20 Companies and Over 1 Billion Dollars Later

Brent Freeman was 23, fresh out of USC and carrying a quarter million dollars in student debt, when he closed a $10 million deal in Dubai.

He celebrated that night and the next morning he woke up expecting to feel fulfilled.

Instead, he felt empty.

“Full stop. Money does not make you happier,” he told me on Founder’s Story.

Going From $1 Billion in Deals to Total Burnout

Freeman went on to co-found 20 companies that generated over $1 billion in revenue. Italy’s former royal family knighted him, and he founded the world’s number-one Airbnb experience.

But he is quick to puncture the highlight reel. “We had way more failures than success,” he said.

The wins came at a cost he did not see accumulating. “I had all of the things, but I was alone. I was surrounded by people, but I felt completely lonely,” he said.

Hitting Rock Bottom

It eventually got dark. In the middle of a divorce, with a struggling company, Freeman stood in a San Francisco penthouse and thought about taking his own life.

Then he watched the fog roll in and cover the sun. He realized his dark thoughts were like those clouds, temporary and always passing, with the sun still shining behind them.

“If I need everything to change, then maybe I need to change everything,” he asked himself that day.

He went to Baker Beach that evening and watched his first sunset in years. He cried, then wrote a list of everything that brought him joy and realized he was doing almost none of it.

Understanding the Impacts of Chronic Stress

Freeman spent the next decade turning that discovery into a method, which he lays out in his book The Alchemy of Joy. It starts with understanding what burnout actually does to your brain.

He explained that chronic stress parks you in high-beta brain waves, the fight-or-flight state evolution designed for escaping predators. That alarm was built to switch off after 90 seconds, not to run all day on Slack, email, and social media.

“Our organism hasn’t evolved as fast as our technology has,” he said.

Living in that state floods your body with cortisol. Digestion, immunity, and sleep all suffer while you tell yourself the pressure is normal.

“It’s like driving 100 miles an hour on the freeway in first gear,” Freeman said. “It’s just going to blow up at some point.”

His answer is not more willpower. He argues the subconscious mind is 40 to 50,000 times more powerful than the conscious mind, so lasting change means working with your nervous system instead of forcing it.

Overcoming the Stress Through Reliable Strategies

The tool he shared is one you can use in the middle of a board meeting. He calls it the reset breath.

You inhale for six seconds, hold for four, and exhale for eight, finishing with a small audible sigh. “The exhale that’s longer than the inhale, it calms your nervous system and tells your nervous system you’re safe,” he said.

Do it for one full minute. Freeman says that minute stimulates the vagus nerve and widens the gap between stimulus and response, which is where good decisions live.

For extra credit, he adds two steps he calls stop, see, soften. After the breath, zoom in on one small detail near you as if you have never seen it before, then bring up a feeling of gratitude.

Sixty seconds. No app, no subscription, no cost.

Integrating the Key Lesson Into the Bigger Picture

The bigger lesson is about the story the startup world keeps selling. Freeman calls it “the number one lie we’ve been sold and told,” which is “once I make money, it’ll solve all my problems.”

He is not against money or exits. He is against deferring every ounce of joy to an imaginary finish line, because as he put it, “we’re not promised the destination.”

His advice for founders is to treat joy like a compounding asset and invest in it daily. A sunset, he reminded me, is free.

“We defer joy for one day,” Freeman said. “My message is make one day today.”