Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Chris Thomajan, a CFO with 35 years of experience across 100+ startups, discusses his career path from English major to finance leader in Boston's biotech ecosystem. He shares frameworks for evaluating founding teams, navigating venture capital cycles, and preparing companies for IPO, emphasizing that betting on the right 'jockey' matters more than the business idea itself.

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Beyond Resumes: The Case for Talent-First, Human-Centered Hiring | Teja Yenamandra, Ep 29

Teja Yenamandra, founder of Gun.io, discusses building a talent-first freelance marketplace that connects senior software engineers with companies based on merit rather than price. He shares insights on remote work culture, AI's impact on software development, the importance of relationship-focused venture capital partnerships, and how the developer job market is shifting toward backend and AI implementation work.

Grit Becomes Growth: The Path from Pain to Transformation | Bart Foster, Ep 09

Grit Becomes Growth: The Path from Pain to Transformation | Bart Foster, Ep 09

Bart Foster shares his journey from corporate executive to founder of SoloHealth, a health screening kiosk company that scaled to 4,000 Walmart locations before he was forced out by his board. He discusses the emotional trauma of losing his company, his intentional relocation to Boulder, and founding Business Outside—a consulting practice that uses nature-based experiences to help leaders build authentic connections and live more intentionally.

From Rowing to Venture Capital: Lessons in Teamwork and Growth | Mark Flickinger, Ep 04

From Rowing to Venture Capital: Lessons in Teamwork and Growth | Mark Flickinger, Ep 04

Mark Flickinger, partner at BIP Ventures, discusses his journey from mechanical engineering and competitive rowing to venture capital. He explains BIP's platform-heavy approach to supporting portfolio companies, the firm's focus on high-net-worth investors, and strategies for navigating the current venture market. Flickinger emphasizes the importance of board governance, team-based competitive experience, and building sustainable businesses during economic downturns.

Want to go deeper?

Work With Me