Skipping The Line in Podcasting | James Altucher

James Altucher shares stories from his inspiring up and down journey in life and business and how he's leveraged these experiences to lead him to where he is today. In this keynote talk, James shares how you can skip the line in podcasting (on either side of the mic) through the use of unique ideas and constant reinvention of yourself. This is how James grew his podcast to be one of the largest in the world. Whether you're a podcast host or podcast guest, this talk will inspire and motivate you to take your podcasting game to the next level!

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Transcript

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I don't normally wear a tie, but for this event, I figured it's very opportune I wear a tie. But, how to skip the line to succeed in podcasting. One of my favorite topics. I did not want to be a podcaster. I don't really like talking to people, and I really like to just sit in my house and read and write all day. That's what I like to do. And, but then I had the opportunity to do a podcast. Someone said, "Hey, we'll produce it for you." And I figured, okay, this is a good chance for me to call up all of my favorite people. And I have an excuse, you could you should talk to, so you could be on my podcast. You have a new book out, no problem. Be on my podcast, so you promote your book. Oh, you have a new investment that you're working on. No problem, come on my podcasts we'll talk. So it was a great way to call people that I would normally never call and get them to get a chance to talk to them and ask all the co they'd be a captive audience, and they'd have to answer every question I had. So I, it's been an amazing experience, but I'm going to kind of rewind a little bit and start off with, how did this all happen? And some of you might know a little bit of, you know, what I've talked about before, you know, how I got started writing, how I, became an entrepreneur and so on. And there was one time, the very first time I built a company was in the mid nineties and I was doing a website for HBO. My, I will argue, I did the very first podcast actually. So this was 1996, and hbo.com didn't even exist. I convinced HBO the television network to buy hbo.com the URL. They had homeboxoffice.com, but there was a medical supplies company in Atlanta, Georgia called HBO and company, and they owned hbo.com. So in 1995, HBO spent, I'll give you a chance to guess how much money think about it for a few seconds. How much would they spend in HB on hbo.com in 1995? So they spent $250,000 even then for the URL hbo.com, but it was worth it of course and, I was, I, I was running HBO's website. I convinced HBO to make a website. And, then I wanted to convince HBO to make web shows the way they made TV shows. I mean, the reason I wanted to work at HBO was because I just loved their TV shows. And at that time I think it was, there was the Larry Sanders show. There was a show called Dream On that was a very HBO-like, there were a couple of other interesting shows and I just loved watching HBO. So I applied to work there and I, for whatever reason, they accepted. And my title was junior analyst programmer. I was the lowest of the low on the totem pole. And I think it was my boss's boss's boss's boss's boss's boss's boss was the CEO of HBO. So one day I decided I was going to go talk to the CEO of HBO, his name was Jeff Bewkes. He later became the CEO of Time Warner and about a year or two, he retired. So I'm on my way, to talking to Jeff Bewkes CEO of HBO, and I, you know, the the, IT, I was a programmer in the IT department and the IT department, no one cared at all about the IT department at HBO. We were even in another building, nobody cared about us. And so I'm walking over there between the buildings, and I ran into a friend of mine who was one of the heads of marketing of HBO. And she said, where are you going? And I said, I'm talking, I'm going to go to the CEO's office. I have this idea for Jeff Bewkes. And she said, you can't, you can't just go to the CEO's office, what are you going to talk to him about? And I said, well, I have an idea for him to do shows on the web the way they do shows on TV. Kind of like cutting edge, innovative, sort of a little bit edgy kind of shows. And she's, "You can't do that like, you're just a programmer. You're not going to, he's not going to listen to you." And it was the, it was one of many times before, and many times since up until the present day where people tell me, you can't do something because of X, Y, or Z. And sometimes they have good intentions. They don't want you to make a fool of yourself. They don't want you to get fired or whatever, or they want you to keep your expectations realistic because maybe you can't do something. I, if I said, oh, I'm going to be, you know, a leading score in the NBA next year. If someone told me you can't do that, they would be right. But still what's wrong with me trying. Usually when someone tells you, you can't do something it's because they can't do it, and they don't want you to succeed where maybe they have not even tried or where they have tried and failed. And again, they might not have malicious intent, but you can't, you can't listen to the people. In fact, the, the, the path to'can' is usually filled with cant's. So I kept on going to Jeff's office and I walk into his office and he looks up and he says, "Who are you?" And I said, "Well, I'm building hbo.com and I think HBO should do shows like on the you know web shows." And I had an idea for a particular web show and he's like, "I don't care. Just do it. It's your generation. I was young, then it's your generation just do it." And so I went back to my boss and I said,"Jeff Bewkes said, I should do this." And he said, "What?" And I said, "I ca you know, I ran into him and I told him this idea and he said, I should do it." So now suddenly I had this idea, I called it III:AM, where I would interview people at three in the morning, in the streets of New York city on a Tuesday night. Not a Saturday night, because everybody was out at three in the morning on a Saturday night or a Friday night, but on a Tuesday night, why would you be out? You're either working the next day or a student, like how could you be out at three in the morning? So I had this feeling that it would be interesting stories at three in the morning. So I did this for two and a half years where every Tuesday or Wednesday night I went out at three in the morning and with a camera crew and we would record the interviews and I would just interview random people I came across. So I interviewed prostitutes, drug dealers, pimps. One time I went on the bus that goes back and forth between Queens, New York and Rikers island, which is a jail. And I would just interview everybody on the bus. Another time, I don't know, just, I had so many stories. I, I basically turned over every rock in New York city in between 1996 and 1999 say. And it was a real big experience. HBO even gave me money to shoot it as a pilot, and we had a really fun experience shooting it as a pilot. But I interviewed, I interviewed about 20 people a week and I took the four best each week. I transcribed the interview interviews and had designers design around it. And you can find it still on archive.org somewhere, if you search hbo.com and, it was really fun. I probably interviewed well what's 20 people times, I went out about 120 weeks, so it's almost like 3000 people I interviewed during this time. And I was really nervous at first, like going up to people at three in the morning. Like one time, this couple was arguing with each other. And I went up to them and I said,"What are you guys arguing about?" And they started chasing me. So HBO for a while, wanted me to have a bodyguard go with, with me on these interviews. And so one time I was in this one, bar doing interviews. I was secretly doing interviews, and it was a kind of a, let's call it a transgender bar. And people like, you know, husbands from the suburbs were in this bar picking up transgender prostitutes. And I was asking them, why are you doing this? And I dunno, the answers were interesting, but I remember the, I don't know what you call it, the security in this bar found out what I was doing, and they started chasing me. And the bodyguard was like three blocks ahead of me, by the time we stopped running. So that didn't really work at all, it was an interesting insight into private security, but, I did that for a while and it was really fun. It was fun doing interviews and then putting writing stories around those interviews. And so anyway, other companies came to me at this point and said, "Hey, can you do for us what you did for HBO or kind of an exciting sort of website." And at that time, no one knew that the internet was going to be this e-commerce, you know, behemoth like that's really the main purpose of, of the internet right now is either e-commerce or marketing. And so, I really thought of the, of the web then, it's like this artistic medium, where you should do shows and you should like do interesting things with hypertext and links and so on. So, just on the side while I was a full-time employee at HBO, I was making, let me see, I was making 40,000 a year was my salary, and I thought I was rich at HBO. And I, and in New York City, I could tell you, I couldn't even, there was no apartments for rent even then I couldn't afford anything. I was sleeping on people's couches. And, but meanwhile, I started, all these companies started asking me to do their websites because nobody knew how to do websites back then. I remember American Express asked their accounting firm do their website. The accounting firm asked a huge ad agency. The huge ad agency asked a consulting firm, and the consulting firm asked me if I knew how to make a website. And so I said, sure. So I got my brother-in-law, who was a designer and myself, I was on the software side and we made their website and I had never had a single dollar in my bank account in my life, and I was making 40,000 a year. American express paid us$250,000 to do this website. And then we did timewarner.com. Then we did conedison.com. We did dozens of websites and we started hiring people. We built a company and, you know, we ended up with about 30 or 40 employees and millions of dollars in revenues. I had left HBO by this time and we sold the company and I made a lot of money. But unfortunately I didn't really know anything about money. There's, there's three skills to money, making it, keeping, it growing it. So, I didn't even really know any of these skills. Like I made it because of a fluke, like the internet was this fluke at the time, and I certainly didn't know how to keep it or grow it. So I kind of went broke really quickly. But before I went broke, I bought an expensive apartment to live in and did all sorts of other expensive things and made a lot of bad investments, you know, I can't even describe some of the investments, but they were all bad. And I lost everything. I lost all my money, millions and millions of dollars. And I got really, really, I was losing my house too, the IRS was after me and I don't know, I didn't have, I had two small babies. I didn't know how I was going to pay for them. I had no opportunities. The internet was busted happen. So there was everybody thought the internet was a fad. So I didn't even have any internet opportunities. And I was just really depressed because I couldn't even sell this house. I lived one block away from ground zero, 911. And you know, I was going broke because I not only did I not have any money, but I owed the IRS and I couldn't pay my mortgage. So my house was going to get taken and everybody, I, you know, everybody who was your friend on the way up is no longer your friend on the way down. So I didn't even really have any opportunities or networks or anything. And so one time I was taking a walk and I saw this restaurant supplies store and I went in and I saw this box of waiters pads for a $10, I had a hundred waiters pads so 10 cents a pack. And so I bought the waiter's pads and the next day I started writing down 10 ideas a day. So every day, 10 ideas a day, I remember my first list of 10 ideas a day was a book idea like 10. So the book idea was called,'beat your friends and family at every game in the universe'. And so my first idea list was 10 games, where I could figure out the tricks needed to win those games, and I would write a book about it. So for instance, Scrabble, if you know all the two letter words, like a ZA or XI or XU, or QI, you would, you would win a Scrabble. You'd beat basically your friends and family at Scrabble. Monopoly, if you own the orange properties and focus on that, you're going to win in monopoly because if you know, monopoly jail is the most is the square year on, most of the square is the, jail is the square you're most likely to land on because you can get there from the dice or the community chest or the go to jail, square. And then seven is the most likely dice roll, which puts you right in the middle of the orange properties. So you should own all the orange properties and charge a lot of rent and build hotels and so on. So anyway, I had, that was my first idea list. And every day I would write 10 ideas, 10 ideas. Did I have any good ideas? Probably not. But I found that I was exercising this idea muscle. I didn't realize you had to exercise your creativity, but it turns out creativity is a muscle. It doesn't just strike you like lightning and it doesn't come from talent. You have to exercise it every day. And, suddenly with all these neurons connecting like, oh, I'll connect my interest in writing with my interests in games. I'll connect my interest in investing with my interest in software. I'll connect all these different ideas up. I started feeling really excited about these ideas that I can potentially work on. And then I started writing ideas for other people. Like I wrote a list to one writer. Here's 10 ideas for articles you should write. And he wrote back to me and he said, "This is great. Why don't you write these articles for me?" So I started writing for Jim Cramer's website, thestreet.com about finance. And then I wrote to this one hedge fund manager, here's 10 ideas for hedge fund strategies you should do. And he said, "This is great. How about I allocate money to you? And you do them?" So I started a hedge fund and more and more things started happening. And eventually it lifted me out of my depression and I had opportunities and new career possibilities. And so I kept building up from that. I always wrote 10 ideas a day. One day, many years later, I wrote 10 ideas for a website I wanted to create about financial news. So I built that it was called StockPickr. I sold that. I went broke again because I still hadn't learned the skill of keeping it. And, I had to start from scratch again and very depressed again. And I lost my house again. And I started, I kept doing the 10 ideas a day, 10 ideas a day, and eventually that led to more opportunities and more connections. I wrote 10 ideas for Google. I wrote 10 ideas for Amazon. They both asked me to come out and visit and consult with them. I wrote 10 ideas for LinkedIn, 10 ideas for Quora. All the way up to the current day. I remember, I had this podcast guest Charlamagne Tha God, he's a radio host in New York city. He's got millions of people in his audience and he had interviewed Joe Biden and I had watched it. And I remember Joe Biden said to him, if you haven't decided who you're going to vote for, then you ain't black and Charlie and said, "But we have questions." So I wrote Charlamagne my list that day. It was 10 questions Charlamagne could have asked Joe Biden. And I said, "Charlamagne, you should make this into a book. You don't need to respond. Just, you know, if you want, if you're interested, just steal this idea." You always want people to steal your ideas because how are you going to execute on all your ideas? Share the wealth and ideas are a true currency. Ideas are like the currency of the 21st century. So Charlamagne said, this is just a year Charlemagne said, "Oh, why don't you help me write the book?" And so we wrote this together and, it became a best-selling book on Audible and Audible Originals. So opportunities happen all the time because of me writing these idea lists. And ultimately, I, you know, back in 2012, 2013, writing these idea lists led led to this book I wrote called Choose Yourself. And the book sold very well. A lot of people liked it. It was about how I kind of dug out of the hole I kept putting myself in and how I came back and, and survived and survived enough to feed my family and create opportunities for myself. And this one guy liked it enough. He flew up to New York and he said, how about you do a podcast, and we'll produce the whole thing. I didn't know anything about producing up podcasts. And so I said, No. And we kept in touch. And eventually though I realized, oh, like I said earlier, this is a great way to call up people that I admire. And so I started doing the podcast and it was back in December, 2013. I started and I started interviewing some, you know, there weren't a lot of podcasts back then. So I had it on some great guests I had on and they, the people who were producing my podcasts, they thought I was just going to have like financial people to investors and hedge fund managers. And maybe I should have stuck with a niche like that, but I really wanted to talk to everybody that I ever wanted to talk to. So some of my guests have been Gary Kasparov, who is the former world chess champion, Kareem Abdul Jabbar, who's the best basketball player in history, Danica, Patrick, the best female car racer in history. Wayne Dyer was on the podcast, Tim Ferris. So many, so many great people, a bunch of congressmen and governors, politicians, writers, all my favorite writers have been on my podcast and, and it's such a pleasure. And again, why do they go on a podcast? Well, several reasons. One is they want to promote something. So, I always look for, who's publishing a book in the next six months and then I'll write to every single one of them. Hey, I've had on so-and-so so-and-so and so-and-so and, I see you're, having a book come out. Why don't you come on my podcast and we'll talk about it. And a lot of, you know, and I always list people who have been New York times bestsellers. They've been on my podcast, so they see, oh, it's a good crowd to, to be in the same group as oh, people who've been on James Alvelda's podcast. So I don't know if anybody actually increases any book sales by being on my podcast, but maybe they do, maybe they don't, I don't know. But again, I get to interview like all these people who I've admired since I was a little kid, like, you know, I play chess for instance, so having the best chess player in world history on my podcast, was such a treat or, you know, I like to write, so having, you know, great writers, whether they're Tim O'Brien author of a really beautiful short story collection, The Things They Carried or, Ken Follett who's re who sold 150 million copies of his thrillers. So I've had on great writers, I've had on great hedge fund managers, like Ray Dalio who runs the largest hedge fund in the world, or Steve Schwarzman, who runs the largest private equity firm in the world. I've had on Peter Teal one of the best entrepreneurs and venture capitalists out there. And again, all of it comes from, I really credit everything from this practice I do of writing 10 ideas a day, and it's such a simple practice to do. It takes 20 minutes, to do every single day. And it's been, it's created so many opportunities for me. It's changed my life in so many different ways. And even now to this day, I write here's 10 guests I should have on here. Here's 10 questions I would ask each guest or here's, you know, the other day I wrote an idea for, you know, what, if I made a piece of software to keep track of all of my ideas. So here's 10 features that that would have, I might implement that and launch that soon, we'll see. And whenever I have, I wrote a book last year called Skip The Line, which was about how everybody always tells me, oh no, you need, if you want it, you can't go from being a hedge fund manager to a stand-up comedian, that's crazy. Well, I would write you know, again, I would write 10 ideas for things I need to learn if I wanted to be a comedian or a chess player or an entrepreneur. And, but everybody said, oh no, you need the 10,000 hours. If you switched careers, you need to put in, there's the 10,000 hour rule. Yeah, I have to put in 10,000 hours to be good at something. And I figured this is BS. What if you're 40 years old, 50 years old, 60 years old, you mean you can't change interests and, and do something you love and monetize it? So I wrote a book, Skip The Line about how I've switched careers over 10 times, and always had to figure out how to get good at something and how to monetize it. And I wrote about something, I call the 10,000 experiments role. So instead of just doing 10,000 hours, it's better to do experiments. Like for instance, one time well, when I made the website Stock Pickr, that was just an experiment. What if I allow people to enter their portfolios into a website and then everybody can compare and comment on each other's portfolios. Well, that got a mil I launched it very cheaply, less than $2,000 it cost me to build it, launched it and had over a million users the first month. So it was an experiment that worked. Most of my experiments fail miserably, but they turn into good stories. Like one time I remember there was one time, Trump tweeted how he wanted to buy Greenland and the prime minister of Denmark tweeted it's not for sale. And I'm like, what the heck is this? Like, I didn't know A, you could buy a country. And what does Denmark have to do with Greenland? And why would, why would they tweet? It was, was this just a tweeting negotiation? So I did some research and I, I realized, oh, there are reasons to buy Greenland. So I made an idea list, 10 reasons one should buy Greenland. So here's an experiment I did. I started a Kickstarter, so that I could buy Greenland and I was going to try to raise a hundred million dollars to, to start off. Greenland I think would cost much more and Kickstarter shut me down instantly, but Indiegogo, let me, I think it was Indiegogo or maybe it was GoFundMe, one of them, let me run the campaign for a while, and it was an interesting experiment about writing. I was using the structure of a Kickstarter to write down. The reasons why I would buy, why would want to buy Greenland instead of letting kind of, a president or prime minister buy it. And, it was a fun experiment. It failed because I didn't buy Greenland, but it was an interesting story. And I learned how to do a Kickstarter. I'd never done a Kickstarter before. So experiments have huge upside and very little downside and every podcast I do, I try to experiment with things. Like maybe I'll interview somebody, and you know, I'll try different interview styles, or, or, or maybe I won't have anybody on at all and I'll start a new series. Like I started a series called I Was Wrong. And I talk about all these issues that I've written about in the past. And maybe I've been wrong about some of those issues. And that turned out to be really popular. I did, I did one about housing, owning a home. I was wrong colon, you know, housing or another one I'm about to do is I was wrong about going sending kids to college, which I always wrote articles; I would never send my kids to college. And unfortunately, two or three of my kids went to college against my against the advice of their father, but maybe I was wrong, maybe not about to do an episode on that. So I'm always experimenting with different formats and, always experimenting with new types of guests or new ways to talk to the guests. There's one guest we decided to do a little mini series called Good or Bad where we talk about very topical things and discuss whether they're good or bad for society. And so that's about to launch. And so 1500 podcasts later or more, I've been doing this for eight years, about 150 podcasts a year. So a little, it was about 1200 podcasts and always trying to find new ways to reinvent it because otherwise you'll get bored if it's not, I find it's not worth doing something, you know, it, it, it, this is doing a podcast is not a longevity race. It's not like who does it for the longest, or who does the most podcasts, or even who has the most downloads. You do a podcast because it changes you as a person and it makes you a better person. I've had on 1200 great guests and I've learned from every single one of them. And I don't always remember everything I've learned, but I try to remember at least one thing from each one of them that I can implement in my life. And, it's been a great experience. This is a little bit of a story of how I've skipped the line towards podcasting, but I hope it's been helpful and thanks very much, Alex Sanfilippo for inviting me to come to this. And if anyone wants to contact me @JAltucher on Twitter and I try to respond to tweets and thanks very much.