Alright – so today we’ve got the honor of introducing you to Caitlin Fine. We think you’ll enjoy our conversation, we’ve shared it below.
Caitlin, thank you so much for joining us today. Let’s jump right into something we’re really interested in hearing about from you – being the only one in the room. So many of us find ourselves as the only woman in the room, the only immigrant or the only artist in the room, etc. Can you talk to us about how you have learned to be effective and successful in situations where you are the only one in the room like you?
I joined the Navy when I had just turned 18, so I am used to being either the only woman or one of a few women in a much larger crowd of men. I am confident that my accomplishments stand for themselves and demonstrate my abilities. In the Navy and in school, I was always a hard worker and top performer, and people respected that regardless of my gender. I’m told I was sometimes belligerent when I needed things to get done- in a masculine environment, assertiveness typically works well (although sometimes when women do it, it’s called “being bitchy”). On motorcycles and the offroading/4×4 world, I know the places I have gone and the sticky situations I have overcome out in the wilderness. I also know I probably had to work harder to learn how to ride motorcycles offroad with my shorter legs and not being as strong as most male riders, but still, my stories can stand up there with anyone’s. I think confidence and outworking the competition goes a long way!
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
Based in San Diego, Edge of Adventure Tours offers BMW GS motorcycle rentals, custom guided single and multiday motorcycle tours, and a range of logistics support, everything from route planning to a chase truck, in Southern California, Arizona, Utah, and Southwestern Colorado. We aim to provide a seamless fly and ride experience to maximize your time off. If desired, tours can be all-inclusive, with guide, airport pickup, booking your hotels for you or providing camp gear and setup, a ride-along mechanic, and a luggage chase truck. Or, we can just provide panniers or soft bags and a GPS programmed with routes for your desired difficulty level if you want to be self-sufficient. We also offer family-friendly single day offroad truck tours based out of San Diego with no experience necessary, and can help plan your hiking or backpacking adventures as well!
Edge of Adventure Tours is woman veteran owned and operated. Team members have lived in Arizona, Colorado, and California. You can adventure with confidence with our well-maintained BMW GS rentals and guided tours or GPS tracks on trails we have personally scouted with our decades of experience in the Southwest!
We will have a booth at the premiere overlanding event in the country, Overland Expo West in Flagstaff, AZ, from May 17-19! We will be offering long weekend tours of Southern California and Northern Arizona this summer on demand, visiting destinations like Big Bear Lake in California or Sedona and the Grand Canyon in Arizona. These tours can be point-to-point or base out of a central location and ride day loops. We can also craft a custom tour for your group on dates that work for you in Southern California, Arizona, Utah, or Colorado. Single day tours and motorcycle rentals are always available in San Diego. Additionally, we offer half-day truck tours of the wilderness near San Diego year-round, and full day desert offroad truck tours from fall-spring.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
I think perseverance has always been one of my more distinct qualities. From getting my black belt in high school, to slogging through the U.S. Naval Academy, deploying on a ship, or falling over and over and over again on a dirtbike in the mud, I needed to grit my teeth and get back up- and sometimes pick up my 300 lb motorcycle too. Now, did I literally ship my motorcycle away from Hawaii to get it out of the mud after too many of those experiences? Yes. And then the Navy sent me to muddy Mississippi, joke was on me. But I digress. I think persevering through hard times and long days in pursuit of starting a business is a key attribute. You don’t always get to be the “technician” working on the fun part of your business. Doing any sort of hard experience for an extended amount of time, showing up again and again, will build perseverance (or it will “build character”, as the military says). Being an entrepreneur adds an extra hurdle to this, though, as there likely is nobody forcing you to do the hard things and you must find internal motivation! For me, external motivation abounds in the military where I spent most of my adult life, so not doing the hard thing was not an option.
In the realm of motorcycles especially, I think humility is key. I know I’m not the best or fastest motorcycle rider, but riding within my abilities and at a safe speed lets me not crash and break all my bones like my friends sometimes do. Most recreational riders could probably still learn something in a targeted class or on a hard enough trail! Adventure bikes especially are usually over 400 lbs- 250 lbs more than me. Sometimes there’s no forcing my bike to do what I want, and in that moment I just have to accept whatever is going to happen and try to ride it out. I think humility helps me be more empathetic when customizing routes for my tour guests. I understand when they may be nervous to go offroad or do a more challenging trail. I’ve been on too many rides with guys who swear the route is “easy” or “moderate” and gotten thrashed for my trouble. As far as business goes, I know I’m not the most knowledgeable business person either! My master’s degree is in Atmospheric Science, not an MBA. I acknowledge that I can learn from more experienced business people and am even taking some business classes with my GI Bill to help me improve the administrative side.
What would you advise – going all in on your strengths or investing on areas where you aren’t as strong to be more well-rounded?
I, personally, try to strengthen the areas in which I am deficient to become a more well-rounded business owner, and I think that strategy works in life as well. I am and always have been great at predicting the weather and getting good grades, for instance, but those are not the only skills that I ever need in life. I was always “book smart”, but did not have a lot of practical skills to fix or make things. I learned how a combustion engine worked in thermodynamics class, but couldn’t have told you what the parts of my car engine were for a while besides the battery. I didn’t even know how to change a flat tire until 2017 (I asked my dad once, and he told me to stand on the side of the road and look sad until a man stops to help me). Now, I consciously work on my practical skills like car and motorcycle maintenance, which transfer over to my business and also make me less susceptible to being conned into unnecessary services at a mechanic shop! I’ve had a few pitfalls along the way, like changing the rear brakes on my Subaru Outback and having them fall off on the highway. Oops! With some subsequent brake changes, I think my success rate is somewhere around 90% now, but you really want that one to be 100%. Potential guests, don’t worry, my business partner deals with all our high-consequence maintenance items and his success rate is 100%. Mistakes aside, I derive a lot of satisfaction from seeing the tangible results of my labor and knowing how to do things and how systems work and interconnect that I didn’t know a few years ago. Or for another example, learning some accounting to run this business helps me understand the financials better and strategize appropriately. I am trying to learn some marketing to broaden my reach, even though I am not a creative person and all my schooling was in science and math. If I just focused on my strengths (route planning, weather prediction, and riding motorcycles), the administrative side of the business would suffer.
Contact Info:
- Website: https://www.edgeofadventuretours.com/
- Instagram: @edge_of_adventureco
- Facebook: https://www.facebook.com/profile.php?id=100095554358564

