Selling A Business For $3.7 Billion Was A Mistake For 46-Year-Old–He Recounts It As His 'Saddest Day' Of Regret

Jyoti Bansal, the mastermind behind software company AppDynamics, lived out a fantasy many entrepreneurs can only dream about – launching a startup and selling it for a staggering $3.7 billion. However, what should have been a triumphant moment quickly turned into one of his biggest regrets.

Bansal, now 46, had spent years as a Silicon Valley software engineer before finally achieving his goal of becoming an entrepreneur. AppDynamics, the company he founded, solved a critical problem faced by large companies: fixing broken apps and preventing outages. 

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But when Cisco swooped in with a last-minute acquisition offer in 2017, Bansal found himself at a crossroads. The deal would make him and hundreds of his employees immensely wealthy. Despite that, he says it became his "saddest day."

Bansal had always dreamed of building a company for financial gain while solving a problem that plagued his industry. “When I started [AppDynamics], I didn't think about a financial outcome,” he explains. “I just thought in terms of: This problem needs to be solved.” And solve it he did – AppDynamics became known for its ability to help companies troubleshoot and prevent software glitches.

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The sale of AppDynamics to Cisco came as a surprise. The company was on the verge of going public when Cisco made its offer. “We weren't stopping our IPO," Bansal recalls. “We had six days to figure out how to go about it.” 

He describes sleepless nights agonizing over the decision, juggling conversations with the board, investors and other stakeholders. “People think it must've been an easy decision, but it was the hardest.”

The factors Bansal had to weigh were complex. There was the financial aspect – hundreds of employees stood to gain life-changing sums of money. "We had about 300 employees who made more than a million dollars," he says.

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"Dozens walked away with $5 million or more." Beyond the financials, Bansal was concerned with whether Cisco would allow AppDynamics to continue its mission and keep its company culture intact. To Cisco’s credit, they offered AppDynamics a high degree of independence, but something still didn't sit right for Bansal.

After the sale, Bansal found himself grappling with feelings of loss. "I spent nine years of my life fully dedicated to what we were building," he reflects. "Suddenly, it's the end of a chapter." Walking home from the celebration party, he realized he wasn't ready to let go. “It was bittersweet – it felt like we were closer to the finish line, but not quite there.”

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In the months that followed, Bansal tried to find solace in travel. He trekked the Himalayas, hiked Machu Picchu and went on safaris. But after six months, his bucket list was checked off and he was left feeling aimless. "Everyone told me, ‘You should retire. Go to the beach,'" he says. "But that's not me."

Determined to continue solving big problems, Bansal founded another company, Harness, which also creates software tools for developers. Ironically, it was valued at $3.7 billion in 2022 – the same price Cisco paid for AppDynamics. But this time, Bansal says the story is far from over.

When asked what he would do if he received a similar offer for Harness, Bansal didn’t hesitate. "We'd have to entertain it, but I know the answer is most likely no," he says confidently. "At AppDynamics, it felt like we were closer to the finish line. At Harness, our journey is just starting."

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