#565 Startups Are Chains, Not Ropes: Lessons from 70+ Investments with Andrew Ackerman

In this episode, Mehmet sits down with Andrew Ackerman, two-time founder, early-stage investor with 70+ investments, accelerator leader, entrepreneurship professor, and author of The Entrepreneur’s Odyssey.

Andrew shares hard-earned insights from running accelerator programs, investing across decades, and coaching founders at their most fragile moments. The conversation dives deep into why startups fail, what truly separates winning founders, how coachability beats ego, and why storytelling is more powerful than advice.

They also explore how AI is reshaping entrepreneurship, why the bar for founders keeps rising, and why building faster is no longer a competitive advantage on its own.

⸻

👤 About the Guest

Andrew Ackerman is a seasoned entrepreneur, investor, educator, and author.

• Two-time startup founder

• Investor in 70+ early-stage companies

• Former accelerator leader (DreamIt)

• Entrepreneurship professor

• Author of The Entrepreneur’s Odyssey: A Novel Approach to Startup Success

Andrew has spent decades working at the intersection of founders, investors, and large enterprises, giving him a rare inside view of what actually makes startups succeed or fail.

http://www.linkedin.com/in/andrewbackerman

⸻

🧠 Key Takeaways

• Startups fail due to broken links, not a single bad idea

• Coachability matters more than confidence or experience

• The best founders hold strong opinions loosely

• Storytelling drives action better than direct advice

• AI lowers the cost of building, but raises the bar for funding

• First-mover advantage is weak without a real moat

• Empathy is the hidden superpower behind great founders, salespeople, and storytellers

⸻

🎓 What You’ll Learn

• Why startups should be viewed as chains, not ropes

• How accelerators compress the learning curve for investors and founders

• How to spot coachable founders early

• Why experimentation beats gut instinct

• How to test ideas cheaply before building

• Why many founders hide in their comfort zone instead of doing the hard work

• How AI changes the “why now” question for startups

⸻

⏱️ Episode Highlights & Timestamps

00:00 – Introduction and Andrew’s background

03:00 – Why running an accelerator changes how you see startups

07:00 – Angel investing vs accelerator investing

10:00 – Startups as chains, not ropes

12:30 – Why startups fail in different ways

14:30 – The one trait that separates great founders

18:00 – Coachability, ego, and founder decision-making

22:00 – Can entrepreneurship really be taught?

25:00 – The “looking for money under the streetlight” founder trap

28:00 – Why storytelling beats direct advice

32:00 – SeatGeek origin story and early validation lessons

36:00 – Empathy as a core founder skill

40:00 – AI, hype, and what’s actually changing for startups

45:00 – Why the investor bar keeps rising

50:00 – Final advice for founders and investors

⸻

📚 Resources Mentioned

• The Entrepreneur’s Odyssey by Andrew Ackerman: https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0

• Andrew’s website: https://www.andrewbackerman.com/