Jean-Denis Greze: CTO of Plaid, the $18B Fintech Startup; How to Hire, Fire & Build Great UX | E1038

1. 0:00 – 0:39

   Intro

   1. JGJean-Denis Greze0:00

      There's great hiring and there's great firing. One of the things you realize about founders is first time founders, they don't realize they have to be great at firing. They just think they have to be great at hiring. But you have to be great at realizing when your talent's not working out and identifying that and working with them and moving on. And initially, founders don't do it early enough, and then they learn their lesson a few times and then get really good at it.

   2. HSHarry Stebbings0:20

      Jean-Denis, I'm so excited for this. I heard many good things before we started the conversation. So thank you so much for joining me today, first.

   3. JGJean-Denis Greze0:28

      Cool. Thank you, Harry. I'm super excited to be here. I, I feel like, uh, I'm, I'm getting the benefit of, uh, being on here more than you're getting the benefit of having me on the show. But, uh, I'm excited to do my best to impress.

2. 0:39 – 8:30

   Resume and What to Look for When Hiring

   1. JGJean-Denis Greze0:39

   2. HSHarry Stebbings0:39

      Well, I'm about to extract a decade of knowledge, so I think I'm the one winning. But I want to start with your career. And I think careers are often made actually with more singular moments. So when you reflect, what would you say was the single biggest break in your career, and how did it impact your trajectory?

   3. JGJean-Denis Greze0:55

      That's a good question. I think... Look, I think objectively the answer would have to be joining Plaid as, you know, to, to lead engineering, um, which was about six and a half years ago, just because I joined when the company had, you know, 40-ish people, and, you know, less than $10 million in ARR. We've had f- we've had a crazy trajectory. And it means, like in terms of my career and my ability to be successful long term, I have a lot of options now that I never would have had if I hadn't joined Plaid. But actually, it's not... Joining Plaid is not what I consider the, the lucky break that I had. That would be joining Dropbox, which was my first job like truly in Silicon Valley. Um, yeah, so before, before Dropbox, I kind of had a weird career. I worked in tech for a bit, and then I'd been a lawyer for a bit. Then I helped a friend kind of grow a company, like a fintech company in New York, but more on the hedge fund side of things. And I hadn't had, like what you would call like a triple A employer on my resume. You know, I was smart, but, you know, I was kind of a weird outsider with, you know, a little bit of an attitude. And I realized at some point that if, if you want to be an engineer and you want to do great engineering work, at the time at least, I felt like you had to move to Silicon Valley. And I was in my early 30s. You know, I don't think I'd had a great success. And I knew a friend at Dropbox, and so he got me in the pipeline to apply. And, you know, I applied there, and I, I know 'cause they told me after the fact, I actually didn't do that well on the interviews. I did well on half of the interviews, and I didn't do well on, on the other half of the interviews, especially on some of like the people skills and, you know, I think I came across as a little too smug and, and sure of myself. And there's two people at, at Dropbox that saw something in me during the interview process, uh, this guy Albert and, and this guy Ramesh, and they, they went to bat for me. Um, and, and they, you know, they, they were like to me like, "Maybe we'll structure it as like, like an apprenticeship where you, like join for a few months and we see how it works," and whatnot. And they were like, "Look. No, listen, like we should hire this guy. He's got some spikes. Like he's weird, but that's what we need at, at the company." And a lo- I'll give a lot of credit to the culture that Drew and Arash, the founders, created. Like I think Dropbox was very good not just at getting the standard talent, but at, like looking at people that weren't quite conventional that they thought could really accelerate the business. And I'm, I'm ex- like eternally thankful for it, 'cause, you know, after that, you get Dropbox... People don't realize now maybe, but Dropbox, like 2010 to 2017 on your resume, that really just opened all the doors. And I learned a ton there. It was an amazing company, amazing talent, uh, and I think it's, you know, it admitted that I can keep working here for a very long time.

   4. HSHarry Stebbings3:29

      JD, you were a talent, but your CV did not show it at the time. My question to you is, when you look at LinkedIn profiles today, what makes you excited? So for me, duration makes me excited. I hate bounces is what I call it, where they've done a year, a year, a year, 12 months, 18 months, 12 months. I like 10 years, like duration. What makes you think high quality when you see a CV or a career?

   5. JGJean-Denis Greze3:56

      It's a really tough question. And I think already in an interview process, you're trying to recap someone's talent in four to five hours, right? Looking at a resume, it's just, it's just so, so surface. So what you talked about is more the red flags. For me, there's a, there's a ton of red flags that I look at, for sure, so like staying too long in level, like not having a good trajectory, jumping around from company to company. You can jump around s- once or twice, but if, if you do it over and over again and you never find a place where you're able to like really hit that velocity, that, that really bothers me. I look at online things that you've built, right? I, I like, I like people who are curious, so frankly, like your GitHub, the projects that you've shipped, maybe even your blog. I think that stuff can get me excited. But what I want quickly is, is interaction with, with, you know, the interviewing team. What I want is like time in a room with you. Like the, the resume screen for me is, is fairly limited. And you have to always ask the question with, with talent, which is like, "Are they the right person for my business?" Not, "Are they a great person," right? And, and I think there's a big delta here. Like I always give this advice to startups. They all... You know, startups, they're like, "Oh, I want the best engineers." And I'm like, "You're building a crud app. What is the best engineer for a crud app?" The best engineer might be the person who's like great at React or great at Rails or whatever. They don't have to know distributed systems. They don't have to, like know all that complex technology. So let's look for someone who's got an amazing track record of like the kind of front end work that you have or the kind of full stack work that you have. And, and when you do that, it's no longer like a great resume. It's like you have things you're looking for, and you ask yourself, "Does the experience on this resume seem to match what I'm looking for? Do they have enough time doing the things that I'm looking for?" And I think that's how you find, quote unquote, "great," you know, for your, for your business.

   6. HSHarry Stebbings5:53

      How do you advise founders in terms of hiring ahead of time? You spoke about the best engineer there for your business. Often VCs, it claim to be able to show the problems before they become problems and help you hire ahead of time. Do you think founders should hire ahead of time, or actually it's hiring for the here and now?

   7. JGJean-Denis Greze6:12

      I've... I think I've changed my mind on that. I, I think for ICs...... very early on, like first, like, 15 people, you wanna hire for the here and the now. You want people who are hungry, who can solve the problems you have right now, 'cause you're trying to get and expand your- the amount of product market fit that you have, and the amount of product momentum. I think at most companies, the advice that I give is somewhere between 15 and 30 people, things will break on the management side, and the problems that you encounter are not cookie cutter. Like, you can't ask someone who's grown a company to 200 and ask them to give you a roadmap of the changes they had to make and be like, "Those are the changes I'm gonna have to make." No. 'Cause every business pretty quickly ends up looking different. So at that point, what I generally say is like, "Hey, you need to hire your first few managers and your first head of." Like the first person who's kind of gonna grow your product team or grow your engineering team. And I think there, there, there are two choices you can make. One, you can hire what I call the four-year candidate. The person who's run like a 75 to 100-person team. So they're gonna come in at 20 and you're gonna be, as a founder, you're gonna be like, "Cool, this person is gonna be able to grow us for a while. They- they're smart, they're a problem solver, they'll get in front of it." Or you can hire what I call the two-year candidate, maybe a person that's managed a 35 to 40-person team, much easier to hire, but that person, at least you know like, hey, listen, like, they're gonna be able to get the next year and a half, two years, they're gonna be great, and then I'll have to reevaluate. So I used to be in the four-year camp, but it's just such a hard hire, and there's actually this thing that happens where the person who's running a really large team may once upon a time have been good at running a small team, but they may not be anymore, you know? Like, I don't think I would be a good manager for a 20-person team anymore. I was when, when I joined Plaid, but I'm like so out of ... That was six and a half years ago. Like, I've lost all those muscles. And so, you know, if you go too long term, if you don't hire for the here now, sometimes you get someone who's not that excited about the here and now, not willing to roll their sleeves back. Maybe even their technology understanding is, is behind where it needs to be, right? Like, things are changing on the ground. So, you know, I, I think it's always easier, faster to make the shorter term hire get the impact, as long as you're honest with yourself when they stop scaling, right? And so you either recognize they're still scaling, I'm gonna s- I'm gonna support them, mentor them, get them to the next stage, or you're like, hey, maybe it's not quite working out. I need to, I need to think about, you know, every two to three years upgrading my, my exec

3. 8:30 – 10:59

   How to Scale Your Company

   1. JGJean-Denis Greze8:30

      bench.

   2. HSHarry Stebbings8:30

      We always say about like, stop scaling, and it, it's like rom-coms. It ends there. What happens when they stop scaling? Do they, do they move on? Do they remain in the org and we layer them? How do you think about efficient handling of that kind of trajectory-based scaling with those kind of categorized characters?

   3. JGJean-Denis Greze8:50

      Yeah, I mean, how unfrench can I be on the podcast? It ... Look, it's capitalism, and your responsibility is to shareholders, right? And you do, you can do right by people in the transitions, but, you know, sometimes you get someone who realizes that they need a better leader, that they're gonna learn from a better leader above them and they're ready for it. And that's awesome, and that's what you should try to do when that moment comes. And, and sometimes for everybody it makes sense for them to just go find another gig where, where they've grown at your company and they can now do another stage. It's not the stage that you have. And it's okay. Like y- y- you know, you can ha- I think as adults you can have these conversations. I think where you get in rough waters is when you don't give the person a chance. I p- I call that like putting the person in a box-

   4. HSHarry Stebbings9:31

      Mm-hmm.

   5. JGJean-Denis Greze9:31

      ... where you have this image of them from when they joined and, you know, y- the company hits some kind of rough patch and you, you don't give them some chance at like seeing if they can grow out of it. I think the human thing to do is to give them the chance. But you're a founder and you've, uh, hired all these other people, and if one of your function leads isn't scaling, yeah, you might give them three months, but pretty quickly you gotta realize, hey, it's not working, 'cause next thing you know, you might have, you know, if you wait like 12 months and then you make a new hire and that person onramps, next thing you know, you've wasted 18 months of potential momentum at, at your company. And that's, that's dangerous. And I, I think I always ... This is like not a super podcast, like, like happy, happy, uh, makes me look great kind of statement, but I, I think there's great hiring and there's great firing.

   6. HSHarry Stebbings10:16

      Mm-hmm.

   7. JGJean-Denis Greze10:16

      And I think founders, one of the things you realize about founders is first time founders, they don't realize they have to be great at firing. They just think they have to be great at hiring. But you have to be great at realizing when your talent's not working out and identifying that and working with them and moving on. And initially founders don't do it early enough, and then they learn their lesson a few times and then get really good at it.

   8. HSHarry Stebbings10:37

      Listen, uh, uh, by the way, it's a really interesting thing. People think about like, oh, it doesn't sound good on a podcast. What founders love the most and what makes them like people the most is actually the honesty, the not BS, selling your company, you know, it's all about mission and vision. That doesn't sell. That makes people dislike you. The truth like that is what makes people like you. My question to you is, I suck

4. 10:59 – 20:00

   How to Fire Someone

   1. HSHarry Stebbings10:59

      at firing, so much so that I've had s- my COO fire people because I don't want to do it. How ... What does being good at firing mean, and how can I get good at it?

   2. JGJean-Denis Greze11:10

      It's like having a breakup. No one ever likes doing it. I don't think you truly get good at it, and I don't think you ever have a playbook where both sides come out of it like super happy humans. That's just th- that's just reality. So first thing, you gotta realize that. When I say good at, I actually don't mean the conversation with the other person. I mean identifying at the right point in your company that the odds of success of that individual in the role is no longer right for the business.

   3. HSHarry Stebbings11:36

      Mm-hmm.

   4. JGJean-Denis Greze11:36

      Because I- if you can look at someone in the eye and, and you're convinced yourself that it just doesn't make sense for the business, you've given a shot to pro- a shot for them to improve and prove themselves and they haven't, you're just doing what's right for the business and they will understand that and they will respect you for it, even if they don't like you in the moment and they don't feel like it's fair. 'Cause they're shareholders, they joined a startup, they understand the risks, they understand it's, it's a very, very difficult job. I just think that's how you have to treat it, right? There's a human level, wh- you know, how you deliver it, how open you are in communication, that those things matter, but at the end of the day, it's, it's about what's doing right for the business. Probably the biggest mistake is not giving feedback.... right?

   5. HSHarry Stebbings12:18

      Oh. Oh, no.

   6. JGJean-Denis Greze12:18

      That is-

   7. HSHarry Stebbings12:19

      No. No. I disagree with you. Don't give feedback. That's a-

   8. JGJean-Denis Greze12:22

      Oh.

   9. HSHarry Stebbings12:22

      ... terrible thing, JD, because they'll always argue with your feedback. (laughs)

   10. JGJean-Denis Greze12:26

       Oh. Uh, no. I mean before, meaning, it-

   11. HSHarry Stebbings12:28

       Uh-huh.

   12. JGJean-Denis Greze12:28

       ... it shouldn't come out of left field. The person should know that their performance is not quite meeting the bar that you have anymore, like, a couple of months before. If it comes out of, say, in your head, you're just like, "Ah, it's not working out. It's not working out. It's not working out," and then you show up at one-on-ones, and you're like, "High five. Let's go watch, like, a soccer game. You're the best," it, y- you know, then when you deliver the news, th- m- that's, that's just not, that's not gonna feel good o- Yeah. In the moment, no, you've made the decision. There's no argument, right? If you've made the decision, you know, they try to argue with you, and you're like, "Look, listen, like, I'm doing what I think is right for the business. This is my role to do what's right for the business. I've thought about it. This is, this is what we're doing. I'd like to work with you on, like, a transition plan that works."

   13. HSHarry Stebbings13:07

       JD, w- when, when you reflect on hiring, what have been your biggest mistakes?

   14. JGJean-Denis Greze13:14

       I think it, f- the first one is not being crisp about what we need in the role.

   15. HSHarry Stebbings13:18

       Hm.

   16. JGJean-Denis Greze13:18

       You know, it's the difference between, "I need someone to run data science," and, "I need someone to run data science. Our major data science initiatives are around risk and fraud. I'm really gonna value somebody who's done that in industry for a bit, but I want an out-of-the-box thinker because at Plaid, we're not doing fraud and risk like every other bank." The second, that second thesis, like, culls the space significantly. It's like, okay, they've gotta have worked at a traditional institution, but then I've gotta have seen them work in a really creative environment, right? It, it, it's fraud and risk, so I'm not gonna hire a data science person who's done, who's not had any of that experience. Like, you've, you really gotta get the requirements really crisp, first. Second is, your interview panel needs to be aligned on what you're looking for. I've seen too often, especially with senior hires, where all the interviewers are, like, you, you know, heads of things, and they're all asking the generic question, like, "Oh, tell me a great success in your career. Tell me about a time you failed," and you don't get real signal from that. Like, you need to be like, "Hey, head of HR, I need you to talk about how they can, have they worked teams through difficult execution challenges. Hey," like, you know, GTM person, like, "I really care about, can they work with PMMs on, on, on pulling out data requirements for data products?" Like, make it, make the interviews really specific. And then number three, you have to have interviewed enough people that you know what great looks like. And so if you have the perfect candidate be your first hire, like the first person you interview, it's really hard to pull the trigger, because people don't have any comparison points. But if people have, if that panel has seen seven or eight candidates before, and they'll have a feel for what good is and what great is. And so this, this sounds unfair again, but, like, the, the way I really feel about it is, you kinda need to put the interview process through rounds, like right through work. And so what you do is if you have your first great candidate and they come really early, at that point in time, you gotta interview three or four other people. You gotta find three other, four people to interview, because you want your panel to feel confidence that someone truly is great. Otherwise, it's, it's hard to, to pull the trigger. I think that's the first hiring, and then everything else is on the recognizing if they're successful. I think setting them up to succeed and having, having an objective data point pretty early on, like two to three months in, that really tells you, like, this person is gonna work out or not. Don't leave that to chance. Don't be like, "Oh, they're hired. They've started. They've, like, onboarded their team." You gotta have, like, a reminder in your calendar three months in, four months in, five months in or whatever, that, where you objectively sit down, and you're like, "I asked them to do these things. Are these things done? I thought would change the trajectory of this function. Has the trajectory changed?" And if you can't answer yes to the questions, then we may be into the conversation you and I just finished having.

   17. HSHarry Stebbings16:02

       I, I love doing what I did 'cause I just write these schedules, and then fuck them. Uh, I'm so enjoying this. Uh, like-

   18. JGJean-Denis Greze16:08

       (laughs)

   19. HSHarry Stebbings16:08

       ... and so two questions I thought on the, like, negotiation pre-joining side. One of my biggest lessons is when people are really difficult on the title, "I want chief of staff, not EA. I want head of engineering, not VP of engineering," or whatever that title, it's never a good hire. Do you agree? And have you felt the same, or actually am I wrong?

   20. JGJean-Denis Greze16:31

       Certainly, the most of the envir- environments I've worked in, we try to be kind of low ego, low title. We want the best ideas to win, not just the most seniority. So even at Plaid amongst ICs, for example, there are no titles. Even in managers, outside of the person who leads, like, a, a giant area, we have don't, we don't have directors and, and things like that. So I've been very much in the, like, it's, it's not a red flag, but it's a little bit of yellow flag when people really care about those things. The, the flip side of it, which I think is, is really, really important, is it actually, it matters in the industry. And you can never fully divorce yourself from the industry, especially when you get to a certain size, right? When you get to, like, 1,000 people, 2,000 people, you're gonna recruit people who have titles. You're gonna recruit people for whom titles matter. So, like, a, like, a thing for you is, um, there's bias and unfairness in the industry, right? And so there are some underrepresented groups for which being a staff engineer on LinkedIn is truly meaningful career-wise. It... You know what I mean? It, it matters not... It's not about ego, right? It's a, it's a, it's a, it's about this feeling that the industry hasn't, like, done right by you, and, and when you achieve this thing that is truly meaningful, you wanna, you wanna celebrate it. So I think at scale, when you're, like, at our size right now, like, we're, you know, 1,000 people total, like, transparently, I think you wanna go with the grain of the industry, not against it, because it- it's just too much fighting to go against it in some places. So you have to be picky around where going against the grain really accelerates the business versus the places where you should just, like, be more default. I think when you're very small, I, I, I think it's, it's, it is a red flag. People should care about impact. Everything's gonna be fluid, all that stuff.

   21. HSHarry Stebbings18:18

       Where does going against the grain accelerate the business?

   22. JGJean-Denis Greze18:21

       I think that's very, like, business specific. My...... over-arching thesis is that a lot of people things, and a lot of people matters, how you level, how you title, how you comp, um, how you organize your org, like your manager to IC ratio, remote/hybrid, it's like pick a thing, pick one of the three options on the menu for each of those, and just, like, move forward with your life. I- I just don't think it's the difference between a good and a great business. Like, bad strategy, bad product plan, going into the wrong market, they're y- you, the efficiency gain or loss is like 100% or 0%. You know, you build the wrong product for, like, two years, you're slightly better at leveling people, like, I don't know your Pulse Score's like three points higher, and your retention is like one and a half percent higher. Like, I just don't think that fundamentally matters.

   23. HSHarry Stebbings19:21

       How much does speed of execution matter, JD?

   24. JGJean-Denis Greze19:24

       That's the most important thing. It's shots on goal, right? You execute faster, you get more sho- shots on goal against your competition. So I th- I think given the constraints of your business model, right, like you're Plaid, you're doing, or Stripe, or whatever you're doing, banking and payments thing, like you're not, you- you can't move fast and break things. You have to move fast, as fast as you can while not breaking things. Within the constraints of not breaking things 'cause it's people's money, you wanna be the fastest person because you get more shots on goal against the competition.

   25. HSHarry Stebbings19:53

       What are the single biggest barriers to fast execution do you think?

   26. JGJean-Denis Greze19:56

       I mean, technical debt, lack of focus, like lack of clarity from

5. 20:00 – 26:20

   Remote vs In-Office Work

   1. JGJean-Denis Greze20:00

      leadership about what you need to do, like a not- not a concrete plan. Technical debt gets in the way for sure.

   2. HSHarry Stebbings20:06

      You- you mentioned some, uh, crucial, crucial topics there, which I- I do wanna discuss 'cause we touched on them a little bit before. One of them, which I'm actually very passionate about and not in a friendly way either, but it's the in-person versus remote versus hybrid. Um, talk to me about how you think about this, and do we have an opinion here?

   3. JGJean-Denis Greze20:25

      One opinion I have is we've talked too much about it.

   4. HSHarry Stebbings20:28

      (laughs)

   5. JGJean-Denis Greze20:28

      So there was, uh, l- I think I spent a lot of the last two years in these CTO dinners where we, or CPO dinners, or president dinners, or whatever, VC dinners, you name them, and we would spend half of the time talking about what we're doing, when are we returning to office, are we not? Are we- are we hybrid? Are we remote first? Are we moving back to in-office? And when I say it doesn't matter, I- I think- I think there are plenty of really successful companies before the pandemic that were really going hard after fully remote first. And it worked for them 'cause they had a- the people who went to work there were people who went remote first. What happened in the pandemic is we forced people into working models that maybe they didn't like. So on my team, I have people who like remote first and I have people who wanna be in the office 'cause I didn't pre-select in my hiring criteria, like, a- a specific persona. Now, you kinda make a decision, and I'm not saying it doesn't matter, but again, I don't think it's the difference between success and failure. You make a decision, you make sure your hiring and your culture matches the decisions. There's a few areas where I think you should be careful, so I'll- I'll give you example. Highly creative, fast-moving work where you're not sure what the requirements are, and where your customers are local, meaning where you can go and talk to your customers by, like, walking over to their office, so this is like historical new company, new startup in Silicon Valley, I think in-person is better because I think you collaborate more effectively, you have- y- it's easier to get everyone on the same page, you can go talk to customers by, like, you know, taking a car, walking over. And so if you have a lot of work like that at your company or you have teams that look like that, I think getting those teams to operate in-person is beneficial. However, at scale, incremental improvements to existing products where you care about efficiency of the team, and you have clarity of roadmap, personally, I think almost in remote we're much more effective. Like s- definitely I have no difference in like PR success rate. I think the only thing in remote that's hurting me is Pulse Score in terms of belonging and how much fun people are having on the work. Like, I think that has gone down from before, but I think in terms of quality of the work and the productivity, it's the same.

   6. HSHarry Stebbings22:45

      I- I- I- I totally disagree. I-

   7. JGJean-Denis Greze22:48

      Oh, I love it. Let's- let's go.

   8. HSHarry Stebbings22:49

      I- I- I- I- I- they do not work as hard, and they do not work as well, and they do not feel the same culture, togetherness. The idea sharing is totally different, whether you're in marketing, whether you're in sales and the camaraderie, your retention is fucking slammed. You have a bad day, you go down to your other half and they say, "Oh darling, well, what about those LinkedIn recruiters who are offering you jobs at the same pay?" Versus when we're in the office together and you and me go out for a drink at the end of the day and you say, "Dude, I love working with you." And I go, "Ah, you know what? JD is good and Plaid's a good place to be. I like it here." And so I think it fundamentally changes the creativity and retention fabric of a company, and I think we're gonna see a load of- Sorry, I'm on my high horse. We see a load of VCs who made a load of investments without ever meeting the company, and they are unraveling faster than ever now, and that is in large part because they didn't spend the time in person, I think.

   9. JGJean-Denis Greze23:41

      I agree with you on the culture side b- but I think you can... there's hybrid models where you come in like two to three days a week and you make the office awesome for those days where you can get a lot of the benefits that you're talking about, and I- and I think a lot of people are trying with that. I disagree on the productivity front, um, on- on, again, on work that has like clear roadmap and is more incremental. I think w- we've had a lot of success there, but, you know, we'll see. Like I just... I think for early stage is where, and that you look at all the early stage comp- like a lot of 'em are going back to in-person. I mean, that is like, it is- it is happening right now. There's an exodus from New York to SF, um, that's happening, and from, I'm not saying Miami, but from other places where- where people went. And it's around AI because the zeitgeist is here. All the AI folks are like getting together in the evenings, they're going to the same places, like all the gen AI stuff, it's like it's sucking a lot of people back to SF.

   10. HSHarry Stebbings24:41

       But do you have to be in the Valley n-... to be doing AI startups today?

   11. JGJean-Denis Greze24:45

       So, I was in Europe for a trip, like, a few months ago. And a lot of the trip was talking to startups and fintech around, you know, the UK and Netherlands and etc. And I think what was really fascinating to me is how much of the culture of how you build a company and scale a company is now internationalized. I think the- 10 years ago, there was this knowledge about, like, "What does your first PMM do?" And, like, "What's growth hacking or PLG, and how does it..." Now, kind of everyone knows that stuff. It's pretty impressive. I think there's still more people who've seen through it here, who've done it, like, four times. But there are a lot of other places in the world that have proven that they can export the- the company, the startup building, and the culture of Silicon Valley. The AI stuff is a l- I'm not saying it's different, I'm not- don't know enough, but you can feel right now that the Zeitgeist is in SF. Like, there are just a ton of people here doing the work. And I don't know if it means that you can't do the company elsewhere, 'cause I- I- I think it's much easier to do a company where you're- you don't have to meet your first customers in person and things like that nowadays. But I think it's still an advantage to be here.

   12. HSHarry Stebbings25:54

       I call it the battery, which is like I go to SF, I get charged with a load of optimism that you can change the world with a few people, and then I come back to Europe with this idealistic view of the world and what we do, which can be realistic for a small few. And I- I like that, like, optimistic take of the world, and that's why the Valley is so helpful for me. I do want to ask, you know, a lot of people who love, uh,

6. 26:20 – 33:53

   Work-Life Balance

   1. HSHarry Stebbings26:20

      remote and hybrid, I think love it because of the work-life balance that it brings. You've said before work-life balance is good for people who do not care about work-life balance. When I w- reading this, I was like, "Either I'm thick or I just don't get it." Can you help me understand this, JD?

   2. JGJean-Denis Greze26:38

      Yeah. So- so you mentioned earlier that you've- you've made a lot of investments in France, right?

   3. HSHarry Stebbings26:42

      Yeah.

   4. JGJean-Denis Greze26:43

      Um, so I'm gonna say some things that people are gonna like probably on the podcast, um, but maybe my team won't like it, uh, at Pod. I don't think my team is this way. But France is interesting, right? Because as a country, there's kind of this ethos about, it's not cool to talk about work, and you don't wanna work too hard, right? Life is- y- y- you work to live, right? That's like the- the Frenchness, right? And the result of that is, if you are a person willing to work 80 hours a week in France, if you try to work for a big company, you get- you get hammered down. They, like, won't let you work that hard. Like, you know, people are like, "You're making us look bad." Like, you know, they're like, won't let you use your workstation off hours. Like, it'll be weird. But if you're a startup, or if you're doing something new, or if you're like an independent, you have your own little company, like a law firm or a small investment bank, you can crush it, because your competition's working 40 hours a week, and they're going on vacation all of August. And s- so if you're the- if you're the law firm who's willing to be available from July 15th to September 15th, like, welcome. Like, pe- people will go and work with you. And so the way I would talk about tech is, you know, tech 20 years ago, the software tech, right? Obviously, the Valley's existed since the '50s. But like, you know, software, cloud, internet tech, you know, 20 years ago, it really truly was techbrosi in the sense, like, everyone was in their early 20s. Everyone was working all the time. There was no work-life balance. And as tech grew and had a lot of success, there was this movement around like, hey, if we want- if- if people with kids want to be successful here, people from different walks of life, like, we want to create an environment where, you know, you can work 40 hours and still do great work and have, uh, great remuneration. And that's what's happened, right? Like, people have fought these battles, and the culture has changed. But the ch- culture has changed so much that now I have people who want to work hard who are like the French person at the big company. They're like, "It's hard to work hard." Like, "It's hard to go... I- and I feel guilty doing it," and all these things. And what I always tell them is like, "You're thinking about it wrong." Like, it is much easier for you to get a promo. It is much easier for you to look good if you're willing to do those things, because the average now is- is truly going into this, like, you know, 40-hour week kind of thing. And I feel the- the- the relationship of many tech employees to their tech employer is the same as, like, a French citizen to the French government, which is like, the employer shall provide. All the big problems in life are the fall, or the f- you know, the fault of the employer. Like, kind of this weird, like, lack of ownership mentality. So, I-

   5. HSHarry Stebbings29:15

      And an entitlement mentality.

   6. JGJean-Denis Greze29:18

      It- it has- it has the entitlement in it, for sure. And look, it- it's awesome that we've earned the work-life balance. I love the work-life balance, right? I still work really hard, right? But now I'm less constrained of- th- than I used to be. And- but what worries me, right? For exa- overall, and why I think innovators in small companies will continue to have an advantage, is because I do think if you care work- care more and you're more focused and you're willing to go the extra mile, you will build better things, right? And can't ask everyone to do that. So I like the fact that we have work-life balance. But I think for the people who really, like, want to push, they're- they'll have more career success. And one of the, it's not a story, but it- like, one of the situations that I find always interesting are, like, new grad hires across the industry who are r- really these brilliant, brilliant people, right? And- and who join the tech companies. And the first time in their life when there's not equal treatment is the first promo cycle at their company, when some people get promoed to the next level after 12 months, some it's 18 months, some it's 24 months, some it's 30 months. And it happens, and they're like, "But I'm as smart as the other people." And then suddenly it's like, "Well, I don't- no one cares that you're a smart." What people care about is, are you a top producer? And there's different ways you can be a top producer. But when everyone's as smart as you are, what's- what's gonna differentiate your, you know, your- your success? And I think hard work will matter. Now, everyone's gonna get the promo eventually, right? Or most people are. So you'll still have a good life if you get paid a lot. But you can't be surprised when someone outperforms.

   7. HSHarry Stebbings30:52

      Do you know what separates the- the one that does get the promos and the one that doesn't most often? And this is not a me being an old man boomer.It's the one who's in the office more as well. Sorry. Sorry.

   8. JGJean-Denis Greze31:04

      (laughs) There you are. You're back to it.

   9. HSHarry Stebbings31:06

      Uh, it's just, it's just true. Um, I totally agree. Um, I, I, I do wanna ask one final one on people, and it's just a question around, do you believe that you can be truly great and have work/life balance? And when I say truly great, let me put a placement around it. Build a $10 billion plus company. I don't.

   10. JGJean-Denis Greze31:27

       Well, so I know a few truly great people who I think are... have the right viewpoint and are really good at motivating and delegating, meaning they create the structure for success, like the North Star, the product roadmap, and then they're able to motivate other people to go in that direction. So that person can do it, and that person could be a great CEO. Like, it's, it's possible. But as a whole, no. You need... Y- I think to, to do great things, you, you... there's a, there's a great sacrifice. You'll find exceptions, like one-offs, but I think on average, it, it doesn't play out. And, uh, the analogy that I would say is to, like, a professional, a professional athlete, like a, a LeBron James or, or whatnot. There's plenty of people who are professional athletes who, from a pure physical understanding of the game, they're there, and who just don't put in the work, and there's people who put in the work. And with athletes, we're totally okay to make fun of the ones that don't put in the work, right? They get... Like, the, the, the sports writers, like, just, like, make fun of them all the time. They're like, "Ah, it's a 15-year career. You get one shot at this." Like, "You get your big payday and then you stop trying as hard." Your idea, like, love digging into them. But, like, what's the difference? You know, we're like, "Oh, the athlete's career is so short," you know? So, so, like, they shouldn't... "They should tr- work as hard as they can for that period." Man, life is short. Life is short for all of us. You think, you think, you know, your professional career of 40 years is, like, much longer than the professional basketball player's 15 years? It's not that much longer, dude. Our life is short. Our time on Earth is short. So you choose how you wanna spend the time on Earth. And if what you care about the most, right? Is, like, having a great life and, and it's... the work is not what gives you fulfillment and not the thing that you care the most about, I think tech is awesome, because we allow you to do that and still do great work and be creative and work with awesome people, right? But I think if you, if you really, really wanna have, like, the outsize impact, I do think the incremental hour works, the incremental focus, the caring more, the thinking about it, like, in the shower, at night before you go to sleep, writing the extra email, talking to an extra founder, caring about the market a little bit more, reading an extra book, like, it all matters.

   11. HSHarry Stebbings33:41

       It totally matters. I, I think, you know, I try and think about people who buck the trend, and I think the founder of Patagonia is, like, the only one that comes to mind. Um, and I'm sure he didn't have much work/life balance, but it's purely from reading.

7. 33:53 – 39:47

   Startup UX (User Experience) Deep Dive

   1. HSHarry Stebbings33:53

      I do wanna go a layer deeper beneath people, though. And I wanna discuss something that you said which I thought was fascinating. You said product differentiation is not sustainable differentiation. Rare from a product person and a CTO. So help me understand this one.

   2. JGJean-Denis Greze34:08

      Great products have won for the last 15 years, and I, I think that's what we see. We see that in consumer for sure, but we see that in, in B2B SaaS, right? If you look at, you know, c- companies of the '90s and 2000s like PeopleSoft and, like, Oracle, like, the UX is not good, right? But it solves business problems.

   3. HSHarry Stebbings34:28

      Coupa or Bill.com suck.

   4. JGJean-Denis Greze34:31

      Yes, good point, but let- let's... Workday also sucks, right? But Workday is much better than PeopleSoft. It's just night and day. And actually, Bill.com versus, like, a non-internet billing system is incredible. It is like earth shattering, right? So here... L- here's a couple of thought experiments. Imagine pre-s- pre-Stripe to Stripe, right? Like, oh, you, you wanna process credit cards? Cool. It's like $100,000 down payment. It's gonna take you six months to do through the contractual. You're gonna get this shitty form. Compare that to Stripe. Stripe, it's like you sign up on the website. You can use the API immediately. Once you have this amount of, uh, of traffic, they do a little more KYB on you, blah, blah, blah, you scale. The delta in that in value is like going from one value to 90 units of value out of 100. If you go to the Stripe website now and you look at what they've launched on the developer experience, it's awesome, but it's the difference between like 90 and 93.

   5. HSHarry Stebbings35:31

      Mm-hmm.

   6. JGJean-Denis Greze35:31

      And so I think over the last decade on a lot of product experience, we went... because of the cloud, right? Because people moved to things being available everywhere, because before all the hosted solutions had no incentive to iterate on UX because, you know, it, it was really hard to migrate to someone else, w- we moved to the cloud where it's easier to migrate and test different providers, so there's been a lot of com- competition on UX. But I think given the current technology trends, AI may change it, but if you just, like, put that in a box for a bit, a lot of competition has happened in UX, and I'm not seeing UX ideas that are like 10X to where we are today. And so number one, and number two, you can copy UX. And this is really important, and there's a couple companies that are doing this right now. I think the most famous would be Rippling, where, like, Rippling's building, like, the next Workday, and they've taken like, "Oh, this company does HR analytics? We'll, like, copy 90% of their good features, and we'll make an integrated version that works with your employee directory. Oh, you wanna do, like, global billing? Like, we'll do, like, a 90% as good version of global billing, but we'll make it even easier because, like, we'll deal with all the inter-country thing on our own." And they do that, and they're building a suite that basically takes all the vertical products that have won for verticals, integrate them into a combined experience, and they don't have to innovate on, on pure UX for any vertical, they can just copy the best. Now, they're selling a suite, right? And that's where the value will come from. I think the value won't come from out of this world UX.... I think it will come from, like, a suite of things that is cheaper, like works better together than the highly verticalized products that we've done today.

   7. HSHarry Stebbings37:09

      Can I make a case, uh, an alternative case, which is UX-

   8. JGJean-Denis Greze37:12

      Of course.

   9. HSHarry Stebbings37:13

      ... isn't innovated on now as it was before because of the maturation of platform kind of life cycles. Like, we are at kind of-

   10. JGJean-Denis Greze37:24

       (laughs)

   11. HSHarry Stebbings37:24

       ... far into the PC, far into the mobile, and my question is, do enabling technologies like Apple Vision and AI allow us new dimensions of UX that will recreate product differentiation as a sustainable?

   12. JGJean-Denis Greze37:41

       Yeah. And that, that, and I think that's a, like the open question. I'm talking about the current waves. And so I think startups that are being founded now, because new models, be it like talking and speaking because of things like generative AI, like LLM's ability to deal with, like, ambiguous human language to get to action, be it, like, vision, you know, AR, um, VR, et cetera, those things may change the game. But I'm putting those in a box 'cause I don't, I don't, I don't know, right? It's like I'm not, like, creating a startup somewhere where that's my thesis. I think for the existing startups, what you've gotta look at is, it, it probably isn't gonna be UX, and there's probably gonna be consolidation because we've over-verticalized things by going after every, like, bit of the software with a slightly bit better UX here or there. And I think the value now is gonna be from tying it all together. And there's a f- there's a few companies that are doing that, and I think those are gonna be the big winners.

   13. HSHarry Stebbings38:35

       What do you mean tying it all together? Like, there's the compound startup like Rippling there.

   14. JGJean-Denis Greze38:39

       Yeah.

   15. HSHarry Stebbings38:40

       What do you mean by tying it all together being where the value is?

   16. JGJean-Denis Greze38:43

       That's a perfect example. I think you have to ask yourself, like, who's gonna do that to Salesforce, right? Who's gonna do that to, to that software? 'Cause it's been, you know, who lives in so- in Salesforce versus lives in, like, Gong and a handful of oth- other tools. So that's like another area that's ripe. I think security tooling is the same way.

   17. HSHarry Stebbings39:00

       Are you long or short Salesforce?

   18. JGJean-Denis Greze39:02

       Salesforce, to me, feels like it's an- increasingly a, a, like a database, like a, a store and not where the UX happens. But because everyone still has to store the data in Salesforce, it's still, like, the base thing that everyone buys. But HubSpot, like pe- people are going after them. You know what I mean? And so I, I just think there's too much market cap, there's too much money to be made there that s- I think someone's gonna figure them out. And, uh, yeah. So I, I would say I am bearish on Salesforce's ability to stay number one over the next decade.

   19. HSHarry Stebbings39:36

       Can I ask you, I think a lot of companies, when we think about kind of bluntly what it takes to win, if it's not around product, it, it does focus on setting the right North Star or understanding where to focus.

8. 39:47 – 44:55

   North Star Metric

   1. HSHarry Stebbings39:47

      How do you think about how to set the right core metric and what effective North Star identification is?

   2. JGJean-Denis Greze39:55

      I think now compared to five years ago, I'm more wary of, like, the one metric to rule them all. Um, yeah, I, because, just 'cause I've seen it... I've seen w- what I would say the difficult part of product n- not be solved by setting the right metric. It certainly helps, but it doesn't answer all the questions. So I'll give you, like, like an a- a applied example, which is actually, I'm giving... We have a metric around conversion, and it's the metric that matters the most to our customers, meaning when someone tries to connect their bank account, are they able to connect the right bank account for that use case? And w- we do a ton to track conversion. But if you think about the work that we do on conversion, imagine, um, you're trying to go from Manchester to London, okay? Maybe it's not the best example. Let's, let's, 'cause they're a little too close in proximity. Let's say you're trying to go from, um, uh, Paris to Milan with Alps kind of in the way. So one way to go from one to the other is to walk. Say your metric... So you're, say your metric is like amount traveled, like percentage of distance between Paris and Milan traveled. So you go walking. So that one's awesome because every day, it goes down, and you can predict very clearly when the person will get to Milan. And then there's another person that decides to take a train. So what that person looks like is, they're like walking kind of in the right direction because the way train stations work in Europe, they're generally in the right direction where the destination is, and they go slowly and then they stop there, and then they go really fast, right? And then you have another person that's taking the airport. So they're like j- going in the wrong direction, then they stop for a whole while and you don't understand what's going on, and suddenly they zoom over to Milan, right? Now, clearly the best mode of transportation, right, the fastest mode of transportation consistently is the airplane. Uh, and in this hypothetical universe are no strikes. Um, and we know the airplane is better because we've like done the work and I know they exist and they go, but a lot of product work actually at most companies, right, on a metric, will incentivize the walking kind of behavior because it's measurable, it's clear that it's gonna get you in the right direction, and every day you see progress. And that's awesome. But the best work, the best work is the work where you're like building an airport and inventing airplanes, and then a few years later you can hop over from one place or another not in 27 hours, but in one hour. So whatever metric you set, and you should have a metric and counter metrics to make sure people don't abuse it and don't game the system, you should do all that correctly, I think the really hard decision always is like, hey, do you do incremental work that has more guaranteed payoff? And how much are we willing to invest in things that could be real multipliers to the product goal, but like, you're not gonna know for a bit if it's successful, right? And, and sometimes you won't know for a while and it's gonna feel like it's failing. And what happens is your, your PM is at the airport and he's been waiting for his flight that's delayed, and suddenly he gets this text message from the boss and the boss says, "Okay, well, just take the train." Right? And that's stupid because he goes and take the train and then the airport, the airplane's ready to go and you miss the airplane. And that's what happens, right? Like, you like start the project, it's ambitious, you work on it for nine months, the metrics aren't moving, you have revenue pressure, and you're like, "Ah, we are, we're not gonna do it." Right? Or, and so I- I- I think the metrics are amazing because you need them because you need to judge, you have to, you need some way to judge whether you're making progress. So you need lin- leading indicators. You need North Star, then you need leading indicators of your North Star. But you need judgment and gut-... right? You can't abdicate the judgment and the gut to a metric. You need someone to go on a limb and say, "I believe that this will work. I will, I will put my promotion and my career on the go, like, we are gonna have five people work on this thing." I think that's the part of product that's really hard.

   3. HSHarry Stebbings43:42

      Do you do incremental work today at Plaid-

   4. JGJean-Denis Greze43:45

      Yeah.

   5. HSHarry Stebbings43:45

      ... given the size?

   6. JGJean-Denis Greze43:47

      For sure.

   7. HSHarry Stebbings43:47

      Yeah.

   8. JGJean-Denis Greze43:48

      For sure, yeah. And as a matter of fact, m- this year, we have a conversion goal, and we hit our annual goal on conversion in six months. And we did it mostly through incremental work, because people were smarter about looking for opportunities. And it's a huge win for the business. But we still have a home run on that, and the home run matters more over any time, over any timezone, 'cause if we get the home run, it's not just conversion, it's differentiated conversion for us. It's conversion that's very difficult for competitors to, to get.

   9. HSHarry Stebbings44:15

      If you achieved it in six months, would you not say that's ineffective goal-setting? Like, it's so far off, you, you capped what could be done significantly.

   10. JGJean-Denis Greze44:27

       If I knew the future, I would bet everything on the moonshots. You know? Like, I, you know, it's like, this is why, you know, Google has the 70-20-10 or whatever. Like, you know, everyone's got their frameworks for how much you invest and, like, moonshot-y thing. But I think it's the hard part, right? Like, I, I really fundamentally think that's the hard part of the job. The, the thing for me that's always clarifying, and I, I, I'm not good at doing this in practice is, I'm not nearly as good a product leader on this as I wish I were, it's ...

9. 44:55 – 47:24

   How to Think about Competition

   1. JGJean-Denis Greze44:55

      we're building businesses, and long-term what matters is competitive advantage. It's a thing that you can do that is hard for someone to copy or expensive for someone to copy or, or who l- lasts a certain amount of time. And when you're a company like Plaid where you already are better across the board than most of your competitors, I think the one rule for us is, what can we do to extend the window of our competitive advantage, even if we're giving up short-term opportunities to short-term increase the competitive advantage? And I think it's hard to say no to the obvious short-term wins. It's, like, really, really hard. And I wish I were able to do it more and to convince more people that we needed to look more at the, at the, like, things that over two to three years really win. 'Cause we have that luxury. We're ahead enough that we can invest in the two to three-year thing, whereas if you're catching up to someone else, you may not have that luxury.

   2. HSHarry Stebbings45:46

      On one of your angel investments, how should I think about competition? Should I be intensely aware of it and monitor it, or should I run my own race?

   3. JGJean-Denis Greze45:55

      I'm, I don't think I'm a very good angel investor, 'cause I do it 'cause I like the founders and the ideas more than I do it for, you know, like, financial optimization of the gain. I think in a lot of spaces, things change so much, right, in the early phases, that I think if you're too focused on competition initially, you, you usually just don't build the right thing or you don't figure out the wedge that gets you to win and go to market. At any scale, like at Plaid's scale, like, 50 ... I mean, we're much more than that, but, like, when you get to 50, 100 million in ARR, you're living in a world of competition. If you're making a lot of money at high margins, like, people will come after you, right? And, and then, I think it starts to become important to have things that are difficult for others to do. And, you know, we were talking about product and product differentiation. You're, the saying is always, like, distribution is your product, right? And so your ability to get new customers and to sell more to existing customers, I, I think often at, like, a certain scale is what ends up allowing a lot of companies to, you know, to grow more and more and more and more. Like, that's like a, that's like a high confidence way to grow. Reputation, network effects, like, if you can have brand, like, much better brand or much better network effects, those are incredible, but those are rare. There are a lot of successful companies that don't have, like, huge network effects. So, you know, there's a hierarchy to competitive advantage, and ideally, you start to develop it, but, like, at an angel with some- someone who has, like, a million in ARR, I don't know. If you disagree,

10. 47:24 – 54:32

    Jean-Denis on Venture Capital

    1. JGJean-Denis Greze47:24

       tell me. I just haven't focused on it, 'cause then I think very few companies would pass the filter. Like, I would make, like, three investments a year and not 20.

    2. HSHarry Stebbings47:30

       No, I, listen, I totally agree with you. I'm just intrigued by something you said before though to me, which is your startup is a zombie, and life is too short to keep trying. It's just, you know, we always hear, "Never give up," and I'm always an advocate for never give up, uh-

    3. JGJean-Denis Greze47:45

       Yeah, 'cause you're a VC.

    4. HSHarry Stebbings47:47

       Pfff, well, I mean, like, VCs say, I mean, a lot of VCs are saying, "Give me the money back. I'll take 60 cents on the dollar."

    5. JGJean-Denis Greze47:54

       I don't think that most of the VCs care. Like, I, I have, I love, um, good friends, a lot of, like, true friends, you know, like, hang out on the weekends at venture firms. I love them. They're great. I always, you know, uh, I make fun of them a little bit, but, uh-

    6. HSHarry Stebbings48:07

       Well, who do you make fun of them for?

    7. JGJean-Denis Greze48:08

       ... I, I have a lot of respect for them.

    8. HSHarry Stebbings48:09

       What are we, 'cause I'll, I'll, I'll defend this. We can-

    9. JGJean-Denis Greze48:11

       I don't think they work as hard as I do, but they make more money. Um ...

    10. HSHarry Stebbings48:15

        Oh, 100%, you just chose the wrong business. It's your fault.

    11. JGJean-Denis Greze48:18

        Yeah, I know. Uh, 100%, I just wouldn't be, it wouldn't make me happy. Um-

    12. HSHarry Stebbings48:21

        No, no, I, no, I would find it so boring being a VC and not-

    13. JGJean-Denis Greze48:24

        Oh.

    14. HSHarry Stebbings48:24

        ... a media founder too. Like, I run a media business, which keeps me busy as well (laughs) .

    15. JGJean-Denis Greze48:30

        That's true. The way I think about venture capitalists and, and the value overall is, they're distributing the chance at an outsized return. And you find a lot of smart founders if you give them money, and then some of 'em really hit it o- out of the park, and you keep, you know, supporting them as they grow and make giant businesses. And, and, and so if you think about it on a human level, it's like, well, a bunch of founders are gonna fail. Like, and if you, if your measure for success is a $10 billion company, like, 95, 98%, I don't know, some really high percentage of founders are gonna fail. And that's just life, right? And so if you're a founder, you know that you're just part of a capitalistic machine to get to innovation. And you do it 'cause you love it and 'cause you believe in the mission. For all these irrational reasons, you do it. But you always have to ask yourself, like, is this worth my time on earth? And as we said earlier, life is, life is short, right? And right now, what's happened is there's a bunch of founders who've raised a lot of money with businesses that, in reality, don't quite have the product-market fit that they thought that they would. And when that happens, you gotta be really, really careful, because it's easy when you have three years of runway to spend another three years-... of your life trying to make a thing that has a very low chance of getting to product market fit to work, and I think a lot of founders that I should ask similar question, like reset, just do a totally different idea, right? Or, like, return your money and then decide if you wanna be a founder again or, like, start a product with a bigger company or whatnot. And there's a lot of these, I think they're zombies, where they have some revenue but they just don't have venture growth. So you could turn it into a lifestyle business, but, like, is that really why you wanted to start a company? It's not. Otherwise, you wouldn't have taken venture capital funding. And I think people are gonna take good years of their life and of creativity and they've been fooled into thinking they're close to product market fit because of the zero interest rate environment, and the zero interest rate environment is, is gone, and they're actually much further than they thought. And, like, the, the key for me is product market fit isn't a binary thing. Like, you don't have product market fit or not have product market fit. You have degrees of product market fit, right? And how, how easily people thing- buy your things and, you know, that, that shows up in stats like CAC to LTV or whatnot, but it's not, it's not like you have it or you don't. So I'll give you, like, a weird big company example, but it's really im- I think it's, it's interesting. You think of Snowflake, it's a data warehouse, right? So I'm the CTO of a company. What's happening if you look at the Snowflake numbers, it appears that their current customers' s- rate of usage of Snowflake, like, the growth of what an existing customer would spend on Snowflake isn't going up nearly as much as before. Right? So last year, before, like, if you were u- like, average customer of, of Snowflake that gave them a hundred dollars in year one, they might give them maybe $130 in year two. Just existing usage, no new sales, just including usage. But now that seems to be going up less. At least that's what the, like, numbers look like. What's happening? What, what, what is happening? Or, like, Gong is another example where I think, like, f- for Gong, I know, I l- we like them 'cause they make the team more efficient, but we're also aren't hiring more salespeople, and their, their model is seed-based and so they're not gonna see as mu- much intrinsic growth from all these companies not hiring as many salespeople. But le- let's go back to the Snowflake example. What's happening? Okay, here's what's happening. Before, when my team was like, "We want to put more data in Snowflake," I was like, "Hmm. Can..." Zero interest rate, so f- like, funding is free, like, literally putting more data in Snowflake. I pay them, but they're zero interest rate on what I put in there, so it's easy to raise funds again, so I'm like, "Well, if in the future I can generate return on this data that is above 0%, it is worth it for me to pay for the cost of the data going in the data warehouse." Now suddenly, I wake up and I'm like, "Well, the hurdle rate is 8% and I'm trying to get to cash flow positive as quickly as possible." And so I'm like, "Yo, people, like, first, no more data into Snowflake until you're really sure that you can generate much more value relative to the cost in the next, you know, 12 to 18 months. And number two, what are we storing in Snowflake where we have really low odds of making more value out of it?" And there's a whole bunch of stuff that shows up, and so, you know, we're like, "We don't use Snowflake as another data warehouse," but we're like, "Okay, we're gonna reduce how much data we store there." Because the hurdle rate and, and the amount of value I c- I think I can get from data products is, is just higher, like, the hurdle rate's higher. The value I need to show is higher. And so the product market fit for Snowflake, as a data warehouse product, that's the same, binary, but the value of a data warehouse in-industry just went down because the value that I need to generate from that data needs to be higher for me to be willing to spend that cost. And so everywhere right now in tech, what's happening is products that were top three value creation for businesses are now fifth on the list or seventh on the list. These companies that thought they had product market fit, their, there's a structural thing that's changed that's made their product ma- market fit less, and in many cases less so that it's not a growth business anymore. And I think people are not... like, they aren't thinking through it like that. They're thinking like, "Oh, it's a little harder to sell until there's more money in the market or until these companies start growing." And I'm like, "No, actually, like, I'll still spend less on my data warehouse when I'm at cash flow positive b- because I need to get more value out of that data for it to be worth it for me to store it." And so it's... I think it's a m- I think it's a more fundamental change in, in how people look at, at returns.

    16. HSHarry Stebbings54:03

        Would you be a long or a short on Snowflake?

    17. JGJean-Denis Greze54:06

        I don't know what their stock price is right now. Um-

    18. HSHarry Stebbings54:09

        I can tell you.

    19. JGJean-Denis Greze54:11

        I- you can tell me?

    20. HSHarry Stebbings54:12

        Yeah.

    21. JGJean-Denis Greze54:12

        I mean, is it, like... what is it, like, 25, 30 billion?

    22. HSHarry Stebbings54:15

        It-

    23. JGJean-Denis Greze54:15

        I'm not a public company s- stockholder.

    24. HSHarry Stebbings54:17

        It's 60 billion.

    25. JGJean-Denis Greze54:19

        60 billion? I'm short. But, look, I don't... you know, I'm a long term S&P 500 investor.

    26. HSHarry Stebbings54:27

        My friend, listen, I totally get you. Uh, I, and I actually... I thought it was fascinating analysis

11. 54:32 – 57:15

    Jean-Denis on Artificial Intelligence

    1. HSHarry Stebbings54:32

       there, and I haven't thought of it in that way before. Speaking of, kind of differentiated opinions, you said another differentiated one to me before, which is, "I don't have a mental model for generative AI and that is a problem, but neither do you." Again, these cliffhangers are banging, but what did you mean by it?

    2. JGJean-Denis Greze54:50

       I mean, what is a great product or engineering leader or great business leader, right? You, you need clarity on what, what is possible and what is not possible, like, what can you build with software, what can you not build with software, right?

    3. HSHarry Stebbings55:02

       Sure.

    4. JGJean-Denis Greze55:02

       'Cause I'll give you a good startup idea right now, like teleportation. That's a 10 trillion, 100 trillion dollar business, but like no one knows how to build it, right? So it's, it's not useful. So what's really interesting about gen AI for me is it makes really cool demos, but I actually have a lot of trouble on- answering the question, like, where can we build great products with it and where can't we? And I used to have a very s- very good model of what you could do with software and, and to a certain extent hardware. Like, I, you know, I understand what computers are good at doing, what they're bad at doing. Now suddenly with gen AI, there's a bunch of stuff they used to not be able to do, like deal with ambiguous human language or create new images based on words, that they're really good at doing. I just don't know quite what really good is, like, I don't have a sense for what they can or can't do there. Um, and so...... look, that's my problem, right? And I need to develop that intuition, 'cause if I don't develop it, I will, I'll be out of a job, like, pretty quickly. And I think that's true of a, a lot of people in tech. Like, you really need to understand the bounds of technology so that you can know what business problems you can, you can answer with, with software. Uh, uh, but I think everyone's in this, everyone's in this situation, and so we're, we're in the early stages of it, right? And, and so it's okay not to know.

    5. HSHarry Stebbings56:15

       What's been the biggest career bet you've made that didn't work out?

    6. JGJean-Denis Greze56:18

       I was in tech, and then I was a lawyer for four years, and then I went back to tech. I learned a lot, but, you know, four years of your life is, uh, quite a long, quite a long time. So that's, that's definitely one, and then, uh, when I was at Dropbox, k- uh, I was responsible internally for kind of ch- trying to build a Slack-like product, basically a, a product that would allow communication on top of, like, the documents that are in, in, in Dropbox. And we just r- we really, really didn't figure that out. Like, that was, like, big flop. I think we were too far from the customers. There's a ton of stuff in terms of, like, early product that I, I got way wrong on that one and learned a ton from it.

    7. HSHarry Stebbings56:53

       JD, I love this. I could talk to you all day, which, um, is, uh, uh, wonderful for me, but I'm a VC, so we both figure that I have more time. Uh, I, I wanna finish with-

    8. JGJean-Denis Greze57:01

       You're a media entrepreneur. You're a media entrepreneur. I thought we'd establish that.

    9. HSHarry Stebbings57:04

       I wanna finish with a quickfire round, my friend. So I say a short statement, and you give me your immediate thoughts. Does that sound okay?

    10. JGJean-Denis Greze57:10

        It sounds okay.

    11. HSHarry Stebbings57:11

        So tell me, you're a prolific angel as well. What's been your biggest lesson

12. 57:15 – 1:00:43

    Quick-Fire Round

    1. HSHarry Stebbings57:15

       from your angel investments?

    2. JGJean-Denis Greze57:17

       It's really hard to predict, at angel stage, who's gonna be successful, and I've been, like, renewed belief in humanity. When I see founders that I'm like, "Uh, the idea is good, but I'm not sure this founder can do it," and then you see the founder change into, like, a unicorn of a human. And that, uh, I, I think inability to predict people's ability to grow has been, like, a real, ro- you know, eye-opener.

    3. HSHarry Stebbings57:42

       If you could put all of your money in one company that you invest in, what would it be?

    4. JGJean-Denis Greze57:47

       I think it's these two. It's Rupa Health and Atlas. I love the mission. The founders are awesome. They, like, power through anything, and I don't do it for the money. I do it for, like, I think they'll have successful outcomes, but I do it for how interesting the founder and the product is, and I think those two are, are doing very cool things.

    5. HSHarry Stebbings58:02

       What's the biggest piece of startup advice that you hear that's total BS, and why?

    6. JGJean-Denis Greze58:09

       I don't know, 'cause I don't even know what the startup advice is. I, look, I mean, I don't think anyone giving advice is trying to give BS. We're all starting, trying to s- sound smart on the internet, right? So th- the thing you should realize about all advice and the most important thing is, does the fact pattern of the advice match up with the fact pattern of your situation? And often it doesn't, right? And so what you take from the advice is like the delta between the advice and where you're at in, in reality.

    7. HSHarry Stebbings58:34

       Which seed fund do you invest in, if you could own-

    8. JGJean-Denis Greze58:36

       First Round. First Round.

    9. HSHarry Stebbings58:38

       Why?

    10. JGJean-Denis Greze58:40

        I just like, I like those guys, and I think they, um, I think they really care about g- helping founders get to product market fit. Like, I think they're, uh, they will sit and spend more time with the founders to help them get there than other funds that I know, so that's why I have a, a ton of respect for them. But I know, like, a bunch of people there, so bias.

    11. HSHarry Stebbings58:58

        If you could invest in a series A firm, which would it be?

    12. JGJean-Denis Greze59:02

        Well, it was e- once upon a time, you could just say Benchmark to that, and I do like, I do like Benchmark. But, um, I, it's h- it's hard for me to say not s- not Sequoia. I mean, Sequoia, I think just, the, they just do, they just, they've done it. You know, even like, you know, Brazil and stuff, it's like, "Oh, Nubank. Of course, Nubank is with Sequoia." Like, while we were all doing other stuff, you know, they're out securing that stuff, so yeah.

    13. HSHarry Stebbings59:25

        What do you know now that you wish you'd known when you started?

    14. JGJean-Denis Greze59:28

        I, uh, there's this piece of advice, which I think is good advice, that I give to, to people at larger companies, which is like, the best thing to work on is the thing that has impact for the business, but that leadership doesn't care about.

    15. HSHarry Stebbings59:39

        Huh.

    16. JGJean-Denis Greze59:40

        And I think you should, uh, e- someone can, uh, you can unpack that piece of advice for a, a while. If you're a leader, you can unpack that piece of advice and ask yourself sometimes whether the best things for your business are happening where you're not looking, and what does that say about you as a leader? And I think f- for employees, it tells them, like, the north star is having impact. And it, having impact at any business is really hard, 'cause there's all these forces that get in the way, like politics and internal incentives and whatnot. But ultimately, the impact is what matters, and so you gotta find, you gotta find a way to work on something that allows you to have it.

    17. HSHarry Stebbings1:00:10

        What would you most like, final one, what would you most like to be remembered for as a leader?

    18. JGJean-Denis Greze1:00:15

        I would, uh, uh, hope that people who've worked for me or on my teams or with me, uh, feel they did the best work of their life up to that point while they were working with me. That, if I could achieve that, I would, that would make me very proud.

    19. HSHarry Stebbings1:00:30

        JD, I've loved doing this. As you saw, you prepped for the schedule. I, mm, didn't stick to it so well, but this has been a joy, so thank you so much, my friend.

    20. JGJean-Denis Greze1:00:39

        Yeah. Thank you so much. It was great, it was great to chat and, uh, yeah, look forward to hearing the episode.

Episode duration: 1:00:43