Jason Preston
@jrpreston.com
Early stage venture investor, Co-Founder of Dent. Longer thoughts at https://jasonp.substack.com
I dig @emollick.bsky.social ‘s suggestion to interview your AI agents (regularly). But also I think many AI benchmarks are still functionally binary: can it do this thing, or not? Below the line, I don’t care what the idiosyncrasies are, or the benchmark score www.oneusefulthing.org/p/giving-you...
November 12, 2025 at 4:11 PM
I dig @emollick.bsky.social ‘s suggestion to interview your AI agents (regularly). But also I think many AI benchmarks are still functionally binary: can it do this thing, or not? Below the line, I don’t care what the idiosyncrasies are, or the benchmark score www.oneusefulthing.org/p/giving-you...
I’m embarrassed to admit that I have two copies of ‘Zen and the Art of motorcycle maintenance’ but I only started reading the book for the first time this week! I am enjoying it thoroughly; somehow the writing has a timelessness to it, and it reminds me of Gödel Escher Bach (which is a good thing)
November 5, 2025 at 5:02 PM
I’m embarrassed to admit that I have two copies of ‘Zen and the Art of motorcycle maintenance’ but I only started reading the book for the first time this week! I am enjoying it thoroughly; somehow the writing has a timelessness to it, and it reminds me of Gödel Escher Bach (which is a good thing)
I realized that I have the Maker's Reflex -- I am too easily inspired by my experiences. But luckily, I've also figured out how to wrangle it: jasonp.substack.com/p/the-makers...
The Maker's Reflex
On being too easily inspired
jasonp.substack.com
October 10, 2025 at 5:20 PM
I realized that I have the Maker's Reflex -- I am too easily inspired by my experiences. But luckily, I've also figured out how to wrangle it: jasonp.substack.com/p/the-makers...
I think I spend more time walking through bookstores than I do reading books.
September 30, 2025 at 1:58 AM
I think I spend more time walking through bookstores than I do reading books.
My wife and I share a home office, but I’ve noticed that AI makes our work increasingly audio-based.
July 22, 2025 at 9:51 PM
My wife and I share a home office, but I’ve noticed that AI makes our work increasingly audio-based.
So true. If only we could be omni-attentive!
I feel this a lot these days when I see people angry that other folks are not focused on the same atrocity they are, with the same intensity they are. I regret to say there's more than one genuine atrocity in the world at the moment; it doesn't minimize the others if one chooses another to focus on.
don’t get distracted! | patreon.com/lubchansky
June 30, 2025 at 2:53 PM
So true. If only we could be omni-attentive!
I would very much like AI to remove the friction from taxes, photo organizing, unsubscribing from anything that makes you call to unsubscribe, and switching cable providers. Did I say cable providers? What’s that? I meant internet providers! open.substack.com/pub/jasonp/p...
Friction remover
One way to think about AI is as a friction remover.
open.substack.com
June 24, 2025 at 2:08 PM
I would very much like AI to remove the friction from taxes, photo organizing, unsubscribing from anything that makes you call to unsubscribe, and switching cable providers. Did I say cable providers? What’s that? I meant internet providers! open.substack.com/pub/jasonp/p...
The CEO of LinkedIn uses copilot to fine tune his emails to Satya. 👀
June 21, 2025 at 2:42 PM
The CEO of LinkedIn uses copilot to fine tune his emails to Satya. 👀
Have any of you successfully used an AI agent or workflow to acquire a Switch 2?
June 14, 2025 at 3:49 PM
Have any of you successfully used an AI agent or workflow to acquire a Switch 2?
www.theinformation.com/articles/ope... here’s an example of how private / public doesn’t prevent liquidity for founders, early employees. Probably also for early investors if they wanted to sell.
OpenAI Employees Have Cashed Out $3 Billion in Shares
My colleague Sri Muppidi broke the news Wednesday of OpenAI’s latest fundraising talks as it seeks to raise an unprecedented $40 billion. One previously unreported detail is that SoftBank bought about...
www.theinformation.com
June 13, 2025 at 1:49 AM
www.theinformation.com/articles/ope... here’s an example of how private / public doesn’t prevent liquidity for founders, early employees. Probably also for early investors if they wanted to sell.
As a user, when I use OpenAI and ask it to find or use something from the internet, I sort of imagine that it’s going to Google on my behalf and searching for me, vs Perplexity, which I think of as AI native search. I doubt this is accurate, but it’s the result of their respective branding.
June 12, 2025 at 4:28 PM
As a user, when I use OpenAI and ask it to find or use something from the internet, I sort of imagine that it’s going to Google on my behalf and searching for me, vs Perplexity, which I think of as AI native search. I doubt this is accurate, but it’s the result of their respective branding.
It took me a few months to figure it out, but the lack of liquidity for VCs isn’t really a structural problem. In other words, yes things have changed, but VC is actually the same and it’s just hard to do well: open.substack.com/pub/jasonp/p...
The Market Has Changed. VC Hasn't.
The financial markets have changed: successful companies can now stay private forever.
open.substack.com
June 11, 2025 at 2:14 PM
It took me a few months to figure it out, but the lack of liquidity for VCs isn’t really a structural problem. In other words, yes things have changed, but VC is actually the same and it’s just hard to do well: open.substack.com/pub/jasonp/p...
Smell is such a wild sense. I am making a custom trail mix and I added sunflower seeds… and now I’m surrounded by memories of little league baseball.
June 5, 2025 at 5:42 PM
Smell is such a wild sense. I am making a custom trail mix and I added sunflower seeds… and now I’m surrounded by memories of little league baseball.
Having a clause that allows investors to convert after an expiration period is standard for convertible notes and should be standard in SAFEs as well. www.theinformation.com/articles/one...
Why One Startup Is Telling Investors Not to Wire the Money
A few months ago, I wrote about a number of early-stage startup founders who chose not to raise venture capital after an initial seed round, instead running their startups on the sales their businesse...
www.theinformation.com
May 30, 2025 at 3:11 PM
Having a clause that allows investors to convert after an expiration period is standard for convertible notes and should be standard in SAFEs as well. www.theinformation.com/articles/one...
This is fascinating. @joannastern.bsky.social's experience with AI filmmaking mirrors my experience with AI app-making, and demonstrates why GenAI is more about expanding what's possible than replacing a person www.wsj.com/tech/ai/ai-f...
We Made a Film With AI. You’ll Be Blown Away—and Freaked Out.
We tried to direct an AI film. The tools are magic. The process is madness.
www.wsj.com
May 28, 2025 at 2:39 PM
This is fascinating. @joannastern.bsky.social's experience with AI filmmaking mirrors my experience with AI app-making, and demonstrates why GenAI is more about expanding what's possible than replacing a person www.wsj.com/tech/ai/ai-f...
Here's a novel thought: I'm going to go through my inbox in order of most important to least important, instead of easiest to hardest.
May 27, 2025 at 9:40 PM
Here's a novel thought: I'm going to go through my inbox in order of most important to least important, instead of easiest to hardest.
Hardware is going to be a huge part of how we use AI going forward, but this valuation seems out of line with what’s known of the company. It is of course Sam Altman’s hardware company as well as Ives’. No doubt that affected the deal.
OpenAI will acquire the AI device startup of Apple veteran Jony Ive in a nearly $6.5 billion deal, part of a push into hardware technology
OpenAI to Buy AI Device Startup From Apple Veteran Jony Ive in $6.5 Billion Deal
OpenAI will acquire the AI device startup co-founded by Apple Inc. veteran Jony Ive in a nearly $6.5 billion all-stock deal, joining forces with the legendary designer to make a push into hardware.
bloom.bg
May 21, 2025 at 5:16 PM
Hardware is going to be a huge part of how we use AI going forward, but this valuation seems out of line with what’s known of the company. It is of course Sam Altman’s hardware company as well as Ives’. No doubt that affected the deal.
My minimalism vs my computer geek: MacBook Air with all the upgrades, or mid-tier MacBook Pro?
May 21, 2025 at 12:17 AM
My minimalism vs my computer geek: MacBook Air with all the upgrades, or mid-tier MacBook Pro?
Somehow, without noticing, I've ended up using Discord, Slack, Telegram, WhatsApp, and Signal, each for basically one groupchat. This is frustrating.
May 19, 2025 at 10:51 PM
Somehow, without noticing, I've ended up using Discord, Slack, Telegram, WhatsApp, and Signal, each for basically one groupchat. This is frustrating.
Two tears ago, my mom gave me a copy of "Tomorrow, and Tomorrow, and Tomorrow" by Gabrielle Zevin. I read ~half of it and then put it down because I thought it might break my heart to finish it. But I've picked it up again & it will break my heart, but it is so beautifully written I can't help it.
May 17, 2025 at 11:49 PM
Two tears ago, my mom gave me a copy of "Tomorrow, and Tomorrow, and Tomorrow" by Gabrielle Zevin. I read ~half of it and then put it down because I thought it might break my heart to finish it. But I've picked it up again & it will break my heart, but it is so beautifully written I can't help it.
I think the real implication of AI generated and summarized text is that we’ll end up with more signal and less noise: posting will be for people, content marketing will be eaten by GPTs. open.substack.com/pub/jasonp/p...
Signals, not summaries
This is a fascinating experiment: Tom Tunguz put a prompt box on the top of his web site that will generate a custom blog post to answer your query — based on his body of writing.
open.substack.com
May 15, 2025 at 8:35 PM
I think the real implication of AI generated and summarized text is that we’ll end up with more signal and less noise: posting will be for people, content marketing will be eaten by GPTs. open.substack.com/pub/jasonp/p...
I love Tom Tunguz’ experiment in dynamic blog post generation from his back catalog. I agree, nobody wants to read your stuff. BUT, I think people want to know what’s on your mind. Maybe that puts video in the catbird seat going forward. tomtunguz.com/nobody-wants...
Nobody Wants to Read Your Stuff by @ttunguz
Nobody wants to read your stuff.
Writing is about the reader - the infinitely busy reader who has a thousand things to do & three goals to accomplish by the end of the quarter. What will attract the r...
tomtunguz.com
May 15, 2025 at 7:48 PM
I love Tom Tunguz’ experiment in dynamic blog post generation from his back catalog. I agree, nobody wants to read your stuff. BUT, I think people want to know what’s on your mind. Maybe that puts video in the catbird seat going forward. tomtunguz.com/nobody-wants...
I imagine that there is no “best” answer to a search query, and probably no single “best” app for notes, design, photos, etc. Search has collapsed the individuality of those answers over the past decade because people aren’t going to look through more than 10 links.
May 13, 2025 at 4:03 PM
I imagine that there is no “best” answer to a search query, and probably no single “best” app for notes, design, photos, etc. Search has collapsed the individuality of those answers over the past decade because people aren’t going to look through more than 10 links.
youtube.com/watch?v=qEjT...
This is a fascinating interview with Meta’s Andrew Bosworth and it has me rethinking the near future of how we interact with both technology and the world around us.
This is a fascinating interview with Meta’s Andrew Bosworth and it has me rethinking the near future of how we interact with both technology and the world around us.
What Comes After Mobile? Meta’s Andrew Bosworth on AI and Consumer Tech
YouTube video by a16z
youtube.com
May 13, 2025 at 3:47 PM
youtube.com/watch?v=qEjT...
This is a fascinating interview with Meta’s Andrew Bosworth and it has me rethinking the near future of how we interact with both technology and the world around us.
This is a fascinating interview with Meta’s Andrew Bosworth and it has me rethinking the near future of how we interact with both technology and the world around us.