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.<p></p><p>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).</p><p>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.</p><p>Plus: hitchhiking 5,000 miles across America in an era when that was still possible.</p><p>ABOUT OUR GUEST: </p><p>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.</p><p>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.</p><p>Chris has extensive experience in raising debt and equity. He has also been involved in numerous M&amp;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.</p><p>CONTACT:</p><p>https://www.linkedin.com/in/chris-thomajan-1879143</p><p>What is THE SKY LOUNGE?</p><p>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.</p><p>ABOUT OUR HOST:</p><p>Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.</p><p>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&amp;L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.</p><p>Subscribe and turn on notifications to listen to new episodes as they launch!</p><p>YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6</p><p>Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN</p><p>Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658</p><p>Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge</p><p>Follow Tales From The SkyLounge on Social Media</p><p>X/Twitter: https://x.com/TFTSkyLounge</p><p>Instagram: https://www.instagram.com/tftskylounge/</p><p>Learn more about TechCXO: https://www.techcxo.com/</p><p>Production/Design: James Liebman</p><p>Music: Soundstripe/Cody Martin-Sunrise</p>