This is Startup Grind, baby. 😜 If you were there, you know. And if you weren’t, make sure to join us next year as we make the Startup Grind Conference anniversary the biggest one yet, together. Early interest list is open now. Link in reply.

A close friend amassed 5M rabid followers/fans as an expert in a specific enterprise vertical. He wants to partner with a team to co-found and build a product in the space. If your small team is amazing, and your startup isn’t working and you’re willing to pivot, DM me!

the world rewards the courageous. James Dumoulin (@tvmjames) got rejected by billionaires and A-listers. kept going. built the credibility. same people said yes later. credibility kills all bad attitudes. founder of School of Hard Knocks, 22M followers. live from the @StartupGrind conference w/ @DerekjAndersen. full ep in the replies.

The best investor question I ever received was in a pitch was with Sequoia when @gradypb asked: "If everything goes right, where will the company be in 10 years?" I have thought about that in so many different situations since. Think big, be positive, go get it.

Thank you @DerekjAndersen

Here is my story about Vinod Khosla. In May 2017, I was six weeks from running out of cash. I had over extended myself funding a software project inside of Startup Grind that later became Bevy. One night at midnight on the couch I said to my wife, "I'm about to run out of money and we're going to lose everything," She said, "You'll figure it out." I stayed up all night sending emails and praying. I had interviewed Vinod a few times at SG and barely knew him but I emailed him at 1:39am. He emailed me back at 7:34am asking for my number. He ended up calling me later that day in a ride to a meeting. His advice and encouragement helped propel me to raising $1M in 6 weeks and saved the company. I will never forget his willingness to answer an immediate call from a near stranger in my most desperate professional moment.

he posted 400 times on Instagram with 50 followers. didn't make money for 3 years…then found the pivot. doubled down. went from $100k/month to $1M/month in one year. now doing $1.5M to $2M/month. James Dumoulin (@tvmjames), founder of School of Hard Knocks, 22M followers. full ep w/ @DerekjAndersen in the replies.

This week on @Divotdotorg I interviewed @tvmjames from @hardknocksedu why 3 seconds decides everything in going viral, turning rejection into fuel, how he's interviewed 50 billionaires at only 23, and how he is building his media empire on billions of views one clip at a time. Timestamps: 01:48 — How School of Hard Knocks Started 03:56 — 400 Posts With Only 50 Followers 04:41 — From $100K Months to $1M Months 06:15 — How Small Teams Can Win With Content 09:24 — The Only Metric That Matters Online 10:20 — Why the First 3 Seconds Decide Everything 13:03 — How Travel Shaped James’ Ambition 14:25 — Turning Rejection Into Fuel 15:41 — Interviewing 52 Billionaires by 23 15:52 — How James Got Mark Cuban 17:30 — Tom Cruise, Brady, Shaq, and Bigger Asks 20:08 — Why Business Takes Courage 20:50 — Building One of the Biggest Business Media Networks Hashtags: #jamesdumoulin #schoolofhardknocks #contentcreation #goingviral #watchtime #entrepreneurship #businessmedia #founderjourney #creatoreconomy #divotpodcast

sold @Twitch to @amazon for ~$1B. achieved everything he thought he wanted and more. and it didn't create a lasting sense of fulfillment. @justinkan on what actually drives happiness for him. full ep @divotpod in the replies

nothing will ever hit like a jordan and Josh Luber nailed why. @joshluber co-founded @stockx, a $4B sneaker platform, and created Ghosts. brands control supply, but demand is the whole game. Jordan built that before social media took over, when he was the most popular athlete on earth and it was just him, all organic. full ep in the replies 👇

He was on fire!! 🔥

at @StartupGrind Conference mainstage, Navin Chaddha articulates why claude mirrors netscape's moment. the first browser organized the internet. claude's organizing work itself. companion, AI teammate, gateway. this is how the world shifts. full conversation w/ @DerekjAndersen ⤵️

My @Divotdotorg chat this week is with @MayfieldFund Managing Partner @NavinChaddha, one of the most thoughtful AI people I know. We talk about the AI infrastructure gold rush, OpenClaw, the Claude ecosystem, and the rise of personalized software. 01:14 — Why AI Is a “100x Force” for Humanity 02:27 — Where the Biggest Value in AI Is Being Created 04:19 — Nvidia, Infrastructure & the AI Gold Rush 06:02 — The Next Massive Opportunities Beyond Compute 08:03 — Why Claude Changed Software Engineering 10:05 — Claude as the “New Browser for Work” 12:31 — AI Agents & the End of Traditional SaaS 15:08 — The Rise of Headless Software Explained 18:12 — Why Everyone Can Now Become a Builder 21:05 — Human AI Teams Will Replace Old Workflows 23:16 — Navin Chaddha’s Biggest Advice for Founders #aiagents #claudeai #artificialintelligence #futureofwork #openai #anthropic #saas #navinchaddha #nvidia #machinelearning #futureofsoftware #startupfounders #techpodcast #airevolution #siliconvalley #automation #founderjourney #venturecapital #aiinnovation #divotpodcast

My @Divotdotorg interview with @shardul_shah from @IndexVentures. Shardul is one of the best venture investors in the world backing Datadog, Wiz, and others. We talk about engineers being measured by token usage, when you should never sell, the trait all great founders share. Timestamps: 02:43 — How a Random Encounter Changed His Entire Life 05:16 — Why Great Startup Founders Can Come From Anywhere 08:06 — Why Shardul Refuses to Invest Over Zoom 13:32 — Why Engineers Are Being Measured By Token Usage 14:39 — The Trait Every Billion Dollar Founder Shares 20:09 — The Brutal Truth About Boardroom Disagreements 24:03 — How Building Communities Led To Billion Dollar Companies 27:11 — Why Datadog Looked Like a Terrible Investment 29:03 — The Mindset Required To Invest Before Everyone Else 33:29 — Inside Wiz’s Historic $32 Billion Acquisition 35:40 — The 2 Questions Every Founder Must Answer 36:24 — If You Can 10X Your Company, Never Sell 40:17 — The Difference Between Your Heart & Your Mind 42:00 — The Ancient Philosophy That Changed How He Thinks 49:34 — Why Michael Jordan Obsessed Him With Competition 52:23 — Dave Chappelle, Nas & The Best Night of His Life 54:00 — The Truth About Intuition & Great Decisions

Hosted one of the biggest tech conferences in Silicon Valley @StartupGrind and also the world’s largest Community conference @CMX this week. Building community with people in person is still highly underrated!

Every chapter has a heartbeat. And behind it, a person who shows up. Month after month, city after city, opening the door so no founder ever has to walk this path alone. With over 600 chapters around the world, Startup Grind is only as strong as the people leading them. This year's Directors of the Year. 🌟 Alexandra Poelstra, Carlos Zarate, David Stengle, Rajiv Nathan, Corey Hart, Daniel Gomez, Michael Thaney, James Gee, Sid Khaitan, Reuben Levinsohn, Emma Loedel and Jason Kraus. Thank you for everything you give to this community. 🫶

"Long term, autonomous mobility is going to become a trusted part of infrastructure—a foundation society can build on top of. That’s going to be a phenomenal shift." – @dfergusonnz, co-founder & co-CEO of Nuro, on stage with @stevejang of @KindredVentures at @StartupGrind 2026.

Thanks @aplusk for being at Startup Grind this year.