Ryan Holiday admits that, having led American Apparel’s marketing during its meteoric rise and subsequent downfall in the 2010s, he has good reason to have practiced Stoicism.

During an early June keynote at the ThreadX 2025 conference for apparel decoration pros, Holiday shared how he was thrust into the spotlight first in his early 20s when he faced verbal lashings for American Apparel trying to move into a San Francisco neighborhood opposed to big box stores, and then as someone who was tasked with wrangling in American Apparel’s Founder Dov Charney and finally as an author – first reflecting on his skills at weaving not-entirely-true stories for media attention, and later the practices of Stoic philosophy.

Ryan Holiday

“Philosophy was the thing that I used the most when I was director of marketing for American Apparel because it was an insane place, as you can imagine,” he said. “I can’t tell you how important something like Stoicism is when you’re riding this kind of curve,” Holiday added, showing a graph depicting American Apparel’s stock price plummeting.

At ThreadX, Holiday’s fundamental lesson for business owners, having gone through the wringer himself, was that managing ego and maintaining good mental and physical habits outside of the office are pivotal to high-level success in business.

Overcoming Obstacles

Difficult times are inevitable in business and in life. One of Holiday’s central tenets, and the theme of one of his books, is that “the obstacle is the way.” Challenges will always present themselves, but in business and life, we all have choices, Holiday said, in how we react to them.

“We think that we want things to go one way, we think that we’ve suffered a disaster,” he said. “But in fact, depending on how we respond, we get to decide what that means.”

“The idea is that we don’t control what happens, we control how we respond to what happens. We control who we are in the situation.” Ryan Holiday

Holiday quotes a passage from famous Stoic Roman Emperor Marcus Aurelius’ Meditations: “Our actions can be impeded, but there can be no impeding our intentions or our dispositions.”

“In every situation, even if it’s not what we want it to be, even if it’s not our fault, even if it’s something we warned against, we now have a chance to respond to it well,” Holiday says. “We can respond to it with excellence, and there is always something we can do with it. There’s something we can do because of it.”

He draws another example from history: Frida Kahlo. The renowned painter was in a bus accident at 18 that left her bedridden for months, and with the help of her parents she set up a specially made easel and mirror system so she could paint lying down. And it was that challenging period that inspired some of her great work throughout her career.

“The idea is that we don’t control what happens, we control how we respond to what happens,” Holiday says. “We control who we are in the situation.”

Managing Ego

Holiday says that ego is the greatest adversary for a businessperson.

“I’ve seen lots of companies succeed and I’ve seen lots of companies fail,” he says. “You find that it’s not about competition, it’s not about regulatory changes, it’s not the rules, it’s not the weather, it’s not the economy, it’s not market conditions. We get beaten by something closer to home. Most empires collapse from within.”

Ego, he says, is easy to spot in others but difficult to see in yourself.

“If you think you don’t have one, you probably have an enormous one,” he says. “If you think you have mastered it, you almost certainly have not. That’s the first thing that ego would want you to think.”

“Our actions can be impeded, but there can be no impeding our intentions or our dispositions.” Marcus Aurelius

The issue is that often ego pairs with ambition, something that successful people have in spades. The challenge, as Holiday spells out, is recognizing your ego and where it hinders your path to success as you see it, and where you’re maybe ignoring opportunities to learn and grow even if it feels uncomfortable.

Ego can trick you into thinking that everything is about you, every unfortunate occurrence is a personal slight directed at you specifically, and that you deserve much more than you’re getting and it’s some outside force’s fault that it hasn’t happened for you. It can also cause someone to take unnecessary risks when they don’t see it as risk, but rather a certainty or inevitability.

He again goes back to the story of American Apparel as an example of pride coming before the fall.

The company’s model was U.S. manufacturing, cutting, dyeing and sewing; basic T-shirts sold for $30 in 2007; no visible brand names on clothing; and the same basics every year rather than re-upping to create demand.

“All of this stuff shouldn’t have worked, and yet it did,” Holiday says. “So you can imagine every step of the way people are telling Dov Charney, ‘This isn’t going to work. Let me tell you the realities of this business.’ And he didn’t listen to them, and he succeeded, which is how almost all success goes. If you listen to the doubters, if you listen to the haters, if you listen to the critics, you never get anything done. And yet, what happens when you succeed in spite of those people? You learn a very dangerous lesson, which is, ‘Don’t listen to conventional wisdom, don’t listen to criticism, don’t listen to doubt, don’t listen to your own legal department.’ You end up driving off of the cliff that people are telling you you’re about to drive off.”

Charney founded American Apparel. The company, a former Counselor Top 40 supplier, ultimately entered bankruptcy. The brand was acquired by Counselor Top 40 supplier Gildan (asi/56842) and is now part of that corporation. Charney and Holiday are no longer associated with American Apparel.

Ego-Less Leadership

Great leaders, Holiday says, push ego away and create other leaders.

Citing Aurelius again, Holiday tells the story about how the ancient Roman was supposed to be the emperor after only a few-year period under Hadrian’s adoptive son, but instead it turned into a decades-long period. Rather than becoming frustrated waiting to ascend to the position, Aurelius studied and learned as much as he could under Antoninus. And while Aurelius was emperor, he regularly left the palace to attend other lessons from scholars and philosophers, even when he could’ve had anyone in the world come to him.

“They learned from each other, they didn’t try to kill each other,” Holiday says. “How we can be the people that our shareholders, investors, climate and children need us to be is by doing this work and keeping our egos at bay. It’s by keeping our desire to always learn.”

The bottom line in Holiday’s lesson is to try to keep your own emotions in check while making business decisions. Regularly ask yourself, “Is this essential?” when dealing with tasks or even your own reactions to a problem. When faced with obstacles, don’t get bogged down trying to move them or climb them, but instead recognize that that’s part of the path and respond accordingly.

And, when a lot of people whose opinions you should trust are telling you that you are destined for a cliff, maybe hit the brakes.