Episode Description

In this season one finale, I sit down with Lee Garber, our General Partner at NewSpring Capital, to get under the hood of calculated bets and strategic decision-making. Lee takes us through his fascinating journey from being ”the guy behind the guy” – starting as a newspaper-selling kid who became his fraternity treasurer – to becoming a seasoned private equity professional making million-dollar decisions.

We dive deep into the evolution of a PE career, from analyst to partner, and how the role transforms from connecting dots to making complex risk assessments. Lee shares raw insights about their biggest mistakes, including a telecom deal that went sideways, and how they turned it around through sheer perseverance. He breaks down the difference between perceived and real risk, the art of knowing when to pull the plug on deals, and why their Monday investment committee meetings can get pretty heated – but in the best way possible.

What struck me most was Lee's philosophy: ”Act like it's yours, and maybe one day it will be.” This episode reveals the human side of high-stakes investing, the importance of running toward problems rather than away from them and why being present – both professionally and personally – might be the most valuable skill of all.

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