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"Being a Founder Is Lonely AF Sometimes"—A Young CEO Gets Real About Life at the Top

When Ellyette Gheno launched her company Bootaybag, she was excited to fill much-needed whitespace and disrupt an outdated industry while building a community that lifts each other up and feels empowered. Now, her side hustle is changing the game, giving the $52 million underwear market a run for its money with its innovative monthly subscription model and women everywhere are loving the modern styles and positive messaging. 

Despite her success, Gheno’s entrepreneurial journey hasn’t been without its challenges and setbacks but it’s how you handle those missteps and move on from the haters that define who you are, your brand, and its future. In our chat, Gheno shares some of the failures and challenges she experienced along the way, how she turned them into opportunity, and her tip for handling haters (and turning shade into positive business development.)  

On a time she failed and how she turned it around…

Every time we launch a new monthly style drop it's an opportunity for our community to give us their honest feedback (publicly). You wouldn’t believe how easy it is for people to be mean on social media (behind a fake username, with a touch of a button). There have definitely been times we’ve seen hate (not just around the style drop) on social. We’ve learned you can’t please everyone. We are lucky to have such a large community of subscribers, however, we only release four styles every month, so we do our best to release a little something for everyone. We’ve taken all of the negativity and hate and “failure” that social media brings and turned it into a platform of positivity. We pride ourselves in our customer service and our brand language, and how we talk to our girls. We read every comment, DM, and we listen. We keep it real and allow our brand to be human.

On the biggest challenge, she’s faced since becoming a founder…

Every chapter, every “next” level is a challenge. Let’s be real, this shit ain’t easy. There are many times where I don’t love the feeling of being uncomfortable, but in these situations, I live for it. I am not afraid to be vulnerable, especially with my team. As a small business, we are all juggling a million things and figuring them out as we go with no shortage of mistakes along the way. I like to take that opportunity to show them that even though I may be “the boss,” I am riding the same wave. It’s okay to make mistakes, it’s the recovery that matters. 

On the biggest lessons, she’s learned along the way…

The biggest lesson I have learned is to have confidence: in myself, in the brand, in my team, in everything that we do, and stand for. Especially in the beginning, I allowed the classic imposter syndrome to kick in and  I allowed other, more “qualified” people to call the shots. I think the best thing that has happened is that I’ve validated the confidence I needed in myself as a leader, I stand true to my brand and I know that no one else will ever know the brand the way I do. 

Photo: Courtesy of Bootaybag

On the hardest professional decision she’s had to make…

Firing—so not fun. Every fire is hard. I’d like to say it gets a little easier as you begin to realize you are making the best decision for yourself, the brand, and typically the person on the other end as well. I also made a personal choice to keep the hiring very transactional—don’t get me wrong I love my team, but hiring and maintaining the relationships from respect and professional manner, allows me to not only have hard conversations but make the best decisions. 

On the traits, you need to succeed as an entrepreneur or founder…

I’ve always heard that I’m hard-headed so I guess that’s helped me get to where I am today? I definitely think it’s important not to be distracted by what others are doing around you and to focus on what you’re building is key. So many times I have to remind myself to stay in my zone. 

On the money mistakes, she’s made…

Oh yes, money mistakes, how much time do you have? You know, although we are fortunate to be a  profitable company, every dollar earned goes back into reinvesting in the business. Every target has to be hit for us to be able to grow and every dollar counts. I’ve made plenty of large mistakes because of the amount of wiggle room is so narrow—I’ve actually almost failed my business entirely a few times. Oops! The more those instances arise, the more confident I am that I’m just missing the solution. Tapping into my network has been huge for me. Mostly to find someone who has already gone through it and made the same mistakes. Utilize them to ask the hard questions, and be vulnerable to the situation truths. You aren’t the first and you won’t be the last—it’s okay to not know and be scared.” 

Photo: Courtesy of Bootaybag

On her #1 money tip for small business owners… 

Get a cash flow sheet done by a professional. I’d highly recommend hiring a consultant or somebody that could educate you around how cash flows in and out of your business and what levers you have. Understand your P&L sheet and ask all the questions when you don’t. You should be able to read your cash flow sheet and P&L as well as your accountant. Cash is king.

How she works around the worst-case scenario when it comes true…

Things never go as planned. Lesson number 1. I go back and remember in the beginning how dramatic every mistake felt. If I could tell myself one thing it would be “chill, it gets worse’,” ha! The way I react and move forward in these situations now has definitely come from past experiences. As a founder, you have to welcome that “here we go again” feeling with open arms. Not to say it’s all bad, there are definitely exciting moments and successes to welcome as well, but I feel those are often the ones highlighted so just trying to be real. My biggest learning and note for others out there is to take a moment to breathe before putting out the fire.

On how she deals with criticism and customer complaints…

The best tactic is to get in front of it. Own up to being wrong, own up to making mistakes, be vulnerable and truthful about who you are as a brand and what your mission and goals are. There are always going to be some haters under the bridge that come out at sundown… but for every one hater, we’ve found a hundred babes on our side. I think vulnerability and authenticity are really what differentiates small biz brands from corporate companies. We have the advantage to show face, and use our platform to directly talk with our community, so why not?

We actually just went through an experience where we made a mistake that really upset our members (which was never our intention) and we got a lot of hate. I decided to personally show face, apologize and own up to the mistake that was made, and that was really all I could do. We received an outpouring of respect, however, haters gonna hate. Just make sure you’re real and true to yourself and your brand and those who genuinely support you and your mission will show up. 

On founder depression and advice for young founders going through it…

I can’t stress enough how important it is to have someone to talk to. I have a life/business coach who I can vent to because honestly, being a founder is lonely AF sometimes. Then you realize, wait, I’m not the only founder out there, other people must be feeling this way too. It’s been unreal to see the reactions from other founders who are so open to helping one another. You can almost always get someone to meet for coffee, grab a drink, or hop on a quick call to chat if you are straight to your point on what your intention is and show value in their time. In addition to having someone to talk to, it’s equally important to make sure you’re practicing a healthy work/life balance. Set your non-negotiables, morning routine, midday workout, evening journal—put them in your calendar so you are constantly reminded to take this time for you.

On how she stays inspired and motivated on challenging days…

Time management is key—this keeps me organized and motivated. The moment my day is open it’s the Wild Wild West. Structure has been a necessity for me, but when it comes to blocking out creative time and I am not feeling creative, I skip it. You can’t force creativity. I stay motivated and inspired by other brands and people in the industry.

On the reality of being an entrepreneur today, behind the filters…

It’s definitely not for the faint of heart. You have to be passionate, that’s number one. Then you have to be profitable, hire the right people, be a boss, and also not get distracted by what others are doing and saying about you. I think the biggest reality is that social media and what you read on the internet are highlight reels, just like anything else founders show a lot of the “fun, flirty” side of the biz and not the “I am running out of cash” or “I haven’t slept in 12 days” sides. Social media makes success look like “luck” but there is a lot of blood, sweat, and tears behind that filtered post.

On the one thing, she would go back and tell herself…

More “no” and less “yes.” I’ve always had the mindset to always say “yes.” Just go for it, wing it. Well, needless to say, this year I am working on saying “no” a lot more, lol. Be sure to really vet out opportunities and sources. There are a lot of things that are marketed well whether its a single contractor or an event that is going to do “x, y, and z “ for your businesses. Check it out thoroughly, always lean on resources and references, case studies, etc. Generally, if an opportunity is “so good” it’s not going to be desperate for your small businesses. It’s like dating, the good ones are hard to find. I’ve gotten burned taking deals with contractors, software, events, influencers just because I fell for what they were selling. More “no”  in 2020.

On her definition of success…

I personally do not measure success in dollar amounts. Success to me is creating a life that you enjoy, and seeing through that your passions become your reality. Nothing is more fulfilling than being able to work with amazing women, create a really good product, and have an impact on a community. Even having an impact on one person would be a success, but we’re lucky enough to have an impact on an entire community, and a pretty badass one if you ask me. The cliche “If you love what you do, you won’t work a day in your life.” is the truth. 


To learn more about Gheno’s amazing company, visit bootaybag.com.

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