Dot Com Bubble

topic on 14 shows · 26 statements across 25 episodes

the Y Combinator Startup Podcast Cheeky Pint the Knowledge Project My First Million the Official SaaStr Podcast the Startup Ideas Podcast Invest Like the Best Capital Allocators Top Founders the MAD Podcast the a16z Podcast Big Technology All-In 20VC

26 statements about Dot Com Bubble, every show

Loeb: Current AI Tech Does Not Have a Dot-Com Valuation Bubble
“So, I, it's very different from the dot-com bubble, which we were short, you know, going into and had good numbers in those years. I just don't see, you don't have the valuation bubble now on those companies that you had on, on, on those companies back in thos…”
Dan Loeb May 28, 2026 ▶ 44:18 Legendary Investor Dan Loeb on AI, Credit, & Third Point’s $25B Strategy · Invest Like The Best
BIG TECHNOLOGY Prediction Not checkable as stated
Sorkin: AI Faces Potential Dot-Com-Style Bubble And Bust Timing Mismatch
“The bigger question is whether there's going to be like a timing mismatch, that there's going to be some period of time. Same way, by the way, we had a dot com bubble and bust where the economics didn't match the investments at that time. Now, Amazon is still …”
Andrew Ross Sorkin Mar 18, 2026 ▶ 40:09 Are We Screwed If AI Works? — With Andrew Ross Sorkin
CAPITAL ALLOCATORS Assertion Supported
Mahr: Dot-com brokerages distributed hot IPO shares first-come, first-served
“There were a lot of IPOs in that market environment, the dot-com bubble. They would go up a hundred percent, 200% or more on the day that they priced, and there were a small number of investment firms that would get allocations to these IPOs, and they would of…”
Daniel Mahr Nov 20, 2025 ▶ 4:20 Daniel Mahr – Glass Box Quant at MDT Advisers (EP.472)
CHEEKY PINT Assertion Not checkable as stated
Andreessen: The 2000 dot-com crash was almost entirely a telecom credit bubble
“It was almost entirely a telco bubble, and it was almost entirely a telco crash, and you know that for two reasons. One is the sheer amounts of money involved were so much greater on the telco side, and then the other is telco is where the debt came in. To get…”
Marc Andreessen Oct 1, 2025 ▶ 41:26 Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
BIG TECHNOLOGY Prediction Not checkable as stated
Ranjan Roy compares the OpenAI-Oracle deal to the dot-com fiber buildout
“I think for the market to have reacted that positively, it just, I don't know, it feels like in, you know, the internet bubble, there was so much that happened around fiber build fiber capacity build out that seems to start to echo this, that it this I don't k…”
Ranjan Roy Sep 16, 2025 ▶ 31:40 Do We Care About The iPhone Air?, Nepal's Discord Revolution, San Francisco’s 996 Culture
20VC Opinion
Micha Kaufman: The AI startup hype cycle mirrors the dot-com bubble
“I feel that we are in a period that is very similar to the .com, but it's now .ai. So it used to be pets.com, it's now pets.ai. Whatever, it's the same bullshit.”
Micha Kaufman Jun 9, 2025 ▶ 10:28 Fiverr CEO & Founder, Micha Kaufman: "If You’re Not Adapting to AI, F* You. You’re Done!" · 20VC with Harry Stebbings
MY FIRST MILLION Assertion Supported
Puri: 80% of Ron Conway's dot-com portfolio went to zero
“And basically what he says is that when that dot-com bubble burst, 80% of our companies just went to zero.”
Shaan Puri Jan 16, 2025 ▶ 16:45 The Crazy Story of Google’s 7 Angel investors
20VC Opinion
Taylor: AI bubble will rhyme with dot-com era, where excess was justified
“And I think the AI bubble will rhyme with the dot com bubble. And I believe with the benefit of hindsight, Most of the excess of the.com bubble might have been justified.”
Bret Taylor Oct 2, 2024 ▶ 7:40 Bret Taylor: Why Pre-Training is for Morons & Companies Will Build Their Own Software | E1209 · 20VC with Harry Stebbings
SAASTR Opinion
David Sacks: The 2021 tech market was the biggest bubble since 1999
“It's, you know, it's just never gonna be like it was in twenty-twenty-one. I mean, that was like the biggest bubble Since the dot-com bubble in 1999.”
David Sacks Sep 13, 2023 ▶ 25:54 What the Future of SaaS Holds with David Sacks, Founder & General Partner, Craft Ventures
Lamont: Google and Amazon wouldn't exist without 1990s internet mania
“If we hadn't had a mania, we wouldn't have funded things like Google and Amazon, some of the great companies of today.”
Annie Lamont Mar 7, 2022 ▶ 13:56 Annie Lamont – A Lifetime in Venture, Venture is Eating the Investment World 9 (Capital Allocators, EP. 238)
STARTUP IDEAS Assertion Not checkable as stated
Friedberg: Most dot-com crash M&A deals he worked on sold below cash
“I started with 11 people in my analyst class. There were two of us left at the end of two years. It was a pretty crazy time. I worked on probably 20 deals, most of which were companies being sold for less than cash, right? They were like, they were such distre…”
Dave Friedberg Mar 3, 2022 ▶ 3:58 Anything Is Possible with Dave Friedberg | Where It Happens
ALL-IN Assertion Not checkable as stated
Chamath: 2022 tech stock downturn matched dot-com collapse magnitude in months
“In the dot com bubble, It took somewhere between three to five years for most stocks to bottom. And they bottomed, I think, peak to trough somewhere, you know, towards 80% of where they were in 2000, right? So it took three to five years to go basically -80%. …”
Chamath Palihapitiya Feb 19, 2022 ▶ 43:09 E68: Trudeau invokes emergency powers, Bitcoin vs. government, Tiger Global's new strategy and more
Caldwell: Every modern startup idea has a 1990s dot-com analog
“Every idea that you see today has some analog from the nineties.”
Dalton Caldwell Feb 2, 2022 ▶ 11:37 How To Change The World? Get The Small Things Right – Dalton Caldwell and Michael Seibel · Y Combinator
Andreessen: Every failed late-1990s dot-com idea has now worked
“Entire, I think at this point, catalog of all of the failed.com ideas of the late 19 nineties, and I believe they've now all worked.”
Marc Andreessen Jan 25, 2022 ▶ 35:22 #129 Marc Andreessen: Interview with an Icon
20VC Assertion Supported
Eisenberg: Post-1999 Tech Crash Occurred in Two Phases Including Fiber Optics
“People forget that there were two phases to the bubble coming undone. There was the.com, which has become famous because of the pets.com commercial, right? So that's what we all think.com.com. But there was a second one in fiber optic communications, which was…”
Michael Eisenberg Dec 6, 2021 ▶ 7:28 20VC: Bill Gurley and Michael Eisenberg on The First Signs of an Impending Bust, What Happens with a Market Crash, How Do Public Markets Impact Private Valuations & The Biggest Lessons from 20 Years Investing in Venture
20VC Prediction Held up
Hartz: Speculative SPAC deals will collapse like the dot-com bubble
“What we do see, and what we do predict, unfortunately, is something akin to perhaps the dot-com bubble in 99 and 2000, where you saw a lot of bright, shiny objects, and big flash in the pan market seeming successes, and then you'll see a lot of these coming do…”
Kevin Hartz Aug 31, 2020 ▶ 17:44 20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*
a16z Opinion
Evans: Sovereign wealth funds ordered 3x IPO free float in dot-com bubble
“I remember floating a company for which a Middle Eastern sovereign wealth fund put in an order for the whole of the free float with us and each of the two other banks on the deal, so they ordered three times the entire number of shares on the offer, and I reme…”
Benedict Evans Jan 2, 2019 ▶ 1:24 a16z Podcast | The Rise of the Quasi-IPO
a16z Assertion Not publicly verifiable
Evans: 55% of dot-com bubble VC went to companies under two years
“55% of all the money in the bubble was going to companies that were less than two years old.”
Benedict Evans Jan 2, 2019 ▶ 15:06 a16z Podcast | The Rise of the Quasi-IPO
CAPITAL ALLOCATORS Assertion Supported
Mauboussin: Manager Return Dispersion Spiked During Dot-Com Era Before Reverting
“So that standard deviation had been going down, down, down, sixties, seventies, eighties, into the nineties. And then there was a massive reversal where the standard deviation went way back up around the dot com period. And so there's a spike, and then it come…”
Michael Mauboussin Jan 8, 2018 ▶ 15:36 Michael Mauboussin – Active Challenges, Rational Decisions and Team Dynamics (Capital Allocators, EP.36)
20VC Opinion
Schuler: High late-stage tech valuations are not a dot-com bubble
“All these prices, all these unicorns, this must be just like the dot-com bubble was, when it's nothing like the dot-com bubble. You were probably quite young for those of us who lived through it, I was exactly, exactly. You have to read the history. We are the…”
Barry Schuler Jul 5, 2017 ▶ 13:39 20VC: How To Get Back To 200 Tech IPOs Per Year, Why We Are In A 'Bulge" Not A Bubble & The Impending Flat & Down Rounds To Come with Barry Schuler, Partner @ DFJ Growth
Caldwell: Holding a dot-com peak portfolio long-term still yielded decent returns
“If you would have held and you had a decent portfolio, then you actually, even if you were the dumbest money at the top of the market, you would have done okay.”
Dalton Caldwell Jul 1, 2017 ▶ 1:07:29 IPFS, CoinList, and the Filecoin ICO with Juan Benet and Dalton Caldwell · Y Combinator
20VC Prediction Not checkable as stated
Schrömgens: Tech market will not repeat the 1999 dot-com crash
“And I think today we are definitely in a different stage of that market. So I think there is probably less volatility today. So I would not assume that the same thing happens today again that happened 15 years ago or so, yeah?”
Rolf Schrömgens Jun 2, 2017 ▶ 5:14 20VC: Trivago Founder on Why Incumbents Have Lost Their Main Business Model, Why You Have To Destroy Everything Ego Related & Why Transparency Is The Key To Capital Flow
20VC Insight
Rabois: Dot-com bubble forced startups to hire non-tech talent
“I think there was so much hype and so much interest in technology and internet innovation that, and so many companies were being funded that the companies were desperate for talent. So they were willing to hire like people like me who might've had some skills,…”
Keith Rabois May 15, 2017 ▶ 4:04 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
TOP FOUNDERS Assertion Not checkable as stated
Hawk: Dot-com founders went bankrupt paying taxes on phantom stock gains
“I had good friends that had you know, gone public, actually exercise their options to pay the tax on the lower tax basis saw their value go all the way up and then down to zero. And they'd already paid tax on a phantom gain and, you know, were bankrupt, lost t…”
Kenny Hawk Jun 12, 2016 ▶ 9:27 EP 323: He took his company public for $1b
MAD Prediction Not checkable as stated
Startup valuation correction will be a long tail, not a crash
“This is not like, 99 to 2001, where it went like that. I think it's much more of a long tail”
Peter Fenton Mar 18, 2016 ▶ 36:29 A Fireside Chat with Benchmark General Partner Peter Fenton (Data Driven NYC / FirstMark)
20VC Insight
Lipman: Tech market bubbles yield long-term benefits and valuable lessons
“A lot of people are looking at it through a negative lens, but there are lots of benefits to a potential bubble, and I think that in the long-term perspective, if we look from 2000 to now, I think that the 2000 bubble, or the, you know, dot-com bubble, has giv…”
Brandon Lipman Apr 20, 2015 ▶ 3:37 20 VC 029: The Potential Upside To A Technology Bubble with TechCrunch's Brandon Lipman

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