The secret to raising $2 billion in funding

DealMaker CEO Rebecca Kacaba shares how her company’s online platform makes it easier to invest in innovation projects.

To Rebecca Kacaba, selling shares online should be as simple as buying a pair of shoes.

For more than a decade, Kacaba worked as a securities lawyer on Bay Street, where she witnessed how difficult it was for founders to raise capital through traditional channels. She wanted to make that process easier, so in 2018 she launched DealMaker with co-founder Mat Goldstein. The cloud-based platform empowers users to generate capital by drawing on their own networks and through strategic online marketing campaigns.

As Kacaba explains, this framework effectively lets companies set up online stores so that they can invite people to invest and build a community. “It allows customers to get behind the businesses that they love,” she says. Recently, the Green Bay Packers decided they wanted to build a new stadium, and they turned to DealMaker for help. By using the platform, the NFL team was able to raise $65 million for the project while bringing dedicated fans into the shareholder base.

To date, DealMaker has helped clients raise more than $2 billion; last year, the company landed in the top 10 of the Globe and Mail’s round-up of Canada’s fastest-growing companies and was ranked second in Fast Company’s list of the top 100 workplaces for innovators.

Here, Kacaba discusses how her time as a lawyer inspired her to help founders, the unique challenges inherent to the Canadian innovation ecosystem and what it means to be recognized as one of Canada’s top leaders.

What was the inspiration behind DealMaker?

The idea was born out of a desire to help entrepreneurs with a problem we saw they were having: raising capital was difficult and cumbersome, and it cost them too much. We were deep in the capital market space and could see that something fundamentally wasn’t working.

It seems like there would be a stark contrast between the world of a securities lawyer and the scrappy startup ecosystem. What did you bring from your previous life into this project?

Bay Street really drilled into me the importance of hard work and having passion for what you do. I had the pleasure of working with so many amazing, smart lawyers as well as CEOs, CFOs, company leaders and investors. I’ve always felt very fortunate to have had that experience. And I saw the power of resilience. Nothing is ever easy — getting a deal over the line requires a lot of late nights. I saw the difficulties companies were going through and I grew to really respect and admire the resilience I saw in the founders I worked with.

What are some of the challenges Canadian entrepreneurs face when it comes to scaling companies?

Keeping a business funded isn’t easy. More than 65 percent of startups fail because they run out of money. And there’s limited capital in Canada simply due to the size of the country. In particular, tech scales better with tons of users and you need deeper pockets to get that user count. We knew very early that you have to go international so that you can get more customers and scale your tech product to be the best in its class.

I’d love to see more access to early-stage opportunities for investors in Canada. We have a challenge in that securities laws are provincially regulated but there are different things we could do with tax incentives on a federal level.

What is it like navigating the complexities of the Canadian investment ecosystem?

The rules that have really benefited DealMaker allow every individual — not just accredited investors — to access private companies and early-stage investment opportunities. Those rules are modelled on European ones. The U.K. ecosystem grew in part because of the tax incentives for people to invest in early-stage companies — now, more than 40 percent of the capital that closes there is through online platforms.

I would love to see the provincial regulators get together and streamline the system. We’ve seen it working really well in lots of democratized countries around the world, from Brazil to Australia. In America, where the rules have been in place for more than a decade, tons of companies get funded; American venture capitalists back 21 to 26 percent of the ecosystem. Everyday Americans can fund the businesses they’re passionate about, and a community can build around these businesses. Additionally, more than 30 percent of digital capital fundraising goes to minorities and female founders, versus less than two per cent in venture capitalist or bank deals.

What advice would you offer to entrepreneurs who are just starting out?

I don’t think about things as mistakes — they’re just steps that move you forward on your journey. Human adults make over 35,000 decisions a day. Are all of those going to be right? A lot of women have impostor syndrome or fear of failure, and you have to just jump through that. Every decision is taking you where you need to be. When you get into that mindset, you can be what I like to call “unapologetically ambitious.” I also think it’s important for women to be vocal about what they want to accomplish — that’s going to lead them to achieve great things.

Waterstone Human Capital named you Most Admired CEO in 2023. What does it mean to win an award like that?

To be thought of for such an honour.… Words can’t describe it. But I wouldn’t be here without my amazing team. So I’m really proud of the Workplace for Innovators Award as well. It’s really tough to get on Fast Company’s list, so to be there as a Canadian company is a really important testament to the DealMaker team and the workplace they’ve made, which I absolutely love.

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Photo courtesy of DealMaker