In short
Dick Costolo (Twitter’s third CEO) reflects on Twitter’s early “growing pains” and the leadership tactics he used to speed execution, reduce dysfunction, and manage scale—covering decision velocity, communication, feedback, hiring/performance, and competing with larger rivals. He also shares regrets, especially not acquiring Instagram.
Guest backgrounds
Dick Costolo is a former Twitter CEO (served five years), previously COO, and earlier sold his company FeedBurner to Google. He joined Twitter after Ev Williams pitched him the COO role; he later led product/ops changes and management practices. The host is not fully identified in the transcript, but interviews Costolo and references prior CEO guests (Jack Dorsey, Ev Williams, Parag Agrawal, Elon Musk, Linda Yaccarino).
Key claims
Twitter was dysfunctional and slow due to group decision-making and “organizational barnacles.” Costolo’s fixes: push decisions down the stack, replace consensus voting, use “bias to yes” (only direct managers can block), minimize process bloat, and correct mistakes quickly (don’t punish errors). He emphasizes “priorities and context,” management by walking around, and disciplined priority changes.
Notable examples
Android app boot-time slowdown traced to a directive (“Dick said remove the JSON file”). Experiments stalled awaiting security sign-off until “bias to yes” enabled faster launches. He describes walking around late nights to reprioritize work, and a regret: Twitter tried to buy Instagram shortly before Facebook’s acquisition and missed it.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Drama of Twitter's Growth
0:47 to 2:14
Discussion on the challenges and dynamics of leading Twitter during its hyper growth phase.
“He's a rare bird in Silicon Valley these days.”
Dick Costolo's Journey to CEO
2:14 to 4:32
Dick shares his journey to becoming Twitter's CEO and the challenges he faced.
“I want to wind the clock back to Twitter, of course.”
Chaos and Decision-Making at Twitter
4:32 to 7:14
Insights into the chaotic decision-making process and the culture within Twitter.
“Or was it about what the press was saying?”
Accelerating Velocity at Twitter
7:14 to 11:06
Dick discusses his strategies to increase decision speed and operational effectiveness.
“If this takes six weeks, what could, what would have to be true for it to be two weeks?”
Removing Barriers to Growth
11:06 to 14:07
Strategies to eliminate fiefdoms and enhance collaboration across teams at Twitter.
“And particularly, like, companies seem to slow down as they are in hyper growth.”
The Approval Bottleneck
14:07 to 16:48
Learn about the challenges of getting approval in large organizations and the need for faster decision-making.
“Like, great, let's go ahead and launch this to, you know, X percent of users and see what happens.”
Implementing a Bias to Yes
16:49 to 18:58
Discover the concept of 'bias to yes' in decision-making and its impact on productivity.
“Some step gets added to some process that's like, before you do, I remember at Google, famously, the launch checklist got to be like 17 pages long or something.”
Scaling Communication in Growing Companies
18:59 to 22:39
Understand the importance of clear communication as a company scales and the role of leadership in this process.
“And I didn't come to that immediately, but I came to realize that that was an important artifact, if you will, of pushing decisions down the stack and bias to yes.”
Learning from Steve Jobs
22:40 to 24:26
Explore management techniques inspired by Steve Jobs and their effectiveness in team dynamics.
“one last thing that i picked up from steve a steve jobs trick okay so i love a steve job yeah so when Steve was managing both Pixar and Apple.”
Balancing Focus and Opportunity
24:27 to 27:46
Examine the tension between maintaining focus and seizing new opportunities within an organization.
“Like we might die as a company if we make the wrong decision.”
Show all 33 chapters
Management by Walking Around
27:47 to 28:00
Learn about the effectiveness of management by walking around and its implications for workplace culture.
Cultural Change Through Visibility
28:00 to 29:45
Learn how Dick Costolo used late-night walks to change Twitter's culture.
“It started because Bill Campbell, for people who don't know or listening to the podcast, Bill was on the board of Apple and famously coached Larry, Sergey, and Eric at Google.”
Strategic Mindset in Management
29:45 to 31:28
Explore the importance of strategic thinking versus tactical management.
“So I would just go, you know, up to engineers and go like, what's going on?”
Direct Communication in Leadership
31:28 to 32:58
Discover how to give effective feedback without being overly negative.
“You know, like and they would start talking to me like, OK, stop.”
The Art of Honest Feedback
32:58 to 34:24
Understand the significance of writing down feedback before delivering it.
“I thought that was great feedback and I would do that.”
Hiring Strategies in Fast-Growth Companies
34:24 to 35:57
Learn about the hiring practices and challenges in high-pressure environments.
“So I used to do a thing in my management class where it was a six hour course.”
Recruitment Insights from Twitter's Growth
35:57 to 37:28
Uncover the recruitment strategies that led to Twitter's key hires.
“So Kevin Wheel, for example, was promoted from within from an IC when I got there in 2009.”
Navigating Difficult Terminations
37:28 to 39:28
Understand the emotional challenges of firing employees in leadership roles.
“I was COO and I went to the board and Ev and said, I got the perfect person to run revenue at Twitter.”
Pitfalls of Hyper-Growth Companies
39:28 to 41:21
Explore the common pitfalls faced by CEOs of rapidly growing companies.
“It's a whole, you know, it was a whole layout of how to go about it.”
Financial Oversight in Rapid Expansion
41:21 to 42:00
Learn why financial efficiency is crucial during periods of rapid growth.
“One of the real pitfalls, especially for these hyper-growth AI companies that are going from, you know, a single-digit revenue to 100 million.”
Challenges of Hypergrowth Management
42:00 to 43:30
Learn about the difficulties companies face when scaling rapidly and the need to manage talent effectively.
“We're going to be super capital efficient.”
Competing with Giants: Strategies Against Facebook
43:30 to 46:05
Discover how to navigate competition with industry giants like Facebook and the importance of understanding customer needs.
“But as you move down the stack and you've got inexperienced managers who are first-time managers, first-time directors, man, there's nothing that they want to do less than let someone go.”
Missed Opportunities: The Instagram Acquisition Story
46:05 to 48:05
Reflect on the missed opportunity of acquiring Instagram and its implications for Twitter's future.
“And he would sit down with the CMO from Unilever before the meeting and say, how'd the Facebook meeting go?”
The Complexities of Content Moderation
48:05 to 51:12
Understand the challenges of content moderation and the subjective nature of what constitutes acceptable content.
“And well before Mark made his offer to them, I pulled Kevin, went out to dinner with Kevin and Mike and told them we wanted to buy the company and would end up giving them basically well over 10 percent of Twitter.”
Navigating Public Perception as a CEO
51:12 to 54:02
Explore the impact of public perception on CEOs and the importance of maintaining authenticity.
“with an understanding of the situation, like our GC, you're going to just have a bunch of judgment calls and you're going to get a bunch of them wrong, and that's life.”
The Evolving Role of CEOs in Founder-led Companies
54:02 to 56:00
Discuss the trend of replacing founders with seasoned executives and its implications for company direction.
“And there's some, you know, these stupid awards that come out, come out.”
The Evolving Role of CEOs
56:00 to 56:40
Discussion on the fluctuating presence of experienced CEOs in startups.
“is replaced or just that they don't hire the adult external CEOs.”
Career Aspirations and Preparation
56:40 to 57:50
Advice for aspiring CEOs on positioning themselves for leadership roles.
“Even the public companies like MongoDB, but I'm on Workday recently, but like maybe one a year.”
Communication Styles of CEOs
57:50 to 59:00
Exploration of passive aggression in leadership and examples of effective communication.
“I think there's a lot of passive aggressiveness.”
Nature vs. Nurture in Success
59:00 to 1:00:30
Debate on the influence of genetics and learned skills on individual success.
“And I feel the same way about Reed Hastings, a totally different executive at Netflix.”
Authenticity in Leadership
1:00:30 to 1:02:00
The importance of being genuine as a leader and avoiding imitation.
“The CEO rulebook feels to me to be changing.”
Building a Strong Board
1:02:00 to 1:03:30
Advice on forming a board of directors and the value of independent members.
“This reporter's in the Houston Rockets locker room.”
Going Public: Challenges of IPOs
1:03:30 to 1:05:30
Insights into the difficulties of taking a company public and the benefits of staying private longer.
“You're building that, you're a$100 million company going to$400 million.”
Transcript
Automatic transcript. May contain errors.0:00I just felt like Twitter was such a drama. Twitter is like the drama queen of hyper growth companies. You know, it was like when I took over as CEO that year, the Twitter bird had hanged itself and exploded on two different magazine covers. So I went up to our head of communications, Gabriel Stricker, and I was like, Gabriel, great news. Next year's goal, no dead birds on magazine covers. You know, low bar.
0:47Hey, everybody.
0:47Brian Halligan:We have Dick Costolo on the show. He's a rare bird in Silicon Valley these days. He was CEO of Twitter, but he was the third CEO. The first one was Jack Dorsey, who you probably met on the pod a couple weeks ago. The second was Ev Williams, the other founder. And Dick took over as COO and then ultimately as CEO of Twitter, and he ran it for five years. It was a really extremely fast-growing organization. They created a category, didn't have a revenue machine, and was famously dysfunctional. I think Dick did a really nice job, and he was sort of the adult in the room. And he kind of ran the scale-up CEO master class.
1:26Brian Halligan:He talks all about in this podcast. He talks about increasing velocity of decisions and execution, which is tricky as you scale. He talked about how he managed by walking around. This is something I did. I think it's a really good idea. He talked about how do you give very tough feedback to very tough people. There's some gems in there. Dealing with the press, particularly a press that doesn't like you. He talks about focus and how much focus you really need in the era of AI when you can build stuff so quickly. He talks about how do you manage the forest instead of fighting all the fires. He's got a lot of wisdom in here.
2:01Brian Halligan:He also talks about his regrets, including a whopper, his regret not acquiring Instagram. That one hurt. If you're scaling your 100 employees, you're ripping, growing fast, you've got a lot of growing pains, maybe you feel a little out of control. This episode is for you. Welcome to the show. Thanks for having me. Appreciate it. I want to wind the clock back to Twitter, of course. Of course. I watched a documentary recently. Was it the one I was in? Yes. I thought you were really good at it. Thank you. You were great in the documentary of yourself. You came off as rational in knowing what the hell you were doing.
2:39Brian Halligan:But you're in a long line of interesting CEOs of Jack Dorsey and then Ev Williams and yourself and Jack Dorsey and Parag and Elon Musk. Parag and Elon. And don't forget, you know, the Elon hired hand, Linda Yaccarino. Okay. Of course, of course. You joined as COO. What was the pitch? What was the pitch to me? Yeah, Ev pitched you. I mean, yeah, Ev pitched me. The initial pitch was I'm taking paternity leave for a couple weeks. I, Ev Williams, am taking paternity leave. I need someone to come in and just hold down the fort for a couple weeks while I'm out. Interim. Yeah, interim. Would you do that?
3:16But then while we were having that discussion, he's like, well, what if it was permanent? You know, what if you were a COO? And I was going to go start another company. So rewinding the clock a little bit further, I'd sold my previous company FeedBurner to Google. It's where I rebumped into the Twitter guys because they were all there from Blogger and getting ready to leave and start Odeo, which became Twitter. Anyway, I'm leaving now. I'm leaving Google a couple of years later. Ev texted me that. I was like, I'm going to go start another company again with one of my FeedBurner, one or more of my FeedBurner co-founders.
3:51and then have said, what if it was permanent? What if you were COO? And Twitter was already, so it's summer 2009. It was already like had hit the, you know, Ashton Kutcher and Oprah Winfrey are, you know,
4:07Brian Halligan:fighting for the who's going to get a million followers. I can see why you wanted to do it. But zero, zero revenue model, zero business model. All the articles were, sure, Twitter is interesting, but they don't have a business model and they'll never make money. And I just kind of had the, man, you don't get an opportunity to go to these, to get on these rocket ships. And when you get the opportunity, you should do it. So I did it. So it was famously dysfunctional and chaotic. I assume you knew that going in. Was it much more so than you thought? Or was it about what the press was saying? It's always both, you know.
4:44it was it was the things that were different were it was very much a collective by which I mean like decisions were kind of made as a group yeah it wasn't okay well you're responsible for engineering I don't know make it figure it out and you know figure out what the right answer is or should we you know have should we make retweet a native thing or should it be you know just you write you had to write RT at the time and rewrite the tweet. I remember that. And there was a discussion about, well, should we just have retweet be a thing you can do in Twitter? And it would be kind of sit around the table and talk about it and decide.
5:24The group would decide. Okay. You know, so things moved methodically is a diplomatic way of putting it. I see. And decisions were reached over a period of time. It was chaotic, and then it was also just – we just didn't move very quickly. It didn't move quickly at all. In the documentary, it went through the pushing Ev out and giving you the CEO job.
5:50Brian Halligan:It sounded awful, the whole process. It was awful. What's your side of it? What was going on? I don't really have a side of it other than it was an awful – like it's – these things in hindsight are – it happened very, very quickly. It happened super slowly. and painfully and and um you know i was informed like in the driving rain on the road home by you know evan jason that the board decided that you should be the ceo yeah but i hadn't been told and then bill campbell called me and like you should just quit you know and then and then like why am i quitting you know and like anyway what and then this went and then like the board decided actually know ev is going to remain ceo um but you've been great and we're going to invest a bunch of your options and so long okay and that i mean no kidding yeah over many many days and weeks and finally it was like listen just write up the separation agreement and you know i'm good i'm good like whatever i'll go find something i'll go do something else and then you know to make a long story short the board got back together it was like oh no no no no remember bijan sabay from spark texted me don't quit okay i was like i'm not quitting like okay you guys told me you wanted me to leave because i was gonna stay anyway it was super crazy yes um and there was obviously a ton of stuff going on and anyway um long story short they're finally like look you got to do it anyway and you know i get really long story short i was like all right i'll stay and do it okay you take over you're the adult what did you do initially yeah like it's very tricky the situation yeah and I think the current the existing founders are hanging around probably looking over your shoulder if not breathing down your neck well Jack was the chairman of the board right still have had made Jack chairman of the board when he made himself CEO um Ev still on the board so two of the founders Ev and Jack are still on the board in business in the company and business in the company and Jason Goldman's in the company running product and you know and a bunch of other people yeah the the first thing that I felt and I've sort of foreshadowed this the first thing that I just felt we had to do is like velocity velocity velocity and and that remained a concern of mine throughout my time they're like faster faster faster cadence cadence cadence like how can we go faster?
8:19Why do things take so long? If this takes six weeks, what could, what would have to be true for it to be two weeks? We just, I did stuff like that constantly because I was always like, man, this is like dental surgery. But it was starting from a position of, we're not going to make, we're not going to sit around the table and vote on things anymore. I remember vividly the status, like the status line changed from like, what are you, what's going on or what's happening to something else? Or maybe it changed to what's happening. I don't even remember. I wasn't even involved in it. And one of the front engineers, Britt Savetaville, came into my office and was like, hey, man, what's going on?
8:56I was like, what are you talking about? He's like, the status bar changed to what's happening. I was like, okay. He's like, no one asked me what I thought about that. And I was like, oh, man, yeah, we're not doing that anymore. There's going to start being a lot more of that. So that was thing number one. Okay. Thing number two was there were a set of operating principles that were written on a whiteboard that Biz had been involved in with either either on his own or with other people. But they were like, you know, like sometimes you'll get on a United Airlines flight or whatever, and they'll say, here are United Airlines.
9:33We believe in integrity and honesty. I'm like, OK, who cares? Like, that doesn't help me. That tells me nothing about you. Every company says exactly the same. Like, whatever. And also it doesn't help me make any decisions and these things are meaningless and they're usually weaponized against management by like, you know, well, it says right here. Anyway, so it's like, all right, we got to get rid of these things. They're like, they're like not useful.
9:56Brian Halligan:Did the founders push back? No, they didn't really. Okay. And so. Good for them. We got rid of those. Like there was, there were just, I remember there were just like, everything was just kind of like messy, you know? I remember there was this kitchen and there was like, it was just kind of a mess. And there were like dirty dishes in the sink and everything. And I think I sent out an email. I was like, this is why the fucking site crashes. Like, you may not get it, but like this is why the site crashes. Because everything's just kind of fucking like, oh, well, someone else will clean it up. And I was like, this is ridiculous.
10:31And I just tried to get this sort of like, we're not going to do this like, oh, well, we'll get them next year's stuff anymore. There was a poster on one of the floors that was like, we'll make better mistakes next time or something like that. You know, and I was like, get that poster out of here. It's not I don't really care about it, but it's just sort of indicative of, oh, well, you know, and then the site would crash again and people would go like, oh, well, we'll figure it out. You know, hopefully we won't happen again next year or whatever. So it was a lot of cleaning that up. Yep. And a lot of velocity, velocity, velocity.
11:05Brian Halligan:All anybody CEO wants to talk about now is speed. Yeah. And particularly, like, companies seem to slow down as they are in hyper growth. Yeah, because you – It's like you get bigger and get less done. Yeah. Because barnacles build up on the – you get, like, organizational barnacles. So a couple things. Initially, when we were smaller, this is sub 200 people, what I did to speed things up was, one, we're not going to make decisions as a group. We're going to push decisions down the stack. By the way, I don't have to – like, don't come to me and ask me what you should do about this. unless you have no idea and want my opinion, like figure it out, you know, and don't tell your team what to do.
11:44Tell them to figure it out and push as many decisions down the stack as you can. And I don't want to hear, you know, I remember I would talk to Jack Dorsey at these dinners we would have from week to week when he was chairman and was CEO of Block down the street from us. We would get together on Tuesday nights and have dinner. And I remember telling him, God, I hate hearing Dick said in the company as a reason for things. Because what would happen was, I'll give you an example. I remember this example really well. The Android app started taking longer and longer and longer to boot. And so we would have a metrics meeting.
12:22I was like, hey, man, you can see the usage numbers going down almost linearly with Android boot time going up. people are firing up twitter and it's taking too long and they're moving on to something else like over here on ios that doesn't happen it's got to be the same boot it's got to take just as long to boot android as it does ios okay so two three nights later week later i'm walking around like one of the engineering floors after hours and this android engineer comes up to me and goes hey can i ask you a question like yeah he goes hey did you say um remove the json file from the android boot system?
12:58I was like, I didn't. I know what a JSON file is, but I couldn't tell you what's in the Android boot JSON. And he's like, okay, because I was told Dick said remove that. And I was like, aha, I think I know what's going on here. Right. And you, this would happen throughout the company. Some manager director decides here's a way to solve this problem. And the engineer pushes back against them and they just go, you know what Dick said, do it. And it became like this reason for doing things. So part of the speed was, no, we're not going to have someone so said it's push the decisions down the stack.
13:36And by the way, if your team makes a decision and you can't defend it to your manager, like that's don't go well. So-and-so said, like have the engineer, talk to the director, whatever.
13:47Brian Halligan:The second thing I did is we got bigger and bigger is I started realizing, oh the organization is slowing down because there are all these fiefdoms in the organization that want that want like ball control over their stuff so very common very common so so here's here was here's how it surfaced um we ran an experiment and i was like oh this is actually really super interesting what are the hypotheticals about what this experiment would do in production The engineer runs through it in experimentation meeting. Like, great, let's go ahead and launch this to, you know, X percent of users and see what happens.
14:25Yeah. One week, two weeks, three weeks go by. I'm like, hey, where's I'm like looking at the app. I'm like, where's the you know, where's this engagement experiment running? And I find the engineer is like, oh, I'm waiting for, you know, trust and safety to sign off on. I'm like, what? It's like, oh, yeah. Well, I asked so-and-so if we could launch this, if ready launch. And they didn't say no, but they said you have to go get approval from yours of security. And I started realizing that when people would try to go do something, they wouldn't be told, no, you can't do that. It was something much, much worse and slower than that.
15:05You need approval from security. You've got to get approval. You've got to go ask these 14 people. You've got to ask your mom. Go ask these 14 people. And if they all say yes.
15:13Brian Halligan:Okay, everyone's got this problem. How do you fix it? So what I did was, it's very similar to what Bezos used to do at Amazon with bias to action. I had, it was from my improv background. I was like, we're going to have a bias to yes. And bias to yes is only your direct, the person you report to is allowed to tell you you're not allowed to do that. Or legal can tell you if you do that, you'll be fired because it's illegal and a violation of the privacy policy. But no other organization, period, is allowed to tell you you can't do that or you need to go ask these people for permission. Just your direct manager.
15:51And that means if you have an idea for an experiment and your manager signs off on it and you have time to do it because you're done with whatever else you're working on, no one can tell you you can't do that. Or, you know, the marketing team's not allowed to tell you you can't use the MailChimp software we licensed because that's the marketing team, right? And so bias to yes was I don't want to hear about something being stalled because organization X said you have to go to get approval from organization Y. And that was great. Experiments started flying out. the flying out um in fact engineers started going like wait i don't have to necessarily get designed to build all these wireframes for something i can just do it myself since we're only launching it to one percent and see if it works and so that was just great it worked throughout the organization and i would repeatedly get on stage at all hands meetings and like talk about like bias ds and what it means and what it doesn't mean it doesn't mean you can go do stop doing what you're supposed to do because it's priority and do whatever you want to do because your manager is going to go like if you do that i'm going to fire you because you know the you're being okay measured on no group
16:57Brian Halligan:decisions dris and bias action anything else that all these ceos that work with are like we're slowing down how do we speed up yeah don't solve problems with processes so it happens all the time in organizations like some customer problem happens the customer churns out or the advertiser quits And the CEO goes, that can never happen again. And so what happens? Some step gets added to some process that's like, before you do, I remember at Google, famously, the launch checklist got to be like 17 pages long or something. And Larry was like, this is insane. I was like, yeah, it's because it's like the FDA, never another thalidomide or the TSA.
17:41Make sure there's no water bottle on the plane. And pretty soon you're not managing the outcomes. you're managing to the processes, and you got to go through nine steps before you, you know, instead of just managing to the outcome of make sure there's not a bomb on the plane. So the way we did that, the way you do that is you solve problems with DRIs, operating control, and not processes. You should probably only really have a couple organizational processes, and everything else should be span of control and decision making. When you do that, you can't. And this was a this was something I had to under come to understand and adapt to.
18:24When you do that. You can't punish people when things go wrong. Yeah. You want them to take risks. You want them to be bold. You want them to have this like bias to action and doing things and not going around and asking for tiptoeing around, asking for permission. But one of the implications is you can't punish people for making mistakes. And I got to the point where I would tell the team, it's not the job of leadership to prevent mistakes from happening. It's the job of leadership to correct mistakes quickly when they happen. So if you screw something up, like by all means, tell us so we can help you fix it.
18:57But no one should get in trouble for screwing something up or making a mistake. And I didn't come to that immediately, but I came to realize that that was an important artifact, if you will, of pushing decisions down the stack and bias to yes. And we're not going to have lots of processes.
19:13Brian Halligan:Love it. So many of the CEOs I work with, I just was at a, I won't say the company, but here in New York City and spoke at their company meeting. And here's how we just describe every company. When it's, call it under 50 employees, everybody knows what's going on all the time. When it's over 150 employees, nobody knows what's going on anytime. How did you fix? How did you scale communication, keep people on page? Tell me a little bit about the management by walking around. Yeah, well, I did two things. First of all, I taught this management class at Twitter. It was actually based on Ben Horowitz teaching a management class at LoudCloud.
19:54Fascinating. And Ben had in his outline from his management class, a statement that I like highlighted and underlined and circled three times was make sure everybody understands what you understand. So I would always tell my managers that like your job is to make sure everybody understands what the priorities are and what it means for them and their team, how they fit into those priorities. And more importantly, for your team, what it means for them personally and professionally, if we achieve what we have to achieve. Those those kinds of things are great. I remember somebody telling me a story of taking a factory tour at a Tesla shop and seeing some guy who's like screwing a widget into the car and asking the guy like, what are you doing?
20:40And the guy didn't just say screwing the widget into the car. He said, well, if I do this and we're able to build these kinds of cars and these kinds of cars can become more popular in America. I mean, the guy understood the story. And I thought that was great. It's like the analogy.
20:55Brian Halligan:Somebody asked a bricklayer, what are you doing? And the bricklayer says, oh, I'm laying bricks. and the other book player says, I'm building a beautiful cathedral. I love that. Yeah, like you want people to under, I mean, how much more motivating is it to work in a company where you know, if I'm successful in my work, I understand what the implications are for both me personally and the company. Okay, priorities and context. Priorities and context. Good news travels fast, bad news travels slow. And as the org gets bigger, it slows down. And the signal gets distorted. How does CEO deal with that?
21:27Yeah. I said earlier, it's not the job of leadership to prevent mistakes from happening. It's the job of leadership to help correct them quickly when they happen. So I would always communicate, you got to tell leadership if something's screwed up. If your situation is screwed up or your team or some decision is a mess, you have to communicate that constantly. And then secondly, I would regularly communicate the priorities to the team over and over and over at all hands meetings. Here's what the priorities are that we're working on. this is how we're going to measure them this is why they're important and this is what they mean for us as a company if we're successful you always wanted p i always wanted people to understand not just what we had to do but why it was important to do it and i think that scaling communication architecture is like one of the most important things in any company and part of it is never saying because so and so said that's not context that doesn't help your team understand context for why some decision was made or what or what they should do or how they should go do it so that combination of pushing decisions down the stack making sure that everybody understands what you understand and that a lot of that is context and always communicating problems or issues up the stack as a means of helping get helping get it resolved quickly were the ways we dealt with that
22:45Brian Halligan:one last thing that i picked up from steve a steve jobs trick okay so i love a steve job yeah so when Steve was managing both Pixar and Apple. So he's CEO of Pixar still, but now he's back in the seat at Apple. So now he's only at Pixar one day a week because there's all this stuff I got to go fix at Apple. So they're making like Toy Story 2. And what Steve would do, so he's got one day to come up to speed on what the heck's going on at Pixar. So he'd go into the office on Friday and he would say, all right, today I want to sit down with like the illustrators. you know without lassiter the director of the movie john without lassiter in the room i just want to sit down me and the you know illustrators and it would go there's like eight or nine or whatever of them it's a you know janet um tell me something that's not working well at pixar and then you know bob do you agree with that you know taking notes like okay phyllis tell me something that's working well at pixar not on the movie not about your job you know and at the end of the meeting 45 minute one hour meeting would say okay here's what i heard um you know people having these kinds of issues.
23:49This is going really well. I'm going to go talk to John about it and he'll deal with it on, he'll deal with the rest of this on Monday. You know, you can follow up with him. So he's not saying, oh yeah, that sucks or, or, you know, no, you're wrong or whatever. He's taking notes, making sure he hears everything that was said. And then going to talk to the last speaker about it. I started doing that with teams. You quickly find out if that team knows what the priorities are, is in sync with what you're hearing from the leadership of that team. and some of the leaders of the company hated it and i was like well now i'm concerned about why you why you hate it because yeah but i wouldn't you know you're not in that meeting doing things like throwing the director under the bus you're going okay here's what i heard i'm going to go talk to my management team about on monday and you know chris or whoever will follow up with you
24:34Brian Halligan:let me switch to you on priorities so all these ceos i coach they have their list of priorities it's january 1 but oh my god there's so much opportunity so much interesting stuff and this employee has this thing going on how often did you rejigger those priorities yeah were you disciplined about yeah over the course of whatever that period was yeah you can rejigger them once in a while once in a while i don't know like you know if you've got four huge priorities for the first four to five months of the year you can't you can't get to to february and go these two are stupid and we're you know once or twice a year you can go uh this one is let's let's actually change that one to this other thing if you start doing it regularly people are like well we can get to work on the direct messaging architecture but dick's probably gonna you know 50 50 he's gonna change you just can't do stuff like that by the way that's another way companies slow down is because people are just like look i'm not gonna bust my ass on this thing when there's a 50 percent chance dick's gonna throw it out the window in in a month yes let me test something on you a lot of these hyper growers it used to be that there were a lot of one-way doors in the software industry stuff took a long freaking time to get out the door even to test yeah and you had to kind of do things serially yeah now you can do so much so fast yeah and so they're just doing more and it's more parallel and a lot of those one-way doors are two to two-way doors is focus overrated now no focus is focus i don't think focus is ever overrated however however the fact that you can do more quickly and since they're two-way doors you're like great nope i mean this as the old Jeff Bezos, only take a long time to make decisions that are existential.
26:15Like we might die as a company if we make the wrong decision. There's fewer and fewer of those. Decisions that can be like, if we screw it up, we can go back and do the other one. Do those right away. So focus is still important. But it's also true that you should feel like you can do a lot more now with less because you can. There was a point in 2011 when we wanted to try to get Jeff Bezos to join the board of the company. Like, we have an independent seat open. Who would be the best possible independent director? Jeff Bezos. So Jack and I go meet with Jeff Bezos. I think it was like at the Ellen Company conference or something like that.
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26:53And Jeff asks a question about strategy. And Steve Jobs was still alive at the time. And Jack said, well, Steve says the most important part about being a CEO is focus. and you should say no to almost everything. And in fact, it's the CEO's job to be the editor-in-chief and you should say no to almost everything and do very, very few things. And Bezos looks at Jack and goes, oh yeah, well, I like to do everything. And he does the big Bezos laugh and he goes, my team has to talk me out of stuff. He goes, you know, there's lots of ways to be successful. And I remember that like it was yesterday and he's right.
27:35there's many ways to climb the mountain yeah I think it's true that today he would say great I can do even more now we can still we can still be focused but I can do even more things I think those I think those things can both be true okay just want to get back to some of your management
27:49Brian Halligan:techniques because I think they were great this management by walking around which are very old school Hewlett Packard concept just talk about it sounds like you did the same time every week no I did it at all hours. Okay. And mostly late night. It started because Bill Campbell, for people who don't know or listening to the podcast, Bill was on the board of Apple and famously coached Larry, Sergey, and Eric at Google. I wrote a book about him called Trillion Dollar Coach. The benchmark folks had also brought him into Twitter before I got there. um and bill um famously said um when i took over as ceo like you could um roll a grenade into twitter at 5 30 p.m and only take out the cleaning people so and he was right and he was and he was right so i was like okay how do you you can't tell people you just can't tell people work harder you know they're like okay you work harder yeah you know so what i did was i just i mean it's so such a stupid thing but I was like all right I'll walk around tonight I'm gonna start well I'm gonna go out get dinner I'm gonna come back at like 9 p.m 9 30 p.m I'm gonna walk around and whoever's here I'm gonna talk about the stuff they're doing at the next all hands meeting and I'm gonna like I'm gonna like bump up the prioritization of that yeah and I remember like Marcel Molina at no radio on Twitter that's a that's a little promotion for Marcel there Marcel was always working late on stuff and I would like what are you working on and you know I'm working on native retweet or whatever and I would get in front of the company go like but Mars the work Marcel is doing and people like how can how does he always know what Marcel is doing okay and other people go like oh dick comes back after dinner at night and walks around with people's slowly slowly slowly started to change the culture of okay the people who are around when dicks walking around are getting their stuff prioritized I did I copied you I walked around Friday afternoon yeah and I I learned a lot.
29:46Brian Halligan:Yeah. And you, yeah. So I would just go, you know, up to engineers and go like, what's going on? What are you working on? Yeah. Yeah. You have an interesting expression that I don't understand about forest fires in forestry management. Yeah. What the hell are you talking about? Yeah. I, I had, I was trying to help a director in the company be more strategic. They were super tactical. Okay. And it's fine. Like you're like your job as a director as you grow in this company is you can't just say like, well, I put out this forest fire. But like your job is to map the territory and start to do forestry management.
30:25Like what are we going to do so that next year, if there's a fire over here, that highway is not going to be in trouble. Like you can only work so many hours a day and stamping out fires isn't going to work as we scale. You need to push those down the stack. Your team should be like fighting the fire that's over there because it might, you know, burn a house down or something. You need to be focused more on like thinking about this whole pie and what what's going to be true. What has to be true 24 months from now. So this whole pie is in this whole territory is in better shape. And I just that was the way I that was the metaphor I had for helping people try to think strategically versus like, well, I'm doing, you know, I'm chopping down the trees.
31:11Look, I'm look at all the trees. but that's not like leadership and strategy that's tactics like that okay now i get it one of the
31:17Brian Halligan:people i connected connected to connected with before interviewing uh you said something interesting about you oh boy i can hardly wait i'm sure most people did but anyway in both sides of this are interesting he's both both sides he said you know silicon valley san francisco everyone's passive aggressive and so i'm curious your take on that um because i'm i'm i don't live in silicon valley and the second thing he said dick's not passive aggressive dick's aggressive yeah what's give me both sides of that it's just like i'm super imp i know this is a personal flaw but i'm super impatient like people would come in and go here's why i'm you know why i think or whatever I'm sad.
32:02You know, like and they would start talking to me like, OK, stop. Like, it seems like you don't like working here. You should quit. OK, no, I want to tell you I'm sad. You know, like, OK, I don't like I don't care. Who cares? I'm sorry. I'm not trying to be a jerk, but like we have a million things to do. I remember. And then, you know, I just like this is just direct and blunt with people. I'm not a jerk. You don't have to. You don't have to. People think like, I think a lot of times, especially maybe engineering leaders who, you know, come up in the organization like coding and programming and doing stuff on my own.
32:40And now I have to manage people. They think when you tell them you have to like, look, you have to manage performance in your team and have to manage poor performers out. They think you have to be a jerk when you do that. You don't have to be a jerk about it. You just have to be direct about it and forthright and not, you know, no one's sadder than this about than me. You know, don't say stupid stuff like that.
32:58Brian Halligan:okay you can be empathetic and still be straightforward okay a lot of these ceos i coach are in there they'll call it in their mid late 20s um and like in their whole life they haven't given they don't go to like mom i got some feedback on dinner or like you're playing you're hogging the basketball you've just never given the homo sapien feedback it's unnatural yep advice for that ceo yeah my advice for that ceo bill campbell actually gave me this advice early on is like write down what you want to say and then say that and don't say anything else so the night before if you write back down the honest feedback that you know i would give brian especially if i have to give brian a bad performance review the night before if you write it down i guarantee you 99 out of 100 people if they go into the meeting the next day they don't say that okay they're like listen brian instead they're like you know it's really hard time here for everybody we're all working you know just shut the fuck up like the person knows you're about to like hit him over the head or something and you also don't have to say like hey brian that's just the way it is you know too bad if you don't like it you just just write down what you want to say and be forthright and honest and you know you can say like i understand it's like if you can't don't want to deal with it anymore i get it and say those things and don't add a bunch of fluff around it.
34:22I thought that was great feedback and I would do that. Sit with the silence. Yeah. Sit with the silence.
34:27Brian Halligan:Sit with the silence is hard. Yeah. So it's unnatural. It's unnatural. The best person. So I used to do a thing in my management class where it was a six hour course. There was a ton of stuff in it. But one of the things I would do, it was about giving people feedback and like, okay, you're like, Brian, you're going to give Dick feedback. And the feedback is you've been working on this thing for six weeks and busting your ass and you've been here in middle mid till midnight every night and we have to cancel the project because it's no longer a priority yeah for what something horrible that no one wants to hear yeah you know some made up made up of course the only person who did the role play that was ever good at sitting in silence was elad gill current uh venture capitalist elad sat in the chair and gave the person the feedback and i and And I say to the employee that I see before the role play, I kind of pull them aside and go, you're this is bullshit.
35:20And you're going to tell Dick and you don't want to hear this. And it shouldn't be canceled. They need to look at the data, whatever. And Elad was great at just sit there. It's hard. And then eventually the other person runs out of gas and stops, you know, talking. And Elad was great at that. And the only person who ever did it.
35:40Brian Halligan:Okay. One of the things I want to ask you about is you had some very talented folks, some of which you brought in, probably others brought in, like Adam Bain and Kevin Wheel, Anthony Noto, Elad. How did you guys recruit? What did you look for? Are you looking for slope or experience? Like, what was your filter? It's a great question. I actually tried to promote from within as much as possible because you want people inside the company to feel like we're not going to get capped out at which point, you know, I can only get to this level because anything above that dick just goes out and finds someone.
36:13So Kevin Wheel, for example, was promoted from within from an IC when I got there in 2009. Well, there were only a few people, 40 people or so in the company when I got there, to eventually running all the product. after running all of Ad's product. So he was promoted from within. Noto was, I just felt like Twitter was such a drama. Twitter is like the drama queen of hyper growth companies. You know, it was like constantly in the news. When I took over as CEO that year, the Twitter bird had hanged itself and exploded on two different magazine covers. So I went up to our head of communications Gabriel Stricker and I was like Gabriel great news next year's goal no dead birds on magazine covers you know low bar yes uh anyway but it was just constant drama and Noda was so good at Goldman Sachs where he ran technology and media at dealing with investors and communicating with them etc that I had been I'd been trying for a while to bring him into Twitter and I was I was finally able to.
37:23And he was, of course, he's fantastic.
37:25Brian Halligan:How about Adam? Adam was funny. Adam was a non, what you call a non-consensus hire when I first recruited him because it was while I was COO and I went to the board and Ev and said, I got the perfect person to run revenue at Twitter. It's this guy, Adam Bain. He's in LA and he works for Fox Interactive. And everyone was like you're gonna bring in someone you're selling ads so you're gonna want to bring in someone who works at fox in la and bring them to san francisco to run our like you know revenue side of the business but he was the perfect person to do it i must have flown down there to la for five or six months before i i could convince him to do it um but i met him while we were in the process of selling feed burner and um his his employer news corp was one of the interested parties before google bought it and i got to know him and it was just like man this guy is like tireless and we're gonna be in like a constant dog fight and and fighting from behind against facebook for social ad dollars and adam was just he's just like one of those people who's got a motor that doesn't stop and who's the perfect person for the role there's an old adage uh fire fast.
38:46Brian Halligan:Yeah. Hire slow. Yeah. I always said that out loud. I didn't do that. I fired slow. And almost every time I was like, man, I should have been six weeks. I knew. Yeah. Yeah. Were you disciplined about that? Yeah. We, I tried to hold myself accountable to that and it's horrible. Like there's horrible. There's nothing worse than having to do something like that. I remember one of my board members, David Rosenblatt, you know, I was, I was, um, I'm a little bit like, come on when people are like oh i like firing people because you know it's it's the right thing for them like that's just sounds like you're an asshole because it's horrible yeah um but you have to do it yeah and um i remember i asked david rosenblatt because i had to terminate someone with global operating responsibility it was like wait a minute if i fire him in the morning the people in japan are going to be in bed but if i fire him in the afternoon then you know whatever whatever and so i was like i gotta figure out and and i was talking to my board about it and david rosenblatt who had been the ceo of double click before it sold to google was like oh i had to do that i actually saved the calendar date from that because i had a whole series of communications i had to roll out this is we're now a couple thousand person company etc with like 30 offices around the world so i get his day i get his day of communications and the only thing i remember from it.
40:05It's a whole, you know, it was a whole layout of how to go about it. The only thing I remember from it is 6 a.m., wake up in a cold sweat. You know, it's just horrible. Yeah. You know, it's not fun. You can't wait till it's over. Yeah. And you just have to be, but you have to do it. And most, Jeff Wiener's old analogy from, he was LinkedIn CEO when I was running Twitter, Jeff Wiener would call it the, for those of you who are baseball fans, he was like, you know, sometimes you're watching a baseball game and you see the pitching coach or the manager walk out to the mound and talk to the pitcher and the pitcher's like no no no i don't worry coach i still got it and the manager walks back to the dugout and this guy cranks one out of the park again and you can see the manager walking out like i knew it i knew it and jeff was like i never i always tell myself don't be the manager having the first conversation with the person when you know what you should be
40:56Brian Halligan:doing is having the second conversation with the person as a red sox fan that really hits really hits home. I think his example is actually Pedro. Pedro Martinez from the Red Sox. Grady Little didn't take him out. Yes. I work with all these hyper-growth companies. I think you do too. What are the pitfalls when you're in hyper-growth? And what are your tips for the CEOs listening today who are growing incredibly fast? One of the real pitfalls, especially for these hyper-growth AI companies that are going from, you know, a single-digit revenue to 100 million. is it's very, very easy to take your eye off the ball when you raise too much money.
41:37And by taking your eye off the ball, I mean, we're thinking about operating leverage and operating efficiency. Because once the money is there, you're like, don't have to worry about that. I'll go worry about this thing over here. And next thing you know, the burn is like, what are you worried about? It happens all the time. And Ryan wrote this great post saying, look, I thought I was like Mr. Efficiency. It's not going to be the same for us. We're going to be super capital efficient. But when you don't have to worry about it at all and there are a million other things to do, you stop worrying about it and you start getting -
42:11Brian Halligan:Are people raising too much money? I think so in many, many cases. I don't know that the models are. The models probably need all the money for compute. But like an app company going from 10 to 100. Yeah, I think people are raising too much money. I think a lot of companies are raising too much money Because, you know, raising$100 million Series B is the new$20 million Series B. What else in hypergrowth? Like, what breaks in hypergrowth? Hiring. Hiring almost. I mean, my favorite thing is you talk to, you know, you talk to like a CEO who's like, I don't know, whatever, pick some number. You know, it's first company.
42:48They were lead product manager at awesome fintech company X. and now they're CEO and they're like, we're only going to hire eight players. You know, I'm like, yeah, PS, guess what? Everyone says that. Yeah. Come back to me when your customer success team has to hire twice as many people next quarter because you just turned to venture customers because no one checked in with them last quarter because you're growing like a weed and then tell me, you know, and you just end up not doing that. And so one of the things that you have to do when you come to the realization that we don't only hire A-plus players is you have to get, like, religious about you have to manage out low performers.
43:39But as you move down the stack and you've got inexperienced managers who are first-time managers, first-time directors, man, there's nothing that they want to do less than let someone go. They'll do anything to not do it. you prevent them from transfiring people you know transfiring is like janet would be great on the ads team she loves ads you need people yes and then you're like no no no so i had a you know we had sort of performance reviews i was like if your review is below x number you can't switch teams yeah like that's a good idea you know you know whatever let's say it's one through four four is amazing one is you're got to go if you're a two you can't move teams until you're no longer a two p.s if you go two to three to two i'm going to talk to your manager again and go don't let me guess this person can be a three again this next term so you don't have to put them on a performance plan so we would after performance reviews always go through as a senior team like okay i can see from the way these people these couple people or these eight people are bouncing from two to three to back to two to back to three like you're just trying to not fire people and i can see that your curve is inflated and blah blah blah so we would just be super hardcore about that's like you can't
44:54Brian Halligan:do that you know let's talk about competition for a second you had some i mean you're competing with with facebook yeah they were the juggernaut that we just had the hardest time like in like tomorrow i'm speaking at another company meeting i'm not gonna say the name of the company but they're they're going to be competing with open ai and anthropic almost every board room i'm in is talking about that everyone's anxious about that employees are anxious about that advice about that first of all you have to acknowledge it and then you just have to i mean one of the things i would always do is like they're like huge and mark is the most competitive person on the planet trust me when i tell you like they don't like they don't say to themselves oh whatever twitter won that thing that's fine they're like that can never happen again yeah so we have to be like Like, and we're way smaller than them and have far fewer resources and can, you know.
45:47And so it was just like, we just have to be, we have to think about them. We have to talk about them, have to understand what they're doing, and have to try to figure out how to out-hustle them. And Adam Bain on the revenue team was great at that. He would come into company meetings at Consumer Electronics Show at the beginning of the year and go to one of the first big customer meetings. like let's say it's Unilever. And he would sit down with the CMO from Unilever before the meeting and say, how'd the Facebook meeting go? Oh, great. What are they psyched about? What are they psyched to show you this year?
46:24And then he would learn all that. And then he would go into the meeting with the Unilever and say, even if we had a bunch of things to show them, he would say, we have some things we want to show you, but we really want to spend the next two hours today just understanding your business and what you guys are concerned about, what your problems are. I mean, knowing that she just told him that the Facebook people came in and showed us this and this and this and weren't asking those kinds of questions. Now, Facebook wised up to that over time, et cetera. But Adam had just come up with a great way of thinking about how to compete with this juggernaut.
46:53And the juggernaut's rolling out new things every quarter. That's really good. It's just good salesmanship. He's like, I can't compete with their eight new things and their micro targeting and blah, blah, blah. So I'm going to totally come at it from a different angle. And it was just smart about learning how to do that by talking to the customer beforehand.
47:10Brian Halligan:You guys picked the advertising model to make money. As you look back at that, good call? Yes. Advertising is undefeated. The ARPU is higher. It just is on versus subscription revenue, et cetera. I think we would do the same thing over again. Any other, as you look back, like, man, I wish I had a do-over on that one. Oh, yeah. We tried to buy Instagram the month and a half before Facebook bought it. And by the way, for a much higher percentage of the company, Facebook's offer is famously a billion dollars. And I think it was 700 of stock and 300 million of cash. They only had eight or nine employees at the time, Mike Krieger and Kevin Systrom.
47:50But we knew well before that, like these guys are – Kevin is an extraordinary product manager. Kevin and Evan Spiegel, I think, are probably two of the best product thinkers in Silicon Valley. And so I knew that. And well before Mark made his offer to them, I pulled Kevin, went out to dinner with Kevin and Mike and told them we wanted to buy the company and would end up giving them basically well over 10 percent of Twitter. And, you know, something equivalent to 700 million in stock and were maybe valued at five billion dollars at a time. and, you know, I would have gone and could I go back there and talk to Kevin?
48:30I would say, like, you can run the company when I leave. Like, congrats, you'll get to BC. I mean, may still not have done it. And I would also say, also, I'll go borrow$300 million from JP Morgan and give it to you. I see. And you can have it all and we'll pay them back later. Because that was a game changer. Once they had Instagram, I was like, oh, man, we're like boxed out on that is the future. of rich media, social media feeds. We have Vine, but it's much, much smaller. And they're now going to come at us on Instagram with video, which of course they did. And that was sort of checkmate.
49:11Brian Halligan:Other regrets. Any regrets on, man, the content moderation stuff has been in the news over the last five years. It wasn't as hot while you were there. As you look back at that, regrets? It was always like, the thing I'll say about content moderation that people get wrong all the time. It's like, this is really easy. Just prevent people from doing that. They're like, okay, well, that is a lyric in a Kanye song. Can you not tweet his lyrics or whatever? Or it's easy. I'll give you a specific example that I always think highlights why it was such a pain in the ass. And it's so hard and you can't just come up with a set of, these companies try to come up with a set of rules and like, well, if it violates the rule, you have to kick it off.
49:51And if it doesn't violate the rule, you can't kick it off. Like that's you just can't think about it that way. These things are so subjective. So ISIS, the terrorist organization, captures three pilots from some some air force and puts them in cages, basically on a beach and lights them on fire and kills them. Basically burns them to death. And they post these to Twitter photos and videos. And my general counsel comes to me and goes, hey, these terrorist accounts are I'm like, great. She's like, suspend the accounts, right? Like, yeah, of course. like right away anyone that posts the you know media of these pilots being lit on fire like suspend the account well the freaking new york post an hour later post the picture huge photo of this pilot being lit on fire and suspend you know and then i get this like hey what you suspect you know kara or someone like why did you suspend the new york post what we didn't suspend the new York Post.
50:50Yeah, you did. And you're like, okay, wait, I guess the New York Post can do it, but now who can't do it? And that was one tiny example. It was just so, so infinitely hard. And you just can't, my, the big, if I could go back again, is you just can't have these hard and fast rules. There has to be, again, pushing, you know, having operating control and somebody with an understanding of the situation, like our GC, you're going to just have a bunch of judgment calls and you're going to get a bunch of them wrong, and that's life. And like after your tenure, and like I don't know what to believe,
51:31Brian Halligan:but it looks like there was a lot of conversation between the Biden administration and that group, and then a lot of accusations from Elon that that group was just very left of center in their orientation. Any reaction to that? Was that the case when you were there? I mean, yeah, probably it was left of center. But I don't think that I don't think when I was there that I don't think it impacted the way we thought about abuse. I mean, it wasn't like you, you know, we didn't have any like, for example, we didn't have any like, oh, you're not allowed to dead name trans people. I like that stuff was all post me being there.
52:10At the time, it was mostly what we were dealing with. or what kind of happened after you left yeah the the yeah the stuff we were dealing with and i went when i was there were ridiculous amounts of russian bots which at the time were not election stuff it was maybe they were preparing for it to preparing the groundwork for 2016 but it was mostly like fishing attacks and just massive bot farms that were doing fishing attacks on on people and trying to hack into their accounts or get credit card information etc most of the ceos who have been
52:40Brian Halligan:around a while i've got a shit ton of bad press you got a metric ton of bad press it must i got a bunch of bad press it impacted me i tried to show a face like yeah but yeah it was soul crushing to me yeah how did you handle it i don't know i like i had been a i had had the fortunate um opportunity to be a performer and do improv comedy and stuff and audition for snl a couple times before I went back into business. And I had been like, you know, I remember I was at the Adelaide Comedy Festival with my improv group, and we had this midnight show at the Opera House, the Adelaide Opera House. Adelaide, Australia?
53:20Yeah. And the crowd is hammered drunk, maybe 1 ,000 people. And it's like an hour and 10-minute show, completely improvised. we get on stage and like five minutes in the crowd starts yelling like you suck get off and like man we got 80 more minutes or whatever and uh and uh so i don't know i just became resilient to like oh well i see yeah like did it hurt inside i don't know like we got good
53:52Brian Halligan:i remember my daughter called me the good press never hit for me no no i'll tell you i'll tell My daughter called me. This is at the end of 2014. So 2013, go public. IPO is successful. Everyone's super excited. Go yay us. And there's some, you know, these stupid awards that come out, come out. And like CEO of the year, Dick Costolo. End of 2014, my daughter texts me. She's like, I have bad news and good news. And I was like, what's the bad news? She's like, Yahoo Finance says you're one of the five worst CEOs of 2014. It's like, what's the good news? She goes, nobody reads Yahoo Finance. Okay, got it.
54:38Brian Halligan:Okay. I just felt like, I don't know. It's like you're like, okay. And I'll say one last thing on it. I've said this a bunch, but I think it's important. I got invited to go to like the Vanity Fair Oscars party one of the year. By the way, that must have been cool. Well, I got invited to go. I didn't go. And I told my daughter, good question. So I told my daughter, I don't want to start going to a bunch of stuff that I get invited to because I'm the CEO of Twitter. Because then I'll be like, oh, I don't want to not be the CEO of Twitter because I won't get invited. So I went to the NBA All-Star game because I knew Adam Silver and he invited, I felt like it was a Dick Costolo invitation.
55:16I was like, I'll go to things I get invited to because I'm Dick Costolo. I don't want to go to things that the CEO of Twitter gets invited to because then I'll be like. Wasn't it part of your job? no i mean i mean going to the white house sure like hey the president wants to talk to you about you know edward snowden and abuse on the platform and what are we going to do about terrorists using the services yeah you got to go to that as part of the job but go into the like go into these things you know like the oscars or whatever like i don't know i don't know any of these people
55:46Brian Halligan:they don't care about i totally would have done it yeah i totally would well you would have been standing over in the corner going like no one's talking tom totally nobody's tom cruise isn't talking to me. It's exceptionally rare these days that somebody bring a founder led company is replaced or just that they don't hire the adult external CEOs. Is that, should it be happening a lot more? I think it goes in waves. And it's not, doesn't happen at all these days. Yeah, I know. I think it goes in waves and I think it will continue to be, there all, something will happen and people will start going, you know, we really need for these companies that are making, you know,$4 billion in revenue after three years and the 26-year-old founders are, they'll just, something will happen and there will be a wave of, you know, operating executives coming back in and run some of the companies.
56:39It happens a little bit like Slootman and Sloan, you know, they look like. Pretty rare. Yeah, yeah, rare.
56:44Brian Halligan:Even the public companies like MongoDB, but I'm on Workday recently, but like maybe one a year. Yeah, it's true. i do think it goes in waves we'll see if it we'll see if it okay you're a vp a blah blah company and you want to be a dick costello what should you do you want to be that adult you you oh you want to be that adult i want to be you when i grow up i'm gonna do it anthony noto did you know when he was cfo twitter he started it like telling making it clear to you know executive recruiters like i want a ceo role like start you know when you start cnc roles i i might not get one right away but like i want to i want to talk to you about ceo roles when you get them i got it get your name out there and just i never and anthony would tell you this too about his own career i never took like a risk that i didn't you know that i wasn't super psyched i took even i was like trying to get on snl and wasn't successful it ended up benefiting me down the road because it's like all right like like live tv on cnbc are you okay doing that i'm like look at the camera like i've got booed at midnight in australia by a thousand people i can look in the camera and talk about should all ceos take my co-founder took a comedy class in business school yeah it really helped him yeah being on stage and you know being uncomfortable being on stage make i mean you got you stand up at all hands meeting we're like i know exactly what i'm gonna say at the all hands meeting i'm just gonna talk about the priorities yeah that's easy after doing that okay let me give you a fun one hit me is san francisco passive aggressive is everyone passive aggressive our CEOs passive aggressive.
58:16I think there's a lot of passive aggressiveness. I think I know I know the person you talk to and I think and I know the other companies has been at. I think he's generally right, but there are some great exceptions. I think the Collison brothers at Stripe are. Are both that rare combination of. Really, really widely read and and and and polymaths and have a broad perspective on humanity and biology and the human condition and are forthright communicators and are neither passive-aggressive nor hyper-aggressive. They're just forthright and straightforward and blunt, and I think those guys are great.
59:03And I feel the same way about Reed Hastings, a totally different executive at Netflix. Reed is always like, this is just how it is. You know, I like I'm not I don't I'm not trying to be mean about it.
59:16Brian Halligan:This is just the way it is. And I think it I think you rhyme with read in my head. Yeah. Yeah. Yeah. I take that as a huge compliment. I love that guy. I always thought those three people, John and Patrick at Stripe and read at Netflix are extremely self-aware. I remember it was a table with read at a dinner once and he went around the table and said, I want to hear everybody's opinion on this. how much of your success do you think is based on your DNA and how much of it is based on like, I just learned how to kick ass and be amazing. And I kind of, I was like, I think I know where he's going with this.
59:53And of course, when he got around to himself, he was like, I think it's basically like 80 % DNA.
59:58Brian Halligan:Interesting. How would you answer that? I think similarly. And I think that's a result of him being - How much is luck versus skill? Yeah. I think there's certainly a bunch of luck, but I don't think he was saying luck versus skill. I think he was sort of saying like, you're not like some, you know, exceptional person who came out and like, I'm going to fight against the, like, it's basically encoded in you to be this way. And, you know, it's, it's ended up helping you. And sure, there's like 20 % luck along the way that put you in the position to get this role that you might not have otherwise had, but you were always going to do something like this.
1:00:30Brian Halligan:Okay. You brought up some good CEOs. The CEO rulebook feels to me to be changing. your take on how jensen huang runs that with like 60 direct reports no one runs yeah criticizing yeah he's got a whole different playbook the thing that surprises me is i work with all his ceos yeah nobody's copying him yeah i think's interesting your take on that i go back to the jeff bezos comment to jack dorsey jack there are lots of different ways to be successful i think that i think that the mistake that ceos make is they read the walter isaacson book on Elon Musk or they read the one on Steve Jobs and they think this is the map.
1:01:09Brian Halligan:Yep. And Walter's just left out a whole bunch of stuff, you know, and that's not. Did you have an archetype? No, I didn't have an archetype. Steve Jobs was mine. He tried to copy everything he did. I did it quite poorly. I mean, it goes again to the like, well, Steve says you have to be an editor and you said and, you know, and Jeff saying like, oh, yeah, well, there's lots of different ways to do it. I think the and the reason I say that about the books is not just because they're more mythology than they are. What really happened? Some of it's, of course, this happened, but it leaves out a bunch of stuff.
1:01:42But more importantly, you just if you try to be someone you're not, nobody is fooled. Like you think people are fucking fooled. Nobody is fooled. Everyone knows you're spinning them or you're playing some role and you're not yourself. And nothing is more miserable than trying to be someone you're not. One of the things I used to do, I used to do this in my management class, actually, during one of the NBA finals back in the 90s. This reporter's in the Houston Rockets locker room. And it was at a time where Charles Barkley did this ad for Nike where Charles dunks a basketball and he looks at the camera and goes, I ain't no role model.
1:02:17Something like that. And this reporter's in the Houston Rockets locker room and asks Hakeem Olajuwon. He wasn't wrong. He wasn't wrong. He wasn't wrong. Although he appears to be on Ozempic or something. He's got to have his suits retailed. This reporter's in the Houston Rockets locker room and goes up to Hakeem Olajuwon and says, you know, Charles Barkley says that kids shouldn't, you know, idolize, look up to NBA players, role models. What do you think about that? And Hakeem Olajuwon goes, I'm happy to be a role model. I love being a role model for kids. He's like, well, what do you? And Hakeem says, well, here's the deal.
1:02:51Charles is a different person in public than he is in private. it. And so he's got this anxiety and tension in his mind about whether he's supposed to be public Charles in this moment or private Charles in this moment. I'm always the same person. So if people want to look up to me as a role model, that's fine with me. I just think that it's nothing but misery if you're trying to, you know, look at some written down playbook of how Steve Jobs did things. And I got to go do that when it's almost him. It was impossible for Steve to do it almost. And you're certainly not going to be able to do it.
1:03:23You'll be miserable trying.
1:03:24Brian Halligan:Okay, last question I have is like, the Twitter board, man, there was a lot of frigging drama there. Tons. So much. So much. You're building that, you're a$100 million company going to$400 million. You're building a board. Advice, like, should you bring in independence early? Should you wait? I had two board members that were immensely helpful to me. Peter Chernin, who had brought in from News Corp as an independent director because he'd managed tens of thousands of people, and I need someone with operating experience, global operating experience. and Peter was great at always like always did the sort of the Jeff Bezos let's talk about this from the user's perspective instead of like how are we going to do xyz he would always back up and say you know wait if I'm the chief if I'm the chief user officer at this company you know and I'm thinking about this from the and so that was immensely helpful in lots and lots of cases And then secondly, Peter Fenton from Benchmark would always help me interview candidates and either close them or help me with, hey, how should I think about this candidate?
1:04:27And having someone on your board who's not in the day-to-day at the company and who can also give the candidate a sort of a third-party perspective on why I think this is going to be a monster and why I think you should do this was like crazy helpful and helped convince numerous execs like Adam Bain and Anthony Odo.
1:04:47Brian Halligan:Do you bring in – okay, you're at$100 million. You're doing your Series B. Do you bring in an independent? What happens now is they wait right before the IPO. No, I think it's helpful to have people with operating expertise in there much sooner than that. Okay. And just while we're on IPO, you took Twitter public. It's very hard to take companies public. It's become very unfashionable to take companies public. I would have kept it private longer if I could go back and do anything over again. I would have too. It's just so much easier running a private company and not having to like, okay, well, that's going to mean we're going to miss the revenue number by a percent.
1:05:22It's the right thing to do, but the employers are going to be running around like, what's wrong when the stock goes down 8 % after hours? And as you know, you don't have a daily ticker that the employees are freaking out about when you're a private company. And it's just a lot more you can be. it's so much easier and stress-free to focus on the long-term as opposed to, okay, now we have to make a long-term versus a short-term to have a discussion about this because everything's going to go sideways if we do this in Q1 instead of blah, blah, blah. You get it. It's just a lot easier to run a private company.
1:05:59Brian Halligan:I wanted to talk to you for a long time because you are kind of a rare species these days. The adult CEO brought into a hyper-growth company and you delivered. Thanks for coming on the pod. Thanks for having me. Okay. I thought Dick was great. It's a masterclass on how do you scale and be a terrific scale up CEO. There's a few things he talked about that I think are worth reviewing. Some of which I did, some of which I wish I did when I was CEO of HubSpot. One thing he did that I totally did was management by walking around. I'd wait until like seven o 'clock at night and I'd walk the halls of HubSpot through the dev organization support sales who was around and really hear what what was happening that was super useful for me it was great context and it was also good to see who was from the midnight oil um i liked his feedback around giving tough people tough feedback i was never very good at this and his advice is good it's you know the night before you're going to get feedback for that tough person it's not great feedback you write it down the night before practice it in the mirror I think that's good advice.
1:07:00Brian Halligan:And when you deliver it, you deliver it and you sit in silence. No fluff. You sit in silence. Really hard to do, but I think that's great advice. He talked about killing committees and using DRIs. A lot of the CEOs I've interviewed are talking about similar things. Particularly important as you've got silos in your organization and the important stuff cuts across boundaries of those silos. He gave a great quote from another pod guest, Ben Horowitz. He said, make sure everybody understands what you understand, not just the what, the why and what success means for them personally. Priorities without context are useless.
1:07:41Brian Halligan:I thought that was a gem from Ben, and I thought it was really cool that he repeated it. He accused the Silicon Valley of being passive aggressive. He said he's not. He's aggressive. I think that's good advice. like a lot of CEOs he says you should hire fast and fire slow he didn't fire slow almost no other CEOs don't fire slow I did not fire slow and so he wishes he did that some gems in there hope you enjoyed it and looking forward to having you in the next pod
From the publisher
Dick Costolo took over as CEO of Twitter in 2010, inheriting what he calls "the drama queen of hypergrowth companies." Hired as the adult in the room behind founders Jack Dorsey and Ev Williams, Dick spent five years dragging Twitter from a chaotic collective into a public company, and learned a scale-up CEO playbook in the process.
We get into how he killed group decision-making and replaced it with what he calls "bias to yes"—only your direct manager can tell you no. Why he stopped solving problems with processes ("the launch checklist was 17 pages long") and started solving them with DRIs and operating control. How he managed by walking around the engineering floor at 9:30 PM to figure out what was actually getting built. And the Steve Jobs trick he stole from Pixar for finding out what's really going on inside a team.
Dick is candid about the misses, too, including trying to buy Instagram for around $700 million before Facebook did, and his own struggles to fire fast. When I was running HubSpot, I fired slow almost every time and regretted it. Dick did better, but he'll tell you it never gets easier.
If you're scaling past 150 people and feeling the organizational barnacles build up, this one's for you.




