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.

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Scott Voss, Senior Market Strategist at HarbourVest Partners, joins The Venture Capital Podcast (VC.fm) to discuss the future of venture capital, AI investing, SaaS valuations, private equity, secondaries, and private market liquidity.

Scott shares insights on why companies stay private longer, how mega funds are reshaping venture, what AI means for SaaS business models, and where investors may find opportunity outside the crowded consensus trades.

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Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789
Website: https://www.venturecapital.fm/

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In this episode of The Venture Capital Podcast (VC.fm), hosts Peter Harris and Jon Bradshaw talk with Wally Wang, Founding Managing Partner at Scale Asia Ventures and a Business Insider Seed 100 (2025) investor, about identifying AI winners early — and scaling them across the U.S. and Asia (Japan, Korea, APAC).

Wally brings a unique mix of experience as a machine learning scientist (NYU / CMU / Microsoft), a former operator (YC-backed Pebble, acquired by Fitbit), and an enterprise founder who helped grow DataVisor (raised $150M+). Today, he backs AI infrastructure, enterprise AI agents, cybersecurity, developer tools, and robotics, with a strong cross-border thesis that helps founders expand globally and access strategic distribution partners in Asia.

We discuss:

• How to evaluate “real” AI founders vs hype
• AI moats: why product-market fit isn’t enough anymore
• What actually creates defensibility in enterprise AI (data, trust, workflows, integrations)
• Build vs buy in AI: when enterprises DIY vs purchase software
• Why vertical AI agents are safer than horizontal AI wrappers
• Cross-border expansion strategy: U.S. → Asia vs Asia → U.S.
• Robotics + physical AI opportunities and Asia’s hardware advantage
• Why enterprise + government budgets are still under-targeted

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  Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789
  Website: https://www.venturecapital.fm/

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