Thinking Solo

Variable income can make financial planning feel messy, especially for solo entrepreneurs, freelancers, private practice owners, and self-employed professionals. When income goes up and down, it can be hard to know how much to pay yourself, how much to save, and how to keep building wealth without letting fear drive every decision. In this episode of Thinking Solo , Ryan Derousseau, CFP®, EA break...

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 financial traps business owners fall into: getting paid, feeling flush, and forgetting that taxes are coming. If you’re running your own business, estimated taxes are not optional planning fluff. They are part of running the business like an...

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 business bank accounts, taxes, insurance, retirement savings, cash reserves, and figuring out how much you actually need to earn to make the whole thing work. In this episode of Thinking Solo, Ryan Derousseau breaks down five key financial sy...

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 name, other than the business they created. This is something he dubs entrepreneur syndrome, and it's the common strategy of only investing in the businesses you create, instead of diversifying out. It's something that takes hold i...

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 longtime entrepreneur. Wendy shares her unconventional path: from CPA to restaurant owner (running seven locations and managing hundreds of employees), to walking away from that industry after a major turning point that impacted both her business...

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 uniquely combines her experience as a CPA and a licensed therapist (LMFT) to help small business owners (particularly therapists) understand their finances, run their businesses confidently, and create stability in both life and work. Jennie sh...

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, it's likely a spending concern. But for those solopreneurs or small business owners out there, the problem actually may be linked to how you're evaluating the success of your business. It really comes down to whether you're c...

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 growth strategy agency serving mental health private practice owners. Ryan and Brie first connected at a psychotherapy conference not to meet clients, but to connect with professionals who support mental health practitioners. At the time, Boss Co...

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 markets right now, due to the impact of the Iran War and rising gas prices. But how you manage the volatility will be key to determine whether you end up successful through this time or get stuck regretting what occurred. There's man...

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 Advisors, to unpack his journey from investment banking to building a strategic consulting firm that has now endured for nearly 17 years. Gregory shares how Fortuna Advisors was born out of the financial crisis, after his specialty group at Credit...

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, it's easy to look on last year and think there's nothing that can be done or nothing to look out for. But in reality, there are regular, common mistakes that solopreneurs and small business owners make on their taxes. It's imp...

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 takes to succeed as a solopreneur. Elaine has been running her solo business since 2007 and is the author of Tiny Business, Big Money and The Million-Dollar One-Person Business. She shares how building a solo business allowed her to be present...

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 business to the next level. It's one of the hardest parts of the business journey: Simply starting. Too many times, we think too far ahead and it can overwhelm the process, destroying any effort to move forward. Ryan shares best prac...

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 businesses. What's the right business for you? LLC? Sole Prop? S-Corp? Ryan shares best practices for the selection, and explains why you should use the entity choice as a tool - not a signpost to reach. That's because there are good reasons for e...

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 it’s for: solo operators and very small business owners — therapists, private practice doctors, engineers, marketers, tinkerers, and side entrepreneurs — who are building a business (and a life) on their own terms. Ryan shares why he loves wor...