Travel, in my view, is a transformative experience that goes beyond mere escapism; it’s a conduit for meaningful connections and personal wellness. This belief became crystal clear during my travels with my children. Before we set out on our journeys, my kids had a ‘frenemy’ relationship — sometimes friends, sometimes more like adversaries. However, the shared experiences and challenges of our travels turned them into an incredibly close-knit group, almost like a band of brothers.

As part of my series about “developments in the travel industry over the next five years”, I had the pleasure of interviewing Jordan Monroe.

Jordan Monroe is a serial founder and previously the co-founder of Owlet Baby Care. He is currently the CEO of after a year long sabbatical where he traveled with his family. He has a vision to improve the travel experience leveraging technology and the advances of AI.

Jordan attended Brigham Young University and graduated with a degree in Business Management. He is passionate about helping people and spent two years doing service in Mexico, helping him become fluent in Spanish.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

After taking my first company public, I fulfilled one of my lifetime dreams: taking my family on a trip around the world. During our travels, friends would often ask what I was doing when I wasn’t traveling. For about 18 months, my answer was:” I am planning my next trip.”
 Planning became a full-time job: figuring out distances, open times, and attractions. 21 grueling itineraries later and with the advent of Generative AI, the idea for iplan came about.

Can you share the most interesting story that happened to you since you started your career?

I was fortunate enough to be on a panel that flew to Richard Branson’s Necker Island. Spending a few days with Richard Branson, a personal hero of mine, was amazing. 
 His playful nature and zest for life made me realize the importance of enjoying what you do, both as an entrepreneur and an innovator.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I have made countless mistakes while building new companies. The journey is filled with ‘pitfalls’ that can make you feel foolish. But the reality is, when you are creating something new, mistakes are inevitable.

Which tips would you recommend to your colleagues in your industry to help them thrive and not burn out? Can you share a story about that?

Burnout was a significant issue for me at my last company, which led me to take a travel sabbatical. Time-boxing my week and setting realistic expectations for what can be achieved has been helpful. Treating life and business as a game also helps; if I finish early, that is a bonus. This approach has significantly alleviated my burnout.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My college professors were invaluable mentors. Many were entrepreneurs themselves and took adjunct roles just to help the next generation. They gave their time to refine my business plans and shape my worldview. Additionally, the entrepreneurial community has been incredibly supportive. Every entrepreneur I have reached out to for advice has been willing to help.

Thank you for that. Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

Planning a trip has historically been a complex problem. With advancements in large language models and generative AI, we now have a chance to simplify this for users. 
 Our aim is to make trip planning easy and customized, as each person travels differently.

Which pain point are you trying to address by introducing this innovation?

The pain point we are addressing is logistics planning. While some aspects of planning can be fun, like discovering new places and activities, logistics are tedious. 
 Our software functions like a Tinder for travel. Users swipe through attractions, and we handle the logistics like opening hours and distances.

How do you envision that this might disrupt the status quo?

The travel industry has seen many evolutions, particularly with the rise of the internet and Online Travel Agencies (OTAs). While OTAs solved the initial problem of price comparison, they only scratched the surface of what travelers really need: comprehensive trip planning. Our innovation aims to disrupt this status quo by shifting the focus from merely ‘booking a trip’ to ‘owning the entire travel plan.’

Imagine a future where travelers no longer need to have 20 browser tabs open, meticulously stitching together various elements like flights, hotels, and activities. Our planning tool aims to be the ‘one-stop-shop’ for all your travel needs, with the added benefit of customized recommendations. Since the tool knows your preferences, whether you’re traveling with children or looking for a culinary adventure, it can suggest relevant hotels, experiences, and even dining options.

The key disruption here is a shift in how travel is sold and experienced. Traditionally, OTAs have been the go-to source for price comparisons. However, the next wave in travel will likely be defined by platforms that offer comprehensive solutions tailored to individual needs. By owning the ‘plan,’ we not only solve the customer’s most significant pain point but also position ourselves to win their bookings. In this new paradigm, the power shifts from generic, price-focused platforms to customized, experience-driven ones.”

You are a travel insider. How would you describe your perfect vacation experience?

The perfect vacation varies. Sometimes it is about spending quiet moments with a loved one away from the kids. Other times, it is about venturing off the beaten path, exploring nature, or visiting iconic world-influencing places. Each experience offers a unique joy. However I tend to really get a thrill from going to countries like Nepal, and Tonga that take 5 flights to get there and feel like you are going back in time.

Travel is not always about escaping, but about connecting. Have you made efforts to cultivate more wellness-driven experiences? We’d love to hear about it.

Travel, in my view, is a transformative experience that goes beyond mere escapism; it’s a conduit for meaningful connections and personal wellness. This belief became crystal clear during my travels with my children. Before we set out on our journeys, my kids had a ‘frenemy’ relationship — sometimes friends, sometimes more like adversaries. However, the shared experiences and challenges of our travels turned them into an incredibly close-knit group, almost like a band of brothers.

The term ‘wellness’ often conjures images of yoga retreats or spa vacations, but wellness can also encompass emotional and relational health. For instance, overcoming challenges together during travel — be it navigating a foreign city or tackling a strenuous hike — brings about a unique form of wellness. It cultivates resilience, fosters deep connections, and often leaves us with a shared sense of accomplishment that strengthens our bonds.

Moreover, travel allows for the kind of deep, uninterrupted conversations that are often missing in the hustle and bustle of daily life. Whether it’s a heart-to-heart talk during a long drive or the quiet moments spent watching a sunset, these are the times when real connections are made. And ultimately, isn’t that what wellness is all about? Creating a life rich in relationships and experiences, not just material possessions.”

Can you share with our readers how you’ve used your success to bring goodness into the world?

We have not been successful yet, but I believe that making travel planning easier will lead to more people traveling, which in turn creates better global citizens. The barrier of planning often deters people from embarking on journeys that could otherwise be life-changing.

You are a person of great influence. If you could start a movement that would bring the most good to the most amount of people, what would that be?

If I could initiate a global movement, it would be to shift our focus from measuring Gross Domestic Product (GDP) to Gross Domestic Happiness (GDH). The current paradigm assumes that increased wealth will naturally lead to increased well-being, but this has proven to be a flawed metric. Countries with booming economies often show a rise in issues like mental health problems, environmental degradation, and social isolation. Take marketing, for instance; while it may drive consumerism and boost GDP, it often negatively impacts mental health by creating unrealistic expectations. Similarly, the use of plastics may contribute to economic activities, but it wreaks havoc on our oceans. Social media, too, although a boon for connectivity and business, has had detrimental effects on the mental health of our younger generation. If we were to focus on Gross Domestic Happiness, these aspects would be considered, and appropriate measures — possibly even taxation or regulations — could be implemented to ensure a more holistic societal well-being.

What kind of readers follow you on social media?

You can follow me on Instagram at @JordanJMonroe

This was very inspiring. Thank you so much for joining us!


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.