It's Not About The Money

How to read a pay stub

Steve Nay and Tyler Smith — Thu, 15 Aug 2024 05:00:00 -0500

Reading a pay stub can be confusing. What are all the things that get taken out before the money hits your bank account?

Let’s go through the most common line items on a pay stub and explain what they mean, which ones you can adjust, and how they affect your tax refund.

IRS withholding calculator: https://apps.irs.gov/app/tax-withholding-estimator

(00:00) - A spreadsheet of pay stubs
(05:02) - Federal income tax withholding
(06:47) - Social Security and Medicare
(09:28) - State and local taxes
(11:57) - Other pre- and post-tax deductions
(14:06) - What percentage are you actually taking home?
(16:59) - How and when to adjust your federal tax withholding

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Steve Nay:

Tyler Smith:

Task management is not project management

Steve Nay and Tyler Smith — Thu, 08 Aug 2024 05:00:00 -0500

Todoist, much as we love it, is a task management tool, not a project management tool. What if we treated it that way?

Today, Tyler explains a shift he’s recently undertaken in project management that has made it easier to keep the proper perspective and get the right things done.

Steve confesses that weekly reviews are probably worth his while.

And Tyler unexpectedly falls in love with Apple Mail because of Focus Modes.

(00:00) - A list of technologies
(02:38) - Steve still needs to do some weekly reviews
(06:36) - Project management versus task management
(15:20) - Projects in a Todoist Kanban board
(22:55) - Lists of descending temporal importance
(26:43) - Tyler tried Apple Mail and fell in love with Focus Modes

Links:

Carl Pullein: https://www.youtube.com/watch?v=YJZkYNlp_bA
Slow Productivity by Cal Newport https://www.goodreads.com/book/show/197773418-slow-productivity

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Steve Nay:

Tyler Smith:

A train wreck of email

Steve Nay and Tyler Smith — Thu, 25 Jul 2024 05:00:00 -0500

This one is a bit, um, wide-ranging. And nerdy. It’s a window into the minds of your esteemed hosts.

We talk about email management and apps and workflows.

We talk about podcast management and apps and workflows.

Tyler agrees to try an experiment with Apple Mail.

(00:00) - The travails of corporate job email management
(07:28) - Newsletters and email open statistics
(11:57) - Apple Mail
(18:31) - Email before bed
(23:03) - Tyler acknowledges that he might be an "Apple person" now
(24:35) - Podcast listening

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Steve Nay:

Tyler Smith:

Retrospective on the "Many Hats of an Entrepreneur" interviews

Steve Nay and Tyler Smith — Thu, 18 Jul 2024 05:00:00 -0500

We take a few minutes to look back on the interviews we had during the “Many Hats of an Entrepreneur” series over the past few months.

Steve resonated with growing slowly and intentionally. Tyler learned a lot about marketing.

And we’re both looking forward to future episodes with just the two of us: book clubs, nerdy deep dives into our tech stacks, reports of home maintenance projects, and probably at least one mention of McDonald’s.

(00:00) - Retrospective on the Many Hats of an Entrepreneur interviews
(00:05) - Tyler started another business
(04:11) - Retrospective of the Many Hats of an Entrepreneur series
(07:00) - Steve's takeaways
(10:57) - Tyler's takeaways
(16:12) - Future episodes: just Tyler and Steve

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Steve Nay:

Tyler Smith:

Business website design, with James Hagen

Steve Nay and Tyler Smith — Thu, 11 Jul 2024 05:00:00 -0500

You know you need a website, but maybe it’s a daunting task. Today’s guest explains everything you need to know to get started on your business website, whether you decide to DIY it, hire a professional, or something in between.

James Hagen is a web designer who works with business owners and budgets of all sizes to make sure the right thing gets built to do the right job for the right customers.

We discuss:

Using analytics to guide where you invest your time and money in the design process
Understanding your buyer’s needs and expectations
Wix, Squarespace, WordPress, and Webflow
And many more great tools

James Hagen:

jameshagen.design

Timestamps:

(00:00) - Business website design, with James Hagen
(02:33) - Tyler is a tinkerer, and James suggests using data to guide the tinkering
(07:38) - Empathy: Understanding your buyer
(10:10) - Web design trends and home renovations
(16:14) - Tools and platforms for a DIY website
(20:32) - What does all this cost?
(24:43) - Webflow
(31:16) - Website analytics
(34:54) - Don't forget about the cookies

Links:

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Steve Nay:

Tyler Smith:

Superpower Storytelling, with Stephen Steers

Steve Nay and Tyler Smith — Thu, 20 Jun 2024 05:00:00 -0500

Whether you think you're a good storyteller or not, it's a skill worth developing. Today's guest, Stephen Steers, is the author of Superpower Storytelling. He walks us through how to get better at storytelling and why it's such a powerful tool in sales, in business, and in life.

Along the way, we discuss why it's so important to reframe sales not as a battle to be won with the right pressures and tactics but as a collaborative problem-solving exercise that helps everyone.

Stephen Steers:

https://www.stephensteers.com/podcast
https://www.linkedin.com/in/stephen-steers
Stephen's book, "Superpower Storytelling": https://www.amazon.com/Superpower-Storytelling-Tactical-Telling-Stories/dp/B0CH26LR56

(00:00) - Tyler gives a sermon, and our guest uses his book as a business card
(05:13) - Golden age of radio
(13:03) - What if you're not "good" at storytelling?
(18:01) - The P.E.A.R. Method
(21:49) - The A.R.E.A. Framework
(22:57) - The Magnificent Seven Reasons People Buy
(30:18) - Structuring a great sales call
(40:24) - What Stephen does: context selling

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Steve Nay:

Tyler Smith:

Human Resources Operations, with Vanessa Gutierrez

Steve Nay and Tyler Smith — Thu, 13 Jun 2024 05:00:00 -0500

For the business owner, transitioning from being a soloist to being an employer is tricky and full of potential pitfalls. How do you navigate it successfully?

On this episode, we speak with Vanessa Gutierrez, a human resources expert who helps startups implement, streamline, and optimize their people operations. That covers everything from writing job descriptions and offer letters, to keeping employees apprised of local labor laws, to making sure payroll runs properly.

If you're thinking it might be time to hire someone--whether full-time or part-time, W-2 or contractor--this conversation will give you some ideas to explore and some questions to ask as you evaluate your options.

Vanessa Gutierrez:

(00:00) - Human Resources Operations, with Vanessa Gutierrez
(03:31) - The role of a fractional HR expert
(08:12) - When is it time to hire for a solopreneur to hire?
(11:43) - Contractors vs. employees
(14:16) - Hiring overseas
(16:51) - What policies and procedures do you need before you hire?
(19:48) - Posting labor laws
(23:02) - What are the bottlenecks in your business?
(26:53) - Fractional HR vs. Fractional HR Operations

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Steve Nay:

Tyler Smith:

Navigating health insurance as a solopreneur, with Mitchell Underwood

Steve Nay and Tyler Smith — Thu, 06 Jun 2024 05:00:00 -0500

Health insurance can be intimidating, especially when you first go out on your own and don't have an employer-sponsored plan to fall back on. In these transitions, having a health insurance broker can be a huge help.

Today, to discuss the complexities of individual health insurance, we speak with Mitchell Underwood. He helps solopreneur and small business clients evaluate their options in private insurance as well as government-subsidized marketplace insurance.

What do you need out of a health insurance plan? What is your budget? Where do you live? What doctors and networks are available in your area? When do you need coverage to start?

These questions will help guide you toward the right choice for yourself, your family, and even your employees (if you have them). Mitch walks us through each of them and their implications.

Mitchell Underwood

Find him on LinkedIn: https://www.linkedin.com/in/thehealthadvocate/

(00:00) - Navigating health insurance as a solopreneur, with Mitchell Underwood
(01:34) - Making the jump from an employer health plan to an individual health plan
(08:23) - How price is determined
(11:15) - What Mitch does for his clients
(17:34) - Open enrollment periods and qualifying events
(20:41) - How do insurance brokers get paid?
(27:25) - Mitch's ideal client

Links:

Mitch's interview with Paul Ranieri on Tax Strategy Digest: https://www.linkedin.com/pulse/mastering-health-insurance-paul-ranieri-oyjic/
Mitch's "thanks so much for being honest" post we discussed at 24:17 https://www.linkedin.com/posts/thehealthadvocate_thanks-so-much-for-being-honest-this-activity-7199799949079846912-hwep/

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Steve Nay:

Tyler Smith:

Selling without "commission breath," with Landon Pitcher

Steve Nay and Tyler Smith — Thu, 30 May 2024 05:00:00 -0500

You're probably already allergic to manipulative sales tactics, and your customers are too. So how do you get better at sales without pushing prospects away?

Today we interview Landon Pitcher, Co-Founder and Chief Revenue Officer of Listo Global, who has a wealth of sales experience. He talks about transferring enthusiasm, selling without "commission breath," practicing the craft, and keeping your sales pipeline full.

Solopreneurs have a particular advantage when selling our services, because we're also the people in charge of delivering the service. We're deeply in touch both with what our customers need and what it takes to get them there.

Landon Pitcher, Co-Founder of Listo Global

https://www.linkedin.com/in/landon-pitcher34/
landon@listoglobal.com

(00:00) - Introducing Landon Pitcher
(02:22) - Sales is the transfer of enthusiasm
(13:08) - How to "dequalify" a lead during a sales call
(20:25) - Developing your sales pipeline
(30:29) - Asking for referrals
(38:10) - How Landon became a co-founder

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Steve Nay:

Tyler Smith:

Developing your marketing strategy, with Juliana Weiss-Roessler

Steve Nay and Tyler Smith — Thu, 16 May 2024 05:00:00 -0500

While it might be easy to jump straight into marketing tactics (posting on social media, making videos, running paid ads), your marketing will be much more successful with the proper strategy in place.

Today, Juliana Weiss-Roessler talks in depth about getting the right business strategy, brand strategy, and marketing strategy for your business. Once you have those, you can follow the experimental process of plan--implement--measure--repeat to find the marketing channels and approaches that consistently find and convert the right kind of clients for you.

Whether you need tools to DIY your marketing or you're ready to hire (fractional) help but don't know what you're actually buying, Juliana's advice will get you on the right path.

Juliana Weiss-Roessler, founder of WR Digital Marketing

https://wrdigitalmarketing.com/

(00:00) - What is marketing?
(06:13) - Business strategy -> Brand strategy -> Marketing strategy
(11:08) - Social media
(16:58) - Marketing channels
(21:49) - Stages of the marketing strategy: awareness, consideration, conversion, loyalty
(26:00) - How to get started with a limited budget
(30:14) - You NEED a website
(33:22) - What are you buying when you hire marketing help?
(41:26) - Closing thoughts

Links:

Juliana's worksheets and resources
PeopleFund (nonprofit small business lender and educational resources)
Find a Small Business Development Center near you

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Steve Nay:

Tyler Smith:

Growing your business at the right pace, with Erica Goode

Steve Nay and Tyler Smith — Thu, 09 May 2024 05:00:00 -0500

How much money does your business need to make for your life? Would you rather have an extra $50k this year or get back 10 hours a week? What time bucket of your life are you currently in?

Erica Goode, CPA, is a fractional CFO serving coaches and consultants, but she offers so much more than just financial guidance to her clients.

Her own journey to business ownership is unique and refreshing, and it embodies her mindful and intentional philosophy. The kids will never be young again, the teenagers are only this way right now, and maybe your travel preferences will evolve over time. So recognize what phase of life you're in now and strike the balance that best aligns with your values.

This conversation started with what a fractional CFO can do for you, but it evolved into something much more personal and meaningful. Come along for the ride!

Erica Goode, CPA

(00:00) - What is a fractional CFO?
(04:42) - Cash is flying everywhere
(08:37) - All of a sudden, you can see them relax
(12:05) - Money affects our emotions
(18:11) - Erica's business journey
(26:17) - Growing slowly, on purpose
(27:47) - Would you rather make another $50k or have an extra 10 hours a week?
(36:35) - Die With Zero

Links:

"Die With Zero: Getting All You Can from Your Money and Your Life" by Bill Perkins
Erica's podcast episode about "Die With Zero" (Episode 42 of "Coaches, Consultants, and Money")
"How We Decide" by Jonah Lehrer

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Steve Nay:

Tyler Smith:

Managing your equity compensation, with Alex Crouch

Steve Nay and Tyler Smith — Thu, 02 May 2024 05:00:00 -0500

If you're a tech professional at a big company or a small startup, chances are good that you get at least some of your compensation in equity: stock options, restricted stock units, ESPPs, etc.

All these forms of equity have their own nuances and tax implications, and figuring out how they fit into your larger financial picture can be confusing.

Today our guest is Alex Crouch, CFP, the founder of Tech Financial Planning. His firm specializes in helping tech professionals answer these complicated questions in the way that best suits their financial goals.

We discuss the major forms of equity compensation, what's unique about each, and what factors to consider if they're part of your compensation package.

Alex Crouch, CFP

(00:00) - Steve still hasn't heard back from the IRS
(01:57) - RSUs, stock options, and ESPPs
(12:07) - Tax implications of RSUs
(18:20) - Taxes on stock options
(20:29) - Taxes on Employee Stock Purchase Plans
(21:33) - How does this money fit into your life?
(27:57) - Alex's approach to financial planning
(33:16) - 1099-B basis on your taxes
(36:40) - Don't pre-spend your equity

Links:

Episode 34, "Steve gets a letter from the IRS"

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Steve Nay:

Tyler Smith:

Cybersecurity basics for solopreneurs, with Don Sesler

Steve Nay and Tyler Smith — Thu, 25 Apr 2024 05:00:00 -0500

What do a meteor strike, a laptop in a canoe, and a cyberattack have in common?

They all require you to have a business continuity plan, both so you don't lose your data and so you can continue operating the business even in a disaster.

Today we welcome Don Sesler of Sageplan Technology Consulting to talk about the nuts and bolts of cybersecurity and IT for solopreneurs. Whether you want to DIY or you're ready to hire it out, Don shares a wealth of information that will point you in the right direction.

Small businesses like ours usually aren't the target of cybercriminals, but we can be collateral damage. And the way you recover from a cyberattack is the same way you recover from any other catastrophe, so having good systems and plans in place will protect you no matter what comes your way.

Don Sesler, owner of Sageplan Technology Consulting

(00:00) - Interview: Don Sesler (IT, cybersecurity)
(03:00) - Introducing Don Sesler
(05:18) - Cyberattacks and business continuity risk
(11:41) - Vetting your cloud software vendors
(16:31) - Picking the right DIY hardware and software
(20:09) - Google Drive and OneDrive are not a backup solution
(22:24) - The last line of defense against social engineering
(29:17) - When should you hire fractional IT?
(35:32) - Choosing the right office suite
(38:42) - Written disaster recovery plan (on paper!)

Links:

Do It Yourself IT? Here's Some Tips (sageplan.com)
How To DIY A Secure IT Network (sageplan.com)
Why Backups Matter, And How To Do It Correctly (sageplan.com)

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Steve Nay:

Tyler Smith:

The Many Hats of an Entrepreneur

Steve Nay and Tyler Smith — Thu, 18 Apr 2024 05:00:00 -0500

We're back with a new series of interviews, and this episode introduces the theme: the many hats of an entrepreneur.

Our framework is the "five parts of every business" proposed by Josh Kaufman in "The Personal MBA": value creation, marketing, sales, value delivery, and finance.

What are each of these things? What does it look like to perform all of them as the solo entrepreneur? What does it look like to hire out certain functions to fractional specialists? What do each of those things look like in Steve and Tyler's businesses right now?

In the next episode, we'll start the first of the interviews in the series.

(00:00) - The Many Hats of an Entrepreneur
(02:12) - A business is a repeatable process that...
(04:40) - Five interdependent processes
(11:40) - What does it look like for a soloist to do all these things?
(17:03) - Hiring fractional help

Links:

What Are The '5 Parts of Every Business'?
The Personal MBA: Master the Art of Business by Josh Kaufman
Episode 10, “Book Club: The Prosperous Coach”
Episode 16, “Should you outsource your chores?”

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Steve Nay:

Tyler Smith:

Coming soon: Interviews about the many hats of an entrepeneur

Steve Nay and Tyler Smith — Thu, 21 Mar 2024 10:00:05 -0500

Coming up in a few weeks: a new series of interviews with experts in areas of business where you might want help: marketing, finance, IT, management, operations, insurance, and so forth.

You, as a solopreneur, have to wear all the hats of a functioning business, even if you're not an expert at all of them. Sometimes you'll want to outsource a particular function and hire a professional to do just that piece. Sometimes you'll want to keep doing it yourself, but you want to get better at it. Sometimes you don't even know that it's important for the business and you need someone to give you an introduction.

Wherever you are in your business journey, this series will give you ideas, milestones, guideposts, and practical tips to continue growing and getting better at what you do.

We're taking off a few weeks to prepare, but we'll be back soon to share this exciting series with you!

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Steve Nay:

Tyler Smith:

YNAB Rule 4: Age your money

Steve Nay and Tyler Smith — Thu, 14 Mar 2024 05:00:00 -0500

What if you could put all your bills on autopay, treat your credit card like cash, and step back from the stress of worrying about when your transactions happen?

That's the peace of mind available when you get to YNAB Rule 4: Age your money.

When the money you're spending today was earned long ago, you can suddenly let go of a whole category of money stress that you might not even realize you have.

Tyler and Steve demystify the "credit card float" and illustrate with cafeteria-style cereal dispensers.

If after all this you'd like one-on-one guidance through your money journey, Tyler is the coach for you.

(00:00) - Girl Scout cookies
(03:18) - Rule Four: Age your money
(06:16) - The magic of getting to 30 days old
(09:05) - Demystifying the trap of the "credit card float"
(17:08) - What is an age of zero?
(18:21) - How to increase the age of your money
(19:57) - How old should your money be?
(23:59) - Aging your money isn't out of reach
(26:23) - You can hire Tyler as your YNAB coach

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Steve Nay:

Tyler Smith:

YNAB Rule 3: Roll with the punches

Steve Nay and Tyler Smith — Thu, 07 Mar 2024 05:00:00 -0600

Best-laid plans rarely survive contact with reality, but getting your budget to reflect reality is where the clarity comes from.

Tyler and Steve have both had aspirationally-too-small budgets for groceries and eating out. What to do?

Rule 3 empowers you to get your budget to show what's actually happening and align the way you spend your money with the things you actually, truly value.

(00:00) - Dogs and their exercise
(03:39) - Where contact sports intersect with personal finance
(06:11) - Underestimating groceries
(10:17) - Reflecting reality is the goal
(13:48) - Your priorities change all the time
(18:12) - Where is the money going to come from?
(19:51) - Can you roll with the punches too much?
(22:05) - Conscious tradeoffs
(23:50) - "Recent moves" feature
(27:31) - Modifying behavior, not just changing a number
(30:29) - Honesty and alignment

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Steve Nay:

Tyler Smith:

YNAB Rule 2: Embrace your true expenses

Steve Nay and Tyler Smith — Thu, 29 Feb 2024 05:00:00 -0600

In part two of our series, we discuss YNAB Rule 2: Embrace your true expenses.

Not every expense happens regularly or predictably. Budgeting for the infrequent or high-impact purchases that happen throughout the year increases your resilience. It can even take circumstances that used to be emergencies and convert them into mere inconveniences.

(00:00) - Auditioning in a quartet
(03:36) - Rule 2: Embrace your true expenses
(08:17) - Categories of true expenses: Predictable and unpredictable-but-inevitable
(10:49) - How to have fewer emergencies
(15:41) - The joys of auto-pay
(19:47) - True expenses vs. an emergency fund
(26:53) - Some of Tyler and Steve's true expenses
(34:01) - Debt payoff
(36:50) - How Tyler got converted to YNAB

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Steve Nay:

Tyler Smith:

YNAB Rule 1: Give every dollar a job

Steve Nay and Tyler Smith — Thu, 22 Feb 2024 05:00:00 -0600

The first episode in four-part series on the YNAB Four Rules.

Today: Giving every dollar a job, and why embracing the reality of your financial picture empowers you with clarity about your priorities.

(00:00) - Cute, little dogs
(02:17) - Rule 1: Give Every Dollar a Job
(05:47) - A plan, not a forecast
(10:21) - Scarcity and priorities
(14:08) - Building the muscle of decision-making
(15:53) - The three approaches to personal finance: Accounting, forecasting, and allocating
(20:23) - YNAB excels the best when you reflect reality inside of it

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Steve Nay:

Tyler Smith:

Steve makes a spreadsheet of McDonald's points

Steve Nay and Tyler Smith — Thu, 15 Feb 2024 05:00:00 -0600

Tyler and Steve have a McDonald’s…problem? And Steve dives into the numbers to figure it out.

Along the way, they discover the value of McDonald’s rewards points, what lessons Tyler learned from how McDonald’s prices different sizes of fries, and how to run what-if scenarios.

(00:00) - Another weird spreadsheet
(01:40) - Different prices at different McDonald's locations
(04:09) - How much are the points worth?
(07:37) - "Optimal" ways to spend points
(10:38) - Using McDonald's pricing as a model
(16:28) - What-if scenarios

Links:

Episode 18, "Optionality"

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Steve Nay:

Tyler Smith:

Tax brackets (and why they're not as scary as they seem)

Steve Nay and Tyler Smith — Thu, 08 Feb 2024 05:00:00 -0600

Steve attempts a dubious analogy to explain how tax brackets actually work. It involves buckets, a garden hose, and a very tall ladder.

(00:00) - Inspiration from a client's budget categories
(03:25) - Buckets and a garden hose

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Steve Nay:

Tyler Smith:

Book Club: Essentialism: The Disciplined Pursuit of Less (Greg McKeown)

Steve Nay and Tyler Smith — Thu, 01 Feb 2024 05:00:00 -0600

Steve might have too many things going on.

“Essentialism” by Greg McKeown provides ideas on how to focus your efforts on the things that truly matter.

Along the way, Tyler and Steve discuss a few aphorisms to jumpstart your thinking. “No is a complete sentence.” “Less but better.” “Half of the troubles of this life can be traced to saying yes too quickly and not saying no soon enough.”

(00:00) - Steve might have too many things going on
(06:34) - "Very few things are exceptionally valuable"
(09:31) - Focused forward movement
(12:32) - Unacknowledged workaholism?
(15:05) - Evaluating opportunities on multiple levels
(20:45) - Tradeoffs
(22:46) - "No is a complete sentence"
(26:55) - Intentional time for strategic thinking
(34:15) - Who would this book be good for?

Links:

"Essentialism: The Disciplined Pursuit of Less" by Greg McKeown

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Steve Nay:

Tyler Smith:

Steve gets a letter from the IRS

Steve Nay and Tyler Smith — Thu, 25 Jan 2024 05:00:00 -0600

Steve gets a surprise letter from the IRS, and it’s not good news. But with his wits about him, and with copious documentation, he’ll ride out the storm in style.

Getting IRS correspondence is never fun, but as long as you keep your records, have a good tax pro on your side, and don’t panic, it’s totally manageable.

In this episode, Steve explains the basics of dealing with IRS correspondence, and it’s less scary than you think.

(00:00) - Literal guinea pigs
(02:27) - Steve gets some ominous mail
(04:29) - What went wrong?
(07:37) - What if Steve didn't have his documentation?
(09:27) - Open your IRS correspondence!
(10:46) - Should you hire a tax pro to do this?
(13:22) - Taking the deductions you're entitled to, as long as you can back it up
(16:00) - Who's liable for your taxes?

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Steve Nay:

Tyler Smith:

Book Club: You Need a Budget

Steve Nay and Tyler Smith — Thu, 18 Jan 2024 05:00:00 -0600

As much as Steve and Tyler talk about You Need a Budget, it was finally time to review the book written by YNAB founder Jesse Mecham, which explains the mindset and process of this beloved budgeting method.

Reading the book (again, in Tyler’s case) has already changed how they budget. Tyler has freed himself up to make quicker progress on his financial goals by simplifying his focus on true expenses. Steve gave himself permission to be less obsessive about his budget, and got ideas about teaching kids money management skills.

Links:

(00:00) - The virtues of paper notepads
(04:55) - You Need a Budget, by Jesse Mecham
(09:48) - Make budgeting sacred again
(15:27) - Reframing "can I afford this?" to "does this move me closer to my goals?"
(18:13) - Balancing True Expenses with the flexibility to budget for emerging priorities
(29:14) - Budgeting for future months
(35:16) - Teaching kids to budget
(39:56) - What makes the YNAB Method different?

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Steve Nay:

Tyler Smith:

Solopreneur Taxes 101: From W-2 to Schedule C

Steve Nay and Tyler Smith — Thu, 11 Jan 2024 05:00:00 -0600

How are taxes different when you’re self-employed? Steve discusses how things change when you go from a W-2 job to being your own boss.

The biggest changes are the way you pay your taxes (withholding versus estimated tax payments) and what things you can deduct.

There are a few gotchas and surprises on the journey, but you, armed with this knowledge, can go forward prepared to face them.

(00:00) - On Resolutions and Journaling
(06:20) - Set the scene: You have a W-2 job but are considering starting a business
(07:57) - W-2 jobs and withholding
(12:21) - Withholding vs. estimated tax payments
(13:56) - Rules of thumb for estimated tax payments
(19:52) - Deductions for individuals
(23:49) - Deductions for businesses
(26:19) - Self-employment taxes
(28:46) - The way to avoid all taxes

Links:

It's Not About The Money episode 27: "The philosophy of tax deductions"

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Steve Nay:

Tyler Smith:

Retrospective: The first year(ish) of the podcast

Steve Nay and Tyler Smith — Thu, 04 Jan 2024 05:00:00 -0600

Tyler and Steve discuss the first year of “It's Not About The Money,” including numbers (surprisingly not zero!), popular episodes, favorite episodes, paradigm-shifting episodes, and advice.

Consistency is probably the most important factor, and the barriers to entry may be lower than you think. Pursuing creativity for its own sake has been rewarding.

(00:00) - Tyler gets mistaken for an older person
(02:58) - The most important number
(07:28) - Downloads, "followers," impressions, etc.
(10:30) - Which episodes have received the most attention?
(13:43) - Advice for starting a podcast
(16:22) - Get better at it by doing it
(21:42) - Steve and Tyler's favorite episodes
(28:20) - Episodes that changed Tyler's perspective

Episodes mentioned today (in release order):

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Steve Nay:

Tyler Smith:

Zapier and business process automation

Steve Nay and Tyler Smith — Thu, 14 Dec 2023 09:00:00 -0600

What processes could you automate in your business? Steve, a software developer turned tax professional, talks through several automations he’s built recently using Zapier. Tyler gets excited about the possibilities, and the two brainstorm some other ideas to “work on the business” and free up time for higher-value activities.

(00:00) - Tyler's annual review retreat
(03:05) - What is Zapier?
(05:28) - LLC consent form automation
(09:50) - Podcast production automations: breaking it down into manageable pieces
(13:32) - Using AI to write JavaScript (it got pretty close)
(19:06) - Other automation ideas
(21:35) - Choosing tools for their automation potential

---
Steve Nay:

Tyler Smith:

Side hustles to start with minimal capital

Steve Nay and Tyler Smith — Thu, 07 Dec 2023 09:00:00 -0600

Steve and Tyler have both learned so much from actually starting businesses, rather than just learning about starting businesses. So if you want to start one yourself, how should you begin?

This episode goes through some business ideas that need varying levels of skill and varying amounts of capital. Maybe one will spark an idea for you and inspire you to try something of your own.

(00:01) - Steve buys a battery pack and Tyler buys some lightswitches
(04:53) - Starting a side gig with limited capital
(08:53) - Under $1000: pet sitting, personal shopping, music instruction, language translation, content creation
(13:23) - Coaching
(16:03) - Tax preparation
(17:18) - Are these numbers bare minimums?
(18:35) - Other interesting finds: medical claims billing, car detailing, lawn care, pressure washing, home cleaning, vending
(22:17) - Home cleaning on YouTube
(24:02) - Vending machine businesses
(27:43) - Risk, capital, and experience

Links:

58 businesses to start with $10k or less

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Steve Nay:

Tyler Smith:

Revealing our business finances for 2023

Steve Nay and Tyler Smith — Thu, 30 Nov 2023 09:00:00 -0600

Steve and Tyler pull back the curtains, open up the closets, and get very vulnerable about how much it has cost to start their businesses.

Tyler proposes a rubric for evaluating expenses, which proves extremely useful: 1) Essential, 2) Have to Have, 3) Nice to Have, and 4) Shouldn’t Have. They break down what exactly is in each of these categories for them, as well as the totals and percentages for each category.

The last 20 minutes is full of introspection about the experiential value of starting a business and the various phases a young business goes through.

(00:00) - "If I understand your inflow and outflow of cash, I know exactly what's in your heart."
(01:55) - Opening up the closets on Steve and Tyler's business expenses
(04:40) - Essential, Have-to-Have, Nice-to-Have, and Shouldn't-Have
(07:26) - Tyler's expense breakdown
(14:35) - The power of retrospectives
(17:09) - Client experience, and other things we care about
(21:44) - Steve's numbers
(29:16) - Steve debates about his payment processing platform
(34:58) - Growing and experimenting versus optimizing profitability
(39:45) - Ratios of essential to non-essential expenditures
(41:36) - Tool churn, operationalizing, and more growth vs. profitability
(45:08) - Differences between personal finance and business finance
(50:46) - Learning business through experience

Links:

Planet Money episode containing Min Jin Lee quote: "Economic fact in literary fiction"

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Steve Nay:

Tyler Smith:

The philosophy of tax deductions

Steve Nay and Tyler Smith — Thu, 16 Nov 2023 09:00:00 -0600

Sure, that big business expense may land you a tax deduction, but that doesn't make it a good idea.

On this episode, Steve describes how the tax code is a tool to achieve policy goals by incentivizing certain behaviors. This might mean you should have kids or buy a truck, but don't do it just for the tax benefits.

(00:00) - The Dad-a-Base
(02:16) - Should you buy that truck for your business?
(06:33) - Taxes as a tool for policy goals
(09:34) - The philosophy of tax deductions
(18:08) - Tax planning season

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Steve Nay:

Tyler Smith:

Implementing "Getting Things Done"

Steve Nay and Tyler Smith — Thu, 09 Nov 2023 09:00:00 -0600

Steve has had a few weeks trying to implement Getting Things Done and has lots of questions for Tyler, the resident GTD veteran. Capturing actions, weekly reviews, selecting the right ticklers, and the surprising joy of physical file folders for actual pieces of paper.

(00:00) - Pilgrimage to the Ramsey studio
(03:29) - Initial capturing
(07:03) - Unexpected love for the general filing system
(11:54) - Capturing actions
(17:45) - Weekly review
(26:53) - Picking the right contexts
(31:22) - "Waiting" and "tickler" lists
(39:35) - Inbox processing

Links:

David Allen's "Getting Things Done" https://www.goodreads.com/book/show/1633.Getting_Things_Done
The episode in which Tyler convinces Steve to read the book: https://notaboutmoney.com/episodes/how-do-we-get-things-done

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Steve Nay:

Tyler Smith:

Everything is budgeting

Steve Nay and Tyler Smith — Thu, 02 Nov 2023 09:00:00 -0500

In this episode, we acknowledge that maybe we love the word "budgeting" too much and what we really mean is "making better decisions". Allocating resources (time, attention, money, nutrition) are all about scarcity and opportunity costs. It's about defining your values and the results you want, and then making the decisions that will lead you to those outcomes.

(00:00) - Roller coaster change management
(03:51) - Finite resources
(11:54) - Food opportunity costs
(14:11) - Steve's PTO budget
(18:25) - Scarcity and opportunity costs in resource allocation problems generally
(21:07) - Making better decisions (aka budgeting)

Links:

Tyler's newsletter https://newsletter.tylersmith.io/posts/why-we-feel-lost-sometimes

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Steve Nay:

Tyler Smith:

Boredom in all its forms

Steve Nay and Tyler Smith — Thu, 26 Oct 2023 09:00:00 -0500

Boredom typically means your brain is telling you something is not sufficiently meaningful or engaging, and once you recognize that you can decide how to deal with it. On this episode, Tyler and Steve discuss the research into various types of boredom and our brain's responses to them. It's about finding meaning, whether you rediscover it or reintroduce it or find it elsewhere.

(00:00) - Backwards roller coasters
(03:25) - Three types of boredom
(09:08) - Boredom provides us information
(14:12) - The fork in the road after boredom
(16:17) - Vitality: the opposite of boredom
(20:54) - Man drives tank into supermarket
(22:39) - Finding meaningful projects
(27:02) - Avoiding overcommitment

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Steve Nay:

Tyler Smith:

Creativity and the drive to create

Steve Nay and Tyler Smith — Thu, 19 Oct 2023 09:00:00 -0500

The desire to create is a core human impulse. Tyler and Steve talk about things they've created that they're proud of, whether it's a family, a business, an early-2000's blog, or a "failed" project.

(00:00) - Plastic bags and double-suspension gallops
(05:56) - The desire to create
(12:38) - Anyone can create
(18:40) - Self as community
(22:32) - Trying things that didn't work out
(26:34) - Don't let the voice of critics paralyze you

Links:

"Create" by Dieter Uchtdorf https://www.youtube.com/watch?v=RhLlnq5yY7k
"Why We Sleep" by Matthew Walker https://www.goodreads.com/book/show/34466963-why-we-sleep

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Steve Nay:

Tyler Smith:

How do we get things done?

Steve Nay and Tyler Smith — Thu, 12 Oct 2023 09:00:00 -0500

Steve describes his process for managing work, and Tyler convinces him to read Getting Things Done.

(00:00) - Halloween costume outsourcing
(03:19) - What is Steve's process?
(11:20) - David Allen's Getting Things Done
(14:03) - Tyler's process

Links:

David Allen's "Getting Things Done" https://www.goodreads.com/book/show/1633.Getting_Things_Done

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Steve Nay:

Tyler Smith:

The power of focus

Steve Nay and Tyler Smith — Thu, 05 Oct 2023 09:00:00 -0500

Tyler has a breakthrough in saving for his true expenses, and it's about more than just rearranging the financial deck chairs.

What are the benefits of focusing on one goal at a time? Why do high net worth individuals still benefit from budgeting? And why does Steve allocate some of his "fun money" to an emergency fund?

(00:00) - Dog talk
(03:06) - Too many goals
(06:44) - Doubling down on an emergency fund
(11:41) - A reverse debt snowball
(14:32) - Steve's fun money emergency fund
(16:46) - A tool for understanding opportunity costs

Links:

Our episode about Dave Ramsey's "The Total Money Makeover": https://notaboutmoney.com/episodes/book-club-total-money-makeover

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Steve Nay:

Tyler Smith:

Appliance Repairs, or, What is the Client Really Buying?

Steve Nay and Tyler Smith — Thu, 28 Sep 2023 09:00:00 -0500

Steve has repaired a handful of appliances himself, but others he won't touch without hiring a professional. Why the difference, and what is he really trying to buy?

Whether it's purchasing parts and watching YouTube videos to do the repairs himself (a little money and a lot of time) or outsourcing to an expert (a little time and a bit more money), sometimes he's buying peace of mind, sometimes hands-on experience, and sometimes convenience.

When you consider your clients, what are they really trying to buy with your products or services? It might be different than you think, and it's worth considering.

(00:00) - Steve's dryer
(05:14) - A/C disaster averted
(09:30) - What am I actually trying to buy?
(15:37) - How do you decide whether to DIY or outsource?
(17:07) - Trying to buy a green lawn
(23:59) - Hiring a milkshake

Links:

"The Innovator's Dilemma" by Clayton M. Christensen, https://www.goodreads.com/book/show/2615.The_Innovator_s_Dilemma

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Steve Nay:

Tyler Smith:

Tyler hires a coach

Steve Nay and Tyler Smith — Thu, 21 Sep 2023 09:00:00 -0500

Tyler is a coach, and now he has hired a coach. Steve asks him about how it works, what he's learned, and how it's making him a better coach to his own clients.

But first! A brief diversion into dog grooming. 🐶

(00:00) - Steve's dog requires grooming; Tyler's does not
(02:14) - Tyler hires a health coach
(09:44) - What Tyler (the client) has learned about being Tyler (the coach)
(14:46) - Business, executive, and career coaches

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Steve Nay:

Tyler Smith:

Optionality

Steve Nay and Tyler Smith — Thu, 31 Aug 2023 09:00:00 -0500

Steve discusses an iPad purchase and its accompanying sheet music adventures. Tyler finds a surprise bank account. An acquaintance buys a house for cheap.

Having cash available is doubly beneficial--it protects you from unexpected risks and it lets you take advantage of unexpected lucky opportunities.

(00:00) - Esoteric spreadsheets
(05:37) - What is optionality?
(10:16) - Risk and luck
(13:19) - Savings gap
(15:33) - Steve buys an iPad for sheet music
(19:52) - Tyler squirrels away money so he'll forget about it
(21:31) - How do you define financial independence?

Links:

The Psychology of Money, by Morgan Housel https://www.goodreads.com/book/show/41881472-the-psychology-of-money
YNAB Rule 2: Embrace Your True Expenses https://www.ynab.com/the-four-rules/#rule-two

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Steve Nay:

Tyler Smith:

Book Club: Psychology of Money

Steve Nay and Tyler Smith — Thu, 24 Aug 2023 09:00:00 -0500

Steve and Tyler discuss Morgan Housel's 2020 book, "The Psychology of Money". It distills a lot of financial wisdom into an easy-to-read anthology of advice and, especially, cogent explanation.

Embrace risk but beware of ruinous risk. Get the goalposts to stop moving. Be wealthy versus rich. Don't let your ego stand in the way of accumulating wealth.

(00:00) - Lemonade stands
(01:19) - Psychology of Money
(06:03) - Experience vs. perception
(09:42) - The newness of "retirement"
(14:35) - Rich vs. wealthy
(17:58) - Getting the goalposts to stop moving
(25:47) - Luck, tail events, and risk
(33:28) - Ego

Links:

The Psychology of Money, by Morgan Housel https://www.goodreads.com/book/show/41881472-the-psychology-of-money

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Steve Nay:

Tyler Smith:

Should you outsource your chores?

Steve Nay and Tyler Smith — Thu, 17 Aug 2023 09:00:00 -0500

Should Steve outsource his lawn maintenance? What did Tyler think of hiring house cleaners? And why is that so different from going to a car wash? Today, we talk about outsourcing in business and in life, and the tradeoffs of time and money it entails.

(03:44) - Outsourcing in personal life
(07:33) - Tyler hires a house cleaner
(11:29) - Meal kits
(13:22) - Outsourcing as leverage
(16:30) - Steve hires a billing platform
(17:52) - Steve doesn't hire a lawn company
(22:16) - Life is about tradeoffs

Links:

Tax Strategy Digest episode, "Marketing The Right Way": https://www.linkedin.com/pulse/marketing-right-way-paul-ranieri/

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Steve Nay:

Tyler Smith:

Why coaching and taxes make good side gigs

Steve Nay and Tyler Smith — Thu, 10 Aug 2023 09:00:00 -0500

What characteristics make a good side gig? How do you strike a balance between your day job and your side project? How much is enough?

(00:00) - Japanese curry
(03:31) - Flexibility
(07:32) - Remote work
(10:27) - Choose how many clients to take on
(13:21) - Low barriers to entry
(16:56) - Keeping it intentionally small
(20:55) - Low capital investment
(25:00) - Skills for your primary career
(27:29) - Try it out!

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Steve Nay:

Tyler Smith:

Book Club: Total Money Makeover

Steve Nay and Tyler Smith — Thu, 03 Aug 2023 09:00:00 -0500

Today we review that classic personal finance book, Dave Ramsey's Total Money Makeover. Credit cards, sustainable journeys, Murphy repellant, budgeting, and behavior.

https://www.goodreads.com/book/show/78427.The_Total_Money_Makeover

(00:00) - Credit cards
(02:20) - Total Money Makeover
(07:02) - 20% knowledge, 80% behavior
(12:18) - Making the journey sustainable
(17:47) - Emergency funds
(21:40) - 12% returns?
(24:14) - Living on the financial edge with credit cards
(29:05) - Murphy repellant
(29:49) - The role of a budget
(32:29) - The heart of a teacher

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Steve Nay:

Tyler Smith:

Finding a niche in HVAC, with Jeremy Wells

Steve Nay and Tyler Smith — Thu, 27 Jul 2023 09:00:00 -0500

Jeremy Wells, EA, CPA is the owner of JWellsCFO and recently launched a new business called The HVAC CPA focused on the particular needs of HVAC business owners. In this episode, Jeremy talks about his journey into accounting, how he selected this niche, and how he becomes the trusted advisor his clients need.

Jeremy Wells, EA, CPA:

(01:11) - Jeremy's path into accounting
(09:33) - Deciding to become a CPA as well as an Enrolled Agent
(19:22) - Doing things differently in the industry
(24:25) - Niching and developing expertise
(29:45) - Starting The HVAC CPA
(43:55) - Venn diagram of finding a niche
(46:56) - Book recommendations
(51:03) - Don't try to be everything to everyone

Links:

David C. Baker, the "expert for experts": https://www.linkedin.com/in/dcb/
The CPA Advisory Show, episode "Our Top Books to Learn and Deliver Advisory Services": https://podcasts.apple.com/us/podcast/our-top-books-to-learn-and-deliver-advisory-services/id1627272813?i=1000570577451
Building a Second Brain, by Tiago Forte: https://www.goodreads.com/book/show/59616977-building-a-second-brain
Time's Up!: The Subscription Business Model for Professional Firms, by Paul Dunn and Ronald J. Baker: https://www.goodreads.com/book/show/63352831-time-s-up

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Steve Nay:

Tyler Smith:

To niche or not to niche

Steve Nay and Tyler Smith — Thu, 20 Jul 2023 09:00:00 -0500

Should you find a niche in your business? When is it too early? How should you figure out the "right" niche? And will Tyler change his mind about it?

(00:00) - Recovering grammar nerd
(02:54) - Should you even niche?
(15:11) - Horizontal vs. vertical niches
(17:00) - Steve's current niche
(17:55) - Tyler's current niche
(22:57) - To niche or not to niche?

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Steve Nay:

Tyler Smith:

Optimizing for serendipity

Steve Nay and Tyler Smith — Thu, 13 Jul 2023 09:00:00 -0500

Do the best things in life come from planning or from serendipity? Tyler and Steve explore this question and give some ideas about how to welcome more serendipity into your life.

(00:00) - Fitness
(02:31) - "Everyone has a plan until they get punched in the face"
(04:21) - Spontaneity
(07:42) - Building your network
(18:17) - Social media
(21:01) - Reading books
(23:15) - "Successful careers are not planned. They develop."
(25:24) - Boredom and creativity

Links:

Jason Daily: How To Become The Luckiest Accountant https://share.transistor.fm/s/2b8e607a
Video from Jason with more actionable advice, which I didn't discover until after we recorded: 4 Ways To Become a Luckier Accountant https://www.youtube.com/watch?v=GZeE3qpsteE

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Steve Nay:

Tyler Smith:

Book Club: The Prosperous Coach

Steve Nay and Tyler Smith — Thu, 06 Jul 2023 09:00:00 -0500

Tyler mentions it often, and it's high time we had a proper discussion about it. The book is "The Prosperous Coach" by Steve Chandler and Rich Litvin. From getting better at selling to working with extraordinary clients, there's something in this book for every business owner, whether or not you consider yourself a coach per se.

(00:00) - Gardening
(02:30) - The Prosperous Coach
(05:38) - People don't buy hours of coaching
(11:38) - Coaching and the business of coaching
(17:17) - Talk about your accomplishments
(21:39) - Extraordinary clients

Links:

The Prosperous Coach: https://www.goodreads.com/book/show/18934115-the-prosperous-coach

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Steve Nay:

Tyler Smith:

Bookkeeping: YNAB vs. QuickBooks

Steve Nay and Tyler Smith — Thu, 29 Jun 2023 09:00:00 -0500

What are some good tools if you want to get started keeping the books of your business?

Steve and Tyler discuss YNAB and QuickBooks: their strengths and weaknesses, their similarities and differences, and ultimately which one you might want to choose for your business.

(00:00) - iOS automations
(02:50) - Two bookkeeping tools: YNAB and QBO
(05:13) - What is YNAB great at?
(09:55) - What is QuickBooks great at?
(12:47) - Setting aside money for taxes
(16:57) - Equivalent concepts in YNAB and QBO
(20:15) - What does your tax pro need from your books, really?
(26:07) - Handling (or not) merchant fees in YNAB
(29:17) - QBO gotchas
(32:32) - Steve and Tyler's recommendations on which to pick: YNAB or QBO (or both?)
(37:21) - Pricing

Links:

Tyler's thorough review of YNAB: https://www.tylersmith.io/blog/ynab-vs-everydollar

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Steve Nay:

Tyler Smith:

Bookkeeping: What is it? Why do it?

Steve Nay and Tyler Smith — Thu, 22 Jun 2023 07:00:00 -0500

What is bookkeeping? Why do you need it as a small business owner? How do you get started?

In this episode, Steve and Tyler dive into these questions and give you practical tips, whether you're just starting out, you are doing the books yourself, or you're ready to hire a bookkeeper.

00:00 Cashflow problems as a factor in business failure
01:35 What is bookkeeping?
07:31 How do you start keeping the books for your business?
11:09 Okay, you have a separate business account. Now what?
14:41 Common bookkeeping mistakes
20:02 What are the benefits of good bookkeeping?

Links:

"What to do when you can't afford a bookkeeper" from "By the Books" podcast: https://www.youtube.com/watch?v=Sdv0qO4kUVQ

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Steve Nay:

Tyler Smith:

How to close clients

Steve Nay and Tyler Smith — Thu, 15 Jun 2023 02:00:00 -0500

Once you've found prospective clients, how do you get them to decide to hire you?

On this episode, Tyler and Steve discuss two sales techniques and what works and doesn't work about each of them for their particular businesses.

00:00 An embarrassing sales call
02:15 The CLOSER method
09:20 Aspects of the CLOSER method that resonate with Steve and Tyler
13:52 Following up with a prospect after the call
16:51 "Send a gift and a note"
22:18 Tyler tries a CLOSER script
23:26 The "Creating Clients" approach
34:25 Steve gets nervous talking about pricing
40:23 What to do if a client is driving the bus

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Steve Nay:

Tyler Smith:

How to find clients

Steve Nay and Tyler Smith — Thu, 08 Jun 2023 02:25:11 -0500

How do you find clients as a solopreneur running a virtual service business like coaching or tax prep?

Tyler and Steve describe many of the things they've tried, as well as which ones actually worked.

00:00 Harrison Ford's job before Star Wars
04:14 Social media marketing
10:26 Paid ads
15:43 SEO and chatGPT
19:54 Networking IRL
23:03 Being a jack-of-all-trades as a solopreneur
25:09 Benefits of having a local network
28:44 Referrals
31:34 Where did Steve's actual clients come from?
34:16 Where did Tyler's actual clients come from?
36:05 Pre-qualifying clients before they even talk to you
43:31 Supply and demand in qualifying leads

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Steve Nay:

Tyler Smith:

The Person is the Program

Steve Nay and Tyler Smith — Wed, 31 May 2023 21:00:00 -0500

Tyler has an epiphany about coaching.

We explore his discovery and what it means for how he connects with his clients, whether they need consulting, teaching, or coaching.

Things we mentioned:

Beginning Balance with Mark Butler and Jesse Mecham
The Prosperous Coach by Steve Chandler and Rich Litvin
Coach with Tyler

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Steve Nay:

Tyler Smith:

When is it time to hire a tax pro?

Steve Nay and Tyler Smith — Thu, 25 May 2023 02:00:00 -0500

TurboTax is great for a lot of people, but how do you know when you've outgrown it?

Steve and Tyler discuss when it's time to find a good accountant who's worth the price to save your sanity and get your taxes done right.

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Steve Nay:

Tyler Smith:

Do I need an LLC?

Steve Nay and Tyler Smith — Fri, 19 May 2023 15:00:00 -0500

One of the big decisions when you start a business is how to structure the legal entity.

Do you need an LLC?

What is a DBA?

Why do people have S Corps?

All those details and more in this episode.

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Steve Nay:

Tyler Smith:

Meet Tyler

Steve Nay and Tyler Smith — Fri, 19 May 2023 14:00:00 -0500

Steve Nay interviews co-host Tyler Smith about building a financial coaching practice while pursuing a career as a localization professional.

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Steve Nay:

Tyler Smith:

Meet Steve

Steve Nay and Tyler Smith — Fri, 19 May 2023 13:40:59 -0500

Tyler Smith interviews co-host Steve Nay, a tax professional and owner of Daybreak Tax, about his career in software and building a tax practice that serves small business owners.

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Steve Nay:

Tyler Smith:

Introduction

Steve Nay and Tyler Smith — Wed, 17 May 2023 23:45:11 -0500

This is “It’s Not About The Money,” a podcast for current and aspiring solopreneurs and small business owners.

You'll hear stories of building a tax practice and a coaching business.

You'll learn a wealth of things business owners need to know: Leadership. Entrepreneurship. Operations. Productivity. How to create clients. And so much more.

Join Steve and Tyler on this journey of discovery, and figure out why "it's not about the money!"

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Steve Nay:

Tyler Smith: