The Exchanges

Q You're, I'm sure, an advisor and a mentor to many. Who's your biggest mentor, and how did that come about?

A There were lots of them. Bill Campbell have famously worked with me at Twitter, but there are a number. Like, I remember, you know, I learned an immense amount from Susan Wojcicki at Google. In the couple years I was at Google working for Susan, the things I learned from Susan were she was always calm and thoughtful, irrespective of the other emotions in the room. You know, if the volume was raised, or the tensions got higher, or Somebody else started getting, you know, more aggressive in tone of voice or in language about some topic. Susan was always and is always calm and thoughtful, and I just thought that was, it was just really, really impressed me. Something I ended up telling my managers at Twitter is people, your people are always watching you, and they're always looking for cues, physical cues, emotional cues, language cues from you as a sort of Stress signals. Is Dick stressed out? Um, if Dick's stressed out, we should, we should be stressed out. And the real lesson from Susan for me was this sort of a hundred percent all the time, calm, thoughtful tone that she had that was reassuring to everybody who worked for her, uh, irrespective of what was going on around her. So I could go on and you're asking me for a lightning round.

AI assessment note: “I learned an immense amount from Susan Wojcicki at Google.”

Q Speaking of kind of that self-questioning ability within the culture, how do you, and maybe thinking now with culture building with course, and then looking back to Twitter as well, how do you think about building a culture where kind of ambitious goal setting is key, without a Fear of significant accountability placed upon that. How do you, again, balance between those two?

A You know, I always try to tell managers inside a company, your job is to create and set the conditions for success. So one of the things I would try to do at Twitter and here at Chorus and elsewhere is push ownership of a decision and the metrics down the stack, right? If I tell the team, you have to improve the Android startup time of the Twitter Android client by 40% next Tuesday, you're just asking for trouble. They're going to do something foolish in service to this ridiculous dick said metric that probably is even going to hurt the way the Android client works even if it starts faster. Just to give a sort of very specific example, if you instead say, look, you know, our Android startup time is lagging compared to the iOS startup time and has degraded by this percent over the course of the last 10 months, I want you guys to come up with a solution for how we can go ahead and fix that and improve it and make it a lot better and come back and propose something to me by Monday and let's try to be aggressive about it. By doing that and not being prescriptive about the solution, but giving the team ownership and authority over the solution, they're going to be a lot more creative. They're probably going to be aggressive and creative and, you know, and then it's easy to hold them accountable to the solution they've proposed and they want to be held accountable to the solution the…

AI assessment note: “it's easy to hold them accountable to the solution they've proposed”

Q Can I jump in and ask, what do you think it was about that acting and that stand-up comedy? That made you have such an attraction to it, combined with computer science, which maybe may not go hand in hand traditionally.

A I just sort of learned via the acting classes and doing stand-up that I was good at it, that I was a good improviser, that I was quick on my feet, that it was fun, that it was exciting. It was theater without a net. You know, there's no safety net. There's no script when you're improvising, when you're on stage doing stand-up by yourself. So the thrill of that and the excitement of it and actually being good at it Sort of opened up that side of me that I loved and wanted to pursue a lot more and knew that if I didn't pursue it right after graduation, I probably would never do it. You know, once you start making money and have a salary, you don't want to go back to scraping two pennies together. So I did that, scraped two pennies together for a long time, eventually put my degree back to use. And, um, when I didn't get some of the auditions, I, I tried to get, you know, audition for Saturday Night Live, didn't get that, a couple other auditions like that, and didn't get either of those. So I decided to All right, I gotta go back and put my degree to use, and I did in the very late eighties, and then when the internet, really at the beginning of the internet, the beginning of the web, and Netscape, the mosaic in 93, when the web really started taking off, I decided to start my own company, and had been an entrepreneur ever since.

AI assessment note: “learned via the acting classes and doing stand-up that I was good at it”

Q Speaking of kind of that self-questioning ability within the culture, how do you, and maybe thinking now with culture building with course, and then looking back to Twitter as well, how do you think about building a culture where kind of ambitious goal setting is key, without a Fear of significant accountability placed upon that. How do you, again, balance between those two?

A You know, I always try to tell managers inside a company, your job is to create and set the conditions for success. So one of the things I would try to do at Twitter and here at Chorus and elsewhere is push ownership of a decision and the metrics down the stack, right? If I tell the team, you have to improve the Android startup time of the Twitter Android client by 40% next Tuesday, you're just asking for trouble. They're going to do something foolish in service to this ridiculous dick said metric that probably is even going to hurt the way the Android client works even if it starts faster. Just to give a sort of very specific example, if you instead say, look, you know, our Android startup time is lagging compared to the iOS startup time and has degraded by this percent over the course of the last 10 months, I want you guys to come up with a solution for how we can go ahead and fix that and improve it and make it a lot better and come back and propose something to me by Monday and let's try to be aggressive about it. By doing that and not being prescriptive about the solution, but giving the team ownership and authority over the solution, they're going to be a lot more creative. They're probably going to be aggressive and creative and, you know, and then it's easy to hold them accountable to the solution they've proposed and they want to be held accountable to the solution the…

AI assessment note: “it's easy to hold them accountable to the solution they've proposed”

Q we did reference your time at Twitter there, and you've said before about very interesting take in your commencement speech about the Medvedev visit. I'd love to hear though, taking from that visit, more a question of how do you deal in, in times of intense pressure and stress? What's your coping mechanism? How do you look to kind of prioritize and execute? What does that look like for you?

A I have a, maybe a sociopathic ability to compartmentalize. I really have to. And as an entrepreneur and a CEO, you have to be able to compartmentalize. Otherwise, you know, you go insane because there are always 50 fires you can be thinking about fighting and worrying about. You have to choose what you're going to focus on. Focus on those couple things that are the highest leverage things you can be focusing on right now and really block everything out, block everything else out. You know, you can be aware of it, but try to, like, sort of set it aside and focus on the one or two things you need to focus on without revisiting anywhere else in your life where you feel like the walls might be closing in. That can sometimes be perceived as, well, Dick doesn't care about X, Y, Z, but you just have to have this ability in those high-stress positions to compartmentalize and focus on the two or three things that are the highest priority things you need to be worrying about.

AI assessment note: “I have a, maybe a sociopathic ability to compartmentalize.”

Q You said before that you can't plan your script, uh, In that case, what advice do you have for young professionals today starting out their career entering the workforce?

A The camp plan your script came from when I was younger, I would hear these speeches and you'd have these graduation ceremony speakers who would tell you to go out there and make an impact in the world. And I always felt like that left me with not knowing what to do, because most of the time you don't know the impact you're going to have until after you've had it. You can't just decide I'm going to do this thing because this will make an impact. So if you do the thing you think you're supposed to do instead of what you're excited about doing, then when things go wrong, as the inevitably do, you end up sort of frozen there on the stage of your own life, wondering what you're supposed to do next. And so what I mean by that, you can't plan the script of your life is you have to be doing things that you want to be doing and are excited about doing because when things go wrong, as they inevitably will in that case as well, you'll be resilient because this is what you wanted to spend your time doing.

AI assessment note: “you have to be doing things that you want to be doing and are excited”

Q we did reference your time at Twitter there, and you've said before about very interesting take in your commencement speech about the Medvedev visit. I'd love to hear though, taking from that visit, more a question of how do you deal in, in times of intense pressure and stress? What's your coping mechanism? How do you look to kind of prioritize and execute? What does that look like for you?

A I have a, maybe a sociopathic ability to compartmentalize. I really have to. And as an entrepreneur and a CEO, you have to be able to compartmentalize. Otherwise, you know, you go insane because there are always 50 fires you can be thinking about fighting and worrying about. You have to choose what you're going to focus on. Focus on those couple things that are the highest leverage things you can be focusing on right now and really block everything out, block everything else out. You know, you can be aware of it, but try to, like, sort of set it aside and focus on the one or two things you need to focus on without revisiting anywhere else in your life where you feel like the walls might be closing in. That can sometimes be perceived as, well, Dick doesn't care about X, Y, Z, but you just have to have this ability in those high-stress positions to compartmentalize and focus on the two or three things that are the highest priority things you need to be worrying about.

AI assessment note: “I have a, maybe a sociopathic ability to compartmentalize.”

Q In terms of making that gut decision and running with something, I'm intrigued, you said about kind of making the transition and utilizing your degree in the end after trying in Chicago. What do you think is the kind of inflection point and the balance between a kind of vision for what you want to do, and then also realism when something's not working?

A That's a fair question. I think for an entrepreneur, you have to overweight optimism and pursuit of the vision. Of course, you have to be honest with yourself. And one of the things we talk about at chorus all the time here at course all the time is make sure we're always being honest with ourselves and make sure we're learning as quickly as possible. Sometimes one of the reasons that startups and companies don't learn quickly is because they have some vision that becomes dogma because you're not allowed to question it. So what was the vision and a North star becomes dogma because it's, well, as our founder, John always says, X, Y, Z, and we're not allowed to question that. So I think the way you deal with the struggle is you want to be a relentless optimist, but always make sure that everyone on the team is allowed to question things and make sure you're getting at the truth and that anything that's held up as a North star, people can poke and pry at and question and make sure they're interrogating to ensure you're getting at the truth. So As a long-winded way of saying, you have to have this really aggressive dose of optimism that's offset by, we always have to be able to tell each other the truth, and we always have to be able to interrogate what we believe to be true.

AI assessment note: “you have to have this really aggressive dose of optimism that's offset by”

Q Can I jump in and ask, what do you think it was about that acting and that stand-up comedy? That made you have such an attraction to it, combined with computer science, which maybe may not go hand in hand traditionally.

A I just sort of learned via the acting classes and doing stand-up that I was good at it, that I was a good improviser, that I was quick on my feet, that it was fun, that it was exciting. It was theater without a net. You know, there's no safety net. There's no script when you're improvising, when you're on stage doing stand-up by yourself. So the thrill of that and the excitement of it and actually being good at it Sort of opened up that side of me that I loved and wanted to pursue a lot more and knew that if I didn't pursue it right after graduation, I probably would never do it. You know, once you start making money and have a salary, you don't want to go back to scraping two pennies together. So I did that, scraped two pennies together for a long time, eventually put my degree back to use. And, um, when I didn't get some of the auditions, I, I tried to get, you know, audition for Saturday Night Live, didn't get that, a couple other auditions like that, and didn't get either of those. So I decided to All right, I gotta go back and put my degree to use, and I did in the very late eighties, and then when the internet, really at the beginning of the internet, the beginning of the web, and Netscape, the mosaic in 93, when the web really started taking off, I decided to start my own company, and had been an entrepreneur ever since.

AI assessment note: “So the thrill of that and the excitement of it and actually being good at it”

Q In terms of making that gut decision and running with something, I'm intrigued, you said about kind of making the transition and utilizing your degree in the end after trying in Chicago. What do you think is the kind of inflection point and the balance between a kind of vision for what you want to do, and then also realism when something's not working?

A That's a fair question. I think for an entrepreneur, you have to overweight optimism and pursuit of the vision. Of course, you have to be honest with yourself. And one of the things we talk about at chorus all the time here at course all the time is make sure we're always being honest with ourselves and make sure we're learning as quickly as possible. Sometimes one of the reasons that startups and companies don't learn quickly is because they have some vision that becomes dogma because you're not allowed to question it. So what was the vision and a North star becomes dogma because it's, well, as our founder, John always says, X, Y, Z, and we're not allowed to question that. So I think the way you deal with the struggle is you want to be a relentless optimist, but always make sure that everyone on the team is allowed to question things and make sure you're getting at the truth and that anything that's held up as a North star, people can poke and pry at and question and make sure they're interrogating to ensure you're getting at the truth. So As a long-winded way of saying, you have to have this really aggressive dose of optimism that's offset by, we always have to be able to tell each other the truth, and we always have to be able to interrogate what we believe to be true.

AI assessment note: “you have to have this really aggressive dose of optimism that's offset by”

Q up, I'd love to hear your thoughts just in terms of really building that groundswell culture from the beginning again, and something that I often get positive with on the show is that certain people are destined for certain areas of company lifecycle. Would you agree with that thesis? And how has it been for you transitioning back in such a shift from the mighty multinational Twitter to now Chorus?

A No, I don't agree with that thesis. I think that people surprise you and people who were in very specific functional roles in company X when it was 10,000 people, uh, can jump into a startup and be a, you know, what I would call a stem cell and play multiple roles and wear multiple hats and then switch back into specific functional roles. And I've seen people be able to bounce between those two things quite successfully. So I don't agree with that thesis, and when I am starting a company, I do look for willingness on the early employees' parts to be able to wear multiple hats and do lots and lots of things, and not just be tied to one specific, a functional role. You just need to be able to operate that way when you're getting started.

AI assessment note: “No, I don't agree with that thesis. I think that people surprise you”

Q What do you believe that most around you disbelieve? Penultimate question.

A Oh gosh, there's probably a million things there as well. The thing that I believe that maybe many people in the industry disbelieve, I think that as opposed to the mythology of Silicon Valley of there are these sort of superheroes out there, and they have these amazing superpowers that the rest of us don't have, the reality is that all of us have a few superpowers, and all of us have a few probably super weaknesses, and There's much less difference between those we mythologize and those we hold up as heroes and everybody else. The best advice I probably ever got from another entrepreneur was Jeff Bezos, who was talking about a particular figure who was mythologized and said, you know, there are lots of ways to be successful. And I think that's probably my, you know, in addition to it's always hard, my, my single piece of advice for most entrepreneurs, there are lots of ways to be successful and trying to copy what the media or Where the rest of the industry is held up to be, uh, this is the way you do things out here. It's probably not going to work for anybody except that one person.

AI assessment note: “The thing that I believe that maybe many people in the industry disbelieve”

Q up, I'd love to hear your thoughts just in terms of really building that groundswell culture from the beginning again, and something that I often get positive with on the show is that certain people are destined for certain areas of company lifecycle. Would you agree with that thesis? And how has it been for you transitioning back in such a shift from the mighty multinational Twitter to now Chorus?

A No, I don't agree with that thesis. I think that people surprise you and people who were in very specific functional roles in company X when it was 10,000 people, uh, can jump into a startup and be a, you know, what I would call a stem cell and play multiple roles and wear multiple hats and then switch back into specific functional roles. And I've seen people be able to bounce between those two things quite successfully. So I don't agree with that thesis, and when I am starting a company, I do look for willingness on the early employees' parts to be able to wear multiple hats and do lots and lots of things, and not just be tied to one specific, a functional role. You just need to be able to operate that way when you're getting started.

AI assessment note: “No, I don't agree with that thesis.”

Q I do want to touch on one element that you discussed there, being kind of the acting element, and in an acting class, you were once presented with an empty stage, and this story has had a profound difference on my life. So what did the class respond to the professor who discussed the stage with, and how did the professor respond to the student's responses?

A When you're improvising, you're always presented with an empty stage. I mean, that's, that's all you have. When you're improvising, you're at Second City, you know, is sort of the famous shot of Second City in Chicago is it's an empty stage with a couple chairs on it, and every single thing that the group does over the course of the next 90 minutes is just, you know, made up and improvised. And the only thing that's real on the stage are the two chairs that people might use to sit in. And that's what starting a company is like. You're given the blank slate and you got to make it up as you go. You have to make up everything as you go. There's nothing there. You start off without space, without a strategy, without a team, without anything. Some of the things I learned about improvising helped me being an entrepreneur. 100%. There's no question about it. Things like you just have to run with whatever you've got to go on. Any, whatever your first idea is, whatever your instincts are, Run with those. And, you know, when you're an entrepreneur, your people are constantly second guessing you, you know, they're like, this isn't going to work. There are lots and lots of reasons. It's not going to work. You know, Ben Horowitz in his book, the hard thing about hard things always talks about the struggle and waking up at three AM and wanting to scream. And I mean, he always talked about op…

AI assessment note: “When you're improvising, you're always presented with an empty stage.”

Q I do want to touch on one element that you discussed there, being kind of the acting element, and in an acting class, you were once presented with an empty stage, and this story has had a profound difference on my life. So what did the class respond to the professor who discussed the stage with, and how did the professor respond to the student's responses?

A When you're improvising, you're always presented with an empty stage. I mean, that's, that's all you have. When you're improvising, you're at Second City, you know, is sort of the famous shot of Second City in Chicago is it's an empty stage with a couple chairs on it, and every single thing that the group does over the course of the next 90 minutes is just, you know, made up and improvised. And the only thing that's real on the stage are the two chairs that people might use to sit in. And that's what starting a company is like. You're given the blank slate and you got to make it up as you go. You have to make up everything as you go. There's nothing there. You start off without space, without a strategy, without a team, without anything. Some of the things I learned about improvising helped me being an entrepreneur. 100%. There's no question about it. Things like you just have to run with whatever you've got to go on. Any, whatever your first idea is, whatever your instincts are, Run with those. And, you know, when you're an entrepreneur, your people are constantly second guessing you, you know, they're like, this isn't going to work. There are lots and lots of reasons. It's not going to work. You know, Ben Horowitz in his book, the hard thing about hard things always talks about the struggle and waking up at three AM and wanting to scream. And I mean, he always talked about op…

AI assessment note: “When you're improvising, you're always presented with an empty stage.”