Jul 19, 2024 · 45m · more-or-less
#56: Trump and the PayPal Mafia · More or Less Podcast
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the More or Less podcast, co-hosts Dave Morin, Jessica Lessin, Brit Morin, and Sam Lessin dissect Silicon Valley's growing political influence and venture endorsements for Donald Trump, alongside shifting venture liquidity mechanisms and the transferable value of athletic grit.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 99.6% of the talking time here. How this is scored →
The hosts as informed peer 5.1 Guest teaching 0.3 Guest disagreement 0.3 The hosts pushing back 2.4
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 40:43 SPEAKER_05 interjects over Brit
SPEAKER_05 breaks into the conversation forcefully to insist 'No, they are! They are!' contradicting Brit's claim that swimming in the Seine has not been approved.
Hardest push from the hosts ▶ 22:53 Dave rejects Sam's fatalistic election framingDave directly rejects Sam's claim that the presidential race is already over, arguing that undecided swing voters will not switch simply due to the assassination attempt.
Biggest teaching moment ▶ 40:42 Correction on Olympic Seine swimming statusSPEAKER_05 emphatically corrects Brit's statement that Olympic athletes will not be swimming in the Seine river.
The host holds their own ▶ 17:20 Jessica dismantles rational policy assumptions behind tech endorsementsJessica challenges Dave and Sam's analysis by citing Trump's erratic record on TikTok bans and hostility toward EV subsidies to demonstrate that endorsing tech leaders are gambling rather than securing predictable policy.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| 'More or Less' Title Sequence and Theme Song | 3 | 0 | 0 | 1 | The hosts engage in lighthearted banter over podcast merchandise slogans and venture capital acronyms like DPI vs AUM. The listed guests provide only brief background utterances. | |
| Sam Lessin's Rapid Mount Kilimanjaro Hiking Expedition | 3 | 0 | 0 | 1 | Sam shares details of completing the Mount Kilimanjaro hike in under three days and explains the local guide and porter regulations. | |
| Trump's Tech Endorsements and PayPal Mafia Political Influence | 7 | 0 | 0 | 5 | The hosts analyze Silicon Valley's political realignment around Trump and the PayPal mafia. Jessica challenges the notion that tech leaders are guaranteed favorable policy outcomes under Trump, while Sam and Dave debate whether Trump's victory is inevitable. | |
| Heels Versus Faces: Democratic Disarray and Tech Alignments | 7 | 0 | 0 | 5 | The group debates the wrestling heel-versus-face dynamic of Trump tech endorsers compared to Reid Hoffman and Democratic donors. Dave and Brit push back against Sam's cynical stance that the election outcome is already sealed. | |
| Media Frenzy: Campaign Coverage and the Bullet Photo | 6 | 0 | 0 | 3 | Jessica defends mainstream journalism institutions covering the assassination attempt and predicts subscription spikes, while Sam and Brit tease the New York Times for self-aggrandizing coverage of the bullet photograph. | |
| The Return of Tech Deal-Making and Venture Secondaries | 6 | 0 | 0 | 2 | The hosts discuss tech M&A dynamics, examining Goldman Sachs earnings, the likelihood of an FTC block on Wiz, Figma's secondary valuation, and Sequoia re-investing in Stripe. | |
| Debating Carlos Alcaraz's Wimbledon Triumph and Sponsorships | 4 | 2 | 2 | 1 | The hosts discuss Carlos Alcaraz's Wimbledon championship and upcoming Olympic events. When Brit doubts that athletes will swim in the Seine, SPEAKER_05 cuts in to correct her. | |
| Pitching an Exclusive LinkedIn Platform for Former Olympians | 5 | 0 | 0 | 1 | Sam pitches an exclusive recruiting platform for retired Olympic athletes, and Dave backs up the premise by citing Tom Weisel's historical Wall Street hiring policies. |
Statements from this episode (15)
Sam Lessin: AUM is for losers, DPI is for winners
“AUM is a game of politics for losers. DPI is the game of winners. That's how it works. So you can coast by being a political AUM person for a while, but you have nothing to be proud of because all you are is a salesman of stories versus someone who delivers re…”
Sam Lessin says he was the first financier of Venmo
“As, you know, as the first financier of Venmo, let's just talk about this story.”
Lessin: Tech 'mafias' cannot form today because talent is too dispersed
“Now the problem is, is like, there, it's very hard to build mafias because there's just too much going on. Like, there are too many good places for talent to go. It's not concentrated the same way”
Morin: The Biden administration became extremely anti-technology
“Somewhere along the way, the Biden administration became extremely anti-technology.”
Jessica Lessin: Musk times planned business moves to match sensational political headlines
“Musk, in my mind, you know, makes strategic business decisions all day long and then waits for a headline to announce them to make it seem like the assassination attempt got his endorsement or that a new law in California around LGBTQ kids caused him to move a…”
Reid Hoffman and Peter Thiel had a legitimate falling out
“What we probably didn't call was that Reid Hoffman and Peter Thiel would have a legit falling out, and that would be the talk of the conference, right?”
Sam Lessin: The 2024 Presidential Race Is Effectively Over for Democrats
“I just feel like this is over, right? Which I know is not what you're supposed to say, and, like, that helps purpose with town out and the whole nine yards, but, like, you know, Trump just had, like, one of the all-time ten-day periods ever, right?”
Jessica Lessin: Vocal Democratic Tech Donors Have Gone Silent
“Last seven days, they have gone quiet. And many of these people, when I reach out to them, I get, like, a note back from their EA's being like, oh, they're on vacation. You know, like, they don't want to talk.”
Sam Lessin: TikTok's Presence in the US Benefits Meta
“To get rid of TikTok is to point out the fact that its presence in the U.S. Is actually a net positive for Meta.”
Jessica Lessin: Google is highly unlikely to acquire Wiz for $23B
“Like, is Google for twenty-three billion dollars gonna buy Wiz security company? I think it's highly unlikely, but.”
Figma is valued at $12.5B with $700M in ARR
“Not made it through the twenty billion dollar Adobe acquisition is now being valued at 12 and a half. But from, you know, good firms, they have KOTU, General Catalyst, and their ARR's at seven hundred million now.”
Sequoia buying secondary Stripe shares signals a weak venture landscape
“No, Sequoia, like, I don't know what this says about the ecosystem, that there's that few interesting things to invest in, that Sequoia is going back to 2009 to buy Stripe shares. Like, that's pretty wild.”
Morin: Tom Weisel's firm had a standing policy to hire any Olympian
“Tom Weisel, the You know, the famous tech investment banker from the eighties and nineties. He actually was the one that first said this to me and he said he had a standing policy at the firm to hire any Olympian that wanted a job.”