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Sometimes lightning really can strike twice in one day. From the 175-company YC class in March 2019, I made just two personal investments, both on the same day- founded by visionary male/female co-founders: Kalshi and Deel. Six years later, Deel is a decacorn valued at $17.3 billion, and Kalshi would be a decacorn too if they raised today. @Kalshi (@mansourtarek_ & @luanalopeslara ) and @deel (@Bouazizalex & @shuoshuooshuooo ) were both pre-launch when I invested at $10 million post for Kalshi and $15 million post for Deel. The reasons you back a founder can sometimes be unusual, but when you recognize a familiar pattern, it’s best not to overthink it. 🎥 Here’s @mansourtarek_ recounting why I wanted to take Kalshi’s entire seed note and why I decided to invest so quickly. The answer might surprise you: @mansourtarek_ @luanalopeslara @Kalshi

Whop just crossed $2B in GTV and $142 mil in ARR. Gen Z doesn’t want traditional jobs. Whop is becoming the backbone for how they earn. I’m slightly biased… I invested in @WhopIO at a $3M valuation in 2021 and remain the largest shareholder outside the founders. Even from that seat, I still don’t fully understand how Gen Z makes a living. Most investors are asleep. They’ll notice when ARR goes from $142M toward $1B within 18 months. The CEO Steven is one of the most naturally talented leaders of his age group. A world class engineer with unusual range, speed, and instinct. He has the kind of raw, unstructured talent you can’t manufacture: randomly insane piano skills but no Ivy League polish. Whop is a hidden gem… a generational company built by generational founders.

Story Time: Deel was an incredible investment - but also a massive fumble. Months after investing, I passed on the Series A at 4× my entry price. The math is ugly: Series A was at $60M post… and today Deel is worth $17.3B. The next year I met the founder of Rise. It wasn’t through my usual channels, I hesitated, and checked with @Bouazizalex to confirm it was ok. I invested in Rise at a $3M valuation. Basically a crypto focused Deel. In October Rise hit: • $11.5M ARR • 83% margins • 25% growth from Sep Started slow, but on this trajectory, they’re ~18 months from unicorn territory @hugfink congrats on hitting $1 billion in total payroll volume. Determination pays off. Huge space with room for multiple category leaders.

Have backed @connorzwick and @adhsu founders of @speak since 2016- invested in 6 consecutive rounds starting at $10M. Pretty damn slow to become a unicorn, but now it’s on. 🚀 • $100M ARR • 15M downloads • 40% daily retention • 120 team Fun story: on a 2018 call with Connor (while overseas and on the toilet) I upped my investment three times- kept realizing I needed to own more. They were talking AI and machine learning long before it was trendy.

My first long form podcast! Enjoyed chatting with @hdubugras

This is what quietly scaling to $150 million ARR looks like. Impressive growth @slashapp

I'm waiting for my right swipe @katyperry

My wife moved here from the U.K. years ago, and yesterday, the same day a self-described socialist became mayor of the financial capital of the world- she finally became an American. In that room of new citizens, you could feel pure hope… the belief that you can build something from nothing. That’s the American Dream. A promise of handouts may sound compassionate, but it quietly trades ambition for dependence, and that’s how great nations decline. Of course the majority will vote for someone promising things for free, but that illusion always ends up costing opportunity, ambition, and freedom. What moves society forward are the builders… those who take responsibility, take risks, and create opportunities that lift others. America became the world’s beacon because it rewarded that spirit- the courage to dream, to innovate, and to build a better life. We need to protect that mindset. Educate better. Think longer-term. Inspire the next generation to build, not depend. You can see that spirit in companies like @WhopIO (ironically based in NYC, but likely not for long) giving a new generation the platform and confidence to build their own future. Teach young people the power of equity, not just in markets, but in their own lives. Encourage saving, investing, and home ownership. Celebrate those who build slowly, brick by brick, creating generational stability. The American Dream isn’t dead, but it needs defending. And it’s worth defending. 🇺🇸🙏

Join me and @YahooNews live right now as we talk about how tech is reshaping the college experience: yhoo.it/15UPjCr #BornDigital

Sometimes lightning really can strike twice in one day. From the 175-company YC class in March 2019, I made just two personal investments, both founded by visionary male/female co-founders: Kalshi and Deel. Six years later, Deel is a decacorn valued at $17.3 billion, and Kalshi would be a decacorn too if they raised today. @Kalshi (@mansourtarek_ & @luanalopeslara ) and @deel (@Bouazizalex & @shuoshuooshuooo ) were both pre-launch when I invested at $10 million post for Kalshi and $15 million post for Deel. The reasons you back a founder can sometimes be unusual, but when you recognize a familiar pattern, it’s best not to overthink it. 🎥 Here’s @mansourtarek_ recounting why I wanted to take Kalshi’s entire seed note and why I decided to invest so quickly. The answer might surprise you: @mansourtarek_ @luanalopeslara @Kalshi

Spazz attack vine.co/v/b1ptrz00qvE

Activity on one of 20 servers at tinder vine.co/v/bJ6HTL1QwnX

My first long form podcast! Enjoyed chatting with @hdubugras

Sometimes lightning really can strike twice in one day. From the 175-company YC class in March 2019, I made just two personal investments, both on the same day- founded by visionary male/female co-founders: Kalshi and Deel. Six years later, Deel is a decacorn valued at $17.3 billion, and Kalshi would be a decacorn too if they raised today. @Kalshi (@mansourtarek_ & @luanalopeslara ) and @deel (@Bouazizalex & @shuoshuooshuooo ) were both pre-launch when I invested at $10 million post for Kalshi and $15 million post for Deel. The reasons you back a founder can sometimes be unusual, but when you recognize a familiar pattern, it’s best not to overthink it. 🎥 Here’s @mansourtarek_ recounting why I wanted to take Kalshi’s entire seed note and why I decided to invest so quickly. The answer might surprise you: @mansourtarek_ @luanalopeslara @Kalshi

Whop just crossed $2B in GTV and $142 mil in ARR. Gen Z doesn’t want traditional jobs. Whop is becoming the backbone for how they earn. I’m slightly biased… I invested in @WhopIO at a $3M valuation in 2021 and remain the largest shareholder outside the founders. Even from that seat, I still don’t fully understand how Gen Z makes a living. Most investors are asleep. They’ll notice when ARR goes from $142M toward $1B within 18 months. The CEO Steven is one of the most naturally talented leaders of his age group. A world class engineer with unusual range, speed, and instinct. He has the kind of raw, unstructured talent you can’t manufacture: randomly insane piano skills but no Ivy League polish. Whop is a hidden gem… a generational company built by generational founders.

I'm waiting for my right swipe @katyperry

Have backed @connorzwick and @adhsu founders of @speak since 2016- invested in 6 consecutive rounds starting at $10M. Pretty damn slow to become a unicorn, but now it’s on. 🚀 • $100M ARR • 15M downloads • 40% daily retention • 120 team Fun story: on a 2018 call with Connor (while overseas and on the toilet) I upped my investment three times- kept realizing I needed to own more. They were talking AI and machine learning long before it was trendy.

Story Time: Deel was an incredible investment - but also a massive fumble. Months after investing, I passed on the Series A at 4× my entry price. The math is ugly: Series A was at $60M post… and today Deel is worth $17.3B. The next year I met the founder of Rise. It wasn’t through my usual channels, I hesitated, and checked with @Bouazizalex to confirm it was ok. I invested in Rise at a $3M valuation. Basically a crypto focused Deel. In October Rise hit: • $11.5M ARR • 83% margins • 25% growth from Sep Started slow, but on this trajectory, they’re ~18 months from unicorn territory @hugfink congrats on hitting $1 billion in total payroll volume. Determination pays off. Huge space with room for multiple category leaders.

Join me and @YahooNews live right now as we talk about how tech is reshaping the college experience: yhoo.it/15UPjCr #BornDigital

My wife moved here from the U.K. years ago, and yesterday, the same day a self-described socialist became mayor of the financial capital of the world- she finally became an American. In that room of new citizens, you could feel pure hope… the belief that you can build something from nothing. That’s the American Dream. A promise of handouts may sound compassionate, but it quietly trades ambition for dependence, and that’s how great nations decline. Of course the majority will vote for someone promising things for free, but that illusion always ends up costing opportunity, ambition, and freedom. What moves society forward are the builders… those who take responsibility, take risks, and create opportunities that lift others. America became the world’s beacon because it rewarded that spirit- the courage to dream, to innovate, and to build a better life. We need to protect that mindset. Educate better. Think longer-term. Inspire the next generation to build, not depend. You can see that spirit in companies like @WhopIO (ironically based in NYC, but likely not for long) giving a new generation the platform and confidence to build their own future. Teach young people the power of equity, not just in markets, but in their own lives. Encourage saving, investing, and home ownership. Celebrate those who build slowly, brick by brick, creating generational stability. The American Dream isn’t dead, but it needs defending. And it’s worth defending. 🇺🇸🙏

This is what quietly scaling to $150 million ARR looks like. Impressive growth @slashapp

Spazz attack vine.co/v/b1ptrz00qvE

Activity on one of 20 servers at tinder vine.co/v/bJ6HTL1QwnX

Sometimes lightning really can strike twice in one day. From the 175-company YC class in March 2019, I made just two personal investments, both founded by visionary male/female co-founders: Kalshi and Deel. Six years later, Deel is a decacorn valued at $17.3 billion, and Kalshi would be a decacorn too if they raised today. @Kalshi (@mansourtarek_ & @luanalopeslara ) and @deel (@Bouazizalex & @shuoshuooshuooo ) were both pre-launch when I invested at $10 million post for Kalshi and $15 million post for Deel. The reasons you back a founder can sometimes be unusual, but when you recognize a familiar pattern, it’s best not to overthink it. 🎥 Here’s @mansourtarek_ recounting why I wanted to take Kalshi’s entire seed note and why I decided to invest so quickly. The answer might surprise you: @mansourtarek_ @luanalopeslara @Kalshi