Hear how going broke taught her to value time and mobility and why letting go of control became essential to growth. ============================ Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds. ============================ ON THIS EPISODE 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. → Full show notes with direct links to everything discussed are available here. ============================ FIND YOUR NEXT EPISODE Explore The Maverick Show Starter Packs — some of my favorite conversations curated by theme so you can easily find the episodes that match your interests. ============================ FREE RESOURCES FOR YOU See my Top 10 Travel Apps See my Top 10 Books that Shaped the Way I Travel See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual) Watch my Video Training on Stylish Minimalist Packing so you can join #TeamCarryOn See the Travel Gear I Use and Recommend See How I Produce The Maverick Show Podcast (The equipment, services & vendors I use) ============================ ENJOYING THE SHOW? Follow The Maverick Show on Instagram and DM Matt to continue the conversation Please leave a rating and review — it really helps the show and I read each one personally Support the show by buying me a coffee — espressos help me produce significantly better podcast episodes!

From Rocket Scientist to Real Estate Entrepreneur: The Inside Story of Hipster Investments with Ali Boone (Ep 09)

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Hear how going broke taught her to value time and mobility and why letting go of control became essential to growth.  ============================  Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.  ============================  ON THIS EPISODE  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.  → Full show notes with direct links to everything discussed are available here.  ============================  FIND YOUR NEXT EPISODE  Explore The Maverick Show Starter Packs — some of my favorite conversations curated by theme so you can easily find the episodes that match your interests.  ============================  FREE RESOURCES FOR YOU  See my Top 10 Travel Apps  See my Top 10 Books that Shaped the Way I Travel  See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual)  Watch my Video Training on Stylish Minimalist Packing so you can join #TeamCarryOn  See the Travel Gear I Use and Recommend  See How I Produce The Maverick Show Podcast (The equipment, services & vendors I use)  ============================  ENJOYING THE SHOW?  Follow The Maverick Show on Instagram and DM Matt to continue the conversation  Please leave a rating and review — it really helps the show and I read each one personally  Support the show by buying me a coffee — espressos help me produce significantly better podcast episodes!

The Maverick Show is a global travel podcast about what really happens when people cross borders and build lives across cultures. Hosted by full-time world traveler Matt Bowles, each episode features intimate, unfiltered conversations (often over a bottle of wine) exploring the human stories behind global travel and what the journey teaches us about the world and ourselves.  Guests include expats, digital nomads, women and diaspora storytellers, worldschooling families, and human rights advocates, all sharing travel stories that are funny, moving, and deeply human.  In addition to hearing about extraordinary places and the people who live there, you’ll learn what it’s really like to move abroad, build an expat life, or travel long-term, as guests open up about their personal journeys navigating culture, race, power, identity, and belonging in an unequal world. If you’ve ever felt that travel changes you in ways no one talks about, you’re in the right place.  The Maverick Show hit the Top 100 on Apple Podcasts (including #1 in Places & Travel), was ranked in the Top 1% of podcasts globally by Listen Notes, and was named the #1 Digital Nomad Podcast and #1 Remote Work Podcast by Million Podcasts — with hundreds of five-star listener reviews.

The Maverick Show: Global Travel Stories & Life Beyond Borders

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