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EP 98: How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets
Description
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 Introduction
00:04 Andrew's Transition from Founder to Investor
00:52 Early Angel Investment Experiences
02:43 Joining DreamIt Ventures
07:18 The Evolution of Startup Accelerators
13:43 Selecting Startups for DreamIt
26:15 Evaluating Startup Teams
27:10 Switching Focus: From EdTech to PropTech
32:17 Challenges in Accelerator Programs
42:56 The Entrepreneur's Odyssey: A Novel Approach
50:52 Connecting with Andrew Ackerman
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ABOUT ANDREW ACKERMAN
Andrew 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: andrewbackerman@gmail.com (Subject line: “Fundraising Demystified Listener”)
ABOUT JASON KIRBY
Jason 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.