Do Hard Things Podcast

Do Hard Things A Podcast With Gabe Lullo Ft. David Robinson

Do Hard Things Podcast

Show Notes

"Every business owner takes all this advice from bigger companies to grow, but when it comes to technology, they suddenly think they know better and try to do it themselves." - David Robinson, Founder of Stratos

David’s career started as a lighting technician for concerts featuring Katy Perry, Tiesto, Jay-Z and others.

Then unexpected fatherhood pushed him into "a real job."

A family connection brought him into healthcare technology, where he helped build one of the first electronic medical record systems for reproductive endocrinology.

The catch?

He’d never done anything like it before.

So he figured it out through weeks of sleepless nights.

Then came a chance conversation at a pool bar in Palm Springs. David approached WebMD’s former CFO and somehow knew enough about his struggling company to get his attention.

That conversation led to a job offer in New York, and eventually to working alongside the Big Four consulting firms.

That experience became the blueprint for Stratos:

Take the technology, expertise, and infrastructure that Fortune 500 companies spend millions on, and make it accessible to the mid-market businesses that are often overlooked.

David has a pretty blunt take on those businesses.

They'll follow proven advice from bigger companies when it comes to banking, sales, hiring, and structure.

Then they get to technology and think:

“This is the one area I can figure out myself.”

So they hand it to a nephew.

So they hand it to a nephew, a freelancer, someone "good with computers." A few years later, they're paying for that decision.

David’s filter for business is simple:

“If we’re not helping you make money or save money, it’s probably not a good thing to be involved in.”

His view on AI is just as pragmatic.

Vibe coding isn’t going away.

But it can’t vibe-code compliance.

Deploying an AI-built tool without a technical partner behind it is rolling the dice, and for most regulated companies, that’s a bet they can’t afford to make.

More from Do Hard Things Podcast

Oct 21, 2026

"People don't change because you give them housing. People change because they're given community, accountability, purpose, work, and people around them who actually believe in them." - Moe EganPreston and Moe Egan came to The Other Side Village from opposite ends of the problem.Moe grew up in East Oakland, surrounded by addiction and crime, and became a lifelong addict and criminal himself. He went through six or seven recovery programs and graduated from every one. Each time he relapsed. Then came his seventh arrest, and the officer who cuffed him was his old football coach. The coach told him about Delancey Street, and facing San Quentin, he wrote a letter begging for help.Preston has spent 30 years in nonprofit work and never lived any of that. He's upfront about it. His problem is with the systems around the work, which measure beds filled and boxes checked instead of whether people reach long-term independence.Together they lead The Other Side Village, a permanent community built on peer accountability, where residents run social enterprises like a donut shop. Preston brings the strategy and Moe brings the lived experience, and neither is enough alone.Recently Moe took a group of people who spent decades on the street to New York. For some it was their first flight. On the way home they asked him how to get a passport."People don't fundamentally change when they feel temporary... When people know they have a permanent place in the community, they start thinking about next year instead of next week." - Preston L. Cochrane

Oct 19, 2026

"None of us engage perfectly with technology when we're overwhelmed or stressed. You shouldn't build a system that requires perfect engagement in order to be useful." - Ellie Gordon

Oct 15, 2026

"If there's something I can do and should do, then I have a responsibility to do it. That is what I signed up for when I became a nurse." - Melinda Yormick

Oct 12, 2026

"It didn't matter what I had accomplished before, what I had achieved, what awards I had. None of that mattered. It only mattered what I brought that day." - Mary Crafts

Oct 7, 2026

"Don't make an assumption, ask the question. Ask your senior people two things: what's slowing you down, and what would make you consider leaving. That pattern is your real priority list." - Alex Seiler

See all episodes →