What does the entrepreneurial path to meaning look like? 

Today I’m sharing my friend Paul Lightfoot’s (highly abbreviated) story—of searching for belonging in various careers and ultimately becoming an exec at Patagonia, hell-bent on saving the planet. 

It’s a story about following your Eros (desire) even if it leads you down dark alleys, about seeing your life as an integrated whole—a movie where all the acts weave a complete narrative and it all makes sense in the end. 

I hope this story helps you see your own movie. 

With love, 

Dave

The Evolution of an Entrepreneur…and a Human

Paul Lightfoot is one of the most driven people I know. 

Like me, Paul was a product of the ’80s male industrial complex: from Schwarzenegger and Stallone to Gordon Gekko and misogynous metal bands, our generation was raised to believe a good life was a financially and materially rich success-fest. 

Underneath that noise, however, was a desire for love and belonging. Paul’s quest began with that deeply held need. He wanted recognition, to be liked.  

He did just enough to get through college and law school and into the real world. He joined the “Ivy League” of the legal industry: a corporate firm in New York. Finally, he would earn the respect of his community. 

A year in, Paul looked at the partners around him. “They were making tons of money but were the unhappiest, unhealthiest people I’d ever seen. When my favorite lawyer left to become a banker, I had a haunting realization I’d made a big mistake,” he said. 

Around this time, his father passed away. He traveled home to California to be with his family. With the passing came reflection. He decided to leave the firm. 

This was 1998, the rise of the dot-com boom. It didn’t take long to be lured into the promise of fast fame and success. Having worked in the food industry for years, he had an idea to streamline restaurant reservations. He raised money and began building. 

Soon, Paul had what he’d always considered success, at least on paper. He was wealthy, featured in magazines, and celebrated by his peers. He thought he had found what he was seeking. 

When the market collapsed in March of 2000, he went from paper wealth to real debt alongside earned wisdom: “Money and fame are fleeting. It's not gonna buy you good relationships, or a good relationship with yourself.” 

Still, entrepreneurship, with its uncertainty and control over one’s destiny, had hooked him. But this time he would do it the old-fashioned way with profits, humility, and hard work. He took on a turnaround CEO project and transformed two companies into healthy, growing enterprises. 

He loved building and supporting his team and acting as a servant leader, but something was missing: his work was fueling consumerism, not making things better. He’d proven he could build a company, but he wanted purpose. 

A period of thoughtful inner work showed him it had always been there: Food. He loved cooking and had become an activist for organic food and environmentalism. His epiphany was that he could do it for work. 

In a “burn the bridges” decision, he went all in on a new business to transform the food system for human health and environmental impact.

Paul’s business, BrightFarms, took on the inefficient and environmentally damaging oligopoly of organic food businesses by creating hyper-local food suppliers.

At first, convincing stores to carry their product was a Sisyphean battle. But with a belief in the mission, grit, hustle, and time, BrightFarms slowly became a gorilla in their space (I told you this story was abbreviated 😃). Copycats jumped into the fray and raised billions, and the old-guard companies fell apart. 

For the first time, he felt the energetic flow of purpose, mastery of his craft, and building something meaningful. But success also meant that to survive and thrive, the company would need to transition from a pirate ship to a Navy vessel. It had to grow up. 

And while Paul was proud of it all, he was more of a pirate than a sailor. In 2018, he made plans to move on. 

Over the next few years, he reduced his hours at BrightFarms and began exploring regenerative agriculture and its role in fighting the climate crisis and ensuring humanity's future. 

Now, he had a mission and a thesis: consumer demand would drive the transition to regenerative agriculture. He planned to become an investor in businesses that supported this thesis. 

Then he got an unexpected call from a recruiter. Patagonia needed a leader for its new food business. In just 30 minutes, Paul’s life changed forever. One of the most inspiring and purpose-driven companies had the exact same thesis around the future of food. He was all in. 

He would no longer run the show, and his family would have to sell two houses, move across the country, and be separated for a year during the transition. But for the first time, Paul felt the confluence of a deep desire to create mixed with a profound sense of belonging and peace. 

The rest is history. 

While it’s not a utopia, the truly elemental things are in place. “I've been here for two years,” Paul said, “and I've never been more certain that I'm never gonna work anywhere else if they give me the chance to stay. I would fold sweaters at the Fisherman's Wharf store if that was where I was needed. I’m with my fellow weirdos, on a shared mission, infused with love. What else is there?”

What’s Your Patagonia? 

A Question that May Help

Here’s something I ask myself a lot to make sure I’m on track: Can you draw a palpable connection between your five-year-old self's aspirations and your current work?

Whether you wanted to be a baseball player, dancer, or paleontologist, what did your younger self want most deeply? Camaraderie? Connection? Curiosity? Play? Find that common thread, and you’ll be closer to the answer of why you’re on this planet.

ATTN PORTLAND PEEPS!

I’ve partnered with Portland Seed Fund, Marco Law, and Stifel Bank for an event you won’t want to miss! Join me Monday, June 10 at 5pm at Kiln (1120 SE Madison), for a special session on the hidden patterns that lead to startup failure and how to avoid or recover from them.

Free books, fireside chat, stories of success and failure, and plenty of food, drinks, and networking. Learn how to optimize your company’s trajectory (and your happiness).

LIMITED SPOTS LEFT! CLICK TO SECURE YOURS!

Thanks so much for reading. If you know someone who you think should hear these stories, please share it with this link.

With Love,

Dave