Episodes
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How to read a pay stub
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…
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Task management is not project management
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...
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A train wreck of email
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…
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Retrospective on the "Many Hats of an Entrepreneur" interviews
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...
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Business website design, with James Hagen
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...
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Superpower Storytelling, with Stephen Steers
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...
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Human Resources Operations, with Vanessa Gutierrez
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...
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Navigating health insurance as a solopreneur, with Mitchell Underwood
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...
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Selling without "commission breath," with Landon Pitcher
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…
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Developing your marketing strategy, with Juliana Weiss-Roessler
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...
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Growing your business at the right pace, with Erica Goode
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...
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Managing your equity compensation, with Alex Crouch
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…
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Cybersecurity basics for solopreneurs, with Don Sesler
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…
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The Many Hats of an Entrepreneur
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...
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Coming soon: Interviews about the many hats of an entrepeneur
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…
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YNAB Rule 4: Age your money
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…
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YNAB Rule 3: Roll with the punches
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...
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YNAB Rule 2: Embrace your true expenses
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...
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YNAB Rule 1: Give every dollar a job
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...
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Steve makes a spreadsheet of McDonald's points
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...
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Tax brackets (and why they're not as scary as they seem)
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 --- Steve Nay: https://daybreaktax.com/...
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Book Club: Essentialism: The Disciplined Pursuit of Less (Greg McKeown)
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...
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Steve gets a letter from the IRS
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...
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Book Club: You Need a Budget
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...
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Solopreneur Taxes 101: From W-2 to Schedule C
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...
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Retrospective: The first year(ish) of the podcast
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....
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Zapier and business process automation
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…
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Side hustles to start with minimal capital
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...
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Revealing our business finances for 2023
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...
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The philosophy of tax deductions
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...
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Implementing "Getting Things Done"
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...
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Everything is budgeting
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…
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Boredom in all its forms
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...
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Creativity and the drive to create
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)…
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How do we get things done?
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"...
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The power of focus
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…
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Appliance Repairs, or, What is the Client Really Buying?
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…
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Tyler hires a coach
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...
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Optionality
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...
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Book Club: Psychology of Money
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.…
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Should you outsource your chores?
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…
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Why coaching and taxes make good side gigs
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)…
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Book Club: Total Money Makeover
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) -...
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Finding a niche in HVAC, with Jeremy Wells
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...
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To niche or not to niche
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)…
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Optimizing for serendipity
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) -...
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Book Club: The Prosperous Coach
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...
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Bookkeeping: YNAB vs. QuickBooks
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...
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Bookkeeping: What is it? Why do it?
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…
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How to close clients
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…
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About this show
Solopreneurs and small business owners: learn about leadership, operations, entrepreneurship, productivity, taxes, client creation, marketing, bookkeeping, and more.
Hosted by
Steve Nay and Tyler Smith
Categories