We were already impressed with the great work Kay Rodriguez was doing as Founder and CEO of Urban Outdoors before we were a mentor for the cohort she was in with the Waypoint Accelerator program. After meeting her, we were even more impressed with what she’s accomplished with Urban Outdoors, building outdoor communities in urban areas. Even though she’s been busy traveling from her HQ in DC to the WNC area for her Waypoint Accelerator graduation and the upcoming Outdoor Economy Conference, she was able to take some time for a quick interview with the Darby team. In this installment of Coffee Talk, Kay tells us what she’s up to and shares some fun personal facts, like how she emails Shark Tank presenters with critiques of their pitches (spoiler: none of them have ever responded to her emails). Read more below!
Kay, thank you for taking time out of your crazy schedule to chat with us, let’s kick it off with a question we make most Coffee Talk interviewees answer, what’s your birth sign, and do you think it fits your personality?
Taurus! I think it totally fits me from a stubbornness perspective, but I like to think I’m a little more willing to get out of my comfort zone than the typical Taurus stereotype.
Urban Outdoors is such a cool concept! Can you tell us how you founded it and where you see it growing in the next 5 years?
The idea for Urban Outdoors was born when I was living in Chicago in 2019 and aching for some time in nature. If you know Chicago, you know the winters can be brutal, and it was starting to get darker and darker every day.
I couldn’t find any good information on hiking trails and outdoor areas in Chicago, so I jumped in my car to find the best local spots for hiking and published a few guides on it on the internet. I also wrote up guides to DC and Houston, cities I’d lived in before. Fast forward a few months, and our website was getting over 10,000 visitors a month. I knew at that point we might be onto something.
I realized that most cities don’t have a central hub of information on urban outdoor activities in the area, so many people have to resort to traveling far away to get their outdoor fix.
At that point, I hired a writer in New York, moved into my campervan, and we were off on our mission to share outdoor activities in cities around the United States. Two years later, we’ve got an audience of over 150,000 unique monthly readers, 17,000 newsletter subscribers, and we’ve just opened our waitlist for the Urban Outdoors community app, which we’re launching later this year.
We’re also considering seeking investment funding to help us scale quickly and serve more cities around the United States. In the next 5 years, we want the phrase “Urban Outdoors” to become synonymous with taking an adventure in your own city, with an enthusiastic community of members on our platform who are passionate about their local outdoor spaces.
You list activities in 50 cities in the US and Canada, how do you source all of this material? It is all you or do you work with writers across the nation to vet the activity suggestions?
We use a mix of personal experience, an extensive personal network of outdoor enthusiasts, audience suggestions, and in-depth online research. We gather information from various sources because we want to paint the most detailed, robust picture for our community members. We want them to feel as confident as possible when they get out for an adventure.
Tell us about Outdoor Happy Hour, what is it and where are they held?
The “Outdoor Happy Hour” is the idea that you can replace your normal social activities with outdoor activities. Whether it’s a walk in the park, a hike, or a sunset paddle, there are so many ways you can get outdoors after work or in your limited free time.
Since we started Urban Outdoors right at the beginning of the pandemic, the Outdoor Happy Hour hasn’t yet become an in-person event. But once we get our app up and running, we’re hoping to organize these during the week for our community members in many of the major cities we operate in.
We saw that you were a vanlifer for a while, are you still living out of your van today? If not, do you still have your van, and do you still go out on extended road trips?
I was! I converted my 2011 Mercedes Sprinter at the very beginning of the pandemic and lived in it full time for just under two years with my husky, Aurora. We traveled all over the United States, to over 30 states, before settling back down in the Washington, DC area. Luckily, I still have the van and am planning on using it as a “vacation home” of sorts.
What’s your favorite city and what is your fave outdoor activity to do there?
It’s a tie: I love San Diego and Seattle. Both have awesome outdoor activities (in different ways) and a fun local vibe. Plus the van life options are great in both places!
We read that you taught yourself to snowboard and to surf, that’s so cool! If you could only do one or the other for the rest of your life, which one would you choose?
I’d definitely choose surfing (sorry, snowboarding!). I love the sunshine and the fact that every wave and break is different.
What song/artist is on replay for you right now?
I’ve been really enjoying Kishi Bashi lately – I’m a former violinist and the way he incorporates orchestral instruments into his music is so mesmerizing.
Top 2 favorite hikes?
The O Circuit in Torres del Paine, Patagonia, and McCullough Gulch in Colorado. Both absolutely stunning, yet totally feasible for the ambitious (and less experienced) hiker.
Are you into podcasts? If so, what podcast should we check out that you’ve been into recently? If not podcasts, what book are you reading right now?
I love podcasts AND books, but I’ll share a book. I recently read “Never Split the Difference” by Chris Voss and it was awesome – so full of interesting tips on how to negotiate from a former FBI hostage negotiator.
If you could share anything with your 16-year old self, what would it be?
Take conventional advice with a grain of salt! If I listened to all of the advice I’ve gotten over the years, I’d be in a completely different place right now. But because I stubbornly forged my own path, I feel very confident that I’m exactly where I need to be.
Tacos or Pizza?
What’s something people would be surprised to learn about you?
I’m a huge houseplant nerd! When I’m not doing all things Urban Outdoors, I’m probably spending time doting over my growing collection of tropical plants. Ask me anything about houseplants and I probably know the answer.
Anything else you’d like to share that we didn’t ask today?
We’d love to have you as part of the community! You can join the waitlist for the Urban Outdoors app here.
Find Kay at: (include website and any social channels you’d like to share)