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. 3d ago

    Self-Employed Mortgages: How to Actually Qualify

    Getting a mortgage when you are self-employed can feel like an uphill battle. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, breaks down how self-employed professionals, business owners, and freelancers can accurately demonstrate their financial strength to lenders and qualify for a home loan. In this episode: • How lenders evaluate two years of self-employed income • How annual income averaging affects your qualifying home loan amount • The impact of co-signing or applying with a W-2 spouse • Balancing tax write-offs with net income requirements for mortgage approval • How depreciation and business add-backs increase your total qualifying income • Strategies to lower your debt-to-income (DTI) ratio before applying • Working with mortgage brokers who understand self-employment income • The entrepreneur mindset and navigating daily business growth If you found this video helpful, please subscribe to Thinking Solo for more financial planning tips for self-employed professionals! #SelfEmployedMortgage #ThinkingSolo #RyanDerousseau #MortgageTips #Entrepreneurship #FinancialPlanning #BusinessOwner #HomeBuying — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com  LinkedIn: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

    Self-Employed Mortgages: How to Actually Qualify

  2. Sep 24

    Health Insurance for Self-Employed Professionals

    In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, explores health insurance options for self-employed professionals, freelancers, and small business owners. Managing healthcare costs and understanding tax strategies can significantly impact your business bottom line and household budget. Learn about the primary coverage options including: spousal employer plans, the ACA Health Insurance Marketplace, and association or trade group plans. Ryan also discusses strategies for managing adjusted gross income (AGI), utilizing Health Savings Accounts (HSAs), and navigating tax deductions based on your business structure (Sole Proprietorship, LLC, or S Corp). In this episode, you’ll learn: • Primary health insurance options for self-employed professionals • Evaluating spousal employer-sponsored health coverage • How the ACA Marketplace works for small business owners • The impact of income levels and AGI on health insurance subsidies • Association and trade group plans as coverage alternatives • Health insurance tax deductions for Sole Proprietors, LLCs, and S Corps • Utilizing HSAs and retirement contributions to manage healthcare costs • Aligning healthcare planning with cash flow and tax strategy Ryan emphasizes that self-employed professionals cannot control changes to healthcare rules or subsidy levels, but they can plan around those rules. Understanding how income, business expenses, retirement contributions, and health insurance interact can help business owners make more informed decisions and potentially reduce the overall cost of healthcare. Whether you are launching a new venture or growing an established business, this episode provides educational insights to help you make informed decisions about your health insurance and financial plan. #SelfEmployed #HealthInsurance #FinancialPlanning #TaxStrategy #ACAMarketplace #HSA #SmallBusiness — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    Health Insurance for Self-Employed Professionals

  3. Sep 3

    When and Why To Use Roth Conversions

    In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, explores the fundamentals of Roth conversions and how they may serve as a strategic tool for retirement planning. Understanding when and why to execute a Roth conversion can help self-employed individuals and business owners manage future tax liabilities and create long-term tax flexibility. By carefully evaluating current tax rates against potential future tax brackets, individuals can make informed decisions tailored to their unique financial goals. In this episode: •  Understanding how Roth conversions function and how they impact your overall tax strategy •  Comparing traditional retirement accounts with Roth accounts for long-term retirement and tax planning •  Evaluating whether paying taxes today for tax-free future withdrawals fits your situation •  Exploring how lower income years may create opportunities for strategic Roth conversions •  Managing future required minimum distributions through thoughtful and targeted Roth conversion planning •  Avoiding potential tax burdens by converting the right amount in a single year •  Why individual circumstances matter when creating a balanced and effective retirement strategy Developing an effective Roth conversion strategy depends on your specific financial timeline, income level, and retirement goals. Consulting with a qualified financial advisor or tax professional can help you evaluate your options safely and effectively. #RothConversion #RetirementPlanning #TaxStrategy #FinancialAdvisor #ThinkingSolo #TaxPlanning — Connect with Ryan Derousseau, CFP®, EA Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    When and Why To Use Roth Conversions

  4. Aug 27

    Solo 401k vs SEP IRA

    Welcome to Thinking Solo with host Ryan Derousseau, CFP®, EA, where we talk about ways to succeed in business and life. In this episode, we break down the key similarities and differences between the Solo 401k and the SEP IRA to help self-employed entrepreneurs choose the right retirement plan. We also discuss how business structure and employee rules impact your decision, followed by a movie review of Pig. In this episode: 🔸 Learn how both options allow solo business owners to build long term retirement wealth 🔸 Discover how the flexible contribution limits work for employee and employer portions 🔸 Understand why high earners often benefit more from choosing a Solo 401k 🔸 Explore critical employee rules that could create unexpected tax penalties for SEP IRAs 🔸 Compare startup deadlines and documentation needs for setting up your retirement account 🔸 Learn how your S Corp structure impacts your maximum potential retirement contributions 🔸 See why a Solo 401k often encourages consistent ongoing retirement saving habits 🔸 Gain key lessons on entrepreneurial passion from a review of the film Pig Be sure to subscribe to the channel and share this episode with other solo entrepreneurs looking to optimize their retirement strategy. For more insights on building business wealth and reaching your goals, visit thinkingcapfinancial.com today. Thanks for tuning in, and in the meantime… keep grinding. #ThinkingSolo #Solo401k #SEPIRA #RetirementPlanning #Solopreneur #SmallBusiness — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/

    Solo 401k vs SEP IRA

  5. Aug 20

    Understanding The Power of the Health Savings Account

    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/

    Understanding The Power of the Health Savings Account

  6. Aug 13

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

    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/

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

  7. Aug 11

    Building an Estate Plan for Your Business

    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/

    Building an Estate Plan for Your Business

  8. Jul 30

    The Private Practice Checklist

    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/

    The Private Practice Checklist
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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
    2026
  • Episodes
    24
  • Rating
    Clean
  • Copyright
    © Ryan Derousseau, CFP®, EA
  • Show Website
    Thinking Solo