Dickie's Digest - The Best of 2020
Inside you'll find the most popular links, articles, podcasts, and tweets from the first 52 editions of Dickie's Digest.
Hey there - happy Sunday!
52 weeks ago I started Dickie’s Digest. It started with a simple goal: write a newsletter every Sunday for 52 weeks. If no one was reading it after 52 weeks, I would hang it up.
52 weeks, 52 Digests, and 1,701 readers later, here we are. What a year! The Digest is a staple of my weekly routine, something I look forward to writing every week. It means a lot that you let me occupy some space in your inbox every Sunday. And it’s been a pleasure to get to know so people who reached out after reading.
🚀 The Best of 2020
This weekend I combed through all 52 editions, recounting everything I’d shared and reminiscing on 2020. I’ve shared over 100 articles, podcasts, and books over the last 52 weeks.
For those who have been reading since the beginning, you’ll find many old favorites to revisit. For more recent subscribers, you’ll get a taste of everything I’ve shared throughout this year. There’s a little bit of something for everybody.
In this week’s Digest, you’ll find:
The 17 most popular articles
The 12 most popular podcasts
My 10 favorite books from 2020
My seven most popular tweet threads
My seven most popular tweets
Thanks again for reading the Digest. Here’s to many, many more!
Have an epic week and an epic 2021,
Solitude and Leadership
So what I saw around me were great kids who had been trained to be world-class hoop jumpers. Any goal you set them, they could achieve. Any test you gave them, they could pass with flying colors. They were, as one of them put it herself, “excellent sheep.”
The obvious benefit to working quickly is that you’ll finish more stuff per unit time. But there’s more to it than that. If you work quickly, the cost of doing something new will seem lower in your mind. So you’ll be inclined to do more.
10 Things You Should Know About Money
Look around you. At the end of the month people have no money. In between they are giving up freedom to have no money left at the end of the month. It’s obscene. It’s a raw deal. Look what they are doing in return for that lifestyle. Is that working for them?
Six Harsh Truths That Will Make You a Better Person
Either you will go about the task of seeing to those needs by learning a unique set of skills, or the world will reject you, no matter how inoffensive and courteous you are. You will be poor, you will be alone, you will be left out in the cold
Wise People Have Rules for Themselves
Self-imposed rules aren’t constraints, they’re good decisions made in batches—they’re behavioral boundary markers you get to position yourself, through your own experience and wisdom.
The Ladders of Wealth Creation
Eight principles to grow your wealth and income over time
Extra time and money need to be reinvested
You can skip ahead, but you still have to learn the lessons from each step
Apply your existing skills in a new way to build wealth
There’s a difference between working for a better wage and truly building wealth
Using an earlier rung on the ladder to fund the next one
Moving between ladders often means a decrease in income
Each step is easier with an audience
It takes longer than you think, but the results can be incredible
How to Write Like the Great Entrepreneurs
Delete half the words. Say more with less. That’s good customer service. “If I had more time, I would have written a shorter letter.”
The Ultimate Guide to Writing Online
When you publish ideas, you create your own “Serendipity Vehicle” – a magnet for ideas and people and opportunities from potentially every corner of the globe.
The Technium: 68 Bits of Unsolicited Advice
To make mistakes is human. To own your mistakes is divine. Nothing elevates a person higher than quickly admitting and taking personal responsibility for the mistakes you make and then fixing them fairly. If you mess up, fess up. It’s astounding how powerful this ownership is.
11 Frameworks Every Entrepreneur Should Learn
Big Mario Marketing
Say your business sells the “boosts” that take Little Mario to Big Mario.
No one cares about your product. They care about becoming Big Mario.
Don’t sell your product. Sell the type of person your customer will become when using your product.
How to Ask Useful Questions
There are five types of questions:
Asking for Information
Asking for Clarification
Asking for Assistance
Asking for Agreement
Asking for Advice
The Unusual Ambitions of Chamath Palihapitiya
“Chamath wore the same jacket every day — a light-tan velour jacket — and jeans,” one former colleague recalls. When the colleague asked Palihapitiya about his sartorial choices at the time, the young analyst talked about “low ROI,” meaning he didn’t want to spend his time and money worrying about clothes.
Why You Should Start a Blog Right Now
This fact is very frequently lost when discussing writing: writing not only helps you to understand what’s going on and to crystallize your thoughts, it actually makes you think of new ideas and come up with solutions to your problems.
Seven ways to overcome the fear of failure:
Switch poles entirely
Be slightly overconfident
Find the right feedback group
Focus on the rate of change
See it as a learning opportunity
Recognize everyone else started in the same way
Seven Timeless Tips on Sales
This Hacker News post went viral last week, and for good reason. This anonymous commenter wrote an entire book on sales in seven bullet points. My three favorites:
Sales is a lot like golf. You can make it so complicated as to be impossible or you can simply walk up and hit the ball. I've been leading and building sales orgs for almost 20 years and my advice is to walk up and hit the ball.
Naval Ravikant on the Tim Ferriss Show
This episode dropped like a bomb out of nowhere. Naval has refused to be on anyone else’s podcast since he was on the Joe Rogan Show 18 months ago. I had high expectations going in, but this one was truly top-notch.
Invest Like the Best with Sam Hinkie
This is the second time I’ve heard Sam Hinkie on Invest Like the Best and the second time I was blown away. Sam and Patrick chat about two things: the importance of writing (especially creating digital breadcrumbs) and the importance of forming strong, highly vetted relationships. Two things I’m focused heavily on at the moment.
Chamath on the Knowledge Project
Chamath has defined a niche that resonates with me: he’s a baller who is clearly ambitious and looking to bend the world to his will, but he’s open and transparent and shares his struggles far more than any other successful investor and operator. You can see my takeaways in this tweet thread.
Dickie Bush on the Steal My Marketing Podcast
This was the most spontaneous thing I’ve done in a while. Abhishek reached out on Twitter and bang, we were on Zoom the next day recording this episode. This was a fun and wide-ranging conversation talking about my journey growing this newsletter, habits, routines, my favorite books, and a quick deep dive into SPACs and Rolling Funds. You can also check out the blog post version.
Superhuman CEO Rahul Vohra on Invest Like the Best
This was the highest-signal podcast I’ve listened to this year. I’m fascinated by the email company Superhuman. Their CEO is rewriting the playbook of launching, growing, and scaling a B2C productivity app. If you’re into startups, this one is a must-listen.
YCombinator CEO Michael Seibel on Invest Like the Best
I’m fascinated by YCombinator and the incredible resources they provide. Listening to the CEO talk about what they look for in an application, what most founders get wrong, and what he thinks the future of startups look like is well worth your time.
Balaji Srinivasan on the North Star Podcast
This was the most fascinating podcast I have listened to this year. Balaji Srinivasan is the former CTO of Coinbase and General Partner at a16z. His thoughts on the future of technology, inflation, writing, hiring, and decentralization had my mind spinning for hours. Highly recommend this one.
Oliver Cantin on the Mastering the Attention Economy Podcast
This was a masterclass on copywriting from my friend Ari Lewis. No matter the industry you work in, the ability to write convincing sales copy is a tremendous personal differentiator. Oliver is a top tier salesman, and the advice is very practical.
Derek Sivers and Shane Parrish on The Knowledge Project
Derek Sivers is one of my favorite thinkers and writers on the planet. Every time I listen to an interview with him, I walk away a little bit happier, a bit more curious, and a bit smarter. In this episode, Derek and Shane talk about mental models, ideas versus execution, how Derek reads books, and turning ideas into directives.
Tim Ferriss with Hugh Jackman
I really enjoyed this interview between Tim Ferris and Hugh Jackman. They talk morning routines, meditation, decision making, and the 85% rule. I could listen to these two guys talk for hours.
Maria Konnikova on The Knowledge Project
This was an epic conversation between poker pro Maria Konnikova and Shane Parrish talking decision making, poker, mentorship, and luck. You can find my takeaways in this tweet thread.
The Almanack of Naval Ravikant
The only book you need to read on building wealth and happiness in 2020. Dense, practical, and filled with wisdom, this is the best book I've read this year. If you apply every principle from this book, victory is guaranteed.
The War of Art by Stephen Pressfield
Resistance is the powerful, universally experienced force that keeps individuals from realizing their potential. The only way to overcome resistance is to go from being an Amateur to being a Professional. At any moment, you can decide to become a Professional and begin to defeat the Resistance— but the battle is fought every day.
What I Talk About When I Talk About Running
A captivating memoir from renowned fiction-writer Haruki Murakami. Haruki eloquently connects his passion for running with his passion for writing and explores how these two are habits have shaped his life. The prose, word choice, and first-person writing style make for a delightful read.
The Boron Letters by Gary Halbert
The only book you need to read on copywriting. Quick, entertaining, and a true pleasure to read. A great mix of practical life advice and actionable marketing, copywriting, and sales strategy.
Your Music and People by Derek Sivers
Simply a masterclass on marketing, selling, building, creating, and forming relationships. In 88 short, punchy chapters, Derek Sivers gives you everything you need to know to make it as a creator.
The Ride of a Lifetime by Disney CEO Bob Iger
A captivating autobiography from legendary Disney CEO Bob Iger. Bob takes the reader through the ups and downs of his career, exploring the lessons he has learned along the way. Iger's path from a stage assistant at Capital Cities to the CEO of Disney is one of persistence, excellence, and creativity. The best parts are the behind-the-scenes looks at becoming CEO, acquiring Pixar, Marvel, LucasFilm, and Fox, and becoming best friends with Steve Jobs.
Indistractable by Nir Eyal
Every action we take is either aligned with our broader intention (traction) or misaligned (distraction). The root of distraction is the avoidance of pain, moving away from the Resistance. Only awareness of avoidance can lead to long term focus. Being Indistractable means we consistently do what we say we are going to do.
Already Free by Bruce Tift
A deep dive into the interaction between Western therapy and Eastern Buddhism. Bruce Tift explores how we can use the best of each of these practices to dramatically improve our awareness and the quality of our experience.
Radical Acceptance by Tara Brach
A compelling and practical read on committing to the fullness of our experience. Told through the lens of her personal journey and journey of those she has worked with, Tara Brach compassionately lays out a framework for engaging fully with our emotions.
The Inner Game of Tennis by Timothy Gallwey
A practical, no-bs book on developing the proper mindset for optimal performance. Gallwey describes the necessity of quieting our hyperactive Self 1 in order to let our naturally performing Self 2 function at its best. Packed with applications towards performance, behavior change, and mental focus, I highly recommend this one.
✏️ My Most Popular Articles
My 10 Go-To Reflection Questions (and Where I Found Them)
Grab a Shitty Rod and Start Fishing
22 Questions To Have Great Answers To (And My Answers To Them)
🐦 My Most Popular Tweets
🧵 My Most Popular Tweet Threads
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Thanks Dickie, great stuff as always.
Amazing roundup, so much value. Thanks!