June 13, 2022

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

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

Gokul Rajaram serves on the executive team at DoorDash, where he leads the Caviar product line. Previously he worked at Square, where he was also on the executive team and led a number of key product lines, and as a product director at Facebook, where he helped the company transition its advertising business to become mobile-first. Earlier in his career, Gokul was a product director for Google AdSense, where he helped launch the product and grow it into a substantial portion of Google’s business.

Gokul also serves on the boards of Coinbase, Pinterest, and The Trade Desk and is a prolific angel investor, having invested in companies like Airtable, Khatabook, and 100+ more.

In this episode, you will learn:

1. How to navigate your next career

- What should you focus on in order to improve your optionality?

- What should you consider as you look for your next career adventure?

- Why join winners in a space?

- Why should people entering the workforce join mid-stage companies?

- Why there are many paths to success.

2. How to build a product development process at early-stage companies

- What does the best product development process typically look like at different company stages? 

- What are some common pitfalls when building these processes?

3. Hiring PMs

- When should you hire your first PM? What should you look for?

- When should you wait longer to hire a PM?

- What’s the number one secret for hiring a product leader, regardless of industry? 

- How much time should you allocate for hiring as a founder?

- How might job titles impact your company’s work culture?

4. How to start angel investing 

- How did Gokul start investing in startups? What would he have done differently?

- What does he look for in a startup pitch? 

- How much time should you spend as a part-time investor? 

- How do you find deals as a new investor?

Where to find Gokul:

- Twitter: https://twitter.com/gokulr 


- Gokul’s current favorite app, Coinbase Wallet: https://www.coinbase.com/wallet 

- Favorite book, Playing to Win: How Strategy Really Works: https://rogerlmartin.com/lets-read/playing-to-win 

- TED talk: TEDxConcordia - Lenny Rachitsky - Losing Serendipity 


Thank you to our sponsors for making this episode possible:

Amplitude: https://amplitude.com/

Flatfile: https://flatfile.com/Lenny

• Productboard: https://Productboard.com/

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe


Lenny (00:00:00):

I sometimes wonder how someone like go Gokul Rajaram can exist. He has an intense full-time job at DoorDash where he leads a significant part of the product in 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 seemingly on the cap table. 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 just 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.

Lenny (00:00:47):

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Lenny (00:01:35):

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Lenny (00:02:46):

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

Gokul Rajaram (00:02:53):

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

Lenny (00:02:54):

It's absolutely my pleasure. You're on the boards of Coinbase and Pinterest, you're a really big deal at DoorDash. You're 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 what was your journey like to becoming this luminary of tech?

Gokul Rajaram (00:03:24):

First of all, let's not start use the word luminary. I think it's people like Elon and Mark who 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. Crazily 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 seven software is for wimps. I'm going to go hardcore.

Gokul Rajaram (00:03:50):

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. Was my second choice after Cisco. So literally you can see some of these decisions. You're just saved from yourself by [inaudible 00:04:08], and 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 searches results and ads and then syndicating it to other properties like AOL back in the day, Yahoo, et cetera.

Gokul Rajaram (00:04:21):

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'd 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," Serge Brin, the co-founder had given them a project of essentially reversing what Google had done with search. You type in a phrase, set of keywords and then Google identifies the webpages that are most relevant to the set of keywords. So we have an index that matches keywords and webpages, so why don't we extract those keywords for any given webpage and basically see if we can target ads based on that? So that seemed interesting. Google's AdWords product, which was such, ads had just started scaling up and I was like, "Hey, do you have any PMs working with you?"

Gokul Rajaram (00:05:09):

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 help them talk 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 realized is that it's very important to do a 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 relationship with the company, because those are what will lead to the next set of opportunities.

Gokul Rajaram (00:05:57):

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 fundraiser in Google. And Jack, the CEO of Square, asked the founder who was 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 of something in the company. I just helped them out because they reached out to me because it was a former colleague and I said, "Sure, I'll help you out."

Gokul Rajaram (00:06:38):

And then that resulted in him saying good things about me and that led to the inbound from Square. So I think you got to prioritize this stuff. I mean you 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. I realize in today's world there are lots of crazy serendipity things that happen. If you take inbounds from smart people and you just chat with them and you help them out.

Gokul Rajaram (00:06:58):

Paying it forward is the other thing, paying it forward. Lenny, you're a great example to this, you pay it forward so much. Your articles, stuff you write, good things happen in ways that you don't even realize. You build up a reservoir of goodwill that comes back to help you in different ways.

Lenny (00:07:12):

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 Your Serendipity. It's out there on the internet, in case people want to-

Gokul Rajaram (00:07:21):

I'm going to check it out. Wow.

Lenny (00:07:22):

Long time ago. But I 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 passion that's pulling them in?

Lenny (00:07:36):

Or more, I just think there's 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 somewhere. Or some, right in the middle? How do you think about that?

Gokul Rajaram (00:07:46):

I think you 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 until they actually start doing the work. I could never ever 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 affected a small business or basically people or small business that I can relate to. It is harder for me to get energy solving problems of big enterprise and companies.

Gokul Rajaram (00:08:28):

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 for 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 more than the problem because I've saw different kinds of problems, but I realize 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. They would be hundreds of thousands of them back then.

Gokul Rajaram (00:09:10):

It's probably 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, "Gokul, I know you right? We used to make a hundred thousand dollars a year based on purely 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, it's very important if you think... 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.

Gokul Rajaram (00:09:48):

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 build a really large company. And so if you look at everyone, whether it's... You've 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. Mark at 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.

Lenny (00:10:18):

That's a good segue. 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 what 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?

Gokul Rajaram (00:10:35):

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's 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 sat on the board of Coinbase, and I think that person still thanks me because I think they were focused too much on the title, that they were going to be the super senior person at this company on the management team, et cetera. But I said, "Ultimately you don't realize this, but the value of working at a leader in any space, the quality of talent you work with, the brand, the network effect, so many things accrue to you. I would much rather be the number two or number three person."

Gokul Rajaram (00:11:25):

If you think of it that way, and the leader in a space, than the top person. Say 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 probably want to be the ICPM at Google. I bet you all day long, all day long. Yahoo is a great company, but Google is just a different caliber and different class. So I think it's very important to try to work at, obviously you don't know who the winner is, but if you think that's that something is a winner in a space, in large space, so many benefits that recruit 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.

Lenny (00:12:07):

So along those lines and kind of touching on your investor experience, what should folks look for 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 for either a new person joining the workforce, maybe PM, let's say, or even later?

Gokul Rajaram (00:12:25):

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.

Gokul Rajaram (00:12:46):

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's 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.

Gokul Rajaram (00:13:12):

So because, looking back on a career, always without really thinking about it, as employee number six, seven or 800 at Google, employee number, few hundreds at Facebook, employee number seven, 800 at Square. DoorDash was slightly later because just 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.

Gokul Rajaram (00:13:35):

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.

Lenny (00:13:43):

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

Gokul Rajaram (00:13:48):

I think unless you know the founders very, very, very well, joining a very 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 around, few weeks after raising your prior round, of couple of months without much movement, without much company progress have... Are probably gone for most companies. And we all have seen now companies that have raised round 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.

Lenny (00:14:29):

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?

Lenny (00:14:46):

Things you've taken away about how to run a company, build a product? Or anything else that's just taught you a lesson about how to do what you're doing?

Gokul Rajaram (00:14:54):

One of the most interesting things I've 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 I have actually worked at. Google would be technical. It is very, very technical, technology focused, because Google believe, 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, then 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.

Gokul Rajaram (00:15:46):

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 Shoe at DoorDash or Jack, they all had their 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 tried to build a company that sold enterprise software, I don't think that would've 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.

Gokul Rajaram (00:16:33):

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 bunch of young companies are coming to me saying, "What do we do now?"

Gokul Rajaram (00:17:01):

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."

Gokul Rajaram (00:17:16):

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 means at some point that the music is going to stop.

Lenny (00:17:27):

Unless you've got some magical insight or someone that's just killing it.

Gokul Rajaram (00:17:31):

A growth pack, right? Everyone's looking at this growth tag, but there is no... There's nothing like the silver growth tag bullet.

Lenny (00:17:37):

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.

Gokul Rajaram (00:17:45):

Yeah, those are exceptions that prove the rule.

Lenny (00:17:48):

What I think of when you talk about this is that something Seth Godin shared a while ago that I always come back to you, this idea that your product has to be remarkable where 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.

Gokul Rajaram (00:18:04):

Exactly. Very well said.

Lenny (00:18:06):

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?

Gokul Rajaram (00:18:30):

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 the first several quarterly plan. They just did 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.

Gokul Rajaram (00:19:13):

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 your founder that you update with 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 surviving, 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.

Gokul Rajaram (00:19:55):

The product and company strategy are the same. As you start growing, you have a go-to market strategy, product strategy, et cetera, et cetera. 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 10 engineers or so. Anywhere between five and 10. 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 20, 23 person stage, and the product strategy then makes choices. What customers are we serving? More clearly articulates what have been implicit hopefully earlier.

Gokul Rajaram (00:20:51):

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 doc, 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 the 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.

Gokul Rajaram (00:21:38):

As you go 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.

Lenny (00:21:49):

Wow. So much good advice. There's a couple 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 some of the more common mistakes that founders make? That early teams make?

Gokul Rajaram (00:22:04):

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 shaping 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's 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 a 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 it dictating them.

Gokul Rajaram (00:23:00):

Why should we build an iOS app, while the actual problem to solve is we want to increase the percentage of people using a 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 shaping 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.

Lenny (00:23:41):

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 eight to 10 engineers. What 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?

Gokul Rajaram (00:24:04):

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 smaller teams are always good. Smaller companies are always good, part of the problem. 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 playing the role of a product manager, then the eight to 10 person engineering team is not being cared for and fed.

Gokul Rajaram (00:24:39):

Engineers are by far the most expensive resources in the company. By far, right? I mean if you look at the composition of engineers versus... And PMs versus any other function, it's two to three, equity, cash, everything.

Gokul Rajaram (00:24:52):

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. In some ways you got to think about yourself. Am I, as the founder, is this 10 person team or 8 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, et cetera?

Gokul Rajaram (00:25:25):

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-

Lenny (00:25:36):

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.

Gokul Rajaram (00:25:43):

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 move from their role to being a PM. Why? Because many cases, the role of the PM is actually to be the liaison between the founder, 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 the engineering team work.

Gokul Rajaram (00:26:16):

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 would be the best PM from a cultural assimilation. And getting the engineers just to understand the value of a PM and getting the founders to be comfortable, slowly being more hands off. Was it true of Airbnb, also? Was Joe not the first PM?

Lenny (00:26:46):

He was. And he was actually an engineer when he joined, so that's exactly how you describe. So say that you hire, or you transition someone from PM into their... Being the first PM. What are some signs that maybe they're not doing too well and things aren't going well and maybe you should go in a different direction?

Gokul Rajaram (00:27:03):

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're very, very quick to tell you, "Look, this person is not working, they're not being effective."

Gokul Rajaram (00:27:27):

What value are they adding? And I think just number one thing you have to do is you have to, just because you hire a PM doesn't... 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.

Gokul Rajaram (00:27:53):

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 are a PM. There's a 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.

Gokul Rajaram (00:28:45):

And so I personally believe in the growth mindset a lot. The reason that hopefully this person was chosen to be the PM is the founder saw that this person has the characteristics, traits, which is curiosity, the 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.

Lenny (00:29:21):

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

Gokul Rajaram (00:29:23):

Good work.

Lenny (00:29:25):

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, we got to get a PM in ASAP." What are some signs or reasons to wait a little bit longer before you hire your first PM?

Gokul Rajaram (00:29:39):

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, the whatever, your 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.

Gokul Rajaram (00:30:04):

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 defined product team. So I think you need an empowered product team that takes ownership and can take a problem, figure out all the options 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 really that partner to help facilitate that for the most part.

Lenny (00:30:39):

That's awesome advice. And yeah, I think that's going to be-

Gokul Rajaram (00:30:42):

I think infrastructure is a great example. I think Stripe for example, is famous for not hiring PMs because I think when your audience is developers, they know their audience really well. And so I think many dev ops and developer facing companies, they don't have that many PMs. The PM to engineering ratio is very small. Even in Stripe today I bet it's much smaller than other companies. So those are exceptions that engineers truly understand the domain better. So the machine learning companies, infrastructure companies generally I think need fewer PMs. And this is true for any consumer product company. 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.

Lenny (00:31:27):

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Lenny (00:32:15):

Yeah, I have a post where I 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 a PM.

Gokul Rajaram (00:32:27):

There we go, that's right. The designers played the role of the PM.

Lenny (00:32:30):

Somebody's got to be doing the job, right? Hopefully they enjoy it, sometimes they don't.

Gokul Rajaram (00:32:35):

That's right.

Lenny (00:32:36):

Okay. So say you've hired your first PM, you're building a product team. Something I wanted to get your take on is, as PM teams grow, sometimes they end up changing who they're reporting to. Sometimes it ends up being a CPO, sometimes a GM, sometimes like 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?

Gokul Rajaram (00:33:03):

Yeah, I've worked at companies where it's both functional, products orgs are functional. Where all the PMs report into the head of product, reports to a 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 errors from a good PM, but a bad PM can really screw up, can screw up the work of 10 engineers.

Gokul Rajaram (00:34:01):

So it's much more important to hire good PM than it is to hire a good engineer. Any good one. Because there's so few PMs for every engineer, that one good or bad PM can really screw up everything, compared to the impact of one good or bad engineer. So what that means for me is that if you have four or five PMs, and 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.

Gokul Rajaram (00:34:32):

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 five PM team, they probably should report to a dedicated of product manager 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.

Gokul Rajaram (00:34:57):

That product manager, I think they could report to the CTO, they could report to the CEO, they could report to the GM. I don't think 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 a certain size.

Lenny (00:35:12):

Awesome. I could not agree more. Another thing I've seen, as 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 try something. See if that works. You can always change it in the future. That's super common.

Lenny (00:35:30):

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.

Gokul Rajaram (00:35:49):

That post actually was triggered by, that morning, one of my company CEO messaged me that, "Wow, I hired someone from this company. How'd you know this person was available from 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 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."

Gokul Rajaram (00:36:19):

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 that's keeping them at night, "I want to hire a leader for X, Y, Z 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."

Gokul Rajaram (00:36:48):

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 the 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... Or consumers. And then say, "Okay, I want to hire a head of marketing." Great. This is the hardest thing. Go 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.

Gokul Rajaram (00:37:31):

You hire the person who's reporting to them, the lieutenant. And actually, Adam Zamos, who was the head of people at Square chimed into say, "At Square, early days we used to go..." He used to run people, the people team at Square. "We used to go and hire the up and coming lieutenants of the lieutenants." And so I think you basically have to build almost an org chart and it's not that hard. You just have to spend 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 a 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.

Gokul Rajaram (00:38:16):

And so my goodness, our teams were raided. The next two years, I literally saw the full team, a huge chunk of a team in different parts of payments, compliance, risk, just being raided by other fintechs. And I saw that this was being followed. Because you say, "Okay, who's the company who's best in being in 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, et cetera. They didn't go after our head, they went after the lieutenant and the lieutenant of the lieutenant, et cetera.

Lenny (00:38:46):

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 leaders should spend on hiring? What percentage of their time have you seen the best founders and leaders spend?

Gokul Rajaram (00:39:07):

Obviously you've got to always be hiring. Even today, I think Tony and DoorDash, 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 in hiring is, you've got to build a process first of all, and that takes a lot of heavy metal work, the right process for you to make sure you do reach out. And again, there are two parts of hiring, 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.

Gokul Rajaram (00:39:56):

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 LinkedIn reach out? Or whatever tools you use to reach out to. Who are the types of profiles, what roles you want to prioritize. So you need to find the right hour to do that in. The second hour should be devoted to actually meeting one or two people on a daily basis, and that's two half an hour conversations.

Gokul Rajaram (00:40:26):

So I think if you just do that, you'll actually, over even 30 days, think about it, you'll meet with 60 people. And you'll do 30 hours of LinkedIn's, just two hours out of say 10 hours a day. And let's say 20 hours, 20 days. So instead of 30. Because of weekday, 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.

Lenny (00:40:50):

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?

Gokul Rajaram (00:40:57):

One hundred percent. I think putting in the process upfront is really important because you can flounder around, and then just spending a few, four, five hours upfront, talking to a few folks, coming with a good process can massively improve the because they say, right, it's all about once you aim the strategy or the direction you're going is much more important than the speed you go in.

Gokul Rajaram (00:41:18):

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.

Lenny (00:41:38):

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.

Gokul Rajaram (00:41:48):

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 would titles. The titles I'm most opposed to, to be honest, I'm not opposed to titles. I think, tweeted about this and people interpret to 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 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.

Gokul Rajaram (00:42:39):

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 hear who general counsel is, but I was meeting with a 25 person company today and that CEO told me... I was like, I always talk about what keeps you up at night? And this company's in somewhat of a legal heavy space. He is 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. Or 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.

Gokul Rajaram (00:43:22):

You just don't want them to be the general counsel. She's over and over again. And so, there are certain times you only can give once and if you give it to early, you can't then... That's the reason to avoid title 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.

Lenny (00:43:50):

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. Clearly you live that yourself.

Gokul Rajaram (00:44:01):

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 and never had a single discussion at Square with my team about what the title should be. And that was amazing. At other companies, 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.

Gokul Rajaram (00:44:37):

Had stuff of course around scope, impact, compensation, that's great. I want to have conversation about that, but title? No.

Lenny (00:44:45):

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

Gokul Rajaram (00:44:51):

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

Lenny (00:45:00):

Easy. And then delay it, meaning have-

Gokul Rajaram (00:45:02):

Very simple. [inaudible 00:45:05]

Lenny (00:45:04):

And delaying titles, meaning like anything other than just software engineer, product management?

Gokul Rajaram (00:45:08):

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 Caviar 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 that 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.

Gokul Rajaram (00:45:40):

It's head of block, a block leader I would say probably should be more appropriate. He's a leader block, and then so on, it premieres down.

Lenny (00:45:48):

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?

Gokul Rajaram (00:46:09):

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 I literally, without going much, I just wanted to support them because I'd worked with them. And so I just put a small check into their 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. [inaudible 00:46:56] is amazing and they are very much believe in a big market.

Gokul Rajaram (00:46:59):

I strongly believe that great founders, and Airbnb's a great example. They 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 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 with all my friends. I'm going to look to see what the market they're in."

Gokul Rajaram (00:47:25):

So I basically just started making these assumptions, "Oh, well, I should not invest in this company." And turns out, almost all of them were sins of omission. I much more care about sins of omission because you can only lose one X your money. But for me, the relationship with the person, a person I know and respect and good friends with, and I'm not investing in them, I don't want to lose that.

Gokul Rajaram (00:47:48):

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 the 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 their first company, even though you thought they were great because the marketers are great, they won't probably come back to you for the second company either.

Gokul Rajaram (00:48:16):

So very, very founder centric style of investing, almost like YC, I would say. Closer to YC than anything else because YC invest in 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 under that excitement, you'll find your product market fit four times. I see this again and again.

Lenny (00:48:41):

I love that advice and it's 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.

Gokul Rajaram (00:48:55):

You've got to really make sure what the motivation. That's what I really want to understand. 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.

Gokul Rajaram (00:49:18):

Versus, it's something they read about in Tech Crunch or it's a new US Web three 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 their idea for... The reason they're starting the 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... Or paper maybe, and read it to fully understand why you want people who really immerse themselves in an industry and live and breathe it before they tackle it.

Lenny (00:49:50):

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

Gokul Rajaram (00:49:55):

The ability to hire talent before even you have... Or 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 you need to start a company. And it's also a lot of things to do.

Gokul Rajaram (00:50:18):

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... There are obviously one person founding teams that have worked well, but I think the two or three person founding teams, I feel much. Two is the ideal number. So I look for the two person founding team, complementary skills.

Lenny (00:50:43):

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 and not just to go crazy and burn yourself out?

Gokul Rajaram (00:51:00):

Time boxing. Exactly what you said, Lenny, it's time boxing. Most of the time ironically is spent on DoorDash and... Not ironically. Logically is spent on DoorDash even though it may not appear it. So I spend 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 that are needed to do my work?

Gokul Rajaram (00:51:25):

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 4... 28 meetings, that's a lot of meetings you can do with people, et cetera, et cetera. Yeah, so I think 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.

Lenny (00:51:59):

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.

Gokul Rajaram (00:52:08):

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 start with, "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 or multiple founders, how they knew each other, and how they came up with this idea that they're going after. Versus what problem they're tackling.

Gokul Rajaram (00:52:36):

I have a standard set of questions I 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 into the next meeting. So compartmentalizing well.

Lenny (00:52:52):

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

Gokul Rajaram (00:52:56):

No, I think it seems... Yeah, it seems too formulaic then. I think there's questions that then change based on what the 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 introduce myself and then asked them for their founding story. They're all nervous, pitching, et cetera 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 your top three problems."

Gokul Rajaram (00:53:23):

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. How was it? Tell me the last time you took a payment, credit card payment. Tell me about your last customer." People love telling stories about themselves. Everyone likes talking about how they did something.

Lenny (00:53:40):

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

Gokul Rajaram (00:53:49):

See, the number one thing you need is, I think, besides... Number one thing is capital. Number zero thing. Number one thing is then you need to have deal flow, as they call it, or companies that you're 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 pick them. 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 to companies. One, you build your own brand. 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, social media channels."

Gokul Rajaram (00:54:29):

There's so many channels. And you have the person here who can teach the masterclass in that. You can build your brand. And just by doing that, you'll get people coming to you. Second, you have a lot of... Anyone in technology has other people they know who are angel investors. So it's just tell them, "Hey, I'd love to help companies. If they're investing in a company, please let we 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 capitals or investors, many of them are looking to bring on... There's typically a round when they lead companies around, 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?

Gokul Rajaram (00:55:13):

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, their rounds are over subscribed. It is hard enough to get even $1 into their round, let alone a hundred thousand dollars 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.

Gokul Rajaram (00:55:44):

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.

Gokul Rajaram (00:56:02):

What should come up is an article you wrote. Is a tweet you published. Is someone mentioning you on something else, et cetera. Because that's when, clicking on it, they know what you stand for by that content about you, by you, et cetera. Yes, Mike Morritz 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. For 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 add 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.

Gokul Rajaram (00:56:46):

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 X, Y, Z, worker drone at A, B, C company, that's not enough. You've got to be X, Y, Z expert in A. Or whatever that A is, even if it's a niche thing, that's okay. Every company leads... So many companies come to me, "I want a payments expert." 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 obvious insights on payments. Doesn't need to be a functional discipline like, Lenny and I are doing 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.

Gokul Rajaram (00:57:33):

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.

Gokul Rajaram (00:57:50):

Never met the guy, but I was like, this guy knows what he's doing. Watch his LinkedIn. Oh my God, he's never worked at a company. He's basically been out of school for four years, but he has incredible insights.

Lenny (00:58:00):

Wait till he hears this podcast. He's like, "Holy shit, they're talking about me."

Gokul Rajaram (00:58:04):


Lenny (00:58:06):

I hope he's a listener and if not, we got to find him. Okay, we are now at the lightning round. And so what I'm going to do, I'm going to 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?

Gokul Rajaram (00:58:21):

Perfect. Ready.

Lenny (00:58:22):

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

Gokul Rajaram (00:58:27):

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.

Lenny (00:58:34):

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 other function?

Gokul Rajaram (00:58:44):

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. Operational excellence, unparalleled.

Lenny (00:58:56):

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.

Gokul Rajaram (00:59:02):

I would say Coinbase, if you're 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 a company they called Bison Trails, which does infrastructure. So you can truly, it's like Google, worked on 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 spectrum, crypto ecosystem.

Lenny (00:59:37):

Also an Airbnb alumni founder.

Gokul Rajaram (00:59:39):

That's right.

Lenny (00:59:40):

What's your favorite app right now?

Gokul Rajaram (00:59:42):

Over the last few weeks it has been Coinbase wallet. I've been playing around. I just was a hoarder. 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... In the Coinbase board meetings, you listen to all of these things. I'm like... Got to now diverse and beyond and actually got to start staking stuff, going on distributed exchanges, or decentralized exchanges and just basically playing around with Coinbase wallet because earlier I wasn't using wallet. I was just using Coinbase dot 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 every day. But Coinbase wallet is one I'm using a lot now.

Lenny (01:00:24):

Awesome. I got to 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?

Gokul Rajaram (01:00:38):

Exactly. [inaudible 01:00:40].

Lenny (01:00:39):

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

Gokul Rajaram (01:00:44):

All of them. I've learned different things through them. So no easy choice there.

Lenny (01:00:49):

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 hiring.

Gokul Rajaram (01:00:56):

What are you most proud of? 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 X, Y, Z feature," they're talking about the impact and the kind they value it. Something about that. Or if they talk too much about them versus the team, et cetera. So you get a lot from that question. It's a loaded question.

Lenny (01:01:24):

Amazing. I love that question. Okay. Where can folks find you online and how can people listening be helpful to you?

Gokul Rajaram (01:01:31):

I am on Twitter, G-O-K-U-L-R at GokulR on Twitter. And I always say the best way to help me, just help the broader ecosystem. Pay it forward, and if you pay it forward, at some point, whoever you paid forward helps 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.

Lenny (01:01:58):

Oh boy.

Gokul Rajaram (01:01:59):

Serendipity, paying it forward.

Lenny (01:02:01):

Amazing. What a great way to wrap it up. Thank you so much for being here. Gokul.

Gokul Rajaram (01:02:05):

Thank you, Lenny. Thanks for having me.

Lenny (01:02:06):

That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You could also learn more at Lenny's podcast dot com. I'll see you in the next episode.