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Female Founders: Cheyenne Smith of Dakota Ridge On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Candice Georgiadis

You will fail I am a perfectionist so failing and learning as I go is hard. You will fail but the key is to learn from it and improve upon it so that next time you try you will succeed.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Cheyenne Smith.

Cheyenne is an ex -marketing agency kid turned entrepreneur. She is the founder of Dakota Ridge- a fashion forward rubber cowboy boot that cowboy boot that is stylish without compromising functionality. Cheyenne also runs a marketing agency specializing in paid media in the e-commerce space.

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?

I’ve been in advertising since I got my first intern at an agency when I was 19 but started my entrepreneur journey after I had my daughter and couldn’t go back to work after maternity leave to a job I hated. I needed to find a way to
financial help support my family while being able to stay at home with my daughter.

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

My favorite stories to tell are around spending the entire first year at home with my daughter while taking zoom calls. We called her my executive assistant.

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?

It’s not a funny mistake but I tried to pack so much in a day every day that I would just lose track of the house and
would forget to eat myself because if I wasn’t in a meeting I was feeding or napping or changing my daughter! So, the learning there is make sure to schedule in breaks for walks or eating!

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?

My best friend and ultimately co-founder of Dakota Ridge Kylee. She is also a mom and saw how much I was struggling to schedule time for myself, so she came in and really made sure I was taking time for myself and taking A LOT off my plate.

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?

I think our society tends to see women as mentally split between having a family and having a good career. Each one is not individualized, and women can have one or the other or do both without sacrificing pieces of themselves.

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?

I think it starts with those around us and supporting us. Women tend to take the brunt of the housework according to
studies just based on past societal structures and expectations. Offer help to women in your family and always always support them in their endeavors without pushing what society says a good woman should be. THROW THAT OUT THE WINDOW. Allow the women in your life to be who they are whole heartedly.

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?

In my opinion women are extremely great at problem solving and multi-tasking to get to the right solution quickly. It feels like most of the women I know have 15 tabs open in their brain in any given instance worrying about their partners, their job, their clients, their children, their dogs, and then on top of that themselves.

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

I think people always think I know what I’m doing. To me that is the biggest myth about founders. I feel like we all are just shooting in the dark. Taking WAGs. wild ass guesses and hoping that it works.

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?

I think founders need to be willing to do anything to not fail in the long run. Hustle for lack of a better term. Everyone will have small failures when starting a company but the biggest thing that sets founders apart I believe is the willingness to fail in the short term to learn something for the long term.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. You will fail I am a perfectionist so failing and learning as I go is hard. You will fail but the key is to learn from it and improve upon it so that next time you try you will succeed.
  2. You need to take time for yourself Not slowing down and breathing every once in a while will actually slow you
    down in the long run. I wish someone told me to take more time for myself.
  3. It is harder than I ever expected but the cost is worth the prize of flexibility I have stayed up until 2a more times than I’d like to admit but I wouldn’t trade being able to volunteer at my daughter’s school on a week day without having to ask permission for anything.
  4. once you pop you can’t stop I feel like I was bit by the bug and now all I want to do is start businesses and learn the ins and outs of them
  5. you will meet amazing people along the way I have met some of the smartest most amazing women while becoming a founder.

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

I am doing my best to support other women in starting their own business and helping them realize they can have everything they want out of their life whatever that is.

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.

Supporting women who want to run their own businesses in a man’s world while also following other dreams.

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.

Brene Brown!!

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

Female Founders: Cheyenne Smith of Dakota Ridge On The Five Things You Need To Thrive and Succeed… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.