Writings

Operator

Can I Make $250,000 in 90 Days With AI?

A 90-day experiment to build $250,000 in new revenue with AI while running an existing business—and to discover how much one person can direct.

Operator

The New Divide: Why Learning AI Now Will Change Who Gets Ahead

AI is making knowledge, communication, software creation and data analysis available to almost everyone. The real divide will be between people who learn to use it and those who do not.

Operator

A Working Business Is Not Enough

Why the person running a company must keep building its next source of growth before the current model reaches its ceiling.

Network

Borrowed Trust

How trust moves through people, institutions, and networks—and determines which opportunities reach you.

Machine

Build the Machine

How a small clothing brand and a high-ticket consultancy built very different systems for turning attention into customers.

Operator

Buying Madoff

How I acquired Bernie Madoff’s market-making business—and learned that creating value and retaining it are entirely different skills.

Operator

Growth Is the Operator’s Job

Growth should be a permanent responsibility of every operator. How to review offers, customers, acquisition, competition, market changes, and growth constraints each quarter.

Simply Alpha Capital: Case Study

Why Darin Oliver founded Simply Alpha after serving as an iGaming regulator—and how the firm helps operators enter difficult markets with fewer mistakes.

Source

The Opportunity I Couldn’t See

While I was consumed with buying Madoff’s market-making business, one of the best opportunities of my career called me directly. I told him I did not have time.

Source

The World May Be Teaching You Something

The facts of an experience and the meaning we assign to it are not the same thing.

Operator

Do Not Pivot Before You Understand the Business

Before pivoting, founders should distinguish weak execution from a failed business hypothesis. Learn how to use evidence to decide whether to persevere or change direction.

Network

You Have to Give the Miracle Somewhere to Land

A story of faith, work, introductions, and the chain of human connections that made an unexpected career possible.

Operator

The Path I Did Not Take

A reflection on Boston, San Francisco, responsibility, and the difference between a successful path and an aligned one.

Source

The Spokes of the Wheel

A philosophy of spiritual connection: how faith, action, and other people become the channels through which life changes.