#105 20 Minute Playbook: Gokul Rajaram – Prolific Angel Investor and Product and Business Helper at DoorDash

Gokul Rajaram is an angel investor and Product and Business Helper at DoorDash. In this episode, Gokul and Daniel discuss crypto, international investing, and habits and routines.
Last updated
August 13, 2023
Min Read
In addition to his work at DoorDash, Gokul is an active member of several Boards, including Coinbase, Pinterest, and The Trade Desk.
More ways to listen to Outliers
Episode artwork

#105 20 Minute Playbook: Gokul Rajaram – Prolific Angel Investor and Product and Business Helper at DoorDash

“I always believe the hierarchy of anyone, any individual should be health, then family, then work. Why not family before health? Because if you're not healthy, you become a burden to your family and you can't help them. So, your health is actually very, very important.” – Gokul Rajaram

Gokul Rajaram (@gokulr) is an angel investor and Product and Business Helper at DoorDash. He started his career as a Technical Lead at Juno, and has since led product development at Google, Facebook, and Square. He is an investor and advisor in many companies, and is an active member of several Boards, including Coinbase, Pinterest, and The Trade Desk.

Topics discussed with Gokul Rajaram

  • 00:01:21 – The evolution of crypto
  • 00:02:44 – Superpowers and struggles
  • 00:06:08 – Inspirations and the importance of exercise
  • 00:08:24 – Recommended books
  • 00:10:19 – Tools and routines
  • 00:12:26 – Defining success
  • 00:14:32 – International investing

Gokul Rajaram Resources

Books Recommended in This Episode


Daniel Scrivner (00:06):

Hello, and welcome to another episode of our 20 Minute Playbook Series, where each week we sit down with an elite performer from iconic founders to world-renowned investors and bestselling authors to dive into the ideas, frameworks, and strategies that got them to the top of their field, all in less than 20 minutes. I'm Daniel Scrivner, and on the show today, I'm joined by the one and only Gokul Rajaram. He's a prolific angel investor in over 300 companies in counting, and an executive at DoorDash, which he joined after DoorDash acquired Caviar from Square in 2019. I was fortunate enough to get to work with Gokul at Square, and I am beyond thrilled to have him on the show today.

Daniel Scrivner (00:40):

In this episode, Gokul shares what he thinks his investing superpowers are, why he loved Marc Andreesen's interview on the Good Time Show, why he loves Andre Agassi's book, Open, and the advice he'd give his younger self if he could go back 20 years to the start of his career. You can find the notes and transcript for this episode at outlieracademy.com. 105. That's 105. You can follow Gokul on Twitter, which I highly recommend, at GokulR. That's G-O-K-U-L-R. With that, let's dive into Gokul Rajaram's playbook. Gokul, I'm thrilled to have you back on 20 Minute Playbook. Thank you so much for the time. Thanks so much for joining me again.

Gokul Rajaram (01:19):

Thank you. Good to be here, Dan.

Daniel Scrivner (01:21):

So, this is a little bit faster paced than the long-form interview that we did. I'm going to ask you the same 10 questions that we asked to every guests, and we're going to try to do this in 20 minutes. The first question is around a recent fascination. Is there anything that you've been fascinated or obsessed by recently?

Gokul Rajaram (01:38):

I would say crypto, but it's been probably two or three years that I've been fascinated by crypto.

Daniel Scrivner (01:43):

... and confused?

Gokul Rajaram (01:45):

Yeah, I think it's just the evolution of crypto, I think. The NFT, the rise of NFTs, the just the myriad ways in which essentially the Web 3 world has just sprung it. Right now I'm fascinated by, I'm seeing essentially that every web to infrastructure product, whether it's analytics, CRM marketing, email even, messaging is being rebuilt in Web 3. So, I'm trying to uncover what are the other Web two protocols or infrastructure layers that have still to be built for Web 3? So, it's been really fascinating to me to see really be rebuilding of all of these things that have been built over 20, 25 years for Web 2. Now, within like two years or a few months, they're being rebuilt by entrepreneurs.

Daniel Scrivner (02:32):

Yeah. It's a very short time. I know, and you're certainly see companies too that are, have this kind of hybrid Web 2- Web 3 model where it's like we have traditional cloud infrastructure, but also blockchain. It's going to be interesting, I think, to see those play out as well, too.

Gokul Rajaram (02:44):


Daniel Scrivner (02:44):

Yeah. I love that. Second question is around your superpower, and I think that what we're trying to get at there is, we're all uniquely gifted in some ways. What do you think your superpowers are, and how do you harness those? How do those show up day to day?

Gokul Rajaram (02:59):

It's a good one. I don't know. I don't know if I have any, but if there is one, I think it is to be able to take almost any, I would say business problem, and be able to find a way forward to solve it. So, I think it's problem-solving, business problem-solving around taking a business outcome and being able to brainstorm a few different ways in which we can have customer behaviors. The other one is really breaking down a problem. I think I never felt that I, when I was an engineer, I would be given a very specific problem to solve, and I would solve it. I really want to learn how to be given the more open-ended problem, and figure out what are the ways to solve it versus just doing X. I trained myself, I think over several years. So, I got better at that, which is taking open-ended problems, and putting structure around how to solve them, maybe the best [inaudible 00:03:56] particulation.

Daniel Scrivner (03:56):

Yeah. I think that definitely qualifies as a superpower, and I also love no one's no one's given that answer before. So, I love that. On the flip side, what do you struggle with, and this is just this concept that no matter how talented, no matter what we've been able to achieve, we all struggle with some pretty fundamental things. What do you struggle with, and how have you worked around or improved those things over time?

Gokul Rajaram (04:15):

Saying no. Saying no to people. I want to help people, so when anyone reaches out, my first reaction is to say yes, and the problem is there's only X number of hours in the day, X number of days in the week. So, I have started using, over the last few months, calendar to really prevent me. I literally block off times where I need to do deep work myself. I can't be in one on ones with folks. I can't meet with folks. I'm also putting guardrails around the number of hours I spend meeting with entrepreneurs or meeting with other folks versus working myself on stuff that matters, because if ... Yeah, so I think not saying no, to be honest, has been the source of many incredibly serendipitous discussions, meetings, and great things that have happened, but also leads to incredible amount of stress around time management and being able to be productive.

Daniel Scrivner (05:05):

Yeah. Well said. I identify with that, and I definitely agree. It's a two-edged sword. Is there any book? Is there anything you read or listened to that helped you get better at that? Like, what comes to mind is you talk about saying no is The Courage To Be Disliked, which has been on my reading list for a long time. I haven't read yet.

Gokul Rajaram (05:21):

I think it's, there was a podcast with Marc Andreesen, which was done on the Good Time Show, I think by Sriram, who's now at [inaudible 00:05:29]. I think that really talked about how Marc essentially uses calendaring to completely manage his day. Everything, anything he needs to do is on calendar. So, it inspired me. I was doing some soft version of it, but I became much harder-core about saying, well, if I have to do something, if I'm doing meetings and they're on calendar, why does almost everything I need to do not be in calendar? So, it should be half an hour block or one hour block on calendar if I have to do something. So, I've started being much more aggressive with calendaring things and saying, well, you're going to do this now. You've got to eat the frog in the morning. So, eight to nine, you've got to write whatever it is you've got to write, this memo or document or performance video, whatever the case may

Daniel Scrivner (06:08):

Yeah. Thanks for sharing. Is there, I want to talk about habits and routines, and the way I'm going to frame this up is as I've explored how people have incorporated habits and routines, what I found is there's a massive spectrum, and actually most people, I don't think, are very focused on habits and routines. So, what I want to try to ask now is kind of scoping it way, way, way down, and just ask the smallest version of the question, which is what tiny habit of routine has had the biggest positive impact on your life. This could be at work at home, any angle.

Gokul Rajaram (06:38):

For me, it's been exercising six days a week, five to six days a week, has had the biggest impact, because I've seen that, I always believe the hierarchy of anyone, any individual should be health, then family, then work. Why not family before health? Because if you're not healthy, you become a burden to your family and you can't help them. So, your health is actually very, very important. Then your family, because you can't help [inaudible 00:07:03], and then finally, work. I think many of us who have families and who work quite a bit ignore health, and you don't realize how much just focusing on your health has a trickle-down effect on making you just happier, more productive. Even things that are not, you don't feel excited about, you feel more excited if you're healthy.

Gokul Rajaram (07:24):

So, being able to just have some kind of exercise, five to six days a week on a consistent basis has been the most transformative thing I've done. Probably a common thing, I'm sure many people have said on your show, but for me, it started when I was starting to commute to Square nine years ago, where I realized that by day I would no longer just have a ... I live in the South Bay area, would no longer just have a 15 minute commute. I would have a one hour commute, which means two hours of my day was taken up. 10% of my day was taken up by commute. So, I needed to really find time to exercise before getting into the car. I started doing that, and that persisted hopefully, thankfully, over the last nine years.

Daniel Scrivner (08:01):

Yeah. I feel like exercise is one of those things, counterintuitively too, that a lot of people don't have time for it. Yet, what I find is when I make time for it actually gives me time back in the day. Because to your point, I'm more productive. I show up just in a better version of myself.

Gokul Rajaram (08:15):

Look, it's a date with yourself, essentially. So, give yourself a treat and put, if you can do a one on one with someone else, why can't you do a one on with yourself for a half an hour?

Daniel Scrivner (08:24):

Yeah. That's well said. Okay. I want to talk about favorite books, and what I'd be curious is if you find yourself sharing the same books, the same types of books with founders and investors that you work with, and just if you have any all- time favorites. This can also be, these don't have to be business books. It can be anything.

Gokul Rajaram (08:42):

My favorite books are things that are written, that are written with a point of view, and have more of a storytelling nature to it. In addition to teaching, they also entertain. So, The Hard Thing About Hard Things, which is Ben Horowitz's book, is probably my all-time favorite book, because it just has such a, because people remember stories. That's why I tried to read a few years ago, I started to read book summaries, but book summaries take away the stories that underlie the books. So, you don't remember it, because you remember the stories and not the actual lesson. So, The Hard Thing about Hard Things.

Gokul Rajaram (09:17):

Then, the other one I really like is a book called, Open, by Andre Agassi. That book is just, he starts with talking about how he hates tennis. He truly hates tennis, and having somebody who's one of the greatest ever to play a sport saying he hates a sport, and why he hates it was just, just incredibly powerful to see how overdoing something can lead to this love-hate. Everyone has a love-hate relationship with what they do in some ways. So, it's given him so much, yet, he hated it in many ways. He also loved it.

Daniel Scrivner (09:50):

I love that you brought up the point about book summaries, because I similarly have tried those, as has I think anyone who's pressed for time. I think my experience of it reminds me of the quote of, I was listening to an interview with Tony Deden, who's an investor I really like. He talks about one of his, the thing he harps on a lot is, man's constant search for getting something without expending any effort or any energy. I feel like that's the perfect definition of book summaries, because you're not investing in it. You're not really going to get anything.

Daniel Scrivner (10:19):

I want to ask about tools now. Typically, we talk about software tools. I don't see it today, but I know back in the Square days, you would keep a field notebook in your pocket all the time, and just have this notebook that was with you constantly. So, I would be curious, do you still have kind of paper and a notebook is a big part of your, the tools and the way that you do work, and you kind of think and write down to- dos, and if there's any software components or any of those worth sharing.

Gokul Rajaram (10:47):

I replace, because I don't move around as much. I mostly in at home, and I sometimes going to work, rarely. I use my phone and the notes app as substitute for that. So, I basically update my notes app on a, basically on a constant basis. I don't use any fancy things. So, notes is, it's a close as it looks like the most [inaudible 00:11:07] thing. You can kind of configure it a little bit, and it has check boxes. I checkbox after I do it, digitally. So, it's basically the, it's become a proxy for basically carrying around the book, because I always have my phone on me.

Gokul Rajaram (11:20):

So, I'll quickly jot something down. So, basically, I have a note that is the to-do for the day. It's essentially, the biggest discipline there has been to cut down the to-do to two or three versus to have 10, because you got to like, do you know what the top one or two things are that you need to get done today? Then for everything else, I use just a different note, but really every day, the biggest struggle is, what are the top one or two things, that if you do, that you feel you had a good day, and made progress.

Daniel Scrivner (11:51):

Do you have, as part of your routine, doing that the night before, or do you try to make time to do that in the morning? Is there a specific time you do that kind of prioritization?

Gokul Rajaram (12:01):

In the morning, when I wake up. In the morning, when I wake up, that's one of the first things I do within the first half an hour of waking up. Exercise, toothbrush, et cetera, and then basically, what's got to be done, and exercise actually plays a good clarifying goal, because you can get a lot of stuff out, and you can think about it and then you are like, you're determined, and it actually gives you more motivation. Write down that big thing that you've been maybe dreading. I'm going to do it. [inaudible 00:12:26]

Daniel Scrivner (12:26):

Then the rubber meets the road, and you have to actually put down the list, and start checking things off. I want to talk about success, and what I want to talk about there is your definition of success, and how that's changed over time. I think for you, it would be really interesting just to talk about that at the highest level, because you do a lot of things. You're an investor, you're an operator, you have a family. What does success look like for you today, or how do you think about that? Then how has your definition changed over time?

Gokul Rajaram (12:53):

Yeah, I think again, 15 years ago, I would've said success means to run a large organization and to essentially be an important part of an organization, et cetera. But now, as I really crystallized it for me, the most three most important things are health, family and work. Success truly follows on that dimension. First is, be healthy. Anyone, all of us have gone through injuries or whatever it is, or had pain, and only when, I've seen that we really don't think about how lucky we are to be healthy until we have some terrible pain or physical. So, it's really to be physically and mental ... I think all mental health is just as important, I think, as physical health. So, be physically mentally healthy and active, number one. Number two is essentially make sure that I'm there for my family and see my kids succeed, do well, be happy in whatever they want to do, and have a good relationship and have a loving relationship with my wife and parents and just general family.

Gokul Rajaram (13:53):

The third one is, I think, at this point success at work for me is about being helpful and being known. I think if I were to distill it, it would be being known as a value-added, helpful part of the broader tech ecosystem, globally. I think I would probably initially have said just the value a few years ago, but now I've worked with many entrepreneurs across the world. So, I want to have a, be known as someone who's basically helpful. [inaudible 00:14:22] if we come here, I work with, I say my goal is not to make money off of you. My goal is to really make sure that you think of me as one of the top, most helpful people on your cap table.

Daniel Scrivner (14:32):

Yeah. As someone that knows a few of the founders that you've invested in, I think you already have that reputation. So, I think you've got a good head start there. I want to ask one followup question, which is, I know that you alluded to it there, that you've been investing, working with more founders, entrepreneurs around the world. I want to just stop for a second and ask the question of one, what are you seeing there? What excites you there? Then I think just for people that maybe don't spend as much time focused outside of the US as inside of the US, just share a little bit of what that perspective gives you, what it shows you about the world and about founders around the world.

Gokul Rajaram (15:09):

Yeah. To be honest, until March of 2020, 95% of my investments were in the US. As soon as Zoom happened, COVID happened, literally the whole world opened up, and didn't matter whether the founder was staying in Bogota, Columbia, or Jakarta Indonesia or Bangalore, India or New York, they all were essentially the same at that point. What I realized was two things. One, founders across the world, just because of the rise of internet and just information dissemination, they're just as hungry just as now, I would say, aggressive like it's visionary. They work just as hard as the best founders in the US, the best founders across the world now are at par with the best founders in the US. Second, the market opportunity, I would say in the US, there is like, there's tons of companies being started. I think still the number of companies per capita is much lower in these countries.

Gokul Rajaram (16:06):

So, each company has a much bigger opportunity to win. In other words, for example, if you look at all of Latin America, there's 800 million people across these countries. Similarly, India is 1.1 billion people. In Southeast Asia, Indonesia itself has 300 million people, more than 300 million. So, each of these regions is massive, but the number of companies attacking these problems are much smaller. So, then I think, coming from the US, I think folks who are in US, you don't know how much they value your lessons, your experience, et cetera. It's incredible. So, competing with like thousands of investors and advisors to get attention of a value company versus it's, they're hungry. They reach out. They're much easier to kind of, I would say, get time with, because they want that time. So, I think there's a lot of benefits to having to working there. We just, it takes you back to simpler times.

Gokul Rajaram (17:04):

I mean, they're just focused on, also, the Maslow's hierarchy. There's many basic ... in the US, I think many of the infrastructural challenges have been generally solved. I think many of the companies are doing more self-actualization kind of things you would say. But in most of these countries, basic fundamental, infrastructure, things are being created. So, you also feel like are truly having impact on the lives of people in foundational ways, much more so than in the US. That said, I mean, the US is still the epicenter, but these regions together, I think 50 ... I almost say that if you're an [inaudible 00:17:40] probably 50% in the US, 50% rest of the world.

Daniel Scrivner (17:45):

I love the points you made. Last question. I'd be super curious to know what advice you would give to your younger self. So, if you could go back even to Gokul in 2002, and whisper just a couple words, either of encouragement or just a reminder to yourself, is there anything you would tell kind of a younger version of yourself?

Gokul Rajaram (18:05):

Be curious. Continue to be curious. I think curiosity, and be open to new ideas. I think that's something that I need to keep reminding myself, because as you get older, you sometimes get jaded ,and you realize that you sometimes you're, well, this has been tried before. I think that danger with pattern matching, I'm an investor in enough companies that I'm like, well, I've seen that movie play out before, but every time it's a different outcome. Jack started a company. Jack and Jim started a company in payments, one of the worst areas that a company ... Hundreds of collapses, graveyard, one of the best companies, iconic company. The same is true for something like Grocery, where Webvan and Instacart a decade later. So, I think from first principles, don't be influenced by patterns. Use the right lessons, but don't just ignore new ideas or ideas that have been done before, just because they've been done before. Look at the entrepreneur. Always be people first.

Daniel Scrivner (19:00):

Yeah. So well said. Thank you so much for the time Gokul. For anyone listening. I highly encourage you to follow Gokul on Twitter. You can find him at GokulR. G-O-K-U-L-R. Thanks for of the time Gokul. This meant a lot. Thanks.

Gokul Rajaram (19:11):

Thanks. Thanks again, Daniel.

Daniel Scrivner (19:11):

Thank you so much for listening. You can find the show notes and transcript for this episode at outlieracademy.com/105. that's 105. For more from Gokul Rajaram, listen to episode 102, where he joins me on our investor spotlight series to go deep on how he thinks about product management, and his incredibly popular Spade Framework for making transparent decisions as a company. In that interview, we cover what product vision and leadership looks like in action, the difference between product managers and analysts, how his Spade Framework came out of a failed meeting with Sergey Brin, Larry Page and Eric Schmidt at Google, and his advice for teams from how to test your hypotheses with no code tools and no engineers, to why small teams win, and why speed is the ultimate competitive advantage for startups.

Daniel Scrivner (19:59):

You can now also find all of our interviews on YouTube at youtube.com/outlieracademy. On our channel, you'll find all of our full-length interviews, as well as our favorite short clips from every episode, including this one. So, make sure to get notified whenever we share new videos each week on YouTube. Thank you so much for listening. We'll see you right here next week on Outlier Academy.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outlier Academy, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

Enjoy reading this? Share it.
Be the first to receive new articles and episodes as soon as they’re released.
Popular Articles
Be the first to receive new episodes when they’re released. And get our favorite quotes, tools, and ideas from the latest episode.
You're in! Thanks for subscribing.
Hmm, something went wrong. Can you try again?
By subscribing, you agree to our privacy policy.