The Twenty Minute VC

Kalshi CEO Tarek Mansour: How to Build Moats Against Incumbents; How to Hire Engineers | 20VC #931

Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Tarek has raised funding from some of the best including Alfred Lin @ Sequoia, Ali Partovi @ Neo, Ron Conway, Charles Schwab and Henry Kravis. Before founding Kalshi, Tarek worked at the likes of Citadel, Palantir and Goldman Sachs, in various different roles. ------------------------------------- Timestamps: 0:00 Intro 0:36 The founding of Kalshi 3:23 What are you running from and towards? 5:03 Leading and parenting 6:13 Work-life balance 10:35 How has your style of work changed? 14:20 Is naivety a superpower? 16:10 How do you hire? 18:19 Terrible hiring mistakes? 19:48 How long do you give someone before letting them go? 21:25 Biggest insecurity in leadership 24:24 How are you so good at hiring engineers? 28:15 Why is B2B SaaS is a ponzi scheme 31:22 What would you like to change about venture? 33:55 Where do founders go wrong when fundraising? 38:37 How much money have you raised? 41:37 Biggest learnings from the people you work with? 44:25 What’s your favorite book and why? 44:45 Biggest strength and weakness 45:20 Hardest element of role with Kalshi today 46:25 If you could be CEO of any other company 47:47 What angel investors have been most helpful? 48:13 What do you wish you knew when you started? 49:28 What would you like to change about the world of startups? 51:08 Where do you see Kalshi in 5 years? ------------------------------------- In Today’s Episode with Tarek Mansour We Discuss: 1.) Entry into Startups: How did Tarek make his way from a nerdy kid in Lebanon to having his first startup funded by Sequoia and billionaires likes Charles Schwab and Henry Kravis? How did his mother’s continuous desire for excellence change Tarek’s mindset? What are the biggest lessons that Tarek took from his mother’s strict parenting and how did he apply them to how he manages the team at Kalshi today? 2.) What it Takes to Succeed: Why does Tarek believe that the world does not want your startup to exist? In that case, what are the core traits that founders need to fight this headwind? Does Tarek believe in work-life balance? What are some of the struggles of this? Does Tarek believe you should work on your weaknesses or double down on your strengths? 3.) Building the Team: Does Tarek believe that naivete is a strength or a weakness? At what point does it change between being a strength to being a weakness? Does Tarek prefer to hire more senior experienced people or younger hustlers with more energy? What have been the single biggest hiring mistakes that Tarek has made? How has it changed his approach to team building? What is the one single trait that if Tarek sees, he will not hire? How does Tarek make the interview process both fun but different and challenging? Where do so many founders make mistakes in how they construct the hiring process? 4.) Tarek Mansour: AMA: What have been the single biggest lessons from working with Ron Conway and Alfred Lin? What are some of Tarek’s biggest insecurities in leadership today? What does Tarek know now that he wishes he had known at the beginning of his time with Kalshi? What would Tarek most like to change about the world of startups? ------------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/tarek-mansour/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Tarek Mansour on Twitter: https://twitter.com/mansourtarek_ ------------------------------------- #Kalshi #TarekMansour #Predictionmarkets #Predictionmarket #founderadvice #founderstory #HarryStebbings #20VC

Harry StebbingshostTarek Mansourguest

Sep 30, 202252mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Kalshi CEO on ruthless focus, hiring killers, and regulatory moats

Kalshi co-founder and CEO Tarek Mansour explains how a trading-desk insight at Goldman led him and his co-founder to create a regulated exchange for trading directly on events, pulling them off a traditional finance career path. He digs into his upbringing, intensity, and views on imbalance and sacrifice as prerequisites for outlier outcomes, including his skepticism about work–life balance. Mansour lays out how Kalshi built deep regulatory moats, how he thinks about prioritization, naivete versus experience, and why he optimizes for expanding a new asset class rather than near-term company metrics. He also shares detailed views on hiring engineers, common hiring and fundraising mistakes, and what makes truly valuable investors and angels.

IDEAS WORTH REMEMBERING

5 ideas

Outlier outcomes usually come from outlier imbalance and sacrifice.

Mansour argues that doing something exceptional almost always requires giving up a conventional, ‘balanced’ life for long periods; intense focus and 120% effort are recurring themes from his upbringing and his approach to startups.

Frame priorities around the ecosystem and category, not just your company.

He optimizes decisions by asking whether they expand the overall events-asset ecosystem (new markets, new participants) rather than chasing short-term revenue or user metrics, trusting company outcomes to follow from category growth.

Balance brute force with deliberate prioritization as the company scales.

Early Kalshi was built on sheer brute force and all-nighters; now, Mansour pauses to prioritize and avoid ‘greedy algorithms’—still willing to brute force when needed, but only on the highest-leverage problems.

Hire for drive, self-awareness, and cultural contribution—not just IQ.

He sees over-indexing on raw intellect as a major hiring mistake; the most damaging hires are brilliant but low on self-awareness and cultural fit, because they’re hard to manage, coach, and eventually part ways with.

Use real problems and elegant puzzles to attract and assess engineers.

Kalshi’s interview process minimizes generic algorithm questions, instead using actual, scoped problems from their exchange and intellectually beautiful math challenges to both excite candidates and test deep problem-solving.

WORDS WORTH SAVING

5 quotes

If you want to achieve outlier results, you need some sort of outlier imbalance.

— Tarek Mansour

A startup is intrinsically something that the world does not want to exist.

— Tarek Mansour

You don’t get to just show up and work smart. You have to work very hard first, and then you can optimize into working smarter.

— Tarek Mansour

There are people who want to make it happen and there are others who need to make it happen.

— Harry Stebbings

Most people that look like they have it all figured out… they’re like you. They stumbled into things with a lot of grit and ambition.

— Tarek Mansour

Founding story of Kalshi and the vision for event trading as an asset classPersonal psychology: upbringing, intensity, imbalance, and work–life tradeoffsBuilding moats in heavily regulated markets and leveraging naivete vs. experienceHiring and evaluating engineers, culture fit, and avoiding hiring pitfallsLeadership insecurities, being respected vs. liked, and communication styleFundraising philosophy, round sizing, and the role of angels and VCsCritique of B2B SaaS dynamics and broader startup/venture ecosystem trends

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