The practice of repeatedly founding and scaling multiple ventures over time, applying lessons learned from previous startups to new opportunities.
19 episodes
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.
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.
Lewis Gump, a fractional CEO/COO and author of 'Gorilla Marketing Tactic,' discusses his career building mobile and digital businesses at CNN and The Weather Channel, the critical differences between entrepreneurs and intrapreneurs, and how founders can successfully transition into larger organizations post-acquisition. He emphasizes that innovation requires leadership commitment, cultural fit, and the ability to build bridges across diverse teams.
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.
Virginie Glaenzer, a fractional CMO and author, shares her journey from Paris to Silicon Valley in 1998 with four suitcases and no English, building tech companies through the dot-com era. She discusses AI's transformative impact on business, the shift from scarcity-based to abundance-based thinking, and why future-proof brands must build communities into their DNA rather than treating them as marketing tactics.
Joe Gruca shares his journey from corporate VP of Sales at Computer Associates to co-founding Higher IQ, an AI-powered interview automation platform, after being laid off in 2008. He discusses pivoting the business model, raising venture capital, successfully exiting, and now helping early-stage tech CEOs as a fractional revenue leader at Tech CXO. The conversation covers sales methodology evolution, startup lessons, and navigating economic uncertainty.
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.
Jeff Haynie, serial entrepreneur and founder of Appcelerator (Titanium), discusses his journey from pioneering JavaScript mobile development in 2006 to launching Agentuity, an AI agent cloud platform. He shares insights on Silicon Valley's unique ecosystem, the evolution of software development, and his belief that AI agents will fundamentally transform cloud infrastructure from human-centric to agent-optimized systems.
Adam Lehde, co-founder of Happen Technologies, discusses building a hybrid software development company that partners US-based strategy with Ukrainian technical talent. He shares his journey from mobile developer to entrepreneur, the cultural strengths of Ukrainian developers, and his philosophy of building a family-first company culture while maintaining high performance through direct communication and ownership mentality.
Ghazenfer Mansoor, founder of Technology Divers, shares his journey from Pakistan to the US, building a mobile app development company that evolved into a product development consultancy. He discusses his 'blueprint methodology' for converting napkin sketches into production-ready software, managing distributed teams across multiple continents, and helping non-technical founders navigate the complexities of software development. The conversation covers entrepreneurial mindset, AI's impact on software development, and the importance of peer groups for founders.
Rob Reesor shares his four-decade technology career journey from early AI expert systems at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive leadership roles across multiple private equity-backed companies. He discusses the evolution of software development, the challenges of technical debt management, building trust with non-technical stakeholders, and navigating acquisitions while emphasizing transparency and team empowerment.
Chris Caparon shares his 20-year journey building Sephoria Software, an accounts receivable automation company that grew from a garage startup in 2001 to serving Fortune 500 companies across 110 countries before its private equity exit. He discusses navigating multiple economic crises, evolving technology platforms, and the critical importance of customer-centric product development and maintaining strong founder relationships throughout the company lifecycle.
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. After moving to Boulder, Colorado, he founded Business Outside, which uses nature-based experiences to help corporate teams build authentic connections and develop intentional leadership approaches.
David Morczinek, CEO of Airworks, discusses his journey from aerospace engineering at Airbus to co-founding a geospatial AI company at MIT. He explains how Airworks uses computer vision to analyze aerial data from drones, satellites, and aircraft, pivoting from pure automation to a hybrid service model when customers struggled with AI adoption. The conversation covers fundraising progression from friends-and-family to private equity, balancing technical innovation with market readiness, and building a sustainable company culture.
Jan Heybroek, partner at TechCXO's exec ops practice, shares his 17-year journey building and selling a medical market research company to a medical education firm in 2021. He discusses M&A negotiation tactics, the importance of transparency during due diligence, post-acquisition integration challenges, and healthcare industry trends including AI's role in diagnostics and the shift toward personalized medicine.
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