PayPal, every mention
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every year anyone David Sacks 86Jason Calacanis 57Chamath Palihapitiya 14David Friedberg 12Keith Rabois 4Elon Musk 4Brian Armstrong 3Mark Pincus 2Peter Thiel 1Patrick Collison 1
Verbatim, from the transcripts: the passages where PayPal comes up
Chip Stocks Crash, $20B Fund Margin Called, Frontier Labs: SLOW DOWN AI, Mamdani's Grocery Stores
- ▶ 11:01 David Sacks I mean, you know, back in the PayPal days with the PayPal mafia, we would think in this way of exponential increases because we would see an exponential growth curve.
Can the AI Industry Regulate Itself? Stripe Wants PayPal, China Catches Up, NY Bans Datacenters
- ▶ 20:18 Jason Calacanis Fifty three billion for your alma mater, David Sacks PayPal, which is a public company. 8 times in the scene
- ▶ 21:41 Jason Calacanis PayPal has PsyUSD, which is already in circulation.
- ▶ 26:44 David Friedberg To the cash investors, that cash is then going to buy a PayPal. 5 times in the scene
- ▶ 30:28 Jason Calacanis Why didn't you make a bit sacks for PayPal? 7 times in the scene
- ▶ 33:56 David Sacks But it seems to me that the existential issue for PayPal is that you're dealing with a product that's 25 years old. 10 times in the scene
GameStop CEO Ryan Cohen’s $56B Plan to Take Over eBay
- ▶ 37:57 unnamed speaker They bought PayPal and then later spun it out and divested and they bought Skype for 2.6 billion in 2005 and then sold 70% of it for two billion in 2009 and then they got lucky with Microsoft overpaying in 20 11 and they made another two… 2 times in the scene
World's First Trillionaire, Anthropic Fable Banned, The New Oligarchs, Iran Peace Deal
- ▶ 18:00 Jason Calacanis You've been friends with Elon since PayPal days, obviously, and, um, you obviously were an investor in SpaceX for a long time.
The Future of Everything: What CEOs of Circle, CrowdStrike & More See Coming in 2026
- ▶ 32:15 Jason Calacanis There'll be an Amazon one, obviously PayPal's added one.
Coinbase CEO's Top 3 Crypto Trends for 2026 + More from Davos!
- ▶ 11:28 Brian Armstrong We also support PayPal, Stablecoin.
- ▶ 11:28 Brian Armstrong We also support PayPal, Stablecoin.
- ▶ 28:17 Brian Armstrong I think, you know, he did the thing with, um, PayPal and X and, um, and then, you know, he went into these, like the world of atoms, not bits, right?
Europe's Free Speech Failure and the "Censorship Industrial Complex" with Sarah B. Rogers
- ▶ 37:47 Jason Calacanis Uh, hey, you're PayPal.
Adam Carolla on California’s Collapse: Fires, Failed Leadership, and Gyno-Fascism
- ▶ 1:06 unnamed speaker PayPal Open is the platform designed to help you grow into yours with access to business loans so you can expand and reach hundreds of millions of PayPal customers worldwide. 2 times in the scene
- ▶ 1:06 unnamed speaker PayPal Open is the platform designed to help you grow into yours with access to business loans so you can expand and reach hundreds of millions of PayPal customers worldwide. 3 times in the scene
Grok 4 Wows, The Bitter Lesson, Third Party, AI Browsers, SCOTUS backs POTUS on RIFs
- ▶ 1:49 Jason Calacanis Another brilliant PayPal alumni and, uh, dare I say, a GOP supporter, Heath Raboy.
Trump Rally or Bessent Put? Elon Back at Tesla, Google's Gemini Problem, China's Thorium Discovery
- ▶ 34:51 Chamath Palihapitiya So like the Indian Amazon work, the Indian PayPal kind of work, the Indian DoorDash kind of work.
Howard Lutnick | All-In DC
- ▶ 42:00 Howard Lutnick And if all the guys who did PayPal, like Elon knows this by heart, right?
The Stablecoin Future, Milei's Memecoin, DOGE for the DoD, Grok 3, Why Stripe Stays Private
- ▶ 3:30 Patrick Collison People just didn't think that, I mean, you know, teenagers weren't actually teenagers at the time, but you know, people in their early twenties, college kids taking on, you know, PayPal or the incumbents or regulated financial services or…
- ▶ 1:40:02 John Collison PayPal, 80% off their 20, 21 peak.
From Skeptic to Supporter: How This Billionaire Got ‘Red-Pilled’ by Trump
- ▶ 8:54 Mark Pincus But do you remember when he would be on Twitter all the time post PayPal, trying to correct the story and just write long, long diatribes.
Red-pilled Billionaires, LA Fire Update, Newsom's Price Caps, TikTok Ban, Jobless MBAs
- ▶ 15:47 Mark Pincus But do you remember when he would be on Twitter all the time post PayPal, trying to correct the story and just write long, long diatribes.
Trump's Cabinet, Google's Quantum Chip, Apple's Flop, TikTok, State of VC
- ▶ 3:17 Jason Calacanis Saks and Peter Thiel went on to do PayPal. 4 times in the scene
- ▶ 23:58 Jason Calacanis They'll look at PayPal if they worked in finance.
Inflated GDP?, Google earnings, How the media lost trust, Rogan/Trump search controversy, Election!
- ▶ 1:27:46 David Sacks Let me explain how this actually works since I was founding CEO of PayPal.
Ingo Uytdehaage, Adyen | All-In Summit 2024
- ▶ 24:02 David Sacks Do you ever see PayPal on the market? 6 times in the scene
- ▶ 24:12 Ingo Uytdehaage So, uh, we work closely with them also offering, um, we just did a press release on their new Express checkout that we do together with them.
Peter Thiel: The Coming Collapse No One Is Prepared For
- ▶ 0:16 Peter Thiel Changed money with PayPal, was the first outside investor in Facebook, uh, backed Palantir, which is, I believe they helped find Osama bin Laden.
"Founder Mode," DOJ alleges Russian podcast op, Kamala flips proposals, Tech loses Section 230?
- ▶ 13:21 David Sacks I mean, I remember way back in the PayPal days, over 20 years ago, we had a rule that we weren't, wouldn't hire MBAs.
In conversation with Reid Hoffman & Robert F. Kennedy Jr.
- ▶ 2:07 Jason Calacanis He's got his own podcast, Masters of Scale, and, uh, he, he and David Sachs work together at PayPal. 7 times in the scene
Break up Google, Starbucks CEO out, Kamala’s price controls, Boeing disaster, Kursk offensive
- ▶ 3:01 David Sacks Well, it's where PayPal got its first funding round, where John Malloy from Nokia Ventures beamed the money to Peter and Max at Bucks.
The Besties Take Napa | All-In Special
- ▶ 19:28 David Sacks I went anyway, and, but it ended up not mattering because I ended up joining PayPal after I graduated from law school, so I wish I had a better story.
GPT-4o launches, Glue demo, Ohalo breakthrough, Druck's Argentina bet, did Google kill Perplexity?
- ▶ 1:12:32 David Sacks When we did PayPal, none of us knew anything about payments, that was one of the reasons we were successful.
E170: Tech's Vibe Shift, TikTok ban debate, Vertical AI boom, Florida bans lab-grown meat & more
- ▶ 39:32 David Sacks With PayPal, just to launch really what was an MVP, we had, I'd say, a dozen developers, and it was pretty expensive, and we had to set up our own colo.
E167: Google's Woke AI disaster, Nvidia smashes earnings (again), Groq's LPU breakthrough & more
- ▶ 26:38 David Sacks I mean, look, when we were developing PayPal in the late nineties, really around 1999,
E164: Zuck’s Senate apology, Elon's comp package voided, crony capitalism, Reddit IPO, drone attack
- ▶ 3:44 Jason Calacanis I mean, you're still riding on that Yammer and PayPal.
E163: Market rips, Media RIFs, Texas defies Biden, Fintech reckoning, ARkStorm 2.0 & more
- ▶ 1:23:30 David Sacks And certainly we saw this at PayPal, where the margin on any particular payment was pretty low. 2 times in the scene
E160: 2024 Predictions! Markets, tech, politics, and more
- ▶ 1:15:12 David Sacks Is Jimmy Soni's book, The Founders, which is the story of PayPal and the entrepreneurs who shaped Silicon Valley. 2 times in the scene
E156: Ivy League antisemitism, macro, SaaS recovery, Gemini, Figma deal delay + big Friedberg update
- ▶ 58:58 Jason Calacanis And now with PayPal, right?
E151: WW3 risk, War with Iran?, 4.9% GDP, startup failures growing, new Speaker & more
- ▶ 43:33 Chamath Palihapitiya PayPal is down 30%.
E146: Did the Fed break the VC model? Plus IPOs, M&A, revaluing unicorns & more
- ▶ 59:32 David Sacks By the way, that was PayPal's problem back in the day, 20 years ago.
E142: "Rich Men North of Richmond" hits #1, upward mobility, real estate capital crunch, Trump RICO
- ▶ 1:25:24 Chamath Palihapitiya The thing to remember about all these businesses, Stripe, Adyen, PayPal, is that they're middlemen businesses, which by definition means that they don't have pricing power. 2 times in the scene
E141: State of Series A's, VC dry powder, IPO window opens + more with Bill Gurley & Brad Gerstner
- ▶ 11:04 David Sacks Back in the PayPal days, you know, I didn't have any real business education.
E124: AutoGPT's massive potential and risk, AI regulation, Bob Lee/SF update
- ▶ 37:17 David Sacks I remember when, like, PayPal got to, like, a hundred billion a year of payment volume, and now it's, like, hundreds of billions, so.
E104: FTX collapse with Coinbase CEO Brian Armstrong + election results, macro update & more
- ▶ 29:34 David Sacks I mean, I remember when I was doing PayPal, like, 22 years ago, and the company was, like, six months away from running out of money.
- ▶ 1:17:13 Jason Calacanis The number of hours that was expected at a startup was what, Saks, when you were at PayPal?
E102: Elon closes Twitter deal, $META uncertainty, Zuck's historic bet, big tech decline & more
- ▶ 11:27 Jason Calacanis Well, Sax, you were the COO of PayPal with Elon and Ruloff and TL and everybody in that crew over 20 years ago, uh, and verified you understand pretty well because you yourself have been brigadooned of late 2 times in the scene
- ▶ 13:45 David Sacks I mean, 20 years after PayPal,
E99: Cheating scandals, Twitter updates, rapid AI advancements, Biden's pardon, Section 230 & more
- ▶ 0:36 Jason Calacanis Weren't you the same guy who was responsible for scaring PayPal? 2 times in the scene
- ▶ 1:14:48 David Sacks Do you think the average consumer, the average user of PayPal is demanding that they engage in all of these restrictive policies, throwing off all these accounts who have the wrong viewpoints? 2 times in the scene
- ▶ 1:23:34 David Sacks You have companies like PayPal, which are just engaging in retaliation, basically financial retaliation, purely on based on what political viewpoints they have. 2 times in the scene
E98: Big tech starts making cuts, Fed incompetency, global debt, Russia/Ukraine & more
- ▶ 21:44 David Sacks PayPal was built largely during the downturn.
- ▶ 46:02 David Friedberg You would take all the data from Intuit, from PayPal, from Visa, from MasterCard, from the internet.
E95: Winter is Coming, Europe's energy crisis, Kim Kardashian's new PE firm & more
- ▶ 59:47 David Sacks In the past, the consumer products I've been involved in like PayPal or investing in social networks like Facebook, they were viral.
#AIS: Bestie AMA with Valor's Antonio Gracias
- ▶ 32:34 unnamed speaker I have a question for the 17th most important person from PayPal.
- ▶ 58:50 David Sacks Um, so, you know, this question of micropayments has come up all the way since, you know, back to when I was working on PayPal, and one of the problems with micropayments is, as the name suggests, the amounts are very, very small, so you… 2 times in the scene
- ▶ 1:15:34 unnamed speaker Um, so my question is, Amar talked about these, like, startup generating systems like Stanford or PayPal.
#AIS: Pear VC’s Mar Hershenson on making successful founders
- ▶ 7:47 Mar Hershenson And one of them, perhaps, is the PayPal mafia.
- ▶ 18:03 Jason Calacanis And, you know, when you look at what happened at PayPal, and I'm really interested in hearing David's perspective on this, they got to see each other at Stanford, and 40% of the speakers have been to Stanford here at this event.
- ▶ 23:02 David Friedberg Like, being the 17th most important guy at PayPal.
- ▶ 23:40 David Sacks So the, the, the answer is that at PayPal, we recruited our friends to work at the company because literally nobody else like was willing to come work at this crazy startup. 6 times in the scene
#AIS: Tim Urban on political discourse + Keith Rabois on early-stage investing in 2022
- ▶ 1:05:59 Keith Rabois So, for me, it was easy because these were people that we worked, David and I worked with at PayPal, and I was smart enough to at least, you know, follow the people that were launching companies after PayPal and give them some money. 4 times in the scene
E81: All-In Summit: Bill Gurley & Brad Gerstner on markets, downturns & investment cycles
- ▶ 4:00 Bill Gurley Elon mentioned PayPal, but like oh five, oh six.
Elon Musk: Twitter's bot problem, SpaceX's grand plan, Tesla stories & more
- ▶ 28:24 Jason Calacanis This seems to me, uh, based on your work with, with David at PayPal, like a, a pretty brilliant idea. 2 times in the scene
- ▶ 1:06:55 Elon Musk I mean, David, do you remember this one from the, from the PayPal, you know, ex PayPal days, 2 times in the scene
- ▶ 1:18:53 Elon Musk Um, you, you want, and really like you said, what, what did PayPal really, really do that helped improve the, the, the bandwidth, the speed at which money could move, um, instead of, of mailing checks back and forth, which amazingly, that… 2 times in the scene
E80: Recession deep dive: VC psychology, macro risks, Tiger Global, predictions and more
- ▶ 2:36 David Friedberg Hey, pal, it's the 17th most important guy from PayPal.
- ▶ 1:22:55 David Sacks You know, PayPal was built during the dot-com crash.
E77: Tech work culture, crypto regulation, stablecoins, $NFLX & more w/ Coinbase CEO Brian Armstrong
- ▶ 1:03:24 David Friedberg Of PayPal.
E75: Fast shuts down, board culpability, Elon buys 9% of Twitter, deplatforming's evolution & more
- ▶ 15:16 David Sacks I mean, look, PayPal had this situation back in, uh, 2000, the year 2000, right after the dot-com crash.
- ▶ 43:06 Jason Calacanis Saks, you worked with Elon at PayPal thoughts on what this does for 2 times in the scene
E68: Trudeau invokes emergency powers, Bitcoin vs. government, Tiger Global's new strategy and more
- ▶ 45:15 Jason Calacanis What's your best advice being one of the great operators in the history of Silicon Valley as a CEO of PayPal.
- ▶ 46:37 Jason Calacanis And then I tie my top two sacks, as a PayPal, and Zenefits, even though it didn't work out, it was still a great run at the time.
- ▶ 58:54 David Sacks Roloff, who worked with us at PayPal, is there. 2 times in the scene
E67: Revisiting Rogan, Canadian truckers' protest, fusion breakthrough, $MSFT's savvy move & more
- ▶ 1:03:41 Jason Calacanis And if you're on, you know, Microsoft, you can use PayPal as an example.
E66: $FB's big drop, Rogan/Spotify mess, Xi/Putin meetup & supply chain issues with Ryan Petersen
- ▶ 0:36 David Sacks I'll tell you, that was the day of PayPal's IPO.
- ▶ 46:15 David Sacks PayPal dropped 25%, too.
- ▶ 54:18 David Sacks So PayPal was just down 25%. 7 times in the scene
- ▶ 1:37:44 Jason Calacanis David Friedberg, and the Rain Man himself, triumphant, versus Peter Thiel in that PayPal match.
E62: Elizabeth Holmes verdict, fraud origins & takeaways, navigating "The Great Markdown" & more
- ▶ 54:23 David Sacks And you know, so PayPal was predominantly built after the dot com crash.
E59: Twitter's content warning algo, equity audits, politicians trading stocks, Fed's next move
- ▶ 18:53 David Sacks So recently, you know, I wrote a piece called the, the no buy list where I basically, you had companies like PayPal and some of these other financial firms were starting to deny service to customers, to users based on their political…
E56: Constitution DAO, Rittenhouse trial coverage, private sector efficiency vs the government
- ▶ 6:21 Jason Calacanis PayPal or Venmo or many other solutions out there.
E55: Valuing crypto projects, Rivian worth $100B+, inflation: causes and corrections and more
- ▶ 1:13:30 Chamath Palihapitiya And we sketched out a plan for what PayPal should do. 5 times in the scene
- ▶ 1:17:58 David Sacks Right, and this is just a, just to close the thought out on the whole eBay PayPal thing. 3 times in the scene
E51: Supply Chain Shortages, Inflation, DeSantis, Ted Sarandos Netflix Memo, Cancel Culture, Fan Q&A
- ▶ 1:29:05 David Sacks Uh, well, I mean, obviously what we did at PayPal has gone on to become a legend, and then, you know, PayPal, I was the founder CEO, he led that to a unicorn exit, so. 2 times in the scene
E49: Coinbase CEO reflects on controversial blog, state of the markets, 1000 unicorns & more
- ▶ 56:50 David Friedberg And Elon sold PayPal and he was able to use that money to reinvest in Tesla and SpaceX.
Balaji Srinivasan: role of decentralization, China/US breakdown & more
- ▶ 1:22:21 Balaji Srinivasan Whereas let's say something like Twitter or PayPal, the root password is not public.
E44: USA's Afghanistan embarrassment, China's new algo laws, future of robots + Italy recap!
- ▶ 8:49 David Sacks It's better than PayPal.
- ▶ 1:20:21 Jason Calacanis You worked with Elon at PayPal.
E43: Innovative venture strategies, Zymergen's implosion, Square acquires Afterpay & more
- ▶ 1:07:38 David Sacks Okay, so, well, first, I mean, if we're going to call somebody out, first, I want to call out PayPal.
- ▶ 1:12:35 David Friedberg There's a company called Bill Me Later, that was bought by PayPal in 2008 for a billion dollars. 2 times in the scene
- ▶ 1:20:53 David Sacks PayPal is already well down that road. 3 times in the scene
E41: Vaccine policy, Big Tech, DeepMind's latest breakthrough, wealth creation, opportunity & more
- ▶ 1:32:44 David Sacks If I just stayed at PayPal for 20 years, my stock would have been worth many, many billions, right?
E36: New FTC Chair, breaking up big tech, government silent spying, Jon Stewart, wildfires & more
- ▶ 27:53 David Sacks Um, my experience at PayPal really changed my thinking on this because PayPal, you know, was a startup that launched effectively as an involuntary app on top of the eBay market. 4 times in the scene
E35: Biogen's controversial Alzheimer's drug approval, the billionaire space race, Bitcoin & more
- ▶ 1:20:16 David Sacks I actually wrote, in 1999, when I joined PayPal, I wrote an article called Silicon Valley's Fight Clubs, in which I basically said that startups were the answer to this sort of, you got, remember Fight Club came out in 1999,
E31: Post-vaccination virtue signaling, pandemic lessons, immigration, Caitlyn Jenner for CA & more
- ▶ 40:42 David Sacks So we've seen, you know, like PayPal, I think, you know, there were like three or four immigrants on the founding team, you know, Peter,
E26: State of Venture Capital, plus fan questions on longevity, decentralization & quantum computing
- ▶ 42:47 David Sacks I mean, I did PayPal when I was still in my twenties, but I wasn't the founder of the company. 2 times in the scene
E23: Radical DAs, breaking down FB/Google vs. Australia, sustained fear post-vaccine & fan questions
- ▶ 1:00:51 David Sacks I would say that around the time that PayPal hit a two hundred billion dollar market cap and Slack had a twenty seven billion dollar outcome, I started realizing, you know, if I just stuck with my ideas longer, you know, I probably would…
E18: Inauguration talk, breaking down the $1.9T stimulus, the case for recalling Gavin Newsom & more
- ▶ 7:56 David Sacks You had an announcement from a whole bunch of finance companies, PayPal, Stripe, Square, that said they would, uh, cancel the accounts and,
- ▶ 1:00:53 Jason Calacanis Every single Uber driver, Lyft driver, Postmates driver, Airbnb host, uh, or a person who used the Cash App or PayPal would have said, I can, as one of the first users, I have access to buy shares.
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