In this episode, Dave is excited to welcome Jesse Maddox. Jesse has a really cool story. He is the founder of TripLingo, one of the most awarded apps in the travel space. TripLingo is the ultimate tool to help travelers communicate when they don’t know a language. It allows you to Learn essential phrases, instantly translate your voice or connect to a live translator, get a crash course on the local culture and so much more.
TripLingo was born, as many of the most useful things in our lives are, out of necessity. For nearly two years ending in 2010, Jesse lived, worked, and traveled in 10 different countries throughout Asia. When he arrived in Vietnam, it didn’t take long to learn that without any language skills it was going to be rough. Lacking language skills, he often found himself frustrated. Perhaps worst of all, he had no sense for the culture he was now living in.
Something had to be done. Yet after an exhaustive search for options in app stores, bookstores, and websites, it became quickly apparent that each option had some fatal flaw. They were either ridiculously expensive, or they tried to teach Jesse phrases that he would never use, or they were simply impractical and difficult to use. Out of this need, the idea for TripLingo was born.
When he got back to the states, he made it his mission to help travelers better communicate and created TipLingo which is now one of the most decorated apps ever in the travel sector and has been featured everywhere from Fast Company, Forbes, Fox Business to Lifehacker.
But the story of how everything came together and the lessons Jesse learned is priceless.
Jesse originally started out wanting to be a lawyer, but saw an opportunity to help make it easier to search for textbooks and started a company around it, his first. That is how he fell in love with entrepreneurship – to take an idea and make it become a reality.
After college, Jesse wanted to spend time abroad. He spent almost 2 years in Vietnam working for Caterpillar. He had a huge problem understanding he language and culture. He had to hire 2 tutors to work with him every day for 9 months. It was out of this experience he learned some important things:
Triplingo became a side project at first for Jesse and he continued to work on it as he came back to the states. He left his job in Vietnam and lives in India for 6 months working on the business plan and then came back to the states.
He then began to raise money and found out it was much harder than he thought. He learned quickly that he could not raise money without having a team and readiness to execute.
At the 8 min mark, Jesse tells a great story of how he got TripLingo off the ground. It is a great example of hustle, perseverance, drive, and how you can be “professionally” persistent.
At the 10:50 mark, Jesse talks about transitioning an app from a total consumer focus to a business focus as well as how they did it.
Jesse talks about how challenging it is to start and monetize an app. He talks about how an app really is a delivery vehicle for a service that you are delivering. He also talks about the difference between individual consumer downloads through an app store vs. a business focus. But again, it is the service that they are buying. The app is the vehicle. So think about the service you want to deliver first, then build the app around that.
Jesse discusses the challenges of figuring out a market and selling a product while also developing it out per the feedback they were getting in near real time. They also had to take into account that there were multiple parties involved that affect the tool and how to get them on the same page. He also talks about getting partnerships off the ground.
Jesse offers advice when it comes to raising capital. As he says, “Raising does not only take a tremendous amount of time and energy, but it can be a very soul-sucking endeavor.” Jesse says to avoid unless you absolutely must have it. He also talks about how startup costs for anything technology related are so small compared to years ago that you should exhaust everything there first. It is a lot easier to start a company, but a lot harder to raise money based on just an idea. Investors want to see that you have a good team, good plan, and that you are executing on it. Get some proof and traction first. Lastly, Jesse makes it important to note that people try to raise money too early.
“Do not raise money unless you absolutely have to.”
At the 28 min mark, Jesse talks about marketing and hustle and gives some great tips on business in general.
Elements of a great pitch:
Best Quote “Whatever you initial idea, it is not going to be what the ultimate idea is. Don’t be afraid to throw your baby out.”
Jesse's Misfit 3