All Episodes

Displaying episodes 1 - 30 of 54 in total

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 slo...

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 de...

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...

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 ...

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, hav...

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 ...

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 ...

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 ...

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, restricte...

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 da...

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...

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, insur...

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'...

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 aspirati...

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...

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 wi...

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...

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. --- Steve Nay: https://daybreak...

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, T...

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. Gett...

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 pr...

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...

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-shiftin...

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 Za...

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,...

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 ...

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 achi...

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, sel...

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, atte...

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....

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