The Exchanges

Q So then is the next step to build a podcast or to start selling lessons to these guys?

A We accidentally started the podcast in the way that guys were like, you should write a book, you should write a book, you should write a book. AJ was a cancer biologist. I was studying for the bar exam. Nobody was, ain't nobody gonna write a book, right? So we decided to make some sort of CD audio thing and maybe hand it to guys that were asking us for this stuff. Because we thought this, this information must be free. I mean, it was just so good. And, uh, so AJ was like, hey, listen, there's this thing called podcasting. There's like 800 of them in the new iTunes that's, that's out. It's real cool. We should just buy some microphones from Guitar Center and just record some stuff and put it online. And then when people want it, we can just tell them the website to download it. So he made a website. We recorded some stuff, outlined a few episodes, put it online. And we were one of, you know, 800 or 8000 or however many podcasts were there in 2005.

AI assessment note: “We accidentally started the podcast in the way that guys were like”

Q Is that the first thing that you did? Took people up on their offer to fly in and

A Yeah, they flew in and learned, but they didn't stay with us, and then after that was phone coaching, and then after that, guys were flying in and staying with us. We were based in Manhattan at the time. They would stay in my apartment in Manhattan, and they would sleep there, and there were like one or two guys every week, because we had no real, I mean, our audience was tiny. And they would do that, and then they would tell their friends, and like, fast forward to now, now it's eight guys every single week, seven or eight guys every single week, For four months, six months in advance, depending on the season, were booked out completely.

AI assessment note: “Yeah, they flew in and learned, but they didn't stay with us”

Q So what do you do? Let's suppose tomorrow you wake up and you're number three. What do you do to fix it?

A If I, that's a great question. What I would do is I would reach out to my network and say, hey, I know you've been trying to interview me for a while, I would love to come on, or I would get a high profile guest and I would interview them. I, honestly though, what I typically then do is call app, and this is the unfair advantage that I have now that I've been doing this for a long time. I call Apple and I go, hey, who would you like to see me interview? I've got these ideas and who can you, who would you put on the front page of iTunes? And they give me a list out of that list. And then I call those people's PR or have my, I have my people call their people, you know, and then we set it up, and then I go on the front page of iTunes.

AI assessment note: “What I would do is I would reach out to my network and say”

Q pounding, and I really didn't expect it. I feel like this should be old hat for me right now, but I still feel a little insecure at times. I still feel like I don't have it. I told you via email when I invited you on here, you look like Mr. Confidence to me. You never seem to break a sweat. Is there anything that makes you shake your confidence?

A Oh, absolutely. I think that, uh, as one example, for instance, before I do any type of public speaking, I still feel like I'm going to vomit, and I pace like a caged animal before every speaking engagement. Um, but I feel like I would have to worry more if I weren't nervous before events like that, and it made me feel better to know that even Dean Martin used to vomit before every performance. Mike Tyson felt very similarly, and I think that Uh, we can delve into confidence, but I think that as Custom Auto, Tyson's trainer, would say, it's, it's not that the hero and the coward feel different. They feel the same way. It's, it's how they respond to that feeling that makes them different. Uh, so I, I, I have self-doubt. I have, ah, crises of meaning all the time, ah, and I think it's, it's important for people who only see the highlight reel, like maybe they only watch some of my presentations, or they see, you know, the Tim Ferriss highlight reel, to realize that it, it, it is a roller coaster, and those, there are those ups and downs, and that's just part of the ride that you sign up for in a lot of ways.

AI assessment note: “before I do any type of public speaking, I still feel like I'm going to vomit”

Q ah, of Dropbox. Is gonna be coming on here. Um, I wanna, I'm wondering from you, how do you learn from these extraordinary entrepreneurs? I wanna try to bring back some of your way of breaking down with they, with what successful people do. I wanna bring that to my interviews so that I can pull out ideas from my audience that they can use the way that you might.

A Yeah, I, I have a set of questions that I tend to ask, and they include, you know, what, what is the biggest mistake that novices make, the biggest waste of times, a waste of time that you see entrepreneurs making in, in the beginning, or it doesn't have to be entrepreneurs, but novices in any field, could be bobsledding, could be anything. Um, secondly, if you were to start over again, what would you do, what would you do differently? Uh, if you had to choose one or two people to emulate, who would they be and why? Uh, if you had, say, four to eight weeks to train me for fill in the blank, huge audacious goal, raising ten million dollars in funding, building a hundred million dollar company, whatever it might be, uh, how would you prepare me? I understand it's impossible, but if you had, you know, ten million dollars of your own money on the line, how would you train me? If you had to. Uh, and there's a set of questions like that, many of which seem absurd, uh, like the, you know, how would you train someone for an ultramarathon in eight weeks type of question, uh, that turn out to be possible if you force someone, uh, to answer the question. They have no option but to try to make that work. And, um, that, that's generally how I approach it. And, uh, If you had to choose, say, two or three resources, whether that be a book, a series of lectures, a blog to help someone self-stu…

AI assessment note: “I have a set of questions that I tend to ask, and they include”

Q a mutual friend of ours, Ryan Holiday. He said, Tim Ferriss used to talk to, ah, Tucker, Max, and Ryan before they, ah, before he made it, and you'd ask all these great questions, and they wanted to help you out, thinking, you know what, we're gonna help this guy get started. And I always wondered, what was it that you said that made them want to help you out?

A Oh, that's a great question. I'd say, number one, I did my homework. So I, I knew that Tucker, for instance, had done some Brazilian Jiu Jitsu. I had background and was current, was then training in Brazilian Jiu Jitsu. So I viewed that as a way to differentiate myself, especially at a place like South by Southwest Interactive. Uh, secondly, I didn't try to impress, I didn't try to impress him. I said, look, this is totally out of left field. You have no idea who I am. But I know you've done A, B, C, D, and E. You know, I'd love to buy you a drink and just ask you three or four questions. I'm not going to, like, pick your brain for an hour. I know you don't want that, but I have a couple of really specific questions. You know, in exchange, maybe I can do blah, you know. But gave them an easy out, I think, is another thing. And, you know, I was, I was really, uh, identifying with what Seth said about Rarely rewarding persistence, because then you're just asking for more of that sort of slamming a head against the wall behavior, even if you say no. Um, but, uh, you, you tend to get more bites with a softer cell, so I always give them an easy way out. I'm like, hey, look, if you don't have time, it's no problem at all, but, you know, this is one of three sessions I wanted to come to. I'm happy to, you know, maybe I can help you with this, this, and this. I have literally two or th…

AI assessment note: “number one, I did my homework... secondly, I didn't try to impress him.”

Q more megabytes, and so I joined, and then when I bought, I just put my credit card on, and now I've been a subscriber, I think, for two or three years, but you're saying that that's not the way it works with bigger companies. Do you call out to them, or do you wait for them to, to request a call? How are you getting big companies to sign up?

A So, so step one is a story more like yours, where, you know, someone who's just working in a department starts to adopt the product and share it with their group, and, and then it kind of mushrooms out from there, uh, and then, uh, often it will get the attention of IT, who's like, well, okay, how, how do we, you know, deploy this in a formal way and get some of the visibility and the control that we need, um, and so usually the first adoption is, is organic, and, and often it'll be Clumps of people or individuals just buying pro accounts, um, for themselves, maybe using the corporate credit card. And then, uh, to answer your question about is it do we call them or they call us? It's, it's a mix of both. So smaller customers will often call us and then We'll, we'll often have companies that have hundreds or thousands of Dropbox users. Um, they might just might not realize it yet. And so, um, those are the kind of folks that we'll call them and let them know that we have a business offering.

AI assessment note: “to answer your question about is it do we call them or they call us? It's, it's a mix of both.”

Q helps what he calls micro entrepreneurs build their businesses. Wondering, there are a lot of great companies that are in that micro entrepreneur level, but they're not going to get to the billion and beyond level that you've gotten to. If you could give them advice about how to break through that and go from micro to macro to giant, what would you give them? What would your advice be?

A Um, well, I think the first thing is the reason that companies, the first reason that companies don't become billion dollar businesses, for example, um, is that they don't have billion dollar markets, and so whenever, and this was true of my last company, right, I started an online SAT prep company, and, you know, our audience is limited to, you know, teenagers who have to study for the SAT, right, and you do it once, you're not gonna buy it again next year, hopefully, um, And so that put a cap, I mean, it's still a big market in aggregate, but it's, compared to something like Dropbox, it's pretty limited. And so, the first really important choice is what kind of market do you go after, and, and then, and, and even if you're going after something smaller, is there a way to expand it, ah, expand what you do, Um, or reframe what you do so that you can go after a bigger audience. Cause even if you're going after a massive market, you still have to pick a first niche. Um, we sort of picked Windows file synchronization, uh, as our first niche, um, when we were really trying, aiming at this much bigger problem of like how do you have your stuff with you wherever you are and solve all these other problems. Um, the second is to surround yourself with people, um, who have done this, who have built businesses like that. So, by taking money from Sequoia, um, our first venture investor, um…

AI assessment note: “the first really important choice is what kind of market do you go after”

Q Why do you think that Adley, ah, it sounded like you're saying that there were, that there are things you wish had gone differently. Ultimately, why do you think it ended up the way it did?

A Well, Adley is still around, I should say, ah, and we've got a stable company, but I think we did a couple things wrong. So, Very early on, I was very public, Sean was very public with our belief that in-stream advertising would be the way that ads were delivered, as opposed to at the boundaries of your periphery where nobody looks. And everyone at Twitter said it would never happen, everyone at Facebook said it would never happen, but of course that's where all their money is coming from, so we nailed that. Um, I think we made a couple mistakes. One is, I always believed we should focus on long tail, and we did build a long tail business, but as we became incredibly well known, every celebrity wanted to work for us, so we started Focusing on the celebrity business, and I think that was harder to build. Number two is platform risk. As an entrepreneur, you just can't put all your eggs in one platform. You really have to have three or four different platforms, and I don't think we were quick enough to recognize Pinterest, Reddit, YouTube, and other platforms we could have, uh, monetized through.

AI assessment note: “I think we made a couple mistakes. One is... Number two is platform risk.”

Q down becomes a chore, and I don't follow up. That remembering to go and look it up, often I forget, and if I do remember, I don't have the time to go and quickly sneak off and find out what Rob's wife's name is, for example. Rob Walling was on earlier. Is it just that you have a gift, Mark, or do you have some process for systematically remembering it?

A I don't have a process, so I will tell you a couple things. Number one is I do, in my contacts, try to write people's, spouses' names down and kids' names down if I, if I can. If I'm there and if I remember, I'll just write it down. Um, and I don't do it, like, I don't go to see somebody and say, let me look at their wife's name before I see them. I don't do that. But where it happens, honestly, is I'll see them out with their wife and I'll go, oh crap, what's her name? And just knowing that I can get my alternate brain out and remember her wife's name so I don't feel embarrassed. But no, I would say to you, first of all, all of our brains are wired very differently. Uh, and I think some people are just able to remember or not. I'll tell you a trick that they teach you in sales. When you meet someone new, you're supposed to use their name in a sentence three times within a minute of meeting them. It's what politicians do, what salespeople do. So if I say Andrew, you know, that's an interesting name because my son's name is Andrew, and so I should always remember that name Andrew, but you tend to go by Andrew or Andy. And just by saying that, I'm not likely to forget your name. And number two is association. So if I can associate you with something, that makes me more likely to remember your name. But regarding names, names I'm not always great on, but I always remember circumst…

AI assessment note: “I don't have a process, so I will tell you a couple things.”

Q But you start from scratch, writing out your post, and then they edit?

A I, okay, so the process goes is I write, I come up with a topic or a reader wrote email saying can you write on this topic. I'll write the post. After I write the post, someone goes, takes my screenshots that I did because most of my posts have screenshots. They'll add, they'll go to Fotolia, add in a generic image at the top, right? They'll go and format the content I wrote into WordPress. Then an editor goes in at the end and corrects it all because there's a lot of grammar and spelling errors even though I write in Word. And then the third blog post a week is an infographic. The infographic, I have someone who works for me. I pay him five or six grand a month. They do the research. Then they go find designers from Dribbble. We pay the designers. They create the infographic. I just add a quick intro paragraph and a conclusion, then the editor edits it. But the infographic post literally takes me 20 minutes to post. The blog post takes me around like four hours to write each one.

AI assessment note: “I'll write the post... Then an editor goes in at the end and corrects it”

Q Hey, ah, so, Noah asks a good question. Do you write your own content on Quick Sprout?

A So I do, I write, there's a caveat to it. Um, I publish three posts a week. Out of the three posts, two of them are blog posts, which I write myself. Uh, I do have an editor. I have terrible grammar and English, and without that, the post just, people used to always complain, like, most of my comments used to be, hey, you spelled this wrong, or you did this wrong, and then I also have someone who takes my post, because I write in Word. I can't write in WordPress. I write in Word, and I can take screenshots of images, and they'll go put it up and make it look pretty, right, and they'll format it, so I don't have to do that, because that was taking me around 30 to 45 minutes.

AI assessment note: “So I do, I write, there's a caveat to it.”

Q It's an inspiring story, and people are going to watch in this interview step by step as you built this up, but I want them to know a little bit about you, starting with where you came from. Can you tell them about that story where, about the sneakers that you wanted your mom to buy for you?

A Well, absolutely. I grew up in the inner city of Long Beach, so I won't say it was a war zone, but I won't say we had green manicured grass either. And, uh, you know, we didn't have the luxuries that my other friends had, and one story that comes to mind was when I wanted these new Nike shoes by a football player named Rod Woodson. All my friends had, we went to Target, and we found a rip-off. I didn't know it was a rip-off. They looked just like those shoes. They were by Zoic. Some people don't know what I'm talking about. And I remember I put those shoes on, I was so proud, because I had to ride Woodson's, so to speak, and the next day I went to school, and I got, I got the experience of a lifetime. All my friends, they laughed, they poked fun at me. I, I don't know if I ran to the corner and cried, but I felt like crying, and that was a turning point for me. Um, there were many things like that, but that's something that, 15 years later, I still remember, like it was brand new. Got me fueled about changing things.

AI assessment note: “one story that comes to mind was when I wanted these new Nike shoes”

Q How did you get people in the early days? How'd you get customers?

A Okay, well, I figured there's a ratio between time and money, or, I didn't have money, so obviously it was time, so. I'd become a moderator, I remember, of every piano music form I could find, and I would go to work with the time that I had, answering questions and using my signature, um, to promote my site, you know, if you want free lessons, head over to hearandplay.com, but I'd make sure I really answer their questions. If, if I knew it was in my knowledge base to answer, I'd go for it, and I remember just having a bookmarked folder Um, of every site, and every week, like every Saturday morning, I would just call it, doing my dudes. Every Saturday morning, I would go one by one, and try to post at least five times in those message boards. Some of them just had straight out places that you could advertise. Other ones, I would just, you know, be that person in the forum, helping out, you know, giving, and Hoping that it would come back to me, and soon, you know, thousand visitors a month, you know. We did the Yahoo directory. I'm still paying for that. I don't even know if that still works. I'm still paying for that same listing. I think they get me for 70 bucks a month. I mean, I'm working. I mean, 10 years of that, you know, from day one, and every time my card expires, I go in, and I think it's just a, uh, ritual for me now, you know, and, um, we were in D Moz. I remember, …

AI assessment note: “answering questions and using my signature, um, to promote my site”

Q Was she inspired by, by these little businesses that you started? What was her reaction to them when you said, Hey, you know what? I think I'm gonna write a book and sell it about how to, um, how to play piano by ear. Or when you said something else, what was her reaction to all that?

A You know, surprisingly, she was very supportive because when, when you, when you're that innovative at that age and You know, family already had it set up for what I was supposed to do, right? I was supposed to be like the next Johnny Cochran. I had a knack for speaking, and I, I went to school, undergraduate for law and criminology, and this was the path everybody laid out for me. But here we were working on these books on how to play piano, and she was in the copy shops with me. Our dates consisted of going to copy shops, copying these 300 page books, binding them, Going to the post office, waiting in line with our little cards, I mean, those are the glory days, and then going to Mickey D's afterwards. And she, she doesn't cease to remind me of those days, you know, when, when, when I get a little, you know, You know, on her nerves. She'll remind me of those days. And, but she was very supportive and very inspired, and, um, she said my ambition, you know, even though I was like that little nerdy boy that didn't fit in, she said my ambition made me look very good to her. So, you know, ambition goes a long way.

AI assessment note: “surprisingly, she was very supportive because”

Q You gotta love it. Running is, is not for people who don't love it. Um, I said that you started the business with 70 bucks. Where did the 70 bucks come from, and what were you using the 70 bucks for?

A Well, as I retell the story in my head, the 70 dollars must have come from A church gig, because, you know, I'd get 50 dollars here, 25 dollars there. They call it the love offering. Let's, let's take up a collection for our musician, our young fifteen-year-old. So, you know, that's the only way the money would have come from, from a gig or a piano student or something like that, but 70 dollars was a big deal to me. Gave my mom it, and she gave me her debit card number, and I went to Network Solutions. Now it's all about GoDaddy and stuff like that, but it was 70 bucks in, uh, August. 2000. I registered that domain name. I asked myself, what is it that I do? And, uh, I had enough sense to have a very descriptive domain name. I'm sure I could have come up with some, you know, fanciful name, like Kaju or something, but it was just simply hear and play, and it was available, and that's been my, my thing ever since. Hear and play. That's what we do. I haven't done see and play, because I don't believe in see and play, You know, my niche is hear and play, and, um, and it opens itself to extensions, hear and play piano, hear and play guitar, hear and play organ, and we have moved that way, so that was my start.

AI assessment note: “the 70 dollars must have come from A church gig... I registered that domain name”

Q you about. So, First of all, thanks for doing this interview, ah, especially so soon after getting acquired. I know that's, that usually after getting acquired, you want to take a step back and, and not do media, and I appreciate you coming here and doing this interview. And second, for anyone who doesn't, who didn't see that wristband, can you explain what it was? What was on your wrist?

A Absolutely. Well, I'll, I'll show it to you now, because I still have it right here, and I had two wristbands on, ah, two years ago, and one said, make poverty history, ah, which is a passion of mine to use business and entrepreneurship to create sustainable economic growth in the developing world, and that's something I hope to pursue for the next three or four decades ahead. The other wristband said, one hundred million in 2012, eye contact. Um, and that to me was a personal goal to either get to a hundred million in revenue or, or get acquired for north of a hundred million, uh, this year in 2012. We started the business, uh, in 2003, and you're right, we did everything we could to keep expenses low, sleeping on futons, eating lots of rum and noodles, um, as we built up eye contact over the years to 70,000 customers, a little over forty seven million in annual revenue. Um, and over a million users in email marketing and social media marketing. And so it was a great adventure. Uh, but certainly having two primary life goals, uh, on your wrist, uh, is a very visible way of focusing your efforts on achieving them.

AI assessment note: “one said, make poverty history... The other wristband said, one hundred million in 2012”

Q How do you get those people to give you so much of themselves?

A It's a great question. You know, I, I, um, in, in my case, um, They were either the people that I hired as my, uh, C-level executives, or they were the folks that invested in eye contact, um, either as equity investors and angel investors, um, or as advisors. Um, and so I think it's, I think it's important to find people that are, have already achieved what you want to achieve and bring them into your life. Um, but in order to get the level of a collaboration, you often need to align economic interests in some way by allowing them to invest in your firm or by potentially paying them on a monthly basis for their advice. Um, and what I found is that by having, uh, a CFO who was, you know, in his mid to late forties when we hired him, had already been CFO of a company that exited for five hundred million plus dollars, uh, about 10 years ago, by having him as a mentor, Um, by having, you know, his name is Tim Oakley, our CFO, by having a guy named Buck Goldstein as a mentor, who'd been a venture capitalist, who'd been a public company CEO, um, by having Jit Sinha from JMI Equity and Carter Griffin from Updated Partners. You know, these were the people, along with my senior team, that really gave me the knowledge I needed to execute and build eye contact into a successful company.

AI assessment note: “you often need to align economic interests in some way”

Q You mentioned earlier having difficult decisions that you have to make on your own. Like what? Um, what's the toughest decision that you felt like you had to make and it was just you? Or the toughest decision in general?

A Yeah, I mean, ultimately, um, um, In 2000 and, uh, 10, April, sorry, April of 2000, November of 2010, we decided that we would launch a free version of eye contact, um, in response to some of the competition in the marketplace, having done that successfully, and, um, ultimately that was my decision. I went to the board, I advocated for what I believed in, I made the decision. Um, and when you have When, when, when a company gets large, it becomes more like a, a cruise ship than a speedboat. Um, and so changing the direction of cruise ship versus changing the direction of speedboat takes a hundred times longer. Um, it's very different for an entrepreneur who has a tendency to have a bias toward action and to act quickly, uh, to try and move an organization with 300 employees versus an organization with three or 30 employees. Um, and so I learned a heck of a lot in how to lead, lead a number of people in organizational groups through a strategic shift. Um, but, I mean, there are decisions like that. There's decisions to raise the forty million dollars from JMI Equity, which ultimately became my decision. Um, decisions to, you know, propose to the board that we go forward with the sale of the company. Um, you know, so these are decisions that ultimately you're, you're, you, you make, um, you know, staring out your window in your office, and it's, it's you making the final call.

AI assessment note: “we decided that we would launch a free version of eye contact”

Q Well, you did it. I have the quotes here from our first interview of what you were going to do, and here you did it. What's next? What's the next big goal? What's the next big wristband?

A Well, I am passionate about creating jobs in the developing world. I'm passionate about being part of, uh, ending extreme poverty in our lifetime. Um, I've been passionate about that for probably the last decade. Um, I still wear that white, uh, wristband that says make poverty history from 2005 from the one campaign and worn it now for About five or six years. Um, and to me, um, I went to Africa in 2008, to Kenya and Uganda for the first time. Since then, I've started investing as an angel investor in companies and in Kampala. What I plan to do with the next, uh, 25 years at least, um, is to become a great venture capitalist and a great private equity investor in companies and countries like Nigeria, Ghana, Kenya, Uganda, Rwanda, Tanzania, Ethiopia, Zambia, South Africa. Uh, and really sub-Saharan and middle Africa. Um, and I think through investing and providing capital to growing businesses, you can often make a huge positive impact and create long-term sustainable economic growth. So that's my passion, and I hope to see a world created in which every human being has access to basic human needs of food, water, and shelter. And I think we'll get there in the next 20 or 30 years.

AI assessment note: “What I plan to do with the next, uh, 25 years at least”

Q coming up with the right questions here. I'm really excited to be doing this interview, and it's showing in my voice. I should be so much more professional and so much more composed than I am right now. But can you give me an example of what's on the list? What kind of things would you have on the list beyond building a hundred million dollar company by 20 12?

A Sure. So it might be travel countries that I want to visit that year. Um, it be, um, personal traits and values that I want to, uh, sort of build into my character over time and work on improving. Um, it might be, uh, experiences. Uh, for example, last year, one of my goals was to go skydiving for the first time and check that off the list. Um, and oftentimes, uh, it sometimes might be educational. Um, and oftentimes many are within the realm of, of business, uh, and entrepreneurship, and, um, in terms of the process of setting the goals, you have those categories, you know, family, personal, experiential, educational, uh, and professional and business, and then you put in a couple goals for each, um, and, and it really doesn't take that long. It really takes maybe a couple hours to do at most, um, every, every year. Um, and then you, I have a personal wiki Which is a password protected sort of like Wikipedia just for me. Um, and I keep my, you know, goals going all the way back to 2002, uh, when I was 18 to the present by year, and then every couple, two times a week I go in and sort of do a journal update to sort of see how I'm progressing each week and whatever I'm learning. So that's the process I go through in the categories I have for the goals.

AI assessment note: “for example, last year, one of my goals was to go skydiving”

Q Do you remember the day when you signed the paperwork, when it was done? What was that like?

A Yes. Uh, I remember actually the day before, much better. The day before was when all, all the lawyers had agreed, and we basically said, tomorrow we're gonna sign the papers. And I remember I got really emotional that day. I was, I was sitting there at my desk in, uh, in Boston, and I just cried. I was just so, uh, I don't know if I was excited or relieved. It was a stressful time trying to sell Reddit, and there was lots of times when we thought, oh, it's not going to work out. We just wasted the last month negotiating with these guys. And that was, uh, that was, that was a pretty emotional time. And then when we actually signed Reddit, it was like, uh, or when we signed those papers, uh, it was almost just like, uh, any other day. I felt like I had already gone through the, uh, The, the, the big, ah, breakthrough the day prior.

AI assessment note: “when we actually signed those papers, uh, it was almost just like, uh, any other day.”

Q Who were the first moderators that you brought into Reddit?

A Hmm. That's a good question. Um, I know one of the first outside moderators that sticks in my mind is QGYH too. Um, he, he was, uh, this insane Reddit user. I shouldn't say he was insane. He spent insane amounts of time on the site and we always thought he was a bot for, for a long time because we would look at his, his usage and there was never, there was like never an hour during the day where he didn't check Reddit. We're like, this guy like never sleeps. He's just always on Reddit. And so, in my mind, he's one of the first. Uh, Alexis would be the, would probably have a better answer to that. Um, but, but I know we brought him in to, uh, just keep an eye on things because we, we, he was spending more time on the site than we were at that point.

AI assessment note: “one of the first outside moderators that sticks in my mind is QGYH too”

Q When I asked Paul Graham about how, about Hacker News, he said that it takes a lot of time for him to manage that community. Here you guys have a much bigger community with Reddit, and I see that you interact with people via email, you're active on the, on the site itself. How do you do that?

A You know, we, we started off, when, when we launched, Alexis and I would just answer every single feedback email we got. And, and for a while that was sustainable. It, it, unfortunately, is no longer sustainable. But, ah, the community also, ah, one of the, there's, there's kind of an interesting backstory between Hacker News and Reddit. And one of the decisions that we made on Reddit is that we don't want to be moderators. It's, it, it doesn't scale very well. And, and, and on Reddit, a lot of the users are moderators. And especially on all of the smaller subreddits, you know, The vast majority of which I've probably never even seen, or neither have any of the other Reddit, you know, administrators. And the community, Reddit's been very good about self-policing itself, and appointing other moderators and keeping things together. And also, I should say the bigger issue is that there's a distinct lack of moderation on Reddit. To a large extent, it's anything goes. As long as it's not spam, most content will survive. And so that was one of the big philosophical differences between Reddit and Hacker News is, is we didn't want to remove content or we didn't want to tailor, uh, the site to any particular type of content.

AI assessment note: “one of the decisions that we made on Reddit is that we don't want to be moderators”

Q Ok, alright, then what was the next step? You've got now a website that works just for you. What are you doing after that?

A Right. So here we are. It was back in October, 2007. We did it one weekend. No idea of doing a business. All of a sudden, maybe there's something bigger there. Trying to solve our own problem. Then people are saying, well, I have the same problem. At that point, you know, a few months went by, you know, and kind of had other things going on in our lives. And I remember Joe and I, we went home for Christmas. Um, you know, you talk to your families, everyone's like, you know, you go to home for the holidays, people say, well, what are you working on? And, you know, we probably both had similar conversations. Well, you know, I'm doing this project and that project, but we also have this other thing, air bed and breakfast. Air bed and what? And then you get into the conversation, and we started realizing everyone was really excited. They would love to do it. We came back from New Year's, and, you know, I, I remember asking Joe a question. You know, we're both designers by trade. I asked him, who's the best developer you know, best hacker you know? And it turns out that, um, Joe's old roommate, you know, that, like, that moved out so I could take the room, was our third co-founder, Nathan Boczarcik. Um, you know, he, he was a really, really talented developer, um, you know, with, um, from Harvard, and he funded his education by a business he started in high school. Very impressive. …

AI assessment note: “who's the best developer you know... was our third co-founder, Nathan”

Q Alright, um, something that you guys told me in the email before we set up the, before we, um, before the interview was that you have multiple launches. What do you mean by that, and how does that help you get press?

A Right. So, you know, we're not even, we're, we're only like halfway through the, the story, the launches, um, and it was funny because we spoke at Y Combinator and, you know, the kind of thing we tell people, um, whenever we're giving advice is don't go for the Super Bowl launch. Um, don't go for one single thing. Um, you don't have to worry about exclusive story. You think about it. We had our first launch, the one day website. The second launch was South by Southwest. That was like the three week website. The third launch was August of 2008. It was this thing we're just talking about. And we actually had, like, three or four, kind of, like, launches after that as well. So, you know, when you're a really small company, like, you have the opportunity to retell your story many, many times. As long as every time you tell it, there's something different about it. So for us, the first story was in our apartment. That was a different story, right? The next story was we're providing housing for conferences. The next story was we're solving this crisis. After that, what do we do next? Well, logically, the DNC works so well, we did the same exact thing in Washington, D.C. for the inauguration. And it turns out that the people that covered us on CNN did another piece about us, and then even more people covered us.

AI assessment note: “you have the opportunity to retell your story many, many times”

Q up with them one after another, after another, after another, makes me say, how? How are you able to come up with all these ideas? While, by the way, You're not just in college. You're not just smoking a bong. You're not just hanging out. You've got responsibilities. How do, how do you do it? I'd like to, I'd like to be able to crank out great ideas like this.

A Um, how do we do it? Well, I, so, we, we have a background in design, and I remember we used to be in studios together, and we would literally just, I think what happens is, we don't just sit around and have, like, a light bulb idea. This idea came from a conversation, and actually very much evolved. So the first thing was, it would be cool to, like, have, to be able to give a breakfast to somebody, and like, ok, that's cool, we're talking about it for a while, we're brainstorming, we, we don't immediately have the brilliant idea. It's kind of, you know, it takes a bit of time for us to realize, That we should end up doing a serial, right? A non-perishable that we can brand. Ok, we're gonna do a DNC serial, RNC serial. You know, as we're talking about this, then we start saying, well, you know, there's all this Obama's, all this Obama propaganda, and it's like, you know, um, materials. We should create an Obama-themed serial. And, uh, McCain-themed cereal. At that point, we're like, ok, we're creating an Obama-themed cereal, a McCain-themed cereal, we're brainstorming, and then we're, at this point, we're just brainstorming names, but I, I guess the key was, we didn't just one day say, we're going to create, oh, Obama-o's. It was very evolutionary. We're then brainstorming names for Obama-o's, names for Cat McCain's. It's a, I think it's a constant, like, conversation that we h…

AI assessment note: “This idea came from a conversation, and actually very much evolved.”

Q Fried had an interesting blog post the other day. He's probably whipping these blog posts out in his sleep and then waking up and create and just churning out profitable web apps. I can't compete with him. Now intellectually, you know, that's nonsense. You're not really competing with him. You're in your own world with your own customer base, but you can't stop that thought. How do you do it?

A Well, I'd start with Steve Pressfield's book, The War of Art, where he talks about the resistance. This resistance is nefarious. It will never give up. It will use every opportunity it can to find an excuse to get you to yak shave, to spend three more hours checking your status on all these social networks. Just one more time to make sure you're right, the right emotional moment to move forward. And then, you know its name, and you know its tactics. And you know how it does its job. And you're smarter than that. So if it's important to you, you beat it. What did Isaac Asimov do? He wrote 400 books in his career. Right? 40 times as many as me. How did he do it? Every morning he woke up at six o'clock, and he wrote till 10 a.m., and then he was done. Right? Robert Parker just died. He wrote the Spencer novels. Every day, day in and day out, he wrote five pages. That's all. Five pages. That's how he beat the resistance. He can spend as much time as he wants at the keyboard, but he cannot get up until five pages are done. There's a million ways to beat the resistance. After all, it's a 100,000 years old. It's very primitive. You just gotta decide that that's your job. Once you decide that that's the job, you'll figure out how to beat the resistance. If I tell you how I beat it, it will not help you. You have to beat it your way.

AI assessment note: “Well, I'd start with Steve Pressfield's book, The War of Art”

Q I pay attention to the people who work for you guys, say, are they really snowing the public, and then when I'm under the hood, I see where the dirt is? No, she's phenomenal. So, If you don't mind, how do you, what's your relationship to her? How is she so phenomenal? What's the deal here? Because I'd like to be able to have people like that on my team.

A Ashita does not work for me. I work for Ashita. She was one of my MBA students. And when the, the semester ended, I asked her to, to come on as head of hoopla for this project. And what I said is, you're in charge. You're the head of hoopla. Tell me what to do. And I worked for her. She says, you're going to talk to Andrew. I show up. And so you start by hiring somebody who loves to be like this. Not someone you have to tell to be like this. And then you completely get out of the way. You get out of the way and say, you are better at this than I am. And that's the secret of Skidoo, by the way. Six people, all of them are better at what they do than I am, so I don't bother them. And I work for her. If I can support what she's doing, that's my job. It is not my job to tell her what to do. Because then she becomes a compliant cog in the factory of Seth Godin. That's not the deal.

AI assessment note: “She was one of my MBA students... you start by hiring somebody who loves to be like this”

Q techniques. I went on a meditation retreat where they forced me not to talk for seven or so days, and they taught me about the monkey brain, they called it. By the way, you name things, right? Like lizard brain. I'm going to be talking about lizard brain with my wife tonight, and we're going to be talking about it in the chat room, and you did it intentionally, right?

A Well, I didn't invent the lizard brain. It's from somebody called Triune Theory. You can check in Wikipedia. But yeah, I name stuff all the time because If there isn't a name for something, we will be unable to take action on it. If permission marketing didn't have a name, you couldn't go to a venture capitalist and say, I'm starting a permission marketing company. If idea viruses didn't have a name, what would we have called them? They're not viral marketing, it's a noun, right? So, by naming things, I'm providing a service, and the service is, I want us to have a conversation, let's just agree to call it this, go, talk among yourselves. I think that's pretty valuable, it's not particularly difficult, and other people should do it too.

AI assessment note: “But yeah, I name stuff all the time because If there isn't a name”