How He Built 3 Startups, Backed 70+ & Now Advises a $250M VC Fund | Andrew Ackerman - E59

In this episode of Funds and Founders, we sit down with Andrew Ackerman, a seasoned founder, venture studio operator, and author of The Entrepreneur’s Odyssey. Andrew shares real, gritty stories from his journey building startups, transitioning into VC, launching a venture studio, and why he decided to write a novel-style business book that actually teaches while entertaining. He breaks down the harsh truths of buyouts, mistakes first-time founders make, the fundraising game, and the one question every VC is silently asking—why now?

If you're a first-time founder, a startup dreamer, or someone trying to raise your first round—this episode might just save you years of pain.Watch the full episode on  @FundsAndFounders 

Timestamps

00:00 - Intro to Why Andrew wrote The Entrepreneur’s Odyssey

01:15 - The "Goal" book inspiration & startup storytelling

01:59 - How Andrew actually wrote the book

04:11 - Using GenAI for book marketing

08:10 - Prompt engineering and AI frustration

10:56 - Andrew’s unfiltered startup journey

15:00 - The myth of glamorous exits

20:00 - Behind-the-scenes of sourcing Facebook stock

24:15 - Portfolio performance and founder expectations

26:27 - Fundraising truth bombs & understanding VC incentives

28:00 - How VCs actually evaluate founders

30:20 - What Andrew is up to now & why construction tech excites him

32:00 - Thoughts on building standout VC firms

33:30 - The #1 question VCs ask: Why now?

35:05 - Should you build a better version of a mediocre product?

38:00 - Who the book is really for (first-time founders & their moms!)

39:13 - Fundraising advice for first-time founders

41:00 - Why cold emailing VCs doesn’t work

42:30 - How to actually do VC outreach the right way

47:00 - Final thoughts + how to reach Andrew

49:10 - Why most business books suck (and how Andrew wrote differently)

50:16 - Bonus: Get access to his startup masterclasses

54:06 - Closing words from Andrew

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