Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
Shownote
Shownote
This week is a special episode. Only David Senra [https://x.com/davidsenra]
could get me to be on the other side of the mic. Because I don’t plan on being
interviewed often, I wanted to share this conversation, which I so enjoyed, with
our audience.
It went in a very different direction than I expected. We barely talk about
investing or interviewing. Instead, we talk about finding an organizing
principle for life, undiscovered talent, and the idea that “the reward for good
work is more work.”
We also discuss the principles that guide how I think about building Invest Like
the Best, Colossus, and Positive Sum.
This conversation was originally recorded and released on David Senra
[https://www.davidsenra.com/episode/patrick-oshaughnessy], and I wanted to share
on the Invest Like The Best feed as well. Please go follow
[https://www.davidsenra.com/] what he’s doing, there’s no one like David.
Enjoy!
For the full show notes, transcript, and links to mentioned content, check out
the episode page here
[https://colossus.com/episode/creating-on-principle/].
-----
This episode is brought to you by Ramp
[http://ramp.com/invest]. Ramp’s mission is to help companies manage their spend
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This episode is brought to you by Rogo [https://rogo.ai/]. Rogo is an AI-powered
platform that automates accounts payable workflows, enabling finance teams to
process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest
[http://rogo.ai/invest].
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This episode is brought to you by WorkOS [https://workos.com/]. WorkOS is a
developer platform that enables SaaS companies to quickly add enterprise
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This episode is brought to you by
Ridgeline [https://www.ridgelineapps.com/]. Ridgeline has
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Editing and post-production work for this episode was provided by The Podcast
Consultant (https://thepodcastconsultant.com
[https://thepodcastconsultant.com/]).
Timestamps
(00:00:00) Welcome to Invest Like The Best
(00:04:26) Intro
(00:05:14) The Joy of Championing Undiscovered Talent
(00:07:33) How One Tweet Changed David's Life
(00:10:16) The Upanishads Passage That Shaped Patrick's Worldview
(00:15:32) Growth Without Goals
(00:17:24) Why Media and Investing Are the Same Thing
(00:33:05) The Search for True Understanding
(00:35:36) The Daniel Ek Dinner That Launched David’s Podcast
(00:39:02) Making Your Own Recipe From the Ingredients of Great Lives
(00:43:46) The Privilege of a Lifetime Is Being Who You Are
(00:52:06) Bruce Springsteen
(00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition
(01:01:43) The Unfair Advantage of Podcasting
(01:04:12) Relationships Run the World
(01:11:10) The Origin Story of Invest Like the Best
(01:12:45) Building Colossus: Why Start a Magazine in 2025
(01:18:42) People Are More Interested in People Than Anything Else
(01:22:12) Hiring Through Output
(01:26:23) Learn, Build, Share, Repeat
(01:30:01) The Daisy Chain: How Reading Books Led to Everything
(01:33:15) Red on the Color Wheel: Sam Hinkie's Observation
(01:40:17) Finding Your Superpower and Becoming More Yourself
(01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership
(01:48:11) Life's Work: A Lifelong Quest to Build Something for Others
(01:52:00) The Ten Roles Game and What Matters Most
(01:59:12) Husband, Father, Grandfather
(02:01:52) The Kindest Thing
Highlights
Highlights
In this deeply reflective conversation, the host steps into the role of guest, engaging in a rich dialogue that transcends typical discussions of investing or media. Instead, the focus turns to the personal principles that shape a meaningful life and creative work.
Chapters
Chapters
Welcome to Invest Like The Best
00:00Intro
04:26The Joy of Championing Undiscovered Talent
05:14How One Tweet Changed David's Life
07:33The Upanishads Passage That Shaped Patrick's Worldview
10:16Growth Without Goals
15:32Why Media and Investing Are the Same Thing
17:24The Search for True Understanding
33:05The Daniel Ek Dinner That Launched David’s Podcast
35:36Making Your Own Recipe From the Ingredients of Great Lives
39:02The Privilege of a Lifetime Is Being Who You Are
43:46Bruce Springsteen
52:06Clean Fuel vs Dirty Fuel: The Source of Your Ambition
57:23The Unfair Advantage of Podcasting
1:01:43Relationships Run the World
1:04:12The Origin Story of Invest Like the Best
1:11:10Building Colossus: Why Start a Magazine in 2025
1:12:45People Are More Interested in People Than Anything Else
1:18:42Hiring Through Output
1:22:12Learn, Build, Share, Repeat
1:26:23The Daisy Chain: How Reading Books Led to Everything
1:30:01Red on the Color Wheel: Sam Hinkie's Observation
1:33:15Finding Your Superpower and Becoming More Yourself
1:40:17Repetition Doesn't Spoil the Prayer: Teaching as Leadership
1:45:06Life's Work: A Lifelong Quest to Build Something for Others
1:48:11The Ten Roles Game and What Matters Most
1:52:00Husband, Father, Grandfather
1:59:12The Kindest Thing
2:01:52Transcript
Transcript
Patrick O'Shaughnessy: Here's an interesting question to think about. If your finance team suddenly had an extra week every month, what would you have them work on? Most CFOs don't know because their finance teams are grinding it out on lost expense report...

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