Couple sold their company for $745 million, but felt numb after: 'We just couldn't process it'

CNBC

5 days ago

From the outside, it seemed like Mike and Kass Lazerow had made it.
It was 2012, and the couple from New York had sold the social media marketing platform they co-founded, Buddy Media, to Salesforce for $745 million. To celebrate, they had a lavish party for their employees where Mike walked out on stage to a 20-minute standing ovation, Kass says.
They were supposed to feel euphoric, yet they didn't. Instead, they felt a "numbness," Kass, now 54, tells CNBC Make It.
"We get into the Uber to go home … and [Mike] looks at me and goes, 'OK, so which doctors' appointments do we have tomorrow for the kids?'" Kass says.
Since 2007, the entrepreneurial couple who started Golf.com during the dot-com bubble had been working relentlessly on their new company. Kass gave birth to their third child just before her husband Mike, now 51, came up with the business idea for Buddy Media. She even nursed her newborn while building desks for an office.
After three pivots, they finally landed on a business model that worked, and once they did, the momentum was "incredible," says Kass. By the time they sold the company, it was generating at least $50 million in annual recurring revenue, Kass says.
Kass, who left her job as chief operating officer of the company after the sale to become a stay-at-home mom, says it took her a full year of small revelations — and therapy — to fully recognize what they had accomplished.
"I don't want to compare it to real trauma, but it was like a version of PTSD, because we just couldn't process it all at once," Kass says. Outside of work, "you're the same old schmuck you were before you sold the business," says Mike.
They lost their sense of purpose as entrepreneurs, Mike says. "We wanted freedom; that we weren't tied to one business. We didn't want to sit behind a desk."
Mike, who was CEO of Buddy Media, transitioned to leading marketing and strategy initiatives at Salesforce. But after four years, Mike says his health started to take a toll from his demanding travel schedule and he missed spending time with his kids.
Kass joined several charity boards, but realized that while the work was meaningful, it didn't give her the sense of purpose and excitement she was seeking.
"The joy in creating themes and building businesses and winning customers and hiring people, all that stuff that is really exciting," Mike says.
Kass and Mike aren't the only entrepreneurs to feel a sense of aimlessness after selling their company. Jyoti Bansal said selling his company, AppDynamics, to Cisco for $3.7 billion was the "saddest day" because he felt he hadn't solved the problem that drove him to build the company in the first place, he told CNBC Make It last year.
Jake Kassan lost his drive and identity after selling his watch business for $100 million in 2018, relating the feeling to the movie "Groundhog Day," where the main character wakes up to the same day over and over again, he said in January.
To get out of their ruts, Bansal, Kassan as well as Kass and Mike all shifted to careers that got them excited again. Kassan said he's building out his YouTube channel, and Bansal is working on a new startup called Harness, he said.
As for Kass and Mike, Kass says they're back in the entrepreneurial game in their own way — supporting founders through personal equity investments and sharing insights in their new book, "Shoveling S---."
"I don't think I could do another standalone company again," Kass says. "Those two companies and leading the people part of it — which I take very, very seriously — took just about everything out of me."