Rachel of Rent My Wardrobe


When it comes to women in business, we get really excited. As a girl boss herself, our founder D’Andra Simmons loves being able to connect with and lift up other women who are crushing it in the business world. In fact, our inspiration this month, Rachel Sipperley of Rent My Wardrobe, also shares that love, and we are inspired by the fact that this camaraderie and encouragement is becoming increasingly important amongst women in business.


Rachel believes that there are many incredible things that can happen when women “drop our egos and fears and make an effort to genuinely and authentically support one another.” She has had many women come into her life and help in her journey without wanting anything in return. She says that getting to do that for other women at this point in her career is the most rewarding and fulfilling part of her life now.


As an entrepreneur and “female founder”, Rachel always has busy days and lots of work to be done. “I usually have 5-8 meetings a day with partners, vendors, investors, and other founders. I usually work 80-100 hour weeks, and on top of running the business, I maintain my side hustle as an Airbnb and Turo host. I often get 3-5 hours of sleep a night. I know it's a huge sacrifice right now, but while I am missing out on opportunities to go out with friends or rest, I think about the greater good and what we are building and the lives that we are impacting. I always tell myself I'm banking hours now before I have a family, so one day when I (hopefully) am blessed enough to have children, I can spend more time with them.” We love her dedication and willingness to do what it takes to make her dreams happen.


It’s basically a known fact that when you’re working 80-100 hour weeks running a business AND a side hustle, there are bound to be some hard nights. “As an entrepreneur, we have so many hard nights and hard days. I recently had an experience with an employee whom I thought I could trust and rely on and had pure motives. It turned out that was not the case, and I learned one evening about the disparities occurring. I was heartbroken and felt so duped and betrayed, and so so stupid for not waking up sooner to see the sheep in wolves clothing I was dealing with. I couldn't sleep, actually vomited, and was so hurt and angry. In that moment, I had to find the inner strength to stand firm in the mission of our business. I was really just baffled and so taken aback that something like this could happen. The next morning I learned that there were significant character and reputation issues with this individual that were precluding a number of other business deals and growth in our company from happening. What felt like the biggest hurt was actually a huge blessing and learning moment for me.”


When asked about her favorite thing about her business, Rachel says, “My team! The people I get to work with and the founders I get to mentor and help out.” It’s obvious that Rachel is very people-focused, which we know is an important part of being a business woman and CEO.


Killer instinct. Grit and tenacity. The constant forethought of putting others before self. These are the things that Rachel believes are important when it comes to being a girl boss or power player. She knows that business is all about working towards your mission and finding people that will support it with you. Like she said before, big things can happen when women support women!


About Rachel:


Rachel Sipperley is the CEO and Founder of Rent My Wardrobe, a peer to peer marketplace that empowers women to generate additional income while becoming more financially savvy. The daughter of a youth pastor, Rachel came from humble beginnings and was a born entrepreneur. She completed her undergraduate degree at 19 years old, was a top executive for a Fortune 500 company by age 22, and had purchased three homes by age 25. Her corporate success and never-ending side hustles allowed her to completely self-fund the startup, now backed by Venture Capitalists and TV personalities Court and Kameron Westcott. Her mission is to inspire and equip women and girls to become their own entrepreneur in a women-supporting-women culture and share her testimony of financial stewardship.

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