EP 98: How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets

What really happens when a founder crosses the table to become an investor?In this episode, Andrew Ackerman, former Managing Director at DreamIt Ventures and author of The Entrepreneur’s Odyssey, joins Jason to discuss what he has learned backing more than 70 startups across ed-tech, prop-tech, and beyond.Andrew shares how he went from writing angel checks that disappeared to running one of the top accelerators in the U.S. He breaks down what founders get wrong about “value-add” programs, how he built a deal-flow system that attracted over 1,000 startups for just 12 spots, and what separates truly scalable founders from the rest.He also breaks down how to spot real accelerator ROI, why most programs aren’t worth it, and how experienced founders think differently about equity, advisors, and long-term value creation.Here’s what you’re in for:00:00 Introduction and Guest Introduction00:04 Andrew's Transition from Founder to Investor00:52 Early Angel Investment Experiences02:43 Joining DreamIt Ventures07:18 The Evolution of Startup Accelerators13:43 Selecting Startups for DreamIt26:15 Evaluating Startup Teams27:10 Switching Focus: From EdTech to PropTech32:17 Challenges in Accelerator Programs42:56 The Entrepreneur's Odyssey: A Novel Approach50:52 Connecting with Andrew AckermanRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode98&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode98&utm_id=%24100M++ExitsABOUT ANDREW ACKERMANAndrew Ackerman is a VC, SPV syndicate sponsor, and former Managing Director at DreamIt Ventures, with over a decade of startup investing and 70+ portfolio companies. A former founder turned investor, he’s built and scaled verticals in EdTech, PropTech, and ConstructionTech, creating DreamIt’s Customer and Investor Sprint programs to help startups raise capital and close enterprise deals faster. Andrew has advised CVCs, developers, and corporate innovation teams worldwide and published 60+ articles in Forbes, Fortune, AlleyWatch, and Propmodo.You can reach out to Andrew through:LinkedIn: https://www.linkedin.com/in/andrewbackerman/ Website: https://www.andrewbackerman.com/ Email: [email protected]  (Subject line: “Fundraising Demystified Listener”)ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.