EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram

In the 32nd episode of Cartoon Avatars former Twitter CEO Dick Costolo discusses his time at Second City with greats like Tina Fey, Amy Poehler, and Steve Carrell, successfully managing and running Twitter as a non-founder, and trying to buy Instagram. (0:00) Intro (0:58) Mark Cuban canceled (4:08) The editing room (6:07) Logan’s engagement (9:22) Welcome Dick Costolo (13:54) Dick’s time at Second City (28:16) After Second City (32:44) Why Twitter is a unique challenge (35:06) Treating all Twitter accounts equally (40:09) Social Media Regulation (42:06) Twitter monetization (44:06) Trying to buy Instagram (48:37) Social media platform Saturn (52:01) Expectation setting (57:10) Leading a company you didn’t found (59:53) Role vs identity (1:02:15) Bill Campbell’s mentorship (1:07:57) Letting people go (1:12:47) Successful managing (1:15:42) Marxist vs Darwinian management (1:19:13) Assume best intentions (1:24:40) Getting unfollowed by Elon Musk (1:30:31) Rapid fire (1:35:14) Outro Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/5WqBqDb... Google Podcasts: https://podcasts.google.com/feed/aHR0... Follow on Socials 📸 Instagram - https://instagram.com/cartoonavatars 🐦 Twitter - https://twitter.com/cartoonavatars 🎬 Clips on TikTok - https://www.tiktok.com/@cartoonavatars About the Show A Saturday morning podcast hosted by Logan Bartlett (Partner and Managing Director at Redpoint Ventures) covering the tech news with his friends and other people with industry expertise. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Logan Bartlett?

  Welcome to the 32nd episode of Cartoon Avatars. I'm your host, Logan Bartlett. I am joined today by producer, occasional guest, TikTok man Rashad. How are you doing today, Rashad? Rashad, I know this is embarrassing. We've been working together for nine months. Assir?

• 0:22Speaker 01

  Yeah, you got it.

• 0:23Logan Bartlett?

  Yeah, okay, that's what I thought. I held off not confidently to say that.

• 0:28Speaker 01

  That's cool. I go by TikTok guy. You know, I'm fine with that.

• 0:31Logan Bartlett?

  Yeah, exactly. That's like actually your moniker at this point. I am embarrassed. We've been working together for nine months and I haven't actually had to say your last name yet.

• 0:40Speaker 01

  It means prisoner of war in Arabic, so.

• 0:44Logan Bartlett?

  Does it actually?

• 0:45Speaker 01

  On fact, yeah.

• 0:46Logan Bartlett?

  That's pretty badass, right?

• 0:49Speaker 01

  Doesn't really suit my whole vibe, but I feel like it. I'll take it.

• 0:53Logan Bartlett?

  I, prisoner of corporate humor, Rashad Assir. Well, Rashad, we took our first week off last week, which I actually, I was a little heartbroken about it. I was pretty proud of like the, you know, the every week releasing an episode streak. And I guess a little bit of inside baseball, we had Mark Cuban set to come on and then he rescheduled. And unfortunately, when you're the owner of the Dallas Mavericks and on Shark Tank and whatever, I'm very much beholden to your schedule. So when he sent me the note, it was like an hour before and I was like, oh, great. I, well, I guess.

• 1:34Speaker 01

  I know. I had done some research. I had learned all about his come up and I was actually planning to ask. I mean, it would have been cool to join even, but I don't know. I guess we'll get him back sometime.

• 1:45Logan Bartlett?

  Yeah, I think we've already scheduled the follow-up. Thankfully, I had done no prep. So it actually kind of worked out, but it should end up being a better, better next episode, but.

• 1:55Speaker 01

  You know what's funny is that the only celebrities I've ever had like an actual exchange with, I don't know about like likes and stuff, but like comments back and forth on TikTok are Joe Jonas commented on one of the first videos that I made that one viral.

• 2:08Logan Bartlett?

  Wow.

• 2:08Speaker 01

  Yeah.

• 2:09Logan Bartlett?

  That's like, that's like a big, Joe Jonas is big. Joe Jonas is big. Would you say Joe Jonas top? Uh, 500 most famous person in the world, probably, maybe 250?

• 2:20Speaker 01

  Yeah, I think so.

• 2:22Logan Bartlett?

  I mean, I guess you throw in the world and like that gets hard, but, but US, US top 250, I would guess.

• 2:29Speaker 01

  Yeah, maybe 500. The aggregate of the three of them, I feel like they're all kind of interchangeable.

• 2:32Logan Bartlett?

  Yeah, yeah, I actually have no idea. Joe Jonas is an amalgamation of all of them, yeah.

• 2:36Speaker 01

  Right, exactly. And then the other one is Barbara, because I've made a couple like Shark Tank videos and she seems super engaged. Like she'll comment, we've gone back and forth a couple of times and uh, yeah, she's super nice.

• 2:48Logan Bartlett?

  That's funny. Yeah, Cuban seems like uh, seems like an entertaining guy. I uh, yeah, that'll be a fun, fun one to do. But bummed to miss an episode, but this week, uh, I guess, I mean, we, we just finished recording with uh, with Dick Costolo, former CEO of Twitter, which uh, which was awesome, super entertaining.

• 3:07Speaker 01

  Yeah.

• 3:08Logan Bartlett?

  He's clearly a funny, witty guy. All his anecdotes about like Steve Carrell and Rachel Dratch and uh, yeah, all those guys uh, working in Second City. Um, it's just, it's fascinating that he just like, worked at Improv for five years or whatever. We'll let people actually hear the interview, but uh, super, super entertaining.

• 3:27Speaker 01

  Yeah, I mean, that definitely makes him an amazing interviewer. His ability to just like off the cuff, share anecdotes and stories. Like, I feel like that's what makes these things super interesting is when you can pull from like, distinct memories from when he was running Twitter and even before that, like was, was pretty amazing. And like his, the Carrell stuff, I mean.

• 3:47Logan Bartlett?

  He was low maintenance too. I actually didn't send him anything in advance, nor did he ask uh, for anything. So that was actually like a hundred percent. I, I would say, I don't know, two thirds of the time I try not to do that. Or maybe just send it right before to let someone react or give him some topics that were gonna hit or whatever. Uh, he, I don't think had any idea what he was stepping into.

• 4:09Speaker 01

  I think I know the answer to this, but like, most of the time, I, I'm sure people are curious like how much editing goes into this. And I feel like we run pretty close to a hundred percent of what we shoot without like, with some ums and ers, you know, cut out. But like, you get a lot of compliance asks or people not wanting to run stuff?

• 4:26Logan Bartlett?

  Uh, no, I, I've never, I kind of haven't been beholden to anyone uh, having edit control. Uh, I've had one or two people. Um, after an episode say, hey, can we, I wish I didn't say that and like cut a tiny snippet at their request.

• 4:48Speaker 01

  Right.

• 4:48Logan Bartlett?

  And then I've had one or two people ask, uh, to go back and listen to it, but not actually make any edits to it. I would say that for the most part, uh, it's any editing is more stylistic editing of just like, hey, that bit dragged a little bit. Let's cut it down by a minute or two, or we've done some reordering. I feel like if there's like a, a topic that we hit at the end that actually they, I feel like we've done that once or twice. The one time that someone really regretted, uh, an episode was, uh, was the Packy, uh, episode after where he was like, dude, that wasn't good, was it? And it was funny. I was like, no, no one's gonna, no one's gonna care.

• 5:33Logan Bartlett?

  I thought it was fine. Right. It was like, meanwhile, that video's still a viral.

• 5:37Speaker 01

  50,000 impressions on Twitter later and I don't even know how.

• 5:41Logan Bartlett?

  Dude, we're in the, we're, we're like on the millions at that point, but I was like, no one's gonna care.

• 5:48Speaker 01

  So I mean, that's probably what ignited the whole, uh, web three debates.

• 5:53Logan Bartlett?

  Oh, I think it a hundred percent did. Oh, yeah, yeah, no, I, I, I don't even think kind of.

• 5:57Speaker 01

  You have Packy, yeah, I guess Packy and Zach on that episode to either blame or think. I guess if people stuck around till now, then think.

• 6:05Logan Bartlett?

  Yeah, exactly.

• 6:07Speaker 01

  Logan, we've got, uh, you, you had some big life news recently. Uh, I thought that the post on Twitter was hilarious. The, I'm not super into college football, but I feel like I got enough of it.

• 6:19Logan Bartlett?

  The joke behind that is so, so for people that didn't see, I did get engaged, uh, to my girlfriend of, or I guess fiance now, girlfriend of three years, Tori. And, uh, the joke behind it is like college football recruits will, uh, like high school, 17 year olds or whatever will tweet out like these commitment, did he, or commitment videos or like infographics or whatever, uh, when they pick what school they're going to go to. And it's always like a hundred, a thousand percent committed, respect my decision, no interviews, you know, whatever. And then it says their school. And so I got, I got someone to edit it as if I was committing, uh, but instead it was, uh, it was her.

• 7:00Logan Bartlett?

  I, I was trying to think of the, like the corniest VC thing I could, I could come up with.

• 7:05Speaker 01

  Oh, there were so many. I read through a couple of the comments on Twitter and they were all, uh, yeah, I forget. Close the deal or whatever it was.

• 7:15Logan Bartlett?

  Yeah, exactly. I was, you know, whenever anyone's like, uh, uh, has a kid, it's always like, oh, we welcomed like a new, uh, investment to the portfolio or something, right?

• 7:26Speaker 01

  Yeah, yeah, yeah.

• 7:27Logan Bartlett?

  I was trying to think of like what the corniest one was and it was like, oh, I signed the forever term sheet. You know, like something like that. That's just like so cringe.

• 7:37Speaker 01

  I think you made the right call ultimately going with the call Logan Vols, the much, uh, your Finsta basically at this point, but.

• 7:44Logan Bartlett?

  That's right. That's right. I, I only had two things that define my personality. One is being a VC and the other is being a college football fan. And like, I, uh, I, I went with the college football fan one for this one.

• 7:56Speaker 01

  What about the, that there was this wall, I'm remembering it from either Instagram or something where there was like a bunch of business cards of, was that like a restaurant thing?

• 8:05Logan Bartlett?

  Oh yeah. Gosh. Uh, yeah. You're, uh, so I, I, uh, I had, I saved a bunch of stuff from, uh, restaurants we went to or whatever. And then one of our friends, uh, turned it into a, uh, a collage for, uh, for us. So it came out pretty cool. It's, uh, it's sitting out there. I guess maybe we'll put a picture in here of it. Um, but it's, uh, yeah, it was cool. Same business cards, game tickets, uh, hotel keys. So we've got like Logan VC. We've got Logan Vols and then this is like romantic little rom com Logan. We didn't know that. That's right. That's right. I, I don't know who would play me, uh, in, in the rom com, but yeah, no, that's the, uh, that's the other version of it.

• 8:49Logan Bartlett?

  It's, uh, hopefully it's not that it's not, uh, I always got, uh, Will Forte is who I've, who I've gotten the most, uh, in terms of like celebrity doppelganger. Um, and so I, you know, I don't know if Forte does rom coms or what, but, uh, it seems like a reasonable ask.

• 9:04Speaker 01

  Fun man. Well, congrats.

• 9:06Logan Bartlett?

  Thank you to a, uh, to, to a wedding. Uh, I guess I'll probably take off that, uh, that week as well. So that'll be the next time I take off is the, the wedding week, uh, here, but, uh, yeah.

• 9:17Speaker 01

  Maybe we'll do a guest host situation.

• 9:20Logan Bartlett?

  That's right.

• 9:20Speaker 01

  Me versus Zach.

• 9:22Speaker 02

  What's happening?

• 9:23Logan Bartlett?

  Dick, how are you, sir?

• 9:25Speaker 02

  Good. How are you guys?

• 9:26Logan Bartlett?

  Good. Good. Thanks for doing this.

• 9:28Speaker 02

  Happy to.

• 9:29Logan Bartlett?

  You know, I've watched like every interview and podcasts I could find of yours over the course of the last like Yeah, no, it's a lot. You're like, uh, there was a while there. You were like a professional talking head while being a CEO and, you know, you end up getting a lot of content out of that.

• 9:48Speaker 02

  I would be afraid to go back and watch any of that.

• 9:50Logan Bartlett?

  You know, there's two hours and 20 minutes of you and Sarah Lacy talking to one another and that led me down a rabbit hole of like, what happened to Sarah Lacy? You know, like, once upon a time, I, uh, it seems like she just kind of checked out.

• 10:02Speaker 02

  I'm not sure. I haven't spoken to her in forever.

• 10:04Logan Bartlett?

  She used the term shit show to describe Twitter to you quite a few times and you did it. You were very noble, in the entirety of the interview, um, just kind of, uh, passing on that, but she, uh, she, she does it with a smile, uh, and like good, good natured laughter, uh, but I mean, this is really, this is July 8th of 2014. So we're really going way back.

• 10:26Speaker 02

  It's always been everybody's favorite company to trash.

• 10:29Logan Bartlett?

  I feel like, uh, I feel like there's, there's two requisites of what I found, uh, in, in any conversation that people seem to have with you of any length. It's one, you're actually, I don't know if you know this, but before I sent across the invite to schedule, you actually have to ask about Second City and improvs and all that and like Rachel Dratch and what Steve Carrell like, like, it was, it was in the terms of service of you coming on. So that's like, that's like one. And then two, you have to like, kind of throw some negative, uh, shade at Twitter as a product. It's like, you have to do both.

• 11:07Speaker 02

  When I took over as CEO in October 2010, we had already been, the Twitter, the Twitter logo, the bird had already been, um, executed on the cover of two magazines that this is 12 years ago. 2010, I think it was business 2.0 and like fast company. It was, it was hanging itself on business 2.0 and it exploded on fast company or something. And you know, the death of Twitter, um, it's funny, you know? It's just crazy. It's been like, it's always been like that. That was before I took over.

• 11:41Logan Bartlett?

  I kind of want to know what like, in your opinion, why all that's the case, but uh my, my first and most important question, what was the closest you actually ever came to deleting your first tweet? Like, there had to have been one moment in there, because everyone brings that up as well, right? Every single time?

• 11:57Speaker 02

  Well, I just always thought like, all that stuff's already out there, you know? Who cares?

• 12:01Logan Bartlett?

  It seems to boomerang back around, though. Every time Twitter makes the news for some way, like, you know? After Parag takes over, it boomerangs back around and then Elon Musk.

• 12:11Speaker 02

  Yeah, it doesn't matter. I've been searching for my name, you know? And it was like typed it into the search, the UI, the first web UI was, this is like 2007, I think. The first web UI was like, oh, that's not the search box, that's the tweet box. Well, whatever, of course.

• 12:27Logan Bartlett?

  Yeah.

• 12:27Speaker 02

  14 years later, it's like, how come you didn't? It's like, well, it was very different back then. Anyway, what are you gonna do? You can't, it doesn't matter, you know? Who cares?

• 12:37Logan Bartlett?

  You actually don't even need to set alerts if like something's happening with Twitter? Like, you just know that tweet's going viral again? It's just like, it's like, oh, great. What's going on uh with the company? That thing's recirculating at this point.

• 12:49Speaker 02

  I, I live most of the time in Napa now. Um, I moved up here during the pandemic. I woke up the morning that the, I guess, the first um Elon news came out. And I looked at my phone and it just had my mess, you know, I always clear my messages. I had like 49 text messages. And I just immediately knew like, uh-oh, something, something happened. Something happened to Twitter.

• 13:14Logan Bartlett?

  You're like, someone died or, or?

• 13:19Speaker 02

  Or something happened to Twitter.

• 13:21Logan Bartlett?

  Yeah, exactly.

• 13:23Speaker 02

  One of those two things. Or somebody, yeah, it's exactly right.

• 13:27Logan Bartlett?

  Well, I guess, I guess someone dying, you probably get like one uh text or like a call me, call me text?

• 13:33Speaker 02

  Yeah, call me. One call me text. No, I knew, I knew it was, uh-oh, something, something happened.

• 13:41Logan Bartlett?

  Yeah, well, I I'll try not to ask you the I want to play back some of the the more, I don't know, different, interesting stuff, but I appreciate you doing this and Adam nudging nudging this along. I guess maybe to level set. What can you just give a quick primer on your your background? Even though I've heard it from every podcast interview you've ever done over the last two weeks. So I could probably do it, but maybe maybe from your words, it might be better.

• 14:10Speaker 02

  Sure. I born and raised Detroit, Michigan, family is all automobile industry folks, dad, grandfather, cousins, etc. Went to University of Michigan, studied computer science and graduated with a CS degree. Decided that I didn't want to take any of the job offers. I had to go be a programmer. And I went to Chicago. And and I started hanging out and and and going through the Second City Training Center and then performing at Second City because I wanted to get on Saturday Live. Actually showed up, as you will have heard from other interviews, I showed up at Second City the same day Steve Carrell did. So Steve and I were in the went through the whole Training

• 14:54Speaker 02

  Center together and and perform when when we first started out performing, perform there together in the same group.

• 14:59Logan Bartlett?

  Could you tell, by the way, with Carrell at that point, like, could you tell you had a star quality?

• 15:04Speaker 02

  Yes, but yes, but so the yes, but is I became friends with, you know, a bunch of those folks who were all there at the same time. Rachel Dratch, Adam McKay, who went on to direct a bunch of the Will Ferrell movies and the Big Short. All those all those people were there. And it was some, you know, it was amazing. You operate Citizens Brigade was formed at the time. So Amy Poehler was there and all those guys and Tina Fey was there at the same time. It was just amazing. So you could tell that Steve was you could tell that he was great. I mean, he was always a great improviser. He and Tina were like remarkable improvisers. But the big but is there were a number of people there who were world class good. And

• 15:46Speaker 02

  you always thought, man, this person's going to be like straight to SNL and films and everything else. And I would say that the people who

• 15:55Speaker 02

  All of us thought were maybe the funniest, you know, are people who didn't make it for one reason or another. Um, either they did their, you know, they auditioned for SNL and they're like, we already have a fat guy, you know, I think like, or we, you know, we already have the, the straight guy. We already have Will Ferrell who plays the, you know, straight guy or whatever. Um, so just all sorts of random reasons, you know, Steve auditioned for SNL a couple of times and didn't get it, you know, he, um, he ended up going and kind of grinding and, and got the Dana Carvey show, but then that got canceled and got, was a roving reporter on the Daily Show and then finally got, um, for, you know, Judd Apatow cast him in Forty Year Old Virgin and then it was off the races. It got the office after that.

• 16:38Logan Bartlett?

  Has that informed a little bit of like your perspective to investing now? Just like you see this randomness associated with greatness and like Correll had to grow. I always think about like George Clooney, you know, and breaking through at like 42 or something. And the lack of linearity in the acting world of careers where you're like Jon Hamm and it's like, I'm this handsome, charismatic, good actor who at 38 like has nothing to show for it. Right. It's this very weird lack of linearity in profession. I think it would drive me insane, but did that actually inform like your investing mindset that like, hey, you know, even if all this talent aligns, you still actually have to get really lucky with things?

• 17:17Speaker 02

  I think it's informed more than just my investing mindset. It informed my mindset about everything. Like it informed my mindset about the fact that when you're like the CEO of a major company and you're in the news every day and you know, and whatever says you're, you know, some, I don't know, Vanity Fair puts you as, you know, you're number eight on whatever list. Like you just, it informs like, hey, man, this could be anybody. Like I could be, this could be, this is randomly me. It could be anybody. I am lucky to be here. Just gotta, you know, keep my head down and keep going. And so I never got like,

• 17:53Speaker 02

  I never got like too wrapped around the axle on any of that stuff just because I yeah, it informed the fact that man like it's just a you know it's you need to be working hard and need need to be um doing everything you need to do but then you also need to be a little bit lucky so that always helped keep me grounded I think.

• 18:12Logan Bartlett?

  Yeah, it's interesting. Now, now Second City for people that uh don't know it, uh I guess I sort of grew up in the watching the Bill Murray's or the Chris Farley's or the I mean Tina Fey's as well uh of the world from a comedy standpoint but it it's brought through so much talent in SNL specifically improv that broad right was there some formula or like structure to it obviously there's these compounding network effects that exist with something when it becomes a brand like that like SNL has like Sequoia Capital has right or whatever it is but like or was there anything unique to it?

• 18:49Speaker 02

  No, the it had it had the impact that it had was everyone knew that was it was kind of a little bit it was you you couldn't really yet use the groundlings as an on-ramp to SNL at the time I was there it wasn't really a big deal yet in LA so Second City which is um for people don't know it this famous improv comedy um theater in Chicago was the place to go you know so um Dratch and Tina came in from the East Coast there were people who came in from the West Coast lots and lots of people from big 10 schools ended up coming there Steve I think had gone to college at Denison went right there so anyone who was trying to get

• 19:31Speaker 02

  work their way onto SNL who wasn't doing stand-up and you know this is like again it's improv theater not stand-up um came to Second City um just because they all knew this is this the path to get to get to SNL and this is where SNL will cast most of its cast from and and they did.

• 19:49Logan Bartlett?

  Got it. Was there, so there are all those precedents of John Candy. I mean, I guess Candy wasn't on SNL, but Chris Farley and Belushi and Bill Murray and all those guys, I think were all SNL people.

• 19:59Speaker 02

  Yep. They were all Second City.

• 20:01Logan Bartlett?

  And they were all Second City as well. And then there was that next generation.

• 20:05Speaker 02

  Rachel, Tina, Amy Poehler, you know, a bunch of the other UCB founders, Matt Walsh has been quite successful on Veep. Again, Adam McKay, Dave Keckner, who is in Anchorman with, that Adam directed as the sportscaster with the cowboy hat. All those people were at Second City at the same time. It was amazing. And you know, and Correll and lots of that, lots of Steve Colbert. We were all there at the same time. It was, it was funny because it was like, really the second big heyday of Second City. When you're there, you're, at the time, you don't think of it, you're not looking around going, this is the heyday of Second City, but it, but it was.

• 20:45Logan Bartlett?

  Yeah, it's funny. You like calibrate to like, I'm the, I'm the lower mid of the pack, right? And it turned out, well, the lower mid of the pack is actually like on SNL as well, right?

• 20:55Speaker 02

  Yeah.

• 20:56Logan Bartlett?

  Full calibration thing. Was that, was that just a unique moment in time that the stars kind of aligned?

• 21:02Speaker 02

  I don't even know. It was just like, we were just kind of all doing our thing and not really, you know, it's like when you're doing it, you can't really, you don't really have a sense of, this is like, these are, these are the funniest people that we're, that will ever come through here. You're just like, you know, you're grinding away and you're all trying to figure it out and make it. I did know when you would see McKay on stage, or, or, or Correll, or Tina, you know, you would just think, you would be in the audience, you know, any, any of the other improvisers in the audience, you'd just be like, wow, that was, I don't know if I could have, I don't know if I would have, I don't know if I would have been able to do that, or I don't know if I would have, you know, been able to come up with that. Just amazing, like just genius improvisers and really.

• 21:47Speaker 02

  Always on and always great. Like when they would come on stage, you'd know, I mean, this will be like, pay attention, this will be good.

• 21:53Logan Bartlett?

  Yeah, that's interesting. I have a handful of friends that you just sort of, they have a celebrity star quality to them. And I'm not really sure if they're ever actually going to end up being celebrities or stars in their own right. But you sort of know that like when they walk in a room, they just have a presence about them. I think people have always sort of described like Bill Clinton as that way that he sort of just captivates a room. And I can imagine that these people just have to be so quick on their feet. And well, I guess that's an interesting point. Like in improv itself, is there any trait that like spikes them? I mean, being funny, obviously, but like, is there anything that you found was uniquely consistent across the people that actually made it?

• 22:33Speaker 02

  No. The people who are good improvisers are not planning ahead what they're going to say. They're just literally, really in the moment and going with the flim, whatever, reacting to whatever's been said. And they're not like thinking ahead. They're just coming, saying what comes next to them and it comes up. And but there's nothing, there's nothing that you can, there's nothing you could define as a characteristic you go learn or a trait you could train that would teach you to help you be one of them. There were just people like, you know, and again, talk about, you know, you may or may not know these names. I mean, Eric Hoffman and Jody Lennon, who are also at Second City in the Annoyance Theater, they were another two people who would get on stage and everyone would go, okay, be

• 23:16Speaker 02

  quiet. Like, stop, no more side talking. I want to watch this. Because they were just like, you knew it was going to be one of the funniest things you'd seen that night. And to be able to do that consistently in improv is, you know, crazy hard.

• 23:28Logan Bartlett?

  Yeah, it's an interesting analogy. And I've heard you draw this in the past, but like, not pre-planning thing. Like, if you end up being too scripted, I have my notes, I want us to improv this, but I have my notes up in front of me. So not all of this is from my mind. But if you end up being too scripted, you just, and that's of your career, that's of like a conversation with someone else. Like, it sort of loses the element. I remember one time I was doing this and I was like, well, let's, we don't, we can Cut and we can break and like, let's just try to put the best of it together. And it was so awkward and it just, it was a total disaster. And so I actually had the guess, we both went and grabbed a beer.

• 24:08Logan Bartlett?

  And we're like, hey, let's throw all that out. Let's start over here because of the awkwardness associated with it. But I guess it's a kind of interesting analogy to your career path that I've heard you draw in the past. So, so you did this for five years-ish?

• 24:23Speaker 02

  A while, six, five, six, seven years, something like that. Yeah. I had a lot, had a few auditions. I just didn't get anything. And so I was like, all right, I gotta like, go get a real job.

• 24:33Logan Bartlett?

  What was the closest you came?

• 24:35Speaker 02

  I mean, I had, I mean, the closest I came wasn't very close. Had auditions for SNL and, and Mad TV, which was another sort of sketch comedy, a scripted, a sketch comedy thing on TV like SNL, um, back in the day in the, in the nineties. Didn't get either of those.

• 24:52Speaker 02

  You know, you have to get, for SNL to get it, you, after first auditions, they'll call a select few people to New York and do readings on set with cast members in New York. And I didn't, I didn't make it to that point. Um, um, you know, and, and if you, if you did, it was, you had a much better chance of getting cast, obviously. But even, even if you did, you didn't, it wasn't a, it wasn't a guaranteed thing. Um, so I didn't get very far. And after a few of those, I was like, all right, I gotta go get a job.

• 25:20Logan Bartlett?

  Yeah. Well, I mean, I don't know, a lot of, a lot of famous people came out of Mad TV as well, right? I think Artie Lange and Keegan, Michael Key or whatever his name is. Uh, and you know, there's, there's a handful of, I mean, those are, you, you, you're, you're pretty modest on, uh, you came close to like two of the iconic things, I think. Out there, but I, uh,

• 25:43Logan Bartlett?

  So you were part timing at the, uh, you were doing some packing at like a Crate and Barrel or?

• 25:50Speaker 02

  No, I worked in, I worked behind the register at Crate and Barrel because I had to have like odd jobs where I could. You know, we would perform at night and then rehearse during the day. So you're like, all right, well, I can't get a full-time job where I work regular hours during the day. And I can't get a full-time job where I work regular hours at night. So I had to have odd jobs. You know, you don't make any money performing in the, I don't know what they make now, but you just didn't make any money. Even if you kind of made it to the main stage at Second City, there are sort of three or four different casts. Um, before you're on the main stage.

• 26:22Logan Bartlett?

  And so, so you're sitting here thinking, I have a CS degree from Michigan.

• 26:26Speaker 02

  Like I was working in a coat check room at some club in random hours. And this guy in my graduating class in Michigan like comes in and hands this coat to me and recognizes me. And you could tell it's like, oh man, like what happened? I think he thought I was like a meth addict or something like, oh man, he's really, things really went south for you. It's only been like 18 months. What happened?

• 26:46Logan Bartlett?

  Yeah. What substance did you get into in between here and there?

• 26:50Speaker 02

  Yeah, right.

• 26:51Logan Bartlett?

  Was that like a, okay, I guess it was only 18 months at that point. So, so, uh, was there any moment that you were like, all right, now I gotta go, I'm gonna go get a, a real job?

• 27:00Speaker 02

  No, it was only after the, I mean, you know, you just didn't have it. I remember just the constant stress of not having money was a drag, but I was just grinding it out. And, and I thought like, well, I'll just keep, keep it going. But once I, once I auditioned a few times, didn't get it. I was like, all right, like this was getting ridiculous. I've been here, you know, six, seven years, I gotta go get a job.

• 27:21Logan Bartlett?

  Do you look back with like some nostalgia about that moment in time? And you're like, I didn't know any better. I was just, you know, I was just poor and trying to make it around funny people and all. Or is it kind of like, gosh, my life is so much better now. I'm living in Napa and you know, bouncing back and forth. What, which one Eric?

• 27:40Speaker 02

  No, I don't have any, I don't like, I've never had that like, I don't know, I'm not one of those people who ever was like, God, weren't those, those were the best years, you know? I'm not like, I just don't think that way. I don't think that way about anything. I've always felt like, man, this next year is going to be amazing. And I don't have that, but I also don't have any regrets about it. I mean, it was, it was. You know, crazy. Again, you ended up being there in the heyday of Second City, which we didn't know at the time, but those people were all, they were all great and all like so fun to be around.

• 28:12Logan Bartlett?

  Yeah. Yeah. So, so I know I cut you off in the middle, but thanks for going through all that. So, so you did that. You said, all right, I'm going to go get a real job. You went into consulting for a little bit.

• 28:21Speaker 02

  I went to Anderson Consulting and worked in their technology services division, which is basically means you're not a consultant. You're just working in the headquarters on software.

• 28:29Logan Bartlett?

  Got it.

• 28:30Speaker 02

  Well, then the internet took off and I quit there and started my own company doing, you know, built one of the million of web design companies that was doing basically web design for hire and development. I'm going to from there started, you know, I started several companies, one of which was Feedburner, which we started in 2004, sold that to Google in oh seven, worked for Susan Wojcicki on, on the ads team. Susan, before she was CEO of YouTube, was basically ran, ran all of ads for, for, for Google on the product side. And is great. I loved working for her. She's so, she's a great executive. She's no nonsense. She's super common sense.

• 29:12Speaker 02

  She doesn't get emotional about stuff. She's calm, thoughtful. I think she is fantastic.

• 29:18Logan Bartlett?

  And she's still running YouTube today, right?

• 29:20Speaker 02

  Yeah, she's still CEO of YouTube. I just think she's a super underrated executive and probably doesn't get enough credit for how good she is.

• 29:27Logan Bartlett?

  And you dovetailed at that point, your, your career crossed again with Ev Williams, who you, in the past.

• 29:34Speaker 02

  Yeah, he was at Google where they had sold Blogger with Biz Stone and Jason Goldman and some of those other guys. When they were first looking to acquire Feedburner, so I got reacquainted with him. By the time we actually got to Google, Ev and company had left and started Odeo, a podcasting company, which was just a little bit before its time, obviously. And then, and then pivoted to Twitter in, in oh, in oh six. And then when I left, when I left Google in July of 2009, Ev basically reached out and said, hey, would you,

• 30:18Speaker 02

  you know, be interested in, in coming here for a few weeks when I take parental leave and kind of wash it over the fort for a while? And I said, sure. And then before that even started, he called me back and said, hey, what if, you know, what if it was more of a full-time COO gig and the rest is history?

• 30:34Logan Bartlett?

  And so, so you were COO for a little while, then ultimately?

• 30:36Speaker 02

  A year.

• 30:37Logan Bartlett?

  A year and then became CEO, which, you know, whatever has been chronicled more than enough. And then you had five-year, uh, five-ish years. Is that right?

• 30:46Speaker 02

  Five, five, five and a half. I think it was like five and a half. Yes.

• 30:49Logan Bartlett?

  And took the company from zero in revenue to two and a half billion.

• 30:53Speaker 02

  Two and a quarter.

• 30:54Logan Bartlett?

  Who's counting?

• 30:55Speaker 02

  Well, yeah, we took it from zero to two and a quarter billion in five and a half years. And that was at a time we were fighting, you know, where we were second fiddle to Facebook. It's one thing to go from zero to a billion that fast and zero to two and a quarter billion that fast. It's another thing to do when you're like, you know, everyone you're trying to sell to is like, well, I can buy those same ads on Facebook for much better, you know, um, cost per transaction and cost per click, whatever, you know, cost per interaction. And so, um, it was a grind, you know, that was, um, I had all credit on that stuff to Adam Bain, who I had brought in shortly, um, after I got there as COO to be, um, basically, you know, president of revenue and, and build out the entire Boto Market

• 31:39Speaker 02

  team. And Adam's just, um, you know, Adam was, um, at Fox Interactive in LA and nobody in, I shouldn't say nobody, most people in the valley didn't really know him. Um, and I remember I told, you know, I told Evan on the board, hey, we should hire this guy from Fox. And they were all like, Fox? What? What? Like, no, he's great. Um, and he was, and he was, um, so all credit to him on that front.

• 32:05Logan Bartlett?

  Hey, now I've heard him described as the nicest person in Silicon Valley. I've heard, I've heard him referred to.

• 32:11Speaker 02

  He gets all the credit for being nice. What he doesn't get enough credit for is he literally knows everybody. You could get off a plane with him in Guinea Bissau and the, you know, the baggage guy would be Bain, you know, like, hey, like, oh, the heck. Like everywhere you go with him, you're like, how in the world do you know this person? But anyway, but that's, I mean, that, that's what, it's one of the reasons.

• 32:35Logan Bartlett?

  There's a reason makes for a good partner right now and when you're investing in companies and all the stuff you're up to today. But before we go there, and I do want to go there, what, what question that I can't, I can't pass on asking as an avid Twitter user as well. Like, what do you think makes a uniquely hard business in a way that, I don't know, Facebook's different, Instagram's different, and Snapchat's different? Like, it seems to have this uniqueness of like, difficulty in scaling and monetization and a bunch of stuff that I think is maybe not entirely unique to Twitter, but kind of has its own challenges. What do you think that is?

• 33:14Speaker 02

  Um, well, um.

• 33:17Logan Bartlett?

  By the way, I know we've only blocked, like, we need to keep it under a couple hours, so I, I, no need, not all of them, the short version of it.

• 33:26Speaker 02

  Um, I'm not sure it's so much different. I just think that, um, you know, it's, uh, you've got everyone who works in media and writes about technology and writes about media is on the platform, talking about technology and talking about the environment we work in on that platform. And, and, um, social media has, has the distinct problem of, of trolling, which hasn't been successfully addressed.

• 34:05Speaker 02

  And trolling and the amplification of trolls and the ability for trolls to be trolls, which I continue to think is just

• 34:16Speaker 02

  solving and addressing that more aggressively would go a long way toward tackling. So let's set aside monetization for a second, and I'll come back to that, because I think that's important.

• 34:27Logan Bartlett?

  Well, you know, on the Twitter side, to give Twitter credit or blame, uh, there's more anonymity on Twitter and text is the means of communication, which is easier to, I think, troll rather than, I mean, Instagram comments, you know?

• 34:44Speaker 02

  Yeah, yeah, yeah, I agree. I remember I told Hunter Walk when he was running YouTube product, I was like, why do you guys have? Before I was at Twitter, I think I was like, why do you guys have comments? They're all just horrible on the videos.

• 34:55Logan Bartlett?

  Yeah.

• 34:55Speaker 02

  Burn them off. They're stupid. The most people are just like this. Most of the comments are just like either first or this is stupid. Why do you do this?

• 35:03Logan Bartlett?

  And you're like, what if, what if that was the whole company?

• 35:06Speaker 02

  I remember telling him, you should just turn these off. So the challenge is, I just think that the idea on all these platforms that users should be treated the same, and in fact, you know, the, the, um,

• 35:21Speaker 02

  the frequently promoted belief that we should treat every user equally, I just think is a naive idea. Like, why should you treat

• 35:33Speaker 02

  the Washington Post account the same as an account that was created one day ago with an unverified email that doesn't have a phone number attached to it? Like, why would, why should those be treated equally? Like, why should they show up? Why should they both be able to respond, you know? And why should they both be given equal weight in, in, in a conversation thread? And the, the companies are getting better and better about that, obviously. Twitter's done a, a much better job about weighting things in search and weighting things in responses and weighting conversations. But, um, you know, they should be also weighted differently in the way you think about, you know, whether you're going to suspend some account or not. Like, the idea that, well, we're gonna, you know, we're gonna apply these rules equally to every single account just strikes me as like, it's not, it doesn't work.

• 36:16Speaker 02

  I mean, I remember again, the example, I, I think I used this example of Kara Swisher when she was asking me about like, why don't you just do X? Everyone's always got a, why don't you guys just do this? You know, and it's some stupid, simple thing that they think no one's ever thought of. Um, but I think it was, I might get this, I might get the specifics about this bit off, but I think ISIS had, um, had a journalist in a cage and they like, you know, burned him to death, lit him on fire in the cage and burned him to death. And, and posted those videos and, and photos of those things to Twitter and YouTube and everyone else. And when I found out about that morning, I was like, all right, well, obviously we shouldn't suspend all those accounts. They're like these terrorist accounts. Let's just, if you post that video, you're, or retweet it, your terrorist account,

• 37:01Speaker 02

  delete the account or suspend the account. And then we, you know, um, my general counsel came to me and said, hey, the New York Post is using that as their cover of their, you know, New York Post tomorrow. And it's, they just posted that thing to Twitter. And I was like, oh, right. Well. Don't delete, don't suspend the New York Post account. That, that's a bad idea. Well, it was, it was really the day I would remember learning like, okay, we should really have to stop treating these things as rules you apply equally to everything.

• 37:32Logan Bartlett?

  And then people will say, well, just do what's illegal. And it's like, all right, well, a beheading video isn't illegal, right?

• 37:38Speaker 02

  The problem there is the rules are different. You know, everyone says use the First Amendment. Like, Germany doesn't have the First Amendment.

• 37:43Logan Bartlett?

  Yeah, First Amendment to US.

• 37:46Speaker 02

  Germany has a tweet about Nazi stuff and you don't take it down, you're violating the law and we're going to arrest your people who are working in the Berlin office. So you have to, you know, you have to adhere to the laws in the countries in which you operate. Then, but then you also have to be careful not to, you know, to protect the privacy of your users as much as you can. You know, there would be people in places like Turkey or Pakistan or wherever that would tweet things, you know, anti-government things. And we'd get these requests that were, hey, give us all the information about this user or we're, you know, gonna arrest you if you ever land and, you know, uh, if you ever land in, in, in Pakistan. Um, and, uh, you know, then you're like, okay, well,

• 38:27Speaker 02

  we're not just gonna hand over our user information either. So there's constantly, you're constantly battling this like, all right, well, we need to adhere to the laws in the countries in which we operate, but we're not gonna just, you know, kneel down and hand over information to the government of India or the government of Pakistan. Uh, you know, uh, so, but I, but long story short, on the, on the just health of the platform, I just think that all of these companies need to be a lot more aggressive about, hey, we're not gonna treat all the accounts equally. And, you know, these things are subjective. Um, we're just gonna have to, you know, have some common sense rules about trolling we're gonna remove. Um, and I think it has to, it has to be as apolitical as possible. It shouldn't be like,

• 39:11Speaker 02

  We're going to apply these social justice rules. It should be like you can't, you know, if you start swearing at somebody or telling them they're, you know, um, you know, I'm going to kill you or, you know, whatever, like, you know, we're going to delete your account.

• 39:22Logan Bartlett?

  I think there's some inherent issues with social media in general, and one of which is like, what might make sense in near-term incentives, uh, might actually be problematic for the

• 39:32Speaker 02

  Of course, 100%.

• 39:34Logan Bartlett?

  And then also, might not be good business in the long term.

• 39:37Speaker 02

  Totally.

• 39:38Logan Bartlett?

  Is, is probably.

• 39:39Speaker 02

  Notifications are the classic example of that. Like, hey, let, if we notify people that this thing happened, they'll use the platform more. And that works great, right up until they turn notifications off because they stop, want to stop getting alerted about everything that happens on the platform. I mean, there's, so there are a bunch of things like that. This is going to work great and drive engagement, right up until the point, I mean, you could make an argument that Facebook has been the textbook case of, they do everything they can to drive engagement and it's ruined the platform.

• 40:09Logan Bartlett?

  Yeah, exactly. It's sort of like, you know, measure, you'll manage to what you measure, and wherever those incentives exist, like, suddenly that's where the OKRs are going to be managed towards, and then that's the business you're going to build. But, so, do you think there needs to be like a regulation for some of these businesses as like, utilities in some way?

• 40:31Speaker 02

  No, because they'll regu, like, what's, give me an example of like, government regu, I don't know, it's a bad way to go with this. There's, the chances that, all you have to do is go watch the questions that the House of Representatives and the senators asked of Zuckerberg and Susan Wojcicki and Jack, to know that they have absolutely no idea how to regulate these platforms, and would do the wrong thing.

• 40:54Logan Bartlett?

  No, I agree. I mean, the level of sophistication on some of these questions are obviously tough there, but there are elements, I feel like, of, uh, utility that exists i- in some way, like, when you're starting to, uh, when you're starting to litigate who can have access to a Twitter account, or who can have access to a Facebook account. I guess the question, I, I like your common sense rules and all that. The only question that I, I have is like, who, who is the arbiter of, of common sense, right?

• 41:22Speaker 02

  Yeah, I know. I get, I mean.

• 41:26Speaker 02

  Facebook in many ways had the genius move of we're going to punt it to a third-party organization that we put together that also will have that also has no idea what they're doing, but at least tonight and go, hey, ask those guys, they're the ones that make the rules.

• 41:38Logan Bartlett?

  It's great. If the senators in Coggy, like, yeah, you're right. They don't know what you're doing, but then it's not your problem.

• 41:43Speaker 02

  I don't know. It's got to be the people, you know, ultimately, it's the CEO of the company has got to have a team, but they put together that's making some common sense rules and trying to stay away from the politics of it. I think some of the things have gotten way too, like, as I said, some of the things that people are getting suspended for are a little too, like, social justice warrior for my taste, but, but I'm not running the company anymore, so I don't get to make those decisions.

• 42:06Logan Bartlett?

  You said two things on the engagement side and then the monetization side. What was the monetization point?

• 42:11Speaker 02

  Well, on the monetization side, I just think the company, um, you know, we bought a data, a data company when I was CEO called GniP, um, that has become the data business for Twitter, and that's a great business. It's a great nine-figure business and has grown quite successfully since, since we bought it. I just think that, you know, um, were it me, and it's not me, so I don't get to, you know, I don't get to decide, I just would have, um, liked to have, I would like to see it, um, fork out into some, you know, have to have some different business models on top of not get rid of advertising on Twitter. I just think it's been, it's been very successful, but you would like to have a couple other

• 42:51Speaker 02

  lines of business, um, by now. I'm always hopeful, um, back in the day that Fabric, um, the, the mobile platform, um, that ended up getting sold to Google, uh, would become this a SaaS platform, uh, for us and, and do well and make money. And I think Google's doing pretty well with that now. Um, but, you know, the company decided after I left, like, hey, Dick's trying to do too many things, um, we're going to focus and shut some of these things down. And, you know, the market, the market likes that stuff in the near term because it drives profits and shareholders love that.

• 43:22Logan Bartlett?

  Fabric was, uh, it was Crashlytics and a few other things, and then Speciallytics, and then they had Jeff Seibert, who came over and then ran, uh, was the CEO of that and came and ran Fabric for us. It was basically, um,

• 43:35Speaker 02

  Um, a mobile login, you know, using, using phone number login for your, so you could use your app to do both. We could, you could use fabric to do all of the beta testing for your app. Instead of test flight, you could use fabric to do, you know, hey, we're going to have mobile login using fabric. We're not going to have to build our own login and identity. And then all the, all the, all the crash and crash, crash analytics, analytic stuff as well. So it was a mobile development platform that just made launching a mobile app a lot easier.

• 44:01Logan Bartlett?

  Interesting.

• 44:01Speaker 02

  And Google, Google still runs it and it's quite successful and we have a bunch of portfolio of companies that use it.

• 44:06Logan Bartlett?

  Yeah. Was there anything you look back on? Just, I know you like looking forward and don't think, but like any, any one thing that would have done differently or like?

• 44:15Speaker 02

  Well, I mean, you know, I famously tried to buy Instagram in March of, uh, um, February and March of 2012, um, and, and made an offer to Kevin and Mike, um, that they didn't accept. And I was in a hotel in Tokyo and woke up in the morning to the news that, um, market bought it for, I think it was a billion dollars, 700 million of Facebook stock and 300 million of cash. I was like, oh, man.

• 44:44Logan Bartlett?

  Yeah.

• 44:45Speaker 02

  Man, I would have gone to JP Morgan and I think my, I think our offer, I'm going to get this wrong because it's a while ago, but I think our offer was like 10% of Twitter, which at the time was 600, 650 million dollars. And I was like, oh, man, I would have like called JP Morgan and asked to borrow, you know, 350 million dollars to give you, you know, to match the offer or make it, make it spend more. But that, you know, they didn't, Mark wisely, I think, knew about the conversations we had had with them. And wisely, uh, you know, said, hey, um, you know, you need to take it or leave it. And the offer expires in this amount of time or something like that. And such that they couldn't go out and shop it and we didn't get the chance to do that. Obviously the internet would be a lot different.

• 45:29Speaker 02

  If we had had then Instagram, Vine and Twitter, um, and that would have been text and video and, and photos and that would have been great, but it didn't happen.

• 45:40Logan Bartlett?

  What do you, what did you see? Cause people made fun of Facebook, uh, at the time.

• 45:44Speaker 02

  The moment they bought it for a billion dollars and everyone was making fun of them for buying it for a billion dollars. We were all like, oh man, we're like super outflanked right now. Um.

• 45:53Logan Bartlett?

  But they had only been a market, how many, they, I think they had.

• 45:57Speaker 02

  They, I think they had eight employees. They didn't have an Android app yet. They had eight employees. But it was just, you can see these things when they start to go. It was, here's the deal. Kevin, Kevin is Systrom. Kevin Systrom is an amazing product executive. Might be one of the best. I think he and Evan Spiegel are probably two of the best product CEOs. I just think they're both consumer product CEOs. I just think they're both great. Their ability to see the right, the right question to ask and the right problem to address with the solution that they launch, um, is just, I just think it's, there aren't many people like that.

• 46:39Speaker 02

  And I remember, um, people saying like, oh, it's filters. Anyone can do filters on photos and it, but it wasn't filters. It was, they've made it easy by just making every photo the same square format.

• 46:56Speaker 02

  Um, and not having to go deal with camera, you know, this camera nonsense. They've made it easy for everyone, everyone to take beautiful photos and make everything they're doing look amazing. And they've turned, and they've made that a feed and it's going to be like, of course, everyone's going to use, of course, everyone's going to want to use that. And then it's exactly what happened. Even though it didn't look like that at the time, when they bought it for a billion dollars, we knew they'd gotten it. They, we knew it was a steal and we wished we had had it and would have paid, would have borrowed the cash to go make the same offer. Um, and, and.

• 47:31Speaker 02

  You know, it was obvious to us that that was going to work and that Kevin was amazing and could be super successful inside a company.

• 47:37Logan Bartlett?

  Yeah. And for people that don't know all, like this was uh, reported contemporaneously. This isn't just pure revisionist history. Uh, like I think there was a lot of reporting at the time that you guys had this regret. I forget if Nick Bilton covered it in his book or whatever, but like even at the time now it looks like, oh my God, what? Like, how did that possibly happen? But even then you guys were like, oh shit.

• 48:00Speaker 02

  We knew it and we were like, oh, I mean, I was, I woke up in a, in the hotel in Tokyo. I got the news and I was like crestfallen. It's like, oh man, we're gonna wish we, we're gonna really, really, really wish we had had that.

• 48:13Speaker 02

  It wasn't like, it wasn't for lack of trying. We're like taking them out to dinner, you know, going to meeting them at this hotel. Going back out to dinner again, bringing this board member up to dinner. I just couldn't, you know, couldn't, couldn't punch through.

• 48:27Logan Bartlett?

  Yeah. Well, it's obviously worked out for, uh, for them where they, they land or I guess philosophically, depending on how you think about it, it either worked out or didn't, but it's certainly been very successful within Facebook. Have you had that lightning in a bottle, sort of like insight where you've seen around either something now that's not patently obvious or another company that had come up over the last couple of years that you're like, oh my gosh, this reminds me of that.

• 48:49Speaker 02

  Well, I'm talking my own book now, but I'm, I'm wearing the T-shirt actually Saturn. It's a, uh, social media platform, um, up, built around the calendar for a high school or a high school students. It's a calendar-based social platform, essentially like you, you know, here's my school, here's my, here's my schedule. Um, and it matches that to your friends' schedules in, in school and it's, um, an event-based social network, basically.

• 49:14Logan Bartlett?

  It goes in at a user level and kind of integrates with your calendar and allows for chat among your friends and like a bunch of stuff at the high school level.

• 49:23Speaker 02

  Yeah, exactly. And then you know, you can imagine, um, um, it will at some point be open beyond high schools, but the two founders, Dylan and Max are, um, they would just remind you of great, you know, they're just, they're great. They're great. They're, um, They're not satisfied with, you know, whatever success they're having. Um, they constantly are thinking about and working toward, how could this be better? How could this be grow even more quickly? How could we make, how can we make it more safe? How can we learn from the, you know, the mistakes that these other platforms have made in the past? And make sure our platform doesn't have uh this kind of bad behavior on it. And I think they're already doing an amazing job of that. And they remind me of the Collison Brothers um in the

• 50:08Speaker 02

  in the way that the Collison Brothers didn't just accept like, well, this is the way it's always been done. Or Patrick's like, you know, well, who cares? That's not the way, well, that's doesn't mean it's the right way to do it. Um, so they're just, they've got that great like, well, what do you mean? Why, why do the lawyers, why do lawyers tell you have to do it that way? I don't want to do it that way. Um, so they've got that just great curiosity about, and you know, you know, they might end one of the things that people who do that do is they eventually, they inevitably try to go reinvent HR. And then after like a year, they find that wasn't, it wasn't worth going and trying to reinvent HR. But you know, great, like go trying to rein, going and trying to reinvent stuff that's broken is a smart thing to do and some of it will work and some of it won't, but that's fine.

• 50:53Speaker 02

  So these guys, Max and Dylan, remind me of the Collison Brothers in that way.

• 50:56Logan Bartlett?

  You just tripled their next round, by the way. That's like, uh, what is it in Step Brothers where it's like Fergie mixed with Jesus? That, that's like exactly what you just did for these guys in their next round, so.

• 51:05Speaker 02

  Well, they're both also super smart, you know? Remember I had dinner with Patrick and John right before COVID, the Collisons, right before. Um, so it must've been around like January 2020, so right after the holidays. Um, right before COVID and we're having dinner in downtown San Francisco. And they're talking about Christmas presents and Patrick was like, yeah, I got John the history of accounting for Christmas. And I started laughing and they looked at me and they're like, what's so funny? It's great, you should read it.

• 51:35Speaker 02

  They're just like, you know, they're on another, they're on another level of like curiosity and like the history of accounting, like I got, there's too much to do to go. But they love it.

• 51:48Logan Bartlett?

  I'm glad there are people like that out there in the world, uh, doing that stuff.

• 51:52Speaker 02

  No, it's a testament to their curiosity about stuff and how they're willing to go like, there's probably some interesting lessons to learn here. And that's why they've been so successful.

• 52:01Logan Bartlett?

  Hey, one thing, the, the Twitter experience makes me think of, of like, you guys, uh, it was, it was interesting where when you were at the helm with public at a time that you were like the darling, among a few other darlings at the time, but high valuation. And I think has been covered with this whole Elon Musk saga of how much value has been created and all, all of that stuff. Um, did, did that change your opinion about, uh, when to go public or how to go public? Or expectation setting and going public, or what you can do in the private markets versus public markets? I guess it just makes me think about talking about the Colisons as well, who are famously kicking the can on going public.

• 52:45Logan Bartlett?

  Although we're a very happy portfolio company. We love you guys, Sean and Patrick. If you ever, if you ever see this clip, I just keep doing your thing.

• 52:54Speaker 02

  Uh, yeah, there, it's definitely the case that if you're taking a company public for the first time, there's a bunch of things you don't realize that it would be good if people like were more helpful about in, or more forthcoming about and, and helped you understand more. For, for example, um, I just, I mean, there's a ton of things. So I would, if I had it to do over again, I would have definitely spent more time understanding the importance of communicating, um, constantly, um, post IPO, uh, to retail and the sell side. Um, because if you don't, uh, you know, the people who are short the stock are out there working the journalists constantly.

• 53:38Speaker 02

  And you're like, ah, just gonna, you know, look, we'll let the results speak for themselves. But they're out there working the, working the journalists and, and working retail and working the sell side. And you, you, you need to be doing that. CEOs who do that, I remember early on, Benioff, when Salesforce went public, Benioff would go on like Kramer on CNBC. And, you know, talk about Salesforce. And I remember thinking like,

• 54:04Speaker 02

  Why is he going on, why is he going on CNBC and talking to Jim Cramer about Salesforce? His company is like gonna work or not gonna work. It's not gonna really matter.

• 54:11Logan Bartlett?

  It's like you're selling B2B. Why, you know?

• 54:15Speaker 02

  He was super smart. He just got the street and retail investors in the sell side to like, here's my story. I'm gonna keep telling a story over and over and over. It's gonna be the same story every quarter. And here's where we're going. This is why I'm doing this. And the people who say this don't understand, don't understand these other three things that I know that they don't know. And I just, and it was super smart and successful and the right thing to do. And I am constantly advising people like, don't think when the roadshow is done, you're, you know, you're done spending time with the, with the, with retail investors and reporters and everything.

• 54:53Logan Bartlett?

  But you did a good job. I mean, I guess the revenue ultimately caught up to, well, you could say it was inflated. There was almost too much hype initially behind it, right? And then the revenue has caught up to it. And so in some ways, I guess, would you have, like in doing that, let's say you did that and worked the, the audience a little bit better there? Do you think the revenue multiple would have held up better throughout that period? And so it would have led to better employee retention or like what would the impact? Or would it just, you would, your kids wouldn't have had to hear their dad yelled at on television as much as they did or whatever?

• 55:36Speaker 02

  I don't, I have no idea. That's the short answer. I think that, you know,

• 55:41Logan Bartlett?

  Yeah.

• 55:42Speaker 02

  When it went up to 75, like two months after it went public, I was like, this is like insane. The price to revenue ratio is insane. We've got, we're even growing 100% year over year. Like we're trading in a multiple now that's, you know, greater than.

• 55:57Logan Bartlett?

  It was like, what, 75 times or 100 times reminiscent, reminiscent of some of these SaaS companies recently, by the way.

• 56:03Speaker 02

  Yeah. It was just at a, at a, at a, at a multiple that wasn't, you know, was, was obviously crazy. I mean, it was going up like $5 a day while, you know, where it was. Holiday break, um, uh, 2013, like December, end of December, um, and it was closed around 75 end of the year. I remember getting back January, beginning January 2014 and sending my assistant like, man, we got, we, what's gonna be, this is gonna be a hard next six months. We got a lot of work to do and we're the multiples priced to, you know, executing what we've said we're gonna do to perfection and apparently a bunch of things that we don't even know about that we need to do, uh, and get started on is that are starting to make your money on. So we just,

• 56:48Speaker 02

  you know, the, the thing that again, I would go back to that, um, um, would be helpful for the company is to have, you know, more than just the advertising, uh, line of business and the data business that we started and, uh, that we bought and started and is doing quite well now. And a platform business likes, like a fabric or something else would be great.

• 57:08Logan Bartlett?

  Yeah, uh, makes, makes a lot of sense. Um, one thing I guess that, that, that sort of brings up or makes me think about as well is, uh, you were leading a company of which you were not the founder, right? And I, I think similarly Jeff Weiner was around the same time doing it for LinkedIn as well. And Eric Schmidt did it for Google with, with Larry and Sergey still, still around. But was that, um, was that challenging in its own right? Cause like I sort of think about this now where at Redpoint, right? I inherited things that someone else started. And so I'm perpetually worried when I'm like fucking around on Twitter or something. Am I actually,

• 57:51Logan Bartlett?

  am I changing the brand that the founders wanted our firm to have and therefore like it sort of leads to some paralysis if you think about it too much, right? And like willingness to, hey, this, I didn't start this thing. And so you feel this, this John Sculley with, uh, with Apple thing of like, I need to shepherd this rather than take the risks. Did you ever feel that or were you able to sort of push through it?

• 58:17Speaker 02

  I felt like I had to run it the way I would run it. Like you can't be, I always would tell my managers at Twitter, like, Don't pretend to know answers if you don't know the answer. Like, the worst thing you can do in, it's gonna create misery for your team is if, you know, they ask you a question, or that you need to make some decision, and you're acting like you know the answer, and you don't know the answer. Just say you don't know the answer, or like, I don't know, or say like, I don't know, what do you, let's, let's talk about it, what do you guys think we should do? Like, when you, when you, when you try to be someone you're not, or know something you don't know, or act like something you, you know, that you don't understand, it just creates misery for, for everybody, because everyone sees right through it. So, I felt like I had to run the company the way I was gonna run the company, and that was different than the way probably anyone else would run the company, and that didn't

• 59:02Speaker 02

  bother me at all. But, I always knew, I'm not the founder of this product. Like, you know, Ev and Jack and Biz are the founders of the product, and they'll always be the founders of Twitter. I'm gonna be the CEO of Twitter for like, five, six years. And, then there'll be someone else to be, it turned out to be Jack, but then someone else will be the CEO, but you guys are always gonna be the founders of the company. So, and when you speak to the employees, and I, I tried to have them speak, you know, frequently, come and talk to the team frequently. They were on stage with me in New York, and in front of the company in San Francisco the night of the IPO, I wanted them there, you know? Like, this is your company. I'm running it right now, but it's your company, you created it, you gotta get on, you know, you gotta get up here and talk to the team.

• 59:48Speaker 02

  Cause you guys speak with the fluency, you know, the fluency of the founders of the company. And, so, and that actually helped me a ton also, in, in my personal life, cause I would get, you know, when I was running Twitter, like, you know, you'd get invited to things that you wouldn't get invited to if you weren't CEO of Twitter. I remember I got invited to the Oscars one year, and I was like, I'm not, I was like, I'm not gonna go, and my daughter was like, what do you mean? You know, you gotta go. Like, uh, I wanna go to things I'm invited to because I'm Dick Costolo, not because I'm the CEO of Twitter, cause eventually I'm not gonna be the CEO of Twitter, and I don't wanna like, hold on to the job, so that I get, because if I don't have the job anymore, I won't get to go to the Oscars.

• 1:00:33Speaker 02

  So, I'm just not gonna go to things that... The CEO of Twitter is invited to, I'm gonna go to things that Dick Costolo is invited to.

• 1:00:39Logan Bartlett?

  Did you pass on going to the Oscars?

• 1:00:41Speaker 02

  Yeah, I didn't. Yeah, I passed on a bunch of stuff.

• 1:00:44Logan Bartlett?

  I don't know if I, I philosophically hear and agree with what you're talking about. I think the Oscars, I would.

• 1:00:49Speaker 02

  Well, I wouldn't pass on the Super Bowl invitation from the NFL. I protected that that was for Dick Costolo.

• 1:00:56Logan Bartlett?

  Yeah, yeah, this is, this was sent.

• 1:00:57Speaker 02

  It's not Dick Costolo in the chair. It didn't say CEO Twitter.

• 1:01:00Logan Bartlett?

  Yeah, that's right. That's right. Uh, that's interesting.

• 1:01:03Speaker 02

  I just mean generally speaking, I tried not to like, you know, get my identity too wrapped up into the role.

• 1:01:11Logan Bartlett?

  Yeah.

• 1:01:11Speaker 02

  It just, that's how, that's how these things start to go. That's how these people start to go off the rails.

• 1:01:16Logan Bartlett?

  Totally. And that's where ego starts to play.

• 1:01:19Speaker 02

  Yeah, you're like the smartest guy in the room. It says right here on this invitation.

• 1:01:23Logan Bartlett?

  Yeah, exactly. That's right. That's right. And then everyone, because that's one of the things when I switched, I was at a boutique investment bank that a lot of people hadn't heard of at the time and, uh, and it's a boutique investment bank. So you're doing sell-side advisory. And so most of the time, people haven't heard of you. It's end of life service because you're giving advice, right? Uh, at the end of selling a company. And then I switched over to VC and like suddenly I was funnier and smarter and like more entertaining. And all I did was switch my domain address, like all it was, you know, went from Logan to Logan at, at, uh, the VC firm. And it's amazing. Like everyone treated me, my jokes were better and I was far smarter and all that.

• 1:02:05Logan Bartlett?

  And being cognizant of that fact of like what your role, uh, is versus who you are, I feel like that could lead, uh, if you're not careful, it can lead to you going crazy.

• 1:02:15Speaker 02

  Yeah.

• 1:02:15Logan Bartlett?

  Now, one thing that, uh, Bill Campbell was a mentor of yours, who I've always been fascinated by. What, for people that don't know, Bill Campbell's like the consummate, I think CEO coach, right? I mean, he coached, uh, Steve Jobs and Eric Schmidt and Larry and Sergey. And I, I don't know, you probably know the list better than, than I do at this point. But basically everyone that was important from, you know, some point in the Silicon Valley to today-ish, right? Uh, he was kind of, and recently passed away a couple of years ago. Is that right?

• 1:02:45Speaker 02

  He passed away a few years ago.

• 1:02:47Logan Bartlett?

  Yeah.

• 1:02:47Speaker 02

  Was, so he was, he was an executive vice president at Apple. And then when they spun Claris software out of Apple, Bill became CEO of Claris. Um, and that's going ways back, obviously.

• 1:02:59Logan Bartlett?

  Yeah.

• 1:03:00Speaker 02

  Well, he was, um,

• 1:03:03Speaker 02

  In the in the 2000s, he was on the board of Apple. He was Steve's, he was Steve's friend, Steve Jobs' friend, but also on the board of Apple. And then he was Eric, Larry and Sergey's coach at Google. I think John Doerr at Kleiner had brought him in there. He was at Twitter when I got there, and he was working with us and the executive team at Twitter. Bill was, he was called, it was called Coach Campbell, but he was called Coach because he had been the coach of the Columbia Football Team. And so he had, so he wasn't an executive coach in the traditional sense of like, you know, psychologist, or, you know, lie down on the couch and tell me, you know, why you hate

• 1:03:45Speaker 02

  your board. He was much, he was more of a like, management practices and leadership and like, don't tell people what to do. Stop making all the decisions. You know, I remember my first sort of staff meeting in my direct reports as CEO. It's like, we gotta like, really work on the cadence of how, how, how, how the company, how fast the company is moving and pace of execution and everything. And made a bunch of decisions in the meeting and got out and thought I was super, super impressed with myself. And I was like, what did you think? And Campbell goes, stop making all the decisions. I was like, what? He's like, let me tell you a story. When I became CEO of

• 1:04:25Speaker 02

  Claris, Donna Dubinsky, who had left EVP role at Apple, came with me. And after the first two weeks, I was CEO at Claris. She came up to me and said, hey, Bill, if you're gonna keep making all the decisions, I'm gonna go back to Apple and you can hire someone, you have to pay a lot less money, it's too much job. He's like, you know, don't tell people what to do. It's just, give them ownership of the problem and create the own, create the solution for themselves. Otherwise, you're gonna be a bottleneck for everything. And, and if the thing that you tell them to do doesn't work, they're just gonna sit there and wait for you to tell them to do what next, instead of figure out what the solution is. And, you know, push everything, to push decisions down the stack and only make the decisions that only the CEO can make. He was just great at that kind of stuff.

• 1:05:03Logan Bartlett?

  It's

• 1:05:04Speaker 02

  No, it's no nonsense. He swore all, he swore all the time, which I found hilarious. He was constantly swearing.

• 1:05:10Logan Bartlett?

  That, maybe that's why I've heard Lorne Michaels doesn't like that on interview.

• 1:05:14Speaker 02

  He doesn't like it at all. And one of the, one of the funniest, talk, going back to Saturday Night Live, one of the funniest auditions in Saturday Night Live history, who's, who I will not name to protect the guilty, um, was crushing it in his SNL audition, um, and had the audience, including Lorne and Stitches, and then came out and did a third monologue, um, of Rush as impersonating Rush Limbaugh, but swearing constantly. And that was it for him. Never got called back.

• 1:05:44Logan Bartlett?

  Has this person, is this person famous, uh, today?

• 1:05:48Speaker 02

  Um, nah.

• 1:05:50Logan Bartlett?

  Yeah, got it. Wow. Bill Campbell not gonna be on SNL. Wow. Yeah. Um, well, so, so what, um, so like what, was it just an intuition of how to read people and how to like?

• 1:06:01Speaker 02

  He was, he was pretty, he was, I think he was, he was, um, strangely, I say strangely because it was non-obvious that he was like this. He was strangely high EQ. Like he would, he would tell you something about, you know, he would, he would come in after talking to someone on my team for a half hour and say, and I would say like, a person's, you know, amazing, right? They're great at blah, blah, blah, blah. And he would say, yeah, but, you know, they're, they're this, this adjective. I don't go like, man, I don't see that. He's like, yeah. At some point, you know, you'll, you'll see it. I think it's going to cause a problem a little bit down the road.

• 1:06:41Speaker 02

  And then like literally three years later, you know, um, that exact thing would blow up. And it happened, that happened on two or three occasions. Um, so he was just,

• 1:06:52Logan Bartlett?

  Yeah.

• 1:06:52Speaker 02

  Swallow people that's.

• 1:06:55Speaker 02

  Super high IQ and the thing about Bill is he liked to actually sit in on all the meetings, but also would kind of, but also would kind of like armchair quarterback in the back, which bugs me, you know, he would like, I'll sit on management team meetings now, but I just, I literally say like, I'm just gonna sit in the back of the room and observe and take notes, just trying to help you guys create more efficient meetings. I'm not gonna say anything, please don't look at me and ask me questions. That was not Bill. Bill would let go, you know, if he didn't like some, if he liked something someone said, he would go clap, like sitting there trying to run the meeting going, oh, God. So it, there was, you know, there was, it wasn't all wine and roses. There were some like, hey, can you not clap?

• 1:07:35Logan Bartlett?

  Yeah, or not call that person a fucking idiot or whatever. Yeah. As the case may be, no, that, and, and he, uh, he gave some interesting advice. And I know there's been a book written about him on, on like, you know, some of the advice that he's given or leadership lessons and all that. But I think he gave you some specific advice on how to give bad feedback to people. And then also the, I don't know if this is him, but the two by two matrix of communication.

• 1:08:02Speaker 02

  Well, the two by two thing is Kim Scott, who wrote the book Radical Candor and I, um, did all that. Bill was like very, Bill's, Bill's whole thing was really forthright communication. Like, don't tell people what, don't manage by trying to be liked, you know? Managing by trying to be liked is just gonna create misery and is the path to ruin. Doesn't mean you have to be an asshole. Doesn't mean you have to be a jerk. But like, don't tell, you know, Logan A and then tell Matt A prime, you know? Don't tell Logan like, hey, Logan, uh, I went into that meeting with the CEO and, you know, was able to get you that pancake you wanted, you know, congratulations.

• 1:08:44Speaker 02

  You get to have the pancake out there and then go tell Matt, Matt, nobody wanted you to have that pancake more than me, you know, you know, hopefully next time. People go out and talk and you know, obviously is a stupid example, but this happens all the time. Someone, someone comes in and like, hey, I don't want to work on internal tools anymore. I want to build a new feature. I want to build user features. And like, if I can't work on user features, I'm going to quit. You know, and instead of saying like, hey, man, internal tools are literally the highest leverage thing anyone in the company can be working on. It makes all the engineers, you know, more productive. It's the most important thing to work on the company. Instead, they say stuff like, just keep doing it for whatever, some version of, look, just do it a little more longer and then I'll go talk to Dick or, you know, everyone needs to rotate

• 1:09:29Speaker 02

  through this. Maybe just another eight weeks and then I'll try to get you on the so and so teams. Doing stuff like that just creates, then people end up quitting anyway and just creates misery.

• 1:09:39Logan Bartlett?

  Yeah, I think the, the specific thing I think I credited to him in listening back, uh, but was when giving bad feedback, just have it written down exactly.

• 1:09:47Speaker 02

  Yeah. Yeah. That's correct. He did. He did tell me that and it's great advice. Bad feedback or worse, like write down what you're going to say and make those words come out of your mouth. Right? It's true. He was like, when I had to give really negative feedback, I would write it down a few days before when the meeting wasn't like an hour from now. And then I would sit down with the person and make myself say exactly those words. And so that we're communicating as forthrightly as possible.

• 1:10:16Logan Bartlett?

  One of my friends is a, a CRO of a company and has had to fire so many people over the years, right? Just like, that's kind of the job when you manage lots of salespeople. And I was like, how do you do that emotionally? Like, how do you deal with this? And he was like, listen, Logan, the first thing I do is I tell them that we're going to have a hard conversation and then I get the words out of my mouth. You're going to be moving on. And it was like, once you say that, then you just read the script and say whatever you want. They're not going to hear anything else. Like, once you get through that, you're kind of in the clear because they're, they'll be thinking about their family or the next steps or what they're going to hit, punch you in the face or whatever they're thinking, but they're not thinking about exactly delivering the message. And I was like, oh, that's interesting. Like, just

• 1:11:00Logan Bartlett?

  get those words out of your mouth, which is so hard, especially I think inherently I have a bias to like, try to be, uh, Friendly and try to try to get through a conversation and antagonize people. Whereas I have friends, a co-host on this podcast occasionally, Zach Weinberg, who's much more willing to be an antagonist to people. And it just, you know, stylistically, you got to sort of know yourself in dealing with people and giving feedback and all that stuff.

• 1:11:27Speaker 02

  Yeah, I, I, um, I remember I had to let somebody go with global operating responsibilities. So I was like, wait a minute, I like people in Tokyo are going to be asleep and people in Europe, it'll be night. If I do it at night, the people in Europe will be asleep, the people in Tokyo. I was like, trying to figure out, okay, I have to like, let this person go. And then there has to be a communication, sort of a waterfall of who tells who what.

• 1:11:54Speaker 02

  And David Rosenblatt on my board, who had been the CEO of DoubleClick and is now the CEO of First Dibs. He's like, oh, I had to do that. I actually had a schedule that a half hour by a half hour schedule for the day of what went down. I can send it to you. It might be helpful. I was like, oh, it's great. Yeah, please do. And the only thing I remember about the sketchful is it's at, you know, 6:30 AM, wake up in a cold sweat. And when I remember thinking like, it's so, it's so helpful to see that and just realize, oh, I'm not the only one who's like, this is just absolutely. You know, you can't tell the person you're firing, this is hard for me too. You know, you can't do that.

• 1:12:30Logan Bartlett?

  Totally.

• 1:12:30Speaker 02

  Horrible, but it's just horrible. It's like the worst day and you're like, oh God, this is just sucks. I think people don't realize, you know, some people don't realize like it's hard for everybody. You just have to fight through it and realize it's going to be, it's going to be a bad day.

• 1:12:47Logan Bartlett?

  One thing that I've, I've heard you talk about as well, and I, I, I texted back and forth with Ryan Sarver. This, this morning before you were coming on, just about like his experience working with you and Twitter and all that. And he gave you a ton of credit for upleveling the management style within the company and just how professionally Twitter actually operated. And I think you taught a class internally or something.

• 1:13:10Speaker 02

  Yeah, I did. Ben Horowitz had a class at CloudFlare managing it, not CloudFlare, geez, LoudCloud, CloudFlare.

• 1:13:18Logan Bartlett?

  Ben, Ben.

• 1:13:19Speaker 02

  Ben Horowitz from Manreesh Horowitz.

• 1:13:21Logan Bartlett?

  I don't know.

• 1:13:23Speaker 02

  Don't know him?

• 1:13:24Speaker 01

  Never heard of the guy.

• 1:13:25Speaker 02

  Never heard of him? It's a different Ben Horowitz.

• 1:13:27Speaker 01

  Yeah, okay, got it, got it.

• 1:13:29Speaker 02

  Ben had a class called Managing a Loud Cloud and I was like, that's a great idea. I'm gonna do that. And what happened was I had this engineer come up to me and he's like, uh, should we have one on ones with our manager at Twitter or not? And I was like, I said, well, I mean, I have one on ones with my directs, but why are you asking? They kind of asked it in this very pointed way. And he said, well, I was on the ads team and on the ads team, we have one on ones with our engineering managers and I just transferred to um, platform engineering and platform engineering says we don't have one on ones at Twitter. Anyway, that was a real eye opener for me because I began to realize that everybody managed based on wherever they had just come from. If you know, you'd come from eBay, you did this. If you came from Google, you did that. If you came from Facebook, you did this other thing.

• 1:14:15Speaker 02

  So I built this managing a Twitter class and it was about six hours long and it was, you know, communicating, um, decision making, uh, you know, um, not, again, not managing by trying to be like, making sure everybody understands what you understand, you know? Make sure everybody has the context for decisions that are made.

• 1:14:36Speaker 02

  Doesn't mean you have to, it doesn't mean it's a Freedom of Information Act. You know, you don't have to read a transcription of the meeting that happened, but help people understand, hey, it was a tough decision as to whether to do A or B. And, you know, we talked about it for a while and decided to do this for these reasons. You know, that's just make sure everybody understands what you understand. Then people are walking around knowing how to be successful in their roles, knowing how to be productive in their work and then knowing what that success means for both them and the company. And that's hugely valuable. I think Ben says, Ben said basically the same things in his outline. I just changed the contents of it mostly to be stuff that was relevant to stuff we were doing at Twitter. Improving your team, making your team better, you know, also a bunch of the stuff we've talked about like.

• 1:15:19Speaker 02

  Don't try to be, it's not your job as a manager to be omniscient. People think they get promoted to manager and then have to have all the answers. Like, again, you think you're gonna spit, if you're spitting people, they, and you think they don't notice, you're, you're mistaken.

• 1:15:31Logan Bartlett?

  Yeah, well, I'm gonna credit you with it, uh, for, forever henceforth, uh, the, the Dick Costolo, uh, model of this, uh, versus that Ben guy, whoever that was.

• 1:15:41Speaker 02

  Right, fine.

• 1:15:42Logan Bartlett?

  What are the other things you said, uh, uh, what about Marxist versus Darwinian management? I think, I thought that was such an interesting, uh, mindset because it's, it's, it's inherently, uh, I think the gravitational pull would be towards more Marxist management of people, but actually what you want to do in a company is more Darwinian management. Can you talk a little bit about that?

• 1:16:03Speaker 02

  Yeah, it's not, it's not dissimilar to investing. Um, Marxist management style is like, well, these three people are lagging behind. They need to go spend time with them and help them like catch up to the other kids and make sure they're, you know, to each, Marxist method of management is to each according to his needs and going and spending time with their sub performers to try to elevate them and get them to be as, you know, up to some adequate level of performance. And what you want to do is improve the entire team. And the way to improve your entire team is to invest in the people who are performing. You invest time and energy and effort into the people who are performing and make them, help, help them make themselves even better and help make them even better. And that's how your whole team gets better. Um, it's, I think

• 1:16:45Speaker 02

  good investors would sell you the same thing about their portfolio. Man, I gotta spend, I gotta spend time with my winners and understand like what we can be doing to help them do more and what I can be doing to help them do better and try to spend time with the one that's really lagging back here and limping along and barely gonna make it to the, you know, halfway mark is just not gonna get me anywhere and not gonna be what delivers returns to my investors.

• 1:17:06Logan Bartlett?

  Definitely. I mean, it's one of those things you feel, uh, inherently.

• 1:17:10Speaker 02

  Sorry, I'm interrupting you, but like, that's not naturally the way things will go, right? Your top performers are like, I don't need any help. I'm kicking ass. And your poor performers are like, wanna talk to you every two hours. So you gotta, you know, you have to, you have to, don't necessarily just be in reaction to who spends, who wants to spend time with you, but be much more, um, active about spending time with the top performers and making sure they're getting what they need, even if they don't need time with them.

• 1:17:34Logan Bartlett?

  I use as an analogy, I'll always bitch about like Camden boards or Asana or Trello or Smart Sheet or Monday.com or whatever, because for the most part, and I'm sure there's ways you can figure this out, but like for the most part, the to do item shows up in the same text size and the same font and the same like, you know, screen size it's taking up when the prioritization of how you should spend your time is ultimately wildly disproportionate, right? Of like what those tasks are. And so I, I have people internally at times will like use these things to track and it's like, well, that's, that's fine, but we should actually resize this one thing to take up

• 1:18:14Logan Bartlett?

  the entire screen, right? And all these other things should exist in a very small line across the bottom, because that's how you should prioritize your time. And again, when you, when you work in these task management systems, I totally get why. I mean, they, they serve a really good purpose. But if you, if you're too indexed to like just, just knocking off tasks, you're going to lose sight at times of like what's actually impactful or important to your job.

• 1:18:40Speaker 02

  Yeah, 100% totally agree.

• 1:18:42Logan Bartlett?

  Now, what about, I know you're not managing a big company at scale, but one of the things you've, you've got yourself in, I don't know if trouble is the right word, but culture and, and managing, you know, your whole self and all of that stuff. We don't need to rehash the specifics of, of that. But how do you think about, obviously you don't have to run a company today and dealing with people and their political or religious or ideological views and all of that stuff in the discourse, but you coach companies. How do you think about that?

• 1:19:13Speaker 02

  There's going to be more of it, but there was a bunch of that when I was at Twitter. I used to tell the company, um, the following things. Um, you have to assume that your coworkers are working in the best interest of the company. I want you to assume, always assume. Start with the assumption that whether someone did something stupid or smart or whatever, always assume that your coworkers have the best, are trying to do the right thing for the company and have the best interest of the company at heart. You know, it's the, remember there's a great, well, there's one David Foster Wallace commencement speech, but you know, he talks about like being in a car behind someone at a red light

• 1:19:57Speaker 02

  and the light turns green and people just start laying on the horn. It's like, why do people just assume the person, you know, what if the person had a heart attack? But people just, when they don't know the person in the car in front of them, they immediately assume the worst, like that asshole, go. You know, and if meanwhile, if I was behind you and we're like driving a group of people somewhere and I'm behind you at a red light and the light turns green and you don't go anywhere, I'm probably thinking like, uh oh, what's going on with Logan? And so I would, so it was specific to like, hey, if you're, if you're in engineering and you're like, you know, what are those salespeople doing? The salespeople are working hard, you know, you think it's fun to like, I don't know, you have to go, you know, sit in a meeting with this consumer brand for nine hours and

• 1:20:42Speaker 02

  pitch them nine different ideas about things they can do on the platform and get yelled at about how some porn tweet showed up behind Egg McMuffin yesterday. Like it's not, it's not fun. You want to go sit in the meeting and listen to that and get, you know, and then, and then take notes and say you're going to come back and talk to me about it? And you know, and then the same goes, and then the salespeople are like, when are the engineers going to fix these bugs? Which, which one of the 10,000 are you referring to? So I would get up in front of the company and say, you have to assume that your colleagues that you don't know are, have the best interests of the company at heart, just as you assume that about the people you work next to every day. Insist that you, and so I'm not going to tolerate like anonymous questions anymore

• 1:21:27Speaker 02

  in the all hands meeting that assume in the question that the people in, you know, organization X are doing something nefarious. And then secondly, I would just tell them, you know, and this is obviously specific to companies, don't weaponize the core values. You know, every companies have core values. We, we had a bunch we worked on for a while to help us make decisions. Um, and I wanted them to be things that actually we looked to, to help us make decisions, not stupid, you know, like, I don't know, you get on the, you get on airlines and they're like, here at United, we value honesty, integrity, like, okay. So what? That doesn't tell me anything like who val- who doesn't value like anyway.

• 1:22:08Speaker 02

  Um, don't weaponize those, you know, you hear more and more CEOs going, oh my God, we've got score value blah. And people use it as a hammer to, you know, hit, hit me on the head at all ends meetings with it. And I would just tell the team like, don't weaponize, you know, don't we- you can't weaponize the core values or the mission of the company against me or other people.

• 1:22:30Logan Bartlett?

  Yeah, it's interesting. I, I, the one that I struggle with or I've seen, I'm glad there's different people running these experiments at scale like Brian Armstrong doing what he's doing, or Toby Lukey doing what he's doing and all these different uh, styles of approaching some of the, less on the, the assuming best intent around your employees

• 1:22:52Speaker 02

  Yeah, yeah.

• 1:22:52Logan Bartlett?

  with regard to their job, but from a cultural standpoint, I um, I do think that there uh, thi- this whole, like I, I'm just seeing it manifest itself in all my companies in some way, shape or form, right? And it's, and it's always a, it's some small group that starts some Slack channel that galvanizes behind some person or cause or something, right? That always rears its head. And so I understand where people are coming from in their frustrations uh, with this.

• 1:23:24Speaker 02

  Yeah, as you know, though, the problem is, and as every CEO knows, the problem is there's always a next thing you're not doing. So, once you start, once you start allowing people to weaponize that and um, and you know, well, what are you going to do about this? Like, I'm not on the witness stand, you know, we're running it. It doesn't mean, it doesn't, however, I will say that where, where I, where I wildly diverge from some of the others you just talked about is, I don't think that means you shouldn't talk about, you know, stuff at work. Like work is literally one of the last places in America where you can have like actual discourse, where people who think differently about things are in the same room, talking to each other.

• 1:24:06Speaker 02

  So I, I don't think it's particularly healthy to say, this is, you know, you can't talk about that stuff here because I think it's probably the last place we can. Talk about that stuff. Um, I just think that, you know, weaponizing it or putting, you know, uh, putting leadership on the witness stand or putting a colleague on the witness stand. There's always, there's always another thing you're not doing. Doesn't mean you're not trying to do the best you can. Um, but there's, you can always weaponize another, what about, there's always another, well, what about X?

• 1:24:34Logan Bartlett?

  Yeah, no, it's interesting.

• 1:24:35Speaker 02

  That's just, that's just true.

• 1:24:37Logan Bartlett?

  Yeah, totally. No, it, it makes a lot of sense. Um, I, I, I guess one of the anecdotes, uh, the, the elephant in the room, literally, uh, right now with regard to your, your prior business is someone that no longer follows you on, on Twitter.

• 1:24:55Logan Bartlett?

  And I had heard you tell a story of, uh, of Elon Musk, maybe, uh, his decision to unfollow you.

• 1:25:03Speaker 02

  It was when I got in from the company and tell like, look, I'm going to step down. Um, um, been doing this for six and a half years. It's time for, you know, I've stopped my company, not the founder, the one of the founders of the company. Jack's going to come back and run the company. I was up in front of the company telling them that at a sort of an all hands meeting. I said, you know, I'm going to stay on the board and I quickly realized like, by the way, three months later, staying on the board. When someone else is now CEO is stupid thing to do because I'm sitting in the room and Jack's got to be able to run the company away if he wants to run it. And he can't look at across the table and go, that moron didn't screw this up. So I was like, I had it. So after, after that meeting, I was like, I gotta get out of here. This is just a whole idea. So I resigned from the board as well. But anyway, when I was up in front of the company, telling him I was resigning.

• 1:25:47Speaker 02

  Um, I got off stage right afterwards and you know, I had these internal dashboards that tell you, you know, followers and unfollowers and stuff. And I looked at my phone, million text messages, of course, because people were tweeting what was happening. And the dashboard was, the dashboard alert was Elon Musk has unfollowed you on Twitter. It was like, wow, it was a half an hour. It was pretty quick.

• 1:26:06Logan Bartlett?

  I'll tell you what, he was not following Dick Costolo. He was following the CEO of Twitter.

• 1:26:11Speaker 02

  Thank you.

• 1:26:12Logan Bartlett?

  That's the lesson in all this.

• 1:26:13Speaker 02

  Good callback.

• 1:26:14Logan Bartlett?

  Do you have any, I mean, I'm sure you have a million opinions about all the stuff that's, that's going on right now, but any, uh, like, do you, do you think he ever wanted to buy the company and has sort of accidentally found himself in a situation he doesn't want to end up in or any perspective on that?

• 1:26:30Speaker 02

  I kind of do, but I have no idea whether I kind of feel like that's where we are. Cause it seems like that's the way he's acting, but I don't really have any idea whether that's true or not. But I, it feels like, that feels like where we are. Um, you know, the thing, the thing that's weird is when you see Lon in a small group setting or and people ask him questions, he responds in the, in this, in this thoughtful way that makes you realize this guy's like really thoughtful and crazy smart. And um, his ability to think at another level about these things is amazing.

• 1:27:09Speaker 02

  And then he's kind of a totally different person on Twitter, you know, responding with the poop emoji to the CEO of Twitter. So it's strange. It's just weird like dissonance to know persons like, you know, um, really thoughtful and a careful thinker and, and super, super smart. And then, and then, but seems to obviously gets a kick out of poking around the edges on Twitter. And you know, I, I, I've talked to people who say, you know, what, who know him a lot better than I do. Or like, I think he's, you know, he's testing the boundaries. He's trying to see how far he can push here and there. And it's just, it's just this strange juxtaposition of the person you see in private versus the person you see on Twitter.

• 1:27:52Speaker 02

  Personally, I'd gladly for is Parag, who woke up as CEO of the company in his first CEO role. And is dealing with one of the weirdest situations in corporate America last hundred years.

• 1:28:06Logan Bartlett?

  First full day as Twitter CEO tomorrow. Yeah, there's, uh, there's something.

• 1:28:11Speaker 02

  Yeah. I mean, wow. Talk about, uh, talk about right into the, right into the fire.

• 1:28:17Logan Bartlett?

  Uh, yeah. And then the whole, I mean, uh, you don't need a comment, but the whole Jack situation is a fascinating one. Where I, I don't even really know what's, what's going on at this point. I sort of just wanted to end, uh, and move on. And I, I have a feeling that's probably where it's headed is some very large fine. And, uh, everyone goes their separate ways, but.

• 1:28:37Speaker 02

  You'll like it. Feels like that's probably what happens, but I mean, it's hard. I mean. It's hard. They can't. It does. Anyway, it's hard. Who knows? We'll see.

• 1:28:47Logan Bartlett?

  Was it Ev that tweeted out like, hey, can we all just move on from this, this situation?

• 1:28:53Speaker 02

  Yes.

• 1:28:53Logan Bartlett?

  Which is hard because that's not like the fiduciary, like-

• 1:28:57Speaker 02

  Of course, the answer is you can't because the board has fiduciary duty to accept this offer that's much, much higher than where, than where the stock was trading. And if they didn't accept that offer, then they would be subject to these insane shareholder lawsuits that you can, you know, they would get sued for immediately. And then you'd, they would be the ones paying some huge fine for not accepting an offer that was, you know, 35%, 40%, 50% above where the stock was trading. So they kind of, they're, they really, they had to, they had to do that.

• 1:29:27Logan Bartlett?

  They have to. Yeah. No, they have to run it to ground. And now there's the whole mon Jeff TC thing, which I'm sure, I mean, that's, you know, a whole nother thing, but-

• 1:29:35Speaker 02

  Yeah. I've never, I've never met that person. Jack, I believe hired him. But one of the things in there that was weird to me, I read that whole thing. One of the things in there that was like, mm, again, I don't know anything about the facts of any of this stuff, but I do know that like, when the country of India or Pakistan or whatever would, would say, you know, hey, you need to like, give us this person's phone number, you know, take down these tweets. We would say, you know, we, and it wasn't necessarily a specific law. It was just something the prime minister wanted. We would say, no. So I have a hard time believing that while we wouldn't delete a tweet, the prime minister wants to delete it.

• 1:30:19Speaker 02

  We would hire one of his spies to come work in the company. It just strikes me as like, that's not possibly true.

• 1:30:27Logan Bartlett?

  Yeah. Never, never a dull moment, it seems though, for, for the business. Well, I have some quick hitters here. Let's see how fast we can do them. And then, then I'll get you out of here.

• 1:30:38Logan Bartlett?

  Edit button.

• 1:30:39Speaker 02

  It's much more complicated than people think, but you could have a short turnaround on it. I think the quick, I think the half hour turnaround on it's probably a good idea. You have to go delete all the retweets and blah, blah, blah after that though.

• 1:30:49Logan Bartlett?

  Yeah. I, uh, did you ever think you would see the day, uh, the edit button would come to Twitter?

• 1:30:55Speaker 02

  Yeah, you can do an edit button. You just have to make it, you have to have a time window on it. And then like, you have to go, again, you have to go delete anyone who's retweeted it and everything because obviously they're retweeting something different now.

• 1:31:06Logan Bartlett?

  Yeah. Silicon Valley. The the show.

• 1:31:09Speaker 02

  Oh, what a blast. My favorite thing about Silicon Valley, the show, when I was in the writer's room there was they thought it was endlessly funny that they would come up and interview companies and CEOs in Silicon Valley. And they would go, you know, why, why is it important to be working here at, I don't know, pick the company Yelp.

• 1:31:27Logan Bartlett?

  Yeah.

• 1:31:28Speaker 02

  I'm making it up just because I thought of it.

• 1:31:30Logan Bartlett?

  Right point.

• 1:31:30Speaker 02

  Um, because, you know, because we're change, like, we're changing the world. We're changing the way people see and interact with their community and the way people are able to deal with local businesses. Okay, go down, go up to the next floor, you know, Pinterest. Why is it important to work here at Pinterest? We're changing the world. You know, I'm picking on Pinterest and Yelp. We just thought it was, they thought it was, the writers were like, you guys realize that you all say that, right? Like, you know, don't you, that every company we go to says they're changing the world, when in fact, what you're doing is painting, you know, so they literally, and I think it was season three or season four, have Richard temporarily go to work for this company where they're painting virtual mustaches

• 1:32:13Speaker 02

  on people. That's the app. And they're like, Richard, we're changing the world. We're changing the way people see each other. Anyway, they just thought that was, they thought that was, they thought that was hilarious, and they weren't wrong.

• 1:32:24Logan Bartlett?

  You gotta get people to buy into the corporate, uh, mission and all that stuff, because otherwise, what are we doing here on this earth?

• 1:32:31Speaker 02

  The other great thing about Silicon Valley is the people that say that someone in the show is them.

• 1:32:38Logan Bartlett?

  Oh, totally.

• 1:32:39Speaker 02

  That's not. Um, and it would get that all the time. Like, this is obviously so and so. It's not so and so. It's actually this, it's actually, it is based on somebody, it's based on this other person. No, no, no, it's based on so and so. Okay, well, I've seen the, I've seen the headshot of the person it is based on in the writer's room, but they'll be happy to know it's not based on, it's based on you instead.

• 1:32:59Logan Bartlett?

  Yeah, well, you'll send me the full list after, right? Of, uh, yeah, that's the VIP thing. What about, uh, what about TikTok and, uh, and Vine? Just like, do you, do you see, do you see TikTok's success and you think God bless them? Or do you think like, gosh, Vine should have been that in some way? What's your, what's your sentiment on those two?

• 1:33:20Speaker 02

  I mean, you know, lots of things are there first and then don't end up being the winner. I see TikTok's success and I say, God bless them. You know, we'll wish, I wish, um, you know, um, Vine had gone on to have the opportunity to do a bunch of that stuff. Um, but TikTok's algorithm obviously is the algorithm that got going there works. Again, you know, the, the thing about algorithms is they, it works until it becomes a, you know, sometime, well, we've all seen what happens with algorithms. They work until they just become, they just become this echo chamber of the same stuff. You're seeing the same stuff over and over again.

• 1:33:56Logan Bartlett?

  Yeah, be careful what you wish for. Well, uh, well, that's all I have. Dick, thanks for, thanks for doing this. This was, uh, this was super entertaining. I feel like in a, uh, in the amount of time we played all the hits and I appreciate you graciously playing back some of the stuff that I had heard, uh, heard you talk about in the past, but it was fun.

• 1:34:15Speaker 02

  Happy to do it. Yeah, it was fun. Thanks, Logan. Appreciate it.

• 1:34:22Logan Bartlett?

  So that'll do it for the 32nd episode of Cartoon Avatars. Thank you to Dick Costolo for coming on and talking through experience with Twitter and Second City and all that stuff. Thank you to, uh, Rashad Prisoner of War for, uh, for talking through, uh, the episode and, uh, the engagement and all that. And, uh, thank you to everyone for listening. We look forward to seeing you all next week on the 33rd episode of Cartoon Avatars.