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Jason Preston

@jrpreston.com

Early stage venture investor, Co-Founder of Dent. Longer thoughts at https://jasonp.substack.com

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28.11.2023
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Latest posts by Jason Preston @jrpreston.com

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Cardinal in Wake Forest, NC

02.01.2026 01:18 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I dig @emollick.bsky.social β€˜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...

12.11.2025 16:11 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I’m embarrassed to admit that I have two copies of β€˜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 GΓΆdel Escher Bach (which is a good thing)

05.11.2025 17:02 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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The Maker's Reflex On being too easily inspired

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...

10.10.2025 17:20 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I think I spend more time walking through bookstores than I do reading books.

30.09.2025 01:58 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

My wife and I share a home office, but I’ve noticed that AI makes our work increasingly audio-based.

22.07.2025 21:51 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

So true. If only we could be omni-attentive!

30.06.2025 14:53 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

It’s New York! I had to complain first.

25.06.2025 20:20 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I’ve been visiting NYC the last four days and the temps are wild! The first night the hotel gave me a room without A/C 😬

24.06.2025 15:12 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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Friction remover One way to think about AI is as a friction remover.

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...

24.06.2025 14:08 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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The CEO of LinkedIn uses copilot to fine tune his emails to Satya. πŸ‘€

21.06.2025 14:41 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Have any of you successfully used an AI agent or workflow to acquire a Switch 2?

14.06.2025 15:49 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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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/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.

13.06.2025 01:49 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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.

12.06.2025 16:28 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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The Market Has Changed. VC Hasn't. The financial markets have changed: successful companies can now stay private forever.

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...

11.06.2025 14:14 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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.

05.06.2025 17:42 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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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...

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...

30.05.2025 15:11 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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We Made a Film With AI. You’ll Be Blown Awayβ€”and Freaked Out. We tried to direct an AI film. The tools are magic. The process is madness.

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...

28.05.2025 14:39 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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.

27.05.2025 21:39 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I just realized that this makes a lot more sense if you consider it an acqui-hire.

21.05.2025 17:19 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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.

21.05.2025 17:16 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

My minimalism vs my computer geek: MacBook Air with all the upgrades, or mid-tier MacBook Pro?

21.05.2025 00:17 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Somehow, without noticing, I've ended up using Discord, Slack, Telegram, WhatsApp, and Signal, each for basically one groupchat. This is frustrating.

19.05.2025 22:51 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

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.

17.05.2025 23:49 πŸ‘ 1 πŸ” 1 πŸ’¬ 0 πŸ“Œ 0
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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 β€” based on his body of writing.

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...

15.05.2025 20:34 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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...

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...

15.05.2025 19:48 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

An interesting implication of AI replacing our search habit is that the model can get to know your idiosyncrasies and, without even telling you the brand name, individualize the choice of brand or product.

13.05.2025 16:03 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I imagine that there is no β€œbest” answer to a search query, and probably no single β€œbest” 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.

13.05.2025 16:03 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Before the internet, the question was do you know how to use software features to do what you want. The internet & mobile made it: the software exists to do what you want, can you find it? So now AI is: here is the way to accomplish your intent.

13.05.2025 15:47 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0