Gary Gulman: The Evolution of Talent (in 3 steps)

Gary Gulman's Evolution of Talent In 3 Steps

Episode 170

I was trying to cheer someone up. “The sun feels nice,” I said.

“I don’t even notice those things,” he said.

My friend was depressed. But I thought I could help.

They say you can’t make everybody happy. But really, you can’t make anybody happy.

I know this. But it doesn’t always stop me from trying.

Six months ago, I did my first stand-up show. Now I have a new experiment. I take one photo a day. And I tell a story.

But I haven’t stopped thinking about stand-up. And I want to get better.

So I interviewed Gary Gulman. He’s one of my favorite comedians. Top two. Him and Louis C.K.

I’ll throw Amy Schumer into the mix. Top three.

Gary started 23 years ago. And I’ve watched his Netflix special, “It’s About Time” twice (so far).

The best way to learn anything is to study the masters.

Studying Gary taught me there are three steps to developing talent in anything:

Step 1: Start somewhere

Gary first tried stand-up in 1993. But that’s not how he got started.

Before that, he watched comedy. He repeated jokes to friends and got laughs. That’s how all successes start. You just do it for fun.

That’s how Derek Sivers started CD Baby and how AirBnB began. They were experiments.

Gary only had five minutes on stage.

“Back then I did impressions,” he said.

He did one of Seinfeld and Kramer playing basketball.

But “within a year, I had decided my impressions were not very good.”

That’s step 2: Evolve.

Doubt is a leader. It can take you away from what you don’t love and into what you do love.

“That’s how I got on the track I’m on now,” he says.

If you’re “good,” you’ll just sit back. And someone who’s no good will get better.

  • They’ll get a mentor
  • They’ll reinvent themselves
  • They’ll practice for 10,000+ hours
  • They build a love for it

If the “good” ones don’t evolve, they’ll remain just that… good.

Step 3: Tell your story

“I have symptoms of depression,” he said. “I almost feel like I’m moving in slow motion. There doesn’t seem to be any amount of sleep that satisfies me.”

I can’t sugar coat it. It sounds miserable. But it’s also the source of his comedy.

“I guess if I didn’t have a depressive view of the world, I wouldn’t have the premises to go off,” he said.

“But at the same time, if I didn’t have the depressive nature, I would have more confidence and more energy to write more and maybe expand into more acting or podcasting or writing a book.”

It’s a balance.

“On the days you get out of it, how do you get yourself out of it?” I asked.

There was a long pause.

“Or have you never gotten out of it?” I asked.

I wanted to find out what works for him.

And it came back to helping people.

“Stand-up comedy gave me a lot of reward,” he said, “as far as making people feel a little bit better and forgetting about their problems for a short time.”

He turns pain into humor, which morphs back into pain.

That pain becomes a bit. And that bit becomes a laugh.

You can’t make people happy. But if you tell your story, maybe you can make them laugh.

Resources and Links:

Also mentioned:

  • Gary’s favorite comedians:
  • Gary’s book recommendation for people interested in comedy: “True Story: A Novel” by Bill Maher
  • Gary’s favorite comedy-related documentaries:

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  • Linda Johnson

    Just a note — Not a fan of Amy Schumer. She body shames intact (not circumcised) men, and then wants people to refrain from body shaming her for being chubby.

  • Great stuff as always James – Where did the “share” buttons go?

  • Julie Carr

    Awesome read. Love #2 the most. I’ve been plagued with sel-doubt and when I read #2 it hit me like a ton of bricks. The doubt has made me work at my craft more than ever.

  • I loved this podcast, James. I wasn’t familiar with Gary Gulman, so I immediately went to Youtube and looked him up. He’s hilarious and in a very interesting way – I get what you were saying when you mentioned his tangents… he seems to purposely veer off during his stories and then circle right back around to the original point. And it’s very funny! Excellent stuff! I also wanted to comment on his mental health – he sounded very depressed. I hope he finds a treatment that works for him.

  • snowyowl

    Those who make others laugh are special. Once again, thank you for all your skills and sharing them.

  • ninja265

    James, could you please interview KRS-ONE or DJ Premiere, would be a very interesting and different episode. I am personally interested to learn more about their mastery. DJ Premiere is perceived as the headquarters of Hip Hop. Alot has changed in the hip hop world but Preemo stands out by his own style from the 80’s and every new rapper considers working with him as an achievement.

  • The three steps – start somewhere, evolve and tell your story – provide a simple yet powerful framework. If you don’t get started, you will stay where you are. But if you get started, it is certain that you would reach somewhere else!

  • Linda Sand

    I will never forget the first time I saw Gary Gulman on TV; he did his bit about what happens in the gym and made a male judge blush. Thanks for linking to his video; I enjoyed it, too.

  • Susan Reynolds

    So interesting! I did my first stand up gig at a singles night at Wisdom 2.0 in SF in February. I’d rehearsed my entire dating story, my Sri Lankan Tinder date, it was half scripted/half rehearsed. I knew what I was doing, and then in a conversation 10 minutes before I was to go on, I changed my story. I wasn’t telling the right story. The real story. The story of heartbreak and redemption, but not the type you might think.

    I lost the love of my life, soul mate over lifetimes love. We awakened together, and then he went back to sleep. In my need to get the awakened one back, I was grabby, clingy, and needy. He had an affair and left me. But in that leaving, I found Steve. I hated going to conferences alone, so on a message board at in 2014, I connected with Steve Mark, a 6’3″ married man. He taught English, yoga and was married to the love of his life Jim for many year.

    I found my Plus One for this conference, one of my best friends in our campaign for love, tonglen, and equality. My role model in putting your heart our there to the world, letting them see your joy and sorrow, and loving the world no matter how cruel it can be.

    Steve and I practice Ubuntu, Tat Tvam Asi, I am you, You are me. We are we. We are One. I am Steve. Steve is Me. I reached out to Steve on a message board. I trusted the Internet to deliver me the friend I needed, when I needed one. You can, too.

    Try it and join the Open Mind Challenge put forth in the Dartmouth College Commencement Address by Leymah Gbowee!