Reminder: I'm raising my newsletter prices tomorrow. This is the first time I've ever raised prices What you get with an annual subscription: 1. Full access to every newsletter post, including the 5-year back catalog 2. An invite to a thriving members-only Slack community 3. A year free of Notion, Superhuman, Linear, Perplexity, and Granola If you subscribe now, you'll stay at the current price as long as you stay a subscriber. Sounds like a no-brainer to me.

ART OF THE DEAL: After Softbank CEO Masayoshi Son will announced a $100 billion investment in the US, President Trump asks him on the spot if he'll double it: TRUMP: "I'm going to ask him right now, will you make it $200 billion, believe it or not, he can actually afford to do that." MASAYOSHI SON: "With your leadership and my parternship and your support, I will try to make it happen." TRUMP: "Alright, $200. He'll make it happen." MASAYOSHI SON: "He's a great negotiator!"

Vamos, @RafaelNadal!   As you get ready to graduate from tennis, I’ve got a few things to share before I maybe get emotional.   Let’s start with the obvious: you beat me—a lot. More than I managed to beat you. You challenged me in ways no one else could. On clay, it felt like I was stepping into your backyard, and you made me work harder than I ever thought I could just to hold my ground. You made me reimagine my game—even going so far as to change the size of my racquet head, hoping for any edge.   I’m not a very superstitious person, but you took it to the next level. Your whole process. All those rituals. Assembling your water bottles like toy soldiers in formation, fixing your hair, adjusting your underwear... All of it with the highest intensity. Secretly, I kind of loved the whole thing. Because it was so unique—it was so you.   And you know what, Rafa, you made me enjoy the game even more.    OK, maybe not at first. After the 2004 Australian Open, I achieved the #1 ranking for the first time. I thought I was on top of the world. And I was—until two months later, when you walked on the court in Miami in your red sleeveless shirt, showing off those biceps, and you beat me convincingly. All that buzz I’d been hearing about you—about this amazing young player from Mallorca, a generational talent, probably going to win a major someday—it wasn’t just hype.   We were both at the start of our journey and it’s one we ended up taking together. Twenty years later, Rafa, I have to say: What an incredible run you’ve had. Including 14 French Opens—historic! You made Spain proud... you made the whole tennis world proud.   I keep thinking about the memories we’ve shared. Promoting the sport together. Playing that match on half-grass, half-clay. Breaking the all-time attendance record by playing in front of more than 50,000 fans in Cape Town, South Africa. Always cracking each other up. Wearing each other out on the court and then, sometimes, almost literally having to hold each other up during trophy ceremonies.   I’m still grateful you invited me to Mallorca to help launch the Rafa Nadal Academy in 2016. Actually, I kind of invited myself. I knew you were too polite to insist on me being there, but I didn’t want to miss it. You have always been a role model for kids around the world, and Mirka and I are so glad that our children have all trained at your academies. They had a blast and learned so much—like thousands of other young players. Although I always worried my kids would come home playing tennis as lefties.   And then there was London—the Laver Cup in 2022. My final match. It meant everything to me that you were there by my side—not as my rival but as my doubles partner. Sharing the court with you that night, and sharing those tears, will forever be one of the most special moments of my career.   Rafa, I know you’re focused on the last stretch of your epic career. We will talk when it’s done. For now, I just want to congratulate your family and team, who all played a massive role in your success. And I want you to know that your old friend is always cheering for you, and will be cheering just as loud for everything you do next.   Rafa that!   Best always, your fan, Roger

The ex-PayPal mafia is still the most insanely talented group of people we’ve ever seen. It just astounds me how ambitious and good at execution they all are after two decades. They ran with it.

We have some news. @sunilchhaya and I are delighted to announce that Kearny Jackson Fund III is live with $65M in committed capital (above our $60M target). We started fundraising for Fund III in Jan 2023 and had our first close of $55M in Dec 2023. We’re thankful to our LPs and founders who empower us to do what we love most: backing early-stage B2B software startups. Some high-level notes on our Fund III: ❌ No product, no problem. Happy to back founders pre-product or revenue 🧵 B2B focus: SaaS & Infrastructure as a core focus, with Fintech 💰 Investing $1.5M+ in pre-seed & seed stage startups ⚡️ Leading or co-leading rounds 🪙 Targeting 6-10% ownership 🇺🇸 Market focus: North America (USA) as the primary customer market 🔢 Investing in 30-35 companies over 3.5 years ❄️ Made one stealth investment in an ex-Snowflake team 👯‍♀️ 50/50 partnership across management company & GP between Sunil and I 🏫 Our LPs include four university endowments, pension funds, funds-of-funds (FoFs), and many VC partners and tech founders/operators 🐥 Kearny Jackson's portfolio: Motherduck, Cortex, Unit, EigenLayer, Comulate, Rythms, RelayFi, Sprig, and more Sunil and I are a bi-coastal team [I’m based in NYC, and Sunil is in SF], and we're excited to be backing the next-generation B2B startups!

There's a great joy in building a hard thing. Even if it goes nowhere, just the act of pouring your all into it + its creation is a process worth being grateful for in the moment. The more you try/fail, the more you don't fear failure which is usually a theft of that joy.

Pro tip: Whenever you take help, mentorship or advice from someone regarding career, work, life, relationships or anything else, make it a point to drop an update whenever you make progress irrespective of whether their advice helped or not. Always makes the other person feel valued and your protectiveness also makes them think highly of you. A small win-win gesture :)