The 3 Game-Changing Truths I Discovered Too Late That Could’ve Saved My Startup—and Your Sanity—20 Years Ago
To fix this imbalance, you must recognize that you have precisely one window to fix it, and that’s now. It means having the hard conversations about revisiting vesting, adding performance cliffs and making room for future partners. The pain of doing it now is nothing compared to the pain of explaining a broken cap table to new investors. We survived a similar case because we ripped that band-aid off, just before our next round made it impossible to do so.
Today, I tell founders to treat equity like a reserved seat at the board table: only give it to people whose judgment you’ll still respect a decade later. If only I had known that timing and value alignment in equity partnerships mattered so much, I would have saved myself countless hours of renegotiation had it been available back then.
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