Into the Den

Constantine runs Self Inspection, which uses AI to figure out the condition of a vehicle from a few photos taken on a phone.

The funny thing is they started out building software to make human inspectors better, and pretty quickly learned how biased humans are when they inspect a car.

So they took the inspector out of the equation entirely.

Growing up in Ukraine, he planned on living in California, but not necessarily San Diego.

He windsurfed for 15 years in Ukraine and came to California thinking he'd open a windsurfing school for kids, then found out we don't really have the right type of wind.

He landed in Chicago first, then Arizona, then took a road trip down the coast with his sister and decided this was it. That was 20 years ago.

We recorded this one under a tree at Superbloom.

We got into the 94-year-old grandmother in Alaska who became their proof of concept, why a sedan has 257 panels, and why the boring legacy industries might be the ones actually worth building in.

Connect with Constantine: Self Inspection · LinkedIn
Follow Into the Den: New episodes at TheCoyote.co or wherever you get your favorite podcasts

Rylie plans some of the coolest events in San Diego, and the funny thing is she never wanted to be in the events business.

But growing up in a huge Polynesian family with 27 cousins kind of forces you to organize large groups of people, and she got really good at it (thanks, Mom).

The bigger shift came from a major injury in high school. It changed how she thinks about risk and made it obvious that our time here is relatively finite.

We're planning a tech event together now, talking about what we've each picked up from attending and planning things and trying to build something a little more fun.

That's the hope anyway.

This one is about event philosophy and getting a little more connected in San Diego.

Connect with Rylie on LinkedIn

Follow Into the Den: New episodes at thecoyote.co or wherever you get your favorite podcasts

Hussein Yahfoufi sold his company to a Bay Area firm in 2022.

He was fully remote and a bit lonely in his home office in Encinitas. All the interesting events required a drive through the infamous 52 freeway.

So he hosted his own. Twelve people showed up to the first one.

He sent around a Google sheet so he could introduce people properly at the next one. People complained they had to fill it out every time. He added tabs. They complained about the tabs. So he built a landing page. They complained about managing two sites. So he added ticketing. The ticketing needed Stripe. Stripe needed reminders. Reminders needed calendar invites.

Eventship now has 22,000 users, just signed a defense conference that nobody from San Diego goes to yet, and is hosting startup weeks outside of our city.

We recorded this one in his home office in Encinitas.

We talked about why 99 percent of Eventship's features were not his idea, why recurring events are the only kind that actually build something, how to tell when a community is dying versus dormant, what the in real life LinkedIn actually looks like, and why he chose a dive bar where all the drug deals used to happen as the permanent home of his mixer.

Hussein is the kind of person who builds infrastructure for a city without meaning to. He wanted to meet people and he ended up making it easier for twenty-two thousand of us to find each other.

Connect with Hussein: Eventship · LinkedIn 
Follow Into the Den: New episodes at TheCoyote.co or wherever you get your favorite podcasts.

Sam Hodgson moved to San Diego when he was three and a half years old. He flew in from New Zealand. He has lived here ever since, except for four years in New York covering the country for the Times. He came back when his first kid was born.

He founded Uptown 11 Studios in 2024 out of a coworking space in North Park. It is a nonprofit creative agency that helps community organizations in San Diego tell their own stories.

Before that, he ran the photo and video team at the Union Tribune. The photo department had 47 people when he was born. It had 6 when he took over.

We recorded this one at the Hardy Hood in North Park. We biked over to record.

We talked about what it was like to fly on the Golden State Warriors private jet (the story was supposed to be about the equipment manager), what happens when DeMarcus Cousins comes flying down a stadium hallway trying to fight Kevin Durant underneath the arena in New Orleans, why San Diego gets in its own way by constantly telling people it is a big city instead of just showing them, and why AI will never be able to find the one woman in San Diego who can explain why an entire neighborhood's violent crime data traces back to a single house.

We also talked about what it costs a city when nobody is watching, why the tech world in San Diego has some of the best stories that nobody is telling yet, and what it would look like if the Howl got a little bit of growl.

Sam is the kind of person who, at the end of a conversation about the future of journalism and the soul of a city, says: "I hope you hit record."

Connect with Sam: Uptown 11 Studios · LinkedIn Follow Into the Den: New episodes at howl.thesocialcoyote.com or wherever you get your favorite podcasts

Kris Lichter grew up in Bird Rock. His dad had a small boat at a slip in Mission Bay, and on Saturdays he'd drag Kris down (sometimes willingly, sometimes not) while he tinkered. Kris would fish off the docks for halibut, or whatever he could catch.

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

James Zanewicz didn't plan on San Diego. He'd lived in Louisville, LA, New Orleans, DC, Illinois, and New Orleans again. He changed his phone number to a 504 area code. He was not leaving.

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

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

Alex Waters got connected in San Diego by getting sandwiches.

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

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

Ross Young built Clinically AI from his living room. Literally. When Jonah showed up to plan a bootstrappers event at Ross's house, it was also the office. This conversation starts there, and goes deep on what it actually takes to build something from scratch in San Diego when you could have stayed comfortable.

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.