Patrick O’Shaughnessy Twitter AMA Summary

  • Reading time:18 mins read

Patrick O’Shaughnessy did an AMA on Twitter today (27/04/2019), so I’ve compiled and sorted into categories for easier reading.
Personally I hate reading through Twitter threads so thought someone else might find useful too.

I haven’t included all questions and answers from the thread. Just pulled the ones I found most interesting and insightful.
Only edits I’ll do will be for capitalization and punctualization purposes.

Education & Improvement

Do you have any readings you recommend on the topic of asking better, more insightful questions?

There’s nothing, you just have to do it. Figure out how to ask questions that yield information you haven’t heard before.

Professionally – What would you regret not starting or finishing in the next 3 years?

Not really how I roll. When something seems like it must be done, I do it.

What’s the biggest piece of advice you’d give people who are early in their careers?

Learn in public, fanatically. 

That means find something you can’t stop thinking about and know it better than anyone, and share everything you learn along the way. Once deep enough, start building something too. Make something you have to sell as early as possible.

What do you regret? Who/what inspires you? What advice would you tell your 20yr old self? What was your learning process like joining OSAM after school?

Regret: no selling something earlier, not minoring in computer science (i’d keep the philosophy major).

Inspiration: my family, and those who build long and deep friendships.

Advice: build and sell, immediately.

Learning: firehose.

Do you wish you had started out in your career as a technology exec knowing everything you now know?

No, but I wish I had discovered technology and software earlier (say at 25 instead of 30)

(Following on) Would you still have focused on finance or some other applied domain w/ software?

Finance. I believe finance and software are the two highest leverage areas for ambitious people (see @matthewclifford episode), so the intersection is deadly interesting and full of opportunity.

Growing up, did you feel pressure following your fathers footsteps into a financial career?


How do you balance learning and soaking up information with actual productivity and getting things done?

Use specialization…don’t keep work that I don’t like or am naturally bad at.

Has there been anything you’ve learned about software investing that’s felt counterintuitive?

Most of what @chetanp has taught me about “going slow to go fast.” I’m generally not a “go slow” kind of person, but he’s been right on every aspect and has materially improved our trajectory with his advice (you can listen to that in our podcast convo).


What scares you most about COVID’s impact on the economy, globally and domestically?

What various types of inequality look like on the other side. within countries, between countries, wealth, knowledge, everything.

After the lockdown and with many devs demonstrating work from home is feasible , are we going to see a “virtual Silicon Valley “ ? Where networks of distribuited devs build the next gen of product/services ?

I don’t know…but I’m already working with remote researchers, designers, and devs and its seamless and easy…maybe ever better. 

What event of the last 2 months has surprised you the most?

Increasing productivity and zero real slippage with my firm working from home.

What has been the best part of being quarantined for you? What is the best and hardest part of working with family?

Family, nature, natural sleeping patterns, lots of time talking to friends, lots of very focused work. 

Hard part is feeling bad if mid situation is audibly bad and I can’t go help.


Why did you start a podcast?

I’d been playing with concept of repetitive creative structures–some consistent format (container), but constantly evolving content or filling. I experimented with many versions, and only two lasted (weekly podcast and monthly book email). I believe in sharing one’s learnings

How do you source the newsletters you subscribe to? What are favorite newsletters right now?

I don’t read many. ones I love right now:

When meeting someone for the first time, what characteristics make you think ‘this person is a force of nature?’

Domain knowledge, energy, and kindness. Competitive spirit. Clear access to some “source.” 

Maybe best indicator is what percent of what they say is something I’ve heard elsewhere. Lower the better.

Do you ever regret starting a podcast?

Only that I didn’t start it earlier

Which of your guests surprised you the most by the end of your interview?

Interesting question. @AliBHamed maybe…

Fun story: @tseides told me “trust me, just interview this “kid” (he was 25 or so at the time I think)”

Couldn’t believe his energy and intelligence. Talking to him almost weekly since.

3 guests you’d like to have on the podcast?

@sherylsandberg @JeffBezos @BillGates

How do you prepare for a podcast?

Usually by the time I invite the guest, I’ve already prepared (meaning its the content/learning from them that makes me want to invite them in the first place).

What’s the most annoying thing about podcasting?

Everything but the preparation and conversation itself, though I’ve outsourced almost all of it. 

Convincing guests to come on is also fun.

Does the interviewee have your questions before hand?  Amazed at the depth of answers if it’s just riffing.

No, very rarely someone will insist on some topics which i’ll provide but almost never stick to. I don’t prepare a list of questions.

How much do you attribute your success to your childhood, family, education, connections? Do you think economic / political opportunity needs to be talked about?

I was born sliding into home, so I attribute a great deal of my success to an unfair starting position. I attribute a lot of it to an intolerance for boredom, too. 

Yes I think it needs to be talked about and addressed, and always will be

(Following on) What makes you think it was unfair?

Maybe fair isn’t the right idea. Point being, I had more unearned advantages than almost anyone.

In the years since your Hash Power series on crypto, how if at all, have your views on Bitcoin changed? If you were to release the series again today, would you change anything?

I’m pretty proud of how it turned out and recently listened to it and feel not much has changed. Still just as interesting conceptually and about as interesting in terms of use cases (which isn’t many). Remain fascinated with it all, but need to see uses.


Best book you’ve read in the last year?

Siddhartha (for Nth time)

How has the Katha Upanishad influenced your life? And have you dived more deeply into Indian philosophy since reading it?

The Katha was the standout on my first reading of the Upanishads, and no collection of writing has affected my life so much. 

I was selfish and scared before reading it, and like to think I became more generous and less scared after.


How do you balance (1) trying to produce excellent work at home with (2) your responsibility & desire to invest in & spend time with your wife/kids/family?

I don’t accept that one has to come at the expense of the other. 

One great book on this is Three Marriages.

How do you prioritize family, work, personal interests, side projects? No one can balance it so what’s the model for picking how you allocate your time?

I try to do only things that I enjoy doing and outsource the rest, so I don’t actually have to prioritize much. 

That said, family and friends above everything else when it counts. Big believer that “showing up” and communication are everything, so prioritize those.

Listen to @photomatt on @SamHarrisOrg for more.

Best @jposhaughnessy story from the family canon?

So rare for him to lose his temper or get angry, that those stand out. Specifically when I stole a coat of his without asking, forcing him to wear an old coat from the 80s in which he was equal part ridiculous looking and furious.

It looks like you were relatively young when you had kids. Why?

Met @laurenoshag when I was 19, we spent lots of time together before kids (I was 29 when my son was born). Waiting until it felt like the right time. That’s all.


What’s your personal asset allocation across equity/bonds/others (crypto?) as rough %?

Basically all equities, cash for security, tiny bit of crypto as a plaything.

What do you ignore that others don’t?

Doubt about my convictions introduced by people that know less than me.

Will the passive trend lead to ever greater outperformance of growth/large caps and a melt up in their valuations?

A question I’ve pondered maybe more than any other with zero answers. I just don’t know. I am not in the “passive distorts prices” camp too much.

Would you rather be a VC than a quant?

luckily I do almost exactly what I want to do in my career, so no. I’m doing exactly what I want. I’ve made early stage investments before and will do more in the future. How that looks I have no idea.

What about quant investing do you think fundamental investors misunderstand the most?

Not sure, but an interesting question. Probably base rates (even though most fundamental investors understand the concept well, its hard to implement).

Do you use alt data at OSAM?

We’ve tried a million things. Most “alt data” isn’t helpful in a pure quant setting (more useful for fundamental investors deepening their company models).


You can see 25 years into the future… what are you up to besides tweeting gifs?

Same things. Hiking, reading, eating, building, convincing, asking, and hopefully lots of traveling and meals with our closest friends.

where is your favorite place to hike in America?

California. Matt Davis trail ending in Stinson Beach.

If you could interview one historical figure who would it be and why?

with zero thought first three answers that pop to mind:
Ben Franklin

If you could hang out with any scientist that ever lived who would it be and why?

Feynman, Oppenheimer, Da Vinci.

How do you view data vs. instinct in your creative process. Has that changed over the years?

For starting something new, instinct is more powerful. I’ve never done anything super interesting that started with cold analytics. Once you have a hold of something, that’s when data becomes critically important–though role of creativity never dies.

Philosopher you most admire and follow?


What fascinates you about India? (history, culture, current events, anything…)

Of the places I’ve never been, I am most interested in India. 

I love the people, the food, the colors, the history, the apparent energy, the religious roots.

Do you see yourself in the future with a business in an area other than finance?

Never say never, but there is so much of investing, let alone finance, I’ve yet to explore or build within.

How much do you sleep?

8 hours.

What is one or two simple things you have to constantly remind yourself of?

Slow down.

Want some more AMA’s?