When I originally founded Cherry Willow Apparel I didn't know exactly how I was going to contribute towards my mission of ending homelessness. My experience in the business world enabled me to be confident in my ability to create value through apparel as it is something I have already done successfully. Beyond that I knew my mission was important enough that I had to give it my all! Before I get into my career and what led me to the point of starting my own business, I want to give you a glimpse inside my brain and how I operate.
I got my first job when I was 16. It was an awesome job! I worked in concessions at a Drive-In movie theatre. Granted I was only making $7.30 an hour as that was minimum wage (and still is 16 years later, craziness). I have always been a big fan of movies and one of the perks of the job was on my days off I could bring a carload of my friends and we would all get in for free! I worked there for 2 summers and saw every movie that came out. The second summer I was at the Drive-In I picked up a 2nd job working on a farm detasseling corn. I would be at the farm from 6AM-2PM come home, eat & nap, then go to the drive-in from 7PM-2AM. Looking back I don't know how I had the energy for it but I was young and I had no stress. Whereas many Americans today have to work two jobs just to afford rent, I can't imagine the toll that working two jobs, caring for children and stressing about finances would take on a person. Those are some of the mentally strongest people I have met. I digress.
I was working so hard and saving up because I knew I wanted to leave Ohio for college. I loved growing up in Ohio, specifically Dayton, and most of my family and a lot of my friends still reside in the state. However I felt drawn to a big city as my dad grew up in Brooklyn and I was very curious what that experience was like. The money I earned from my jobs I put into a Certificate of Deposit (aside from what I used for beer) because I was fascinated by the concept of my money making more money for me detached from my time. This fascination led me to study Finance at Loyola University Chicago. I also majored in Sports Management but have used neither of my degrees in a professional capacity. A bit of an aside, don't feel like you have to have your whole life figured out in college. Learn as much as you can, follow your heart and your intuition and you'll find yourself in a great place.
I took one year off from working, my freshman year of college, that didn't go well for me. I have a tendency to stay busy and the activities I chose to fill my time with were not academic. I got in trouble for drinking and was given 50 hours community service. This led to my first experience volunteering with the homeless. I had volunteered through church all my life, serving as a greeter for mass, serving migrant workers, going to food pantries but always with my mother. After my freshman year I decided to get a job (I had also burned through all of my savings). I worked at our schools fundraising operation called Phonathon for a year, tough job, non-stop calling for 3 hours. Felt a little scuzzy raising funds for a school with an endowment of a billion dollars but mainly I just didn't like to have to ask people 4 times for money. That was the job though and it was very valuable experience. After that I got a job working 30 hours a week as a bank teller at a local bank. I needed to get a job to afford rent as after sophomore year in Loyola there are no options for on campus housing, other than becoming an RA which I probably would not have been allowed to even if I was interested, which I wasn't. I enjoyed working at the bank and this was my first real experience interacting with entrepreneurs.
After graduating I wanted to work in sports, however this was not in the cards for me. My college girlfriend found out she was pregnant about 3 weeks before graduation. Hard pivot for me as entry level sports jobs did not pay well. Thankfully I always knew I wanted to be a dad so I was very excited. I started applying for all different sorts of roles and ended up being offered a remote outside sales representative job. My first eight years I was a commission only rep and if I didn't sell then I wouldn't be able to provide for my kids. This was my first experience that is similar to that of an entrepreneur. I had bet on myself and my ability to be successful and failure wasn't an option. I came in and had success right away, I won Rookie of the Year and earned two more Presidents Club trips in my first 4 years. I then became stagnant, I was seeking new opportunities to continue to grow and was told to just keep doing what I was doing. I ended up leaving a few years later when I was recruited by a French start-up working to support small business owners. This is where my entrepreneurial instincts really began to evolve.
I began talking to many small business owners everyday. I learned that I thought and approached my work in a very similar way with an entrepreneurial mindset. My life started to change drastically when I realized there was a community of people who thought similarly to me. I started to read books written by successful entrepreneurs. I started networking which is something I never thought I would be excited about doing. One of the business owners that I was prospecting for my full time job was an apparel shop. I walked in and met the owner and he ended up offering me a commission only sales job. I had never considered having a second job in addition to my full time job but I had built an apparel business within my last role and was excited about the prospect of helping a small business grow. I ended up taking the role and helped bring in a few customers for him before I realized that I wanted to do something on my own. The owner of the shop had a few successful apparel brands and he helped me get started with my idea.
The name Cherry Willow comes from the two streets I lived on growing up in Dayton. I really liked the concept of nature being beautiful all the time, not just when flowers are in bloom and that was my original brand concept. After I started volunteering at the homeless shelter I thought what a cool way to embody that concept than by highlighting the beauty of the homeless people I served. Despite society not valuing them and many people casting homeless folks aside, I saw their inner beauty. I began working out how I could positively impact the people I served through apparel and started sharing my idea with a few people I had made connections with on LinkedIn. When I was laid off last November I reached out to one of the connections Nick Reed Smith and he got me connected with my Co-Founder David Gray. We have been working on making the idea a reality since then and I am very excited with the progress we have made!
One of the philosophies that is a cornerstone of Cherry Willow Apparel is "Who Not How" a great book by Dan Sullivan & Benjamin Hardy. The concept is simple yet extremely powerful. Simply put it is retraining your approach to problem solving. Instead of thinking "how am I going to solve this problem" train yourself to think "who is great at this and would love to help me solve this problem." This concept has helped fuel the growth of Cherry Willow exponentially as I never would have gotten this far with David's help and technical expertise. I am someone that has struggled to ask for help for most of my life but embracing this concept has been so rewarding and as David reminds me he loves to help!
I hope after reading this you have a little better idea of the path I took to get here. Thank you for reading and for your support! Please keep an eye out for my book "From Fog to Foge: My Journey to Inner Peace" which I am currently working on editing. You will enjoy the book if you enjoy reading these blogs, particularly this blog as it is similar to my writing style in the book. I will put out another blog when I publish, explaining what inspired me to write the book! I am hoping to publish by the end of the year but I am not going to rush the process. I will write more blogs on my personal and business philosophies to give you a better understanding of how my brain operates! Thanks again for your time and interest in Cherry Willow. Please feel free to reach out to me directly if you feel like you want to contribute to our mission!
