How We Started A $300K/Month Business Organizing Trips For Young People

Published: December 6th, 2020
Matt Wilson
from Austin, TX, USA
started April 2012
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Hello! Who are you and what business did you start?

I’m Matt Wilson and my co-founder Jared O’Toole and I own Under30Experiences, a travel company for people aged 21-35. We run small group travel excursions around the world to destinations including Costa Rica, Iceland, Thailand, Greece, and US National Parks.

The key to our business is bringing young people together to step out of their comfort zones and have the time of their lives on our trips that range from four to twelve days.

We’ve been named on Inc Magazine’s list of the fastest-growing private companies in America and number 198 on Financial Times 1000 list of America's Fastest-Growing Companies. Before the COVID-19 pandemic, we were closing in on $5M in revenue and plan to be back to that level and more soon.


What's your backstory and how did you come up with the idea?

In 2012, I was living in New York City, stressed out, working on our startup I was burned out from the unhealthy lifestyle, working long stressful hours, and partying too much. I was invited on a trip to Iceland and I hadn’t been out of the country as an adult, so I jumped at the opportunity. That experience in Iceland blew my mind! I hiked an active volcano, went ice climbing on a glacier, saw the northern lights, and made friends with people from around the world.

The “aha moment” happened to watch the sunset over the Eyjafjallajökull glacier with my Icelandic mountain guide Siggi. He was trying to attract more people from North America to visit Iceland and I knew we could work together. Jared and I had nearly 500K, monthly readers, at Under30CEO, and we thought it’d be a perfect opportunity to bring our community members on a retreat. Sure enough, in less than two months, we organized a trip to Iceland for entrepreneurs and it was a smashing success. We made life-long friends and the idea caught on.

People started asking us “do we need to be under 30 to attend your trip” or “do we need to own a business to come?” It was a huge decision for us at the time, but we decided to open our doors and become an inclusive community rather than an exclusive one. We started running trips that were open to anyone who wanted to come and have a good time.

An attendee on our Iceland trip happened to have a business in Costa Rica and invited me to Central America… I spent a month there and scouted out locations for our next trip. After that I went to Nicaragua, Indonesia, Belize, France, England, Ireland, Spain, and Brazil, continuing to scout out locations for Under30Experiences. My life was changed and the business took off!

At the time, Under30CEO was earning us low six figures in revenue. It wasn’t bad for two guys right out of college, but we knew that Under30Experiences had much greater potential and were a lot more fun. We put Under30CEO on autopilot and used our profits to fund our new business and our lifestyle traveling the world. We were really fortunate to have a business that gave us consistent income, taught us valuable skills we could apply to our next business, and gave us the freedom to be “digital nomads” before work from anywhere was the norm. Under30CEO was acquired in 2016.


Take us through the process of designing, prototyping, and manufacturing your first product.

Our product has gone through lots of iterations. To this day, we keep speaking to our customers until we get it right. We have an active brand ambassador program, an alumni council, a referral program, and a Facebook community where we always ask for feedback from our travelers. We also have a feedback form that we send each traveler after the trip that rates the hotels, activities, transportation, guides, etc. Under30Experiences takes customer experience very seriously.

The original product was much different from what it is today. For our first trip, we recruited high-end entrepreneurs to join our retreat, attended the Startup Iceland Conference, and even organized a private meeting at the President of Iceland’s home. We realized that although the high-end entrepreneur crowd is a very valuable market, it is a small one. We found that successful entrepreneurs are normally very independent-minded, so they travel on their own or are extremely busy with business travel and other commitments. Our first trip went really well, but we knew we had to open up our doors to a larger audience to scale.

Our next trip was for our general blog readers at Under30CEO, they were mainly young entrepreneurs who weren’t ultra-successful yet. This trip went very well too, and the feedback we received is that the travelers really just wanted to go on vacation, and not have any type of business “programming” during the trip. The connections just formed naturally from hanging out, not by doing any “mastermind” activities, or visiting local businesses.

We even tried crazy ideas that were way too niche like the “Nicaragua Microfinance Surf Camp”, luckily our readership on Under30CEO was large enough that the trip sold out anyhow. Most people weren’t that interested in surfing or microfinance--they just wanted to go on an active trip that made an effort to give back to the local community. I had follow-up conversations with nearly all the travelers on that trip, and with their feedback, we really dialed in on what our community wanted from us.


The great part about the business is that after giving up my expensive cost of living in New York I was able to travel the world on a budget, scouting out locations for our next trips. After those initial research and development costs, our only costs were putting together the website and depositing at the hotel to reserve our group booking. If a trip didn’t fill up, we could simply give the money back to the travelers, or hold it as credit for the next trip. Startup costs were low for this business, but the local knowledge it took to run a successful trip was a large investment of time. Luckily this was a lot of fun for me getting to know locals and learning to speak Spanish, for example.

It’s too easy to compare yourself to others and feel like you aren’t getting ahead fast enough. Remember that lasting success is built brick by brick, and it’s difficult to understand that in today’s age of instant gratification, Insta-fame, and overnight success.

Describe the process of launching the business.

Our launch process has been the same from the beginning. We promote our next destination on social media and our blog to build a segmented email list for the product. Our first website was built for free by a company in Colombia that was trying to grow their portfolio and knew that working with us would give them good exposure. As they say, “there is no such thing as a free lunch” and nothing is perfect, but these types of arrangements in the early stages of startups can work well.


In the early days, we knew we had a very large following at Under30CEO and very limited seats, so for our first few launches we built urgency on the offer and told people to sign up at 12:01 am, as soon as the product went on sale. This demand led to sold-out trips and the marketing concept of scarcity worked to our advantage. To this day we have waiting lists for many of our trips.

Since launch, what has worked to attract and retain customers?

One of the biggest lessons learned growing a high growth business is that your systems break every time your business triples in size. For example, when we were running five trips per year, we could do things a lot differently than when we were running fifteen trips. In year three of the business we were already running 45 trips, so just imagine how many times our systems failed! For reference, last year we ran nearly 250 trips, so we’ve gone through lots of iterations of our systems.

We are really careful to document all our processes in Standard Operating Procedures (SOPs). We have very specific onboarding and training procedures, and anything we are going to need to do more than once should have a document that will explain to someone in the future how to do it. The E-Myth by Michael Gerber influenced our thinking on this and I highly recommend the book.

Word of mouth marketing has been by far our biggest driver of growth. We are a product-driven business and obsess about each small part of our itineraries until they deliver the perfect customer experience. Our customer service team goes above and beyond with every single customer and prides itself on “doing the right thing” so they tell all their friends about their positive experience.

Under30Experiences has over 800 five-star reviews on Facebook, Google, and Yelp combined, and almost no reviews of four stars or lower. Quite simply, we show people the time of their life and know this will come back to reward us.

We also identify travelers who want to get more involved after their trips and “bring what we do on Under30Experiences trips to their home city.” These event managers host meetups that range from happy hours to hikes, outdoor movie nights, wine tasting, food festivals, and more. At Under30Experiences meetups, people make friends in their city with people who’ve traveled with U30X in the past. These travelers can’t help but gush to the people they meet what a great time they had in country x, y, or z.

We incentivize our Event Managers by giving them credit towards their next trip. We also have a referral program that over 1,000 people joined in the first few months of launch that rewards people with credit towards future travel. With these types of programs, it is easy to figure out if you are getting an appropriate ROI by knowing your lifetime value of a customer.

Under30Experiences has had some PR in places like Forbes, Inc Magazine, The Financial Times, and I’ve been a guest on many podcasts, but the ROI is more difficult to measure. I also wrote a book, The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life, and am the host of the Millennial Travel Podcast.

While these are huge passion projects of mine, I wouldn’t recommend them for people looking for measurable ROI to grow their business quickly. These are long-term branding plays for us. For immediate, measurable, ROI on marketing spend, spend money on Google and Facebook Ads. We contract a PPC expert to set up all our ads and then our marketing team monitors them internally.

How are you doing today and what does the future look like?

Today, our operations have been dramatically impacted by COVID-19. Pre-COVID there were about ten of us working in our Austin, Texas office working on customer service and marketing, four Regional Managers on different continents handling operations, and more than twenty tour guides working seasonally around the globe. Since then, our operations have been semi-paused, but we continue to be patient and push forward…

Photo of our team in February

We had to dramatically reduce our overhead and then decided to pivot towards running trips to US National Parks, as the immediate trend of people traveling closer to home showed itself. Under30Experiences is continuing to focus on outdoor locations like Yellowstone, Yosemite, Joshua Tree, Lake Tahoe, Acadia, Great Smoky Mountains, the Grand Canyon, etc. On these trips we do temperature checks, have disinfectant foggers for the van, wear masks, put travelers in their own single tents, and follow guidelines from the World Health Organization (WHO), Center for Disease Control (CDC), World Travel & Tourism Council (WTTC), and local governments.

While I think new-age terms like “follow your bliss” or “do what gives you joy” are overblown and out of touch with reality, finding meaning and purpose in what you do makes life so much better.

Our biggest tech investment in the company has been in understanding our data, so we can make better decisions about inventory management. It is extremely difficult to predict demand for trips, and our trips are most profitable when they are full (16 passengers maximum on most trips). Under30Experiences has 30+ products and each one behaves differently. For example, a trip to Portland Maine at $895 will see many more last-minute bookings than our $2495 trip to New Zealand. Of course, we’d rather run more New Zealand trips because they net more money, but we need to be realistic, so we don’t schedule too many departures and end up with trips that don’t sell.

Our team loves to nerd out data points like how far out people book, the average age of our customers per trip, where they live, and if they are repeat customers. All this data is extremely valuable for us.

We also invested a lot in understanding our discounting model. Last-minute seats are very profitable for us, but flights are expensive for people who book last minute. It’s important to understand the peak time customers will book a trip and then offer discounts as the departure approaches to offset lower demand.

Through starting the business, have you learned anything particularly helpful or advantageous?

I’m proud to say we’ve always worked very hard to build a solid foundation for Under30Experiences, and as many “growth hacks,” as we’ve tried, the biggest return on investment always comes from investing in our community. Even though we saw 600%+ growth over a three-year period, we were always able to keep the customers’ best interest in mind and find deep meaning in what we do. Our team understands the life-changing magic of travel, and we focus on delivering that to every traveler on every trip.


We invest heavily in training our team on how to pay forward the “Under30 Magic” flying someone to train our guides, or bringing our international staff to our headquarters in Austin each year. We’ve also seen a great return on investment in our Under30Experiences ambassador program that hosts our meetups around the United States and recruits new people to be part of our community.

Under30Experiences also sends our customer service team to attend trips and find that this investment makes them part of the community, understand our customers, tour guides, and product better.

As you can see, we’ve invested in creating lots of opportunities to speak with customers. I even lived in Costa Rica for 5+ years, so I could fully understand how our operations on the ground worked, and speak with a new group of customers each week. One thing that we learned is that what a customer says they want and what they will pay for are two different things.

For example, a two-week trip to Patagonia with Under30Experiences may be on everyone’s bucket list, but there are only so many people in our age demographic who can pay for this. We’ve developed a specific product formula that we know works, so we don’t just blindly follow what the customer tells us they want but may not necessarily have the time or money to purchase it.

What platform/tools do you use for your business?


Customer Service:

Accounting and Legal:

General and Misc:

What have been the most influential books, podcasts, or other resources?

A few books that give a framework for a high growth business that has been extremely helpful have been Traction by Gino Wickman, The Customer Funded Business by John Mullins, and Scaling Up by Verne Harnish.

Two books that give seasoned advice on how to deal with people and manage a team are High Output Management by Andy Grove and The Hard Thing About Hard Things by Ben Horowitz. These two books have cult followings and are read by all the big Silicon Valley CEOs and venture capitalists.

I’m a voracious podcast listener and a few of my favorite podcasts for startups are The Tim Ferriss Show, Masters of Scale with Reid Hoffman, Noah Kagan Presents, Starting Greatness with Mike Maples Jr, and the Naval Podcast.

More valuable to me than the business shows are the ones that help me improve my health--mentally, physically, and spiritually. Without a new set of healthy habits, I personally would not be able to operate the business we run while traveling all over the world, writing a book, and now raising a daughter. Some of my favorite wellness podcasts are Bulletproof Radio by Dave Asprey, Ben Greenfield Fitness, and The Drive by Dr. Peter Attia.

Advice for other entrepreneurs who want to get started or are just starting?

My biggest advice to entrepreneurs who are just starting is to make sure they are playing the long game. It’s too easy to compare yourself to others and feel like you aren’t getting ahead fast enough. Remember that lasting success is built brick by brick, and it’s difficult to understand that in today’s age of instant gratification, Insta-fame, and overnight success.


Living below my means in Costa Rica allowed me to pay off my student loans and get ahead financially. Too many entrepreneurs upgrade their lifestyle too quickly and try to enjoy the material things that money can buy instead of investing this money back into their company and paying less in taxes.

I’ve been heavily influenced by the Financial Independence community, and even though I don’t ever want to retire, I value my freedom to be able to do whatever I want, whenever I want, with whomever I want. As sexy as that sounds, remember when you have employees, you have to answer to them, which is much more difficult than answering to a boss.

Finally, it sounds cliché, but it's so important to do something you love. While I think new-age terms like “follow your bliss” or “do what gives you joy” are overblown and out of touch with reality, finding meaning and purpose in what you do makes life so much better. “Doing what gives you joy” is a self-centered, naive approach to work, while doing difficult things to move you towards your goal of serving others with your product or service is a much more sustainable approach to business that will be more fulfilling in the long run.

Are you looking to hire for certain positions right now?

We are not hiring anyone full time at the moment, but we’d be interested in speaking with a PPC marketer with expertise in Google and Facebook Ads.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!