E11: Election Night Special featuring Phil Hellmuth, Bill Gurley, Brad Gerstner & more!
Jason Calacanis (host), Chamath Palihapitiya (host), Phil Hellmuth (guest), David Sacks (host), Phil Hellmuth (guest), John Couvillon (guest), Jonah Gottlieb (election / betting analyst friend of Sacks; exact identity less certain) (guest), J. C. Polls (John Couvillon / pollster guest referenced in description) (guest), David Friedberg (host), Guest (farmer / lockdown-impact commentator, name not clearly stated) (guest), Host (short interjection, likely one of the four besties) (host), Brad Gerstner (guest), Jason Calacanis (host), Phil Hellmuth (guest), Antonio García Martínez (guest), Bill Gurley (guest), Brad Gerstner (guest), Host (very brief aside, one of the four besties) (host), Bill Gurley (guest), Host (single-word interjection) (host), Jason Calacanis (host), Host (single-word interjection) (host), Host (very brief aside) (host), Alex Tabarrok (or similar policy/econ analyst; exact identity uncertain, but guest commentator) (guest), David Friedberg (host), Host (very brief aside) (host), Brad Gerstner (guest), Joe Biden (guest), Phil Hellmuth (guest)
In this episode of All-In Podcast, featuring Jason Calacanis and Chamath Palihapitiya, E11: Election Night Special featuring Phil Hellmuth, Bill Gurley, Brad Gerstner & more! explores all-In Besties Live-Analyze 2020 Election Shock, Polling Collapse, Realignment This live All-In Podcast “Election Night Special” tracks the 2020 U.S. presidential race in real time as results, betting odds, and markets swing dramatically from an expected Biden win toward a potential Trump upset and back to a near coin flip. Regular hosts Jason Calacanis, Chamath Palihapitiya, David Sacks, and David Friedberg are joined by guests Phil Hellmuth, Bill Gurley, Brad Gerstner, pollster Jon Cohen, and others to dissect polls, betting markets, and state-by-state vote tallies.
All-In Besties Live-Analyze 2020 Election Shock, Polling Collapse, Realignment
This live All-In Podcast “Election Night Special” tracks the 2020 U.S. presidential race in real time as results, betting odds, and markets swing dramatically from an expected Biden win toward a potential Trump upset and back to a near coin flip. Regular hosts Jason Calacanis, Chamath Palihapitiya, David Sacks, and David Friedberg are joined by guests Phil Hellmuth, Bill Gurley, Brad Gerstner, pollster Jon Cohen, and others to dissect polls, betting markets, and state-by-state vote tallies.
They explore why polling and media narratives were so wrong, emphasizing missed dynamics among working-class voters, Latinos, men of color, and voters’ reactions to lockdowns, cancel culture, and perceived condescension from coastal elites. The group also discusses market reactions, the likely shape of divided government, and critical ballot initiatives like California’s Prop 22.
Despite deep disagreement about Trump’s character and legitimacy, there is broad consensus that the night represents a massive upset for Democrats’ expectations and a loud protest vote against cultural and political elites. By the end, they see the race as extremely tight, leaning slightly toward a Biden presidency with a Republican Senate, and warn that final results may take days and involve legal battles.
Key Takeaways
Betting and financial markets often reacted faster than TV networks or polls.
While networks still had Biden ahead in several states, UK betting markets and U. ...
Get the full analysis with uListen AI
Lockdowns and COVID tradeoffs were a major, underappreciated driver of Trump’s strength.
Guests argue that prolonged and inconsistent lockdowns in states like Michigan, Wisconsin, and Pennsylvania created intense resentment among small business owners, workers, and rural communities who saw the crisis more as an economic than purely health issue. ...
Get the full analysis with uListen AI
Pollsters corrected some 2016 mistakes but still fundamentally misread key voter blocs.
SurveyMonkey’s Jon Cohen explains how education-weighting and methodology improved, yet polls still overstated Biden’s margins, especially in the Midwest and among Hispanics. ...
Get the full analysis with uListen AI
There is a powerful protest vote against coastal elites, cancel culture, and media bias.
Multiple speakers describe “sanctimony” from urban, educated liberals and the sense that rural and working-class Americans are mocked, overruled, or silenced on issues from guns to speech to COVID rules. ...
Get the full analysis with uListen AI
Democrats’ long-term “demography is destiny” strategy and identity politics look fragile.
Chamath, Sacks, and guests argue that assuming nonwhite voters would reliably form a permanent Democratic majority was a strategic error. ...
Get the full analysis with uListen AI
A Biden presidency with a Republican Senate is seen as a ‘soft landing’ scenario.
Several panelists view a narrow Biden win plus a GOP-controlled Senate as the most stabilizing outcome: Trump’s temperature and chaos would be lowered, radical policy swings (left or right) would be constrained, markets would like the gridlock, and the country could potentially “ignore Washington” for a few years.
Get the full analysis with uListen AI
California’s Prop 22 may become a national template for a new worker ‘third way’.
Bill Gurley and Brad Gerstner frame Prop 22 (carving out app-based drivers from AB5 and creating “IC-plus-benefits”) as a prototype solution that balances flexibility with portable benefits for gig workers. ...
Get the full analysis with uListen AI
Notable Quotes
“This is a massive upset, relative to expectations. Win or lose, this is a massive upset by Trump and a massive misread by the progressives and organizers in the Democratic Party.”
— Brad Gerstner
“I think 2016 was an economic repudiation of the elites; 2020 is a cultural repudiation of the elites.”
— David Sacks
“Maybe, just maybe, we’ve moved past color, and now ideology and social policy and economic and monetary and fiscal... all of these things are what matter. You take a thousand brown people and put us in a room—we’re not all the goddamn same.”
— Chamath Palihapitiya
“Ordinary people are made to feel bad about themselves by people living in these parts. The sanctimony that exists in urban areas and coastal elites is just... This is what we’re seeing people vote against.”
— Brad Gerstner
“If these motherfuckers want a single goddamn dollar from me, what I want first is a root cause analysis to understand what is actually going on.”
— Chamath Palihapitiya
Questions Answered in This Episode
How much weight should we give betting and financial markets as ‘real-time polls’ in future elections, given how quickly they adjusted compared to media narratives?
This live All-In Podcast “Election Night Special” tracks the 2020 U. ...
Get the full analysis with uListen AI
To what extent did lockdown policies versus Trump’s COVID messaging actually drive vote shifts in key Midwestern states, and how could either party have handled that tradeoff more effectively?
They explore why polling and media narratives were so wrong, emphasizing missed dynamics among working-class voters, Latinos, men of color, and voters’ reactions to lockdowns, cancel culture, and perceived condescension from coastal elites. ...
Get the full analysis with uListen AI
What concrete steps could political leaders and media organizations take to reduce the perceived ‘sanctimony’ and condescension toward rural and working-class voters without abandoning core principles?
Despite deep disagreement about Trump’s character and legitimacy, there is broad consensus that the night represents a massive upset for Democrats’ expectations and a loud protest vote against cultural and political elites. ...
Get the full analysis with uListen AI
If the Democratic Party’s demographic and identity-politics strategy is failing, what would a successful, non-woke, economically populist Democratic platform look like in practice?
Get the full analysis with uListen AI
How should policymakers redesign the social contract for a gig and freelance economy—beyond Prop 22—to provide security without sacrificing flexibility or crushing innovation?
Get the full analysis with uListen AI
Transcript Preview
Hello, everybody. Welcome. Uh, we are live at the All In headquarters, and the All In podcast is now live. We have 63 people watching already, and bear with us while we get the besties on the line. I'll be doing my introductions in just a moment after I tweet this. Um, but it is an eventful night, and we had to start early because, uh, it's looking like this could be another shocker. And I am not, uh, being facetious here, I am not, uh, happy about this, obviously, but, uh, Trump looks like he's been underestimated again. This is not a blowout. Um, we are going live early. Um, this could be a shocker, folks. Okay, so, uh, with me early on the pod is regular David Friedberg. Uh, David, you're watching this early action, and what's your early, uh, reaction to what we're seeing?
Um, you know, Trump's moved. We- there's no- nothing definitive yet, but, uh, he's moved, uh, in the results and he's moving markets. We're seeing forex markets show a sharp indication, um, that, uh, Trump has a real shot at winning here, treasury markets, and as Phil Hellmuth will share with us, betting markets as well. So-
All right, well-
... it is more, it is more of a nail-biter, um, than a game seven of the Warriors, Cavs. So here we go.
This is a hell of a nail-
Thi- this is a hell of a nail-biter, guys, and I'm just gonna say this. Uh, the UK markets had it first. They sw- he was five to two, uh, you could, you could get Trump at five to two, two and a half to one. Then it hit five to four, and I thought that was quite crazy. You're watching CNN, you're watching these networks and they're saying, "Oh my God, Biden's winning this." No, they're not even in the right neighborhood. I'll never watch a network again on election night. And now, the market from five minutes ago, 368 million pounds wagered, 368 million pounds. Trump is now a three to ten favorite. Uh, which means-
Okay, so for people, uh, Phil, who are not gamblers...
If you bet three dollars-
Let's put this in dollars. You bet $3...
No, no. J- Jason, you have to understand. If you bet $13, okay? You don't-
Yeah.
... get 13 back. You only get, uh, 10 back, okay? Now, if you wanna bet Biden, it's seven to four. So if I bet $70, uh, if I bet $40, I can get $70 back on Biden. Now, the shocker is, right around 6:28 PM, uh, the betting odds, the markets were, have been in Biden's favor for three straight months. I've been live posting them on my Twitter all day. The worst I saw was, uh, was Trump was, uh, was, Biden was -$1.25, still a big favorite to win, and then boom. And, uh, you know, there are people in my house that are actually crying. Uh, you know, I'm very more, much more in the middle of this thing, but all of a sudden, uh, Trump, uh, uh, all of a sudden it was five to four, then it was even, and then all of a sudden Trump was nearly a, a two to one favorite. I'm getting live information from my friends right now, um, I'm seeing that, uh, that it's, uh, it's a little bit lower on some of these sites. Um, I saw 267, that's for a $200 bet, so he's a pretty big favorite. Um, I saw the lowest I've seen is 217. But Jason, if you're watching the a- odds, and I put some stuff on my Twitter, it's amazing how it went from, you know, -$1.70, you know, all the way down, -30, then it came all the way up to -$1.70. This is crazy. And, and I've seen this movie before, in 2016, actually.
Install uListen to search the full transcript and get AI-powered insights
Get Full TranscriptGet more from every podcast
AI summaries, searchable transcripts, and fact-checking. Free forever.
Add to Chrome