venture

32 statements across 31 episodes · 6 bullish · 13 bearish · 22 people on the record · first statement May 7, 2015 by Jon Staenberg · across every show →

Everything said about venture, oldest first

May 7, 2015 positive
Insight
Staenberg: Five years of operational experience makes for better venture capitalists
“You can do venture, but why don't you get some real world experience first? Why don't you go somewhere for five years? And actually know what it means to go through cycles, know what it means to hire and fire people, know what it means to have to work on a tea…”
Jon Staenberg May 7, 2015 ▶ 2:16 20 VC 034: 250 Investments, AngelList Syndicates and Microsoft with Jon Staenberg
Feb 10, 2016 bullish
Prediction Not checkable as stated
Venture capital knowledge will become distributed rather than insider-only
“Maiden Lane is being built and AngelList is being built, you know, in the middle of a city center of a major city, and I think that's sort of the bigger trend of where venture is going. It is no longer going to be a skill set or knowledge of the very few. It's…”
Dustin Dolginow Feb 10, 2016 ▶ 7:19 20VC: The First Online Venture Fund Built On AngelList with Dustin Dolginow @ Maiden Lane
Mar 14, 2016 positive
Insight
Mazzeo: Venture capital is shifting toward public personality and thought leadership
“Increasingly, I think we're seeing, we've been talking a little bit about this, Harry, like that shift in venture towards being more of a personality and expressing yourself and not being you know, a wilting lily and sort of going out there. And being more fro…”
Matt Mazzeo Mar 14, 2016 ▶ 7:42 20VC: Lowercase's Matt Mazzeo on Being Chris Sacca's Partner and The 3 KPIs to Successful Investing
Aug 29, 2016 negative
Insight
VCs judge startups in hours, while studios evaluate founders over months
“If you look at venture, in a lot of ways, they're just kind of judging you inside of 30 minutes, and wow, I have data of thousands of hours with the CEO. In this company, and they're judging it in, in a 30 minute moment, whether it's just, they want to continu…”
Peter Pham Aug 29, 2016 ▶ 14:37 20VC: Science Inc's Peter Pham on Why The Battle Between Entrepreneurs & VCs Is Unfair, How To Even The Playing Field & How To Tell When A VC Really Is Interested
Aug 31, 2016
Insight
Evaluating venture capital investor performance takes five to ten years
“Knowing if you're any good at venture takes, you know, five years, seven years, sometimes 10 years, so I can't really speak for if I'm”
Jesse Middleton Aug 31, 2016 ▶ 14:48 20VC: Why Great Founders Are Both Visionary & Stubborn, The Investment Mindset Shift From Angel To VC & How To React When The 'S*** Hits The Fan?' with Jesse Middleton, General Partner @ Flybridge Capital Partners
Mar 27, 2017
Insight
Gur: Entering venture capital is like deciding who to marry
“You can decide you want to do venture, but that's like deciding you want to get married. You know, these are like, you know, it does depend who the girl is or the guy”
Saar Gur Mar 27, 2017 ▶ 6:08 20VC: How Investors Can Build Relationships with Founders In Organic, Non-Transactional Ways & How VCs Should Handle Founder Disputes with Saar Gur, General Partner @ CRV
Sep 4, 2018 bearish
Prediction Held up
Eggers: Venture returns will suffer due to 2018 capital oversupply
“I do think, though, that we've got too much money coming in, and so I do think returns are going to suffer a bit. For these vintages, and that we probably need some kind of a correction to decrease the amount of capital that's coming into venture.”
Barry Eggers Sep 4, 2018 ▶ 9:15 20VC: What It Takes To Found and Scale A Global Venture Firm Like Lightspeed, 3 Ways Firms Do Not Succeed in Generational Transition & What Makes The Truly Special Board Members Like Jim Goetz with Barry Eggers, Founding Partner @ Lightspeed Venture Partn
Feb 28, 2020 negative
Insight
VC Twitter echo chambers destroy the mental space needed for original thought
“I think social media in general, like, you know, the amount of information, the amount of opinions, the amount of knowledge out there has a lot of positives, but it also has some negatives, and we talk a lot here about being in a bubble, and kind of the echo c…”
Tomer London Feb 28, 2020 ▶ 7:34 20VC: Gusto Co-Founder, Tomer London on Why Most Founders Approach Fundraising With The Wrong Mindset Today, How To Construct A Values/Motivation Alignment Test To Determine The Right Investors For You & Why Delight Is So Crucial To The Success of Any Con
Jun 8, 2020 neutral
Insight
VCs lack operational leverage and must aggressively filter their time
“In most of my working experience, I've been a leader and a manager and someone who had not just the leverage of a team around her, but also the leverage of the software that we were building, and so in venture, you have to be incredibly choosy with how you spe…”
Merci Victoria Grace Jun 8, 2020 ▶ 6:35 20VC: Lightspeed Partner, Merci Victoria Grace on The Future of Collaboration Tools, Bundling vs Unbundling, Synchronous vs Asynchronous & What It Means To Productise The S*** Out of Venture
Jan 11, 2021 negative
Assertion Not checkable as stated
Stebbings: Capital glut forces VCs to invest without thorough diligence
“In venture, there's so much money today where you need to move so fast that by the time you make the investment, actually, you don't know them very well at all because we're all just throwing money so fast around because there's just too much money.”
Harry Stebbings Jan 11, 2021 ▶ 12:19 20VC: Annie Duke on Reversible vs Irreversible Decisions, How To Evaluate Risk, The Theory of Sunk Cost in Venture & How to Optimise Both the Discussion and Quality of Investment Decisions
May 24, 2021 negative
Opinion
Nigel Morris: Private equity investing is much easier than venture capital
“Private equity is much easier than venture.”
Nigel Morris May 24, 2021 ▶ 11:52 20VC: Why Bundling Does Not Work, How The Best Founders Analyse Unit Economics, Why The Way We Approach Mental Health in Venture and Startups is Wrong with Nigel Morris, Co-Founder & Managing Partner @ QED Investors
Jun 2, 2021 negative
Opinion
Glyman: Venture capital is overly gossipy rather than future-focused
“It's so gossipy. For all this talk about being focused on the future, I feel like half the industry is wondering what are the other people working on or thinking about at this very moment.”
Eric Glyman Jun 2, 2021 ▶ 36:19 20VC: Ramp's Eric Glyman on Why You Should Never Take The Highest Price, Working With Venture Funds vs Crossover Funds and How To Determine What To Buy vs Build as a Founder Today?
Feb 14, 2022 bearish
Opinion
Geoff Lewis: The 2012-2022 venture capital expansion wave is cresting
“This wave that might be cresting now in venture was really just starting back then in 2012.”
Geoff Lewis Feb 14, 2022 ▶ 4:05 20VC: Bedrock's Geoff Lewis on Whether VCs Actually Provide Value or Not, Why Bedrock Does Not Have An Ownership Focus and The Difference Between Principles and Rules When Building a Firm or Company
Nov 4, 2022
Assertion Supported
Mauboussin: Buyout funds consistently beat venture capital on a PME basis
“Buyouts, by the way, have consistently been a little bit better than private equity have been a little bit better than venture. They're much less episodic or dramatic, and they tend to chug along a little bit over one PME.”
Michael Mauboussin Nov 4, 2022 ▶ 29:08 Michael Mauboussin: The Single Biggest Mistake Investors Make In Decision-Making | 20VC #945 · 20VC with Harry Stebbings
Nov 30, 2022 positive
Insight
Lemkin: Top VC Brands Yield One to Two Quality Deals Annually
“If you have a top brand, you're going to get into one or two good deals a year by hook or by crook. If you play the game and it's enough, that's the beauty in venture.”
Jason Lemkin Nov 30, 2022 ▶ 1:07:00 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
Mar 4, 2023 neutral
Assertion Partly supported
Somerville: Venture secondary discounts reached 12% in 2021 and 34% in 2022
“The average discount to venture ticked up as high as just 12% in 2021, so quite low overall, but if you were to fast forward that forward to 2022, it's back down at an industry level to 34%”
Hunter Somerville Mar 4, 2023 ▶ 23:13 Hunter Somerville: Biggest Mistake LPs Make; Deep Dive into Secondary Markets | 20VC #985 · 20VC with Harry Stebbings
Mar 17, 2023
Assertion Supported
Stebbings: Major European pension funds and universities lack venture capital allocations
“Fundamentally, you know, some of the largest pension funds in Europe don't invest in venture. I mean, that's like, unthinkable in the US. You know, I think when you look at a lot of educational facilities in Europe, we don't have any allocation to venture.”
Harry Stebbings Mar 17, 2023 ▶ 44:27 Ophelia Brown: How We Raised $432M in a Pandemic; What's New in European Venture Capital | E990 · 20VC with Harry Stebbings
May 9, 2023 positive
Opinion
Paik: Market selection matters far more than founders in venture capital
“I tend to agree. I think that markets are significantly more markets are huge, huge, huge input into outcomes, particularly in venture.”
Chris Paik May 9, 2023 ▶ 53:12 Chris Paik: How I Raised $400M; Substack's Broken Business Model; Music on TikTok vs IG | E1011 · 20VC with Harry Stebbings
Aug 23, 2023 positive
Prediction Not checkable as stated
Zullo: Venture capital will transition to asset management model
“But I think it's splintering off of professionalization of turning into asset management is really going to happen in venture in the next couple of years.”
Rick Zullo Aug 23, 2023 ▶ 7:49 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Aug 23, 2023
Assertion Not checkable as stated
Lemkin: Every Elite Long-Time VC Has a $10B Outcome
“Everyone that's been doing venture for a while that is elite has at least one ten billion dollar outcome.”
Jason Lemkin Aug 23, 2023 ▶ 3:36 Jason Lemkin & Rick Zullo: How "Mark to Market" Corrupted Venture Capital | E1052 · 20VC with Harry Stebbings
Sep 20, 2023 negative
Opinion
Lemkin: Founders lost perspective on next-round risk as VC gamified
“I don't think, I think founders have lost all perspective on the risk they're taking in the next round. Venture has been so gamified the last five years, and everyone's to blame.”
Jason Lemkin Sep 20, 2023 ▶ 41:54 Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062 · 20VC with Harry Stebbings
Mar 25, 2024 bearish
Prediction Open · timeframe Mar 2029
Clark: M&A regulatory chill will concentrate VC returns in fewer companies
“I think the impact that will have is that the concentration of returns in venture is going to be even smaller as they're going to be fewer companies that ultimately account for that, that performance.”
David Clark Mar 25, 2024 ▶ 22:55 David Clark: Lessons from 32 Years of Fund Investing - Why Exits Will Be Larger | E1131 · 20VC with Harry Stebbings
Jun 3, 2024 bearish
Insight
Lemkin: VCs can't profit on >$100M valuations without multiple reflation
“I think for the math to pencil out in venture, we do need a rebound. The math. And this is, forget about the unicorn rounds and the crazy. We just, we do need some, we do need a 30 to 40% multiple reflation, or we just can't make any money on any round north o…”
Jason Lemkin Jun 3, 2024 ▶ 27:23 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Jul 24, 2024 negative
Opinion
Lemkin: VCs are pretending market liquidity has returned to 2021 levels
“In venture, we're all pretending. You know, early-stage folks have never worried about liquidity, and the late-stage guys gotta deploy money. The time's ticking on these funds, so you gotta deploy them. We're praying, we're hoping liquidity comes back. We're i…”
Jason Lemkin Jul 24, 2024 ▶ 0:00 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
Sep 16, 2024
Insight
Stebbings: Investors fail by copying others instead of leaning into unique strengths
“After 2700 shows, I've learned that one of the biggest mistakes people make is they try and copy someone's style that's not authentically theirs, and think that's the right one. And actually, it's about finding where you are uniquely great in the three pillars…”
Harry Stebbings Sep 16, 2024 ▶ 0:55 Shardul Shah: How Index Makes Decisions & Why Benchmarks & Averages in VC are BS | E1202 · 20VC with Harry Stebbings
Nov 27, 2024 negative
Insight
Klaus Hommels: Venture capital isn't about sitting back and passing judgment
“Venture is not sitting in a nice office with borrowed power of LPs and playing like in old Caesar's times, thumbs up, thumbs down.”
Klaus Hommels Nov 27, 2024 ▶ 0:00 Klaus Hommels: Why "Portfolios are Merely a Construct to Make LPs Happy"? | E1231 · 20VC with Harry Stebbings
Apr 17, 2025 neutral
Prediction Not checkable as stated
O'Driscoll: Megafund growth ends only when institutional CIOs halt VC allocations
“It won't stop because the venture guys will be mature. It won't stop because the founders will kind of be more careful. It won't even stop because the LPs will stop. It will stop because the LP's bosses, the overall CIOs will stop allocating capital to venture…”
Rory O'Driscoll Apr 17, 2025 ▶ 30:40 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
May 22, 2025 neutral
Insight
O'Driscoll: Venture Fund Profits Are Concentrated in Rare Seven-Year Cycles
“One of the depressing facts about venture is we make an embarrassingly large percentage of our money once every seven years when you're in the white heat of must acquire, must own high growth venture assets.”
Rory O'Driscoll May 22, 2025 ▶ 26:38 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
Aug 28, 2025 negative
Insight
O'Driscoll: Great tech operators should stay in operating, not VC
“I always tell the great operators who talk about coming into venture, don't be crazy. Your highest and best use is operating.”
Rory O'Driscoll Aug 28, 2025 ▶ 29:21 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
Oct 27, 2025 neutral
Insight
Cahn: Venture investors cannot force a startup to succeed
“The lesson that punches you in the stomach in venture is you can't make a company succeed.”
David Cahn Oct 27, 2025 ▶ 35:30 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Apr 30, 2026 neutral
Insight
O'Driscoll: VC returns are mostly generated in rare hype years
“The dirty little secret adventure I get is how much of your money you make in that one year in 10 when everybody buys the dream.”
Rory O'Driscoll Apr 30, 2026 ▶ 0:32 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Aug 5, 2026 neutral
Insight
O'Driscoll: VC holding periods now outlast tech platform cycles
“Now the holding period of venture is longer than the technology platform chain cycle.”
Rory O'Driscoll Aug 5, 2026 ▶ 10:48 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
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