In this edition of “Ask the Board,” we asked Stephen J. Cloobeck, the Founder and former CEO of Diamond Resorts, how entrepreneurs can seize overlooked opportunities and set themselves up for success.

November 22, 2024 – In this edition of “Ask the Board,” we feature Stephen J. Cloobeck, a California-based entrepreneur, philanthropist, and Founder of Diamond Resorts International, which began as an independent timeshare and vacation ownership company. Stephen shares his insights on how entrepreneurs and small business owners can seize overlooked opportunities and take calculated risks.

As the Founder and former CEO of Diamond Resorts, I’ve made significant contributions to the business world and am passionate about financial literacy, education reform, and innovative investment strategies that benefit California’s growth and success.

Through my unique experience as a self-made businessman and deep commitment to improving California’s future, I’ve uncovered how to view life through a hospitality-driven lens, seize overlooked opportunities, and take calculated risks. Here are my insights for current and aspiring entrepreneurs.

Don’t let failure scare you

Embrace failure. It’s the best learning tool. The one thing that tough situations have taught me is that a “parade of horribles” makes you stronger and smarter. The more rockets that you hit me in the face with, the more I like it because you learn. If knowledge is power, then experience is a gold mine. Both are keys to becoming a great leader. You gain experience to guide your team because you know how to handle what’s coming.

You have been there before and can pivot accordingly. There is a reason why our military constantly does drills. It preps you and them. In business, these drills are real-time, and the more you experience, the more you are targeted for failure, the more you learn and become stronger as a business, a culture, a team. Through failure comes opportunity. Frankly, I love the chaos it brings. It’s where great businesses and leaders are made and thrive.

Prioritize transparency and communication

Transparency and integrity are what builds a good team. My employees know I have their backs, and vice versa. When we win and succeed, they get the trophy, not me. When we lose, I take the hit. That’s just how it works. I also expect integrity without compromise. You lie, you die. I can handle the good, the bad, the ugly. The mistake is part of the job, but if you don’t tell me the truth, then you bust the trust. One and done.

Communication and transparency: you cannot survive without either. These are the keys to any brand or leadership success. They become the building blocks for your credibility and accountability as a leader. Open communication and radical transparency are what builds loyalty and trust with your teams and your customers. Without either of those two stakeholders, there is no company.

“The one thing that tough situations have taught me is that a ‘parade of horribles’ makes you stronger and smarter.” -Stephen J. Cloobeck, entrepreneur, philanthropist, and Founder of Diamond Resorts International

Maintain resilience during tough times

I am at my best in chaos. It’s a learning opportunity, but more importantly it builds culture. It brings different teams together. Voices that you might not always get to hear or interact with every day assemble during tough times. I encourage it. They feel heard and important. Most importantly, I learn by listening. I’m good with the crazy. In the end, it builds character and strong leaders. I think all excellent leaders are at their best during difficult times.

Be a leader

As the leader, you set the weather for the organization. Great leaders don’t dictate, they lead by example. They roll up their sleeves and get the work done. They pick cigarette butts off the ground if they see it before a customer walks by. They don’t point and ask someone else to handle it. You must be willing to play every role and understand what everyone does and be willing to assist at a moment’s notice. That’s resilience, that’s loyalty, that’s being a leader.

Realize challenges are inevitable

If you are in any kind of business, there will always be challenges. But with the right strategies, you can turn obstacles into opportunities. Stay agile and be ready to adapt your strategies based on changing circumstances. Flexibility allows you to pivot quickly when necessary. Focus on communication and maintain open lines with your team, stakeholders, and customers. Transparency can build trust and foster collaboration. Establish specific, measurable, achievable, relevant, and time-bound (SMART) goals to guide your response to the challenge. And allocate resources—time, money, and personnel—effectively. Focus on high-impact areas that will drive results.

Use your success to make an impact

My journey is not just about business success; it’s about using that success to make a tangible impact on my community and state. My ability to merge entrepreneurship with philanthropy and political involvement offers a multifaceted perspective that is rare among leaders today.

I have a deep-rooted passion for financial literacy and education reform, combined with experience in scaling a global business. As such, I recently worked with the political action committee Save Our Schools to launch a non-partisan organization to help educate voters on the need to refocus California classrooms with syllabi that prepares its students with practical, real-life skill sets such as civics, financial literacy, and entrepreneurship.

Build a diverse network

Connect with people from various industries and backgrounds. They can offer unique perspectives and may highlight opportunities you haven’t considered. No one wants a sea of the same. To build a diverse network, you want to create an ocean of creativity, of different waves of thoughts and a deep understanding of different cultures and life-pools so you can help grow a habitat for all. One must always step out of one’s comfort zone to be truly educated. Attend events, conferences, churches, union meetings, and other functions to understand a different viewpoint. You might end up networking with future partners, employees, or companies that can help you and your business innovate, expand, and be more profitable.