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  1. Invest Like the Best with Patrick O'Shaughnessy
  2. William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]
William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy · Mar 17, 2026

Plaid co-founder William Hockey shares his contrarian playbook: build without VCs, embrace extreme personal risk, and master a boring niche.

Banks in Emerging Markets Attract Top Talent That Western Banks Cannot

In markets like the Congo, the smartest graduates lack local Big Tech options. They flock to the most stable and lucrative industries, often banks. This results in executive teams at emerging market banks that can be superior to their Western counterparts.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

The Most Innovative Financial Services Emerge from Highly Constrained Nations

Countries like Argentina or Iran, facing extreme economic pressure and isolation from global markets, are forced to build bespoke financial systems from scratch. This necessity drives leapfrogging innovation not seen in more stable, developed economies.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Inefficient Legacy Brands Will Be AI's Biggest Beneficiaries, Not AI Startups

The biggest winners from AI will be entities with massive distribution and significant cost inefficiencies. Legacy banks and large brands are prime candidates, as AI can drastically cut their operational costs while they retain their powerful brand and distribution moats.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Banking Friction Is a Deliberate Feature to Protect Vulnerable Users, Not a Tech Bug

The slowness in traditional banking is often intentional, not a sign of outdated technology. These "bugs" are features designed to protect the most vulnerable 5-10% of customers from fraud like romance scams or elder abuse, which is a massive liability for banks.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Owning a Bank Creates a Powerful Regulatory Moat for Software Companies

Fintech infrastructure company Column bought a bank to gain a unique regulatory advantage. This allows them to build products that non-bank competitors cannot, by handling all backend complexity with the Federal Reserve and card networks for clients like Ramp and Brex.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Founders Can Escape Consensus Thinking by Immersing in Emerging Markets

Plaid co-founder William Hockey argues that Silicon Valley is a "consensus society." He travels to constrained environments like Kinshasa to find unique creativity and non-obvious ideas, which are impossible to generate within the abundant and insular tech hubs.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Y Combinator's "Request for Startups" List Signals Oversaturated Markets to Avoid

William Hockey suggests that YC's public list of desired startups should be treated as a signal of what *not* to build. By the time an idea is consensus enough to make the list, it attracts a flood of smart people and capital, making it intensely competitive.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Silicon Valley's Insular Culture Results in Elites Building Products for Other Elites

Silicon Valley has become an "elite-dominated society" where insularity causes founders to build for each other. This creates a disconnect from the needs of the broader population, limiting the real-world applicability and resonance of many new products.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Venture Capital Is Like "Heroin" Forcing Startups to Chase Short-Term Trends

The venture capital fundraising cycle is addictive. It forces founders to optimize for the next round by chasing trends like AI or stablecoins, creating a "windy way" to their goal instead of a direct path. Self-funding enables true long-term investment.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Use Company Earnings for Annual Employee Share Buybacks to Provide Liquidity

Instead of relying on venture-led secondary sales, Column uses 25% of its annual earnings to conduct its own tender offers. This provides regular liquidity to employees, enhances retention, and aligns the team long-term without the dilution from new funding rounds.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

The Best Founders Sustain Fascination with Extremely Boring Problems for Decades

True entrepreneurial success isn't about chasing hot topics like AI. It's about finding a niche, boring problem and developing a deep, multi-decade obsession with it. This requires a unique ability to find interest where others see none, which is a powerful competitive moat.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

US Adversaries China and Russia Still Use the Dollar for Their Own Trade

Despite political tensions, a vast majority of global trade, including oil sales between US adversaries China and Russia, is denominated in US dollars. This reliance gives the US an unparalleled national security tool and soft power, as the trade must cross through US financial institutions.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Early Startup Employees Take On More Financial Risk Than Today's De-Risked Founders

Today's founders can easily raise seed funding and have safe fallback careers. In contrast, an early employee gives up a high, stable salary for years in exchange for a small amount of illiquid equity. The employee's personal financial risk and opportunity cost are far greater.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Founder William Hockey Pledged $1B in Plaid Stock for a $70M Loan to Start Column

Despite being a co-founder of Plaid, William Hockey had minimal liquidity when starting his next company. He funded it by taking a high-interest loan against his private Plaid stock at a 5% LTV, pledging over a billion dollars for $70 million and facing multiple margin calls.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago

Find Your Competitive Edge in Obscure, 2,000-Page Books on Your Niche

William Hockey develops his business strategy by reading extremely deep, boring, historical texts, like a 2,000-page book on 19th-century Chinese banking. He finds that extracting one unique insight from such a source can create millions in value and is a moat that AI cannot easily replicate.

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463] thumbnail

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]

Invest Like the Best with Patrick O'Shaughnessy·a day ago