The Ledger

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Opinion
Ehrenberg: Polymarket and Kalshi Are Pure Regulatory Arbitrage Plays
“This is the purest regulatory arbitrage play of all time. Okay. If you can look at the cumulative market cap of regulated sports betting and look at how it has dropped in response to the rise of Polymarket and Calci, who are not subject to the same rules and r…”
Roger Ehrenberg Oct 16, 2025 ▶ 47:05 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2027
O'Driscoll: Kalshi will not reach $100B valuation within 12 months
“I doubt it.”
Rory O'Driscoll Jul 2, 2026 ▶ 39:57 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Insight
O'Driscoll: Political prediction markets are too small to build $100B companies
“I don't think predicting who's the next Who's going to win the general election in the UK or who's going to be the next president in the US is a huge, enormous, ginormous business. I love it. I find it fun. It's actually the most interesting part of Polymarket…”
Rory O'Driscoll Jul 2, 2026 ▶ 41:14 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: 90% of Kalshi's prediction market activity is actually sports betting
“90% of what they do is sports betting.”
Rory O'Driscoll Jun 25, 2026 ▶ 58:55 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Assertion Not checkable as stated
Mansour: Only 1 to 2 percent of prediction market users actively trade
“Out of every hundred prediction market users, maybe there's like one or two traders that are actually trading on the market, but the rest of the users are getting informed about the world.”
Tarek Mansour Dec 8, 2025 ▶ 23:10 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Partly supported
Mansour: Kalshi resolves election outcomes 5-7 hours faster than news networks
“You go on the traditional news networks and like, You don't know who won until five, 6:07 hours after Kalshi, right?”
Tarek Mansour Dec 8, 2025 ▶ 23:31 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Open
Mansour: Kalshi is currently profitable
“We are at a point right now where, so we're growing incredibly fast. We are also profitable right now.”
Tarek Mansour Dec 8, 2025 ▶ 2:28 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Disclosure
Mansour: Kalshi lost team members twice before suing the US government
“The next day we came back, and we were like, we're gonna try again for the twenty-twenty-four election. And then we tried another year till the end of twenty-twenty-three. Then the government blocked it again. And then, so that's the second time. And then God …”
Tarek Mansour Dec 8, 2025 ▶ 18:18 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Not checkable as stated
Mansour: Kalshi is the fastest-growing non-AI US company at scale
“Kalshi this year is at this scale, at least, you know, the, I think the fastest growing company in America outside of AI. I think Anthropik is growing faster, and I'm not sure about Merkur and Cursor, but we're, you know, growing at that sort of, at that pace,…”
Tarek Mansour Dec 8, 2025 ▶ 1:20 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Partly supported
O'Driscoll: 90% of Prediction Market Business Is Sports Betting
“This is two non-sports betting companies who are doing quote prediction markets where all we talk about is the 10% of the revenue that's political, and 90% of their business is sports betting, but we're not calling it that, and they're just killing it because …”
Rory O'Driscoll Oct 16, 2025 ▶ 49:36 Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
Assertion Supported
O'Driscoll: Multiple US states are actively suing prediction market Kalshi
“There are currently some states suing Kalshi, saying you really are doing betting, so we should regulate you.”
Rory O'Driscoll Jun 25, 2026 ▶ 1:03:08 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Insight
Mansour: Kalshi's election growth was prediction markets' ChatGPT moment
“Kind of what happened with Kalshi in the election was a bit of a Chad GPT moment for our industry.”
Tarek Mansour Dec 8, 2025 ▶ 0:00 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Opinion
Mansour: Culture prediction markets represent a massive unaddressed TAM
“I actually think like what's happening with Taylor Swift, you know, movies and how successful they're going to be, anything around culture like that, that is massive unaddressed, unaddressed tam right now.”
Tarek Mansour Dec 8, 2025 ▶ 6:05 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Partly supported
Mansour: Kalshi sued the CFTC and won in October 2024
“So in 24, we won the fight against the government. We won that, that we sued the government and then we won that fight in October seven, 24.”
Tarek Mansour Dec 8, 2025 ▶ 7:04 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
What-if
Mansour: Kalshi and Polymarket pushed each other's product and marketing harder
“Without Polymarket, we wouldn't have I think like, Pushed our marketing and pushed our product as hard. And without us, they wouldn't have pushed their marketing and their product.”
Tarek Mansour Dec 8, 2025 ▶ 12:05 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mansour: Sports betting dominance is temporary; culture markets will scale
“And it's a matter of time to like, you know, we scale the number of markets, we scale the liquidity, and I think those one day will be very big. So sports is very big right now, but I don't think it's kind of like a, I think it's a moment in time.”
Tarek Mansour Dec 8, 2025 ▶ 6:15 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Insight
Mansour: Superior products will always defeat competitors with more capital
“I, I'm maybe, maybe I'll lean a little bit more on the other side, which is like a better product will trump. Any day.”
Tarek Mansour Dec 8, 2025 ▶ 3:44 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Opinion
Lemkin: Kalshi is a safer long-term bet than Polymarket
“So based on my limited knowledge, I'm going Kalshi because I feel like it is a safer long-term bet than someone that is writing the current political vibes, which are all in favor of everything here. It just could, it was a lot different a couple of years ago,…”
Jason Lemkin Nov 6, 2025 ▶ 1:16:08 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Insight
Stebbings: Employees who 'need' to succeed will pull three consecutive all-nighters
“There are people who want to make it happen, and they want to see Kalshi succeed, and then there are others who fucking need to make it happen, and the ones that need to make it happen do the three all-nighters in a row and get it done, and the ones that want …”
Harry Stebbings Oct 1, 2022 ▶ 17:48 Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931 · 20VC with Harry Stebbings
Assertion Contradicted
Randle: Prediction markets show 70% odds of Tesla-SpaceX merger in two years
“If you look at the poly market Calci odds on a Tesla SpaceX merger, again, you know, not, not that those markets are so big that they're that indicative, but I think the probability that they have on there is something like 70% in the next two years or somethi…”
Everett Randle Jun 18, 2026 ▶ 19:07 Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Kalshi announced a $1B raise at an $11B valuation
“In the last week, they announced their one billion dollar raise and an eleven billion dollar valuation.”
Harry Stebbings Dec 8, 2025 ▶ 0:06 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Disclosure
Mansour: Robinhood is a partner of Kalshi in prediction markets
“They've been incredible partner of ours on the prediction market front.”
Tarek Mansour Dec 8, 2025 ▶ 8:22 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Supported
Mansour: Kalshi secured exclusive media partnerships with CNN and CNBC
“So this week we've announced well, we found the first and then the second large scale news network partnership with the prediction market. So we announced CNN exclusive partnership and then CNBC, the same thing the next day.”
Tarek Mansour Dec 8, 2025 ▶ 13:40 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Insight
Mansour: Excessive capital causes company inefficiency and unforced errors
“Oftentimes a lot of money can create like inefficiency and like, you know companies start making a bunch of unforced errors when a lot of money comes in.”
Tarek Mansour Dec 8, 2025 ▶ 4:33 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mansour: Kalshi can build its own news network while partnering with legacy media
“I think we can. They're not mutually exclusive. Like I think we can do both.”
Tarek Mansour Dec 8, 2025 ▶ 25:37 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Insight
Mansour: Company Scaling Requires Shift From Sprints to Consistent Habits
“I think like it's less about some specific department lacking, but more about like consistency now. How do we move that into like a scaled, consistent set of habits in the company rather than like a series of sprints?”
Tarek Mansour Dec 8, 2025 ▶ 20:35 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Insight
Mansour: Prediction markets must balance broad inventory with concentrated liquidity
“You cannot go fully vertical because then your product offering is not diverse and interesting enough, and you cannot go fully wide because then you don't concentrate enough liquidity in specific events.”
Tarek Mansour Dec 8, 2025 ▶ 26:39 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Insight
Mansour: The best senior hires retain a childish curiosity for new tech
“We tend to, Try to focus on people with a lot of experience and wisdom that still, I mean, I don't mean that, I really mean this in a good way, that still have a little bit of like, I call it like the childish fascination aspect. And there's a lot of those peo…”
Tarek Mansour Oct 1, 2022 ▶ 16:59 Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931 · 20VC with Harry Stebbings
Disclosure
Mansour: Kalshi replaces standard algorithm interviews with real exchange problems
“We try to limit the kind of algorithm interviews and all of that. We don't do money of those. We do everything. It's either one, it is something that we're actually tackling today in exchange.”
Tarek Mansour Oct 1, 2022 ▶ 26:14 Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931 · 20VC with Harry Stebbings
Disclosure
Mansour: Kalshi's worst hiring mistakes came from prioritizing raw intellect over culture
“And I think we over indexed on this a little bit earlier on. I mean, I think it was really about like, okay, what are the smartest people who can get into the company? And I think we would put aside a little bit of the cultural aspects and you know, whether th…”
Tarek Mansour Oct 1, 2022 ▶ 18:57 Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931 · 20VC with Harry Stebbings
Disclosure
Partovi personally pitched nearly every early hire at Vanta and Kalshi
“In almost all my portfolio companies, if I didn't source their early recruits, I certainly helped close them. At companies like Vanta, Kalshi, Copercure, I think not a single person they hired was without a phone call, at least from me, to help convince them t…”
Ali Partovi Jan 21, 2022 ▶ 12:13 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
Disclosure
FOMO Would Build Prediction Markets on Polymarket or Kalshi
“We haven't integrated prediction markets yet, and I'm not sure exactly where it fits in on our roadmap. I think it's very interesting there. I think our first version of the product would be built on something like a poly market in Calci.”
Paul Erlang Jun 27, 2026 ▶ 7:02 How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong · 20VC with Harry Stebbings
Disclosure
Mansour: Kalshi is in active partnership discussions with Lionel Messi's team
“We have talked to, I think we are talking to his team right now, so we'll, we'll figure something out”
Tarek Mansour Dec 8, 2025 ▶ 38:26 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Supported
Mansour: Kalshi currently has 110 employees
“A hundred and change. A 110.”
Tarek Mansour Dec 8, 2025 ▶ 44:50 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
Assertion Partly supported
Mansour: Kalshi's first hire was former CFTC official Jeff Bandman
“The first person on the company was Jeff Bandman who's, who's actually pretty publicized now, which was really cool. I love that. But Jeff, you know, is the only lawyer that basically took up our kind of like gays at the time. And he was ex CFTC.”
Tarek Mansour Oct 1, 2022 ▶ 16:34 Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931 · 20VC with Harry Stebbings
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