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Can You Still Win in Venture Without a $1BN Fund? Menlo’s Venky Ganesan on the New Rules of VC

Venky Ganesan is a Partner at Menlo Ventures, whose portfolio includes Anthropic, Lovable, Legora and Higgsfield, alongside earlier hits Uber and Roku. Venky's own investment track record includes Palo Alto Networks, Upwork, Poshmark and Rover. He is a three-time Forbes Midas List investor and former Chair of the National Venture Capital Association. ----------------------------------------------- Timestamps: 00:00 Intro 1:15 - Venky’s 90% Loss That Changed His Investing 4:21 - Venky On Whether Venture Capital Is Broken 5:28 - Should You Keep Playing When The Market Is Crazy? 6:59 - The New Rules Of Venture Investing 7:55 - Is Seed Investing Still Possible? 9:19 - Can AI Revenue Metrics Be Trusted? 11:20 - Does “King Making” Really Work? 12:47 - What Could Finally Crack The Market? 14:11 - Innovators, Imitators And Idiots 19:17 - Venky On When It’s Worth Paying Up 20:24 - Venky’s Most Expensive Missed Investment 23:13 - What Makes A Great Founding Team? 25:09 - Venky On Whether Ownership Still Matters 28:25 - When Should You Size Up An Investment? 29:57 - The Problem With Only Betting On Home Runs 33:21 - Is “Downside Protection” A Dangerous Mindset? 35:41 - Are Investors Facing A New Era Of Dilution? 38:39 - Why IRR Matters More Than Ever 41:58 - Are Faster Investment Cycles A Warning Sign? 48:24 - Venky On When To Take Chips Off The Table 51:41 - Are We About To See A Wave Of M&A? 54:11 - The Most Important Skill For Founders At Scale 55:24 - Does Money Change People? 56:34 - Why Are Bay Area Housing Costs So High? 59:40 - Does Being Rich Make You A Better Investor? 1:02:43 - Is Private Equity Facing An AI Reckoning? 1:06:44 - Venky’s Advice To Venture LPs ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Venky Ganesan X: https://twitter.com/venkyganesan Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #ai #venkyganesan #menlo #anthropic

Venky GanesanguestHarry Stebbingshost
Oct 5, 20261h 11mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Venky Ganesan: Winning VC in AI means options, concentration, and IRR

  1. Venky Ganesan describes today’s AI venture market as disorienting—mega-rounds and fast markups are common, but investors shouldn’t build long-term strategy from a single “snapshot in time.”
  2. He argues VCs must keep investing through frothy markets because timing is unreliable, yet they should shift tactics: treat early checks as options and only concentrate capital once objective proof indicates an outlier.
  3. He warns that metrics and revenue labels (ARR/run-rate/retention) will be gamed when investors over-index on them, so diligence should emphasize real business building and terminal value over short-term markups.
  4. He explains “kingmaking” and rapid tranche rounds through Soros-style reflexivity that works until it stops—often triggered by leverage or debt stress rather than equity repricing.
  5. He contends the new AI stack imposes “taxes” to public-market giants, raising the bar for VC to deliver faster DPI and higher IRR, while ownership, dilution, and time-to-exit have become even more central to outcomes.

IDEAS WORTH REMEMBERING

5 ideas

Keep playing, but change how you play—don’t try to time the market.

Venky argues that “calling timeout” can backfire because timing cycles is extremely hard; firms that stepped out in 96–97 missed 97–99 and re-entered at the peak. Instead, stay in the market but adjust selectivity, portfolio composition, and position sizing to manage risk.

Treat seed as options; concentrate only after proof emerges.

He frames seed checks as option bets: you buy the right (not the obligation) to keep investing if the company proves it’s an outlier. The discipline is to reserve real concentration for moments when quantifiable evidence (revenue/usage) supports higher conviction.

If a metric becomes a target, it will be gamed—verify underlying reality.

Venky notes that once investors overweight a metric, founders will optimize (and sometimes distort) it—he cites net revenue retention gaming via purchase-order structuring as an example. In AI, he’s wary of murky “run-rate” and “contracted ARR” claims and pushes diligence toward true business quality and “terminal value” thinking.

Reflexivity drives bubbles; debt/leverage is what often breaks them.

He views rapid markups and successive rounds as a reflexive loop: momentum attracts capital, talent, and attention, which can become self-fulfilling—until it stops. A common trigger for cracks is leverage/debt stress rather than equity write-downs, because debt requires repayment on a timeline.

Ego is expensive—optimize for returns, not status in the round.

Venky rejects ego-based dealmaking: if the investment can make money, syndicate dynamics and “who got in cheaper” matter less than returns. His point is that VC’s public, personality-driven nature can pull investors away from their fiduciary job: return capital to LPs.

WORDS WORTH SAVING

5 quotes

At this point in Menlo's history, right, we are going for broke. We are going for the grand slam home run. We want to see everything. We want to win everything. Full stop.

— Venky Ganesan

Each seed investment is an option bet. You're buying an option to see if it's an outlier.

— Venky Ganesan

If any metric is measured by an investor and they put a lot of weight on it, it's gonna be gamed.

— Venky Ganesan

The problem is venture is an asymmetric game. You can lose the dollars you invest, but you can make 10X if you're right. And that asymmetry means that the sins of omissions are way higher than the sins of commissions.

— Venky Ganesan

Money doesn't change people, but it reveals them.

— Venky Ganesan

AI venture mega-rounds and valuation inflationOption-bet model for seed investingPosition sizing and concentration over timeGaming of SaaS/AI metrics (ARR, NRR, run-rate)Reflexivity and “kingmaking” dynamicsOwnership, dilution, and time-to-exitIRR vs DPI and competition with public-market Mag 7

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