Lenny's Podcast: Product | Career | Growth
00:48:32 · Lenny Rachitsky, Keith Rabois
[00:48:32] S1: Tweets, basically. [00:48:33] S0: ... picking, editing, reprompting. It's a little bit like when I used to be a litigator 25 plus years ago, the hardest part of writing a brief or all the art and all the magic was the first paragraph. If I could write that first paragraph really well, the chance I would win the case and convince the judge would go through the roof. So what I would actually do is I might have three weeks to write a brief. I might spend the first week or more walking around the office, thinking through, "How am I going to nail the first three sentences?" Once I figured out how I wanted to frame those first three sentences, I could write 30 pages in two days, but getting that right could take a week or two. Sometimes it would occur to me in the shower or literally the shower or in the middle of a run. It's like, "Oh my God, here's how I distill it." Then I could just sit down and power through the rest of the brief. And I think it's a little bit like that. The powering through the rest of the brief works well, you still need the first three sentences. [00:49:36] S1: Is there a story from that time in your life that would be interesting to share? I didn't even know about that.
00:49:36 · Lenny Rachitsky, Keith Rabois
[00:49:36] S1: Is there a story from that time in your life that would be interesting to share? I didn't even know about that. [00:49:40] S0: So yeah, not everybody knows. I spent the first four and a half years of my professional career as a law clerk and then litigator, which occasionally comes in handy truthfully. Sometimes trading off business risk against legal risk is a valuable thing to do. Sometimes it's not accidental that many of my best investments are in financial services in heavily regulated areas because I think I can sort of do the legal risk assessment in my own brain. This was definitely true back in the day when I invested in YouTube. But I think most things that lawyers learn are very inconsistent with being entrepreneur. So when you're graded as a lawyer, you learn every exam in law school virtually is issue spotting. So you get credit for identify ... There's fact patterns and identify all the issues and then resolve them. So you learn to identify everything that can go wrong, moderately useful, but very not useful as an entrepreneur. I mean, sure, you can identify all the reasons a company could fail, not that difficult to do. The art is solving those. So not the best training. And then you also measure your productivity by hours worked. Literally, you bill per hour. It took me two years, maybe a year and a half after converting to technology to stop tracking all my time. I used to literally write down in my notebook, "Oh, half hour of this meeting, 20 minutes on this, blah, blah, blah." I just couldn't get that out of my brain.
00:49:40 · Keith Rabois, Lenny Rachitsky
[00:49:40] S0: So yeah, not everybody knows. I spent the first four and a half years of my professional career as a law clerk and then litigator, which occasionally comes in handy truthfully. Sometimes trading off business risk against legal risk is a valuable thing to do. Sometimes it's not accidental that many of my best investments are in financial services in heavily regulated areas because I think I can sort of do the legal risk assessment in my own brain. This was definitely true back in the day when I invested in YouTube. But I think most things that lawyers learn are very inconsistent with being entrepreneur. So when you're graded as a lawyer, you learn every exam in law school virtually is issue spotting. So you get credit for identify ... There's fact patterns and identify all the issues and then resolve them. So you learn to identify everything that can go wrong, moderately useful, but very not useful as an entrepreneur. I mean, sure, you can identify all the reasons a company could fail, not that difficult to do. The art is solving those. So not the best training. And then you also measure your productivity by hours worked. Literally, you bill per hour. It took me two years, maybe a year and a half after converting to technology to stop tracking all my time. I used to literally write down in my notebook, "Oh, half hour of this meeting, 20 minutes on this, blah, blah, blah." I just couldn't get that out of my brain. [00:51:08] S1: That is so funny. And David Sacks was a lawyer too. It's interesting. [00:51:11] S0: That's true. Peter was a lawyer.
00:51:11 · Keith Rabois, Lenny Rachitsky
[00:51:11] S0: That's true. Peter was a lawyer. [00:51:12] S1: Peter too. [00:51:14] S0: Peter was smart enough to quit after five months and four days, I think. David never practiced so maybe even smarter than both of us. [00:51:23] S1: Okay. I'm going to hit on some hot takes, contrarian takes that you have. You have a number of these. I heard you share on a podcast recently. They asked you, "Why don't you have as many contrarian takes these days?" And you're like, "Well, they've just all been proven right." [00:51:35] S0: And that's the problem is if you have good ideas, eventually you want them to be adopted. It's a little bit like when you're an investor, you want to be contrarian. So Airbnb, you start with a contrarian take, but eventually if the company's going to succeed, it has to become consensus. Everybody in the world has to use it and believe in it and trust it. So you want that inflection. You don't want to just have contrarian takes and then nobody believe it. So you do need a refresh rate. And then the question is, how do you find new ideas? But you want to actually exhaust them. [00:52:06] S1: Okay. So one that I think people still just would disagree with is that your advice is for, unless you're building an enterprise company, you don't actually want to be talking to customers.
00:52:06 · Lenny Rachitsky, Keith Rabois
[00:52:06] S1: Okay. So one that I think people still just would disagree with is that your advice is for, unless you're building an enterprise company, you don't actually want to be talking to customers. [00:52:17] S0: Yeah, I hate talking to customers. I refuse to allow colleagues about and talk to customers. You can talk with the famous stuff and the Steve Jobs, the horses and the faster horses and all this stuff. But I think it's more important is it's often directionally wrong. Customers don't know what they want and they're very bad because it's a subconscious decision, especially for consumers. What I purchase, what I wear is not a conscious decision. And when you're consciously trying to answer a subconscious decision, you actually give misleading information even when you're trying. The proverbial example I like to use, but it's instructive is ask anybody who drives a super fancy car like a Porsche or a Lamborghini, why they bought the car. 99% of the time they will tell you every reason except the real reason. Once you realize that, you're like, "I'm never asking customers anything." Now, a hardcore enterprise, customer development does work because there is a decision maker. And the decision maker is mostly making utilitarian decision. And yes, there's political forces within the organization and you may or may not be able to tap into those, but fundamentally, extracting that information is valuable, but a consumer, SMB, micro-emergent product, unmitigated disaster.
00:52:17 · Keith Rabois, Lenny Rachitsky
[00:52:17] S0: Yeah, I hate talking to customers. I refuse to allow colleagues about and talk to customers. You can talk with the famous stuff and the Steve Jobs, the horses and the faster horses and all this stuff. But I think it's more important is it's often directionally wrong. Customers don't know what they want and they're very bad because it's a subconscious decision, especially for consumers. What I purchase, what I wear is not a conscious decision. And when you're consciously trying to answer a subconscious decision, you actually give misleading information even when you're trying. The proverbial example I like to use, but it's instructive is ask anybody who drives a super fancy car like a Porsche or a Lamborghini, why they bought the car. 99% of the time they will tell you every reason except the real reason. Once you realize that, you're like, "I'm never asking customers anything." Now, a hardcore enterprise, customer development does work because there is a decision maker. And the decision maker is mostly making utilitarian decision. And yes, there's political forces within the organization and you may or may not be able to tap into those, but fundamentally, extracting that information is valuable, but a consumer, SMB, micro-emergent product, unmitigated disaster. [00:53:36] S1: And so the implication here is you need to rely on your instincts and gut and experience.