For a founder facing an exit that’s falling apart, this talk explains why the habits you build today determine whether you survive tomorrow, and why the exit almost never goes as planned.
Every SaaS owner/CEO will eventually face an exit, and it is rarely a smooth process since personal, family, and professional life all keep moving while the deal unfolds. Raj will share his journey through growing a company, to a busted sale, unexpected crises, and a creative exit to highlight the habits and mindsets that matter most.
You’ll learn how to navigate the pressures that come with exits, how to factor opportunity cost into every decision, and to reflect on their why.
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Transcript
The Setup: Building to Exit
Every SaaS CEO will face an exit at some point. The hard truth: exits are fragile and rarely smooth. But the lessons you learn on the way define everything that comes next.
I acquired Super Salon, a vertically focused SaaS business serving the salon industry with point-of-sale software. If you’ve checked in at a Supercuts, that was us. My goal was simple: scale it. Professionalize the product. Build a real management team. Invest in sales. Put money back in and watch it grow.
For four years, we did exactly that. We tripled revenue. We stayed profitable the entire time. We assembled the team, built the systems, optimized the operations—everything I’d set out to do. We weren’t perfect, but the chart was up and to the right. It felt like victory was just a matter of time.
The Deal
Around 2019, valuations looked good. We went to market. We got multiple offers. I sat courtside at a Bulls game with one PE firm. Everything felt solid. Diligence was moving. Documentation was underway. We were heading toward closure.
Then Monday before Christmas 2019 happened.
Our largest customer decided to compete with us. A buyer invoked the material adverse change clause. The deal collapsed. Our equity value was suddenly uncertain. No one would touch the business.
My financial freedom dreams were delayed. But we were still up and to the right. We could recover.
It wasn’t fine. We found out a couple months later—from a whistleblower—that the customer had stolen our IP. They’d reverse-engineered our database schema. We tried to buy them out. They said they’d just drain our legal fees. We had no choice: we filed a lawsuit.
Then April 1st, 2020 hit. Haircuts were not essential. We went from serving 10,000 locations to nearly zero overnight. Seventy percent of our revenue vanished in days.
At the same time, our competitor—the one stealing from us—found Tiger Global and secured $150 million in venture funding.
I lived in Minneapolis. The city was burning. It felt fitting.
The Crisis
Every decision became massive. I was overwhelmed. I didn’t know what to do. I had to get vulnerable with my leadership team—probably for the first time ever. I didn’t know what they’d say.
They stepped up. They jumped into the foxhole. Every single person on our hundred-person team stayed. Nobody left.
It wasn’t the strategy that held us together. It was the culture. The openness. The honesty. That aha moment crystallized everything: culture was what was carrying us.
But we still had to make a choice: fight the lawsuit indefinitely—we’d probably win, but courts were closed and the timeline was uncertain—or take the pragmatic path and settle. Everything I’d built to sell the company had to be taken apart. We split the business. We settled one side. We sold the other. It wasn’t the home run I’d imagined. But everybody made money at the end. More importantly, our customers and team were protected and cared for.
The Lessons
When you’re tested, you fall to your habits, not your ambitions.
Build good habits now, while things are good. Do them consistently. It’s the little things that matter. If I hadn’t built the right culture, none of this works. We wouldn’t have survived.
Opportunity cost is very real.
Every decision you make as a CEO is a trade-off. Every yes is a no to something else. Most of us think about trade-offs only on the big deals. We don’t think about them on the small things. But those small things are what create your habits. Think constantly: What am I saying no to?
Process is fragile and rarely smooth.
Build your company when you’re good and ready, not when you’re burned out. Prepare for things to go wrong because they will. Waiting has its own cost—if I’d sold two months earlier, the IP theft would never have surfaced. Everything would have been clean.
Know your why.
When things were darkest, I got out of bed because I love building people. I love creating culture. I loved the impact we had—ten thousand locations times eight stylists times a hundred customers a day. We touched billions of people. That was what made me proud. That’s what I’m coming back to now.
Exit Reflection
Exits are fragile. Selling or waiting won’t create certainty. The only thing that will is asking yourself: Why now? Why this buyer? Why this business? What will I do next? What am I going to see when I turn around? Build your answer to those questions today.
Raj Mahajan
Founder, Jaan Capital
Raj has over 20 years of leadership in entrepreneurship, finance, and M&A, shaped by experiences across multiple industries and continents. Raised in Palos Verdes, CA, he earned his undergraduate degree from Boston University and later his MBA from the University of Southern California with a focus on Entrepreneurship and Strategy. Don’t hold his early career in New York and Southern California as an investment banker against him – he learned things that will be useful for you.
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