Feb 2, 2026 · 1h 15m · 20vc
Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
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In this deep-dive interview, veteran solo capitalist Oren Zeev challenges mainstream venture capital conventions, detailing his contrarian investment philosophy, his pragmatic outlook on the AI revolution, and the critical structural misalignments between LPs and GPs in today's market.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 15.4% of the talking time here. How this is scored →
Harry as informed peer 4.6 Guest teaching 4.6 Guest disagreement 3.4 Harry pushing back 3.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:41 Disregarding LP vintage concerns
When Harry brings up LP complaints regarding fast deployment pace and lack of vintage diversification, Oren unhesitatingly agrees that he doesn't give a shit, telling LPs to opt out if they dislike his style.
Hardest push from Harry ▶ 13:39 Host siding with growth investorHarry directly refuses Oren's premise about acceptable growth metrics, interrupting to flatly state 'Because I think he's right' when discussing an investor passing on a 100 percent growing startup.
Biggest teaching moment ▶ 42:41 Second grade math lesson on secondariesWhen Harry attempts to justify selling secondary shares early to optimize IRR, Oren patronizingly breaks down 'second grade math' to show Harry that his underlying valuation logic implied poor future performance.
Harry holds his own ▶ 17:38 DoorDash and OpenAI counterexamplesHarry demonstrates strong market knowledge and pushes back against Oren's strict margin requirement by pointing to category-defining outliers like DoorDash, OpenAI, and Anthropic that succeeded despite terrible early margins.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome Back & The Nature of Contrarian Investing | 3 | 3 | 2 | 2 | Harry opens by acknowledging his own growth as an interviewer and asks why top venture investments look non-consensus at inception. Oren explains that contrarian bets with low competition build real moats if correct. | |
| AI Fundamentals and Beneficiaries vs. Victims | 4 | 4 | 2 | 2 | Harry asks if Oren's investment criteria changed in the AI wave, prompting Oren to outline his framework of evaluating whether a startup is an AI beneficiary or victim. Oren uses Navan as a concrete example of an AI beneficiary. | |
| AI-Driven Operational Efficiency & Customer Experience | 3 | 5 | 4 | 2 | Oren details how AI drastically improves gross margins in operationally complex businesses like Navan and rejects the hot-take narrative that all incumbents will be destroyed as provocative thought-leadership fluff. | |
| Why the "Incumbents Will Die" Narrative is Provocative BS | 6 | 4 | 4 | 6 | Harry presses Oren on an apparent contradiction, noting that AI customer support is a crowded consensus market which contradicts Oren's anti-competition stance. Oren clarifies that he avoids early-stage crowded support startups because picking the winner among thousands is impossible. | |
| Debunking Crazy Startup Growth Rate Expectations | 6 | 5 | 5 | 6 | Harry highlights how growth expectations have skyrocketed and directly agrees with a growth investor who passed on a 100 percent growing company. Oren forcefully defends compounding math and healthy 2x growth over hollow 3x growth. | |
| The Danger of Growth-at-All-Costs & Circular Deals | 5 | 5 | 6 | 5 | Harry argues that large funds face opportunity costs when companies like Harvey or Cursor grow exponentially fast. Oren rejects the premise and criticizes circular revenue deals designed to artificially boost top-line growth. | |
| When to Prioritize Top-Line Growth vs. Margin | 6 | 4 | 3 | 6 | Harry challenges Oren's focus on margins by citing DoorDash, OpenAI, and Anthropic as category winners that operated with poor early margins. Oren acknowledges that market-capture dynamics sometimes require prioritizing top-line growth over early unit economics. | |
| Power Laws, Conviction, & Admitting Mistakes | 4 | 5 | 3 | 3 | Harry brings up his own past deal rejections, prompting Oren to discuss suppressing social proof and operating with intellectual honesty. Oren quotes Annie Duke on how humans act as self-validation machines rather than truth seekers. | |
| Case Study of a PropTech Failure | 4 | 5 | 4 | 4 | Oren shares a PropTech failure caused by rapid interest rate hikes, but resists Harry's attempt to extract a conventional lesson. Oren argues against outcome bias, citing poker decision-making where good decisions can still lose individual hands. | |
| Staying Emotionally Grounded During Existential Crises | 3 | 4 | 2 | 2 | Harry asks about managing stress during Navan's existential crises such as Delta Air Lines disputes and COVID lockdowns. Oren explains his deep trust in CEO execution and his ability to emotionally detach from founder mistakes. | |
| Capital Concentration & Disregarding LP Vintage Pressures | 6 | 5 | 6 | 6 | Harry confronts Oren with LP feedback about deploying funds too quickly and ignoring vintage diversification. Oren candidly admits he does not care about LP vintage complaints and invites dissatisfied LPs to leave his funds. | |
| Lessons from the 2021 Market Peak | 4 | 5 | 2 | 3 | Oren reflects on overpaying for deals in 2021 and explains how LP vintage diversification occurs across multiple fund cycles. He details why he cut his 2024 fund size back to $250M. | |
| The Future of Venture: Boutique Artisans vs. Giant Platforms | 5 | 4 | 3 | 4 | Harry poses a thesis on venture bifurcation into mega-platforms versus artisan solo GPs, predicting the middle will suffer. Oren agrees and forecasts that over 50 percent of mid-tier venture funds will fail to raise future capital. | |
| How GPs Inflate Book Values & Why LPs Can't Trust Paper Marks | 4 | 6 | 4 | 3 | Harry asks if LPs face a reckoning on inflated unicorn valuations. Oren explains how middle-tier GPs inflate paper marks to stay alive while top-tier GPs have no incentive to exaggerate numbers. | |
| LP Liquidity Drought, IPO Pipelines, and the DPI Fixation | 6 | 6 | 5 | 6 | Harry defends selling secondaries early to lock in IRR, but Oren counters with basic math to show that secondary buyers demand discounts that strip away future upside. Oren also reveals his complete fee reinvestment and radical LP alignment. | |
| Principal-Agent Misalignments in Venture Partnerships | 4 | 6 | 4 | 3 | Oren outlines structural misalignments in venture, highlighting how mega-fund management fees dwarf carry incentives and how junior partners manage personal careers over fund performance. | |
| Valuations at Series A and the Danger of the "Optics of Progress" | 5 | 5 | 3 | 4 | Harry calls Series A the worst stage to invest due to high valuations without proportional business progress. Oren agrees, cautioning against being fooled by the 'optics of progress' versus genuine product-market fit. | |
| Preemptive Rounds, Boardroom Pressure, and the "Uncapped Safe" Story | 5 | 5 | 4 | 5 | Harry quotes Jason Lemkin saying modern founders reject investor advice. Oren pushes back by emphasizing that advice delivery and non-judgmental environments dictate whether founders listen, sharing an anecdote about his own LP interaction. | |
| How to Deliver High-Value Advisor Advice to Founders | 4 | 5 | 4 | 3 | Harry asks why Oren does not invest solely his own capital like Homebrew. Oren explains he wants to be the primary backer in deals. The segment transitions to a quickfire round where Oren critiques anti-wealth political sentiment. | |
| The Excitement and Concern Over AI | 5 | 3 | 1 | 3 | Harry asks if Oren shares his anxiety over AI labor displacement and whether this technological shift feels fundamentally different from past cycles. Oren validates Harry's perspective, agreeing that AI is uniquely transformative. | |
| Biggest Misses and the Anti-Portfolio Fallacy | 6 | 5 | 4 | 5 | Harry discusses his biggest misses, leading Oren to break down the anti-portfolio fallacy where 20 VCs all claim they could have done the same winning deal. Oren then reminds Harry that Harry personally passed on Riverside. | |
| Respect and Admiration for Mickey Malka | 3 | 2 | 0 | 1 | Harry asks Oren about his admiration for Mickey Malka. Oren praises Malka's leadership and authenticity before expressing long-term optimism for AI-driven transformation, closing with mutual appreciation. |
Statements from this episode (56)
Zeev: The growth-at-all-costs mindset is dangerous
“I think this notion that only growth matters is a very dangerous one, and I've seen this movie many, many times.”
Zeev: I am the largest LP in every one of my funds
“In every one of my funds, I'm the biggest LP. Every single one.”
Zeev: I take zero income from fund management fees
“By the way, I pay myself zero. I don't see anything, which is very unusual. I don't know any VC in the world that has zero income. From the management fees.”
Zeev: AI is the biggest change in human history
“Listen, AI is the biggest change ever in the history of humanity.”
Zeev: Weird-looking startup ideas gain 2-3 years without real competition
“Look, I think if they're long, if they look weird and they look wrong, then probably there aren't gonna be 15 or 20 or a hundred other startups doing it. So you're probably gonna have two or three years without real competition.”
Stebbings: Every startup currently faces at least 8 to 10 competitors
“Now, for every company I meet, there's legitimately eight to 10 at a minimum.”
Zeev: Consensus in investment sectors is a reason to avoid them
“If everyone is doing something, it's a reason not to do it, not a reason to do it, you know?”
Zeev: Pass on AI-neutral companies, only invest in AI beneficiaries
“The one thing maybe you could argue that change, I don't know if it's 24 months or 36 months, is that every investment I have to ask myself, is this company a likely beneficiary of AI or not? The answer is not. Well, if the answer is that they're a victim of A…”
Zeev: SaaS multiples are at 10 to 12 year lows
“SAS multiples, for example, are lower than they've been in the past 1012 years.”
Zeev: Navan faces zero risk of AI disruption and will benefit hugely
“Now, specifically with Navan, which a company I know well, I'm a hundred percent convinced that there's zero chance that we get disrupted by AI, and there is a hundred percent chance that we're huge beneficiaries of AI.”
Zeev: Navan's gross margins were around 50% before AI adoption
“Gross margins you know, three years ago before AI, our gross margins were around 50%. It was all the cost of support.”
Zeev: Almost all customer support at Navan will be handled by AI
“And ultimately I believe that If not all the, almost, almost all the support is going to be done by AI.”
Zeev: Technology is only 5% of defensibility in complex businesses
“The more operationally complex a business is, the more it's about distribution. The more it's about integration with source and with other pieces of software or content in the case of Navan or part of the ecosystem, the more the more it's in a regulated, this …”
Zeev: Predictions that AI will kill software incumbents are provocative BS
“So the bottom line is, I think this notion that all the incumbents are going to die, you know, this notion that is being promoted by some People who I think whose main motivation is to make provocative statements, you know and get attention as thought leaders …”
Zeev: Adapting incumbent software companies will be huge AI beneficiaries
“Companies that on one hand are not, many companies are not easy to disrupt, and as long as they don't fall asleep on the wheel, and as long as they navigate, you know, they adapt they're going to be huge beneficiaries of AI.”
Zeev: Only one in thousands of AI customer support startups will succeed
“One, you know, one of them is going to be successful, but there's a thousand or two, but there's a thousands that are not. So I'm not, at the very early stages, I don't trust my intuition enough to know which one of the thousand is going to be successful.”
Zeev: AI does not change compounding startup growth math
“Because the math doesn't change. If you have if you have a company that can double every year for the next five years, it's gonna be 32 X what it is today, because two to the power of five was 32 before AI and after AI. That has not changed.”
Zeev: 2x growth with strong economics beats 3x hyper-growth with poor economics
“I prefer a company that's growing two X with very healthy economics and a company that's growing three X with unhealthy economics.”
Oren Zeev: Very few $20M ARR startups are doubling with healthy economics
“I will tell you, even this day and age, there aren't many twenty million dollar companies that are doubling with, you know, with very healthy economics, you know, just not so many of them.”
Stebbings passed on Deel's seed round
“You know, I turned down deal at the seed round, because I was like, payroll? Really? Paychecks? ADP? Come on, this is ridiculous. With this kid, Alex, who's now a friend, he won't mind that.”
Zeev: A 50% VC hit rate is great given 100x upside asymmetry
“In my, in 50% of the time I'm right and 50% I'm wrong, that's actually a great result because a winner is so much more important than the loser. Because you know, as you know, if we lose something, we only lose one X our money. If we win, it could be a hundred…”
Zeev: PropTech investment failed after underestimating interest rate hike speed
“In hindsight, I overestimated the resilience of the business, and I underestimated the speed what I called the worst case scenario, what I modeled as the worst case scenario, was actually not as bad as the real the real scenario that happened. You know, the ri…”
Delta Airlines refused to work with Navan in 2018 existential crisis
“In 2018 or 19, we had an existential crisis when Delta Airlines decided that they hated us, and you cannot really succeed as a travel company when one of the three major airlines in the U.S. Is not willing to work with you in the swing and all that, and luckil…”
Navan was the first company to conduct COVID layoffs over Zoom
“They were the first company to let people go. And they got so much shit on, ah, for it because they fired people Over Zoom, as if there was any other way they could have, and they still got a lot of shit from the press”
Zeev lets go emotionally when portfolio founders mishandle crises
“If I have a company where maybe the founders are not doing the right things, and I'm, you know, and, ah, they're not reacting to a crisis in the way that I think they should, I don't get too worked up about it, and I, you know, at the end of the day, I just, a…”
Zeev caps single-company fund concentration at 20%
“I'd say 20% is my limit of a fund in one company, which, you know, I think industry standard is probably 10%, I'm at 20%.”
Zeev: GP-level diversification provides no value to LPs
“By the way, from the LP perspective, diversification at the level of the GP makes no sense, because they have multiple GPs, so, so the diversification gives nothing to LPs.”
Zeev will not change deployment pace for LP vintage preferences
“I'm going to do my thing, and if it works for them, fine, and if not, they can opt themselves out, and some of them have, and it's fine. Good people opted out, and it's fine. I'm not going to do things differently.”
Zeev regrets deploying capital too quickly in 2021
“And then, by the way, sometimes looking back, you know, if I look at 2021, I would say I did, I invested too fast. You know, I wish I didn't, ok?”
Zeev: Overpaid by 3x to 4x on every 2021 deal
“Well, I think in general in twenty-twenty-one, pretty much every deal that I did, most actually I shouldn't because these are quality companies, but every single deal I probably paid. Three or four X, what I should have, because that was the market.”
Zeev: Cut fund size by half following peak $500M+ funds
“And I think that I have two bubble sizes. Publicize funds. One of them is going to be okay, the other one is actually going to be good despite that, but I have two funds that were over five hundred million from 20 21 and 2022, but my 20 24 fund already, ah, cu…”
Oren Zeev: Traditional mid-sized VC partnerships are in deep trouble
“If you are traditional five, six person partnership without anything Very, very, very unique and special in the friendship that you bring to the table, then yes, I think you are in trouble because it's almost like, you know, worse off. On one hand, you're not …”
Oren Zeev: Over 50% of VC funds will fail to raise again
“At least 50% of the funds today, and maybe more, either cannot raise, or at least are not sure that they can raise, or they're trying to stall and, you know, not test the market, and I think many of them are not gonna be able to raise.”
Zeev: Top VC Funds Like Sequoia Have Zero Incentive to Inflate Paper Marks
“If you're a fund that's, let's, let's say Sequoia, for example, they know that they can raise any time, right? So they have zero motivation to inflate numbers. They have all the motivation in the world to show things as conservatively as possible, right? Becau…”
Zeev: Mid-Tier VCs Inflate Paper Marks to Survive Fundraising
“However, if you if you are a fund that is more middle of the road and you're not sure how Is it gonna be a raise or not? You're gonna find any excuse to keep the prices up, right? To look good on paper.”
Zeev: Accountants Cannot Effectively Audit Venture Valuation Marks
“Are not good rail guards from that perspective, because even if they challenge valuations, they always challenge the wrong things, and they always, it's complete lack of understanding what, you know, because how, why would they know what, you know, what compan…”
Zeev: Venture liquidity could surge in 2026-2027 driven by mega-IPOs
“By the way, that might change in twenty-twenty-six, in big way, in a big way, because there are a host of a host of huge, unprecedented size IPOs in the works now. You know, companies like SpaceX, and Stripe, and Databricks, and, you know, and others. So there…”
Zeev: Most LPs have suffered a 4 to 5 year liquidity drought
“But right now, there's been a drought of liquidity for most LPs for a long time, five, four, five years.”
Zeev: LPs are excessively focusing on DPI while discounting paper marks
“Because of that, I think there is, I would say too much focus even, but understandably on DPI, and where, you know, people hardly talked about it three years ago, and now some LPs, oh, it's just DPI. It's just DPI. We don't believe anything.”
Zeev: Secondary buyers only purchase positions expected to double or triple
“The assumption that I'm going to sell something, you cannot assume that the buyers are stupid, so they're only going to buy things that they can think they can, they think they can double or triple within the next two or three years.”
Zeev: Management fees exceed carry value in mega VC funds
“Look, especially in the larger funds the compensation that the V, that the GP gets from the management fee, especially if you account for time value of money is typically greater than the than the upside.”
Zeev: Partners in large VC firms prioritize personal deals over fund performance
“You know, if the typical, if a partner in a in a partnership, especially large partnership with some, with politics and all that they're much more interested in their investments succeeding than anything else because that's their career.”
Stebbings: Series A is currently the worst stage for venture investing
“I look at Series A today, dude, and I think it's the worst place to be investing, and so I'd love your thoughts on this. You know, we have 200 XAROs, 150 XAROs, there's very little company progression from the seed round, but there's a very steep price increas…”
Zeev: Overvalued Series A rounds with no progression have existed for 30 years
“It's always been the case. It's always been the case, even 30 years ago, that someone invests you know, you have a seed round basically founders in the idea it's priced low. And then a year and a half later, basically, they have now 20 people, they have an off…”
Zeev: Startups lacking PMF after two years should be valued below their seed round
“The very fact that after a year or two they don't have signs of product market fit, maybe it means that, you know, it should be worth less than what it was worth at the seed, because at the seed you had the option value of maybe within a year or two you will h…”
Zeev: Founders should accept preemptive rounds but maintain low burn
“My advice is take the money. But continue to behave as if you didn't. Don't spend money just because you have it. You know, companies can be overfunded, and, ah, it can lead to loss of focus, so if the founder's mature enough and strong enough to take the mone…”
Zeev: Refuses to give LPs strategy promises to maintain investing flexibility
“And that's exactly why I don't tell LPs anything in terms of what I'm going to do, because I feel that if I tell LPs something, I would feel too committed to that specific strategy, which I may have thought it was the right strategy, but then there's a situati…”
Zeev: Made exception to invest $1.5M in AI startup Decart via capped SAFE
“I normally don't do safes at all, but in this case I said, you know what, I'll do it, but I needed to be capped and we capped it which Luckily, because otherwise, at least for the investors, it was lucky because, you know, the next one was at much, at a very h…”
Zeev Ventures has backed only 40 total companies across 11 funds
“So I'm now in fund 11, and I only have 40 companies.”
Zeev: Anti-rich sentiment is rising in America, following Europe
“I find that there is an increasing level of hating the successful, hating the rich. I see it on Twitter. I think in Europe it's even worse, but it's come to America, unfortunately.”
Zeev: Progressive movement is undermining American meritocracy
“Let's say that I'm not a fan of the movement or the work movement that is You know, dragging or trying to drag America in the other direction.”
Apax Partners rejected Zeev's early pitch to invest in Facebook
“I, now, now I do have misses from the Apex days where I saw something that I wanted to do, but I knew that there was no way I could get it approved, including Facebook, by the way, in the very early days, you know, I saw it, I could have done it. I brought it …”
Apax rejected Zeev's attempt to take Audible private before Amazon sale
“I try to convince the partnership to buy, I made the investment in Audible was my first big home run, and then it went public, and it was a good, a great, we sold not all the shares, but enough to make it the home run and then the stock price dipped, and it wa…”
Zeev: VC anti-portfolios are fallacious because seeing deals doesn't mean winning
“This is one thing that is, Consistent fallacy within VCs that they think that just because they saw a deal, they necessarily would have been able to do it. No, you know with all due to anti-portfolio, it doesn't make sense that the same deal appears in 20 diff…”