Episode Details

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode #474 "Matthew McConaughey — The Power of 'No, Thank You,' Key Life Lessons, 30+ Years of Diary Notes, and The Art of Catching Greenlights" and #327 "Aisha Tyler — How to Use Pain, Comedy, and Practice for Creativity."

Please enjoy!

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Timestamps:

[00:00] Start

[04:58] Notes about this supercombo format.

[05:51] Enter Matthew McConaughey.

[06:19] The words forbidden in Matthew's house growing up.

[08:58] The book that changed the course of Matthew's life.

[17:27] Matthew's 10 goals in life (circa 1992).

[22:20] Why take more risks?

[26:04] The evolving purpose of keeping a diary.

[29:48] The art of running downhill.

[33:56] Learning to say "No" to rom-com typecasting.

[47:50] Enter Aisha Tyler.

[48:19] Aisha's role in The Tim Ferriss Show's existence.

[49:43] Aisha's trademark podcast question.

[51:06] Aisha's unorthodox childhood and family relationships.

[52:06] How did Aisha answer the questions "Whose day is it?" and "What are you going to do?" every morning?

[55:34] From where does Aisha get her general sense of optimism?

[57:25] Following father's advice and views on regret.

[59:22] Free-range parenting vs. modern overprotection.

[1:03:33] Having a bad day? You're not special!

[1:05:27] Young Aisha's career aspirations.

[1:06:52] Why was Aisha miserable at what she thought was her dream job?

[1:08:51] Why did Aisha pick standup comedy to break into show business?

[1:10:08] What it was like to keep a day job and do standup comedy as a hobby.

[1:11:50] Commuting for comedy in San Francisco.

[1:14:03] What made the comedy club bubble of the '80s burst?

[1:18:11] How did Aisha practice to get better at standup?

[1:19:01] A memorable set Aisha bombed and the gift it gave her.

[1:22:22] Dealing with hecklers Bill Burr and Kenny Moore style.

[1:28:20] Aisha shares some of her own heckler stories.

[1:32:31] Aisha's academic approach to the math of comedy.

[1:34:43] What's the Rule of Threes?

[1:35:36] Gauging comic evolution.

[1:36:46] Comedians compared to other artists.

[1:38:04] Changing success metrics and creative traps.

[1:40:41] How fear-based people-pleasing affec