Earlier this summer, delegates to Toronto’s Collision conference were stuck. The flashy gathering that bills itself as “North America’s fastest growing tech conference” was plagued by logistical issues stemming from the pandemic that were preventing or slowing international visitors from arriving. One lucky group from Africa did manage to snag visas at the last moment – but on such short notice, had nowhere to stay.
Enter Isaac Olowolafe. Among his many pursuits – including being an entrepreneur, real estate developer and venture capitalist – Mr. Olowolafe also owns Dream Suites, a hotel and event space. He donated hotel rooms to the grateful delegates.
It is a gesture that reflects much of Mr. Olowolafe’s life and work, which melds an unapologetically capitalist ethic with a concern for social impact.
His entrepreneurial spirit began early. While in his second year as a University of Toronto student, Mr. Olowolafe started a real estate business. That initial venture became successful enough to transition from selling houses to real estate development.
His portfolio now includes a real estate arm and Dream Ventures, a venture capital firm. Additionally, along with managing partner Lise Birikundavyi, Mr. Olowolafe is also responsible for BKR Capital, the first Canadian venture firm with a mission to invest in Black-led companies.
Key to Mr. Olowolafe’s path was making important connections and capitalizing on them. After getting exposed to the startup scene at the DMZ accelerator, part of the Toronto Metropolitan University (formerly Ryerson), Mr. Olowolafe saw a need.
“Right off the bat, I saw a lack of diversity within the tech space,” he says. “That’s when I decided to go back to Ryerson and say, ‘You know what, there’s a big push in tech and innovation. Let’s launch the first black tech incubator.’ "
That became the Black Innovation Fellowship, a $20-million fund to invest in Black-led companies, which in turn became its own venture arm, BKR Capital.
What drives Mr. Olowolafe’s focus on diversity and Black businesses specifically is laying the groundwork for future entrepreneurs, both in tech and other sectors.
“I was fortunate to get exposed to the space, even though there weren’t any mentors in my community who were able to open up doors for me,” he says of his early connections to the startup scene.
“I want to make sure the next individual, or the next generation of venture capitalists and tech founders don’t have to be fortunate to get into a space that most get into simply based on the environment that’s created for them.”
To date, BKR has invested in four firms, while Dream Ventures, a more broad-based venture firm also part of Mr. Olowolafe’s group of companies, has invested in 18 tech startups since 2015.
Among the companies in BKR’s portfolio is Goodee, a curated homewares and lifestyle marketplace. Started by twins Byron and Dexter Peart in 2017, Goodee gathers sustainably-made products from around the world, which the Peart brothers often discover when travelling the globe.
Goodee’s connection to Mr. Olowolafe is one Dexter Peart describes as inevitable, in part because of an unfortunate paucity of Black founders.
“I think inside the business community as well, unfortunately, there are not a lot of us,” says Mr. Peart.
“It takes a person like Isaac to be able to put the pieces together,” he says. “You can imagine the amount of perseverance it would take to be able to put this into play.”
The sense that Mr. Olowolafe enabled something that should ideally have happened long ago is an opinion shared among others whom he has helped or invested in.
Miq is a community lending platform founded by three former international students. It too is a recipient of funding from BRK, but for co-founder Johah Chininga, investments aren’t always financial in nature.
“Connecting with Isaac, who has worked in the industry, and also has that affinity for identifying a group that is historically marginalized, and then willing take that bet on us was really inspiring and encouraging,” he says.
Miq also has a clear social dimension to its mission. Community lending is pooling together capital outside the purview of traditional financial institutions. It allows people, such as newcomers to Canada, who are often excluded from those realms, to both access and build credit.
That social impact is what Mr. Olowolafe says drives him. His entrepreneurship has led him to not just invest in companies but also fund the first endowment for African Studies at U of T and be the jersey sponsor for Canada Basketball – so that “those within our community can aspire to do more than just play a sport,” he says.
This mix of both business and social mission defines Mr. Olowolafe’s work, and also melds with his focus on Black or BIPOC communities that have been historically overlooked.
“Right from day one, the underlining factor of Dream Maker is having a social impact as well,” he says, “and seeing how the relationships we’ve built can be for the betterment of not only my business, but also the community that I’m from.”