Adam Sher – Why Your Tax Accountant Is Killing Growth
In this week’s episode, host James Kennedy is joined by Adam Sher, a seasoned CFO who has worked with some of the most exciting growth-stage companies in the startup ecosystem.
Adam shares what it’s like to parachute into high-growth environments as a fractional CFO, where finance meets chaos, and strategy meets reality. With a background that spans e-commerce, SaaS, and AI, Adam brings a refreshingly honest take on how CFOs can balance operational excellence with founder vision – especially when the numbers tell a different story.
From managing investor expectations to rebuilding financial infrastructure after layoffs, Adam’s war stories offer valuable insights for CFOs, founders, and operators alike.
Tiffany Vogel – The 3-Year Plan to Build and SELL a CFO Empire!
This week James sits down with Tiffany Vogel, founder of Insight CFO Services, to explore what it means to build a scalable, values-driven fractional CFO firm from the ground up. Tiffany shares her unconventional decision to take on debt and build a team from day one – defying the typical solo CFO path.
They dive into her background in healthcare analytics, her real estate investing success, and how those experiences shaped her approach to financial leadership. Tiffany also talks candidly about setting boundaries, managing burnout, and keeping her mission at the center of everything she builds.
Stick around to the end to hear how she’s planning retreats for founder transformation – and why every CFO should be thinking about their exit, too.
Kyle Smith – The Balance Sheet Red Flag That Could Bankrupt You
This week James sits down with Kyle Smith, founder of Strata Advisory and seasoned fractional CFO, to explore what it takes to help fast-growing service businesses thrive. With a background in management consulting and a knack for navigating complex financial waters, Kyle breaks down the strategies he uses to guide his clients toward clarity, confidence, and profitable decision-making.
They discuss building financial infrastructure from scratch, the difference between being busy and being successful, and why most business owners need to stop trying to do it all.
Stick around to the end to hear Kyle’s take on how fractional CFOs can make themselves indispensable to the CEOs they serve.
Jason Andrews – One Cold Email Changed His Career Forever
This week James sits down with Jason Andrews from FloQast to unpack the unexpected journey from accounting to marketing – and the lessons learned scaling a finance function through hypergrowth. Jason opens up about his time at Twilio, where he helped guide the company from $650M to over $4B in revenue, led a massive ERP migration, and managed a global team across five time zones. He also shares why he made the surprising leap into marketing at FloQast and how his accounting DNA continues to drive his impact.
Whether you’re navigating messy month-end closes, leading through explosive growth, or considering a career pivot, this episode is full of wisdom on process, people, and perspective.
Garon Goodspeed – QuickBooks to NetSuite: The REAL Nightmare
This week James sits down with Garon Goodspeed, co-founder of Treaty Oak Financial Services, to explore three essential areas every finance leader should understand. First up: what it’s like to prepare for an IPO – and then walk away just before the bell rings. Next, Garon shares battle-tested advice on designing sales compensation plans that motivate teams without blowing the budget. Finally, Garon reflects on launching his own fractional CFO practice and reveals what fueled its rapid growth in just a few months.
Whether you’re scaling toward a liquidity event, managing a fast-moving sales team, or thinking about starting your own CFO consultancy, this episode is packed with lessons from the trenches.
Hillel Steiner – This Israeli CFO Secret Could Double Your Profits
This week James sits down with Hillel Steiner, founder of ProfitUp Financials and a fractional CFO based in Israel, to discuss the surprising advantages of working with international finance talent. Together, they dive into the differences between U.S. and Israeli business cultures, what founders often get wrong about funding, and how having a strong financial strategy can be the difference between staying stuck and scaling up.
Hillel also walks through a real-life case study of a BI company stuck in a high-revenue, low-profit cycle – and how he helped them transform by refocusing their service model and aligning their team more efficiently.
Stick around to the end for a massive bonus offer from Hillel that’s perfect for growing service-based companies.
Patrick Arnold – 7M Sales, Zero Profit: The Fix
This week James sits down with Patrick Arnold, Director of Client Advisory Services at Elliott Davis, to explore the power of Client Advisory Services (CAS) and its game-changing impact on business profitability. Patrick shares an engaging case study of how he helped a golf cart business in South Carolina go from stagnant growth to seven-figure annual distributions – all by optimizing inventory, restructuring financial processes, and leveraging technology for smarter decision-making.
They also dive into the role of CAS in modern accounting, the evolution of public accounting firms to include more strategic, forward-thinking advisory, and how business owners can unlock hidden cash flow by better managing working capital.
Chris May – Fake CFOs Exposed: How to Spot the Difference
This week James sits down with Chris May, founder and CEO of Quadrant Advisory, to explore what separates real CFO strategy from everyday accounting. From turning around a $50M political consulting firm to navigating tricky incumbent finance teams, Chris shares practical advice for business leaders and fractional CFOs alike.
Together, they unpack key finance tools like sensitivity analysis, working capital management, and how to tell whether your books are just “done” – or actually useful. Chris also walks us through his own acquisition of a bookkeeping SaaS and what it taught him about keeping services laser-focused.
Aaron Mills – The Transparency Secret to 3X Growth!
This week James sits down with Aaron Mills, founder and CEO of Daaxit, to discuss the realities of running a profitable construction business – and how the right financial strategy can be the difference between barely surviving and scaling with confidence.
Aaron shares his journey from 20 years in the construction industry to founding his own successful fractional CFO firm. Together, they dig into smart pricing strategies, incentivizing field teams, and how he helped one business owner go from burnout to working just one day a week.
Stick around to the end to hear Aaron’s surprisingly controversial business hero pick – and why it inspires him to push further every day.