There is no doubt that the pace of change today, whether technological, political, economic or cultural, requires leaders with an inspired (x-ray) vision, tenacious drive, and a steady hand. While our national leaders have had to navigate global conflict and crisis over the last few years, founders across borders have engaged in some of the most significant value creation and impact we’ve seen in recent history. As we zoom out with the benefit of historical perspective, we are reminded that great progress has always been fueled by the energy and imagination of great leaders with the strength and conviction to lead through both the good and more challenging times. It’s these uncertain times that leave consumers, investors, and businesses alike feeling as if their strength is being tested each and every day.

Despite the risk factors that exist in challenging times, according to the U.S. Census Bureau, nearly 5.5 million businesses were started in 2023. In our business, we see this spirit of entrepreneurialism every day and it excites us, but we also know that for founders and their startups, times like these can make or break. Getting it right in cloudy times can be a difference maker.

On the heels of National Leadership Day and President’s Day, it feels fitting to turn back in time to George Washington, one of our Founding Fathers and our first leader, for some inspiration. He once said, “Leadership is not only having a vision, but also having the courage, the discipline, and the resources to get you there.”

This enduring wisdom remains as relevant today as ever, particularly within the realm of founding and scaling durable businesses. The true measure of a founder’s leadership lies in their ability to steer their business through both the good and the bad times while fostering and preserving its culture.

At Drive by DraftKings, we are fortunate to have a close working relationship with the visionary leaders of DraftKings - Jason Robins, Paul Liberman, and Matt Kalish. They joined us at our last annual meeting to share their founding and scaling story with our LPs and portfolio companies. Over the past decade, their collective vision and partnership offer insights into the importance of visionary leadership, courageous thinking, and motivating others in making that journey possible.

First, An Irrational Sense of Belief

Great ideas are conceived every day. Ideas that might just have the power to change the world. At the same time, not all great ideas become successful ideas. The key is in figuring out how exactly to nurture a great idea and what ingredients are needed to make it successful.

It starts with that irrational sense of belief that a given idea can change the world. Surround yourself with passionate people who share your unwavering belief in the idea and are individuals in whom you irrationally believe. This is who you want to go into battle alongside. They are your tribe.

This is especially true at DraftKings, where all three founders continue to be very involved in running the company, continue to believe in the great idea, and most importantly, continue to believe in each other.

As important, find investors who share that vision, who push you out of your comfort zone, and who have the tools and know-how to help you see around corners.

Culture is King (and Queen) - It Carries All

The importance of building a company culture cannot be overstated. Nor can the importance of maintaining that culture as you grow. The tone at the top can – and will – be the real driver of any culture.

DraftKings’ founders (and our portfolio founders) agree that their success has been driven in part by maintaining a distinct culture. One that starts with knowing they as leaders are aligned with each other and have a shared awareness of agreements and disagreements. A culture where alignment is evident to the broader team also brings a sense of clarity to everyone around company values.

Strong leaders live the values of their culture every day and have high expectations that others do the same. It is when the rest of an organization behaves the same way as its leaders that you see the lived expression of those values.

The Road to Success is Never Without its Bumps

As in life, business, and of course in sports, it’s the struggles that help a team grow stronger together and truly appreciate their successes.

Understanding that there will be bumps in the road and always looking around corners for what might lie ahead is critical for every leader. There will be tough moments along the journey, but embracing those times only strengthens the bonds of your team. Robins, Liberman, and Kalish emphatically agree, having experienced their share of struggles as a startup, they will tell you it is the tough times that have had the most influence on their growth.

It is also during those times that a sense of trust and transparency is established. The ability to trust and to be candid plays an important role in taking risks and running thoughtful experiments in the name of growth and commitment to the vision. Capitalizing on the challenging moments to foster a stronger leadership bond and company culture can ultimately set a company – and its leaders – up for long-term success.

A few shared learnings from conversations with our founders and partners

1. Building an A team starts with trust and respect.
2. Divide and conquer – swim lanes are key, understand them.
3. Disagreements will happen - assume positive intent.
4. Great teams respect that different views are critical stepping stones to the best solutions.
5. Your North Star drives direction and alignment - never lose sight of it.

We would love to learn what great leadership means to you!