Prompted by a Twitter exchange, the group debates the idea that all businesses, especially investment firms, are turning into media businesses, and how long that competitive dynamic can last.

The trend was catalyzed by the internet removing gatekeepers between businesses and their end audience
Patrick is skeptical about universally adopting the 'one right way' once everyone agrees a channel works, citing Facebook/Google ad cost inflation as a cautionary parallel
Once a niche brand is established, its content acquisition channel remains cheap relative to new entrants

“It's not just the investment business, it's every business is turning into the media business in some way, shape, or form.”
Ben Gilbert

“I'm always hesitant when everyone's starting to agree that the one right way of doing things is X, Y or Z, because that's happened to…”
Patrick O'Shaughnessy

#media-business#distribution#content-strategy

Explainer· 2

Explainer

How a Traditional Asset Management Business Actually Works

Patrick breaks down the simple, SaaS-like economics of long-only asset management: recurring asset-based fees, no accounts receivable, and why capacity constraints determine whether a firm charges flat fees or performance-based carry.

Asset managers take discretion over client assets and charge a small recurring percentage fee, similar to SaaS revenue
There are no accounts receivable since fees are stripped directly from managed assets
Capacity-constrained strategies (venture, hedge funds) favor incentive/carry fees; large-capacity public strategies favor flat management fees

#asset-management#business-models#fees

Explainer

Canvas: Turning Internal Quant Tools Into a Software Platform for Advisors

Patrick explains how OSAM repurposed a decade of internal quantitative infrastructure into Canvas, a software product that lets financial advisors design fully customized investment strategies for their end clients, echoing the AWS origin story.

Canvas exposes OSAM's internal quant infrastructure as a client-facing product for RIAs and advisors, not end investors directly
Advisors can customize portfolios around tax preferences, sector exposure, and client-specific risk factors
The build was fast (a few months) only because it drew on roughly a decade of pre-existing internal infrastructure

“I think of us today as as a software business that happens to monetize through asset management.”
Patrick O'Shaughnessy

“This is awesome. Like it truly is a AWS story.”
Ben Gilbert

#canvas#fintech-product#platform-strategy

Story· 6

Story

From Microfiche to Model: The Original Dogs-of-the-Dow Research

Patrick describes his father's original quantitative research, hand-collecting decades of stock data from microfiche to test the simple 'Dogs of the Dow' strategy, which became the seed of O'Shaughnessy Capital Management.

The original research was the simple 'Dogs of the Dow' strategy: buy the 10 highest dividend-yield Dow stocks annually
Data was collected by hand from microfiche going back to the 1920s
The strategy's edge came from strict discipline plus buying at lower prices, not modeling sophistication

#origin-story#quant-investing#research

Story

Netfolio: The Robo-Advisor That Was Too Early

Before Wealthfront and Betterment existed, the O'Shaughnessy team built Netfolio, an early attempt at a direct-to-consumer automated investing platform in the late 1990s that ultimately didn't survive the dot-com bust.

Netfolio was like a hybrid of Motif Investing and Wealthfront, built in the late 1990s
It offered active, rule-based strategies rather than passive index rebalancing
The business raised significant capital but was ultimately too early for its market

“Netfolio was a version of like if Motif Investing and Wealthfront had a had a baby, uh it would have been Netfolio back in the…”
Patrick O'Shaughnessy

#fintech-history#dot-com-bust#robo-advisor

Story

Spinning Out of Bear Stearns Days Before the Financial Crisis

OSAM was spun out of Bear Stearns as a 'friendly divorce' in July 2007, just months before Bear's collapse, requiring a delicate structure to preserve continuous track records for clients.

OSAM's first official day was July 3, 2007, called 'OSAM Independence Day'
14 team members plus Patrick left Bear Stearns to found OSAM as dual employees during the transition to preserve track record continuity
Patrick, as first employee, spent the early months transferring thousands of client accounts

“So technically the first day of OSAM was July 3rd, 2007, which we called OSA. OSAM Independence Day.”
Patrick O'Shaughnessy

“We actually had portfolio management team members as dual employees of Bear Stearns and O'Shaughnessy Asset Management.”
Patrick O'Shaughnessy

#bear-stearns#2008-financial-crisis#spinout

Story

From Rejected Applicant to Philosophy Major at Notre Dame

Patrick recounts being rejected from every reach school he applied to out of high school, then discovering a love of self-directed learning through philosophy at a smaller school before transferring to Notre Dame.

Coasted through a large public high school doing minimal work and was rejected from every college he applied to
Found philosophy at University of St. Thomas, which allowed fully self-directed reading and argument-based learning
Transferred to Notre Dame, which had an unexpectedly elite secular philosophy department

#education#personal-history#philosophy

Story

How Invest Like the Best Started as a Seven-Episode Experiment

Patrick recounts the accidental, low-key origin of Invest Like the Best in 2016, committing to just seven episodes with no strategy, which found 'product-market fit' by the second episode.

The podcast began as an audio companion to a friend's book, 'Dear Chairman'
Patrick committed to only seven episodes at first because of his need for a concrete habit-forming goal
Growth was organic with no deliberate marketing, driven by niche focus rather than broad appeal

“By the third episode, I was like, oh, I'm gonna do this the rest of my life.”
Patrick O'Shaughnessy

“Turns out on the internet, like the more focused you are and the more wonky and niche you are, the bigger your audience is.”
Patrick O'Shaughnessy

#podcasting#origin-story#invest-like-the-best

Story

The Kindest Thing: Touring Canada at 23 to Explain Losses

Patrick shares his answer to Acquired's signature closing question: at 23, right after the financial crisis, he was sent on a three-week tour across Canada to explain steep client losses, mentored by RBC's Bill Hill.

Patrick, at 23, gave roughly 50 presentations across Canada explaining performance losses of up to 60% to everyday investors
Bill Hill of RBC accompanied him, letting him struggle through mistakes and coaching him afterward rather than rescuing him mid-presentation
The experience was formative for Patrick's resilience and communication skills

“I was legitimately scared. Like I I was really worried flying up to this trip.”
Patrick O'Shaughnessy

#kindest-thing#mentorship#personal-history

Q&A· 2

Q&A

Why Not Sell Canvas to Competing Asset Managers?

David asks whether OSAM should license Canvas horizontally to competitors; Patrick explains the tension between platform economics and staying focused on RIA advisors as the core client.

Patrick references Keith Rabois's observation that tool-builders sometimes end up competing against the 'merchants' they built tools for
OSAM's long relationship with the RIA community shapes its choice to serve advisors, not build the full end-client experience
Focus is prioritized over maximizing every possible use of a powerful product

“I like one definition of a of a platform, which is that you're not using the same tools to compete against your clients.”
Patrick O'Shaughnessy

#platform-strategy#distribution#focus

Q&A

Grading OSAM's Canvas Era So Far

Asked to grade his own tenure as CEO, Patrick gives OSAM a tentative B+, crediting the team's execution on Canvas while acknowledging it's still early and leaving room for growth.

Patrick attributes most of the Canvas build to his team rather than himself
The Canvas engineering team is surprisingly small (about five full-time engineers) relative to perceptions
Patrick avoids long-term (5-10 year) goals, preferring near-term 'boss battle' framing over fixed targets

“I think I'll give us uh a tentative B plus to give us lots of room for improvement.”
Patrick O'Shaughnessy

“The furthest I'll go is is think about them like boss battles.”
Patrick O'Shaughnessy

#self-assessment#canvas#company-building

Tool· 1

Tool

Launching Founder's Field Guide: A New Weekly Show for Builders

Patrick previews Founder's Field Guide, a new Thursday sub-series on the Invest Like the Best feed dedicated to conversations with founders and CEOs, distinct from the Tuesday investor-focused episodes.

Tuesdays remain investor-focused conversations; Thursdays will feature founders, CEOs, and builders
Patrick notes founders are easier to get talking in depth than investors, unlocking richer conversations
The show is part of a broader plan to publish more of his own diligence conversations transparently over time

“Thursdays will be for conversations with founders and CEOs and and builders.”
Patrick O'Shaughnessy

#podcast-launch#founders-field-guide#content-expansion

Takeaway· 1

Takeaway

Patrick's Rapid-Fire Lessons From His Guests

Patrick runs through a stream of portable ideas he's collected from past guests, including Bill Gurley on marketplaces, Charlie Songhurst on sourcing labor in uncompetitive markets, and Kat Cole's chicken-wing story about disarming difficult customers.

Charlie Songhurst's advice to search for labor in uncompetitive markets rather than Silicon Valley
Kat Cole's Hooters chicken-wing story about inverting a challenging customer dynamic with unexpected generosity
Matthew Ball's idea that the metaverse is about interoperability of value, not just virtual worlds

“I find that that I've seen that a lot of ways, like this inversion to deal with challenging people by going right back at them…”
Patrick O'Shaughnessy

#lessons-learned#invest-like-the-best#guest-highlights

Frameworks in this episode

Be the Muse, Not the Hero (Media Flywheel)

Directional Arrow of Progress

Go Slow to Go Fast (Enterprise Customer Discipline)

Marketplace Penetration-Benefit Test

Seven Powers Diagnostic

Insights & moments

◆Hot Take· 1

"Every Business Is Becoming a Media Business"

✶Explainer· 2

How a Traditional Asset Management Business Actually Works

Canvas: Turning Internal Quant Tools Into a Software Platform for Advisors

❝Story· 6

From Microfiche to Model: The Original Dogs-of-the-Dow Research

Netfolio: The Robo-Advisor That Was Too Early

Spinning Out of Bear Stearns Days Before the Financial Crisis

From Rejected Applicant to Philosophy Major at Notre Dame

How Invest Like the Best Started as a Seven-Episode Experiment

The Kindest Thing: Touring Canada at 23 to Explain Losses

?Q&A· 2

Why Not Sell Canvas to Competing Asset Managers?

Grading OSAM's Canvas Era So Far

✦Tool· 1

Launching Founder's Field Guide: A New Weekly Show for Builders

▲Takeaway· 1

Patrick's Rapid-Fire Lessons From His Guests

Hot Take· 1

Explainer· 2

Story· 6

Q&A· 2

Tool· 1

Takeaway· 1