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

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.ABOUT OUR GUEST: Chris Thomajan has been a CFO for over 30 years in a variety of industries, including: biotech, medtech, healthcare tech, software, digital media, Internet services and investment banking.Chris was a founding partner of America’s Growth Capital, a boutique investment bank focused on emerging growth technology companies. He was the early-stage CFO/VP Operations for Asurion Corporation, which is a closely held, multi-billion-dollar private company. He was also the founding CFO for a pioneering Internet company, Delphi Internet Services, which was acquired by News Corporation in 1993.Chris has extensive experience in raising debt and equity. He has also been involved in numerous M&A transactions and has managed the operations of several start-up companies during rapid revenue growth. He received a B.A. from Dartmouth College and an M.B.A. from Columbia University.CONTACT:https://www.linkedin.com/in/chris-thomajan-1879143What is THE SKY LOUNGE?Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.ABOUT OUR HOST:Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.Subscribe and turn on notifications to listen to new episodes as they launch!YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzENApple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-loungeFollow Tales From The SkyLounge on Social MediaX/Twitter: https://x.com/TFTSkyLoungeInstagram: https://www.instagram.com/tftskylounge/Learn more about TechCXO: https://www.techcxo.com/Production/Design: James LiebmanMusic: Soundstripe/Cody Martin-Sunrise