The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: How I Lost a $125M Deal with Yahoo by Being Too Honest, The M&A Meeting with Steve Jobs That Did Not Go Well and How U2's Bono Saved The Day For One Tech Startup with Ali Partovi, CEO @ Neo

Jan 21, 2022

Ali Partovi, CEO of Neo and early investor in Dropbox and Uber, shares intriguing stories from his career. He recounts how an overly honest conversation cost him a $125M deal with Yahoo and the regrets that followed. Ali also reflects on a challenging meeting with Steve Jobs, discussing the fine line between hype and reality in negotiations. He emphasizes the importance of communication for founders and shares lessons learned from investment misses and high-stakes negotiations, showcasing his journey in the venture capital world.

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ANECDOTE

Lost Yahoo Deal

Ali Partovi lost a $125M Yahoo deal after praising a competitor, Viaweb, to Jerry Yang.
This happened after accepting Yahoo's term sheet, highlighting the importance of discretion in M&A.

INSIGHT

Importance of People

Recognizing talent and potential is crucial, even if it's in a competitor.
Partovi correctly identified Paul Graham's brilliance, emphasizing the importance of people over ideas.

ADVICE

Patience and Alcohol

Avoid alcohol during crucial business discussions, especially M&A negotiations.
Impatience can lead to mistakes; waiting for the right moment is key.

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Ali Partovi is the CEO @ Neo, a mentorship community and communal VC fund that announced their new $150M fund last year on the back of early hits from Fund I including Vanta and Kalshi. As an angel, Ali has made personal investments in Dropbox, Uber, Airbnb, Facebook, Convoy and many more. Prior to investing, Ali founded 2 companies, the first; LinkExchange which he sold to Microsoft for $265M in 1998 and the second, iLike which was acquired by Microsoft in 2009.

In Today’s Episode with Ali Partovi You Will Learn:

1.) How Ali made his way into the world of startups with the founding of his first company? How Ali made his way into angel investing and then starting and raising Neo, as a fund?

2.) How To Kill a $125M By Being Too Honest:

How did Ali lose this $125M with Jerry Yang and Yahoo?
What led Ali to believe that Paul Graham was so special in 1995? What would Ali have done differently with the benefit of hindsight?
How does Ali feel about investment misses today? What are his biggest misses? How has it impacted his mindset and approach to investing?

3.) The Meeting with Steve Jobs Did Not Go Well:

Why did the meeting with Steve Jobs not go well?
What was wrong with the way Ali phrased his final statement? What did this teach Ali about how founders should communicate the difference between hype and reality?
What did this experience teach Ali about how founders should run both fundraising and M&A processes? How does Ali build trust with every touchpoint?

4.) U2, Airbnb and Google at Seed:

How did Bono come to save the day for Ali for his startup in 2009?
What did this teach Ali about how to frame risk and when to go all in vs hold back?
How did Ali miss investing in the seed for Airbnb? How did he make up for it with a later investment?
How did Ali come to miss investing in the Google seed round? Does FOMO haunt Ali today?

Item’s Mentioned In Today’s Episode with Ali Partovi

Ali’s Favourite Book: Sapiens: A Brief History of Humankind