Thinking Solo

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

Thinking Solo is a business podcast hosted by Ryan Derousseau, CFP®, EA, with 19 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Ryan Derousseau, CFP®, EA hosts Thinking Solo, a business show with 19 episodes published.

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  Thinking Solo

  TS 23 - Understanding The Power of the Health Savings Account

  Aug 20, 202616 min

  Is your Health Savings Account (HSA) doing enough for your financial future? Many people view the HSA merely as a way to pay for current medical expenses, but it is actually one of the most powerful tax-advantaged tools available for long-term wealth building. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, breaks down why the HSA deserves serious consideration as a core component of your healthcare and financial planning strategy. We explore the "triple tax advantage" of HSAs, how to invest funds for long-term growth, and why this account is a hidden gem for retirement planning. In this episode, you’ll learn: • What a Health Savings Account (HSA) is and how it functions. • The "triple tax advantage" that benefits you today and in the future. • Why HSA funds should be invested for long-term growth. • How an HSA can serve as a powerful retirement planning tool. • Best practices for tracking qualified medical expenses to create future flexibility. • How to evaluate whether a high-deductible health plan aligns with your financial strategy. An HSA is not automatically the right choice for everyone. This episode helps you compare health insurance plans and understand how an HSA fits into your broader financial and tax landscape before you make a decision. #ThinkingSolo #HSA #HealthSavingsAccount #TaxPlanning #RetirementStrategy #SoloEntrepreneur #FinancialPlanning #WealthBuilding #SelfEmployed #SmallBusinessFinance — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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  Thinking Solo

  What You Should (and Shouldn’t) Write Off for Your Business

  Aug 13, 202616 min

  Are you maximizing your small business tax deductions or leaving money on the table? In this episode, we break down how to navigate IRS business expenses so you can stay compliant and keep more of what you earn. Ryan Derousseau, CFP®, EA, clarifies the often-confusing world of "write-offs." We dive into the specific rules for solo entrepreneurs, helping you distinguish between legitimate deductions and common tax mistakes that could trigger an audit. What you'll learn in this video: • The IRS definition of "ordinary and necessary" business expenses • How to correctly claim the home office deduction and travel expenses • The truth about business meals and entertainment write-offs in 2026 • Critical record-keeping habits to protect your small business from audits • Why tax planning is more effective than just chasing deductions Stop relying on social media for tax advice. This guide for 1099 contractors and freelancers provides a strategic framework for reporting income accurately while utilizing legal business tax breaks to support your long-term financial health. Whether you’re a new business owner or have been self-employed for years, this episode helps clarify what you can (and can’t) write off so you can avoid mistakes and feel more confident at tax time. — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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  Thinking Solo

  Building an Estate Plan for Your Business

  Aug 11, 202615 min

  In this episode of Thinking Solo , host Ryan Derousseau, CFP®, EA, discusses why entrepreneurs may need to look beyond their companies for long-term financial security. While building a business is a major milestone, creating a personal financial strategy that exists independently can help mitigate risk and protect your family's future. Learn how intentional planning outside of your business operations can provide the flexibility needed for life's many transitions. In this episode: • Why relying solely on your business for retirement may create significant financial risks • How separating business success from personal wealth can improve your long-term security • Understanding how retirement planning strategies differ for the self-employed and entrepreneurs • Why protecting your income and family should be a priority in every strategy • How diversifying investments outside your company could lead to more stable outcomes • Common financial planning mistakes that business owners might consider avoiding for growth • Ways a comprehensive plan provides essential flexibility during major life and business transitions • How intentional planning helps you pursue the freedom you initially built your business for Building a successful business is a significant achievement, but creating a personal legacy requires careful, intentional strategy. Speak with a qualified financial professional to determine which planning options may be appropriate for your situation. #EstatePlanning #BusinessOwner #FinancialPlanning #Entrepreneurship #WealthManagement #ThinkingSolo #RetirementPlanning — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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  Thinking Solo

  The Private Practice Checklist

  Jul 30, 202616 min

  Starting a private practice comes with unique financial responsibilities. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, walks through a practical financial checklist that can help business owners build a solid foundation. While this discussion is particularly relevant for therapists, psychologists, physicians, and other healthcare professionals, the principles can be applied to entrepreneurs across various service-based industries. In this episode, you'll learn: • Why taking action while planning can be critical for your business launch • Considerations for choosing the right business structure for your profession • The importance of separating personal and business finances from the start • Bookkeeping tools that may help your business stay organized • Approaches to preparing for self-employment taxes • Replacing benefits when transitioning from a traditional job • How to calculate the revenue your business may need to generate • Why pricing strategies should account for taxes, insurance, and overhead Whether you are launching a private practice or a new service-based business, this episode offers a roadmap to help you navigate your early entrepreneurial journey and focus on building a business that supports your long-term goals. #PrivatePractice #FinancialPlanning #SmallBusinessTips #Entrepreneurship #ThinkingSolo #FinancialChecklist — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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  Thinking Solo

  Fiduciary Advisor

  Jul 23, 202613 min

  In this episode of Thinking Solo, I’m cutting through the industry jargon that confuses so many business owners. We’re breaking down the critical differences between fiduciary, fee-only, and fee-based financial advisors, and why choosing the wrong one can cost you more than just fees. It can cost you your business growth. Financial planning isn't just about investments; it's about making sure your advisor's compensation model aligns with your family’s and business's goals, not theirs. Plus, I share an unexpected business lesson on innovation and avoiding complacency inspired by Toy Story 5. In this episode, you'll learn: • The Fiduciary Standard: What it actually means for your money. • Fee-Only vs. Fee-Based: Spotting the hidden conflicts of interest. • The "Advisor Interview": Questions every business owner should ask before hiring. • Holistic Growth: Why your financial plan must go beyond just insurance and portfolios. • Innovation Lessons: How to avoid the "Toy Story 5" trap of stagnation in your business. Whether you're hiring your first advisor or questioning your current relationship, this episode provides the practical framework you need to make an informed, confident decision. #FinancialAdvisor #Fiduciary #FinancialPlanning #FeeOnlyAdvisor #BusinessOwnerTips #ThinkingSoloPodcast #ToyStory5 #WealthManagement #SmallBusinessFinance — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

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