Brian Chappon knows how to turn setbacks into success. After the 2008 global financial crisis, he lost everything – his business, his home, his relationships. Burned out and forced to start over, he learned the hard way how to let go and search for a new purpose. So, when the next global crisis hit (COVID-19), he saw it as an opportunity instead.

As the travel industry came to a halt, the same people Chappon had long tried to reach – who were now stuck at home–picked up the phone to hear his ideas.

Chappon recognized the value of person-to-person relationships, not the frustrating person-to-server-to-person dynamic that had become the norm in travel. With direct conversations on the upswing, he saw a chance to rethink how travelers and businesses connect.

That’s when he launched Ask a Concierge: a platform built to restore the human side of travel by eliminating outdated, impersonal concierge systems.

Ask a Concierge aims to simplify the travel experience by giving users access to lounges, dining, wellness, and more without the middlemen, inflating fees, or robotic booking systems. Through the app, local businesses can gain direct access to high-value travelers, allowing them to market themselves cost-effectively and build strong customer retention.

Chappon started his career in capital markets, working across the Middle East, Africa, and Asia. His work not only gave him an international business lens, but it also afforded him with a global perspective and a flare for travel that became the foundation for everything he built next. His journey across industries, continents, and crises taught Chappon how to adapt, rethink, and build solutions to make travel smoother and more human.

What inspired you to start Ask a Concierge? Was there a specific gap in the market you saw?

After a decade in the travel, hospitality, and wellness sectors, we've pinpointed key challenges for travelers and merchants such as airport lounge operators, restaurants, and wellness studios. We're changing how travelers can discover trusted businesses and how to create outstanding experiences for them.

Traditional concierge models can be expensive and often fail to deliver the curated, authentic local experiences that travelers desire. The technology needed to efficiently connect users and merchants is also lacking. Ask a Concierge addresses these issues by offering a matchmaking service that directly connects users with merchants, fostering trust by ensuring options aren't skewed by paid search results.

How does Ask a Concierge stand out from other travel concierge services?

What sets us apart from traditional concierge services is our user-to-merchant matchmaking. We've dedicated seven years to building relationships with restaurants, wellness studios, and airport lounges. By prioritizing our merchants, we ensure our users receive excellent service. We also empower our merchants by giving them control over pricing and scheduling, without requiring discounts.

Our technology revives the personalized service of a maître d, offering a superior guest experience. Just as it feels special when a maître d remembers your name and guides you to your table, we're bringing back that level of real-life hospitality through effective technology.

What is the biggest piece of advice you have for aspiring entrepreneurs who are just starting out?

If I were to write a book about my entrepreneurial journey, it would be titled "What Not to Do While Failing Forward." My advice to any entrepreneur is to position your business so you're working from the outside in, rather than the inside out.

Looking back to when I started 20 years ago, I had passion, energy, and drive, but I was striving too hard. There's a balance in both life and business in letting things come to you. Gain a higher perspective before making big decisions. Remember to take a breath and remain calm, as there will always be crises and drama. And lastly, learn to take criticism, even when it feels personal. If you can do these things, you will grow and create something special.

What’s been the toughest challenge in your career so far, and how did you push through it?

The toughest parts of my career were in 2008, when the market crashed and my first company was on the brink of collapse. At the time, my ego led me to believe I could save it, but in reality, it wasn't worth saving. I lost friends and my partner, and was evicted from my apartment, but that difficult time ultimately showed me that what I thought I wanted in life wasn't what I actually needed. All the pain and failure pushed me to where I am now.

When the next big crisis happened with the COVID-19 outbreak, I had the experience to deal with it and thrive. Ask a Concierge was one of the few travel companies that launched and found success during that time.

You’ve worked in capital markets across the Middle East, Africa, and Asia. Tell us about that experience and what you learned from it.

Living in different countries and working within various cultures provides you with a broader worldview. I love discovering new places and working with people who don't speak my language. Life is enriched when you can live and work with people who have different perspectives. Anyone wanting to grow a global business must immerse themselves in new places and build genuine relationships. This experience stays with you and enables you to solve problems more quickly.

How did you identify Heathrow Airport as the ideal place to pitch your services?

When we started, Heathrow had layovers around four hours, which presented a great captive audience. We researched what travelers were looking for and noticed nothing wellness-related was offered. I questioned why traveling had to feel so terrible, which led to our tagline, "Arrive Better." I cold-called Heathrow, and when they didn't respond, I took a flight to their front door. Two years later, we had a lease signed.

What consumer space do you think holds the biggest opportunities right now? How do you plan to tap into it?

I believe artificial intelligence has created a massive disconnect from real-life experiences and connections. The reason people cancel reservations is often because no relationship was established; it's just a transaction, which hurts small businesses. There's a great opportunity for merchants, travel advisors, online travel agencies, and others to use our technology to make the experience effective while still building trusted relationships. People keep going back to their favorite spots because we are built to connect with each other. Businesses that can connect with guests and make them feel good will have a client for life.

What is next for Ask a Concierge? Any exciting projects or expansions on the horizon?

We have a few exciting projects underway, including working with American Express to create better merchant relationships and experiences in their app. They support our mission to put small businesses first, so there are many exciting developments coming soon. We're also working with a travel content app that is changing how users create travel content and find merchants.

I can't share too much yet, but a new product update will be live soon (App Store and Google Play). We believe users finding travel destinations through social media content will be able to see our curated merchant offerings and book them. Lastly, we are raising capital for the first time due to exciting growth and the need for more team members.

As the expert on all things travel, what has been your favorite destination?

As for my favorite type of travel, for city travel, I love Rome for its food and history. I enjoy running there and discovering new places. I also love hiking in the Alps, especially in the summer when it's less busy. I could spend months exploring new trails and small villages. This August, I'm mountain biking from the French Alps to the French Riviera.

Brian, thank you for your time and insights.