An Interview with James Asquith: World Traveler & Entrepreneur

Today, we’re chatting with James Asquith, who holds the Guinness World Record as the youngest man to visit all 196 countries. Now a successful business owner, he’ll share his travel tips and advice for starting your own venture. Let’s dive in!

1. The Travel Bug: How It All Began

What first inspired you to travel, and how did that lead to visiting every country?

I never planned to visit every country—it just happened! At 18, I flew to Mombasa without much interest in travel. Later, I volunteered in Vietnam with friends, building houses for a few months. That’s when I fell in love with exploring cultures, religions, and meeting new people. My first solo trip to the Middle East sealed the deal—travel became my greatest education.

2. Balancing Travel and Studies

You studied Economics at the London School of Economics. How did you manage travel and school?

It wasn’t easy, but worth it! I maximized long weekends and holidays to squeeze in trips whenever possible.

3. Preparing for New Destinations

How much prep did you do before visiting a new country?

• Visa requirements varied—some took ages to arrange.
• Longer trips required careful saving and planning.

4. Funding the Journey

How did you afford your travels? Is travel expensive?

I’ve always self-funded—no sponsorships. Since 15, I’ve worked multiple jobs, saved, and invested. Travel is costly, which is why I founded Holiday Swap to make it more affordable.

5. A Born Traveler?

Did you always love travel?

My dad was an airline pilot, so you could say it’s in my blood!

6. Life on the Road

What was your daily routine while traveling?

No routine! I loved the freedom—being open to surprises, new places, and people. Strict schedules? No thanks!

7. Hidden Gems

Any underrated countries you’d recommend?

Cartagena, Colombia—amazing culture and one of my favorite places.

8. Cultures That Stole Your Heart

Which cultures resonated with you most?

The South Pacific—places like Tuvalu and Tonga. Life there is family-focused, simple, and content. No obsession with money—just beautiful islands, abundant food, and warm weather.

9. Best Food in the World?

Which country wins for cuisine?

Hands down: Italy!

10. Travel Scrapes

Any tight spots during your travels?

Plenty! Visa issues, airport prison in Mauritania, even visiting Libya and Afghanistan during conflicts. But people worldwide were overwhelmingly kind and helpful.

11. Most Memorable Moments

What’s your standout travel memory?

• Riding a motorbike on Tuvalu’s airport runway (also a sports field!).
• Volunteering in Vietnam—where it all began.
• Yemen’s humanitarian crisis—heartbreaking but important to witness.

12. The #1 Life Lesson

What’s the biggest takeaway from your journey?

There’s never a “perfect” time—just go for it, or you’ll regret missed chances.

13. Travel Essentials

What’s always in your suitcase?

I pack light! Work gear and a few suits (for meetings), but I’m not materialistic. Fitting everything in a carry-on is a win!

14. Advice for Aspiring Travelers

What would you tell someone who’s hesitant to start?

Just go! The world is vast and always changing. It’ll reshape how you see everything—including yourself.

15. Loneliness on the Road?

Did you ever feel lonely?

Occasionally, but I’ve made lifelong friends everywhere. Loneliness never lasts long.

16. Life After 196 Countries

How did things change after your record?

Not much! I’m just a guy who got hooked on travel. The journey taught me more than any classroom. Now, I travel even more for work and to inspire others.

17. Pandemic Travel Tips

Any advice for traveling now?

Research is key, but it’s doable. I’ve taken 75 flights during COVID—just take precautions.

18. Solo vs. Group Travel

Do you prefer traveling alone or with others?

I’m fine alone, but sharing experiences with loved ones is special.

19. Living Like a Local

How can travelers immerse themselves?

Embrace the culture fully! Stay with locals, try traditions, and stay open—you’ll learn incredible things.

20. From Traveler to Entrepreneur

What inspired your shift to business and Forbes writing?

After my record, I wanted to make travel cheaper—so I created Holiday Swap.

21. What Is Holiday Swap?

Describe your business in a nutshell.

It’s a global home-exchange platform. Users swap homes for just $1 per bed per night—now in 185 countries. Travel becomes affordable, and you connect with fellow explorers.

22. The Holiday Swap Origin Story

How did the idea come about?

People kept asking how to travel more. With rising hotel costs, we built a way to use your own bed to explore the world.

23. The Future of Holiday Swap

Where’s your company headed?

Post-pandemic, travelers will seek savings. We’re focusing on domestic/regional swaps, which are booming. Our community makes travel both affordable and inspiring.

24. Why Choose Holiday Swap?

What are the key benefits?

• Saves money on accommodations.
• Connects you with a global community.
• Everything we do encourages exploration.

25. Top Tip for Aspiring Entrepreneurs

Your best advice for starting a business?

Success takes years—failures are part of the journey. Learn from mistakes, stay persistent, and prioritize your business. It’s not glamorous, but passion keeps you going.