Three guys, one bedroom office, zero guarantees — that’s how Andromeda Technology Solutions kicked off its 30-year journey. CEO Jeff Barrella shared how he and his co-founders grew a side hustle into a 50-person MSP powerhouse with millions in revenue and a spot on the MSP501 list.

His take? No magic tricks — just old-school commitment to taking care of customers, something he calls a “lost art” these days. While others chased every shiny new business line, Andromeda’s success came from staying true to what they do best, even after learning the hard way that growing too wide can backfire.

Jeff talked about what it really takes to lead through growth. Early on, it was all startup hustle — long nights and all hands on deck. But as they scaled, they invested intentionally in culture, benefits, and the kind of workplace people actually stick around for — which is why their average tenure is seven years, nearly unheard of in the MSP space.

His advice to founders feeling stuck? Play the long game. There’s no “four-hour workweek” here. It’s about putting in the time, pivoting when things don’t work, and doubling down when they do.

If you’re going to work this hard, Jeff says, you might as well build something you love so much you have to force yourself to stop working. That’s the real measure of success.

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“You can’t transform your business if you won’t transform yourself.” That was the big takeaway in this conversation with Ted Santos, the turnaround expert behind Turnaround Investment Partners.

Too many CEOs try to “fix” their people without ever looking in the mirror. Ted has seen it at every level — from Fortune 500 boardrooms to struggling family businesses. Culture change starts at the top. If the leader won’t shift, nothing else sticks.

Ted calls himself “in the business of producing miracles.” His approach? Teach CEOs to intentionally create problems worth solving — like Henry Ford did when he turned the auto industry on its head. Real breakthroughs demand disruptive strategies, not incremental tweaks.

We talked about how corporate cultures get stuck in “busywork excuses” — people claim they’re overloaded just to keep new ideas away. Ted’s advice: uncover the blind spots and toxic narratives that hold people back. Breakthroughs fail when the culture quietly sabotages them.

One great story Ted shared was how he helped a third-generation food manufacturer avoid shutting down an empty plant by pivoting into co-manufacturing. Instead of just making their own products, they produced for other brands too — driving a 30% revenue increase in year one.

The conversation took a surprising personal turn too: Ted’s book Here’s Why You Can’t Find Love shows how the same skills that build strong companies — conflict resolution, clear communication, self-awareness — also build strong relationships. If you can’t lead at home, it shows up at work.

And the wildest leadership tactic Ted ever used? An unplanned ultimatum during a team mutiny that turned dissenters into loyal allies — all because he’d built so much trust beforehand.

Transform yourself. Create problems worth solving. Build cultures that don’t kill big ideas. Great reminders for any leader ready to get out of their own way.

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Everyone loves to talk AI and cloud.
Juan Lucas Barbier talks about what actually keeps the world running: COBOL.

Known in the enterprise world as the “COBOL Whisperer,” Juan is on a mission most tech leaders don’t even realize is critical—modernizing the legacy infrastructure that still runs the global economy.
$7 trillion in daily transactions.
85% of the world’s transactions.
96% of airline and hotel bookings.
That’s not a relic. That’s the backbone.

In his GTLE appearance, Juan lays out why modernization efforts keep failing—99% of the time.
Too many companies skip documentation.
They put Java devs on systems they don’t understand.
They chase shiny tools instead of understanding their own architecture.

Juan’s team fixes that with a human-in-the-loop AI process, a deep documentation-first strategy, and a framework he calls “maintain, maximize, modernize.”
They’ve translated over a million lines of COBOL into clean, reliable Java—without creating “Jobble,” the broken hybrid mess big consultancies leave behind.

He also drops fire insights on how AI actually scales inside legacy orgs:
— Why data is more important than infrastructure
— How agents will replace assistants
— How his team works 35% faster than most dev shops using structured planning and automation

If you think legacy systems are dead, this conversation will flip your worldview.

Juan’s not just talking modernization.
He’s leading it—quietly powering the systems that keep everything from your mortgage to your medical records alive.

Full GTLE episode is out now.
Don’t miss it.

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What if the difference between stalled chaos and real progress is simply someone brave enough to say yes?

In this week’s Gaining the Technology Leadership Edge, I had the chance to sit down with Frank Carone—former NYC Chief of Staff, powerhouse business litigator, and founder of Oaktree Solutions. His approach to leadership? It`s not about ego or red tape. It’s about tactical empathy, real listening, and building a culture where forward motion is the default setting.

Frank shared how the "City of Yes" mindset helped reshape New York—from bringing to life the once-stalled Willets Point project to reimagining Kips Bay as a thriving biotech hub. The results? Affordable housing, infrastructure breakthroughs, and the first-ever privately funded MLS stadium in NYC. Not bad for a guy who leads with listening.

We unpacked:
How starting with “yes” opens doors others don’t even knock on

His high-pressure decision-making framework rooted in empathy and curiosity

Why mutual respect and long-term relationships are his secret weapons

What it takes to lead change in government, tech, and law—all at once

Also… yes, the Brooklyn accent is real. So is the grit. And yes, Frank might rather be golfing with a glass of wine in hand—but for now, he’s busy building smarter, more collaborative futures.

Curious how to get things done in high-stakes environments without steamrolling people in the process? You’ll want to hear this one.

Watch the full episode! Let’s build more Cities of Yes.

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Everyone talks about AI and cloud like they’re the future.
Juan Lucas Barbier is here to remind you: the future still runs on COBOL.

Known as the “COBOL Whisperer,” Juan isn’t chasing trends—he’s rebuilding the foundation the rest of tech forgot.
His agency helps modernize the legacy systems that move $7 trillion in transactions every single day.
Banking. Insurance. Healthcare. Airlines.
The mission-critical stuff no one brags about on Twitter—but everyone relies on.

In his GTLE interview, Juan dismantles the myth that COBOL is obsolete.
He explains why 99% of modernization efforts fail: they skip documentation, ignore domain expertise, and throw modern devs at 60-year-old systems they don’t understand.
Juan’s team does it differently—with a “maintain, maximize, modernize” approach that’s backed by human-in-the-loop AI and 1M+ lines of successful COBOL-to-Java translation.

He calls out the biggest problem in modernization: "Jobble"—machine-generated code no one can maintain.
His agency avoids that trap by focusing on functionality first, not line-by-line translation.

Juan also dives into AI, agents vs assistants, and why the future of automation depends on clarity, planning, and domain-driven architecture.
He’s built an operation that moves 30–35% faster than most dev shops—by using AI everywhere and pairing it with strong internal knowledge systems.

If you think legacy means irrelevant, Juan proves otherwise.
His clients aren’t just upgrading code—they’re securing the backbone of the global economy.

Full episode’s up on GTLE.
If you touch enterprise systems, this is a must-watch.

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What if the key to cutting through chaos is simply learning how to say yes?

In this week’s episode of Gaining the Technology Leadership Edge, I sat down with Frank Carone—former Chief of Staff to NYC Mayor Eric Adams, top-rated business litigator, and founder of Oaktree Solutions—to talk about building real progress in government, business, and tech without losing your soul (or your sanity).

From launching the “City of Yes” mindset to negotiating multi-billion-dollar urban transformations like Willets Point and Kips Bay, Frank’s strategy is rooted in two deceptively simple ideas: tactical empathy and listening like you mean it. No buzzwords. No fluff. Just actionable wisdom from decades on the front lines of law, politics, and private industry.

We dove into:
Why every negotiation should be win-win (and how to make it happen)

The framework behind high-stakes decision making under pressure

How to lead with curiosity, confidence, and compassion—even when stakes are sky-high

Why “starting with yes” changes everything in government and tech

Oh, and if you`re wondering what the most Brooklyn thing about Frank is? Spoiler: Everything. Accent, attitude, and unapologetic realness.

If you’re leading through complexity, navigating bureaucracy, or just trying to build better relationships in your business, this is a conversation you don’t want to miss.

Check out the full episode and grab a copy of his book. Let me know what your “City of Yes” looks like.

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Nurture your network like your houseplants, babe—water it, talk to it, don’t ghost it.

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Manifesting main character energy with one word: YES
Legal?
Doable?
In budget?
Then why the hell not? We’re not here to babysit the status quo—we’re here to bulldoze it with open minds and a lil’ creative chaos. Welcome to the City of Yes, where “that’s never been done before” is just code for “watch us.”

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There’s a big difference between hearing me and actually listening to me. One`s just noise... the other`s a skill. If you`re giving Charlie Brown teacher energy (blah blah blah), don’t be shocked when no one’s impressed. Listening means understanding—not just waiting for your turn to talk. Do better.

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