Equity Crowdfunding & Digital Capital Formation: Dealmaker’s Playbook (Rebecca Kacaba)

Rebecca Kacaba (CEO & Co-Founder of DealMaker) joins The Venture Capital Podcast (VC.fm) to explain how capital formation is moving online — and how founders can raise money directly from their communities in a compliant, scalable way. Rebecca started her career as a capital markets attorney working on IPOs, M&A, and fundraising, where she saw a painful truth: even after an investor says “yes,” deals can die from complexity, delays, and compliance friction. DealMaker was built to fix that — powering digital fundraising and investor management for brands and high-growth companies. DealMaker has helped drive $2B+ in digital capital raised, was named one of Fast Company’s Best Workplaces for Innovators, and recently closed a $20M round. In this conversation, we cover: DealMaker’s “Shopify vs portal” approach to equity crowdfunding Why regulated markets innovate slower — and how the JOBS Act changed the game The rise of community capital as a complement to venture capital Sports ownership, fandom, and why fan-owned teams can build outsized brand value Why crypto retail adoption exploded — and how private investing can catch up How AI will streamline investor onboarding, accreditation, and compliance workflows Founder lessons: ruthless prioritization, Scaling Up / Rockefeller habits, and building a high-experiment culture What fundraising looks like in 2026 as public/private markets blur Keywords: DealMaker, capital formation, equity crowdfunding, Regulation A+, Regulation CF, JOBS Act, retail investors, fintech, startup fundraising, community investing, sports team ownership, venture capital, AI in finance. Follow the Podcast Instagram: Twitter: LinkedIn: Spotify: Apple: Website: Follow Jon Bradshaw LinkedIn: Instagram: Twitter: Follow Peter Harris LinkedIn: Twitter: Instagram: Youtube:

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Equity Crowdfunding & Digital Capital Formation: Dealmaker’s Playbook (Rebecca Kacaba) is an episode from Venture Capital by Jon Bradshaw.

This episode is 41:01 long.

This episode was published on Mar 16, 2026.

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