Episode 60

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

Published on: 10th June, 2025

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

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About the Podcast

Funds and Founders: Untold Journeys Behind Their Breakthroughs
Welcome to "Funds & Founders: Untold Journeys Behind Their Breakthroughs," where we dig deep into the stories of successful Austin founders. Instead of focusing on their successes though, we dive into their journeys, particularly the struggles and obstacles they had to overcome.

This weekly podcast is tailored for Austin founders navigating the early stages of their entrepreneurial journey and hosted by fellow Austinite Abhinav Sinha. Here’s what to expect by tuning into Funds & Founders:

🚀 Embark on a Journey to Success
Join Abhinav as he takes you behind the scenes, exploring the highs and lows of building a company. This isn't your typical success story – we dive into the failures, the struggles, and those pivotal breakthrough moments that define a founder's path.

🌟 Real Conversations, Real Insights
Abhinav's approach is refreshingly different. Rather than dwelling on success, he crafts casual conversations that unravel the untold stories. Identify the setbacks that helped them grow, the lessons learned from failures, and the breakthrough moments that fueled these founders.

🤔 Why Didn't They Quit? Learn and Apply.
At the heart of each episode, Abhinav delves into the 'why' behind the perseverance. Why didn't they throw in the towel during tough times? And, most importantly, how can you apply their insights to your own journey? Get ready to be inspired and equipped with practical takeaways for your entrepreneurial adventure.

🤝 Decoding Venture Capital
Ever wondered what goes on in the minds of Austin's venture capitalists? Abhinav sits down with local VCs to decode their criteria for investing in early-stage companies. Gain valuable insights into the world of venture capital, understand what investors look for, and appreciate the vital factor of founder-investor compatibility.

🎙️ Meet Your Host, Abhinav Sinha:
Abhinav's soft-spoken yet inquisitive style creates an intimate atmosphere, allowing guests to share their authentic stories. His genuine curiosity and insightful questions make each episode a captivating journey into the minds of Austin's most successful founders.

If you're a budding Austin entrepreneur seeking the inspiration and insight needed for building a successful company, "Funds & Founders" is your go-to podcast.