Writings
Perspectives on life, business, technology, and the hidden forces that shape outcomes.
Writing
12 essays
8 min listenOperator
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.
8 min listenNetwork
Borrowed Trust
How trust moves through people, institutions, and networks—and determines which opportunities reach you.
8 min listenMachine
Build the Machine
How a small clothing brand and a high-ticket consultancy built very different systems for turning attention into customers.
8 min listenOperator
Buying Madoff
How I acquired Bernie Madoff’s market-making business—and learned that creating value and retaining it are entirely different skills.
9 min listenOperator
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.
9 min listenSimply 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.
8 min listenSource
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.
8 min listenSource
The World May Be Teaching You Something
The facts of an experience and the meaning we assign to it are not the same thing.
5 min listenOperator
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.
8 min listenNetwork
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.
8 min listenOperator
The Path I Did Not Take
A reflection on Boston, San Francisco, responsibility, and the difference between a successful path and an aligned one.
9 min listenSource
The Spokes of the Wheel
A philosophy of spiritual connection: how faith, action, and other people become the channels through which life changes.