From Compton to the Cloud – Darrick “DJ” Johnson: Breaking Barriers, Building Futures

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Every successful human endeavor is a saga wherein inspiration is inbuilt at the very foundation of the journey, throughout. Like the quote in Darrick ‘DJ’ Johnson’s email signature says: “The highest human act is to inspire.” — Ermias Asghedom.

That is DJ’s mission—to inspire through action, access, and effort. “If I can do that, both professionally and personally, then I know I’m walking in purpose,” he insists. Because, when he thinks about his broader purpose, he always aspires to create the greatest possible positive impact, professionally and personally.

For DJ, it’s always been bigger than just the job or the title — it’s about creating a legacy of access, belief, and opportunity.

He’s from Compton, California, a place where the odds weren’t built in their favor. However, he made a promise early on: if he ever made it out, he’d reach back and build platforms, not just resumes. That mindset has shaped everything he does — from his work in big tech to founding Sherpa Clouds Inc., a software company built to empower sports agents and teams with data, insights, and tools that have traditionally been out of reach for so many.

Divine Detour: From Cloud Sales to Calling

When asked what drew him to focus on the intersection of data, AI, and human potential, DJ says, “To be honest, it wasn’t something I intentionally set out to pursue — it felt more like a divine detour than a carefully mapped-out plan.” Like many people in tech, he originally aimed to sell cloud infrastructure because that’s where the money was. But as the saying goes, ‘You make plans, and God laughs.’

DJ was fortunate enough to be one of the first AI-focused sellers hired at Microsoft, and that experience placed him right at the intersection of AI and data. He witnessed firsthand how emerging technology could transform industries, not just in theory, but in real-world use cases. That exposure pushed him to deepen his understanding: He went back to school, earned his master’s degree from Georgetown University, and even took computer science courses at Grand Canyon University to learn how to code.

The Birth of Sherpa: Turning a Pivot into Purpose

Those experiences sparked curiosity. DJ started wondering: “Why aren’t more people exploring the intersection of technology and sports? Why aren’t we equipping agents and teams with the tools they need to make smarter decisions for the players they serve?”

That led him to build Sherpa, a modern CRM, or what DJ calls a PRM (Player Relationship Management System). After 15 years of playing football, running his own agency, and working with some of the biggest software companies in the world, he realized this wasn’t just a pivot — it was purpose.

In DJ’s words, he didn’t find this path — it found him. And now he’s all in. Whether he’s mentoring, speaking, or building tech, he wants people to see what’s possible.

“I want them to know that the journey from adversity to innovation is real. Or as I call it:”

“From Compton to the Cloud: Breaking Barriers, Building Futures!”

Being a Technology Executive, while learning and building AI & Data Platforms, DJ’s professional journey has spanned dynamic roles in technology and leadership. However, growing up playing sports taught him one lesson he’s carried into every stage of his career: effort is the one thing you can always control. In both sports and tech, there are plenty of uncontrollable — layoffs, office politics, product setbacks—but DJ has learned to focus on how he shows up. That means being on time, showing up as a true team player, never assuming he’s the smartest in the room, and always striving to be just 1% better every day.

That mindset has taken him far, from roles at Dell, SonicWall, Cloudera, Apple, and Microsoft to now building his own SaaS company, Sherpa. “Effort got me here. And effort will keep me here,” he emphasizes.

DJ has been in tech since 2012, right after returning from the CFL. “But the true turning point came when Jason Carter, now CRO at SonicWall, gave me my first real shot. He hired me as an ISR and later promoted me to Account Executive.” That role changed everything. DJ learned not just how to sell cybersecurity solutions, but how to think critically about how customers protect, store, and leverage their data.

He shares, “Now, I’d be lying if I said I foresaw generative AI back in 2015 — but what I did recognize was that every customer cared deeply about three things:

How will we protect our data?
Where will we store our data?
How can we do more with our data?”

Fast forward to today — everyone’s talking about AI. But what people often overlook is this: AI is only as good as the data it’s built on.

If AI is the quarterback of the team, data is the offensive line. And no matter how talented the quarterback is, they can’t operate without protection. That analogy has stayed with DJ throughout his career because in both football and tech, the fundamentals matter most.

Leading with Faith, Anchored by Family

DJ lives by four core principles: Faith, Family, Health, and Wealth — and he carries these with him in every decision he makes, especially as a leader.

Faith is about believing — not just spiritually, but in the mission, in the people you lead, and in the vision you’re building toward. Leading in tech requires faith that what you’re working on will matter, and that your team will execute when it counts.
Family has always been DJ’s anchor. He’s worked at some incredible organizations, and learned that what truly defines a company is its culture. He treats his team like family “because at the end of the day, we’re all more than just titles — we’re parents, sons, daughters, and friends.”
Health keeps him grounded. If he’s not well physically, mentally, or emotionally, he can’t lead others.
And Wealth to him isn’t just about money — it’s about creating value, building a legacy, and helping others rise.

DJ may not be the flashiest leader in the room, but he’s consistent and cares deeply. He insists, “I bet my salary on that.”

Authenticity Over Applause

Recognized as a leader who leads with intention and authenticity, to DJ, authentic leadership means everything to him. He grew up in South Central Los Angeles — a place where many of his peers lost themselves to gang violence, the streets, or prison. “I saw early on what happens when you try to become someone you’re not just to survive or fit in.”

That experience shaped how DJ leads today. He never wants to lose himself in a title, and doesn’t want the people on his team to feel like they have to either. Being authentic doesn’t mean ignoring structure — it means showing up as your full self while still delivering results. “Whether I win or lose, I want to make sure I’m still me when it’s all said and done.” That’s the mindset he leads with every day. If DJ can be himself and still win, he wants his team to know they can too.

From Rock Bottom to Rising Higher

Furthermore, DJ’s passion for mentorship and community-building always drives him ahead. Most people don’t know this about him, but before DJ was in tech, he spent over five years as a sports agent representing athletes in the NFL, MLB, NBA, and Olympic track and field. In 2019, DJ lost everything — his agency, his home, and for eight months, he was sleeping in his car.

During that time, DJ reached out to people on LinkedIn and in his network, not for handouts, just guidance. But he kept hitting walls. Breaking into companies like Microsoft, Google, or Meta isn’t just tough — it’s statistically harder than getting into Harvard. DJ told himself: If he ever got back on his feet, he’d build something that made the road easier for the next person.

That’s what inspired DJ to create iTech, his nonprofit dedicated to providing access to tech education and career resources. Since launching, they’ve helped over 2,500 students, professionals, and underserved youth gain exposure to opportunities they wouldn’t have had otherwise.

They ran computer drives with Apple, partnered with Microsoft Azure and Google Cloud to help people get certified, and even built a coding game for kids using tools like Angry Birds and Minecraft.

DJ has always believed in giving more than he takes. “If I’ve left any blueprint behind, I hope it’s one others can build on — and one that proves your past doesn’t have to dictate your future.”

AI, Data & Trust: Rethinking the Real Future

In DJ’s view, today, to embrace AI responsibly and effectively, the biggest shift leaders need to make is moving from a tool-based mindset to a trust-based mindset. Too many still see AI as just another feature to bolt onto their tech stack. But AI isn’t just software — it’s infrastructure for decision-making. And when you delegate decision-making to machines, even partially, trust becomes the currency.

That trust starts with data — its quality, its governance, and how it reflects the people and processes behind it. If your data is biased, fragmented, or misunderstood, your AI will reflect that. So leaders must start thinking: Are we building systems that are fair, transparent, and accountable — or just fast and flashy?

You don’t need to become a data scientist, but you do need to ask the right questions:

How is this model trained?
What’s the feedback loop?
Who’s being impacted?

Embracing AI responsibly means understanding that it’s not just a tech upgrade — it’s a culture shift. And leaders who lean in with humility, curiosity, and accountability will be the ones who lead real change, not just headlines.

Sherpa and the Rise of AI Agents

DJ is incredibly excited about the rise of AI agent frameworks — intelligent systems that go beyond one-off tasks and evolve into collaborative, reasoning-driven teammates. “We’re moving from AI as a tool to AI as a co-pilot, strategist, and decision-making partner.” That’s not just a tech shift — it’s a paradigm shift.

Right now, most people are still using AI like a smarter search engine. But the future is about autonomous agents that can plan, reason, and execute across systems — all while understanding the context, goals, and intent of the user, believes DJ.

This shift becomes even more powerful when you layer in domain-specific intelligence. “We’re entering an era where AI won’t just assist — it will advise, predict, and act with deep industry knowledge.” That’s exactly why he built Sherpa — to serve the overlooked but high-impact intersection of sports, data, and decision-making. Imagine AI agents that not only store information but proactively surface contract risks, benchmark NIL deals, generate recruiting pipelines, or flag compliance issues — all in real time. That’s the future: multi-agent systems orchestrating high-stakes, high-context environments.

The Character of AI: Ethics in the Age of Automation

But with that power comes real responsibility. The greatest challenge in the next few years won’t just be performance — it’ll be trust, transparency, and control. AI agents must be explainable, ethical, and accountable to real people and real-world outcomes. “If we don’t build with integrity, we risk replacing bias with black boxes.”

Another trend DJ is energized by is the democratization of AI development. “We’re finally seeing tools emerge that empower non-technical users — teachers, coaches, entrepreneurs — to build intelligent systems without needing a PhD in machine learning.” That’s when AI becomes transformative, not just impressive.

And finally, he’s bullish on privacy-aware AI models built with data ownership, consent, and contextual awareness at the core. “We can’t scale this technology responsibly if we don’t respect the humans behind the data.”

The next 2–3 years won’t just define AI’s capability — they’ll define its character. And DJ wants Sherpa to be on the front lines of that movement — building vertical AI agents that help real people make better decisions, faster, and with more clarity than ever before.

Building Movements, Not Just Meetings

Thus, in such a scenario, DJ’s advice to the next generation of tech-savvy leaders navigating their own journeys is straight from his heart: being a leader isn’t about leading — it’s about coaching and inspiring. Titles don’t move people — vision, consistency, and care do.

Too many young leaders get caught up chasing clout and control. But if you’re not building others up while you’re moving forward, you’re not leading — you’re just managing. “And we don’t need more managers. We need more builders, listeners, and servants.”

Remember this:

There’s no such thing as a bad kingdom — only bad kings.

So ask yourself — are you creating a space where people feel seen, challenged, and empowered? Or are you building a castle for yourself while your team drowns in the moat?

“DJ’s advice?”