Over 50 flights in one year. That’s how much Alex and Karla once traveled while running their businesses. Was it worth it?

In this episode of Rich and Remote, Alex Booth and Karla Singson Booth get honest about the side of location freedom nobody posts about. Between business layovers, time zone swings, and a three-week Europe trip they just got back from, they unpack what travel really costs a business owner beyond the flight and the hotel.

Karla has been a business owner since 2009 and has built a seven-figure business she can run from anywhere. Alex left over a decade in corporate to build his own. Their travel styles could not be more different, and that’s what makes this conversation so useful.

They share the trips that cost them real momentum, what held up while they were completely offline, and the personal rules they now follow before booking anything.

In this episode:

• The five-month stretch abroad that almost brought Alex’s business to a halt
• What Karla discovered about a team member while she was on vacation
• The one hire that closed deals while Karla was offline
• Why you should never try anything new right before you travel
• Alex and Karla’s “magic number” of flights per year (they don’t agree)

If you’ve ever wondered whether your travel plans are helping or hurting your business, this episode will give you a few rules to live by.

Listen to Rich and Remote

• Website: https://richandremote.com/
• Spotify: https://open.spotify.com/show/0nXHDZ2qeYszkrrVoVHMfY
• Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-and-remote-with-alex-and-karla-booth/id1879811727

Work With Us

Want a steadier pipeline and a team you can rely on? That’s what Proximity Outsourcing helps founders build. Book a call: https://proximityoutsourcing.com/book-a-call

Want clients who stay longer, renew, and refer? GetCSM helps you find and hire experienced Customer Success Managers who keep your clients happy, even when you’re on the other side of the world. https://getcsm.com/

Not ready for a full-time hire? Hire An AI VA offers AI-powered virtual assistants for research, content, admin, ops, and marketing, an affordable way to buy back your time. https://hireanaiva.com/

Work-Friendly Stays Around the World

Remember the hotel notes Alex mentioned? Our Rich and Remote stays page features remote-work-friendly hotels, Airbnbs, and third homes around the world. We scout them ourselves and write honest recommendations. Browse the list: https://richandremote.com/stays/

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• (00:00:01) - Intro: Living the Travel Freedom Dream
• (00:01:08) - Setting Up the Episode: How Many Flights Is Too Many?
• (00:05:00) - Sponsor: Hire an AI VA Playbook
• (00:06:22) - What Does Freedom Really Mean?
• (00:10:03) - Defining 'Too Much' Travel
• (00:13:26) - Staycations and Scratching the Travel Itch
• (00:14:53) - Most Flights Ever Taken and Business Impact
• (00:17:48) - When Travel Cost the Business: Alex's Philippines Story
• (00:23:00) - Carla's YouTube Lesson from the Philippines Trip
• (00:25:08) - Europe Trip Debrief: What Held Up, What Broke
• (00:30:06) - Systems and Habits for Traveling Entrepreneurs
• (00:34:51) - Tools, Communication, and Clear Expectations
• (00:37:41) - Managing Teams and Clients Across Time Zones
• (00:46:58) - The True Cost of Travel Beyond Flights and Hotels
• (00:49:30) - Should You Travel Early in Your Business?
• (00:51:31) - Deciding If a Trip Is Worth It
• (00:56:53) - The Magic Number: Flights Per Year Revealed
• (01:01:22) - Closing Thoughts and Sign Off

My passport gets me into fewer countries than yours. I went anyway.

I carry what I call an “ugly” passport: visas, bank statements, embassy interviews and fees I don’t get back if they say no. Still, I traveled the world, closed global brands before 23, and built a multi-million dollar remote business.

In this solo episode, I share the exact playbook I’d hand to any Founder who wants more freedom (especially for my sisters and brothers in developing countries):

Why making more money is your real passport upgrade
✈️ How to build a travel history that gets you approved
Starting with visa-free, inexpensive countries
️ Designing your ordinary days, not your dream vacation
❄️ Why you should visit in different seasons before you move
How to score a country: culture, safety, food, climate, time zone and more
Why trying two or three places isn’t a mistake

Grab a pen, take notes. Then ask yourself: is your “ugly passport” really a wall, or just paperwork you haven’t finished yet?

Know a Founder who thinks “people like me don’t get to do that”?

Send them this.

Get first dibs on our podcast, our latest discoveries, tips, and exclusive discounts and promos from all of our Rich and Remote™ partners all around the world. Sign up for our weekly newsletter: RichandRemote.com

• (00:00:25) - Intro and Show Welcome
• (00:01:45) - The Ugly Passport Story
• (00:03:36) - Weak Passports and Social Mobility
• (00:05:51) - Lesson One: Making More Money
• (00:08:16) - Learning Yourself Through Local Travel
• (00:10:00) - First International Trip: Sydney, Australia
• (00:12:56) - Starting Easy: Nearby Countries for Filipinos
• (00:14:30) - Exploring Culture, Food, and Fit
• (00:17:15) - Moving to Countries That Require Visas
• (00:18:37) - US Visa Experience and City Scouting
• (00:20:15) - Choosing Where to Settle: Key Factors
• (00:21:09) - Digital Nomad Visa Options Around the World
• (00:25:46) - Lifestyle Considerations: Food, Safety, Hobbies
• (00:27:26) - My Journey to Mexico Residency
• (00:28:01) - Next Chapter: Moving to the US
• (00:28:52) - Final Reflections and Encouragement
• (00:33:12) - Closing and Sponsor Messages

What if the biggest risks in your business aren't the bold moves, but the small habits you never question?

In this solo episode of Rich and Remote, Karla Singson Booth talks about the risks she has taken: a career as a competitive poker player, moving to a new country with barely any friends (twice), and starting her first business in an industry she knew nothing about.

After running businesses since 2009, Karla has learned that taking risks and being reckless are two very different things. In this episode, she shares the habits and principles she relies on to lower the odds of failure in business and in life.

Some are simple. Some are uncomfortable. One involves a treadmill and reality TV. And a few of them apply as much to finding the right partner as they do to finding the right clients.

In this episode:

• The step many businesses skip, even after five or 10 years in operation
• What dating has in common with understanding your target market
• The "shortcut" Karla always takes, and why it isn't what you think
• How her competitive debate training changed the way she handles conflict at work and at home
• Why your defaults may be shaping your results more than your motivation

If you've been playing it safe because you're afraid of getting it wrong, this episode offers a smarter way to take the leap.

Listen to Rich and Remote

• Website: https://richandremote.com/
• Spotify: https://open.spotify.com/show/0nXHDZ2qeYszkrrVoVHMfY
• Apple Podcasts: https://podcasts.apple.com/us/podcast/rich-and-remote-with-alex-and-karla-booth/id1879811727

Explore More

• Rich and Remote Newsletter: https://richandremote.com/
• GetCSM: https://getcsm.com/

Work With Us

Want a steadier pipeline and a team you can rely on? That's what Proximity Outsourcing helps founders build. Book a call: https://proximityoutsourcing.com/book-a-call

Not ready for a full-time hire? Hire An AI VA offers AI-powered virtual assistants for research, content, admin, ops, and marketing, an affordable way to buy back your time. https://hireanaiva.com/

• (00:00:00) - Intro and welcome to Rich and Remote
• (00:01:19) - Travel update and episode intro
• (00:02:19) - Life transitions, pandemic, and risk-taking journey
• (00:05:43) - Episode preview and support the podcast
• (00:07:39) - Sponsor: Hire an AI VA playbook
• (00:09:09) - Poker, risk-taking background, and business history
• (00:10:24) - Tip 1: Do market research
• (00:13:04) - Applying market research to finding a partner
• (00:15:20) - Tip 2: Crunch the numbers
• (00:18:56) - Being friends with numbers in business and health
• (00:20:24) - Tip 3: Surround yourself with successful people
• (00:21:57) - Tip 4: Be friendly and influential (Dale Carnegie)
• (00:23:57) - Tip 5: Take the shortcut - hire mentors and experts
• (00:28:03) - Tip 6: Argue from the other side
• (00:29:39) - Debate background and seeing both perspectives
• (00:32:15) - Applying devil's advocate to relationships
• (00:34:03) - Tip 7: Write goals daily and track diligently
• (00:36:45) - Tip 8: Manage your defaults
• (00:41:51) - Defaults in daily routines and sleep habits
• (00:43:12) - Recap of all tips and closing thoughts
• (00:45:16) - Outro and sponsor credits