Narrator: What if the most common story we tell about poverty—one of helplessness and dependency—is fundamentally wrong? Imagine a young woman, disillusioned by the impersonal nature of charity, who travels to East Africa. Instead of finding victims, she discovers a vibrant ecosystem of resourceful entrepreneurs: a man building a brickmaking business from the dirt beneath his feet, a fishmonger tripling her profits by taking a single, calculated risk. These encounters sparked a revolutionary question: What if the poor don't need handouts, but a hand up? What if they are not problems to be solved, but partners to invest in?

This is the central inquiry at the heart of Jessica Jackley's autobiographical book, Find the Courage to Question. As the co-founder of Kiva, the world's first person-to-person microlending website, Jackley chronicles her journey from a skeptical observer of traditional aid to a pioneering social entrepreneur. The book dismantles our preconceived notions about poverty, charity, and what it truly means to create change, arguing that the most powerful tool for transformation is the entrepreneurial spirit that exists in all of us.

Narrator: Jackley’s journey begins not with a solution, but with a profound sense of disillusionment. Raised on Sunday school lessons about helping the "least of these," her early understanding of charity was shaped by impersonal donation requests and heart-wrenching infomercials. While well-intentioned, these efforts felt disconnected and transactional. The cycle of giving money to large organizations provided a temporary relief from guilt but failed to create a genuine connection or a sense of lasting impact.

This feeling intensified during a high school volunteer trip to whitewash a house in Pittsburgh. While she and her friends worked, the able-bodied resident sat idly by, creating a confusing and frustrating dynamic that made her question who truly decides what help is needed. Later, a service trip to an orphanage in Haiti exposed her to the stark realities of extreme poverty, leaving her with a sense of hypocrisy and helplessness as she returned to her privileged life. These experiences planted a seed of doubt: Was traditional charity truly effective? Did it honor the dignity and agency of the people it was meant to serve? Jackley realized that before she could help, she first had to find the courage to question the very systems designed to do so.

Narrator: A pivotal moment in Jackley's journey was her encounter with Howard Stevenson's definition of entrepreneurship: "the pursuit of opportunity without regard to resources currently controlled." This idea radically reframed her understanding. Entrepreneurship wasn't about having wealth, a prestigious degree, or a perfect business plan; it was about the will to act.

This principle is vividly illustrated through the stories of the entrepreneurs she met in East Africa. Consider Patrick, an orphan in Uganda who lost everything in a rebel attack. With no home, education, or resources, he saw opportunity not in what he lacked, but in what he had: the clay-rich earth beneath his feet. He began experimenting, shaping mud into bricks with his bare hands. Through perseverance, he saved enough to buy a wooden mold, then learned to fire his bricks in a kiln, dramatically increasing their value. Patrick eventually built a thriving business, constructing a new home and employing his brother and neighbors. He created something from nothing.

Similarly, Katherine, a widowed fishmonger in Uganda, was struggling to support her seven children by buying fish from a middleman. Realizing she could earn more by going directly to the source, she took a risk and traveled over 100 kilometers to Lake Victoria. The journey was costly and uncertain, but it paid off. By buying directly from the fishermen, she nearly tripled her profits, allowing her to expand her business and even innovate by smoking fish during the rainy season to reach new markets. Both Patrick and Katherine embodied the essence of entrepreneurship: they pursued opportunity with courage and action, using the limited resources they had to build a better future.

Narrator: While working in Tanzania, Jackley learned one of her most profound lessons from an entrepreneur named Innocent. During an interview to assess the impact of a $100 grant, Jackley expected to hear about business expansion or increased profits. Instead, Innocent spoke with pride about a seemingly small purchase: sugar for her tea.

This wasn't a frivolous expense. Innocent explained, "When I have this sugar, I can use it, and also give it to my neighbors. I can invite them into my home and offer them tea. And I can feel proud." For Innocent, sugar was not just a sweetener; it was a tool for building community, fostering relationships, and cultivating dignity. It was a symbol of her ability to be a host and a provider. This "micro-epiphany" taught Jackley a critical lesson: to be truly helpful, one must listen between the lines and value what matters to the people being served, rather than imposing one's own assumptions about their needs. The goal wasn't just to alleviate material poverty, but to empower individuals to define and achieve their own vision of a dignified life, whether that meant a new roof, a padlock for security, or simply sugar for tea.

Narrator: When Jackley and her co-founder Matt Flannery launched Kiva, they had no prestigious qualifications, no venture capital, and no polished strategy. Jackley herself had just been rejected from Stanford Business School and felt deeply "unproven." Their first year was a testament to embracing imperfection. The Kiva logo was designed by a friend in exchange for an old guitar. When their internet failed, they worked from a 24-hour donut shop. The first loans were funded by friends and family, some of whom handed Jackley cash because they didn't use online payments.

This chaotic, scrappy beginning was not a source of shame but a badge of honor. Jackley argues that waiting for the perfect moment or the right qualifications is a form of inaction. True progress comes from starting with what you have and learning as you build. This willingness to "embrace the rough edges" and move forward despite uncertainty is a hallmark of the entrepreneurial mindset. The story of Kiva's launch serves as a powerful reminder that great ventures are rarely born from perfect plans; they are forged in the messy, iterative process of trial, error, and relentless forward motion.

Narrator: In 2007, Kiva faced its first major crisis. A Kiva fellow in Uganda discovered that a trusted local partner, WITEP, led by a close friend named Moses, was engaged in fraud. Borrower profiles were falsified, and funds were being embezzled. For Kiva, an organization built on trust, this was a devastating blow. The team was faced with a choice: hide the failure to protect their reputation, or be radically transparent with their community of lenders.

They chose transparency. They sent an email to every affected lender, explaining the fraud in detail and offering a full refund, an exception to their policy. The response was overwhelmingly positive. Lenders expressed gratitude for the honesty, and many immediately re-loaned their refunded money to other entrepreneurs. This experience solidified a core Kiva principle: transparency is more valuable than perfection. By admitting their mistake, fixing it, and implementing a new five-star rating system to improve their vetting process, Kiva didn't just recover from the crisis—it emerged stronger, with a more resilient and trusting community.

Narrator: Years after Kiva, Jackley co-founded ProFounder, a crowdfunding platform for U.S. businesses. The venture faced significant regulatory hurdles. As she and her partner navigated the complex legal landscape, they felt like climbers on Mount Everest, pushing toward a summit that was becoming increasingly dangerous. Drawing an analogy to the 1996 Everest disaster, where climbers perished after pushing for the summit in a deadly storm, Jackley realized that the ultimate goal is not always to reach the top at any cost. Sometimes, the most courageous and responsible decision is to turn back.

Faced with an "approaching storm" of regulatory pressure and personal priorities, Jackley and her partner made the difficult decision to shut down ProFounder. While it wasn't a financial success for investors, the venture was not a failure. They redirected their efforts to support the passage of the JOBS Act, a piece of legislation that would ultimately make crowdfunding easier for everyone. ProFounder "took one for the team," paving the way for future climbers. This redefines success, suggesting that sometimes the greatest impact comes not from achieving your own goal, but from making the path safer and clearer for those who follow.

Narrator: The single most important takeaway from Find the Courage to Question is that entrepreneurship is not a job title reserved for a select few, but a mindset accessible to all. It is the fundamental human drive to see opportunity in the face of constraint and to take courageous action to create a better reality. Jessica Jackley's journey, and the stories of the entrepreneurs she champions, reveal that the most profound change often begins with questioning the world as it is and daring to imagine what it could be.

The book leaves us with a powerful challenge: to unearth our own "buried coins"—our talents, our resources, our time—and invest them in what we care about most. It asks us to stop waiting for permission and to start building, iterating, and walking our own path, no matter how imperfect our first steps may be. What is the one assumption you hold that, if questioned, could unlock your own entrepreneurial journey?