Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173

Financial Performance & Strategy

• Entrez invested approximately $15 million in Monday.com over its lifecycle, resulting in a distribution exceeding $1.5 billion.
• The fund operates on a model where the single best return (Monday) vastly outweighs the aggregate gains of the next ten successful investments combined.
• Entrez manages a portfolio concentration of roughly 23–24 companies per fund, rejecting the "spray and pray" approach of holding 30+ seed deals.
• Funds utilize an "angel and core" strategy, deploying smaller checks ($250k+) in angel deals to gain optionality for follow-on leadership in core deals.
• The firm maintains a loss rate of 12% to 15% across its mature funds (10–13 years old), despite critics arguing they do not take enough risk.
• The best-performing fund achieved a DPI (Distributions to Paid-In) of 38x, while two $80 million funds achieved a DPI of 5x–6x.

Investment Thesis & Methodology

• Entrez employs the "Four Ts" valuation formula: (Technology + TAM)^(Team^2) × Timing, with Team prioritized as the primary factor, followed by Timing, then Technology and TAM.
• Avi Aviram rejects the reliance on market "size" over "quality," preferring to back founders who can dominate a smaller market as a number one or number two revenue/profit player.
• The firm favors insiders with intimate industry knowledge over outsiders with "naivety," citing successes like Roy Mann (Monday.com), Ido (Riskified), and Ron Cohen (Breezometer).
• Aviram argues against high pre-valuation seed rounds in Israel ($6M–$12M on $15M+ pre-money), asserting that excessive early capital creates unnecessary dilution and reduces the incentive for lean operational execution.
• The firm actively leads Series A rounds for companies where previous tier-one investors lacked conviction, citing their ability to sustain capital through financing droughts.

Operational Philosophy & Founder Relations

• Aviram views early-stage VC engagement as critical for guiding product-market fit, specifically helping founders narrow their ICP (Ideal Customer Profile) and acquisition channels.
• The firm enforces strict exit discipline: selling one-third of positions when valuations rise 6x–8x, selling another third at pre-IPO, and distributing the remainder post-lockup to avoid the risks of public market speculation.
• Aviram admits to losing 100% of capital ($4.5M) in a 2010 robotics investment (Harvest Automation) due to falling in love with the technology rather than understanding the ag-tech market dynamics.
• Entrez acts as its own largest Limited Partner (LP), ensuring alignment and allowing the firm to invest at its own pace without pressure to build Assets Under Management (AUM).
• Aviram believes that "price is a mental trap," warning that expensive deals at early stages limit future fundraising permutations and foster poor decision-making.

Market Outlook & Geopolitical Stance

• Aviram identifies a shift in venture capital from a boutique industry to an "institutionalized, commoditized asset class" dominated by mega-funds (Sequoia, a16z) that treat early checks as a fraction of massive funds.
• He expresses deep concern over the fragmentation of Israeli civil society, attributing it to misaligned expectations between population segments and a failure to maintain collective morality.
• Aviram characterizes modern anti-Semitism as a direct response to Israel's existence as a nation-state, framing it as the "canary in the coal mine" for broader societal hatred.
• He calls for a new generation of Israeli leadership (ages 18–30, comprising 25% of the population) to replace current political structures and drive a vision based on empathy, tolerance, and fixed borders for peace.
• Aviram asserts that the Israeli startup ecosystem is not dead, noting that capital flows are already returning, though full recovery remains a work in progress.

Personal Drivers & Future Outlook

• Aviram credits his independence and work ethic to being sent to school in South Africa at age five and a half, where he had to integrate into a new culture and language without parental support.
• He attributes the survival of himself and others during the 2004 Indian Ocean tsunami to his prior scuba diving training, which allowed him to escape an underwater hut.
• Aviram rejects the notion that VCs should "get in and get out" without engagement, arguing that founder-VC partnerships are essential for navigating the early stages of business growth.
• He defines success in parenting by his adult children actively choosing to spend time with him, noting the danger of parents inadvertently shifting from providing wisdom to exerting control.
• Aviram states his personal goal for the next decade is to retire to the beach with his wife and adult children, though he acknowledges he will likely remain active in deal-making out of passion.