‘I am rich and have no idea what to do with my life’
When people talk about startup exits, they usually talk about the number – the headline figure, the valuation, the kind of win that looks good on paper and perhaps even better in a tweet. What they talk about far less, however, is what often comes next.
When your identity has been built around routines, late nights, and the daily ache of being needed, who are you supposed to be when your calendar suddenly clears – and no one needs you in the morning?
When the company becomes the self
It’s a reality many founders eventually confront. For Vinay Hiremath, co-founder and former CTO of Loom, it arrived after the $975 million sale of his company – when the urgency, the responsibility, and the sense of being needed all but vanished overnight.
“Life has been a haze this last year,” Hiremath wrote in a blog post titled “I am rich and have no idea what to do with my life” early last year.
“After selling my company, I find myself in the totally un-relatable position of never having to work again. Everything feels like a side quest, but not in an inspiring way.”
Hiremath, who left Loom following its acquisition by Atlassian in October 2023, spent nearly a decade building its foundations. After dropping out of the University of Illinois, he teamed up with Joe Thomas and Shahed Khan in 2016 to chase the idea that making workplace communication easier through quick video sharing would be the one that changed their career trajectories.
And it did, because it was that simple idea that soon grew into one of the most widely used video messaging tools in tech.
But like many founders, Vinay didn’t just work on Loom – he became Loom. The company scaled rapidly, reaching more than 25 million registered users and roughly 200,000 paying customers. At its peak, users were recording over 1.5 billion minutes of video every quarter.
With nearly $200 million raised from major firms like Sequoia Capital and Andreessen Horowitz, Loom’s valuation climbed to around $1.5 billion by 2021.
Growth at that scale often raises expectations not just externally, but internally as well – shaping founder identities around speed, intensity, and momentum.
When freedom creates friction
In October 2023, Loom was acquired by Atlassian for close to $1 billion. For Vinay, this came with a familiar offer to stay on, help with the transition, and earn a reported $60 million compensation package. But he said no.
From the outside, that choice can look baffling. But for Vinay, it was less about money and more about meaning. Staying would have extended a role he already felt done with. Leaving meant freedom – but also uncertainty.
As the company grew faster and larger than he ever imagined, expectations, both internal and external, began to compound. The business became intertwined with his sense of self, leaving little room for distance when things went wrong.
Hiremath wrote that as Loom “continued to skyrocket to new heights,” he began to feel those expectations weigh on him. “When we went through our first round of layoffs, this company my ego was hitched to had suffered a massive blow, so I lost myself.”
The experience, he added, left behind “a complex web of internalized insecurities” that he soon felt the need to unravel.
Walking away, then, wasn’t just about closing one chapter. It was about creating enough space to separate who he was from what he had built. And that’s where the story gets uncomfortable in a very relatable way.
When the silence is too loud
When Loom was finally behind him, Hiremath did what many newly exited founders do when structure disappears and experimented.
He spent time exploring public policy. He dabbled in robotics startups. He traveled. He climbed Himalayan peaks. He even enrolled in physics courses in Hawaii. Each pursuit offered novelty, stimulation, even moments of excitement – but none offered permanence.
In retrospect, Hiremath has described that period less as rest and more as drift. The projects were interesting, but unanchored. Without the pressure of deadlines or the gravity of responsibility, everything felt optional – and therefore strangely weightless.
And that feeling is more common than the startup world tends to admit. Hiremath put words to a private experience many founders carry quietly, because when the all-consuming mission disappears, so does the structure that once made life feel purposeful.
Financial expert Robert Pagliarini has also written about the experience, calling it “sudden wealth syndrome,” a pattern where financial success arrives faster than emotional readiness. The problem isn’t money itself, but what its arrival removes when it comes to daily direction, urgency, and the sense of being needed.
After years spent measuring progress through growth charts, shipping deadlines, and investor updates, the absence of noise can feel less like peace and more like disorientation. Silence, it turns out, can be pretty loud.
But that doesn’t mean the exit was without its quieter rewards, either. Using proceeds from a secondary sale following the acquisition, Hiremath gifted $1.7 million to his parents so they could retire.
He later described the moment not in terms of money, but expression – watching their faces as the significance settled in, and seeing pride replace years of worry.
“That was probably the coolest thing that money has bought for me,” he said during a podcast episode with Moneywise.
Searching for the next “why”
Hiremath’s experience highlights something the startup ecosystem rarely lingers on: exits don’t automatically deliver fulfillment. They may serve a greater purpose for financial security, but they too often expose a deeper, less comfortable question.
Who am I when I’m no longer building this company?
Many founders assume purpose will reappear on its own once the pressure lifts. But more often than not, it doesn’t. It has to be rebuilt – slowly, deliberately, and without the familiar scaffolding of metrics and momentum.
For some, that process might involve public service, learning something entirely new, or starting all over again. For others, it might mean doing nothing for a while.
At the end of the day, there is no single correct response to an exit – only honest ones.
