The Ledger
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Jamison: Venture capital's heyday is over due to excess capital
“And also when it comes to venture, I think venture's heyday is kind of over, at least for now. I think there's too much money has entered the space, so too many companies that shouldn't have been funded have been funded.”
Jamison: AI Will Not Materially Impact Physical Trades Like Plumbing
“AI is not going to change how, you know, someone remodels a house, how a plumber changes the pipes, like that type of thing, and at least not in a material enough way to make a difference.”
Jamison: AI Venture Bets Resemble Airlines With High Capital and No Moats
“If you take all the profits of all the airlines over time, it's negative for investors. Like shareholders have had a negative return for that because they've just kind of competed themselves away. There's no giant moat to get those monopoly profits. And it's a…”
Jamison: AI foundation models will be commoditized without monopoly profits
“All of the big tech companies right now that are investing very, very heavily into building their own models. It's just going to be commoditized at the end. And no one really gets that monopoly profits where it's like, you know, a search, like Google got monop…”
Jamison: AI Model Niches Like Claude for Coding Lack True Differentiation
“I think even though the different companies are trying to niche down, you know, like Claude for coding as an example, I still don't think there's enough of differentiator to matter for that.”
Jamison: Creators can train LLM recommendations via self-published third-party content
“Cause you know, the LLMs are looking at Google results. We know that you can slowly but surely like train it on what is best and you have control that entire process. It doesn't have to be reliant on actual third party people. It can just be you on third party…”
Jamison: Holding 10-20% cash pays off by preventing panic selling during crashes
“There's a drag on your portfolio, but having, you know, you keep 10, 20% in cash or something like that, treasure bills, you know, there's going to be a drag on your portfolio, but if that drag lets you purchase when things crash, or even more correctly, proba…”
Jamison: Recent deals include dry cleaners, HVAC, and rehab centers
“Like I'm investing in the companies that don't really care about AI, the things that can't be disrupted, think more boring businesses, blue collar businesses stuff like that. The, I go for more of the small business thing. So some of my more recent deals was l…”
Jamison operates a Generative Engine Optimization firm targeting LLM product recommendations
“I have a company that we are very actively Basically doing SEO for the different LLMs. You know, essentially there's different names for it. There's AEO, GEO, AIO, whatever you want to call it. But we're essentially training the LLMs to answer the way that we …”
Jamison: Ranking across top search results forces ChatGPT product recommendations
“Can you go and like maybe five or six out of the top 20 results say that your iPhone wallet is the best one? What's ChatGPT going to recommend? They're clearly going to recommend your wallet.”
Jamison targets 30%+ IRR by passively acquiring profitable small businesses
“Started building up a portfolio of these small businesses that I could own passively. You know, targeting like 30% plus IRR.”