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Eric Schmidt, former CEO of Google, has had extensive experience working alongside some of the most brilliant and daring entrepreneurs in the world. His insight into the unique challenges of working with founders goes beyond their creativity and brilliance—it’s about understanding their mindset, and how to balance guidance with giving them the space to grow.
Photo: Christophe Morin/IP3 | Getty Images
The Bold Nature of Founders
One of the trickiest parts of working with founders is that they are often bold risk-takers. They’re aggressive in pursuit of their vision, headstrong, and willing to leap into uncertainty where others might hesitate. While these qualities are essential for breaking new ground, they can also lead to an intense focus on pushing boundaries, sometimes to the point of overlooking critical details—like legal requirements.
Schmidt recalls moments where he had to gently nudge founders toward realizing potential missteps. For instance, there were times when he'd point out that a certain action was illegal, and the response would be, "Really?" instead of immediate concern. This attitude often comes from a place of optimism and determination. Founders are so consumed by making things happen that they may not fully grasp the broader consequences at first glance.
Letting Founders Learn Through Experience
Rather than insisting on his way, Schmidt learned that sometimes, it’s essential to let people discover things on their own. He shares an example where there was an ongoing email debate among the team about an HR issue. Schmidt knew the correct answer, but he decided to let the debate play out. In the end, the team came to the right conclusion by themselves. This taught Schmidt that not every situation requires immediate intervention—especially when you’re working with intelligent, innovative people.
Being the Adult in the Room
He calls this balance “being the adult in the room.” It’s about recognizing when to step in with firm guidance, such as ensuring the company remains compliant with the law, and when to sit back and let founders work through challenges, even if they take the longer route. In a way, it’s about trusting the process and allowing magic to happen through trial and error.
Encouraging Growth Through Trust
Founders and entrepreneurs, while brilliant, often need room to grow into the responsibilities of leadership. Schmidt’s approach was to create an environment where learning could happen organically. By observing the natural process of problem-solving, he allowed founders to strengthen their skills, which ultimately benefited the company in the long term.
Some Examples
Entrepreneurs who have exhibited boldness, learned through trial and error:
1. Tobias Lütke – Shopify
Tobias Lütke, founder of Shopify, embodies the bold risk-taking nature of an entrepreneur who learned through experience. When Lütke first started Shopify, he had little experience in the field of e-commerce. His initial goal was to build an online store for selling snowboards, but when he realized existing platforms were inadequate, he decided to create his own software solution.
Shopify didn’t take off immediately, and Lütke faced many challenges. Instead of giving up, he iterated on the platform, trusted his instincts, and grew the company into one of the most successful e-commerce platforms in the world. Like Schmidt's founders, Lütke didn't always have the answers but learned from trial and error, taking feedback and evolving over time.
2. Julia Hartz – Eventbrite
Julia Hartz, the co-founder of Eventbrite, had to navigate the tough world of tech entrepreneurship without being a coder herself. Initially, she and her team struggled with scaling and building a product that could handle the demands of a growing user base. Hartz, much like the founders Schmidt describes, had to figure out how to delegate tasks effectively while keeping the company on track.
In the early years, Hartz had to learn to trust her team to solve problems on their own and figure out solutions to technical and operational challenges. Today, Eventbrite is a leading event management platform, with Hartz continuing to emphasize a culture of learning and growth within the company.
A Leader’s Job: Balancing Patience and Pressure
In the world of entrepreneurship, sometimes the best way to lead is by stepping aside and giving people the opportunity to evolve. Schmidt’s method of balancing pressure with patience is a reminder that leadership isn’t about knowing everything—it’s about fostering an environment where people can discover the right path on their own while still having the safety net of someone experienced when they need it.
Listen to Eric Schmidt:
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