Darryl Kulwin
Owner
T-Bird Jewels
I didn’t build my path on certainty—I built it by stepping into the unknown.
Early in my career, I was living in Los Angeles and had carved out a strong role with a restaurant manufacturing company. I was growing quickly and managing a major territory; there was stability, momentum, and a defined next step.
Then my father unexpectedly introduced the idea of getting into the jewelry business. It meant walking away from a career that was working and stepping into an entirely different industry where I didn’t have the same foundation. It was a risk. But the decision came down to perspective—I wasn’t focused on what I might lose, but on what I might gain.
Looking back, that decision changed my trajectory. It reinforced something I now carry into leadership: early in your career, you often have less to lose than you think. The bigger risk is staying comfortable for too long.
It shaped how I think about risk today. I don’t see it as being reckless—I see it as strategic optimism. Opportunity often sits just outside of what feels secure, and the decisions that feel most uncertain are the ones that end up defining your path.
Chet Buchanan
Emmy Award Winning Announcer, Auctioneer & Broadcast Professional
I originally came to Las Vegas in 1999; and within months we launched the first Toy Drive. My first contract was up in 2002, and I accepted an offer I couldn’t refuse in Portland, Oregon—a place where I had previously found success. This time, it didn’t unfold the same way.
Things became difficult for me personally and professionally. As much as I love the Pacific Northwest, where I grew up, and as meaningful as it was to be close to family, I knew by 2004 I had to move on. There were strong opportunities across the country, but the only real choice for me was Las Vegas. On the surface, it may have looked like the safe move. It wasn’t. It was calculated. I believed Las Vegas was on the verge of explosive growth, and I wanted to be part of it.
I returned more battle tested. I had faced real adversity and gained a clearer understanding of my weaknesses—areas I once thought were strengths. I learned that nothing is permanent, not the highs or the lows, so keep your circle tight. Stay vigilant. Not everyone that is on your team is on your side. Commit to getting a little better every day, but give yourself grace. Life is hard enough without being your own enemy. I can’t guarantee that if you work hard enough and smart enough that you'll win. But I can guarantee what will happen if you don't.
Edward A. Vance
Founder & CEO
EV&A Architects
One of the most defining inflection points in my career came when I chose to step away from a secure leadership role to start my own firm. It didn’t make sense: I had stability and a clear trajectory. But I felt a disconnect between the work I was doing and the impact I believed architecture could and should have.
At that moment, what was at stake wasn’t just financial security. It was reputation, credibility, the risk of stepping out on my own, and the possibility of failure in a relatively small professional community. I was also acutely aware others would eventually depend on that leap.
What pushed me forward was a conviction that architecture is about more than buildings—it’s about shaping human experience and creating places that respond to their environment and the people who inhabit them. I realized that if I didn’t take that risk, I would spend the rest of my career wondering “what if.”
So, I chose the harder path—uncertain, exposed, but aligned with my values.
That decision changed everything. It gave me the opportunity to build a practice grounded in clarity of purpose, where design excellence, responsiveness, and client trust are inseparable. It also reshaped how I think about leadership.
What I learned is that risk isn’t the enemy; unexamined risk is. Early on, I learned to recognize red flags misalignment in values, unclear expectations, or a lack of transparency in partnerships. Those are things I no longer ignore.
Before making major decisions now, I ask critical questions:
- Does this align with who we are and what we stand for?
- Are we being honest about the risks, or just hopeful about the outcome?
- Will this decision strengthen trust with our clients, team, and partners?
The advice I give younger leaders is this: don’t confuse comfort with clarity. The safest path often leads to stagnation. Be disciplined, surround yourself with people who challenge your thinking, and never ignore what doesn’t feel right because the opportunity looks good on the surface.
In the end, leadership is about making decisions that hold up over time and having the courage to own both the successes and the missteps that follow.
Al Pitts
Deputy CIO, Digital Services
Clark County
A defining moment in my career came during the City of Las Vegas’ 2015 search for a new Director of Information Technology. At the time, I was serving as an IT Business Partner and later as an IT Business Relationship Manager, bringing more than two decades of experience across both public and private sectors to help align technology with enterprise outcomes.
Contributing my perspective to the City Manager role during the search process became more than an exercise in professional insight, it became a moment of clarity. Writing candidly about what the organization truly needed reinforced a conviction I’ve carried throughout my career: sustainable innovation is only possible when built on strong fundamentals. Governance, information management, process discipline, and organizational readiness matter just as much, if not more, than emerging technologies and ambitious modernization initiatives.
That same moment also demanded personal resolve. A cancer diagnosis forced me to evaluate not only my readiness for the role but my responsibility to the organization. After thoughtful reflection, I chose not to pursue the director position—not from a lack of capability or aspiration, but out of respect for the city and the importance of leadership continuity during a critical period. I prioritized my health and ensured the department would have a leader fully able to meet the demands of the role without uncertainty.
That decision reshaped my definition of leadership. True leadership is not defined solely by title or advancement, but by judgment, timing, and stewardship. It requires discipline to step forward when needed, and the wisdom to step back when doing so best serves the mission and the people behind it.
Today, that perspective defines how I lead today. I focus on building durable foundations, enabling meaningful transformation, and balancing technology, people, and process to deliver long-term value. My career is guided by integrity, resilience, and a commitment to decisions that align purpose with performance—especially when stakes are high.
Dr. Andrew Sheep
Owner
Outlive Concierge Medicine
I was a lieutenant in the Navy, stationed in Guam as an Undersea Medical Officer. It was a good life with a clear path forward, but I knew I wanted civilian emergency medicine, not a military residency, because the training and patient volume would be different. I was willing to risk everything, including separating from the Navy with no backup plan, for that distinction.
I had an uncomfortable truth to face. I had not seen a genuinely sick patient in over four years. I applied to only five programs. I had a new wife, a young child, and no backup plan. What was at stake was not just my career, it was the physician I had decided to become. I had made a promise to myself, and this was the moment when I either honored it or found a comfortable reason not to. I bet on myself. I got into my top program. Everything that followed came from that one decision.
What strikes me most looking back is how much clarity came from having no safety net. When retreat is not an option, you stop second-guessing. You go.
The red flag I will never ignore again is the voice that says the timing is not right, that you should wait for better circumstances. Circumstances are never better. The people I have watched fail at big decisions are rarely those who moved too soon. They are the ones who waited for certainty that never came.
What I tell younger physicians now is this: separate the fear of the outcome from the quality of the decision. I was terrified of rejection. But the decision itself was sound, and I knew it. You do not control what happens, you control the quality of your thinking going in.
Know what you want before you are under pressure to decide. That clarity is what made the choice clean, even when it was frightening. When you are willing to bet on yourself, the people around you learn what is possible. That lesson has shaped every patient I have cared for and every person I have led since.
“I learned that nothing is permanent, not the highs or the lows, so keep your circle tight. Stay vigilant. Not everyone that is on your team is on your side. Commit to getting a little better every day, but give yourself grace.”