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The Twenty Minute VCAvi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173
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At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasA few extreme outliers drive venture returns, so you must be in them and size them correctly.
Eyal’s $15M invested into monday.com returning over $1.5B illustrates how one company can outweigh the next ten winners combined; portfolio construction must assume a power-law and be designed so you can own and double down on those rare breakouts.
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.
Avoid over-capitalizing and overpaying early; too much money too soon closes future options.
Eyal dislikes large, high-priced seed rounds (e.g., $6–8M on relatively high pre-money) because they encourage sloppy decision-making, unnecessary burn, and make later fundraising and exit paths harder to achieve at attractive multiples.
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.
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.
WORDS WORTH SAVING
5 quotesWe 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
High quality AI-generated summary created from speaker-labeled transcript.
