20VC: Turning a $15M Investment in Monday into $1.5BN in Cash | The Strategy Behind a 37x DPI $45M Fund | The Three Step Process to Selling Positions that has Netted Top Percentile Returns with Avi Eyal, Co-Founder @ Entrée Capital

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

The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 3 July 2024

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

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Summary

Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about.

In Today's Episode with Avi Eyal We Discuss:

1. The Biggest BS "Rules" in Venture Capital:

Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund?
Why does Avi believe that signalling is real and it is BS to suggest otherwise?
Why does Avi believe that it is BS that ownership is crucial to make mega venture returns?
Why does Avi believe that you do not have to win every deal to be one of the best in venture?
Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public?

2. What Makes the Best Founders:

Does Avi prefer first or second time entrepreneurs? Why?
Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard?
Are the best CEOs the best fundraisers?
How does Avi rank the following when investing; team, market, traction and technology?
When Avi has misread a founder, what was it that he missed?

3. The Biggest Hits and Biggest Misses:

Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree?
Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount?
PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership?
Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?

Transcript

Click on a timestamp to play from that location

0:00.0	Since the beginning of Monday, we invested approximately $15 million.
0:04.2	The distribution from that was over $1.5 billion.
0:08.0	I'll tell you that the next 10 investments that were successful didn't equate to the gain on Monday.
0:14.5	You don't have to win every deal.
0:16.0	You just have to win enough of the good deals.
0:18.3	This is 20 VC with me, Harry Stbbings, and I could not be more
0:21.4	excited for the show today. Our guest is one of the greatest venture investors that you might not
0:26.4	have heard of. He turned a $15 million investment into $1.5 billion in cash. He has a 37x
0:35.1	DPI, 37X on a $45 million fund. I'm thrilled to welcome a dear friend of mine,
0:42.4	Avi IL, co-founder and managing partner of Entree Capital. I'd also want to say Avi has been a
0:48.0	long-term supporter of mine in 20 VCs, and I so appreciate our relationship, Avi. But before we
0:53.7	dive in today, all of you listening
0:55.5	use tons of software every day. Sometimes it fills us with rage. You can't figure something
1:00.4	out. The chatbot in the bottom right is useless. You keep getting bombarded with these
1:04.4	useless pop-ups. And for those of you who build products, no one wants their product to feel like
1:09.2	this. Thankfully, a company exists to help users without annoying them. Command Bar. It does a couple of very helpful things. First, it's a chatbot that uses AI to give users extremely personalised responses and deflect tickets. But it can be beyond just text. It can also co-brows with the user and show them how to do things inside the UI, magic.
1:29.1	But it can also detect when users would benefit from a proactive nudge, like a helpful hint,
1:33.7	or an invitation to start a free trial.
1:35.6	Command Bar is already used by world-class companies like Gusto, Hashikorp, Yotpo and Angelist.
1:41.1	If you're a product CX or marketing leader, check them out at command bar.com
1:45.4	slash harry. And talking about incredible companies with Commandbar, we need to talk about the
1:50.6	information. When a promising startup files for an IPO or a venture capital firm loses
	...

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