He left San Diego plenty, though. He went to AOL, where a small team of interns built the first dating site on the internet and spent their days moderating everything that came pouring into the holding tank. He went to IBM, where he worked across 81 countries and helped roll out Java. He went to San Francisco to run Ardica Technologies, a clean hydrogen startup selling fuel to the Department of Defense. An industry he had zero experience in when he took the job.

He is now the CEO of TL Foundation, San Diego's philanthropic venture fund with no management fee or carry. 100% of returns go back into the fund and back into the city, forever. It's named after the Tree Lady: Kate Sessions, who planted the first trees in San Diego in 1892 and never saw the canopy she created.

We recorded this one outside at Superbloom on East Mission Bay. Crown Point is straight ahead. Kate Sessions is on the hill.

We talked about what it means to call yourself a failed scientist, what actually came out of that dating site holding tank, how you become CEO of a hydrogen company with zero defense background, why San Diego should stop trying to be Silicon Valley, and what this city looks like in 2040 if TL does what it's supposed to do.

Kris is the kind of person who, when you ask if he'll live long enough to see TL's flywheel reach its full potential, says: "I'm a very healthy person, Jonah. I intend to be around."

If you believe in what TL is building, there's no minimum to get involved. Reach out to Kris directly.

Connect with Kris: TL Foundation · LinkedIn
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Then his friends started blowing up a group chat with a job posting. He applied mostly to make them stop. He got the job.

He's now the CEO of Connect San Diego, the first intentional innovation ecosystem ever built. Not just in the US. In the world.

We recorded this one at his patio table, which was the only furniture in his new apartment. We talked about why San Diego feels more like New Orleans than LA, the PhD sociologist who built Connect's community DNA at the founding in 1985, and why Austin and Miami have roughly 5% of San Diego's innovation output and four times the press coverage. We also got into what it actually feels like to be handed a 40-year legacy and told to reimagine it.

James is the kind of person who does office hours at a wine bar and hands out bottles of wine because that's what you do in New Orleans, and it turns out it works everywhere. San Diego got lucky when he said yes.

Connect Summer Social is June 16. Tickets are around $60. James says it's the one to go to.

Connect with James: Connect, James on LinkedIn

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Not metaphorically. He was volunteering at Startup Week when nobody could figure out who was going to feed the volunteers. He raised his hand. Walked down the street. Problem solved.

That's the whole philosophy, and it turns out it works.

Alex is the founder of The Program Labs, a nonprofit that helps organizations build entrepreneurship programs across San Diego. But before that, he spent years becoming one of the most connected people in the city by doing the things nobody else wanted to do. Moving chairs. Checking people in. Showing up every Wednesday to 1 Million Cups for eight months before ever asking for anything.

In this episode: why the most connected people in any ecosystem are almost always the ones who give the most, the difference between transactional networking and actually building community, the yacht theory of social capital, and why consistency is the strategy most people skip.

Connect with Alex: The Program Labs Alex on LinkedIn

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Ross is the Co-Founder and CEO of Clinically AI, a platform that reduces clinical documentation time for behavioral health providers by up to 80%. The mission: help the people who help people.

The origin: a school district drowning in unread alerts, kids falling through the cracks, and one question: "If I built you something that could fix this, would you use it?" He built a prototype in a weekend. It went viral.

In this episode: bootstrapping vs. raising, building a team in San Diego on purpose, AI in the most human conversations that exist, and why Ross eventually moved his company out of his den and finally got a real office... that admittedly has way too much space.

Connect with Ross: Clinically AI Ross on LinkedIn

Follow Into the Den: New episodes every week at howl.thesocialcoyote.com or wherever you get your favorite podcasts.