A Founder’s Journey Requires Understanding Things Happen for a Reason With Diane Gilman

A Founder’s Journey Requires Understanding Things Happen for a Reason With Diane Gilman

VENTEUR spoke with Diane Gilman about her entrepreneurial journey. The seventy-seven-year-old Gilman writes about finding her most tremendous success at age sixty, when she sparked a denim revolution: designing blue jeans for real women with natural bodies. She's sold nearly nineteen million pairs of her DG2 jeans on HSN, one of the top-selling designers on the network, with over $100 million in sales each year. With evergreen advice that can apply to all women, Gilman warmly and frankly shares her triumphs and defeats—delving into her battle with breast cancer and the other heartbreaks that could have easily caused her to call it quits in her memoir, “Too Young to Be Old: How to Stay Vibrant, Visible, and Forever in Blue Jeans: 25 Secrets from TV's Jean Queen” (Amplify). 

In the book, Gilman shares her electrifying life story and the empowering twenty-five lessons that not only made her a household name but also helped her create a community of 700,000 women who feel simply too young to be old. In her memoir, Gilman provides actionable and straightforward tips for a vibrant, visible, and relevant Act 3.

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

Earlier in my career, I learned that my weakness was industry networking. Though essential, it wasn't my favorite thing to do. My strength was always that I had an enduring love of fashion design, and because of this, I worked 24/7 and loved it.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? If yes, what was that experience like, and how did you overcome it? If not, why do you think this is the case?

I often found myself working alone all weekend in my design studio. I was doing the jobs of two or three employees while my friends and workmates were out and about, playing, and relaxing. Being a 24/7 entrepreneur was isolating, but I never doubted it was worth the sacrifice. 

What role has intuition played in your success as an entrepreneur, and why do you think this is the case?

Intuition has played a significant role in my career and has been foundational to my success. It has even led to some of my bestsellers. I utilize my intuition, especially when forecasting fashion, which is 12-18 months ahead of production for the public. It has been crucial to my success as an entrepreneur and in the fashion world. 

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur? 

I indeed let my health slip as I built my business, DG2. I was diagnosed with breast cancer late in the disease progression because I never had "time" to take care of myself (or so I told myself). That treatment led to almost a year off, which allowed me to concentrate only on my health. That amounted to new insecurities. 

There is also the added pressure of being not only a designer but also on-air talent selling my designs. When things aren't selling as well, and I'm standing in front of a TV camera, there is nowhere to hide, and it can be somewhat of an emotional roller coaster. But on the other hand, when things sell well, and viewers love an item, it truly is a great feeling! 

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid them?

Number one would be bargain shopping for a lawyer. 

Number two would be signing contracts without thorough understanding or excellent legal guidance. 

And number three would not be profoundly researching partners before signing a contract.

These can all be big mistakes! But, over the years, I learned that contracts didn't have to be one-sided, that a brilliant lawyer can be life-changing, and perhaps the most important lesson of all, never to judge your self-worth but what other people offer you when it comes to money! 

I was once told I was unemployable, which is a true story! But I had a vision for my career and I refused to compromise, which placed me on the entrepreneurial road. I was always under-capitalized and money was a stress point, which led to several stressful partnerships over the years. 

Throughout the earlier parts of my career, I was always waiting to be "discovered." I went from "understudy" to "star” at 60 years old, way out of the expected timeframe for the fashion business! Nevertheless, I never gave up on myself. My advice to other entrepreneurs is to know that your best armor is an unshakeable belief in yourself.

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning?

I rarely meet entrepreneurs with an overview or a pragmatic breakdown of their business. Instead, envision your niche within an industry that services a need. For example, my DG2 brand focuses on jeans for the middle-aged. I had yet to meet a fellow entrepreneur willing to be in that space until they hit 60–when their "aha moment" happens. Don't overlook an entire market segment just because you're not in it.

Diane Gilman, Owner of D2G and TV's Jean Queen / Josh Lehrer

The Successes

What are three seemingly insurmountable obstacles you've faced as an entrepreneur, and how have you overcome them?

For starters, in 1945, I was a female who wanted to be a career woman at a time when that wasn't the norm. I started dreaming of being a successful businesswoman in the early 1950s, which was very against the mold at the time. 

My family was highly opposed to my will to work at all. Back then, proper girls only had one route to success: to marry a doctor and become a housewife. Not only was I fighting public opinion, but I was standing up for what I wanted against my family's wishes. In addition, I had no financial capital to work with. I worked two jobs to save up money to be able to buy fabric and sew my own Diane Gilman collection samples. 

My Achilles heel was always being dependent on others to fund my fashion business, and subsequently, not owning most of it was frustrating and challenging. Over time, these experiences led to lessons that have helped propel me forward. One of my most significant obstacles was my breast cancer journey, which initially appeared insurmountable, but eventually became a tremendous strength for me as it forever bonded me to my female audience in ways I couldn't have anticipated. 

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

I believe my life is a musical, and I am writing the soundtrack. Create a series of tunes that touch your soul as a starting point. I also created my "25 Rules for Women Who Don't Like Rules," and rule number seven is to "Commit to No-Guilt Self Maintenance." Block time for yourself, whether for family, hobbies, or exercise. Everyone needs "True-You" time.

What three critical pieces of advice would have made your entrepreneurial journey more manageable, and why?

1. See Life’s Most Significant Challenges As Valuable Lessons

Sometimes the seemingly worst imaginable event turns into the best of luck. That's how I found my true place in the fashion world. Losing the right to use my name on my label led me to exactly where I needed to be and worked out better than I ever could have imagined.

2. Stay True to Yourself

If you genuinely believe in an idea, don't allow people to talk you out of it. Chances are that they don't understand, and one idea may become the key to success for the rest of your life.

3. You’re Never Too Old To Dream

It doesn't matter if you're a late bloomer. What matters is that you bloom. Let time take its course. The right business fit may take more time than you imagined, but the key is to do something you love, and every moment will feel well-spent. 

What is the most significant difference between how an entrepreneur sees their career path versus how an employee at a company sees their career path, and why?

As I see it, most entrepreneurs are the star and the essential component of their own business, while being an employee is more the culture of a beehive–you are part of a whole. Entrepreneurs are directly connected to their products and business, whereas employees can be subject to endless layers of red tape. Entrepreneurs are all about the direct response.

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