From Scaling DreamIt Ventures to Making 70+ Startup Bets
When most founders think of venture capital, they picture gatekeepers. But Andrew Ackerman flips that script. In this episode, the Dreamit Ventures and Second Century Ventures partner reveals how he went from running startups to leading one of the most respected accelerators in the country, and the mindset shift founders need to attract real investors.
He breaks down the real pathway into VC, why most angel investors fail, and how Dreamit helped scale hundreds of startups across PropTech and EdTech. Andrew’s “luck and purpose” philosophy is something every founder raising capital should hear.
🎧 Watch the full episode to learn how to scale your company — and your career — the Dreamit way.
👉 Watch now: YouTube link
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
ABOUT Andrew Ackerman
Andrew Ackerman is a veteran venture capitalist and startup accelerator leader who’s helped scale hundreds of early-stage companies. As a Managing Director at Dreamit Ventures, he launched and led programs in EdTech, PropTech, and ConstructionTech, driving Dreamit’s growth into a top-tier accelerator. Today, Andrew is a Partner at Second Century Ventures, one of the most active PropTech investors globally, where he backs category-defining founders at the intersection of real estate and technology
Get in touch with Andrew:
🔗 Connect with Andrew on LinkedIn
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