PayPal

includes PayPal API, PayPal Credit, PayPal UK

40 statements across 32 episodes · 13 bullish · 6 bearish · 24 people on the record · first statement May 11, 2015 by Jay Acunzo · said 289 times in 108 episodes since 2015 · across every show →

Mentions by year, the whole family

brought up most by Harry Stebbings (107), Matan Bar (14), Keith Rabois (13), Lee Hower (11), Reid Hoffman (8), Kevin Hartz (8), Mitchell Green (7), Matt Lerner (7)

tap a year for its mentions
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01020201520162017201820192020202120222023202420252026episodes it came up in
002.510520201520162017201820192020202120222023202420252026episodesmentions per episode
2026 48 mentions in 12 episodes 4 per episode
2025 14 mentions in 10 episodes 1 per episode
2024 51 mentions in 18 episodes 3 per episode
2023 22 mentions in 13 episodes 2 per episode
2022 13 mentions in 9 episodes 1 per episode
2021 25 mentions in 7 episodes 4 per episode
2020 50 mentions in 12 episodes 4 per episode
2019 4 mentions in 1 episode
2018 4 mentions in 3 episodes 1 per episode
2017 38 mentions in 12 episodes 3 per episode
2016 7 mentions in 5 episodes 1 per episode
2015 13 mentions in 6 episodes 2 per episode

every mention, scene by scene, with the transcript →

Everything said about PayPal, oldest first

May 11, 2015 positive
Insight
The PayPal Mafia's Success Was Driven by Early Talent Aggregation
“So I think it's just like a few founders who were able to attract a lot of talented people together. And those people were going to be doing very successful things anyway. And they just followed the best talent initially.”
Jay Acunzo May 11, 2015 ▶ 18:45 20 VC 035: The Ultimate Marketing Guide for Startups with Jay Acunzo, VP of Platform @ NextView Ventures
Oct 26, 2015 positive
Assertion Supported
Major tech companies scaled without traditional sales or marketing
“There's a bunch of companies like PayPal, Airbnb, Facebook, Hotmail, Twitter, LinkedIn, Dropbox, WhatsApp, Quora, Reddit. A bunch of companies who've gotten really big, really fast, without doing any traditional sales or marketing.”
Matt Lerner Oct 26, 2015 ▶ 10:22 20 VC 082: 500 Startups Week: Growth Hacking 101: How To 10x Your Conversion with Matt Lerner, Head of Distro Dojo London
Feb 8, 2016
Assertion Supported
Gil Penchina's early investments include PayPal, LinkedIn, and AngelList
“Some of Gil's investments include some pretty well-known companies that you might have heard of, including PayPal, LinkedIn, AngelList themselves, Indiegogo, and many, many more.”
Harry Stebbings Feb 8, 2016 ▶ 1:14 20VC: Gil Penchina on Building The World's Largest AngelList Syndicate with Flight.vc
Feb 10, 2017
Assertion Not checkable as stated
NatureBox pre-sold 100 boxes via Facebook ads before the product existed
“The first thing that we did is we put a landing page up that was Naturebox.com, it showed a picture of what the box looked like, and then you could click a buy now button. And if you clicked that buy now button, you actually got sent to PayPal, where you could…”
Gautam Gupta Feb 10, 2017 ▶ 5:53 20VC: How Startups & VCs Can Build Relationships with Potential Corporate Acquirers? The Challenge Of Operating Both A B2B & B2C Business Model & Why Fundraising Is The One Element Founders Cannot Control with Gautam Gupta, Founder & CEO @ NatureBox
Mar 8, 2017
Assertion Supported
Hower: PayPal went through three CEOs and burned $10M+ monthly in 2000
“During my first year working there in 2000, you know, we had essentially three different CEOs over the course of that year. You know, at our worst point, we were burning, you know, more than ten million dollars a month.”
Lee Hower Mar 8, 2017 ▶ 6:24 20VC: Why Valuation Is Of Critical Importance At Seed, How To Understand Innovation Cycles & Having 3 CEOs and Burning $10m a Month with Lee Hower, Co-Founder @ NextView Ventures
May 15, 2017 negative
Insight
Rabois: Startups should avoid general managers in favor of functional experts
“Some management lessons about avoiding general managers. We didn't really subscribe to the view that someone was a quote unquote good manager versus someone who was excellent in a particular discipline. And I think there's a lot of truth to that.”
Keith Rabois May 15, 2017 ▶ 9:21 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
May 22, 2017 positive
Assertion Supported
Stebbings: Kevin Hartz's Angel Portfolio Includes Airbnb, Uber, and Pinterest
“Kevin's also a prolific angel investor, with one of the most successful angel portfolios in the valley, with the likes of Airbnb, Uber, PayPal, Pinterest, and Yammer, all in Kevin's personal angel portfolio.”
Harry Stebbings May 22, 2017 ▶ 1:02 20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Nov 15, 2019 negative
Opinion
PayPal feels like outdated technology due to lagging checkout innovation
“If you've used PayPal, you know, in the last few years, you know that it doesn't feel like an experience that was made in the last few years. It feels like older technology.”
Dom Holland Nov 15, 2019 ▶ 11:41 20VC: Why Speed Is The Biggest Differentiator a Founder Can Have, How To Hire Seasoned Tier 1 Talent To An Early Stage Startup & How To Start, Scale and Manage Remote Teams with Domm Holland, Founder & CEO @ Fast
Jun 15, 2020 positive
Insight
David Sacks: Top Startup Outcomes End Up 10x Larger Than Founders Expect
“Probably just that the outcomes are going to be 10 X or bigger than you think. When we were doing PayPal, it was hard to envision that it would be a hundred billion dollar plus company in 20 years. We thought a one and a half billion dollar outcome was great. …”
David Sacks Jun 15, 2020 ▶ 34:21 20VC: Craft Ventures' David Sacks on How To Assess Founder Psychology, How To Accurately Evaluate CAC, Burn and Churn & What Makes The Very Best Startup Boards
Oct 26, 2020
Assertion Partly supported
PayPal Raised $100M at $500M Valuation Days Before the 2000 Crash
“The company had raised a hundred million at 500 pre at the height of the bubble. We literally closed the financing right at the beginning of April, 2000, I think, 1516 days before the Nasdaq started to slide.”
Roelof Botha Oct 26, 2020 ▶ 6:05 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success
Oct 26, 2020
Assertion Supported
PayPal Burned Over $10M Monthly With Seven Months Runway in 2000
“We raised this hundred million dollar round that I referenced in March, and then by June, we had seven months of runway left. We were burning over ten million a month, and Mike Maritz actually was the one who really rang the alarm bells for us and got us to fo…”
Roelof Botha Oct 26, 2020 ▶ 7:34 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success
Oct 26, 2020
Disclosure
Mike Moritz Recruited Botha to Sequoia Despite Lacking a CS Degree
“Meg Whitman gave me an offer to remain a CFO of the company, and Mike Moritz gave me a call and asked whether I'd interviewed Sequoia, which is kind of strange because they were looking for a computer science major who'd done product management at an enterpris…”
Roelof Botha Oct 26, 2020 ▶ 3:46 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success
Dec 7, 2020 negative
Disclosure
Reid Hoffman passed on Stripe over valuation and regulatory payments risk
“Having been, you know, part of the five-person executive team at PayPal through its, you know, dogfight Existence of survival or death. I knew all the landmines in the payment industry. So they came to me and said, hey, we've got this deal, which is, you know,…”
Reid Hoffman Dec 7, 2020 ▶ 33:43 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset
Feb 11, 2021 positive
Insight
Bar: Ubiquity drives winner-takes-all dynamics in payment networks
“And ubiquity wins. Like Venmo, PayPal, Zelle, Square Cash, all these payment networks, they became ubiquitous around the US, As more and more people started using them, and that's how its winner takes all, or winner takes most, I guess, with these types of pay…”
Matan Bar Feb 11, 2021 ▶ 6:28 20VC: Scaling to a $1.3Bn Valuation While in Stealth, The Power of Different Network Effects Within Payment Platforms & How To Leverage Your Board and Investor Base for the Most Value with Matan Bar, Founder & CEO @ Melio
Jul 26, 2021 bullish
Assertion Supported
PayPal and Square surpassed Bank of America and Goldman Sachs in 2020
“Last year, you probably know this, but you know, you've heard some of these stats, like PayPal became more valuable than Bank of America and Square became more valuable than Goldman.”
Nick Shalek Jul 26, 2021 ▶ 23:38 20VC: Ribbit Capital's Nick Shalek on How To Think Through Ownership and Price Sensitivity, When More Money and Pre-Emptive Rounds are Good vs Bad & Investing Lessons from Yale's David Swensen
Jan 21, 2022 negative
Disclosure
Partovi passed on PayPal despite recognizing Max Levchin's genius
“At my first startup, LinkExchange, we had this brilliant contractor who was younger than us, so I was 25, Max Lefton was 22, and when we sold our company, he left to start PayPal. We all knew Max was, like, just a whole next-level brilliance. I mean, when he w…”
Ali Partovi Jan 21, 2022 ▶ 24:25 20VC: How I Lost a $125M Deal with Yahoo by Being Too Honest, The M&A Meeting with Steve Jobs That Did Not Go Well and How U2's Bono Saved The Day For One Tech Startup with Ali Partovi, CEO @ Neo
Nov 26, 2022 neutral
What-if
Jaswa: A $50B PayPal acquisition would have killed the PayPal Mafia
“If PayPal sold to eBay for fifty billion, I doubt the intensity and commitment to pursuing startups would have stayed that, would have been as high for as many of them. Certainly some, but not most.”
Sujay Jaswa Nov 26, 2022 ▶ 26:54 Jeffrey Katzenberg & Sujay Jaswa: Takeaways from Dreamworks; What happened with Quibi? | 20VC #952 · 20VC with Harry Stebbings
Nov 28, 2022 positive
Insight
Kuusi: A tech company's biggest impact is its talent ecosystem, not its product
“Like if you think about like, you know companies like PayPal and Skype and so forth, like, you know, these companies, I would argue the biggest impact of those companies wasn't the services they created. It's the people that they touched and what those people …”
Miki Kuusi Nov 28, 2022 ▶ 1:13:00 Miki Kuusi: How I Scaled Wolt to $8B; Why I Sold to DoorDash | 20VC #953 · 20VC with Harry Stebbings
Apr 14, 2023
Assertion Partly supported
PayPal launched its first hardware product within six months under Marcus
“And in the span of six months or less, we basically had our product in the market, which was the first hardware product that PayPal had shipped.”
David Marcus Apr 14, 2023 ▶ 13:55 David Marcus: How I Came to Lead PayPal; Why FB's Crypto Failed; How AI Fixes Inequality | E1001 · 20VC with Harry Stebbings
Apr 14, 2023
Disclosure
Marcus intentionally shocked PayPal's culture to force non-aligned employees out
“I proactively decided to do it in a brutal way as I wanted it to be a shock to the culture so that it became uncomfortable to the people who wouldn't be a cultural fit for the company.”
David Marcus Apr 14, 2023 ▶ 16:17 David Marcus: How I Came to Lead PayPal; Why FB's Crypto Failed; How AI Fixes Inequality | E1001 · 20VC with Harry Stebbings
Nov 27, 2023
Assertion Not checkable as stated
Rabois: Only 3 of 254 early PayPal employees lived in San Francisco
“There was three people out of 254 people in the company that, when we sold the company, that could live in San Francisco because the company was based in Palo Alto. There was no extra time to commute between Palo Alto and San Francisco.”
Keith Rabois Nov 27, 2023 ▶ 5:55 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Mar 11, 2024 neutral
Assertion Not checkable as stated
Max Levchin Initially Rejected Joe Lonsdale at PayPal After Whiteboard Argument
“Max rejected me the first time as a freshman. We had an argument on a whiteboard and I thought he was going to bring me in anyway.”
Joe Lonsdale Mar 11, 2024 ▶ 4:10 Joe Lonsdale: The Future of TikTok; Is it a Danger to US National Security? | E1125 · 20VC with Harry Stebbings
Mar 13, 2024 positive
Insight
Narayanan: Growth teams must use counter metrics to balance competing goals
“One of the things that we don't do enough is counter metrics, and I think I saw that at PayPal and at Facebook, where you would grow a metric like at PayPal, for example, there were two teams. One was growing revenue, and then one was actually stopping revenue…”
Chandra Narayanan Mar 13, 2024 ▶ 1:19:27 Chandra Narayanan: Top 5 Lessons from Leading Analytics at Facebook | E1126 · 20VC with Harry Stebbings
May 3, 2024
Assertion Partly supported
Rabois: PayPal had virtually no successful external executive hires
“And this was definitely the PayPal model. We basically had no external hires that thrived, and so everybody was internally groomed from within.”
Keith Rabois May 3, 2024 ▶ 19:07 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 31, 2024
Disclosure
Lerner: 90% of PayPal's growth came from 10% of initiatives
“When I look back on my time at PayPal, 90% of our growth came from, like, 10% of the stuff that we did.”
Matt Lerner May 31, 2024 ▶ 2:31 Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159 · 20VC with Harry Stebbings
May 31, 2024
Insight
Lerner: Organizational alignment accounts for 90% of success in big companies
“When you're in a big company where having the right answers like five or 10% of the problem and getting the entire organization and to change people's mindset and align resources ends up becoming like 80 or 90% of the problem.”
Matt Lerner May 31, 2024 ▶ 2:08 Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159 · 20VC with Harry Stebbings
May 31, 2024 positive
Assertion Not checkable as stated
Lerner: PayPal's best growth hires had zero marketing or product background
“The best, I'll say categorically, the best growth people I hired and managed in my time at PayPal had no marketing experience, had no product experience at all.”
Matt Lerner May 31, 2024 ▶ 33:09 Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159 · 20VC with Harry Stebbings
May 31, 2024 negative
Assertion Not checkable as stated
Lerner: PayPal wasted hundreds of millions on unused marketing and products
“They spent hundreds of millions of dollars on marketing campaigns, building products that, frankly, nobody ever used”
Matt Lerner May 31, 2024 ▶ 3:03 Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159 · 20VC with Harry Stebbings
Jun 10, 2024
Insight
All Hyper-Growth Startups Are Chaotic Hot Messes
“Having done this at PayPal, having done this at LinkedIn, having done this at Airbnb, having done, like all of this stuff, it's always a chaotic hot mess.”
Reid Hoffman Jun 10, 2024 ▶ 36:21 Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163 · 20VC with Harry Stebbings
Jul 22, 2024
What-if
Hartz regrets turning down Peter Thiel's invitation to join Palantir at inception
“The day that acquisition of PayPal by eBay was announced Peter had resigned, and I met him up at the Sundeck restaurant in up on Sand Hill Road, and he said, you know, Kevin, I'm working on this business, and, you know, we're taking kind of the fraud algorithm…”
Kevin Hartz Jul 22, 2024 ▶ 52:04 Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings
Aug 26, 2024
Assertion Supported
Alibaba Pitch Framed Company as eBay, Amazon, and PayPal of China
“The story was positioned very simply that, hey, it's the China consumer play, and they are the eBay plus Amazon plus PayPal of China.”
Imran Khan Aug 26, 2024 ▶ 54:50 Imran Khan: Why the IPO Market is Not Closed & Lessons From Taking Snap & Alibaba Public | E1194 · 20VC with Harry Stebbings
Dec 16, 2024
Disclosure
Hoffman passed on early investments in Stripe and Square
“I got pitched early in stripe and square, and I Didn't do the investments because I knew how hard payments was from PayPal.”
Reid Hoffman Dec 16, 2024 ▶ 1:00:28 Reid Hoffman, LinkedIn & Paypal Founder: Trump Administration, Elon Musk and DOGE | E1239 · 20VC with Harry Stebbings
Nov 10, 2025 neutral
Assertion Open
Thiel paid bonuses to PayPal employees living near the office
“He had, like, a bonus system for PayPal employees. If they lived within, like, a couple miles of the office, you'd give them more money.”
Everett Randle Nov 10, 2025 ▶ 6:10 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Dec 18, 2025 positive
Assertion Contradicted
Calacanis: Peter Thiel fully vested Elon Musk's stock when firing him
“He fired him, but he treated him like a human being. Okay. He vest fully vested all his stock, took nothing out of his pocket, thanked him for it and told him that was the way it was going to be.”
Jason Lemkin Dec 18, 2025 ▶ 1:15:15 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Mar 16, 2026 positive
Assertion Partly supported
Rajaram: PayPal raised prices five times in three years early on
“And he told us that PayPal back in the day, raised prices five times. In three years, because there's such stickiness. They knew their customers really couldn't do anything.”
Gokul Rajaram Mar 16, 2026 ▶ 40:34 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Jul 16, 2026 negative
Assertion Not checkable as stated
Lemkin: Faking affiliate attribution is standard practice across startups
“Doing basically what everyone in your industry does, doing scammy affiliate marketing when it's basically part of your thing. I mean, startups cut corners, right? It's not, this isn't Delvesque, but everyone cuts a corner. When everyone in your industry is sli…”
Jason Lemkin Jul 16, 2026 ▶ 55:59 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Jul 23, 2026 neutral
Assertion Supported
O'Driscoll: Stripe and PayPal Each Process $1.8 Trillion Annually
“They both process kind of 1.8 trillion dollars a year, right?”
Rory O'Driscoll Jul 23, 2026 ▶ 52:50 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Jul 23, 2026 neutral
Prediction Open · timeframe Jul 2029
Lemkin: Stripe-PayPal Acquisition Premium Will Land at Around 35%
“So it's probably just a dance from 28 to 35. And then it gets parked with advent to while they figure out antitrust and capital issues.”
Jason Lemkin Jul 23, 2026 ▶ 1:02:58 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Jul 23, 2026 bullish
Prediction Open · timeframe Jul 2029
Lemkin: PayPal's Board Will Ultimately Accept Stripe's Acquisition Offer
“The board rejected it, right? And the fact that the board rejected it means to me that they're going to accept it.”
Jason Lemkin Jul 23, 2026 ▶ 58:36 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
Sep 3, 2026 positive
Opinion
Stripe Was Smart to Pursue PayPal but Refused to Overpay
“Smart deal to try and do, but they're clearly not willing to overpay as they see it.”
Rory O'Driscoll Sep 3, 2026 ▶ 1:04:54 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
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