Last Friday, Vinay Hiremath, founder of Loom (USD 900M exit to Atlassian), shared on his blog about leaving Loom, leaving $60M payout, breaking up with his girlfriend, dealing with insecurities, a brief stint at DOGE, and how he is now in Hawaii self-studying physics.
I, along with a few founders I know who had substantial exits at a fairly young age (late 20s to early 30s), experienced something similar. Post-acquisition, most of us underwent—and many are still going through—a self-discovery phase largely centered on finding a 'purpose' and determining the best possible use of our time at this point in life. Does it mean taking risks that nobody else can, building more companies, accumulating more wealth, reaching the pinnacle of mental and physical health, building a family, getting involved in social impact, or leaving everything behind to sit on an isolated island?
Capital does give you freedom and excessive optionality in life choices, especially if you're still unmarried. However, it is difficult to find your anchor, and most of the time, the abundance of choices becomes overwhelming. I was fortunate to meet a few exited founders who had gone through the acquisition process, and they were kind enough to share what worked for them.
In one of my conversations with David Haber, he said: "As entrepreneurs, we build companies, but while we do that, we can't discount life. And life is what happens outside our companies."
That thought has stuck with me. Today, three years after exiting Recko | A Stripe company to Stripe, I feel there are multiple ways to make life more fulfilling. It is not just the single-minded, unidirectional professional pursuit, which more often than not is driven by a chase for external validation rather than an internal desire to become better at your craft or to do something that uplifts people around you.
Until the time you find that burning desire, restlessness, or drive to pick up the shovel again, take that family trip, get in shape, try something that you always wanted but never could, embrace the nothingness, enjoy the boredom, and keep exploring!