We had the good fortune of connecting with Ashley Crenshaw and we’ve shared our conversation below.

Hi Ashley, what was your thought process behind starting your own business?
My business was created out of a necessity. I needed a way to track the customers I was getting from a business that I had fallen into but there wasn’t anything that met my needs. I wanted a planner that would help me manage my money and my projects but it just didn’t seem to exist. Inspiration struck while I was scrolling through YouTube. A girl had created her own business binder using templates from Etsy and Dollar Tree supplies. I was impressed and thought “You can do that!” so I did. I met up with a friend a while after that and told her about what I’d created and expressed that it still felt a bit lacking. I wanted to hire someone to turn my binder into a coil bound planner but didn’t know where to start. My told me to ‘just make it yourself’ and I laughed at her. But she was serious and continued to motivate me until I took it seriously.

The truth is my business chose me. I, honestly, never thought I’d be here. Becoming a business owner was not a goal I had growing up. I wanted to be a lawyer as a child, then an optometrist in college but ultimately fell into Business Management and Accounting. I guess the universe knew me better than I knew myself and positioned me to be where I am today. I spent several years not knowing where I wanted to be, who I wanted to be or what I want be. My only real goal in life was to be fulfilled. So when the idea of Boss Made began tumbling around in my head, it didn’t seem as outlandish as it would have earlier in my life.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I own what I call a Micro Business because even small businesses have employees. Unlike those businesses, I am a one woman show. I am customer service, the graphic designer, the marketing team, I process and ship orders, and I hand make every planner. The idea for Boss Made Planners started in 2018 but I didn’t release a product until two years later. Building a business/brand from nothing has been the hardest thing I’ve ever done. Things rarely ever go as planned and every failure is on me. And I feel the stress. I’ve been emotionally drained more times than I can count. Which is pretty often since I am an introvert that suffers with reoccurring bouts of depression and anxiety. I’m constantly thinking that I’m not enough. Or I’m not doing enough. Or that I’m not where I should be (wherever that is). Me 10 years ago, would be in utter disbelief in who I am now. Me 15 years ago, would tell me to get away from her lying like that! I wouldn’t blame them though. I ask myself who gave me a business every day. As if I wasn’t the one who chose to ride this rollercoaster of creativity and taxes.

My brand is minimalistic by design. My products are simplistic and highly customizable. My goal was to create a brand with products that everyone could use and make their own. I truly believe that planning is for each and every one of us. And it should be accessible to every one of us. Although, we are still growing and coming into ourselves more each day, I do believe that I achieved that goal. We should all experience what it’s like to work hard and achieve a goal.

It’s been tough, but each day I wake up and choose to be a business owner. I go to my office and I print pages and I send emails and I create things that fill me with dopamine. Then I go to bed just so i can get up and do it all over again. It’s messy. It’s exhausting and I love it.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
As an introverted homebody, I am the last person you should call for tourism advise or to be a tour guide. However, if my friend needs seven days worth of fun spots to visit, I’d first start with food. On day 1, we’d go to the fish market and get some fresh, Gulf Coast seafood. Both fried and steamed. On day 2, we’d visit the Mobile Carnival Museum and learn about the history of Mardi Gras. See the royal regalia and more. On the third day, we’d go to a locally owned movie theater called the Crescent Theater. It’s a small theater with only one screen where one movie plays at a time. It’s a super cool experience. On day 4, we’ll have brunch at SOCU’s Southern Kitchen. SOCU is owned by a Black, woman who was born and raised in Mobile. It is high end dinning, centered in downtown Mobile. She’s also a master chef. By day five we’d need some sun so we’ll head to the Medal of Honor Park. It’ll be a great way to get some exercise and see nature via the many trails in the park. Maybe even have a picnic for lunch. On day 6 we’d get our friends and go to the Soul Kitchen and catch a show, concert or poetry night. After the show we’d walk the strip downtown, get some drinks and food. On the last day, we’d take a quick trip out of town. I’d let my friend choose the location and we’d just let the experiences find us. Luckily, Mobile is close to New Orleans, Mississippi Casinos, Gulf Shores Beach, and the Florida panhandle.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
The biggest reason Boss Made Planners got off of the ground, was due to my best friend and fellow creative, Kiearstan. When I was struggling with managing my furniture flipping business, I’d vent to her about my needs and how there wasn’t anything on the market for me. I’d find myself super frustrated and annoyed. But she’d just look at me and say, “Girl, if you don’t just make for your own planner”! Her exact quote was, “Your name is Ashley Makes It, so Ashley needs to Make It’! I just stared at her for a moment and then I laughed. I laughed because she’s hilarious and I laughed because I thought that whole idea was absurd. I couldn’t make my own planner! However, in the back of my mind, I was starting to believe it wasn’t so farfetched. So I came up with another excuse, “Where would I even start”?! She was like, “YouTube it”! So I did.

Not long after, I had a personal business planner. Then she said, “You should sell it”! Now I’m convinced that my friend crazy and six months later I had a prototype. I was so excited and she was the first person I called. I sent her pictures and videos and she was not impressed. I’m laughing just remembering the day. At the time it hurt, but she gave me some honest critiques. A year after that, I had my flagship product, The Boss Made Planners Business Planner. It’s my best selling product to date and I wouldn’t have it or my business without Kiearstan and her crazy faith, high expectations and wild imagination.

She believed that I could do something that I never even dreamed about. It’s been almost four years since I first vented to her that day and here I am now. Still asking her if this looks good or not.

Thank you, Kie.

Website: www.bossmadeplanners.com

Instagram: www.instagram.com/bossmadeplanners

Twitter: www.twitter.com/bossmadeplanner

Facebook: www.facebook.com/bossmadeplanners

Youtube: https://www.youtube.com/channel/UCSZSetTReUEk7qqcdjyBOtQ

Other: www.tiktok.com/bossmadeplanners

Image Credits
Larry Mosely Cesar Moffatt

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