Therapists help tech start-up co-founders resolve disputes and save their businesses
When Jon Chintanaroad and Mike Prestano started their own tech-worker recruiting business a little over two years ago, there were a lot of things they did not expect.
They didn’t expect their business to take off so quickly. They didn’t expect to wear so many hats — accounting, business licensing, insurance. They didn’t expect to be at each other’s throats six months down the line, seeking help from a therapist.
They’re not alone. For all the careful planning co-founders put into their businesses, the growing number of start-up leaders seeking partnership counseling suggests many are running into similar relationship problems. Tech entrepreneurs may be smart, but any Silicon Valley therapist will tell you it doesn’t mean they can navigate the emotional complexities of a co-founder relationship.
Chintanaroad and Prestano were longtime friends who lived and worked together. They’d always been chummy. But they became constantly irritated and impatient with each other. As Prestano put it, they were “always home and always working together.”
“It’s like when you travel with your best friend,” he said. “It’s the little things that bug you.”
Soon, they started assuming the worst, concluding that the other didn’t value their contributions.
“Like, if I wanted to buy a printer and Mike said no, I’d think, ... I’ve brought in thousands of dollars in revenue, why won’t you let me buy an $80 printer?” Chintanaroad, 36, said.
“And I’d think he was being reckless, and that we should be thinking long term and making sure we have enough to last us through the winter,” said Prestano, 33.
Only months earlier, everything had been fine. In fact, Chintanaroad and Prestano couldn’t believe their luck.
The San Francisco pair had always talked about leaving their jobs to start their own business. So in 2013, after a string of contracting gigs, they took the plunge. Prestano finished his contract for a large tech firm on a Wednesday, and by Friday the two had registered their business, Aspire Recruiting, and were taking their first client meetings. By the following Monday, they had their first job orders. After three months, their recruitment start-up was profitable.
“It was crazy,” said Prestano, who described their business like “any other start-up” — a little scrappy with a lot of uncertainty.
For a while, the pair really couldn’t believe their luck. In a town where the majority of start-ups fail, their bet seemed to be paying off. Until it didn’t.
“About six months in, things were a bit off,” Chintanaroad said. “There was definitely tension.”
It only got worse when the realities of the business kicked in.
“We’d set a revenue goal, and we’d write a big number on the wall, and if we didn’t hit that goal I’d be stressed and upset about it,” he said.
It didn’t help that their business was commission-based, which meant if neither of them closed a recruitment deal, there was zero income.
Already annoyed with each other, the two were now highly strung and looking for someone to blame. Maybe one person was working harder than the other, they thought to themselves. Maybe one person didn’t appreciate the other’s contributions. They started bickering over things that were previously non-issues.
Eighteen months ago, they started working with Sunny Sabbini — a Silicon Valley family therapist and partnership coach — on resolving their conflicts and, more importantly, figuring out a way to prevent future problems.
“There was definitely a degree of conflict avoidance with their partnership,” Sabbini said of Chintanaroad and Prestano with their permission. “When you’re friends with your co-founder, there’s more risk and the stakes are higher. There’s a tendency to not have difficult discussions because you don’t want to hurt the other person.”
But the problem with this, Sabbini said, is the small problems aren’t quickly resolved, and they often snowball into big, unmanageable problems.
“If you don’t address problems while they’re still small and you wait for them to happen five, 10 times, then there’s a blow-up, and it can lead to a bitter feud, even if a relationship typically isn’t like that.”
In fact, co-founder relationships — particularly those in Silicon Valley where it’s not uncommon for co-founders to live together in tech incubators and hacker houses — can share striking similarities to marriages, according to licensed family therapist and engineer Howard Scott Warshaw, who specializes in working with people in the technology industry (“I’m fluent in English and nerd”).
Co-founders spend more time together than co-workers typically do. They make big decisions together that will affect their financial and emotional health. And they’ve made a significant promise — either to themselves or investors — that they’ll achieve something that the typical person might struggle to achieve.
“A couple says, ‘We’re going to buy a house. We don’t know how we’re going to get the money, but we’re going to buy a house.’ So they set a goal, and do it,” Warshaw said. “This is a common situation in a marriage because if you think of it, a marriage is two people getting together to define a life and a growth path together, and they commit to it. They don’t know how it’s going to unfold, but they’re going to do it.”
“That’s what co-founders are,” he said.
For some co-founders, the goal is to build a company that will go public. For others, it’s to build a business that another company will acquire for millions of dollars. And then there are those such as Chintanaroad and Prestano, who want to hit that big number written on the wall. Whatever the goal, if two people have decided that they will reach it together, communication is key.
And when that communication fails, therapists such as Sabbini, Warshaw and Jonathan Horowitz — a family therapist whose Silicon Valley practice primarily works with clients in the tech industry — step in, sometimes to mediate a conflict or to provide the co-founders with tools to resolve future disputes.
“There have been some situations where it seems like one party is being dragged in and they’re already over it,” Horowitz said. “It’s become adversarial, and companies that have gotten to that point — where they walk into the room and you just feel this awful tension — I’ve never had much luck with those companies,” he said. “They just end up breaking up — a lot like a divorce.”
Horowitz said the more successful companies are those that seek help when an issue first emerges; that’s when he has most luck getting them to see a situation from each other’s perspectives. Some companies are even now preemptively seeking counseling before any problems have arisen to safeguard against petty fallouts and personality clashes.
For Chintanaroad and Prestano, they needed only a handful of sessions with Sabbini to resolve their problems. They now use a numbering system to help them be more communicative about their priorities. When discussing an issue, each will assign a number from 1 to 10, with 1 being they could not care less and 10 being important. It’s helped them understand what they care about and where the other person is coming from.
“I also feel like I’m now less quick to jump to conclusions about anything,” Chintanaroad said. “Instead of assuming the worst, I’ll just ask, ‘Hey, what’s going on?’”
They debrief each other every morning and catch each other up on what’s happening in their personal lives so if one person is in a foul mood, the other knows why. They’ve also come to understand that their differences — Chintanaroad’s risk-taking and Prestano’s risk-aversion — are crucial to running their business.
Two years in, their start-up is thriving.
As for their friendship?
“If someone punched Jon, the first thing I’d do is punch that guy. That’s how it works,” Prestano laughed. “And if Jon saw someone hit me, he’d come out of the cuts and knock them out.”