(in)Frequently Asked Questions

Questions nobody asked, answered anyway.

Stephen, in glasses and a green Upstream Alliance shirt, talking to a TV reporter holding a microphone on a Chesapeake beach, with a teammate beside him.

What's the most surprising thing you've learned in sales?

The most shocking professional fact of my life is that I've made friends with people I met cold calling. It's hard enough to keep someone on the phone for more than 11 seconds. So when I do close, I'm invested. I know their situation, their tone, and the angle that gets their team excited. The hardest part is passing them off just as they're getting started. I don't want to sell them a treasure map that automates the worst part of pirating on the high seas. I want to grab an eye patch and get on the boat.

Stephen in a blue jacket and bright knit hat sits on a bench beside his wife in a green jacket, both with their feet in flood water in front of a white house.

Where did you meet your wife?

Short answer: college. Real answer: sea kayaking around the Delmarva Peninsula. Roughly 500 miles (opens in a new tab) while I worked for a brand-new nonprofit called Upstream Alliance (opens in a new tab).

Stephen in a ranger uniform and blue pack, standing on a rock ledge high above a green forested gorge.

Why did you get your MBA? It's not the 90s anymore.

I went to the best forestry school in all the land, and I spent years creating content to convince people to adventure responsibly. It didn't prepare me for the career I wanted for the rest of my life. Western Carolina's MBA was a stellar multi-tool, full of working professionals and real problems to solve. I thrived in the night-school format and graduated near the top of my class.

Stephen in red sunglasses and a life vest, smiling from the front seat of a two-person sea kayak with a paddler in a green sun hat behind him.

Why should we pick you over someone with more experience on paper?

I've taught trail crews, volunteers, and a 77-year-old volunteer to build a Salesforce dashboard. I can teach your customers. Give me a task with as much information as you can, and I'll get it done.

Three huskies in harnesses looking at the camera on a snowy trail, with more dogs and sleds behind them.

What's working with sled dogs like?

Spectacular. There are more ears to scratch than minutes in the day. You do scoop literal tons of poop. It's not as complicated as you think to learn 40 names at a time. It's harder to tell their butts apart when you're flying on a sled behind an 18-dog team.

Stephen in a yellow hard hat walking across a snowfield above an alpine lake and mountains.

Why did you go from working on a trail to punishing a keyboard and cold calling?

I thoroughly enjoyed working outside for a decade, but I needed to step away for a better balance between work and life. I still volunteer on my local trails. I don't plan on going back to the work, because I need the trail to be where I teach my daughter, not where my work stress lives.

Any professional dreams?

Already accomplished. I have been Smoky the Bear on multiple occasions.

Did you really walk from Georgia to Maine?

You bet, buddy! I started in 2014 and finished 2,189 miles later. I would later join the Appalachian Trail Next Generation Advisory Council and work for the ATC for years.

A hand-drawn map of the Appalachian Trail from Amicalola Falls and Springer Mountain in Georgia to Katahdin in Maine, with a red line through the 14 states and little drawings along the way: Max Patch, the Mount Rogers ponies, the Homeplace restaurant, McAfee Knob, the half-gallon challenge at the trail midpoint, a mother bear and cubs, the Hudson River, a beaver, Mount Washington, and a moose.