Leader Spotlight Series: Ellen Oshinsky, Founder of Circle and Spoke
Jacinta Gordon | May 26, 2025.
This month, we sat down with Ellen Oshinsky (she/her), founder of Circle and Spoke, to learn how she’s creating meaningful connection through cycling retreats. We’re excited to share Ellen’s story—where she is on her journey now and how Wild Gift inspired her to bring greater intention to community building. Ellen was a 2024 Wild Gift Fellow.
Ellen Oshinsky (she/her)
Founder of Circle and Spoke
Wild Gift Class of 2024.
Wild Gift: What is Circle and Spoke’s mission, and what kind of impact are you hoping to have?
Ellen:
Circle and Spoke empowers women through bike rides and retreats that uplift movement, rest, community, and reflection. “Spokers” tap into their inner power and truth to shift gears in and out of the saddle and carry that energy from retreat to life.
While Circle and Spoke is about women’s empowerment, the impact that we really want to see is for people to feel less alone and more connected in our world.
One of the reasons we center retreats in our work is that retreats are a space for pause and reflection alongside others. As an adult, some of my most meaningful friendships have been sparked thanks to a retreat — even ones that occurred over 48 hours. My hope is that, thanks to Circle and Spoke’s work, folks walk away from our gatherings feeling less lonely, with new authentic friendships and pals to explore in the outdoors and slow down and connect on a heart-to-heart basis.
Wild Gift: What are you currently working on or excited about? Any recent accomplishments we can celebrate with you?
Ellen:
In July, Circle and Spoke is hosting its first overnight retreat: Pedal, Paddle, and Pause on July 18–20th. We’ll be saying yes to adventure and community in stunning Ohiopyle, Pennsylvania, which is home to one of the most picturesque state parks, the wild and fun Yough River, and the Great Allegheny Passage. Baked into the weekend is going to be a lot of fun: we’ll be whitewater rafting and biking and tapping into our individual and collective resilience through coaching and guided reflection.
The big accomplishment for Circle and Spoke is we recently wrapped up a 3-part series for women and non-binary folks in partnership with a DC bike shop. The series was specifically for women who were hoping to dust off the cobwebs and feel less anxious biking. It was so powerful to hear at the end of the series how people were deeply moved by the experience. The series sold out with 12 women and non-binary folks enrolled, and 9 folks joined for all three classes. 100% of individuals who joined for the entire series felt more confident biking on trails and in the city thanks to the series. I’m really proud of this accomplishment and how these women courageously stretched themselves and leaned into the community.
Wild Gift: How did the Wild Gift Fellowship help in your journey as an entrepreneur?
Ellen:
Circle and Spoke is a young business, having recently turned one. Prior to the Wild Gift Fellowship, we offered one-off bike rides in order to build up our brand and community. That being said, a core aim of our work is to build community. I genuinely want people to walk away from Circle and Spoke’s gatherings and say, “I’m so excited to go hang out with that other gal I met today and get coffee or go for a bike ride.”
During the fellowship, I remember Noemi Florea, of my cohort, expressing how if my desire is to build community, I should be offering a series rather than one-off experiences. That way, people organically connect with one another on multiple occasions, catch the good vibes, and feel more comfortable and less bashful asking to hang out outside of our rides and retreats. When Noemi shared that, a light bulb went off! She was totally right.
The recent series that we put on was designed intentionally as such, so folks could get to know one another naturally. After two of the classes, we had an opt-in dinner, and many folks stuck around to eat together. It was exciting to see people vibing with one another, laughing, and connecting socially out of the saddle.
Wild Gift: What are some of the biggest lessons you’ve learned since your fellowship?
Ellen:
One of the biggest lessons I have learned since the Wild Gift Fellowship is that choosing the right partners to collaborate with is important for the success of this work.
Over the course of the fellowship, we had a Lumina Spark assessment to better understand our strengths and sticky spots. The assessment produced a mandala of my traits and a mandala of my psychological opposite. What gave me the biggest giggle was that a member of my cohort and I were literal opposites of one another. We treaded some turbulent waters at first, and after some honest conversations, we were able to get over the hump and partner together. Truly, one of the greatest joys of the trek was getting over that hump and laughing together as we prepared dinner, as wind blew and a drizzle fell outside our cooking tent.
What I learned from this — and what I’m continuing to learn since my fellowship — is that I will work with and partner with individuals who are vastly different from me. However, to make that partnership a success, a necessary underlying trait that I need from myself and from my teammate is a willingness to communicate and work through the challenging moments, be self-reflective, and with a shared commitment to our mutual goals and what our community needs, show up anew.
Wild Gift: What’s next for you and your organization in the coming year?
Ellen:
As I was sharing before, I’m stoked to go from vision to reality on Pedal, Paddle, and Pause, our upcoming retreat in July, and make this overnight retreat happen. We are building off some good momentum from a day-long retreat that also involved whitewater rafting and biking last year, and it’s a huge growth point for us to extend this second edition of Pedal, Paddle, and Pause to a weekend-long retreat.
Wild Gift: Are there any opportunities or needs you are actively recruiting for?
Ellen:
Spreading the word and getting our brand out there can be a very vulnerable exercise. A friend of mine, when I was telling her about some of the bumps in the road to get folks to sign up for the series earlier this spring, shared with me, “Ellen, it’s hard because you want it to be fast.” Her words really helped me understand that I was holding unrealistic expectations. Now, when I start marketing a series, I focus on the vision + the vibes. Not every bike ride is a coast down the hill. Sometimes it’s a climb, and it’s important for me to stay true to my values and remind myself what I’m building towards, as I’m marketing and selling our retreats.
That’s a long way of saying, I’m always open to mentorship — especially from folks who’ve walked the line of getting out the word on your events and experiences and keeping the faith in what you are building, even when things can be slow.
Circle and Spoke cares deeply about building up community, and at the core of making that possible are rad partnerships with aligned brands that know magic happens when community is built over shared experiences in the outdoors. Through our rides and retreats, we love to highlight aligned brands, so please reach out if you are interested in sponsoring a future ride or offering your product to be shared with our community.
I am also looking for a rad human to help with retreat support for our overnight retreat July 18–20th. If you are a woman or non-binary individual that loves giving high fives and cheering people on with a Jane-of-all-trades attitude, email me at retreats@circleandspoke.com. I’d love to talk!
Wild Gift: Can you share any metrics or milestones you’ve hit?
Ellen:
In the past year, we have held 5 different rides/series/retreats and brought together 50 women and non-binary individuals.
Wild Gift: How can the Wild Gift community follow and support your work?
Ellen:
Circle and Spoke publishes a Monday Musing newsletter every week! It's a weekly dose of inspiration to support you in shifting gears.
You can subscribe to our newsletter → https://circleandspoke.beehiiv.com/subscribe
Follow Circle and Spoke on Instagram → https://www.instagram.com/circleandspoke/
Visit our website → https://circleandspoke.com/
Find me on LinkedIn → https://www.linkedin.com/in/ellen-oshinsky/
You can learn more about our upcoming retreat — Pedal, Paddle, and Pause — and register here: https://bit.ly/WGcircleandspoke2025
We love having Ellen as part of the Wild Gift community and can’t wait to see Circle and Spoke’s continued growth. Stay tuned for their first overnight retreat and more joyful connection on the road ahead. 🚴♀️💫
Thanks for reading the Leader Spotlight segment of the Wild Gift Blog! If you are a Wild Gift Alumni and want to be featured, please email jacinta@wildgift.org.