The Art of Holdings #4

CONCEPT
Lessons in Trust from the Front Lines

After selling my company, Hilani, to a private equity firm, I joined their team to help refine their larger portfolio strategy. That chapter of my life was one of the most fascinating and transformative experiences I’ve had. While the full story is worth telling another time, today I want to focus on one key lesson that has stuck with me ever since.

This wasn’t your typical private equity firm—it was run by some of the most decorated military veterans in the country, including Navy SEALs, Green Berets, and Special Ops forces. These were people whose expertise in operations transcended anything I had encountered. I’d listen to their stories of missions in war zones like Iraq and Afghanistan, where precision and adaptability were literally the difference between life and death.

Their approach to operational planning was remarkable. Every mission was planned down to the second, the inch, the millimeter. Yet, they also knew that no plan survives first contact with the enemy. Their ability to pivot under pressure and trust their training and teammates allowed them to survive and succeed in situations far more intense than anything I’ve experienced in business.

One lesson they taught me, however, is surprisingly simple: trust is everything. They called it the “thumbs-up” system, and it’s a concept I’ve carried into every aspect of my professional and personal life ever since.

The “Thumbs-Up” System

In the chaos of battle, you don’t always have time for long conversations or detailed check-ins. When you’re taking fire from all sides, you rely on quick, subtle signals to communicate and maintain momentum.

Picture this: you’re on a rooftop under fire, and your counterpart is stationed across the way. You’re both exposed, but you can’t pause to ask, “Are you okay? Do you need anything?” Instead, you give a quick thumbs-up. If they respond in kind, you know they’re good to go. That simple gesture conveys trust, confidence, and the ability to move forward.

Applying It to Business and Life

In the business world, the stakes may not be life or death, but they can still feel monumental. Whether you’re navigating a high-stakes deal, scaling a company, or facing a crisis, success depends on trust—trust in your team, your partners, and yourself. Without it, you’re exposed and vulnerable.

Sometimes, there isn’t time for lengthy discussions or hand-holding. You need to know the people around you can handle their roles, communicate clearly, and have your back. A “thumbs up” in business might look like a brief update, a confident decision, or a quick signal that allows the team to stay in sync and keep moving forward.

Ask Yourself:

• Who do you have in your corner?

• Are they people you trust with your career, your goals, even your livelihood?

• Can they support you when things get tough and decisions have to be made in real-time?

If the answer isn’t a resounding “yes,” it might be time to reassess. Building a trusted circle—whether it’s employees, partners, friends, or family—is critical to your success and resilience. Trust isn’t just a luxury; it’s a necessity, especially when you’re in the trenches of business or life’s toughest moments.

The Takeaway

The Special Ops forces I worked with taught me that trust isn’t just about competence; it’s about communication, accountability, and knowing that everyone is aligned toward a common goal. When trust breaks down, everything else follows.

My wish for you is to cultivate the same level of trust and confidence in your team as those warriors had in theirs. And if something isn’t working—whether it’s a relationship, a process, or a team member—don’t hesitate to make a change. You don’t always get a second chance.

In life and business, success isn’t just about strategy; it’s about the people you choose to go into battle with. Choose wisely.

What I’m into this Week

• 🙌 Appreciating: With everything going on in the world, I’m grateful for my good friend Mike O’Dowd, founder of Defense Strategies Group and inspiration for this week’s edition. DSG is a collective of Special Operations Combat Veterans providing world-class tactical training, private instruction, and executive security solutions, drawing on decades of real-world Special Operations experience to empower individuals and communities. If you’re in Los Angeles, they also have a badass training center in Beverly Hills - The Training Center LA.

•  🔨 Tool: Clay.com was recently introduced to me, and I’m exploring it as a tool for lead generation. It’s an AI-powered platform that promises to streamline the process of finding and connecting with prospects—perfect for anyone looking to level up their outreach game.

• 📺 Watching: To be honest, I’m more of a Google Sheets guy myself (Don’t @ me), but if you’re a spreadsheet nerd like me, you’ll appreciate the artistry in the Microsoft Excel World Championships 2024. Watching these masters at work is like seeing the Olympics of formulas and data. Pure genius in action!