Dan Sullivan

"The Strategic Coach founder whose decades of entrepreneur coaching became the Gap and the Gain."

Dan Sullivan is a Canadian entrepreneur and the founder of Strategic Coach, the coaching program he built in 1974 to help ambitious business owners think and plan like founders rather than employees. Over five decades he has worked directly with tens of thousands of entrepreneurs, refining a body of tools and frameworks inside Strategic Coach workshops long before most of them ever reached print. Sullivan's central insight — that unsuccessful people measure themselves against an ever-receding ideal while successful people measure themselves against how far they have come — began as a coaching exercise for his own clients. In the 2020s he partnered with organizational psychologist Dr. Benjamin Hardy to translate decades of that workshop material into a series of bestselling books, including The Gap and the Gain, Who Not How, and 10x Is Easier Than 2x. He continues to run Strategic Coach from Toronto with his wife and co-founder, Babs Smith.

3 books featured·Founder of Strategic Coach·Coaching entrepreneurs since 1974

Books by Dan Sullivan

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Key Ideas & Recurring Themes

Measure backward, not forward

Successful people gauge progress against where they started, not against an ideal that keeps moving away — the core distinction of the Gap and the Gain.

Three lenses distort progress

Most people measure themselves against an ideal or against other people — both put you in the Gap. Only measuring against your own starting point puts you in the Gain.

Wins compound into confidence

Confidence is not a personality trait — it is a byproduct of consistently registering your own progress, a habit anyone can build.

Ask who, not how

Bigger goals stall when you volunteer to be the method. Find a Who who already owns the How and keep Unique Ability work.

2x keeps the wrong 80%

A modest goal lets you keep almost everything you already do. A 10x goal makes most of it illegal.

Notable Quotes

"Your gains are always greater than your goals — if you take the time to measure them."
— The Gap and the Gain
"Confidence isn't found by reaching the ideal. It's built by measuring backward."
— The Gap and the Gain
"When you have a goal, don’t ask how. Ask who."
— Who Not How
"The smaller goal is the harder life."
— 10x Is Easier Than 2x

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Book Author Dan Sullivan