How to Skip The Line to Succeed in Podcasting (Lessons From James Altucher)

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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How to skip the line to succeed in podcasting? That’s what I want to talk about today. Interestingly, I did not want to be a podcaster. I wouldn’t say I like talking to people that much. At least not as much as I like to sit in my house to read and write all day. But then, one day, an opportunity to do a podcast came along.

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

So I figured this was a good chance to call up all of my favorite people.

I now had the perfect excuse to talk to people I would normally never speak to. More than that, I got a chance to ask all the questions I had.

It’s been one fantastic experience so far.

But I’m getting ahead of myself. How did all this happen? Let’s 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 company was in the mid-nineties. I was doing a website for HBO. So this was 1996, and¬†hbo.com¬†didn’t even exist. So I convinced HBO to buy the URL. Back then, their website URL was¬†homeboxoffice.com.

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

So I found myself running HBO’s website. But I wasn’t done. Now I wanted to convince HBO to make web shows similar to how they made TV shows. After all, I wanted to work at HBO because I loved their TV shows!

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

So I decided I wanted to go and talk to the CEO, Jeff Bewkes. I have to point out that I was only a junior analyst programmer, and no one cared at all about the IT department at HBO. We weren’t even located in the same building!

So 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 marketing of HBO. She asked me, “where are you going?”

I said, “I’m going to go to the CEO’s office. I have this idea for Jeff Bewkes.” Then she said, “You can’t just go to the CEO’s office. What are you going to talk to him about?” I quickly responded, “Well, I have an idea for him to do shows on the web the way they do shows on TV. Innovative and sort of a little bit edgy shows.”

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

This was one of many times before that moment, and afterward, people have told me I couldn’t do something because of X, Y, or Z. Sometimes, they have good intentions. They don’t want you to make a fool of yourself, or they don’t want you to get fired. Sometimes, they want you to keep your expectations ‘realistic’.

If I said, “I’m going to be a leading scorer in the NBA next year,” and somebody told me I can’t, 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. They don’t want you to succeed where they have not even tried or where they tried and failed.

Again, they might not have malicious intent, but you can’t listen to such people.¬†The path to ‘can’ is usually filled with cant’s.

So I kept on my journey to Jeff’s office. When I walked into his office, he looked up and said, “Who are you?” I answered, “Well, I’m building hbo.com and I think HBO should do web shows.”

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

I went on to share my idea for a show called III: am. I would interview people in the streets of New York City at 3 am Tuesday. Not a Saturday night, because everybody is out on the weekend. I went on to do this for two and a half years! Every Tuesday or Wednesday night, I went out at three in the morning with my camera crew to record interviews of random people.

I interviewed prostitutes, drug dealers, pimps, you name it. One time I even went on the bus that goes back and forth between Queens, New York and Rikers Island jail. I basically turned over every rock in New York City between 1996 and 1999, interviewing about 3000 people!

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

At one point, HBO hired a bodyguard for me because you never knew when the person I was interviewing would turn on me and chase me away.

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

Soon after, other companies started approaching me, asking if I could do their website for them. No one knew that the internet would become this e-commerce behemoth at that time. In fact, very few people knew how to do websites back then.

I remember American Express asked their accounting firm who 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 the website.
Together with my brother-in-law, who was a designer, we worked on the website and got paid $250,000.

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

Unfortunately, I knew nothing about keeping and growing my money. So I went broke really quickly. But before I went broke, I bought a fancy apartment, all sorts of other expensive toys and made a lot of bad investments.

At one point, I was almost losing my home. The IRS was after me, and I didn’t know how I was going to pay for them. I couldn’t even meet my mortgage payments. The dot-com bubble had happened, which meant everyone thought the internet was a fad.

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Rebuilding Again From The Ground Up

One day I was taking a walk when I came across this restaurant supplies store. I went in and bought a waiter’s pad for $10. The next day I started writing down 10 ideas a day.

My first idea was a concept for a book titled ‘beat your friends and family at every game in the universe. For instance, if you know all the two-letter words, like a 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 every day, I would write 10 ideas. Were all these good ideas? Probably not. But I found that I was exercising this idea muscle. I didn’t realize you had to exercise your creativity.

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.

Suddenly with all these neurons connecting, I could now link my interest in writing with my interest in games or my passion for investing with my passion for software. I started feeling excited about all these ideas that I could potentially work on.

Soon after, I started writing ideas for other people. For instance, I wrote a list for one writer. He wrote back to me, and he said, “This is great. Why don’t you write these articles for me?” That’s how I started writing for Jim Cramer’s website,¬†thestreet.com.

Then I wrote to one hedge fund manager sharing 10 ideas for hedge fund strategies he could try. He responded, “This is great. How about I allocate money to you? And you do them?” That’s how I started a hedge fund. More things started working out for me, eventually lifting me out of my depression.

Many years later, I wrote 10 ideas for a website I wanted to create about financial news. I built that and called it Stock Pickr. I sold that for a couple of millions but went broke again because I still hadn’t learned the skill of keeping money. I had to start from scratch again.

However, I kept doing 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 big-time radio host in New York City. I had watched his interview with Joe Biden. So I wrote a list of¬†10 questions Charlamagne could have asked Joe Biden. When I shared it with him, 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.”

Remember, you always want people to steal your ideas because how will you execute all your ideas?

Ideas are like the currency of the 21st century.

So Charlamagne said, “Oh, why don’t you help me write the book?” So we wrote this together, and it became a best-selling book on Audible and Audible Originals. Opportunities always come my way because of me writing these 10 ideas lists!

How I Got Into Podcasting

Ultimately, back in 2012, writing these lists led me to publish a book called Choose Yourself. It is about how I dug out of the holes I kept putting myself in and survived enough to feed my family and create new opportunities for myself.

This one guy liked it enough to fly up to New York and tell me, “How about you do a podcast, and we’ll produce the whole thing.” I didn’t know anything about producing a podcast. So I said No, but we kept in touch.

Eventually, I realized this is a great way to call up people that I admire.

So I started the podcast in December 2013. The people who were producing my podcasts thought I would have financial people to investors and hedge fund managers on the show.

Maybe I should have stuck with a niche like that, but I really wanted to talk to everybody. Some of my guests have included Gary Kasparov, the former world chess champion, Kareem Abdul Jabbar, the best basketball player in history and Danica Patrick, the best female car racer in history.

Wayne Dyer, Tim Ferris and so many other great people. I have also interviewed a bunch of congressmen, governors and politicians. Not to forget, all my favorite writers have been on my podcast!

So why do these people come on my podcast? Well, for several reasons.

A common one is because they want to promote something. I always look for who’s publishing a book in the next six months. Then I’ll write to every single one of them. “Hey, I’ve had on so-and-so, and I see your book is coming out. Why don’t you come on my podcast and we’ll talk about it?”

A lot of the time, I drop the names of people who have been New York Times bestsellers. I don’t know if anybody actually sees a bump in their book sales by being on my podcast. Maybe they do, perhaps they don’t, I don’t know.

But again, I love to write, so having great writers on my show is always a bast. Whether they’re Tim O’Brien, the author of a wonderful short story collection,¬†The Things They Carried¬†or Ken Follett, who’s sold 150 million copies of his thrillers.

I’ve also had great hedge fund managers, 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, all of it comes down to this practice I do of writing 10 ideas a day.

It’s such a simple yet really powerful practice. And it only takes 20 minutes, yet it’s created so many opportunities for me. It’s changed my life in so many different ways. Even now, to this day, I still write my lists.

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

The other day I wrote an idea for a piece of software to keep track of all of my ideas. On my list were 10 features that the program would have. I might implement that and launch that 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’ve switched careers over 10 times and always had to figure out how to get good at something and monetize it.

I’ve done this through a strategy I call the¬†10,000 experiments role. So instead of just doing 10,000 hours, it’s better to do experiments.

For instance, 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? It cost me less than $2,000 to build it. A month later, I had over a million users! This was an experiment that worked.

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

Like this one time Trump tweeted how he wanted to buy Greenland, and the prime minister of Denmark tweeted it’s not for sale. I thought to myself,¬†what the heck is this?¬†I didn’t know you could buy a country! Also, what did Denmark have to do with Greenland? So I did some research and realized there are reasons to buy Greenland.

Then I made a list of 10 reasons one should buy Greenland. My experiment was to raise a hundred million dollars through Kickstarter to start off. Of course, Greenland would cost much more and Kickstarter shut me down instantly. Even if it failed, it was a fun experiment. For one, I learned how to do a Kickstarter!

How I’ve Skipped The Line to Success in Podcasting

So experiments have huge upside and minimal downside. Every podcast I do, I try to experiment with things. Sometimes, I’ll try different interview styles. Sometimes I won’t have anybody on at all. A good example was when I started a series called¬†I Was Wrong, where I talked about all the issues I’ve written about in the past. It turned out to be really popular. I also did one about owning a home.

I’m always experimenting with different formats, new types of guests or new ways to talk to the guests.

There’s one guest we’ve decided to do a little mini-series called¬†Good or Bad. We talk about very topical things and discuss whether they’re good or bad for society. And so that’s about to launch.

Eight years and 1500 podcasts later, I’m always trying to find new ways to reinvent it.

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

You do a podcast because it changes you as a person, making you a better person. I’ve had 1200 great guests, and I’ve learned from every single one of them. 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.

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.

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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