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Tim Ferriss
Host, The Tim Ferriss Show; Author and Investor, The Tim Ferriss Show

I Asked AI What to Do With the Next 5 Years of My Life

📅 Jul 28, 2026 Tim Ferriss 11 MIN 24274 VIEWS 45 SEGMENTS · 2 SPEAKERS
In this edition of The Random Show, Tim Ferriss and Kevin Rose reunite over tequila to talk Zen retreats, learning to rock climb at (almost) 50, mortality and grief, why you should stop saying "one day," AI predictions , and much more. Please enjoy! This episode is brought to you by: Incogni, which removes your personal data from the web, helping shield you from fraud, scams, and identity theft: https://Incogni.com/Tim (use code TIM at checkout and get 60% off an annual plan) Wealthfront high-yield cash account: https://Wealthfront.com/Tim New clients get 3.30% base APY from program banks...

What Tim Ferriss said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Tim Ferriss discussed how AI tools like Claude Code and Gmail APIs are being used for personal data analysis, including a 20-year retrospective of angel investing. He noted that AI can reveal how memory is often about 20% off from reality, citing a wearable device that tracks conversations. Ferriss said AI-generated writing is so good that it drains his motivation to write, comparing it to AlphaGo's effect on a Go player. He praised asking AI open-ended personal questions, like what to do in the next five years, and said the answers were outstanding, with one business idea he urged a friend to pursue. He cautioned against outsourcing thinking entirely, but found value in treating AI as a close friend for advice.

Key takeaways

  1. Ferriss said AI-generated writing is so good it drains his motivation to write, as it can do in 30 seconds what takes him 30 hours.
  2. Ferriss found AI answers to 'what should I do in the next 5 years' outstanding, with one business idea he urged a friend to build.
  3. Ferriss said memory is about 20% off from reality, based on a wearable device that tracks conversations.
  4. Ferriss said AI can do in 30 seconds what takes him 30 hours, making it a powerful but demotivating tool.

Numbers and commitments

FigureWhat it refers toTypeAt
70% of what we think we know is actually true metric 1:10
20% how far memory is off from reality metric 1:27
30 seconds time for AI to produce what takes Ferriss 30 hours metric 5:43
30 hours time for Ferriss to write what AI does in 30 seconds metric 5:43
3 to 6 months of AI use needed for it to have enough history on you timeline 7:29
10% of AI input that could inform a major next chapter metric 9:53

Chapters

  1. 0:00AI and memory accuracy
  2. 1:33Startup genesis stories and sanitization
  3. 2:05AI for health and investing insights
  4. 5:43AI's impact on writing motivation
  5. 7:29Asking AI for life advice
  6. 9:53AI as a close friend for questions

Questions asked in this interview

5
  1. 0:20Which did I turn down that ended up being really important?
  2. 0:32And I'm like, but is it true?
  3. 2:47What if I had done that?
  4. 6:43But it's not going to come up with the original thesis for the whole thing, right?
  5. 7:29In my case, I didn't do that, but if it has enough history on you, you can just ask, 'What do you think I should do in the next 5 years?
Tim Ferriss 0:00 ↗
What are you doing now with the eye stuff?
Kevin Rose 0:02 ↗
Well, I mean, I'm more curious to hear your thoughts and predictions, frankly, because I think you're better at it. But I mean, I'm using Claude Code with Ferris APIs to do tons of like inbox analysis and stuff.
Tim Ferriss 0:15 ↗
Yeah, yeah, yeah.
Kevin Rose 0:15 ↗
Right? I'm doing a 20-year retrospective analysis of angel investing.
Tim Ferriss 0:20 ↗
Mhm.
Kevin Rose 0:20 ↗
It's like, who made what introductions? Which companies did I not reply to that ended up being successes? Which did I turn down that ended up being really important?
Tim Ferriss 0:31 ↗
Do you really want to do that to yourself?
Kevin Rose 0:32 ↗
Well, I suspected it'd be worse than it was. I actually have not — I haven't missed that many explicit opportunities. I wanted to test my own stories against data, right? Because I have all sorts of stories about why I did certain things and why certain things worked out. And I have certain stories about my batting average. And I'm like, but is it true?
Tim Ferriss 0:56 ↗
Right.
Kevin Rose 0:57 ↗
Really?
Tim Ferriss 0:58 ↗
Is it really true?
Kevin Rose 0:59 ↗
Let's look at some hard numbers.
Tim Ferriss 1:01 ↗
The sad truth, and I have a buddy that wears the bracelet and you've seen me with the necklace around, that categorizes your AI and listens to you 24/7.
Kevin Rose 1:09 ↗
Yeah.
Tim Ferriss 1:10 ↗
It's about 70-ish percent that we think we know, but is actually what we know. Out of the 100% of like what we think we know, this is the truth. I said I wanted a dark chocolate bar at 7:00 p.m. It's like, no, you said it at 5:00 and you said it this way.
Kevin Rose 1:26 ↗
And you said it was milk chocolate.
Tim Ferriss 1:27 ↗
Yeah, exactly. So, it's always about 20% off from where you actually think your brain's at.
Kevin Rose 1:32 ↗
Which is brutal.
Tim Ferriss 1:33 ↗
Well, plus, I mean, that's like last week, right? If you're talking about 15 years ago. I mean, if you listen to any genesis story of any startup, you're like, oh my god. Wait a minute now. Like, this is like a startup comic working on material, but he's been working on this one 5-minute bit so long that now he believes that's actually truth. The sanitizing and the editing of these startup genesis stories is hilarious, and there's no reason to think that I would be or you would be exempt from it. Right, when you're telling your own story, even if you're just telling it to yourself.
So, what's the number one thing that you've learned by applying AI to your life in this fashion? Like, what's the thing where you walked away and said, 'Damn, that was insightful, and I'm going to change my behavior,' or 'I learned something new about myself that I wouldn't have if I had not used AI'?
Kevin Rose 2:20 ↗
Well, I think from a holistic health perspective — by holistic I mean having enough data related to medications, supplements, predispositions, side effects, what happened to me 2 weeks ago — the LLMs have been incredibly helpful. I mean, the picture that they get and the speed with which they can deliver an answer that I can interrogate is just incredible.
Tim Ferriss 2:44 ↗
What did you learn? Like, what was the thing that you...
Kevin Rose 2:47 ↗
I mean, honestly, it's mostly avoiding disaster, right? It's like, are any of these things contraindicated with one another? Could A, B, or C explain D? And you have to keep in mind, these things can still hallucinate, but you can — I don't want to say eliminate that, but minimize it by just fact-checking across LLMs. There's that. I would say that there's a lot of insight on, hopefully, that can translate to future decision-making related to investing, which investing for me is not just amassing more chips. What's fun about investing to me is it's a way to scorecard your thinking and decision-making. It's just a very objective way to decide if something was the right or the wrong decision. And you can fine-slice that, and there are ways that you could maybe question that, but if you're asking yourself, 'Was I thinking well last month?' That's not a very helpful question. Where do you go from there? If you're logging maybe every decision you make every day and then trying to cross-reference outcomes with blah blah blah. Like, yeah, but you're never going to do that. But when you're making relatively frequent investments, you can do that. You can also run counterfactuals, right? What if I did the opposite? What if I had not sold that? What if I had kept that? What if I had done this? What if I had done that?

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Cite this transcript

APA, MLA, BibTeX
APA

Ferriss, T. (2026, July 28). I Asked AI What to Do With the Next 5 Years of My Life [Interview transcript]. Tim Ferriss. CEOInterviews.AI. https://ceointerviews.ai/interview/3004384/

MLA

Tim Ferriss. "I Asked AI What to Do With the Next 5 Years of My Life." Tim Ferriss, 28 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3004384/.

BibTeX
@misc{ferriss2026_3004384,
  author       = {Tim Ferriss},
  title        = {I Asked AI What to Do With the Next 5 Years of My Life},
  howpublished = {Interview transcript, Tim Ferriss. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/3004384/},
  note         = {Speaker-attributed transcript with timestamps}
}