Gokul Rajaram shares specific characteristics he looks for in entrepreneurs who range from former coworkers to founders he never met in-person. He describes his unique journey in the Silicon Valley leading product development at Juno, Google, Facebook, Square and Doordash.
Gokul Rajaram shares specific characteristics he looks for in entrepreneurs who range from former coworkers to founders he never met in-person. He describes his unique journey in the Silicon Valley leading product development at Juno, Google, Facebook, Square and Doordash.
Highlights:
More details at https://podcast.sure.ventures
This person, Max, is going to do whatever it takes. He just cannot eat, sleep, or breathe unless he's just thinking about the problem all the time. He even got me and our board member, Roelof at Sequioa, to brainstorm about how to grow this program. That's the kind of person he is.
And so I knew that when he told me he was planning to leave Square a few months out, I wanted to invest in his company, whatever the company is.
[00:00:28] Gopi Rangan: You are listening to The Sure Shot Entrepreneur,
a podcast for founders with ambitious ideas, venture capital investors, and other early believers tell you relatable, insightful, and authentic stories to help you realize your vision. Gokul Rajaram is the head of products at Caviar, a division at DoorDash. He has held leadership roles at Google, Facebook, and Square, and has led the launch of many important products.
Gokul is considered the godfather of AdSense, which revolutionized the ad tech industry. He's a successful entrepreneur. corporate executive, board member, and an angel investor. In this episode, Gokul and I discuss his journey in the Silicon Valley, how an MBA helped him, and his experience as an angel investor.
You will learn the specific things that Gokul looks for in an entrepreneur when he makes angel investments. You will also see an insider view into the expectations of an angel investor, what he expects to achieve through his angel investments. Gokul, welcome to The Sure Shot Entrepreneur. Tell us about yourself.
[00:01:46] Gokul Rajaram: Thanks, Gopi. It's great to be here. Well, it's the classic story of an engineer turned product manager turned business executive. I got my undergrad education in India where I got a bachelor's degree in computer science more than two decades ago. I then came to the United States to get a graduate degree in computer science.
I went to UT Austin and I have to say that going to a state school which has a good football team was a great way for me to get acclimatized to the U. S., to college. and to American culture broadly. I am very grateful that I went to UT Austin. It has a great football team and so I wear my Longhorns hat more proudly than anything else out there. I met lots of Longhorns fans over the years. But after UT Austin, after I got my computer science degree, I was faced with an interesting challenge, which maybe we'll talk about later, but ended up with me going into the software industry, becoming a software engineer, got my MBA after two years.
And again, we can talk about the reasons for why I went for an MBA and what I recommend on the MBA front. I got my MBA from the Sloan School at MIT. And then moved out to the valley immediately after that, ended up getting a job at Google, leading product for a young product and not yet launched product, which became known as Google AdSense.
I was lucky enough to work on it, helped grow it over the years, and then left to start my company with my brother, which got acquired by Facebook. And so I ended up leading ads at Facebook for three, three and a half years. And, uh, from there moved to Square and, um, ended up leading first the point of sale team.
And then Caviar, which is a food delivery service that Square acquired. I was a GM for Caviar for a few years. And then Caviar was acquired by DoorDash. As part of that I moved to DoorDash about seven months ago and have been at DoorDash. So, I joked that I've only worked at companies that are private.
So I've worked at Google when it was private, Facebook when it was private, Square when it was private, now DoorDash when it's private. And typically I've been employee between 500 to 1000 at a company. Google I was, I think, employee 600 or 700. Facebook also around 700, 800. Square around 600, etc. So that's, that seems to be the sweet spot for me.
[00:04:02] Gopi Rangan: You have this knack of finding opportunities at companies; you join them before they go IPO. And you did that with Google, with Facebook and Square. Tell us about that experience. Maybe you can also touch on the MBA part of it and how that helped you.
[00:04:18] Gokul Rajaram: Yeah, crazily enough, even the first job after my master's in computer science, I ended up joining a pre-IPO company, and this is at a time when I didn't even know what an IPO was really.
And the reason I joined the company, it's the same as the reason I joined Google, Facebook, Square, etc. is two things. One, I was excited by the mission of the company. The first company I joined, Juno, had the mission of making the internet free. So it was a free email service. Back then, people pay for AOL and access to the internet email.
And this company, Juno, had the mission of making the internet free and accessible. And that really resonated with me. And the same with Google's mission, Facebook's mission, Square's vision. And the second one is the leadership. The CEO. In every company, I've had the chance, even when I was an engineer working at Juno, I had a chance during the recruitment process to actually meet the CEO and the leader of the company. And I was really impressed by and really felt a personal connection with them and felt that they are the right leader for this company and that I can learn a lot working with them, whether it was Charles at Juno, Larry at Google back then, Mark and Cheryl at Facebook and then Jack Dorsey at Square. All four of them just epitomized the mission in a way I thought was really compelling. So the mission and the leader are the two reasons I've always chosen companies and somehow it's led me to pre IPO companies, strangely enough. The MBA question is a good one. I've basically come to the realization after this many years that the right reason to do the MBA, and I think the only reason to do the MBA is if you want to change your career; if you want a different career direction than what you're going down, and if that new career path that you desire is not available within your current company.
So at Juno, for example, I knew that I wanted to go into more of a product management style role. But ironically, Juno didn't have product managers. In fact, the reason I even knew of product management was because I got to do (at Juno since they didn't have the product manager role) I ended up talking to customers myself as an engineer and a tech lead, I ended up doing mockups.
They didn't even have a clear design function, so I ended up doing the mocks. They had a design function that was for high fidelity designs. But who would do the sketches? So I ended up doing actually the sketches of what the product should be. I ended up writing the requirement documents, talking to customers and so on.
I realized I enjoyed that part of the process much more than I did just building the product. And this led me to say, well, what, what does this role? Is there a role like this? Did some research turns out there was a role called product management. And Juno didn't want to have product managers for various philosophical reasons.
And the only way I could make that change was by changing companies, which was hard. I always say that it's hard to change companies and change tracks or career paths at the same time. You can do one or the other. So, you know, there was no opportunity to do that. So I decided to go to business school in order to become a product manager.
And I've seen this happen many times. Investment bankers or consultants might go to business school to become a product manager or vice versa. Engineers go to school to become bankers or venture capitalists or something else. So I think that's the number one reason and, I think, really the only reason to change career paths if you wanted to go to business school, if you want to change your career track and you can't do it in the company you are at.
[00:07:28] Gopi Rangan: You described many things here. What you look for in a company when you joined, and you see a common thread between many different companies you joined. The mission of the company and the leadership. Both of them impressed you. And you also talked about the MBA experience and what can be the best way to use the MBA experience. It's mainly for transitioning from one area to another area in your career. You also became a very active angel investor. You've invested in more than 100 companies. How did that come about?
[00:07:56] Gokul Rajaram: I think almost every angel investor I've talked about has started with one common theme, which is the people that they've worked with.
So in my case, also, it was basically based on a person. In this case, there was a guy, Satya Patel, who worked for me at Google. And in 2006/7, he left Google to become a venture capitalist at Battery Ventures. I kind of knew vaguely what venture capitalists do obviously, but I didn't really pay much attention until Satya Left Google, which I thought was a great company, and he became a venture capitalist.
I was like, "Satya, why are you doing this? Why are you going to be a VC?" And Satya, of course, now is an amazingly successful and one of the top seed investors in the valley as part of a firm called Homebrew, which he co founded. And Satya told me, "Gokul, I like working at Google, but what I really like is working across a bunch of different problems across different spaces with different entrepreneurs."
And he said, "well, you know, why don't you try it?" I said, "well, I don't know. I I'm really busy." He's like, " We're leading our investment in a company called World Golf Tour. It was a virtual golfing game. Why don't you look at it if you're interested in investing?" And I said, "well, that seems interesting."
And so just working with Battery and Satya to basically look at this company World Golf Tour. And even though I don't play golf, I'm an avid golf watcher. So I love watching golf. I don't have the time to go out to the golf course. I hit balls occasionally. It was a great entrepreneur. Really liked the company.
Really liked the product itself. And because Satya and Battery were investing, I decided, you know, let me make an investment and at the very least I'll get to learn more about the art of company formation and stay close. And that's what happened. I ended up doing it. Yeah. It really just got me excited about helping entrepreneurs, being involved in early stages of a company formation, supporting them.
And it's all started with Satya. So Satya is either to credit or to blame for my becoming an angel investor.
[00:09:53] Gopi Rangan: This is very interesting. When you make these angel investments, what I hear is that you're looking to connect with people that are building interesting things.
So that kind of sparks some ideas in you and you keep your mind fresh. But what kind of people do you like to invest in? Are they people like you? Are they people who are very different from you? What do you look for?
[00:10:15] Gokul Rajaram: Hmm. Good question. What kind of people do I like to invest in? I think I look for two characteristics of founders.
One, I I think Paul Graham came up with this term 'relentlessly resourceful'. Relentlessly resourceful means the founder will do anything possible to surmount an obstacle. They will never give up. They're going to figure out how to move heaven and earth to get around the problem.
Grit is another way to look at it, or just never give up. Walk through walls. Do whatever it takes. So that determination to just break through walls. They're just hellbent on achieving success. You cannot stop them. You almost feel like there's a gravitational pull towards them when you meet them, when they describe what they've gone through.
So you want to, for example, assess this by asking them for examples of tough problems they face in their life and how they've overcome it. It could be in life, it could be in their career, it could be personal. And you want to see: have they been really resourceful? Have they used whatever they can to do that?
Obviously, another way is to see them in action if you work with them. So I look for relentlessly resourceful people. The second thing I look for is founder market fit. By this, I mean, the founder has a unique non-obvious insight about the market. Non-obvious is very important.
It can't be something that you or I have just read in TechCrunch or some blog. And we saw the container market, which is in a computer technology infrastructure is x big and here's the player that that's not an insight. But if you say the container market is prone to disruption because this is the weakness in the market, and this is the existing players. And it can be disrupted by the specific need which customers have and existing players are not meeting, but it's very tiny today, can be much bigger. And here's how I know this because I was a buyer of these products or a user of these products before. That's an interesting insight that only people who actually encountered this problem in their work or in their life can come up with. That's why I think the best way to start a company is not by sitting in a room and iterating and bouncing off ideas with other people, but actually to just work and live life and keep your eye open for problems that you encounter in work or life and then say, Hey, is there an interesting product or company here that can tackle this problem?
[00:12:34] Gopi Rangan: Can you pick maybe one or two examples and show how you test for these two things, how entrepreneurs are relentlessly resourceful, and how you look for that founder market fit? What comes through in those conversations?
[00:12:48] Gokul Rajaram: Yeah, let me take an example, a company called Indigo Faire. The founder, Max Rhodes, was a product manager at Square. He was instrumental in launching many of the top products at Square. And at the last part of his career at Square, he worked for me on Caviar and he was a product manager on Caviar for the consumer product, consumer set of Caviar as a product lead for it.
Max is someone who literally, when given an outcome or a metric to hit, he will figure out what it takes to hit the metric. For example, we said "we need to figure out how to scale user acquisition without spending money on traditional channels." He figured out how to build a referral program and just scaled it so fast, so quickly that we almost fell down. We couldn't support the volume. We couldn't support that scale. And that's the kind of person that Max is. Every person who's managed him knows that given an outcome, given an objective, this person, Max is going to do whatever it takes. He just cannot eat, sleep, or breathe unless he's just thinking about the problem all the time.
He even got me and our board member, Roelof Botha at Sequoia, to brainstorm about how to grow this program. That's the kind of person he is. And so I knew that when he told me he was planning to leave Square a few months out, that I wanted to invest in his company, whatever the company is, and made sure that I gave him opportunities. You know, when someone's wanting to leave the company, my philosophy on that is that you don't just say, "well, what will it take to get you to stay here?"
If their mind is made up, you want to support them. And so I said, "Max, what can I do to support you?" He said, "I want different kinds of experiences besides just product general manager, sell experience, et cetera." And so, you know, we gave him those experiences in the last six, nine months at Caviar, but he was kind of the GM of our new corporate business unit that we were starting up.
He did a great job there and I think it gave him some good experience. It was good for him and for Caviar. So that was relentlessly resourceful where, you know, we knew, I knew from experience that he was this kind of person.
But I'll tell you about founder market fit with Max. The first 6 - 9 months after leaving Square, he was brainstorming a bunch of ideas.
Exactly the wrong way to go about it, in my opinion. He was brainstorming, there was an auto insurance idea that he had, another idea around something in the dental space. You know, it's basically, he heard about the problem from someone else, and I think he was exploring it. It was all very academic, and I think that's why I'm very happy he didn't start a company on any of those things.
What happened at the end is that he realized he was running a business all through Square. He had graduated from Yale many years ago before Square. And he was running a business. He was, he started an umbrella company. It built these custom umbrellas, really high quality umbrellas. I don't know how he got into that, but he was running this company as a side side business all through Square.
And the big challenge he faced an umbrella maker was that it was very hard for him to find, beyond his own website, retail stores to stock this umbrella. And how does he go and sell to these retail stores? It's very hard. He has a job at Square. He's making umbrellas. How does he find retailers and how do retailers find him?
Very hard. He knew he has a good quality product, but he needs to get connected to retailers. So he thought, "Hey, you know, I have this pain point. Why don't I work on something? Is there enough other people who have this pain point of them being manufacturers not being able to reach retailers?"
And the more he dug deeper into it, he learned, yes, there's tons of manufacturers who are able to connect to retailers. They would love to have the product stock to retailers. They don't know how to connect with them. And then because he had been at Square, he was able to connect to local retailers, and the retailers had the exact same problem, which is they don't know which products to stock. They don't know how to get access to products. And they basically are worried that if they stock a product, the reason the fundamental reason retailers would not stock Max's product is because what if it doesn't sell? Then they're stuck with inventory that basically they can't sell. And they have to write it off. You know, for a small retailer, it's very painful to do that. They'll be out of business. So they only stock the same old, same old versus trying some new products which could be good for sales.
So that's a problem he said, "you know, I'm going to solve this because I feel I've faced it myself for years." And that was the origin of Indigo Faire, which became Faire later. And so that's a great example of founder/market fit. Solving a problem you felt deeply. And he didn't realize he had this problem. It's when he really said, "I'm going to start a company" and he was brainstorming all these other ideas and he realized, "you know what, I have this problem, crazy problem, painful problem. I should solve this problem."
[00:17:13] Gopi Rangan: This is very interesting. The part that you mentioned where he went through an academic exercise after he decided that he wanted to start a company.
And he went through a lot of ideas and researching those ideas. Eventually he landed on something that he was already passionate about. And that's a great fit for a founder where the founder already knows the space enough to know that there is some possibility for a creative solution. I resonate with that and I see that quite often with startups. You have made more than a hundred angel investments. Are they all teams with people that worked with you in the past, or do you also invest in companies that you haven't met the founders. You haven't had a strong relationship with them.
[00:17:54] Gokul Rajaram: No, I think it's impossible because with that many investments, there's no way that I could have invested only in founders that worked for / with me.
I think a good example is a company called Emailage. And the reason I got to know this company was when I joined Square after about a few months of getting on boarded to Square and settling down, I basically would go and talk to different teams at Square. And the risk team or the payments team would basically do these checks.
One of the big challenges that most payment companies have is when somebody applies for a payments account, how do you make sure they're not just a fraudster who's setting up an account to get access to, you know, a card reader to basically then defraud customers or whatever the case may be.
And so fraud and risk and making sure we know identity of a person so that they can't sign up with many different identities, very, very important. And email address is a very easy way for people to kind of defraud you and you can create lots of email. It's a very easy vector. One of the tools that the Square payments and an onboarding team was raving about was a company called Emailage.
So someone applies for Square and Square will send that email address to Emailage and Emailage returns a risk score for that email. That risk score tells you what is the degree of risk on a zero to a hundred scale off about the scale? Exactly. But if it's very risky, not very risky, low risk, et cetera.
And they were almost complaining about the product because they were like, it's such a good product, but it's almost a lock in product because the more data we are sending to them, the more they're getting smarter because all the companies that they work with, they were apparently working in all the companies, the reason they were able to do this is because they built a database of email addresses and risk profiles from all their customers.
So in some ways, it's a self perpetuating database of email address and risk scores, which is all being fed by their customers. And so in order to access the database, you have to also give back your risk score. So Square had to give back, "Hey, you know, what did I learn about this email address?"
Was it risky or not? Any signals that we captured? And so Emailage was over time able to build this great defensible asset. And so I heard about this and I was thinking that's interesting. And then just a few weeks later, serendipitously, uh, Felicis Ventures, which is a venture capital firm, emailed me saying, "Hey, we are leading a round in this firm company called Emailage.
Uh, would you like to join? There's some space for angels." I was like, "Hang on. Emailage? You mean the email risk company?" They were like, yeah. I was like, "Oh my gosh, you know, this is a company that's used by Square." Then I didn't even meet the founder, but the product and the customer love for it was so strong and I did get to meet the founder after I committed. But I knew that the product was amazing. And that is a reflection on the founder that built a product that got a company like Square, which is a very conservative company in terms of adopting something that's in the payments flow.
That's a pretty high bar there, but still they were using it and had been using it. That's the opposite example where I didn't know the founder at all, but because I had unique insight into the founder/market fit, which was evidenced by the product itself, I invested in them.
[00:20:55] Gopi Rangan: Oh, you, you are talking about something that's, uh very unusual. Often we hear that, especially at angel investment stages, when there's really not much to show, it's the charm of the entrepreneur that wows investors and others also, other early believers.
But here in this case, you never met the entrepreneur until you mentally formed the conviction on this. It's the product and the solution, the objective view on what it can do. That really impressed you.
[00:21:25] Gokul Rajaram: Yes, exactly.
[00:21:27] Gopi Rangan: That's not the usual story we hear with angel investments. It's very interesting.
[00:21:32] Gokul Rajaram: Yeah, it's different stages, you know, different stages.
[00:21:35] Gopi Rangan: How is the portfolio doing? You've made a hundred angel investments. What expectations do you set for entrepreneurs when you make those investments? Do you expect to generate huge returns? Is that a motivation in addition to other things you mentioned?
[00:21:46] Gokul Rajaram: For me, the motivation is threefold. I think everyone does angel investing with different reasons, but I think if it's done only for financial reasons, I don't think it's the right frame of mind. I think you won't be a great angel investor. Because in angel investment, there's a lot of work needed and it's also being part of a community. If you're too focused on financial returns, entrepreneurs get turned off by that. So I do it for three reasons. Financial is the last one.
The first one really is around giving back to the community and being part of the community. I want to be part of the entrepreneurial community. That's what I really enjoy doing. And this is my way to give back to the entrepreneurs. I know I support and I want to keep doing that regardless of I made investments that I am almost certain that the company maybe will not be a massive outcome or anything else like that.
But I know the entrepreneur, I want to support them for various reasons, and, and I will do that. And so that's, that's the number one thing: giving back, being part of the entrepreneur ecosystem, being part of the entrepreneur community. Second one is learning. For me, learning matters a lot.
Every company I work with, every founder I work with, I try to see what can I learn from them that I can bring back into my day job. I do work at DoorDash, for example, and I do see a lot of things that can benefit every company I've been at, that can benefit from my angel investments and from companies I've worked with.
So, and then financial returns. And so I think every one of us who's doing angel investing has to think about what really matters and why are they in it. But financial returns as the number one thing is the wrong thing. I think it's probably the number two or number three things, but something like learning, giving back, et cetera, is probably the top thing you should focus
on.
[00:23:19] Gopi Rangan: How are you doing on all those three metrics with your portfolio?
[00:23:23] Gokul Rajaram: Y Combinator has a ranking of angel investors and rating of angel investors rather, and, uh, which only the Y Combinator, um, I've made a bunch of investments in YC companies.
And so someone read it out to me and I was quite happy to see, uh, the, the comments that people had made. So it makes me feel that I am contributing and I am a value added number, I should say, of the entrepreneur community. On the second front learnings. I feel that my job, my ability to do my job well has been massively increased and improved as a result of this.
And I have brought tons of insights back to my job and and my company as a result of it. I feel that's probably the strongest of all. On the financial front, it's done very well. I think of angel investing cohorts as annual cohorts. So I'll track it as one of the angel investments I made in say 2010, 2011, 2012, 2013, each year separately and look at the cohort together.
It's too hard to look at one company. As a cohort overall, each of the cohorts overall has done extremely well and has outperformed my benchmark is, say, the S& P 500 or one of the stock benchmarks, and it has massively outperformed those benchmarks. Of course, liquidity, you know, many times things are on paper, so the older cohorts have had liquidity and have outperformed from an actual realized return.
The younger cohorts are outperformed, but much of it is on paper, so we'll see how it goes when it actually comes to returning.
[00:24:43] Gopi Rangan: Oh, that's really nice to hear. As an angel investor, you take the highest risk in the journey of supporting an entrepreneur. This is one of the most important roles that the startup ecosystem values.
So you're doing a fantastic service to the community by actively playing a role as an angel investor. Uh, let me try to summarize what we talked about now and then we'll move to the next part of it. You started with how you started as an engineer, became a product manager, and then became an executive.
And along the way you had your own startups. But you also went through an MBA experience, which helped you transition your career from engineering to more into deeper into product management and especially opening opportunities at companies like Google, Facebook, and later at Square.
The examples that you gave, starting with Juno, how mission was very important and the leadership is also very important. The two are the qualities that you look for in any company before you consider joining them. And that's a great metric to have. I really liked the two filters that you use when you look for angel investments.
You mentioned relentlessly resourceful and the second is founder/market fit and the examples that you gave through Indigo Faire and Emailage showed those type of things that you look for and what what goes on in those conversations.
You did mention watching golf as a sport. I had to resist the urge to pull your leg on that one, but I am going to spend some time to understand how interesting that is. But it's nice to see that you make something out of everything where you are looking for interesting things outside what you normally do.
And towards the end, you mentioned the metrics that you set for yourself with your own angel portfolio: how you can contribute to the community; how you can learn; and how you can generate financial returns. And it was very clear that financial returns is not the main motivation.
Well, we can certainly talk more, uh, for a longer time, but I want to switch to the next segment where I ask you about community leadership. Is there a nonprofit organization that you're passionate about?
[00:26:50] Gokul Rajaram: Yes. So I contribute to many. One that we've gotten involved with is an organization called Second Harvest of Silicon Valley. We support it both through giving as well as, uh, through volunteering. Its work is about making sure that people have access to the most basic need. If you look at Maslow's hierarchy, most basic need, which is food. It is one of the largest food banks in the nation and provides food to more than a quarter of a million people every month.
And due to COVID now their work is even more important as people have lost their jobs, become homeless, etc. And so more than half the people they serve are kids and seniors. I've been very impressed with their mission, with their execution, and overall hope to be involved, and over time I've developed an appreciation of food banks across the country and the critical role they play.
[00:27:41] Gopi Rangan: You would think that Silicon Valley, which is one of the most prosperous places in the world, would take care of everyone around us, but it's sad to see a lot of homelessness and a lot of people struggling for food. It's great that you support this organization. Gokul, thank you so much for your time.
A lot of insights in this episode. It's always great to talk to you and learn from your experience.
[00:28:04] Gokul Rajaram: Gopi, just talking to you as a treat and I'm excited to be part of this podcast. And thank you very much for having me here.
[00:28:13] Gopi Rangan: Thank you for listening to The Sure Shot Entrepreneur. I hope you enjoyed listening to real-life stories about early believers supporting ambitious entrepreneurs.
Please subscribe to the podcast and post a review. Your comments will help other entrepreneurs find this podcast. I look forward to catching you at the next episode.