TFTSL Ep42 — Chris Thomajan
Today in the Sky Lounge, we are joined by Chris Thomajan, a CFO who’s spent 35 years with startups and has worked with over 100 companies—mostly in biotech, mostly venture-backed, always as the steady hand while everyone else loses their minds.
Chris didn’t start in finance. English major, disco worker in London, law firm (hated it), Columbia Business School, then three decades of pattern recognition in the startup world. He’s developed a particular skill: knowing which CEOs will make it and which won’t. He’s even categorized them like wine—from Beaujolais Nouveau (enthusiastic first-timers) to Port (dictators you really don’t want to work for).
We explore what makes Boston’s biotech ecosystem unique, why nine out of ten boards need to be “managed away,” and what it really takes to prepare a company for IPO. Chris breaks down the current VC landscape (“too many capital calls, not enough distributions”), why he’d never personally invest in early-stage biotech, and the one quality that separates great CEOs from the rest: the ability to delegate.
Plus: hitchhiking 5,000 miles across America in an era when that was still possible.
TFTSL Ep39 – Neal Miller
Today in the Sky Lounge, we are joined by Neal Miller, partner emeritus at TechCXO and one of the firm’s earliest members. Neal shares stories from 19 years working with over 70 companies, including the legendary Cloud Sherpas journey that started with a Monday morning Starbucks meeting in 2008 and ended with an Accenture acquisition. He reveals the simple napkin drawing that transformed Boomtown from chaos to clarity, why the 1983 IPO market let an $8 million revenue company go public, and his unusual career path from KPMG auditor to software sales to CFO. Plus, hear about his transition to Costa Rica, lessons from owning a microbrewery, and why uncertain economic times actually strengthen the fractional executive model.
TFTSL Ep38 – Louis Gump
Louis Gump joins us in the Sky Lounge to explore a question every founder and executive faces eventually: what happens after the acquisition? In this candid conversation, Louis shares how he helped build the mobile business at CNN.com, led digital transformation at The Weather Channel, and became the steady hand guiding post-acquisition innovation at startups and growth-stage companies alike.
We unpack the differences between entrepreneurs and intrapreneurs, what makes someone thrive inside a big company post-acquisition, and how timing and self-awareness shape every meaningful career move. Louis also discusses the importance of clarity in strategy, the value of not rushing change, and why keeping founders involved after a deal often leads to better outcomes.
Louis is also the author of The Inside Innovator, a practical guide to driving innovation from within established companies — ideal for leaders navigating post-acquisition roles or scaling without the founder title.
Whether you’re scaling, selling, or staying to build the next chapter — this episode will meet you at the crossroads.