Patrick OShaughnessy Profile picture
Aug 20, 2021 24 tweets 10 min read Read on X
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
2. Life’s work

To borrow a concept from @nikiscevak, it is thrilling to find someone doing their “life’s work.” When someone's personal path lines and formative experiences line up with the problem a company is solving, I get excited. "Life's work" is a source of perseverance
3. Synchronized team

Well managed internal communication is a huge advantage.

This is often evident

1) in internal routines, words and phrases with unique meaning

and

2) consistent answers to questions about the company’s plans from a variety of different insiders
4. Jobs as a product

I like when management teams view jobs inside their business as a product to be built, designed, and sold like any other product.

Everyone is struggling to hire great talent, so a differentiated strategy in hiring matters as much as anything.
5. Static to streaming

Companies that turn useful information from occasionally measured to constantly measured.

This could be software security compliance (@TrustVanta) or pantry inventory levels (@bottomless)

Streaming data unlocks new product possibilities
6. Busted but booming

@gabrielleydon told me his favorite investing scenario is when a product is constantly breaking, but demand STILL grows like crazy. This tells you that there’s some real potential innovation happening.
@gabrielleydon 7. Accident to asset

I love when a company repurposes internal tools to serve external customers. Often this applies only to older companies or those in a “second act.” But the path required to have built a useful internal tool is often what allows for a unique product.
@gabrielleydon 8. Not best, only

The easiest way to be the best in a category is to create it. We love when we observe outsiders trying to compare a company to others via analogy, but hearing lots of different, unrelated companies used in those analogies. This is often a sign of a new category
9. Simple task, complex guts

A company like @stripe offers to complete a simple job (accept a payment), but hides and solves the insane complexity behind that simple task.

This usually manifests as API-first companies in software, which are among my favorite.
10. Lazy, Vain, & Selfish

I love @scottbelsky observation that in the "first mile" of a product experience, customers are lazy, vain, and selfish.

Bob Pittman taught me that quality is great, but increased customer convenience is more often the story behind successful products
@scottbelsky 11. Design partners

A concept learned from @chetanp and Dave Duffield. Companies which carefully pick a small batch of early customers (usually in B2B) and work with them for an insanely long time (1-3 years) to mature a product before opening to more new customers.
@scottbelsky @chetanp 12. Regulatory unlock

Whether a company is actively fighting to change some ruleset or regulation, or taking advantage of a recent change, companies operating near a regulatory unlock typically face less competition.
@scottbelsky @chetanp 13. One thing

This is the @Costco principle. In every company--especially one that is working--it is tempting to do more. Companies that stick to one major thing (like constantly improving Costco warehouses and membership value) can become among the most enduring franchises.
14. World building

I love @photomatt description of companies like Salesforce that build whole worlds:

joincolossus.com/episodes/67865… Image
@photomatt 15. Unique distribution

I deeply respect leaders who focus on unique ways to reach their customers.

So many problems are ultimately marketing and messaging problems, yet we tend to look down on sales and marketing relative to product.

GTM should be developed like product.
@photomatt 16. Float financing

Any time a company is paid early or up front, I'm interested. It signals clear demand from customers, and indicates that a company may be very capital efficient.

This can be dangerous, too, but its a feature that I find rarely despite much searching.
@photomatt 17. Culture of service

My favorite element of culture is a focus on service.

This shows up as fast response times, lack of defensive behavior or blaming, and constant learning via productive feedback.

Leaders tend to be tough + fair, hardworking, and humble, not flashy
@photomatt 18. Medium over message

I love companies which enable creative building or output for others (rather than the company producing the output itself).

A good litmus test for this is for the company to be surprised by how users create things with their product.
19. Data

OKRs, KPIs, and other quantitative measures of a company’s success are commonplace

What’s interesting to me is how fast a CEO can answer the question “what few metrics do you measure and why do they matter most?”

It is very hard to fake a good answer on the spot
20. Operating Systems

I love the idea of “first tab open, last tab closed”

Toast for restaurants, Squire for barbershops, etc

OSs handle the repetitive, undifferentiated heavy lifting and become critical + hard to remove

@arampell lays it out well here joincolossus.com/episodes/90737…
21. Accumulating Benefits and Mounting Losses

If products have a core action that users repeat over and over, that action should, over time, make the product better AND more painful to leave

Here's @sarahtavel classic post on the hierarchy of engagement

sarahtavel.medium.com/the-hierarchy-…
22. “Maniacs on a mission”

This was one of my favorite definitions of the kind of founders we are after

Others:

“Relentlessly resourceful” @paulg’s summation

“Disagreeable”

“Driven to win”…🦄 are often byproduct of founder sense of inferiority, insecurity, and trauma

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More from @patrick_oshag

Aug 12, 2023
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.
Life’s work is upstream of many of the other things people obsess over, like great leadership.

It’s much easier to be a great leader if you are doing your life’s work

Mike Moritz has my favorite quote on this topic:

“Great leadership has many different attributes, but it starts with knowledge of a particular pursuit, because without the knowledge and mastery of that particular pursuit, I don’t think you have the authority to convey it with conviction to others. It usually is associated with an obsession, because to be a great leader, you have to be obsessed by something, otherwise everything seems false and hollow. You have to then be able to convey your obsession to people in a manner that inspires and encourages and motivates them to perform at a level they didn’t think they were ever capable of performing at. All of those, when knitted together, help to define what separates a great leader from a very capable manager.”
Read 4 tweets
Apr 27, 2023
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
Questions 5-8

Distributor model, profit pools, global banks, and serving the elderly ImageImageImageImage
Read 5 tweets
Feb 3, 2023
Is producing original content a good business model?
Why MTV is so important:
Why study Warner Brothers:
Read 11 tweets
Jan 13, 2023
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?
2. The pros and cons of the SaaS business model
Read 14 tweets
Oct 30, 2022
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
You cannot just follow playbooks
Read 9 tweets
Oct 29, 2022
Art of War is pretty simple set of ideas

Don’t show your cards Image
Use enemies temperment Image
Trench warfare is bad Image
Read 10 tweets

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