PayPal

5 statements across 3 episodes · 0 bullish · 2 bearish · 2 people on the record · first statement Jan 26, 2024 by Sam Lessin · across every show →

Everything said about PayPal, oldest first

Jan 26, 2024 negative
Opinion
Sam Lessin: Venmo has become a broken user experience under PayPal
“It is still big, but it's like, kind of shitty. The app's kind of broken now. It's been, you know, owned by PayPal for the last decade, and they've kind of like, I don't know, I wouldn't say it's not usable. I certainly use it, but it's like, pretty terrible e…”
Sam Lessin Jan 26, 2024 ▶ 32:55 #31: Fintech Struggles, Netflix Rises and 'Big' is Winning · More or Less Podcast
Feb 27, 2026 bearish
Prediction Not checkable as stated
Jess Lessin: Rumored PayPal acquisition won't happen due to trial balloon leaks
“My spidey sense of why it won't happen is just the, it's the nature of the leaks have been like trial balloons galore.”
Jessica Lessin Feb 27, 2026 ▶ 42:23 Apple, OpenAI & Why Nobody Makes Money in AI | The SaaS Apocalypse · More or Less Podcast
Feb 27, 2026 neutral
Opinion
Sam Lessin: Current administration is Stripe's only window to acquire PayPal
“It's like, this is the one chance for Stripe to sneak through becoming effectively a U.S. Monopoly on payments.”
Sam Lessin Feb 27, 2026 ▶ 37:56 Apple, OpenAI & Why Nobody Makes Money in AI | The SaaS Apocalypse · More or Less Podcast
Jul 24, 2026 neutral
Assertion Partly supported
Jessica Lessin: Stripe is attempting to acquire PayPal
“The Information has a big Stripe financial scoop that is worth discussing because. We have not discussed Stripe in a while and it is trying to buy PayPal.”
Jessica Lessin Jul 24, 2026 ▶ 37:45 Stripe Is Trying To Buy PayPal For $150b | OpenAI Cyber Incident, Frontier Model Economics, Peptides · More or Less Podcast
Jul 24, 2026 neutral
Assertion Supported
Lessin: Stripe Is Teaming Up With Advent for PayPal Bid
“So what they're doing for this PayPal takeover offer, which, you know, is, is just that, like, no sign that any deal is done, and I'm sure other bidders will emerge and whatever, but they're teaming up with Advent, which is a private equity firm,”
Jessica Lessin Jul 24, 2026 ▶ 43:19 Stripe Is Trying To Buy PayPal For $150b | OpenAI Cyber Incident, Frontier Model Economics, Peptides · More or Less Podcast
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