You can't be successful in business without taking risks. It's

Host: The evening feels calm, the conversation taking on a straightforward yet profound tone as Jack and Jeeny reflect on Adena Friedman’s words. The simplicity of the statement seems to resonate with the inherent truths of entrepreneurship and success. Jack takes a slow breath, clearly thinking about the deeper meaning behind the quote.

Jeeny: "Adena Friedman once said, 'You can't be successful in business without taking risks. It's really that simple.' It’s such a straightforward statement, but I think it hits on something really important. Do you think risk is truly that fundamental to success, Jack?"

Jack: He nods, a thoughtful expression crossing his face. "I do think it’s that fundamental. Success in business, or really in anything, involves stepping into the unknown and taking chances. If you play it too safe, you might miss out on opportunities. Taking risks means making bold decisions, often without knowing what the outcome will be, but trusting that you’ll find a way through." He pauses for a moment, his tone shifting slightly. "But it’s not just about reckless risk—it’s about calculated risk, knowing when to push boundaries and when to seize the opportunity. It’s about having the courage to step into the unknown with a plan, and understanding that failure is often part of the process."

Jeeny: "Exactly. There’s a difference between jumping into something blindly and making an informed decision to take a risk. It's about weighing the potential rewards and the risks involved, and deciding if the risk is worth it. And sometimes, it’s not about being certain—it’s about being confident in your ability to handle whatever comes. If you never take risks, you never discover new possibilities." She pauses, her voice softening with reflection. "I think this idea applies to life beyond business, too. Every time we step outside of our comfort zone, we’re taking a risk. Whether it’s trying something new, investing in an idea, or simply putting yourself out there in a new way."

Jack: "Yeah, you can’t grow without taking risks. It’s the risk that forces you to adapt, to innovate, and to face challenges that you otherwise wouldn’t. But I think the real value of taking risks is what you learn from them, regardless of the outcome. There’s this idea that failure is a negative thing, but in reality, it's just another part of the journey to success. Every risk you take is an opportunity to learn, and every lesson you learn from taking a risk brings you closer to being better at what you do." He smiles slightly. "In business, as in life, sometimes it’s the risks you take that define you and set you apart."

Jeeny: "That’s so true. Some of the best ideas, the most innovative changes, come from people who took big risks. But it’s also about how you handle those risks—how you recover, how you pivot, how you learn and adapt." She smiles, her voice gaining confidence. "Risk is like the fuel for progress. Without it, you’d be stuck in the same place. And whether the outcome is a success or a failure, it pushes you forward."

Jack: "And it’s not about taking risks recklessly, but strategically. In business, you have to assess the risks, measure them, and make sure you’re not just gambling. But the fact remains—you have to take some form of risk if you want to break through to something bigger." He pauses, his tone becoming more reflective. "The risk itself is what separates the ones who are content with mediocrity from the ones who want to build something extraordinary."

Jeeny: "Exactly. It’s the people who are willing to take those risks, who are willing to embrace uncertainty, that end up changing industries, creating movements, or building incredible companies. If you stay comfortable, you stay stagnant." She smiles warmly, as if seeing a larger picture. "Risk isn’t the enemy—it’s the catalyst for growth."

Host: The room feels lighter now, as Jack and Jeeny sit with the understanding that risk is not just a necessary part of business, but a fundamental part of progress. Whether in entrepreneurship or in life, taking calculated risks opens the door to new opportunities and growth. Adena Friedman’s words remind them that while risk can be intimidating, it is the key to achieving greatness—in business and beyond.

As the conversation continues, the idea that success in any field requires a willingness to step into the unknown, to learn, and to grow with each risk taken becomes clearer. Risk isn’t something to be feared—it’s something to be embraced, because it’s the path to discovery and innovation.