Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more

I sometimes wonder how someone like Gokul Rajaram can exist. He has an intense full-time job at DoorDash, where he leads a significant part of the product and business. He also served as a board member at the Trade Desk, Coinbase, and Pinterest, all public companies. He's also a prolific investor and is seemingly on the cap table of every successful startup that I come across. And at the same time, he's one of the most humble and nicest people you'll ever meet. If you look him up, you'll notice he always calls himself a startup helper. And I know that he makes a lot of time to mentor and help a lot of founders. We cover a lot of ground in our conversation, including picking where to work, how to do product development startups, structuring your product teams, hiring, and angel investing. I hope that you enjoy our chat. This episode is brought to you by Amplitude, the number one product analytics solution. Amplitude helps product teams, growth teams, marketing and data teams build winning products faster, and turn products into revenue. Amplitude has everything you need, including an integrated CDP, self-service analytics, and even an experimentation platform to help you better understand your users, drive conversions, and increase engagement, growth, and revenue. Amplitude is built for teams that want to learn as fast as they ship and ship as fast as they learn. Ditch your vanity metrics, trust your data, work smarter, and grow your business. With over 1700 customers like Atlassian, Instacart, and HBO, Amplitude is helping companies build better products. Try Amplitude for free. Visit amplitude.com to get started. This episode is brought to you by Flat File. Think of the last time you imported a spreadsheet. Did it work the first time? Chances are it did not. You probably got some weird error and had to try a bunch of things like removing the blank title rows above your column headers or Googling how to save with UTF-8 encoding. What even is UTF? Who cares? You're just trying to get your file where it needs to go so you can do your actual job. Your customers run into the same issues when it matters most. right after signing up for your product. Enter Flat File. Flat File is the data onboarding platform built to take the acute pain out of importing customer data into your product so they can see the magic that you promised them. Flat File is SOC Type 1 and 2 certified, GDPR compliant, and even HIPAA compliant, ensuring your customers, no matter where in the world they're located, are sharing their data securely and in compliance every step of the way. No more emailing files back and forth, No more help articles that just don't land. Just clean data on day one, when it matters most. Get started importing millions of rows of customer data in minutes at flatfile.com/lenny.

Gökçel, thank you so much for doing this. I know that you're an intensely busy human and I really appreciate you being here.

Thank you, Lenny. It's awesome to be here. Thanks for having me.

It's absolutely my pleasure. You're on the boards of Coinbase and Pinterest. You're a really big deal at DoorDash. You're an even bigger deal at Caviar. You worked at Square, at Facebook, at Google. Plus, you're an incredibly prolific investor. I'd probably put you in the top 1% of investors based on what I've seen. And so I'm just curious kind of just to set context, how did you get into tech and product originally? And then just like, what was your journey like to becoming this luminary of tech.

First of all, let's start using the word luminary. I think it's people like Elon and Mark Andreessen are luminaries. I think I've just been lucky to work at good companies and observe the creation and growth of these companies. I'll give you an interesting story. Crazy enough, I joined Google as a PM after I applied to Cisco. This was in 2003 and I wanted to be a hardcore networking product manager in the layer three, layer two of networking. I was like, Layer 7 software is for WIMPS. I'm going to go hardcore. Cisco had a, in 2001, 2002, right after the bust, the first dot-com bust, then Cisco actually rescinded my offer. They made me an offer, they rescinded it. And then basically that's how I ended up at Google as my second choice after Cisco. So literally you can see some of these decisions, you're just saved from yourself by extreme necessity. Otherwise I would have been in networking probably, maybe still at Cisco. But at Google I got put on something called Syndication, which is taking Google search results and ads and then syndicating it to other properties like AOL back in the day, Yahoo, et cetera. And I was working on that product. And at about 6:00 PM, we had offices then back then at Google, 2002-2003. People would go home and some people would stay back. I just walk around and a few doors from me, I basically found a group of engineers in an office and they were working on something. I was like, what are you working on? They said, well, Sergey Brin, the co-founder, had given them a project of essentially reversing what Google had done with search. You type in a phrase, instead of and then Google identifies the web pages that are most relevant to the set of keywords. So we have an index that matches keywords and web pages. So why don't we extract those keywords for any given web page and basically see if we can target ads based on that? So that seemed interesting. Google's AdWords product, which is search ads, had just started scaling up. And I was like, Hey, do you have any PMs working with you? They said, no, can I be your PM? They said, aren't you working on syndication? I said, yeah, but I can do this nights and weekends. So I basically became a part-time PM for them and helped them talk to to customers, even did presentations with them, and while my full-time job was this other thing. And essentially within three months, this thing grew big enough and fast enough and became a product that my boss saw this and she moved me over to full-time work on this. And that became Google AdSense. So a lesson for me I've realized is that it's very important to do your core job really well at any company, but it's equally important to have curiosity and be open to serendipity. I think Zoom makes it harder, but it's very important to understand what else is going on at the company, what else people are working on, and just keep talking to people and build relationships with the company. Because those are what will lead to the next set of opportunities. I think many opportunities don't come linearly. Just working in your job and making sure you get promoted. That's not how I think great careers are built. I think great careers are built by knowing a lot of people, doing great work so they know and want you on their teams. and just waiting for serendipity and then seizing it and jumping. Another example is I had advised a company which was acquired by Square and the founders worked with Google and Jack, the CEO of Square, asked the founder who's one of the best product people he knows. My name was mentioned. So then they reached out to me and I would never have really, I mean, informal advising, I didn't have any equity or something in the company. I just helped them out because it was a former colleague and I said, sure, I'll help you out. And then that resulted in him saying good things about me and that led to the inbound from Square. So I think you've got to prioritize this stuff. I mean, you've got to be careful. It doesn't take up your life, but I think it's very important to be curious and open to serendipity. That's, I realize in today's world, there are lots of crazy serendipity things that happen. If you take inbound some smart people and you just chat with them and you help them out, paying it forward is the other thing. Paying it forward. And Lenny, you're a great example of this. You paid forward so much your, your articles, stuff you write. Good things happen in ways that you don't even realize.

You built up a reservoir of goodwill.

That comes back to help you in different ways.

I love this advice. I don't know if you know this already, but I actually did a TEDx talk once about Serendipity. It's called Losing youg Serendipity. It's out there on the internet in case people want to check it out. Wow. A long time ago. But I love, love, love that concept and it's such a good story. Just kind of pulling that thread a little bit. I'm curious, when you're looking for opportunities, would you suggest people focus on things they're excited about and kind of like passion that's pulling them in or more? I just think this is a big opportunity and maybe I'm not so excited about doing the work, but I'm just going to follow it because It may lead to some or some right in the middle. How do you think about that?

I think it's, you've got to think about the day to day. In many cases, I feel people don't realize whether they're passionate about something or not till they actually start doing the work. I could never imagine that I could be passionate about payments ever in a million years. But the environment of the company Square was so infectious and great and the culture was so good that we even made working on payments and you're serving these small businesses. I always think of not what you're working on, but what problem you're solving. In many cases, I get more energy from the problem I'm solving and who I'm solving it for. And I realize that I get much more energy from personally solving problems that affect either a small business or long tail, basically people or small business that I can relate to. It is harder for me to get energy solving problems of big enterprises and companies. So I've always somehow ended up working at companies like DoorDash or Square or even Facebook, building ad product for small businesses, Google AdSense for small publishers. And so consumers of small businesses, is what I've seen. And so I think it's important to know what kind of problems you get energy from and really think about the problem versus the customer segment, maybe even. So maybe even more than the problem because I've solved different kinds of problems, but I realized that it's those kinds of customers I enjoy because you can meet them in the day to day. You can see them on the street or you read their articles, a small blogger. For example, I remember I used to go to a lot of blog conferences when I was a PM for AdSense. It was great to meet these bloggers. There would be hundreds of thousands of them back then. I mean, it's probably different. different medium and so on now Substack. But back then it was blogger. I think the word doesn't even exist today, but it's amazing to meet them. And they literally till today, I have people emailing me, local, I know you're at, we used to make $100,000 a year based on purely ads from AdSense. And that was our living. And that's how we built this other company on that. So big companies, you don't ever get to hear something like that. So I got energy from things like that. The other one is founder. I think Lenny is very important. If you're talking about company, is to have a founder, when you talk to them, you don't get the sense that they're in it for the money. I think it's very important for founders to really live and breathe the mission themselves in an authentic way. And if people are smart, and I think you've got to really honestly think, if this person is constantly talking about revenue and trying to convince you that you're going to get wealthy or they're going to get whatever the case is, that's not the kind of founder that's going to build a really large company. And so if you look at everyone, whether it's, you worked with Brian Chesky, I'm sure he embodies that, Jack at Square, Tony at DoorDash, Larry at Google, all of these folks. embody that mission, market Facebook, that they care about winning. They will win and money will come, but it's a side product. It's not the main thing they're aiming for.

That's a good segue to a question I wanted to talk about is when someone's looking for a company to join, knowing that you've worked at a lot of really successful companies, what else should people look for when they're trying to decide where to go? So we've talked about so far is a founder that really wants to win and is really driven and then a problem that you want to solve. Is there anything else?

I think those are the two things. One thing to look at, I would say is that it is important to see if this company can become the number one player in its segment. I'll give you an example. I convinced someone who was going to take a very senior role, let's just say a tier two or tier three e-commerce company, to become a not so basically take one step down at different company, which is at Coinbase basically. I said on the board of Coinbase. And I think that person still thanks me because I think they were focused too much in the title that they were going to be the super senior percent, this company on the management team, et cetera. But I said, ultimately you don't realize this, but the value I would much rather be the number two or number three person, if you think of it that way, at the leader in a space than the top person. It's like Google versus Yahoo. I saw even if you're the VP of product at Yahoo or the head of product at Yahoo versus a ICPM at Google, you'd probably want to be the ICPM at Google, I bet you all day long. all day long. Yahoo was a great company, but Google was just a different caliber and different class. So I think it's very important to try to work it. Obviously you don't know who the winner is, but if you think that there's something is a winner in a space, in a large in a space, there's so many benefits that accrue from working at winners. You get unfair brand halo because you worked at a winner. People attribute a lot of the, oh yeah, you worked at a winner, hence you must be a winner.

Probably not the case, but you can, I'll take it. So along those lines and kind of touching on your investor experience, what should folks look for it to think about, is this going to be a winner or should they maybe join when it's like a series B, series C, when it's kind of clear that it's doing well? Do you have any thoughts? Maybe like for either like a new person joining the workforce, maybe PM, let's.

Say, or even later. Personally, I feel like Hunter Walk wrote a very good post on it. He said that people who are joining the workforce new should generally join mid-stage companies because mid-stage companies, you get some mentorship and it's not just basically whatever needs to be done and ultimately you don't build any deep skills. so mid-stage company I would define as something that is a multi hundred person company, but not maybe a thousand person company, somewhere from 300 to 500 people that has not just reached product market fit, but product market channel fit. And the first product ideally is the current product is on the way to becoming almost bulletproof. It's going to be a very, very strong product. And then it's really a path to becoming a platform beyond a product where the company is thinking about how do I become a platform? they have multiple products that serve the same customer, different problems, and they all complement and interlock with each other. So because looking back in a career, I've always without any thinking about it, I was employee number 6, 7 or 800 at Google, employee number few hundreds at Facebook, employee number 7, 800 at Square. DoorDash, I was slightly later because it was through an acquisition. So it was like, I think, 1,500 or something like all around. But DoorDash also, I think, yeah, But I think that's basically, at least for me, has worked. And this is even when I was not a newbie as I was in my career. So it's really a good spot, I feel, if you're joining a company for many reasons.

And this advice is for, you're saying new people, but also maybe people kind of further along in their career.

I think unless you know the founders very, very, very well, joining a very early stage, early stage company is, especially now for the next one or two years, it's going to be a brutal market out there. So you've got to be really careful. There's going to be the days of raising a round, a few weeks after raising a prior round of a couple of months without much movement, which has much company progress are probably gone for most companies. And we all have seen now companies that have raised rounds at crazy valuations, deflate or die quickly. And so that's happened very quickly. You might just join and your company could die a week from now. So I think the other one is to really look at the financials and really understand that better.

Awesome. That's really helpful advice. You mentioned Brian Armstrong, Brian Chesky, and some of the other folks that you have worked with and gotten to know. I'm curious of the companies you've worked at, say now Coinbase on the board, Google, Facebook, Square, DoorDash. What are some things that have kind of stuck with you? Things you've taken away about maybe how to run a company, build a product, or anything else that's kind of just.

Taught you a lesson about how to, how to do what you're doing. One of the most interesting things I realized is there are multiple paths to greatness. What I mean by that is if I were to look at one word to describe each of the companies have actually worked at, Google would be technical. It is very, very technical, technology focused, because Google believed if you build great technology, they will come. Facebook was very growth focused, very much here's a goal, we want to hit 1 billion MAUs. Let's work backwards from there. Square was very design focused. Let's build the Cleanest, minimalistic design, the most well designed product, think good things happen. DoorDash by nature is more operational, probably the right word to use where product and operational intertwined. Uber probably is the same word. So I think there are multiple paths to greatness, but I think the founder and market fit in terms of even the type of company that's needed is very strong. In other words, I think founders have to be authentic to themselves. The other thing I saw is that each founder, whether it's Tony Hsieh at DoorDash or Jack, they all had the distinctive styles, but they didn't try to change their style. In some ways, the company was built almost in their image in some ways, and that was fine. I think if you try to build a company that's inauthentic to who you are as a founder, that's not going to work. So ultimately you want to, if Jack had tried to build a company that sold enterprise software, I don't think that would have worked. That's not who he is. And so you want a founder and a company culture that are essentially synonymous and founders to be authentic. And I think finally the one other thing that I've seen is the product itself ideally needs to have some remarkability. What I mean by that is it needs to be better than anything else that solves that pain point along a few dimensions that really matter, even if it's worse along other dimensions. So I think every great product it needs to have a lot of word of mouth. I think especially nowadays, I'm seeing a lot of consumer companies challenged because they relied on Facebook or paid media to drive customer acquisition. And a bunch of companies are coming to me saying, Google, what do we do now? I'm like, look, the biggest thing you did wrong initially was you didn't pay enough attention to organic growth. Basically, was this product compelling enough that people talk about it and bring other people along? and you completely relied on paid and that's coming back to bite you. So a good metric is that 40 to 50% of your new customers should ideally come from organic channels and 50% from paid. If 90% come from paid, that is at some point that the music is going to stop.

Unless you've got some magical insight or someone that's just- Or a growth hack, right?

Everyone is looking at this growth hack, but there is nothing like the silver growth hack bullet.

It's interesting. There are a couple companies I'm an investor in that are actually still working really well through paid. And so it's definitely possible, but incredibly hard.

Yeah, those are exceptions that prove the rule.

What I think of when you talk about this is something Seth Godin shared a while ago that I always come back to, this idea that your product has to be remarkable or people want to remark on it for it to have a chance, especially in consumer, because that's how things start to grow. People just can't help but talk about it.

Exactly. Very well said.

Easier said than done. Okay, so getting a little tactical, I'm curious to get your take on just the product development process at companies? How do you think about founders setting up a product development process? What do you recommend usually? And then maybe further down the line when they get to like 25 people, maybe 50 people, how do you advise founders? Think about their product development process in the early stages and then as they evolve?

I think first of all, the planning period is different at the very early stage. At the very early stage, it needs to be a weekly plan where while as you grow the granularity, you still need weekly plans, but you also need quarterly plans that wrap around that. You start with quarterly goals. In fact, I was talking to a series A company and they were just starting their first ever quarterly plan. They just did a series A round. So they need to plan at a quarterly level and then it translates back into the weekly level. When you're very young, you're literally going week to week. And then once you become much bigger, you get to annual planning, which then leads to quarterly goals and so on. so the granularity is different. The second thing is the tools you actually use. I think initially you just have a very simple spreadsheet. I am a big believer that you can have all these fancy project management tools. Whenever I've been a leader in a product team, I've never imposed a certain tool because I feel different PMs and teams find the right tool for them. It's about keeping it super simple. If you have too many complex tools, people don't know how to use them. engineering teams typically use something like Jira. And as a product person, you don't want another complex tool for them to use to figure out things. So a simple spreadsheet and you're a founder that you update the things to do and people who are going to do it. And then that's basically it. I think as you grow, you start wanting to write a little bit more stuff. I think the first thing you start doing, and then as a very young company, you don't have a separate product strategy from a company strategy. The product and company strategy are the same. as you start growing, you have a go-to-market strategy, product strategy, etc. Etc. So you start more clearly separating out the company strategy from the product strategy. The first thing you start seeing is when a product manager joins. So I think, of course, what happens is that the 25 person status, you have a PM who sometimes joins the company. I think the right time for PMs to join the company is about eight to ten engineers or so, anywhere between five and ten. but 10 engineers is unless the founder themselves wants to be the PM. But that's when you start seeing a professional PM join. And the PM typically wants to clearly articulate, good PMs want to articulate what the product strategy is based on company strategy. So you start seeing the emergence of a separate product strategy doc that is written at the 2025 person stage. And the product strategy then makes choices. What customers are we serving? More clearly articulates what have been implicit, hopefully earlier. and then that guides product development. And then I think when you get really large, you have essentially multiple interlocking products that there are multiple product strategy docs and then you get into more cross-functional strategy docs, into product strategy docs, et cetera. But I think at the very core of it, there are two things. One, the team still needs to meet on a daily basis. There is a standup cadence and that atomic team of six, seven people which is engineers, product person, designer, hopefully an analyst. They are the product development team and they still review their tasks on a weekly basis. But where it emanates from, when you're young, it doesn't have any roots. It's literally they're just living and dying on a week by week basis, trying different things till they get product market fit. As you grow bigger and you have product market fit, you start building plans around that. And these iterations, these sprints, then emanate working back from the goals that you set on a quarterly basis.

Wow, so much good advice. There's a couple of things I want to follow up on there. What are some common pitfalls you've seen in startups trying to set up product development processes or the way they build product? What do you find are kind of some of the more common mistakes that founders make, that early teams make?

The biggest one I think is the founder becomes too tactical and disempowers their team. I think the founder thinks they know what customers want. I think they don't empower their teams enough and they basically just tell the engineers what to build. And I think that leads to teams that are basically tactically just shipping feature after feature without truly solving problems. And I think that then creeps into when you hire a PM, they see this is how the company is working and they then also start working the same way. I think the best founders early on trust their engineering teams and product development teams to solve problems and more clearly present the problem to them and help them. And this is true for PMs also. They help them brainstorm solutions and try to work with the team to understand why we chose a certain solution versus another solution. And then the team feels empowered to go build it versus dictating them, which should be an iOS app. While the actual problem to solve is we want to increase the percentage of people using our service. to five times a week versus two times a week and building an iOS app is one tactic, but there are many other tactics which is improving our web experience, et cetera. So decision making and transparency of decisions around how products change customer behavior is probably the, and that leads to the culture of what is called a feature factory where product teams basically are very proud of shipping feature after feature without truly knowing how much impact the feature has. If a feature is shipped, but it doesn't change customer behavior at all, is it really a feature? Or no, it's like a tree falling in the forest.

Oh my God, I love that. And I've definitely seen these teams that you're talking about, and that only becomes worse once they hire a PM. I like your rule of thumb of hiring a PM when you've gotten like 8 to 10 engineers. What it kind of points to, it's time to hire a PM. Other than that, is there other things you've seen of just like, oh my God, this team really needs a PM? Or, They should wait longer. What have you seen there?

I always feel that you should hire to solve a problem you're facing. You should never hire or you feel you're going to face. But especially I think just over hiring, especially you want to be efficient and you smaller teams are always good, smaller companies are always good, but in the problems. So there are many teams. First of all, the question is if the founder is able to play the role, someone needs to play the role of a product manager. If the founder is able to and willing to play the role of product manager, the problem is with eight to 10 engineers, if the founder is doing other things besides being the role of a product manager, then the eight to 10% engineering team is not being cared for and fed. Engineers are by far the most expensive resource of the company by far, right? I mean, if you look at the composition of engineers versus and PMs versus any of the function, it's two to three equity, cash, everything. And if you think of it that way, then if you're not caring and feeding and not leveraging this amazing, most expensive resource well, that's a crime. That's a crime. And so in some ways you've got to think about yourself. Am I, as a founder, is this 10 person team or eight person team being leveraged? Are they solving the right problems? Do they know how to brainstorm? Do they know how to solve problems? Do I have the bandwidth to sit with them and present the right problems, talk to customers, figure out the right sequencing, the right prioritization of problems to work on, etc. and if you're not able to do that, you've got to have someone who can do that full time. And it might be someone from the team. I mean, there are two, we can talk about how to hire your first PM and there are many, many different-.

Yeah, let's do it. I definitely wanted to ask that. I know you wrote a great post about this, just how to actually hire your great PM and you have a.

Strong opinion about that. So- yeah, I have a strong opinion and it might be just based on every single company I've been at. The first PM at every company has been someone who's either been an analyst or an engineer or a designer who's worked there already, and they just moved from their role to being a PM. Why? Because many cases, the role of the PM is actually to be the liaison between the founders and the engineering team. And so it needs to be someone that the founders trust and the engineering team trusts. And also they know how the founders and engineering team work. And many times, if you bring a PM from the outside with a completely different process, many times the organ can be rejected by the body. And so they may not be the best PM you could get in terms of just functional skills, but they're going to be the best PM from a cultural assimilation and getting the engineers to just understand the value of a PM and getting the founders to be comfortable, slowly being more hands off. Was it true of Airbnb also? Lenny was Joe bot the first PM?

He was, and he was actually an engineer when he joined. So it's exactly how you describe.

Yeah.

So say that you hire or you transition someone from PM into there being the first PM. What are some signs that maybe they're not doing too well and things aren't going well? Maybe you should go in a different direction.

I think the biggest one is I always feel with PMs, it's actually two or three things you can look at. One is you can actually just ask the engineers themselves. Engineers are fairly blunt and when I manage PMs, I've seen that they always tell me engineering managers in particular, they are very, very quick to tell you, look, this person is not working, they're not being effective. What value are they adding? And I think just number one thing you have to do is you have to just because you hired a PM, you can't abdicate that responsibility of understanding how the team is doing. It's not gone. You've got to talk to the engineers and designers constantly to see is the product manager adding value. Second, if you see the PM, the newly anointed PM, still get too much into the how to build the product, which is really the domain of the engineers and designers. See, that's the other failure case where you've got to, and this is something through coaching comes. Obviously, they just were an engineer or designer two weeks ago, and now they're a PM. There's an immediate impulse to start going back into their comfort zone. And the key is to really push them to go more strongly biased towards customers and push them more towards talking to customers, understanding customer problems. And I think every PM, we all know this, all of us as PMs, there was no class to be a PM. So there are some people who joined APM programs directly out of school, but most of us are engineers, marketers, analysts, designers, and we became PMs after that. So we all come with inherent biases and ways of doing things. and it's only a function of how long it takes us to shed, or at least to not be that persona, but to actually take on a PM persona. And so I personally believe in the growth mindset a lot. The reason that hopefully this person was chosen to be the PM is A, the founder saw that this person has the characteristics traits, which is curiosity, customer centricity, communication skills, being able to facilitate discussion, all of those things that a PM should have, problem solving skills. And so hopefully those are things they didn't just pick a random engineer out of the 10, but they picked the right engineer, the right designer. And I think if you do that and you surround them with some good mentors, I think in six months they'll make good PMs.

I love that. Maybe just try randomly. You never know.

Good work.

Just to close the loop on the idea of when it's time to hire a PM, somebody may be listening to this and feeling like, oh shit, we gotta get a PM in ASAP. what are some signs or reasons to wait a little bit longer before you hire your first PM?

If everything is going well, in other words, if your product team is clicking, if they're empowered, and if you feel that they can take problems that you're giving them, not just tactics, but they're able to take a problem, hey, we need to improve new user acquisition. And the product team, whatever you do, product development team, which is just engineers, able to take that and essentially act on it, and suggest three different ways to improve user acquisition. For example, choose the one that has the best ROI, how you measure it, and then execute on that, and then run a test to say, look, it did improve user acquisition. That's a well-proven product team. So I think you need an empowered product team that takes ownership and can take a problem, figure out all the opportunities to solve the problem, and then prioritize them. And so if you feel that's happening, you don't need a PM. but I've seen that it's hard as engineering teams grow to engineers. I think they do need that partner. They do need that partner to help facilitate that for the most part.

That's awesome. And yeah, I think that's gonna be.

I think infrastructure is a great example. I think stripe, for example, is famous for not hiring PMs because I think when you audiences developers, they know their audience really well. And so I think many devops and developer facing companies, they don't have that many PMs. The PM to engineering ratio is very small. Even Stripe today, I bet it's much smaller than other companies. So those are exceptions where engineers truly understand the domain better. So really machine learning companies, infrastructure companies generally I think need fewer PMs. And this is true for any consumer product company also. I bet Airbnb's infrastructure team had zero PMs or very few PMs because they are serving other engineers. so I think those products, I think you need much fewer PMs than consumer-facing products.

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Have a whole table of how long companies waited before they got their first PM. I think Snapchat had like 200 people also, but I think it's because their designers basically played the role of the product manager.

There we go.

That's right. The designers played the role of the product manager.

Yeah.

Somebody's got to be doing the job.

Hopefully they enjoy it. Sometimes they don't. That's right. Okay, so say you've hired your first PM, you're building a product team. Something I wanted to get your take on is SPM teams grow. Sometimes they end up changing who they're reporting to. Sometimes it ends up being a CPO, sometimes a GM, sometimes even a CTO in some cases. Do you have any thoughts on when it makes sense for product teams to report to, say, a GM versus a chief product officer or something else? Do you have any advice there?

Yeah, I've worked at companies where It's both functional, product orgs are functional where all the PMs report into the head of product who reports to the CEO, as well as a GM structure where PMs report into a GM as do an engineering leader and a design leader and even a sales leader, marketing leader, et cetera. So both can work. But ultimately you want, I do think once you have three to four PMs, you do want those three to four PMs to report to a functional product leader just because I feel they want a mentor. First of all, they want a coach and you want to build a product culture and hopefully discipline across those four or five PMs. Because the leverage you get, someone said this, I think a few years ago, I remember this. Engineers are obviously very important to hire, but a bad PM, you can get incredible leverage from a good PM, but a bad PM can really screw up your like can screw up the work of 10 engineers, right? So it's much more important to hire a good PM than it is to hire a good engineer. Any good one, because there's so few PMs, every engineer that one good or bad PM can really screw up everything relative to the impact of one good or bad engineer. So what that means for me is that if you have four or five PMs, then the one way to up level them is to actually make sure the four together are sharing best practices, learning, hopefully building a culture. And I think it's hard for a GM who's also managing other functions to do that. So I would say, yes, maybe one or two PMs could report into a CEO or a GM or someone else. But once you get into a four or 5 PM team, they probably should report to a dedicated of product managers whose job is to be a mentor, be a coach, attract strong new folks to the team hire, build a strong culture, et cetera, et cetera. So, and that product manager, I think they could report to the CTO, they could report to the CEO, they could report to GM, anything that matters. But the ICPMs is what I'm more worried about. Who do they report into? I think they should report into a dedicated manager once it gets to a certain size.

Awesome. I could not agree more. Another thing I've seen is a lot of companies go one direction, they go GM models, then they go back to something else where it's completely business unit oriented and functional reporting, and then they go back. So I found it just like try something, see if that works. You can always change it in the future. That's super common. I wanted to transition to hiring, talk about hiring. You recently had this incredible thread on Twitter about how to hire a leader, and I think maybe just a product leader, maybe broadly leader. And so for folks that haven't seen that or have time to go on Twitter, I'd love to just hear your advice on how to hire a leader for a company.

That post actually was triggered By that morning, one of my company's CEO messaged me that, Wow, I hired someone from this company. How did you know this company? How did you know this person was available at this company? I was like, I didn't know about this person. I just knew this company was really good at sales. And so that's why I recommended the company. And he said, this is the third time I've hired based on advice you gave. And these are all senior leaders here. How did you do that? I'm like, actually thinking about it, you're right. When companies ask me, because the number one, if you ever ask a company, what's the thing that's keeping you up at night? They'll always say, one of the things always is keeping them up at night. I want to hire a leader for XYZ function. And I never respond with, here's a person. I'll always say, well, you're in this space selling to this kind of customer or serving this kind of customer. Let's think about the best in class companies who's also, who's very good at functionally the thing you're hiring for, serving the similar type of customer. And so basically that was the origin of the post. And really what it says is in order to hire, if you want to have a playbook for hiring good leaders or strong leaders for any function, look at best of class companies or companies that are best of class at that function in a similar space, not your competitors, but you've got to look beyond your competitors. You've got to look at folks who are serving SMBs or enterprises or whatever this are consumers. and then say, okay, I want to hire, say, a head of marketing. Great. This is the hardest thing. Got to find the top three or four companies who are excellent at marketing to Consumers, if that's what you're. Then you don't hire the person, the head of marketing at these companies. You hire the person who's reporting to them, the lieutenant. And actually, Aaron Zamos, who was ahead of people at Square, chimed in to say at Square early days, we used to go. He used to run people, the people demon Square. We used to go. and hire the up and coming lieutenants off the lieutenants. And so I think you basically have to build an almost an org chart. And it's not that hard. You just have to spend some time on LinkedIn to say, who are all the people in the org who reports to? And you can ask some of your friends who work at the company to better construct the org chart. And you just literally go through that company and pick out the people. And I saw this in practice because once Square went public, we were the only public fintech in 2015, one of the very few public fintechs. And so my goodness, our teams were raided with the next two years. I literally saw the full team in like a huge chunk of a team in different parts of payments compliance risk just being rated by other fintechs. And I saw that this was being followed because you see, okay, who's the company who's best in being compliance? Square. And I'm sure there are other companies also, but Square was well known because it was public and it was large. They had done it at scale, etc. They didn't go after our head. They went after the lieutenant and the lieutenant of the lieutenant, et cetera.

I see. So you saw this happening to you and then you've weaponized it in reverse. I love it. Great advice. I've never heard this advice before and it sounds incredibly good. And so thank you for sharing all that. Thank you. On the front of hiring, how much time do you think founders and just, I guess, leaders should spend on hiring?

What percentage of their time have you seen the best founders and leaders spend? When obviously you've got to always be hiring, even today, I think Tony and Dordash, if you have good strong people, you'll always say, please make the intro if you have some amazing people because you never know what you learn from these people, even if you don't end up hiring them. So always want to meet great people. But I think in general, a founder of a young company should spend, I think, two hours a day hiring. And you should do it during the time. I think the challenge with hiring is you've got to build a process, first of all, and that takes a lot of heavy mental work, the right process for you to make sure you do reach outs. And again, there are two parts of hiring, right? There's a lot of reaching out to people, and then there's actually talking to people. So I would suggest spending one hour a day doing the reach outs. And there it should almost be busy work because you almost figure out the process. So you should do it during the time of day where you don't have to put a lot of mental, like, you don't need to be fresh because you need the fresh work for your actual company that you're running, but you need some time, fresh time to come up with the right process. How do you do the LinkedIn reach out or whatever tools you used to reach out to? Who are the types of profiles, what roles you want to prioritize? So you need to find the right R to do that. And the second R should be devoted to actually meeting one or two people on a daily basis. And that's two half an hour conversations. So I think if you just do that, you'll actually over even 30 days single, you'll meet with 60 people. And you'll do a 30 hours of LinkedIn. It's just two hours out of say 10 hours a day. And let's say 20 hours, 20 days, sorry, instead of 30 because of weekdays. That's still a lot of time. So I think two hours, use calendar. Calendar is your best friend there. Use calendar. And I think that's more than enough.

To do really well on recruiting. I'm guessing that you can see a pretty big difference between the founders that you work with that do this sort of process and put in the time and don't.

100%. I think putting in the process up front is really important because you can flounder around and then just spending a full four or five hours up front talking to a few folks coming with good process can massively improve the because they say, right? It's all about once you aim, you know, the strategy or the direction you're going is much more important than the speed you go in. If you go in the wrong direction, it doesn't matter how fast you go, you're screwed. But if you go in the right direction, even if you go slightly slower, you're going to get there. So I think it's very important to set the direction of hiring, how exactly are you going to hire, what the process is, what your messaging is going to be, and really make sure you nail that before you do stuff.

Once you've hired someone, you give them a title. I know you have some strong opinions about titles and how to think about titles at startups, and I'd love to hear your take on that.

Yeah, I think on titles. I personally feel that if you're young, you have a unique opportunity as a founder to set a culture in place where people care about scope and impact much more than they were titles. The titles I'm most opposed to, to be honest, I'm not opposed to titles. I think tweeted about this and people interpreted this, think no one should have any titles. Titles, people, you want someone to be called a software engineer so you know what they're doing. But the titles I'm most against are director and VP titles, director, senior director, because those are the titles that lead to the most contention in the company that lead to the most conflict, that lead to the most like disgruntlement and heartache and managers having to constantly and people basically staying on for the title to put it bluntly versus because their scope and impact isn't. So, but I'm also against giving titles too early in a company. For example, I think the general counsel is a good title. I think Wall Street cares about it. It's important to your general counsel, but I was meeting with a 25 person company today and the CEO told me, I was like, I always start with what doesn't, what keeps you up at night? And this company is in somewhat of a legal heavy space. He's like, I need to hire a general counsel. Instantly I said, listen, yes, I know you need to hire a lead lawyer, whatever you call them, a head of legal. But do not give the general counsel title at a 25 person company because the person at a 250 person company, hopefully you're going to be that in two, three years, it's going to be very different than the GC now. And you might, you still want to retain this person most likely because they're good. You just don't want to be the general counsel. See this over and over again. And so there are certain titles you only can give once. And if you give it too early, you can't then, that's the reason to avoid titles as long as possible. If you give the VP engineering title, at 25 people, how the heck are you ever going to have upgrade that person, upgrade that role? You have to basically let them go because you can't then say, this VP of engineering, now you're going to be made director of engineering or something, et cetera. It's very challenging.

When I look at your LinkedIn, it's always funny because I think you're just like startup helper or when you were running caviar, I think it was like someone at caviar or something very vague. If clearly you live that yourself, and.

I saw the impact of it. I saw at Square, I think was the company. And I think Jack came up with this because he saw that Twitter titles were weaponized in different ways. And so he started this at Square. And that's where I truly saw the impact. I never had a single discussion at Square with my team about what the title should be. And that was amazing. At other companies, as always, I want to be promoted director. I want to be promoted to senior director. It's always during promotion time. If you ask person what their goal is, even personal goals, sometimes they'll even write, I want to be promoted to director, but never had that. Had stuff, of course, around scope, impact, compensation. That's great. I want to have a conversation with that. But title, I don't know.

And just to summarize your advice, there is what's kind of the rule of thumb of titles if someone hasn't read that post.

Delay it as long as possible. and try to avoid granting director and VP level titles as long as possible in particular.

Easy. And then delay it, meaning we have- Very simple.

Direct and VP level titles.

And delaying titles meaning anything other than just like software engineer or product manager.

Software engineer lead. The word lead or head of are both good because the head of very clearly describes what they do or lead also very clearly describes what they do. So my title was Cappy or lead. and then the people who reported to me were caviar product lead, caviar engineering lead, caviar strategy and operations lead, caviar sales lead, et cetera. And so the more words there are in the title, the more focused their role is. In fact, you can look at Jack's new title, it's block head. So it's literally not senior anymore. It's head of block. A block lead, I would say, probably should be more appropriate. He's the leader block. and then so on it permeates down.

Amazing. That's incredibly valuable advice. And thank you for getting into the details there. I'd love to transition in to talk about investing a little bit before we get to our exciting lightning round. And so you spent a lot of your time angel investing, investing in a bunch of different ways. What's been your trajectory from just starting to angel invest early on to the scale you're at now?

I started angel investing in 2007, 15 years ago. And like many people, I started because my friends and colleagues were leaving to start companies. This is when I was at Google and they were leaving to start companies. So literally without doing much, I just wanted to support them because I'd worked with them. And so I just put a small check into the companies and some failed, some did really well. But ultimately I realized that for me, investing is all about supporting people much more so than companies themselves, the company itself. It's about the entrepreneur and the person. So till today, I think I have enjoyed the most and I've really come to believe in myself that I am a founder centric. I believe in the founder much more than I do the market. I think there are market centric investors. Sequoia is amazing and they are very much believe in a big market. I strongly believe that great founders and Airbnb is a great example. They either create new markets themselves or they pivot. I mean, if they realize that a certain market is not good, they'll figure out a way to move. And I'm basically with my check. The biggest mistakes I've made early on were after a few checks, I said, oh, I'm going to be much more selective. I'm not just going to write checks to all my friends. I'm going to look to see what the market they are in. So I basically just started making these assumptions, oh, well, you know, I should not invest in this company. And turns out almost all of them were sins of omission. I much, much more care about sense of omission. because you can only use 1x, lose 1x your money. But for me, the relationship with the person, a person I know and respect and I'm good friends with, and I'm not investing in them, I don't want to lose that. And it's an optionality for me to invest in not just this company, but in every other company they start. Because one of the most interesting patterns I see is folks who are unsuccessful the first time around, but then use those learnings to start a company. in a same or similar space and then succeed. And I'm seeing this more and more happen. And I want to have, if you don't invest in that first company, even though you thought they were great because the market was not great, they won't probably come back to you for the second company either. So very, very founder-centric style of investing, almost like YC, I would say, closer to YC than anything else, because I see investing just founders. At this point, they don't care about the idea. They just care that you're a builder and that you can pivot fast. And if you're a team of builders who can pivot fast, they will invest because they know within three weeks, if you don't have product market fit, they'll get you to pivot three times. And like how many times the next segment, you'll find your product market fit four times. See this again and again.

I love that advice and the way I think about it too. The only downside is if you have worked at an awesome company or two or three, it becomes a very expensive hobby because you end up knowing a lot of awesome people that are doing great things. so you have to be a little bit careful.

You've got to really make sure what your motivation is. That's what I really want to understand. Like you don't want folks, there are awesome people, but I do want to make sure they're doing it for the right reason. In other words, they're doing it to solve a problem that they've experienced themselves or seen. So I really try to get into why they're starting the company. And I want to make sure the reason for starting the company is authentic in that it's a problem that they have observed deeply versus it's something they read about in TechCrunch. or it's the newest web3 or crypto thing or NFT thing. So I think that's how I suss out. So I don't invest in people even if they're awesome, when I feel the idea for the reason they're starting a company is mercenary and they're doing it because they haven't immersed themselves in the space. Famously, I think the Collison brothers bought a book, I think on payments, very old book or something, I think, and paper maybe, and read it to fully understand. You want people who really immerse themselves in an industry. and live and breathe it before they tackle it.

Are there other things like that that you look for that are just like, oh, wow, I really need to invest in this?

The ability to hire talent before even you have our ability that if you can show me that you have this set of amazing people lined up to join you or that you have commitments or even your founders, I mean, the other thing I look for is definitely two-person founding team, at least two is the ideal I've seen. Solo founders, I'm very nervous about because I think no one person has all the skills needed to start a company. and it's also a lot of things to do. So I do like to see a really good mix of basically a builder and a seller or a hustler and a hacker, whatever you call them. And I think that two person, I really feel comfortable. However good the one person is, I just feel it's, they're obviously one person funding teams that have worked well, but I think the two or three person funding teams, I feel much two is the ideal number. So I look for the two person funding team, complementary these are really, really.

Handy rules of thumb that everybody could use. How do you find time to do this? So you have a full-time job, I imagine it's extremely demanding. And then you're also doing a lot of investing. For folks that are thinking about doing this on the side, how do you time box this and keep it sustainable.

Not just go, go, go. Time boxing is exactly what you said, Lenny. It's time boxing. Most of our time ironically is spent on DoorDash and not ironically, logically is spent on DoorDash, even though we're not a period. I spent it on DoorDash and what I do is a small percent of my time. I basically, I keep looking at my calendar to see am I spending more than, I've worked say 10 hours a day, am I spending more than two to three hours, maximum three, ideally two hours a day on things in order to do my work. And three hours actually is a lot. If you think about half an hour meetings with people, that's six meetings you can do a day out of 10. And I also do two hours each on both Saturday and Sunday. so that I can do four meetings each. So if you think about it, six times five is 30 or four times five is 20 plus another four plus four eight 28 meetings. That's a lot of meetings you can do with people, et cetera, et cetera. Yeah. So I think it's, it's really time boxing and knowing, I think it is knowing what matters because if you find yourself doing the opposite where 70% of time is investing, then you should actually.

Become a full-time investor. That's amazing. I don't know how you keep your brain capacity focused on so many things. Meeting with that many founders, even outside the time, is a lot of mental load.

I enjoy it. I think the thing is I enjoy it because I have been a founder myself, not a very successful one. So one of the things I love hearing, I always started, tell me your founding story. And every founder likes to tell the founding story. And that's where I listen closely for authenticity, to understand how they met each other, the two founders, hopefully multiple founders, how they knew each other and how they came up with this idea that they're going after versus and what problem they're tackling. And so, A, I have a standard set of questions they ask. So that way I can spend my time not thinking of questions to ask, but just listening and just learning. And then I also have a good ability to forget instantly. I take notes and then I just forget and go on to the next meeting. So compartmentalizing well.

Have you thought about publishing these questions that you ask or do you think that would hurt your these chats?

No, I think it seems, yeah, it seems too formulaic then. I think there's questions that then change based on what they answer. So it's not exactly a set of questions, but it always starts with, tell me about your founding story of the company. I introduced myself and then asked them for their founding story. They're all nervous, you know, pitching, Etc. When they pitch someone who could be an investor, we ask them to tell stories. It's the same for customer interviews, right? You never ask customers, tell me top three problems. That's no one knows what they are. But tell me the last time you used a food delivery service. Tell me the last time you used a payment service. Like how was it? Tell me the last time you took a payment, credit card payment. Tell me about your last customer. They love telling stories about themselves. Everyone likes talking about how they did something.

For somebody that's thinking about getting into angel investing, other than having capital and fighting capital, what advice would you give folks?

See, the number one thing you need is, I think, besides number one thing is Capital, number zero thing. Now, one thing is then you need, you need to have deal flow, as they call it, or companies that you are meeting with and deciding. And then you need to know how to pick these companies. So you need to meet companies, you need to know how to pick them. And then, you know, as an angel is generally easy. So I think you need to figure out how to get deal flow. And there are three ways to get deal flow companies. One you build your own brand. Like you can be like Lenny who's built an incredible brand or none of us can be like Lenny, but you can try to, we can all publish. The reality is I used to tell every single person, you can build your brand on the internet. You can build your brand, there's social media channels, there's so many channels and you have the person here who can teach the masterclass and that. You can build your brand and just by doing that, you'll get people coming to you. Second, do you have a lot of anyone in technology has other people they know who are angel investors. So just tell them, hey, I'd love to help companies. If you're investing in a company, please let me know. And the more people you tell, the more likely it is they'll remember you. And every time you meet them, reinforce that. And third, investors. If you do know Venture capitalists or investors, many of them are looking to bring on. There's typically a round. When they lead a company's round, there's typically an allocation for angels. But for all of those, the first and most important thing is you need to understand how are you going to add value to these companies? What is your differentiation? What do you stand for? Why should a company take your money? The best companies have much more than, as Lenny and I both know, the rounds are oversubscribed. It is hard enough to get even $1 into the round, let alone $100,000 or $5,000. So why would they take your money? And so that's the thing you have to really figure out. What is your unique differentiation? What do you bring to these companies that no one else can? And I know that's hard, that's painful to figure out, but that is the introspection each of us needs to do. And that's the way you do that is by just sharing your non-obvious insights and don't just like basically just write. That's why I think writing is so powerful because it shows the world. My rule of thumb is when they do a search for you on Google, if your LinkedIn profile is the first thing that comes up, you've probably done something wrong. Once it comes up, it's an article you wrote. is a tweet you published, is someone mentioning you on something else, etc. Because that's when clicking on it is they know what you stand for by that content, about you, by you, etc. Yes, Mike Moritz can get away with LinkedIn because no one needs to know what he has done. But for the rest of us, we need to build our brand, what we stand for, and it'll change over time. I used to basically believe I should just think about product development, how to lead product teams, engineering teams. But over the last five years, since I've led broader teams, I now share stuff which is much broader than that. And so what I stand for and what value I had has changed and evolved and hopefully increased over time. The same will happen. But you've got to take ownership of your brand on the internet. No one else can. No one else can. It's not your company. You've got to transcend the companies you work for. If your identity is XYZ worker drone at ABC company, that's not enough. You've got to be XYZ expert in a or whatever that is. Even if it's a niche thing, that's okay. Every company leads. So many companies come to me. I want some payments expert, you know, and then I'll find someone who's a payments expert for them because they're trying to build a fintech practice or something. So be an expert in payments. If that's what you know, write about non-average insights on payments. Doesn't need to be a functional discipline like then you and I do in product or something can be a domain, risk, payments, crypto. Think about crypto, right? The people who got into crypto and I just read a post by this guy, Richard Chen. He graduated from Stanford. I don't know him, but I read incredible post. He runs this firm fund called one confirmation, which is a top fund. He graduated from undergrad four years ago. That's all he did. I mean, he was head of Stanford blockchain. He wrote, he writes amazing stuff. He's built a brand for himself. Kudos to him. 25 years old, probably never met the guy, but I was like, ah, this guy knows what he's doing. What's his LinkedIn? Oh my God, he's never worked at a company. He's basically been out of school for.

Four years, but he's incredible insights. Wait till he hears this podcast. He's like, holy shit, they're talking about me. I hope he's a listener. And if not, we're gonna find him. Okay, we are now at the lightning round. And so what I'm gonna do, I'm gonna ask you a bunch of questions real quick, whatever comes to mind. Let me know if nothing comes to mind, that's also cool. And then we will wrap up. Are you ready?

Perfect.

Ready. Okay. What's a book that you've recommended most to other product leaders?

Playing to Win: How Strategy Really Works. It's a book called Playing to Win.

And the subtitle is How Strategy Really Works. Very good book. Amazing. I have not read that. I will check that out. What's a company that you recommend to people that are looking for new gigs?

Maybe product managers, maybe any another function. DoorDash, incredible operational excellence and what you learn here, I have myself learned a lot in the two years I've been here about new ways of the attention to detail, ex operational excellence unparalleled.

I usually include, you can't mention the company you're working at now, is there another company by any chance? And if not, you can have that.

I would say Coinbase, if you are interested in crypto, I am technically a board member, I truly believe, I think if you are interested in crypto, Coinbase has such a diverse set of things that they work on that it is literally you can work on almost any part of crypto from NFTs to wallets to custody to infrastructure. They have companies called Bison Trails, which does infrastructure. So you can truly like, it's like Google worked on like everything. You could work in YouTube, you can work in search, Coinbase, I think the same thing. You can work in 10 different products and within two years or three years learn the complete specter crypto ecosystem.

Also an Airbnb alumni founder.

That's right.

What's your favorite app right now?

Yeah. Over the last few weeks, it has been Coinbase wallet. I've been playing around. I just was a HODLer. I basically just had held Bitcoin Ether for many, many years. But then over the last couple of months, I just said, got to just. And the Coinbase board brings you listen to all of these things. I'm like, got to now diversity of Beyond and actually got to start. sticking stuff, going on distributed exchanges and or decentralized exchanges and just basically playing around with Coinbase Wallet. Because earlier I wasn't using Wallet, I was just using coinbase.com where you can't do any of this stuff. And then DoorDash is the other one. I think I truly use it to order food. We use it to order food every.

Day, but Coinbase Wallet is one I'm using a lot now. Awesome. I gotta check that out. I just got access to the Coinbase NFT stuff. And so, yes, it'll pull me into the Coinbase ecosystem. okay, a couple more questions. Who is a favorite person to follow on Twitter or Instagram, especially these days? Exactly.

Easy Choice. All right.

All right. Who's a favorite manager that you've had over the years? All of them.

I've learned different things to them, so no easy choice there. No favorites.

All right. Taking the easy way out. And then what's a favorite interview question that you like to ask in interviews?

Not with Founders, but with, with hiring. What are you most proud? The interview question is a good one. Tell me about something that you're most proud of. What is the accomplishment, career accomplishment you're most proud of? Because it tells you how they measure their impact, tells you a lot about what they care about, how they measure their impact. If they say, as a PM, I launched XYZ feature, they're talking about the impact and they can't evaluate it. You know something about that. Or if they talk too much about them versus the team, et cetera, et cetera.

So you get a lot from that question. It's a loaded question. Amazing. I love that question. Okay, where can folks find you online and how can people listening be helpful to you?

I am on Twitter, G-O-K-U-L-R@GokulR on Twitter. And I always say the best way to help me just help the broader ecosystem paid forward. And if you paid forward at some point, whoever you paid forward to help me at some point, but if all of us paid it forward, the world would be a better place. Pay it forward. And then, like I said at the very beginning, believe in the power of serendipity. And I need to listen to Lenny's TED Talk on that.

Yo, boy. Serendipity, paying it forward. Amazing. What a great way to wrap it up.

Thank you so much for being here at Gokul.

Thank you, Lenny.

Thanks for having me. That was awesome.

Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast.

You can also learn more at lennyspodcast.com I'll see you in the next episode.