Lenny's Podcast: Product | Career | Growth
00:55:47 · Tara Seshan
At OpenAI, I think I still write as thinking all the time. But the shareable artifact here is not really a long doc or a proof of work in that way, partially because times have changed and a long doc is not a signal that you thought through something. Because you could easily produce a long doc that indicates that you haven't. Maybe one of the biggest changes I've experienced personally in my day-to-day, which has been a big, maybe jarring change, is I used to think in a document and then do some translation of that into a presentational artifact, and that would be my indication that I thought through a problem and this is what we're going to do and the team moves in that direction. And now I am way more on mocks not docs, or prototypes not docs. And if I have something that people can try and interact with, or even better, I have results where we tried this, we ran an AB, here's the results, this is why I think we should go in this direction, that is a way better communication tool than the doc itself. And so I still write hundreds of docs all the time, but I do it for me and I no longer do it for other people really. That no longer is the best way to talk and communicate. That is probably the biggest change I've experienced personally in this era versus the previous era.
00:57:12 · Lenny Rachitsky, Tara Seshan
[00:57:12] S1: It is so interesting. I really liked your tip of getting tons of feedback on a doc. It sounds obvious, but you can get to an iconic doc/brief by just cheating almost and getting lots of feedback on it as you're iterating it to make it stronger and stronger stronger versus, cool, here it is first time and it's rarely going to be amazing. [00:57:29] S0: I previously had a manager who told me that the right thing to always do is write a doc to 70% completion and then take it to the people that you need buy-in from and get it from 70% to 100%. And that still is a thing that I do all the time. Because very few great people want to interact with a perfectly polished finished idea. A perfectly polished idea, their new ideas just bounce off of it versus something that has more crags and more rough edges that they too can polish with you together. And I think that bringing people into the process that way where a doc is an underlying artifact for that is one of the best ways to collaborate that I found. [00:58:08] S1: How do you think about AI brain rot and starting to over rely on AI that's just a challenge everybody's going to have? Why not use this magic to help look at something and then we start to lose our ability to write, read long documents? Is there anything you do that you are trying to avoid that?
00:58:08 · Lenny Rachitsky, Tara Seshan
[00:58:08] S1: How do you think about AI brain rot and starting to over rely on AI that's just a challenge everybody's going to have? Why not use this magic to help look at something and then we start to lose our ability to write, read long documents? Is there anything you do that you are trying to avoid that? [00:58:28] S0: Yeah, I think this writing as thinking discipline is one of the main pieces that I employ in my day-to-day to make sure I'm not overly atrophying my thinking abilities. I think I will, again, outsource all writing as reporting as much as possible to the model. But writing as thinking I have to do myself. I have this personal belief that, if I'm going to make someone read my document, I have to at least write it first that number of times. Or I think about this in meetings too, that if I'm going to call a meeting with a set of people, I need to have prepped the collective amount of time that people are going to spend in that meeting before the meeting. And so when it comes to keeping my thinking sharp, I do that writing for the document myself first and make sure I've invested the collective amount of time I expect people to read it at least in writing it and producing it. And I don't really rely on the model either for polishing my prose, which I don't think it really does, or especially not in generating the first version. But I do, of course, have the model help me a lot when it's summarization or translation of content from one format to the other all the time.
00:58:28 · Tara Seshan, Lenny Rachitsky
[00:58:28] S0: Yeah, I think this writing as thinking discipline is one of the main pieces that I employ in my day-to-day to make sure I'm not overly atrophying my thinking abilities. I think I will, again, outsource all writing as reporting as much as possible to the model. But writing as thinking I have to do myself. I have this personal belief that, if I'm going to make someone read my document, I have to at least write it first that number of times. Or I think about this in meetings too, that if I'm going to call a meeting with a set of people, I need to have prepped the collective amount of time that people are going to spend in that meeting before the meeting. And so when it comes to keeping my thinking sharp, I do that writing for the document myself first and make sure I've invested the collective amount of time I expect people to read it at least in writing it and producing it. And I don't really rely on the model either for polishing my prose, which I don't think it really does, or especially not in generating the first version. But I do, of course, have the model help me a lot when it's summarization or translation of content from one format to the other all the time. [00:59:42] S1: So what I'm hearing is write the idea, the brief, the plan yourself as a human, write it yourself, don't start with AI, and even don't use it to improve on the writing, just keep that all human. [00:59:56] S0: Yeah. At least for me, I start myself and I end myself. I might use AI in the middle to research specific elements or drop in some data or go pull some data or help me with-
00:59:56 · Tara Seshan, Lenny Rachitsky
[00:59:56] S0: Yeah. At least for me, I start myself and I end myself. I might use AI in the middle to research specific elements or drop in some data or go pull some data or help me with- [01:00:08] S1: Or push back on some ideas. [01:00:09] S0: Yeah, push back on some ideas. But start yourself and yourself with a piece of- [01:00:09] S1: Awesome. [01:00:13] S0: ... writing and that doesn't deteriorate your thinking. [01:00:16] S1: Okay. One last question. I want to ask about Sutter Hill. You had this very unusual career step. Your PMPM, founder person, and then just like, okay, EIR at Sutter Hill Ventures, which is a iconic VC. People can look it up. A lot of amazing companies came out of Sutter Hill. It has a very unique way of approaching founding where basically they incubate companies, Snowflake as an example. What was that about? What'd you learn from that experience?
01:00:45 · Tara Seshan
[01:00:45] S0: Sutter Hill is an iconic firm and is intentionally a very illegible firm. If you go to the Sutter Hill website, you will see nothing on the website. It is a firm that doesn't operate loudly. It tries to operate as under the radar as possible, as modestly as possible, yet is somehow responsible for some of the most iconic successes that Silicon Valley has seen. And they have this very unusual incubation model, which Mike Speiser, who is one of the amazing partners there, started and has rolled out success after success. I think the thing that was most iconic to me about Sutter Hill is that people look at finding product market fit as a dark art or building a tens of billion dollar company as a dark art, like, "Oh, it's luck. Oh, it's chance. Oh, it's all these things that must come together." Yet Mike Speiser has done it multiple times. And so there's clearly a way to do it. There's clearly a roadmap for making that possible. There is a set of things one can do to get this repeatably. It's not just luck. It's not just a dark art. There is a playbook, as it were, and that playbook lives inside of the firm Sutter Hill. And they have figured out how to be right a lot in terms of calling shots and making bets. And they've learned how to be right a lot in terms of the daily compounding things that one does to create a successful company, whether that's how you set up your enterprise sales team, how you position your product, how you build the initial founding team. The recruiting at Sutter Hill is an unparalleled, excellent thing. They have a secret tool called Redical where they have a map of everyone that they've interacted with and the 10 best people that those people have interacted with that helps them be so, so effective at this. So I went to Sutter Hill because in some way my career has been about how do I try to find product market fit as many times as possible, whether that was as a founder or in starting new products at Stripe or in joining a startup like Watershed. And so Sutter Hill is the place where they've figured out how to find product market fit on B2B products, and I wanted to learn what I could from them.