Overdraft: When Divorce Forced This Founder to Redefine the Meaning of Success

Portrait illustration of Vivek Jain

In this series, I speak with people who know what desperate feels like. While now blooming into success, these founders share with me their deeply personal financial struggles and lessons learned on their way back to black.


Vivek Jain was living his dream, married and working as a venture capitalist—against the tropical backdrop of Bermuda. But when the couple decided to slow their pace in preparation for kids, they moved back to their prairie hometown in Canada, and their dream began to unravel. Vivek put his own interests last, taking safe jobs that provided for his growing family. The strain impacted his marriage. At 34, Vivek found himself living with his parents and starting over.

A risky investment introduced him to a world of contacts that would later help him build FANchise, a fan-controlled football league, as well as LOKO, a dating app he co-created with comedian Norm MacDonald that’s designed for people like him—those restarting the pursuit for love later in life. Six years and two startups later, Vivek is creating a fulfilling life for his family and doing work that he loves. But to get there, he had to learn the hard way.

In Vivek’s words:

“I was working 90 hours a week, 52 weeks a year, and traveling most of the time. That lifestyle didn’t lend itself to having a family. My parents were highly involved, and I kind of wanted to be that same way. So, we moved back to Regina. It was kind of hard to find something there that I was truly passionate about. The jobs I took allowed me to take care of the family in the manner I wanted to, but I was totally going through the motions. It was really tough.

I’d be silly to say it didn’t put a strain on our relationship.

You’re raised to believe materialistic things are what you strive for, right? Money gives you power and things, and that’s a false measure of success. We had this five-bedroom home with a screening room in it and all the fixings. And then, I got divorced. I was 34 years old, a proud venture capitalist, and I ended up in my childhood bedroom—living in my parent’s house for a year. I couldn’t even afford rent, never mind living expenses. Most of my assets were not liquid.

Divorce kind of gives you the chance to reinvent yourself.

When you get divorced, your life turns upside down. I had a 4-year-old and a 1-year-old at the time. There’s no other way to put it other than it was utter hell. You always try to put up a good front to your parents, right? You never want to let them know that you’re struggling. But inside, I was just a disaster. Every Sunday, I had to drop my kids off at my ex-wife’s house, and it was the hardest thing. I didn’t want to see my parents. I didn’t want to see my friends. I just wanted to sulk. It’s [been] six years, and I’m still not used to that moment when I drop my kids off.

But divorce kind of gives you the chance to reinvent yourself and use all those things you’ve learned over your life. I was in Toronto in 2014, and I came across this homeless man. He asked me for money. I was not in the place to be charitable at the time. But I gave this guy $20, and he lit up. I had this warm and fuzzy feeling for the first time in 18 months. And that was an epiphany moment: this is what I want to feel like. I realized, OK, from now on I’m only going to do things that I’m passionate about, and I’m going to say yes to every opportunity that comes my way. I’ve never forgotten the look on his face.

It was an utter disaster. We didn’t make it to the first season, and I saw my money evaporate.

Saying “yes” led to so many neat things and meeting so many different people. Eventually an opportunity presented itself to buy a football team in Las Vegas. By this time, we had settled our divorce, so I had access to funds again, but this was going to take a meaningful amount of my net worth to do it. To be honest, the numbers didn’t add up. It was an utter disaster. We didn’t make it to the first season, and I saw my money evaporate. It turned into the most incredibly expensive season tickets.

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But I never felt more alive. I had just lost a big chunk of money, but that first day of walking into the owners' seats in this packed arena was this magical feeling that no one can ever take away from me. And it opened up a world of connections—I met people that I never would have had access to. That opportunity led to six of us starting FANchise.

Now, all my decisions are based on: does this make my children’s lives better in some way?

I went through a period for, like, two years where I didn’t sleep more than three or four hours a night. I had a full-time job, my kids, and FANchise as well. At the start, you’re just terrified. ‘How am I going to keep these two kids alive?’ Now, all my decisions are based on: does this make my children’s lives better in some way?

The reality is that I could make more money by just going and working at a job again. When I broke away from my job to focus on my business, it was scary because I spent most of my life having a steady income. For the longest time, the way I looked at things was: ‘how much money do I have left till I go bankrupt and I have to go back to living in my parent’s house?’ I’m putting in time, and I’m trying to do all the right things I’m passionate about and hope it works out in the end. I mean, I don’t think there’s a better recipe for success.”

Illustration by Germán González