Thinking Solo

Welcome to another episode of Thinking Solo with Ryan Derousseau, CFP®, EA, where we explore the best financial strategies for high earning entrepreneurs. Today we dive into the most powerful retirement vehicles for a one person million dollar business to reduce taxes and maximize long term savings. Discover how combining specific accounts can significantly boost your net worth while providing inc...

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 Derous...

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...

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 you...

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 c...

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...

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 Ins...

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...

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 revi...

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 componen...

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...

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 o...

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...

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 s...

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 break...

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...

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 sy...

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 i...

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...

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 sh...

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 c...

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...

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 man...

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...

Welcome to Thinking Solo — hosted by Ryan Derousseau, CFP®, EA.In today's episode, we take a moment to talk about taxes. In the midst of the 2026 tax season, it's easy to look on last year and think there's nothing that can be done or nothing to look out for. But in reality, there are regular, common mistakes that solopreneurs and small business owners make on their taxes. It's imp...