Jason Preston

Strangely, using AI is making me want to buy more computer monitors. And it's not like I don't have screen real estate.

Charisma isn’t magic — it’s a set of habits and choices. A recent piece by @rex_woodbury nudged me to unpack my own take: open.substack.com/pub/jasonp/p/t…

Experience is funny; the more of it I have, the more I value it. Without experience, it's hard to know what's true vs what's marketing. open.substack.com/pub/jasonp/p/c…

I love good decision making frameworks, and breaking larger decisions into smaller decisions is great because it's *so easy to implement*. Good advice from @collinwallace on Substack: collinwallace.substack.com/p/the-hidden-r…

Honest question: if US senator insider trading is very profitable, is it a good strategy to monitor and mirror the positions of an index of US senators? Is someone doing this?

My partner @salsop and his son have a podcast, and this one interviewing Denter & Meow Wolf Founder Vince Kadlubek is fascinating a fun: linkedin.com/posts/salsop_s…

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/f…

Really interesting. Adding tollbooths to AI crawlers actually shifts the work of monetizing content from the producers to the tech companies. crazystupidtech.com/2025/06/22/why…

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

theinformation.com/articles/opena… 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.

I wonder if closed data + open source + vibe coding = way more on prem enterprise software services?

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/t…

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 into equity after an expiration date is standard in convertible notes and should be standard for SAFEs too. theinformation.com/articles/one-s…

This is fascinating. @JoannaStern'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: wsj.com/tech/ai/ai-fil…

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.

This makes a lot more sense when you think of it as an acqui-hire.

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. I've picked it up again & it will break my heart, but it is so beautifully written I can't help it.