Very Fine Day #52: Mike Isaac
"I am not getting invited to Uber parties."
VERY FINE DAY features weekly interviews with writers, creators, reporters, and internet explorers. Learn more about the people who keep the internet humming – and check out previous editions here. Follow us on Instagram and Twitter, or just follow Brad. Subscribe now and never miss an edition.
“If the early years were marvelling at a techie in his dorm room creating these enormous, multi-billion dollar companies, now we’re in this era of perhaps disillusionment about what we have created.”
When Uber first broke onto the scene, the world was still obsessed with the idea that the internet would make everything better. Yes, there were bad things on the internet, but the idea that the platforms and apps we built – designed to push us into the future – could somehow have a detrimental effect. That idea was allowed to lay dormant for a while. Mostly, we ignored it in place of the flashing lights and the big audience numbers and the funny memes. Of course, we know better now. But it’s largely too late to put the genie back in the bottle.
Mike Isaac is our guest on Very Fine Day this week. Mike is a reporter at the New York Times and the author of Super Pumped - The Battle for Uber - which may sound familiar to you because of the new TV show about the origins of Uber and the gig economy that is… also called Super Pumped. What can I say – it’s a good name.
Mike and I spoke about reporting on the 2010-era Silicon Valley, and what it was like to watch Uber, in particular, grow from an idea into a billion-dollar Unicorn into whatever the hell it is now.
Despite a collapse a few years ago (which Super Pumped documents so well) Uber is still riding in the pocket. Though it may not have turned out as fresh as everyone had hoped, its impact on the way culture thinks about delivery, work, employment, and… a bit of decency and patience, is obvious.
This is the 52nd edition of Very Fine Day – a full year of the damn things. Thanks for coming along for the ride. Tell a friend, subscribe today, stick around why don’t you. The water’s warm. You might as well swim.
See you down the road.
INTERVIEW BEGINS
Mike Isaac: There’s a lot of tech money out here…
VFD: It's good. It's worked out really well. I was in San Francisco before the pandemic, it seemed like everything was under control and totally fine. Definitely no long-term institutional impact to deal with.
Mike Isaac: Going great. Going great here.
VFD: It's a good walking city, though. Which I thought was nice.
Mike Isaac: Yeah, I mean if shit wasn't so fucked up in so many different ways. It is a beautiful city. I have a lot of criticisms. There's a lot of baggage around San Francisco in general. But I've been here since 2004 and I really love the city and really love California. There's this movie actually called The Last Black Man in San Francisco and he had this really good line, he was like: You don't get to hate San Francisco unless you love San Francisco. Right?
That's how I feel around a lot of this city. I complain all the time. But as soon as I hear some random tech guy come and complain about it, I'm like: Hey, fuck you!
VFD: Keep your mouth shut! Were you born there? Did you grow up there?
Mike Isaac: I was born in Florida, of all places. I grew up in Fort Worth, Texas and went to high school there. I moved like 30 times in my life all around the States, mostly.
VFD: Military family?
Mike Isaac: My dad was in sales. That kept the family moving and then we ended up deciding to stay in Texas. And so that was childhood. Then ,with journalism, when you're coming up – or at least for me, when I was coming up – it was just sort of like: “Okay, you go where the next internship or job is.” And so I went to DC, to Atlanta, to New York, then I finished my undergrad in California and then lucked into a job out here, basically.
But yeah, I would say Texas and California, the two places that I spent the most time.
VFD: Right, which is now becoming a new modern migration pattern.
Mike Isaac: Totally, yeah, in the opposite direction. Honestly, it's wild. A lot of tech libertarians-slash-conservatives live out here, the politics out here are… very strange.
VFD: I mean, it's just rich people.
Mike Isaac: Honestly, you're exactly right. People with money are migrating southward.
VFD: Yes. To watch that from the outside is a very bizarre thing, especially when the narrative is about how Texas is like, not old America, but it's free and wild. And then all we have over here is reading the paper and looking at the facts. So Texas seems like a conservative state with a bunch of conservative laws. And yet…
Mike Isaac: I have a few friends who live there and they're like get the fuck out of here to all this tech money. I guess it just depends on where you land in Texas. Austin is this liberal bastion, but even now because it's a tech hub, it's getting taken over with rich people value sets and stuff. It's very culture wars all over the place here, I guess.
VFD: Yeah. Those are really fun to be a part of. That's the best part about it.
Mike Isaac: You do a bunch of different stuff for VICE? I was gonna ask, what is your normal coverage? My wife used to work for Motherboard back in the day.
VFD: Oh cool.
Mike Isaac: You might overlap, do you know who Sarah Emerson is?
VFD: Yeah, I think I do. I think I probably follow her on Twitter? The name sounds right.
Mike Isaac: She was at Motherboard for years and then moved to - where did she go? - she got into Medium and now is at BuzzFeed basically.
VFD: Oh, she’s reverse me, I guess. I was at BuzzFeed for six or seven years. So I was part of things when we kicked it off here in Australia and talked a lot about how dangerous it is and how we're all going to die but also…you should come here!
Mike Isaac: No, you guys did amazing hard hitting work. I remember on Boonta Vista they were talking about The only good journalism coming out of Australia right now is the BuzzFeed Bureau basically.
VFD: Yeah, it was a real bummer when they shut it down because I agree. I guess I was like: this is kind of the antithesis of the Ben Smith vision, though I don't think it was because of Ben. There's some financial decisions, I'm sure. But I was just like: guys, in three years, we've become part of an entire country's media ecosystem, which is not easy.
Mike Isaac: Amazing. It sucks they had to do that. I mean, their plans now are weird.
VFD: It's quite a lot. But I am a - what would you call it - non-vested equity holder of BuzzFeed. And it's doing so well! So I'd encourage them to continue. If anyone's reading this, please continue what you're doing! It's really great. That was a lovely parting gift of my redundancy: I get to watch my worth continue to descend.
Mike Isaac: Are you in those slacks? The Ex-BuzzFeed slacks?
VFD: Oh, I was, I had to leave. I was like, this isn't healthy.
Mike Isaac: It was definitely not good.
VFD: And I get it. I get it. I think it's like the natural evolution of hiring a bunch of early 20 year olds. And then being like, Oh, and you get equity. And then that was the end of the conversation. So all these early 20 year olds walk away and think that means I'm going to be rich. Because this is doing so well. Therefore, I'll do well. And it’s like, uhh, not really.
Mike Isaac: I have never been a part of anything - Well, no, I take that back, I used to work at All Things D which became Re/Code and there was a period in which they were going to give out stock to employees. But I left before we got that and so I've never been a part of that. But yeah, Sarah got equity at one place she worked.
I talk to VCs for my job and they're like: Getting equity doesn’t mean anything, especially when you don't know the outstanding shares. And what the value of these are. It’s a good way to seem like something good is happening, but have no clue what's actually gonna happen, you know?
VFD: Yeah. It's definitely on the favourable side for the C suite to be like Oh, no, okay, come on, in. Enjoy this.
But yeah - I did that and then I went and worked at a tech company for two or three years because I broke my brain, working in media. And then it was so sufficiently broken that after two or three years working in a tech company, I was like - in October last year - Oh, I'll come back. But no, it's been really good.
Australia is a weird place because you basically have these two publishing companies that publish everything, and VICE is now kind of part of one of those here.
Mike Isaac: Oh, interesting.
VFD: Not so much in a tone of voice or any sort of institutional way, just in a funding way. But it's been really interesting for me to leave media and also to have been part of that Facebook go brrr era of digital media, which I'm sure you were also a part of, where it was like Everyone's doing well, okay, cool. And everyone's reading everything! Great! What could go wrong!
Mike Isaac: Mmhmm, I remember 2014, man, I wrote a story for The Times when I first got there on Buzzfeed raising like $100 million and everything was going great. I was like: The Times need to watch out because the Vox’s and BuzzFeeds of the world are gonna kill you and all this stuff. And I think digital media in general was just sort of, Everything's awesome. And then, you know, obviously…
VFD: Until it's not. Yeah, yeah, I remember when BuzzFeed published the future plan of the New York Times. I look back at that and I'm like, man, getting ahead of yourself, really.
Mike Isaac: So wild.
VFD: But no. It's been cool to see us, particularly with VICE, where the challenge is that this brand is countercultural and now - it isn't as much because everything that was countercultural is now just like: you should be that way. To be like: Pro gay rights! And everyone's like: Uh yeah?
Mike Isaac: Yeah, yeah, yeah, well, now you get to create a Substack and be countercultural through that. No, don’t do that.
VFD: I mean the temptation is always there. I was talking to someone last week where it was like: I think almost everyone working in media has at least a little devil on their shoulder that is like, You know you could do this. You could be on Fox News or you could be the Substack reactionary and it would be so, so, revolutionary to your bank account and to your lifestyle.”
[Around here the internet dropped out. But we pick back up a few minutes later]
Mike Isaac: My internet dropped out.
VFD: Well it could equally be on my end. We’re currently experiencing torrential rain unlike anything that has been seen in 50 years or more.
Mike Isaac: Oh, holy shit, I did see some flooding photos come out of there.
VFD: Where my housemate went to college is now under. 18 metres of water or something. It’s unreal. And our oil baron politicians continue to just say it's not about the climate. They're like, No, this is not a new issue and it happens every couple of years and we've just got to deal with it. Anyway, we'd be talking a while if we went into the climate denialism of our politicians.
Mike Isaac: Yeah, Jesus.
VFD: Also I just looked up your - no, that's a weird sentence. I looked up your wife hahaha. But I do remember Sarah because of her dog. Which is also your dog? Maybe?
Mike Isaac: Yeah, the big burmese mountain dog?
VFD: I just remembered that was part of my internet digest for quite a while because there'd always be tweets of this huge dog just hanging out.
Mike Isaac: That’s Bruna! She was on the couch behind me, but she went somewhere else.
VFD: Okay, man, well, what are you up to at the moment? I feel like I kind of know the answer to that question, because of the show and everything. But it must be pretty hectic.
Mike Isaac: Yeah. It is kind of wild. I think the show just premiered. And it's funny because it's sort of like traditional TV in the sense that it's episodic and will come out one episode every week for seven weeks. It’s funny that it now seems quaint in the age of Netflix, or like, some HBO stuff where they just dump it online - but I actually like serialised TV where you wait, and then each week you get more. So yeah, for the next seven weeks or six weeks it’s going to be all about that.
VFD: Are you an anxious person? Is that a delayed bit of anxiety? Like a weekly rating of your ability and whether you've judged the situation well?
Mike Isaac: God, yeah. I think the other thing that's throwing me is, obviously, the fact that the world has been thrown into chaos by Russia starting a war. And that has just sort of fucked up my sense of what is normal right now. And what I should be doing.
Am I able to do my job? I'm really excited for this thing that the showrunners worked really hard on and that I was part of and got to support as it was being made.
And then, at the same time, nothing feels like enough, everything else feels like it pales in comparison to what is going on in Ukraine. So yeah, it’s hard to get work done. And I am doing work. But I prioritise things, basically,
VFD: Are you guys all at home still?
Mike Isaac: Yeah man. I think in the States there's varying degrees of COVID safety stuff. On the East Coast folks are much more out and about, and I think people in the Times office in New York are going in again, to varying degrees. And you have to be vaccinated and all that.
VFD: Yeah, yeah.
Mike Isaac: But in the bureau that I'm in, we have a satellite office and some folks go in more often than others. I'm more of a homebody, but I'll do source meetings or go out and meet people at cafes or whatever.
VFD: It's kind of like normal life now.
Mike Isaac: Yeah, it's definitely getting back to a sense of normalisation, I think, that wasn't there for a very long time.
VFD: So, with Super Pumped, walk me through how that happened. I'm imagining a man with a Monopoly money kind of vibe. And he gives you a call and he's like, Would you like a TV show? and you’re like Yes!
Mike Isaac: Hahahah, actually, it was the opposite. It did kind of happen by accident.
Super Pumped, I get the book out in 2019. And I'm preparing to promote it. I'm sort of like: Okay, I have no idea what I'm doing. Promoting a book is crazy. Promoting a book is super hard because if you're not, like, Barack Obama or some celebrity who has a built in fan base, you have to get people interested in what you're doing. And asking people to A) buy a $30US book, B) read, fuckin, read the book - which no one does. Or no one does beyond short, Twitter-length sentences, so that is also very hard.
So, an uphill battle from the beginning. But I think we ended up doing okay. In that process, I was like, Okay, where do I promote this? I'll try to send it to podcast people, because podcasts are a thing and people listen to them. And in retrospect, I'm glad I did. Because I think that's more important than - save for a few like humongous TV shows, or like morning shows where normies watch and buy stuff on there - I think people listening to things, Public Radio and podcast, is really important as far as readership and stuff.
So this guy, there's this TV show runner named Brian Koppelman, who I had followed on Twitter for years, who has a podcast called The Moment where he interviews celebrities, important people, people in his industry and other industries. And he also created the show Billions, which is big in the US.
VFD: Oh, wow.
Mike Isaac: Yeah, and so he and his partner, David Levein, and then another showrunner Beth Schachter - I didn't know David or Beth but I knew Brian just through Twitter - we’d bantered over the years and I listened to his podcast. So I was like, I'm gonna send him my book. Because fuckin, maybe he'll have me on his podcast.
At this point, I'm desperately throwing it out to everyone. And then didn't think about it. Didn’t have a second thought about it. And then a few weeks later, probably, it turns out he ended up opening it and reading it.
VFD: Wow.
Mike Isaac: I know. I guess he read like, 100 pages. And he was like, Holy shit, I gotta get my partner to read this. And so they both read it and really liked it or really loved it. And so he basically DM’d me back, he's like, Read your book, it’s great. We think there's probably a TV show here. And I was like, Whaaaa…? And so I'm sure he thought that I was trying to get to making a TV show from the beginning.
VFD: Hahaha, yeah.
Mike Isaac: It was more just my naivete on how this shit works and desperately trying to promote my book, but it really worked out. And I lucked out, because I honestly never thought two people like them, who are super talented, and have a hit TV show, would be at all interested in this, at all. It was more just sort of like: Please have me on your podcast.
VFD: Yeah.
Mike Isaac: So I could not have gotten luckier. And they've been lovely and super, super creative and super curious and interested in learning about the industry even more as this whole process has gone on, basically.
VFD: I think you've just sent a bunch of early young creatives to this guy’s Twitter account.
Mike Isaac: Uh-ooooh.
VFD: Like, That's all I need to do. All right. Okay. Sending DM’s, sending manuscripts.
Mike Isaac: I think it’s like the digital equivalent of in LA when you hand someone your script when you're driving them in the car.
VFD: Same level of cringe.
Mike Isaac: Basically, oh man.
VFD: Well then, on the book itself; I know that obviously you covered startups and Uber for a long time and what must have felt like a long time - You’re just nodding sagely - what is that like, sticking to a very focused story area for so long? How long were you writing about Uber? Three years or something?
Mike Isaac: Sure. It's funny, in my early career I did a bunch of random stuff. I was a music journalist for Paste Magazine, I was briefly a political journalist as my first internship.
VFD: Oh, not for you then?
Mike Isaac: Which I did not like. I don't think I could survive in DC - like every town has its own sort of personality and I don't think I would fit in there. And music journalism was actually a lot of fun because - it's just fun - you get to go to shows, you listen to music, interviews, that I enjoyed. But, unfortunately, there was zero money in it.
VFD: Oh, what???
Mike Isaac: Right, as in most areas of journalism. When I graduated high school, I fucked off and flunked out of college, did too many drugs, sort of wandered into retail land and was like, What do I do with my life? I have no idea, I'm going to try to write, but also I was working at coffee shops and restaurants three days a week and then doing these writing internships. Which I don't recommend except you have to do it to pay rent, which is what I did.
And so after I got my shit together, I went to community college and transferred to UC Berkeley out here. Thankfully, they accepted me, and then I just sort of kept doing random internships. I graduated into the financial crisis, which was awesome.
VFD: Yeah, that's cool.
Mike Isaac: I graduated in 2010, everything was fucked. The roommates I had were applying for jobs for a year and then - nothing. It was like: Great.
But I got lucky with an internship in San Francisco, and they were like, Well, we need someone to write about tech, because obviously, we're out here. And it was a business reporting internship, but on technology, and I was like: I don't know anything about business.
I'm 37 now. And so I straddled the non-tech era. And when I was young we had a PC in our house, a Gateway 2000, which was a big deal. And then AOL slowly came up with tech coming from not a part of our lives to very much part of our lives. Blackberries, iPhones.
I had enough intuitive knowledge of how tech works to be okay with writing about the industry to some degree. And then just weirdly got lucky writing about tech as an intern in 2010 when Facebook was on the rise.
VFD: When it was cool.
Mike Isaac: Yeah, these Web 2.0 companies were becoming formidable things that people cared about, rather than just a passing internet fad. So I found a niche there and just pursued it pretty aggressively, basically.
Wow, that was a long way of saying that I’ve been writing about tech and startups since 2010. And in 2010 it was still Uber Cab, and it was this new thing that all the venture capitalists and techies were using.
I weirdly went to college with one of their first employees. We were English literature majors together in the same classes at Berkeley and it was very much a two paths diverging moment where she was like: I’m going to work for a startup and I was like I’m going to be a journalist! And one of us has a much bigger bank account now.
It was wild to be lucky enough to be on the ground floor of a very transformative time in tech.
VFD: Yeah, and to watch it, like you said, turn into this cultural thing, and then also collapse a little while still maintaining its foothold as a cultural thing. Which I think is interesting, right?
Uber didn’t fail. But it didn’t reach what was expected of it. Uber did not become what it was meant to. But we’re still using it as a verb. You get an Uber. You Uber to places. It’s had such an impact.
Mike Isaac: Yep, hundred percent.
I think we’re in a different era of tech now where – exactly what you said – if the early years were marvelling at a techie in his dorm room creating these enormous, multi-billion dollar companies, now we’re in this era of perhaps disillusionment about what we have created.
And I think we're gonna move through that, again, to a phase of reckoning with what has been built. But it's not going away. I think it's just going to be used differently, perhaps regulated differently, perhaps contained in different ways and accepted for both the good and bad parts of what it can do. So people are a lot more sceptical now than they were 10-15 years ago, I would say,
VFD: Yeah, a reckoning would be good. I think we’re due a good reckoning - Everything else is so calm. Might as well.
Mike Isaac: Yeah, exactly!
VFD: And then - Uber, specifically - as you had that connection through the college friend - At what point did you realise: I'm gonna pivot pretty much all of my reporting to this. This is more than just a thing that I also do, it’s the thing I do?
Mike Isaac: I think it was when I got to join The Times in 2014 covering startups, broadly. And this was the era where unicorns were becoming a thing – companies valued at more than a billion dollars. And so that used to be a rarity.
Companies like Facebook and Twitter – before unicorn as a word existed – those were the unicorns. By 2014, Uber and its class of companies: Airbnb, Dropbox, there were multiple unicorns and dozens – even hundreds – of unicorns coming up.
So that was a different sort of class of companies. I think if you’re a startups reporter you have to pick and choose your targets. Or else you’re just going to be writing about different companies all of the time. Which is fine. But I don’t think at a national newspaper that’s the best way to go about it.
So I was like: Alright, what are the biggest companies right now that I should be paying attention to? Uber happened to be expanding like crazy, raising tonnes of money. It was just a very dramatic story. There's a lot of upheaval around its expansion, whether it's cities and how they work, how transportation works, how labour and the gig economy was specially created, or at least popularised by this very new model of working, or an old model of working but made more popular by this company. And then it spread to other different companies. Like you said: Uber became a verb at that time. There was also the whole Uber, but for X phenomenon.
VFD: Oh, god, yeah.
Mike Isaac: Uber for fuckin laundry, or whatever. So I was like: Alright, this company is important. I don't know quite how important it's going to be. But I think I need to keep an eye on it. And so I just picked it, and I told my editors - thankfully, the editors at The Times generally trust me - and so I was like: We need to follow this closely.
So the consequence of that was by the time the story was huge, and the company was imploding in a way, I had already been writing on it for years and was lucky enough to have sources at the company. Which was just a luck thing.
VFD: Well, there's a bit of work involved.
Mike Isaac: I did work for it but I mean, it's all timing and luck. And then busting your ass, I guess is what I would say.
VFD: Yeah, own your successes! That's good. I'm sure you're not invited to a lot of Uber parties anymore, or ever.
Mike Isaac: I am not getting invited to Uber parties.
VFD: No, but were you ever? You were talking about Facebook and Twitter, and that early period where people were like, This is fun, and nothing will go wrong and we’re just enjoying the internet. Was there ever a phase there where Uber was like: Oh, Mike, yeah, let's have a chat. Things are great. Drivers love it. So good.
Mike Isaac: Sure, sure. I think tech PR has gone through different phases. I think that relationship was much cozier in the early era of tech. How tech journalists talked to companies meant they didn’t really ever expect any insanely critical coverage in the same way that they anticipate it now.
And I question my career. I question my coverage during that era and what it looked like.
The thing about Uber is that I maintain a cordial relationship with them to this day. Even if a lot of people hate me, or some folks will never sit down with me, that's fine. But they know that I'm not going away, and I have to deal with them. I've moved away from covering the company since the book and now it's not my beat anymore. But they always know that I'm going to write, they're going to know what's coming, I'm gonna give them a call and walk them through it. I will try to be as fair as possible. And I think that's as much as you can ask for. My goal is just to be straightforward, upfront and fair, even if the facts are not pleasant for them.
So I think that's always been true. But there's definitely been an arc of the relationship. As you know, press has become more oppositional to these companies in the Valley over, let's say, the past five years or so.
VFD: Well oppositional in general, which is also just another great thing to see happening. Real good signs of a healthy democracy. How would you describe your beat now, then?
Mike Isaac: Well, I mostly cover Facebook, Meta. That's like my main beat company.
VFD: You've got another book, is that right?
Mike Isaac: That's right, yeah. So I announced a little while ago that I'm working on another thing on Facebook and the people there. I think the thing that worked for Super Pumped was to just focus on the characters and the drama. There’s a dramatic tension inside. And so I think you can do that, hopefully. I can do that for Facebook, if it's not too overexposed.
VFD: Yeah.
Mike Isaac: And so that's part of it. The good thing is the editors give me a wide berth, so I get to pick and choose interesting stuff that's going on. Like, because everyone in tech is obsessed with crypto right now there’s so many good stories on how insane it is.
VFD: God, yeah.
Mike Isaac: You’re in it, whether you love it or hate it. And I'm more of a skeptic than some people in the Valley. But there's tonnes of stories around it. So they're just like: Yeah, go for it.
But I think I'm anchored to Facebook/Meta, and then kind of trawl around for other good stories.
VFD: In a way we all are, which is great. Anchored to Facebook.
Mike Isaac: Exactly
VFD: Well I won't keep you any longer. I appreciate your time and thanks for doing this.
Mike Isaac: Well, thanks for having me, super fun.