Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173
Avi Eyal (guest), Harry Stebbings (host)
In this episode of The Twenty Minute VC, featuring Avi Eyal and Harry Stebbings, Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173 explores avi Eyal Reveals Monday.com Windfall, Venture Discipline, And Zionism Avi Eyal, co-founder of Entrée Capital, breaks down how a $15M total investment in monday.com turned into over $1.5B in distributions and why one extreme outlier can outweigh a decade of other wins. He explains Entrée’s disciplined, concentrated approach to early-stage venture: a small number of core and “angel” positions, strict rules for selling, and deep, hands-on involvement with founders pre–product-market fit. Eyal outlines his investment framework (technology + TAM to the power of team, multiplied by timing), his aversion to over-capitalized, overvalued rounds, and how he thinks about ownership, signaling risk, and follow-ons in an era of institutionalized mega-funds. The conversation ends with his views on Israel’s political crisis, antisemitism, and the need for a new generation of leadership and moral renewal.
Avi Eyal Reveals Monday.com Windfall, Venture Discipline, And Zionism
Avi Eyal, co-founder of Entrée Capital, breaks down how a $15M total investment in monday.com turned into over $1.5B in distributions and why one extreme outlier can outweigh a decade of other wins. He explains Entrée’s disciplined, concentrated approach to early-stage venture: a small number of core and “angel” positions, strict rules for selling, and deep, hands-on involvement with founders pre–product-market fit. Eyal outlines his investment framework (technology + TAM to the power of team, multiplied by timing), his aversion to over-capitalized, overvalued rounds, and how he thinks about ownership, signaling risk, and follow-ons in an era of institutionalized mega-funds. The conversation ends with his views on Israel’s political crisis, antisemitism, and the need for a new generation of leadership and moral renewal.
Key Takeaways
A few extreme outliers drive venture returns, so you must be in them and size them correctly.
Eyal’s $15M invested into monday. ...
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Use a clear, repeatable investment framework: technology + TAM, powered by team, multiplied by timing.
Entrée evaluates (Technology + TAM) raised to the power of Team, then multiplies by Timing, with team and timing ranked above product and market size; this gives them conviction quickly while staying systematic about what really drives outcomes.
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Avoid over-capitalizing and overpaying early; too much money too soon closes future options.
Eyal dislikes large, high-priced seed rounds (e. ...
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Concentrate in a small number of companies and actively earn your luck through heavy involvement.
Entrée runs funds with ~20–24 companies, splitting “core” and smaller “angel” positions, and spends disproportionate time on core companies, believing that deep operational support, fundraising guidance, and hiring help directly improve odds of success.
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Institutional VCs are public-asset managers in disguise; boutique VCs must play a different game.
As firms like Sequoia and Andreessen manage tens of billions, their attention shifts to very large checks and PE-like targets; Eyal sees an opening for smaller, “artisanal” VCs who can give sustained partner-level attention to sub–$50M positions.
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Impose strict selling rules to avoid falling in love with paper markups.
Entrée typically sells about a third once a holding is 6–8x their entry price, another third at pre-IPO/IPO, and distributes the rest after lockup ends, on the belief that VCs are paid to win in private markets, not to time public stocks.
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Great founders with deep domain knowledge in even modest markets can still build fund-making outcomes.
Eyal prefers insiders who intimately know the problem space and is comfortable backing category leaders in smaller markets, arguing that being #1–2 in revenue and profit in a “non-massive” market can still yield strong exits and multiple reasonable wins make a fund.
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Notable Quotes
“We invested approximately $15 million in Monday and the distribution from that was over one and a half billion dollars.”
— Avi Eyal
“You don't have to win every deal. You just have to win enough of the good deals.”
— Avi Eyal
“High-priced deals with a large amount of capital early in a startup's life close opportunities for it.”
— Avi Eyal
“The point of VC is to get companies to an exit or to get public. It’s not to be a public markets investor.”
— Avi Eyal
“Our returns are top fifth percentile VC returns, but our losses are private equity losses.”
— Avi Eyal
Questions Answered in This Episode
How would Avi’s strict selling discipline have changed outcomes for VCs who held onto overvalued IPOs during the last cycle?
Avi Eyal, co-founder of Entrée Capital, breaks down how a $15M total investment in monday. ...
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In an era of mega-funds, how can smaller managers practically compete to win or maintain ownership in the next monday.com?
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What concrete frameworks can founders use to avoid the trap of raising too much, too expensively, at seed and Series A?
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How might Entrée’s 4T framework need to adapt for AI-native or capital-intensive frontier technologies where timing and TAM are more ambiguous?
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Given his concerns about Israel’s political and social fractures, how does Avi see the future of the Israeli startup ecosystem over the next decade?
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Transcript Preview
Since the beginning of Monday, we invested approximately $15 million. The distribution from that was over one and a half billion dollars. I'll tell you that the next 10 investments that were successful didn't equate to the gain on Monday. You don't have to win every deal. You just have to win enough of the good deals.
Ready to go? Avi, I am so excited for this, dude. Listen, we've been friends for many years. We get to do this in-person, which is so much more special. So thank you so much for joining me.
It's lovely to be here. Thank you for having me.
Not at all. Now listen, man, I think childhood shapes a lot of who we are and how we think. And given we know each other, and we've been for walks in the park, and we have that relationship, I thought I'd just dive straight in. M- my mother's MS and actually my bulimia really shaped a lot of who I am today. When you think about maybe hardships in your childhood, what was the most prominent that shaped how you think today?
So, I didn't have a, uh, extremely challenging childhood. Um, but, uh, I was born in Israel at a tough time, and, um, I grew up in a lower middle class family with a father who was mostly away in the military. At the age of five and a half, I was whisked away by my family, my parents, my, uh, to South Africa, and, uh, pretty much dumped in a school, um, and left, uh, left to figure out a new language, figure out new friends, things like that. And integrate i- i- into, into a new environment. So it caused me to become very independent at a young age, um, and I had to figure out what w- what needed to get done, so I worked hard and, um, and I tried to get results in. And I think that shaped me.
So funny. You know, one of the biggest commonalities in successful entrepreneurs is they moved in childhood. Because you're forced to assimilate with new people, new environments, new cultures, and you have to make it work. And very much like a business with teams, you have to adjust and develop with everyone. And so it's a really interesting kind of commonality. I think there's a question of luck versus skill in this business. I think we're often too fake humble, if I'm honest. (laughs)
(laughs)
Um, where like, "Oh, it's, it's mostly luck." How much of your success would you give to luck versus skill, and how do you think about that?
I can't lie, I have some skill. Um, I was a serial entrepreneur, um, I started a bunch of businesses. Um, but nothing came easy. Um, when my friends at school were surfing and going to the beach on holidays, I was working part-time jobs. I strongly believe that the harder you work, the luckier you get. I would say it's, uh, 20、30% luck.
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