Episode 68: "We're in the '94 and '95 Era of the Internet. Well, for AI.": 26 Years Building Orases with Nick Damoulakis

Apr 24

"We're in the 2024, 2026 era of AI. Nobody knows where it's gonna go. Nobody really understands the power of it. But you gotta use this technology, bring it into your culture, reskill your people, or else you and your people will become obsolete."

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TL;DR — Key Takeaways

Grit compounds across generations. Nick's father immigrated from a small Greek island, worked on Apollo 13 trajectory math, and built a life from nothing. That template (keep going past what looks impossible) is the engine behind 26 years of Orases.
The first big break came from the weirdest side project. Nick built the first-ever online guitar tablature site in the '90s, which led to meetings with the Harry Fox Agency, Sony, and BMG. Specialized obsession generates doors that general ambition never opens.
The NFL became an Orases client from a chance lunch at the Ritz Carlton in DC. A former partner introduced Nick to a friend who worked at the NFL. Nick had no money, no company infrastructure yet, and won the pitch on conviction alone.
Culture starts with the leader knowing themselves. Most agencies try to write values on a wall before the founder has done the self-reflection. That order is backwards and it shows.
Marriage and business partnership with Amy has worked for 26 years because they can't do each other's jobs. Nick runs sales and vision. Amy runs operations, legal, and finance. Neither tries to cross the line.
AI is not the 2012 social media moment. It's the 1994-1995 internet moment. Everyone was still on Prodigy, AOL, fax machines, and Yellow Pages. Most people missed the shift because they couldn't see the shape of it yet.
The leadership job right now is reskilling. Most organizations are using AI to increase efficiency and then downsize. Nick's bet is the opposite. Use AI to reskill your team so they and you don't go obsolete.
Comfort is the enemy of progress. Companies that do nothing with this transformation will be obsolete inside a decade. The next generation of leaders is already moving.

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Does This Sound Familiar?

You've been building for a while. Long enough to have lived through a real inflection or two. Maybe you watched the 2008 collapse reshape your client list. Maybe you watched mobile rewrite what a website was supposed to be. Maybe you watched the 2020 digital boom drop a wall of new competitors into your space.

Now it's AI. Your peers are split. Half are laying people off and calling it a strategy. The other half are freezing and hoping the hype cycle ends. Your gut says neither is the right play but you can't quite name what is.

You've also started to notice something uncomfortable. The founders who survived the last two inflections aren't panicking. They're reskilling. They're investing. They're talking about AI like it's 1995 and they already know how the story ends.

Nick Damoulakis is in that camp. 26 years into building Orases with his wife Amy, he's clearer than ever on what matters. This episode is the unfiltered version of what longevity actually teaches a founder about the current moment.

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Meet the Guest

Nick Damoulakis is the co-founder of Orases, a custom software development and AI consulting agency he started in the mid-90s with his wife Amy and has grown to five-time Inc. 5000 recognition, 950+ clients, a 96% retention rate, and an 84 NPS. Orases serves mid-market clients including the NFL, MLB, Kimberly-Clark, Johns Hopkins, and Walter Reed. Nick's current focus is AI transformation for established service organizations and he invests time coaching young entrepreneurs on the side.

Visit orases.com →

Episode Summary

1. Grit as an inheritance

Nick opened the conversation where most founders wouldn't: with his father. Born on a small Greek island, Nick's dad immigrated to the US with nothing, earned his way to Rice University for engineering, and ended up on the team that worked on Apollo 13's trajectory math to bring the crew home safely. That context matters because it frames everything Nick said later about grit. He didn't choose grit. He inherited it. And he sees his 26-year run at Orases as the smaller, quieter continuation of the same template: keep going past what looks impossible.

His own first swing at that template was the guitar tablature site he built in college during his first computer science class. He took his passion for music, his new passion for software, and put the first online guitar tablature community on the web. That weird side project earned him meetings with the Harry Fox Agency, Sony, and BMG. Specialized obsession opens doors that general ambition never does.

2. The Ritz Carlton lunch that became the NFL

The origin story of Orases as a real business was an accident of relationships. Nick was teaching, renting a house from two guys who ran a furniture store, and starting a company on the side with Amy. A former partner asked him to lunch at the Ritz Carlton in DC. Nick had never been inside a Ritz Carlton in his life. Over that lunch, the partner told Nick that in thirty minutes a friend from the NFL would walk through the door, and asked if Nick wanted to partner on pitching some tech work.

Nick said yes. The NFL became a client. They remain a client today. Nick was candid about what made that moment possible: it wasn't his pitch deck or his infrastructure. It was his conviction. "I thought I knew so much back then. I was so confident in myself. That rubbed off on others, and they believed it." Twenty-six years later, he says he feels like he knows less every day. The grit and the people are what carried the rest.

3. The marriage that doubles as a partnership

Amy Damoulakis co-founded Orases with Nick and still runs operations, legal, and finance. Nick runs sales and vision. They've made the partnership work for 26 years for a specific reason: neither tries to do the other's job. Nick comes back from a deal with "can you go execute this, can you do the legal, can you make the math work." Amy makes it real. Nick is clear-eyed that he couldn't do her job, and she couldn't do his. That mutual inability is what keeps the boundary clean. It's not a technique. It's a temperament match that held up for a quarter century.

4. Conviction after 25 years

When asked what he'd tell his younger self, Nick's first answer was honest: "I don't know if I'd even start a company if I knew what I know today." He meant it as a joke and also as a truth. The early years of Orases were the happiest ones. Broke, looking for work, building an agency up, figuring things out one problem at a time. He misses that version.

He channels the nostalgia into coaching young entrepreneurs now. Just this month he lent his space and bought equipment to help someone start a podcasting company. His rule for those coaching relationships: no expectations. Just show up, help, and see what happens. "That's how the snowball starts. You go out, meet people, help them, see where it goes. You can't have expectations."

"Back then I thought I knew so much. 26 years later I feel like I know less and less every day. The grit and surrounding yourself with great people is what it's all about."

5. Culture starts with the leader knowing themselves

Nick's framing on culture cuts against the typical agency approach. Most companies try to write values on a wall before the founder has done the self-reflection. That order is backwards. "Leaders need to really know who they are, what their values are, what their non-negotiables are. That's infectious. That becomes your culture."

The cultural result at Orases is a 5% turnover rate sustained over 15 years in an industry averaging 30%. Nick credits it to leader-level self-knowledge first, then to putting words to those values, then to leading by example so consistently that the team absorbs it. You can't shortcut any of those three steps. Skip the first and the other two are performative.

6. The 1994-1995 era of AI

Nick's strongest framing in the episode, and the one most worth stealing, was his positioning of AI as the 1994-1995 era of the internet, not the 2012 social media moment. In 1994 most people were still on Prodigy, AOL, fax machines, and Yellow Pages. The shape of the shift wasn't obvious yet. Only in hindsight did it become clear that the people who started building early had permanently different outcomes from the people who waited.

AI has been publicly available for about 1,200 days. Nick is betting we're at the same inflection point, with the same narrow window to start building. "Nobody knows where it's going. Nobody understands the full power yet. But you gotta use this technology, bring it into your culture, reskill your people, or else you and your people will become obsolete."

7. Reskilling as the main leadership job

Most companies, in Nick's read, are using AI to increase efficiency and then downsize. He sees that as the short-term extraction play that ends badly. The harder and more durable play is reskilling the team you already have. Give them the tools, the training, and the runway to become people who work with AI rather than people AI replaces.

He pointed to the Sequoia thesis of "services as a software" as a signal worth tracking. Software as a service can be increasingly commodified by AI. Human judgment and taste cannot. The agencies that win the next decade will be the ones that promise outcomes to clients and use AI aggressively on the back end to deliver those outcomes faster and cheaper than anyone else. The ones that do nothing will be obsolete. "Comfort is the enemy of progress."

Notable Quotes

"We're in the 2024, 2026 era of AI. We're in the '94 and '95 era of the internet, just for AI."
"Back then I thought I knew so much. 26 years later I feel like I know less every day."
"Reskill your people, or you and your people will become obsolete."
"Comfort is the enemy of progress."
"My wife and I can't do each other's jobs. That's why it works."