When Your Co-Founder Asks You to Leave - And you have 60 Days to Figure it Out
From YC success to startup fallout - how Pranav Piyush bounced back to build something even bigger.
Hey 👋 I’m Andrew. Welcome to Delivering Value - the newsletter and podcast where I share stories from SaaS leaders about the toughest moments of their careers and how they turned them around. You get to learn from their mistakes, without the pain.
Things aren’t always what they seem.
The beginning of Pranav Piyush’s startup journey is incredible. The press release would read something like: “Entrepreneur creates a product while working full-time at Paypal. Gets into Y Combinator. Goes all in on the business. Rapid growth follows.” On paper, it reads like the ultimate startup success story. But behind the scenes, cracks were forming and pressure was slowly building.
Then one day, his co-founder said he had to leave.
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Pranav was working at PayPal, when a buddy from college reached out with an opportunity.
He had been quietly working on a side-project for a few years, and suddenly, it was growing - fast.
It had no marketing engine, other than a few posts on some niche forums, but it taken off organically. The numbers told a pretty compelling story: 50,000 monthly active users. His friend had recently quit his job to go full-time on the business, and asked if Pranav was interested in building together.
It was an opportunity that seemed too good to pass up, so they applied to YC.
The moment they were accepted felt like stepping into a different world. YC was the ultimate validation, the golden ticket to venture funding, the fast track to building something massive. Pranav also quit his job, leaving behind a stable paycheck and a comfortable role.
And for six months, it was all or nothing (which can feel like a lifetime at an early-stage startup).
YC’s incubator program was intense. Months of nonstop pitching, iterating, and proving that their startup wasn’t just another experiment, but a company worth investing in. But it was working.
But they experienced the classic YC success story, 10x growth in six months.
Everything should have felt incredible. But something was off.
The warning signs weren’t obvious at first.
There was no screaming match. No dramatic betrayal. No investor fueled conflict. Just small, accumulating moments of misalignment, and a creeping feeling that something wasn’t right. Something had shifted. He just didn’t know what.
They were sitting in their small office in Sunnyvale.
No investors. No team. Just the two of them, just like when they started. Pranav’s co-founder wasn’t angry. He wasn’t frustrated. He was just…certain.
“We need to part ways.”
Pranav didn’t react right away. His brain wouldn’t let him. Because this wasn’t just a business decision. This was his identity. His career. His future. For six months, they had been on the same path, chasing the same dream. And now, suddenly, it wasn’t his anymore.
“‘Holy shit!’ was my first reaction,” Pranav shared.
At first, they each slept on the decision. Then tried to give each other feedback and work through things. Then it became clear parting ways was probably the right decision.
“What choice do I have, right?” he shared.
He walked out of the meeting without a job - and no idea what to do next.
“In retrospect, there were some signs of trouble, but I didn’t see that coming,” Pranav shared.
Instead of sulking, Pranav focused on making it a smooth transition. They quickly figured out the paperwork, and he exited the business. But then, he had a new problem.
Pranav was on a immigrant visa, which meant he had 60 days to find another job.
He didn’t have time to properly process everything that happened. He applied to Dropbox, got into the BizOps and Growth team, and had a great 3 1/2 year run there before going to Magenta, Pilot, and Bill.com - before eventually starting his current company Paramark (where he is the CEO and co-founder) .
“Ironically, I probably wouldn’t have gotten that Dropbox job if I didn’t have YC on my resume,” he shared.
It’s easy to connect those dots afterwards, but in the moment was a really challenging situation. Pranav hasn’t spoken publicly about this situation before our podcast and was quick to point out that there’s no bad blood between him and his previous co-founder. He’s still at it, and Pranav wishes him all the best.
But these types of co-founder challenges are nothing new. They’re one of the most common reasons that startups fail.
Professor Noam Wasserman wrote in The Founder’s Dilemma, that “65% of high-potential startups fail due to unresolved tensions and conflicts among co-founders”. That challenge has influenced a whole category of Co-founder Coaches and Therapists.
At the time, Pranav thought getting pushed out of his company was the worst thing that could happen. But it set off a chain reaction and turned out to be the reason his next opportunities were even bigger.
I hope you take the time to listen to the full-version in his words.
Catch Pranav’s full story on YouTube
Or listen on Spotify
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