Thinking Solo

By Ryan Derousseau, CFP®, EA

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Category: Entrepreneurship

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Episodes: 28

Description

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 learned the hard way, and what they do to stay sharp — plus solo-focused episodes from Ryan with tip

Episode Date
Why Your Accountant Isn’t Saving You Money (And What Tax Planning Actually Looks Like)
Oct 29, 2026
You Made $1 Million Last Year. So Why Is Your Savings Account Empty?
Oct 22, 2026
When (and How) to Hire Your First Employee
Oct 15, 2026
Backdoor Roth IRA
Oct 08, 2026
Self-Employed Mortgages: How to Actually Qualify
Oct 01, 2026
Health Insurance for Self-Employed Professionals
Sep 24, 2026
When and Why To Use Roth Conversions
Sep 03, 2026
Solo 401k vs SEP IRA
Aug 27, 2026
Understanding The Power of the Health Savings Account
Aug 20, 2026
What You Should (and Shouldn’t) Write Off for Your Business
Aug 13, 2026
Building an Estate Plan for Your Business
Aug 11, 2026
The Private Practice Checklist
Jul 30, 2026
Fiduciary Advisor
Jul 24, 2026
Managing Variable Income as a Business Owner
Jun 25, 2026
Estimating Taxes
Jun 18, 2026
Setting Up Your Business
Jun 16, 2026
Episode #13: Managing Entrepreneur Syndrome:
May 29, 2026
From CPA to LinkedIn Strategist Featuring Wendy Shore
May 13, 2026
Merging Therapy and Accounting with Jennie Schottmiller
Apr 23, 2026
I Make $200k and I Still Feel Broke. Why?
Apr 16, 2026
Betting on Yourself — Brie Chrisman on Building Boss Co. and Leading with Intention
Apr 09, 2026
Dealing With Volatility, In Business and Life
Mar 26, 2026
Gregory Milano on Strategy, Resilience, and Long-Term Thinking
Mar 17, 2026
Three Tax Issues to Watch For, Solopreneurs - Episode #6
Mar 11, 2026
Freedom, Flexibility, and Financial Reality — Succeeding as a Solopreneur with Elaine Pofeldt
Mar 04, 2026
Getting Started With Your Business Idea: Thinking Solo Episode 4
Feb 24, 2026
Choosing the Right Entity for Your Business - Episode #2
Feb 10, 2026
The Solo Business Journey Isn’t Straight — Thinking Solo Is Back
Feb 02, 2026