After 23 years building his business, the co-founder of Creative Apparel Concepts decided to step away and start over. Follow along on Jeff Gray’s entrepreneurial journey.

It is January, 2023 and I am beginning the process of starting over. It is daunting. I am anxious, a little scared and spend many sleepless nights struggling with self-doubt and worrying about the future. I continually have to remind myself that I am a seasoned apparel business owner and leader who has worn many hats, and at my very core, I am an entrepreneur. Entrepreneurs have the gumption to act on an idea. Yes, it may be risky, but there is an excitement and thrill to start a new journey and to create, problem solve and put all the puzzle pieces together to make something great. This becomes my daily affirmation as I delve into the discovery process of what will soon become my new business venture, RoboArt Labs.

I discovered the world of Artificial Intelligence text-to-image art generation while researching new opportunities. I was so amazed and excited about this game- changing technology that I decided to dive right in and learn as much as I could. I spent my days researching AI Art by trying different art generators, playing with different AI tools, and reading as much as I could find, going so far as printing samples to check quality and investigate the problems when printing on physical products from art created online with AI. I felt like I was on to something. I have spent my apparel career passionately pursuing “white space” and innovative product ideas to bring to retailers. This new technology could provide a unique opportunity. How exactly, I didn’t know but I was going to figure out how to bring AI to the apparel world I know so well.

The power of networking

When you are toying with the idea of starting a new business, no matter what that business is, it’s crucial to network. One of the benefits of being an old dude is that I know a lot of other entrepreneurs, decision makers and accomplished individuals. I called on old friends, friends of friends, relatives, business acquaintances, LinkedIn connections and anybody who would talk to me. I spoke to scores of people. I felt like Dorothy in the Wizard of Oz following the yellow brick road and meeting all sorts of characters while trying to find the connections that would bring me home to making income again. It’s amazing how many people took the time to listen to me and let me “pick their brain,” as the saying goes. Networking helped me zero in on the concept of what I wanted to build. Next, I put it to a spreadsheet.

When I began this venture, I knew that I had at best, a year’s worth of living and potential start-up expenses. Since I’m not a “tech-guy” I had no idea how much it would take to make my vision a reality. I called my cousin Jordan for advice. Jordan is the co-founder and CEO of a successful tech company in California. Jordan not only gave me great advice regarding tech, but also recommended that I call Josh Frank, a seasoned tech chief product officer whom he worked with in his past. Josh is a co-owner of Mythic Insight, a fractional tech company, with Robert Prehn, their CTO. I needed to know if my concept was feasible. With AI being so new, the three of us decided the best way to move forward was to start with a discovery phase and a deep dive. Suddenly, this pursuit became very real.

“I continually have to remind myself that I am not required to have all the answers. It’s the journey of putting all the pieces together.”

Building a business plan and team

As March drew to a close, my technology team successfully concluded the discovery phase, outlining a detailed timeline and deliverables for the development of an innovative artificial intelligence-driven art platform. This platform is designed to enable customers to effortlessly craft custom artwork and order their creation to be printed on various products. This all comes with a big fat price tag.

I had some decisions to make. It would get very financially uncomfortable having to dip into savings, use credit cards, and take loans. I needed some time to evaluate my next move but I also needed to get focused on putting together a professional business plan. I hadn’t made a business plan since I started my apparel company over two decades ago. I researched how to write one, looking for tools (hoping AI, but not yet) to help create it. I spent a week on my plan and then realized I needed help. I posted an ad on freelance platform Upwork seeking help with writing a professional business plan. I hired a team of two to help me with the discovery, value propositions, market research, financial modeling, business plan, and pitch deck. When starting a business on your own, it can get pretty lonely and I missed working with others. It is nice to have this team with whom to bounce ideas around. We began to meet once a week to map out my future business. I was excitedly optimistic with a tech team to validate my concept and a business team helping me prepare to sell it.

But by April, 2023, my excitement was tempered by the battles going on in my head. I read an article about Imposter Syndrome, which, I’m here to tell you, is very real. It was nice to hear that my feelings were not unique, but shared with many entrepreneurs. My inner voice questioned whether I was capable or simply crazy for taking on this challenge. I continually have to remind myself that I am not required to have all the answers. It’s the journey of putting all the pieces together. It’s about building a robust support system of exceptional team members and advisors who can complement my strengths and provide guidance when needed. The best way for me to handle my inner conscience is to focus on the present and take one day at a time.

One of the most helpful allies early on in my adventure also happened to be one of my closest friends and college roommate. Dan Neuwirth is one of the smartest people I know. He’s founded and sold med-tech companies, he has worked for Fortune 50 companies, pitched VCs for funding and has been in charge of acquisitions. He has great experience working for large companies, startups and fundraising, all of which I lack. In my many conversations with Dan, I finally just asked him if he was interested in investing and helping me turn my vision into a reality. He came up with a proposal for being my chief operating officer and member of the board of directors, investing his time for equity. Dan helped me to set up the company as a C-Corp., explaining all the benefits just like a lawyer or accountant. He would lead accounting and financial management activities, advise on strategy and product development and fundraising. This was huge for me. Not only did it level up the entire operation, but more importantly, he is someone I can trust. Dan reviewed the work my business plan team helped me put together and basically told me to scrap it. The plan was just too long (46 pages) and cumbersome for any bank or investor to digest. He began helping me re-create a financial plan and pitch-deck. Dan became a shareholder in May 2023.

“Feeling like a teenager asking someone on a date, I arranged a meeting with him to see if he would be interested in helping me in exchange for equity…”

Around this same time, I was introduced to Kyle Shannon, who is based in Denver. Kyle is one of those rare individuals who has both an uncanny understanding of new technologies and is exceptionally creative. He is a tech innovator who co- founded and was the chief creative officer of Agency.com in the 1990’s, a firm that played a significant role in shaping the modern digital marketing landscape. Kyle is deeply invested in generative AI, and leads AI Salon, an-in person and virtual meet-up community that I joined. I needed Kyle on my team. His insight and experience would be invaluable to my platform. Feeling like a teenager asking someone on a date, I arranged a meeting with him to see if he would be interested in helping me in exchange for equity. After keeping me waiting for a week, he agreed to be a consultant and a content adviser. By the end of May, I had a tech team, a COO, a super creative AI leader, UI expert and creative strategist. I am loving our team! Now, all I needed was something to show and some more capital.

My team began meeting weekly to brainstorm and share ideas as we worked on a prototype that we could start testing. This continued through the summer. Things weren’t moving as quickly as I would have liked. By September, we were about two months behind plan and I was extremely frustrated. I was anxious to get in front of investors and get potential customer feedback. I also knew I needed to be patient. My financial clock was ticking, but as I always remind myself: just take one day at a time.