We had the good fortune of connecting with David Woods and we’ve shared our conversation below.

Hi David, we’d love to hear about how you approach risk and risk-taking
The scariest, most heart-wrenching decisions that I’ve faced in my life have led to the most transformative moments in my life. As I was coming up the ranks in my first career path at Whole Foods Market, and as I began applying for promotions, I quickly learned that fear of the unknown can be a stifling feeling. I also learned that stepping into the unknown, and putting myself out there leads to explosive growth. Every time I got ready to apply for a job I would question myself. Am I good enough? What if I don’t get along with my new boss? What if there is too much pressure? And so on. There are a few lessons I learned from this process. One, it’s normal to have these feelings, and it’s vital to not let them stop me from trying. Two, in almost all of my new roles I have gotten over the years, after about three to six months the fear is eradicated. Not only do I not have fear of whatever job or task it is that I was worried about, but I am now confident with that job or task. Three, the speed of learning accelerates rapidly when I’m in a new, uncomfortable environment. I had to adapt to the new skills, the new team dynamics, and so on. This helped to put my brain in overdrive to make sure I was positively contributing to my new team, which accelerated my learning process. Four, whenever I felt I was one of the lead performers in my job and beginning to get comfortable, usually around the 2-year mark, I would get ready to pursue the next challenge.

I applied this methodology to my path at Whole Foods Market, working my way up from a pizza cook at the age of 18, to a Global Buyer for the Grocery Department at the end of my 14-year tenure. I was always terrified of the new jobs I applied for during that time. I had thoughts of doubt, uncertainty, fear, insufficiency, imposter syndrome, and all that goes along with those thoughts. But, that didn’t stop me from moving forward into the unknown, with every promotion leveling up my skillsets, expanding my network, and opening doors I never thought were possible in my life.

I had been with Whole Foods Market for 14 years and began fearing that I would be a ‘lifer’. I never wanted to be the guy who was too scared to jump from my safe career into another opportunity out of fear of the unknown. I knew deep down inside that I was capable of more, that the learning opportunities were beginning to slow, and that I needed to make a wholesale change if I wanted to be fulfilled in my life.

As a buyer I frequently met with brands that would sell to big food for hundreds of millions of dollars. Brands like EPIC Bar, who sold to General Mills for over $100M, RXBar, who sold to Kellogg’s for $650M, and Primal Kitchen, who sold to Kraft Heinz for over $100M. I would work closely with these brands, help get them cranking at Whole Foods, and then one day would see the press releases come out that another huge acquisition has just taken place. I was tired of sitting on the sidelines and seeing this all happen right before my eyes. While for every one brand that sells, one hundred others go out of business or fail, I thought it was worth a shot. I wanted to at least be in the arena with the other players and have the opportunity for this upside.

After months of deliberation on whether I should leave Whole Foods, an opportunity came up to join LesserEvil Snacks as VP of Sales. LesserEvil was one of my favorite brands that I worked with in my tenure managing the Salty Snacks category at Whole Foods. They were vertically integrated, used all organic ingredients, used high-quality oils, have biodegradable packaging, and their sales were on fire. Additionally, I consider the CEO of the brand to be a dear friend and someone who I could absolutely see myself working for.

I ended up accepting the role, and I was more scared than I’d ever been of a new job. Not only was I leaving my safety net at Whole Foods Market, but I grew up at Whole Foods. I bought my first car, opened my first retirement account, met prior girlfriends, and made lifelong friends – all through Whole Foods. That is precisely the reason I felt I needed to go – it was time to leave the nest. I wanted to take a chance to see what I am truly capable of in this life.
On my last day on the job, I addressed the team, who had grown significantly while I was there. The crippling fear began to sink in and the tears began flowing. This was by far the most terrifying moment of my career.

In June 2020, Six months into my new role at LesserEvil, something was happening in the other half of my life at CrossFit. CrossFit’s CEO, Greg Glassman, made some insensitive comments in the wake of George Floyd’s death and was receiving major backlash from the community. Gyms were de-affiliating from the CrossFit brand, athletes were speaking out and boycotting our CrossFit Games competition, and sponsors were backing out of deals with CrossFit. On top of all of this, Greg was also accused of ‘me too’ that same week. The brand was at a breaking point.

During this time, I thought back to someone I met along my journey whose name is Eric Roza. Eric was a successful tech CEO that sold his company Datalogix to Oracle for over $1B, and he was obsessed with CrossFit. He was so obsessed with CrossFit that he tried to buy the brand many years ago, something Greg wasn’t willing to do at that time.

One night in the midst of all of this turmoil I had an epiphany. I don’t use the word ‘epiphany’ lightly, either. I’m talking about one of those moments where every cell in your body, every brainwave in your head, and every feeling in your heart and gut are marching in the same direction. It’s a moment of clarity that hits you like a ton of bricks. You have no idea where it came from, but you are thankful you are experiencing it. Was it God? The Muse? The Universe? I don’t know, but I do know that it’s some cosmic shit.

My epiphany was this. CrossFit is in trouble. CrossFit saved my life and I am eternally grateful for the methodology and community that Greg Glassman forged. What if I could help Eric get a seat at the table to speak with Greg about buying CrossFit? I was in sales and getting seats at the table for meetings was a huge part of my job. Why not try doing this for CrossFit? Why not me?
I ran with this epiphany and ended up cold messaging Eric on LinkedIn. I hadn’t spoken with him in a while, but I asked him if he was interested in buying CrossFit with everything that was going on and if there was anything I could do to help. He replied that he was in fact interested and that if I could help break through to anyone at CrossFit HQ that he would take any help he could get. After receiving this message I had a bit of an ‘uh oh’ moment. I was happy that Roza was interested, and I was happy that he asked for my help, but I didn’t know what I was going to do to actually help.

After thinking about what the best approach was I ended up pursuing something I learned in my years as a Buyer. A cold email with the right subject line, the right structure, and some heartfelt content that will connect with the other side. I teed up a cold email that I sent to Greg and other members of CrossFit’s executive team titled “Serious Offer to Buy CrossFit, Inc.”. Within that email, I explained how much I love what they had built, how much CrossFit had transformed my life, and, sadly, that the organization was in big trouble – and I had a possible solution in Eric Roza. Roughly 5 minutes after sending that email I received a phone call on my cell from a California phone number. Lo and behold it was Greg Glassman. We spoke for 35 minutes, established rapport, and ended that conversation agreeing that Eric and I would travel out to Santa Barbara to meet with Greg the very next day to consummate the deal. Greg happily obliged and sent his private jet to pick up me and Eric in Broomfield, CO roughly 24 hours later.

On the second day of our trip to Santa Barbara, Greg and Eric had struck a deal on the acquisition of CrossFit, and I got to witness the entire process. The handshake was done, and then the real due diligence and the legal process began. After our meeting, Roza and I sat on the beach of Santa Barbara, taking everything in, and he offered me a job as Chief of Staff for CrossFit. As someone who has loved CrossFit for 12+ years, and someone who followed CrossFit on LinkedIn for well over five years for any possible job opportunity, this was the chance of a lifetime for me to join the brand I most loved. I gleefully accepted. On July 24th, 2020 the deal became finalized, and Roza was now the CEO of CrossFit.

The road that life takes you down, and how everything connects when you look back in hindsight, is mind-boggling. What if I had listened to my fears of inadequacy prior to applying for the various positions at Whole Foods? What if I had been too scared to leave my safety net at Whole Foods to join LesserEvil? And what if I had that epiphany to help connect Eric to Greg, but didn’t take action on it? These are all risks that have led to bigger and brighter opportunities. These are all risks that have expanded my skill set in both business and life.

When I think about my past, and about risk-taking in general, there is one quote that has stuck with me. Anytime my friends are faced with those ‘big’ decisions in life, this is what I share with them, which happens to be the same words my brother shared with me during my wife and my elopement:

“Nature loves courage. You make the commitment and nature will respond to that commitment by removing impossible obstacles. Dream the impossible dream and the world will not grind you under, it will lift you up. This is the trick. This is what all these teachers and philosophers who really counted, who really touched the alchemical gold, this is what they understood. This is the shamanic dance in the waterfall. This is how magic is done. By hurling yourself into the abyss and discovering it’s a feather bed.”
― Terence McKenna

I’ve learned to not fear the abyss. While I’m certainly nowhere near perfect with this philosophy, I’ve learned to seek the hard decisions in life that my heart is pleading for. This is where the magic is done.

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?I grew up in a creative household surrounded by art. My dad has been an artist since he was a child so I grew up in an environment where there was always something creative going on. Additionally, my mom is creative through interior design and other avenues. We had everything from a toilet seat with crazy Elvis art on it, to full-blown murals painted on the walls, to funky coffee tables, to eclectic antiques, and other unique things all around the house. We also would regularly go to art galleries in downtown Denver like The Pirate, Fish Head Soup, Erin Johnson Antiques, and other places like that. The combination made for a unique experience whenever my friends came over and exposed my mind to a different way of living from a young age. My dad still paints full-time and exhibits around Denver. You can find his art at https://www.johnwoodsstudio.com/ . When I met my wife, one of the things that I loved about her was her artistic expression and creativity. She owns a small business called Sugar Mad, https://sugarmad.com/, where she makes jewelry from Japanese glass beads. She is constantly exploring her creativity through her business, including making her own displays for her jewelry, building her exhibitor booth from scratch, creating all of her video content for social media, doodling on a variety of mediums, and much more. She also grew up in an artistic household with her mom being a full-time artist for much of her childhood.

Art is an extension of my life and is something that I find to be critical to self-expression. I pursue my own artistic expression through my work, CrossFit training, and skateboarding. During my years at Whole Foods what I loved most was merchandising. How shelves are laid out, how cleanly brands and items flow into each other, how much air space is between the product and the shelf above, and all those little details that many don’t think about. I also loved building displays when I was in the stores. I spent many overnight shifts building end caps, and floor displays, always putting my personal touch on how these were set up. With my current job at CrossFit, I express my creativity in several ways. One is how I share CrossFit’s message with new partners. I love being in high-pressure situations where I am educating executives from other organizations on what we do, why it matters, and how they can get involved. I also express my creativity through how our partners show up in our media coverage. This includes how sponsor inclusion is structured in each show, what types of on-screen graphics we use, and what types of segments we include.

With CrossFit training, there is always an element of personal style and creative expression that each athlete brings to the table. Due to the complexity of many of the movements in CrossFit, like gymnastics and Olympic weightlifting, this gives each athlete the opportunity to showcase virtuosity and style in their movement. Coupled with the clothes that one wears, the music they listen to, their physique/body, and the equipment brands that they use, this allows for each athlete’s personality to shine through.

Lastly, I find skateboarding to be the most artistic thing that I do. Everything from the art on the skateboard decks I choose, to the grip tape design I put on each deck, to the trick selection I do, to the locations I choose to skate, and to the music I listen to while skating. The bounds are limitless with skateboarding which provides a blank canvas for skateboarders to make their own mark.

Now that my wife and I have a one-year-old son, we fully intend to share our love of art and creative expression with him throughout his childhood.


If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
– Favorite workout: Alpine CrossFit – Favorite haircut: Tried & True Barbershop
– Favorite coffee: Corvus Coffee
– Favorite restaurants: Farmhouse Thai, Uncle Ramen, Sushi Den
– Favorite Neighborhood for food and drink: The Highlands (just west of downtown Denver), RiNo
– Favorite Neighborhood Architectural Tour: Arapahoe Acres, which is a historic mid-century modern neighborhood in Englewood
– Favorite skatepark: Golden Ulysses Skate Park
– Favorite Hike: Mt. Sanitas trail in Boulder
– Favorite Art Museum: Kirkland Museum of Fine & Decorative Art

Who else deserves some credit and recognition?

My parents, whom I put through the wringer as a teenager, have stuck with me through thick and thin. They always supported me to be the best version of myself and not settle in life. They are the ones that pushed me to apply for my job at Whole Foods. Who knows where I would be without them? 

“The Alchemist”, by Paulo Coelho. I’ve found tremendous inspiration through this book, and it’s helped me to hone in on what my personal legend is.

Whole Foods Market and the incredible team members that work there. I learned almost everything I know from the passionate group of individuals that make up Whole Foods’ workforce. A number of folks there took risks on me as I was coming up the ranks and I wouldn’t be where I am without them.

Eric Roza for allowing me the opportunity to help on his adventure to buy CrossFit, and for the opportunity to join the team. Justin Bergh and Dave Castro for giving me a chance to lead partnerships for CrossFit when I moved out of my role as Chief of Staff.

Website: https://sugarmad.com/ and https://www.johnwoodsstudio.com/

Instagram: https://www.instagram.com/kelloggwoods/

Linkedin: https://www.linkedin.com/in/davidkelloggwoods/

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