‘This is Your Life in Silicon Valley’: NYT’s Mike Isaac discusses his upcoming Uber book, Leaks from Facebook and More

Welcome to this week’s transcribed edition of This is Your Life in Silicon Valley. We’re running an experiment for Extra Crunch members that puts This is Your Life in Silicon Valley in words – so you can read from wherever you are.

This is your Life in Silicon Valley was originally started by Sunil Rajaraman and Jascha Kaykas-Wolff in 2018. Rajaraman is a serial entrepreneur and writer (Co-Founded Scripted.com, and is currently an EIR at Foundation Capital), Kaykas-Wolff is the current CMO at Mozilla and ran marketing at BitTorrent. Rajaraman and Kaykas-Wolff started the podcast after a series of blog posts that Sunil wrote for The Bold Italic went viral. The goal of the podcast is to cover issues at the intersection of technology and culture – sharing a different perspective of life in the Bay Area. Their guests include entrepreneurs like Sam Lessin, journalists like Kara Swisher and politicians like Mayor Libby Schaaf and local business owners like David White of Flour + Water.

This week’s edition of This is Your Life in Silicon Valley features Mike Isaac, whose upcoming book about Uber –  ‘Super Pumped’ –  is sure to generate controversy. Isaac conducted hundreds of interviews for the book, and answers some pointed questions about his research during this podcast. Isaac also talks about press leaks, Facebook hacks and more during this interview.

If you want to hear what Mike would ask Travis Kalanick if he had the opportunity for a sitdown, you don’t want to miss this transcript.

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Sunil Rajaraman:

Welcome to season three of This is your Life in Silicon Valley, a podcast about the Bay Area, technology, and culture. I’m your host Sunil Rajaraman, and I’m joined by my cohost, Jascha Kaykas-Wolff-Wolff. This is your Life in Silicon Valley is brought to you by The Bold Italic.

Jascha Kaykas-Wolff:

Hey, Sunil.

Sunil Rajaraman:

Hey.

Jascha Kaykas-Wolff:

How’s it going there across the table?

Sunil Rajaraman:

Going just fine.

Jascha Kaykas-Wolff:

Have you ever met somebody in real life that you’ve only ever known online?

Sunil Rajaraman:

I have, a few times, and I have to say, the Internet I believe is a place where you can meet wonderful people, actually.

Jascha Kaykas-Wolff:

That is like the most glowing, shining, happy sunshiny thing I’ve ever heard you say. These things don’t always end well, right?

Sunil Rajaraman:

They don’t always end well, but today I’m especially positive because I met my Twitter idol, Mike Isaac, who’s a New York Times reporter.

Jascha Kaykas-Wolff:

Not just a New York Times reporter, but what else?

Sunil Rajaraman:

He is writing a book on Uber.

Jascha Kaykas-Wolff:

On Uber, probably one of the most controversial and maybe most impactful technology companies in our lifetime.

Sunil Rajaraman:

And what I really love about this interview is just how transparent, how accessible, and how human Mike is.

Jascha Kaykas-Wolff:

Yeah, maybe we get to learn a little bit about the anatomy of a leak from inside of a company.

Sunil Rajaraman:

This is one of those that you don’t want to miss. We really hope you enjoy our interview with Mike.

Jascha Kaykas-Wolff:

Enjoy.

Sunil Rajaraman:

Thanks for being here today.

Mike Isaac:

Hey. Thanks for having me.

Sunil Rajaraman:

Are you a San Francisco native?

Mike Isaac:

No. I was born in Florida of all places. And then I grew up in Texas. And then I moved here in 2004.

Sunil Rajaraman:

Florida, to Texas, to here. Was there a point in your life, maybe in Florida, maybe in Texas, where you grew up where you were like, “I have to be in San Francisco. I have to be in the Bay Area”?

Mike Isaac:

No.

I mean, I’m glad I landed here. I got here because I did too many drugs in college and flunked out and then found my way over here. And my brother was here, and built my grades back up and went to Berkeley and ended up like staying out here. But I had like zero plan to be here.

Sunil Rajaraman:

What kind of drugs and what school?

Mike Isaac:

I’m actually kind of proud of this. I went to Arizona State and flunked out of Arizona State, which I think is … I think they were the number one party school in the country, so that was like an accomplishment. Sorry. I’m like warm. And then-

Jascha Kaykas-Wolff:       

This closet is tiny. It’s tiny. It’s really warm.

Mike Isaac:

No. It’s all good. And then just whatever was there.

Sunil Rajaraman:

All right, well, look, I got start off-

Mike Isaac:

Don’t judge me.

Sunil Rajaraman:

No judgment at all. I just want to start off with a statement if it’s okay, and just I want to declare that there’s no better company at privacy in the world than Facebook.

Mike Isaac:

Did you see me flip out about that too?

Sunil Rajaraman:

Let’s talk about this. So you were a victim of the recent hack.

Mike Isaac:

Yeah, yeah, man. They-

Sunil Rajaraman:

Which one? Which recent hack?

Mike Isaac:

The one that affected like 50 million people, I think. Or it was 90 million, then 50 million, but one of Facebooks many hacks where people could have full access to your account, and-

Sunil Rajaraman:

By the way, we need you to be in direct line with the mic.

Mike Isaac:

Got it.

Sunil Rajaraman:

Otherwise, Tyler is going to … Tyler, our sound guy is here. He’s on top of-

Mike Isaac:

He’s going to be mad.

Sunil Rajaraman:

Yeah.

Mike Isaac:

I don’t want to piss off Tyler.

Sunil Rajaraman:

No.

Mike Isaac:

Am I allowed to swear?

Sunil Rajaraman:

Yeah, you are.

Jascha Kaykas-Wolff:

Yeah.

Mike Isaac:

Okay. Great.

Jascha Kaykas-Wolff:

Look at him. He’s getting out of his chair like he’s going to come fight us.

Mike Isaac:

Do you need me to get closer?

Jascha Kaykas-Wolff:

So you were involved in all of the hacks, all of them, some of them, one of them?

Mike Isaac:

No, just one.

Jascha Kaykas-Wolff:

Just one.

Image via Flickr / Jimmy Baikovicius / https://www.flickr.com/photos/jikatu/22339401336/in/photolist-A34gJ1-tbg2ww-c447rh-9rVkmt-c446PY-drfLrA-8GPeQt-8GSp3Q-8GPeZH-fLwg8z-crTVRs-crTUqo-crTUKd-crTNNS-crTSRu-crTXbh-crTQKm-crTW9Y-crTStw-crTWQA-crTTGw-crTPxy-crTVwh-crTRXY-crTRwY-crTR8b-yHeXnK-qKHcjw-qKP7yr-crTNu3-crTThs-69QLbR-8nKecC-bujxBY-vo7yv8-qZvydh-qXi9z5-qZrggD-anD7us-anD7T7-anNLAE-o52TVj-oa3UUZ-crTQnJ-crTVbs-crTWvG-crTU5U-bnMHRS-dBSEhr-avuLzz

Mike Isaac:

This was a bad … I mean, this was also right in the middle of Facebook’s prolonged crisis after crisis. And they had the Cambridge analytic stuff. I think the Times did some big story. It might’ve been before that. And then they released this info saying that there was this vulnerability that essentially let hackers take over everything in your account. And they did that to me. And I have no idea what, if they took over my account or whatever, but I probably would’ve noticed it by now. But so, yeah, that was fucked up. And now they have this, they’re on this privacy tour like apology tour, and this marketing VP essentially said privacy is the foundation of Facebook, which I just found laughable.

Sunil Rajaraman:

So you cover Facebook. You cover a lot. One thing I’m really curious about is just not speaking specifically about Facebook but the companies you cover, Uber, et cetera. Tell me about leaks. So employee leaks, so there’s this whole phenomenon of you get these leaks. Are they increasing? How does a leak even work? I mean, I don’t have any sources obviously, but just tactically speaking, when someone leaks something to you, how does that even work?

Mike Isaac:

I have found, you know what’s really funny? Historically Facebook is not a leaky company. They have actually had a really good reputation for being super tight. It’s hard to break in there. And I’ve written about them for probably like 10 years now. I starting writing about them in 2010.

Jascha Kaykas-Wolff:

That’s back when everything was happy.

Mike Isaac:

Right, no, when Facebook was still like cool, when youngs were on it, when it wasn’t just old guys like us farting around and taking picks. And so back in the day, you sort of like bought into this cult of Facebook. Everyone loved it, and all the people that were there working there really liked it. The thing that I notice with companies, and I wrote about Uber last year during its insanity and downfall is that leaks are just a symptom of bigger problems inside of the company.

When people leak, when people talk to people like me, it’s because they’re usually unhappy or they have some sort of motivation to do so because they’re trying to get some sort of result. I mean, that’s one of the reasons: They’re trying to get some sort of result. So Facebook is having, if you just watch the news, more leaks than they ever had probably in their history, and that’s because people are just not happy. And they’re starting to really grapple with the idea that maybe things they’re doing are not all good, or maybe the company is not entirely a positive force for the world.

Jascha Kaykas-Wolff:

I’m really curious about the anatomy of a leak. How does that work? If Sunil, because Sunil is known for this kind of stuff, if he wanted to leak something to you-

Mike Isaac:

Is he an owner?

Sunil Rajaraman:

No, I’m not an owner here.

Mike Isaac:

Are you like an owner leaker?

Sunil Rajaraman:

Just for the record, I only have done just start-up companies. So I would be leaking on like a company of 14 people, so it’s not-

Mike Isaac:

It would be easy to find you.

Sunil Rajaraman:

It’d be very easy to identify me.

Mike Isaac:

You’d be the guy in the trench coat in the basement.

Jascha Kaykas-Wolff:

But what are the mechanics of it? I think it’s kind of fascinating. How does it actually go down?

Mike Isaac:

I mean, it’s probably less sexy than you would imagine. I don’t look like Robert Redford in All the President’s Men back in the day. It’s like it’s not me in a trench coat in a basement, it’s more like I’m in my sweatpants at home texting with someone, which is pretty much emblematic of my entire life. But I think it’s the way that … I don’t want to give too much away, but I think it’s just there’s so many ways to get in touch with the reporters now. And I think reporters are a lot more visible than they ever were before. I think the times specifically, but then a lot of other reporters across different outlets just have this mandate to brand themselves and be very out there.

You guys talked to Kara Swisher before, and Kara is her own thing. My old boss is very Kara. And people gravitate towards that. And I think for the same reason you were interested in having me on to see if I’m like actually funny or just a horrible sweating mess.

Sunil Rajaraman:

Yeah, so listeners need to understand that I’ve idolized Mike on Twitter.

Mike Isaac:

Oh my God. Stop it.

Sunil Rajaraman:

Yeah, very like a year plus.

Jascha Kaykas-Wolff:

When we started, we’re now in our third season, in the first season he was like, “Someday we’re going to be big enough, and when Mike’s going to join.” I’m not joking.

Sunil Rajaraman:

Here he is.

Mike Isaac:

You’re very kind.

Sunil Rajaraman:

Here he is.

Mike Isaac:

Well, I’m just … This is-

Jascha Kaykas-Wolff:

And you’re sitting here in your sweats, which is cool.

Sunil Rajaraman:

Not in a weird, stalkerish sort of way. I don’t want you to get the wrong idea.

Mike Isaac:

I mean, it’s fine. I understand.

Sunil Rajaraman:

Like that-

Mike Isaac:

I understand if you want to stalk me.

Sunil Rajaraman:

I was in your apartment a little earlier, but-

Mike Isaac:

I would like one or two at least. That’s real fame.

Sunil Rajaraman:

It’s interesting, though, but when we’re talking about it’s just not a big deal, it’s just not a thing. You’re out there. People know who you are because of the quality of the work that you put out. And so they’re just like, “I’m going to DM you on Twitter.”

Mike Isaac:

I think it can be. I think everyone, the funny thing is some of my biggest stories have come from the most unlikely places. And I think one of the things in journalism is that stories always lead to more stories. So the way you start out or the way I started out is just I used to write for Recode; and before that, AllThingsD; and before that, Wired. And it was just you start with small scoops, and then people start noticing that you care about the same stuff.

And my personal thing is just letting my ideas run wild into Twitter all day long. And some people seem to respond to that. Other people think I’m crazy or awful. But I think it’s not … I wouldn’t call it a tactic, but it just seems to give people a more of an idea of who I am even if they’ve never met me before. And I think that people respond to that. I think they just want to sort of … Or at least the folks that I talk to can be like, “Oh, I know this guy,” even though I don’t. I know that he just complains about his dog or the poop on the streets or whatever. And I could tell him whatever. So it’s kind of helpful in that sense.

Sunil Rajaraman:

So you get a lot of these. Let’s just say it again, Signal, you have Signal open on your Twitter profile. But you get so many of these. Then what does the investigation process look like? Because I’m sure you get a lot of bullshit.

Mike Isaac:

Yeah. I mean, it is … Well, I would say two things. One, I do get bad tips, or things that just don’t pan out, or people trying to spread … The other thing you have to use is just discretion over what is appropriate to report out or like just people trying to like, “You could talk to someone else,” or whatever.

Jascha Kaykas-Wolff:

Grind some axes.

Mike Isaac:

Yeah, totally. And then also you can get just too much information. There’s just too many leads for me to chase and, too, I have to sort of triage what I think is a reportable thing and what is realistic for me to do or if I need it to be a longer-term project, or if I’m working it with other people. So it’s really just sort of … And thankfully I work on a team of like probably 15 or 20 people in the tech section at a time. So I can pass tips to other folks and whatever. So we’re lucky to have the luxury, we actually have a team, but I think it’s a lot of like managing and triage at this point.

Sunil Rajaraman:

I asked a similar question to Kara, and I’ll ask to you. And I’m very curious to hear your response. I won’t tell you how she responded.

Mike Isaac:

Oh, you got to tell.

Sunil Rajaraman:

I’ll tell you after. How would you respond to someone who told you that, all right, of course the Times is going to run negative Facebook constantly because of just naturally there’s an incentive for you to do so. You probably as a publication, it would be beneficial to have Facebook broken up because they control distribution. So what would your response be to that?

Image via Bill Clark / CQ Roll Call

Mike Isaac:

To that sort of … I get that a lot actually. You are obviously like, “Look, we’re stealing …” Sometimes Facebook employees get actively angry at me and yell at me in my DMs or whatever, which is fine. I’m here for your abuse. But I think it’s like the thought process for them is you’re writing things that get a lot of hate clicks or get a lot of like outlandish clicks. And it’s better for you guys to destroy us because we destroyed you first. Right?

Sunil Rajaraman:

Yeah.

Mike Isaac:

And I totally get that thinking. And I think it’s fair to say that the backdrop to all of this is that publishing is sort of changing and crumbling around us as we try to work through it. I don’t know. I mean, that’s just not how … It’s hard. It’s hard to really argue against. That’s not how we do things. That’s not how I approach a story. For me, it’s more my mandate is like, “Aye, I’m the beat reporter for Facebook. So I just covered them anyway, but, B, it’s like what is the story? What are people doing or talking about that is not out there? And what should be told? And it’s likely not going to be positive a lot of the times because Facebook I think did have a very positive upward trajectory for a very long time. And now not just them but like everyone is sort of grappling with what the other side of the largest network in the world can do.

So I think a lot of Facebook employees are getting defensive, and that’s not to say that all coverage is equally good or valid. I think in any industry, there are people that are bad at their job. And so if I get something wrong or if someone’s piece is entirely wrong, we have to stay accountable for that. So I totally am open to that too. But that’s not how I think, at least.

Jascha Kaykas-Wolff:

Maybe a bit of shift in direction, do you like living in San Francisco?

Mike Isaac:

Yeah, man. I mean, I don’t like making a good amount of money and still feeling broke, but it’s different. I mean, I moved here in 2004, and then I’ve been here on and off since then. So it’s been interesting to watch the change so far.

Jascha Kaykas-Wolff:

Do you live in San Francisco proper?

Mike Isaac:

I do. I live in like the Castro, Duboce Triangle area.

Jascha Kaykas-Wolff:

Do you think you’re going to live here a decade from now?

Mike Isaac:

I don’t think so. I can’t see it just because-

Jascha Kaykas-Wolff:

Back to Texas or Florida?

Mike Isaac:

Yeah, probably not that either. I mean, I think about this a lot. I have a wife and a dog. And so, but we don’t have kids. I’m 34, she’s 30. Bruno, my dog is four. And so that’s our family. We live in a one-bedroom. We have a deal for rent control, but it’s still like not a deal literally anywhere else in the world or country. There is a limit to which we can grow or change our lives. And at some point, unless I go be like head of Comms for Uber or something, which will not happen, but unless I went and did that and made some drastic changes in my lifestyle or whatever, it’s just there’s a point to which I either have to, I don’t know, move to Vallejo, or move out of the city, or something.

Sunil Rajaraman:

Do you get asked to join the private sector quite a lot? Sorry. You know what I mean.

Mike Isaac:

Yeah, yeah, yeah. Right.

Sunil Rajaraman:

Yeah, tech.

Mike Isaac:

The other side?

Sunil Rajaraman:

The other side is what I actually meant.

Mike Isaac:

Yeah. It’ll come in … Yeah, some people make overtures or kind of want to feel me out, and it sort of comes in waves. There was a while where a lot of journalists were getting hired as they call them, I think journalists have like a point of pride that they don’t want to become PR, so they call them like marketing partners or something. But you’re basically PR, which is fine. It’s an entirely legitimate career path. You could do that, but I think it’s just like a pride thing for journalists.

Sunil Rajaraman:

So we’re not going to see you as a partner at a VC fund or-

Mike Isaac:

I just don’t … I’m already like unhireable by my Twitter feed. I’m surprised I still have a job.

Sunil Rajaraman:

No. Clearly not.

Jascha Kaykas-Wolff:

I think you’re looking at this the completely wrong way.

Sunil Rajaraman:

Yeah.

Mike Isaac:

I don’t know, man. I feel like I’ve insulted like every brand that would potentially … I don’t know. I don’t think I would do that.

Sunil Rajaraman:

Is your book coming out before or after the Uber IPO?

Mike Isaac:

Excuse me.

Sunil Rajaraman:

Here, tell listeners a little bit about your upcoming book. How about that?

Mike Isaac:

Yeah.

Sunil Rajaraman:

More context.

Image via Justin Sullivan / Getty Images

Mike Isaac:

So I started writing about Uber pretty much right after I got to the Times in 2014. And I feel super lucky for that. I was probably … It was the middle of Uber’s ascent, probably like the apex of its ascent because it was still on the rise. People sort of like nebulously thought Travis was a douche but not like fully solid. Everyone still was like, “Uber’s cool,” or, “This is great. I don’t have to like wait for a taxi, blah, blah, blah.” And then I got to cover it through the insane period of 2017, and that arc sort of changed. And Travis became this super controversial and … Sorry, knocking things over.

Sunil Rajaraman:

No, you’re good.

Mike Isaac:

Interesting, crazy flawed characters. And got-

Jascha Kaykas-Wolff:

Was he always that? I mean, clearly he was always that. But was it really hidden well, or was it just like the exuberance of all the things that they were doing just kind of masked it?

Mike Isaac:

I think he’s always been like that, man, for years and years and years. But they were able to ride this sort of … Honestly, it was like some of the VC that talk about it was like it was the perfect product-market fit. It hit at the right time. Everyone loved it. People still use it like crazy, even if they feel weird or something about it. But Travis, it worked. And some people argue he was the right CEO that had to go as far as he did until he no longer was the right CEO, and you got to change from wartime to-

Sunil Rajaraman:

Peacetime, yeah.

Mike Isaac:

Yeah, and he only has one mode. That’s what I have discovered over reporting. He only has one mode.

Sunil Rajaraman:

Have you spent a lot of time with him?

Mike Isaac:

No. He is not a fan. And I don’t know if that’ll change. I just don’t think he’s going to talk to me.

Sunil Rajaraman:

Now, okay, so let me-

Mike Isaac:

Which is kind of fun anyway because you have to do your job around someone, which is its own challenge.

Sunil Rajaraman:

Let me try to defend him a little bit here.

Mike Isaac:

Do it.

Sunil Rajaraman:

So you kind of need these mercurial personalities. You have him. You have Elon. You have these people who are just so insanely committed and driven to a mission and to build something like that. Maybe you need to be a little bit off. Not only that, but wouldn’t you say that there is a little bit of a press halo around Lyft, for instance, and around Airbnb, which we just spoke to the SF city attorney about, and sure they’ve made some changes, but they almost took a similar approach, which was blatant disregard for … So what’s your take on that?

Mike Isaac:

No, this is a great question. And I think actually this is where I even kind of maybe defend Uber in a weird way. I think Uber became … Uber and Travis became a symbol for a greater level of angst that people have towards tech in general and a lot of different tech companies. And combine that with the anxiety folks had for Trump being elected and this sort of nebulous idea that Facebook maybe might’ve helped him get elected or tech might’ve had something to do with it.

But people were, and think of late 2016, we didn’t fully grasp what happened with Russia, what happened … Did Trump … Everyone was still trying to figure this out. And this is a scene in my book: The Trump stuff gets melded together almost by accident with Uber in this one moment where the immigration shutdown happens, the travel ban, and someone notices this tweet saying, “Uber’s trying to essentially profit off of people going to the airport.”

And the two become conflated in this moment. And I think it was just a lot of pent-up angst and anger from people kind of at tech but not really sure why. And then they were given a concrete action, which is delete Uber. And people were like, “Fuck, I can’t do anything. I’m angry. I’m sitting at home. There’s this travel ban. What do I do? I could delete my Uber and then take a screenshot and post it.” And then hundreds of thousands of people did that. And it hit the company hard. So I agree with you. I think it’s wider than just them.

Jascha Kaykas-Wolff:

I’m kind of curious about Sunil’s question, and maybe go back after that. You talk to and/or around lots of CEOs for big, powerful companies. Do they all have to be assholes?

Mike Isaac:

I mean, that’s another good question. I wouldn’t say assholes, I think. I think you’d have to be unflinching in your drive and maybe even optimism that you can … You have to be crazy to think you can do some of these things at the scale that they do them. Everything in a startup, and this is the empathy that I have for founders is everything in a startup is like designed for your failure. There are incumbents. This is why Travis hates taxi. Travis hates big government, and Uber was never … was not always as big as it was. They have so much against them. And you have to believe that you can break up these cabals slowly but surely over time.

And that’s why they hate people like me so much, because I just see all the ways you’re going to fail or at least see all the ways that this is probably not going to work out. So I do think I wouldn’t call it like an asshole, you just sort of have to be like in an optimistic version of la-la land to think this is all going to work out.

Sunil Rajaraman:

Do you think that they’ve turned it around with the CEO change? What’s your view of Uber now?

Mike Isaac:

I mean, Dara, so Dara Khosrowshahi, he is the CEO. He came from Expedia. He got installed late last year, I guess. And he’s definitely the right guy to take Uber public. And Uber going public is sort of this big moment for them because they’ve been private for nine years. It’s a bunch of people who want to cash out. They want to just sort of … It’s a big public market milestone anyway. And then normal people can actually get in on this investment potentially.

And Dara is like “the adult in the room,” and I think he actually is. I don’t want to … The hard part too is that he’s very likable if you meet him. And you just sort of have to be careful of that because whatever; they still have similar problems to whether Travis is there or not. They still have-

Sunil Rajaraman:

You’re likable.

Jascha Kaykas-Wolff:

Am I?

Sunil Rajaraman:

Yeah.

Jascha Kaykas-Wolff:

I’m likable? Okay. That’s-

Sunil Rajaraman:

Got to be careful around

Jascha Kaykas-Wolff:

Thanks, Sunil. That’s nice of you to say.

Mike Isaac:

No, I like you. I think, but no, I think he’ll get it across the finish line. It’s more like are the markets going to be receptive to this company, and are people going to buy into ride sharing as a long-term investment?

Jascha Kaykas-Wolff:

Is that the thread in your book?

Mike Isaac:

I think-

Jascha Kaykas-Wolff:

Is that the thread that pulls through the book?

Mike Isaac:

I think it’s more, I think mine is if I have to … I need to start like preparing how to do this in an elevator pitch because I have to sell this

Jascha Kaykas-Wolff:

We’re here for you.

Sunil Rajaraman:

Here we go. This is your chance.

Mike Isaac:

So not looking forward to marketing this book. My elevator pitch would just be the sort of the rise and fall of this idea of the cult of the founder, and the founder knows all. I think this other thing in the valley is like founders can do no wrong, and know everything, and are sort of praised by their boards, by their investors, and given all this leeway. And Zuckerberg for a very long time was like the top example of that. And I feel like Kalanick is the version of that going like drastically wrong when everything bad about capitalism and Silicon Valley startups, is turned into one guy. So I try to follow that arc.

Sunil Rajaraman:

So after this-

Mike Isaac:

Cult of the Founder is a pretty awesome title.

Sunil Rajaraman:

Cult of the Founder, there you go.

Jascha Kaykas-Wolff:

That is a good title.

Sunil Rajaraman:

Good title for a podcast. We should all bring them all.

Mike Isaac:

Yeah, seriously. Then we get you into podcasting.

Sunil Rajaraman:

Yeah. You convert a bunch of founders into a cult, cult of the founder.

Mike Isaac:

Plural.

Sunil Rajaraman:

Yeah, cult of the founders. So let’s just say, all right, you’re satisfied, you’re done with your work on Uber, you’re done with your work on Facebook. What are the next two companies that you would want to cover, that you feel are drastically undercovered?

Mike Isaac:

That’s a good question. I think this is like my life shit, what do I want to do sort of thing. And I’m trying to figure that out too. I think Uber and Facebook are probably two of the most important companies right now. I think Amazon should probably get more scrutiny than it does just because it is so undergirded as a part of our life and like now, I mean, I read a piece the other day about someone who tried to not use Amazon for a week or a month or something. And it was like impossible or at least very difficult.

And so I think the level of scrutiny that they get is kind of surface level because of how many things they have going on. But that would be … I don’t know. You have to make that be fun and interesting, and maybe I could do that. That would be fun.

Amazon sign

Image via Getty Images / Smith Collection / Gado

Jascha Kaykas-Wolff:

Seattle’s not the funnest place in the world to live.

Mike Isaac:

You don’t like Seattle? I like Seattle.

Jascha Kaykas-Wolff:

I lived there for a long time.

Sunil Rajaraman:

I lived there for-

Mike Isaac:

Really?

Jascha Kaykas-Wolff:

It is lovely to visit. It’s awesome.

Mike Isaac:

Maybe that’s why. I only visited. I dated someone there, and I would go like for a week at a time.

Jascha Kaykas-Wolff:

“This is beautiful, and this is amazing.”

Mike Isaac:

It was awesome. Kurt Cobain was here.

Jascha Kaykas-Wolff:

50 sunny days a year.

Mike Isaac:

Yeah. I would probably want to die.

Jascha Kaykas-Wolff:

My wife’s going to kick me when I say that. She’s a Seattle native. I’m like waa.

Mike Isaac:

Where did you live in Seattle?

Jascha Kaykas-Wolff:

A couple places. We were in Queen Anne when I first moved there, the South Side of Queen Anne back before it got all cleaned up, which was pretty cool, and then Capitol Hill.

Mike Isaac:

Oh man.

Jascha Kaykas-Wolff:

Capitol Hill is awesome. It’s a little bit different now. We bought a condo way, way, way back in the day because we were kids, and we still have it. And it’s like the whole neighborhood has completely transformed. We can’t even recognize when we show up there, like, “What just happened?”

Mike Isaac:

It’s probably like the mission now basically. It’s like just very different.

Jascha Kaykas-Wolff:

Yeah, unbelievably different. And now it’s like Amazonville. Back when it wasn’t Amazonville, Paul Allen had started to do some development work downtown. And he was like the I’m the person who is thinking about like commercial real estate and people actually working and living here. And I’m going to do it. And he made all these investments that he never really got to appreciate. But have fun living there. All respect to our Seattle listeners.

Mike Isaac:

I do want to go there, but thanks for walking me back

Jascha Kaykas-Wolff:

Yeah, yeah, yeah. It’s just a personal choice.

Mike Isaac:

You just lost a whole market.

Jascha Kaykas-Wolff:

It’s just a personal choice. Seattle’s great, though. I made bad choices. It happens. So you’re going to release the book. The book is going to come out, sorry, when? We didn’t get that part.

Mike Isaac:

No, it’s next year probably around if not after the IPO. I’m still … It’s sort of … Things are in motion right now. So it was the IPO actually came sooner than … So they were supposed to IPO in September, and they are going to be in like April. So I’m as influx as they are.

Sunil Rajaraman:

Are people at Uber worried about the book? Do you get reached out to by the Comms team there a lot? Or what’s the situation?

Mike Isaac:

I think it’s funny because I have a good relationship with their Comms in that they know I will not be unfair and just set them on fire for no reason. I might set them on fire for a reason. But I think they’re probably like nervous but not like terrified. Part of this whole last year was them sort of self-flagellating and coming clean with all their dirty laundry and being like “We are sorry. Please forgive us. Dara is Jesus come alive, and everything is going to be great now.” So unless I find some crazy dead body in the closet that even they missed, which I might’ve, but I think they are just sort of like trepidation but not terrified.

Sunil Rajaraman:

And are you going to take time off, or are you going to just hop back, just jump back into it?

Mike Isaac:

To go like on the road or whatever with the book and stuff or-

Sunil Rajaraman:

Yeah, so after the book tour, the book sells 1 million copies or whatever it is. Then what?

Mike Isaac:

Oh, I don’t know, man. I honestly, I have no idea. I have no idea if anyone is going to want to read this. I have no idea what’s going to happen. I’m just like, all I’m thinking about is to get it done, get it out the door, cover this IPO, and then … I mean, I literally live my life one day at a time. I can barely get clothes on and come here. I don’t ever know how to.

Jascha Kaykas-Wolff:

He is wearing clothes I swear.

Mike Isaac:

I am naked right now.

Sunil Rajaraman:

This is the first naked-

Mike Isaac:

Making this podcast great.

Sunil Rajaraman:

… podcast where we are in San Francisco.

Mike Isaac:

Yeah. Oh man, I live in the Castro where … Before I moved here, it would probably phase me to see naked people on the street. Now I’m just-

Jascha Kaykas-Wolff:

Not at all.

Mike Isaac:

I’m a San Franciscan. I feel like-

Jascha Kaykas-Wolff:

We’ve got three kids, and our youngest is 10 now. We used to live in Noe Valley, and we would walk through the park. And as we were walking through the park, the beach side of the park where everybody is out in their thongs kind of hanging out, we’d always like walk through the middle of it. Not a big deal. And then or a while there, a bunch of guys that were naked protesting on the corner market and where the main drag there.

Mike Isaac:

Castro?

Jascha Kaykas-Wolff:

At Dolores.

Mike Isaac:

Oh, Dolores. No, no, no. Yeah.

Jascha Kaykas-Wolff:

Wait. What are the streets on Dolores? It’s happening. I can’t remember things. That’s what happens when you get older. It’s going to happen to you someday.

Sunil Rajaraman:

I can’t even remember our interviews this morning.

Jascha Kaykas-Wolff:

And he was like, “Dad, all these naked people, they’re everywhere.” And now it doesn’t even phase him. He’s like, “Man, whatever. It doesn’t matter.”

Mike Isaac:

“It’s Jimmy.”

Sunil Rajaraman:

Another story. So a couple of other questions to wrap up with, and this has been great. I asked this one day to Kara, and I’ll also … I’m not going to tell you the answer. If you could interview any three people, they all agree to a sit-down interview with you, and no questions off-limits, who would they be?

Mike Isaac:

I’m so bad at these. Mine would be totally just from my own sort of.

Sunil Rajaraman:

Yeah. Good. That’s great.

Jascha Kaykas-Wolff:

Yeah, totally.

Mike Isaac:

It would be you know George Saunders? You know the author George Saunders? He’s so good. He’s probably my favorite living author right now—or no, one of them. He wrote a book called Tenth of December, which was a bunch of short stories. Anyway, that’s mine … I was an English major, so I love all that foofy shit. And then I wouldn’t want to do tech because I think I just have tech all the time, and I still get star struck by like real celebrities, like non-tech people. But-

Sunil Rajaraman:

Do people get star struck by you, by the way?

Mike Isaac:

Oh God, I don’t think so. I think it’s more-

Sunil Rajaraman:

Like you could show up to a party, or people are like, “Oh, look, there’s the New York Times reporter.”

Mike Isaac:

I think I’m dumb enough in my public personality that I diffuse any mystique about me.

Sunil Rajaraman:

I’m not star struck right now at all.

Mike Isaac:

Yes, exactly. Totally.

Sunil Rajaraman:

I’m like sweating. My hands are sweating. I’m shaking.

Mike Isaac:

I do get like random … I think that’s the fun thing actually. I do get like random people to come say hi when I’m at dinner or something out here, but it’s mostly my dog. Honestly, people care about my dog more than me. I have a very large Bernese Mountain Dog that I use to pimp my work.

Sunil Rajaraman:

You got two more people that you were supposed to

Jascha Kaykas-Wolff:

And you’re going full celebrity, which is all cool, like Hollywood celebrity.

Mike Isaac:

No. I think it would probably be … Who are my like … It would be some writer.

Sunil Rajaraman:

Or musicians? Musicians.

Mike Isaac:

Oh, yeah. Okay. You know what? I’m a big like Josh Homme fan from Queens of the Stone Age, like a super big fan of theirs. And that would be one, and then probably, oh man, maybe Trent Reznor would be a good one too. He’s very opinionated, which I like.

Jascha Kaykas-Wolff:

Very. Super outspoken.

Sunil Rajaraman:

So not Trump, Chrissy Teigen, or Angela Merkel.

Mike Isaac:

No. I’m not into world leaders.

Sunil Rajaraman:

No?

Mike Isaac:

I don’t know. I just think I would probably go the celebrity route. That’s the other thing. So if I have to move out of here, everyone is moving to L.A. should I move to L.A.? That’s the question.

Sunil Rajaraman:

Yeah. The answer is yes.

Mike Isaac:

Is it?

Sunil Rajaraman:

Yeah.

Mike Isaac:

I feel like there’s haters here that’ll be like, “No, man, it sucks.”

Jascha Kaykas-Wolff:

Clearly.

Sunil Rajaraman:

I mean, it’s nice. L.A. is great. L.A. is in a…

Jascha Kaykas-Wolff:

The commute. It’s just the traffic kills it.

Mike Isaac:

It’s the driving.

Jascha Kaykas-Wolff:

Like it’s any better here. The traffic just kills it. You were like texting me this morning, “I’m going to be late. I’m going to be late.” The traffic here is miserable.

Sunil Rajaraman:

Yeah, but at least it’s predictable. It’s like there’s the 181 and there’s 280. That’s it. There you got like 405-

Sunil Rajaraman:

… 605-

Mike Isaac:

They’re all miserable.

Sunil Rajaraman:

… 105.

Mike Isaac:

Any freeway you get on anywhere in California is miserable, period. End of story.

Sunil Rajaraman:

Yeah.

Mike Isaac:

L.A. is great: great food scene. It’s warm all the time. They don’t have any water. That’s all good.

Image via Getty Images / Mike Windle / Vanity Fair

Sunil Rajaraman:

You know what? I have a good one here. We can’t let Mike get away without answer … So just pretend I’m Travis for a second. Let’s role-play.

Mike Isaac:

Are you going to throw something?

Sunil Rajaraman:

He sits down. He agrees to an interview with-

Mike Isaac:

Oh, I should’ve said Travis, shouldn’t I?

Sunil Rajaraman:

… us or the book.

Mike Isaac:

Yeah, that’s right.

Sunil Rajaraman:

Okay. Let’s just say he agrees. What is the one question that you ask him.

Mike Isaac:

Oh man.

Sunil Rajaraman:

You have one question you can sit down, put it on the record in the book. And you need to know the answer to this.

Mike Isaac:

It would be probably simple, just like do you have any regrets as to what you did or would you change anything over 2017?

Jascha Kaykas-Wolff:

What’s your answer, Travis?

Sunil Rajaraman:

I’m not really going to answer. I wasn’t actually going to role-play.

Mike Isaac:

I thought you were really going to role-play.

Sunil Rajaraman:

No, I’m not going to really role-play.

Mike Isaac:

I don’t think he does, though. I feel like he would just keep maybe like some strategic stuff, but he like owns it, man. And there’s something really, I think he’s … This is what I decided to write about. I think he’s a tragic character. I think he’s like a billionaire now, but he also kind of alienated himself. He doesn’t really have a whole lot of friends. All the people at the top of the company turned on him at the end. And it’s the perfect sort of dramatic arc, but it’s kind of lonely at the top in some ways. So-

Sunil Rajaraman:

Yeah. It’s lonely everywhere. It’s lonely in the middle. It’s lonely on Instagram.

Mike Isaac:

That’s correct.

Sunil Rajaraman:

It’s very lonely on Facebook-

Jascha Kaykas-Wolff:

So this has been awesome, and we have one question that we want to make sure you answer for all of our listeners that we ask everybody. You spend time on Twitter. We know that. Maybe you place time on other social networks. On either Twitter or another social network, what’s at least one person you’d recommend, or company you’d recommend, or brand you’d recommend following?

Mike Isaac:

I mean, so maybe I’ll just do … because the origin of my … So on Twitter, my avatar is a toilet paper bear, the Charmin bear. And I get asked-

Sunil Rajaraman:

I’m going to admit that I didn’t know that until just now, and a light bulb just went on?

Mike Isaac:

Oh my God, did you really?

Sunil Rajaraman:

That’s awesome. Oh, I get it now. I get it.

Mike Isaac:

That’s great. So this is not me officially endorsing a brand, by the way. I think I would get fired for that, but I would say the Charmin toilet paper handle on Twitter is one of my favorites. And I adopted that avatar just because it was the first time I ever saw like a brand that literally you have to like wipe your ass with their product, fully embodying the spirit of it. They would just make poop jokes all day on Twitter. And they were not embarrassed. And I had just found that noble. So Charmin at Charmin.

Sunil Rajaraman:

I get it. I just feel like I get it now. I-

Mike Isaac:

You get me, right?

Sunil Rajaraman:

I get it now. I completely get it. Well, this was awesome.

Mike Isaac:

Cool. Thank you.

Sunil Rajaraman:

This was great.

Jascha Kaykas-Wolff:

Thank you very much for spending the day with us.

Mike Isaac:

No, this was fun. Thanks so much.

Jascha Kaykas-Wolff:

That was fun.

Sunil Rajaraman:

That was a lot of fun. I’m just so surprised by how humble and how accessible Mike is.

Jascha Kaykas-Wolff:

Yeah. I want to hang out with him, and I also want to go adopt a Bernese Mountain Dog.

Sunil Rajaraman:

I do too. I don’t want to tell my daughters that because they’re going dog crazy right now. But I am excited to read Mike’s book when it comes out.

Jascha Kaykas-Wolff:

Maybe if you listened to the podcast and you liked it, you might consider tweeting Mike with your ideas for the title for his book. But I kind of like Founder Cults.

Sunil Rajaraman:

Founder Cults would be a great name for this one. We really hope you enjoyed this interview.

Jascha Kaykas-Wolff:

I always like to end on this too: If you like Sunil as much as I like Sunil, wherever you listen to this podcast, whatever app you found it on, if you rate us five stars, and share that with your friends, it actually helps the podcast a lot.