DWAVC: Andrew Ackerman | Ep. 36

What do tiddlywinks, a quarter trick, and a failed Palantir deal have in common? They all show up in Andrew Ackerman’s one-of-a-kind path from founder to family office director, accelerator operator, and venture capitalist to now SPV syndicate lead and author.   Andrew pulls no punches on what most startups get wrong — from pitch decks that waste space to market slides that make investors roll their eyes. He shares lessons learned from backing 70+ startups on how to actually stand out in a noisy fundraising environment, why EdTech broke his heart, and how day drinking helped him write The Entrepreneur’s Odyssey — a startup guide founders might actually finish. Also in this episode: - His “accidental” real estate empire - EdTech’s big COVID moment (and what came after) - The one thing every founder should know about market sizing - And yes, Andrew answers the Fidelity Five Questions. If you’ve ever wondered what VCs really think when they see your deck — this one’s for you! Episode links: www.AndrewBAckerman.com Entrepreneur"s Odyssey Episode timestamps: 00:00 DWAVC Episode: Andrew Ackerman 03:28 Guest Introduction and Background 05:25 March Madness Predictions 07:42 Andrew"s Origin Story 16:18 Parenting in the Digital Age 30:27 Andrew"s Unique Skills 31:01 Discussing the New Book 31:52 Inspiration Behind the Book 32:15 Writing Process and Challenges 37:23 Character Development 40:37 Market Sizing and Go-to-Market Strategies 44:14 Importance of Value Proposition 01:13:52 Fundraising Insights 01:15:27 Navigating VC Funding Strategies 01:17:19 Challenges for Non-Ivy League Founders 01:20:09 Importance of Warm Intros 01:22:33 Accessing Capital Outside Major Hubs 01:24:37 The Role of Location in Startup Success 01:27:09 Influence of Science Fiction on Entrepreneurship 01:29:56 The Rise of PropTech 01:41:28 Fidelity Five Questions