How to Skip The Line to Succeed in Podcasting (Lessons From 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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Read The Blog Post: How to Skip The Line to Succeed in Podcasting (Lessons From James Altucher)

How do you skip the line to succeed in podcasting? That’s exactly what I want to talk about today. Interestingly enough, I did not really want to be a podcaster. I wouldn’t say I like talking to people that much. At least not as much as I like sitting at home reading and writing all day. But then one day the opportunity came up to do a podcast.

Someone approached me and said, “Hey, we’ll produce it for you.”

I thought to myself, “This is a good opportunity to call up all of my favorite people.”

I now had the perfect excuse to talk to people I would never normally talk to. In addition, I had the opportunity to ask all the questions I had.

So far, it has been a fantastic experience.

But I am getting ahead of myself. How did all this happen? Let us rewind a little bit.

This post is a transcription of one of the talks from our PodPros Quarterly Virtual event.

You Can’t See The HBO CEO

The very first time I built a business was in the mid-nineties. This was 1996, and hbo.com did not exist yet. So I convinced HBO to buy the URL. At that time, the URL of their website was homeboxoffice.com.

HBO ended up spending $250,000 for the hbo.com URL, which at the time was owned by a medical supply company in Atlanta, Georgia.

That’s how I found myself running HBO’s website. But I was not done yet. Now I wanted to convince HBO to do Web shows, similar to what they were doing with TV. After all, I wanted to work at HBO because I loved their TV show!

At that time, there was the Larry Sanders show. There was also a show called Dream and a few other exciting shows. I just loved watching HBO.

So I decided to talk to the CEO, Jeff Bewkes. I should point out that I was just a junior analyst programmer and no one was interested in the IT department at HBO. We were not even in the same building!

I was walking over from one building to the next to see the CEO when I ran into a friend of mine. She was one of the heads of HBO’s marketing department. She asked me, “Where are you going?”

I said, “I am going to the CEO’s office. I have this idea for Jeff Bewkes.” Then she said, “You can not just go to the CEO’s office. What do you want to talk to him about?” I quickly replied, “Well, I have an idea for him to do shows on the Internet like they do on TV. Innovative and a little bit edgy shows.”

But then she told me, “You can not do that, you are just a programmer. He’s not going to listen to you.”

Don’t Let a No Stop You

This is just one of many examples of people telling me I can not do something because of X, Y, or Z. Sometimes they have good intentions. Sometimes they have good intentions. They do not want you to make a fool of yourself, or they do not want you to get fired. Sometimes they want you to keep your expectations ‘realistic.”

If I said, “I am going to be the best scorer in the NBA next year,” and someone told me I could not, they’d be right. But what’s wrong with me trying anyway?

If someone tells you that you can not do something, it’s usually because they can not do it. They do not want you to succeed where they did not even try or where they tried and failed.

Again, they may not have bad intentions, but you should not listen to such people.
The path to ‘can’ is usually filled with cant’s.

So I continued on my way to Jeff’s office. As I entered his office, he looked up and asked, “Who are you?” I replied, “Well, I am building hbo.com and I think HBO should do web shows.”

He said, “I do not care. Just do it. It’s your generation.” So I went back to my boss and said, “Jeff Bewkes said I should do this.” He exclaimed, “What?”

I told him about my idea for a show called III: am. I would interview people on the streets of New York City at 3 a.m. on Tuesday. Not on a Saturday night, because everyone is out on the weekend. I went on to do that for two and a half years!

3AM TV Show

Every Tuesday or Wednesday I would go out at three in the morning with my camera crew to record interviews with random people.

I interviewed prostitutes, drug dealers, pimps, and so on. Once I even rode the bus that goes back and forth between Queens, New York and Rikers Island Prison.

Between 1996 and 1999, I turned over practically every stone in New York City and interviewed about 3000 people!

HBO even gave me money to make the film as a pilot. You can find it somewhere on archive.org if you search for hbo.com.

At one point HBO hired a bodyguard for me because they never knew when the person I was interviewing would turn on me and run me off.

Building My First Multi-Million Dollar Business Only To Lose Everything

Soon after, other companies approached me and asked if I could create their website for them. At that time, no one knew that the Internet would evolve into this e-commerce giant. In fact, very few people knew how to create websites back then.

I remember American Express asked its accounting firm, which in turn asked a big advertising agency. The big advertising agency asked a consulting firm, and the consulting firm asked me if I knew how to build a website.

Together with my brother-in-law, who was a designer, we worked on the website and got a $250,000 cheque for it.

That was just the beginning. From there, we built a company and ended up with about 30 or 40 employees and millions of dollars in revenue.

Unfortunately, I had no idea how to keep and grow my money. I went broke very quickly. But before I went broke, I bought a fancy apartment, all kinds of other expensive toys, and made a lot of bad investments.

At one point I was on the verge of losing my house. The IRS was after me, and I did not know how I was going to pay them.

I could not even make my mortgage payments. There was the dotcom bubble, which meant that everyone thought the Internet was a fad.

Rebuilding Again From The Ground Up

One day while walking, I passed a restaurant supply store. I went in and bought a waiter’s pad for $10. The next day I started writing down 10 ideas every day.

My first idea was a concept for a book called ‘Beat your friends and family at every game in the universe’. For example, if you know all the two-letter words, such as ZA, XI, XU or QI , you can easily beat your friends and family at Scrabble. I wanted to write a book about such tactics.

So I wrote down 10 ideas every day. Were they all good ideas? Probably not. But I found that I was exercising the idea muscle. I did not know you had to exercise your creativity.

It turns out that creativity is a muscle. It does not come like a bolt from the blue, and it does not come from talent. You have to exercise it every day.

Suddenly, all these neurons were connected, and I could now combine my interest in writing with my interest in games, or my passion for investing with my passion for software. I started to get excited about all these ideas that I could potentially work on.

Soon after, I started writing ideas for other people. For example, I wrote a list for a writer. He wrote me back and said, “That’s great. Why don’t you write these articles for me?” So I started writing for Jim Cramer’s website, thestreet.com.

Starting a Hedge Fund

Then I wrote to a hedge fund manager and shared with him 10 ideas for hedge fund strategies he could try. He replied, “That’s great. How about I give you some money to work with? And you implement them?” That’s how I started a hedge fund. More things started working for me and eventually got me out of my depression.

Many years later, I wrote 10 ideas for a website I wanted to create about financial news. I built it and called it Stock Pickr. I sold it for a few million but went broke again because I still had not learned how to manage my money. I had to start from scratch again.

However, I kept going with the 10 ideas a day, which eventually led to more opportunities. I wrote 10 ideas for Google, Amazon, LinkedIn, and Quora.

I remember I had this podcast guest Charlamagne Tha God. He’s a well-known radio host in New York City. I had seen his interview with Joe Biden. So I wrote a list of 10 questions that Charlamagne could have asked Joe Biden. When I presented them to him, I said, “Charlamagne, you should make a book out of this. You do not have to answer. If you want, you can just steal this idea.”

Remember, you always want people to steal your ideas, because how are you going to implement all your ideas?

Ideas are something like the currency of the 21st century.

Charlamagne said, “Oh, why don’t you help me write the book?” So we wrote it together and it became a bestseller on Audible and Audible Originals. By writing these 10-idea lists, I keep getting new opportunities!

How I Got Into Podcasting

Writing these lists eventually led me to publish a book called Choose Yourself. It’s about how I got myself out of the holes I kept putting myself in, and how I survived to feed my family and open up new opportunities for myself.

One man liked it so much that he flew to New York and said to me, “How about you do a podcast, and we produce the whole thing.” I had no idea about producing a podcast. So I said no, but we kept in touch.

Eventually, I realized this was a great way to call people I had always admired.

So I started the podcast in December 2013, and the people who produced my podcasts thought I was inviting financial people on the show, so investors and hedge fund managers.

Maybe I should have stuck with that kind of niche, but I really wanted to talk to everyone. My guests included Gary Kasparov, the former world chess champion, Kareem Abdul Jabbar, the best basketball player in history, and Danica Patrick, the best female race car driver in history.

Wayne Dyer, Tim Ferris, and so many other great people. I also interviewed a number of congressmen, governors and politicians. And let us not forget, all my favorite authors have been guests on my podcast!

Getting Best Seller Authors On My Show

So why do these people come on my podcast? Well, for a number of reasons.

One common reason is that they want to promote something. I always look to see who’s publishing a book in the next six months. Then I write to each of them. “Hey, I see your book is coming out soon. Why don’t you come on my podcast and we’ll talk about it?”

I often mention the names of people who are New York Times bestsellers. I do not know if anyone actually sees an increase in their book sales as a result of being on my podcast. Maybe they do, maybe they do not, I do not know.

But as I said, I love to write, and it’s always a pleasure to have great authors on my show. Whether it’s Tim O’Brien, the author of a wonderful short story collection, The Things They Carried, or Ken Follett, who has sold 150 million copies of his thrillers.

I have also had great hedge fund managers as guests, like Ray Dalio, who runs the largest hedge fund in the world, and Stephen Schwarzman, who runs the largest private equity firm in the world.

Again, it all boils down to my practice of writing 10 ideas a day.

It’s such a simple yet powerful method. It only takes 20 minutes, but it has opened up so many possibilities for me. It has changed my life in so many different ways. Even today, I still write my lists.

Here are 10 guests I should have here. Here are 10 questions I would ask each guest.

The other day I wrote an idea for software that I could use to record all my ideas. On my list were 10 functions that the program should have. Maybe I’ll implement it and launch it soon; we’ll see.

A Different Way Of Doing Things

A while back, I wrote a book last year called Skip The Line, about how everybody always tells me why I can’t do one thing or another. For example, why I couldn’t go from being a hedge fund manager to a stand-up comedian?

In the book, I talk about how I changed careers more than 10 times and always had to figure out how to get good at something and turn it into money.

I have done this through a strategy I call the 10,000 Experiments roll. So instead of working 10,000 hours, it’s better to do experiments.

For example, when I created the Stock Pickr website, it was just an experiment. How about I allow people to post their portfolios on one website, and then everyone can compare and comment on each other’s portfolios? It cost me less than $2,000 to build the website. A month later, I had over a million users! It was an experiment that worked perfectly.

Failed Experiments Are Okay

Most of my experiments fail miserably, but they make good stories.

Like this one time when Trump tweeted he wanted to buy Greenland and the Danish prime minister tweeted it was not for sale. I thought to myself, what the heck is this? I did not know you could buy a country! Besides, what does Denmark have to do with Greenland? So I did some research and found that there are reasons to buy Greenland.

Then I made a list of 10 reasons why you should buy Greenland. My experiment was to first raise a hundred million dollars through Kickstarter. Of course, Greenland would cost much more, and Kickstarter shut me down instantly. Even though it failed, it was a fun experiment. Plus, I learned how to run a Kickstarter!

How I’ve Skipped The Line to Success in Podcasting

So experiments have tremendous advantages and minimal disadvantages. With every podcast I do, I try to experiment. Sometimes I try out different interview styles. Other times I do not have anyone on at all. A good example of that is my I Was Wrong series, where I talk about all the issues I have written about in the past. That’s been very popular. I also did a series on owning a home.

I am constantly experimenting with different formats, new types of guests, or new ways to talk to guests.

With one guest, we decided to do a little miniseries called Good or Bad. We talk about very topical things and discuss whether they are good or bad for society.

Eight years and 1500 podcasts later, I keep trying to find new ways to reinvent the show.

Remember, podcasting is not a longevity race. It’s not about who’s been around the longest, who does the most podcasts, or even who has the most downloads.

You do a podcast because it changes you as a person and makes you a better person. I have had 1200 great guests and I have learned from every single one of them. I do not always remember everything I learned, but I try to remember at least one thing from each of them that I can implement in my life.

It has been a great experience. This is a little story about how I skipped the line towards podcasting, but I hope it was helpful.

Anyone who wants to contact me can reach me @JAltucher on Twitter. I try to respond to tweets.

Want to attend this quarter’s keynote live? Check out our upcoming PodPros Quarterly Virtual event.

About James Altucher:

James Altucher is an American hedge-fund manager, multiple times best-selling author, one of the world’s most successful podcasters, and a serial entrepreneur who has founded or co-founded over 20 companies. He has published 20 books and is a contributor to publications including The Financial Times, The Wall Street Journal, TechCrunch, and The Huffington Post.

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