Avi Eyal on Venture Returns, Selling Discipline and Supporting Founders

Entrée Capital co-founder Avi Eyal tells Harry Stebbings that his firm invested approximately $15 million in monday.com and distributed more than $1.5 billion from the position. He says its next ten successful investments combined did not match that gain, but maintains that a venture investor need not win every deal.

Born in Israel to a lower-middle-class family, Eyal moved to South Africa at five and a half. He describes being placed in a new school and having to learn a language, make friends and find his own way. He believes the experience made him independent and hard-working.

Eyal attributes his success to a mixture of skill, work and luck, estimating luck at 20–30%. His most consequential stroke of luck, he says, was having scuba-diving skills when he survived the 2004 tsunami on Koh Phi Phi. He recalls escaping an underwater hut and helping others.

To make investment decisions quickly, Entrée uses a framework Eyal calls the four Ts: technology, total addressable market, team and timing. He places team first and timing second, with technology and market also important. Experience applying a method can make conviction faster, he says.

He accepts market-timing risk but rejects the idea that an investor can support a company indefinitely. Founders must identify financial milestones and decision points, conserving or deploying capital as conditions change. Fundraising also requires planning which investors or strategic partners to approach and when.

Eyal favors founders with intimate industry knowledge. He cites monday.com’s Roy Mann, Riskified’s founders, PillPack’s TJ Parker and BreezoMeter’s environmental-engineering founder as examples. His preference is an investment judgment, not a guarantee that industry outsiders cannot succeed.

Ownership has to be considered in relation to fund size and outcome. Eyal recalls that Entrée’s PillPack investment, from an $80 million fund, generated roughly $15 million to $20 million in proceeds. It was a contribution to the fund even though the position was not among the largest.

Entrée distinguishes smaller “angel” positions from core investments. A smaller check may give the fund an option to invest more as evidence accumulates, while major successes supply additional multiples. Eyal recalls roughly ten of each type in some early $80 million to $100 million funds.

He says smaller positions can make sense when another capable fund leads, particularly where Entrée would not otherwise win the deal. He claims the firm loses many opportunities it wants and does not need to win them all; the goal is to participate in enough good ones.

BreezoMeter began as a small position, then Entrée led the seed and continued in later rounds as conviction grew. Eyal recalls the business selling for about $250 million and returning roughly $30 million to the fund. He uses it as an example of an angel investment becoming a core holding.

A founder should consider whether a fund leading one round can support the next, especially if conditions deteriorate. At the same time, Eyal acknowledges that successful companies may attract larger firms to lead later rounds. In his view, investors sometimes serve the business best by working together.

He believes signaling risk is real when a prominent early investor does not participate in a subsequent round. He links this partly to large firms’ institutionalization: a small early check may matter little relative to their assets, while later funding decisions have consequences for the startup.

Eyal dislikes high early valuations and large rounds for asset-light companies. He argues that excess capital can weaken financial discipline and narrow future financing options. He makes an exception for capital-intensive businesses such as developing a new GPU, which may genuinely require a much larger seed round.

For a software business able to build an initial product with a small team, he questions whether a $6 million to $8 million early round and the associated dilution are necessary. Entrée’s own investment pace varies, he says, and the firm does not feel compelled to deploy a fixed number of deals quickly.

Eyal says the partners’ personal capital is among the largest commitments in their funds and that they pay management fees. He views that as alignment with limited partners. He also believes limiting the number of core investments allows the team to spend more time helping each company.

Large markets are attractive, but Eyal does not rule out smaller ones. He looks for a company that can become a leading player in revenue and profit, arguing that several reasonable exits can help build a fund’s return. That is his portfolio thesis, not a promise of an exit.

Competitive markets can work if a company controls costs and finds a defensible position, he says, although he is wary of paying up for crowded opportunities. He cites portfolio company SeatGeek’s expansion from ticket sales into software for venues and clubs as an example of a deeper wedge.

If he loves a founder but dislikes the market, Eyal tries to explain his concern and might back the founder in a different opportunity. He also points to monday.com as a business that began with a general product and expanded into more specific areas, including development and customer relationship management.

Eyal’s conviction in monday.com drew on a governance and compliance software company he had built. He had wanted a horizontal product but faced the technical limits of the early 2000s. When he saw monday.com, he recognized a more fully realized version of that idea, enabled by newer infrastructure.

Entrée participated in monday.com’s first round and later supported it with additional financing. Eyal says other investors compared it to existing collaboration products or worried about a lack of enterprise clients. He recalls pushing to keep funding the company when others did not share his view.

A potential outside Series A lead did not materialize. Eyal does not give the reasons; he says Entrée stepped up in a roughly $6 million round, contributing about $1.5 million to $2 million. The company had struggled to find product-market fit in its first eight or nine months and at one point had only about six customers and six months of cash.

After the company gained traction, he believes it could perhaps have moved into enterprise about a year earlier. Entrée remained a large shareholder as later investors joined, and Eyal says he continued as a board member after the company became public. His perspective is shaped by that investment and role.

Eyal estimates Entrée invested about $15 million in monday.com over time and distributed more than $1.5 billion. Stebbings points to the exceptional nature of the return. Eyal credits commitment to helping the company succeed while also acknowledging the good fortune involved.

To avoid falling in love with paper gains, Entrée adopted a staged sale discipline. Eyal describes an illustrative first sale of about a third after a substantial increase in price, another around a pre-IPO round or IPO, and a sale or distribution of the rest when the public-market lockup expires. He does not disclose an exact trigger.

He says the approach helped in Cazoo: the firm sold part before the IPO, about 10% at the IPO because of constraints, and distributed shares after the lockup. He declines to give an exact return. The amounts and values are his recollection, not a complete transaction record.

On Stripe, Eyal says he and Designer Fund’s Ben had each exited close to or about 50% of their holdings by the time of the interview. Entrée was also an investor in Designer Fund. This differs from the video description’s claim of a complete exit; the interview itself supports the approximately half-sold account.

Eyal argues that knowing a private company well does not make a venture investor an expert in how its public stock will trade. Public-market prices respond to many other participants and expectations. In his view, a venture fund’s core competence is helping a company reach liquidity, not managing public securities indefinitely.

He sees an opportunity for smaller venture firms as large managers become more institutional. A smaller fund can devote attention to positions that are modest in absolute dollars. His claim also reflects Entrée’s own business model and positioning.

Founders differ in how much investor help they need. Eyal says Entrée was deeply involved with monday.com early, then became less involved as the company matured. He values experienced mentors because they helped him as a founder, while acknowledging that not every founder needs the same support.

Stebbings argues that investors can help before product-market fit by sharpening customer focus and acquisition strategy; Eyal agrees. He describes helping a technically strong founder recruit and prepare for a Series A, while emphasizing that the founder still did the work.

The best CEO is not necessarily the best fundraiser, Eyal says. Raising capital is valuable but distinct from building a product, hiring and winning customers. Stebbings adds that communicating with investors can require a different language from selling to employees or customers.

His largest investment loss, he says, was about $4.5 million in Harvest Automation, a robotics company founded by former iRobot engineers. Eyal was captivated by the technology but did not understand agriculture well enough. He believes he misjudged both the market and the founders’ fit for it.

When conviction in a founder weakens, Eyal favors an honest conversation. He says explaining concerns and listening to the founder can reset expectations on both sides, even if they disagree. Stebbings questions whether such a conversation always helps; Eyal sees value in clarity.

Eyal says monday.com’s gain exceeded the combined gains of the next ten successful investments. He resists the idea that venture must consist of almost all failures and one winner: in his analogy, a good restaurant has a few exceptional dishes and many good ones.

He reports that older Entrée funds had matured loss rates around 12–15%, as assessed in a fund-of-funds review, and says one approximately $45 million fund had about 38 times distributed capital while two $80 million funds were around 5.6 times. These are his time-specific reported fund figures; the conversation does not independently verify them.

Of sourcing, selecting and servicing, Eyal thinks Entrée could improve sourcing and is strong at supporting companies. His desire to improve, he says, partly comes from strict parental expectations and feeling that he was not praised enough.

As a parent, he tries to preserve what was good in his upbringing and avoid what was not. With older children, he says, parents can mistake a request for wisdom as an invitation to control. He wants to trust the values he has passed on while offering advice.

On missed investments, Eyal recalls discussing a possible SAFE with Lemonade’s founder after its Series A, then forgetting to follow up after a trip. He does not know whether the founder would ultimately have accepted. His lesson is to record a clear owner, action and deadline rather than rely on memory.

He says mistakes are inevitable; what matters is learning to handle them. He is broadly at peace with the experience of building Entrée, even though he would have made some decisions differently.

The conversation turns to Israel, the October 7 attack and antisemitism. Speaking as an Israeli and a Zionist, Eyal criticizes what he sees as divisions, self-interest and failures in Israeli civil society and government. He calls for empathy, accountability and a new generation of leadership; these are his political judgments.

He describes antisemitism as a longstanding hatred and argues that some hostility toward Israel is connected to hostility toward Jewish self-determination. This is his interpretation; criticism of Israeli government policy or military conduct is not inherently antisemitic. The discussion does not establish that all criticism shares one motive.

Asked about the future of Israelis and Palestinians, Eyal calls for defined borders, effective leadership on both sides and agreements that can promote peace. He says he supports assistance for evacuees, hostages, soldiers’ families and Israel’s defense, but does not claim to know a complete solution.

In the quick-fire round, Eyal says he sees the world as more dangerous and believes Israel’s startup ecosystem was beginning to recover, while still having a long way to go. Those assessments were made at the time of the conversation.

He criticizes treating potential future customer usage as if it were already contracted recurring revenue. He also warns that first-time founders can underestimate burn and overestimate their capabilities, and that capital should be deployed with a plan for eventual returns.

Asked where he hopes to be in ten years, Eyal imagines time on the beach with his wife, grown children and dogs. Stebbings suspects he would soon look for another deal; Eyal says he looks forward to being bored.