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From CPA to Business Owner: Lessons You Only Learn the Hard Way
01/05/2026
From CPA to Business Owner: Lessons You Only Learn the Hard Way
From CPA to Business Owner: Lessons You Only Learn the Hard Way | The Financial Operator Podcast | Episode 74 What does it really take to build a sustainable business—and stay sane while doing it? In this episode of The Financial Operator: Cash In, Chaos Out, Jen sits down with Samantha Besnoff, CPA and founder of Your Financial Maven, for a candid, practical conversation every business owner needs to hear. With over 30 years in accounting and more than a decade running her own firm, Samantha shares the real lessons that don’t show up in spreadsheets, how long success actually takes, why boundaries matter more than hustle, and how understanding your numbers protects both your business and your sanity. In this episode, we cover: What it really looks like to leave a stable job and start your own firm Why most small businesses struggle in the first 2–3 years Setting boundaries with clients (and why it’s not optional) Pricing, retainers, and getting paid before the work is done When—and how—to fire clients without blowing up your cash flow What business owners need to know heading into tax season The biggest bookkeeping and tax mistakes Samantha sees over and over This conversation is a must-watch for: ✔ Small business owners ✔ Service providers & consultants ✔ Anyone tired of guessing with their finances If you want fewer surprises, better cash flow, and a business that actually supports your life, this episode delivers. ⏱️ Timestamps 00:00 Introduction & Guest Welcome 02:49 Samantha’s Journey Into Entrepreneurship 07:15 Why the First 2–3 Years Are the Hardest 10:07 Getting Paid, Pricing Right, and Setting Boundaries 15:04 When (and How) to Fire Clients 20:02 Major Tax Changes Business Owners Should Know 26:50 Filing Deadlines, Extensions, and Tax Season Reality 34:45 What Business Owners Actually Need for Their Taxes 41:15 Who Samantha Works With & How to Get Started 44:37 Final Thoughts & How to Connect To connect with Samantha M. Besnoff, CPA & Your Financial Maven: 🌐 Website: 📌 Don’t forget to subscribe for the latest podcast episodes and insights from @mkbcfo Do you have your own financial or business growth questions for MKB? Visit: 🌎 Website: 📸 Instagram: 📘 Facebook: 💼 LinkedIn: #SmallBusinessOwner #Entrepreneurship #FinancialClarity #TaxTips #CashFlowManagement #BusinessFinance #WomenInBusiness #CPAAdvice #FractionalCFO #TheFinancialOperator
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