When Your Exit Falls Apart: Why Habits Beat Ambition

Raj Mahajan, in his lightning talk at BoS USA 2025, shared that he bought Super Salon in 2015, a point-of-sale software business built for salon chains (if you’ve ever checked in at a Supercuts, you’ve used it). For four years, he did everything you’re supposed to do – tripled the revenue and stayed profitable the whole way, hired a real management team, and put proper systems behind the business. Every number pointed the right way.

By 2019, the company was ready to sell. Several offers came in, and Raj was deep into the checks a private equity buyer runs before signing.

The Monday Before Christmas

Super Salon’s largest customer announced it was building a competing product. The buyer pointed to the material adverse change clause, the part of the contract that lets a buyer back out if something big goes wrong before signing, and left.

You can do everything right for four years straight, and still lose the whole thing to one decision somebody else made without asking you.

A few months later, a whistleblower came forward. That same customer had reverse-engineered Super Salon’s database and taken its intellectual property. Raj offered to buy them out nut they told him they’d rather bleed him dry in legal fees, so he sued.

There’s unlucky, and then there’s this bad timing you can shrug off. Getting robbed by the same customer you’ve been serving for years is harder to make peace with.

April 2020

Haircuts were declared non-essential. Super Salon went from serving 10,000 locations to almost none. Inside days, 70% of the company’s revenue was gone. Around the same time, the competitor that had taken its IP raised $150 million from Tiger Global.

He lost 70% of his revenue in days. In the same stretch, the people who robbed him were handed $150 million. I don’t know how you carry both of those at once.

“It Wasn’t the Strategy That Held Us Together”

Raj got vulnerable with his leadership team, by his own account for the first time ever. He had no idea what they would say back. Nobody on the hundred-person team left.

“It wasn’t the strategy that held us together,” he said. “It was the culture. The openness. The honesty.”

He built that culture years earlier with none of this in mind. He was just trying to run a good company. That’s the thing that held when everything else stopped working.

The Settlement

Raj had a real shot at winning the lawsuit outright, but the courts were closed and the timeline was anyone’s guess. Fighting indefinitely meant burning cash and attention the business didn’t have to spare. So he split the company in two, settled one side and sold the other.

Everyone made money, and the team and customers who stuck it out came out protected. It was a smaller ending than the one he had spent four years building toward.

“I Love Creating Culture”

Raj closed his lightning talk with four things he took from the experience.

• You fall to your habits, not your ambitions, when you’re tested.
• Opportunity cost shows up in small daily decisions more than big ones.
• Process is fragile and rarely smooth, so build it while things are good rather than when you’re already burned out.
• And know your why.

“When things were darkest, I got out of bed because I love building people,” he said. “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.”

The habits point is the one I’d actually act on. Ambition is what got the company to a deal in the first place. Habits are what were still standing after it fell apart. Worth asking what you’re building on a normal Tuesday, not just what you’re aiming at.

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