There’s a wealthy Montreal entrepreneur-investor who holds a unique mantra when he writes cheques.

He lives life according to the phrase, “choose a job you love doing and you will never have to work a day in your life again.” He invests in companies that do stuff that he’s really interested in, like travelling, sports, music and entertainment. Generally the startups are seed stage and some of them are from first-time, fresh-faced founders.

It may sound strange in today’s business world, but this is the life of YOLO Ventures founder and CEO, Marco Gomez.

Gomez is a 35-year-old University of Toronto graduate who earned a comfortable living in the world of finance before he started investing. He feels strongly that everything we do in life should in some way be related to things we love, otherwise we’re simply existing and not living.

He makes select $25,000-$50,000 investments in small startups, mostly Montreal-based. One of them was Outpost Travel, a notable startup that was founded by Hamed Al-Khabaz and Ovi Mija. Al-Khabaz was shoved in the national spotlight three years ago when his CEGEP college at the time expelled him for a “Cyberattack” on the school’s server. Outpost Travel, since rebranded as Zilyo, is a site that aggregates peer-to-peer vacation rentals through online community marketplaces like Airbnb.

The other portfolio companies of YOLO Ventures include a reviews website for beaches, called BeachBelievers. “We always review hotels but we never really review beaches, and when you travel you’re always looking for the best beaches to go to,” said Gomez.

As well, the fund has invested in a pair of companies that resemble Zilyo, in Stay22 and likeahotel.

Gomez sees his fund as more of an incubator than a traditional venture capital firm. YOLO Ventures’ headquarters is a sprawling, 3000-sq. ft. open-concept office space in Old Montreal where Gomez said he frequently invites young startups to work out of, whether he’s investing in them or not.

He made it clear he doesn’t simply hand out cheques, saying that many of today’s young university graduates starting a company for the first time are nearly impossible to invest in. However, he will let the work for a few months “with a gentlemen’s agreement that if I see that you’re starting to progress than I may invest.” He likes to help out and get involved, and if he likes what he sees after a few months then he’s open to longer chats.

But what about those 20-something founders who may think they want to run a company only to change compete direction a year later? In other words, is Gomez hesitant to invest in some of today’s millenials, knowing they may not really know what they’re passionate about?

“It’s a huge risk,” he agreed. “Many times they don’t have the marketing experience and they don’t even know how to write an email or talk to people. They may be really good at programming but they don’t know how to run a business. So what I hope for is they will be good at what they do and that if we give them enough guidance they can grow to eventually attract people with more business experience.”

Take Zilyo, or the former Outpost Travel for example. YOLO Ventures partook in the company’s seed round of $200,000. Yet just a few years later, Al-Khabaz and Mija split. They were just 19 at the time of the business’ conception in 2013.

To that point, Gomez admitted that returns aren’t guaranteed in the game of baby startup seed investing. “When I write a cheque, I don’t expect any type of return. I know what I’m getting myself into and I know I may never see that money again,” Gomez told MTLinTech.

Many would agree that these types of bold investors are sorely needed in a startup ecosystems. Perhaps the real gamblers aren’t the ones who partake in $200 million series C rounds along with nine other funds, but those who drop $50,000 on a lotto ticket that they’ll probably never see again.

What motivates me is to see all the greatest technological developments over the past eight years and the fact that I really haven’t been part of that wave of innovation. YOLO ventures is there to at least try to be part of that.

The Innovation we’ve seen has not come solely from business-related startups. We have things that are fun like Snapchat, Soundcloud and all those great apps that really changed the way we live and made it easier for us to do the things we love. So when I look at the great successes over the past 10, 15 years, it motivates me to know that I could potentially come across the next big thing. When you write a cheque it’s really like a lottery tiket. You’re hoping that you may be contributing to the next big thing.

Getting him to chat about his fund is one thing, but finding out about the somewhat-private Gomez was more of a challenge. All we know for now is that Gomez and YOLO Ventures are content to lose on a few small bets and eventually hit a home-run on a special bet. They encourage young startups in those areas of interest that the fund wants to focus on (travelling, leisure, entertainment and sports) to get in touch with them.

“A lot of people come to my office and tell me they don’t know anything about me and I kinda like that,” he said. “It’s nice to remain private because as long as you’re doing good things and you’re happy with what you’re doing then everything will be okay.”