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 crowdfundingWhy regulated markets innovate slower — and how the JOBS Act changed the gameThe rise of community capital as a complement to venture capitalSports ownership, fandom, and why fan-owned teams can build outsized brand valueWhy crypto retail adoption exploded — and how private investing can catch upHow AI will streamline investor onboarding, accreditation, and compliance workflowsFounder lessons: ruthless prioritization, Scaling Up / Rockefeller habits, and building a high-experiment cultureWhat fundraising looks like in 2026 as public/private markets blurKeywords: 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 PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

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.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

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 hypeAI moats: why product-market fit isn’t enough anymoreWhat actually creates defensibility in enterprise AI (data, trust, workflows, integrations)Build vs buy in AI: when enterprises DIY vs purchase softwareWhy vertical AI agents are safer than horizontal AI wrappersCross-border expansion strategy: U.S. → Asia vs Asia → U.S.Robotics + physical AI opportunities and Asia’s hardware advantageWhy enterprise + government budgets are still under-targetedFollow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of The Venture Capital Podcast (VC.fm), hosts Peter Harris and Jon Bradshaw speak with Roberto Bonanzinga, Founder of InReach Ventures and former Founding Partner at Balderton Capital, about how artificial intelligence is transforming venture capital from the inside out.Roberto explains how InReach Ventures built a proprietary AI and machine learning platform to discover early-stage founders across Europe — often before they raise capital, build pitch decks, or even seek investors. Drawing on decades of experience backing companies like Revolut, Depop, Vivino, and Contentful, he shares why discovery is the biggest bottleneck in early-stage VC and how AI changes that equation.The conversation explores:AI-first venture capital modelsInvesting in founders before ideasEarly-stage startup discovery in EuropeGP-only venture firms and fund designWhy pitch decks don’t predict outcomesThe future of junior roles, analysts, and associates in VCHow AI reshapes career paths and investing workflowsThis episode is essential listening for founders, venture capitalists, LPs, and operators interested in AI, early-stage investing, and the future of venture capital.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of The Venture Capital Podcast (VC.fm), hosts Jon Bradshaw and Peter Harris sit down with Olivia Goldstein, General Partner at StartFast Ventures and CEO of Upstate Venture Connect, to discuss venture capital, startup ecosystems, and why the best founders and companies can be built far outside Silicon Valley.Olivia shares her founder journey (including building a startup that used influencer marketing and exiting in 2019), her thesis on investing in overlooked markets like Upstate New York, and practical advice for founders raising venture capital from non-traditional hubs.The conversation also explores emerging opportunities in entrepreneurship through acquisition (ETA), small business succession as baby boomers retire, and how AI and shifting labor markets may push more people toward owning real-world cash-flowing assets.Keywords and topics:Venture capital, StartFast Ventures, Upstate Venture Connect, Upstate New York startups, Buffalo startups, Rochester startups, Syracuse startups, B2B SaaS investing, startup ecosystem, founder-led companies, fundraising advice, entrepreneurship through acquisition, ETA, small business acquisition, SBA loans, VC opinions, investing outside Silicon Valley.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of The Venture Capital Podcast (VC.fm), we sit down with Paul Allen, founder of Ancestry.com, to explore how public-domain data, viral growth, and platform risk shaped one of the most iconic internet businesses—and how AI is about to transform government, media, and civic life.Paul breaks down the original insight behind Ancestry’s billion-dollar IPO, why genealogy was always a massive market hiding in plain sight, and the hard lessons he learned building on top of platforms like Facebook. We then go deep into his latest ventures, including CitizenPortal.ai and Elected.ai, which aim to use AI to bring transparency, efficiency, and accountability to government at every level.This is a wide-ranging conversation on AI, startups, platforms, public data, and the future of governance—with sharp insights for founders, investors, and operators navigating the next technological wave.In this episode, we cover:How Ancestry used public-domain data to build a multi-billion-dollar companyThe hidden size of the genealogy market (and how Paul validated it early)Scaling fast on platforms—and what happens when the platform pulls the plugViral growth loops before paid ads, Facebook, or Google distributionCitizenPortal.ai: turning public meetings into objective local news using AIElected.ai: dashboards for 500,000 elected officials to improve governanceUsing AI and automation to reduce government waste and improve servicesThe future of AI, privacy, and why society may split into two pathsWhy AI could uplift humanity—or deepen control, depending on design choicesIf you care about AI, startups, venture capital, govtech, public data, or building durable companies, this episode is for you.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

Loïc Houssier (CTO, Superhuman) joins VC.fm to unpack the Grammarly acquisition of Superhuman and what it signals about the future of AI-native productivity tools.We talk AI in the workflow vs standalone AI tools (ChatGPT/Gemini), voice-first computing, vibe coding vs production engineering, AI’s impact on hiring, and why UX taste and product design may be the real moat in an era where everyone has access to the same LLMs.Keywords: Grammarly acquires Superhuman, Superhuman email, Loïc Houssier, AI productivity, AI-native software, email AI, workflow AI, OpenAI, Anthropic, LLMs, vibe coding, Cursor, UX design moat, product-led growth, startup defensibility, AI hiring.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812#Superhuman #Grammarly #AI #Productivity #Startups #VentureCapital #Email #LLM #OpenAI #Anthropic #VibeCoding #UXDesign #ProductManagement #Engineering

Dating apps are broken — and AI matchmaking might be the next platform shift.Dini (Nandini) Mullaji, co-founder of Sitch, joins Whitney Hazard (M13) to explain how conversational AI and LLMs are replacing swiping with a matchmaker-style experience: deep onboarding, memory, non-negotiables, and curated introductions.We cover consumer AI defensibility, why Sitch avoids subscriptions (pay-per-setup), growth through referrals + branding, what dating data reveals (politics > height), and why AI should scale the matchmaker — not replace human connection.Keywords: AI dating, matchmaking, dating apps, consumer AI startups, venture capital, M13, Sitch, LLMs, OpenAI, relationship tech, seed investing, Stanford GSB, growth marketing.GuestsNandini Mullaji — Co-founder, SitchWhitney Hazard — Investor, M13 (Seed + Series A)Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

In this episode of The Venture Capital Podcast, Jon Bradshaw and Peter Harris are joined by Stine Mølgaard Sørensen, Partner at Alliance VC, a Nordic early-stage fund focused on AI.Stine—an operator and repeat founder turned investor—shares how Nordic venture approaches contrarian vs consensus investing, why Scandinavia can be a powerful “safe launchpad” for startups, and what founders should consider when scaling beyond Europe. The conversation also tackles a question most investors avoid: when should a board member step down—and how do you make that change without blowing up relationships?They also discuss Alliance VC’s portfolio, including 1X (humanoid robots) and Superside, plus what it takes to build real conviction early.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812

AI is changing recruiting faster than most founders realize — and not always in the way they expect.In this episode of The Venture Capital Podcast, we’re joined by Greg Toroosian, Founder & CEO of Samson Rose and host of Machine Minds, to break down how AI, robotics, and automation are reshaping hiring, why resumes are starting to look the same, and what actually matters when evaluating talent in 2025 and beyond.We unpack:Why AI-generated resumes are flooding hiring pipelinesHow recruiters are using AI (and where it breaks)Why startups are struggling to compete with Meta, Google, and Big Tech for talentThe real reasons great candidates ignore outreachHow founders can hire elite engineers without overpayingWhat’s changing in robotics and AI talent marketsWhich robotics companies Greg is most excited about right nowWhether you’re a founder, investor, recruiter, or engineer, this episode is a no-BS look at what’s actually happening in the talent market — and how to stay ahead as AI rewrites the rules.🎧 Listen for practical insights on hiring, retaining top talent, and building teams in the age of AI and robotics.Follow the PodcastInstagram: https://www.instagram.com/venturecapitalfm/Twitter: https://twitter.com/vcpodcastfmLinkedIn: https://www.linkedin.com/company/venturecapitalfm/Spotify: https://open.spotify.com/show/7BQimY8NJ6cr617lqtRr7N?si=ftylo2qHQiCgmT9dfloD_g&nd=1&dlsi=7b868f1b72094351Apple: https://podcasts.apple.com/us/podcast/venture-capital/id1575351789Website: https://www.venturecapital.fm/Follow Jon BradshawLinkedIn: https://www.linkedin.com/in/mrbradshaw/Instagram: https://www.instagram.com/mrjonbradshaw/Twitter: https://twitter.com/mrjonbradshawFollow Peter HarrisLinkedIn: https://www.linkedin.com/in/peterharris1Twitter: https://twitter.com/thevcstudentInstagram: https://instagram.com/shodanpeteYoutube: https://www.youtube.com/@peterharris2812