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

Raising capital?

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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. He’s transacted over $135M and his firm Thunder has transacted over $200M+.

You can reach out to Jason through:

Email: jason@thunder.vc

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My 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.