20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Ravi Gupta is a Partner @ Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR. In Today’s Episode You Will Learn: 1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia? 2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi's lessons on what it takes to acquire those great talents? 3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart? 4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board? 5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time? Items Mentioned In Today’s Show: Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is the 20 Minute VC with me, Harry Stebbings, and today we have a very special one for me. It really exemplifies why I love what I do so much with the show. I met this guest maybe six months ago. We spent a lot of time chatting and becoming friends and really is such a joy to do this with him today. Someone I respect and admire as much as I do. Therefore, without further ado and enough of the soppy stuff, I'm thrilled to welcome Ravi Gupta, partner at Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UI Path, Zoom, the list really does go on. As for Ravi, prior to Sequoia, he spent four years as COO and CFO at Instacart, playing an integral role in their hypergrowth journey. Before that, Ravi spent 10 years as a director at KKR.

• 0:41Harry Stebbings?

  And I'd also want to say a huge thank you to Pat Grady, Mike Moritz, Will Gaybrick, Mattilde Collin, and Sagar Sangvi for some amazing question suggestions today. Real team effort here on the schedule. But before we move into the show today, I want to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million. Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure, and simple e-signatures.

• 1:23Harry Stebbings?

  And I do have to mention another incredible product-centric business, Digits. Digits has spent the last two years building this incredibly powerful financial engine for businesses. Now they're ready to show you what they can do with it. Back in April, they announced a real-time dashboard to help you manage your company's expenses for free. And recently, a little birdie told me they have some incredible announcements coming up. They've raised almost $33 million from Benchmark and GV, and the team behind Digits is just epic. Personally, I think it's one startup to watch this year and the next. And last but by no means least, has anyone tried to send a business payment recently? Oh my god, it was easier to get into college. You have reviews, you have this never-ending back and forth between colleagues, which just slows the process down. It's a lot of work that continues to pile up as your business payments scale,

• 2:07Harry Stebbings?

  and that's where Rudible steps in.

• 2:10Harry Stebbings?

  apart is not only its focus on digital business payments, but the time it saves on both the accounting and the operations sides. Did I mention that Rootful automatically updates your accounting records, making your finance team's lives so much easier? Request a 15 minute demo and start managing your B2B payments electronically at rootful.com/20vc for free. There's no transaction fees, no seat fees for one full month. Join Rootful in building the best platform for businesses to manage their workflows and send and receive money digitally at rootful.com/20vc. Enough of me though, and time for the show. So now I'm very excited to welcome Ravi Gupta, partner at Sequoia Capital.

• 2:54Speaker 02

  You have now arrived at your destination.

• 2:57Harry Stebbings?

  Ravi, this is such a joy to do. For context for the audience, we met a couple of months ago. Honestly, I just love our discussions and conversations and their many winding turns. So thank you so much for joining me today, Ravi.

• 3:08Speaker 03

  I'm so happy to have met you, Harry, and I'm honoured to be here. Thank you.

• 3:11Harry Stebbings?

  I mean, that is so kind of you. May the bromance blossom. But I do want to start today and pretend to be blissfully ignorant on how you got into Wild Adventure. So for some context, how did you make your way into the Wild Adventure and come to be a partner at Sequoia today?

• 3:24Speaker 03

  Well, I wish the story was as interesting as starting a podcast when I was 18, but you know, we can't all be Harry Stebbings. So I joined Sequoia last year after four and a half years at Instacart and, you know, in 2015, I met a poor guy. And he shared the vision for what he wanted Instacart to be with me. And honestly, Harry, I was captivated. I was inspired. And so it was just a team I wanted to join, a company I wanted to help build. And I was lucky enough to be the COO and CFO there. That four and a half years is a crazy time for Instacart. We went through hypergrowth. We had all the fun that came along with that and we also saw all the issues that came along with that. I got to know Sequoia because Sequoia has been partnered with Instacart since the earliest days. And I just really liked their style and how they partnered with us. And so when I decided to get back to investing

• 4:07Speaker 03

  and really work with the next generation of founders, Sequoia was kind enough to let me join the team.

• 4:12Harry Stebbings?

  I mean, it is an incredible team. And as you said there from there, Johnny, with Instacart, it's been incredible partnership there. I am really intrigued and it is so unfair of me. And whenever I go off schedule in this interview, I'm just gonna put it down to being frank, so I can. But you mentioned the vision element, and I tweeted the other day, and I told you about this earlier before, deleting this when anyone criticised me about it, but I tweeted actually about the dangers of vision, because actually you can often always exceed the vision, and it can almost limit and put mental constraints around what you can achieve. Would you agree with that? And how do you think about the pros and cons of vision and how you evaluate it?

• 4:46Speaker 03

  It's interesting, Harry. I actually, I would tell you I agree with a part of it and I don't agree with a part of it. But I bet if we go through it deeply, you and I will end up in the same place, which is, I think that vision is really important, but I think that you can't be locked to it. Which means you need a vision to get people excited about joining your company. You need a vision to get investors excited. You need to be able to tell the story of why your company matters. But you also need to be able to adapt if things change, and you can't be locked into that when the environment changes around you. And so when I say that I am captivated or inspired by a vision, it's not that that's the only way that the company can be built. It's that that story and that big picture resonates with me. It's a world that I want to live in. And I think that the part of the vision, for instance, that Apurva gave that resonated with me was,

• 5:31Speaker 03

  doesn't it seem crazy to you that we shop for groceries the same way we shopped for them 80 years ago? Don't you want to live in a world where the store changes every time you quote unquote walk into it? That it's built just for you, that it knows what you want, that it recommends different things? Don't you want to live in a world where you could spend all this time with your kids? I have three sons, as you know, where you could spend all this time with your kids rather than spending time at the store? And that the only time you go is when it's fun? That vision is nonspecific to, we're gonna do this, then we're gonna do this, then we're gonna do this. So I thought the part of your tweet that I loved was the, you gotta just keep going. You don't want to be locked into it. But I do think having some vision is important.

• 6:08Harry Stebbings?

  I think you're absolutely right. I think it's more like, it doesn't have to be the grandest of visions from day one, and then also it's appreciating the transient nature of it and being plastic enough to see it change. So I totally agree with you that. God, we always end up in the right place. I'm so glad we're doing this interview. Tell me, I want to start on the team itself. You mentioned Apurva there, and you worked across some incredible teams from KKR to Instacart, and now inside the best in venture with Sequoia. And I'm probably gonna get killed saying the best and not one of the best, but I'll just leave it there for now. So tell me, when thinking about team, what's the most important question to you, Rabby?

• 6:40Speaker 03

  Yeah, Harry, I'm so glad you asked me this because I think deeply about this topic and I'm passionate about it. And I've been so lucky for the people I've been able to work with in my career. And I do think that there is one question that I find more important than anything else. And it's quite simple. I think the question you gotta ask if you're building or evaluating your team is, would you enthusiastically rehire this person if given the chance, knowing everything you know? And I think the word enthusiastically is so important here because it removes this ability to be wishy washy or unclear. If the answer to that question is anything other than absolutely, then your answer is no. And I think that people underestimate what the possibilities are if the answer is yes to, yes, I would enthusiastically rehire this team.

• 7:22Speaker 03

  Because now all of a sudden, you're constantly surrounded by these unbelievable people who can do incredible things together. And I think that the possibilities are actually hard to describe. It's also so much more fun. And so I think it's a mistake that many people make that they don't think deeply enough about their team. And they don't hold it to a high enough standard together by asking this simple question, would you do it again if you could, if you were starting from scratch?

• 7:48Harry Stebbings?

  Can I ask, how often do you think one needs to be self-reflective? Is it a continuous thing where you need to continuously be looking at different people in your team and going, would I enthusiastically rehire them? Is it kind of like annually? How do you think about the importance of that check-in question in terms of cadence?

• 8:03Speaker 03

  I don't know that I have a prescribed point of view on exactly, but I guess my instinct would be at six or 12 months. I mean, I think that in startups, months or like years. But I guess I'd say this, I think the instant that you feel like something is not moving as fast as you'd like in a startup. I think speed is so important. I think the instant you feel like something is not right, I think you gotta be reflective as to what's happening that's making that not right. And what am I doing to fix it? And I think that inertia is a very bad reason to keep doing something.

• 8:31Harry Stebbings?

  I spoke to Will Gabriel before the show. And he mentioned in terms of talent and talent assessment. And I'm gonna put this on him so then it doesn't sound like it's coming from me. He said that in a nice way, you're a talent snob. And in terms of acquisition, though, it's the toughest labor market in tech that we've seen. So I'm really interested, when you think about the self-reflective question there and actually applying that to acquiring the most competitive talent, how do you think about determining the very good from actually the best of the best?

• 8:59Speaker 03

  Well, Harry, I'm gonna have to talk to Will about the way he said that. But Will truly is one of the most talented people I've ever met. And he's also one of my best friends, and so I'm glad you talked to him. I do think it is critically important to seek out the very best when you're building your organization. I think it's important to make sure you're surrounding yourself with people that make you and the team better. Mark Zuckerberg talks about how he only wants to hire people who were the world different that he would work for. And I think that's totally right, because you gotta find people who elevate your organization. They should be better than you at something. And so you asked about how do you determine the very good from the great? I don't think that's a static thing. I think it's about are they great for your org?

• 9:41Speaker 03

  Which to me means, do their superpowers complement your org's weaknesses? And are they somebody that you and the team can learn from? And I think the reason I'm so passionate about this is because this really compounds over time. I think about something my partner Carl Eschenbach says, and it's so simple, but it's so true, which is A's hire A's and B's hire C's. And so I think it is critically important, and I try very hard to be surrounded by A's all the time.

• 10:08Harry Stebbings?

  I have one question for you, and it's just in terms of timelines associated to hiring roadmaps, often founders will push back and say, absolutely, I know I need to hire the best, but I also just need to hit target for next quarter. And bluntly, I don't have the timelines in place to make that happen. How do you think about the balance between filling Cs but also maintaining quality bar? And it's something that I think Stripe's done so well in terms of keeping up just the velocity, but also keeping up the quality.

• 10:34Speaker 03

  Yeah, I think that Stripe is absolutely inspirational on this topic. And I personally think they've done it the right way, which I think they are willing to deal with the pain of not filling a spot, because they respect that spot so much that they're only gonna put somebody great in it. And I think that's the right approach. I personally think that trying to hit targets over hiring the best team, I think it's a real mistake, and I think it's short-term thinking that doesn't scale. And it's very normal. I've done it. I've made that mistake. But the lesson you learn is if you're trying to build something enduring and Great. I think you really do have to focus on getting the right team. And I think that that comment from earlier around the compounding is really important here.

• 11:17Speaker 03

  Because the instant you put somebody in the seat who's not that great for your org, I think that you all of a sudden have a real risk that who are they going to go hire? And I don't think it's something that's that easy to go and fix. So I end up being somebody who pushes pretty hard on, why is this person going to elevate the org? Why is this person going to be somebody who we can learn from? Why is this somebody that we would be delighted to introduce at an all hands? And proud to talk about them coming and joining our company.

• 11:45Harry Stebbings?

  Okay, so we find that incredible candidate that we're going to learn from, that we're proud to call a part of our team. In terms of actually like acquisition, how do you think about winning the very best and winning the most competitive and sought after talent in the current markets and flipping the switch into sell mode?

• 11:59Speaker 03

  Well, I don't flip a switch. I would say I focus on trying to get to know what's really important to them from the first meeting. And I think that is an important part of it, which is you got to really get to know somebody. You spend a lot of time at work. I mean, my family is deeply important to me and I spend a lot of time with my family. But I also spend even more time than that at work during the week. And I think about that for you, Harry, the same thing. And so the first thing is I really try to get to know the person throughout the conversation. And then by doing that, by becoming somebody who they trust, I think that I earn the right to hopefully be a thought partner to them as they're making that decision. I think the one thing I do try to do is make sure that the mission of the company resonates with them. Because when those tough time come, which they certainly will,

• 12:41Speaker 03

  that adherence and that tie to the mission is going to be the thing that makes them excited to keep on working and keep on building the company. But I do think, and I think this is the most important thing I try to do when talking to someone is, I try to remember that as important as this decision is to me as a leader, it's more important to them because it's their career. And so I really try to make sure that they make the right decision for them. And obviously, if it's close, it would be great if they came and joined the company. But I think that I try to remember that it's more important for them than it is for me.

• 13:13Harry Stebbings?

  And this is off schedule, but I'm intrigued because you know, when I spoke to Sagar and to Will and thinking about our conversations, you create this environment where you feel very comfortable to open up and have some of the toughest discussions. And that's a very rare thing to be able to do. What do you think it is that allows you to create that environment? Often like I think about, hey, if I kind of show my vulnerability, then the other person will feel safe and available to open up themselves. What do you think you do to create that safe space for the other person to bring themselves truly to the table?

• 13:43Speaker 03

  To the extent that's true, I think it comes from my parents. I've looked at the relationships that they've built and the friendships that they've built over fifty years now. I love that. I love that some of my parents' friends were like family. And what I observed in my parents was really just this idea of you should be helpful to people. You should try to listen more than you talk. You should be there for them and you should actually care. And that's why that point that we talked about earlier about trying to remember that a career choice for somebody is really stressful. I do think it's important to remember that it's more important to them than it is to you. And I think that on this point of building real relationships, I think people crave real, human, authentic interactions. And I think people want to trust people.

• 14:26Speaker 03

  And so I think it's really just about being helpful and genuine with them along the way. And I think that the outcomes that come along with that and the relationships that you can build are really ones that really can last a lifetime.

• 14:36Harry Stebbings?

  I totally agree in terms of those longstanding relationships. And then I think it just makes the journey so much more enjoyable as a journey in itself. We have mentioned Will a couple of times from Stripe. And he said in particular, on joining Sequoia, how impressed you've been with the team in so many different parts. I really wanted to kind of dig in on this. And in terms of the Sequoia team, I guess a couple of different elements, but like, what have you been most impressed with? Let's start with that.

• 14:59Speaker 03

  Yeah, so I mentioned mission earlier and the most impressive thing to me about Sequoia is this single-minded devotion to the mission, which as far as I know, has been pretty identical since nineteen seventy-two, which is we help the daring build legendary companies from idea to IPO and beyond. And Harry, I mean, everything is built around this. The culture is so purposeful. I mean, it's in the behaviour that's rewarded. It's in the stories that are told and then this devotion to the mission leads to things like partnering with Patrick and John and Will and Claire. But I mean, at the time, Patrick and John at Stripe, when all they had was an idea and not a single line of code. Because they were remarkable and they were daring and Sequoia believed that they were going to build something of consequence and we had to partner with them.

• 15:44Speaker 03

  And so that's the piece that's been most impressive to me.

• 15:47Harry Stebbings?

  Okay, question. There's always surprising elements. What have you found the most surprising?

• 15:51Speaker 03

  Yeah, I knew this coming in, but I've definitely still been pleasantly surprised by it, which is the level of collaboration. Sequoia wins as a team and loses as a team. And to use a sports analogy, I think a lot of places do talk about being a team, a lot of venture firms. But my observation is they seem a bit more like a golf team. Everyone does their own thing and then you add up the scores at the end and hope that you win. Sequoia is more like a basketball team. Your strength or your superpower is added to a team with the sole focus of making sure that companies win. And the only thing that matters is the team's success. This is reinforced by things that seem like they are one-offs, but they're not. They're critical.

• 16:33Speaker 03

  This is reinforced by things like unanimous decision-making, which means we all need to be bought in when we decide to partner with a company. And it's reinforced when entrepreneurs ask somebody at Sequoia, hey, if I work with Sequoia, who will my board member be? And the answer is always the same, which is whoever you want. You get to choose. We just want to support you and no matter who you choose, you're going to get all of Sequoia no matter what. That means that if you need help with go-to-market, we're going to have Carl talk to you, who scaled VMware from 40 million in revenue to 6 billion. If you need help with engineering, we're going to have Bill Corin talk to you, who ran most of engineering at Google. And I am so passionate about teams and it's such an important part of what I think helps companies win.

• 17:15Speaker 03

  And I really think it's the best way to achieve the mission, but I will tell you that it still has been pleasantly surprising as a relatively new member of the team. And it's something that makes me really happy that I get to be a part of it.

• 17:25Harry Stebbings?

  And do you want to kind of ask, every team has a leader and every great company has to have a great leader. And as we said, I spoke to Sigur, who's obviously CFO at Instacart now. And he said that when it comes to leadership, your superpower above all others is your ability to prioritize so ruthlessly. I'm interested in kind of double clicking on this. How do you think about the importance of saying no as a founder and leader fundamentally?

• 17:47Speaker 03

  It's a lesson that comes from experience, Harry, which is you start out, it feels so good to say yes. Somebody wants to do something, yeah, let's do that too. But the problem is, is that that feeling is fleeting because nothing gets done. When you have seven priorities and 10 sub-priorities and it's on a Google sheet. Because nobody knows what's actually important. And so I remember this time at Instacart where we had six company priorities in a quarter. And a month into the quarter or halfway into the quarter, we weren't moving nearly as fast as we wanted on any of them. And so a quarter and I just sat down in a room and said, if we can only get one thing done the rest of the quarter, what would it be? And the answer was so obvious and we were like, well, let's just go do that. Let's not not get that done because we wanted to say we're going to work on more things.

• 18:32Speaker 03

  And so we literally had an all hands the next day and we rallied everyone around that one goal. And that's all it took to get us moving again. And so I think that focus is dramatically underrated. And I think that it's one of those things that it is a little bit more painful upfront to say no and to pick the one thing. But I think the outcomes that you get are so much better. And I think over time you can make that one to two, but I think that people sometimes think that you're going to go from eight to 10. And in my experience, I've seen that to be a bit of a mirage.

• 19:01Harry Stebbings?

  So this is where the show is just such a joy for me to do because I can basically pick brilliant people's brains for free and learn from it. And so I have to pick your brain here and it's like, I totally agree with you in terms of the prioritization and saying no. I'm sure both of us get many emails asking for time, for calls, for coffees, whatever it is. And I say yes to far too many and I need to say no to more. This kind of question for me is what is the right way to say no without losing elegance, grace? And without leaving a bad impression, do you think? How do you do it?

• 19:29Speaker 03

  Well, that's interesting because I think that there's different things. And what I would tell you, Harry, is I actually think it's harder for you to say no to those than it was for a leader to say no to a team member on the goal. And the reason is in a company, I think that a leader saying no to a team member on not wanting to work on something. I think it's actually a bit easier because you can at least get to here is what we want to accomplish in the long term. And I believe that the best way to get there is to work on this thing because it's the most important one. And so you can kind of have alignment on a shared goal. I think that the harder part, when someone asks you to meet up or have coffee or chat with them,

• 20:11Speaker 03

  is you might not actually have a shared goal, right? And that they want you to do something and you don't have the time. And so in that world, I think that I would tell you that I think it's important that people know that you need to do an excellent job for 20VC and you need to do an excellent job for Stride and that those are the priorities for you. And so it's not that you can't do it ever, it's that you can't do it right now. And I think that authenticity in the response, I think people will respect that.

• 20:37Harry Stebbings?

  Yeah, no, I agree. I agree. I think that's the right approach. I guess the kind of secondary question though to that and the prioritization element is, I spoke to Sagar before the show at Insta and he said about your exceptional Excel modeling skills, which I have to say did make me very happy because honestly Excel is not exactly my domain of comfort. When you click Excel on my Mac, it says sign in or register. So but anyway, my question to you on that is like, it is part of our role, both as operators and investors. But my question to you is, how do you think about what to delegate versus what to own and control? And how do you think about that decision?

• 21:12Speaker 03

  To be clear, I would imagine for the audience here that they need to know Sagar was being deeply sarcastic when he talked about my exceptional Excel modeling skills. So I'm with you, Ari. But I think the mistake I've seen people make is needing to do it all themselves. Maybe at the beginning, when it's you and your co-founder, maybe it's possible to do it all. But certainly when you have 100 people or 1,000 people, that approach just does not scale. And I think this ties back to that point about building a team that is better than you and that elevates your org. And my philosophy on this is pretty simple, which is you should hire people who you can actually trust to deliver. I think that as the leader, as your company scales, your job is to set the goal or to set the strategy. Here's what we want to get done. But then you've got to give the team the

• 21:55Speaker 03

  freedom to execute. And so that to me means that you end up delegating a lot, but you don't delegate the here's what we got to go get done, here's the kind of company that we want to be and here's the values. But I do think that you delegate a lot of how are we going to go do that?

• 22:11Harry Stebbings?

  Can I ask, in terms of the delegation, I'm totally with you and I very much agree with it. I guess my question is always on accountability mechanisms where you're like with teams, "Hey, this is your project to own, go make it happen, go run with it within these parameters." And you want them to be as aggressive and to be as ambitious as possible, but you also don't want them to have this fear of failure and not hitting targets. How do you think about kind of having the accountability, but also not constraining ambition when delegating?

• 22:38Speaker 03

  That's tough. I think that the first thing for me is the most ambitious people, they want the hardest problem, they want to have the ball, they want to be accountable for something. And so I try to look for people that really want to have that role. And then what I have found to be helpful is to let them drive the interaction with leadership on the topic, which is to say, "Look, I want to check in with you once a week, but you tell me what you need. We gotta get this done over this time period. And if you tell me you want to go off and do it, that's cool. My normal way of doing it is like this, but you tell me what it is to be helpful." And I think that one of the things for me that I think you have to do is build that relationship of trust where they know you have their back.

• 23:22Speaker 03

  I think one of the things your team needs to know is you desperately want them to succeed. This is not a test. You know, it's funny, people think about this in interviews. When you're gonna go interview somewhere, generally you're nervous because you're thinking that the person wants to find a way to stump you. And Harry, you know this, when you're building your team, when you're interviewing somebody, you desperately want them to be great. All you want them to do is to blow you away. You don't want to stump them. And so interestingly, I think for accountability mechanisms, I think it's important for the team and for the people who are accountable to know, "I want you to succeed and I'm here for you and I'm gonna be here to support you. You tell me what you need and I can tell you what I've seen work in the past."

• 23:59Harry Stebbings?

  I totally agree with you and I think that's a very kind of calming mental transition. I think the canvas to know going into interviews that actually the leader or the interviewer wants to see the best of you. And so I think it's a big thing to remember. I do want to ask, you know, we spoke about kind of challenges or lack of skills around, you know, Excel modeling for me in particular. And it's actually quite a big insecurity for me and it's not so much anymore actually, but it has been over the last few years, especially kind of as I've kind of been developing invention. I guess my question to you is, on the theme of kind of leadership and strong leadership, there's also insecurity within everyone. How do you think about insecurities in leadership? And what have been some of your lessons through, I guess, the Instacart journey? And then also now seeing it on the other side as a VC?

• 24:40Speaker 03

  Yeah, I mean, Harry, one of the things I respect the most about you is your willingness to talk about those things. I mean, I think that that makes a big difference to people to hear somebody that they view to be successful. And someone like you who absolutely has done these amazing things, talking about things that they're not great at, or things that they're insecure about. And so for me, I think it comes down to authenticity. I don't think people expect their leaders to have all the answers. But I do think that they expect their leaders to be honest with them. And I think that is a absolutely reasonable and good expectation. And so when I was at Instacart, I used to share mistakes that I had made with the company in all hands. Because we wanted to have a culture where people would try things. And the best way for me to model that was to tell people sometimes, well, look, hey, we messed up on this.

• 25:22Speaker 03

  At Sequoia, this is not exactly what you asked me, but it is the thing I thought of. At Sequoia, one of our partners late last year shared their 360 feedback with all of us at a partner meeting. And then asked, can you help me get better on these? I mean, I thought that took just incredible strength, and it made me gain even more respect for the person. And so I think on these kinds of things, I think people respond to authenticity. I think they crave these real human interactions in their leaders, because they want to follow somebody who they respect and they trust. And I think sharing that kind of stuff can create even deeper bonds with your team. And so I'm a big believer that kind of honesty and authenticity is quite helpful for leaders.

• 26:03Harry Stebbings?

  I totally agree with you in terms of being helpful. I also think it's super helpful within the boardroom and kind of building that environment of trust, especially between the founder and the board member. And it's another thing that I've actually wanted to ask you for a long time. But I think you have such a fascinating purview, having seen the very best of board operations at Instacart in particular. And then now also again on the other side of the table with Sequoia. And so a couple of different questions, but taking them one by one. It's like, first, you've seen the best of the best. How would you advise me on what makes the truly special board member?

• 26:32Speaker 03

  Oh, I love that question. Harry, the first thing is you already are on boards and you are going to be, and I'm sure you are great. I would tell you, I think the way I would articulate the goal for you is you should seek out to build enough trust from the very beginning with a founder, where you are their first call when things are good or when things are bad. And so to me, when I think about how you can do that, I think there's probably three things that come to mind. The first one is, I think you've got to remember what this means to the founder. You know, one of our values at Instacart was this is your baby. And I think that that is especially true for the founder. I mean, the company is not numbers on a page. It's not the board deck. An analogy that I think would be good for you to think about is this company to the founder is as important as your mom is to you.

• 27:17Speaker 03

  And I think that that will help you empathize in the right way for the founder. The second thing for me is quality is just so much more important than quantity. One of my partners, Michael Abramson, he often doesn't say a whole lot in a board meeting. But when he does talk, everyone's leaning forward in their seat because each comment is incisive and insightful. And it just gets right to the point of, oh, my gosh, we've got to think about that. And I think the last thing is in terms of trust, I think if you remember that the founder almost certainly wants to find somebody they can trust. It's like this interview point we were making earlier. And so I think they're looking for people that they can trust. I think if you show up consistently and just show that you care, which of course you do, then they're going to start confiding in you and you absolutely will be the first call.

• 28:00Harry Stebbings?

  No, I totally agree. And I think kind of the combination of the three creates that very safe environment for them as the founder. So I love that. And the brilliance is that you can invoice me after for the advice.

• 28:11Harry Stebbings?

  In terms of insecurities and vulnerabilities, often new VCs are insecure, concerned, nervous about their first deal. It's a very common thing. I was chatting to Will Daybreak before, and he specifically asked, and we wanted to hear your thoughts on this. And his question was, how did you approach your first deal at Sequoia? Were you nervous? And what did that mindset and process look like for you?

• 28:32Speaker 03

  Yeah, it's a great question, which I actually think, and I don't know what it would be like anywhere else. I think Sequoia helps on this nerves point in sort of a counterintuitive way because the expectation Expectation is that you go all in on the investments that you do. And with that expectation, you get to be super selective on the companies with whom you partner. Because people view it as a 10 or 15 or 20 year partnership. And so you're allowed to keep the bar and are encouraged to keep the bar super high. We actually partnered with them first at the seed and they've just consistently blown us away. I think that when we talk about the people we like to invest in at Sequoia, we talk about investing in slope rather than intercept. And I think Samir and Runic's slope is so incredible

• 29:13Speaker 03

  that it actually made it quite an easy decision for me of yeah, absolutely. We want to go all in on this. And so I would say, I think Sequoia's approach to go all in, keep the bar high, combined with getting to meet Samir and Runic and just believing in them, made it for me a lot easier than it could be.

• 29:32Harry Stebbings?

  I have to ask, sorry, too interested by this. What do you mean by slope not intercept? Is that lines not doors? How do you think about that from an investment perspective?

• 29:40Speaker 03

  Yeah, so I think it's not about where the person is today. It's about where we think they can be in five years or 10 years or 15 years. And so with Samir and Runic, who are very young, I mean, I think we made our Series A investment when they were both 19 years old. Their clock speed, their speed of learning, their speed of generating insights, how much better they are today than they were six months ago and how much better they will continue to be in six months when they're already great. That's the kind of stuff that makes us excited. It's about this, how steep their slope is, is what we get excited about at Sequoia because it's such a long term thing. So it matters a lot less what the business is today. It's about what the business can be in the future.

• 30:24Speaker 03

  And I think that when you have founders who blow you away, you're almost giddy because it's very hard to think about what it could be, but all the possibilities are good.

• 30:33Harry Stebbings?

  Yeah, no, I totally agree with you. I think kind of the rate of development is probably one of the most important but under discussed topics. I do want to ask one more important question before we move into the quickfire, which as you know, I love, but it's kind of the final element. It's in terms of things we've said before, you said to me before, you have to be both demanding and supportive. And they kind of seem at odds when you think about demanding and supportive. So is it possible to be both? And why is it important in your mind to be both?

• 30:58Speaker 03

  Yeah, I think this concept of demanding and supportive is something that I did not make up at all. It was actually the author, Adam Grant, who wrote Give and Take. I don't know if you've read it, if you haven't, or he wrote Originals.

• 31:08Harry Stebbings?

  Yeah, I love it.

• 31:09Speaker 03

  I love it too. I love it. And I was lucky enough to get to have dinner with Adam, with a mutual friend, a couple of years ago. And he was the one who talked about this idea of people think of demanding and supportive as a spectrum. You can either be demanding and push people, or you can be supportive and help them. And he said, it's all wrong. It's not a spectrum. The whole point is you've got to be able to do both. And that's what the best parents do, that's what the best investors do, those board members, the best leaders do. That just resonated with me so much. And so, not only do I think it's possible, I think it's important. And so, let me give you an example. Michael Moritz is on our board at Instacart, and he epitomizes this. And so, the example on pushing us, when we were losing $20 on every order at Instacart, which we were at the beginning, we had some board meetings that really weren't terribly fun, Harry,

• 31:54Speaker 03

  but Michael thought we could do better. And he respected us enough and had enough pride in what we could accomplish to tell us the truth, that, look, this business can do much better than we're doing right now. And we're not living up to our potential. And that wasn't always easy to hear, but it made a big difference. And I think that was an example of pushing us. But he was also really supportive at the right times. And so, when Amazon bought Whole Foods, I mean, that was a crazy time for Instacart. And it's easy to think of Instacart as just always having been so obviously successful like it is now. But I mean, that morning, when Amazon bought Whole Foods, I had 263 text messages. And I'm not you, Harry, that's not a normal occurrence. And so, one of those text messages was from my mom, asking, are you okay? And I think the conventional wisdom at that point was that we were dead.

• 32:38Speaker 03

  And some of those texts and calls were from investors of ours, asking, what does this mean for my investment? And that's not what Michael did. Michael came to our office that morning, and he drafted our response to the press. He's literally sitting at his computer and he's typing it. And then, after he left, he texted a poor man to me his address. And so, we did the all-hands, where we talked to the company about what this meant, which was the most important thing to go and do. But then, the two of us spent the rest of the day at Michael's house with him. And you can imagine that this was a pretty intense day for us. But he was there, and he was there for us when we needed him. And I'll never forget that. And that's the reason that I talk about this idea of being both pushing companies and being demanding, but also being supportive, because that's the kind of partner Michael is and was to us, and that's the kind of partner I aspire to be to the companies with whom I work.

• 33:23Harry Stebbings?

  I mean, I've met Mike and there must have been some tense board meetings for you. I would be terrified. I do want to ask one final thing, and I'm sorry for keeping on going, but it's just too interesting for me. You're such a family oriented person, and both Sagar and Will said this also. How did having children, do you think, change your operating mindset and change you? It's something that I think about a lot, despite obviously being hopelessly single for the rest of my life. It is still something I think about a lot. How do you think it changed your mindset?

• 33:50Speaker 03

  I love that you asked that question because my wife and my kids are the most important thing in the world to me. And so we have three sons, they are seven, seven and six. I'm shocked that on this podcast that you have not heard them yet. But I think in terms of how it's changed me, I think it's really helped me focus on what's important rather than urgent. I read this book called How Will You Measure Your Life by Clay Christensen. And it's just, it's just my favorite book because it helps make sure that you think about this question that's so simple. But I don't think most of us ask it enough. And when I think about how I'll measure my life, the vast majority of the ways that it will matter will be the relationship and impact I have with my family and with my friends and closest people in my life.

• 34:32Speaker 03

  I think having kids has helped me make sure that I focus on the things that are important rather than the urgent. There's always a reason that you should stay late and work on something. Because the impact that you'll make at work will be more visible for that next hour than the impact you'll make at home by the things you do with your kids. And it's more visible and tangible. But over a long period of time, I think it's deeply important to spend that time with my family. And so I think they've helped me a ton maintaining an even keel. They've helped me a ton on remembering what's important. They also are just so fun that I almost can't believe I get to spend the time with them. I'm not telling you it's always roses, but I am telling you that like before we had kids, I don't think I understood what the term you are my pride enjoyment.

• 35:16Speaker 03

  But kids end up being that for you, which is they are your pride and your joy. And I think they help you see work for what it is, which is this incredible thing. And it helps you realize that your job at work is to help serve others rather than just get to an outcome right away.

• 35:31Harry Stebbings?

  I'm so glad I asked that question. Sometimes I'm like, you know, should I ask it? Should I ask it? And then you get bits of magic like that. So I mean, A, amazing to hear, but thank you for opening up like that, Robbie. I'm really pleased. I said, and I actually haven't read Clay's book, so I'm going to add that to the list. And you just nailed the first quickfire question. So well done for knocking that out of the park ahead of time. But the quickfire, so 60 seconds per answer. I say a short statement. Are you ready to rock and roll, my friend?

• 35:54Speaker 03

  I'm ready.

• 35:55Harry Stebbings?

  Okay, so this is often one where people give political answers. So let's see if we can not do a political answer. Most memorable, not best, but most memorable board member you've served on a board with and why?

• 36:06Speaker 03

  I guess I didn't technically serve on the board with him, but it's not even close. I mean, it's Michael Moritz. He's so insightful, but he's also extraordinarily witty and is not even close. Definitely not.

• 36:16Harry Stebbings?

  Love it. I wish everyone was like you in terms of being unwavering. Tell me, the biggest strength and the biggest weakness for you in your eyes?

• 36:23Speaker 03

  I guess one thing for me for sure is, once we've sort of figured out what the answer is, I really like to get there just as quickly as humanly possible. And I really do, I can get frustrated by processes that feel like they're slowing us down. And I think that the reason that I bring that up is processes are important as you get bigger. But I probably am overly resistant to putting them in rather than the way I should be. And on the strength side, I think I help people cut through the noise and get to the root of what really matters. And so I think we get to the so what quickly.

• 36:57Harry Stebbings?

  Tell me, what would you most like to change about the world of venture, Robbie?

• 37:00Speaker 03

  You know, we've touched on it and it's not true for everyone, but I think that some people in our industry treat founders and companies like deals. And I've been on the other end when people call you or email you and tell you they're passing on your company. And I think that's fine. But I think sometimes they feel the need to convince you that your business was bad so that they can feel like they're right. And I think that that just, it misses the whole point of companies are not numbers on a page. They're groups of people devoting their careers to a mission. And after I get off the phone with you as an investor, if I'm working in a company, I gotta go back to my desk and go do work. I gotta go to an all hands and talk about why what we're doing is great. And so I think that investors would be best served to remember. That companies do not exist for their pleasure.

• 37:44Speaker 03

  Companies exist for people to do their life's work. And when you do decide it's not for you, that it's not about proving that you're right. You gotta genuinely hope that this thing does great because the people are still working there, even if you're not gonna invest in it.

• 37:56Harry Stebbings?

  Now, this is probably the hardest one of all. If you were a cocktail, which cocktail would you be?

• 38:03Speaker 03

  Harry, I actually, you know, I have no idea because I don't really drink very much. And so I have no idea what the answer is to that question. But I would love to know what you think or what you'd answer that for you.

• 38:16Harry Stebbings?

  I'm gonna answer it for you. I think you're an espresso martini because you've got this kind of froth on the top, which has a wonderfully, you know, beautiful appearance. But then underneath, there's this like real depth and real meat. And it's surprising and it's kind of sometimes heavy, but actually fun as well. I think you're an espresso martini.

• 38:36Speaker 03

  Well, I will tell you, Mr. Stebbings, nobody has ever said that to me before. And so I appreciate it and I'm gonna take it as a compliment.

• 38:43Harry Stebbings?

  Well, listen, when you actually do get a Twitter profile, you can now put that in your bio.

• 38:49Harry Stebbings?

  But listen, Ravi, as always, I could talk to you for days. This has been so much fun. I really am so thrilled that we got to do this and I can't thank you enough for joining me today.

• 38:56Speaker 03

  Thank you, Harry. I really appreciate it and I can't wait to do many things together in the future.

• 39:03Harry Stebbings?

  I mean, what a fantastic person. I just love doing that show. As you could tell from the fun we had there, I think you really see Ravi's true side when he talks about his family and that was incredibly special to hear. And as I said, I just have so many wonderful things to say about him. If you'd like to see more from us though, behind the scenes, you can on Instagram at H Stubbings 1996 with two Bs. I always love to see you there. But before we leave you today, I want to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million.

• 39:44Harry Stebbings?

  Check out hellosign.com/20vc to join the thousands of companies and founders who value.

• 39:51Harry Stebbings?

  Fast, secure and simple e-signatures. And I do have to mention another incredible product-centric business, Digits. Digits has spent the last two years building this incredibly powerful financial engine for businesses. Now they're ready to show you what they can do with it. Back in April, they announced a real-time dashboard to help you manage your company's expenses for free. And recently, a little birdie told me they have some incredible announcements coming up. They've raised almost thirty-three million dollars from Benchmark and GV, and the team behind Digits is just epic. Personally, I think it's one startup to watch this year and the next. And last but by no means least, has anyone tried to send a business payment recently? Oh my god, it was easier to get into college. You have reviews, you have this never-ending back and forth between colleagues, which just slows the process down.

• 40:34Harry Stebbings?

  It's a lot of work that continues to pile up as your business payments scale, and that's where Rootable steps in. What sets Rootable apart is not only its focus on digital business payments, but the time it saves on both the accounting and the operations sides. Did I mention that Rootable automatically updates your accounting records, making your finance team's lives so much easier? Request a fifteen-minute demo and start managing your B2B payments electronically at rootable.com/20vc for free. There's no transaction fees, no seat fees for one full month. Join Rootable in building the best platform for businesses to manage their workflows and send and receive money digitally at rootable.com/20vc. As always, I so appreciate all your support and I can't wait to bring you a fantastic episode this coming Friday.