Outlier Academy

20 Minute Playbook Episodes

Learn the tactics, tools, and habits of iconic founders, renowned investors, and bestselling authors. As well as the books, figures, and ideas that have shaped them. All in about 20 minutes. Past guests include Scott Belsky (Benchmark & Adobe), Gokul Rajaram (Square & Doordash), Alexandra Zatarain (Eight Sleep), Brian Scudamore (1-800-GOT-JUNK), Adrian Auon (Forward), and James Currier (NfX). New episode every Tuesday.
Adrian Aoun of Forward: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Nov. 8, 2022

Adrian Aoun of Forward: My Favorite Books, Tools, Habits and More | 2…

We deconstruct Adrian Aoun's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Adrian Aoun is the CEO and Founder of Forward. We cover why medical wearables don’t work, focusing on …

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#143 Kettle & Fire's Justin Mares | Identifying Trends, 5-Minute Mini Workouts, 6 To Dos Per Day, Favorite Books, and More
Nov. 1, 2022

#143 Kettle & Fire's Justin Mares | Identifying Trends, 5-Minute Mini…

Justin Mares has a knack for identifying trends and building D2C businesses to own them—including Kettle & Fire, Perfect Keto, and Surely Wine. Learn how he identifies trends, why he focuses on just 6 tasks each day, how he gets …

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Eric Markowitz, Head of Research at Worm Capital | Worm's Two-Step Research Process, Favorite Books, and More
Oct. 25, 2022

Eric Markowitz, Head of Research at Worm Capital | Worm's Two-Step Re…

Listen as we deconstruct Eric Markowitz's, Director of Research at Worm Capital, peak performance playbook. We cover everything from Worm's two-step investment process, to Eric's journey from journalism to investing, as well as his favorite books and more.

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#141 Joey Cofone, Founder & CEO of Baronfig | Favorite Baronfig Products, Skill vs Renown, Daily Disciplines, Favorite Books, and More
Oct. 18, 2022

#141 Joey Cofone, Founder & CEO of Baronfig | Favorite Baronfig Produ…

Listen as we decode daily disciplines, favorite books, favorite Baronfig products, and more with Joey Cofone, Founder & CEO of Baronfig and author of The Laws of Creativity. We also cover the best advice he’s been given by mentors as …

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#139 Nicolas Cole, Co-Founder of Category Pirates and Ship 30 for 30 | Favorite Books and Writing Tools, Enduring Boring Things, and Why Great Writing Changes the Reader
Oct. 11, 2022

#139 Nicolas Cole, Co-Founder of Category Pirates and Ship 30 for 30 …

Listen as we decode favorite books, writing tools, and the advice he’d give his younger self with Nicolas Cole, Co-Founder of Ship 30 for 30 and Category Pirates. We also cover why all great writing changes the reader and how …

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#137 Jivko Bojinov, Co-Founder and SVP of Strategic Projects at ShipBob: On Playing Professional Tennis, Putting in the Work, Resilience, and Taking Things from Zero to One | 20 Minute Playbook
Oct. 4, 2022

#137 Jivko Bojinov, Co-Founder and SVP of Strategic Projects at ShipB…

In Episode #137, we deconstruct Jivko Bojinov's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Jivko Bojinov is the Co-Founder and SVP of Strategic Projects at ShipBob. We cover falling …

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Replay – #105 Gokul Rajaram of Doordash, Square, and Google: My Favorite Books, Tools, Habits, and More | 20 Minute Playbook
Sept. 23, 2022

Replay – #105 Gokul Rajaram of Doordash, Square, and Google: My Favor…

In this Replay episode, we deconstruct Gokul Rajaram's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Gokul is an angel investor and Product and Business Helper at DoorDash. We cover …

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#134 Chris Sparks, Author of Experiment Without Limits: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Sept. 16, 2022

#134 Chris Sparks, Author of Experiment Without Limits: My Favorite B…

In Episode #134, we deconstruct Chris Sparks's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Chris Sparks is the author of Experiment Without Limits. We cover applying game theory to …

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#132 Ben Blumenrose of Designer Fund: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Sept. 9, 2022

#132 Ben Blumenrose of Designer Fund: My Favorite Books, Tools, Habit…

In Episode #132, we deconstruct Ben Blumenrose's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Ben Blumenrose is the Co-Founder and Managing Partner of Designer Fund. We cover how AI …

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#130 Robert Cantwell of Compound Kings: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Sept. 2, 2022

#130 Robert Cantwell of Compound Kings: My Favorite Books, Tools, Hab…

In Episode #130, we deconstruct Robert Cantwell's peak performance playbook—from their favorite book to the tiny habit that's had the biggest impact on their life. Robert is the Portfolio Manager at Compound Kings. We cover longevity in investing, source documents, …

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#128 Andrew Herr of Fount: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Aug. 26, 2022

#128 Andrew Herr of Fount: My Favorite Books, Tools, Habits and More …

In Episode #128, we deconstruct Andrew Herr's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Andrew is the Founder and CEO of Fount. We cover how the brain acts under …

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#126 Saad Alam of Hone Health: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
Aug. 12, 2022

#126 Saad Alam of Hone Health: My Favorite Books, Tools, Habits and M…

In Episode #126, we deconstruct Saad Alam's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Saad is the Founder and CEO of Hone Health. We cover radical transparency, daily gratitude, …

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#124 Andrew Carter of Smallhold: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
July 29, 2022

#124 Andrew Carter of Smallhold: My Favorite Books, Tools, Habits and…

In Episode #124, we deconstruct Andrew Carter's peak performance playbook—from their favorite book to the tiny habit that's had the biggest impact on their life. Andrew is the Co-Founder & CEO of Smallhold. We cover eliminating the ego, building around …

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#123 Steve Vassallo of Foundation Capital: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
July 22, 2022

#123 Steve Vassallo of Foundation Capital: My Favorite Books, Tools, …

In Episode #123, we deconstruct Steve Vassallo's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Steve is General Partner at Foundation Capital. We cover translating non-human languages, enlightened procrastination, and …

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#121 Adrian Aoun of Forward: My Favorite Books, Tools, Habits and More | 20 Minute Playbook
July 15, 2022

#121 Adrian Aoun of Forward: My Favorite Books, Tools, Habits and Mor…

In Episode #121, we deconstruct Adrian Aoun's peak performance playbook—from their favorite book to the tiny habit that's had the biggest impact on their life. Adrian Aoun is the CEO and Founder of Forward. We cover why medical wearables don’t …

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