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

from Funds and Founders: Untold Journeys Behind Their Breakthroughs

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  Timestamps00:00 - Intro to Why Andrew wrote The Entrepreneur’s Odyssey01:15 - The "Goal" book inspiration & startup storytelling01:59 - How Andrew actually wrote the book04:11 - Using GenAI for book marketing 08:10 - Prompt engineering and AI frustration10:56 - Andrew’s unfiltered startup journey15:00 - The myth of glamorous exits20:00 - Behind-the-scenes of sourcing Facebook stock24:15 - Portfolio performance and founder expectations26:27 - Fundraising truth bombs & understanding VC incentives28:00 - How VCs actually evaluate founders30:20 - What Andrew is up to now & why construction tech excites him32:00 - Thoughts on building standout VC firms33:30 - 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 founders41:00 - Why cold emailing VCs doesn’t work42:30 - How to actually do VC outreach the right way47:00 - Final thoughts + how to reach Andrew49:10 - Why most business books suck (and how Andrew wrote differently)50:16 - Bonus: Get access to his startup masterclasses54:06 - Closing words from Andrew#vcfunding #podcast #startup #business #entrepreneur #invest #funding

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This episode is 55 minutes long.

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This episode was published on June 10, 2025.

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