The Spotlight
Rebecca Kacaba
Founder
In this edition of The Spotlight, in partnership with The Scotiabank Women Initiative™, WFW CEO Dr. Sherry Shannon-Vanstone sits down with Rebecca Kacaba, CEO and co-founder of DealMaker. From her roots as a Bay Street securities lawyer to transforming digital fundraising, Rebecca shares how technology is democratizing capital markets, eliminating traditional gatekeeping, and empowering diverse founders to build and engage investor communities.
Dive in to learn how Rebecca transitioned from corporate law to lead a global fintech platform, her take on taking bold risks, and her actionable advice for women founders and new angel investors.
About Rebecca Kacaba
Rebecca Kacaba is the co-founder and CEO of DealMaker, the capital-raising tech platform behind some of the largest online raises in North America. A securities lawyer by training, Rebecca left her partnership at the world's largest law firm to launch DealMaker, a bold bet on modernizing the way companies raise money. That bet paid off.
Under her leadership, DealMaker has powered over $2.5 billion in capital raised, helped brands like the Green Bay Packers, Newsmax, and Pacaso bring retail investors into the fold, and delivered landmark retail-investor outcomes, including Monogram Technologies' Reg A raise, Nasdaq listing, and $177 million acquisition by Zimmer Biomet.
Rebecca leads the charge for regulatory modernization of the capital markets. In 2025, she testified before the U.S. House Financial Services Committee, advocating reforms to Reg CF and Reg A+ to expand founder access to capital. Under her leadership, DealMaker opened its U.S. headquarters in New York City, acquired Rally On Media, and raised $20 million to scale retail capital raising.
Rebecca has been named one of Canada's Most Powerful Women, one of North America's most innovative lawyers by the Financial Times, and Waterstone's Most Admired CEO. But it's not the accolades that define her, it's her mission. She's a relentless advocate for founders, especially those traditionally left out of capital markets. And she's helping founders across sectors, from sports to entertainment to tech, use retail capital as a strategic edge in the new capital stack.
Connect on LinkedIn: Rebecca Kacaba
Company Snapshot
DealMaker is the online capital raising platform. We help companies build and scale their own capital engine, raising directly from the people who love them.
Problem Solved: We redesigned capital raising for the internet. A new path to capital where founders keep control of their terms and their investors.
Unique Solution: One platform runs the entire raise: marketing, compliance, payments, and reporting. Founders own the investor relationship start to finish.
Market Opportunity: Online capital raising is going mainstream. Any company with a real community can fund itself, and we power the biggest raises in the market.
Vision & Impact: A world where everyone can own the brands they love. We get there by making online capital raising mainstream.
The Spotlight: A Conversation with Rebecca Kacaba
Interviewed by Sherry Shannon-Vanstone, Co-founder & CEO, Women Funding Women Inc. (WFW).
Published August 23rd, 2026
Sherry: We’re delighted to welcome Rebecca Kacaba, CEO and co-founder of DealMaker, as our featured founder for The Spotlight. Rebecca, thank you for joining us. You began your career as a securities lawyer. Tell us about your journey and how it led to the creation of DealMaker.
Rebecca: Thank you for this opportunity to be featured in The Spotlight. My co-founder, Matt Goldstein, and I were securities lawyers on Bay Street, working with startups and resource companies on capital raises. The most painful part of every transaction was the closing process - tracking subscription agreements, correcting paperwork, reconciling payments, and managing everything manually in spreadsheets.
When the JOBS Act created new opportunities, we saw a chance to digitize that entire process. Our vision was simple: create an online platform that guided investors through the subscription process, tracked each stage of the raise, and helped companies close financings far more efficiently. DealMaker was born from a problem we experienced every day alongside our clients.
Sherry: Since then, DealMaker has evolved far beyond digital closings.
Rebecca: Absolutely. One of the biggest lessons I've learned is to listen carefully to your customers. As their needs evolved, so did our platform. Today we help companies not only raise capital digitally but also build and engage communities of retail investors.
That requires bringing together compliance, legal documentation, transfer agency services, digital marketing, communications, and investor management. AI has allowed us to integrate those capabilities into a much more seamless experience while reducing costs and improving fundraising efficiency.
Bold Move
Sherry: Starting DealMaker was a bold step. Did it feel that way at the time?
Rebecca: Yes, it did. But Matt and I believed the opportunity was enormous. We saw a market that was largely untapped, and when you truly believe in an opportunity, you have to be willing to take the leap and bet on yourself.
Sherry: What have been the greatest advantages of building the company in Toronto?
Rebecca: Toronto provided exceptional financial talent, supportive regulators, and a vibrant startup ecosystem. Those early advantages helped us build the company on a strong foundation.
Sherry: And what about challenges?
Rebecca: Every founder faces challenges. Rather than focusing on why they exist, I've always believed the key is understanding your own strengths, hiring people who complement your skills, and continually creating momentum for the business. That's how obstacles are overcome.
Sherry: You've often spoken about the value of having a co-founder.
Rebecca: It's been tremendously valuable. Matt and I bring different perspectives, and we challenge one another's thinking. Healthy debate leads to better decisions. Over the past decade we've built a strong partnership, and having someone beside you during both the highs and the lows of entrepreneurship makes an enormous difference.
Vision for DealMaker
Sherry: Looking five years ahead, where do you see DealMaker?
Rebecca: We want to process more than $1 billion in retail investment capital and make retail investors an integral part of company capitalization tables. We believe broader participation in private markets strengthens the economy, creates jobs, and gives more people the opportunity to build wealth alongside the companies they believe in.
Sherry: Recently, DealMaker has expanded significantly, please share more on this.
Rebecca: We've opened our U.S. headquarters in New York, established an office in Los Angeles, and are expanding into Medellín, Colombia. Each financing round has helped support that growth.
Sherry: What is your long-term vision for DealMaker?
Rebecca: We want to create a world where people can own the brands they love. Imagine buying your favourite product, scanning a QR code, and becoming an investor in that company. We want investing to become part of everyday life - not something reserved for institutions or experienced investors.
We help founders build communities around their businesses and transform those communities into long-term sources of capital. Technology now allows everyday investors to participate in companies much earlier in their growth journeys.
Companies that are the best fit for Dealmaker
Sherry: What types of companies are the best fit for DealMaker?
Rebecca: Today we primarily serve U.S. companies, and some Canadian companies that can access U.S. securities regulations. Companies generally have audited financial statements and an existing community that can become the foundation for their fundraising efforts.
Sherry: Women Funding Women works with founders seeking capital. Could DealMaker become another avenue for some of them?
Rebecca: Absolutely, particularly for companies with a U.S. presence. Digital fundraising has proven to be a valuable avenue for women and underrepresented founders because it relies less on traditional networks and face-to-face gatekeeping.
Advice to Women Founders
Sherry: What advice would you offer women founders who are just beginning their entrepreneurial journeys?
Rebecca: Go for it. Entrepreneurship is incredibly rewarding. Don't wait for permission. Take risks early, continue moving forward one step at a time, and you'll surprise yourself with what you can accomplish.
Advice for New Angel Investors
Sherry: As you know as you were on Women Funding Women’s Advisory Council in 2024, Women Funding Women is focused on increasing women's participation in angel investing. What advice would you offer new angel investors?
Rebecca: Start small. Investing is a journey. People don't need to begin with large investments. On our platform, the average investment is about $3,600, with many opportunities starting around $1,000. That allows investors to build diversified portfolios while gaining experience and confidence.
Sherry: We'd love to see that model available in Canada.
Rebecca: So would we. The challenge is Canada's regulatory structure. Unlike the U.S., which has one national securities regulator, Canada has provincial regulators, making digital securities marketing much more complex.
Conclusion
Sherry: Finally, what would you like our readers to take away from your journey?
Rebecca: Building DealMaker has been one of the great joys of my career. There have certainly been challenges, but helping democratize access to capital markets and seeing more women founders succeed has made it incredibly rewarding. I also want to congratulate Women Funding Women for creating such an important ecosystem that supports founders and investors across Canada.
Sherry: Rebecca, thank you for sharing your story and your insights. We are very proud of what you have accomplished with DealMaker. We look forward to following DealMaker's continued growth and appreciate your ongoing support of Women Funding Women.
Key Learnings from Rebecca Kacaba
For the movement
"Go for it. Entrepreneurship is incredibly rewarding. Don't wait for permission. Take risks early, continue moving forward one step at a time, and you'll surprise yourself with what you can accomplish."
Establishing your community
"One of the biggest lessons I've learned is to listen carefully to your customers. As their needs evolved, so did our platform."
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