As Amy and I planned out her shoot, she mentioned she wanted to spend part of it doing what she loves most: backcountry skiing. Our first pick day had considerable avalanche conditions and wind loading on the slopes we were planning to ski - but our second pick day was stable. That morning, I drove up to Coal Creek Trailhead, at the base of Teton Pass. I spent most of the drive paranoid that I forgot to bring my poles.
Amy and I exchanged hugs and spent the morning on a tour with several transitions. I ate my first energy goo, we talked about risk appetite, grit and securing venture capital as a woman... and we skied some deep powder. We did her interview at the top of Teton Pass after touring, as she drank the rest of her coffee and I happily ate the remainder of my breakfast. As a former ski bum and current entrepreneur - there was something extra special about sitting in my car, exhausted with our skis loaded into the back, unceremoniously eating a burrito and talking about start-ups with a woman who had the grit and perseverance to start a small business and go back for round two.
Q: From day one to where you are now in your startup journey, what have you learned?
Amy: It's been a huge learning curve. Even though I've been absolutely clear that this is my path and this is what I want to be doing in life, I had to learn how to start and run a business. Everything from LLC paperwork to filing an annual report.
Also,I think a big one that I vastly underestimated was how much marketing would be required to really get Garage Grown Gear into motion and create that momentum around it. For me figuring out how digital marketing works was like learning to swim while already in the pool.
I think the biggest thing that I've had to learn through all of this is how to approach entrepreneurship. I initially approached entrepreneurship like how I approached academics — which was an attempt to be perfect. I was a perfectionist and straight A student — Valedictorian, Summa Cum Laude — which is actually a terrible background for being an entrepreneur. There's so much trial and error and f-ing up and sometimes having to realize good is good enough. I really had to draw in perspective to what I was doing. I had to learn to soften the edges around perfectionism.
I would say another big one is leaning into the discomfort of saying no and disappointing people. I've had to learn a lot on the fly over the last several years.
Financials are a big one. I cried over a lot of spreadsheets. Now I can whip through financials. It was tears that got me to that point.
I think it is good to learn from other people's experiences. It's really important and you can save yourself a lot of heartache and headache by doing that. But ultimately nobody knows your business better than yourself. At a certain point you have to step into that leadership role and just own your own vision and be like, ‘Yep, I know that this isn't what you recommend but this is how I'm doing it.’
Q: Walk me through your timeline with starting up two businesses and selling them.
Amy: So 10 years ago, almost exactly, I drove 3,000 miles with my dog from Alaska to Jackson hole. I didn't know anyone and had passed through the area maybe once but I had never spent any significant amount of time in Jackson hole.
Up in Alaska, I was the editor at a community newspaper that was owned by a nationwide conglomerate. It was right when papers all over the country were going through bankruptcy. As this was happening, my job very much pivoted from good community journalism to managing corporate constantly. I just had one of those moments where I was like, I don't have a significant other, I'm on month to month with my rent, and I can literally do anything. So I packed up my car and drove 3,000 miles. I'd always wanted to be a ski bum. In my mind, if you're going to be a ski bum, Jackson Hole was where you go. Through a friend of a friend of a friend, I found a room to rent.. I showed up at Jackson hole Mountain Resort and tried out to be a ski instructor and got a job. That's how I ended up here. That was 10 years ago.
After a winter as a ski instructor, I was filling in for someone on maternity leave at the Jackson Hole News & Guide. That's where my husband and I met. Up until that point I thought I was just coming here just for “one winter.”
I started Jackson Hole Packraft in 2011. That was really cool because it was definitely a micro business, but it taught me all the stages of a business — everything from learning how to create an LLC to learning how to set up partnerships. I had a partnership with Rendezvous River Sports, so all the packrafts went in and out of Rendezvous Rivers Sports locally. I had micro investors that helped me with capital to buy the rental boats — so also learning how you manage investor relationships. I eventually hired someone super part-time to do the rentals for me and learned how you hire someone, how you manage someone. Then I eventually sold the business, learning how you have a business exit and what it looks like going through that process.
I started Jackson Hole Packraft was when I was a new mom. My daughter was born in March of 2012 so even if it was a micro-business, having a micro-business while being a new mom was intense. It was a really good experience. We had our local rentals, but we also rented throughout the country, much like a satellite phone rental. We put packrafts in a box and shipped them anywhere in the country. When the renter was done, they put them back in the box, we supplied their rental label, and it came back to my garage. About 70% of our business was out-of-state rentals. It was really cool. Jackson Hole Packraft really set the foundation for me to take on Garage Grown Gear.
I started Garage Grown Gear six years ago. It all started on my kitchen counter. Three years ago, we merged with another online store and magazine, Big Outdoors which was run by Llyod Vogel. We say we're co-founders because we both play that role.
Q: Where are you now, as a freelancer and working for Garage Grown Gear?
It's kinda hard to explain what I do because I have my hands in so many different things sometimes. But if you boil down: I work with other founders and I write. It can come in a lot of different forms.
Currently Garage Grown Gear is an online store and magazine that spotlights small, startup and cottage outdoor gear brands, mostly in the ultralight backpacking space. We're currently closing in on a hundred brands that we sell through our store. We view it as a collaborative platform. Big box brands and big box retailers take up the lion's share of the outdoor industry so it's a space where we can link arms as the little guys and make our voice heard. I also freelance and work directly with some of those small outdoor gear brands. I have four brands that I work with on a consulting basis.
My largest client is Give’r. I do all of their newsletters and general marketing strategy. I’m very much a part of the team over at Give’r. Then my smallest client is a once-a-month phone call and I literally just get paid for an hour where I consult, which is great. I also run PoleClinometer, which is under the umbrella of Garage Growth Gear, but I run most of the business stuff for that as well.
Q: What is your favorite part of being your own boss?
Amy: It's exactly what we did today. We went out to ski on a Monday and I had full discretion to make that decision and didn't have to check with anyone else — even though I'm gonna work my butt off the rest of the week to pull it off. And I love that my work is judged on deliverables and not hours. So it's totally up to me how I meet those deliverables at the end of the day.
Q: What’s the most challenging part about working for yourself?
Amy: I think overall, I'm somebody who works for myself well. I'm not even sure if I'm employable anymore. I think my least favorite part is boundary setting. Work and life can definitely meld together sometimes. I love that I'm always home and my husband's always home (because he works from home too) when my daughter gets off the bus. Love that! That's amazing! What I don't like is when she gets off the bus, gets the snack and then it's like, okay, I need to finish up this project. I need 20 more minutes, please go watch a TV show. I don't love that part.
The other part I don't love, and this is much more on a societal level, but our society is not well set up for people who work for themselves — whether you're talking about how you pay taxes or how you get health insurance or any of these other things. My business partner lives in Minnesota and we’re a Wyoming LLC, but I live in Idaho. And then we also did an event in Wisconsin. So now suddenly we had to pay sales tax in Wisconsin, Minnesota, Wyoming and Idaho.
Q: What does your day to day or week to week look like?
Amy: I'm very structured with what I do. Every single Friday, I plan out my next week. I pretty much know what Monday through Friday are gonna look like for my next week. I always do phone meetings on Tuesday or Thursday afternoons. Mondays and Fridays I generally keep as clear as humanly possible and that's my creative time and space. I feel like there's two very different aspects of what I do. One is the very creative inward journey and the other is very collaborative and outward interacting with people. I have to carve separate time for those two different things. I can't quickly go back and forth between the two.
I am also very, very careful about what sort of distractions there are and who can get to me.
My phone is quite often on silent. There's nothing that can pop up on my computer — all of my notifications are turned off on my computer.
Q: Do you have anyone who has been a pivotal mentor within the startup community or business community at large?
Amy: That's a very good question. I would say that there wasn't any one person but I would say that there were many, many people who have very generously given of their time and expertise.
I cannot tell you how far I got on buying people coffee. People are incredibly, incredibly generous in that way. This is more recent, but last year I participated in Womentum, which is a mentoring program. It's really cool. They pair you with a mentor and then there's also group events every single month. Sometimes it's a workshop, sometimes it's small group dinners, but there's a group event every single month. So you get to know your cohorts pretty well. Then you have your mentor and my mentor and I just completely hit it off. She's awesome. She's a physical therapist, so she's not even necessarily in my professional space, but now even though the program is over, we're still in really good touch. That has been really cool.
Q: What are some skills that you have that you’ve found were really useful in the startup world?
Amy: I would say my background as a journalist and a writer and being able to communicate is great for what I'm doing. In particular, as a journalist you're writing, but you're also constantly reaching out to random people to talk to them. I'm a total introvert but I can also reach out and talk to random people. You get into that cadence and you're realize, yeah I'll get rejected. I'll get told no. But I’ll also get told yes.
Q: As a founder of multiple startups, what is your comfort level with risk?
Amy: For me, weirdly the risk is in identity. What will people think of me? It’s not so much the financial risk. I mean it is partly. But for me it's like I work so hard to promote this vision and believe in this vision and get other people behind this vision. So you want the vision to work. So that fear of failure when you ask people to put trust in you — that's the hard one for me.
Q: Talk to me about work life balance.
Amy: Work-life balance is not something historically that I’ve been good at. At one point when it was just me, Garage Grown Gear literally brought me to my knees. There was definitely a come to Jesus moment during one December, which is holiday sales. For me it was and is mental health like anxiety and insomnia that forced a reckoning. Let's put it that way.
That was right when we merged businesses with Lloyd. That was a game changer. Having someone else to collaborate with and divide and conquer tasks with, to have somebody who cares as much about this thing as you do, to talk through all the processes of the business. That was really a transition.
That was when I started to put really clear boundaries on place. I don't check email on weekends. I don't even have a Gmail app on my phone right now. I do my very, very best to put my phone in a different room at night when I'm with my family, so I'm not even tempted to look at it or check to see what's going on.
I very much like getting out and doing things like skiing, but I have a lot going on and then there is a fine line. Sometimes I’ll stress myself out — like that day of playing was fun, but I can stress myself out too much over it. But sometimes I'll just be like, f- it I'm going skiing. It'll work itself out, you know?
It’s definitely something you have to teach people: I don't respond to text messages right away. I do respond to text messages, but it might take 20 hours, you know? For me it was especially figuring out how to be a founder of a digital business but not have the digital world always in my life. That was important to figure out.
The other thing I would say: I think being a mom and a startup founder is incredibly challenging, but it did force my hand. When you have a kid you just have to say no to things. Five o'clock comes and your kid's home and needs dinner and needs attention and that’s just it. Weirdly enough, being a mother is a good thing for setting boundaries.
Q: If you could go back to the beginning and give yourself one piece of advice, what would it be?
Amy: Don't be afraid to fail. It's not that big of a deal.
Q: If you could convey one message to people, either about Garage Grown Gear or about what you do, what would it be?
Amy: I think there's so much mystique around startups or even creative freelancers. It’s just a very romanticized societal thing. And it is - like my life is amazing. I truly have such an amazing life! So I see why it’s romanticized. But I think like there's two messages that are both important. One: anyone can do it, right? There's nothing that makes me particularly special other than having the gumption to do it and sticking it out. The other thing is: it's not the easy path. It’s not the easy choice. If you are going to do it, which I totally encourage people to do, if that's what's stirring in your soul, just know that there are gonna be some bumpy roads. It’s that ability to step into the discomfort and be in the discomfort. That's what’s going to get you to where you want to go.