Thinking Solo

Ryan Derousseau, CFP®, EA
  • 0.0 (0)
  • Entrepreneurship
  • Updated Weekly

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

  1. Setting Up Your Business

    1d ago

    Setting 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 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 systems every solo business owner or self-employed professional should consider putting in place early. Whether you are just starting out or already earning revenue, these steps can help create more clarity between your business finances and personal life. Ryan covers why separating business and personal expenses matters, how to think about tax savings before tax season arrives, what benefits you may need to replace after leaving traditional employment, and why cash reserves are so important when income is inconsistent. He also walks through how to work backward from your income goal so your pricing is tied to a real plan instead of a guess. This episode is especially helpful for freelancers, consultants, therapists, creatives, advisors, and other solo business owners who want a cleaner financial foundation. In This Episode: ✅ Why mixing personal and business finances creates unnecessary confusion ✅ How to build a tax system before a large tax bill catches you off guard ✅ Why self-employed individuals need to replace employee benefits intentionally ✅ How business and personal cash reserves serve different purposes ✅ Why your target income should influence your pricing and workload ✅ How to create more financial clarity as your business grows Self-employment is not just about earning more revenue. It is about creating systems that help you understand what is working, what needs attention, and how your business can support your personal life without creating unnecessary financial stress. A strong setup does not have to be complicated. But the earlier you create separation, tax discipline, benefit planning, cash reserves, and pricing clarity, the easier it becomes to make better decisions as the business grows. #SelfEmployed #SmallBusinessFinance #FinancialPlanning #SoloBusinessOwner #EntrepreneurFinance #FreelancerFinance #ThinkingSolo — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    15 min

  2. May 29

    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 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 in your 30s, and 40s, but you don't see the impact of the decisions until your 50s and 60s. By then, it's more and more difficult to recover. Ryan shares his thoughts on why this persists and ways to protect against the mindset, so you don't find yourself overly reliant on the business. At the end of the episode, Ryan also delves into his latest movie review: Indiana Jones and the Raiders of the Lost Ark, the 1981 classic from Steven Spielberg.Subscribe and stick around, and in the meantime… keep grinding!Connect with Ryan Derousseau, CFP®, EAEmail: Ryan@unitedfpg.comLinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    16 min
  3. From CPA to LinkedIn Strategist Featuring Wendy Shore

    May 13

    From 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 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 and her health. What followed wasn’t a clean pivot, but an identity shift… one that eventually led her back to consulting, and ultimately into helping small business owners grow through LinkedIn and strategic positioning. This conversation digs into the real challenges of solopreneurship: finding your niche, learning how to sell yourself, navigating income volatility, and building a business rooted in experience. Ryan and Wendy discuss: • Wendy’s journey from CPA to restaurant owner to business growth advisor • Why leaving the restaurant business created an identity shift • The hidden lessons that come from business setbacks • Why niching down is one of the hardest but most important parts of solo business growth • How to get comfortable charging for your experience • Why people pay for access, perspective, and proximity, not just information • How LinkedIn comments can help you build visibility and relationships • Why solopreneurs should not try to build completely alone • Wendy’s new book, Common Currency • Practical advice for anyone going out on their own for the first time This episode is a direct look at what it actually takes to evolve as a solopreneur… not just in strategy, but in identity, confidence, and how you position your value. #Solopreneur #LinkedInStrategy #Entrepreneurship #SmallBusinessGrowth #BusinessGrowth #CareerPivot #ThinkingSolo #WendyShore #RyanDeRusso — Connect with Wendy Shore Website: https://wendyshore.co — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    35 min
  4. Merging Therapy and Accounting with Jennie Schottmiller

    Apr 23

    Merging 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 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 weakness This 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-us Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    42 min

  5. Apr 16

    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, 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: Ryan@unitedfpg.comLinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    13 min
  6. Betting on Yourself — Brie Chrisman on Building Boss Co. and Leading with Intention

    Apr 9

    Betting 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 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 weakness This 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/about Connect with Ryan Derousseau, CFP: Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    32 min

  7. Mar 26

    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 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: Ryan@unitedfpg.comLinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    17 min
  8. Gregory Milano on Strategy, Resilience, and Long-Term Thinking

    Mar 17

    Gregory 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 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 change This 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 Milano LinkedIn: https://www.linkedin.com/in/greg-milano/ Website: https://fortuna-advisors.com/ Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau Website: https://thinkingcapfinancial.com

    31 min
See All (13)

About

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

Information

  • Creator
    Ryan Derousseau, CFP®, EA
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © Ryan Derousseau, CFP®, EA
  • Show Website
    Thinking Solo