The Maverick Show: Global Travel Stories & Life Beyond Borders

Hear how witnessing inequality abroad transformed solo travel into a mission supporting children and local enterprise.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Stella Airoldi begins by explaining why she chose to invest in rental properties and how her lifestyle expenses are now covered by her passive rental income. She then shares her journey beginning with her choice to solo-travel the world and how she was regularly confronted with poverty and injustice, raising her social and political consciousness and inspiring her to pursue dual Masters Degrees in International Law and Human Rights and Democracy. Her passion for children’s rights then led her to Uganda with an academic focus on the rights of girl child soldiers. She explains how her time in Uganda allowed her to meet a talented Ugandan artisan, Susan Laker, who was an illiterate, impoverished, HIV-positive mother of 3, who inspired her tremendously. She explains how she and Susan developed a close personal friendship and eventually a business relationship that led to the launch of 22 Stars Jewelry. Stella then discusses the creation of the 22 Stars Foundation that now sends over 300 kids to school, provides a hot meal, runs after school programs, and provides small business training and micro-loans for local Ugandan businesses. She then explains the social impact “co-workations” that she organizes to bring location independent entrepreneurs to experience Uganda and participate first hand in the 22 Stars project. Stella then talks about why she travels, how it has contributed to her personal development, and shares stories about how she used Tinder for alternative purposes while solo-traveling through Africa. She explains how she deals with stress and optimizes productivity, and shares her top tips for female solo travelers.

→ Full show notes with direct links to everything discussed are available here.

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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)

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Learn how niche marketing, Facebook ads, and strategic partnerships can accelerate growth without scaling too quickly.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Daraja Asili shares her entrepreneurial journey and how the real estate and mortgage crisis of 2009 caused a major life transition that put her on the path to founding Happy Trees Entertainment which currently draws over 100,000 paying customers per year to attend her live events. She explains her unique offerings which include Paint Night, Plant Night and Farm Fresh Goat Yoga, and then discusses how she hires, trains, and manages a fully remote staff of over 30 people. Daraja also shares her personal meditation practice, how and why she varies her day structure, and how she organizes her time for optimal productivity. She also talks about business growth and when it actually makes sense to ‘scale back’. She then discusses ‘Daraja Consulting’, her other business that helps small to medium size companies accelerate their business growth, and shares the most effective ways to improve your sales and marketing to take your business to the next level. She talks about why the best ROI today for your marketing dollars is on social media platforms, how she built her business primarily through Facebook advertising, and shares her single most important piece of advice for optimizing your Facebook ad strategy. She explains how highly targeted affinity-based niche marketing can work for any business, and gives an extended example of exactly how real estate agents can successfully execute this strategy. She then discusses how you should think about establishing the right strategic business partnerships that can really accelerate business growth. She concludes by sharing the advice she would give to her 20 year old self, knowing what she knows now.

→ 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!

Learn how intentional community and relationships can make nomad life sustainable while strengthening remote teams.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Ali Greene talks about being a full time digital nomad for the last 2 years while working as a full- time salaried employee in a senior management position as “Director of People Operations” at DuckDuckGo. She explains the concept of “co-living”, discusses the different lifestyle infrastructure choices available for digital nomads, and shares which ones she likes best and why. She explains the importance of having control over your location and mobility, as well as the importance of curating intentional communities of people who inspire and empower you in meaningful ways. Ali then talks about her passion for street art as a transformative expressive medium. She also shares her analysis about how digital nomadism is transforming work, community and society at large, but emphasizes the importance of pro-active relationship building for long term sustainability of the lifestyle. She then moves on to talk about her professional work in People Operations, and explains how she helped her company grow 80% in 2 years through adjustments in their People Ops with a focus on gender diversity. She gives specific tactical advice on hiring practices, managing an internationally distributed team, and performing as a senior manager from different time zones around the world. She talks about what “company culture” really means, the importance of it, and how to build it meaningfully with a fully remote staff. She talks about some of the unique productivity hacks she uses, including “context switching” by physically changing work locations multiple times throughout the day to correspond with different tasks. She also shares why she dyes her hair pink and blue and once joined an axe-throwing league.

→ 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!

Learn how emotional intelligence, daily routines, and team culture can keep global work-travel communities thriving.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Hacker Paradise CEO Spencer Jentzsch talks about his role running the world’s first international work-travel program for digital nomads. Founded in 2014, HP has taken over 550 people to live, work and play together in 20 countries and has attracted participants from companies like Google, SpaceX and Y Combinator.  On the trips HP provides housing, workspace access and a community of cool people to explore and party with, as well as organizing weekly workshops, talks, skill shares, goal sharing sessions, and networking events to help participants with professional development and goal achievement.  Spencer shares his hiring practices for building the HP team and talks about the crucial importance of emotional IQ. He also talks about how to manage staff across time zones, how to structure a daily routine to optimize productivity, and how to deal with stress. Spencer also opens up about his personal journey of self-discovery through world travel and tells the story of leaving the US for the first time at age 19 on a Mormon Mission to Korea for two years after which Korean language and culture became his passion and the focus of his academic work. Spencer then tells the story of how his Korean language skills led to his role escorting the CEO of Samsung (the most powerful man in South Korea) at the 2010 Olympics, and then hand-writing Samsung’s Christmas cards to top fashion designers like Marc Jacobs. He also talks about his role in co-founding a Tinder Profile Consultancy, and gives specific suggestions for how to immediately optimize your online dating profile.

→ 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!

Learn how buying rental property sight unseen works and why the right team keeps ownership from becoming another job.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

This is Part 2 of the Interview with Ali Boone who is the owner of Hipster Investments and has been a regular contributor to the Bigger Pockets Blog since 2013. In this episode she shares her personal real estate investing journey and discusses why she buys “turnkey” residential investment properties, why she buys them out of state, why she is comfortable buying them sight-unseen, why she buys to hold and not to flip, and why she always uses professional property management. Ali talks about the importance of prioritizing your time and mobility and explains the difference between being a real estate investor vs. a landlord or a rehabber. She talks about how to build your team and manage your property managers. Ali tells the story about how she once dealt with a roof blowing off her rental property in the US without ever having to leave the swimming pool in Nicaragua. She then discusses her degree in spiritual psychology, the benefits of meditation, Kundalini yoga, Tantra, and her specific techniques for dealing with stress. She also talks about her TV Debut on a reality makeover show, and tells the story of how she had to give flight lessons wearing 5 inch stiletto heels. She shares her top book recommendations, favorite travel region in the world, and talks about her top bucket list destinations as well as the advice she would give her 20-year old self if she could go back in time.

→ 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!

Hear how going broke taught her to value time and mobility and why letting go of control became essential to growth.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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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!

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 it's 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!

Learn the watch-time, playlist, and publishing strategies that can make YouTube recommend your videos to more viewers.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

YouTube Influencer Nick Nimmin explains how he grew his personal YouTube Channel by over 100,000 subscribers in under 12 months. He talks about the biggest mistakes people make with YouTube and why most people fail to grow their audience. He gives a detailed example of how a local real estate agent could use YouTube to dominate their local market, and explains the #1 mega-mistake real estate agents make on YouTube. He then explains how to optimize your ‘watch time’ and ‘session time’, why to use a ‘series playlist’, how long your videos should be and how frequently you should publish in order to maximize your authority and increase your chances of YouTube recommending your videos. Nick also opens up about his personal journey, talks about his early days as a hip hop DJ and tells the story of how he got to open a concert for 2 Live Crew. He then shares his pivotal transitionary moment when he got in shape, dropped 100 pounds, sold all his stuff, moved to Thailand and slept on the floor of his brother’s storage room for 4 months as he got on his feet and started his business. He also talks about how his daily practice of meditation over the last 3 years has changed the way he sees everything. He explains the specific details of how he meditates, the science behind it, and then makes recommendations for how beginners can get started. He concludes by naming his top 5 hip hop MCs of all time!

→ 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!

Learn how content monetization and multiple income streams can fund freedom while building a global nomad community.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Nomad Summit founder Johnny FD shares his story of how he decided to quit his corporate job in Los Angeles and move to Thailand to live on the beach, work as a dive master and eventually become a professional Muay Thai kickboxer and an online business owner. He opens up about his personal journey overcoming insecurity and developing the confidence to pursue a location-independent lifestyle. Johnny then talks about his online business journey through drop-shipping, affiliate marketing, blogging, podcasting, and explains how he grew his online income to over $200K/year and got featured in Forbes, Business Insider, Fast Company and Entrepreneur Magazine. He explains the content-monetization strategies he uses and the specific ways he created multiple streams of automated passive income online. He then tells the story of how he founded the Nomad Summit in Chiang Mai, Thailand which has grown from a small local gathering to a major international event attracting over 400 digital nomads each year from around the world. Johnny talks about the evolution of the digital nomad scene in Chiang Mai, describes the cost of living, quality of life, and the social scene in the world’s largest nomad hub. He then discusses how the broader digital nomad eco-system is growing and developing globally. Finally, he pulls back the curtain on how he invests his personal net worth and what percentage he keeps in real estate vs. other asset classes, and shares the biggest lesson he has learned from his hundreds of guests on the Travel Like a Boss and Invest Like a Boss podcasts.

→ 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!

Learn how failures, virtual systems, and workday design can keep a global team thriving across changing time zones.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Jennifer Magee shares her personal journey through the world of architecture, design and real estate development on her way to becoming a location-independent business owner. She opens up about how she navigated repeated business failures and continually implemented the lessons learned until she eventually selected the right business partners, built the right team, and started landing Fortune 500 clients. She talks about how she built her architectural design company, Retail in the City, with a virtual infrastructure that she can run from anywhere in the world while serving clients like Saks Off 5th, Barnes and Noble, and The Sharper Image. As a digital nomad who chooses to live in different time zones across the world for extended periods, she discusses how she structures her workday in order to manage her international team effectively while optimizing her own lifestyle design. Jen also explains why her two most effective techniques for stress-relief over the years have been 1) Dancing (more than any other form of exercise) and 2) Spontaneous travel. She tells the story of how she took a last-minute trip to Peru by herself to do a multi-day hike to Machu Picchu and ended up with a private entourage and cook attending only to her! Jen also names the celebrity she would most like to have dinner with and what questions she would ask at that dinner. She then shares her most influential book, her most impactful productivity app and, after travelling to over 50 countries, she recommends her top 3 travel destinations of all time.

→ 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!