The One That Got Away
What are some of the best investments you nearly did but ultimately didn't close?
I had one I pushed for as a junior VP. It was a pretty unique deal and I got obliterated by the IC in front of the entire firm. Years later I come to find out the business had 15x'ed in EBITDA over what would've been our 5 year hold. Would've been a 20+ bagger and made the fund nearly a 2x MOIC off an undersized equity check. I would've made millions on my small carry allocation. The Partners would've made tens to hundreds of millions. Both kicking myself and feeling vindicated. Unreal.
Who's to say your firm would've/could've driven that growth though? Not throwing shade but many times these kind of deals are just a perfect storm where if one tiny thing changes it doesn't go the way it ended up.
In this instance, we recommended backing the CEO and team who, in hindsight, have successfully achieved this level of growth. Would everything go exactly the same? No, but I think we'd be within a reasonable band.
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