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Jessica Jackley, founder of Kiva and general partner at Untapped Capital, shares her entrepreneurial journey and emphasizes the importance of asking 'What if?' questions. She recounts the story of her daughter's fascination with a repetitive bedtime story and how it inspired her to question the potential for change. Jackley highlights the significance of understanding the people you want to serve and designing solutions around their needs. She encourages entrepreneurs to challenge the stories on repeat and imagine different futures, creating value beyond financial gain. Jackley also advises finding your support network and staying true to your values as you navigate the profit-oriented startup world.