Miles Grimshaw

Adam Fry Verified account @adamhfry · 4d

This week's ChatGPT feature drop - Nov 10:

ChatGPT's been growing a ton – we went from 1B to 1.2B weekly active users in just a few months. The team's been on a roll continuing to make the product better day by day. Here are a small things we're released recently:

1/ Account switching! If you have two ChatGPT accounts, you can log into both and switch between them easily. iOS is 100% rolled out, and we're in progress rolling out on Android.

2/ Images 2.6: It's faster to create images and easier to make precise edits. And you can also make GIFs! In September, when Images 2.5 launched, users were creating 3B images per week in Chat. Now, as of this week, users are creating more than 4B images per week in Chat.

3/ iCloud Mail and Calendar: If you use iCloud Mail and Calendar, you can now connect them to ChatGPT. Ask questions about what’s in your inbox and on your schedule. Gmail and Google Calendar plugins are now also available across all plans as well.

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Simon Eskildsen Verified account @Sirupsen · Sep 11

I was on teams at Shopify subject to this—it was tough, but more often than not, @tobi ended up being correct.

Now, as a founder, I get why Tobi did this more than I ever understood at the time. It is not the easy path.

I have the luxury of our company still being smaller (40-50 headcount), so it's easier for me to intervene early.

I am continually learning to find the best place during a project to insert myself, but sometimes, it ends up being late and painful; that just plain sucks.

But, long-term it is much worse to ship things that are sub-par. The job of a leader is to pull pain forward.

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Dialectic with Jackson Dahl Verified account @DialecticPod · Sep 8

" A great board member is demanding in good times and supportive in tough times."

"In success, you can level up to the next area. You can get the next amazing recruit. You have the capacity to walk into a room with a customer that maybe you shouldn't be the one serving."

"Simultaneously, when things are not working, that founder has thought about all the ways it's not working, all the pain of it not working, way more than we ever will."

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Jackson Dahl Verified account @jacksondahl · Sep 1

Dialectic 56: Miles Grimshaw

@milesgrimshaw is an investor at @ThriveCapital.

He has spent his life hunting change: from "adventure racing" to finding and working with the world's most ambitious companies.

His favorite part: getting to go back down the mountain and begin again.

I talked to Miles about playing infinite games, seeing greatness up close, and the biggest change he's seen so far:

After a career of software investing, all of the underlying assumptions for venture-backed software startups are in question.

What moats will persist? Is software over?

We also discuss:
- Impatient patience: flying to Ottawa for dinner with @Sirupsen and waiting a year to invest in @turbopuffer
- Two fundamental questions: "what is it?" and "who cares?"
- Software's barbell future: Benioff building "sales city" and "the champagne region of Palantir"
- Founder Vision: "you go where you look" and what @mntruell saw for @cursor_ai
- Getting up to speed as a generalist: "I don't know" and "I'll figure it out"
- Intuition for great: committing to SpaceX laser engineers (@meshoptical) in 48 hours, with no domain expertise
- Humility and conviction: leaving Thrive after a ~decade for Benchmark, and coming back

Timestamps:
(0:00) Opening Highlights
(1:37) Intro: Miles Grimshaw
(4:30) Infinite Games, Adventure Racing, and Starting Anew, Over and Over
(11:01) Staying Hungry: Proactive Hunting and the Turbopuffer Story
(17:35) Impatiently Patient: Courtship, Cursor, Recruiting, and Joining the Team
(25:33) Loving Change: London to America, the Himalayas, and Learning New Sports
(31:36) The Genetics of Companies: "What Is It?" and "Who Cares?"
(38:08) House Cats & Tigers: Where Is the Founder Looking?
(47:00) Confidence in Uncertainty and Customers That Pull You Into the Future
(54:25) What Remains for Software: Moats, Cities, Wall-Clock Time, and the Barbell of Scale & Luxury
(1:04:54) Craft, Trust, and Why Software Isn't Over
(1:11:13) Intuition: Gradient Descent and Seeing Greatness Up Close
(1:18:07) "I Don't Know" and "I'll Figure It Out"
(1:22:12) Commitments, Not Bets: Closing People and Board Work
(1:29:06) Joining Thrive, Being a Punk, and Music Studios over Jury Trials
(1:36:18) Leaving for Benchmark and Returning to Thrive
(1:43:18) Dream Bigger: Lessons from Josh, Teaching Agency to Kids, and Going the Distance

@DialecticPod 56: Miles Grimshaw - Back Down the Mountain - is out now below and on all platforms.

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