Thinking Solo

Ryan Derousseau, CFP®, EA
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  • Entrepreneurship
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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. Managing Variable Income as a Business Owner

    5d ago

    Managing 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 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 breaks down practical ways business owners can manage uneven income, create a financial buffer, save for retirement, and avoid the lifestyle creep that can quietly eat away at long-term wealth. He also connects the entrepreneurial mindset to Close Encounters of the Third Kind and explores the difference between healthy ambition and building a business at all costs. In this episode ✅ Why variable income creates fear for solo entrepreneurs and business owners ✅ How to decide what to pay yourself from the business ✅ Why your personal spending directly impacts business profitability ✅ The importance of building a business buffer account ✅ How much cash to keep inside the business for slower months ✅ Why SEP IRAs and Solo 401(k)s can help self-employed professionals build long-term wealth ✅ How lifestyle creep can prevent higher income from becoming higher net worth ✅ Why business growth should also mean increasing your savings rate ✅ What Close Encounters of the Third Kind reveals about obsession, entrepreneurship, and building a business for the right reasons Building wealth with variable income is not about reacting to every strong or weak month. It is about creating systems that help you stay steady, protect yourself during downturns, and consistently move money toward your long-term goals. For solo entrepreneurs, the goal is not just to build a bigger business. It is to build a better life. That means saving intentionally, managing cash flow wisely, and making sure your work supports your family and future instead of becoming an unhealthy obsession. Want help making smarter financial decisions as a solo entrepreneur? Visit thinkingcapfinancial.com, subscribe to the Thinking Solo YouTube channel, and connect with Ryan Derousseau on LinkedIn. #SoloEntrepreneur #VariableIncome #SelfEmployed #BusinessOwnerFinance #WealthBuilding #FinancialPlanning #Solo401k #SEPIRA #Entrepreneurship #ThinkingSolo — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

    13 min
  2. Estimating Taxes

    Jun 18

    Estimating 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 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 adult. Ryan walks through why self-employed professionals need to start with expected profit, account for self-employment tax, set aside money consistently, review their numbers quarterly, and actually pay estimated taxes on time. Because nothing crushes momentum faster than thinking your business is doing great, only to get hit with a tax bill you were not prepared for. What You’ll Learn ✅ Why revenue can give business owners a false sense of success ✅ Why profit matters more than top-line sales ✅ How self-employment tax can surprise new business owners ✅ Why setting aside a consistent percentage for taxes can help avoid panic later ✅ The importance of quarterly reviews and updated estimates ✅ Why actually paying estimated taxes may give you a clearer picture of business cash flow ✅ How penalties and interest can make an already painful tax bill worse If you are self-employed, taxes need to be built into your business process from the beginning. The goal is not to guess perfectly. The goal is to avoid surprises, stay consistent, and understand what your business is actually producing after expenses and taxes. Also in This Episode Ryan wraps up with a review of the 1984 cult classic Repo Man, starring Emilio Estevez and Harry Dean Stanton. It is strange, scrappy, funny, and weirdly fitting for anyone who appreciates the chaos of trying to make your own way. — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    12 min
  3. Setting Up Your Business

    Jun 16

    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

  4. 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
  5. 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
  6. 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

  7. 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
  8. 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
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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
    15
  • Rating
    Clean
  • Copyright
    © Ryan Derousseau, CFP®, EA
  • Show Website
    Thinking Solo