Fireside Chat with Gokul Rajaram

She wrote, uh, Be Brave. I think Brave is the name of the book. It's a good read. I will channel her and encourage you all to read it.

Are you recovered from Demo Day, Reshma, or is it still crazy?

It's nuts. I've silenced all my notifications and stuff, so I think I got all of them, but, um, there were only like 35,000 insurer requests.

You know, not that many.

So we had this bug in the Demo Day website where it was fixed with, and then one of the elements was the number of intros and like, cause it was growing so fast, the site was flickering. Oh gosh. To fix it right before it was, uh, good times.

That's amazing. It's a, it's a not a bad problem to have.

Yeah. A lot of fun.

Good morning, everyone. Thanks for organizing, Reshma. I got my MIT mug here. This is 9 years old, but— oh, you guys can see it right now. Gokul, good to see you too.

Great to see you, Vivek. Good to see you, Bradley, Ricky, Peter. Lots of familiar friends and folks here.

Nice. Yeah, I would say with that, let's go ahead and get started. Start with some intros and take it away with the fireside chat. Yeah, that sounds good. Let's see. So first of all, everyone, welcome to Startup Track. It's the MIT Club of Northern California community for founders, employees of startups, investors, and advisors. And super excited to have everyone here today. We're experimenting with the timing. So thank you all for getting here early in the morning. So the club overall has two goals, of course, to provide a community for MIT alumni. And also, we provide scholarships for students who come from the Northern California region. And we provided over 200 scholarships for needy students to date. So thank you all for coming to a paid Zoom talk. Know that your proceeds go to a good place. And thank you for supporting students. So just a quick plug for the— For the club, we have a lot of online materials. Let's see. First of all, make sure to come to our website, and particularly for founders and for employees, if you are an MIT alum, we're trying to build up our online muscle for the startups that we support, and we put you on a list, a Twitter, Twitter list so we can like keep track of everyone. And so if you have a startup and you are an MIT alum, DM or tweet at us and we will continue to add you to the list so we can just have everybody celebrate your successes and be in contact. On to the main event. Hi everyone, I'm Reshma and it's my pleasure today to introduce Gokul Rajaram here as our Speaker for our fireside chat. So Gokul is served on the— currently serves on the executive team at DoorDash since November 2019, after DoorDash acquired Square's food delivery business called Caviar. And prior to DoorDash, he worked as the product engineering lead from 2013 to 2019 at Square, and he led several development teams and served on Square's exec team. And then before Square, He was a director of product for ads at Facebook, which is how I know him, from 2010 to 2013. And he helped Facebook transition to become— for the ads to go from on the desktop to mobile first, which was like a very, very big deal at the time and continues to be like an incredible business. Earlier in his career, he was on the PM team for Google AdSense. And helped it grow where it's now also a juggernaut. And he served as a— he currently serves as a director of Coinbase and Pinterest and Trade Desk. So a lot of great experiences. And we're thrilled to have him here at the club. So it's a funny story. We have extended an invitation to Gokul to speak at the club several times. But the companies he's at, they keep IPOing. So they go through a quiet period, and he can't come speak. Now the waves have parted, and we have an opportunity to meet with him today. So thank you again, Gokul.

Thank you very much.

And about me, I'm Reshma. I'm one of the volunteers here at the MIT Startup Track, CMC Startup Track, and currently a visiting partner at Y Combinator. So let's kick it off. So Gokul, question 1, you play a lot of roles, obviously. Public boards, you advise a lot of startups, and you currently work at DoorDash. Can you give us a sense of like how you spend your time?

Yep, I work full-time at DoorDash, so most of my time, I would say 80-90% of my time, I spend on DoorDash-related things, related projects. I meet with companies and founders during the early mornings, nights, evenings, late evenings, and weekends. So probably 10 hours a day. I think it's kind of crazy if you start counting up hours, could be 60 to 70 hours, but 10 hours a day, 8 to 10 hours a day on DoorDash stuff, and then 2 to 3 hours a day on founder and company stuff, typically at the extremes of the day. I've used calendar a lot, very aggressively. So when I have to get stuff done, I calendar a meeting with myself to block out a piece of, a chunk of time to get stuff done. And I also aim for inbox zero. So that's in order to— the number of commitments can very quickly swallow your time unless you are very, very aggressive with your time, because it is the most scarce commodity that all of us have. So you just need to have your own set of tools around how to make it work.

And so is it kind of like, do you think of your day as a normal workday, 9 to 5-ish at DoorDash, and then evenings are helping startups, and then you have like big time blocks to work on board activities? Is it something like that?

That's, I think it's very close. The board activities happen once a quarter for the most part, where typically most public company board meetings will happen during the same week for some reason, because they all report earnings the same time. So they typically have board meetings a week or two before. So you'll see a certain week, uh, and it happens during the middle of the day. So a week, basically several days will be taken off, uh, with board meetings. Uh, but other than that, you're absolutely right. It's, uh, 8 to 6, um, DoorDash and those 8 to 6, I have essentially DoorDash meetings, but I've also got to write a lot of stuff because at DoorDash we believe in writing memos. Amazon sells 6-page memos. So I'll always have 1 or 2 memos that I'm working on. So need to block off time to do that. And then in addition, companies, both mornings and evenings. Many companies I've worked with are in either Europe or Asia. And so mornings work well for talking to them. And then evenings are for the US companies.

Wow, what a way to lever yourself up. So you're using the time zone shifting to expand, expand the workday.

Yeah, that's basically right. Yes, next level.

So can we drill in a little bit into the startup time when you're helping startups? So in the evening, like, um, why don't— doesn't the memo style type of feedback work for them? What's the nature of those interactions?

First and foremost, I started helping startups 16, almost 20 years ago when I was at early, within 2 or 3 years at Google, a bunch of startups started reaching out and I just started helping them. And that's my philosophy. But initially when I started helping startups and also started getting on boards, my first board was I think 13, 14 years ago. I was still in the operator mindset when sitting on these boards and I I would almost give them very prescriptive feedback and tell them, you should do this. But over the years, I've realized ultimately it's their company. Whether as a board member or as an advisor, informal or formal, my job is to give advice and they have to make the decision. So I always end everything I tell them with, this is just my advice, it's ultimately your call, because it is ultimately their call. So our job is to give advice, even as board members. Our job is to hold the CEO accountable. That's a fiduciary duty. But broadly, when the CEO or the exec team asks for advice, it truly has to be framed as advice and opinion and thoughts, obviously well-researched, hopefully with a point of view. But ultimately, it's the CEO and the executive team's decision around what they want to do. This is just one piece of advice. They should gather more advice and inputs. So that's, that's a high-level framing. The number one situation that companies face is around people. This is true at the earliest stages, and it's true all the way till for public companies. And hiring people at the early stages, how to hire people well, is something that founders really struggle with and have questions around, especially as they start to bring in executives, and especially in functions that the founders are themselves unfamiliar with. So if it's a technical founder, engineering founder, they may not know how to hire a VP of Sales or how to hire a— sometimes even a Head of Product or even Head of Engineering if you're a sales founder. So they need a lot of help around figuring out how to think about hiring. The second thing they need help with is setting up operational processes, many of them involving people. For example, how to run a one-on-one, how to run all hands, how do I run my staff meetings? Now I have a management team, how do I run my staff meetings? How do I communicate to the company, with the company? Do I do it in a weekly email? In some kind of other setting? What should be in the weekly email that I send out? How do I do reviews and promotions? I have a person who suddenly came and said they're going to leave my company and join Facebook or Google. How do I deal with this? So there's a bunch of planned things and there's a bunch of crazy stuff that comes up. And my advice, I think, it— well, the thing I always try to stress is to have principles or frameworks when dealing with situations. Many founders react when they're faced with a situation, and they do something one-off that they regret later without thinking about the repercussions of the action they take, how it's going to have a ripple effect later. For example, if someone comes and asks you for a promotion or a raise, otherwise they'll leave your company and join some other company, uh, instinctively, if that person is a star, the founder immediately will say, okay, you know, they'll basically say sure, you know, they'll think about it, and then they might negotiate the exact rates, but they'll they'll accede to that. But I think that's a wrong thing to do because you're setting a precedent. And so the right thing to do is to say, look, the review cycle is coming up in 3 months. Typically, every 6 months reviews happen. And, you know, on average, when a person talks to you and has this kind of request or ask, it's average 3 months in the review cycle. Let's discuss at the review and promotion cycle. There's a merit-based review promotion cycle. But if you start doing stuff off cycle, it sets a really bad precedent. And everyone with us at a small company, everyone knows about it. So it becomes very, very hard to keep things contained or secret. It's transparent. So that's— so in general, the capability you need is experiences working with people across many different situations, many different companies, and being able to pattern match. So I've worked at many companies now over the last 15 years and also have involved and been in— seen many situations. So I'm able to pattern match across many different things. I think some founders do need help with very specific functional things, for example, introductions to customers and things like that. And so many people, when they start advising companies, many of you, if you're thinking of advising companies, you typically start in a functional capacity where, you know, you are like an expert in engineering or an expert in sales or an expert in XYZ. And that's how I started out also. I was an expert in monetization because I'd worked at Google on advertising. So there were a lot of media companies back 10 years ago, ad tech companies. So I advised and helped many of them think about their business models. And then slowly you see them and you start becoming a generalist where, you know, any kind of company, you start building competencies that can help any kind of company, not just a company that comes in a domain that you're an expert in. So that's the evolution of being an advisor. You start in a very specific thing. And I think also companies that— my other philosophy I have is paying it forward. Where, you know, you basically— I'm happy to take a 15 to 30 minute meeting with any startup and just give them some thoughts and advice. And I do that on a, you know, part of that time we discussed is actually just meeting with just companies that have reached out and just helping them. And many of those interactions just hopefully help them, and some of those turn into something more interesting. And most, many, many of them just are just an informal help relationship, which is, which is great. And so I think you should just be open to helping. So many people at large companies, you know, want a more structured thing. But I think waiting for these structured things to emerge, it never happens. I think the best way to— if you want to start advising companies is to just put yourself out there. You know, just say, listen, I can help with X, Y, and Z, and just reach out to your friends who started companies and just say, listen, if you need help, I'm here. You know, I can help with this and this and this. And just let me know and just make it completely informal. And if you do a good job helping them, I guarantee you word is going to get out and people are going to proactively— they're going to tell their friends, and then you're going to be an in-demand advisor within a few years. But it takes time. It just takes paying it forward and just being open to opportunities and serendipity.

So if I was to send you 300 startups to pay it forward to, that would be okay?

We'll have to do it one a day for the next year.

Thank you. This is super helpful, I think. Very interesting. I mean, it's also counterintuitive because, like, I'm currently working at YC, and we're trying to get founders to bias towards action, which is actually maybe the opposite of what you're saying. It's like, things are coming at them, they got to keep on, you know, taking action and not be paralyzed in the moment. But in your perspective, there are select instances in time that it actually makes sense to pick your head up, pay attention, and so you don't screw things up for the future. Do you have any framework for like what those events are that need that pick your head up moment?

The simplest framework to use is the Bezos framework of one-way door decisions versus two-way door decisions. One-way door decisions are decisions that are irreversible. Once you make them, you can't really go back. And I think almost everything people-related, if you, if you think about it, it's a one-way door decision because you're setting a precedent, because it's going to happen again and again and again. Two-way door decisions are things that are, you know, many— most things in a company that are not people-related are two-way door decisions. There are some things that are maybe one-way door, but most things are two-way door. Two-way door decisions are things that you can make, decisions that they can make very fast, but you can adjust and adapt as things go along. It's not a set in stone. For example, let's ship this feature versus that feature. You know what, you can ship it to 10%. If it's not working out, you can actually just change course and ship another feature. So those are things where you should absolutely not waste time trying to set principles. Uh, you should have principles around how quickly you test and how much statistical significance you need, but in general, you can do most of the product-related product development work, even many sales things, et cetera. As two-way door decisions and be very, very fast at making those. But one, you've got to be very careful. People-related decisions are one-way door decisions. And then there are some other things around who you raise funding from, who your co-founders are, you know, some things like that that can also become one-way door decisions. So you've got to be very careful about making those decisions, not just take the first term sheet that comes your way, or just because a brand name sounds attractive. You've got to do your diligence, do your work. Before you get a partner for the long term. But yeah, one-way door and two-way door is a reasonable framework to use. For one-way door decisions—

Counterintuitive, because—

Oh, go ahead.

I would have thought that people-related decisions are potentially two-way door. For example, like, you can, if you do wrong by somebody, you can just apologize to them, or But in some ways they are one-way door.

In some cases they are one way. I think in most cases they're one way. Depends on the actual kind of decision. Once you do wrong by them or right by them, it's not about that person, it's about setting a precedent for all future things. And so it's important to understand why you're setting that precedent. And so it, it doesn't need to be a heavyweight process, it just needs to be thinking for a day or two before you get back to this person versus, you know, basically in that same meeting committing to something that you haven't thought through the implications of it down the line. So because the same situation is going to happen again, it's going to happen again, the same person probably is going to come back again 6 months later or 9 months later and ask you for another raise because they have another company, or their friend is going to come and ask that. So you just need to understand your decision, the implication it's going to have. So it's— I don't want to make it seem like you've got to go into retreat and think for 2 months before you make a decision. But I think it's good to not make— I learned this in my first startup, which I joined after I moved out to the Valley, where I was very much focused on just being extremely efficient. And I would send emails out almost instantly after I thought of something. And then I got a pretty stern talking to by my boss, who was the head of product at the company, saying, Listen, just sleep on it. Just sleep on it. Think through the implications and do not send an email with any kind of emotion behind it. And so I think just having those emotions dissipate and making a rational decision, which is, I think, and sleeping on it, I think, is a very good piece of advice, which allows you to see things more clearly in the light of day the next day.

I'm seeing the— potential startup there now. It's like, read your emotional state from your camera and prompt you not to take this. So try and go one level deeper here and understand your motivation a little bit. So you're, you're very sought after for being helpful to founders, for your advice that you mentioned previously. Like, motivates you to play this role? So you're working as an executive, like you could be running your own company or being a venture capitalist where you do this like full-time. How do you think about your motivation to, to help and what you get out of it?

It's a good question. Uh, there are two motivations. One is that I've been helped by many people completely selflessly, as I'm sure many of us have. So I feel it's my duty, having been helped by people, to just give back. And if I can help With 15 or 30 minutes of my time, if I can help another company or another founder or company hopefully change their strategy or get to a better place, that's high leverage for me, because it impacts the life hopefully of many people, just like other people have impacted my life. The second thing is learning. I've seen that, like I said, a lot of good effective advising is being exposed to situations. So the more situations you're exposed to, the better advisor you can become to other companies. So I try to really understand what is the principle here and what I can learn. And so I try to ask a lot of questions, and I think you never know. I think you come across a situation that you're like, that's a once-in-a-decade situation. Then you come across the same one next week, whether it's, like I said, people-related situations, fundraising. I've just seen— it's like, you know, taking, you know, batting practice at baseball or something like that. The more you step up to the plate and take practice, the better a hitter you become. So I think you've got to take meetings. I think if you just advise 5 companies and let's do that, you'll know 5 situations. But actually, that's why I think Y Combinator is such a good investor, because there's so much pattern matching, and they've boiled it down to 2 things: teams that can move really fast and teams that can build really fast. Move really fast means that if you hear from a customer something is not working, you pivot really fast. And build really fast means if you pivot, you've got to be able to build something new. And so they just look for two things now. They don't care about— I suspect they don't care about the market at all, where teams target. They just care about a team that's technical and can build, and they care about teams that can listen to customers and move fast. If you have those two things, great things happen because you get many shots.

You're absolutely right. It reminds me a lot of MIT, where it's like men's at mammoth. Like, if you have good hands, or the equivalent in the technical respect, then, you know, things will fall into place because you can just try so many more things. And if you learn at a decent rate, then this, this is, uh, very promising. So yeah, you're absolutely right.

Tie back to the MIT motto.

That's awesome. And yes, Mens et Manus. I remember that. I actually only learned it after graduation. Um, like You're very— I suspect, I guess I haven't asked you directly, that you are an independent board member of Coinbase and Pinterest. And like, is that correct?

That's right. What happens with most companies is, as they make the transition to becoming a public company, most venture-backed companies have venture capitalists on their board. And so they start essentially replacing some of the VCs with independents. Who can bring expertise or help in different areas. So yes, I'm basically one of those. I took one of those independent board seats at these companies. There are some VCs who still stay on. Typically, one or two VCs will stay on because they are also independent board members after the company goes public. And it's because they have added value in unique and interesting ways. So at Square, Mary Meeker was an investor, from Kleiner, but then stayed on after the company went public, because she was extremely helpful in helping Square see, you know, bunch of trends and things that were happening. She still writes this amazing report on the state of the internet, and so on. So there's always a couple of VCs, but then most of the board seats are taken by independents.

Yeah, I think the operational experience that you bring, and founder experience also valued in that respect, as an independent board member versus one that's represented by the VC.

Exactly, that's companies.

How do you choose which founders that you work with? Like, are you looking for certain traits or sectors?

I think it's so interesting. I— some of the biggest, uh, biggest regrets I have is not even from— I'm also an angel investor— is, um, is basically fixating too much on the market and not enough on the founders. So not using the the motto that we just discussed, and not realizing that this is a person I think very highly of, and I know them, and I— they will figure it out. They will figure it out. So one of my cardinal rules is, if there's a person I think highly of because I've worked with them, I will always have time for them. I will always put money behind them if they're starting a company, blindly, regardless of what idea they have. And, uh, and, and so I have invested in many, many people across Google, Facebook, and Square with nothing more than just the fact that they are starting a company. And so that's my strongest conviction, that when you have a person, you know, who's hung— and so that's one, who you know well. The second one is looking again at the founder. I'm a very, very founder-centric person, and the characteristics I look for— I have to make a decision in 30 minutes. So first of all, most of the companies I speak with, almost 99%, are inbound. I have really no bandwidth to reach out to companies. So most companies ping me or are introduced to me by either other investors, other entrepreneurs that I have helped in the past, etc., etc. So, and there have been a bunch of cold LinkedIn reachouts. So most of these are inbound. So I have to make a determination in that 30-minute call, whether it makes sense, at least from my point of view, to engage more. Formally and say, hey, you know, let's do something together. You know, obviously the founder can make their own determination. And so what I look for is 3 things which are all founder-centric. One, founding story of the company and the authenticity of the founding story. What I mean by that is, if you look at great companies, the founding story is always authentic. They are solving a problem that they have faced at either— in either their life or their work. And so whether it's Mark Zuckerberg at Facebook Larry and Sergey at Google, Jack Dorsey and Jim at Square, or even Tony Hsieh at DoorDash, and Andy and Stanley, they all faced a specific problem. They didn't start out with the intent of building a company, or a big company. They just said, we want to solve this problem that we are facing. They solved the problem, and then it ended up becoming a successful company. So trying to understand why did they start the company, that's always the first question I ask. Why did you found this company? And I try to really look for that authenticity. If the answer is, well, we sat around in a room with our roommates or buddies and brainstormed ideas and, you know, basically came up with this idea because we read about it in TechCrunch, that's not the right kind of authenticity I'm looking for. So authentic founding story is one. The second one is founder market fit. So this goes from these founding stories. So what do you understand about the space that you're entering? That is non-obvious. In other words, which is not just, you know, not just a random person like myself can just read a few, do some Google searches and find out. What is that unique insight you have about this thing you're going after, this problem you're solving, that is different from maybe other attempts that people have made at this problem, or, you know, other ways to solve this problem? So looking for some kind of unique, non-obvious insight about the problem, about the space. And then third one is grit and determination, and this is super hard to evaluate, but it is extremely important. And I think this is the ability to solve problems and make forward progress despite scarce resources. This is a— there's a term called relentlessly resourceful, uh, that Paul Graham has come up with of Y Combinator. I think it applies very well. They are extremely resourceful and relentlessly so. And the way I gauge that now is I basically do a check-in meeting a month later. So I'll say, hey, you know, let's meet up again in a month if the first two things resonate. And then I see how much forward progress have they made in a month. If a month later they are still, oh, I'm still fundraising, or I'm still doing this or that, then I know that, you know, the company is still— you know, I'm still at my job at Google, right? So it's, you know, you basically— it's not the right kind of founder, at least from an early-stage startup perspective, because in one month nowadays, with the speed at which it takes to build a team and build a product, you would expect to see a huge amount of progress being made on many, many fronts. So I basically, I think a second checkpoint, then instantly, because I'll ask them, what do you think you'll accomplish over the next 1 to 3 months? So I'll record that, and then I'll check in with them a month later, and it's crazy. It is very rare to find people who can do what they say they're going to do. I just look for the basic thing. You told me you're going to do this. Have you been able to do this? Not even one year later, just a month later. And that weeds out 80% of people. It's kind of insane. And so it's actually a very good test. If you're uncertain about a company, as an angel investor or just someone who wants to get involved, just say, listen, why don't we check, touch base in a few weeks? What do you think you'll accomplish by then? And if they have accomplished that, that actually is a good sign, because I can tell you 90% of people will not be able to accomplish what they say they're going to. Most of us, I mean, it's just hard because we get pulled into so many directions. But those special founders who've set a goal one month out and can hit that goal, back them, get involved with them, help them.

Oh, this resonates so much. We've just finished the current YC batch, And what people can accomplish in 10 weeks is mind-blowing. Like, you just see that, oh, you know, product doesn't work, it's just some screenshots. Oh, it's built. Oh, it has some customers. Wow. And wow, one of that contracts is 6 figures. What? Like, things like that happen all the time. Very surprisingly delightful. And it really resonates. So I'm going to open it up for questions in a bit, but we're going to play a little bit of a game, which is Gokul has a great presence on Twitter, and I encourage everyone to go follow him. But you've put some interesting tweets, and I would like you— I'm going to read them to you, and I would like you to tell us, like, maybe the context and the background that went into those tweets. Because to me they were interesting. So, I've served on 10 private and public boards in the past 12 years. Two observations: Founders are much more assertive today. A decade ago, investors dominated board meetings. B) Meetings are much more engaging and focus on key strategic issues versus financials and fundraising. What's going on here? Tell me about that.

It's all of these tweets that I do are typically after I have observation through personal experience. So in this case, I had just wrapped up a board meeting, which I was attending as a board member, and I was struck by how the founder CEO ran the meeting. They set the agenda ahead of time with input from the board, so they owned the agenda around, around 2 or 3 meaty strategic topics. So basically they said, here's the 3 topics we're going to discuss. They rotated the key folks on their exec team in and out of the board meeting, so they basically managed the, the whole flow of the meeting really well. They set the stage for every discussion. They ensured there was actionable feedback and next steps. And they also made— they called upon the board to make sure we engaged. So they basically were like an MC running the board meeting in a very tightly run fashion, which added value to their team. And they really leveraged the board as advisors versus as their bosses. So they really— I think the best founders now treat the board as advisors that can add value. And get different parts of the board or different folks on the board involved in different things. Contrast that to, you know, board meetings from the 2008-2009 timeframe, the first boards I was on, where similar founder CEOs would basically take the agenda from the board. The board would basically— the lead investor or investors would set the agenda. Here's what we're going to discuss, mostly financial and fundraising focused. And even at the board meeting itself, the board meeting or the investors around the table would discuss each topic, and the CEO would sometimes participate, sometimes be a passive observer. And such a contrast. I mean, such a contrast. It's— I think that's why I think great companies are truly founder-led in all aspects, including board meetings. I think you attending a board meeting actually gives you a sense of how, you know, how the founder— that's why before committing to join the boards that I'm on, I always try to attend a board meeting or two as an observer just to see the dynamics on the board. And I think it gives you a good sense of how the founder engages with their board. So it's a good mark of a strong founder. They have confidence in themselves. And again, the board is not— the board is your boss in some theoretical capacity, but as a founder CEO, you've got to treat the board as advisors. If you start having a boss kind of mentality with them, it just— it's not the right way to run a company. They advise, and then ultimately it's your call to make the decision. You've got to lean on them for advice, not for instructions, or my—

Yeah. I mean, truly, like what you described, if the board meeting is once per quarter, you have, they have much less context. You're kind of living it day to day. So there's, as the founder, it completely makes sense. Okay. Tweet 2, founders. "New hack for oversubscribed rounds that I'm seeing companies employ: reserve space for investors who send you employee referrals. For example, $100K allocation for each engineer, PM, or designer they refer and you end up hiring. Worth reserving $500K for this approach." Now, what's interesting to me here is that, are there advisors that can make it rain employees like this? Like, this I have absolutely never heard of. I think that it's seems rare that like someone in their career is working, they're getting them to like jump ship. Are there people like this? Tell me.

This happened to me after a round, after an invest in a round in which the company gave me a certain allocation, and then when I asked for more, they said, well, you know, there's a chunk of allocation reserved for investors or people who basically can help us hire people. That's our top need. We have to hire 5 engineers and one product person over the next 3 months, and it's extremely hard. So if you can send us high-quality candidates and they get hired, we can— we have X amount of allocation per hire. I do think it's hard, but it also, I think, is a good thing for— there's actually now— it's hard enough that there are now talent, boutique talent agencies that have become VCs, and they actually are able to get get an investment allocation in some of the best companies, because hiring talent is so, so, so hard now. If you are known— if your super strength is to help companies hire, you can actually come in and take your fee in equity as an investor instead of on a per-head basis. And so I think for me, thankfully, or I guess I think once you're around for a while, you get certain kinds of resumes. So I get a lot of resumes from product managers and product leaders, and so I am able to— at any given point of time, I'll have 5 to 10 product people who are looking for new roles, and then I can connect them. Now, obviously, fit between the company and the role is always challenging. Different companies need different kinds of people, seniority, etc. But yeah, I think it's not that easy, I think. But I think the same principle can be applied to not just hiring, but to other things that the company wants. So the companies might want maybe mentorship around growth, or they could want, you know, some customer intros or something like that. But you can see as a company what you want to accomplish in your next 6 months and basically have almost a quota-based system for investor allocation, where maybe someone makes a customer intro. And it's almost changing the dynamics again, where 10 years ago, investors— it was the founder's privilege was to get a certain investor. Now it's the investor's privilege to invest in the founder for certain companies. And so founders should take advantage of that, where multiple investors are clamoring to get into the round, and figure out how to make the investors work for the additional allocation.

You know, it's interesting, commentary on this point. This is the highest-tech industry with all this cool technology, but this process sounds super old world. There's these people who broker in talent, and it sounds like something that's from old times, but very, very interesting to get a peek into that. All right. Do you have tips for From what you're describing, it's a very human enterprise, and there's many great talent who's off the grid. Like, they don't have the pedigree to go to a great school, but they have a lot of talent. Like, any tips for that audience on how to get into these type of networks?

I think YC is a great— I think YC is increasingly democratizing entrepreneurship, and there's Startup School at YC, which is even a feeder into YC. And there's also Entrepreneurs First, So I think the good news is now, at least over the last year, geography— geographical boundaries have been completely broken down. So there's no— we could all be, and we probably are all, maybe not in NorCal, but in different parts of the country and maybe even the world at this point. So I think the good news is there's more resources than ever before on how to start a company, how to do almost any function, and free resources and organizations like YC and Entrepreneurs First. So I think The good news is, if you are motivated, it is easier than ever, and it's going to get easier by the year, by the quarter, to get into networks that are not— I think those same alumni networks still apply, but there are new networks. I think people obviously have dropped out of— have never gone to college, and if you look at their LinkedIn, they call themselves graduate of Y Combinator. And so that's, you know, as good a degree for entrepreneurship as going to, you know, a top-tier school nowadays. So There's many other ways to prove yourself. Building and launching an Android app in the App Store that gets, you know, 10,000 people to use it is probably as good as getting a computer science degree now. It shows like you can build a bunch of things together, you know, and so on and so forth. So I think there's so many avenues to now prove yourself that the credential, formal credential of schooling, is becoming less and less relevant. In fact, I've invested in several— one of my, my Most thesis that I believe in most is the disruption of high school and college education over the next 20 years, and invested in many companies that are essentially trying to do that in different ways.

Excellent endeavor. I'm also working on that. It's much harder than it looks. One— OK, one more final tweet dive, and then we'll open it up for questions. Questions. So every leadership role is part clouds—strategizing, inspiring, and vision—and part dirt—doing, executing, details. People who go into leadership role expecting 100% clouds will fail. CEOs for leadership roles screen out talkers who want clouds but no dirt. Um, double-click on this one for me.

This is a good one after a somewhat painful one after a, uh, leadership review I was doing with a company I advise where We were just going through their leaders, and the CEO called me because he realized that during COVID I think a lot of things became apparent to the CEO. They realized that there was a set of leaders who essentially just stepped back and completely delegated, and there were other leaders who worked alongside and really stepped up and worked alongside their teams and helped them and coached them and were much more hands-on. I think COVID actually really accentuated the difference and the difference in styles and the satisfaction that those teams had to see their leader actually working alongside them during this extremely stressful time. And I think it became clear that out of the 7 direct reports he had, the 2 that were— even after repeated feedback, they just couldn't— they thought of leadership as managing from up high and giving directives. And people actually implementing. But the problem is that it might have worked in a physical setting where you have offices, but with COVID a lot of ways of working and getting things done were upended, and everyone had to learn new ways. But these leaders were unwilling to do the work of coaching people how to do it and being hands-on, and essentially led to massive morale issues. Employee NPS scores are poor, and ultimately people were leaving the company, and also the performance of those departments was not good. So ultimately, the leader decided to make the decision to part ways with these two execs who essentially were not able to do that. I think more than ever now, because of remote work becoming a reality, it's going to be more important for people to— for leaders to be even more hands-on and to show people how to do things, because those— you've got to, you know, figure out how to do that in a way that —people learn, because I believe in the 70-20-10 school of learning. 10% you learn from watching classes and sitting in class and so on, observing. 20% you learn from a mentor and really watching closely how someone does. And 70% you learn from doing. And so I think the leader's job is to figure out what continuum of that 70-20-10 different people are, And really that 20%, which is coaching them through, having them really be hands-on. So I'm onboarding someone on my team, for example, at DoorDash, and I'm going to be— the best way to onboard is just having them shadow me for essentially 2 weeks and being on as many calls as they can with me, or Zoom calls, and seeing me do work so they know exactly how I operate and hopefully learn a bunch of the things they need to learn. So I think Leaders who are unwilling to or don't have that— I feel that the best leaders are people who are respected for their mastery of a certain thing and craft, not just people who are respected for being great "leaders" or managers. So as leaders, I think you've got to have— you've got to be the best at something that people can learn from. And that's what I meant by dirt. If you think that leadership is all about just sitting on an ivory tower and basically just giving giving like direction, that's not the current time. That might have worked 25 years ago, but people respect people who can get stuff done and can show others how to get things done. So that was more of a reflection on that. Sorry for the long-winded answer.

Yeah, it completely resonates. We do this a lot at YC. You think like, oh, it's remedial to, you know, read tons of applications or edit, copy edit blog posts or text, but actually it's not, and it's core skill. And if you, You can— it can atrophy really quickly if you don't practice it. So this is a great tip. All right, let's open it up to the audience. Do folks have questions? Just maybe raise your hand and I'll call on you. Vivek.

Yeah, again, Reshma, thanks for organizing. This was great. You know, Gokul, I'm sure a lot of us would agree here that you are perhaps one of the most gifted hybrid product business minds in the Valley. You know, having worked across multiple iconic companies, um, here since the '90s or 2000s— I don't want to date you too much here— but, um, what's— what startup or what emerging technology, um, are you most excited about for the future?

I think we're finally at a point where blockchain, uh, because of decentralized finance, is going to become a reality. I think we've been waiting. There's been a lot of blockchain applications mostly in industry and supply chain, you know, IBM, Walmart, all of these bigger companies have used blockchain. And most of them have relied on companies collaborating because blockchain is ultimately a distributed ledger. I think finally with NFTs and with some of the other applications we are seeing in lending and a few other financial applications, we are finally seeing decentralized finance or DeFi coming out. So I think that is going to be a very, very powerful underlying technology that enables many, many, many applications. It's still nascent. It might always take— it might have an N+1 syndrome for a while where we think it's going to be next year, but it's going to be the year after. But I'm very positive that by 2030, we'll see a bunch of fairly scaled DeFi applications. So that's the 10-year horizon I have. The second one is I think autonomy. I think the There's just too much. We're just too close. I think, again, it's an n+1, where we all thought 5 years ago when we saw the Waymo self-driving car demo that 5 years from now it would be a reality. But it might take another 5 or 10 years. But it is going to happen. It is going to happen. I think there's autonomous— autonomy in many different ways. It will change the fabric of our cities. It'll change a bunch of things once autonomy happens. But those are two things I'm extremely excited— blockchain and autonomy. Thanks. Very helpful.

Anvesha. Hey, Gokul. Thanks so much for doing this. You mentioned type 1 and type 2 decisions. I'm curious if you have any stories from your experiences where there was something that was maybe you thought was type 2 ended up being type 1, or just a decision that you wish you could kind of go back and reverse and kind of your learnings from it, how that might have affected your frameworks.

It's always people-related, all these decisions. I think it was at my first— it was at my startup that I founded that was ultimately after Google, that was bought by Facebook ultimately. But what ended up happening is I must have fired out of the first 10 engineers we hired, I ended up firing 5 of them. Because essentially I moved too fast to hire them, every single one of them, because I felt this urgency around hiring. We had raised a lot of money and we were not able to hire. And so I was overriding again and again my, you know, they did well in the interviews, but there were always one red flag or another red flag. And so it took me 5 of these decisions to realize that actually, at a startup, choosing who to hire as your first 10 employees is actually a Type 1 decision, not a Type 2, because I was very much a bias to action like Reshma described. It's always like hire fast, fire fast. But it turns out that hiring is actually— you've got to hire slow. It's a Type 1 decision, especially early in a startup. Firing is probably a Type 2 decision in many cases, but hiring has to be Type 1. So unfortunately, I made many, many— I unfortunately misconstrued hiring as a Type 2 decision and was like, well, we can always like— and then after, only after firing 5 most painful times of my life, especially because they had to be fired during the 2009 recession. And so it was very, very painful for both sides. But, and we were, every time we would, they were literally fighting, one person was like fighting 20% of your company with a 5-person company, and it would have incredible ripple effects on everyone else. Why is this person not here today? So you'd have to have an all-hands, and unfortunately repeated mistake. And so the problem is that we didn't have a process. I kept evolving after every firing or hiring process, but it still didn't have the intangible of culture. And ultimately the last two we fired based on culture fit, and we had to really codify what we expected from someone from a cultural perspective. We expected, I mean, very candidly, that that person would work. We were never willing to say that, that that person worked at least one day of the weekend. And so we fired two people when they didn't show up, when they were unreachable on any weekend for 3 months in a row. And we had all these fires going on and everyone else was in the office one weekend day. And we realized that that commitment we were too scared of asking people to make ahead of time because we were worried if we told them we had to make the commitment, we would lose them. But it was better to be transparent and just say this job for the first— for the next year requires people to be in the office on weekends because we have customers whose sites are up on weekends. We need to service them and we need to help them. So yeah, we didn't set up the right principles to filter out and to filter in candidates.

Very interesting reflection. Thank you for that. Jamie?

Yes, Rashma, thank you for putting this on. You mentioned that you often help startups with operational processes.

We just wrapped up YC. What types of operational processes do you help early-stage startups with? Aka what are we going to run into that you might be able to help with?

The simplest one is once you get into a— once you get to a point where you can't fit into a room anymore, one room, and you're across— well, that's true even now, I guess, in Zoom. You're no longer in a place where you all are in the same physical space. It's good to have an all-hands on a— even if— even with a 4 or 5 person thing, when everyone gets together. And I think the format of the all-hands obviously evolves as the company grows. —so that's the lightest weight process, right? At the end of the week or the beginning of the week, just outlining, you know, what happened in the last week. People can come up and say their piece, you know, all question-answer session, etc. Especially as you get new hires who've not been involved since the beginning of the company, think about onboarding them. It's a great way to welcome them and so on. So I think that's the most basic thing. The second thing, which again is accentuated by remote work, is The CEO email, you know, I think once you get to again 10-15 people, it's good for the CEO to send an email about what top 3 things there are in their mind on a weekly basis, and it takes 45 minutes to write. And you can keep— but it doesn't— you shouldn't write it all at once. You should actually be thinking throughout the week around what you should be putting in that CEO email, because things, you know, the things that bubble up in your mind happen throughout the week, and then at the end you can— you take raw notes and you synthesize them into an email that you send. But I think communication is the most important thing, even more so because of Zoom. And so just finding ways for CEOs and teams to connect with each other is probably the— you know, even those, you know, probably all of them, how to run an all-hands in the era of Zoom itself, we are all learning how to do that better and how to get teams engaged and how to get CEOs to engage with their teams and even one-on-ones and how they work. So communication is the number one thing, how to communicate between individuals and teams and CEO to company.

Jamie, does this sound like office hours to you? Exactly. Great time. Mark, good to see you. Hey, Mark. Good to see you, Reshma.

Good to see you, Gokul. And I think I'll just say to everyone here, Gokul is one person I called when I was starting PayJoy with some with my co-founders, one of whom went to MIT, and that half hour was extremely useful. And I think the generosity Gokul was talking about in terms of being willing to talk to founders is really important. It's sort of a core infrastructure, I think, for founders when they're in that early stage. I was wondering, you know, I definitely agree with that idea of focusing on the founder and figuring out, you know, which founders can actually, you know, focus, execute, execute and get things done. But I was wondering about the sort of second-order effect of that. So I spend some time now helping emerging market founders through Next Billion Advisors. And one of their biggest challenges is they can't really penetrate the bubble. It's really hard to get access to great advisors or capital because they're not in the MIT network or the Silicon Valley network, the ex-Facebook network. They don't have that lived experience. That you're talking about, that that criteria pattern matching is based on. So how do you balance that founder-first mentality with, you know, basically opening up opportunities to the next wave of founders from emerging markets?

It's a good point. I think first I just do it by being available to them. So, you know, a bunch of founders from countries like Latvia, Brazil, etc., wherever they reach out from, I take the call. The second thing I do is I try to— I now have built a network of other people who also want to help, experts from our Facebook, Google, Square, etc. days. And so I try to, depending on what the founders need, I try to connect them with at least one more person who can be an advisor to them and help them. I just talked to someone in the morning today from India, and so he wanted help with— he has a app that's growing fast, but he doesn't know exactly how to think about growth. So I just connected him with an ex-colleague from Facebook who's one of the leaders on growth to help them think through growth. So I think every founder needs— I think founders don't need 20 people, they need a small group of people, and also the advice they need is different at different times. And so I think hopefully that relationship with— and what I try to do is many of these folks at Facebook and Square and so on, they don't really work and have the opportunity to work with startups. So they're actually excited to work with startups because it's for them, it's something— for me, I do it as a matter of course now every day. For them, they probably work with 2 or 3 startups. No one, you know, no one has reached out to them. So for them, it's a great way to just share their skills and get to engage with another in another context. And many of them want to advise. And so the thing is, there's actually, if you look at these big companies, Facebook, Google, etc., Many of us probably heard— I hear from colleagues all the time, ex-colleagues, how do I advise companies? And so I think there's an untapped wealth of people in all these companies who want to advise, they just don't know how to. So I think that might be something that MIT CMC or, you know, an organization should maybe get people who want to advise even informally and could lead to formal stuff, but experts in different areas. And then, like you said, startups can just tap into those. Those people. But there's so many—

marking that. We have— there's so many startups that need advice. And so yes, let's, let's definitely follow up on that one. And, um, I think it's a really good idea actually, because there's like that type of training that you get at the companies on growth and all those specific domain skill set is really not packaged well in teachable format. And so it needs— there's a vehicle there somewhere. Exactly. Yuchen, please. Oh, you're on mute. Ah, can you hear me now? Mm-hmm. All right, thanks. So thanks, Gokul, for joining us today. I would actually be curious to hear you talk a little bit about how to think about balancing customer centricity and having a disciplined product strategy, in particular for B2B products for really large enterprises, where those enterprises have a lot of pull.

Yeah, it's a good point. The B2B products, B2B products are the most dangerous ones. In other words, they are in danger of becoming feature factories. The most, because you just have a set of feature requests from customers and you just start like building them and you get accomplishment and satisfaction from just shipping features versus truly changing customer behavior. So one way to do that might be to essentially have your goals, and we can actually just feel free to email and we can talk more about this. This is a huge pain that all B2B companies face, Roadmaps, I believe firmly, should not be focused on product features, but should be focused on customer behavior changes or customer outcomes. So that's the fundamental theory of roadmaps I have, that roadmapping and teams should have goals not around features and launching them— those are just tactics— but around changing customer behaviors in certain ways. And so once you, once you think of roadmaps in that way, then features are the management team and the product team, or the CEO and the product team, then negotiate not around heavy ship feature X or ship feature Y, but around what customer behavior do you want to change. For example, I want my customers to open the app, you know, even B2B customers, maybe you have an app for them. I want them to, you know, open the app 5 times a month instead of 1 time a month, something like that. And so I think once you start thinking about that, then all features funnel into are basically solutions to this problem, which is how do I change my customer behavior? And so we can talk more about this, but I firmly believe that going into that mentality— instead, what happens is management tries to micromanage features and says you should launch an Android app, or you should launch this or that, versus really negotiate. The negotiation between management teams and product teams should be around customer behavior. And how those change, and the tactics should be managed by the product teams around how those customer behaviors— customer behaviors can be things like acquisition, retention, engagement frequency, and other kinds of behaviors like those.

Thank you. That's super helpful. So everyone, I'm kind of obsessed with timeliness, so I'm going to cut you short a minute here, but Gokul, thank you so much for joining us today. And as a gift, we have created an NFT for you commemorating this event. No way! And so, um, it's a lovely screenshot of all of us. I'm sure it will be very valuable one day because this is the time when we all decided to mobilize the angels, right, Mark and Gokul? We decided here together on the recording. But great hanging out with everyone, and we hope to see you at events in the future. Looking forward to it.

Thank you, everyone. This is great. Thank you. Thank you, Reshma. Thank you. Bye. Bye.