Thinking Solo

Ryan Derousseau, CFP®, EA
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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. 1d ago

    Why Your Accountant Isn’t Saving You Money (And What Tax Planning Actually Looks Like)

    Is your accountant actually saving you money, or are they just filing your tax returns? As your business grows, tax preparation alone isn't enough to help you keep more of your revenue. Many entrepreneurs rely on traditional tax preparation, only to face unexpectedly large tax bills without a clear strategy for tax savings or wealth building. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, breaks down proactive tax planning vs. tax filing. Discover how proactive tax strategies, business entity structuring (like S Corp elections), and retirement plan options can lower your tax liability and support your long-term financial goals. In this episode, you’ll learn: • Tax Filing vs. Tax Planning: Why tax preparation focuses on past financial activity while proactive tax planning prepares you for future tax savings. • Year-Round Strategy: Why waiting until tax season limits your tax deduction options and proactive strategies. • Business Structure & Tax Classification: How your entity setup impacts self-employment tax and overall tax liability. • Small Business Retirement Plans: When to leverage a Solo 401(k), Traditional 401(k), or Cash Balance Plan for high earners. • S Corp Election Considerations: Why an S Corporation isn't a one-size-fits-all strategy for every business owner. • Tax Deductions & Write-Offs: How health insurance, home office deductions, and business write-offs fit into your plan. • Custom Tax Strategies: Matching strategies to your revenue, business structure, and employee count. • Financial Advisory Alignment: How aligning your CPA and financial planner connects business success with wealth management. • Proactive Execution: Implementing year-round tax management before deadline pressures lock in options. Your CPA and financial advisor play complementary roles in your overall financial strategy. By coordinating tax preparation with year-round planning, business owners can evaluate potential strategies early and make informed choices to support long-term wealth. Ryan also reviews Masters of the Universe and draws a lesson for entrepreneurs: building a business around a financial target alone can leave it without a clear purpose. A strong business needs more than a revenue goal. It needs a meaningful service, product, or mission to guide its growth. — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/ Subscribe to Thinking Solo for more insights on tax planning strategies, wealth management, and financial advice for small business owners and entrepreneurs!

    Why Your Accountant Isn’t Saving You Money (And What Tax Planning Actually Looks Like)

  2. Oct 22

    You Made $1 Million Last Year. So Why Is Your Savings Account Empty?

    Why does high business revenue not always mean personal wealth? Many entrepreneurs generate $1M+ in revenue but have empty personal savings accounts or underfunded retirement plans. Without a structured system to move business profit into personal wealth, business success remains fragile. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, breaks down why successful business owners struggle with personal savings and financial planning. From separating business and personal finances to tax planning and setting a predictable salary, learn actionable strategies for long-term wealth building outside your business. In this episode, you’ll learn: • Why keeping business and personal finances intertwined can prevent you from building wealth outside your company. • How creating a consistent salary can establish better budgeting and saving habits. • Why business structure and tax planning can affect your personal tax bill and available deductions. • The difference between generating $1 million in revenue and actually earning a substantial profit. • How constantly reinvesting in your business can leave your personal financial future underfunded. • Why building retirement savings and investments outside your business can help diversify your net worth. • How a business downturn could affect your financial security if too much of your wealth depends on one source. • Why a trusted financial professional can help connect business decisions with your long-term personal financial goals. • How entrepreneurs can evaluate business performance more clearly by understanding where the money goes. A successful business should support more than its next stage of growth. Establishing a reliable process for paying yourself, saving consistently, and investing outside the business can help you build financial resilience while continuing to pursue your entrepreneurial goals. #ThinkingSolo #Entrepreneurship #SmallBusiness #FinancialPlanning #WealthBuilding #BusinessOwner #PersonalFinance #TaxPlanning #CFP #FinancialFreedom — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

    You Made $1 Million Last Year. So Why Is Your Savings Account Empty?

  3. Oct 15

    When (and How) to Hire Your First Employee

    Taking the leap from solo operator to business owner is a major milestone. In this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA breaks down the framework for evaluating when and how to hire your first employee. Explore essential financial considerations, risk management strategies, and operational steps to help scale your business. In This Episode: · Key indicators for knowing when your solo practice is ready to expand · Why employment agreements and proper business structures help manage risk · Critical differences between full-time staff and independent contractors (W-2 vs. 1099) · How setting clear expectations helps support a smooth onboarding process · Financial timelines to consider when budgeting for team expansion · Themes of focus and discipline from Martin Scorsese’s Cape Fear applied to entrepreneurship Subscribe to the channel for educational insights on growing and managing your practice. For more financial information and resources, visit our official website. #ThinkingSolo #FirstEmployee #HiringTips #SoloEntrepreneur #BusinessGrowth #TeamBuilding — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/  Website: https://thinkingcapfinancial.com/

    When (and How) to Hire Your First Employee

  4. Oct 8

    Backdoor Roth IRA

    In this episode of Thinking Solo, financial planner Ryan Derousseau explores the backdoor Roth IRA strategy for high earners. Learn how to navigate tax planning, avoid common IRA traps, and optimize retirement savings for self-employed professionals. Key Topics Covered: • Why high earners utilize the backdoor Roth IRA to build tax-free wealth • Step-by-step mechanics of executing a backdoor Roth conversion • Understanding the IRS pro-rata rule and how to avoid tax pitfalls • Rolling traditional IRA funds into employer plans to prevent unintended taxation • Benefits of opening a solo 401(k) for self-employed individuals and business owners • Navigating regulatory developments and potential changes to Roth IRA contribution rules • Business strategy lessons derived from entertainment industry trends • Long-term growth and value sustainability strategies for solo entrepreneurs Subscribe to the channel for insights on wealth management, tax optimization, and enterprise growth. For personalized guidance on wealth management strategies, visit the website linked below. #BackdoorRoth #Solo401k #TaxStrategy #FinancialPlanning #WealthManagement #RetirementPlanning #SelfEmployed — Connect with Ryan Derousseau, CFP Email: Ryan@unitedfpg.com LinkedIn: https://www.linkedin.com/in/ryanderousseau/   Website: https://thinkingcapfinancial.com/

    Backdoor Roth IRA

  5. Oct 1

    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

  6. 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

  7. 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

  8. 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
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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
    28
  • Rating
    Explicit
  • Copyright
    © Ryan Derousseau, CFP®, EA
  • Show Website
    Thinking Solo