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TCV Insights

The Entrepreneur's Journey: Notice I Didn't Say "Successful" Entrepreneur

Updated: Nov 14, 2023


By Deb Tillett, TCV Director -


I dare say that most, not quite all human beings have at some time in their life stumbled upon an “aha” moment, great idea, incredible solve to a problem and have thought I could “make that a business”. Whether it was an idea for a problem-solving product or a thought about something you were searching for and couldn’t find, most of us have experienced the thought that “I could do that – and make money”. Try it, I dare you!


The journey to becoming an entrepreneur and launching your business, getting initial seed funding, finding the customers, and setting up shop is a learning process. I myself, have started many companies, taken many other companies from early stage to growth and exit and personally have lived what I am about to write about.


I spent the early part of my career, when I was barely out of college, until1985 when I started my first company, at entrepreneurial companies. Companies that were 1 or 2 people; the founder and 1 employee – me. This was more than a learning experience it was a way of living. I honestly didn’t think there was another way to work. As a result, I was working for an ad agency that was itself a start-up. It was small, local and four guys that had worked together at a larger ad agency and decided to “steal” a client and go out on their own. My first real experience with how it could be done.


During that experience, I was on location in Vermont, doing a fashion shoot for Head Sportswear ski clothing and the fashion photographer that we had hired was a young, talented woman. Her name was Helen and after three days in the snowy environs of Vermont, we got to know each other, we became friends over beer and hot chocolate, and realized the talent that each of us brought to the job. Just as we were ending the photo shoot and packing up – we looked at each other and said, “you know we could do this ourselves, we don’t need all those other guys”! Wow in retrospect, how naïve you can be at age thirty 33. And sure enough, upon return to Baltimore we met many sleepless nights, called an attorney friend, found the name of the company we would use and well, GULP, Helen left her photography studio and I quit the ad agency and we set up our Company – Norman Cheek! Both of our last names.


Well, now what? I walked away from my paycheck, I was in the process of getting a divorce where was my rent, food and spending money going to come from – oh did I mention health care. I always tell my budding entrepreneurs, my journey was that I quit my job, left my husband, sold my car, and launched my business all in the same week. I personally just knew that I could not fail. I was not afraid to “jump off the cliff”. What happened next is the lesson to be passed on.


We had a business, now what? Well, we should get a customer, how, who, what? Shouldn’t we have an office? Again, timing is everything and it just so happened that just as we were getting our act together, Cross Street Partners, another entrepreneurial enterprise in the real estate development market, was renovating an old, abandoned manufacturing space in Hampden called the Mill Center. We took one look at the space and the pricing and said we’ll take it. It was a perfect space for a small office, enclosed and a large open studio space. Thank goodness I had sold my car and had working capital. We signed a lease and were on the way – oh wait we still needed a customer.


That is the key lesson to be learned – who is that first customer and how do you secure it? My partner and I dug deep into companies/people we had worked with and reached out and let them know we were in business. Luckily, Helen’s talent and reputation were solid and all I had to do was secure the jobs. So now we had a business name, a location and were close to getting our first catalog job with Joseph Banks Men’s Clothier. Little did I know at the time that we weren’t quite incorporated, we didn’t have a business bank account or accountant. Mostly because neither of us had done that before. Remember it was also back in the day pre cell phone and internet. We had a landline phone number and typewriters.


Fast forward to securing the job with Joseph Banks but now we had to figure out what we would charge for a day long studio photo shoot. Again, pre internet and no way to google what an average hourly rate would be. So, I got creative. I grabbed a phone and phone book; called around to all of our current competitors and made a call pretending I was a high school student doing a paper on business and practices and asked if they wouldn’t mind answering a few questions. And – guess what they did. Suddenly, I knew the range of pricing fees for many if not all of our regional competitors. Lesson learned, one problem down only a lifetime more to go.

And so the journey goes, one step at a time as an entrepreneur your greatest asset is creativity not just in the field in which you are practicing but in problem solving. For example, the next hurdle, how do you find an attorney to help with your incorporation paperwork, in my case, which I only found out after the company broke up three years later, that my partner and I had not signed any documents about what to do upon ending the company. But again, the financing is so limited as you are getting started that I always tell entrepreneurs that you have to “maximize your resources” – it just so happened that I was a young, not unattractive, single woman and I just happened to know an accountant, an attorney, a banker – all men by the way - you get where I am going. Friends like that will be able to get you set up correctly and affordably.


The lessons you learn from the first venture into starting a business are monumental but priceless and will provide the master’s degree you will need to continue and grow either the first business you start or each subsequent venture.The real lesson to be learned is that starting a business is a process, it is not always exactly the same, but you need a good idea, a large enough addressable market, a reasonable way to charge a fee, a product/idea delivery method (there wasn’t always Amazon) and a long-term plan to accommodate growth.I would also always suggest that a wise, experienced executive who has been down this slope as your go to advisor is always key. I always quote a sage colleague of mine who says “surround yourself with a cold circle” in other words, most entrepreneurs fall in the trap of surrounding themselves with friends and family – but the “cold circle” will always tell you that “your baby is ugly” and thereby advise you and help you discover the right path.


Need help on your journey to business success? Deb Tillett has joined the team at TCV and is now available for consulting services. Contact her at Deb@TCV-Growth.Partners

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