Patrick OShaughnessy Profile picture
backing leaders doing their life’s work @psumvc 🟣 @joincolossus 🎙️ “do unto others…and do it first”
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Aug 12, 2023 4 tweets 6 min read
My definition of “Life’s Work:”

“A lifelong quest to build something for others that expresses who you are”

3 parts to the definition, all important…

“A LIFELONG QUEST” reflects the reality that work isn’t about a series of accomplishments, which ultimately ring hollow. Asimov wrote “past glories are poor feeding”

Those doing their life’s work agree with Kevin Kelly’s brilliant maxim: “the reward for good work is more work,” and want to spend as much time “working” as they can in this short life.

Everything worth doing is worth doing for its own sake.

“TO BUILD SOMETHING FOR OTHERS” is a reminder that work is about service— making others’ lives better. The poet David Whyte wrote “the authentic watermark running through the background of a life’s work is an arrival at generosity.”

Steve Jobs believed this was a central idea, too: “Life can be much broader, once you discover one simple fact, and that is that everything around you that you call ‘life’ was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. Once you learn that, you’ll never be the same again.”

The most important line I’ve ever read is from the Upanishads: “Those who realize that all life is one are at home everywhere and see themselves in all beings…who shares food with the hungry protects me; Who shares not with them is consumed by me. I am this world and I consume this world. They who understand this understand life.”

The giving is the getting.

“THAT EXPRESSES WHO YOU ARE” reminds us that it’s not sustainable to be something you aren’t. The best work comes from people expressing themselves in a way that embraces what makes them different.

“Apple was Steve Jobs with 10,000 lives”

Joseph Campbell, who studied the human story more than anyone, believed this was the key question to ask: “what is it we are questing for? It is fulfillment of that which is potential in each of us. Questing for it is not an ego trip; it is an adventure to bring into fulfillment your gift to the world…”

Rumi wrote: “take off your mask, your face is glorious”

There’s nothing like someone immersed in a field they love, no matter what the field.

***

David Whyte again: “Ambition [for “goals” or “accomplishments”] takes willpower and constant applications of energy to stay on a perceived bearing; but a serious vocational calling [a great reframing of life’s work!] demands a constant attention to the unknown gravitational field that surrounds us and from which we recharge ourselves, as if breathing from the atmosphere of possibility itself.”

I love this image of the field from which we recharge ourselves…everyone's field is different, but it is in discovering our field, or more accurately, being honest with ourselves about the nature of our individual field, that we can begin a lifelong quest.

Whyte continues, “A life’s work is not a series of stepping-stones, onto which we calmly place our feet, but more like an ocean crossing where there is no path, only a heading, a direction, in conversation with the elements.”

Jobs also said: “One of the ways that I believe people express their appreciation to the rest of humanity is to make something wonderful and put it out there. And you never meet the people. You never shake their hands. You never hear their story or tell yours. But somehow, in the act of making something with a great deal of care and love, something’s transmitted there. And it’s a way of expressing to the rest of our species our deep appreciation.”

Life’s work: a lifelong quest to build something for others that expresses who you are.

I sincerely hope that everyone reading this finds their life’s work, and thrives doing it. Some of my favorite questions to ask yourself to triangulate on what might be your life’s work:

1) Where do you feel great resistance or fear?

Steven Pressfield wrote: “Fear is an indicator. Fear tells us what we have to do…Resistance is experienced as fear; the degree of fear equates to the strength of Resistance. Therefore the more fear we feel about a specific enterprise, the more certain we can be that that enterprise is important to us and to the growth of our soul. That’s why we feel so much Resistance. If it meant nothing to us, there’d be no Resistance…So if you’re paralyzed with fear, it’s a good sign. It shows you what you have to do…“I do have a rule that I have learned and that I believe and that is that the stronger the resistance that you feel towards something, the more important it is that you do that thing is. [Puts a bottle of water in front of him] If this is our dream—our novel or our startup or whatever it is—and we set it out in the sunshine…immediately a shadow is gonna fall from this thing. Resistance is the shadow. So the shadow is exactly proportionate to the dream. If it’s a big dream, there’s gonna be a big shadow. IN other words, the more resistance you feel to something, the more certain you can be that there's a big dream there and that you've gotta do it.”

Campbell wrote “the cave you feel to enter holds the treasure you seek”

2) What that you do looks hard to others but feels easy to you?

@paulg wrote “If something that seems like work to other people doesn't seem like work to you, that's something you're well suited for…The stranger your tastes seem to other people, the stronger evidence they probably are of what you should do. When I was in college I used to write papers for my friends. It was quite interesting to write a paper for a class I wasn't taking. Plus they were always so relieved. It seemed curious that the same task could be painful to one person and pleasant to another, but I didn't realize at the time what this imbalance implied, because I wasn't looking for it. I didn't realize how hard it can be to decide what you should work on, and that you sometimes have to figure it out from subtle clues, like a detective solving a case in a mystery novel. So I bet it would help a lot of people to ask themselves about this explicitly. What seems like work to other people that doesn't seem like work to you?”

3) What would you keep doing no matter how much money you had? Or even better, what couldn’t you get paid $1B to stop doing? @FoundersPodcast always brings up this question. You’ll know you are onto something if I couldn’t pay you to stop doing it.

A corollary: @m2jr asked @pmarca , “what’s your advice to people who want to build something great?” Marc said, “The first piece of advice is, ‘don’t do it.’ The reason that’s the first piece of advice is that if you can be talked out of it, you definitely shouldn’t do it. If you listen to advice #1, you shouldn’t do it. If you ignore advice #1, you might have the personality type to be a founder.”

4) what’s the weirdest thing you spend a lot of time on? Or, what’s a passion you’d be embarrassed to admit publicly?

Weird is good. Normal is competitive. The stranger your thing, the more low status, the more unusual…the less competition you’ll face, the more you’ll learn, the more fun you’ll have, and the more you’ll be able to contribute.
Apr 27, 2023 5 tweets 4 min read
Our Screenshot Q&A with @dkimerling on the opportunity in Financial Services

We try to cram a shocking amount of information into a dozen or so questions and answers, with the requirement that the answers fit on a single Notes app screenshot

Let’s dive in … ImageImage Questions 1-4 on the overall opportunity and past + future of financial services ImageImageImageImage
Feb 3, 2023 11 tweets 3 min read
Is producing original content a good business model? Why MTV is so important:
Jan 13, 2023 14 tweets 4 min read
My Screenshot Q&A with @BucknSF

I wanted to see how much I could download from his brain in a dozen questions, with only a screen’s worth of room to answer each

This feels like a mini course on software from someone who clearly lives and breathes the industry… 1. What might happen over the next five years in software?
Oct 30, 2022 9 tweets 3 min read
Chapters 1 + 2 of this are really interesting

Maps pretty clearly onto some ideas popular in business like focus, counterpositioning, decentralization Chaos is a ladder
Oct 29, 2022 10 tweets 3 min read
Art of War is pretty simple set of ideas

Don’t show your cards Image Use enemies temperment Image
Oct 19, 2022 5 tweets 2 min read
1/ Tegus is hiring a VP of Engineering

The formal job post is here: jobs.lever.co/tegus/7c505c94…

...but I'd love to pitch the job with my own spin to those out there that might consider it... 2/ What drew me to this company as an investor were the (twin brother) founders Mike and Tom Elnick

I remember telling a friend about Tegus and its CEO who was an intense, competitive, humble, unassuming, learning machine

But the punchline was "oh, and there's two of them"
Sep 21, 2022 4 tweets 1 min read
Charlie Songhurst on the dominate reasons for failure at each stage of a startup Image Charlie on why you should study failure rather than greatness Image
Sep 12, 2022 12 tweets 7 min read
@samcates @marktrevitt It’s a very short book

THERE ARE at least two kinds of games. One could be called finite, the other infinite. A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play. @samcates @marktrevitt The rules of an infinite game are changed to prevent anyone from winning the game and to bring as many persons as possible into the play.

Finite players play within boundaries; infinite players play with boundaries.
Great
Aug 31, 2022 5 tweets 3 min read
1/ At @joincolossus we are building the best place to learn about business and investing

We profile people (@InvestLikeBest) and companies (@bizbreakdowns, @50Xpodcast, @web3breakdowns)

Now, you can study history’s great founders with @FoundersPodcast joining our network… 2/ I met David Senra, the creator and host of @FoundersPodcast, after listening to his incredible episode on Estée Lauder

I love biographies but never get through them

Founders is my solution for learning about the legendary founders and builders through history
Jul 11, 2022 5 tweets 1 min read
We need some help, so running a March Madness like set of polls to get an answer

Imagine you could know everything on a given company building topic (downloading to brain Matrix style)

Which topic would be the most valuable of 16 candidates?

4 polls in this thread, rest tmrw Second set:
Jun 4, 2022 4 tweets 1 min read
What are the biggest discoveries or innovations that were really led by more than 1-2 people? And I mean the original 0 to 1 sense

First Google result shows kind of what I mean :
May 30, 2022 11 tweets 9 min read
Last week we hosted our third @CapitalCamp

The joke between @BrentBeshore and I is that he’s throwing a food and drink (drink, because wine would be understating it) festival while I throw an investing conference. This is mostly true.

Some highlights from CC ‘22… First a quick ode to the team…I would challenge anyone to hold a candle to what @Clayton_Dorge, David, James and there 120 person team put together

The food, activities, and venues were over the top
Mar 25, 2022 18 tweets 9 min read
Everyone agrees that persistence drives success, but the more interesting question is how to evaluate persistence in someone you are getting to know (and may invest with). What are the sources of persistence?

A favorite source of mine is something I call “The Klara principle” I first heard about Klara Dynamics in 2016. I was at lunch with my smartest friend—a data scientist who ran risk management at a large hedge fund.

Our lunches were always fun and stimulating, but this one was different. He showed me pictures of a new device he’d been building:
Jan 24, 2022 4 tweets 1 min read
What a day of football. My god. !!!!!
Nov 28, 2021 11 tweets 3 min read
Every interesting outcome in my life was unpredictable and was the result of good habits, strictly practiced.

This is the opposite of “vision” “big, hairy, audacious goals” and “accomplishments.”

The best kind of success is continuous, every day, not occasional. BHAGs are incredibly inspiring, and they have a place in the world. But my experience is that those chasing them sacrifice everything, often including their families. Read “Boyd” for a perfect example.

And most BHAGs never come to be. A focus on habits allows for daily success.
Nov 5, 2021 5 tweets 1 min read
Ongoing thread on category creation

1. You want to fill in this phrase:

[your company], the global leader in x

x, the category name, should be 2-3 words. Make one deeply familiar to the audience. Make the others pique curiosity

You want people to feel both safe and interested 2. Frustrate older competitors because your product has something in common.

The best messaging has one foot in the known and one in the unknown / new.

Make competitors explain their product through lens of your category, specifically the new element you’ve introduced.
Oct 6, 2021 6 tweets 9 min read
If you DM me your choice for the most interesting company in the world with <$5m of revenue, I’ll collect them all and share them here. @TryMetafy
kernel.com
supabase.com
gradio.app
Infinite Canvas
Third Wave Automation
Gateway X
Wavve.co
Bidstack
OneSoft Solutions
Emergencymcg.com
CloudNC
Xeal
Soulup
Abaxx technologies
faberinfinite.com
Caba
Rito
Sep 13, 2021 8 tweets 4 min read
Today is a special day for me: the 5-year anniversary of the podcast.

No one is luckier than me. It has been such an honor to learn from more than 300 guests and reach 30 million people.

It is also fun to reflect on what the guests and the process itself have taught me... 1. Growth without goals

Habits trump goals

At the start, I had no idea where this podcast would take me. Its led to 5 companies, investments, new products, and many of my closest friends

I didn't predict (or control) those outcomes. I did control the weekly habit.
Aug 20, 2021 24 tweets 10 min read
Have been lucky to meet with or study hundreds of companies in 2021.

Here's an ongoing list of company attributes that I find interesting... 1. Operations Focus

“Amateurs talk strategy, professionals talk logistics.” A grand vision is great, but the best companies are often focused on challenging but tangible near term goals. If a founder can’t move from vision to on the ground details quickly...bad sign
May 29, 2021 4 tweets 3 min read
“Positioning” is one of the most important books I’ve read.

“The basic idea is not to create something new and different, but to manipulate what’s already in the mind, to retie the connections that already exist.”

E.g. this is how we came up with the term “Custom Indexing” As we tried to name the category for our Canvas platform (since it was first of its kind), we literally spent a year trying category names until Custom Indexing landed.

Here’s my message to the team back in 2019. Funny that I was wrong and we used “indexing”