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Jeffrey Katzenberg & Sujay Jaswa: Takeaways from Dreamworks; What happened with Quibi? | 20VC #952

Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world’s largest animation studio, known for Shrek, Kung Fu Panda, Madagascar and more. In 2016, DreamWorks Animation was sold to Comcast for $3.8 billion. Before founding DreamWorks, Jeffrey was Chairman of The Walt Disney Studios, where he took the studio from last place to first at the box office with hits like Three Men and a Baby, Pretty Woman, Father of the Bride and Sister Act. Most recently, Jeffrey co-founded WndrCo alongside Sujay Jaswa and has led WndrCo’s investments in Airtable, Frame.io, Quibi, Vise, Placer.ai, NexHealth, Deel, and ID.me. Sujay Jaswa is one of Silicon Valley’s leading business innovators. At Dropbox, he created and led the company’s global business and finance organizations. Sujay and his teams raised over $1 billion, launched and scaled Dropbox’s products for businesses, created partnerships responsible for over 100 million users, executed some 20 acquisitions, and scaled the global business team from two to more than 500 employees in seven global offices. During this period, the company significantly scaled overall revenue from $12 million in 2010 to over $500 million run rate, Dropbox for Business revenue from $1 million to over $200mm run rate, and users from 15 million to 300 million. Most recently, Sujay Jaswa and Jeffrey Katzenberg co-founded WndrCo and Sujay has led WndrCo’s investments in Figma, 1Password, Databricks, Pango, Pilot, Rally, Zagat / The Infatuation, and other great companies. ---------------------------------------------- Timestamps: 0:00 Sujay’s Background 1:51 Jeffrey’s Background 3:37 Sujay’s Biggest Takeaway from Scaling Dropbox 4:18 Jeffrey’s Biggest Takeaway from Dreamworks 5:42 How did Quibi impact your risk appetite? 13:31 Advice for Founders during the Economic Downturn 15:16 Why Operating Experience Becomes Irrelevant Fast 18:16 Time Management when Incubating and Investing at the Same Time 20:08 How does Jeffrey manage to have both breadth and depth in his network of relationships? 22:45 Is Silicon Valley dead? 24:57 Recruiting: What do you know now that you wish you knew when you started? 29:08 What do you do when your employees don’t work as hard as you? 31:34 Do you agree that “when there’s doubt, there’s no doubt”? 33:58 Are Gen Z the Most Entitled Employees? 36:15 What do you think is each other’s biggest weakness? 40:20 Jeffrey’s Life Lessons from Fetching Coffee as a PA 40:30 Generative AI: The Future or Hype? 41:09 What worries Jeffrey about the venture landscape today? 41:30 Best Investment Advice Sujay Ever Received 41:55 What Jeffrey wishes he knew when he started WndrCo? 42:23 What does WndrCo look like in ten years? ---------------------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/jeffrey-katzenberg-and-sujay-jaswa/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Sujay Jaswa on Twitter: https://twitter.com/sujayjaswa Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok ---------------------------------------------- #JeffreyKatzenberg #SujayJaswa #HarryStebbings #20VC

Harry StebbingshostSujay JaswaguestJeffrey Katzenbergguest
Nov 26, 202249mWatch on YouTube ↗

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  1. 0:001:51

    Sujay’s Background

    1. HS

      chaps, I'm so excited for this! I have done my research. I've spoken to many, many mutual friends. So first, thank you so much for joining me today.

    2. SJ

      Great to be with you.

    3. JK

      Great to join you.

    4. HS

      Awesome. Well, listen, I'm gonna start and I'm gonna direct questions quite strictly today, 'cause we're gonna have- it's a very rare time for us to have s- two people on the show. So I wanna start with, how did you make your way into the world of tech and come to both, you know, co-found Wndr? And so Sujay, let's start with you, and then move to Jeffrey.

    5. SJ

      Well, I, I grew up in tech, Harry. I've been... Uh, I was basically born into it. My dad was a immigrant engineer. Uh, you know, your classic Silicon Valley story, came with very little. Um, started a company, uh, in 1988, in an era where it was really hard, uh, for, for folks with his background to, to get venture funding. So he actually- he and his three co-founders, who were... They were Taiwanese, he was Indian, uh, couldn't raise a dime. Um, they bootstrapped it, and five years later, it was the world's largest chipset maker. 40% of the personal computers in the world had their chipset. You know, the funny thing about the Valley is these stories get forgotten really fast because of creative destruction. Um, and then he started a software company in 1996, which, um, crazy story, went public on the day the NASDAQ peaked in 2000, the si- the single- the same day. And so it was, uh, not too dissimilar than this last year. It was 100, uh, you know, call it eight- 90, something like that, million or so of, of what you would call RR today, mega enterprise accounts, Cisco, BMW, IBM, LVMH, accounts like that. And in the first day, its market cap was about $5 billion-

    6. HS

      Wow!

    7. SJ

      ... and, uh, they raised something like $200 million in the IPO. Two years later, it was trading for a market cap of $200 million, the cash on the-

    8. HS

      Wow!

    9. SJ

      ... cash in the bank. So I've seen the... You know, I grew up, I grew up in this environment. I've seen the cycle multiple times, and so there's lots to talk

  2. 1:513:37

    Jeffrey’s Background

    1. SJ

      about.

    2. HS

      Jeffrey, hit me.

    3. JK

      Yeah.

    4. HS

      How did you make your way here?

    5. JK

      Sure. Well, h- here's the thing, Harry, which is, as you, uh, well, well know, I spent 40 years in the media, entertainment, movie, TV business, but interestingly, there was a sort of theme through pretty much every chapter of that, where technology was a gigantic enabler of our storytelling. And if you think of the rate of innovation of- that has gone on in, particularly with movies and television, um, over these, say, let's just call it the last 30 years or so, uh, it's pretty astounding. So whether it's in the films, uh, in terms of special effects and the entire process end to end of making films, um, you know, for me, probably the most transformative moment is when, uh, you know, I reached out to Steve Jobs and John Lasseter and brought them into the Walt Disney Company, um, and made a home for Pixar. Uh, so it's just, you know, when I started DreamWorks Animation, um, we had a studio in Redwood Shores of over 800, um, uh, engineers and artists, so I sort of felt like, you know-

    6. HS

      It's a continuation more than anything, yeah.

    7. JK

      Technology has been my, my ally, my friend, my partner in pretty much everything that I've done, and the relationships, um, were established, frankly, 20 years ago, and I've maintained them.

    8. HS

      Oh, um, and we're gonna dive into that, Jeffrey. [chuckles] Don't worry, I heard it from many different people, so have no fear-

    9. JK

      [chuckles]

    10. HS

      ... I'm getting to that, maybe. Um, so I'm gonna like break up, 'cause there's two specific questions I have for both of you on your careers.

  3. 3:374:18

    Sujay’s Biggest Takeaway from Scaling Dropbox

    1. HS

      Sujay, scaling Dropbox, you were instrumental to the scaling. What's the single biggest takeaway for you, which is incredibly hard and unfair of me to ask, but the single biggest takeaway for you, and how did that impact your mindset today and as an investor?

    2. SJ

      The number one takeaway is hire really, really talented people, and I don't mean talented in terms of necessarily what they've accomplished, but rather talented in terms of their potential and work ethic. And then, put them in jobs that are suited to where they spike. So, you know, people are talented in different areas. Everyone has strengths and weaknesses, so figure out what these talented people could be great at and put them in those jobs. And that way, if you don't know how to do anything, they'll figure it out.

    3. HS

      Jeffrey,

  4. 4:185:42

    Jeffrey’s Biggest Takeaway from Dreamworks

    1. HS

      in terms of you, incredible time with DreamWorks. [chuckles] What was your biggest takeaway, and how did that impact your mindset?

    2. JK

      Literally, uh, every day, make sure you're looking around the corner, over the horizon, um, to what's coming at you. Um, you know, change, uh, is part of all of our lives, um, but embracing that change, you know, culturally, uh, is a, is a, is a high bar. Um, and for me, having lived through the disruption of hand-drawn animation to computer animation, um, I would say was, you know, probably one of the greatest challenges, and our survival, uh, literally depended on our ability to make a pivot. Um, it was brutal. We lost a lot of very talented people who were not- actually didn't have the capabilities to be a part of, uh, the innovation that was going on. Um, but I have to say, if we hadn't done it, uh, we would have gone bankrupt.

    3. HS

      I, I, I, I totally get you, and I love those as two takeaways. Now, I mentioned Somash at IVP before the show. Um, [chuckles] he gave me a really tough one, so I'm blaming him. It's not me, it's him, okay? Um, he said, and-

    4. SJ

      Well, he'll pay the price for it, so go for it.

    5. HS

      Okay, well, [chuckles] -

    6. SJ

      We'll get, we'll get even. [chuckles]

    7. HS

      Poor Somash. Um,

  5. 5:4213:31

    How did Quibi impact your risk appetite?

    1. HS

      uh-

    2. SJ

      [chuckles]

    3. HS

      ... he said, when you have something like Quibi, how does that impact your mindset towards risk? Does it make you more or less inclined to take risk? And he said you have different-

    4. JK

      Great question. He's okay, and I'm okay. He doesn't- he's not getting punished for that.

    5. HS

      That's-

    6. JK

      So the reason why it's a great question, Harry, is, is that in many respects, it, it exemplifies, uh, the difference between the culture of Northern California and the culture of Southern California.... in Southern California, you know, so let me just start with the following: We are in a risk business, right?

    7. HS

      Mm-hmm.

    8. JK

      Media and entertainment and technology, uh, founders building new companies, there's a very simple equation. If you wanna do something that is original and unique, it equals risk.

    9. HS

      Yeah.

    10. JK

      If you are going to do something that risk- is risky, it means there needs to be the provision for failure. If you take out the equation, the ability to ever fail, you will not take risk. If you don't take risk, you'll never do anything unique and original.

    11. HS

      Mm-hmm.

    12. JK

      It's true of every pioneer. Okay, so in the Southern California, in the culture that I grew up in, um, failure comes with huge public humiliation. Doesn't matter whether you're in front of the camera or behind the camera, uh, the, the nature of it and the media around it is, you get punished pretty brutally when you, when you fail. You get raked across the coals, and the list is endless-

    13. HS

      Wow

    14. JK

      ... of movie stars and their ups and downs. In Silicon Valley, you know you fail, you get on to the next thing.

    15. HS

      Sure.

    16. JK

      Like, failure makes you smarter, makes you stronger. You know, it's a, it's a, it's, it, it's part of how you grow as an entrepreneur, um, uh, out of it. And so going back specifically to Quibi, um, I, I was never humiliated by the failure of it. I was humbled by it. We never had product market fit. It was a really, really big, bold, audacious, swing-for-the-fence idea. Um, and everybody involved in it understood that. Interestingly, from a content standpoint, I believe it hit a very high mark, and that the quality of work that was done out of Hollywood and out of the best storytellers, they delivered to me. I set a very high bar, they hit it. Where we failed is actually product market fit, and how much of that is... And that's a real- that's a big, big learning lesson for me. It was designed day one to launch almost like a movie, which is, it either opens or it doesn't. Um, and, and that was a mistake. Uh, obviously, doing it in s- a on-the-go mobile product, uh, during a, you know, pandemic where we shut the world down impacted it, but I don't blame it only on that. That certainly was a factor. Um, so a good learning lesson for me. I'm humbled by it, but I wasn't humiliated by it, 'cause I thought we did something that we could be proud of.

    17. HS

      Sujay, what about you? It's almost said that you'd have different answers.

    18. SJ

      So, uh, when I was at Dropbox, one of the large... I won't say who, but one of the largest investors in the world in tech, uh, told me that they had run a survey of all the investments they'd ever made, and, uh, the founders that didn't actually talk to them, refused to take their calls, were the ones that were the most successful, and they didn't, they didn't really know how to process that emotionally. I'm a Silicon Valley guy. I've been around this game for a long time, and the way you would launch a company in, in my in... You know, in my universe, is a little bit different, as Jeffrey [chuckles] knows, and he and I would disagree on this, uh, at the time, and-

    19. JK

      No, Sujay was, Sujay was an incredible, incredible counter, uh, uh, uh, perspective on this that was actually invaluable, and it's, it's one of the things that I love so much about him as a partner, which is, he was able to question and to cajole and to, uh, uh, push me in a way to look at things that, um, I was not able to see. That his experience, and specifically his scaling and go-to-market through Dropbox, um, you know, was actually great insights. Unfortunately, we weren't able to overcome them, but let me tell you, one of the things that happened out of it is, is that when it was clear that Quibi wasn't going to succeed, which was pretty early on, by the way... I mean, it was in 60 days, 90 days of our launch of it, that it was a misfire in this. One of the things Sujay impacted on me gigantically is the fact I shut it down as quickly as I possibly could, because I wanted to return as much of our money to our investors as we could. We returned $600 million, uh, out of the initial billion dollars, um, to our investors, and, you know, so I, I don't think I would've gotten there without him.

    20. SJ

      Harry, here's the interesting thing: There have been a lot of companies that have raised giant piles of cash here over the last couple years. I don't know of a single one that has returned its ca- their capital to people.

    21. JK

      I, I-

    22. SJ

      They'd rather just sit on it and figure it out, and I think, I think they're doing a disservice to a lot of people.

    23. HS

      I, I just got a shitload of, uh, negativity on Twitter, 'cause I tweeted, "There is a whole generation of companies that are at Series B stage with money, like capital reserves, 'cause they've raised preemptive rounds, and they have no product market fit. We're gonna see a wave of Series B investors ask for their cash back." [scoffs] Don't, don't put that on the Twitter sphere. You're not gonna get much love back for that.

    24. JK

      Yeah.

    25. HS

      But my question to you-

    26. SJ

      And I take it back.

    27. HS

      Uh, no, no, I know. I agree with you totally. My question to you is, though, [phone ringing] when you think about that [chuckles] when you think about that, um, you know, we're gonna see kind of the living dead, uh, in this new generation. What do you do if you're a living dead company today? I'm too interested to hear your thoughts.

    28. SJ

      Here, this is the hardest part of the whole thing, is there is no doubt that one or two of those living dead companies will figure out a spectacular pivot over the next decade and build unbelievable products that millions or tens of millions or hundreds of millions of people use, and that's one or two out of probably what will end up being, like, 1,000 living dead companies. And so the irony of it is that-... you basically have a situation where, um, the, the, the found- the people that should fight on, you know, God bless, go for it! Keep, keep trying. But, but there's a whole bunch of people who are doing it for the wrong reasons. Not that they have some sort of profound idea or some belief in the future, but rather feel some social pressure, or they don't know what else they'll do with their life, or things of that nature, and that's gonna be a really bad thing for a lot of people.

    29. JK

      So Harry, for me, my pressure was, in my entire career, I have never lost money for somebody who invested or backed me in what I was doing, ever, before this. Which, for someone who's spent 40 years in media and entertainment, that's a unicorn. There's not many people that can say that.

    30. SJ

      Yeah.

  6. 13:3115:16

    Advice for Founders during the Economic Downturn

    1. HS

      that's great to hear. I think the question is kind of pre-that. There's this question for a lot of companies today, which is they have to make hard decisions. Do we cut costs? Do we reduce teams? Versus do we continue to invest in growth, and risky bets, and progress as a company? How do you advise these founders on leading through this downturn with the continuation versus cutting costs?

    2. JK

      I don't think they're generalities. I don't think you can answer that and just say it's one size fits all. I think every company, every founder, every set of circumstance, you know, has its own unique characteristics. And so what you can do is, is to, is to put a mirror up and help a founder see clearly what the pros and cons are, what the struggles are, what the opportunities are, in order for them to make that, uh, that assessment, but I sure don't... I don't know, Sujay?

    3. SJ

      Yeah, I was gonna say, I'll give a generality. Uh, so- [laughing]

    4. JK

      [laughing]

    5. HS

      [laughing]

    6. SJ

      ... so basically, I think this will, this will be true for what I, I, I might, again, I'm just making this up, but 98% of these companies. Strip the business down to the core, so you generate whate- you know, whatever that means. Don't waste more time on it if it's not working, and then if you're gonna stick it out, absolutely go pursue some risky bets and go take a moonshot, because don't waste your time just keeping a living, dead company alive. If you're gonna go for it and spend your one life on something, and spend investors' capital, and all these employees' time and, and, and career trajectories, and if you're gonna invest all those resources into something, you've gotta do it on something meaningful, not on just keeping a business, you know, kind of floating.

    7. HS

      We love a generality. Fantastic. Well done.

    8. SJ

      [chuckles]

    9. HS

      Uh, media,

  7. 15:1618:16

    Why Operating Experience Becomes Irrelevant Fast

    1. HS

      baby, media.

    2. SJ

      [chuckles]

    3. HS

      Uh, Je- Jeffrey, you said about your 40 years there-

    4. SJ

      Yeah

    5. HS

      ... and that incredible career, respectfully, for someone like both of you with incredible, stellar backgrounds, I would be leaning into the "operators make the best investors, and look at us with our CVs," but you guys have said to me before, "Operating experience becomes irrelevant very fast." [chuckles] Wasn't where I thought you were gonna take that. Why does it become irrelevant fast?

    6. SJ

      Okay, so I'll explain why it becomes irrelevant fast, and then I'll also tell you why we're kinda talking our own book at the same time, 'cause that- that's a piece of it we didn't talk about. So it becomes irrelevant fast because the world changes, right? The tools you use, the platforms you're building on, the platforms you're marketing on, uh, the competitive dynamics, all of those things change really quickly, right? So when someone sees, uh, a marketing trick work, immediately thousands of people pile into that, into that tactic, and they commoditize it, or they make it irrelevant, or the platform gets frustrated by the, by the tactic and the, and the way they perceive it as abuse, and they shut it down. And so what ends up happening is... You know, I'll give you one example. I get asked all the time about something that, um, that Drew had done early in Dropbox about, um, you know, the referral program-

    7. HS

      Mm.

    8. SJ

      ... where, hey, you know, you know that model where, um-

    9. JK

      Yeah

    10. SJ

      ... it was a mutual referral program where if, uh, if, if I recommended Dropbox to you and used it, we would both get extra storage?

    11. JK

      Yeah.

    12. SJ

      And I said, "Yeah, it's great." I mean, I can't think of another company at scale that's been successful with that, but it was an amazing tactic, and it was responsible for a lot of, you know, or, or a good, you know, reasonable chunk of early growth. Um, but you know, we also had, like, 50 other things we did. That's just the one that got publicized. And, and so when you, when you think about that construct, I think the biggest mistake operators make when they give advice to founders is it's purely out of the lens of their experience in the environment and the circumstances, with the tools and the capabilities that they had available to them, and all those macro things are totally different today for an entrepreneur. And so I actually do think it's largely irrelevant. The one area where I've found it to be, you know, useful over time is in people management.

    13. JK

      Yeah.

    14. SJ

      Like, there's just some stuff you have to go through, uh, interpersonally with people to learn, and so I think operators have often given great advice, but the way we solve for that, because we do think the operating is an edge... Like, if you actually have relevant operating advice to give someone, that's a huge advantage. So what we do is we continuously build companies. So half of what WndrCo does is not, you know, venture or growth investing. We actually buy companies and incubate them, you know, kind of one to two a year. Um, the only one anyone ever talks about is Quibi, but we have some others that are wildly successful, and, uh, maybe people will start caring. And, and, and that's how we keep our operating experience fresh, and so that's the operating experience we bring people, even if what they really wanna talk about is, you

  8. 18:1620:08

    Time Management when Incubating and Investing at the Same Time

    1. SJ

      know, The Lion King and Dropbox.

    2. HS

      How do you answer LP's questions in terms of LP- uh, time management across incubation and across investing? Like, incubation done well is-... fucking hard and full-time, how do you manage incubation and investing at the same time? And do-

    3. SJ

      Jeffrey, why don't you tell him what your days are? Just this is, like, one of the more crazy things. [chuckles]

    4. HS

      I've h- I've heard his days are, like, 18-hour days. He doesn't need to do it, respectfully, Jeffrey. Um,

    5. SJ

      Yeah.

    6. HS

      he doesn't need to do it, but he still works harder than everyone else. [chuckles]

    7. JK

      Yeah, well, work, you know, work is my happiness in it, but but the ability to actually help build companies today as well as invest in them actually makes us better at both. And, and for me, it's actually what, it makes WndrCo so exciting for me is is that, you know, we're exercising both, uh, both muscles right now, and the way you do it is by frankly getting the best people and recruiting in the best talent. I mean, you know, the- our, our largest, uh, uh, investment, our largest build, uh, is Aura, and it's run by a just a killer founder CEO, you know, who we're able to bring values to him every day. We're, we're, like, part of his staff. He deploys us on behalf of himself. I always laugh and say I'm his deputy director of sales, [chuckles] you know, and, and, uh, you know, but but-

    8. HS

      Not director of sales. One day, Jeffrey.

    9. JK

      No, one day.

    10. HS

      One day you'll get the promotion.

    11. JK

      Yeah, I-

    12. HS

      I feel it

    13. JK

      ... I'm, I aspire.

    14. HS

      [chuckles]

    15. JK

      Uh, uh, so but but I think it is that balance that of, you know, having that experience, that when we are talking to founders today, we are having the same issues and problems and challenges and seeing the same opportunities in the businesses that we have a, you know, a, a big hand in, a control stake in, that, um, you know, just

  9. 20:0822:45

    How does Jeffrey manage to have both breadth and depth in his network of relationships?

    1. JK

      m- makes it relevant.

    2. HS

      Can I ask, y- you speaking about staying relevant there and keeping mindsets fresh, you know, Jeffrey, everyone said about the strength of your network. The hard thing is with network over many years, it accumulates, and with breadth comes actually a lack of depth. That's not the case for you. How do you maintain network breadth and depth in a way that no other people really can?

    3. JK

      Well, honestly, I just work really, really hard at it. You know, investing in relationships and partnerships and friendships, these are, you know, to me, have always been high priority, and I've always gotten a tremendous ROI from it, and so and I find it enormously rewarding. So, you know, I've- today we have so many different devices available to, to do it, Harry, so some of it comes from my three breakfasts and two lunches and dinners, and uh, uh, some of it comes from, uh, you know, hitting the phone, which is my old-school weapon of mass destruction.

    4. HS

      [chuckles]

    5. JK

      Um, and but much of it today is, you know, just on text, you know, and just staying in touch with people and, uh, being interested in what they're doing and reaching out when I see that people are doing interesting and exciting things and just maintaining it. I mean, it's, you know, it's, it's very rewarding.

    6. HS

      I heard you put your call from-

    7. SJ

      So, Harry, just here's a... I'm just gonna give you a, uh, just a data point on, on Jeffrey and his, uh, keeping, keeping tabs on folks. So my wife and I went skiing with, with Jeffrey and his wife. This is, you know, 2017 or something. We were... You know, just after we'd gotten WndrCo going. And it's Saturday morning, and the way that Jeffrey used to handle skiing is we're first thing out on the mountain, you know, just go up, you know, up and down, not, you know, don't even talk sort of thing, and then come back at lunch, eat lunch, and then on a Saturday, Jeffrey had a call list that was, like, must have been 80 names, and over the next four hours, while the rest of us were being normal humans, he cranked through and called every single person on this call list [chuckles] and that's just a Saturday afternoon for Jeffrey.

    8. HS

      [chuckles] I, I, I, I love that. I, I even heard that Jeffrey actually put his card behind certain, uh, like, breakfast places to stop the weight of paying for things at the end. You know, the five to ten minute wait.

    9. SJ

      All of them. That's not certain bre- that's every restaurant in LA.

    10. HS

      I mean, Sujay, you sh- you shouldn't partner with people that make you look bad in this way.

    11. SJ

      [chuckles]

    12. HS

      You should, you should choose your partners strategically.

    13. SJ

      [chuckles]

    14. HS

      Uh, that's why mine are

  10. 22:4524:57

    Is Silicon Valley dead?

    1. HS

      all lazy. Um, [chuckles] you mentioned, uh, the importance of people. We spoke about Jeffrey's network. The thing that worries me a little bit is, you know, so much of network was in person, and a lot of that was in the Valley, and, you know, everyone talks about, you know, the death of Silicon Valley. You know, Keith Rabois promotes Barry's in Miami. Um, sadly, haven't joined him for a Barry's class yet. Um, but, like, the question is, like, how do you feel about the sentiment that Silicon Valley is dead and that old-school Valley network isn't there anymore?

    2. JK

      Harry, I'm gonna say to you, not only do I feel it's not dead, I'm gonna say... I'm gonna take a contrary point of view, a very contrary point of view, that, uh, what in fact is going on in the Valley today is going to create a whole new crop, a whole new generation, um, because all the downsizing that's going on, there are thousands and thousands of people in Silicon Valley being laid off from jobs-

    3. SJ

      Yeah

    4. JK

      ... who are going to fuel a whole new generation of innovation and creativity and people, you know, heading out on their own and creating, you know, next-generation brilliant companies. You watch.

    5. HS

      Sujay, how do you feel?

    6. SJ

      I totally agree. I, I was, uh, you know, I was open-minded to the Valley is dead argument, like, um, at the beginning of Covid. I think there are certainly elements of Valley culture that had gotten, you know, that a good recession needed to fix, was needed to fix. Uh, entitlement, you know, the, the feeling that everyone should get a promotion and a raise twice a year. You know, that, that kind of general malaise that comes from a huge percentage of the talent working at gigantic companies and not actually accomplishing much.... but that feels like it's breaking really fast. Over the last six or nine months, the idea of hard work became be- you know, being the priority of a startup, it's back to the top of the list. You know, that we've gotta, you know, that your job is to fight for customers and build cool products and, and, and recruit the best people. Like, that... And this doesn't sound like rocket science, but I feel like those three things weren't the top three priorities for most companies here for the last couple years, and I think that's, that's, you know, flipped back to the right way already.

    7. HS

      You said about

  11. 24:5729:08

    Recruiting: What do you know now that you wish you knew when you started?

    1. HS

      recruiting people there, what do you know now that you wish you'd known when you started hiring and recruiting top talent?

    2. SJ

      So the, you know, the, the person who I actually thought was the most insightful interviewer of, um, you know, normal team members was Arash, uh, who was the co-founder and CTO at Dropbox.

    3. HS

      Yeah.

    4. SJ

      Arash is the most, um, you know, most challenging interviewer I think most, you know, most people who interviewed with him have, have ever experienced. Because he'd be on his laptop the whole time, he wouldn't look at you, and somehow he would intuit things about you that you probably didn't even know about yourself. It was... He, he's a pretty remarkable guy in that sense, and he was actually the person who kept the talent bar at Dropbox as high as he did. Like, like, Dropbox has that well-earned reputation for being a pl- a place where lots of talented people worked, and it, it would've- the bar would've easily come down if it wasn't for him. So I would say that, you know, being rigorous on keeping that talent bar high is super important. And then beyond that, work ethic, passion, intensity, finding people who are working for you because they're really excited about what you're doing, and not because you're a hot company, that's, that... I mean, if I was to say one thing, that would be, that would be the one thing.

    5. HS

      Sujay, Somesh asked me to ask, why did none of the great talent stay? I agree with you, it's like the PayPal Mafia, unbelievable talent, but the retention didn't last. Why?

    6. SJ

      Well, I think it's the same as PayPal, right? Like, you... You know, when people join a company and they think it's gonna be worth a trillion dollars, if it's worth $10 billion, that's amazing. I mean, there, there's not gonna be many after this whole recession is done that are worth 10 billion. Uh, but Dropbox will be because it's just a cash flow machine. But you don't make generational wealth if you're employee 500 at a $10 billion company. Whereas if you're at a $100 billion company or a $500 billion company, it's really, really hard to get motivated to go through the full startup grind. Um, and so I think a lot... And it's easy to stay. And so I, I would say that the s- you know, if, if PayPal sold to eBay for $50 billion, I doubt the intensity and commitment to pursuing startups would've stayed that, would've been as high for as many of them. Certainly some, but not most.

    7. HS

      Jeffrey, you've hired incredible teams. What do you know now that you wish you'd known when you started hiring incredible talent?

    8. JK

      I would actually have to say, Harry, that I- there hasn't been a new lesson for me in that I think it's been consistent for, you know, 40 years, and that I've always looked for people with extraordinary passion, driven, Type A... You know, like, here, here's what it takes to come to work, uh, in the environment that I'm in, and I'm building, and what, what I'm trying to do. It's not right for everybody. You know, I'm infamous in this town for having said a line in my early Disney days, "You know, if you don't come to work on, uh, Saturday, don't bother coming on Sunday."

    9. HS

      Tell me about that.

    10. JK

      And, uh-

    11. HS

      Elan told me to ask you about that.

    12. JK

      Well, well, well, I meant it when I said it. [chuckles] So that's the, that's the, uh, the probably... I've learned my lesson, which is I, I actually have come to understand there is a work-life balance that actually makes somebody the best version of themselves. Um, but the sentiment there is, I wanted people who wanted to go to Mars with me, right? I wanted them... We were on a mission, it was a very high bar for us to get to where we were going to. It's not right for everybody, but if you're gonna be in this environment, it's a, I, I, I want you 110%. Um, what I have learned, what I have learned over the years is that, um, different people, you know, some people are night owls, some people are, you know, uh, daytime is where their greatest productivity is. There's... And you need, you need to make allowances for, uh, those things. People that wanted to raise a family. You know, Sujay's in the middle of raising a family right now. It's makes him a better person, a better executive, better rounded, uh, in that, and so I want him to-

    13. SJ

      But I haven't seen them in two weeks because I'm on the road for work, but, you know. [chuckles]

    14. JK

      [chuckles]

    15. SJ

      Just telling. [chuckles]

    16. HS

      [chuckles] I

  12. 29:0831:34

    What do you do when your employees don’t work as hard as you?

    1. HS

      mean, so this is what I was actually gonna say, so I, I get it, Jeffrey, that's so nice that Sujay is so rounded. Mm, nah, I mean, let's face it, I, I fucking crush it 18 hours a day, and I have zero life. [chuckles] Like, I haven't seen someone in weeks. But I... In, in this world, you can.

    2. JK

      But, Harry, I'm gonna say to you, you, I'm gonna give you some advice: That's not great. That's not. It really isn't. You know, how old are you?

    3. HS

      26.

    4. JK

      Okay. You, you, you got time. [chuckles]

    5. SJ

      [chuckles]

    6. HS

      [chuckles] Look at it.

    7. JK

      You got time.

    8. SJ

      [chuckles]

    9. JK

      But I'm telling you, a little corridor there for relationships, for friendships, you know, for people that matter to you, are actually gonna make you better at your job.

    10. HS

      Can I ask, Jeffrey, did you find it hard when people were not as bought in as you are, when they weren't as obsessed as you are? It's... It frustrates me. I don't understand why they're not working like I am. Did it upset you?

    11. JK

      Well, it can't- it's not one size fits all, Harry, and you have to make accommodation. Now, if they have so- a quality or a value that they're able to contribute to what you're trying to get done, you must make allowance for. You must. But if not, then every day they work for you-... is actually a missed opportunity for you and for them, 'cause if they're not gonna work out inside of your enterprise, your company, whatever it is that you're building, the faster you get to that, the better. And by the way, that's one of the lessons I learned along the way, which is I had seen, you know, "Okay, well, let's give them three months, and maybe they'll come around to it," or, "Let's give them six months," or, "Let's give them a year." That shit kills you, [chuckles] you know?

    12. HS

      Yeah.

    13. JK

      And I am telling you, I've had things where I hired a COO of my company, and the day after he arrived, right, two days after he arrived, I went, "Oh, my God, this is not gonna work." I, I... A- and right- and, like... I mean, literally, it was a big headline news in the business and, you know, th- you know, everybody was like, "Oh!"-

    14. HS

      But you got rid of him two days in.

    15. JK

      Oh, no, I knew two days in it wasn't going to work. It, it... And it took me 30 days to actually deal with it, but-

    16. HS

      Ah

    17. JK

      ... you know, normally I would've lived with it for a year or two.

    18. HS

      Yeah,

  13. 31:3433:58

    Do you agree that “when there’s doubt, there’s no doubt”?

    1. HS

      I do.

    2. JK

      Right? Disaster.

    3. HS

      Do you agree- do you agree, when there's doubt, there's no doubt?

    4. SJ

      I mean, m- mostly. I mean, I'm sure there are exceptions, so, a- and I wouldn't... I, I think it's, I think it's a little too simplistic because, uh, look, if you're a rigorous... Like, if you have h- super high expectations, everyone's gonna come up short at some moment in time. So that, you can't, you can't use that as a, as a generic standard. But, you know, it i- you know, especially when you're early, you, you haven't managed many people, and you're an empathetic person. So let's just take that as a... You know, 'cause there are many people in our, in our business who are not empathetic, and for, for them, you know, they're a little Asperger-y, and they can fire someone without thinking too hard about it. But for people who are empathetic, which I think Jeffrey is, and I think I am, firing people is brutal because you can't sleep, right? You're, you're, you're thinking about it all the time 'cause it's, it's like their life, their families, you know, their reputation, all that stuff you're thinking about. And, and so it's really hard, and if you've never done it before, it's even harder. And I remember... So the first person I ever fired, I won't- obviously won't say who they are, but, uh, it was a person in a, in a leadership role, um, at Dropbox and was clearly not delivering results. And, uh, Sequoia basically staged an intervention with me. So Brian Schreier, who was on our board, was like, "You know, what is wrong?" [chuckles] You know, he's like: "What's wrong with you? Why are you not...?" And I had all sorts of excuses, which, you know, there were, like, some- there was some basis to them, but they were excuses. And he said: "Listen, like, Alfred and I are gonna come up and have dinner with you. This is an important function, and we just want to talk to you about it." And, you know, we're sitting down for two minutes, and Alfred's like: "Okay, just walk... Sujay, just walk me through the situation. Walk him through the situation." And Alfred looks at me, and he's like: "Look, so the- just curious, so you're the COO of this company. You've hired, at this point, hundreds of people. What's the best thing for all of them for you to do with this person?" And I was like, "Ah, shit. All right, it's over. I'll deal with it tomorrow." Because... And that, for me, has become the most clarifying thing as an empathetic person. So it's not like what matters to me, it's what's the right thing for all these other people who are bought into this mission that we're do- that we're pursuing together? And if- when I frame like- frame it like that, um, I can, I can make the hard calls.

    5. HS

      That is a hard

  14. 33:5836:15

    Are Gen Z the Most Entitled Employees?

    1. HS

      call, and firing people is tough. Uh, people often say, like, when they look at this generation, millennials are the worst employees. Do you agree with that statement, and is that fair? I'm gonna put my neck on the line here. I'm gonna be contrarian. Fuck it. Why not? I think they are. I think they are entitled. I think they want too much money.

    2. SJ

      [chuckles]

    3. HS

      I think they are arrogant and egotistical. I don't think they actually contemplate the challenges that their manager goes through most of the time, and I think it's appalling. Thank you. Here, I- it's less.

    4. SJ

      All right, so I'm gonna read you... Somebody just texted me this, like, like, 10 minutes ago, uh, no, or 30 minutes ago: "A recent National Society of High School Scholars survey of 11,000 high school and college-age people found that Gen Z..." So not millennial. "Gen Z's highest priorities when choosing an employer were the fair treatment of all employees across genders and races, followed by quality of life, employer flexibility, and corporate social responsibility. They are more likely to leave jobs that don't meet their needs and find better-paying employment elsewhere." I mean-

    5. JK

      Harry, I... Harry, you're fucked.

    6. HS

      I, I forgot my gun. Give me a fucking break. [laughing]

    7. SJ

      [chuckles]

    8. HS

      I mean, whatever happened to ambition, building something of value, of meaning? Co-

    9. JK

      They're there. They're there. That's what you have to go on the hunt for, right? So that's, uh, you know, those people are out there. It's not everybody, but that's... Now you just actually said, "Okay, well, what's the bar that you're gonna set for people you bring into your business, any business?" And, you know, you just answered it for yourself. You want people that have the same conviction and have the same commitment and the same passion to go out and change the world that you do, and that's great, and you'll find them, by the way. They're there.

    10. HS

      How does that mean you feel on the statement about Gen Zs and millennials being the worst employees?

    11. JK

      I, I get... You know, I'm- I hate these, when we're like mass generalities here, and this... I, I don't know. I'm, I'm not buying into it.

    12. HS

      CJ, you love a generality.

    13. SJ

      No, I'm not saying this. This, this is a, this is a Harry comment. I'm not saying anything. [laughing]

    14. HS

      [laughing] Oh, that's brilliant. You let me go first, and then you're like, "Nah, you know what? Peace out."

  15. 36:1540:20

    What do you think is each other’s biggest weakness?

    1. HS

      [chuckles]

    2. SJ

      Yeah. [chuckles]

    3. HS

      I'm, I'm glad... Thank you for that, guys. Really supportive.

    4. SJ

      [chuckles]

    5. HS

      Um, I want to talk about you. So this is not, like, external, so you can say here, but I think partnerships are these very special, um, relationships of trust, and sometimes we disagree. What was the most recent thing you both disagreed about, and how did it get resolved?

    6. JK

      ... what time we were gonna get up in Riyadh to go to w- go, go to a workout. We violently disagreed. I wanted to go at 5:00 AM, Sujay said, "I need to get another hour of sleep." [chuckles]

    7. SJ

      [chuckles]

    8. JK

      And I said, "Come on, sissy, let's go." [chuckles]

    9. SJ

      [chuckles] Yeah, so I, I rolled in there at the late hour of 6:00. Um, the funny, the-- so the funny thing about that trip, so one of our associates, um, you know, we brought him, we brought him with us, and, uh, the first, um, you know, the first day, um-

    10. JK

      He's 26, Harry, your age.

    11. SJ

      He's twen- he's your age. He's your age, and he's, he's just... he's a great kid. And, you know, but remember, we have not had offices for the whole time he's worked at WndrCo, so he's actually not physically spent time with Jeffrey or me. And so I think this might have been actually the first time in, in, like, s- in this kind of a concentrated way. And-

    12. HS

      He's like, he's, he's like: "Who are you?" [chuckles]

    13. SJ

      Yeah. Well, kind of. So, so, so the, so basically, he gets in the one night, Jeffrey and I had had a full day of work at that point, and the next morning, Jeffrey and I are both in the gym at, you know, whatever f- you know, I think it was actually, like, 5:30 or something like that. And we're cranking away, we've-- we were in there for probably an hour at this point, and he rolls in, and he just looks at us, and he was like: "Oh, you guys are already here?" And it was like, you could see, like... He was like: "Oh, this is crazy." And then, and then he left after some period of time, and we were still there. And afterwards, he was laughing. He was like: "You know," he's like, "I, I guess I just realized there's another gear." And I think that's actually the biggest thing that's missing from, from remote work is there are, there are things that I learned from watching, um, f- w- working for some of the best people in our business or other businesses. You know, someone you had on a few months ago, Harry, uh, Scott Sandel-

    14. JK

      Mm-hmm

    15. SJ

      ... uh, from NEA. So s- I worked for Scott, um, in, in... started in 2008, from 2008 to 2010. One of the most amazing people I've ever worked with-- for. And Scott was the kinda guy who could connect dots, like, just the f- the fastest I've ever seen. But if I wasn't with him all the time... The reason he and I got so close is I was one of the later people [chuckles] I mean, it's venture. So I would stay... I was later in the office, and he would always, when he was walking, when he was leaving, would be w- would walk past my office, I was, like, the only one there, and he'd come and sit down, and then we'd just shoot the breeze for a few hours. And that's how we became so close pretty early on, and ended up, I get to, you know, and, you know, he's one of the greats, in my opinion, in this business, and I got to work with him on everything for years-

    16. JK

      Harry, I'm-

    17. SJ

      -and learn from him as a result.

    18. JK

      Harry, I'm telling you, this 26-year-old learned more in six days on the road, everything from how to pack a bag. He rolled in with these giant suitcases [chuckles] and Sujay and I are one little rollie. You know, we don't check luggage. [chuckles] You know, we, we've learned you just don't ever do that. I don't care if you're on the road for a month, right?

    19. SJ

      Right.

    20. JK

      I mean, it's just like lesson after lesson after lesson, he just kept seeing. You know, like, when we say we'll be down at five minutes of 6:00, it's six minutes of 6:00 that we're down, not five minutes of 6:00, right? Like, you, you know, if we have a meeting, you show up early, you don't show up late. Like, all of these l- things that just were revelatory to him. And by the way, he took it all in, and where he was on day six was a changed person from day one.

    21. SJ

      He's a different person. Different person.

    22. HS

      I tell you, I agree with you both. What do you-- how does that make you feel about the future of remote? I don't like it. I, I had some problems with my team earlier this week. It would never have happened if we were in the same office. It's fine now because we met in person, but you miss so much.

  16. 40:2040:30

    Jeffrey’s Life Lessons from Fetching Coffee as a PA

    1. JK

      I think it's gonna... I don't think there... Once again, there's not one size fits all. You know, if you spend an hour, an hour and 15 minutes on a commute in, and an hour,

  17. 40:3041:09

    Generative AI: The Future or Hype?

    1. JK

      an hour and 15 minutes on a commute home, and you are an, you know, an engineer, or you are an accountant, or a lawyer, where in-person isn't actually additive to what you're doing, you don't have daily multiple interactions in the course of your day, it's ridiculous, and it's unproductive, and it's unsatisfying. So the herd, you know, idea that everybody moves in sync with one another, mm, I don't think that makes a ton of sense, but the value of people being together in certain types of

  18. 41:0941:30

    What worries Jeffrey about the venture landscape today?

    1. JK

      functions inside of companies, I think, is invaluable. And I think it's been underestimated, and I think you'll see a, a return to it. It may not happen overnight, but it'll get there.

    2. SJ

      Yeah, we, we tried it for two years at WndrCo, Harry, and just blew it up. I just... I got us new offices st- I mean, starting, well, this month and next month.

  19. 41:3041:55

    Best Investment Advice Sujay Ever Received

    1. SJ

      Um, the only thing I'll say is that there are certain leaders that I observe who seem to be really good at it. So one of, one of the companies that we incubated, uh, with the, with the, with the founding team from Dropbox is called Twingate. And Tony Huynh-

    2. JK

      Yeah, Tony. I spoke to him.

    3. SJ

      Oh, you did? You spoke to Tony. All right, so Tony... Anybody you've ever met who's worked with Tony, is like, he is a rock star. He, and he is tough, you know, he's a tough, tough-as-nails kinda guy.

  20. 41:5542:23

    What Jeffrey wishes he knew when he started WndrCo?

    1. SJ

      He's, he's, like, one of those people who always wins, you know what I mean? Like, it doesn't matter what he's doing, he will win. And, um, Twingate, because it was created during the, you know, it st- in 2020, uh, has been remote from the beginning, and the output is fantastic, and he feels really comfortable with it. I was literally talking to him two hours ago, uh, not about this topic, in general, but I just, he... I can just feel it when he's feeling confident with the rhythm of the company, and I have not seen him feel

  21. 42:2349:22

    What does WndrCo look like in ten years?

    1. SJ

      like an in-person transition would be a valuable thing. So I think it does depend on the leadership and how they are able to make it work. But for us, I mean, and I think probably for most companies, in person is big, is big.

    2. HS

      ... A final one for you both, and it's a, it's like an all-star Mr. and Mrs. question. What do you think is each other's biggest weakness, and how would you like them to work on it?

    3. JK

      Well, Sujay doesn't have any, so I, I, um, I'm, I'm good. [laughing]

    4. SJ

      Oh, Jeffrey, not, not, not letting me-

    5. JK

      So, Harry-

    6. SJ

      You've been married forty-eight years, I now understand why.

    7. JK

      Yeah. Yes, Harry, let me give you the secret of marriage.

    8. HS

      Oh, yeah, tell me. Come on.

    9. JK

      Oh, it's- it couldn't be simpler, couldn't be easier to understand. It just-

    10. HS

      Oh, yes

    11. JK

      ... And it- and by the way, doesn't fail. It's two words: yes, dear.

    12. HS

      [laughing]

    13. JK

      That's it, right? So here's how I- I've been... So Sujay and I have been on the road, and we sort of introduced one another, and this is the thing that makes him the happiest of all. So I actually talk about how, in my career, I have had among the greatest mentors and partners that you could imagine. Barry Diller gave me my first gig, and I worked for him for eleven years. Michael Eisner, uh, David Geffen, Steven Spielberg, right? And now I got Sujay. He's my Steven Spielberg 2.0.

    14. HS

      Sujay, Sujay, I would- I mean, listen, you're married-

    15. SJ

      Drop the mic!

    16. HS

      ... You're married, but if I was dating, I would use that with every date. [laughing]

    17. JK

      [laughing]

    18. HS

      That is amazing. Uh, S- hit me, what is the weakness? What's Sujay's weakness, Jeffrey? Come on.

    19. JK

      Uh, it's not a w- again, I would just say to you, it's not a weakness. I actually think it, it, it cuts both ways. He's an optimist.

    20. HS

      Mm.

    21. JK

      And to do what we're doing, if you're not an optimist, you'll never find opportunity. You, you have to have that in your DNA. But also, you now need to have the balance on the other side of that, which is you need a little bit of being a sceptic, a little bit of being a cynic, and he's got those qualities, so... But what drives him most is his optimism, and that's why I love him.

    22. HS

      Sujay, your turn. Dish the dirt.

    23. SJ

      I mean, I think you can tell... I mean, Jeffrey is one of the most remarkable people on the planet, so it's hard to, it's hard to s- you know, really talk about a weakness. I mean, I guess the only thing I would say is that he always wants to hit the home run, you know, in, in, in baseball analogies. He's like, uh... You know, World Series just finished, so I'll think about baseball. I mean, and sometimes, you know, you could just bunt to advance the play.

    24. JK

      Yeah. [laughing]

    25. SJ

      You know, you don't need to, you don't need to swing the bat that hard every single time. Sometimes you can just delicately move the thing forward, and so I think that, um... I don't know. I think, I think, I think if, you know, just that, that would probably be the one thing I would say.

    26. HS

      It's funny, I, I actually have more weaknesses about both of you. I have a catalogue of them, um, and your strengths.

    27. JK

      Please, you know, you share them with us, Harry.

    28. HS

      Ah, da, da-

    29. JK

      We probably won't, we, we probably won't ever talk to you again, but it would be probably cathartic for us-

    30. SJ

      Well, well, well

Episode duration: 49:22

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