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.”

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Timestamps:

[00:00] Start

[05:14] Notes about this supercombo format.

[06:07] Enter Matthew McConaughey.

[06:35] The words forbidden in Matthew's house growing up.

[09:14] The book that changed the course of Matthew's life.

[17:43] Matthew's 10 goals in life (circa 1992).

[22:36] Why take more risks?

[26:20] The evolving purpose of keeping a diary.

[30:04] The art of running downhill.

[34:12] Learning to say "No" to rom-com typecasting.

[48:06] Enter Aisha Tyler.

[48:35] Aisha's role in The Tim Ferriss Show's existence.

[50:00] Aisha's trademark podcast question.

[51:22] Aisha's unorthodox childhood and family relationships.

[52:22] How did Aisha answer the questions "Whose day is it?" and "What are you going to do?" every morning?

[55:50] From where does Aisha get her general sense of optimism?

[57:41] Following father's advice and views on regret.

[59:38] Free-range parenting vs. modern overprotection.

[1:03:49] Having a bad day? You're not special!

[1:05:43] Young Aisha's career aspirations.

[1:07:08] Why was Aisha miserable at what she thought was her dream job?

[1:09:07] Why did Aisha pick standup comedy to break into show business?

[1:10:24] What it was like to keep a day job and do standup comedy as a hobby.

[1:12:06] Commuting for comedy in San Francisco.

[1:14:19] What made the comedy club bubble of the '80s burst?

[1:18:27] How did Aisha practice to get better at standup?

[1:19:17] A memorable set Aisha bombed and the gift it gave her.

[1:22:38] Dealing with hecklers Bill Burr and Kenny Moore style.

[1:28:36] Aisha shares some of her own heckler stories.

[1:32:47] Aisha's academic approach to the math of comedy.

[1:34:59] What's the Rule of Threes?

[1:35:52] Gauging comic evolution.

[1:37:02] Comedians compared to other artists.

[1:38:20] Changing success metrics and creative traps.

[1:41:01] How fear-based people-pleasing affects creativity.

[1:44:08] If one likes big butts, one cannot lie — even if it might tick someone off.

[1:46:19] Sometimes constructive feedback does make me change my mind.

[1:46:49] Pursuing authentic, meaningful work.

[1:48:48] Comedy's core beyond humor.

[1:49:20] Expecting failures in creative beginnings.

[1:50:08] Why it doesn't pay to emulate a master of a craft in their own field.

[1:52:07] Aisha's transition to filmmaking.

[1:55:03] Aisha believes in personal aggression.

[1:55:44] How Aisha piggybacked resources for her first music video.

[1:56:46] Learning filmmaking through short projects.

[1:58:09] What lessons did Aisha learn from these projects?

[1:59:22] How visiting the sets of Penny Dreadful and Vikings in Ireland led to making AXIS.

[2:01:08] Financing the Ireland trip.

[2:02:54] The email Aisha sent to visit the set of Vikings.

[2:03:34] The impact of fan appreciation.

[2:05:06] Budweiser's "Whassup" campaign origin.

[2:05:54] Why Aisha made AXIS.

[2:07:22] Resources for aspiring screenwriters and tech investors.

[2:08:22] What is AXIS, and did anyone try to talk Aisha out of making it?

[2:10:09] AXIS production experience and methods.

[2:12:16] The magic, intensity, and clarity of operating on an aggressive deadline.

[2:15:16] Aisha's current fears and goals.

[2:16:49] One of Aisha's current struggles.

[2:17:40] "If art imitates life, in order to create art, you have to have a life."

[2:18:49] As a workaholic, how does Aisha manage to live a life that influences her art?

[2:21:14] How would Aisha's life be different if she didn't have exercise as an element?

[2:23:03] What equipment does Aisha use to work out?

[2:23:52] What does a prototypical workout look like for Aisha?

[2:24:09] How does Aisha take her glutathione, and what does it help with?

[2:27:26] Morning routine and exercise timing.

[2:30:35] Does Aisha make New Year's resolutions?

[2:33:01] Aisha likens her first (unwatchable and destroyed) short film to the standup set she bombed.

[2:35:34] When has Aisha been extremely proud of herself?

[2:40:40] Parting thoughts.