Thinking Solo

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 shares how she initially pursued accounting, then later therapy, and how her own journey inspired her to create Simple Profit. She discusses how the business began as an educational resource for therapists, evolved into a flexible, accessible platform for small business owners, and continues to grow through a combination of free content, low-cost memberships, and now traditional tax and bookkeeping services.In this episode, you’ll learn:• How Jennie merged her accounting and therapy skills to serve small business owners• Why so many therapists and small business owners lack formal business education• The concept of “income smoothing” and why it matters for self-employed owners• How to provide yourself paid time off even as a solo business owner• Why starting a business can feel scary, but is achievable with the right support• How Simple Profit grew organically through education, community, and free resources• Lessons learned from scaling services, managing staff, and navigating marketing hurdles• Why the business side of running a company is “straightforward” once understood• How focusing on helping clients can bring fulfillment to work that otherwise feels tedious• Advice for new business owners: “you can do it,” and asking for help is a strength, not a weaknessThis episode offers a practical, empowering perspective for solo and small business owners who want to understand their finances, build confidence, and run their businesses more effectively.—-Connect with Jennie Schottmiller, CPA, LMFT:LinkedIn: https://www.linkedin.com/in/simpleprofit/Website: https://www.simpleprofit.com/pages/about-usConnect with Ryan Derousseau, CFPEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 calculating revenues or profits, and what you need to include when determining how big your business has grown. Ryan shares his thoughts on what may be happening in these cases, and tactics to avoid the pitfall yourself. At the end of the episode, Ryan also delves into his latest movie review: RoboCop, the 1987 sci-fi thriller from director Paul Verhoeven.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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. was preparing for its first conference and in the middle of a rebrand. Since then, Brie has built a business that supports therapists and practice owners who were never taught how to run a business, yet are expected to do so every day.Brie shares how Boss Co. began in 2020 after she was laid off shortly after becoming a new mother, why she chose to bet on herself despite not being a natural risk-taker, and how the company evolved from a virtual operations assistant business into a specialized agency for mental health practices. She also opens up about leading through burnout, building a team and culture that can operate without her, and growing slowly and intentionally.In this episode, you’ll learn:• How Boss Co. was founded during the uncertainty of 2020• Why Brie chose entrepreneurship despite being risk-averse• What led Boss Co. to fully pivot into the mental health space• The “ripple effect” impact of supporting overwhelmed practice owners• Why most therapists receive no business education, and how that gap shows up• How customization (not one-size-fits-all) drives long-term client retention• What capacity-driven growth really looks like in practice• How strong systems and team culture kept the business running during burnout• Brie’s team training approach using the “I do, we do, you do” model• Why asking for help is a strength, not a weaknessThis conversation is an honest look at building a values-driven business, navigating personal challenges, and designing a company that supports both its clients and its founder.—-Connect with Brie Chrisman:LinkedIn: https://www.linkedin.com/in/brie-chrisman/Website: https://heybossco.com/aboutConnect with Ryan Derousseau, CFP:Email: [email protected] LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 many lessons that solopreneurs and small business owners can take from their own business, when considering this volatility. Ryan shares his thoughts on the volatility and how to approach the current fear in the market or in your business. At the end of the episode, Ryan also gives a quick review of How Green Was My Valley an Oscar winner in 1942, beating out Citizen Kane for best picture. It's shockingly relevant to today's times and your business journey (most likely).Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 Suisse was let go. While the moment felt uncertain, it ultimately created the opening to build the exact business he had been envisioning: one that allowed him to work deeply with a small number of companies instead of superficially with many.Drawing on his engineering background, early career experience inside large manufacturing and aerospace companies, and decades as an advisor, Gregory offers a candid look at what really happens inside organizations, and why textbook solutions often fall apart in the real world. He also opens up about the extreme volatility of running a consulting business, the hard lessons learned during downturns, and how Fortuna evolved to survive and grow.In this episode, you’ll learn:• How Fortuna Advisors was founded during the financial crisis• Why walking away from investment banking pay was one of the hardest decisions• How an engineering background shaped Gregory’s approach to strategy and problem-solving• What extreme revenue volatility looks like in a consulting business• Why recency bias is dangerous during good times• How being careful with fixed costs protects a business in downturns• Lessons learned from product ideas that were “too early” for the market• How Fortuna is making value-based management accessible to smaller companies• Why successful leaders balance short-term execution with long-term investment• Practical advice for solopreneurs on timing, flexibility, and rolling with changeThis episode is a grounded, experience-driven conversation about resilience, adaptability, and building a business that can survive both boom times and inevitable downturns.—-Connect with Gregory MilanoLinkedIn: https://www.linkedin.com/in/greg-milano/Website: https://fortuna-advisors.com/Connect with Ryan Derousseau, CFPEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau Website: https://thinkingcapfinancial.com

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 important to remember this, as you review your taxes and consider the impact for next year.Ryan shares three common issues he often sees on the self employed's tax return, so you can look out for it yourself or ask your tax preparer about it. At the end of the episode, Ryan also gives a quick review of Do Not Expect Too Much From the End of the World, and explains the insight he had watching this bleak look at the current working world.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

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 while raising four children, and why she considers that flexibility one of the greatest rewards of working for yourself.Together, Ryan and Elaine dig into the less-glamorous realities of freelance and solo work: uncertainty, discipline, financial resilience, taxes, health insurance, and the constant need to balance client work with business development. They also explore why so many people (at every life stage) are choosing the solopreneur path in search of freedom.In this episode, you’ll learn:• Why solopreneurs rarely feel “fully comfortable” — and why that’s normal• How recurring clients and retainers build confidence and stability• The importance of discipline, planning, and managing multiple roles• Why living below your means creates resilience when clients disappear• Smart ways freelancers can prepare for taxes and avoid surprises• The biggest financial hurdle Elaine faced as a solo business owner• Why “freedom” is the common thread driving people toward solo work• How AI and technology are powerful tools for solopreneurs without capital• Why freelancers often report better health than corporate employees• The value of non-screen outlets and trusted “freelance buddies”This conversation is a grounded look at solo business ownership… The trade-offs, the rewards, and the systems that make it sustainable over the long term.---Connect with Elaine Pofeldt:LinkedIn: http://linkedin.com/in/elainepofeldt/YouTube: http://youtube.com/UCr5VUkqfMpz_JPGnnXu3F8aWebsite: https://www.elainepofeldt.com/Connect with Ryan Derousseau, CFP:Email: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 practices for overcoming this concern, as it can set good ideas back for years or can lead to a very poor early efforts... until you learn what works. At the end of the episode, Ryan also gives a quick review of Predator: Badlands, and explains a lesson from the movie solopreneurs and small business owners can take away from the picture.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFPEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 each entity and downsides to the same business structure. And you will have to operate in it moving forward, depending on which one you select. At the end of the episode, Ryan also provides a movie selection for those in solo business - and this time he takes a quick look at The Mastermind.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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 working with this crowd, how his own solo-operator mindset shapes the show (including compliance through United Financial Planning Group), and why his firm is called Thinking Cap Financial.This isn’t a “tech billionaire” podcast. It’s for grinders, innovators, and go-getters who want freedom, meaningful work, and the ability to afford the lifestyle they actually want — without needing a boss.Going forward, you’ll see two episodes per month:✅ Entrepreneur interviews (journey, routines, what keeps them moving)✅ Solo business & money tips directly from Ryan (uncertainty, growth, and sustainable success)Subscribe and stick around, and in the meantime… keep grinding!---Connect with Ryan Derousseau, CFPEmail: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/