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Power Women:

Betsy Hendershot of Downward Dog Wine On How To Successfully Navigate Work, Love and Life As A Powerful Woman

Power Women: Betsy Hendershot of Downward Dog Wine On How To Successfully Navigate Work, Love and Life As A Powerful Woman

An Interview With Ming Zhao - Originally posted on Authority Magazine

Let it bother you. Sometimes it’s easier to identify what’s bothering you than it is to identify what pleases you. Address what’s bothering you about a situation, a person or an idea and you will more easily identify specific changes you need to make or barriers that need addressed or possibly removed.

How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series I had the distinct pleasure of interviewing Betsy Hendershot.

Betsy Hendershot is the founder of Downward Dog Wine, a boxed wine made from American-grown grapes from Tulsa, OK. She took notice as her 4-year-old Cock-a-Poo performed an ever familiar stretch as she was preparing to leave for her morning yoga class. It just so happened that she was actively searching for a name for a current project- a proprietary wine label that would set an example for quality wine at a value price in the boxed wine segment.

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 childhood “backstory”?

I grew up in Lebanon, MO where my parents owned a pontoon boat company. They both worked very hard and paved their way to success while actively supporting our small town community and raising my sister and me. We traveled quite a bit, mostly determined by work-related opportunities — boat shows, sales calls, dealer meetings, etc. I learned more about business in my teenage years than I did during my four years of college studying business and finance.

My learning came from listening to endless phone calls in the car and listening to sales speeches during professional meetings. I learned the art of selling during simple conversation and perfected a professional phone voice by the age of 16 while working as a receptionist during the summer. My childhood prepared me for the life I’m living now in a multitude of ways.

Can you tell us the story about what led you to this particular career path?

This was not a path I saw coming. My husband, also known for his entrepreneurial efforts, purchased a liquor distributorship in 2013. Even though I had an interest in wine, it wasn’t until I learned more about the business of wine that lead me in the direction of owning my own brand. It was my new found connections in the industry that gave me the knowledge and confidence I needed to launch Downward Dog Wine.

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

My first year in business was the perfect combination of success and disaster. I ordered WAY too much wine, specifically white wine, and had no idea that after a year or so after being in storage it would start to oxidize and eventually go bad. Not necessarily harmful to the consumer, but just taste bad. I was sitting on a couple truckloads of spoiled wine wondering what in the hell I was going to do — and then along came Covid 19 and the demand for hand sanitizer.

Shortly after the pandemic began, a friend of mine who owns OK Distilling Company, Hunter Gambill, reached out and asked if I had any old wine that he could use to turn into hand sanitizer that he could sell (at cost) to our local restaurants and other service-related companies to help keep them in business. We combined our resources and what started as a problem, very quickly turned into a solution.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I’m determined, adaptive and I like to run in the rain. The hardest part of the job isn’t making the big leaps, for instance, major presentations or sales asks. The hardest part is the day-to-day tasks that are on repeat.

Every time I find myself dreading the next task I put my head down, find my determination and work harder knowing the end result is always more rewarding when you put the time in. As a business owner learning to adapt to different working environments, different personalities and I have to be willing to adapt to change in general. Adapting doesn’t mean being a chameleon, it means being accepting and doing the best with what you are given.

I’ve set up wine tastings just about anywhere you can think of, I’ve cleaned up massive wine spills in my warehouse myself and I’ve walked the red carpet. Some of my best runs have been in the pouring down rain. I believe that if you are always waiting for the perfect environment to perform your task in, you are missing out on unbelievable opportunities to succeed.

The economic environment for small businesses right now is far less than ideal. We are dealing with product shortages, transportation challenges and inflated prices– and I’m out here selling boxed wine! What?! I’m not just running in the rain, I’m running in freezing rain, high winds and uphill — both ways! But I’m learning and learning is succeeding, more importantly, learning is setting me up for future success and I truly believe that.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so? I’m not sure if society feels uncomfortable with strong women, or if we (strong women) are still feeling uncomfortable with ourselves.

We are all a work in progress and changing our mindset after enduring decades of biases, is difficult even if we know in the depths of our souls that the change is right. Women have always been strong, the difference is now we are demanding to be heard and trusted and believed in. Of course, this is uncomfortable — but it’s so necessary.

Certainly, there are cultures of people that are unsure about women’s leadership, but I would suspect that these cultures are reluctant to any type of change out of fear of losing control. I have been lucky enough to grow as a strong woman in a very supportive culture that encourages strength and success for everyone, regardless of gender. It’s a mindset based not on fear, but on working really fucking hard.

What should a powerful woman do in a context where she feels that people are uneasy around her? First, she might pause and ask herself some self-check questions. Are these people uneasy about me or am I uneasy about myself?

If I’m feeling uneasy about myself it’s usually because I’m not being truthful with myself or those around me. Secondly, being powerful and being forceful are two very different things. Are you forcing yourself and your thoughts onto people that think differently than you do, or are you listening and educating? Are you speaking to these people or asking them to hear you? Are you taking your audience’s insecurities into consideration? Most of the time I find that people aren’t against powerful women, they are against power-seeking women. Big difference.

What do we need to do as a society to change the unease around powerful women?

Educate, educate, educate. And women need to continue to take on the tough jobs, be more supportive of each other and be there to pick each other up when we fall. As a society of strong women, we need to remove the guilt and the ridiculous expectation that we can do it all. Well, let me rephrase, we can certainly do it all, but it doesn’t all have to be done at the same time.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

The alcohol industry is very cutthroat. I’ve been in some very uncomfortable meetings but I don’t think it was because of my gender, I think it was because I was unprepared. Probably the most annoying conversation that I abruptly ended was after listening to a marketing sales pitch for over an hour, the salesman asked me if I needed time to talk it over with my husband before getting back with him. I just laughed and hung up the phone.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

I have absolutely no idea because I’ve never had the benefit of being a male leader — thank God.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

You are right, this is a familiar challenge for any working parent. This comes mostly into play when I need to travel. True statement: I would be more successful if I were able to travel freely for work. No if, ands, or buts about it.

But, I absolutely hate being away from my kids for long periods of time. Right now I am choosing the success of my family over the success of my company and I’m good with that. However, there are times where travel is inevitable and I find comfort in the fact that letting my husband wear the mom pants and letting my kids see my sacrifice is important for my family as well.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

Unfortunately, Covid. I could no longer work from 9–4, it just wasn’t possible. It was also impossible for me to work and pretend I wasn’t parenting at the same time. In a way, it was such a relief.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

Beauty and appearance are important — no doubt about it, but it will only get you so far. I put a decent amount of time into my appearance, but it’s more for my own confidence than it is for the pleasure of others which does give an inherent value. If I’m good with me, the pressure’s off you, right? We can move on to more important topics. Luckily now, we are starting to accept beauty in many different ways. It’s less about being “perfect” whatever that is, and more about valuing yourself enough to take time for yourself.

How is this similar or different for men? Very similar. Who likes a sloppy salesman? Gross. Get your shit together.

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 Powerful Woman?” (Please share a story or example for each.)

  1. Listen. If you keep pushing away the voice inside your head you will miss out. Listen to that voice especially if it’s something that you don’t want to hear. Face the truth and move on. Also, take time to listen to the advice of people you trust and listen to personal development and “how-to” books. There are some really helpful people out there that know what they are talking about! Lastly, listen to what the numbers are telling you — they are rarely wrong.
  2. Fulfill commitments. These can be personal, professional or financial. If you commit to something follow through to earn the trust of those around you. Proving yourself reliable and accountable is extremely important.
  3. Know when to decline. Spreading yourself too thin is a recipe for disaster. When I get that ever-familiar “I can’t breath” feeling I try to find the one thing that doesn’t fit and drop it. Sometimes this takes a minute, an hour or even a day, but you will find it. And girl, drop it like it’s hot.
  4. Look up! Stop comparing yourself to the fake-ass world on social media, you are wasting valuable time. Do what you want to do and how you want to do it.
  5. Let it bother you. Sometimes it’s easier to identify what’s bothering you than it is to identify what pleases you. Address what’s bothering you about a situation, a person or an idea and you will more easily identify specific changes you need to make or barriers that need addressed or possibly removed.

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