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Jacob Gafner of Lost Travel: “Find mentors”

“Find mentors” — I’ve brought on a couple people to serve as informal mentors and it has been tremendously helpful. Get advice from somebody smarter than you who isn’t emotionally or financially connected to your organization. Advice from these folks is worth more than it’s weight in gold. The COVID19 pandemic has disrupted all of our lives. But […]

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“Find mentors” — I’ve brought on a couple people to serve as informal mentors and it has been tremendously helpful. Get advice from somebody smarter than you who isn’t emotionally or financially connected to your organization. Advice from these folks is worth more than it’s weight in gold.


The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Jacob Gafner.

Jacob Gafner is the CEO of Lost Travel, a company that believes the best adventures are unguided and unscripted. They build software for adventure and have been organizing one-of-a-kind trips around North America since 2018. Prior to that, Jacob held leadership positions at two venture-backed Tech startups as well as Operations leadership roles in Healthcare. He has a Master of Science in Engineering from University of Wisconsin, lives in Chicago with his wife and spends time all over the world when there isn’t a pandemic happening.https://content.thriveglobal.com/media/8a46130cd18de34d32648dcccf6ebd7d


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in Wisconsin and as a kid I spent a lot of time camping, chasing frogs, and building forts with my siblings. My high school class had 32 kids in it and some of my first jobs were on a dairy farm, as a dishwasher, and working at a cheese factory (it’s Wisconsin after all). After college at the University of Wisconsin I moved to Chicago for a girl which turned out to be an excellent decision.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

A principle that I live by is that life is short and unpredictable. There have been people in my life who have passed away too young and/or had the course of their life changed unexpectedly. I believe we should be really thoughtful about how we want to spend our time here and what impact we want to have on others. None of us know how much time we’re going to get.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

“The Lean Startup” by Eric Ries and “Zero to One” by Peter Thiel were both books that changed my perspective on building a business. I read them soon after I joined my first venture-backed company. Prior to that I had been working at a large medical institution and my previous business experience had been in a variety of small businesses that I had started on my own, with friends, or with my wife. These two books, among others, shed light on how fast-growing companies innovate as circumstances change and new marketplace information comes to light.

Another book I would highly recommend is “Braiding Sweetgrass” by Robin Wall Kimmerer. This has nothing to do with business but is beautifully written. It offers a unique perspective on the natural world and how humans (past and present) interact with it. Many of the themes in this book are fundamental to how we operate at Lost Travel.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

We started Lost Travel in 2018 as an adventure travel company. Our goal then (as it is now) is to inspire people to get out into the world, to challenge themselves, and to do some good while we’re at it.

We organize one-of-a-kind travel experiences across North America. Our trips involve camping, biking, kayaking, and more. What is unique about our trips is that we start and end them with festivities but in between participants chart their own course; we call this “unscripted adventure.” We also give 5% of registration revenue to local organizations that are taking care of the environments in which our events take place. Readers can learn more at www.lost.travel.

What did you do to pivot as a result of the Pandemic?

We launched a software product called Wayward. It’s an app for tracking and sharing your adventures.

The pandemic could have killed us (we’re a travel company after all) but it didn’t. Yes, we refunded quite a lot of tickets and cancelled trips when Covid started spreading across the US. Then we reflected and decided to double down on our mission. We got to work throughout May — Sept and in October we launched our app.

Wayward continues our mission by inspiring people to get out into the world by hiking, biking, and taking socially distanced road trips. It’s also a utility that helps event organizers, whose businesses have been disrupted by the pandemic, to coordinate socially distanced trips.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

There wasn’t so much of “Aha moment” as there was a “Ah, now it’s time.” We had known we wanted to turn our internal tool into an open product for individual adventurers and event organizers. We never had the time or resources to get this done with the pace of things before the Pandemic. When the pandemic restrictions first went into effect in mid-March it forced us to re-examine our entire business.

How are things going with this new initiative?

Wayward is off to a great start! Since we launched it’s been used in over 30 countries to track everything from bike rides and hikes to multi-week road trips. We are seeing more trips every week and we’ve got some exciting new features in development.

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?

We’ve been fortunate to have help and support from so many people that there’s no single person to call out. There’s a long list; from our friends and family, to our first few customers that signed up for our trips, to the first people around the world that downloaded our app. Nothing worthwhile is built alone.

Can you share the most interesting story that happened to you since you started in this new direction?

What surprised me is that as soon as we launched Wayward officially we had a few potential investors reach out to express interest in what we were doing. That’s exciting for how new the product is.

What are your “5 things I wish someone told me before I started leading my organization” and why. Please share a story or example for each.

  1. “Learn how to delegate”- This is something that has always been difficult for me but in a young growing company there is always way more work than one person can handle.
  2. “It will take four times longer than you expect.” — Everything, and I mean everything, takes much longer than you expect and it usually costs more.
  3. “Ask for help early and often.” — I am naturally somebody who tries to figure things out on my own. As soon as I started asking for help, I started seeing progress much faster.
  4. “Find mentors” — I’ve brought on a couple people to serve as informal mentors and it has been tremendously helpful. Get advice from somebody smarter than you who isn’t emotionally or financially connected to your organization. Advice from these folks is worth more than it’s weight in gold.
  5. “Have fun.” — Business is serious stuff but there’s no reason it can’t also be fun. Surround yourself with fun and positive people.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

This is a very important question and everybody has to find their balance as it relates to news. There are two things I’ve started doing this year that have helped me stay sane and focused.

First, I have started limiting when I read and listen to the news to just twice per day; before I start work for the day and at the end. I’ve found that spending 10–15 minutes on thoughtfully written and researched pieces is way more enjoyable and more efficient than compulsively checking news apps and social media (I’ve been guilty of this in the past).

Secondly, I’ve stopped ‘searching’ for the news and I’ve stopped using ‘real time’ news sources, like Twitter. Instead I subscribe to a handful of newsletters which do a good job of sifting through the day’s news and surfacing up what’s important. A few that I like are the NY Times newsletters, The Prepared, and Morning Brew. I think it’s important to remember that the most urgent news always has a way of finding us.

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

Our planet is just one of the many things that we all have in common. My goal is to inspire more people to get out and see the world in an effort to protect it. In Lean manufacturing there’s a phrase “Go to the Gemba” which means “Go to where the work is done and see it with your own eyes.” This leads to better decision making. I think the same principle is true as it relates to our planet. My hope is that the more we can get people out into the world through travel, the more they’ll want to speak up for our planet and protect it.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

There is an endless list of people I would love to have lunch with. For one, Ryan Gellert, the new CEO of Patagonia Works would be great to have a conversation with. Patagonia is a company that has long been an inspiration to myself and many others in the outdoor industry. They have a great story with very humble beginnings and they’ve shown that a for-profit company can be a force for good. It will be exciting to watch where Ryan leads the company in it’s next chapter.

How can our readers follow you online?

We’re on all the major social platforms. The best place to start is at https://wayward.travel or https://lost.travel. The links to all of our social channels are there.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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