In this insightful episode of the Startup CEO Show, host Mark MacLeod sits down with Eli Portnoy, a serial entrepreneur with two successful exits under his belt. Portnoy shares his journey from his first venture to his current role as co-founder and CEO of BackEngine, offering a masterclass in navigating acquisitions and building thriving startups. The conversation delves into the psychological aspects of selling a company, the importance of building relationships with potential acquirers, and the challenges of transitioning from founder to employee post-acquisition.

Portnoy's candid reflections on his experiences provide valuable lessons for aspiring entrepreneurs, emphasizing the rarity of acquisition opportunities and the need to carefully consider one's motivations when faced with an offer. The episode also explores Portnoy's current venture, Back Engine, which leverages AI to help companies maintain a strong connection with their customers as they scale. Listeners will gain actionable insights on fundraising, exits, and the evolving landscape of startup leadership in the age of AI.

Tune in to learn from Portnoy's successes and challenges, and discover how to build a company with long-term vision while remaining open to transformative opportunities.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/