Ep42 Chris Thomajan: Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners

Ep42 Chris Thomajan: Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners

Chris Thomajan, a CFO with 35 years of startup experience, discusses his career path from English major to finance leader across 100+ companies, primarily in Boston's biotech ecosystem. He shares frameworks for evaluating CEOs, navigating venture capital cycles, and managing founder transitions, emphasizing that betting on the right team matters more than the product itself.

Ep 39—Neal Miller-Decades of Financial Strategy Across 70 Companies and Still Going

Ep 39—Neal Miller-Decades of Financial Strategy Across 70 Companies and Still Going

Neil Miller, a partner emeritus at Tech CXO with 19 years at the firm, shares his journey from public accounting through CFO roles at multiple public companies to fractional executive work. He discusses his involvement with 70+ companies including Cloud Sherpas and Boomtown, offering insights on fundraising challenges, the fractional executive model's value during economic uncertainty, and how AI is compressing business cycles while changing capital requirements.

Ep36—Ted Stone: Decades of Financial Strategy — Still in the Game and Giving Back

Ep36—Ted Stone: Decades of Financial Strategy — Still in the Game and Giving Back

Ted Stone, a 72-year-old career CFO, discusses his transition to fractional CFO work serving multiple clients across diverse industries. He shares detailed stories from three major private equity deals—Velocity Express (a last-mile delivery rollup), an office telephone company spin-out, and Solucent (a healthcare data integration)—while exploring current trends including the silver tsunami of retiring business owners, ESOP structures, and the value of executive peer networks like Executive Forum.

Ep28 Michael Weinstein—Tariffs and Economic Uncertainty - How We Got Here & What's Next

Ep28 Michael Weinstein—Tariffs and Economic Uncertainty - How We Got Here & What's Next

Michael Weinstein, a fractional CFO with extensive Wall Street experience, discusses the current economic uncertainty driven by tariff policies, Federal Reserve decisions, and structural market challenges. He explains how tariffs function as a massive tax increase, analyzes the compounding effects of policy uncertainty on corporate investment, and examines the clogged venture capital pipeline. Weinstein draws historical parallels to past economic cycles while noting this situation is unique—a self-inflicted late-cycle shock with no clear playbook.

Want to go deeper?

Work With Me