DrinksWithAVC (DWAVC)
Grab a drink and join Vik (Green Cow Venture Capital) and Bree (Cooley) as they sit down with top venture capitalists to uncover the stories behind the spreadsheets. Each episode blends laughter, quirks, and candid conversation with practical frameworks founders can use to build, grow, and fundraise more successfully.
If you’re a startup founder, VC, or LP, this show helps you get to know the people you may be partnering with for the next 7–10 years. From Tuvan throat singing and mini piano playing to our signature “Fidelity Five” lightning round, you’ll discover surprising sides of the investors shaping the startup ecosystem.
We feature leaders from powerhouse firms like Bessemer, Costanoa, Scale VP, and Lightspeed, as well as emerging funds such as Touring, Better Tomorrow Ventures, Hustle Fund, and Precursor. Expect founder-tested advice, real talk about venture, and plenty of laughs along the way.
New episodes drop monthly. Pour your favorite drink and dive in.
DrinksWithAVC (DWAVC)
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
📊 Cap table management needs? Check out Fidelity Private Shares
🚀 Fundraising help: Download The Irresistible Startup
🤖 …or meet Ira, the Irresistible Startup Bot
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