We had the good fortune of connecting with Lauren May Woodruff and we’ve shared our conversation below.

Hi Lauren, how do you think about risk?
The ability and willingness to enthusiastically approach risk in business and life is one of the founding characteristics of all entrepreneurs. We are a breed of people who will sit with the spark of an idea and pour effort, money, time, consideration and drive into it until this small thing begins to breathe on its own. No person at the beginning of the creation process knows if their concept will become a living, breathing business with a life and inertia of its own and yet we all passionately pursue that ending. It’s a special flavor of crazy and without it our society would be without progress or innovation.

Through my own creation process with both businesses, The Hillside Center, and RecoverEASE, I jumped into those industries with both feet after having seen a niche in large markets that I could fill. My passion for business development and ability to market those ideas to the consumer had truly overshadowed the risk of failure or rejection that inherently comes with growing a concept.

When I created The Hillside Center, one of Colorado’s premier dressage training facilities, our family had taken a significant financial risk of purchasing the real estate to house the business. It was my first horse farm, it needed significant investment in the facility itself, I had no presence in the sport horse market at the time and yet I put my head down and poured my life into creating the brand that embodies Hillside. My father, an incredible businessman and true mentor, told me, ‘The only way to eat an elephant is one bite at a time,’ and that is how I have grown my small farm from an idea into a market leader in the face of heavy risk that would scare away most people.

Please tell us more about your work. We’d love to hear what sets you apart from others, what you are most proud of or excited about. How did you get to where you are today professionally. Was it easy? If not, how did you overcome the challenges? What are the lessons you’ve learned along the way. What do you want the world to know about you or your brand and story?
My passion in life is growing ideas and living as an example for other women that a life of entrepreneurial endeavor is both rewarding and POSSIBLE! I have three beautiful daughters and I am proud to raise them in a home where they witness what it really takes to start businesses and develop lasting brand presence.

A life-long equestrian, our family began the search for a small horse property with 4 stalls in 2014. What materialized after much searching was a 50-acre, 21 stall commercial horse farm that far outsized our then herd but we could not resist! That single jump into the property set off a 7-year adventure in horsemanship, leadership, business development and living out my truest passion in service of the dressage community here in Colorado, nationally and ultimately working internationally with Olympic-level clinicians and breeders worldwide.

While operating and growing our equestrian business with my husband working out of state and a small child at home, I encountered health issues that ended in a double mastectomy. That horrific surgical experience was not an ending but a springboard for yet another dive into the entrepreneurial pool. Through my own recovery experience, I invented and patented a new kind of multi-use recovery garment that brings patient comfort to the forefront of consideration. It’s been a fulfilling and healing experience to bring this product to market and while it’s a clear departure from the equestrian industry I have built a career in, I find the variety energizing and learn something new every day.

If I could share one lesson to an aspiring entrepreneur, I would say that my journey has taught me the importance of resilience and adaptability of vision.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Colorado is filled with incredible spots to check out. Most of my life is lived outdoors and that’s no exception for my days off. Check out Dunton Hot Springs in Cortez and Avalanche Ranch in Carbondale for hot springs and glamping on the weekends. There is great hiking and activities to be had no matter the time of year!

My current Denver go-to spot is Comal Heritage Food Incubator. It’s a business incubator and training kitchen to help migrant and refugee women establish lives, learn to run businesses and share their cultural flavor within the Denver community. What could be better in both great meals and purpose?

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
There are so many people who are a part of my creation story! I’d like to thank my father, William G. May, who I watched develop a massive business through my childhood. I spent my youth bonding with him over growing the business and looking at problems in new ways. He is my role model for performance under pressure, success and humility. Without him I would never be an entrepreneur.

I have to thank my husband and our family for the support they have given to me both financially and in immeasurable patience as I spent years singularly focused on the development and needs of the horse farm, growing its various arms of training, breeding and sales as well as building a strong brand and client base. Without my family to champion me when I was exhausted or felt like failure was immanent I would not be at the helm of such a successful equestrian facility.

Shoutout to all of the trainers and clinicians who make Hillside a special place to train and to the boarders of my facility that passionately transform our community of riders into a barn family. Without the people inside of Hillside the barn is simply a building. They are truly the spark!

Without my friend and partner in RecoverEASE, Hannah Kenny, I would not be realizing the garment idea borne of my own double mastectomy experience or be as dedicated to improving the recovery experiences for so many other women impacted by breast cancer. She has always believed in my ability to take an idea and run with it. When she joined me in the development efforts of RecoverEASE she added the support and grounded, pragmatic approach to business scaling that we needed at the time.

Website: www.thehillsidecenter.com & www.myrecoverease.com

Instagram: @hillsidecenter

Facebook: @thehillsidecenter

Image Credits
Katie Damon, Clever Lark Photography.

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