The Twenty Minute VCAvi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173
CHAPTERS
- 0:00 – 0:41
Monday.com’s outlier return: $15M in, $1.5B+ back
Avi opens with the core VC lesson from his biggest win: Monday.com returned over $1.5B in distributions on roughly $15M invested. He frames venture as an outlier-driven business where a single breakout can dwarf the next decade of successes combined.
- •$15M invested in Monday.com yielded $1.5B+ distributed
- •Outliers dominate fund outcomes; you don’t need to win every deal
- •Portfolio success is about winning enough of the right deals
- •Sets up the discussion on conviction, construction, and liquidity discipline
- 0:41 – 1:51
Becoming independent early: moving countries and learning to adapt
Harry and Avi discuss how childhood experiences shape decision-making. Avi describes moving from Israel to South Africa at age five and having to quickly adjust to a new language, school, and social environment, building independence and resilience.
- •Relocation forced early self-reliance and social adaptation
- •Lower middle-class upbringing; father often away in the military
- •Hard work and independence as enduring traits
- •Connection between childhood assimilation and later business adaptability
- 1:51 – 3:39
Luck vs skill—and surviving the 2004 tsunami
Avi rejects performative humility: skill matters, and hard work increases ‘luck.’ He shares his most ‘lucky’ moment outside business—surviving the 2004 tsunami in Ko Phi Phi due to scuba training, and helping others escape drowning.
- •Avi’s view: ~20–30% luck, the rest effort/skill
- •‘The harder you work, the luckier you get’ mindset
- •Tsunami survival story tied to scuba diving skills
- •Luck framed as preparation meeting extreme events
- 3:39 – 5:23
Speed of conviction in VC: the ‘four Ts’ decision method
The conversation shifts to Avi’s reputation for fast conviction on deals. He explains Entrée Capital’s evaluation framework (team, timing, technology, and TAM) and how a repeatable method enables quicker decisions.
- •Fast conviction is enabled by a practiced decision method
- •Framework prioritizes team first, then timing, then technology/TAM
- •Patient capital can underwrite market timing risk
- •Conviction must still be paired with structured milestones
- 5:23 – 6:34
Keeping companies alive through financing droughts: milestones and forks
Avi explains that you can’t fund a company forever, but you can plan for different paths. He emphasizes financial planning, capital conservation vs acceleration, and identifying milestone ‘forks’ where strategic decisions change survival odds.
- •Survival depends on planning milestones and decision points
- •Capital can be conserved or deployed faster depending on signals
- •Fundraising strategy: which investors to approach, when, and why
- •Luck still matters, but preparation improves odds
- 6:34 – 7:37
Insider founders vs outsiders: why domain intimacy wins
Harry probes whether the best founders are insiders to a market or naive outsiders. Avi strongly prefers founders with intimate industry knowledge, citing examples like Monday.com, Riskified, PillPack, and BreezoMeter.
- •Preference for founders with deep domain context
- •Examples: Roy Mann (Monday), Iddo (Riskified), TJ Parker (PillPack)
- •Founder-market fit increases probability of execution
- •Long struggles can still become wins (BreezoMeter’s multi-year grind)
- 7:37 – 11:32
Angel vs core deals: ownership, portfolio construction, and optionality
Avi describes how smaller funds can generate meaningful returns without massive ownership in every winner. He outlines Entrée’s split between ‘angel’ (small checks, optionality) and ‘core’ (higher-conviction, higher-effort) investments, and why they keep portfolio count relatively tight.
- •Small fund math: large outcomes don’t always require large ownership
- •Portfolio model: roughly 10 angel + 10 core in earlier funds
- •Angel deals offer optionality via pro-rata as conviction grows
- •They avoid too many companies because they actively ‘work’ them
- 11:32 – 12:27
Graduating an angel deal into a core winner: BreezoMeter case study
Avi gives a concrete example of starting with a small check when conviction is lukewarm, then increasing exposure as execution proves out. BreezoMeter moved from pre-seed participation to leading seed and following through later rounds, ultimately selling for $250M.
- •Initial small check (~$250K) without leading pre-seed
- •Conviction grew; Entrée led seed and continued through A/B
- •Achieved largest ownership position (~17–18%)
- •Exit: $250M sale; ~$30M+ returned
- 12:27 – 15:15
Competing with mega-funds: signaling risk and why ‘playing together’ matters
They discuss the risk that tier-one funds can outcompete smaller investors for follow-on rounds and the signaling damage when a big-name seed investor doesn’t support the next round. Avi argues the institutionalization of VC changes incentives and founders must plan for investor capacity across cycles.
- •Founder preference: A-round fund should be able to lead B-round too
- •Signaling risk is real if a large seed fund doesn’t follow
- •Mega-funds write early checks easily because they’re immaterial to fund size
- •Smaller/boutique VCs can provide attention and consistency
- 15:15 – 20:08
Valuation discipline: why expensive early rounds reduce future options
Avi lays out his aversion to high-priced early deals and oversized rounds, arguing they encourage poor operating discipline and constrain future fundraising permutations. They also debate Israel’s typical seed pricing and dilution norms, with Avi pushing ‘do more with less’ for asset-light startups.
- •High valuations + lots of early capital can distort decision-making
- •Expensive rounds reduce future fundraising flexibility
- •Israel market context: common $6–12M raises at $15–40M pre
- •Exception: capital-intensive businesses (e.g., hardware/GPU-like)
- 20:08 – 23:59
Markets, TAM, and competition: win by being #1/#2 or finding a wedge
Avi argues that massive markets are helpful but not mandatory if a company can become #1 or #2 in a smaller market with real revenue/profit. On competitive markets, he’s cautious but points to wedge strategies (SeatGeek infrastructure, Monday’s later product lines) as ways to build advantage.
- •TAM is secondary to building a top position with real economics
- •Smaller markets can still produce strong exits and fund returns
- •Competitive markets require cost control and a clear path to winning
- •Wedge strategy examples: SeatGeek (systems), Monday (Dev/CRM expansions)
- 23:59 – 30:24
The Monday.com journey: early skepticism, funding gaps, and PMF breakthrough
Avi explains why he believed in Monday.com when many investors dismissed it as ‘Yammer/Slack’ or too SMB-focused. He recounts stepping in when funding fell through, the early period without PMF, the eventual enterprise push, and why the absence of tier-one conviction left Entrée as a large shareholder.
- •Avi saw Monday as the horizontal platform he wanted to build earlier
- •First round was ~$1.5M; he pushed hard to continue funding
- •Early struggle: 8–9 months without PMF, few customers, limited runway
- •Stepped up to help make the A-round happen; later Insight led the B
- •Result: ~$15M invested over time, $1.5B+ distributed; board role today
- 30:24 – 36:16
Getting out matters: rules for selling, IPO lockups, and Stripe/Cazoo examples
Avi shares Entrée’s explicit liquidity principles to avoid ‘falling in love’ with paper gains: sell portions at major price step-ups, trim around IPO, and exit/distribute after lockup. He applies the logic to Cazoo’s run-up and to Stripe secondary selling, rejecting the idea that VCs have an edge as public-stock holders.
- •Rule-based selling: trim after ~6–8x step-up; trim pre/at IPO; sell/distribute post-lockup
- •VC competence is building to liquidity—not managing public-market trading dynamics
- •Cazoo: sold some pre-IPO; limited IPO selling; distributed after lockup despite price drop
- •Stripe: exited close to ~50% of holdings via secondaries
- •Public-market ‘asymmetric information’ claim dismissed as dangerous/false
- 36:16 – 41:35
VC value-add before PMF: hiring, fundraising coaching, and the boutique advantage
They discuss whether founders want investor help and where VCs can be most useful. Avi argues early-stage companies benefit from mentorship and targeted support—like hiring assistance and fundraising strategy—especially from smaller funds that can spend real time versus institutional giants.
- •Founder needs change over time: high-touch early, lighter-touch later
- •Pre-PMF help: ICP focus, hiring support, fundraising planning and sequencing
- •Example: supporting a highly technical founder who struggled with hiring and fundraising
- •Institutionalized mega-funds vs boutique VCs: attention and craft as differentiation
- 41:35 – 53:37
Mistakes, misses, and operating cadence: product love, founder fit, and ‘who/what/when’
Avi details his biggest loss (Harvest Automation) as a case of falling in love with product/engineering without understanding market and founder-market fit. He also shares a painful miss (forgetting to invest in Lemonade) and the operational principle he pushes—capturing actions with clear ownership and deadlines.
- •Biggest loss: ~$4.5M into Harvest Automation, total loss
- •Core error: engineering fascination outweighed market/founder assessment
- •Hard conversations with founders reset expectations and relationships
- •Big miss: failed to follow through on Lemonade post-A opportunity
- •Operating mantra: ‘who, what, when’ to create action-oriented culture
- 53:37 – 1:03:02
Israel, leadership, and antisemitism: civil society strain and long-term path forward
Avi explains why he’s become more engaged around Israel’s situation post-2022 politics and post–Oct 7, describing a fraying social fabric, governance issues, and the need for a new generation of leaders. He connects modern antisemitism to opposition to Jewish self-determination, and outlines broad conditions he believes are necessary for a future peace trajectory.
- •Israel’s civil society: misaligned contributions/expectations, corruption concerns, weakening services
- •Belief that insufficient lessons have been learned post–Oct 7; need for empathy/tolerance/morality
- •Call for new leadership driven by younger voters; older generation to provide wisdom not control
- •Antisemitism framed as persistent historically, now often expressed through anti-Zionism
- •Long-term: fixed borders, real Palestinian leadership, and mature agreements toward peace
- 1:03:02 – 1:05:51
Quick-fire: worldview shifts, founder errors, and what Avi wants next
In rapid Q&A, Avi says the world feels more dangerous, rejects the idea Israel’s startup ecosystem is ‘done,’ and shares his best advice about psychology and complacency. He critiques ‘contracted ARR’ as misleading, identifies common founder errors, and closes with a personal vision of family time—while acknowledging he may need boredom after years of intensity.
- •Mind changed: the world is more dangerous than he assumed
- •Israeli ecosystem: starting to bounce back but recovery is ongoing
- •Best advice: psychology matters; complacency kills
- •Bad advice: inflated ‘contracted ARR’ comparisons
- •Common founder mistake: underestimate burn, overestimate capability
