The Transition From “Work” To “Passion”

April 24, 2023

During our August Virtual Lunch, VAULT was joined by Jake Gafner, founder of Lost Travel Company and Wayward, on the one year anniversary of leaving his full-time job to pursue his passion.

During the many conversations our team has with founders, entrepreneurs, and innovators, we often see a common theme of questions such as “when does it make sense to take the leap into full-time entrepreneur?” “how do you do it?” and better yet “how do you survive it?” Throughout the event, Jake helped answer these questions and provided tips he’s learned along the way. To download and listen to the entire event click here.

As a company, Lost Travel is known for the events they organize and the special value they place on the “journey of a trip”. All organized events have a start and a finish but the in-between is completely up to the participants. Participants carry their own gear, chart their own course, and are completely unguided. What else makes Lost Travel so unique is that through the software they’ve built, participants can run an application on their phone during the events that allows spectators at home to follow along on the journey.

Jake and his team also care for the environment and gives 5% of all proceeds back to the planet, typically giving back to the areas in which their events take place.

The Factors That Play Into Deciding To Leave Your Full-time Job

Jake and his wife have always dabbled in entrepreneurship and have a shared passion for travel, the outdoors, and the experiences you can create. They’ve always desired to organize the type of events that they’d enjoy because they couldn’t find any other companies that were creating them. So in 2018, the couple created their first event in Wisconsin and from there, they’ve been creating events around the country ever since.

There have been many late nights and weekends over the last year but looking back, Jake can recognize many confidence-building dates. The first big milestone was seeing the company’s first true customer sign up, someone neither Jake nor his wife knew. While their customer base was starting to grow, Jake was working for another company and the responsibilities of his full-time job and that of Lost Travel were starting to become overwhelming.

“There would be times when a Lost customer would email me at 9 AM while I was at my day job and I would feel anxious all day wanting to reply but at the same time wanting to keep a hard line drawn on hours worked at my day job vs. the hours I worked in the evening on Lost,” said Jake. “Everyone always talks about passion but it’s true, there was never a minute spent on Lost, even the boring stuff, that felt like work.”

Once Jake started feeling that tension for competing interest of his time he knew it was time to start evaluating next steps on an exit strategy.

Considerations That May Cause Pause On When You Should Quit

Although Jake is someone who can find the good in most situations, the financial side of things is always something to consider when starting your own business. For Jake and his family, it was important to make sure they had the right amount of saving in place in order to make a transition work.

The original plan was for Jake to talk to his current employer about scaling back his hours but based on his role that wasn’t a good fit. In the end, Jake was able to transition away from his day job within a month which allowed him to finish up items he was working on while continuing to focus on Lost Travel.

How COVID-19 Impacts Business

The travel industry is one that has been massively impacted by the global pandemic we’ve been facing and has required Jake to pivot his company in various ways.

Back in March, Lost Travel had three trips planned for the future months with several customers booked and excited to participate. With the future filled with uncertainty, Jake refunded all customers or allowed them to use it towards a future trip. The pandemic could have acted as the perfect scapegoat for Lost Travel to close their doors but instead, Jake chose to realign and refocus the team’s energy on internal projects that needed to get done.

They decided to allocate time and financial resources to items that had been sitting on the backburner; one of those being the new Wayward application. The company has also shifted how they run future events because Jake knows people will still want to enjoy the art of travel. He knew he needed to find a way they could run events that were safe from a COVID-19 perspective which meant taking social distancing measures and marketing more towards people locally so participants won’t have to fly in.

Why Wayward Was Created

Jake wanted a way to share his and others’ adventures but for the types of trips he was doing and creating, there wasn’t a good solution. So Wayward was designed to solve three problem areas.

  1. A real adventure lasts more than one day. There are a lot of great trackers out there that are used for running and biking but Jake needed something that could track weeks and even months.
  1. The great adventures, in Jake’s opinion, tend to go where cell reception doesn’t, so they needed an application that would continue to work without reception or WiFi.
  1. Jake wanted a solution that didn’t require participants to buy a piece of hardware, such as a GPA tracker, or have to pay the monthly data package that typically comes along with those devices.

Wayward is a mobile application for iOS and Android that is for tracking and sharing your adventures. To share, there is a single button that links to a web map, you don’t need to download the app or register for anything in order to view a participant’s adventure.

Advice For Those Looking To Make The Transition

“The best advice I can give is, if you have conviction in the thing you’re building, have the confidence that you’ll figure it out,” said Jake. “People are willing to help you out and give advice just because they believe in what you’re doing.”

Jake also recommends reaching out and finding an advisor. He says his advisors, like the team at VAULT Innovation, continue to give him valuable and important information on a regular basis.

Want to learn more about VAULT Innovation and what our team of experts has to offer? Send us an email to see if there is a fit to work together.

You can also learn more about our guest speaker, Jake Gafner, founder of Lost Travel Company and Wayward, by visiting his website.

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