Why You’ll Never Succeed at Chip Wilson’s Yoga Pants

This week’s Methods of Prosperity newsletter is going out on Christmas Day this year.

Many people will miss it for that reason. They’re celebrating, which is wonderful (Merry Christmas).

There’s a select few of us who want more. For whatever reason, we’re not satisfied. Instead of relaxing, and taking days off, we’re obsessed.

If you’re like me, you’re obsessed with building something. You’re building your product or service. You don’t yet have it set up to run without your input. That’s called key man risk. The entire operation depends upon you.

If you don’t show up every day, your product fails to ship.

If you say something wrong, you lose customers.

That’s what happened to Chip Wilson.

He’s an American-Canadian billionaire entrepreneur. Chip Wilson is the founder and former CEO of Lululemon Athletica. You know, the yoga-inspired athletic apparel company. He pioneered the modern athleisure trend, turning technical athletic wear into everyday fashion.

Wilson founded Lululemon in Vancouver in the late 1990s. after selling his earlier board-sports apparel company, Westbeach Snowboard. He served as CEO until 2005, then as a senior executive and later chairman. He had to step away from management and the board in the mid‑2010s.

I’ve made the following statement before:

As a teacher of Methods of Prosperity, I approach this as a philosophy. Not as a set of rigid rules, but as a liberating model of how reality operates.

Most people separate materialism from spirituality. Which is a false dichotomy. Prosperity principles apply across all aspects of life.

You can think of this philosophy as spiritual materialism or materialistic spirituality.

With that in mind, let’s first explore the acumen demonstrated by Chip Wilson. Next, we’ll explore his folly.

Chip Wilson is like a coin that can’t exist with only one side.

He embodies the principle of coincidentia oppositorum.

What’s that? It’s the unity of opposites.

It drives both transcendent success and spectacular folly.

New innovations replace outdated systems. This idea comes from an Austrian economist named Joseph Alois Schumpeter (1883–1950). He coined the term “creative destruction.” This term describes how innovation replaces old industries.

Wilson understands and acts on creative destruction:

Attachment to what is prevents becoming what could be.

You must always be plotting against your present self to birth your future self.

This is the mark of one who transcends the merchant’s trap. That is, defending yesterday’s profits at tomorrow’s expense.

Notice the paradox here: To preserve, you must destroy.

Wilson made himself his own most dangerous competitor. Which made sure no external enemy could surprise him. This is strategic paranoia elevated to art form.

Now, the downside risk is that you might become your own worst enemy.

Here’s his catastrophic misstep that reveals the shadow side of the entrepreneur-prophet:

He made this statement when addressing complaints about sheer yoga pants.

It’s an example of what happens when business acumen divorces from human wisdom. Rather than accepting responsibility for a manufacturing defect, Wilson blamed his customers’ bodies.

Here’s a rule that seems obvious: Never mention women’s thighs in a derogatory way.

But wait... he made it worse by his subsequent “apology.”

Wilson apologized not to the customers he offended, but to his employees who had to deal with the fallout.

This reveals a fundamental misunderstanding of accountability and empathy. Which were the very qualities that distinguished Lululemon’s community-building origins, right?

Wilson understood that brands must have boundaries (“you’re not everything to everybody”). But he failed to see that boundaries define what you stand for, not who you stand against. The line between clarity and cruelty is thinner than a yoga pant seam.

Know when to speak and when silence serves better.

Sure, Wilson created a billion-dollar empire. As of March 2025, his estimated net worth is $6.3 billion. Not bad, right?

How much more would it be without his unfiltered pronouncements?

This is coincidentia oppositorum.

One man refused to accept conventional wisdom.

That split the outcome.

He channeled one part of his energy into creation, the other into destruction.

As above, so below. As within, so without.

I like you,

– Sean Allen Fenn

PS: The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here: