The Pomp Podcast - #382: Alex Konrad on The Best Stories In Tech

Episode Date: September 11, 2020

Alex Konrad is a Senior Editor at Forbes covering venture capital, cloud and enterprise software out of New York. He also edits the Midas List, Midas List Europe, Cloud 100 list and 30 Under 30 for VC. In this conversation, we discuss the various stories Alex has written, including Dustin Moskovitz, Lee Fixel, Masayoshi Son, Chris Sacca, Canva, Clubhouse, Zoom, and Snowflake. =============================== ExpressVPN lets you access the internet as if you’re from a different country. There are hundreds of VPNs out there, but ExpressVPN is ridiculously fast. You can stream everything in HD quality with zero buffering! If you use my link right now at EXPRESSVPN dot com slash pomp, you can get an extra three months of ExpressVPN for free! That’s https://www.expressvpn.com/pomp =============================== Bybit currently has over 300,000 users, with the number growing in double-digit percentages monthly. The exchange has no overloads during volatility and low latency trading plus 24/7 customer live support. At Bybit, we listen, care, and improve to provide the best possible trading experience and create a faster, fairer, and more human trading environment. Visit Now! =============================== Pomp writes a daily letter to over 50,000 investors about business, technology, and finance. He breaks down complex topics into easy to understand language, while sharing opinions on various aspects of each industry. You can subscribe at https://www.pompletter.com

What's up, everyone? This is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Let's kick this thing off. Alex Conrad is a senior editor at Forbes covering venture capital, cloud, and enterprise software out of New York. He also edits the Midas List, Midas List Europe, Cloud 100 List, and 30 Under 30 for Venture Capital. In this conversation, we discuss the various stories Alex has written, including Dustin Moskovitz, Lee Fixel, Masayoshi Sun, Chris Saka, Canva, Clubhouse, Zoom, and Snowflake. I really enjoyed this conversation with Alex, and I hope you do as well. Before we get

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Go check out Bybit. And there are over 300,000 users by clicking the link in the description to the podcast. Go check them out. Lastly, don't forget that I write a daily letter to over 50,000 investors about business technology and finance. I break down complex topics

into easy to understand language while sharing my personal opinion on various aspects of each industry. You can subscribe at pompletter.com. Again, Pompletter.com. All right, let's get into this episode with Alex. I hope you guys enjoy it. Anthony Pompliano is a partner at Morgan Creek Digital. All opinions expressed by Pomp or his guests on this podcast are solely their opinions and do not reflect the opinions of Morgan Creek Digital or Morgan Creek Capital Management. You should not treat any opinion expressed by Pomp

as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his opinion. This podcast is for informational purposes only. All right, guys. Bang, bang. I've got Alex here with me. Thank you so much for doing this. Yeah, thanks for having me. Awesome. Let's just start with your background before we get into a bunch of the stories that you've written about. Where'd you grow up and what did you do before you got to Forbes? Yeah, so I'm Alex Conrad. I'm a senior editor at Forbes. I've been at Forbes for a long time now, especially for media, since 2012. Grew up in New York City on the Upper West Side and went to

school at Harvard up around Boston. Otherwise, I've lived in New York City my whole life. At first, I kind of was hoping to follow some sort of Indiana Jones-like career path, but I realized that that was not super practical in the 21st century. So while I did kind of study more that kind of coursework in college and am passionate about archaeology and history, I realized that storytelling was kind of the only skill from that that would meet kind of two requirements. It would keep me fed and, you know, with a house, but it would also allow me to just go deep on a ton of different subjects. And I think for me, that's kind of the way I'm wired is I love to just, you know, learn a ton of different things every day. I'm sure you get to

experience that a lot, you know, in your job too. So I'm gravitated to journalism as a way to tell stories and get paid to do so. And at Fortune Magazine as an intern in 2010, I basically faced a choice. Do I want to do politics or do I want to do business writing? I thought the technology and sort of the business around technology was just going to increase in importance over time. And I think that was right. I mean, 2010, it wasn't that shocking, but there were a lot of exciting companies popping up both in New York, but just everywhere. So just really leaned into the tech writing back then, started covering a lot of the startups that were sort of popping up in the New York scene locally, because most tech writers were out around San Francisco. and the rest is history. I've kind of just grown with that beat over time. It's been 10 years, but it's been a lot of fun. Yeah. So when you say you wanted to follow the Indiana Jones path, what exactly, and most people in college probably don't have like a grand plan,

but like what was the general idea was to go be an archeologist or something else? Yeah. I think the idea was I wanted discovery and I wanted to be sort of sharing the story of like old forgotten civilizations and places uh you know with the world and so i studied archaeology um dug up harvard yard which was really fun we found like an old building from the 17th century you know where just the foundations were underground and the tourists were like who are these people like why are there shovels that it was really fun um and then i was also um you know i studied some arabic for a couple years wasn't that great at it but um that was really interesting, Latin, medieval history. And I kind of just envisioned, you know, in some world I

would be like in Sicily or in Egypt or somewhere, you know, just like finding forgotten things and then, you know, writing about them and sharing them with the world. That's awesome. I can only imagine the approval process it went through to get, hey, we're just gonna like dig up the earth, right? No problem. So you get to Forbes and talk a little bit about what you're doing now on a day-to-day basis, because you've got kind of some of the major lists that you work on, but you also write stories on a pretty consistent basis. So how do you think about your day-to-day job? Totally. So I'm a senior editor, one of the more senior tech folks at Forbes. And so what that means is I kind of have a balance of anchor lists that I oversee, as well as a lot of our,

but not all of our tech coverage. My specialty is more kind of venture capital, and then more of the B2B world, where it comes from startups all the way to the big companies like Microsoft and Salesforce. You know, I've written cover stories on Satya and Mark Benioff over the years. But then also, you know, a lot of small companies I read about too. In terms of the lists, I run the Midas list, which is the sort of most visible ranking of the world's venture capitalists by their returns. I also have co-led our VC 30 under 30 list for a long time. And then in 2016, I created the Cloud 100 list of the top private cloud companies in the world with our partner, Bessemer. And that's really grown over the past few years. It's going to be coming out in a few days.

Awesome. Let's start with the Midas list. It is one of these lists that it almost feels like the higher up somebody is, the less they care about it. And the people who are on the bubble, the people who might get into it or just barely got into it, they really care a lot. And so it it always provides a couple of weeks of fodder on Twitter where everyone is debating who got what, is that legitimate or not? How do you think of the Midas list and kind of the purpose behind it?

And then maybe talk a little bit about the process you guys go through and actually determining who makes the list, who doesn't make the list and kind of where they rank. Well, first, there's definitely something with lists where I think the ultimate mic drop move is when someone wins an Oscar or something and they don't show up.

And so I do think that there's part of that dynamic where if you make the list, it might be considered cool to kind of downplay that. But definitely privately, we get a ton of feedback. We get a ton of feedback from the people who don't make the list privately. So it is one where I know the whole industry is watching really closely, and we feel a lot of responsibility because of that, too. We really want it to be as accurate as possible. In terms of kind of the process, the list is a data-driven list, and I'd say that one of the big complications is we follow it by individual, not by firm. A lot of VCs will say that that is a team sport, which is totally fair. But if Mike Trout ever leaves the Angels, his numbers will follow him. And it's not like the Angels can just write him out of their history. And so I think in VC, there is a bit of a tendency for firms to trade off of the big companies like an Uber forever, even if the people who did that deal have left. And so we do follow it by individual the best we can. And we also are looking at exits or highly valued companies of the previous five years. So private companies don't count as much as a public company because they aren't liquid. But we're looking at basically companies that have raised an up round or gone public or been acquired over the previous five years. That way, we don't get, you know, longtime retired folks. But at the same time,

it's not a popularity contest of like, which VC is meaning the hardest that year? Absolutely. What's the craziest thing? Don't name it any names. But what is the craziest thing somebody has said, who didn't make the list in private? Like, are we talking like, anger? Are we talking about like, kind of posturing and almost like, trying to position themselves to win in the next year? Like, what are those responses? I think I think the most brazen is correction requests, where it's like, we've made a formal factual error. And you know, their PR firm is like, you forgot so and so, please update the list to reflect their name. And it's like, that's not really how it works. Um, but we also get folks who, um, will DM me or email me and be

like, Hey, just had this exit, probably not good enough to ever make your Midas list where, where that salt is definitely, um, apparent, you know, it's really not personal. And I do feel bad when these feelings are hurt to a degree. Um, hopefully they give me good stories because they're trying to get noticed more. So you're saying like in between the list coming out, people will literally send you the deals that they do so that just to double check that you for sure know that the deal happened this morning i woke up to an email from an unnamed vc of an exit for a company saying if this doesn't put me on the Midas list i might as well just give up so i mean look and to be honest like there should be an entire list you should rank all of the uh responses you get through the

year right and like almost like strip out the names and just say hey here was the best things that I got from people who didn't make the list? Because I'm sure that there's some absurd stuff on there. Yeah, I would say it's almost worse with the 30 under 30 list, because 20 something hustlers are possibly even more shameless. I mean, it definitely is always interesting to see really successful, heavy hitters in the VC world kind of taking things personally. But at the same time, you know, it's also kind of flattering. So we don't want to like punch down too much, I'd say with 30 under 30, um, unfortunately people really get the wrong impression that kind of the more annoying or omnipresent they are, the better they'll do.

So, so, you know, we'll get Instagram DMS and stuff like that. And, and it's like, you know, like anything in life, why would, why would seeming, um, like you're a stalker be a good thing? I love that. And talk a little bit about, uh, so the 30 for 30 or 30 under 30, uh, talk a little bit about the process there? Because that seems to be a little less data driven, just given the fact that there's kind of not as much quantitative data to actually analyze. Yeah. So, you know, we are taking nominations right now in the fall. And we're especially looking to have like a more

inclusive, diverse list. Unfortunately, anything where people are nominating themselves or their friends, it can end up a bit of a popularity contest. And, you know, we don't love to see the same faces over and over. So that is something that we are working on intentionally. That list is nomination based. So people either raise their hand or they raise someone else's hand for them. We also do our own outreach. And then there are industry judges. So unlike some other places, we actually don't claim to be the experts. We actually just try to find experts in the domain. So like in venture capital, my world, we've had past judges like Sam Altman, Naval Ravikant, Rebecca Caden, Sarah Tavel, Alexis Ohanian, Arlen Hamilton, a lot of big names.

Every year, we have three or four of those folks who are actually evaluating the people. My job is to make a baseball card of each credible person, hype them as much as I can to the judges, and then see what the judges think. Awesome. And so obviously you're managing these lists and kind of working through all the nuances there and those are coming out on a periodic basis. But at the same time, you've got what I'll call kind of your day job, right? Or what, at least before the list you were doing, which is writing. You do a fantastic job of that. Talk a little bit about the recent story on Dustin Moskovitz, right? So Facebook co-founder, kind of forgotten a little bit, it seems like, and then now comes back with this company that is a multi-billion dollar

business and seems to have really taken the world by storm. But talk a little bit about why write this story and then kind of what that process looked like. Totally. So I first met Asana in 2015. I think they were always able to kind of get in front of reporters throughout their history to some degree because Dustin Moskovitz co-founded Facebook. For a while, he was the youngest self-made billionaire in the world. That obviously is going to have some cachet. Justin Rosenstein, his co-founder, was also one of the sort of key early folks at Google and then Facebook as well. So they had that kind of pedigree and they were on the radar. But Asana itself as kind of a work software team management company wasn't the buzziest over the years. And I think what I

found out is that a lot of that was somewhat intentional. This year, with COVID, it's work software is just so important. I think, you know, when you can't go just walk into someone's office or just like shout across the hallway, you have to be more intentional about how you work. And so we felt like these tools were very important in this moment. And then we also knew that Asana was likely going to go public this fall. And so given that every year for the Cloud 100, we'd like to profile a really interesting company that's doing well on the list, it felt like now or never with Asana. And so I used that multi-year relationship with Dustin and the team there to try to find a way that they could talk to us, even given the IPO constraints,

so that we could tell the story and the issue this year. Got it. And as you're doing this, what were some of the biggest surprises to you? You had already known the company, obviously, since 2015. But any surprises as you kind of went really deep to write the story? Yeah. So for the audience who may have read The Lean Startup, it's always a pleasure to chat with Eric Ries,

who's doing that and long-term stock exchange and a bunch of interesting things. And Eric is an old friend of Dustin's. So one of the interesting takeaways I got from calling Eric was that basically there was a lot of pressure and not super high expectations among the sort of technorati of 2008, 2009, when Dustin and JR left Facebook to build Asana. um you know peter teal sean parker mark zuckerberg matt kohler all those kind of bigwigs who had made money off of facebook or it seemed like they were going to because facebook hadn't gone public yet they all put money into asana but eric told me that they didn't really see work software as like a huge opportunity especially not compared to a social network and you know 10 years ago social networks were one of the big things that you could look at right twitter was still on the

up, you know, there, there was a lot of excitement there. And so Eric told me that a lot of these kind of, you know, very famous influential people thought, oh, they'll work on Asana for a couple of years and they'll probably go move on to something that's a bigger idea. So I think it was really interesting to kind of see now in hindsight, how they persevered there, um, with the huge expectations of having come from Facebook, but without that buzz of, you know, a Facebook or a TikTok or something like that. So that would be probably the first one. And then I'd point to one other, which is, you know, he said that the hot companies, this is Dustin, as they were building were kind of like Palantir, Dropbox, companies like that, at least in his world, they were all

bragging about how fast they were hiring. They were bragging about big customer wins. It was kind of like part of that supercharged culture. And at Asana, they just took a very different approach where they took a week off every quarter to talk about what went well and kind of map the next quarter, which is a long time to take as a startup. I'm sure you probably have a lot of guests who would be like, that's crazy. And they also had like no meetings on Wednesdays, just banned from having meetings. They just wanted people to be in flow state. They brought in executive coaching really fast. So all this kind of mindfulness, and then they also practice what they preach by saying, we're not going to, we're not going to more than double headcount in every

any one year period. So they kind of like, deliberately put these guardrails on how fast they would grow to try to be that kind of like sustainable company. That maybe seems a little cooler now. But especially I think like a few years ago, that was not the Uber approach. It was not the approach that was being hyped. And so I found that kind of interesting to see it paying off today. Yeah. And it feels also like it's just proof point that you can build these enterprise cloud companies in a whole bunch of different ways. There's no one size fits all in terms of you have to build it this way or it's not going to work. Do you feel like that mentality is changing? Obviously, there's this deep profile that you wrote as they kind of look to go into

the public markets and things like that. Do you feel like the, they're more open now and kind of, they almost are being forced to be more public about what they're doing? I think part of that is Dustin growing as a leader, you know, that I think he's more comfortable, you know, people can follow him on Twitter, he shares a lot of points of view. And I think, you know, he has evolved, he calls himself an introvert. And he talks about having an extrovert budget of kind of like, you know, public facing things that he'll do including an interview with a place like Forbes. And I think his managing that budget has helped them be out there. But I also think as you're saying, it's, this is the space that matters a lot to, to not just tech

people, but anyone who's trying to like work in a knowledge worker role right now. And so if they're not out there talking, when would they be like, this is their moment, you know, and so I think they have to be out there. But it's not just Asana. Another company that does well on our list is monday.com. They are like, you know, audience members may know them from their YouTube ads. Like I feel like every other YouTube video I watched, there's a Monday ad. So they've taken like a very consumer approach to getting their word out there. And there are a bunch of these companies doing well, Notion, Airtable. So I think we're seeing this exciting moment for like, workflow companies. And if you want to be in that game, you got to be out there.

Yeah, that makes sense. You also wrote a story about another guy who I think is very well respected in the circles that he operates in, but is not well known to kind of the average person, which is Lee Fixel. Uh, talk a little bit about, um, you know, the, the, uh, business that he built before he left to go on his own and kind of, uh, what that process of writing, uh, that story was like. Yeah. So writing about Lee was tough because he keeps a really low profile. Um, I think, um, uh, your, your partner Polina, um, was like, I finally got him to talk sort of like, which was a fair way to put it. You know, we did really well at Tiger Global. They're one of the big kind of growth investors out there, especially in the tech space. And Lee is one of a couple

kind of people who were really successful there. They started pretty young under Chase Coleman, and then they became these kind of titans of finance. It's Lee and Scott Schleifer being the sort of two biggest ones, perennial Midas list members. And, um, Lee, uh, last year basically was like, I want to do my own thing. Um, this is my, you know, this is my understanding from conversations with a ton of people in this world. Of course. Um, I don't want to make it seem like I'm directly quoting him on a lot of stuff, but basically, um, you can be super successful, be in a ton of cold startups like Peloton, uh, many others, Glossier, um, at Tiger, But you can't run your own shop. It's like a more traditional financial firm. And so Lee has started his own fund addition, Billion Plus Fund, where he can kind of groom the next generation and be doing his own thing, investing in startups with like total flexibility, what stage.

the coolest thing about that was I spoke to a ton of his entrepreneurs for the story and they had some really good, good stories. Like John Foley, the CEO of Peloton, um, told me that he only, the only stock he owns is Peloton. But if he were to venture out from, from that, he would give money to Lee to invest on his behalf. And that there was actually a boardroom push, um, to get rid of John, you know, when Peloton was not a sure thing and Lee defended him and kind of thwarted the coup. So stories like that are just fascinating to hear. And so it's someone like Lee who gave us a statement who I've known just from Midas for a long time, but didn't give me a long on record interview. The fun thing is to just talk to like everybody you can find in

their life to kind of get those anecdotes. And why do you think he's been so much more successful than most? Is it something in terms of the way he thinks about the market? Does he have the ever elusive kind of proprietary deal flow? What is it that makes him special? I think one thing is that Lee is definitely not an ego-driven investor. He's not on Twitter. He doesn't want a public profile. And I think that allows him to basically avoid getting swept up in any trends or hype cycles. And I think that helps him just be a sort of dispassionate investor. I'm a bad poker player because while I think I have decent instincts, eventually my emotions get the better of me and I do something that messes me up.

And I think to be able to just kind of keep that flatline heart rate as an investor is a skill that Lee is probably the best at. And then I would also say he's just really good at spotting market trends. Obviously, there are a million people at hedge funds and everywhere who are reading reports all day trying to see where the puck is going. I think Lee just has really good decisiveness where he can see a couple trends and say, okay, Peloton, you know, like, like he was actually on vacation, reading about different exercise trends and options and saw Peloton. And at the time, it was a deal that was very hard for them to do because the numbers weren't great. But he was just like, I really think this is the rising tide that I want to back.

And I'm going to stick my neck out with my own firm to commit to it. So I think any of us in hindsight can be like, oh, well, I could have seen Peloton. But to actually just put your chips on the table there quietly is what makes Lee so good. Yeah. And the other piece is the billion plus dollar fund that he has, I think is a split, like a third of it's going to go to early stage, if I remember correctly, and two thirds into growth. Is that a trend that you're seeing where more and more investors are kind of blending the early stage and late stage investing into single funds? Or is that something specific to his strategy? It's something that's hard to do when your firm gets too big. So a firm like

Andreessen Horowitz will have a crypto fund, it'll have a growth fund, it'll have, you know, an early stage fund. Because if you have a lot of people whose careers are depending on success, I think, you know, when you get too blended, it can be hard to kind of extricate one person's success from another or the fund performance. So if a growth deal is not going to have the same multiple as a successful early stage investment, how do you adequately reward someone for a great growth investment versus a great early stage investment? So I think there are structural challenges that big firms eventually face there. Look at a lot of the best firms and they are split. Someone like Lee can move faster because it's just him at the top. And it's just

him deciding what is a success and how people should be rewarded. So I think that's where the flexibility is really attractive to him. I would say I think like LPs, like universities or the big foundations of the world who give money to these VCs, they probably see him more as a growth investor. But he would say that some of his early stage wins were actually as good. And so to not let him do that kind of series A check or whatever is just leaving money on the table. And I just think that being a small, especially being a one man or one woman band right now, you get to make that kind of choice. Yeah, absolutely. Another company that I think is, again, known maybe to consumers, but to the average kind of person just paying attention

to tech, didn't know two years ago and now seems to be everywhere is Canva. And this story is fascinating to me because they're not based in the US, took a very different approach to building that business, but now a multi-billion dollar company. When did you first meet them and what was maybe even your first reaction when you came across the approach they were taking, the location they were based in, et cetera? Yeah. So Melanie Perkins, the head of Canva, is one of the most inspiring or impressive entrepreneurs I've ever met. But when I first met her, I probably didn't take her as seriously as I should have. I was at the Cloud 100 dinner that we do most years. This year, we're doing a live event for anyone to join because we can't

do a dinner. But she just made the rising stars list of companies that have raised under $25 million but we think are kind of like on a trajectory to make the cloud 100 in the future and um she came all the way from australia to san francisco for the dinner and i just kind of met her you know casually and was like oh you know design software that sounds interesting she seems like to have a lot of charisma but i didn't have any sense of kind of the community and the numbers that they were pulling. Then I watched as they became a unicorn, they hit a multi-billion valuation, a 2.7 billion valuation when I was talking to them. And I was like, okay, what is the backstory to this company that is not getting taken seriously enough because it's based in

Australia? So I actually flew down to Sydney last June, and I spent a lot of time with her and her partner and co-founder, Cliff, to just try to understand what they had nailed so much to build a community of mostly very small businesses. Because as I'm sure you know well, you can have a ton of small business customers, and you may not get the scale of one of these enterprise companies that only has a few dozen, but they're huge. Canva is both. It has a ton of revenue, and a ton of scale, while also like living off of these mom and pop and small type businesses. So we went there. Fascinating time for me. And I did have a few kind of learnings from that that I'm happy to share. But I would say overall, you know, the number one lesson was

you can build a business like that anywhere with the right ingredients. And so I think being in Australia, they just crept up on a lot of people. Yeah, what were some of the other lessons? Yeah, I would say Canva spent a lot of time really making sure that its customers were ambassadors of the product. So they wanted to make sure that anyone could get up and running in less than 10 minutes. And they would actually track how long it would take someone to actually make a design on Canva. And I think that's an interesting thing to keep in mind is like, how quickly can someone actually take the plunge to use your tool. So they did a lot of work there. And then they also did a lot of work basically paying it forward with their business, where they gave away a ton of their features for free, and they really didn't stress about revenue early on. Um, obviously they, they, they had to stay very lean to do that. And I think being in Australia, their costs were lower, but they, they basically, um,

nailed this kind of freemium model, um, in a, in a better than usual way. Um, so that then when they turned on their enterprise products, you know, businesses started to convert. Um, and then I would say they also nailed, um, the visual trends, right? Like Instagram and the power of strong visuals and video as part of our brand today, whether it's a person or a company like that was something that I think five, six years ago still wasn't quite as obvious to businesses, especially. And so they enabled people to basically start bikini companies by just having like great designs to show off their products. I actually met an Australian bikini company through the process. But they basically saw that in the Instagram world, brands that did not stick out in more than just kind of their text or their products would not get noticed. And they were like, how can we build tools for those folks? And so I think like, they would tell you that social media was not the original end all be all for them, and especially not Instagram, but they just really quickly leaned into that. I don't know how TikTok plays into that in the future, but I'm sure they're thinking about it.

Yeah, it just seems like that's a company where it's very obvious the founders understood, hey, if we can solve problems for the consumer, they'll eventually become our customer, right? And it just seems like, you know, reading through that, you're like, every step of the way, they kept that focus. I recently wrote a piece basically talking about this idea of most of the tech companies seem to have been customer or consumer focused for a while now. and that's playing out now and being a huge tailwind during COVID, a lot of the legacy kind of non-tech companies, whether it's airlines, fast food chains, et cetera, I think they always talked about it, but now they're realizing like, oh, maybe airlines shouldn't charge $200 to let you change your flight, right?

Maybe actually we should just let you do that because that's something that reduces friction and will lead to you increasing the number of flights you book rather than decreasing it. And so it just feels like Canva is like the perfect embodiment of that where they just paid attention to what their customers wanted and have been able to grow, obviously, incredibly fast. I think that's a great point.

I think if you're a business where talking to your customers is fun, that's a huge advantage, right? If it's not fun, that changes the game completely. If it's like, how do we minimize our engagement with you so that you don't cancel? A company like Canva, I think they just really enjoyed being out in the community and talking to their customers.

And I think, especially someone like Melanie, when her users felt like they knew her or that she was one of them, it created a brand loyalty that is powerful because Adobe does have a good leader in its kind of competitive unit in Scott Belsky and it has good products. And design software will not be the most defensible tool

from a moat standpoint forever. But Canva's brand is extremely strong because I think they actually just love working with people. And so if you wrote them, and this is actually the same as Eric Yuan at Zoom, if you wrote these entrepreneurs, and we're like, here are all my problems with your products, they're the kind of founder who wouldn't get upset. They'd be like, thank you so much. I will take all this to heart. I'm so grateful that you would reach out. And that's definitely a mindset thing. Absolutely. Let's talk about Zoom. You wrote the perfectly timed profile there. And they obviously have become the darling of this entire pandemic. What was kind of your experience writing that one? Yeah, Eric is one of the just nicest people you'll meet. He, you know, I should frame a couple of the emails that he's just sent me, whether it was like fact checking, or just feedback, because you can just see how genuine he is, even now valued it. It depends on the stock, but like somewhere around $20 billion or something is his net worth. But I guarantee you that that would not come across, you know, meeting the guy. he is a real kind of just builder creator where like all he wants is his software to be used by as many people as possible so that he can feel like he's helpful like he just wants to be useful

to the world and that really comes off in everything with that company I would say even you know when they've had challenges his genuine self has kind of given them some credibility there to figure things out. But Zoom crept up on a lot of people because it's always been in a crowded market. Video software didn't seem that exciting. And they just decided to build a tool that was a little bit better in as many ways as possible than what was out there. And it turns out you don't have to have the perfect tool. If it's just the best available and you keep improving it, everyone's going to switch to it, right? So I think like Zoom was just perfectly, you know, positioned for the pandemic. You know, I feel bad for folks who didn't read my story at their IPO and missed out

on all that success. I think the stock is up like 6x since we wrote our initial story around their IPO. But it was just perfectly positioned because now it has brand loyalty. And it's hard to see them losing out on features when they can just kind of quickly improve things that become a priority. So like they've been improving a lot of their consumery features right now because they just spent three months focused on security. And I think, you know, their competitive advantage is just they know this space as well or better than anyone, right? I mean, it's now been tweeted a lot, but like a lot of the top engineers that work for Eric at WebEx, you know, jumped to help start Zoom. So just like deep expertise. When I wrote the story, I'm just going to share one

funny anecdote. Eric was going around with these little envelopes because it was the Chinese New Year. And they just had a dollar in them each. But Eric gave one to every employee he could find. He walked up and down his building. And every time he was like, this is going to make you rich. Working at Zoom finally paid off. Don't spend all this at once. And the employee would open it and there'd be like a dollar. And they'd be like, thank you, Eric. And he just laughed every time. He's a corny dad with dad humor. But I loved seeing that too. Just the actual joy he had mixing it up with the employees. And I think they all got the joke. Like if you're a CEO who's kind of not a very nice person and you're going around giving everyone a $1 bonus, that would probably go over very differently. I'm literally imagining the reaction

that some people would have and that would not be good. How much do you think about kind of the financial performance of the companies that you're writing about from the standpoint of, you know, you mentioned, hey, we wrote a piece and then the Zoom stock is basically 6X since then. do you see that as a good thing a bad thing is it kind of agnostic to you like how do you just think of i guess like market impact of the stories that you write yeah i would say um

we're i'm kind of betting reputationally a bit um the way that an investor does i obviously and for those who don't know like i can't own individual stocks um as a reporter so i don't own any zoom or any of these companies um unless it's in like a mutual fund in my 401k or something right um but i don't want to spend a lot of time talking about a company being interesting or doing something well um if they're not right like it's it's irresponsible it makes me look like a chump makes forbes look silly so there is some risk reputationally every time we go deep with a company um so that said it's very validating when the companies end up doing well financially because it helps me feel like I wasn't crazy,

that something stood out about them. Absolutely. Speaking of a company that is crazy in a positive way, Clubhouse, the sweepstakes, as I think you called it. Talk a little bit about, well, actually, before we do that, for those that don't know, Clubhouse is, I think they describe it as a drop-in audio app that is kind of like a conference call with an audience to some degree.

Talk a little bit about the absolute chaos around their most recent fundraising round and the competition. Yeah, so I mean, Clubhouse had the perfect storm fundraise because it's an app that VCs are obsessed with. And as much as VCs should be thinking about markets that are not themselves, it's really easy to see the demand for something when you are the target customer. So, you know, if you go into a clubhouse or you check Twitter to see who's talking about clubhouse, it is a very high percentage of these individual investors, angel investors, venture capitalists. And so that always meant that they were going to have a competitive fundraise. I think it got even more competitive because of COVID and the fact that basically people had nothing to do. They were desperate for a new platform. and you know tiktok was not really like an easy investment opportunity it's such a big company

with bite dance so i think there was a lot of um there's a lot of firepower waiting to back a company like this the founders also had credentials having built social media companies before it's kind of just like it checked every box so there was a bidding war and you know we were hearing that individuals were trying to put together angel list syndicates to give them like evaluation closer to 200 million for a company still in beta with under 2000 users, totally crazy. And Drewson Horowitz gave them evaluation around 100 million. They did not confirm this to us. But we talked to enough folks that we were able to break that story. And then of course, I hear that they're in Clubhouse like that night, like, you know, basically like questioning the

reporting or like, you know, saying, well, that's not the full story. And I was frustrated because I was like, well, you can tell me the full story if you want. But yeah, no, it was, it was just, it was, it feels like a million years ago, but it was just a few months ago that sort of early in quarantine, that app had just kind of struck a nerve with, with a certain part of the tech world. It's so funny too, because a lot of these consumer apps, they naturally want early, you know adopters and kind of beta testers and so who better than to go get people who understand how to build products and you know kind of do all that stuff which many of them now invest and so you go and you get those people on but uh i always joke with friends like you get on one of these

things and if you're one of the first you know 500 or a thousand users on it it's pretty much always investors and you see the same investors right and it's like oh they're so and so and they're so and so okay i got it like the word is out that this thing is uh is being tested That doesn't necessarily mean that all of them become like these hot fundraising rounds, to your point, but I do think that it's this balance between, you know, a Canva that says, hey, look, we're gonna go after small businesses and kind of as far away from Silicon Valley, that user base is possible. Whereas a lot of these consumer applications, that is who the initial user base is, it just ends up being the people who know how to build products. And, you know, people will debate whether that's good or bad, but it's just an interesting trend to see. Yeah, I think Clubhouse is an interesting test case where basically they have tried to game the sort of consumer success trajectory in a bunch of ways. And if it pays off, if it works, we'll see more copycats, but it may not work. And one of the things they've tried is have Oprah have these big name folks on really early on, keep it small, so that you can tinker with a product with a small team getting feedback from these influencer types, but like basically only having the influencers on there, right. And that's very different from apps where it starts out with a bunch of like teenagers or whatever. And then you're trying to bring on an influencer later on to kind of like, confirm that energy. So I think Clubhouse has gone influencer first, and I don't think it's guaranteed that that'll work. And I do think that, of course, communities built around groups that are not obvious could be much more passionate. It's just harder for those of us on Twitter or whatever to find them because we may not be in that community. Yeah, absolutely. Masayoshi, you got the exclusive interview. I remember Polina telling me at one point, she was like, this has got to be the number one interview that everyone wants. One, how did you get them to agree to do it? And then two, tell us everything about that piece.

Yeah, so talking to Masayoshi-san was like top of my list for probably three years, ever since the Vision Fund burst onto the tech scene. And, you know, for those who aren't super familiar, like $100 billion fund to invest in tech companies, that's at a factor bigger than we'd ever seen before. some of the biggest VC firms in the world. Their AUM is maybe $10 billion now. But so $100 billion fund just to invest in these companies, it was just a massive impact. And we were talking about it, the whole tech world, reporting world, we're talking about the impact of this fund for good and bad. But talking to Masa, who's based in Japan and doesn't do a lot of interviews was really hard. I basically found out that he gave maybe one English language interview a year. And so I just had to be that interview at some point. And I tried multiple times and failed. But around the end of last year, the beginning of 2020, there were a lot of doubts

around SoftBank and the Vision Fund. WeWork had obviously been a massive blow up. And Uber, its stock was not doing great. Its shares were underwater from a SoftBank standpoint. there was a lot of doubt. So basically what I did is I said, you know, I am not going to be beholden to any narrative. I'm going to hear you guys out. And if there's a way that SoftBank can still win here or that Masa's misunderstood, I will like take that beginner's mind and I will hear it out and I will try to give you guys a fair shake. And I think my track record and I guess my sales pitch were strong enough that they thought, okay, like, we will try that. And but I think it was definitely nervy on both sides. And I did meet with Masa in March, right before everything

shut down in New York. It was really interesting experience and interview. And he was much more unrepentant than I thought he would be. Now I had a bunch of questions like, what have you learned from this or what would you do differently and for someone like him the answer was kind of like my tactics might have been wrong but my strategy is always right and it's like that is you know that's what's made him so successful but it also is why i think the criticisms can be fair too so that was it was a trip um talking to all the people in the soft bank orbit was a unique experience it was extremely stressful but we were really happy you know with the story that we were able to put together. And I hope that anyone in the audience who goes and reads that story would

think it's a fair look at why they're in tough straits, but also how Masa can always pull himself out of the fire in the end. Yeah. When you met with him in person, was there any other takeaways that you had in terms of... It takes a special guy on the way to pitch somebody for $100 billion to literally say... I think the story is they were on the plane and somebody showed him the deck and it said a 30-year plan and he said add a zero right to it to make it a 300-year plan so anyone who just thinks that way is obviously very different but what were some of the takeaways from a medium person getting talked to well first off masa is is a lot less um imperial than i think he comes off as part of that is because he has an entourage

he's based in japan it's you go through so many hoops to meet him that you've kind of built him up in your head but he's actually you know a relatively you know small smiling you know unthreatening seeming man physically you know just in like his uh you know sweater and everything um and and and he kind of walks serenely surrounded by this constellation of like freaked out intense people so that's kind of that was my first impression is just that everywhere he went It seemed like he was totally calm. And this is someone that if you sat next to him at a ramen place, you could have a beer with him. But all his handlers, all his lieutenants, no, you could not. And they would not let you get close to him. So that was one. I would say in terms of how he speaks, he is definitely one of these big picture folks. Like he'll speak in big metaphors. He'll speak in kind of the arc of history. As someone who studied history, I could appreciate that. But some people love that he can just sort of fit together a future, you know, the technological future of the next 30 years into a coherent narrative. and that just really resonates and then everything he does is kind of fitting the narrative for other

people that is just inflexible and like impossible to actually do anything with like he could say ai is going to have a bigger impact on the world than the you know microchip and you can be like cool that may be right like what does that actually mean for us in the day-to-day you know and and one of the big things that i was trying to understand was like okay if he thinks that data and AI are the future, what does that actually mean for these companies? Can Uber actually benefit from that in any meaningful way? Can DoorDash suddenly beat all its competitors just because we understand that data is important? There are limits to what you can do with data. And in fact, people are much more mindful now about how their data is used. So I think for me,

the interesting thing was that he has this 40,000-foot view of the world, and then he's trying to apply it, you know, on a company by company basis. And I think that's where things can either go great, or they can go really badly. Yeah. Was there any sense of maybe you talked about like him as a person, but any of the views that he held where you felt like he is either really misunderstood, or people just have misconceptions, like he believes a but everyone thinks he believes be? Yeah, I would say that he sees the power law of investing, I think, just a little more nakedly than a lot of VCs who actually probably believe it more in private than they would say. Masa just believes that a lot of markets are a winner-take-all market, effectively,

that one brand is just going to end up crushing most of the others. And obviously, that's true in some industries. It's maybe not so true in other industries. But I think that directionally, he's not as crazy as it seems about that. And so are you really overpaying in the short term if all you're doing is trying to find that outlier winner-take-all market? I would say probably not as much as he's sort of ridiculed for. I think the problem is where you think that maybe a market is winner take all and it's not

and so you put a lot of money into something without it ever really being able to be the breakout you know like like hopefully there will continue to be a lot of podcast companies and so if you would just crazy valued you know gimlet or wondery or whatever like it will crush every other podcast company probably not going to be the case um the other thing I would say is that i think like masa um is more self-aware than i think a lot of people think like he's mindful he knows the criticism he's not like some uh like i don't know naive person who just like doesn't understand what people think about him i just don't think he cares and there is something to admire there of just the person who like knows that a lot of people doubt them and just sleeps

well at night anyway. Like he was like, I was, you know, I asked him like, what do you think about everyone? Just kind of like, you know, making fun of the vision fund or thinking like you're a crazy person for what you're doing. And he was like, oh, I had it worse after the dot-com bubble. He's like, this is nothing. I don't know. Like if, if, if I would feel that way, but I did kind of have to respect him for just being so unperturbed. Yeah. Well, and I think the part that was interesting is a lot of people forget he was nobody. He became the richest guy in the world, lost it all. And then I think he became the richest guy in the world a second time or came close to it. And so he's kind of had this very

epic boom and bust cycles personally. And so I think that that does probably harden you a little bit. I think it's weird for some investors to have an investor who doesn't seem to be motivated just by hoarding money. I don't know if it's a gambler mentality or what it is, but as you said, He claims to have been the richest person in the world briefly during the dot-com bubble. Everything was so crazy that that's very hard to perfectly confirm. But yeah, SoftBank lost over 90%, almost 99% of its stock value in the dot-com bubble burst. And he could have easily just moved on to something else. But he just built it all up again.

And then the question is, why? If you're already the richest person in the world, what is compelling you? And he's not Bill Gates going to, you know, cure malaria or something. He just like, can't stop trying to play out his thesis about like, where tech is going. And I think that is really confusing for a lot of investors who whatever they say are ultimately like money driven. Yeah, it's absolutely fascinating. One other company that you've written about that I think because it's in the enterprise space, people just don't know it as well as Snowflake, but obviously now they're going to go public here and have kind of this big splash. What was your history kind of meeting the company and then writing that story? Yeah, so Snowflake is a database company. I like to think of it as sort of like improving off of the old Oracle data lakes of 20, 30 years ago. A company that I got to know on the enterprise software beat and through my Cloud 100 sort of beat. And I thought it was interesting that they basically were like these French database engineer nerdy guys who built a tool that actually like could be sold pretty well and then brought in a series of a couple aggressive salespeople to basically run the company. That doesn't always go super well. But with Bob Muglia and then Frank Slootman, they've had these elite people basically brought in as mercenaries to sell their tool to the world.

And yet, at least one of the co-founders is still very involved on the deeply technical side of Snowflake. So that was kind of interesting to me. But again, I think one of the most interesting things about this company is that it wasn't really known to anyone until it hit the market. and then people see its numbers and suddenly you know everyone's everyone's like anticipating this IPO or thinking about how they're going to play the stock and all that and it's kind of like funny to me because um I get to watch these companies whether it's Datadog or Snowflake kind of go from boring can't get anyone to care about them to like should I buy this stock like what do I do you know and it's like there there was a lot in between right um but I do think that uh Snowflake

deserves the attention it's getting. I'm excited to talk to Frank Slootman again when they're not in quiet period and I'm allowed to. I think it is a huge company. And the other thing that's interesting about them is that they've kind of perfectly drafted off of the cloud wars between Microsoft, Google, and Amazon. So they will be the biggest independent company in the cloud that is sort of deep in cloud infrastructure, but not one of those big players. Absolutely. It's fascinating to see just a company pop up out of nowhere and be worth billions of dollars. People are like, wait, what is that company? But you're like, look, there's lots and lots of them. I actually saw Patrick O'Shaughnessy

tweeted the other day or recently, he said, who's somebody that is a founder CEO that you'd love to hear from, right? And is basically running a business that you've never known about before. So I saw somebody tweeted, and I forget the gentleman's name. But basically, he ended up taking the company public in the early 2010s. And he owns the Memphis Grizzlies, right? And you're like, like, this guy's like, not trying to hide, right? I mean, he literally owns an NBA team, but just hadn't heard of him before, right? And so you're just like, that is pretty cool to see. Somebody who's literally a multi billionaire is out there in the technology world, but just because of the type of business that he runs you know it's not something that kind of gets covered

every day and i think that a lot of these companies that's becoming more and more popular right yeah i mean i think unless you um are fascinated with like the underpinnings of the internet or you're trying to trade the stocks it's not always obvious like why you should care about these companies that's always been my challenge but i also see it as like a fun intellectual challenge to basically make these enterprise companies relevant and relatable so like when I write about a company like Zoom in 2019, some people care. Then when the pandemic happened and I wrote about their making the tool free for schools, that was my most trafficked article of all time. I couldn't have written that without all that prep work I had done in the years before,

but it was cool to see it finally resonate with people. That's awesome. One of the last stories I want to talk to you about is Chris Saka, probably the most legendary angel investor of all time, depending on how you count. Definitely did things kind of differently, right? In terms of truckie and all of that. I remember reading that piece when you wrote it and just being like, you know, I can't believe somebody got him to talk essentially. You know, what did it take to get him to talk? And then kind of what do you remember from doing that piece? Yeah. So that was again where like the power of my list was helpful I had gotten to know Chris a bit through the Midas list um and kind of uh was talking to him a bit about his holdings and I think he it

was kind of like oh well you know I'll tell my story someday I'll probably you know I'll probably write a book but but then when it became clear that you know he wasn't going to write a book anytime soon I was able to be like okay well you can still do the book later but why don't you talk to me, you know, now. And I think, you know, part of that was that he just felt finally comfortable to share some of his success, you know, his billionaire status, you know, with his holdings. Some people like Ali Fixel would never want to be called a billionaire, even if they may be. But I think Chris was just like, okay, it's time for me to kind of bite the bullet and be more public facing with some of that stuff. And we developed a trust. So just lots of conversations

conversations, talking to his world. And, you know, that was a tough one, because Uber was still very much one of the top stories of the day. And Chris was very involved in the early days at Uber. So I spent a lot of time talking to, you know, all the usual suspects from the early Uber history. And, you know, no one quite had the same story. Yeah, everyone remembers things a little differently. I think Mike Isaac did a really good job with super pumped with this book to try to hit a lot of the main notes there. But even there, I was texting Mike being like, oh, I heard something a little bit different back during the Saka story. And it's just like, it was one of those things that even as it was lived, it kind of became Silicon Valley lore. So that needed

a fun challenge, almost like a game of Clue. What is the full story here? And I think Chris would never lie, but like he maybe just remembers things a little differently. But he was in a unique place where his friends were the founders of Uber, of Twitter, where he was like there for this, you know, 2008 timeframe moment in Silicon Valley that was pretty unique. And I think he and Aydin Senkut and a couple other folks, Mike Maples, were just able to sort of aggressively seized that gap in the market of the early stage investing, you know, where the other firms had gotten a little too risk averse or a little too big. And so these angels kind of were able to build their brand. Steve Anderson is another great person. And now there are a million of these

people, you know, that we talked about Clubhouse, like Clubhouse is full of these like solo investors. But Chris was definitely one of the first people where he had just built a network that allowed him to, you know, get in early to a couple of these really iconic companies. The other thing from a business lesson is that he just really doubled down on himself. He bought out some of his investors to own more of his own funds, even when he didn't have a lot of money. You know, and he was maxing out credit cards. Obviously, I'm not advising people to do that. But he just had total faith in himself and was willing to have an extremely concentrated position in himself. So why did he become a billionaire? Because he didn't just invest in

Uber or Twitter, but he kept doubling down on those companies year after year, buying out his own investors because he was so long the positions he had conviction in. And I think that's where he's a good example. Yeah. I can't remember if it was your story or another story I read uh, where he was at, um, on vacation or whatever with, uh, Travis and, uh, his father and Travis is playing, uh, we, uh, tennis that was at your story. No, I know. Okay. But I think it was, it might've, uh, might've been a Mike Isaac special. I can't remember. Okay. I, I just, I remember thinking about like literally having those people as your friends, right. And you know, one friend ends up building, you know, a $70 billion company. Another friend ends up building,

you know a 30 billion dollar company and all you're basically doing is you're just investing in your friends in the beginning and that's not to downplay the uh kind of the evaluation and you got to believe you got to actually have you know high quality friends that can build this stuff like all of that is important but it is a pretty special um i think network of people that uh he was able to capitalize on um and the other part i think i took away was just uh how aggressive he was once he knew something was working right in terms of buying out the shareholders you're talking about doing all of those things, um, that just seemed to, uh, to, to not have been popular, uh, before he started really doing it. Yeah. I mean, for the audience, the takeaway that I would

say is, is, you know, the tech world felt a lot smaller than where, um, you know, you could have like these small meetups at South by Southwest where all these founders were getting to know each other. Um, you could have, you know, Travis would have people at his house for jam sessions that, you know, went on to be founders of other companies. And so there was this like small network. Unfortunately, like, you know, most of us are not in those networks, right? And so I would just say,

invest in your own network because South by Southwest, everybody knows, but like, what is the next one? It may be virtual. It may be in a game. It may be in a telegram group. But I would say like, hopefully the next generation of Chris Sackos,

there are dozens of these small groups where it's not just like one house in San Francisco is birthing all the big companies. And I think that was as much just about the scale of the tech ecosystem at the time as it was that Chris was better at picking people than everyone else. I mean, obviously coming from Google and knowing entrepreneurs, it became easier for him to meet more entrepreneurs. But I don't think that the next Chris Saka has to be a white dude who worked at Google, you know? Absolutely. Uh, I finished up each conversation, uh, with the same two questions that you'll get to ask me one. Uh, but before we get into that, there was one question that came in through Twitter. That was very important. Uh, Natalie wants to know why Natalie

is so great. And I figured that you would have an amazing answer for her. So, uh, why is Natalie so great? Yeah. So my partner, Natalie Sportelli, um, if you've, if you follow me on Twitter, you'll see we're talking constantly. She's one of the smartest people I know on brands and kind of all things brand marketing in the tech world, working at a VC firm called Lear Hippo. I love having a partner who is in sort of in the industry with me. I love that we can sort of talk the same language and we can bounce ideas off each other. I think Natalie is just so driven that it can, I joke sometimes that she's my Lady Macbeth because she's going to get me killed. But she's just passionate about moving forward and making a difference. And it makes me a better person in my

job. Maybe you have the same thing with your partner. But I'd say that's what I love about Natalie is that she's probably eavesdropping right now. She's going to give me feedback. When this comes out, she's going to tweet about it. And having someone like that in your corner for good and bad is just awesome. That's a fantastic answer. You made no mistakes. Great job. Uh, the two questions I ask everybody else is, uh, first, what is the most important book that you've ever read? Whoa. Um, I should have probably prepared that one.

I would say, um, there are fiction books that have really resonated with me more than nonfiction books. Okay. Um, shadow of the wind and a gentleman in Moscow are two that come to mind. A perfect spy by John look. Hooray is one that I own the first edition of because it's had a huge impact on me. I find that fiction can sort of allow me to see things differently and have perspective that I really need, especially when I'm spending so much of my day reading other news articles or sort of so deep in the tech news world. Um, so while there are business books that I think are valuable, I would really recommend

to the audience, like find a novel that just changes how you think about the world. And that will unlock things that you don't expect perhaps more than like, you know, a book that's like 20 tips that are going to improve your business. Yeah. That's a great piece of advice. Uh, the second question is a little bit more fun aliens, believer or non-believer. Man. So, so I, I, I argue about this with my friends.

I tend to fall subscribe to the theory that there are probably alien civilizations elsewhere in the universe, but that at least under the current laws of physics as we know them, they're insurmountably far away. And we just will not run into them. That makes me kind of sad in a lot of ways, you know, but then I read something like the theory of the dark wilderness theory, but actually that's a good thing because a lot of us would be prey. and there are predators out there. And so it's actually good if people don't know that humans are around. I do think that just it's hard to believe that we're the only ones out there. Unfortunately, I'm not super confident

that we'll ever like be, we may never find out otherwise is I guess the way to put it, yeah. I think that's a very, very fair way to look at it. A friend recently was telling me, he said, humans think that we're great because we're all human. But if you just compare us athletically,

to animals. We're pretty stupid and unathletic and not very impressive. And so the odds that there is something else out there that is less superior to us when there's things on earth that are more superior is not good. And so to that point, I think that I always think of it in terms of do we want to find them or do we want them to find us? And I think you always want to do the discovery, right? You don't want to be the discovered. Unless they want to help us, But I do think that, you know, as much as I'm, I love like space technology, and I love a lot of like the thought about like, the innovation we can do to kind of both explore, but also perhaps like leave the planet. I do think that, of course, encourages thinking that leads us to invest less in our own house. And so I do think like, if we ever want that opportunity, we have to like do a much better job of like protecting our own house from a climate standpoint, from a lot of standpoints

before we can like go like high five with aliens, you know, somewhere else. Absolutely. All right. You get one question to ask me, what do you got for me to finish up? What has been the question that you ask the most to people because it brings the most sort of unexpected or just like gold answers to you that it's become your like favorite question uh so i'll give you two uh the reason why i asked the alien question is because uh i think it is the fastest way to get somebody to explain a lot about them without saying anything and what i mean by

that is just it shows you how they think about you know kind of problems that i don't deal with every day uh you get to see sense of humor you get to see seriousness you get to see scientific versus not you know you get to see kind of um like uh religiosity a little bit like just i believe because i believe type stuff um so it's just a very uh revealing question uh the problem is that uh i've done so many of them now like i pretty much can bucket the answers like it's either like i believe because there's mathematical probability or i don't believe because i haven't seen them yet like those are the two most popular answers so i don't know for me it's like what people say is less important than how they say it with that question. So that's always been one that I enjoy.

But the question now that, and I don't remember where I got this from, this was not like I had some, you know, major aha, and I was like, I should start asking people that. But I really enjoy asking people after they've told me their perspective on something, like, what would change your mind? Right? And so like, especially when it comes to like, you know, technology investing, or business building and finance and stuff like that, somebody will lay out like this amazing argument and like it's pretty compelling right most people i think are like fairly charismatic if you're you know have some level of success you're a good salesperson um you've been able to convince employees and investors like all this kind of stuff and then to have them like okay now

flip around on the other side of the table and tell me like what basically what's your critics argument and like what would have to happen for you to like agree with them and what it does is it like one the smartest people that i've done on the podcast like by far they can say their critic's argument better than the critic can right and like are very clear and like you know a b and c happens that i would change my mind and you're like okay like that's actually pretty cool that you can do that uh then there's people who uh are like so convicted that nothing's going to change their mind and like they say that and so like i i haven't decided yet is that like a good thing or a bad thing because it's kind of situation dependent like sometimes you need the blind faith

that something is going to occur whether you can explain it or not and then other times like i don't know maybe you get we work right like you know like you basically like run off the cliff blindly it's funny you say that because masa would definitely be in the latter camp where you probably aren't going to change his mind but dustin moskovitz um actually is known with for employees for asking how can the opposite be true or okay how could the exact opposite of the story you just told me be true and he actually does play the same kind of empathy exercise yeah i see the same um size of that coin all the time in my reporting as well yeah that's awesome and i don't think either one's like right or wrong right because obviously both of those two people are

highly successful it's just a matter of um to me as i look at this as like a learning exercise it's the fastest way to get the counter narrative uh and you can pretty much tell you know like hey is this person bullshitting or not right and do they actually understand the critics argument But the people who I think are the most intelligent, they really, really can outline like, you know, here's what it would take for me to change my mind. I just enjoy that. Can I sneak one more question? Of course. You've talked to a ton of people now.

Do you ever have a moment where you feel like you just really misread a person? Or how good would you rate your own ability to kind of quickly get the measure of someone just from your pattern recognition? so it's one of these things where uh i think we all want to believe that we're really good at that type of stuff but like we all probably actually suck at it or we're like worse at it than we than we actually uh are or we believe we are um i think that uh you can cut a person in many different ways right so like in one conversation it's really hard to get uh a lot of reads in terms of like all these different things. But being able to make a read, that person is intelligent and has sound decision-making. From one conversation, you can ask enough questions where at least directionally,

you're probably more right than wrong. So that's something that I think you can get out of one conversation. The other thing is, I think of it as salesmanship. And what I mean by that is, especially for founders, everyone wants to know who's the smartest. And being smart is really important. But also being able to convince employees, convince investors, convince the market. All of that is really important as well. And I think that naturally, when you just have a conversation with somebody, you walk away and you're like, oh, that person is charismatic or that person is not. So I think you can read that pretty effectively. The things that are hard are just like, how persistent is this person? And they can tell you stories about their past where they

were persistent or not. And maybe that gives you some signal. But for us, when early stage investing, most of the companies that have failed, at some point, the founders gave up. And maybe there was good reason to or maybe there wasn't but i think like that's the stuff that you know kind of what somebody's made of right is kind of the cliche way of describing it just how do you get that out of a single conversation i think you got to spend a lot of time with somebody to really unpack that um and so you know if i had one wish it would be to be able to get that type of information out of a single conversation but i think it's just you know human nature makes it too difficult awesome thanks thanks for that that's i'd say there's um there's a lot of

important things to keep in mind there that I think reporters, we do the same thing where we can overread, but of course, people are putting their best foot forward with us. And so, you know, trying to understand if you really have the measure of a person, we end up having to sort of try to triangulate it, you know, if you're talking to other people, too. I'm assuming nobody on a list or that you're doing a profile on is like, hey, let me introduce you to all of these companies that didn't work that I was involved with. No, we usually have to do that work ourselves. absolutely all right alex listen thank you so much for doing this where uh where can people

find you on the internet uh or find more of uh of the stories that you're writing yeah so um my twitter handle is alex r conrad with a k um i'm always on twitter if you tweet at me i'll probably be responding um and then if you go to uh forbes if you just google my name you'll find my forbes author page which has all these stories um ditto the cloud 100 we have pretty good seo so um find me there but if you want to talk to me um twitter is probably the best place to be awesome listen thank you so much for doing this and we'll have to do it again in the future all right thanks man really appreciate it