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 (...
Aug 15, 2024•20 min•Ep. 56
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 wee...
Aug 08, 2024•35 min•Ep. 55
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) - Podca...
Jul 25, 2024•30 min•Ep. 54
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 ...
Jul 18, 2024•17 min•Ep. 53
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 Unde...
Jul 11, 2024•39 min•Ep. 52
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:/...
Jun 20, 2024•44 min•Ep. 51
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 mig...
Jun 13, 2024•31 min•Ep. 50
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 i...
Jun 06, 2024•37 min•Ep. 49
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...
May 30, 2024•45 min•Ep. 48
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 cons...
May 16, 2024•46 min•Ep. 47
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 teenage...
May 09, 2024•44 min•Ep. 46
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...
May 02, 2024•40 min•Ep. 45
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 di...
Apr 25, 2024•44 min•Ep. 44
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 lik...
Apr 18, 2024•24 min•Ep. 43
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. Somet...
Mar 21, 2024•5 min•Ep. 42
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 dispe...
Mar 14, 2024•29 min•Ep. 41
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) - Unde...
Mar 07, 2024•36 min•Ep. 40
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-i...
Feb 29, 2024•41 min•Ep. 39
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...
Feb 22, 2024•29 min•Ep. 38
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 mode...
Feb 15, 2024•21 min•Ep. 37
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/ https://www.linkedin.com/in/nsteven/ Tyler Smith: https://www.tylersmith.io/ https://www.linkedin.com/in/tylersmith-io/...
Feb 08, 2024•13 min•Ep. 36
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:...
Feb 01, 2024•38 min•Ep. 35
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 mai...
Jan 25, 2024•20 min•Ep. 34
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 teachin...
Jan 18, 2024•43 min•Ep. 33
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 start...
Jan 11, 2024•31 min•Ep. 32
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) ...
Jan 04, 2024•32 min•Ep. 31
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 man...
Dec 14, 2023•27 min•Ep. 30
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 ca...
Dec 07, 2023•31 min•Ep. 29
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 starti...
Nov 30, 2023•55 min•Ep. 28
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 plan...
Nov 16, 2023•23 min•Ep. 27
