlines when possible. Instead, break projects into small chunks and set targets, but don't put pressure on anyone to hit those targets exactly.
• If someone misses a target, have a discussion about why. Was it poor planning? Did something unexpected come up? Try to learn from that, but don't let it cause you to become impatient.
• Trust is a huge element in terms of working with urgency without being impatience. Building trust with your team is more about the process than the result. Let employees in on decisions you're making and make sure they feel heard.
• Founders need to manage their own mental state. Design the company to be able to handle slower than anticipated progress because things rarely go according to plan.

• It's easier to optimize interactions with existing customers rather than new customers who are onboarding because with new customers, every change is more likely to mess up your onboarding funnel. Existing customers have more isolated support events.
• Start by collecting data from the support team on what they're spending their time on. Iterate on that to find insights about why support interactions can be low value.
• Identify the types of customers who aren't going to be a good fit in a self-service way (e.g. a form when they schedule a phone call) so you don't waste both sides' time with a call that doesn't need to happen.
• Put more information on your marketing site to let people disqualify themselves before signing up for a trial.
• This is a big topic. All you can do is collect information, form a hypothesis, and test it. Do that over and over forever.

Here are some takeaways from this episode:

• There are three possible audiences for a startup manifesto: customers, founders, and employees
• The customer-facing version is very different from the founder/employee version because it should focus more on the problem that your company is trying to solve. Write that type of manifesto can be a great way to get people interested in your company before you have a product. It's mostly a marketing play.
• The founder version is mostly useful as a way of keeping you focused on your core values which makes it easier to make decisions. It is especially helpful for knowing what not to do.
• When you hire your first employee, that's probably a good time to take an informal founder version and write it up in more detail so that you can share your vision with employees.
• Because Rick isn't primarily focused on marketing or internal culture right now, he's going to wait to spend time on a manifesto. Instead, he's going to write a press release about what his product might look like in a few months. This will help unblock his product work, but it's not really the same as writing a manifesto.

• Even if your product is good for a large group of people (all small businesses in this case) it can be helpful to focus on a specific segment rather than "boiling the ocean" because it gets easier to acquire new customers as you become more dominant within the segment.
• There are different ways to segment your customers (industry, job title, age, location, etc.). The specific segment you should choose depends on your company, but it's helpful to pick one that can easily be targeted. It might be easier to reach a specific industry (trade shows, etc.) than a specific age group.
• Once you pick an industry, the key is to commit as many resources to dominating that industry as you can, for as long as you can. You won't see results overnight.
• Do everything you can to be known in the industry. Nothing is off the table. Go to trade shows, run ads, sponsor podcasts, write blog posts, build a referral network, etc. The more touch-points you can get with each person in that industry, the easier it will be to acquire them.

• There are a few main ways to fund a new business without giving up equity:
  • Consult or work a normal job to make money and funnel that into your business
  • Enter pitch contests and apply for grants
  • Take on debt
  • Make enough revenue directly from your customers to pay your expenses (this is ultimately what every bootstrapped company needs to do, it's just a matter of how long it takes to get there)
• It's helpful to understand the different capital needs for different parts of your business. Some things might be risky and uncertain. Others might be proven. Rather than thinking "I need $x to run the whole business", break it down by expense type because some might be a better fit for debt (e.g. scaling proven customer acquisition channels) whereas others might need other types of funding (e.g. paying employee salaries).
• For each type of funding, consider how much you'll get out of it relative to the time it takes to get the money. The most obvious thing you get out is the funding, but there might be other benefits that are harder to measure. For example:
  • Winning a startup pitch could help you earn credibility for things like raising money from investors or finding early employees.
  • Making money directly from customers might be harder at first, but the effort you're putting in is moving you in the right direction vs. something like consulting which is probably unrelated to your startup's business model.
• This episode of the Out of Beta Podcast discusses ways to think about raising debt

• Identify what your most important work is, and devote most of your time to that. Rick was spending some of his most productive hours on reading and blogging, neither of which are priorities for his business.
• If you have things you have to get done (e.g. client work), try to knock that out early in the week so you can focus on your other work without distractions hanging over you.
• There are two types of work: transactional (meetings, phone calls, routine maintenance, etc.) and creative work (writing, strategy, programming, etc.). Transactional work can be done effectively even when you're not at your most productive, but creative work can't. So try to devote your most productive hours to creative work.
• "Flow state" is when you're in the zone and getting a lot of work done. When working on creative work, one hour in flow state can be more productive than a day of normal productivity. But it's hard to get into flow state, so the key is to protect it once you're in it. To do this, try to structure your days to allow max flexibility to stay focused if you do enter flow state.
• The downside to giving yourself unstructured time for creative work is that it can be hard to manage your mental health. It can lead to stress and burnout because it doesn't follow the "hours worked = productivity" equation of more structured work. Combat this by expecting to go hours or even days without being very productive, and give yourself time to recover if you do end up having a productive streak.

• Marketing can be broken down into two categories: (1) bringing new people into the top of your funnel and (2) optimizing the conversion rates within your funnel. A lot of technical marketing projects are more about the second than the first. This can be helpful, but there's a ceiling to how effective marketing can be within increasing the top of the funnel.
• Increasing the top of the funnel is all about figuring out where your potential customers are, meeting them there, and telling your story. This can be done via inbound marketing (content creation, SEO, etc.) and outbound marketing (advertising, trade shows, participating in online communities, etc.)
• In order to know where to target your outreach, it's important to understand your existing customers. Where did they come from? What was their buying journey. This can be done by having one-on-one conversations with them, but it can also be automated by having analytics on your website, asking questions when someone signs up, etc.
• Because Tyler is interested in technical projects that help with marketing, a good approach is to build technology to help collect the right information about existing leads/customers so that the non-technical members of his team can understand where to focus their efforts to drive more people into the top of the funnel.

• There are two goals when acquiring early customers: 1) Growing your business, and 2) Learning what works and what doesn't. Some growth channels might work for one or the other, but the best approach is to do both at the same time.
• Identify what type of person you want to sell to. You can use intuition for this, but if you already have a few customers, it's helpful to start by looking at what they have in common and trying to find more people like that.
• Conversations are key to learning. Even if you don't plan on selling your product one-on-one forever, you need to talk to customers (in person, over the phone, over email, whatever) so you can learn from them.
• If you don't already have access to the right people to have conversations, you can try advertising or cold outreach. Every business will be different, but the key is to identify the right people and go where they are.
• It's very difficult to change someone's behavior, so try to find people who are already doing whatever your product is meant for.

• A financial model is something that takes inputs (e.g. historic data and assumptions about the future) and gives outputs (e.g. how much money might you make this year). It can be as simple as some notes on a piece of paper, or it can be much more complicated.
• There's no standard model that everyone should follow. The key is to figure out what questions you have, and build a model that will answer them.
• In some cases you'll want more than one model. For example, you might make a specific model to help predict what your customer acquisition could look like in the future, and then use the output of that as an input of a higher-level model predicting what your overall profit might be.
• The complexity of your model probably depends on the complexity of your business. Don't compare yourself with other companies.
• Having said that, you might find the process of building a model helpful as a way to force you to think through your business.
• If you're trying to raise money, your model needs to communicate information to them which you might not otherwise be interested in. Things can get more complicated at that point.
• Understanding all of the above, building a model is just a matter of opening up Excel, entering the inputs, and doing your best to generate reasonable estimates for the outputs. Each model is different, so it's hard to be more specific than that.

• Traditional entrepreneurship is already set up well if your goal is to become as rich as possible. Startup to last companies should probably have some other motivation such as enjoying the work, feeling fulfilled by the impact the company has, etc.
• Despite needing to be motivated by something other than money, sustainability is key to survival, and that means that every business needs to at least make enough money to make it worthwhile for the founders. That's the first priority, and then once that "enough" number has been reached, it's time to start focusing on non-monetary goals.
• It's only possible to run a company this way if all shareholders are on board. It's not hard to get founders, employees, and customers aligned. It's harder, but maybe not impossible, to get investors on the same page (venture capitalists specifically are unlikely to want this approach). This is why bootstrapping is common among these types of companies.
• Because the goals of startup to last companies are different so are the rules. We didn't get too deep into how this might impact how you operate the business, but there's a lot to discuss there.
• It's helpful to think about the company as a place you'll work for the rest of your professional life (even if that's not true). That will help you prioritize sustainability, enjoyment and fulfillment. Companies that expect to exit soon can justify burnout-level work environments because they know it doesn't have to last.

• Starting a new job is stressful, and one of the main goals should be to make the new employee feel safe. One way to do this is to set expectations are that (a) small enough to be achieved over a short time period and (b) not related to actual job performance at first.
  • In the case of LACRM, expectations will be set around trust. The goal of the first month is for the new hire to feel safe and trust the rest of the team and the company. This way they know they don't need to worry about their job performance during training.
• It's valuable to give new hires a lot of context about the business (e.g. the history, who you serve, why, etc.) but this can be hard for employees to retain because they're learning so much at once. One way to help with this is to build everything into the same narrative.
  • In the case of LACRM, because "trust" is the theme of onboarding, it might make sense to center all the other company lessons around that same concept. Instead of teaching new hires about 20 random concepts, explain how each of those concepts leads to trust.
• Most importantly: explain to the new hire why you're doing things the way you are. Just giving them info won't be helpful (and might actually be hurtful) if you don't contextualize it. This should be a topic for the first day, or maybe even before the first day.
  • In the case of LACRM, focusing on trust might actually give new hires a reason to distrust the company if it's not explained why trust is so important (they might wonder what happened in the past to cause trust to be such an emphasis).

• What happened in 2019?
  • In our personal lives
    • Rick: Took 7-8 months of to figure out who he is and what his goals are, especially with his new marriage.
    • Tyler: Figured out a sustainable diet
  • In our professional lives
    • Rick
      • Figured out what he wants to do after leaving his previous job of 11+ years
      • Started LegUp Ventures which is a holding company for his various ventures:
        • GroupCurrent - Outsourced member management
        • Startup to Last - This podcast
        • RickLinquist.com - Rick's personal writing
        • LegUp Health - Reducing healthcare-related anxiety for people without job-based insurance
    • Tyler
      • Started the year working on a new project called Sparse which was abandoned in February
      • The rest of the year was spent on a major redesign of Less Annoying CRM which included two major new features: Custom fields and Outlook Calendar Sync
      • This was the best year for the LACRM product team
  • Biggest accomplishment
    • Tyler: Finally built a real product team at LACRM
    • Rick: GroupCurrent turned around the business model of their first client and got it to sustainability
  • Biggest disappointment
    • Tyler: Sales in the second half of the year were below expectations
    • Rick: Wasn't thoughtful enough about getting his wife's buy-in when starting his new ventures
• Looking forward to 2020
  • Personal goals
    • Rick: Get to a point where he and his wife feel comfortable having kids
    • Tyler: Get a dog
  • High-level professional goals / the theme of 2020
    • Tyler: Continue the product teams momentum and establish a rhythm of regularly shipping updates to LACRM
    • Rick: Calm growth. His life is calm right now, and as his ventures pick up, he doesn't want that to change.
  • Biggest worries / what's keeping you up at night?
    • Rick: Making enough personal income to be able to sustain his ventures
    • Tyler: Growth at LACRM needs to pick up eventually
  • Three specific goals for 2020
    • Tyler
      • Exercise moderately three times per week
      • Write code once per week
      • By the end of the year, average 50 paying users per month joining LACRM through the referral channel
    • Rick
      • Play more sports. He has an exercise routine, but it's boring and doesn't involve games or play
      • Be ready to start trying to having kids
      • Get distribution revenue from LegUp Ventures to $10k/month
    • Shared goal: Get this podcast to 250 subscribers
  • Make a prediction for 2020
    • Tyler: Starting a software business without venture capital will become much more mainstream over the next year
    • Rick: An all-in-one leader will emerge in the no-code industry
  • What do you want to read in 2020?
    • Rick: Too many to name, but wants to read a lot about emotions.
    • Tyler: The unicorn project and Obviously Awesome

• In the early days, a founder can easily offer great customer service just because they're an expert on the topic and are empowered to solve every problem. Rick doesn't need to worry about this at first.
• For a low ARPU (average revenue per user) product, it's best to think of support reps as "coaches" so they can be more proactive and replace other functions such as sales and customer success. It's not viable to have separate teams for each function at a low price point, nor is it desirable.
• Rick's first move should be to do all the coaching himself until he has it systematized. Some of it can be automated with things like tutorial videos, but some of it will need to be manual.
• Once he knows exactly how to manually provide the best coaching and he has enough customers that he can't handle any more, it will be time to start building a team.
• Offering great customer service for a low ARPU product will hurt margins. This might mean that certain investors aren't interested in the business, but it's still possible to be profitable enough to bootstrap.

• There are different types of website redesigns, including:
  • AB testing (iterating pages on the site based on performance).
  • Style update (updating the CSS, or look and feel based on a new brand style guide).
  • Restructuring the site (changing the site navigation and pages to better accomplish objectives).
  • Rebranding the site (changing the brand name and/or positioning of the site).
• You want to do the minimum necessary when you're redesigning a website. 
  • Figure out the smallest thing that you know you need and just go do it.
  • If you can get away with basic iterative AB testing, that's awesome. It means you're in a really good place. 
  • If you need a whole rebrand, figure out how to do it as quickly as possible because when you're going through wholesale changes, it's messing with reporting.
• When doing a redesign consider the following questions:
  • Is my brand name or positioning changing?
    • If your brand name is changing, you may need to consider transitioning a new domain. (Note: This comes with significant search engine optimization challenges.)  
    • If your positioning is changing, you may need to review copy on all of your pages. (Note: This might impact SEO if the copy changes are significant.)
  • What are the main functions of the site and are they changing?
    • Is it for users to login?
    • Is it to generate leads?
    • Is it to convert free trials?
    • If the functions are changing, you may need to restructure the site (Note: This can impact SEO in a big way if you are onsite links or removing pages).  
  • How complex is the site?
    • How many unique pages and designs are there on the site?
    • Can you get away with designing a few templates and applying them across multiple pages?
    • Or, is every page unique?
    • More complex sites taking longer to redesign.
  • Does look and feel (style) need to change?
    • Do colors need to change?
    • Do fonts need to change?
    • Do page layouts need to change?
    • Do UI components need to change?
• It’s OK to prioritize a redesign based on a standards without data proof.
  • At the end of the day, if brand is important to you, it's important to you. 
  • If you're failing on your brand promise or standard, that's going to keep you up at night and that's not healthy. 
  • Just go fix it and don’t waste time trying to justify your brand standards.

What else would you add to this list?

Context

Tyler: So what we're going to talk about is ... I'm actually interested, I'm not entirely sure where this is going to go, but Less Annoying CRM, my company, just did this big redesign that I keep talking about, but that was just the app. So when a customer logs in, the experience they have in the logged in part of it has been redesigned. The other stuff, what I'll call the marketing site here, still looks like it did four or five years ago. And so there's this big mismatch between the, first, impression a customer gets when going to our marketing site versus the actual polished and good design that they get once they log in. So we're basically trying to think about some kind of a redesign of the marketing site. This could be really, really small. It could literally just be like go in and make some CSS tweaks, but leave everything else the same. It could be completely, from the ground up, rethink what this website should even be, think about SEO, switch to a content management system like WordPress or something. It could be as big as we want it to be. So that's basically what we're talking about here. I have a little more context, but maybe what I should say is just what I'm hoping is we can talk through, A, how big of a project should this be and then, B, we're not going to plan the whole thing out in this next 40 minutes or whatever, but where should I start? What should some actions be that I can take to really get moving on this project?

Rick: Yeah. So I'm interested in what problems you need to solve by doing this. It sounds like you're mostly concerned about more of a brand consistency or user experience consistency more so than anything else. I'm not hearing, "Hey, we need to get more leads," or, "Man, people are complaining about the website." It seems like it's more of a personal, "Hey, this website is no longer up to my standard," type thing.

Tyler: Mm-hmm (affirmative). There's definitely part of that. And, yeah. I'll say, I'm really skeptical about a lot of marketing. I think 20% of marketing is super valuable and critical to a company and I think a lot of it is just a bunch of overpaid people in suits being like, "Oh, your font doesn't communicate the trust that you're ..." Nobody cares about the font. Shut up. So, yeah. I don't want it to be what a marketing agency would turn this project into. The way I look at it is, it's kind of like if you're single and you're dating and you go to a bar to meet somebody, you know that the things that matter are personality and trust and all this, but all you can see is their physical appearance when you walk into the bar. And so people naturally tend to overemphasize that when it comes to first impressions. The same thing is true with a company. Just the other day, actually, for my wedding, I had to get insurance for the wedding and our wedding planner sent us two websites. I went to both of them. One of them had not been redesigned in a decade and one of them looked nice and I was just like, "I have no information here. I can't tell which insurance is better, so I'm just going to go with the one that looks like a more professional company." So that's really what I'm going for is, once someone uses our product, they like it, we treat them well, everything goes well, the personality stuff in the dating analogy is good, but we need to put on a little makeup and actually try at the bar if we're going to get these customers in the first place.

Rick: So it sounds like your main concern is what's the first impression people have of Less Annoying CRM when they come to your website.

Tyler: Absolutely.

Why is this a priority right now?

Rick: Okay. So flying up a little higher, just for context, why are we talking about this right now over some other priority? Why do you feel like now is the right time to worry about the first impression?

Tyler: That's a fair question. It's possible that it's not. I would say that, probably two years ago was the right time, but the reality was that the app would've let down that first impression either way. So I think it's just, now that the app looks good, I don't think ... Redesigning the app was a nine-month project. I think redesigning the website could be as little as a one-week project. And so I just feel like it's kind of low-hanging fruit because we've done the hard part already.

Rick: Interesting.

Tyler: But, yeah. If it didn't happen for the next six months, I don't think there would be any real consequences.

Rick: Have you talked to any new users who've gone through the existing marketing site experience with the new interface?

...

• There are frameworks out there for emotional intelligence, self-regulation, but there isn’t much stuff out there about how emotions impact company culture, team performance, and leadership.
  • There aren’t a ton of CEOs talking about their own experiences.
  • Most of the stories out there are from therapists about their anonymous clients.
• There isn't agreement on the definition of emotion.
  • One model is Robert Plutchik’s wheel of emotions (see image below) that defines 8 primary emotions: 
    • joy and sadness
    • anger and fear
    • trust and disgust
    • surprise and anticipation
• A leader who priorities trust may be more likely to create a safer culture where people are free to express their emotions.
  • This makes it so that the emotions that you and other people experience happen in a way that is healthy, and has a mostly positive impact on other people (and  team performance / culture).
  • It also makes it safe for everyone to inquire about clarifying the meaning of each others’ emotions (instead of making assumptions).
  • When you're in a distrusting situation, emotions are probably more violent in a negative way.
• Trust relies on character and authenticity.
  • You might experience trust when you see someone do something that's not in their own best interest, but they do it because they think it's right or some set of values.
  • Competence may also play a part.
• Distrust leads to distrust
  • If you hire and keep people who you don’t trust, it can lead to a negative cycle of distrust.
• One source of potentially negative emotion for leaders is the time between becoming aware of a problem and figuring out what to do about it
  • If you have don’t have a high-trust environment, this can be a risky time period when emotions might be misinterpreted
  • Another source of potentially negative emotion is when an employee leaves

What else would you add to this list?

Source: Wikipedia

Context

Rick: It's my week for the topic. I don't really have a critical problem per se to bring you that I want to brainstorm with you, at least not more important than what I'm bringing to you today. So taking a slightly different approach with the topic I'm bringing, and it could be a total bust, so I'm prepared for bad feedback from this from the audience. But maybe this works. I guess listeners out there, if you listen to this and you don't get value, please tell us so that we don't repeat this. But if you do like it, please tell us because we'll have more confidence covering topics like this in the future. Now that I've got my writing cadence going at RickLindquist.com, I spend two to three hours every morning before 9:00 AM researching and writing about a topic of my choice. My goal is not to just throw out content, it's primarily learning through the process of writing. And so I want to write a book about emotions, leadership, and teams, and I'm starting to outline that book in terms of what would the table of contents be so it can drive my research. Because I'm going to be learning a lot as I go because I'm not an expert on emotions by any means, I know that the specific angle I'm going to take and the specific outline is going to change over time, but I hope that by constantly revising the outline based on what I'm learning, it can drive my short-term and short-form writing on a weekly so that I'm killing two birds with one stone. I'm writing and fulfilling what I want to do at RickLindquist.com in terms of outputting content, but I'm also learning the things necessary as part of research for this larger book. It may take me a whole year to write this thing. It's just a question of putting a couple of hours in a day most days. I started this week researching emotions and building the outline. I'm stunned at how little agreement there is on how emotions work and how they impact people. Most of what I'm reading is research and academic papers. I have not been able to find a ton of CEOs talking publicly about the role of emotions in leadership and in teams. Kind of coming back to listeners out there, I personally think that this is a topic that we all need to talk about more because I hypothesize that we can become better leaders if we're more in touch with our own emotions and others' emotions because it's the basis for how we form trust with our strong relationships. And trust is the ultimate success factor for a highly functioning team. But I'm trying to do research. I'm having trouble finding like layman's explanations of the stuff with consensus. I was hoping today that I could, I don't want to say interrogate, but I kind of have a feeling that I need to ask you some tough questions. I want to ask you some tough questions about your experience with emotions, both from how they happen in your head and within your body, as a leader and CEO. Then also, how you react and observe and handle emotions of team members in the day-to-day stuff. We've talked offline I know you've, we've talked offline and made sure that was okay, but is there anything that's off limits in terms of asking you questions?

Tyler: No, I mean there might be ... I'm happy to share my own experiences and I might be a little more secretive if I feel like I'm exposing something about someone else who hasn't necessarily given permission. But for myself, now I think I'm an open book. We'll see.

Rick: Yeah. Cool. Listeners, I think that the other thing that we want to do here is I want to model talking about this openly, so I'll also jump in with my own insights on emotions. I'm a pretty, in terms of like emotional spectrum, I wear my emotions on my sleeve much more than Tyler does. Not to say that we're both not emotional people, it's just we may have very different experiences with emotions because of our personalities. I'll jump in when I can add a personal take. Would you add any anything?

Tyler: I'm curious here, so I don't hear people maybe using the word emotions a lot, but I hear people talking about m...

• Product roadmap planning is easier when you are able to align to clear company goals and constraints. In this context:
  • Goals = what you really want to accomplish during a time frame. E.g.:
    • “Increase signups from word of mouth”
  • Constraints = the things you aren’t willing to ignore / don’t want to drop while you’re pursuing your goals. E.g.:
    • “Spend 10% of development hours paying down technical debt”
• Take time to make sure employees are bought in to the company goals and constraints prior to planning the product roadmap. 
  • One way to do this is to include employees in the prioritization and trade-off process.
    • Company leaders often go through a number of change cycles and trade-off decisions when setting company goals. 
    • If you can allow employees to have a voice in these trade off decisions, they are much more likely to buy in to your prioritization decisions
• When you get to product roadmap planning, allocate resources based on your company goals and constraints. 
  • Once you’ve addressed your constraints, ideally you can put all of your remaining resources toward the company goal(s). 
  • Common (non-outcome-based) allocation buckets include:
    • New feature development
    • Improvement to existing features
    • Bug fixes
    • Paying down technical debt
  • (Note: if you can logically bucket roadmap items into specific business outcomes tied to your company goals and constraints, do it)
• It's nice to think, "What's our top priority? We're only going to work on that." But, even at a one-person company, this is likely unrealistic. 
  • You lose momentum if you ignore parts of the business and this could get you in trouble.
  • Setting constraints on goals is one way to address this problem.

What else would you add to this list?

Context

Tyler: What we're going to talk about is basically the... Like any company, there's a lot of different things I want to work on next. We're finally at the point where we have multiple developers so we can do multiple things at once, which is not really something I've been faced with much in the past, and I'm trying to figure out how to prioritize different categories of things. One category is building totally new features. That's the sexy, fun-to-announce type of thing, like, "Here's something the software can do that it couldn't do before," versus improving existing features in a way that customers care about versus improving features in a way that customers won't even notice, but the idea of paying off technical debt or something like that, so, a bit of context here, we're finishing up this redesign, and, in a couple months, we're going to have all four developers plus myself moving on to other things, and basically, while we've been doing this redesign, which took almost all year, we've cut a lot of corners. The goal is to get it done as quickly as possible. There's a lot of stuff we want to go back and fix. This is normally referred to as technical debt. We have a lot of ideas for just minor tweaks to our current products that our customers would love, little one-week, two-week things, but we could do it for a year and not run out of ideas there, and they're just slam dunks, makes the product better, and then there's the go-out-and-really-do-something-new that our product doesn't currently do and maybe have a bigger splash, but it's a little more risky, so, yeah, I'm interested in basically just, A, figuring out what should I be doing, but, B, coming up with a framework for how I should think about this in the future.

Rick: Yeah. What timeframe are you thinking about? Is it over the full course of 2020 starting in January? Is it next month for a couple of months? What are you thinking?

Tyler: Probably, I think, the next six months. January through June, July would probably be a good... planning the most immediate next things, and then I'd like that the framework I was talking about can inform once... In April or May, when we start planning the next six months, I'd like to be able to apply that framework again.

Rick: Makes sense. How have you gone about this in the past?

Tyler: I just haven't. Partially, I've been very undisciplined about it. It's gone fine. It hasn't been a problem exactly, but, normally, there's just an obvious next thing. Having said that, it's not clear that the obvious next thing is actually the right next thing, but, in the moment, it's like what piece of software, what piece of our product is clearly the worst thing, that's normally what's going to get the most attention.

Rick: It sounds like you want to add some discipline to your planning process and then you also, it sounds like, have some capacity to do more than one thing and in terms of you have more developers that are fully up to speed and capable that you can put on different things and get more done.

Tyler: Yeah, absolutely, and so one of the reasons I say I've never had a system for this, we haven't launched a totally new, little features, but like a new major thing in maybe since 2014 or something like that. The last several big projects we've done, we're just redoing things we already had, so we redid the calendar, we redid custom fields, we did a redesign, so, yeah, it's weird having the resources and say, "Should we actually start adding to the functionality?"

What are the company goals?

Rick: This was a big challenge for me. I went through a similar transition from Zane Benefits to PeopleKeep. At Zane Benefits, it was very much a... I was the dictator of what got done on a monthly to quarterly basis, and there wasn't this engaged planning process that we thought about things over a long period of time. When I got money to fund PeopleKeep and hired a new CTO for that, he brought a whole nother mentality around roadmap planning and thinking through, and the... one thing that was really hard for him to do a good roadmap on... the situation that made it very hard for him to do a roadmap on was a situation in which I hadn't clarified the company goals for the year, so, I guess, what the... where I would start with this is what are the... If we look at the timeframe for a year from a company perspective, at the end of 2020, when you're looking back, what are the things you want to have accomplished and how will you have measured that? That should drive the first six months of the product roadmap.

Tyler: Yeah, so, if I only get to answer one goal, I want 2020 to be the year of the referral. I want it to be word of mouth. We talked about this in a podcast, I don't know, a month ago about how I was thinking, and I had some questions around referrals and word of mouth. From a business standpoint, I want to make that better, but I also think products can have a big role in there. Now, having said that, I've been making a fair number of implicit or explicit promises to the dev team about it's okay to cut this corner, we'll come back and clean that up later, so I have other concerns beyond just this one big goal, but that's the biggest thing.

Rick: Yeah, and are...