Shows / Thinking Solo
Thinking Solo
Thinking Solo is a podcast for solo and very small business owners who are building real businesses in the real world — therapists, private practice doctors, engineers, marketers, creators, and side entrepreneurs. Hosted by Ryan Derousseau, CFP®, EA, the show blends practical money guidance with the human side of going solo: the uncertainty, the momentum, the setbacks, and the habits that keep you moving forward. You’ll hear conversations with entrepreneurs about how they operate, what they’ve…
Episodes
Thinking SoloTwo Powerful Savings Vehicles Your One-Person, $1M Business Isn’t Using
Welcome to another episode of Thinking Solo with Ryan Derousseau, CFP®, EA, where we explore the best financial strategies for high earning entrepreneurs…
Thinking SoloWhy Your Accountant Isn’t Saving You Money (And What Tax Planning Actually Looks Like)
Is your accountant actually saving you money, or are they just filing your tax returns? As your business grows, tax preparation alone isn't enough to help you…
Thinking SoloYou Made $1 Million Last Year. So Why Is Your Savings Account Empty?
Why does high business revenue not always mean personal wealth? Many entrepreneurs generate $1M+ in revenue but have empty personal savings accounts or…
Thinking SoloWhen (and How) to Hire Your First Employee
Taking the leap from solo operator to business owner is a major milestone. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA breaks down the…
Thinking SoloBackdoor Roth IRA
In this episode of Thinking Solo, financial planner Ryan Derousseau explores the backdoor Roth IRA strategy for high earners. Learn how to navigate tax…
Thinking SoloSelf-Employed Mortgages: How to Actually Qualify
Getting a mortgage when you are self-employed can feel like an uphill battle. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, breaks down how…
Thinking SoloHealth Insurance for Self-Employed Professionals
In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, explores health insurance options for self-employed professionals, freelancers, and small…
Thinking SoloWhen and Why To Use Roth Conversions
In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, explores the fundamentals of Roth conversions and how they may serve as a strategic tool for…
Thinking SoloSolo 401k vs SEP IRA
Welcome to Thinking Solo with host Ryan Derousseau, CFP®, EA, where we talk about ways to succeed in business and life. In this episode, we break down the key…
Thinking SoloUnderstanding The Power of the Health Savings Account
Is your Health Savings Account (HSA) doing enough for your financial future? Many people view the HSA merely as a way to pay for current medical expenses, but…
Thinking SoloWhat You Should (and Shouldn’t) Write Off for Your Business
Are you maximizing your small business tax deductions or leaving money on the table? In this episode, we break down how to navigate IRS business expenses so…
Thinking SoloBuilding an Estate Plan for Your Business
In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, discusses why entrepreneurs may need to look beyond their companies for long-term financial…
Thinking SoloThe Private Practice Checklist
Starting a private practice comes with unique financial responsibilities. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, walks through a…
Thinking SoloFiduciary Advisor
In this episode of Thinking Solo, I’m cutting through the industry jargon that confuses so many business owners. We’re breaking down the critical differences…
Thinking SoloManaging Variable Income as a Business Owner
Variable income can make financial planning feel messy, especially for solo entrepreneurs, freelancers, private practice owners, and self-employed…
Thinking SoloEstimating Taxes
Self-employed? Then listen up: revenue is not profit, and profit is what really matters. In this episode of Thinking Solo, Ryan breaks down one of the biggest…
Thinking SoloSetting Up Your Business
Going self-employed can feel exciting, freeing, and completely overwhelming all at once. You’re no longer just doing the work. You’re now responsible for the…
- Thinking Solo
Episode #13: Managing Entrepreneur Syndrome:
In today's episode, Ryan discusses an issue that both drives entrepreneurs and solopreneurs, but can also leave them later in life with very little to their…
Thinking SoloFrom CPA to LinkedIn Strategist Featuring Wendy Shore
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with Wendy Shore, a business growth advisor, LinkedIn and AI strategist, and…
Thinking SoloMerging Therapy and Accounting with Jennie Schottmiller
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with Jennie Schottmiller, CPA, LMFT, founder and owner of Simple Profit. Jennie…
- Thinking Solo
I Make $200k and I Still Feel Broke. Why?
In today's episode, we discuss a growing trend within the US: People who make $200,000 or more a year and still feel broke. For those with regular employment…
Thinking SoloBetting on Yourself — Brie Chrisman on Building Boss Co. and Leading with Intention
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with Brie Chrisman, founder and CEO of Boss Co., an operations management and…
- Thinking Solo
Dealing With Volatility, In Business and Life
Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we discuss how to manage volatility. There's a lot of volatility in the…
Thinking SoloGregory Milano on Strategy, Resilience, and Long-Term Thinking
Stand by, this episode is jam packed full of great info! This week, Ryan Derousseau, CFP®, EA, sits down with Gregory Milano, founder and CEO of Fortuna…
- Thinking Solo
Three Tax Issues to Watch For, Solopreneurs - Episode #6
Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we take a moment to talk about taxes. In the midst of the 2026 tax season…
Thinking SoloFreedom, Flexibility, and Financial Reality — Succeeding as a Solopreneur with Elaine Pofeldt
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with author and freelance journalist Elaine Pofeldt to talk about what it really…
- Thinking Solo
Getting Started With Your Business Idea: Thinking Solo Episode 4
Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we look at how to simply get started in your new business - or growing your…
- Thinking Solo
Choosing the Right Entity for Your Business - Episode #2
Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we look at entity selection, particularly for small and service based…
Thinking SoloThe Solo Business Journey Isn’t Straight — Thinking Solo Is Back
Welcome back to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA. This episode is a reboot of the show and a quick reset on what you’ll hear here and who…