From Corporate Life to the Call of the Wild

Keith Oberlin and Ben Ancher

[Repost from Stride Stories: From Corporate Life to the Call of the Wild | August 8, 2018]

Interview with Stride Health’s Rose-Ann Thomas

Hi, Keith! Can you tell us a bit about your background? 

Keith: I’ve been working in corporate America for most of my life. Even before I graduated from high school, I’d been working in an office environment and geared myself toward pursuing a career in the legal community. I went to college and ultimately popped out on the other end working for a private legal publishing company during the dot com era when life was a bit crazy. I then abandoned my career goals and off I went to pursue a career in technology. Since then, I’ve done a myriad of things: I’ve worked in the legal community—not as a lawyer—and in software development and startups. However, there was always the call of the wild.

My life has always been an interesting balance: while I very much exist in corporate America and big city life, I’ve always enjoyed the outdoors as early on as family trips I took kayaking and canoeing in waters near the Canadian border. I’ve always wound up doing things in and around the outdoors, getting my friends outdoors, and organizing outdoor activities. Ultimately, that led me to creating Get Out And Trek, which is meant to focus in on my passion for being outdoors and turning this into a career. I've been doing this for about a year in an official capacity.

I’m sure that there are growing pains or new areas to constantly learn about for this job. What are some challenges that you’re experiencing during the earlier stages of the company?

Keith: Yeah, absolutely! The biggest challenge that we have is our network. With starting a new company—especially in this day and age with people being overwhelmed with social media—it’s hard to get a level of engagement with the target community you’re trying serve, so networking is definitely my biggest challenge and current goal! That’s how I think we’re going to be able to find the right ways to grow our customer base.

When you talk about networking, are you leaning toward an in-person approach or are you looking more towards digital media?

Keith: Both, quite honestly. We’re looking to create partnerships in reputable organizations that people already believe in, whether those are community based organizations, clubs, nonprofits, or established brands. Working with companies like REI, Burton, and The North Face to create events can help demonstrate our viability as an organization. Brand ambassadorships can help in that aspect as well. It’s important to have that sort of mentality of engaging people in the real world. Then, in the online community, we want to make sure that we have a social media presence and can market to people through social media. We’re early enough that we do not need to be focusing on other marketing avenues, but having content in blogs like this [Stride’s blog], getting articles inside Time Out New York, and producing other online content is another really important way to extend ourselves.

I’m sure you must run into other companies or initiatives that share your desire to provide opportunities that provide a welcoming space for the LGBTQIA+ community. Have you had the chance to reach out to them and collaborate on any projects?

Keith: Absolutely. We’ve been working with local climbing gyms who really want to make sure that they are able to speak to and support the LGBTQIA+ community. When we are able to partner with them on events, we help them with these goals and then while doing this, we’re able to work with them to demonstrate ourselves. We’ve already worked with climbing gyms, cycling organizations, bike shops, and even sports drinks and apparel companies! It’s been about finding those partnerships where people don’t necessarily sit in the LGBTQIA+ community, but want to be able to speak to them. We partner with them to be able to create events and opportunities that they can’t take on. For example, a local sporting organization here in New York City was looking to have a Pride event and wanted to make sure that the people that they brought into the environment was on message, so they brought Get Out And Trek to host their Pride Happy Hour. It brought the outdoor sport community together with what they were offering.

What does a typical day look like for you? 

Keith: It's helter skelter all the time. [laughs] I think planning activities to take people outdoors is very logistics-oriented. We don’t have a single sport that you show up to like skiing, where you’d just drop people off at a mountain and let them do what they need to do. I’m moving from one site to another because doing multi-sport trips require a lot of logistics, planning, thinking through who the right vendors are, and thinking through what the right timing and sequence is—when one vendor doesn’t work out, suddenly that means that the next three that you were going to select might not either. This all really requires a lot of thought process and time to do that, and yet, while you’re trying to do that, you’re also trying to be able to grow the company and reach out to new members, which is all marketing. Those two types of activities oftentimes deal with different parts of your brain: one is detailed project management and then you switch gears to be social and engaging to network and build a brand that reaches more members. These two sides compete for time in my head and everyday it’s just dealing with the prioritization of what’s the most important task for this week or this day, and creating the best balance possible.

That sounds like a ton of work! Have you had the chance to reach out to other self-employed people or maybe the larger self-employed community to get insight on how to run your business or is this a one-man show?

Keith: You know, there are other people inside the LGBTQIA+ outdoor sports community, as well as just other people that do outdoor sports and sporting adventurism in general. What I’ve started to do is connect with others that have been more established within the industry to talk about their challenges and their growth strategy, and seek advice and counsel from them. I don’t have a board of directors as part of Get Out And Trek, so I treat other people in the industry as though they’re my mentors and advice channels. This way, I have a way to know for sure whether an idea that I have is indeed unique or whether something is tried and true. The most important part is definitely listening to other people who are out there creating successful businesses and learning from them, from the industry, and from myself.

What’s been the most helpful piece of advice that you’ve gotten?

Keith: One of the most important things for a strong and stable company is to be very mindful of your finances and how you're managing your books. That will save you from a lot of trouble. There's lots of other trouble that you can get into, but you need to make sure that you're thinking through the financials of your company. Staying solvent allows you to do a lot of different things as an organization, but when you suddenly get into financial trouble, you start sacrificing your principles, the goals of the organization, all of those things.

What would you suggest to a person who’s interested in being self-employed, but may be concerned about challenges such as finding insurance benefits or funding their endeavors?

Keith: Hmm. It's scary! It's scary to take a plunge. I think that thinking through things from a financial perspective allows you to feel significantly more comfortable in making those decisions. If you have a strong business plan—and it doesn't have to be a massive formal write-up—but if you have a strong business plan and a thought process in which you currently have operating capital and a plan to be able to create sustainable growth, then from that comfort you should be able to take a plunge. It will still feel nerve-racking, but from there, you should feel comforted in the fact that you’ve thought through what the necessary steps are and you’ve developed a plan to try to achieve that.