We recently connected with Princess Castleberry and have shared our conversation below.

Princess, thanks for joining us, excited to have you contributing your stories and insights. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?

I launched Castleberry Global in 2019 as a fractional risk management and HR consultancy, just months before the world changed.

I didn’t know a pandemic was coming. What I did know was that I was sitting on over 20 years of experience leading global insurance programs, navigating corporate crises, and guiding senior leaders through high-stakes decisions. I had always seen risk differently—not just as numbers on a spreadsheet, but as behaviors inside organizations quietly eroding performance and trust.

In the early months, I was testing everything: different business models, services, and ways to package the unique mix of skills I brought to the table—risk strategy, learning design, and wellness counseling. I called it The Dilemma of a Multi-Talented Overthinker, because when you’re good at solving multiple kinds of problems, the hard part isn’t doing the work. It’s deciding which work matters most right now.

Then the crisis hit, and I had to pivot fast. My phone started ringing, not because people needed another consultant, but because they needed clarity. Organizations were scrambling to manage uncertainty, teams were burning out, and leaders were under pressure like never before. That’s when I realized the biggest risks they were facing weren’t operational. They were behavioral.

That insight changed everything.

I began developing what has become the foundation of my brand: helping leaders Live, Lead, and Build Leverage™ by identifying the hidden behaviors blocking their growth. I gave those behaviors names—Toxic Drive™, Sinking Ego™, Conflict Waste™, and Fixed-Gear Leadership™—and started teaching leaders how to manage their triggers before their decisions caused unnecessary damage.

In 2022, I co-created a powerful talk with Shawnta Hooks called You Can Break Bad Agreements. That collaboration gave language to the silent, unhealthy contracts we hold with ourselves and others—and it opened doors. That talk led to my first TEDxDetroit appearance and helped position me as a speaker who not only motivates, but also transforms how leaders think and lead under pressure.

My speaking career didn’t begin with a polished brand or a perfect pitch. It began with a message that stuck.

One keynote led to another. Clients started asking me to stay on as an advisor. I built toolkits, assessments, and training programs. One of the smartest things I did early on was treat my intellectual property like a business asset. I trademarked my frameworks, refined my messaging, and aligned every service I offered around one promise: I help leaders solve real challenges, faster and for good. Not just for good, like challenges will never occur again, but for the good of humanity.

Of course, there were moments of doubt. Leaving the predictability of a corporate career for the uncertainty of entrepreneurship requires courage and a plan. I didn’t leap blindly. I applied the same strategic lens I had used in global enterprises: identifying signals, assessing gaps, building systems, and learning through execution.

Today, Castleberry Global is a leadership development company that supports bold leaders across industries. I speak on major stages, train executive teams to decode behavioral risk, and help organizations align performance with purpose, profitability, and well-being.

The business didn’t grow because I followed a script. It grew because I recognized the real risks leaders were facing and offered a different kind of clarity when they needed it most.

Princess, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

For those who haven’t come across my work before, I help leaders and organizations identify the behavioral risks that are quietly blocking their growth—and give them the tools to lead with more clarity, less stress, and fewer unnecessary conflicts.

My company, Castleberry Global, delivers high-impact keynotes, immersive leadership development experiences, and strategic advisory services for executive teams and organizations under pressure. I work with everyone from Fortune 500 companies to regional associations, helping leaders navigate burnout, misalignment, and decision fatigue using simple, repeatable frameworks grounded in risk strategy and behavioral psychology.

What makes my work different is that I’m not a motivational speaker or general leadership coach. I’m a strategist. My talks and training are built on two decades of real-world enterprise experience and designed to deliver long-term impact, not just inspiration. I’ve managed global insurance programs, facilitated high-stakes executive decisions, and seen firsthand how internal behaviors can derail even the strongest business plans. My job now is to help leaders decode those behaviors—and turn them into leverage.

I’ve created a set of proprietary frameworks that drive everything I do:

Live, Lead, and Build Leverage™ – my flagship methodology

The Truth Is in the Trigger™ – uncovering root causes of leadership volatility

Cue to Chaos™ – helping leaders recognize and respond to stress-based behavior shifts

Burnout-Proof™ – equipping leaders to build resilience and make sustainable decisions under pressure

Eliminate Conflict Waste™ – turning mismanaged or avoided conflict into a strategic advantage

These aren’t just models—they’re lenses that help people see differently and lead smarter.

The problems I solve are real and urgent. Leaders come to me when burnout is rising, alignment is slipping, or conflict is costing them time, trust, and talent. I help them name the issue, map the pattern, and rebuild the approach. Every program I deliver is tailored, practical, and focused on helping leaders navigate pressure without compromising performance or well-being.

What I’m most proud of is that my work creates lasting change. Clients don’t just walk away with insights—they walk away with language, strategy, and confidence. They make better decisions. They reduce conflict. They lead teams that trust them, follow them, and grow with them.

For anyone discovering my brand for the first time, here’s what I want you to know:
I’m not here to help you avoid challenges—I’m here to help you leverage them. Because pressure doesn’t have to break you. It can build you, if you know how to lead through it.

Can you talk to us about how you funded your business?

I bootstrapped my business for the first five years—honestly, because I didn’t know any better, and I was afraid to borrow money.

When I first launched Castleberry Global, my overhead was low. I was offering advisory services, facilitating leadership workshops, and building everything myself. At that stage, my biggest investment was time. But as my vision grew, so did the need for capital. I wanted to build speaker assets—professional branding, a high-converting website, a reel that reflected the caliber of stages I was on, content marketing, publishing, you name it. And none of that comes cheap.

I made a common mistake: I tried to fund everything out of pocket. That kind of cash burn nearly put me out of business. I was pouring money into growth without a sustainable financial strategy behind it. I wasn’t just building—I was overextending.

That experience forced me to step back and reassess. I realized that being talented, booked, and in demand wasn’t enough. I had to become bankable—not just emotionally invested in my work, but structurally invested in the health of my business.

That’s when I enrolled in the Goldman Sachs One Million Black Women and later, the Goldman Sachs 10,000 Small Businesses Program. Both experiences were game-changers. They gave me the financial education, business modeling tools, and peer accountability I needed to make smarter decisions, pursue capital with confidence, and treat cash flow like the strategic lever it is, not just a scramble to survive.

Now, I help other entrepreneurs and executives avoid the same trap. Whether I’m speaking to women in leadership or training teams inside major companies, I remind people that access is not the same as readiness. Building a sustainable business requires more than a bold idea and great execution—it requires a solid financial foundation and a willingness to shift from fear-based funding to strategic capitalization.

Bootstrapping gave me grit. But becoming bankable gave me scale.

Can you share a story from your journey that illustrates your resilience?

Every day as a speaker is a test of resilience. People see the stage lights, the applause, the polished delivery—but they don’t always see what it takes to get there.

Behind every keynote is a cycle of high-stakes preparation: managing nerves, learning new material, rewriting content to meet the moment, rehearsing until it lands. Add to that the demands of building meaningful relationships, constant travel, and the need to create content that’s not just smart—but strategic, relevant, and on brand. It can feel like creative overload.

But here’s the truth: I don’t just teach leadership performance. I live it. I use my own systems on myself first.

When I created frameworks like Burnout-Proof™ and Cue to Chaos™, I wasn’t theorizing. I was mapping out how to survive and succeed through seasons of personal and professional stress. I’ve had moments where talks got canceled, travel fell apart, or unexpected life challenges collided with major client events. And yet, I still show up prepared, aligned, and with energy to give. Not because I’m immune to pressure, but because I’ve built the tools to lead through it.

That’s how I know my work isn’t fluff. It works—because it’s been pressure-tested by me, and now by leaders around the world.

Resilience isn’t about perfection or pretending the work isn’t hard. It’s about designing systems that help you recover faster, think more clearly, and stay aligned even when things don’t go as planned. That’s what I teach. And that’s why I’m still here—thriving through every bout of adversity, one keynote at a time.

Contact Info:

• Website: https://www.princesscastleberry.com
• Instagram: @PrincessCastleberrySpeaks
• Facebook: @PrincessCastleberrySpeaks
• Linkedin: https://www.linkedin.com/in/princesscastleberry/
• Youtube: @PrincessCastleberrySpeaks

Image Credits

Shawn Lee, Shaleena Cole, Storyfi, Michigan Restaurant & Lodging Association