On Wednesday night, James Altucher performed with Mark Hayes, Michael Rapaport, Jeremy Piven, and Francis Ellis. I spoke to James about his career in stand-up, his podcast The James Altucher Show, and his least favorite thing about fall. His responses below are sure to both entertain and intrigue you.
1. You’ve done a lot of different things career wise. What drew you to stand-up?
A woman spit wine all over me. I was at a party in 1994. I started talking to a woman and I told her a joke. She laughed so hard mid-swallow of wine that she ended up spitting a mouthful of wine all over my face and shirt. Right then I knew I wanted to make people laugh forever. From 1996-98 I worked with HBO Comedy. I'd go to all the comedy clubs, go to the Aspen Comedy Festival, interview comedians (George Carlin, Rodney Dangerfield, Janeane Garafaolo, Dave Chappelle, etc). George Carlin told me how he switched from telling jokes to telling the truth.
Then as Rodney Dangerfield was arriving he whispered to me, "That guy is high as a kite right now."
I asked Rodney Dangerfield, "What's the craziest thing that's happened to you at three in the morning?"
He said about 0.1 seconds later, "Her husband came home!"
I loved the intelligence, the quickness, the laughter, the subculture.
Then I decided to ruin my life.
I started a business. Made money. Went broke. Got depressed and suicidal. Started another business. Made money. Went broke. Lost three homes. Lost two marriages. Made millions again. Lost them again. Raised kids. Wrote 20 books. Went from being an Internet expert to a hedge fund manager to author to podcaster. Most of my readers thought I was mentally ill which meant I had to write even more crazy stories. I wrote stories about all my failures.
People kept saying to me, "You can't write that!" Which, in translation, means to me, "I have to write that!"
My mother and my two sisters stopped talking to me because they were embarrassed about what I was writing. I was so scattered I stopped renting an apartment and just lived from Airbnb to Airbnb, switching homes every three days for years. I was a mess.
Which meant people trusted me when I went on TV.
I started giving a lot of public talks and regular TV appearances. CNBC would have me on because I was the only person who was always optimistic even in the worst times. People watching would write on message boards, "Watching that guy is like watching a train wreck in real time" or my favorite "Why did CNBC bring that homeless guy on."
Many people would write me and incorrectly encourage me by saying, "you should be a standup comedian".
Finally, in 2015, on a podcast, Stephen Dubner (Freakonomics) and I challenged each other to do seven minutes of Standup.
The day we did it I was so scared I couldn't sleep the night before. I was planning on not showing up. I was planning on skipping town or never speaking to anyone ever again to avoid the shame and embarrassment.
I went. Ten minutes before I was going to walk out of the building and never be seen again. Five minutes before. One minute. Then I went on stage. It was in front of a sold out audience at the Bell House in Brooklyn. Negin Farsad was MC-ing.
I remember one joke. This was around the time Sean Penn was involved with catching the drug criminal El Chapo. I said, "Sean Penn, you were so great at finding El Chapo...if you are listening to this, can you please help me...find...a father."
And then I was hooked. I wanted to go up every chance I could get. I went from thinking I was decent to realizing I was horrible. I started doing stand-up on subways to practice one-liners since the "unfriendly audience" was ruthless in judging me unless the jokes were as tight as possible.
I never realized how hard stand-up comedy was. I'm a nationally ranked chess master, I've played poker professionally, I've been a professional investor for 20 years, software developer for 30, started 20 businesses (17 solid failures), have sold millions of copies of my books over the past 15 years, 80 million downloads of my podcast, and stand-up comedy is the hardest skill I've ever had to learn.
So I started inviting more and more stand-up comedians on my podcast. I asked them every question I could think of to make myself better. It was totally selfish of me. I watch comedy or study it or write it at least three or four hours a day. I still try to perform as much as possible.
What fascinates me is that there is no skill called "Stand-up comedy".
It's a basket of sub-skills: humor, stage presence, crowd work, delivery, likability, improvisation, on top of the practice of observing the events around you in unusual ways to establish a comedic point of view.
The ability to see everyday events, people, things, in a brand new light, and twist it around to express a truth and twist it further to punch it, and then twist it further to make it absurd while still keeping a point of view and a sense of humor.
I've always been proud of the fact that my writing has a unique point of view. And I've always had a good sense of humor. And I've always been a good public speaker. And I've been good in my TV appearances. But the stage in a comedy club is a jungle. Tying it all together is unbearably hard. It's a risk. It's a challenge. It's terrifying. It feels newly impossible every day. It's an addiction.
2. Who is the most memorable guest you’ve had on your podcast?
I have "bucket list" guests. Guests from my childhood that I worshipped: William Shatner (Captain Kirk), Henry Winkler (the Fonz), Garry Kasparov (best chessplayer in history), Coolio and Wyclef (my favorite rappers), Richard Branson, and so many more.
But also I've had on my good friends: Tim Ferriss, Ryan Holiday, Amy Morin ("13 Things Mentally Strong People Don't Do"), Tyra Banks, Mark Cuban, and I've had on many great comedians: Gary Gulman, Sebastian Maniscalco, Jim Norton (who I grew up with), Bonnie McFarlane, Paul Reiser, Marina Franklin (my first comedian guest ever), Tom Papa, Todd Barry, Susie Essman, Jeff Garlin, the list goes on.
I've had 500 guests so far and they are all my heroes.
3. Does anything about stand-up ever come into play when you’re on a podcast?
Once I started doing stand-up, it connected to every part of my life. It became the prism and the prison to see and do everything else.
In a podcast, the hard part is transitioning from interviewing a stranger to interviewing a friend, to both sides laughing at the absurdity of it all. It's only then that the magic in a podcast happens. Comedy has been the best performance enhancer for my podcast.
4. What was your first time doing stand-up like?
I've described my first time doing stand-up in a club above. But I did do a stand-up style show at a talk in January 2014.
It's different from a club because it was a crowd that mostly knew me and they were familiar with my topic. But for the prior 24 hours I watched about ten stand-up comedy specials and I wanted to deliver each point I was making as a joke: setup, punchline, reversals, absurdity, crowd work.
I was a big believer in watching stand-up comedy before delivering a talk. How come?
Because humans have something called mirror neurons. If you have never climbed a ladder, but you watch someone climb a ladder, your mirror neurons kick in and your brain thinks you just climbed that ladder. Now you know how to climb a ladder.
Stand-up comedians are the best public speakers. They use their voice more, they perform more, they have better stage presence, they read the audience better, they move better, and they go that extra step of not just making an interesting point, but stretching that point to find the punchline.
That talk I gave (to a friendly audience) was perfect from beginning to end. I was so happy after! Paul Reiser performed after me and afterwards people came up to me and told me everything I wanted to hear. I was determined then to do stand-up at a club but it took me over a year after that to get started.
5. What is your least favorite thing about fall?
PTSD of school starting again. I start having nightmares that I'm late on my homework and I'm going to get thrown out and my parents will hate me.
All of those events actually did happen, so the first dead leaf brings back the flood of memories of the beatings and the screaming.