Chris Gethard

How to Talk About The Hard Things In Life & Make it Funny

Episode #480

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Four years ago, I started a secret project.

Two years later, I filmed it. And posted it to Facebook. The reaction was mixed.

Mad. Supportive. Confused.

I heard this quote recently (probably from Steve Cohen). “People feel jealous when they see someone else living up to their potential.”

I wasn’t good at the project. (Stand-up comedy). I sucked. But I started.

That’s the trigger.

Chris Gethard started his own TV show. He didn’t wait for a network or agent to “approve” of him.

Years later he got a call from Will Ferrell. He wanted to put in Comedy Central.

My friend Gary Gulman tweeted this article Chris wrote on Medium, “My Personal Opinions Regarding What I Do.”

It’s a list of tips he tells himself. From years of experience. To “try to guide myself towards work and behavior I’m proud of.”

These tips work for any area of life.

Sales, business, connecting with people, etc.

Learning how to be funny, read a crowd, take a hit, bomb, get back up, rewrite, revise, rethink… these are transferable skills every successful person on my podcast knows.

And Chris Gethard is one of the best at breaking them down.

Here’s a list of everything we talked about. Feel free to jump around

  • BONUS: Hear how you can get an exclusive, free copy of my latest book, “The Side Hustle Bible,” which is a collection of proven opportunities (177, to be exact) to turn your hobby or existing skills into an entirely new source of income. – [0:00]
  • Episode preview – [2:20]
  • Hear how I accidentally insulted Christ Gethard the minute the interview starts – [5:29]
  • I introduce Chris and his TV shows, books, specials, etc. – [6:15]
  • When to kill a project or give up… Chris says how he decided to wrap up “The Chris Gethard Show” – [6:40]
  • Stop setting goals. It ruins creativity – [9:30]
  • The best advice Chris got from his therapist – [10:12]
  • Chris says how being ok with fail helped relieve his anxiety – [12:02]
  • The fear of running out of money… how it forces you to get better. And hear what Chris did when he hit zero – [12:30]
  • How to get thick skin, be unapologetic and make things happen – [14:26]
  • I say why I originally wanted Chris Gethard on the show… and how his career tips can apply to any person who wants to get better incrementally at their craft or job or anything – [15:04]
  • I ask Chris about getting over fear – [16:18]
  • Hear why overthinking and self-doubt WILL slow your success. And how to start combating it – [17:47]
  • How to bypass the gatekeepers.. – [19:34]
  • Chris says how he experimented with the classic talk-show format and made something new and unique – [21:49]
  • Behind the scenes of a fake, Hollywood interview vs. a genuine, real conversational show – [24:03]The eye-opening element of Chris’ comedy special, “Career Suicide” – [26:30]
  • Storytelling vs. comedy and how to find your style – [29:10]
  • The key to making “A” material – [30:51]
  • What it takes to be a headliner – [32:12]
  • Chris dissects the two big camps of comedians (art comics vs. club comics) – [37:51]
  • Go out on a limb… Whatever you’re striving to do, don’t just try to be that one thing. For example: Chris doesn’t just try to be funny. He adds extra value around that. Chris calls this “Funny Plus” – [39:23]
  • Why everyone needs to learn the skill of storytelling (no matter what you do for a living) – [42:34]
  • The difference between exploiting your pain and alchemizing it – [43:27]
  • Fighting anxiety, low self-esteem and depression in front of an audience… Chris talks about the time he realized that even if he bombed on stage, he was always still connecting with 3 or 4 people – [45:19]
  • Why Chris’ comedy is the best way to grasp what depression really is – [48:01]
  • “It’s all tools,” Chris says about how he gets people to laugh about darker realities – [50:19]
  • How to bring new things to the table… Chris says, “Whatever field you’re in, the bar has been set. The sooner you can find those things nobody sees coming, this is how you super seed the bar. And once you start to get innovative, you become a little more bulletproof.” – [52:11]
  • Take the pressure off. Chris’ goal is to make his shows 51% funny. Not 100%. He just wants to be past the tipping point – [54:43]
  • I ask Chris how he deals with the volatility of having an unsafe job like comedy and how the industry impacts his depression. He says, “You have to be able to respect the emotions you’re having… as long as the logic exists.” – [55:17]
  • How Chris is dealing with “the biggest financial setback he’s ever had” while waiting for his first child to be born – [57:36]
  • How to have integrity in your work – [59:20]
  • The difference between being disappointed in your life or realizing your living your younger self’s dream – [1:00:40]
  • Where new content comes from – [1:02:15]
  • Chris says he’s scared his kid will get bullied when they hear his comedy – [1:02:54]
  • The moment Chris found out his dad was jealous of him and proud – [1:04:38]
  • Deep dive: We talk about Chris’ article “My Personal Opinions Regarding What I Do” [1:06:35]
  • Tip #1… Chris says how blaming others blocks you from improving – [1:08:19]
  • Do what you do for YOU – [1:12:50]
  • I play devil’s advocate with Chris… is there such thing as a bad audience? – [1:15:07]
  • How a pro turns around a tough crowd – [1:17:04]
  • The importance of re-evaluating what’s happening in your industry, career, personal relationships, etc. [1:19:20]
  • Take the pressure off yourself… I asked Chris how he defines success in stand up… he boils it down to this “did the people in the room have a slightly better chunk of their day than before I started talking on the microphone.” Then he asks himself “How high can I make it go?” – [1:21:25]
  • Set the bar low… we dissect Andy Kaufman’s performance on “The Morning Show” – [1:23:43]
  • Find out why comedy skills are extremely applicable to business – [1:26:31]
  • Persuasion tactic: address what the other person is thinking – [1:27:40]
  • Book recommendation: “Influence” by Robert Cialdini – [1:29:00]
  • Tip #2: every kind of art, business, comedy, etc. sucks sometimes – [1:30:02]
  • The advice Dave Chapelle gives to Will Smith “It’s better to be interesting than funny” – [1:31:56]
  • Tip #3: the importance of making your point – [1:32:54]
  • Tip #4: take time to live some real life and DO – [1:35:50]
  • Comedian recommendation: John Mulaney – [1:37:37]
  • Comedian recommendation: Gary Gulmam- [1:38:27]
  • Tip #5: know the environment you’re walking into – [1:40:14]
  • The most important tip that applies to many areas of life… understand and use the power of free – [1:43:02]
  • Tip #6: appreciate the people who give you their time and attention – [1:46:08]
  • Tip #7: challenge yourself (I say the story of doing stand up on the subway) – [1:49:12]
  • Tip #8: Find honest ways to connect with people (another versatile tip) [1:51:15]
  • Tip #9 and I ask Chris his advice on touring – [1:52:52]
  • Tip #10: be willing to deal with negative reactions to your work – [1:55:05]
  • Comedy special recommendation: Jerod Carmichael “Eight” – [1:57:47]
  • A list of all of Chris Gethard best work including this article: and his special “Career Suicide” [1:59:33]
  • One of my favorite quotes from Chris, “Don’t act like a comedian. Act like yourself.” This is how you go from good to great st anything – [2:00:16]
  • Chris says one of the reasons why it’s so hard to show up with a sense of self is because we try too hard to emulate our heroes – [2:02:11]
  • Interview wraps and I thank Chris for coming on the show – [2:03:34]

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