Talking to a billionaire about how he uses ChatGPT artwork

Talking to a billionaire about how he uses ChatGPT

My First Million

July 16, 2025

Want Sam's playbook to turn ChatGPT into your executive coach? Get it here: https://clickhubspot.com/sfb Episode 726: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Dharmesh Shah ( https://x.com/dharmesh ) about how he’s using ChatGPT.
Speakers: Sam Parr, Dharmesh Shah
**Sam Parr** (0:00)
So that's my advice, is every day, every day, you should be in ChatGPT. I don't care what your job is, right? You could be a sommelier at a restaurant, and you should be using ChatGPT every day to make yourself better at whatever it is you do.
Can I ask you about the story really quick? And you have a list of stuff here that's all amazing. It's actually, a lot of it's very actionable. But the reason I want to ask you about the story is for the listener. Dharmesh founded HubSpot, $30 billion company. You're the CTO, and you're an OG for Web 1.0, Web 2.0. And your first round, or one of your first rounds, was funded by Sequoia. Your partner, Brian, is an investor at Sequoia. So you are in the insider, you're an insider, I believe. You may not acknowledge it, I don't know if you do or do not. You are an insider. The cool part is that you're accessible to us. When did you first see what Sam was working on, and how long have you felt that this is going to change everything? So I actually have known Sam before I started OpenAI, and I got access to the GPT API. It was a toolkit for developers to be able to build AI applications effectively. And so I built this little chat application that used the API, and so I could have a conversation with it. So I actually built that thing that night, it was a Sunday. I had the full transcript two years before ChatGPT came out. So that's four years ago? It was 2020, so five years ago.

**Dharmesh Shah** (1:29)
Wow, okay.

**Sam Parr** (1:30)
This summer. And so even then, it's like, and as soon as you have that moment, it's the same that all of us have with ChatGPT. I just had it two years earlier, and then I'm showing everyone, like, Brian, you are not going to believe, like, I have this thing, you know, through this company called OpenAI, and watch me, like, type stuff into it and see, like, see what happens. And we would ask it, like, strategic questions about HubSpot. It's like, how should it, like, who are the top competitors? And they were, even then, two years before Chat, it was shockingly good, right? But the thing you sort of have to understand, but the constraints of how a large language model actually works is that you type and you have a limited, just imagine this, if we're going to just use the physical analog, their sheet of paper can only fit a certain number of words on it. And that certain number of words includes both what you write on it, this is, I want you to do this, and the response has to fit on that sheet of paper. And that sheet of paper is what, in technical terms, will be called a context window. And you'll hear this tossed around, it's like, oh, this, you know, ChatGPT has a context window of whatever, or this model has a context window, whatever. That's what they're talking about. All right, so why is that, why does anybody care about the context window? It's like, well, sometimes you want to provide a large piece of text, let's say, summarizes for me. Well, in order for you to do that, it has to fit in the context window. So if you want to take two books worth of information and say, yeah, I want to summarize this in 50 words, those two books worth of information have to fit inside the context window in order for the L and the process. Most, the frontier models are roughly 100,000 to 200,000. They measured in tokens, which is like 0.75 of a word, but that's so weird. That's like a book. So yeah, is that a book?
I think the average book is like 240,000 words, I think, but I'm not sure. That's not a lot. So the way that I use ChatGPT is I'll, like let's say a fun ways, I'll put a historical book that I loved reading and I'll be like, summarize this so I remember the details. So you're telling me that if it's a thousand page book, it's not even going to accurately summarize that book? It won't fit. You're like, if you paste something large enough into ChatGPT or whatever AI application you're using, it will come back and say, sorry, that doesn't fit. Effectively, what they're saying is that does not fit in the context window. So you're going to have to do something different. All right. A few episodes ago, I talked about something and I got thousands of messages asking me to go deeper and to explain. And that's what I'm about to do. So I told you guys how I use ChatGPT as a life coach or a thought partner. And what I did was I uploaded all types of amazing information. So I uploaded my personal finances, my net worth, my goals, different books that I like, issues going on in my personal life and businesses. I uploaded so much information. And so the output is that I have this GPT that I can ask questions that I'm having issues with in my life. Like how should I respond to this email? What's the right decision? Knowing that you know my goals for the future, things like that. And so I worked with HubSpot to put together a step by step process showing the audience, showing you the software that I used to make this, the information that I had, ChatGPT asked me, all this stuff. So it's super easy for you to use. And like I said, I use this like 10 or 20 times a day. It's literally changed my life. And so if you want that, it's free. There's a link below. Just click it into your email and we will send you everything you need to know to set this up in just about 20 minutes. And I'll show you how I use it again, 10 to 20 times a day.

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