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Kalshi's Tarek Mansour: Chaos by Design
Tarek Mansour says Kalshi stayed committed to building a regulated exchange, even when that meant betting the company on a lawsuit against its regulator.
Training Data · Sonya Huang & Pat Grady
- Tarek Mansour is cofounder of Kalshi.
The best minutes
- 42:48Kalshi sued its regulator because the upside outweighed the risk5 min
- 20:36Founders should own the company’s biggest problem3 min
- 35:16Marketing works best when it meets the moment3 min
Also worth watching
- 51:35Kalshi uses account limits to reduce risky trading8 min
- 16:46Kalshi shifts its focus as customer demand changes3 min
- 24:37Kalshi prioritized regulation before broad adoption2 min
- 28:29Decide whether the idea is worth the opportunity cost3 min
Skip the four-minute childhood and family background, the CEO role-model discussion, and the work-schedule and office-hours segment.
Full analysis · 7 min read
Real Alpha · Nov 8
Tarek Mansour says broker revenue reached 80% before a reset
- Brokers rose to 80% of Kalshi revenue, then later represented 10% of volume.
- That supports demand-led adaptation, but it does not prove every shift worked.
- Founders should track customer mix, regulatory exposure and user safeguards together.
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Read the rest of the analysis
7 sections, the 6 other voices it tests Mansour against, and what it means for you. Every episode we cut gets one.
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Kalshi changed priorities when channel demand shifted
Kalshi’s operating chaos was not a new company strategy. Mansour said the company never abandoned its broad exchange ambition.
Instead, it repeatedly reorganized around its largest demand pockets and obstacles. That distinction matters. Changing priorities is not the same as changing the destination.
For example, broker business reached 80% of revenue. Mansour said that dependence led the team to rebalance toward direct users. Later, he said brokers accounted for 10% of volume.
Still, the denominators differ, so the later figure does not show broker revenue fell to 10%. In October 2026, Yinon Costica told Sabrina Halper Show that Wiz updated its framework as the company changed.
In November 2026, Amjad Masad told Lightcone to let customers show the next step. Both comparisons favor adaptation. They do not make Kalshi’s revenue and volume figures comparable.
“now we have to go back to focus on the direct”
- YCYinon Costica · Sabrina Halper Show · Oct 7Wiz kept teams aligned by updating its operating framework
Amjad Masad · Lightcone · Nov 7Replit advances its strategy through customer-led increments
Our read
Kalshi’s adaptation was concrete, not just a slogan. Revenue concentration changed the channel priority, but the figures do not show every switch succeeded equally.
Founders should keep the biggest constraint close
Mansour’s ship metaphor puts founder attention on the unresolved problem that can sink the company. A delegated issue can become a covered leak, not a repaired one. That is an argument about authority as much as effort.
He said Kalshi’s issue was trust around regulation and insider trading. He spends pretty much 80% of his time on that work, by his account.
For example, many customers, he said, could not distinguish regulated U.S. exchanges from offshore operators. But that confusion made the industry’s reputation a live business constraint, not just a communications problem.
In November 2026, Rafael Vivas told Founders that leaders can lose focus after delegating too broadly. In September 2026, Anton Osika told Silicon Valley Girl to identify the bottleneck before abandoning an idea.
Those comparisons support staying close to the constraint. They do not mean founders should personally own every function.
“there needs to be at least one founder in any of these big media problems that we need to get right.”
Rafael Vivas · Founders · Nov 1AppLovin leaders stay hands-on to keep work focused
Anton Osika · Silicon Valley Girl · Sep 22Find the bottleneck before you abandon an idea
Our read
Founder ownership is most useful where risk crosses product, policy and reputation. It can keep authority close to unresolved work without making every task founder-led.
Kalshi treated regulation as a product foundation
Kalshi chose a slower route than launching offshore and asking permission later. Mansour said financial markets require compliance and trust, especially for mainstream and institutional users.
That choice also followed his stated ambition to change Wall Street from within. Regulation was part of building the exchange he wanted, not only a hurdle to clear.
The host recapped that Kalshi began in 2018 and opened to the public at the end of 2022. He called late 2024 its proper launch, when election markets became available. Mansour defended waiting for the markets people wanted.
Yet the episode does not separate regulation’s effect from product or growth execution. Mansour credited the foundation alongside superior execution in both areas.
In October 2026, Revolut CEO Nik Storonsky told Founders that a banking license helps earn trust and scale. That parallel supports Mansour’s logic, not identical rules or outcomes.
“I don't really believe in that like I know in silicon valley it's like move fast and break things”
Our read
Mansour’s case is that compliance can be part of the product customers trust. The episode supports that as his reasoning, not as a measured comparison of growth drivers.
The lawsuit was a high-upside bet, not proof
The lawsuit followed two failed efforts to offer election markets. Regulators delayed Kalshi’s 2022 attempt past the midterms, then rejected another application at the end of 2023.
Alfred Lin warned, as Mansour recalled, that Kalshi could lose and incur significant costs. Mansour separately saw a risk regulators might pull the clearinghouse and kill the company before a result.
Luana pushed for filing, while Mansour says he oscillated until the night before. Even then, he judged the upside potentially large enough to justify low odds.
Still, that reasoning differs from treating success as likely. But the company won, and the result cannot establish that the bet was safe beforehand.
Nor did winning produce instant momentum, Mansour said. Usage began slowly, then picked up as Kalshi worked to make the market mainstream.
“if it does work, the outcome is so big and the expected value seems pretty attractive, actually.”
Our read
The outcome vindicated the bet, but it does not make the risk disappear. Founders need to weigh downside survival against potential upside before knowing which way variance will go.
Kalshi timed marketing around moments of attention
Kalshi’s marketing responds to the same changing conditions as its channel strategy. Mansour said public attention shifts too quickly for every launch to follow a fixed calendar.
For example, Mansour said Kalshi launched the Chalamet ad 12 hours after a Knicks-related moment put him in the conversation. He said the team had considered an Oscars launch for the Chalamet ad, then waited.
For Giannis, Mansour said the announcement came a day after he said he would stay with his team.
But that is a tactical account, not a campaign result. The episode gives no reach, conversion or cost data to show whether timing produced better returns.
And speed also creates coordination costs, since partners and internal teams must move faster than standard processes. A campaign’s moment is useful only if the team can test what it changes.
“the timing needs to be like exactly right”
Our read
Timing can make a campaign relevant, but attention is not the same as conversion. Teams should measure whether the moment improved results, not just whether the launch felt timely.
Mansour says persistence must serve the idea
Persistence is conditional in Mansour’s advice. Continue when the idea itself compels you, not because you expect wealth, status or an easy life afterward.
Company-building brings continuing stress and opportunity cost, he said. Some founders should stop when the idea no longer justifies those costs.
But he also calls giving up a serious risk. Those points fit together only if founders test the idea’s value, rather than celebrate endurance alone.
In October 2026, Jean-Denis Greze told a16z Podcast that a nearly $1 million tax business was not venture-scale. That was about its market and sales constraints, not every startup.
In September 2026, Anton Osika told Silicon Valley Girl to identify the bottleneck before dropping an idea. His test makes persistence diagnostic, not automatic.
Kalshi’s long wait shows the bet can pay, but not that every desert ends with a market opening.
“the number one risk is giving up”
Jean-Denis Greze · a16z Podcast · Oct 19A nearly $1M tax business still wasn’t venture scale- Anton Osika · Silicon Valley Girl · Sep 22Find the bottleneck before you abandon an idea
Our read
Persistence is not a strategy by itself. The relevant test is whether the problem still matters enough to justify the time, cost and other paths being left behind.
Kalshi’s safeguards need evidence beyond incentives
Mansour distinguishes Kalshi’s fee model from gambling operators’ reliance on customer losses. He said Kalshi takes a one percent transaction fee whether a user wins or loses.
Still, that reduces one incentive to profit from users losing. It does not remove the risk that inexperienced traders lose to better-informed counterparties.
He acknowledged that not everyone wins on Kalshi. The marketplace can still expose a novice to professional or better-prepared traders.
Kalshi adds tighter limits and verification for traders aged 18 to 20, he said. He said its parent-ID portal addresses 95% of the problem of minors using a parent’s identity.
Those are company-reported safeguards. He thinks the share showing excessive patterns or losses is lower than in options or active stock trading. He gave no denominator or measurement method on air.
That evidence gap matters because different markets can attract different users and risks. Comparisons are useful only when the same harm definitions, user groups and time periods are measured.
“I take a 1% fee whether it's somebody who loses or not.”
Our read
The fee structure may reduce one incentive to encourage losses, but it does not establish low user harm. The episode leaves the safeguards’ measurement and outcomes untested.
What it means for you
- Map revenue concentration. Track revenue and volume separately by channel. Kalshi’s broker shift shows why the denominator matters before changing priorities.
- Name the live constraint. At each leadership review, identify the problem most likely to block the company and assign a founder to own its resolution.
- Measure launch timing. Compare campaigns launched around a public moment with ordinary launches. Track reach, conversion and cost rather than attention alone.
- Audit risky use. Review user limits, verification and loss patterns by age group. Ask for the denominator and measurement method behind any safety claim.
What to watch
- Whether brokers remain a small share of volume after Kalshi’s renewed focus on direct users.
- Whether mainstream customers can distinguish regulated exchanges from offshore markets.
- Whether Kalshi’s reported trading safeguards are supported by clear measurement methods.
Send this to founders balancing regulatory risk with fast-moving product teams.
Watch the minute where Mansour gives the broker concentration and volume figures.
Written by Real Alpha from the episode's transcript and the other moments it links, then checked against the transcript. Quotes are the speaker's exact words.
Minute by minute
- 1:17Disagreement balances risk and innovation
Mansour says he handles high-level strategy, regulatory work, fundraising and detailed marketing, while Luana runs the day-to-day company. They often argue opposite sides by design, he says, to balance innovation against regulatory risk and challenge each other without the incentives employees may have.
- 6:41Volatility shaped his risk instincts
Mansour connects his risk-focused outlook to growing up in Lebanon with a single mother who was intensely protective and pushed her children to succeed. He says that experience made him quick to imagine how things could go wrong, while also teaching him to keep looking for a solution.
- 10:22Chaos helps Kalshi adapt
Mansour says he and Luana make up their own operating approach rather than follow a standard CEO playbook. He describes Kalshi's low-hierarchy structure as chaotic, but says it helps the company shift toward new problems and opportunities without friction.
- 16:58Kalshi resets around its biggest challenge
Mansour says the company organizes its priorities around the most important current challenge, rather than relying on a fixed plan. After the election, Kalshi focused on cross-selling users; broker demand brought more liquidity, but brokers later accounted for 80% of revenue, prompting a renewed push toward direct customers. He says brokers are now about 10% of volume.
- 20:36Founders must own the biggest risks
Mansour argues that a founder should personally face the company's hardest problems rather than hand them off. He compares a company to a fast-moving ship with a leak and says Kalshi's current challenge is distinguishing regulated U.S. markets from offshore platforms and addressing insider-trading concerns. He says he spends about 80% of his time on that work.
- 23:18Regulatory groundwork supported Kalshi's growth
Mansour says competition is rarely a company-killer in a large market and reports that Kalshi has 95% of U.S. prediction-market share. He says Kalshi chose to build within financial regulation rather than launch without a license, and that its growth accelerated after it could offer election markets and execute on product and growth.
- 26:53Keep going only for the idea
Mansour says Kalshi never pivoted from its goal of building an exchange for many kinds of markets, even through years of regulatory setbacks. He advises founders to ask why they are continuing: persistence makes sense when the idea itself matters, but not just for an imagined payoff. He says entrepreneurship brings continuing stress and sacrifice rather than a permanent oasis.
- 31:10Founders set their own pace
Mansour says he is usually at the office from 8 a.m. until 10 p.m. and often works there on weekends, but does not require employees to match his schedule. He says Kalshi has grown to about 150 people and has fewer than 10 support staff for millions of customers, with automation helping the team scale.
- 34:27Marketing depends on timing
Mansour says marketing needs precise execution and should meet people at the moment they are paying attention. He describes live election odds on billboards, refined through about 20 iterations, and a Timothée Chalamet commercial released 12 hours after Knicks news broke. He says Kalshi also timed partnerships around major moments for Messi and Giannis.
- 40:23Kalshi made an asymmetric legal bet
Mansour says Kalshi began seeking approval for election markets in 2021, but the CFTC delayed its decision until after the 2022 midterms; the company then lost employees and made layoffs. After another rejection in 2023, Luana pushed to sue despite warnings from board members that the regulator could cripple the company. Mansour saw a low-probability but high-upside bet, and says a good expected outcome can still lose on one try.
- 49:04The ruling created a narrow launch window
Mansour says he learned by phone that Kalshi had won, and that employees celebrated by throwing chairs and damaging the office. The ruling came three and a half weeks before the 2024 election. He says the launch did not take off immediately, but the team worked intensely to build momentum and then saw growth compound.
- 51:35Kalshi says safeguards can limit harm
Mansour distinguishes Kalshi's market model from gambling businesses: he says Kalshi takes a 1% fee rather than earning revenue from customer losses, and wants informed trading to improve liquidity and forecasts. He says the company adds throttling and verification for 18-to-20-year-olds and uses a parent portal to help prevent minors from using their parents' IDs.
- 59:10A company should reflect its founder
Mansour advises aspiring founders to ask why they want to start a company, since founders are not their own bosses and the work brings little freedom. He says it is hard to build or market a product that does not reflect who the founder is, and argues that the company's character tends to mirror its founder.
Published Jul 9, 2026.
Transcript · 1 h 3 m read
Training Data, hosted by Sonya Huang and Pat Grady, with Tarek Mansour.
Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.
The thing that was unique about us is we never pivoted. It was always Kalshi. I mean, Kalshi is everything in Arabic. We always wanted to build the everything exchange, the exchange for all these different assets. And we didn't build Kalshi to build a company. We built a company to build Kalshi. It's a bit different. We were dragged by the idea. I wasn't the type that wanted to be an entrepreneur. I think if you re-roll the dice multiple times, I'd probably just be a trader or risk manager. I would not be an entrepreneur. But the idea was so gliding in front of us that we just had to do it. We felt like we had to do it.
And so the whole point of doing this whole thing is the idea. Hey, everybody. Today we have Tarek on from Kalshi. He is a gem. This is a really good episode. they walked through the desert for many many years in this company and went sideways then they made a very risky bet to sue the federal government and won and this thing has ripped ever since it's growing you know similar rates to open ai and anthropic but a few years behind i think you're gonna like it i'll be back at the end for my takeaways we just met for the first time a couple ago at david salman's house and it was a ceo dinner and you had some very unusual ideas about ceoing this is why i wanted to have you on the pod yeah and so i want to get into those let's just start with your co-founder yeah it sounded like it's a semi co-ceo relationship how do you two run the company how do you split it up yeah it's interesting you know we've over the years who have constantly been asked this question and we never really had a very clean answer to this and we always thought it was sort of like a weakness and our perspective on that has changed.
I mean, dramatically, I actually think whatever model works for us, works for us. Great, you know, and if you figure that out, then, you know, and, you know, the best way to describe it is that I think, like, I operate at the very high level strategy, make sure that we're going in the right direction, where's the world heading, where are rights to win, And just thinking, a lot of thinking continuously. And then I'm very, very low in the details. Okay, you're high and low. Yeah, extremely high. Head in the sky, feet in the ground. Yeah. Okay. But very, very low. I'm talking like... Coding. Yeah, and more specifically, like marketing and the copy and the details and everything around how we're marketing something, how we're talking about the product, all these little things that the end consumer, whether it's someone looking at a billboard or someone who's in the product, is going to experience. What are they going to feel? And everything else that is actually running the company is Luana. That's basically, I think one of the best ways to describe it. And then I do the external stuff, the regulatory, the policy, the fundraising, all the other external aspects of the job that tie to marketing and sales.
Read the whole transcript
but the day-to-day running of the company like making sure that the company is actually run is luana how do you disagree you must disagree about stuff disagree a lot like all the time so how does that play out i actually think we kind of disagree by design like we have this thing this dynamic over time it's become a thing where like we essentially will always take the opposite side of the argument are you a contrarian i'm the guy in the room that will be sort of the negative like everybody's pumped about a plan i'm like oh here's how it's going to fail and how in all the issues okay i have you know but but we tend to sort of just like disagree with each other often and i think also like you know again it's people like oh you know how you disagree and disagreement like continuous disagreement is an anti-pattern but for us it ended up being a pattern because we're coming this we're this very complicated company that has this constant continuous delicate balancing between how much risk to take on the regulatory front and like you know innovation regulatory and you have to always balance those two those two things out and you see now in ai and safety and innovation all that and And like that sort of debate is a continuous force to drive us to the middle.
We end up getting, you know, not always the right answer, but we're not too far from the right answer and we never oscillate between the two extremes. And I think that's one of the powers of having like two equally powerful, like two co-founders in an organization, because if you're the only one, you know, anyone, like anyone that reports you or whatever, like anyone that you hire that is not a founder, it's inevitable that they won't always tell you the truth. It's inevitable. Like, no matter what culture you build, etc., like, there's different incentive structure than someone who's a founder that owns as much equity as you, etc. And so you can stray, right? And here, it's very hard for either of us to stray.
So I talked to Luana to prepare for the interview. It sounds like you're kind of the more conservative of the two. Yeah. And maybe you're on the regulatory side and she's on the innovation side. Is that the way it sort of plays out? More often than not, yeah. Luana is very faith-based, like, optimist. Sometimes I would say, like, super irrationally optimistic. Like, she sometimes doesn't really do the math on how something is going to work out. Like, on why it's going to work out. And that's continuously happened at Kalshi. And that used to, I mean, for years, it frustrated me. I was like, this really, like, it doesn't make any sense. And I'm the other side. I'm like, I'm a risk manager. I have a paranoid demure, which is also usually an anti-parent for a founder. I think about risk and expected values. And like, I think probabilistically about the world. And here's all the things that could go wrong.
and i think that sort of that tension has led to uh all the decisions that we've made over time but it's interesting because you know like luana's uh approach to things and now i now believe that given enough time horizon is going to end up being true no matter how rational it sounds okay it's kind of it's kind of amazing but i think my side is the thing that like for right you know for a company that has to get regulatory right you have to make sure that like you uh you're doing things the right way like i'm kind of that forcing function in the company and again so i think we land somewhere in the middle where we've managed to achieve the results we've achieved i'm actually very bad at a lot of things it's actually shocking like if you see my day-to-day because you're obsessive you're very good at exactly things exactly you're a lot of founders are obsessed yeah but i'm kind of procrastinator like i'm so disorganized like if like people that work around me ask them it's just like such a shitshow but like you wanna like orchestrates everything she's organized very and like she drops but like i'm like the opposite of what you imagine for an operator but i can get so obsessed with certain things that i want to get
good at that i can get good at pretty fast and i like get good so i don't think i'm a good marketer i just like obsessed about it for long enough that i i work with my co-founder he's very obsessive and goes very deep down a rabbit hole and you can't get him out of that rabbit hole you've had a long strange trip growing up in beirut yeah uh certainly an unusual childhood is the risk a version sort of rooted in growing up in such an unusual place for sure i mean most most things right that end up sticking with you are really how you grew up um this definitely applies to i mean so i grew up with a single mom and i grew up in lebanon and in lebanon you know it's it's not a i feel like oftentimes the headline make it sound like a sounds like a constant war zone if you read the new york times yeah it's not it's actually more of a volatile country yeah like the word is volatility. It's a lot of ups, a lot of downs. You can have a lot of fun, great life. And then all of a sudden you're like, you know, running from a, so, so the mix of those two, my mom was paranoid. She, she, she would, she was always afraid. We would sort of take a lot of issues that would be thrown at.
So the extreme, and we would carry them as like, and I was really young, and I'm the eldest child. We're two brothers. And that doesn't leave you. So my brain is wired to think about all the ways that something is going to, you know, go wrong, right? Like if I get on a hot air balloon, I can like list on a flight, like any, yeah, on a flight to like, I can list you immediately all the 20 ways this thing is going to go south, right? Okay. But it's important for our company, we're a company that, you know, that has financial risk involved regulatory, I mean, all these different things, but that has helped us over time, really, become very hyper attuned to what exactly is our risk in a variety of different ways and where we can take risk and where we can okay i've heard you on other pods bring your mom up just can you just give us some more paragraphs on her oh it's interesting like riff on your mom she's very i mean she's like she's definitely a tiger mom like in that you know so tiger mom very intense like very very intense my you are too yeah i'm very intense too yeah but yeah my way or the highway uh we're like uncom completely uncompromising completely and then it was the sort of thing
where like so what happened is i think she had to basically sacrifice a lot of her life to to because my my dad left us at age six kind of and she had to sacrifice a lot of like her career everything she was wanted to do to basically make sure that we're okay and she wanted us to have the best life we could and come back you know come back to america so i was born in california went to lebanon and she wants to come back and get to the top school etc and so what happened is i think like a lot of her personal pride ended up being attributed to her kids like my kids success are going to be what i deliver in life and so so her bar was so high on us everything like we would do a sport like go play tennis or play soccer and you have to win and if you come silver like it's bad so that just creates like a hyper competitive um uh nature but also there's this this feeling of like there's always an answer like you know whenever we had like a financial issue or like you know like you don't give up you you bang your head against the wall you go up you go left you go right you you go down i mean it doesn't really matter you're gonna figure something out all of that i think ends up you know now like you know decades later right like it's all in me and
it it it matters because there's this sort of higher gear sometimes that like so most people have this thing of like well there's certain things that are within my control and certain things are not i don't really believe there that in that dichotomy okay i think it depends on the person like some people can just make a significantly larger subset of the universe of things that are like I feel like it can make things happen maybe be irrational yeah You can make, you can bring more things into the control. Yes. If you have, you know, like some people just think like, okay, like I. I can do it. Yeah.
And it could, the scale of the problem could even become big. I mean, it's, I mean, Elon has a little bit of it, right? Like. He has a lot. Yeah. Like I feel like Elon sometimes, and I'm not, you know, my sense is like, as long as it doesn't break the laws of physics, like we probably can make it happen. It's in our control. Yes. Yeah. We're going to get into more CEO stuff. We just heard Ken Griffin from Citadel speak at this conference we're at, and he talked about picking best practices from different companies and sort of assembling his CEO playbook from other people he learned from, Jack Welch, et cetera, et cetera.
Do you look up to one CEO? Are you following a playbook or are you just, I'm going to make it up as I go? I have a lot of, I'm going to make it up as I go. Yeah. So, you know, and I think this applies to Luana too. Like both of us, we're probably very sort of like entrepreneurially illiterate. Like we haven't read all the books. We haven't watched all the podcasts. You don't live on Twitter. I do Twitter a bunch just because a lot of our users are on Twitter, but not like in the sort of like here are the four steps to build a company sense. Okay. You're not in that ecosystem. But I have, I look up to, like, there's a lot of aspects, a little bit like Ken, honestly, like a lot of aspects of CEOs I look up to.
Like, I think the extreme boldness of Enon and his ability to attract talent is amazing. I think Tony Eshoo I always go back to because I think his operational discipline and execution, I think, is one of the best. His business is so hard. So hard. So is yours, by the way. Yeah, our business is hard and marketplace and all these issues. I mean, but I think those are two names that consistently come to mind. But there's everyone, like, there's so many people. I mean, like the Colossians have done such a great job at like creating this sort of brand aura around their company to attract like incredibly talented people to build something that just goes beyond what the company is exactly building.
And so I observe a lot of these different things and figure out like what I can take. But then after that, it's continuous iteration. Like what we do well, I think, is like we just try and we try fast and we're continuously like this work didn't work. okay like change it fast whether it's a hire whether it's an approach to things whether it's my own voice whatever it is i think we do this you know and i think that's the best way to find the right answer because oftentimes these things are very like i'm going to say company dependent but as i was saying that it's very like ceo or founder dependent like it's to your image it's very hard, you know, to market even your product if it's not coming truly from.
what you're from who you are because the company is going to be to your image no matter what you do in your headquarters in new york do you think if you were based here you would be more in the mold of every other company probably i also think it would have been harder because you were going to talk down to some of your crazy ideas yeah maybe to some extent the the harder piece i was thinking is just recruiting i mean one of the reasons we moved that time what i like about new york is for our company's mission which is you know like figuring out how to build this idea of infinite market the next generation exchange like fundamentally rebuilding wall street like this new wall street that is more like global more for the people um it attracts it it has a stronger let's call it like uh market fit with the talent in new york yeah much better much better and then there i felt confident we could hire the top one percent of talent whereas here maybe but But I don't see, it doesn't feel like it burns as cleanly.
I think here it's really AI right now. And I think even if, I mean, we didn't necessarily know that in 2020, but like, even if it wasn't AI, it was going to be something that is not finance, right? Okay, you and Luana have, I think it's 130 sort of direct reports. Have I got that about right? Yeah, yeah, pretty much. I mean, there's some functions that like, we sort of let them do like what they do. But pretty much most of the company reports do between the two of us. Okay, that's unusual. yeah it's pretty unusual uh five years from now are you it's unusual because it's small and it's unusual because it's zero hierarchy and it's unusual because they report to both of you um how does it actually work how is it not chaos it's kind of chaotic okay but i i think you could build an organization that's somewhat okay with that because what you get out of chaos is like continuous constant adaptability it's very easy for our company to adapt very easy i mean sam talked about pivoting and pivoting feels like a bit of a strong word but like the point is like you want to constantly reorient and reassemble around the biggest challenges or biggest opportunities for the company and you want to be able to do that with no friction that's inherently chaotic
how do you that's a complex right like it's a complex system like totally it's like organisms and cells are sort of moving around and like floating in the ether and then they you know what i mean yeah and so like that's it like the world is inherently chaotic system so you know i mean and so we're trying to impose structure that is unnatural given how the world is moving And in a way that's accelerating over time, you kind of have to be more sensitive to the fact that it's increasingly more chaotic. Your structure needs to be as adaptable as possible. Okay, this is sort of the crux of the podcast because the CEO playbook that I grew up with, like handed down through the generations, I think is getting a big rethink.
And like Brian Armstrong and Jack Dorsey are talking a lot about this new way to organize where it's not a pyramid. It's a circle. AI is in the middle. You're training the AI. All your systems are legible. Your people are feeding the AI. And the AI makes more and more decisions. Work chart's gone. Compensation is different. all the things are getting thrown out are you following along with any of that or you're just kind of making it up as you go making it up as you go i didn't even know about that i never heard about that but like um it's interesting one of the things i've learned by the way about all this i've interviewed all these ceos there's no one way to do it yeah you look the way jensen does it's totally different than elon it's totally different from yeah it's i was saying imagine jensen running citadel yeah that would be nuts you know or you know so i don't know i mean i think that like um or like even funnier like imagine ken getting dropped into open ai to run it like it would be so crazy but like um i i don't know i'm actually curious to hear your thoughts i mean like the the word is more interconnected than ever and i think just things are accelerating like the rate of learning the rate of change is like if it used to be i mean maybe like you have
to readjust fundamentally every three or four years than every year i mean i honestly think you have to readjust fundamentally what every month or two i kind of agree i'm learning so much faster than i used to learn i'm picking up skills so much faster than i used to learn um yeah the world has changed like january to today like it's it's so crazy i mean like how it's it's hard for me to imagine making a certain set of decisions in january
“now we have to go back to focus on the direct and like really scale that now that we have an extremely liquid ecosystem”
sports then we got into financials then you went to a consumer business and a b2b enterprise motion and we went back and we did all these in the span of like you know what like eight months right and then it was like a lot of the policy stuff and and we should talk about that a little bit but like you know you're like exciting exciting exciting all the way to till you get mainstream and when you get mainstream society all of a sudden is like whoa stop stop right there let's figure out what this is we don't understand it you know now you have the grandmas and feel like that's going on right now yes exactly it's been going on for six months but like an ai you know ai is battling with it like airbnb uber all of them at some point When you get a reckoning. And now, like number one priority since January, and I think we've done a great job at sort of positioning ourselves as a safe, responsible actor.
Particularly right now, after all the news about polymarket recently. Yeah, I think we've done a really good job at always being kind of regulatory first, do the right thing. But we had to kind of tell that story, and that's also hard and comes with all these challenges. But, I mean, think about that, right? Like, it's completely different functions. Like, you know, even if I build the best consumer marketing company, how is that going to help me with the brokers? And if I build the best sales function, how is it going to help me? And so it goes back to like, I think, okay, how do we resolve these problems?
“one where the ceo or the founders are straight up staring at the hole all day every day”
called out by the wall street journal for their marketing practices and congress is taking about you're used to all this stuff is this thing that's happening to polymarket at this moment good for you or bad i think it's bad for us i think it is too yeah for sure i like i i think you know when you start competing you realize competition is actually really never a real problem i really think so i mean unless unless you're in a small market i guess maybe that's a that's a problem but if you're in a small market then you figure out the next big market and figure
out how to go take it and split it with a competition it's okay we used to always say at hubspot we competed with salesforce.com and every time salesforce would like move the ship a little bit everybody in the company like we gotta move the ship in the exact same direction and i would say every time they zig we gotta zag yeah yeah there's always i mean but i just think i don't think that's a and maybe let me like say it maybe a slightly like more nuanced way like i don't think competition will be true like is ever a true sort of like company killer like i i You know, it's like if you're in a big market, you're going to have a big piece of the pie.
And if you're not, you should probably be in a like should be constantly iterating and shipping product and finding new on tap markets to basically go and win in. And and, you know, like there's I believe in abundance. I mean, it's hard not to be in abundance, right? Like, look at the last like five years. It's crazy. And so you were you were well behind them.
“move fast and break things and figure out how to regulate later like not in financial services”
You wandered through the desert for a long, long time. Very long time, yeah. CFTC was smacking you, saying no. Yeah, the government was trying to kill us. Yes. It must have been brutal. What was the lowest point? Honestly, I don't even remember. It was basically like it was truly like just sort of like it was bad. I mean, it was so bad. And it's like you're constantly in a state of grief. and then you start like you know you're like in this desert and you start seeing like you literally start like you're so desperate they start seeing fake mirages mirages yeah you you know you See something, oh, here it is, finally, and then it's not true, and it's disheartening, and it's just hard.
But the thing that was unique about us is we never pivoted. It was always Kalshi. I mean, Kalshi is everything in Arabic. We always wanted to build the everything exchange, the exchange for all these different assets, and we always stayed sort of, because part of it, and looking back, and when I was thinking about it, we didn't build Kalshi to build a company. We built a company to build Kalshi. It's a bit different. We were dragged by the idea. I wasn't the type that wanted to be an entrepreneur. or like i i think if you re-roll the dice multiple times i'd probably just be a trader or risk manager like i would not be an entrepreneur got it but the idea was so like glaring in front of us that we just had to do it like we felt that we had to do it and so the whole point of doing this whole thing is the idea okay so when that's the case and like if you lose the idea then you know a lot of people listening to this are walking through that desert yeah and i i read this book a long time it was called the dip and you're cruising along you get down the dip and you don't know if you're about to hit the bottom and come up.
That's what's hard about it. Or if it keeps going. Everyone thinks you're delusional. Yeah.
“it's a career, right? It doesn't end. You have all sorts of different issues over time.”
depression but like but it's not the life that you like oh you you finally made it you're successful you're on the pedestal like okay so what do people think about what the life of a rocket ship ceo is like versus the reality what do people have wrong it's it's just like like is it glamorous no no i mean especially i mean look some people i think i i see it sometimes it's like when you get to that and it's finally made like they really go enjoy life but it never be then like the company
is going to go sideways what's your life like i work a lot all the time i mean um are you married do you have kids i i have a partner it's been like four four years and some and complains a lot um no she's honestly great but like it's tough right she sacrificed a lot also to for me to get here because she supported me in the hard times supported me in the in the good times which are also hard keep her right yeah yeah she's she's like she's the best i mean i think the the but there's sacrifice on that front i think that i travel a lot i i wake up so basically i wake up every day at seven uh i'm usually at the office by eight and i work i leave the office usually at 10 uh i work a little bit at home i usually like maybe like waste time on instagram reels for like 30 minutes and i go to bed what's that what's the weekend like uh i usually try to like go out for dinner one of friday or saturday um generally saturday because friday i'm so tired like i just need to rest and if i'm not trapped like, I'm basically in the office Saturday, Sunday.
Like, I go to the office Saturday, Sunday. I kind of like being in the office. Is everybody, by the way, you're getting... Most people, most people, like... They're in there. Yeah, I mean, but it's not forced. It's not like, oh, you know, like the hardcore... Yeah. We try to do it in a way of, like... So no one is ever kind of, like, slapped or there's no expectation you're going to need to be in the office with these hours. I don't believe in that sort of, like, put everyone in the office 24-7, hardcore grind. That's gonna... I do believe the founders can do it because we have the most incentive to do it.
And if the founders do it, naturally, others are like motivated they want to be next like they like coming on saturday because there may be a little bit less people and they can sit next to you and ideate about a bunch of things and hopefully you got the right people that would show up but they don't have to you know okay let's just get back to the ceoing since we're there 100 would we say 130 150 direct 130 to 150 now it grew a little bit 150 you're and like 150 is an interesting number because it's dumb bars number it's hard to keep track of anything north of 150 it's hard to interview those people most companies started hiring middle managers what is is it is it like 170 three years from now is it 500 are you like william i i'm friends with william hockey at column yeah he's like at 130 he's like i'm staying at 130 is that you uh william is very good i think he's done a great job i i don't know i mean um i'm just thinking about the things that scale linearly so historically support but we have less than 10 support people you know obviously millions of customers you can automate a lot of that yeah it works really well honestly like if you train the right it's amazing honestly um so that's that's a linear thing that's gone i mean as we scale our institutional side i think
potentially sales could scale somewhat linearly but i don't know you know i'm kind of a believer in i'm actually curious what we think but i'm kind of believer in like a strong marketing and brand marketing as a as a fundamental enable of sales and like enable enabler of top of funnel yeah where's if you do that yeah yeah if you do that very well i i think people just sort of follow each other where does that come from from you you mentioned that a couple times like you're really detailed in the copy and all that you didn't grow up you grew up as a kind of mass cs guy where does that come from and is it all good but the perfectionism that came from my mom like i i'm like i tend to have ocd and obsessive with these things and i want things to be really perfect like as perfect as well and it actually is exactly it really matters this is the key thing like the all the results are in the last 10% like most people 80 20 it that doesn't work everybody's 80 20 okay it has to be Perfect.
And if you, it's like this sort of, especially with marketing, there's like this sort of like a resonant frequency that you have. This is your mom talking right now. But, but this resonant frequency concept is very interesting because I think when you hit it, you get these dramatically improved results. Right. And, and like, Give me an example.
“we were waiting for the perfect moment because then that's when you get the 100x outcome, right?”
The AI ads, I think we've done a lot of work on the, like when we did the news integrations back in the fall, we announced CNN and CNBC and Fox. all of these were like we really wanted to time them at peak moments where people were talking about this debate between is the news sort of like uh gone is it like a thing of the past and for us the angle was never like oh cash partners it was like the news is actually modernizing how did i know you want to time it well but does timothy care does cnn care does the new york times care do the counterparties battle all these different things and you cannot have too much process and you have to break their own processes you know it's all of the same that we discussed That's a shit fight.
If you have had a partnership that's doing, you know, a whole structure and they plan for three weeks, you can't do that. Did you hire any professional marketing person inside your company? Not like I had in any way. I could not. I mean, we have a CMO, Alan, he's incredible. So Alan takes care of all the scientific pieces, very good at spending money to basically with high ROI. And then the rest is like, you know, so the person that leads our brand or leads is doesn't have any direct reports. It's just sort of flying around country and like doing cool stuff. and he he ran a twitter account before that you know the inverse kramer that wait that's where he started he was he's the inverse kramer account remind me like you know the inverse like jim kramer when he yes yes yes yes yes he's like the inverse kramer like index you make more money betting against yeah exactly so and like i thought he was that was him yeah and i hired him i was like you want to come and do our social he started doing our social and he had like a knack for he came up with the AI idea. He has a knack for these sort of like weird esoteric ways to just like be part of the zeitgeist. And you know what's interesting? That has worked equally
for consumers and Okay, I didn't expect you to say that. Yeah, people would think like, oh, you know, institutions want sort of this. They do, and like, they want to be able to talk to a chief risk guy, and like, they will, and we have all that. Like, we have a very strong, robust foundation. But being top of mind just matters. Continuously top of mind is very important. You've got a knack. I'll give you that. Okay, I want to wind the clock back because we haven't completely finished the desert story. at some point the conversation happened inside of the company hey we should sue the cftc whose idea was that and what was the reaction you wanna i mean uh what'd you say i mean it's crazy right like the i mean it is crazy it is actually crazy and also i mean it ended up being crazy all of it even though we won i mean that because like um it's so much more than just being right like it's so much more than just the lobbying you know right it's unfortunate but it's the truth a lot things are political and depends on how the winds are shifting and um and the government is truly all-powerful like they they can just do things for private to private companies or probably or companies just like companies in the private sector because um by the time you hold the
government accountable to that thing you probably will be dead basically or the cost would be so ginormous yes you know the government doesn't really incur any cost they're protected from any cost okay but take me in the room when she brought it so so so you know there's a little context that because we started trying and this goes back to how much foundation we built like people always think overnight success always been two years but it hasn't all of this has been like part of a very long-term plan a bit like jensen right like he's built such a foundation for so long and that's how these things go and we started engaging about the election market before we even launched the general public in the end of 21. we started talking to the government saying we want to do this it's very important here's why it's gonna work it's gonna be the most accurate gauge and here's how it's legal which it is um and they're like okay fine we'll work with you you know whatever month after month they wouldn't give it to us they wouldn't give it to us i had bet all the company on like the election market for 22 the 22 midterms that was what we're aiming towards the board is ready for it etc and they keep like delaying delaying delaying
up until they pushed it after the midterms so they pocket vetoed like they didn't say no they just managed to politely delay us enough that it didn't happen so that was heartbreaking you know it's been like we started in 2018 we finally got to 2021 finally excited about launching the whole company was excited everyone's excited launch and all the issue about launch started working on the election market and gets banned at the end of 22. so now we launched with a very limited set of Things that's going to be very hard to get the exchange running, but they banned us. We lost a lot of the team over it.
And you know, with these situations, what's really hard about these situations- Did you push them out or they left? A bunch of people left. Did you do a layoff? And then we had to do a layoff. And because what happens in these situations is that- I'm going to go on a tangent. I think it's an interesting thing. Let it rip.
“The best poker players, they know when they're playing a good hand and they're okay with the variance.”
what was going on in where were you yeah so you know i the litigator yakov roth who led this and you know we interviewed everybody i picked him because he's extremely smart but the thing that i felt he was really good at he like he had a missionary like this man wakes up in the morning and thinks about how to put the federal government in check okay you know you want that person just like this guy yeah so it's like he's an amazing litigator but like in the summer of 24 you know usually we text and all that he called me and i got really anxious i thought that the court hearing came like i was like what like you know he's like what's up and he like talked to me about something you know yeah and like dude my heart dropped don't ever call me like you should only call me once you have the court decision like never call me ever again text me i don't want you to call me because you know in the 10 seconds where i have to pick up the phone my heart dropped she's like okay fine
i won't call you until the decision and i was sitting you know on my desk and i remember like rayner one of our engineers sitting next to me and like his name pops up on my phone okay and like i could like my entire body like i just could feel you know you know these moments where you feel your entire body just sort of like paralyzed like oh shit and so i pick up the phone and i was i was like why are you calling me you know and then he's like we won and after that i don't remember like we were throwing like chairs in the office i mean yeah we were throwing chairs in the office we like we like basically destroyed the office you know it's like i mean it was unbelievable because you know it's like you want and in that year we suffered so much because you had like the competitor like where you know poly was getting the brand and we were staying true to our strategy we're going to stick with it the government was yanking the clearinghouse from under us um enforcement action after the other they were finding random things to just like great actions against us audits you know the audits that usually take 10 days they were mill to nine months yeah it was just sort of like truly painful like you know the whole
like warfare thing it truly happened and they make your life miserable And not just the company, you own personally. It's like kind of this intimidation tactic up until you cave, up until you're so exhausted. And it was just so vindicating. It was so nice, right? And finally, it felt like we finally had the opportunity to just sort of like win for the first time. Okay, you win. And of course, you knew this was going to work. Did it work like way better than you thought? not in the first few days oh it's like all things yeah it's like all things you have to build the motion and you have to build the brand and you have to so we but this is the thing you win and then oh let's launch it and then nothing happens by the way the time you won this case like four weeks like three weeks and a half before the election was that random timing yeah you gotta get it sometimes you know fascinating you know tony says it sometimes like you you need luck sometimes yeah is it because we're just lucky i think part of it yeah you need to be you need get lucky but i think you took risk and we took five six years of expanding that locked surface area so at some point we could but it didn't work even better than you imagined after we started
compounding so it takes time everything takes time but in those three weeks and a half like look we have three weeks and a half to make this go mainstream yeah everybody's in the office i don't i like basically honestly would shower maybe like once every four days like i was just like i don't care about anything this is my shot and so we worked so hard in those four weeks it was slow slow so but then it started upticking and then the machine started going and then when it started going it was beautiful it was amazing i got a 21 year old son and he and all his friends use calci yeah and i know you're going to say it's trading not gambling but i'm a little afraid
“one of the things we create is a parent portal where moms and parents can give us their ID and tell us don't let anyone else use it.”
and founders listen to it you've had a really unusual like really long strange trip yeah one last piece of advice or tips for folks going through going through the desert i think that like I would say a few things, but like one, like really question really hard why you're doing it, you know, because the thing that you're like, if it's not for the company itself, the thing that you're hoping to get, I don't know if it's really there, which is a glamorous, you know.
I never found it the least, obviously financially rewarding at some point. For sure. There's many ways to do that these days. The opportunity cost is very high, right? Like if you, I mean, you can join a fast growing company. I mean, there's so many ways to do that. Right. Um, so I, I just think the monotech. A reward just feels like a... Risk adjusted is probably a stupid move. Yes. And if you adjust also for lifestyle and amount of pain, it gets pretty unattractive, right? Okay. Okay, your little brother comes to you and says, I want to start a company. What do you say? I just say, why? You push back?
Yeah, why? Like, explain. What is it? Like, oh, I want to be my own boss? You're not really your own boss. You've got a board. you've got you work for all your employees you work for everyone your users i mean if you're a good CEO you're basically you work for everybody yeah i mean i don't think it's that sort of sense of freedom is real in any way actually you're you're the least free right and the more it grows the less free you are right you know so like uh the second thing is like um i really believe in the sort of theory like i really strongly believe in the in the in the theory of like um It has to be true to you.
It's going to be very hard to build a company, market a product, build a product that is not you. It's very hard. I honestly don't see how that works. And it's so interesting because every time you see a big company and then you meet the founder or the CEO of that company, you'd probably agree with me on this. It's shocking. Yes. The office is them. If you meet them, you're like, I totally understand why that company is the way it is. right and and so and i i feel like people i don't know i feel like that's not put into practice enough does that make sense like i think people just try to you know figure out all the right ways to do things i just i mean i wish there was but i if there was and everybody's a really good quote be yourself everyone else has taken you're definitely yourself thanks for coming on thank thanks a lot for congrats on all your success thanks so much for having that's great okay hope everybody liked that. I really enjoyed talking to him. It's the second time I met him. He's a gem.
A couple of my takeaways. Holy crap, is he mission driven. He had a mission of how we wanted to see the world change. And the company was just like, okay, we're going to build a company to pull that mission off. People talk about mission a lot, very much in his case. It rhymes with kind of how HubSpot started. Our vision mission was we wanted to change marketing from outbound to inbound. And we just were like, oh, we need to create a company to pull that off. It wasn't originally a company. It was an idea. So I like that. And I like founders who are, he's very obsessive. And Very mission driven. I feel like today with startups, everyone's trying to win Twitter for the day and sometimes making short term decisions. The thing I like about Kalshi and the thing I really like about SpaceX is they made some big foundational bets and were super patient and were really rewarded once those things paid off. And I think more founders can learn from that. Last thing I would say is he's got a unique relationship with Luana, his co-founder.
Luana's the kind of organized one and very risk-seeking. And he's a little bit all over the place, and he's risk-averse. It was the exact opposite of what I thought those two relationships were, but it's very much 1 plus 1 equals 3. It's reminding me of my relationship with Dharmesh and how complementary the two are. Hope you liked it. You
