))
How He Built 3 Startups, Backed 70+ & Now Advises a $250M VC Fund | Andrew Ackerman - E59
Manage episode 487940424 series 3554714
Content provided by Abhinav Sinha. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Abhinav Sinha or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
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
#vcfunding #podcast #startup #business #entrepreneur #invest #funding
62 episodes
Share
