Samantha Myers of ‘Let’s Dress Up’: “Goals”

Aim high, have a big goal. But also have smaller quantifiable and shorter term goals that will help you to stray on track. As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Samantha Myers. Samantha and Judy Famigletti are the duo behind Let’s Dress Up, […]

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Aim high, have a big goal. But also have smaller quantifiable and shorter term goals that will help you to stray on track.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Samantha Myers. Samantha and Judy Famigletti are the duo behind Let’s Dress Up, a fairytale-themed play and birthday party space for kids in the heart of New York City. Samantha left a lengthy career in Financial Services in 2018 to be an entrepreneur and joined forces with Judy at Let’s Dress Up.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

After graduating from college at Tulane University, I got an entry-level job in the Financial Services Industry and loved it. Twenty years later after various roles, a merger, countless restructurings, and a couple of moves I was burnt out and ready for a change. So I decided to answer that nagging voice in the back of my mind that told me I should own my own business. I approached Judy about coming on as a partner at Let’s Dress Up and an entrepreneur was born.

Can you share the most interesting story that happened to you since you began leading your company?

I will share a feel-good story from couple of months ago. I got an email from someone wondering if we were hiring. She went on to say that she had her 5th Birthday Party at Let’s Dress Up! She still lived in the neighborhood and was coming home from college for the summer. She had such fond memories that she wanted to work with us. So amazing.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One that comes to mind is when three-year-old twins at a birthday party were having a monumental meltdown over a mermaid dress. I somehow ended up in the crosshairs of both the twins and their stressed-out mom who ended up yelling at me in the middle of the event. It was a lesson in customer service. I kept my cool, but took it personally. I would like to think I would handle it better next time (though thankfully nothing on that scale has happened since).

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Obviously, friends and family are key to the whole process, keeping you sane, honest, laughing, motivated, and everything in between. My husband is a serial entrepreneur and he encouraged me to make the leap from my predictable office job to the wild world of entrepreneurship. He helped me believe that I could truly be a successful small business owner.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

It’s intimidating. It’s risky. It’s uncomfortable. It’s sometimes hard to get out of your own head and have the confidence for a big change in structure, lifestyle and routine. You have to get past the fear of failure.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

The attention being paid to the topic as of late is very helpful in raising awareness. As existing woman founders, we have an obligation to go out of our way to share our knowledge and experience. Small businesses should be encouraged to get certified as women-owned. Mentoring, sharing funding opportunities, and highlighting available (preferably low-cost) resources are also key and can be addressed from many angles both private and public.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

It’s so rewarding to bet on yourself. It’s exciting and demanding and stressful and amazing. It gives you more flexibility in some ways (which comes in handy especially for the fellow mompreneurs out there) but can be more challenging in others. It’s all a juggling act, but it’s your juggling act. Never a dull moment.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

The biggest myth in my opinion is that a founder has to come up with the next “big idea” for a product and create it in their garage while working another job or mortgaging the house to do it. This is simply not true. There are many ways to be a founder and business owner, just as there are many types of businesses and industries.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

Everyone is definitely not cut out for it. At the same time, there is no magic recipe and everyone’s journey is different. For example, I worked in an office for many, many years and was a great employee. I was motivated, successful, and happy. Surprisingly many of the lessons I learned in finance translated well to eventually becoming a founder and entrepreneur. Discipline, accountability, work ethic, multi-tasking, and professionalism to name a few. (And, of course, I learned a few “dont’s” along the way).

Ok super. Here is the main question of our interview. Based on your opinion and experience, What are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

1. Goals. Aim high, have a big goal. But also have smaller quantifiable and shorter term goals that will help you to stray on track.

2. Financial knowledge. Know your numbers, costs, revenue. You don’t have to commit them all to memory, but keep them at your fingertips.

3. A Team. Have a key group of trusted employees, advisors, partners, peer groups and friends. You will need them!

4. Resilience. It’s a roller coaster sometimes, try not to get too high or too low. You must be able to adjust, adapt and recover from disappointments.

5. Have an outlet. Find things outside the business that help relieve stress and keep you grounded. And always keep your sense of humor.

How have you used your success to make the world a better place?

I like to start with a narrow definition of “world” and move outward from there. At home, I am a good role model for my daughter and my example will help shape the next generation. I am a good business partner, both Judy and I work to make a successful working relationship. I am an active member of our local community. We participate in local events, collaborate and promote other businesses, and try to be a leader in our local area.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

The more we talk about women being founders and leaders, the more common it will become. This is why I was especially excited to participate in this article. This is the movement.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Marcus Lemonis is someone I look up to business-wise. He is tough but fair and straightforward. He has so much experience and insight regarding small businesses, I would love to pick his brain over lunch.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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