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.
Episode #09: From Rocket Scientist to Real Estate Entrepreneur: The Inside Story of Hipster Investments with Ali Boone
Episode Summary
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About the Guest
Ali Boone
Ali Boone is a 9-to-5 dropout who left a high-paying career as an Aerospace Engineer to start her own business. She is the founder of Hipster Investments, a real estate investment company that opens the door for anyone to invest in real estate.  She has Master’s degrees in both Aerospace Engineering and Spiritual Psychology.  She has written over 170 articles for BiggerPockets—the world’s leading real estate investing website. She has been featured in Fox Business and The Motley Fool, has over 300k views on her “Calculating Rental Property Numbers” video on YouTube and was awarded Top 100 Real Estate Investing Blogs. If you ask Ali what her biggest accomplishment is though, she’ll tell you it’s that she successfully created a completely location-independent business that allows her to live wherever she wants, travel whenever she wants, work whenever she wants, and most importantly—be her own boss. When Ali isn’t helping people buy real estate or coaching other entrepreneurs, she is usually flying airplanes around Santa Monica (and teaching other people to fly as well), hanging out on California’s beaches or the ski slopes, or volunteering in California prisons.
What You'll Learn
- How Ali Transitioned from the Corporate-Cubicle Life to the Location-Independent
Entrepreneur Life - How She Nearly Went Broke Building Her Dream Company, Hipster Investments, But
Relentlessly Persevered Through Hardship - How to Outsource, Delegate, Hire and Manage an Internationally Distributed Team
Links From the Episode
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Time Stamped Show Notes
[”03:44″] HOW AND WHY ALI PUSHES HERSELF OUTSIDE HER COMFORT ZONE
- How Ali conceptualizes her comfort zone and why she pushes herself outside of it
- How it feels to go skydiving for the first time
- Why she feels skydiving is an apt metaphor for both real estate investing and entrepreneurship
[09:38] ALI’S PATH FROM CORPORATE WORLD TO LIVING A LOCATION INDEPENDENT LIFE
- How Ali Designed Her Path from the Corporate World to a Location-Independent Life
- How and When Ali Took the Leap and Left her Corporate Job to found Hipster Investments
- Ali Describes the Difference in Her Life Now vs When She Had a Corporate Job
[31:00] ALI’S CHALLENGES AND FAILURES ALONG THE WAY
- Ali Talks About Nearly Going Broke in Her First Year of Entrepreneurship
- She Talks About The Importance for Entrepreneurs to Endure the Emotional Roller Coaster
[39:04] TIPS WHEN OUTSOURCING, HIRING AND MANAGING PEOPLE
- Ali emphasizes the importance of outsourcing to avoid the self-employment trap
- Ali’s advice on hiring and managing a remote team
- Ali’s tips on hiring the right people and firing the wrong ones
- How Ali Manages and Motivates Her Team
[49:08] COMPENSATING FOR WEAKNESSES AND AUDITING YOURSELF
- Ali Shares Her Biggest Weakness and How She Compensates For It
- The Importance of Auditing Your Entrepreneurial Skills and Aspirations
- The Importance of Setting the Vision and Creating a Plan to Achieve it
- Recapturing Her Time and Creating the Freedom of Mobility
- Why Money is Now Less Important To Her Than Ever
