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The Maverick Show with Matt Bowles


Dec 3, 2018

Hipster Investments founder Ali Boone shares her story of leaving her top-secret government job as an aerospace engineer to move to the beach and start a real estate investment company. She talks about her path from rocket scientist to real estate investor to location-independent business owner. Ali opens up and shares the inside story of her business building journey, including details about her financial struggles in the early days of building Hipster Investments. She talks about her setbacks, failures, going broke and even getting on food stamps in the beginning of her entrepreneurial journey. She gives advice for planning your transition out of the corporate world and how to set expectations for yourself and endure the difficulties of early-stage entrepreneurship. She talks about how controlling her time and her mobility is now more important to her than the income she makes. Ali then talks about hiring and management tips for business-building, emphasizes the importance of relinquishing control, and gives tips on avoiding the self-employment trap. She talks about the required confidence to know that its ok not to know how to do something and the importance of hiring people who are smarter than you in certain areas. Ali also talks about her first skydiving experience, what the scariest part was, and why she continually pushes herself outside her comfort zone.