Like so many great entrepreneurial stories, Rebecca Kacaba’s starts with a pain point.
As a capital markets lawyer, she was no stranger to helping companies go public or raise capital. But as she spent more time in the Toronto start-up scene, something about the venture capital system kept standing out.
“I knew from being in capital markets that there were a lot of systems and processes on a go-public transaction that just didn’t exist in the private markets,” she said. “I realized that whatever technology was built to automate the private markets would have a big, big market opportunity.”
With an entrepreneurial mindset she gained from her dad, Kacaba decided that she could help create that technical solution. Partnering with her eventual co-founder and fellow lawyer, Mat Goldstein, the pair set out to learn about the tech space they were entering – all while continuing their demanding law jobs.
The journey would take years of after-hours dedication but eventually lead them to launch DealMaker in 2018, an online platform that lets companies raise capital directly from investors by providing tools to manage fundraising, compliance, and investment processing in one place.
Essentially, it gives companies a way to raise money digitally while turning customers, fans, and supporters into investors.
“It’s developed a new form of strategic capital which didn’t exist prior to us,” she said. “We help everyday people get access to private investments, which they typically don’t get access to.”
One of the best examples is the work the team did with the Green Bay Packers in 2021.
The NFL team, which had previously sold shares to fans, partnered with DealMaker to raise capital for stadium upgrades. In just a matter of months, they raised over $65 million and turned over 175,000 fans into shareholders.
“That transaction was one that created a lot of awareness for us,” she said. “To see an NFL team raising money from the fans and using DealMaker to do it; that was a really marquee occasion.”
Hitting the billion-dollar mark
Since 2018, DealMaker has been on a growth trajectory that even Kacaba says can be hard to wrap her head around.
The online platform has processed over $2 billion in transactions across more than 650,000 investments. Just last year alone, Pacaso, a vacation home ownership platform, raised over $72 million through DealMaker.
“We’re building a new category, so understanding how the founders and the fans use the platform has been fundamental to me,” said Kacaba. “We’re building something that our customers can use and evolve with them.”
As DealMaker has grown, so has Kacaba’s role within it.
A company that started with a small team around a boardroom table is now approaching 200 people across multiple offices, which has forced her to think differently about leadership, scale, and how teams operate.
A big part of that now is building systems that can support growth, while also staying ahead of how quickly technology is changing. One of the company’s newer initiatives is focused on giving employees access to AI tools so they can experiment, build, and work more efficiently.
“We’re at such an interesting point in history,” she says. “The way that you develop and the entire user feedback to product to development pipeline is shifting.”
For Kacaba, that pace of change is part of the job, as is navigating the inevitable barriers that come with building a company.
As a woman founder in tech and finance, she says she tries not to let that reality shape her mindset.
“I really try not to let it permeate my mental landscape,” she says. Instead, she sees entrepreneurship itself as a challenge, no matter who you are.
“The job of the founder is to create momentum and really roll the boulder up the hill,” she added.
Still, building in the online capital space has given her an interesting perspective on how access to funding can shift when traditional gatekeeping is removed. Because digital fundraising puts the company’s story in front of investors first, rather than relying as heavily on face-to-face relationship building, she says women and minority founders can often see stronger results.
For Kacaba, that ties back to the original idea behind DealMaker: expanding access.
“It just proves there are still some inherent biases in boardrooms,” she said. “But when you take things digital, there’s no opportunity for it. We love that, and we’re really proud of that in the online capital industry.”
With private markets continuing to evolve, her focus now is on building what comes next – both for DealMaker and for the category itself.
As for her advice to other founders? Move before you feel fully ready.
“Take more risks early on because that is what it’s about,” she added. “It’s not going to work every time, but the key is to just keep rolling through it and build the momentum and pivot where you need to. Eventually, you’ll build something great.”
