
Friday 5: Five Weekly Lessons from Bestselling Books, Essays, and Lectures
Every week, we share the 5 best ideas from one of history's greatest books, speeches, interviews, and lectures. Learn how to negotiate from Steve Jobs, how to build strategic momentum from Jim Collins, and mental toughness from Special Operations soldiers. Start learning from the best innovators, founders, and investors in history. Get every new episode delivered via email →
Start learning from iconic founders, renowned investors, and bestselling authors including Brian Scudamore (1-800-GOT-JUNK), Mark Sisson (Primal Kitchen), Carey Smith (Big Ass Fans), Scott Belsky (Benchmark & Adobe), Luke Gromen (The Forest for The Trees), and Verlyn Klinkenborg (Yale & The New Yorker).
Visit OutlierAcademy.com for episode notes, searchable transcripts, videos, and more.
Latest episodes

Nov 24, 2022 • 25min
On Category Creation, Languaging, and Why Competition is for Losers
Welcome to another edition of Cheat Sheet by Outlier Academy. Where each week we compress 6+ hours of research and interviews into 3 big ideas that you can read in 5 minutes. This week we profiled one of the internet’s most-read writers (100M+ views), Nicolas Cole, and his latest book Snow Leopard: How Legendary Writers Create a Category of One with co-authors Eddy Yoon and Christopher Lochhead.
Read the newsletter companion to this episode:
https://www.cheatsheetnewsletter.com/p/category-creation-and-avoiding-competition
Here are the 3 big ideas in this week's Cheat Sheet:
Competition is for losers, avoid it at all costs.
How Eight Sleep created the Sleep Fitness category.
How to find and create your own category of one.
Sign up for the Cheat Sheet newsletter:
https://www.cheatsheetnewsletter.com
Listen, watch, or explore more of this week’s Outlier Academy episodes:
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
Listen Now | Watch Now | Episode Guide | Transcript
Snow Leopard: How Legendary Writers Create a Category Of One | Nicolas Cole, Author and Co-Founder of Category Pirates
Listen Now | Watch Now | Episode Guide | Transcript
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Nov 11, 2022 • 20min
On Obsessing Over Problems, Predicting the Future, and Why Healthcare Should be a Product (Not a Service)
This week we’re profiling Adrian Aoun, who founded Forward into 2017 to turn healthcare from a service into a product and reach 1B+ people globally. Before founding Forward, Adrian served as the Director of Special Projects for Google CEO Larry Page, founded Sidewalk Labs, and served as an advisor to the White House on the President’s Council of Advisors on Science and Technology.
Here are the 3 big ideas in this week's Cheat Sheet:
Principle: Be problem obsessed, not solution obsessed.
Framework: How to predict the future from first principles.
Insight: Why healthcare should be a product—not a service.
Read the newsletter companion to this episode:
https://www.cheatsheetnewsletter.com/p/problem-obsessions-and-predicting-the-future
Listen, watch, or explore more of this week’s episodes:
Forward’s Adrian Aoun | My Favorite Books, Tools, Habits and More
Listen Now | Watch Now | Episode Guide | Transcript
Forward: Bringing Healthcare as a Product to a Billion People | Adrian Aoun, Founder & CEO
Listen Now | Watch Now | Episode Guide | Transcript
Get the Cheat Sheet newsletter in your inbox:
https://www.cheatsheetnewsletter.com
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Nov 10, 2022 • 4min
Trailer: On Obsessing Over Problems, Predicting the Future, and Why Healthcare Should be a Product (Not a Service)
This week we’re profiling Adrian Aoun, who founded Forward into 2017 to turn healthcare from a service into a product and reach 1B+ people globally. Before founding Forward, Adrian served as the Director of Special Projects for Google CEO Larry Page, founded Sidewalk Labs, and served as an advisor to the White House on the President’s Council of Advisors on Science and Technology.
Here are the 3 big ideas in this week's Cheat Sheet:
Principle: Be problem obsessed, not solution obsessed.
Framework: How to predict the future from first principles.
Insight: Why healthcare should be a product—not a service.
Get the Cheat Sheet newsletter in your inbox:
https://www.cheatsheetnewsletter.com
Learn more about your ad choices. Visit megaphone.fm/adchoices

Nov 5, 2022 • 21min
On Spotting and Owning Trends, Wedge vs Ramp Shaped Businesses, and Making Every Dollar Count
This week we’re profiling Justin Mares, who has built 3 direct-to-consumer brands in Kettle & Fire, Perfect Keto, and Surely Wine that have all reached tens of millions in revenue. All by finding and owning emerging health and wellness trends.
Read the newsletter companion to this episode:
https://www.cheatsheetnewsletter.com/p/spotting-and-owning-trends
Here are the 3 big ideas in this week's Cheat Sheet:
How to spot trends and build businesses to own them.
Concept: Wedge versus ramp shaped businesses.
Reminder: Why it pays to bring on a Head of Finance early.
Listen, watch, or explore more of this week’s episodes:
#143 Kettle & Fire's Justin Mares | Identifying Trends, 5-Minute Mini Workouts, 6 To Dos Per Day, Favorite Books, and More
Listen Now | Watch Now | Episode Guide | Transcript
#144 Kettle & Fire, Perfect Keto, and Surely Wine: Spotting Trends and Building D2C Brands to Own Them | Justin Mares, Serial Entrepreneur
Listen Now | Watch Now | Episode Guide | Transcript
Sign up for the Cheat Sheet newsletter:
https://www.cheatsheetnewsletter.com
Learn more about your ad choices. Visit megaphone.fm/adchoices

Nov 4, 2022 • 3min
Trailer: On Spotting and Owning Trends, Wedge vs Ramp Shaped Businesses, and Making Every Dollar Count
This week we’re profiling Justin Mares, who has built 3 direct-to-consumer brands in Kettle & Fire, Perfect Keto, and Surely Wine that have all reached tens of millions in revenue. All by finding and owning emerging health and wellness trends.
Here are the 3 big ideas in this week's Cheat Sheet:
How to spot trends and build businesses to own them.
Concept: Wedge versus ramp shaped businesses.
Reminder: Why it pays to bring on a Head of Finance early.
Sign up for the Cheat Sheet newsletter:
https://www.cheatsheetnewsletter.com
Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 29, 2022 • 33min
The Secret to Eternal Life in Business
Welcome to another edition of Cheat Sheet by Outlier Academy. Where each week we compress 6+ hours of research and interviews into 3 big ideas that you can read in 5 minutes.
This week we profiled Worm Capital, who call themselves “value investors focused on the future.” They’re one of our favorite technology and disruption investors in the public markets. Since Worm’s inception in 2012, they’ve outperformed the S&P 500 by over 2X net of fees—generating 26.73% per annum vs the S&P 500’s 12.08%).
Read the newsletter companion to this episode:
https://www.cheatsheetnewsletter.com/p/the-secret-to-eternal-life-in-business
Here are the 3 big ideas in this week's Cheat Sheet:
Markets provide liquidity, businesses generate value. Or why the game of business has nothing to do with the stock market.
How to find the best companies in any industry. First observe, then deconstruct inputs and outputs.
The secret to eternal life in business. Or why the company that delivers the best customer value proposition consistently always wins.
Sign up for the Cheat Sheet newsletter:
https://www.cheatsheetnewsletter.com
Listen, watch, or explore more of this week’s Outlier Academy episodes:
20 Minute Playbook - Eric Markowitz, Worm Capital’s Head of Research | Conviction vs Opinions, Two-Step Research Process, Favorite Books, and More
Listen Now | Watch Now | Episode Guide | Transcript
Outlier Investors - Worm Capital: Value Investors Focused on the Future | On Worm Theory, Worm’s Investing Algorithm, and The Game of Business
Listen Now | Watch Now | Episode Guide | Transcript
Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 14, 2022 • 25min
On Category Creation, Languaging, and Why Competition is for Losers
Welcome to another edition of Cheat Sheet by Outlier Academy. Where each week we compress 6+ hours of research and interviews into 3 big ideas that you can read in 5 minutes.
This week we profiled one of the internet’s most-read writers (100M+ views), Nicolas Cole, and his latest book Snow Leopard: How Legendary Writers Create a Category of One with co-authors Eddy Yoon and Christopher Lochhead.
Read the newsletter companion to this episode:
https://www.cheatsheetnewsletter.com/p/category-creation-and-avoiding-competition
Here are the 3 big ideas in this week's Cheat Sheet:
Competition is for losers, avoid it at all costs.
How Eight Sleep created the Sleep Fitness category.
How to find and create your own category of one.
Sign up for the Cheat Sheet newsletter:
https://www.cheatsheetnewsletter.com
Listen, watch, or explore more of this week’s Outlier Academy episodes:
20 MINUTE PLAYBOOK
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
Listen Now | Watch Now | Episode Guide | Transcript
BOOK CLUB
Snow Leopard: How Legendary Writers Create a Category Of One | Nicolas Cole, Author and Co-Founder of Category Pirates
Listen Now | Watch Now | Episode Guide | Transcript
Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 29, 2022 • 22min
On Living to 100, Investing in AgeTech, and The Staggering Implications of Living Longer
Starting today, every Thursday we're going to condense down hours of interviews and research to give you the 3 best ideas, questions, and bits of wisdom from our podcast episodes that week in an email you can read in 5 minutes or listen with commentary in 10-15 minutes.
We call it Cheat Sheet, and it won’t cost you a dime.
Read the first issue on Abby Levy Miller & Primetime Partners (Episodes #135-136):
https://www.cheatsheetnewsletter.com/p/agetech-and-living-to-100
Here are the 3 big ideas and questions we're covering this week:
What changes when 50% of the U.S. population lives to be at least 100?
What kinds of investment opportunities does this create?
How should this all change the way we think about and approach our lives?
Sign up for the Cheat Sheet newsletter (sent every Thursday):
https://www.cheatsheetnewsletter.com
For more make sure to listen, watch, and explore the full episodes:
20 MINUTE PLAYBOOK
#135 Abby Miller Levy, Co-Founder of Primetime Partners and Thrive Global | On Living to 100, Getting to the Key Issue, and Choosing What to Major and Minor In
Listen Now | Watch Now | Episode Guide | Transcript
INFINITE GAMES
136 Primetime Partners: AgeTech, The Ripple Effects of Living Longer, and Investing in the Future of How We Age | Abby Miller Levy, Co-Founder & Managing Partner
Listen Now | Watch Now | Episode Guide | Transcript
Learn more about your ad choices. Visit megaphone.fm/adchoices
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