In this episode, host Chris Thornton interviews New York Times technology reporter Mike Isaac, whose Uber coverage won the Gerald Loeb Award for distinguished business reporting. They discuss the troubled internal culture at Uber and the values that helped to perpetuate it. As we encourage organizations to double down on culture, this is a lesson on what not to do as we enter into the future of work. For more information on Mike’s book, Super Pumped: The Battle for Uber, click here.
Transcript
This transcript was automatically generated with artificial intelligence. It’s in the queue to go through a review with human eyes!
00;00;00;00 – 00;00;31;23
Unknown
And Welcome to Change@Work, a podcast about the ever evolving world of work and the human behaviors that drive it. We recorded this episode with the New York Times, Mike Isaac a few months ago before COVID hit, and we hold off on releasing it. Listening to it now, you’re going to hear some things that might sound a little bit out of date, things like just casually walking around an airport bookstore or if you’re in the U.S. hopping on a plane and flying to Europe.
00;00;31;25 – 00;00;55;27
Unknown
But as corporate cultures change and as the skill sets that leaders need right now to be successful also change. We thought we should release this episode as an example of what not to do. So as you look to build your culture, as you enter the future of work, here are some helpful tips of how not to do it.
00;00;55;29 – 00;01;25;25
Unknown
Our guest today is Mike Isaac, technology reporter at The New York Times. Gerald Loeb, award winner, frequent contributor on CNBC and MSNBC and author of Super Pumped the Battle for Uber. Mike, thank you so much for being here. Hey, thanks for having me. So you wrote this book. It’s big and beautiful. And if you’ve been in an airport bookstore recently or any bookstore, you know, this cover says Super Pumped Bright Red Book you cannot miss.
00;01;26;00 – 00;01;47;10
Unknown
And it was vibrates on the shelf when you’re walking by. There’s something really intense here that you’ve got to read. And have you read the book? You deliver. You deliver. Thank you. And it is I think it was funny when we my publisher showed me the, like, early test cover. At first I was like, whoa, this might be too much, you know?
00;01;47;12 – 00;02;05;17
Unknown
But I think I came to like it, and it really works. And it fits the vibe of the book. It really works. It really works. So we’re going to talk a little bit more about the book, but we’re also going to talk about the culture within Uber and leadership there. Before we do that on every podcast, we have to prove that you’re human because of the work that we do at Daggerwing Group is change, but it’s a little different.
00;02;05;17 – 00;02;27;20
Unknown
We really try to lead with being human, so questions What’s the best career decision you’ve ever made? You know, man, I would say simultaneously, best and worst. Yeah. Was creating a Twitter account because I do think I think as a journalist, I mean, my day job is working at the times of the journalists, like kind of in kind of how journalism has gone.
00;02;27;20 – 00;02;52;16
Unknown
It’s this cult of personal branding and just sort of like being out there. And even the Times weirdly has sort of the brand is sort of first, but at the same time, the journalist kind of is distinguishing themselves more. Right? And so I think a lot of my sourcing as an early journalist, I wouldn’t realize how much of my sourcing would come just because I’m being my stupid self on my Twitter account.
00;02;52;18 – 00;03;10;20
Unknown
Yeah, so I follow your Twitter account. It’s really good. I would say it’s very unfiltered. Yeah, yeah, yeah. Especially for somebody who works at the New York Times. I don’t know how I swear I should have been fired a long time ago, but I think I can just have enough insurance for a little. Okay, well, send this to your to your bosses and let them know.
00;03;10;25 – 00;03;38;13
Unknown
Let them know to pay more attention. What career advice would you give to your younger self? I think, you know, I’ve been in this industry for like ten years now, and I think it’s fairly simple. Just be be polite, be nice to the industry is often very small. So like, things can get around really quickly. And if I want to, I never know where I would like to work next or whatever and not like immediately burn bridges at some outlet that I would love to work for.
00;03;38;13 – 00;04;05;18
Unknown
And reporters can be kind of catty at times and dogged on each other’s work. And that aggressiveness can be good, right? Like we always want to get the next scoop or story, but at the same time it you can you can make enemies quickly so. So I just think the industry is small and I think people who have a reputation for being easy to work with or get along with tend to be at least the ones that I want to work with.
00;04;05;20 – 00;04;21;02
Unknown
So where do you live right now? I’m in San Francisco. Did you grow up there? No, I actually grew up in Fort Worth, Texas, and where my parents still are. And I would say probably half my life to have moved like 30 times in my life, but half my life there. And then on and off for the past 15 years in in San Francisco.
00;04;21;03 – 00;04;40;27
Unknown
How’d you end up there in San Francisco? Yeah, I well, I flunked out of my first college, and then I met up with my brother in San Francisco. He was going to school there, and I did some work at a junior college to try to, like, pray that some other college would take me and then transferred to UC Berkeley and just sort of.
00;04;41;03 – 00;05;05;15
Unknown
So some other college did take you. That’s interesting. A little college nearby. It was very much like, please accept this wayward child. And I got back into school and and I think just sort of convinced folks that I loved literature and I loved writing and I was interested in journalism and tried to take that seriously and was just it was either school or or like freelance writing gigs or internships.
00;05;05;15 – 00;05;29;18
Unknown
Yeah. So it was it for like 12, 12 or 14 years. And did you get into technology just because you were there? Total fluke. I was in the Bay Area and the first internship that I got was at Forbes writing for their tech vertical. And I knew nothing about tech except that I kind of grew up straddling. I’m 35 now, so I remember when computers were not in homes, but I also remember getting a cell phone in high school or whatever, so kind of in the middle.
00;05;29;18 – 00;05;58;28
Unknown
So I feel like I had enough intuitive knowledge about tech that I was slightly more comfortable writing about it. Okay. But I totally total crash course, especially in like business writing. I was I was an artsy fartsy kid, too. Fine. Fine. Artsy fartsy. No, I mean, whatever. It was an artsy fartsy kid, too. But I just I spend my you know, if I’m talking about, like, what I would do on the weekend or to chill out, it would be like reading in a cafe or with my dog on the couch or something.
00;05;58;29 – 00;06;19;26
Unknown
What was your favorite age growing up? man. Honestly, it’s. I was thinking about this the other day. Looking back now, I thought I was cool in my twenties, and then I realized that my twenties were terrible. And in my twenties I thought my teens were terrible. And now that I’m in my thirties, I, I kind of enjoy them, you know?
00;06;19;26 – 00;06;42;20
Unknown
And I’m so probably like early thirties. 3132 It’s just sort of the cusp of feeling like, All right, I’m kind of an adult now. I’m where I should be, whatever that means. In my career, I feel like I’ve I feel like a little more stable in knowing what I’m doing. That said, I feel like every day, I don’t know.
00;06;42;20 – 00;07;00;25
Unknown
I’m trying to plan a trip abroad right now and I feel like I’m totally going to get lost in the middle of Europe. So like, you know, figure it out every day as a new job. 33 All right, man. I feel like slightly more in my in my adulthood. Wait till you’re forties. That’s what I hear. Four days are even better.
00;07;00;25 – 00;07;20;29
Unknown
I don’t know. I think you might regress. At least I did. Let’s get into your book. Yeah. So you’re reporting constantly. Viewers out there, they’re huge. They’re always making news. What inside of you said I have to write a book about this? Totally. So I got to the time in 2014 and I would say 2014 was when Uber started becoming a verb.
00;07;20;29 – 00;07;43;00
Unknown
I think outside of San Francisco, in New York, it was like a thing. And Lyft was pushing into New York and had written about the company for a few years. But in 2017 and I had talked to an agent before who was like, Maybe you should do a book on this, But it didn’t feel right. For whatever reason, there was the story was not really there for me, and I wanted it to feel right, you know?
00;07;43;02 – 00;08;09;29
Unknown
And in 2017, I had gotten weirdly wrapped up in the story. The media becomes a large part of how things play out. People are using the media to plant stories to like take each other out at the top of this company. And I’m ultimately there through the end of Travis Kalanick, the CEO, his his reign. And when he’s sort of forcibly pushed out of the company.
00;08;09;29 – 00;08;30;01
Unknown
After I break that story, the next morning, my agent called me. He’s heard me on the Daily The Times podcast and is like, if this is in the book, I don’t know what is, you know, at least a business book. And I agreed. I was like, This really ruled my life for the last few months. And I think there’s so much more in my notes on the cutting room floor that we could do something with.
00;08;30;01 – 00;09;14;23
Unknown
So it felt right, and then we sold it pretty quickly. Up to that, the story almost tells itself, except you’ve done so much reporting here that it can’t tell itself. You’re going in for some pretty, very specific details. One in particular that stood out for me because it’s similar, though different, very different from the work that we do is is when it comes to defining values within an organization, for me, that’s when I start to see and maybe I’m sure it’s the luxury of hindsight, but as I look to see those values and how they were presented at this two and a half hour meeting of 14 values, which we would not recommend, I’m pretty
00;09;14;23 – 00;09;43;19
Unknown
difficult to remember 14, especially when they’re six. It’s a lot and they’re written in a way that just from an outsider’s view, are open to interpretation and perhaps some pretty negative behavior. It’s a very, very vivid retelling as you build trust. I guess when I’m asking a question first about reporting and building trust, how do you build trust to be able to get that detailed with your sources?
00;09;43;19 – 00;10;03;29
Unknown
Like what does that look like? You know, totally. I think I think there’s a few things. One one early on, one editor told me, like people people really latch on to details in stories, right? Like, I think that’s what makes a story work a lot of the time. It’s there’s a story someone wrote about Marissa mayer who was becoming CEO of Yahoo!
00;10;03;29 – 00;10;21;14
Unknown
A while back, if you remember that. Yeah. And I don’t really remember anything about the story except the scene where she’s like sitting at the top of this boardroom table popping like blueberries into her mouth. It was this weird, small detail that still stuck with me because I was like, CEO eating blueberries during this meeting in like a weird way.
00;10;21;21 – 00;10;41;26
Unknown
And so I think that’s just like, that’s the stuff people latch on to or whatever, whatever that is. And in a story, it makes it click. So it made me ask people weirder, more specific questions over time. You know, when I was talking to like, well, what shoes did he wear to the meeting? Or like, what does he like to eat?
00;10;41;26 – 00;11;01;24
Unknown
Or do you know what you know, blah, blah, blah, Just, just random stuff that makes a scene pop out more because I think that’s how people experience, or at least that’s how I sort of read experience stories, right? Yeah. Becomes a thing. Here’s not non to apply our ethos and branding to you, but you are exceedingly human right?
00;11;01;26 – 00;11;22;26
Unknown
So I think you Yeah, I think it makes you really easy to to trust and read because you’re you’re, you are sharing enough of yourself transparent enough right to know that there’s actually a human on the other side typing this out on Twitter. Yeah I could see how people start to trust you to tell the story in a way that will be fair to them.
00;11;22;26 – 00;11;41;25
Unknown
That’s that’s the other real and this is just personally, I mean, besides being a Times reporter, I think just getting the story right and being fair and not necessarily going in with an ax to grind against any one person or side or whatever I think is is what works for me a lot of the time. And it’s what gets people to open up more.
00;11;41;26 – 00;12;07;23
Unknown
But I think you’re right. I think there’s a line about oversharing or under sharing and and I try to hopefully try to strike that balance a lot of the time. When you think about that culture that was created, they’re looking back to me, reading your book, it feels like from the very start, Uber was set up to succeed Gloria slowly and fail in so many ways.
00;12;07;23 – 00;12;31;14
Unknown
Is that a very good framing? No, I think that’s a great framing. I think a lot you know, I get into the book like a lot of things really clicked in place at a specific point in time to make the service work, if you remember. I mean, I just remember back in 2009 in San Francisco or 2010, I was getting I have a first job at Wired, which is their offices are in Soma, which is like a transportation desert.
00;12;31;14 – 00;12;51;12
Unknown
And I would have to leave the office like 45 minutes early for a meeting because I had no idea if a cab was going to come get me or if the trains were running on time. So like, there were enough problems with infrastructure. There are enough people sort of getting on to higher speed networks at the time, 3G and eventually 4G would would come into being.
00;12;51;15 – 00;13;29;27
Unknown
And then, you know, this is trite because everyone says it, but it really is true. The proliferation of smartphones and everyone just starting to have computers in their pockets made this service click for a lot of people, I think. And so that was the positive part. Yeah. And the the sort of I guess the hubris of it all is that maybe it just works so well and it connected with people so well that Travis Kalanick, the CEO, felt this sort of manifest destiny of of that Uber should be everywhere and ubiquitous in not just the United States but around the world.
00;13;29;29 – 00;13;55;10
Unknown
And there was sort of a self justification of barging in to every true country. Right? Truly, that meant breaking rules, bending, if not breaking laws and just sort of flouting regulators all over the place. And I think that did the man in the end, there was almost too much confidence and and he didn’t know how to mature as a CEO when he probably should have been.
00;13;55;11 – 00;14;24;09
Unknown
There’s a there’s a point at which you’re no longer the underdog. You’re kind of like you’ve made it. Absolutely. You know and I think a lot of leaders in tech, especially the best ones, know when to sort of step into that next phase. And I’m not sure Travis ever did. I keep coming back to those values. So when I’d dig into them and if you could tell us how how you saw those play out, having a champion’s mindset and being only wanting to work with the winners, winners only.
00;14;24;14 – 00;14;52;20
Unknown
Can you think of a time where you saw that play out in Aruba in a pretty disastrous way? I think a lot of it just created this real toxic environment internally of the best rise to the top and the weakest or the worst gets sort of filtered out or shut out over time. And it didn’t I don’t think it created a real, you know, anything conducive to like teamwork, right?
00;14;52;20 – 00;15;17;25
Unknown
Like it was more like, I’m going to try to get ahead and maybe undercut someone else in a in this org just so I can end up on top and it turns into this weird, like Hobbesian environment where everyone’s just trying to do nice. The other person. Yeah, to kill or be killed and I don’t. And you know, if everyone’s I don’t know, I just think that that led to real bad H.R. issues, which the H.R. department didn’t really exist in a functional way.
00;15;17;25 – 00;15;45;14
Unknown
And, you know, bad behavior like rampant sort of misogyny or or, you know, slew of subordinates was just went unchecked. As long as you made your numbers. So it you know, there’s this sort of hero worship around, you know, quote unquote, winning in the company that I just think had a lot of after effects that created a bad culture, especially when they grew in size to something like 15,000 people.
00;15;45;20 – 00;16;12;27
Unknown
Yeah, that just doesn’t scale. No, it doesn’t. It doesn’t. And you tell some very specific stories about people being destroyed. Yeah, right. Yep. Lives being ruined. Yeah. Emotionally, physically, Sexually being harmed. Right. And so it’s easy for us to it’s easy for me, I should say, to say, boy, this is this company is made for greatness. And also it’s a disaster.
00;16;12;27 – 00;16;40;08
Unknown
But then there are people’s lives absolutely being destroyed because of the culture and lack of healthy leadership. Super Pumped is the name of the book. It’s also one of the values of the organization. I would also note that super pumped is number 12 on the list. Number 14 is be yourself, which might be a little bit of a contradiction, especially when you make it clear that being super pumped is what actually gets you ahead.
00;16;40;08 – 00;17;05;18
Unknown
So can you describe what super pumped actually means? Yeah, it’s it’s I use this as a quote in the epigraph. It’s just sort of like bringing being super pumped gives us super powers to attack our our day or something like that. I mean, I look at a lot of this list as just sort of a broad translation of like some corporate cultural value statement, you know, I mean, and Travis has always been really obsessed with Amazon.
00;17;05;18 – 00;17;46;00
Unknown
That’s where he drive the number 14, 14 values. Jeff Bezos had 14 initially, but they all had Travis’s sort of bent on them. And I think look, I think the yourself that he wanted people to bring to Uber was probably not the authentic self that many people who went to work there. And some people it was sort of self-selecting, like the people who thrived were probably the ones that that ended up being problematic at certain levels of the company and maybe even had to be, you know, pushed out of the company later on when their investigations and then the folks who just wanted to have a job at this tech company or just do things
00;17;46;00 – 00;18;14;06
Unknown
that were maybe interesting or exciting technical challenges might not have done so well or might not have rose to the top because they didn’t fit that mold of what Travis thought was a leader. Right? And so it was a real it was a real push and pull for a lot of folks there. And a lot of people who is funny now that the current and former employees that I talked to there, it’s like totally mixed.
00;18;14;06 – 00;18;35;13
Unknown
Some people hate me and think that the book is totally unfair. Some people think that the book is more than fair, even if they have even if they still love Uber. And some people wish I would have gone harder on the company. It’s all across the map, you know. But I think it’s I think that’s that’s kind of like the culture that was created inside of there, you know.
00;18;35;16 – 00;19;03;00
Unknown
Mike, thanks so much for your time today, listeners. The book is called Super Pumped The Battle for Uber. It’s a phenomenal read. Just look for that bright red book on bookstores. Charles You’ll know exactly that book when you see it. Mike, thanks so much for your time today. Yeah, thanks for having me. This is great.