It took me a long time to accept myself, having to overcome all those uncomfortable thoughts that it was not OK to be me.

TWO TRUTHS ABOUT ME AND A LIE: I have a sleeve of tattoos, I was born in Australia, I grow oysters. A SOURCE OF INSPIRATION: The ocean! WHEN I WAS A KID, I HAD WANTED TO BE THIS WHEN I GREW UP: Meteorologist. FAVORITE DISH: Sushi.

Jeff Ragovin

Getting uncomfortable to grow

A NATURAL SALESMAN. Jeff Ragovin is currently chief commercial officer at Fyllo, a compliance solutions provider for cannabis companies, but behind him is a wealth of companies he’s founded. These include Buddy Media, a social media marketing platform that was acquired by Salesforce; Social Native, an artificial intelligence-driven content creation engine; and his own venture funding firm.

So why join Fyllo as an executive rather than start another company of his own? “I did have some hesitation in joining Fyllo at the beginning, but when I saw the transformation that the cannabis industry was about to undergo, I did not want to miss out on the energy in this space. I knew nothing of the cannabis space, and I had been used to leading my own companies, but being put in this new position gives me the space to grow,” he says.

Looking back, many of Jeff’s previous ventures followed a similar trend—he thrust himself into spaces that were in flux and, amid the discomfort, he gained his footing. Starting with figuring out email marketing right after graduation, during the dotcom boom, to convincing brand giants such as HBO to advertise on Facebook when social media was just starting. “Without the chance to tackle discomfort head on, I would not have gotten as far ahead as I have today,” he says.

ENCOURAGING OTHERS TO GROW TOO. Jeff knew from a young age he was gay, but he rarely brought it up in conversation. He recalled being with his co-founders, Michael and Kass Lazerow, a month before the launch of Buddy Media, and realizing he had never told them that he was gay. “It wasn’t like I was closeted or anything but I had just never told him, and he was about to start a business with me.” Their response? They already knew. Jeff’s sexuality didn’t matter to the venture they were about to embark upon together.

“Looking back, I wondered why I held back from saying anything. Mike and Kass were my best friends in the world,” Jeff says.

With that affirmation from Michael and Kass, Jeff decided to never again hide his identity with anyone else. “It took me a long time to accept myself, having to overcome all those uncomfortable thoughts that it was not OK to be me,” he says. Perhaps if he had grown up with good representation of gay leaders and entrepreneurs, he might have accepted himself sooner, but he’s glad he had to go through this growth process all the same.

And he wants to pass that growth around, even if it means uncomfortable conversations with his ventures. “I want to make sure that my companies embrace all gender, ethnicities and sexual identities as well.”

As an entrepreneur, conversations tend to fall on certain default norms. There will be moments where people will ask whether you’re married with kids, or what does your wife do, Jeff notes. “Most of the time they don’t mean any ill intent. Telling them I’m married to a man might involve some initially uncomfortable conversation, but the relationship just course-corrects from there,” he says.

As a lifelong entrepreneur, he has not encountered investors reluctant to invest in his good ideas simply because he is gay. “If not, don’t take their money,” he says. “There’s no harm in being upfront about who you are.”

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Gaingels 100 2023