Entrepreneurship, Optimism, and Leadership Built Through Intentional Growth

Hannah Greenberg’s journey, from a ten-year-old running a gift‑wrapping business to CEO of Eleven Software, reflects a life shaped by courage, curiosity, and unwavering optimism. She shares how early entrepreneurial sparks, paired with a love of hospitality, led her from Cornell’s hotel school to consulting, hotel development, and eventually to private equity. Her eight years building nearly a billion dollars in hotels taught her to raise capital, lead teams, and operate with grit, experience that fueled her decision to pursue an MBA and take the bold leap into entrepreneurship.

At Berkeley Haas, Hannah discovered search funds, met her business partner, and embraced the risk of acquiring a company without a guaranteed path forward. That choice led to purchasing Eleven Software and later a major competitor, scaling the business globally. She credits mentors for tough love, belief, and guidance, and now pays it forward through weekly office hours supporting aspiring CEOs. Hannah speaks candidly about rejection, adversity, and the power of taking the high road, holding firm to her mantra: “It always works out in the end.”

Her story inspires listeners to take calculated risks, stay optimistic, and build a personal operating system that sustains success at work and at home.

Notable Quotes/Highlights

• "It always works out in the end."
• "Ordinary people are capable of extraordinary things."
• "What's the worst thing that could happen?"
• "The more you give, the more you get."
• "Be your best and most authentic self."

Closing Reflection

Hannah Greenberg’s reflections remind us that optimism, intentionality, and courage create remarkable possibilities. Her journey encourages every leader to invest in themselves, embrace uncertainty, and show up as their favorite self, because that is where growth begins.