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Cem Sertoglu: Lessons from the Greatest Venture Investment in European History | E1228

Cem Sertoglu is one of the great venture investors of the last decade. Cem is famed for writing the first check into UiPath and over several rounds turning $16.5M into $2.1BN. Cem recently started Bek Ventures, a $250M fund that was 3x oversubscribed. ----------------------------------------------- Timestamps: (00:00) Intro (00:48) Entry Into Venture World (05:43) How Venture Capital Evolved into a Low-Margin Business (13:41) How Cem Prioritizes Founder, Market, and Traction (18:11) Signalling Does Exist? (20:24) When & How to Address Concerns with a Founder (25:32) Advising Founders on Early-Stage Valuations (27:01) Where Founders and VCs Often Diverge (28:52) Do High Prices Lead to High-Quality Investments? (31:32) Are Richer Investors More Successful? (36:06) Making $2.1BN on UiPath (52:39) Cem’s Biggest Loss (56:41) Concerns Over Current Liquidity Markets (01:00:00) Quick-Fire Round ----------------------------------------------- In Today’s Show with Cem Sertoglu We Discuss: 1. Has Venture Capital Been Commoditised: Why does Cem believe that VC has not been commoditised? Why does Cem believe many VCs today are not even VCs anymore? How does Cem advise founders who have offers from large multi-stage firms? What questions should they ask them pre-working with them? How do the best founders select the VC they choose to work with? 2. Price, Reserves, Loss Ratios: Why does Cem believe that price does not matter? How does Cem approach reserves and reserves management? What does Cem know now about reserves that he wishes he had known when he started investing? Does Cem care about loss ratio? Does he do scenario planning when making investments? 3. Making $2.1BN on UiPath: How did Cem meet Daniel for the first time? Was it obvious he was incredible? Why did they only write a $1M check and not take the whole round with $1.5M? Why did 40 of the best investors in Europe all turn down UiPath for the Series A? What did doing the bridge round for UiPath teach Cem about reserves? When was it obvious UiPath was going to be a mega hit? How did they continue to concentrate capital with each round? When did they first start to sell shares in UiPath? What was their approach to the selldown of their position? When the company IPO’d, how much of it did they have? 4. AMA with One of Europe’s Best: Does signalling exist? How does Cem advise founders on this? What has been his biggest loss? How did that change his mindset? What has been Cem’s biggest miss? What did he not see? Why does Cem always believe you should manufacture arguments with founders before investing? Why does Cem believe a high GP commit can actually misalign the GP and the LP? ----------------------------------------------- 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 Twitter: https://twitter.com/HarryStebbings Follow Cem Sertoglu on Twitter: https://twitter.com/csertoglu 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 #cemsertoglu #uipath #bekventures #partner

Cem SertogluguestHarry Stebbingshost
Nov 19, 20241h 4mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Inside UiPath’s $2.1B Win And The Craft Of True Seed Investing

  1. Cem Sertoglu, founder-turned-investor and early backer of UiPath, breaks down how a $16.5M investment turned into $2.1B and what it revealed about power laws in venture. He contrasts focused, “artisan” early-stage firms with multi-stage asset managers, arguing that great founders choose investors for care, alignment, and time—not just price. The conversation covers how to think about valuation, ownership, reserves, signaling, and board behavior, plus why early-stage rounds should be seen as long-term alignment contracts rather than trades. Sertoglu also reflects on missed deals, loss-making investments, AI bubbles, fund structures, and why patience and discipline matter more than ever in today’s market.

IDEAS WORTH REMEMBERING

5 ideas

Treat early-stage rounds as alignment contracts, not stock trades.

Sertoglu argues that seed and Series A checks are out-of-the-money call options on a distant vision; the real substance is a long-term partnership where founders choose who will occupy a tiny number of high-attention slots on a VC’s cap table for a decade.

Founders and markets matter far more than entry price at seed.

He shows that even if UiPath’s seed valuation had been 2x higher, the fund outcome would still have been spectacular; valuation discipline is necessary, but over-focusing on price can cause you to miss power-law winners.

Maintain reserves to support misunderstood but promising companies.

UiPath was passed on by dozens of firms multiple times, forcing his fund to bridge it when the market didn’t understand it; this is precisely what reserves should be for—backing conviction when external capital is unavailable.

Avoid assuming product–market fit too early and over-scaling GTM.

He sees many companies stall between seed and Series A because they raise too much, hire too fast, and lock into a go-to-market script before truly nailing product–market fit, losing the agility to iterate.

Great early-stage investors add value by selective engagement and quiet boards.

Sertoglu emphasizes being deeply prepared but sparing with strong opinions, handling sensitive topics one-on-one, and resisting the social-media-driven urge to “perform value-add” at every meeting.

WORDS WORTH SAVING

5 quotes

Every early-stage check is buying a very out-of-the-money call option.

— Cem Sertoglu

We turned a $16.5 million investment into $2.1 billion in proceeds.

— Cem Sertoglu

Most of the best founders we partner with are looking for co-founder-like partners, not just cash.

— Cem Sertoglu

Venture investing is never easy. It’s a very hard profession… the hardest thing people don’t see is how long things take.

— Cem Sertoglu

I believe UiPath went from one million to one hundred million ARR in twenty-one months.

— Cem Sertoglu

Cem Sertoglu’s journey from founder to early-stage VC and regional focusThe UiPath investment: sourcing, conviction building, pricing, and sell-down strategySeed vs multi-stage funds: commoditization, competition, and what founders really buyEvaluating startups: founder–market–traction hierarchy, fund-return math, and valuationBoard dynamics, “quiet” VCs, and maintaining healthy founder–investor alignmentReserves, follow-on decisions, signaling risk, and loss ratios in venture portfoliosCurrent environment: AI hype, liquidity drought, fund structures, and LP perspectives

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