While still working for the Air Force stationed overseas, Tony Jefferson started a side project that combined his passion for travel and some of his professional knowledge in the IT space. At the start, he didn’t have a fully formed idea of where this project was headed, but he experimented and tested until finally coming up with the TravelingSession.com platform as it is today.
In this interview article, he shares his transition to business and the challenges he overcame creating something that is the first of its kind in the market. He also talks about the people, tools, books, and other resources that have helped him along the way. Check out his top three tips for aspiring entrepreneurs, as well as his insights on time management and handling burnout.
Table of Contents
- Jefferson’s Background
- Jefferson’s Leap Into Entrepreneurship
- Early Business Days
- How Jefferson Grew His Business
- Jefferson’s Advice to Entrepreneurs and Handling Burnout
- How Jefferson Overcame His Biggest Challenge
- Jefferson’s Read-Watch-Listen List
- Wrap Up
- More About Tony Jefferson
What does your business do, and who are your customers?
TravelingSession.com is an innovative platform that is revolutionizing how people share travel experiences. We developed a proprietary review system that empowers individuals to explore, connect, and share their travel adventures in a unique and engaging way. The overall goal is to help people choose better travel destinations.
In simple terms, the website is a social media platform focused on travel, but we’ve created features you won’t find on any other travel site.
The experience centers around travel reviews. Instead of one writer’s opinion, the platform lets everyone rate and review destinations. You can also share photos and videos of your travel adventures. The system allows travelers to find travel reviews and media about destinations from people with similar travel.
I realized everyone isn’t looking for the same thing in a travel destination. So, we also give each traveler a personalized travel rating based on their preferences for every destination. This rating gives you a general idea of whether you should visit a destination based on past visitors’ ratings.
The platform also gives globetrotters and jetsetters a new way to showcase their adventures. Our travel profiles give travelers a place to portfolio their travel reviews and content. Travel styles, countries visited, favorite cities, and more. Visitors can easily navigate content using our intuitive map interface.
Our mission is to inspire people from all walks of life to get out and see the world. But, instead of promoting the most popular destinations, we match travelers with the destinations that are right for them. We created a space where travelers can get unbiased opinions from people who travel the way they do. Through our proprietary review system, personalized approach, and intuitive map interfaces, TravelingSession.com empowers individuals to explore, connect, and share their travel adventures in a way that aligns with their unique preferences and interests.
What first got you started working on your business, and what motivates you each day to do what you do?
My daughter was in 4th or 5th grade when we lived in Germany. One day, she came home from school and mentioned Brugges. I’d never heard of it, but I love a good road trip. So, we packed up and visited for a few days. The old-world charm, the canals, the food; it’s definitely a place I recommend. It still bothered me that I had never heard of the city. I started thinking about the other amazing cities in the world that I’d never heard of. I think that trip planted the seed for TravelingSession.com.
How long have you been in business?
I already owned the domain but started working on the project in 2018. The current version of the site went live in Q2 of 2022.
Jefferson’s Leap Into Entrepreneurship
How did you decide to start your business and take the leap into entrepreneurship?
I served in the US Air Force for 21 years doing IT and cybersecurity. I spent most of my time overseas and fell in love with travel and learning about different cultures. So, I combined what I was good at with what I loved.
TravelingSession.com was a side project while I was in the Air Force, but I didn’t have a clear vision for the project yet. I took a job after I left the service, but I was still working on the site. After a year, I wasn’t satisfied being part of the workforce, so I started working on the platform full-time.
And then the pandemic hit. I gave up everything to work on a travel website, and nobody can travel. Not only that, no one knows when or if people will be able to travel again. I decided to keep going, and I’m glad I did. Travel came back in a big way.
People: Just me
How did you manage your time during the transition to entrepreneurship?
When I switched from being an employee to working on the website full-time, time management wasn’t a factor. There’s so much that you don’t know. I spent a lot of time studying and learning what it takes to run a business. Once I figured out all it takes to run a business, then time management became a factor.
Early Business Days
What were some of the challenges you faced in the first year or early on in your business, and how did you overcome them?
The early years of my business were a challenge. My idea was a unique concept, so I didn’t have another website to use as a reference. There was a lot of throwing things against the wall and seeing what stuck.
First, I tried existing software, but nothing met the criteria. Then, I tried coding the site myself. I soon learned that writing code was not my strong point. After that, I started hiring developers, which became a whole new challenge.
The project is complex, and I had to try out several developers. Most developers could complete part of the project but get stumped by the next task. I eventually achieved the functionality I wanted, but it was a clunky patchwork of programs. Once I found a developer I could trust, I had him rewrite everything into one seamless platform.
People: Just me
How did you manage your time early on?
In the beginning, I didn’t manage my time well. As a new business owner, I was all about saving money and doing everything myself. It was frustrating. I wasn’t getting much sleep. I spent all of my time in my office. I was ready to go off a cliff every time my code didn’t work. And to top it off, I wasn’t seeing any progress.
How Jefferson Grew His Business
Between your early days and today, what have been some of the challenges you faced, and how have you overcome them?
Growing up, they taught us hard work pays off. That’s not always true when you own a business. I didn’t start seeing progress until I learned to stop doing the things I didn’t want to do. In the beginning, I tried coding everything myself. I saved a lot of money, but I was frustrated and miserable. On top of that, I wasn’t hitting any of my milestones.
To me, if I’m going to sit around all day doing something I don’t like, then I may as well get a job.
When I hired a developer to take over writing the code and focusing on the parts I enjoy, life got much better. Once I got my head out of the weeds, I could focus on the site’s core functionality. Now, I’m ahead of my original production schedule.
People: Just me. I have a developer I call in to handle the heavy lifting in building the platform’s features.
How do you manage your time today or since ‘early business’?
It’s easy to let your business consume all of your time, especially when it’s always right in front of you, and no one’s counting your hours. Yes, there’s always a fire to put out in your business, but take time out for yourself. Your business is only as healthy as you are.
My gym time comes first. My entire schedule revolves around those times. Plus, the sense of achievement from my workouts helps fuel my motivation for the rest of the day.
I block off an hour for meals. No work gets done during that hour. That’s when I’ll typically catch up on TV or sneak in a quick video game.
Luckily, my business is travel, so it’s not hard to talk me into a vacation.
Jefferson’s Advice to Entrepreneurs and Handling Burnout
What are the top three tips you’d give someone who’s interested in starting a business?
Start a business you’re passionate about. There will be days in your business that will break your soul. If you don’t love what you’re doing, you will quit.
Starting a business is a good way to find out what you suck at. The things you suck at are the first positions you should hire for or outsource.
Start thinking about marketing early, even if you don’t plan to spend on marketing right away. It’s easier to build your story into your product or service than to go back and add it in.
What is your relationship with burnout?
I experienced burnout from not having a clear vision for the project. If you take off at full speed with no direction, eventually, you’ll burn out before you reach your destination. Once I figured out exactly what I wanted the site to be, I could focus on what was important. It’s much harder to burn out when you have your target in sight.
What is your gross annual revenue in US dollars?
On average, how many hours per week do you work? [in and on your business]:
I honestly have no idea. I’m at a stage where this is still fun.
How Jefferson Overcame His Biggest Challenge
What is one of the most difficult things you have overcome in your business?
The biggest obstacle I overcame was developing the concept. There isn’t any other website like it, so coming up with the idea was challenging. Plus, I was bootstrapping the project.
Instead of attempting to build a platform right out of the gate, I started with a blog-styled website. As time progressed, I worked on adding and developing new features to increase user engagement. As the platform continued to transform, I started letting other writers submit travel reviews.
Now, I’ve gotten the site to a baseline where I’m comfortable calling it a platform. I’m still developing new features and improving the interface. The site has come a long way, but there’s still a lot of work to do.
What are you most proud of when it comes to your business or journey?
The thing I’m most proud of is that I created something new. People around the world are traveling more than ever, but no one has tried to innovate travel recommendations. I wanted to add a more personal touch to how people choose travel destinations, something the industry needed. It’s exciting to create something no one has seen before.
Jefferson’s Read-Watch-Listen List
Are there any other tools, software, apps, etc. you use today that you haven’t mentioned?
Jefferson’s side project turned out to be a true passion project that has become his full-time business now. His story shows us the additional challenge of coming up with a novel business idea – you don’t have anyone or anything to learn from to accelerate setting it up. But persistence, trial and error, and just sticking with it eventually gave him clarity on his vision.
His website needed a lot of custom code, and the search for someone who could deliver what he envisioned was another major challenge in itself. Finding the right person he could rely on and trust for the job was a major step forward. Getting the right people on your team can be the game changer that sets you on the path to further growth and expansion.
More About Tony Jefferson
I was born and raised in Sumter, SC. After high school, I joined the Air Force, working in IT and cybersecurity. I spent most of my time overseas in Japan, Germany, and Korea, which sparked my love for travel. I wanted to combine my IT background and passion for wanderlust after the Air Force, so I started a website as a side project. I took a project management job after the Air Force, but after a year, I knew I wanted to pursue my side project full-time. That’s how I started TravelingSession.com.
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