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From polar expeditions to Twitter’s Longform team, Tony Haile knows how to lead — and when to step back. Former CEO of Chartbeat and Scroll, Tony is now Senior Director of Product at Twitter. This week, he joins Gina and Paul to share wisdom on managing the managers, knowing your weaknesses, and successfully integrating a team after being acquired by a bigger player.



Paul Ford Whenever I hear that metaphor, I just think, but the fox would eat the hedgehog, which I know is not the point. [Everyone laughs.]

Tony Haile Have you tried to eat a hedgehog?

PF I mean, yes, actually earlier today. I’m in Brooklyn. There’s some very interesting restaurants.

TH Good with garlic. Yeah.

[Intro music fades in, plays 10 seconds, ramps up.]

Gina Trapani Hi Paul.

PF Oh my goodness, Gina Trapani, how are you?

GT It’s great to see you. It’s been a while.

PF It has been a while. I don’t see you as much as I used to.

GT No, we don’t. We’re kind of doing different things. It’s good though. It’s important for me to consult with the former CEO of Postlight because I have no idea what I’m doing. [Laughs.]

PF Oh, no. We don’t say that. We say that it’s a constructive learning environment. For people at home, it’s been really fun because I think Gina used to look at me and go, he has no idea what he’s doing. And now she’s taken the job and that’s the job actually. There’s nothing else to it. [Everyone laughs.]

GT It’s not knowing what we’re doing and managing that?

PF How’s it going? How’s technology leadership treating you these days?


GT Oh man. It’s a hell of a thing. It’s a hell of a thing.

PF It is.

GT It’s a great, great privilege and a great challenge on a daily basis, Paul.

PF It’s hard. Running an agency is hard. You’ve got to feed the fire. Got to keep people happy. It’s a lot, but you have a good partner in our president, Chris LoSacco.

GT Great partner in Chris and fun and interesting people that we work with every day, our team and our clients, we’ve got some really smart, great clients.

PF What an amazing segue. I just can’t believe you got us there so quickly. We should actually disclose this is a client and we have taken money from this person to do work for them. We’re not going to be able to really disclose much about that work. So just get ready, everybody.

GT Very mysterious.

PF Welcome to a world of mystery. But this is a friend of the firm, a friend of the media industry. Probably the only technologist that the media industry doesn’t just unilaterally hate. And that is Tony Haile. Tony Haile, thank you for coming on the Postlight podcast. Let’s get the media industry to hate you. Let’s get in there.

GT Hi Tony.


TH Yeah, I think historically, when I was CEO of Chartbeat, the media industry was pretty much 50/50 split on whether they hated me or not.

GT Can I just fangirl Chartbeat for a minute because Chartbeat—we used it on Lifehacker. It blew my mind when I saw that thing. I was like, this is it. This is the pulse of my audience. Like I’m looking at it right now.

PF But that’s because media people, media people had never actually considered that the little ball could move around on the screen. We’re just going to jam the words in the hole and hopefully it will all work out. And then Tony shows up with Chartbeat, which for people at home who don’t know, it was an analytics tool focused on close to real time analytics, who would tell you how your article was doing. Tony, just let me explain your own software to you. Give us a little bit of that before we get to what you’re doing now. So Chartbeat was a company that you founded, correct?

TH I would always say that I came in a little late to the thing really. There’s an amazing, amazing creative called Billy Chase. He’s as much an artist as he’s a technologist and a product manager and he built


PF Sure, a classic.

TH And so he’s just incredibly creative. And initially what he had built is he’d built something called Firefly, which was something where, when you went around the web, you could see the mouse cursors of other people as they kind of like were also on that site in real time. And then you could chat with them. I think Business Insider called it a more ADD version of Twitter, if that’s possible. [Gina laughs.] And the challenge with that particular one was the number one challenge was that someone would see someone else’s cursor as it was kind of wandering around the page and they would take their own cursor and they would go and try and hump it. [Gina laughs.]

PF Yeah, yeah.

GT Because of course that’s what you would do!

TH And so that wasn’t going to be a billion-dollar business. But people really loved seeing what was happening on the site in real time. And so Billy started kind of building out the core of what became Chartbeat. I came along, I was an illegal immigrant who just launched a coup against the CEO of the startup I’d been involved with and had been fired and was in New York because there was a girl who would let me sleep on her floor who’s now my wife, which kind of worked out for me. And met up through a guy called John Borthwick and Andy Weissman. Met up with Billy. And then from there kind of took it on. And Billy actually left very shortly afterwards to go and try and do Turntable and other things. And so I kind of like, I was kind of gifted this early kind of project from Billy and then had to kind of work out what to do within Room.


GT So then what happened? Like tell us what happened.

TH Well, this one was actually a kind of super interesting problem to try and solve from a kind of product perspective, because this wasn’t some situation where Chartbeat could fail because literally who else would hire someone like me to do anything. We were a new little tiny startup within Betaworks at the time. And the biggest problem was that we were paid for analytic service at a time when Google Analytics was great and free and had almost a hundred percent kind of penetration of the market of interest.

GT Right.

TH And so I remember very early on Google like said, Hey, we see you’ve done this new kind of little prototype thing, come visit us. And basically, I didn’t realize why they wanted to see us.

GT Uh oh.

TH I was like, oh, they must be super interested in our tech. They just wanted to laugh at me. They brought me into a meeting where three of them were basically like, you know your thing doesn’t even do this, right? And just kind of like went through—

GT The negging meeting.


TH It was kind of an amazing—it was an amazing session, but they were kind of right. In that we had this huge analytics problem and we had to try and work out how we were going to survive in the market. And I went to see a very wise man called David Kidder, who was CEO of Clickable at the time, which was a kind of easy way to serve ads in the Google world. And I asked him, am I screwed? Am I completely screwed? And he said, possibly, but here’s the thing—if you try to compete with Google and just try and try to be a little bit better, Google will just get a little better. If you try to build better funnel than Google—funnel analytics—Google will just build better funnel analytics. So try doing the exact opposite of everything that Google does and see where it takes you. It may make the world’s worst analytics product, but at least you’ll be different. And that’s kind of where we started is like, okay, let’s make a list of all the things that Google Analytics does. Let’s do the exact opposite of that. And then kind of explore if there’s a new user and a new user case for analytics?

GT Wow.


PF Give me an example—what’s an opposite of something Google Analytics does?

TH Sure. So like Google Analytics gave you full history of all your analytics. Early Chartbeat didn’t have any of that. Google Analytics was focused on your pathway from page to page to page. You couldn’t really do that in Chartbeat. Instead, we were focused on what was happening within the page at that moment in time. Like Google allowed you to sort and filter and do all kinds of functions again, single page, none of that. And one other thing for me that was always interesting, like with Google you—because if you’re an analyst, you need to be able to export the data. You want to be able to put it in, do your own spreadsheets, do whatever you want to do. We didn’t allow any export. We had an API. And the reason why we didn’t have any export was because we didn’t know how people were going to use the product. And we wanted them to get annoyed and email us and say, Hey, I want to be able to do this thing and I can’t. And if they could just take data out and so forth, we wouldn’t know. So we basically created a whole bunch of constraints for ourselves around the product and then kind of put it out there in the world to kind of see what would happen and then tried to learn and adapt from that.

GT I mean, it was really smart. I remember it being so kind of mind blowing to me because it was so different. This was actually good advice? I don’t know, in retrospect, did it feel right to you?

PF Let me diagnose what you just said for one second, right? Cause it’s, you’re doing the opposite of Google and Google is trying to solve the problem for websites, right? Like my real estate company that has listings and I want people to come in and register and blah, blah. And Chartbeat, I remember the first time I saw it—it was like about one article and what that article was doing on the internet and who was linking to it and it was alive. And then you could react and turn that into—you could do your job with it. And your job as a journalist is like, I’m going promote it on Twitter. I’m going to talk about it over here. I’m going to email it to the PR people and tell them that it’s getting some lift and so on. And that was a real revelation at the time. Because that kind of real time action, which is how news works, is very different than how Google Analytics would see the world, which is like this giant infinite funnel.


TH Yeah. I think this was like the first thing that was profound for us was realizing that there was a different audience for analytics than the traditional audience.

PF Yes. And it wasn’t actually even journalists initially it was, it was actually EA—Electronic Arts—and they signed up for Chartbeat and put it across all of their sites and they were spending like a million dollars a year on Omniture. And I had no idea because for us, Omniture was this, which is Adobe’s kind of analytics suite—

PF Oh man—Omniture.

TH It’s a huge beast. So we were just like, there’s no way that anyone who used that would ever want to use our little service.

PF If you want to make developers upset, you can just whisper Omniture in their ear. Like if you meet someone who is like, yeah, I do a lot of frontend web programming, just say, ever use Omniture? And the next 45 minutes of your conversation is taken care of.

GT Watch faces just twist.

​​TH Always pour whiskey before you ask that question

PF Right now, maybe it’s gotten better. Maybe it’s—I haven’t used it in a while.

TH I’d say that Adobe has been doing a lot of really good work recently and I hope that’s been extended to Omniture, but like for us, because we didn’t know why they would be using us. We called them up and we said, look, you realize you have Omniture. Why the hell are you using us? And they said, the analysts all use Omniture. Everyone else looks at you. And it was that notion as well. So we were coming up at the same time as the kind of rise of the social web, that notion of like frontline people being able to react to data in the moment, it was a different audience, a different use case. And we were just lucky enough to unlock that at the right time.


GT Yeah. I mean, this was me and my editorial staff for sure.

PF So fast forward a little bit, you created a company called Scroll. We should talk about what that does. And then Scroll was recently acquired by, um, Twitter, I guess is the right way to put it just Twitter Inc. And now you have a product role at the big blue bird.

TH Yeah.

PF First of all, what the hell do you do all day? When you’re a high-level product person at Twitter—we’ll get to Scroll in a second. I’m just like, what do you do, Tony?

TH I think a few things. There’s what I should be doing. And what I do, I think.

PF Well also at a high level you could seriously do nothing constructively if it’s the right kind of nothing, like it’s very Zen—

TH Yeah. And sometimes it is the desire to—when you desperately want to comment and so forth—is to hold back. Like I still remember something from like Marshall Goldsmith. He said like, you can go along and you can like screw with something or you can give a comment that might make things 5% better, but in making it 5% better, you’re taking away the kind of autonomy and ownership of the person below you who’s doing it. And sometimes it’s just for the long-term health of the product—

PF You want them to learn. You want them to feel that sense of ownership.

TH Yeah. You want to just kind of shut up. And I think so, for me, I think there’s a few things when I think about my level of product management. Because I’m not in Jira. Any day that I’m running a PID is probably a bad day.


PF That is really true. If you touch the thing, oof.

TH It’s bad. My job is to try and provide clarity in all possible senses and also to be able to kind of connect what any individual product manager is doing into the wider picture. So that’s my first goal, is always to provide that clarity. And so that each PM who works with me or each team that works with me is able to kind of say like, I know what I’m supposed to be doing. I can be creative in service of that because I know the constraints I’m dealing with and where the opportunities are. And I know how it funnels up to the overarching strategy that we have as a company. That’s the first—

PF So describe your org to us a little bit, because a lot of Postlight podcast listeners are PMs who are figuring out their careers and where you’re at is one of the places I think they’d like to be. So what does it look like from your point of view and what’s your job actually? Who are you Tony?

TH Sure. So I’m the senior director of product. 

PF Okay. 

TH Which means I get to run a team called Longform, which is Twitter’s hilarious name for anything greater than 280 characters. I genuinely enjoy that fact so much. [Gina laughs.] It’s just glorious. 

GT Amazing. 

TH Longform is a little bit unusual within Twitter in that I have a slightly more kind of GMish role than a normal PM. I think we’re the only part of the product org that has its own dedicated commercial team. And we have our own dedicated editorial team as well. So it’s a slightly different thing in general, but if you think about the way my org works. So I run the product org, I run the commercial team and I run the editorial team. They all report up to me. I then have a kind of a staff. I have a group product manager who’s wonderful because all of my deficiencies, he balances out, like I can be the unfiltered asshole. He’s like the calm wise dad. And it’s incredibly helpful. 


PF What’s his name? 

TH Eric Wuebben. He was actually a founder himself. He founded a company called Highly and was acquired by Twitter a few years before me. And was actually really the kind of the founder of Longform, like I just came in with an acquisition and got to jump into the mix. But this Longform is originally his vision. So he’s been a great kind of product partner.

PF I feel like this is a really critical lesson though, that people should take away. You can spend a lot of time in search for a unicorn leader or you can make a Frankenstein leader out of multiple people who will actually get the job done because the unicorns aren’t real. 

TH Yeah. I’m a big believer in this.

PF You always need that balance.

GT Yeah. Great partnership or a great trio. Critical.

TH Yeah. And, and also of course, knowing when to step back and let someone else be CEO, correct?

PF No, exactly. Right. There’s a lot going on with what you just said obviously. Right? [Everyone laughs.] We’re about six months into the Postlight transition and—maybe no, seven—and it’s been really interesting to watch because I think Gina has become way more aware of where I was at. I think what’s so tricky about these roles. You’ve got it. I’m seeing Gina sort of wrap her head around it. It took me years to wrap my head around it—is that you have a kind of internalized portrait of yourself and you might have started as a practitioner. You’re pretty good at getting stuff done. But the way that stuff gets done has nothing to do with your basic abilities. It’s just kind of like, it’s this space and you keep a lot of balls in the air and people look at you and they’re like, what are you even talking about half the time? And yet, somehow the whole thing is moving forward. And people tell themselves stories about you and some of the stories are positive and some of them are negative and some of them are completely out of keeping with the narrative that you have. And that can all get really, really surreal. And so that’s a very strange job. And there are moments where I get to do things like write a little bit of Python code where I just am unbelievably relieved that I was able to like—no, because I [Everyone laughs.]

GT I mean, you run it and it either works or it doesn’t. It’s a very quick feedback loop. If you don’t get those kind of feedback loops when your job is to align your team with the strategic vision of the company, which is the thing that Tony said he does for his PMs. And I was like, yeah, that’s the leader that everyone wants. And that’s the leader I aspire to be.

TH I was thinking as you guys were chatting at the beginning of this, you talked about this transition and that now you suddenly understand what I was doing. You have a whole new insight.

GT Yes. 

TH And I have to confess. I have long encouraged members of my team from Chartbeat and Scroll on this—so please go start your own companies. Can I help in any way? And encourage entrepreneurial instincts. And we actually had I think it was double digit percentage of employees at Chartbeat at my time, went on to kind of become a founder of their own company. I was so excited. 

GT Oh wow.


PF That’s very cool.

GT That’s something to be very proud of.

TH Yeah I am. But also here’s my secret: every single one of those people after having founded their own company comes back to me, goes like, ah, I get it now. They just have more of an appreciation for the shit they used to give me. And so I’m like, it’s both me trying to help and support them. And it’s also my revenge. [Gina laughs.]

PF Oh, it’s totally revenge. No, it’s beautiful. It’s a wonderful feeling.

GT It’s so true. 

PF It’s not like some actual secret, mysterious knowledge that people don’t have that you get to, you have some like some capitalist miracle you’ve pulled off and you now get to point and say, I know that. It’s just like, you’ve just been humiliated in a really specific way while having power. And it really is a strange feeling, right? You’re just like, your spouse looks at you and is like, what the hell are you complaining about? And you’re like, oh, well, it’s a good point. 

GT This is getting real.

TH I suddenly started reading a lot more kind of Zen and philosophy as a result of being a CEO. 

GT Yeah. 

TH And I found that it really helps. And to your point about the unicorns earlier, when it was like, try seeking out the kind of that unicorn person who can do everything, it’s like everyone is going to have a certain level of strengths and a certain set of weaknesses. And you can spend your time obsessing over the weaknesses. Or you can say, I’m going to give you everything I can to make your strengths awesome. And then I’m gonna go hire this other person over, and they’re gonna do this bit that they’re really good at. And I’m a big fan of kind of like meshing those kind of people together


PF I’ve met a lot of leaders now and you could broadly cluster them into two groups. And I think one, I would call like the narcissistic fireball, who is just someone who is able to create an unbelievable amount of heat and light and people kind of go up to them and get singed. But because the fireball is moving so quickly, an enormous amount. They just do so much damage that things happen around them. And then everybody else are people who like genuinely, if you say, Hey, what are your worst qualities? They’re like, hold on a minute. And then thump, a 300-page book lands on the table. And they’re like, you know, and this used to be a lot shorter. Right? And yet here we are.

TH Here’s the thing though, Paul, I think you kind of have to be both.

GT It’s true.

TH There’s a wonderful book by John Lewis Gaddis called On Grand Strategy where he talks about hedgehogs and foxes from the kind of Berlin story.

PF So the hedgehog knows a lot. Those little—

TH The hedgehog knows one big thing. Hedgehog knows one big thing. And the fox knows many small things. And in the context of strategy and so forth, he talks about Xerxes building a bridge. He was like, I’m going to do this. Nothing’s going to get in my way, I’m going to bring this huge army across. He was a hedgehog in the kind of classical sense. But there were other people who are much more kind of like adaptive, opportunistic. They don’t think about ground strategy and so forth, but they’re just kind of like, they’re just tactically kind of trying to find the water flowing down a mountain. It’s the best pathway. And you’re just kinda shifting around. There’s no real plan other than down. And there are challenges with both things. That egotistical kind of creates energy, creates movements, creates pace, creates focus, but is often also blind and finds it very difficult to adapt to changing environments. And one of the things when you’re building products or startups or whatever, is you’re dealing in an environment of complexity that’s constantly changing. So you have to be a little bit of a hedgehog and you have to be a little bit of a fox as well.


GT Yes. I’d never heard this story. So I appreciate you telling me this one. My progression was personal productivity books to business leadership books to Buddhism books. Like those are the three stages I think of leadership. And in the business book layer, I definitely noticed that there’s like, okay, there’s two types of leaders and one is this. And one is this. And you have to be a combination of the two. So I co-sign, I think that that’s true. You kind of have to be a bit of a chameleon.

TH It’s a constant reminder to me of how I want to show up. As a tall white male, I’m genetically programmed to interrupt people. [Gina laughs.]

PF You sure are! So am I! [Gina still laughing.]

TH And—

PF Hold on Tony, hold on! Let me get in there for a minute.

TH It’s a real, it’s a real challenge. So like—

PF How tall are you?

TH The government thinks I’m 6 foot 1, but I’m pretty sure I’m taller than that.

PF I’ve seen you. I’m six three.

TH Okay. So I’m medium size.

PF Yeah, there we go.


TH But like every morning I kind of write down to myself. I write like, shut up. [Gina laughs.]

PF Yeah. Yeah.

TH My three Ps: it’s like preparation, process and presence. Those for me are like the core. If I’m going to show up for something, it’s like, I want to make sure I’m prepared for it and I’ve thought about it in advance because I’m not very smart and I can’t think on my feet. I’m trying to find a process to make this scalable. And when I’m there, I want to try and be present. It’s also what I expect from other people when they’re in meetings as well. I expect them to be present. Otherwise we’re all just wasting our time.

GT I love this.

PF I could never, it’s very hard for me to be—I’m not light on my feet for a lot of obvious reasons, but in general it takes me until tomorrow to know what the hell I think. Right?

TH Completely.

GT Yeah.

PF I know. So I need to be near good fast operators who are light on their feet. Otherwise I’m not really effective. Cause then the next day I’m like, well what about this, that and the other thing. And everybody’s like, oh, okay. That makes sense. But in the moment I’m tongue tied, I’m just sort of like mreh.

GT Yeah, perfect response like two hours after the meeting. 

PF Yeah, absolutely. That’s what Slack is for.


TH What’s that French phrase? L’esprit d’escalier?

PF Sure, absolutely the French phrase I would use. What’s that mean, Tony?

TH It’s the spirit of the staircase. It’s when you’ve left the room and you’re going down the staircase and then you realize the perfect comeback.

PF All right. Let’s go back to Twitter and the org. We’re getting very meta. So you’re working on Longform and you have three different divisions. How big is this org total?

TH I think we’re like 60 people at the core and then there’s a whole bunch of kind of other people around it.

PFWhat is a good product manager, Tony?

TH Oh my God.

PF Interview me. I’ll try to come work for you. How do I prove to you that I am worth it?

TH I’m afraid we just filled that position, Paul, but we welcome any applications from you. [Paul laughs.]

PF I never wanted to work for the stupid company anyway. No, I mean what’s, what’s good?

TH So I think of it in a kind of few clear ways. The first one is can you kind of combine those elements of analysis and synthesis? Because the first thing you’re trying to do is trying to understand the environment in which your product is sitting. Yeah. So that requires a certain skill with analysis to be able to go deeper, understand from a data perspective, understand from a user research perspective, understand from a whole range of different perspectives. But then the second part of this is no, if you can only do analysis, you’ll only get so far in your product management career. A truly great product manager then is able to synthesize these things into a particular perspective, an orientation of how you see the world and then be able to kind of extrapolate from that and say, given what I know about this environment, everything that I’ve learned, we should like, this is the pathway. This is my kind of theory of how we interact with the world. And once you have that theory and there are also people who are very good at that, but then can fall apart in the next bit, which is actually doing something with it. And that’s being able to translate your kind of airy fairy thoughts and holistic synthesis of the world into very clear, timely, clarity for the team about like, this is how we’re gonna do it and think about the pathway. Like what’s step one to be able to get us towards the place you want to go t?. And you find as we were saying earlier, like people have different strengths and different abilities and sometimes it’s worth pairing them together and so forth, but the truly great PMs of those who can like analysis, synthesis, create an orientation and then communicate that in a way where a team can act. 

GT That’s all.


PF Let me turn that around too. Now that person’s come in, they’ve worked for a couple of months, they’ve got some roadmap in front of them, some things they’re responsible for, and they have a new idea. They have an exciting new idea along the roadmap, might require some resources, might throw things off a little bit, but they think they can get better engagement or more revenue or all the things that we’re kind of in the room for. And they have to convince their boss, Tony Haile. They’re gonna go into that room. What do you look for? What is the way to convince you of something? How does a product manager tell you that they’re right and get you to believe them?

TH So I think a few things. One, when someone does that, I’m always trying to place it in the context of the wider one. I’m like, there’s a set of information that I have also kind of analyzed and synthesized about the world. Does this tell me something new? Do they bring new information that changes my perspective? Does it align with that perspective? And so like the first thing is like—

PF So you’ve got to be a little surprised.

TH Yeah. Does this conform or force me to adapt my models about the world? And then the second thing that I’m looking for is like, is this something which is an optimization towards like a local maxima? Or is this a step change? Yeah. For the effort that we want to put in, can we achieve that? And those are the kind of things that I would think about as a startup anyway. Then there’s the big company stuff as well, which is like, how many freaking dependencies is this going to touch on? 

GT Yeah. 

TH You have this grand idea. Is it gonna involve six teams, four of whom I know have such backlogged things that they’re gonna tell us to just go away. What is the kind of practicality of how to do this in a large org when you have externalities that are not in your control? So I think there’s like a few different pieces of this, because in general, if we wish to move swiftly, reducing the number of dependencies or reducing them down to the places where you know either they’re very keen to work with you or where you, you know they have capacity. Those factors also come in as you’re trying to look through an idea.

GT So what’s most likely to realistically be able to happen? Not just what could happen in a total ideal state, if you had everybody that you could.

TH Yeah. One way to think about this kind of pathfinding is you’re trying to match unlimited ambition with limited capabilities. 

GT Yep. 

TH And trying to find like

GT The place where those meet, yeah.

TH The sweet spot is like, what is the thing that’s gonna realize the grandest possible ambition within the context of what we’re able to do with the resources we have. The other thing of a great product manager is they have a certain pragmatism. And also like people say politics as a pejorative in many ways, especially as it relates to the politics of big companies and it can be. But there’s also: how do I align a group of people who don’t have to work with me to actually work with me? And so a product manager who’s been able to think through that as well, that’s actually a very useful skill.

PF This is something I don’t think people process, what bad form it is and how bad it is for the org. If people who are running different divisions have to go up to the boss to get resources. It’s much better if you can go across the hall and be like, I have something that I think is pretty good, because you’re going to be sharing credit. You’ve built a network and you’re going to be sharing the success and you’re willing to get them to buy into your success, etc. I think people assume, at least I did for a long time, they’re like, well you know, you go up to the CEO and the CEO says we have to do it and everybody rallies around it. And if the CEO is doing that, then the organization is actually not scaling well—that’s a bottleneck.


GT That’s true. Yeah.

TH Do you know the monkey on the shoulders story from Henry Mintzberg? 

PF No. 

TH So every single person in the company has a monkey on their shoulder who it’s their job to feed that monkey and then they’ll come along to the CEO and they’ll say, here’s my monkey. Here’s this problem that I want you to solve. And suddenly the CEO’s feeding two monkeys. And then someone else comes along and kind of gives you another monkey and you’ve got three monkeys and it’s like, oh my God, suddenly I’m feeding and looking after three monkeys and these people are running around and they don’t have any monkeys. And the answer that this great—I think he’s a Harvard professor—gave back in the nineties was to hand back the monkey as swiftly as possible. [Gina laughs.]

PF Oh, absolutely.

TH So when someone comes to you, say I need more data on that. Or go and do this thing. When you go and you try to say, this is going to be the CEO’s problem, the CEO’s going to try and hand it back to you as quickly as possible, or make an arbitrary decision.

GT To make it a monkey that you can feed yourself. Right? 

TH Yes. 

GT The CEO’s asking, how do I make this monkey feedable by you? 

TH Because I can’t feed that.

GT Can’t feed everybody’s monkeys.

PF Gina can attest to this. We refer to that as delegating up. When a person delegates up that is a bad thing because no, it’s exactly that, it’s like well now I have two jobs and what’s your job? And that’s a bad feeling for everybody.

GT There’s something important here. Like you have to have a perception of the org and who does have a little bit of bandwidth and who is willing to—and I guess this is what you meant, Tony, when you said that people don’t like politics, I don’t know if you call this politics—but it is understanding how the org works and who can do what and how taxed people are. And that’s a perception that people don’t often have and don’t often think it’s important to develop until  they can’t get anything done because they can’t collaborate with others. 

PF It’s part of the job, right? But it takes you away from being a practitioner. So when people are coming in and they’re practitioners and they see you doing that job, they’re like, you’ve lost your soul. You’re not a real person anymore. And I used to do that. I’m like, what are they doing? This is just a meeting. It never ends. And then you realize years later, yeah, that was how that had to happen. 


GT They were getting things done. They were clearing the way. They were figuring out how to move forward.

PF All right, Tony, coach me for one more thing here, which is, I’m at a startup, it’s grown to like 50 people and I’m not going to go into a big organization. Maybe I quit. Maybe I got acquired, something like that. This happens a lot. And this is a number one cause of just absolute fatality in an organization as the startup mentality goes into the big org, wonderful optimism. And then six months later, just kaboom. And you’re kind of a veteran of big orgs and startups at this point. So what works? You’re pretty happy. You’ve landed inside Twitter, which is not a baby. Right? And like, it is a big complex matrixed organization, global with all sorts of challenges. But you’re a startup person and yet you’re content. You’re, you’re signaling that there’s lots of good stuff going on. What should people do? What makes that work?

TH I think one is kind of setting your expectations around all the things you get versus the taxes you pay and not thinking that you get everything for free. Like one of the things that’s really interesting: when we took my company Scroll and we brought it to Twitter and made it part of Twitter blue and kind of blew it up to a far larger audience, we had the resources of Twitter and all that kind of stuff was amazing, but you don’t get it for free. You don’t get all the good stuff for free. You also get coordination challenges and having to make sure that your data annotation is correct. And like all of the other kind of bits and pieces that come from a large company. And I think there’s that kind of like that fireball and narcissistic energy you get as a startup founder, when you’re going in, you’re like, I’m going to go in there and I’m going to blaze the trail and I’m going do this kind of stuff. And then you realize that it’s harder and it’s not because the company is bad. It’s because you are dealing with a different set of investment and taxes that will enable you to do more, but also make you pay a price for those things.

PF You know, what you’re describing is this is a pattern that happens a lot. Startups get acquired by very large orgs. Google is a pure example here. And then number one responsibility is to get their software stack and their experience into the software stack and experience of the acquirer. Like Google has essentially its own operating system. It sees data in a certain way. It sees geo in a certain way. It has its own file system. It’s all incredibly scalable. The idea is you’re gonna do that and you’ll get to trade off in the scalability. You’ll be part of the global platform and your idea will be really big. But I think what happens a lot is that the people on the ground, the directors and the engineers who are responsible for doing that, don’t feel the scale. And they’re not excited and motivated by the big picture on the other side because they’re just caught inside this enormous sort of rebuilding effort, without clarity as to why they’re doing it. So given that happens a lot, what should people be doing? How should they be looking at that work?

TH I mean, there’s some fundamental truth to that. There’s going to be a lot of stuff that you have to do when you are integrating that is just not fun. It’s like all the corners you cut when you were a startup, all the things that you put off, plus having to integrate into the big systems, there is a certain period of time and I can totally see why startup founders and startup teams that come in, get frustrated in this where it can be pretty crushing to kind of go through all this kind of stuff. And I’m sure that I have these challenges as much as anyone else when you’re trying to go through these things—


PF You literally built a product in Chartbeat where if you launched a new feature, it would go out to people and you would see—a real time reaction tool that you could see real time reaction to.

TH It was glorious and you could do these things super fast and you didn’t have to worry about all the dependencies and you didn’t have to worry about like, okay, this is our system and we can make these architectural choices without it affecting other people. So you have that freedom. And I think there’s two things that are most important. One is being very upfront when you go into the new company about that thing that is gonna happen. Ideally like, I don’t think as someone who’s both acquired companies and been acquired. If you have a choice between two companies, both roughly attractive to you, I would go with the one who has more experience acquiring companies, because it is an art, not just acquiring the integration. There are whole teams whose specialties around integration, like Cisco was quite classically great at this kind of thing.

And the more support they can give you and the more seriously they take it the better. Because companies that are new to acquisition or treat it in a fairly kind of haphazard way, or it’s a rare thing for them to do that, don’t have the same systems. And so that pain will be prolonged. But I think the other clear part of this is that what you as a startup founder coming into the company have to do for your team is you have to still keep that vision in front of them. And often the startup founder comes in, they get given a senior title and whatever. And so they’re kind of experiencing a lot of the fun and they’re meeting new people and they’ve got new responsibilities and many of the team are kind of like going like, well, you are getting to have that kind of fun. I’m here dealing with new GDPR requirements and it’s so important to be able to still—and this goes back to that kind of clarity as a kind of critical part of the role—to be able to communicate here’s that future that you’re going towards. And here’s why it will not always be like this. And there are brighter futures ahead once we’re through it. That can’t come from an integrations team. It has to come from the people who are the practitioners.

PF Yeah. What is motivating about scale to you? We’re talking about scale. Why are people excited? And I mean, I look obviously, okay, my thing is going to be in front of millions and millions of people, but you know that the process to get there is actually pretty hard. Why do we want this?


TH My possibly naive take is that while there may be people who start startups because they want to make a bunch of money, and I’d argue there’s way, way, better ways to do that. 

PF Literally that’s what Vanguard funds are for—anyway, anyway. Go ahead.

TH I think for most people there’s a change they wish to see in the world. And what scale gives you is an opportunity to better realize that. Like, for me, the kind of animating thing for me has been how do I make sure that journalists can get paid? So they can continue doing the work that upholds democracy and the democracy around the world.

PF I mean, that’s nice, it’s nice when we pay them. It is.

TH It’s really nice when they can pay rent. 

PF Yeah. 

TH And as a function of that, scale enables me to do that in a way that could have an actual, real impact. I could have a tiny little startup and I could like, I could pay the rent for a few journalists, but like, how do I make sure that we can still have a court reporter in Des Moines? Right? Like these are real problems and things where you can attack problems at scale with the resources of scale as well. That where step changes become possible.

PF Fair enough.

GT I don’t think that’s naive at all. I think it’s good. Makes sense.


PF  Tony. So look, I don’t have a better way to end than we should pay journalists and that large tech platforms have a role to play in there. I’m not going even—I can’t top that. 

GT Shouldn’t even try to top that. 

PF Yeah, no. So look, if people want to get in touch with you, what should they do? Is there a social network where they could follow you?

TH There’s a popular microblogging service called Twitter, which now has the vowels in it. I’m at @arctictony on Twitter.

PF Why @arctictony?


TH So prior to my career in startups, I used to lead and manage polar expeditions.

PF Oh, well, I’m glad we didn’t talk about that. That would’ve been boring. Maybe we can talk—

GT Wow, that’s a missed opportunity. We’re just gonna have to do it again sometime.

PF Wait, which pole?

TH North, predominantly, but I spend a lot of time around Siberia, Greenland, high Canadian, Arctic, all over the shop.

PF Well, this is like, when you write the management book, you got it, right? It’s just like, oh, the lessons I learned from, you know—

TH 12 stories you can learn at the North Pole. [Gina laughs.]

PF Exactly. And this translates to product management when you’re building on, you know, using Bootstrap. All right. So that’s how people should follow you. And are you hiring, are you looking for people? Anything?

TH We are. We are hiring for engineers, for engineering managers, for data scientists. We are hiring for partner managers right now, because we like so much of our work is around working together with publishers and writers and creators. We need people who can kind of like collaborate and connect the dots. So yeah, we’re hiring across the board and we need great product managers. They just have to be willing to work with me.

PF That sounds incredibly pleasant actually and really good. It’d be fun to work with you on a day to day basis. And I say that—you were very hands off as a client. You were great. It was just like, all right, this looks good. I’ll see you in two weeks. And I’m assuming if we hadn’t done a good job, you would’ve been very hands on.

TH It’s a function of trust, yeah? Like this is what I think is one of the things for me as a kind of manager. If someone is doing a good job and knows what they’re about, get the hell out of the way.

GT Let them do it. Yeah. Let them go ahead and do that. [Laughs.]


PF Well, Tony Haile, thank you for coming on the Postlight podcast. 

GT This is a lot of fun.

PF Yeah. Come back again. My God. And we need to talk about polar expeditions. Gina Trapani.

[Outro music fades in, ramps up.]

GT Paul Ford. This was a lot of fun. I really like hosting the podcast with you. We’ve got to do this more often. It’s good to see you.

PF It’s good to see you too. It’s nice to communicate with you in public with Tony. It’s fun. So friends, if you want to get in touch with Postlight, a wonderful company that does wonderful work for wonderful, wonderful people: is an incredibly good way to do it. Check out We build things. We do, you know what we do. And we want to hear from you.

GT Tweet at us:

PF That is the way to do it. All right. Back to work.

GT Thank you, Paul. Thank you, Tony.

PF Thank you, Tony. 
GT Let’s get back to work.