Rebecca Kacaba spent more than a decade as a capital markets lawyer on Bay Street before deciding, in 2016, to build the platform she believed the industry was missing. DealMaker, the company she co-founded with Mat Goldstein, has since powered more than $2 billion in online capital raising for brands including the Green Bay Packers and Pacaso.
In this In Profile, the DealMaker CEO discusses testifying before Congress, the case for raising regulatory caps, and why retail investors deserve a real seat at the table.
Tell us more about your company and its purpose
DealMaker is a technology platform that lets companies raise capital directly from retail investors. We built it because the traditional capital raising process was slow, expensive, and closed off to everyday investors. Companies using our platform have raised over $2 billion to date, from startups to household names like the Green Bay Packers and Pacaso. Our purpose is simple: make raising capital as straightforward as running an e-commerce store, and give retail investors a real seat at the table. For too long, access to high-growth investment opportunities was reserved for institutions and accredited investors. We think that’s backwards. Everyday Americans should be able to invest in the companies they believe in, not just watch from the sidelines.
What are some of your recent achievements you’d like to highlight?
Testifying before the U.S. House Financial Services Committee was a career highlight. I presented data showing how the JOBS Act could unlock billions in capital formation and tens of thousands of new jobs. That’s the kind of impact I want DealMaker to have beyond just our platform. Pacaso’s recent raise through DealMaker is a great example: it showed retail investors participating alongside institutional and VCs in a high-growth company. We’ve also been recognised on Deloitte‘s Technology Fast 500 and named one of Fast Company’s Best Workplaces for Innovators. The achievement I care most about though is getting more great businesses funded and giving everyday people the opportunity to own the brands they love, and participate in investing.
How did you get into the fintech industry?
I spent over a decade as a capital markets attorney, most of it on Bay Street advising companies on how to raise money. I saw the same problem over and over: the process was paper-heavy, expensive, and built for institutions, not for everyday investors or the companies trying to reach them. I kept thinking there had to be a better way. In 2016, my co-founder Mat Goldstein and I decided to build it ourselves. Neither of us came from a traditional tech background. We came from law, which meant we understood the regulatory maze better than most, but had to learn how to build software from scratch. That combination turned out to be an advantage. We knew exactly which problems needed solving because we’d lived them from the inside, advising clients through broken processes for years. Being the implementor of tremendous legislation like the JOBS Act is exciting and an honour.
What’s the best thing about working in the fintech industry?
The pace of change. Fintech moves fast, and that means the rules that felt fixed five years ago are being rewritten right now. I get to be part of conversations, in Congress, with regulators, with founders, about what capital access should look like going forward. That’s rare in most industries. I also love that the work is tangible. When a company raises capital through our platform and uses it to hire people, expand, or launch a product, that’s a direct, visible result. The other thing is that fintech attracts people who want to fix something broken, not just build another app. Most people I work with, whether at DealMaker or at the companies we serve, are motivated by making a system more fair and more open. That shared mission makes the work genuinely energising.
What frustrates you most about the fintech industry?
Too much of the industry still treats retail investors as a risk to be managed rather than a resource to be included. That mindset is outdated, and it’s not backed by the data we’re seeing. Founders on our platform have raised a total of $2.8 billion via their retail base, and we’re seeing 23.5 per cent year-on-year growth in retail investors, with almost 90,000 new investors so far in 2026. Ordinary people are hungry for a stake in their favourite private companies. A solid example is that of the Green Bay Packers, whose 176,000-plus fans turned into shareholders and raised a total of $65.8 million via a common stock offering in just three
months. That frustration is fading, though, as larger private companies allocate bigger share allocations to non-accredited investors.
How have your previous roles influenced your career?
My psychology degree turned out to be more useful than I expected. I use it every day, whether I’m reading a room in a negotiation or figuring out what actually motivates an investor to say yes.
Cold sales came first, though. I worked at my dad's business as a teenager, making cold calls. That experience shaped how I think about founders. If you can’t walk in a room and sell something to a stranger, you’re going to struggle. It’s one of the most underrated skills in this industry.
Law is what gave me the opening to start DealMaker. I learned from lawyers who were sharp in a specific way. They didn’t just solve the problem in front of them. They looked underneath it, found the other problems hiding there, and built solutions that closed off all of them at once. That kind of thinking shapes how I approach everything now, from product to strategy.
What’s the best mistake you’ve ever made?
I make so many mistakes it’s hard to pick a favourite! Recently, a departing employee sent me the nicest message about my leadership and what working at DealMaker meant for his career. I regret having to say goodbye to him and his excellent work ethic, but it’s a good reminder that even when you get things wrong along the way, and I have, more than I’d like to admit, the impact you have on people can outlast the mistakes.
That’s the real lesson. Leadership isn’t about avoiding mistakes. It’s about what people take away from working alongside you, even after they’ve moved on.
What has the future got in store for your company?
We’re focused on continuing to give access to everyone to own the brands they love. That includes expanding access to areas like private markets and pre-IPO opportunities, which have historically been closed to everyday investors almost entirely. We’re also investing heavily in the technology side, making the platform smarter and more automated so companies can run raises with less manual work and more visibility into what’s actually happening with their capital. On the advocacy side, we’ll keep pushing for regulatory reform. The Reg CF and Reg A+ caps need to rise to reflect where the market actually is today. Longer term, my goal is for DealMaker to be a core part of how companies think about raising capital, not an alternative path, but a standard one. Retail investors have shown they’re a loyal, engaged source of capital. We want the infrastructure to reflect that.
What are the next key talking points or challenges for your industry as a whole?
Market perception. Retail has a strong role to play in the capital markets that would be good for the economy. The gig economy can also be the investing economy. Regulation caps under Reg CF and Reg A+ are a key issue. The data is clear that raising these limits would drive real capital formation and job creation, and I expect this conversation to keep gaining momentum in Washington. I’d also point to the growing role of AI in investment access and trading. As AI tools become more central to how people invest, the industry needs to make sure retail investors aren’t left behind or given inferior access compared to institutions. Finally, expect continued debate over tokenised and pre-IPO equity access. That’s an area where the technology is moving faster than the regulatory framework, and the industry will need to figure out how to close that gap responsibly.
AI level 2 of 5: drafted by our AI editorial assistant from source material our editor chose; fact-checked, edited and signed off by Mark Walker, Editorial Director. What the levels mean
Facts Only
* Rebecca Kacaba spent more than a decade as a capital markets lawyer on Bay Street.
* DealMaker was co-founded with Mat Goldstein in 2016.
* DealMaker powers more than $2 billion in online capital raising for brands including the Green Bay Packers and Pacaso.
* The company's purpose is to make capital raising straightforward and provide retail investors a seat at the table.
* Kacaba testified before the U.S. House Financial Services Committee, presenting data on the JOBS Act's potential for capital formation.
* Pacaso's recent raise utilized DealMaker.
* The company was recognized by Deloitte's Technology Fast 500 and Fast Company for Best Workplaces for Innovators.
* The platform has facilitated raises from startups to household names.
* Retail investors participated in a $65.8 million offering for the Green Bay Packers in three months.
Executive Summary
Rebecca Kacaba co-founded DealMaker, a technology platform enabling companies to raise capital directly from retail investors, facilitating over $2 billion in fundraising for entities including the Green Bay Packers and Pacaso. The company was founded by Kacaba and Mat Goldstein, who leveraged their background as capital markets attorneys to address the perceived inefficiency of traditional, institution-focused capital raising processes. DealMaker aims to make capital raising accessible to everyday investors, positing that retail investors deserve a seat at the table.
The CEO has advocated for regulatory changes, including testifying before the U.S. House Financial Services Committee to argue for unlocking capital formation via legislation like the JOBS Act. Achievements include facilitating raises where retail investors participated alongside institutional and VC investors, such as Pacaso's raise. The platform has received recognition from Deloitte and Fast Company.
The CEO views the fintech industry's pace of change as a positive element, allowing participation in shaping regulatory conversations, but also notes frustration with the current treatment of retail investors as risk rather than a resource. There is a recognized tension between institutional approaches and the desire for broader public participation, which is reflected in the ongoing debate over regulation and access to private markets.
Full Take
The narrative centers on the tension between institutional finance structures and the potential of democratizing capital access, framed by an individual who operated within the existing system before seeking structural change. The shift from viewing retail investors as a managed risk to recognizing them as a significant, hungry capital resource reveals a deep conflict in industry philosophy. The success stories, like the Packers raising capital through DealMaker, illustrate that the desired outcome—broad participation—is achievable, even if incremental progress is currently slowed by established institutional norms.
The articulation of frustration regarding the status quo, particularly how retail investors are treated as liabilities instead of assets, points to a systemic misalignment between market mechanics and social equity goals. The focus on regulatory action suggests a belief that structural barriers, like regulatory caps, are the primary impediments to realizing this potential. Furthermore, the reflection on leadership mistakes underscores a pattern where personal impact often overshadows procedural errors; true learning emerges from the residue left by the work itself rather than flawless execution.
The future trajectory hinges on whether technological advancement can force an evolution in regulatory frameworks, or if societal shifts will compel institutions to adopt inclusive models. The challenges outlined—AI integration, tokenized access, and regulatory reform—suggest that the industry’s next growth phase will be defined less by platform innovation and more by the successful reconciliation of technological speed with evolving social expectations regarding economic inclusion.
Sentinel — Human
This text reads as a deeply personal interview blending business metrics with reflective philosophy, strongly suggesting it was written by the subject or a carefully guided human journalist rather than pure synthetic generation.