Dylan Gallagher is the founder of Orange Sky Adventures and White Wolf Private Tours, two San Francisco-based travel companies that takes tourists on customized trips across the United States. Whether their budgets are modest or they desire luxury accommodations, Gallagher prides himself on providing customers with the ultimate hospitality and the most unique experiences the country has to offer.
Why did you start your company?
I’m from South Carolina. I went to college for engineering and got a job in engineering. But, I didn’t want to do that. So, I wrote down on a piece of paper what I wanted to do and what I thought was valuable in life – Things like family and travel and freedom. Then, I went and got a job that fit that spectrum better. I moved to California and worked as a tour guide. I traveled all around North America showing people around all the coolest spots. After doing that for five or six years, I realized I could do it better. I moved to San Francisco, started the company, and haven’t looked back since.
How did you fund the company at the start?
I had a little bit of money to start the company. I moved to San Francisco because I knew that was the area that needed the most help. I got a job there and started building the company. I worked a night shift at a hotel. Nobody would be there, so I would spend my time building the website and creating everything I needed. Once I ran out of money, I started putting some expenses on credit cards.
How do you manage cash flow?
You just have to keep it coming in – That’s the trick! You have to always be selling to the next person. You have to build the company online so that you have the reviews and have the support so that people just keep calling you.
What’s the most challenging thing about running the company?
Keeping the money coming in. We are seasonal, so we make a ton of money in the summer. But, we have to be like a squirrel and hoard our nuts for the wintertime. Last year, we had a bunch of fires in Yosemite, which made half of our winter stash disappear. It’s difficult to manage that rollercoaster, especially when you have employees who are trusting you. You have to make sure they’re taken care of first.
What’s the most rewarding thing about running the company?
It’s the support and the friends you make. The support from other business owners is great! They’ll really help you and promote you. It’s cool to do something you believe in and have fun with it. I try to help as many people as I can, and then other people help me and support me.
What’s the biggest mistake you made when you were starting out?
When you go to a bank, you have to ask for money when you have money. What happened is that I had about $9,000 to start the company. I thought when I ran out of that, I would just go to the bank and ask for a loan, because they’re always advertising small business loans. But, when I needed it, I couldn’t get a loan because I didn’t really have a job, so my personal income was zero. Though the business income was good for the first year or so, they needed three years of established tax returns to show enough history and credibility. If I could go back in time, I would have asked for a loan when I had some savings and a personal income.
What’s the smartest thing you did when you were starting out?
I came to San Francisco to start the business. This is where everything happens. If you want to be a movie actor, you have to go Los Angeles, because that’s where everything is. If you want to be on Broadway, you have to go to New York City. I came where everything is in my industry and where my service was most needed. Even though the city is more ruthless and more expensive, it’s where things are happening. You’ll know if you do well here, you’ll do well anywhere.
What advice would you give to a new entrepreneur?
Don’t quit. For a business, you go off on your own and you may be discouraged. In other areas of life, you have other people who have been through the same challenges and who can encourage you. Usually, in business, you don’t have anyone who can relate to your challenges. You have to have the inner strength to keep going and not take disappointments personally. If you take in negative feedback and make changes to your offerings, you’ll eventually start getting more ‘yesses’ than ‘nos’ from customers.
What’s next for Orange Sky Adventures and White Wolf Private Tours?
We want to grow, but we want to grow in a way that’s true to the brand and who we are. We’ve created a ‘mom and pop’ voice. We’re the little guy. There’s a big market of people who want that. We want to grow, but we want to do it in a way that we preserve that feeling.
This article was originally written on July 1, 2019.