Winning as an entrepreneur from Diary of a CEO x How I Built This

When two powerhouse podcasters (and my personal favorites!)—Steven Bartlett of Diary of a CEO and Guy Raz of How I Built This—sit down for a conversation, you can expect insights that define success and the art of building something meaningful. Their recent discussion delivered exactly that, covering the nuanced balance between perseverance and passion, the underrated role of luck, and why the right partner can multiply your chances of success. Here are the highlights to inspire you at every stage of your journey.

The Power of Weathering No
Guy and Steven explore the importance of hearing and embracing the word “no.” As Guy explains, “no” often serves as a moment of truth for entrepreneurs—a test of resilience. Those who succeed learn to treat rejection as part of the game; rather than a wall, “no” becomes a stepping stone, prompting founders to adapt, pivot, and find new paths forward.

A powerful example of resilience comes from missionaries for the Church of Latter-Day Saints, who go door to door, knowing they’ll face rejection far more often than welcome. But they don’t focus on counting the “nos”—they’re seeking that one “yes.” Each closed door is another step toward their goal, making them practically immune to rejection. Many of these church members go on to become formidable entrepreneurs, carrying with them a profound ability to stay the course despite setbacks.

This maverick mindset, where “no” is an invitation to play the game, is what separates those who give up from those who persevere and ultimately succeed.

The Essential Role of Luck
Both Steven and Guy agree that luck plays a crucial role in success. According to Guy, the most successful entrepreneurs don’t just stumble upon luck; they actively cultivate it. They act in “lucky” ways by seeking opportunities, staying alert for patterns, and connecting dots others might overlook. This approach transforms luck from a passive occurrence into an essential skill—what I like to call a “lucky radar.” (And what I teach in Quantum Surfing!)

This “lucky radar” is a trained perception, a constant scanning of the environment for connections, patterns, and possibilities. Steven describes it as a heightened awareness successful founders use to navigate their world, always asking, “What could come of this? Who here could spark something unexpected?” Instead of waiting for luck to “just happen,” these entrepreneurs move through life with curious and open minds, tuned into subtle opportunities that can lead to something bigger.

As Guy points out, certain personality traits seem to naturally boost this lucky radar. Kindness is one of the most powerful of these traits. Genuinely kind, empathetic, and respectful people often attract positive connections and are better positioned to seize opportunities that come their way. Kindness, as Steven observes, creates a ripple effect—it makes people want to help, share resources, and open doors, leading to fortuitous encounters and support when it’s least expected.

This “lucky radar” becomes part of a founder’s strategic toolkit. It’s not about random strokes of good fortune; rather, it’s about intentionally noticing and acting on the subtle openings others might overlook.

Culture Trumps Strategy
Every great founder knows that a strong team is the bedrock of sustainable success. As Peter Drucker famously said, “Culture eats strategy for breakfast”—meaning that teams, and the culture they create, often have a far greater impact on a company’s success than any specific strategy.

Find people who are better than you in areas where you’re weak,” Guy advises, suggesting that humility in recognizing your own limits is key to assembling a well-rounded, driven team. A cohesive, empowered team often outperforms the best-laid plans.

For a venture to reach its full potential, it’s not just about hiring talent—it’s about nurturing a shared culture that binds the team together, creating an environment where people can thrive, contribute their unique strengths, and feel deeply invested in the vision. Just like a team sport, the energy of the team and their ability to play and win together is gold.

Boomeranging from Failures
Failure isn’t final—it’s a reset and often an opportunity. Guy highlights that learning to view failures as part of the journey, rather than the end of the road, builds mental resilience. This resilience isn’t just about bouncing back; it’s about doing so with a refreshed perspective.

A powerful example of this boomerang effect is the story of actress Hilary Swank. She had faced a tough setback after being cut from a television show she’d hoped would be her breakthrough. But with the unexpected free time, she became available for a small indie film that needed someone just like her for the lead role. That film was Boys Don’t Cry, and her performance went on to earn her an Academy Award for Best Actress. What seemed like a failure turned out to be a pivotal moment, leading to one of the biggest achievements of her career. Her story underscores the idea that setbacks often create space for unexpected, bigger opportunities.

This kind of resilience, Guy points out, transforms setbacks into stepping stones. The right perspective allows entrepreneurs to use failure not as a wall but as a doorway to something better. Each low point becomes an invitation to refine and come back stronger.

The Power of Passion
One of the key ingredients to success is genuine passion. Passion is the fuel that keeps you moving forward, even when challenges stack up, and it’s often what helps founders distinguish themselves in a crowded market. “It’s passion that makes the grind feel worthwhile,” Guy explains, noting that it’s an intangible yet essential quality that enables founders to push through when things get tough.

When passion is at the core of a founder’s journey, it creates an authenticity that resonates with investors, customers, and team members alike. It’s this genuine passion that helps founders navigate rough waters and bring their vision to life.

Final Reflection: Build with a Partner
Wrapping up, Guy reflects on the power of partnership in building a successful venture. He shares statistics that underscore this truth: founders with a co-founder are significantly more likely to succeed. A partner brings balance, perspective, and a shared resolve, especially during challenging times. “Success,” he notes, “often doubles when you’re building together.”

In Guy’s experience, the best entrepreneurial journeys aren’t just about a great idea—they’re about the people who share that vision with you, especially when things get tough. His final takeaway: seek out a partner who complements your strengths, shares your values, and is as committed to the vision as you are.

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