We caught up with the brilliant and insightful Dylan Green a few weeks ago and have shared our conversation below.

Dylan, appreciate you joining us today. Owning a business isn’t always glamorous and so most business owners we’ve connected with have shared that on tough days they sometimes wonder what it would have been like to have just had a regular job instead of all the responsibility of running a business. Have you ever felt that way?

I’ve never had a regular job, PTO, insurance, 30-minute breaks, or a complimentary kombucha tap in a brightly painted room. I spent my twenties sharing ideas with others and finding an obsession with pursuing potential, which led to a lot of sleepless nights, grand openings, raucous events, and wondering what the next thing would be. There isn’t any way to compare the two very different lifestyles but I do believe this: if you believe you have a purpose that needs fulfilling, starting a business is a fast track to exploring that. I’ve spent the last decade in this mindset and have had the absolute pleasure of working with countless brands and business owners in a creative capacity that has left us all more curious and fueled than when we started. I don’t think it’s about being happier as a business owner or having a regular job – I think it’s about finding the spaces in life that you can inhabit that continue to spark your interest and inspire others.

Dylan, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

It started when I was 9 years old. I was homeschooled on a farm and my mom signed my sister and I up for an entrepreneurship event, where we launched the 2001 equivalent of a food truck, aptly named Snack Shack. It wasn’t particularly interesting or successful but my developing brain was intrigued by the process. My college experience was riddled with extracurricular projects, including touring with a band, launching a coffee company, and launching a start-up incubator. By the time I was out of college, I was moving on to open a hotel and start my brand design career. I spent the sequential years were filled with working with companies on their brand development, from tractor attachment manufacturers to oyster farmers. I dipped into municipal-level politics for a while, which fried my soul and pushed me to change environments. I moved to Portland, Oregon to expand my design experience and business and was impolitely greeted by COVID-19. After 2 years of forcing a circle into a square, I made my way to Dallas, Texas which is where my real estate career began.

While this may seem absolutely hair-brained and chaotic there has always been a red thread, which is serving people with creative thinking. I believe this is my superpower and am proud of everything I’ve done to nurture this within myself.

We’d appreciate any insights you can share with us about selling a business.

In 2017 I opened a hotel in Bellingham, Washington with a very diverse partnership (Heliotrope Hotel). The partnership was a group of inspired folks, the trouble was that the inspiration was different for everyone. This is common and sometimes difficult to identify in the early stages of funding and launching a complex company. At the beginning stages the rose-tinted glasses are on and it’s common to ignore stark differences in approach. My recommendation in starting a business with a partnership is to take care of the tough parts first, which are the standard operating procedures for how the partnership operates and who owns what (literally and figuratively). Being the youngest member of the partnership it was difficult to find my voice and it was a challenging three years for me. However, the education and experience of it will last me a lifetime. Partners sold their shares internally over a number of years which inevitably led to an acquisition with a larger hospitality group.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I was born in 1992 and the fever dream of being a hustler was a big part of the cultural zeitgeist for my generation. It started with literary protagonists like Artemis Fowl and Harry Potter and was later represented by online personalities like Gary V. The story was always the same – fight to the end, hustle your pants off, and find yourself in the mess. While there are some valuable nuggets in this approach I found that it isn’t a sustainable method (I speak for myself, but maybe this will resonate with others). I realized around turning 30 that life is a lot longer than it is short (as long as you avoid tragedy, which many of us are fortunate to do) and the aggressive “get it done now” mentality leads to an anxious mind that struggles with seeing the bigger picture.

I spent years training myself in the school of hard knocks. Dappling in different sleep and workout routines, injecting myself into every social scenario that I could, and navigating every interaction like a salesman. It took a while but I realized this wasn’t the life for me and that I could be successful, creative, and more importantly happy in knowing that life is long and there’s plenty of time to become the man and business owner that I believe I can be.

Contact Info:

• Website: dylansgreen.com
• Instagram: @dylansantosgreen
• Linkedin: linkedin.com/in/dylansgreen

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