Startup Grind

The leading community for people building, working with and investing in startups.

[Startup Grind @StartupGrind]

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.

[Vinod Khosla @vkhosla]

Thank you @DerekjAndersen

[Derek Andersen @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.

[Divot @Divotdotorg]

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.

[Startup Grind @StartupGrind]

June 4, 10am to 7pm

https://t.co/esm7WbXPbv

[Startup Grind @StartupGrind]

@Snowflake is bringing builders together for a full day of AI, data, and practical learning.

On June 4, our partner Snowflake is hosting Dev Day, a free full-day event for startup founders, AI and ML engineers, data professionals, and builders working with AI.

From 10 AM to 7 PM, attendees will get hands-on with bootcamps, hear from industry leaders, explore new tools, and learn how to take AI projects from proof of concept to production.

The day will also feature the Startup Challenge Finale, where emerging startups will showcase what they’re building.

For anyone building with data and AI, this is a strong opportunity to learn, connect, and leave with ideas you can actually use.

[Derek Andersen @DerekjAndersen]

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

[Divot @Divotdotorg]

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

[Divot @Divotdotorg]

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 👇

[Startup Grind @StartupGrind]

He was on fire!! 🔥

[Divot @Divotdotorg]

new ep is live @divotpod

@justinkan took the @StartupGrind mainstage and said what most founders won't, selling @Twitch to @amazon for ~$1B didn't bring the fulfillment he expected.

link in the replies

[Divot @Divotdotorg]

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 ⤵️

[Derek Andersen @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

[Startup Grind @StartupGrind]

https://t.co/vYstWH0Xh7

[Startup Grind @StartupGrind]

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.

[Derek Andersen @DerekjAndersen]

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

[Derek Andersen @DerekjAndersen]

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!

[Startup Grind @StartupGrind]

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. 🫶

[Nuro @nuro]

"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.

[Derek Andersen @DerekjAndersen]

Thanks @aplusk for being at Startup Grind this year.

[Startup Grind @StartupGrind]

Eoghan McCabe (@eoghan) said what everyone thinks but nobody says out loud.

He hates the "I have a great team" speech. Calls it false humility. But then admits he genuinely has people around him who were closer to the AI shift than he was, and they were the ones who woke him up.

That kind of honesty is rare on a mainstage. Thank you for bringing it to ours, Eoghan!

[Startup Grind @StartupGrind]

@Chicostart530 😄🙌🏻