Alright – so today we’ve got the honor of introducing you to Jacalyn Rae. We think you’ll enjoy our conversation, we’ve shared it below.
Jacalyn , thanks for joining us, excited to have you contributing your stories and insights. So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?
During college, the majority of students have an idea of what they want to do after, but they don’t have a plan to implement in order to get there. If I could go back to college knowing that I wanted to become an entrepreneur, I would actively apply the things I learn to my business.
In College I had already begun my business as a Makeup Artist but never had I focused on growing my business while I was enrolled. This is because the curriculum wasn’t flexible enough to apply to such vast variety of careers.
An Idea to allow students to actively apply their knowledge to their careers or businesses would be having personalized curriculums based on individual preferences. If classes are specialized towards ones personal business, students would be able to retain more information, grow their businesses faster, and better understand the content being taught.

Jacalyn , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
My Name is Jacalyn Rae and I am a Professional Makeup Artist. Being a makeup Artist is not as simple as the application itself. It’s a complex career that requires creativity and many management skills.
I became a Makeup Artist as a young girl exploring my creativity which organically led to doing makeup for friends and family, then friends of family, and now after years of hard work, clients around the country.
I began offering services such as Bridal, Fashion, and Editorial Makeup which has transformed to much more including leading large fashion teams, and becoming the Product and Media Manager for DA Beauty with Jacalyn Rae.
It all began when I was 21 and fled my hometown in Maine to attend Makeup School in Texas, with dreams of moving out west and never returning. Shortly after, I was diagnosed with Giant Cell Osteoblasts in my face that required me to move back home for medical treatment. After a year, I was healthy and felt set back but the fear of regret fueled me to try again.
Living in Maine, it’s hard to make it big in the fashion world, so I began networking in the fashion capital: New York City, through social media. It took some time to get any leads but one random Wednesday, I drove 6 hours to New York for a networking event at which I met my current business partner, Donny. Donny is a photographer, NYFW show producer, and designer of 2 brands, but he didn’t want to complicate his shows with a Makeup team. After months of volunteering and convincing, he finally gave me the roll of recruiting and organizing a Makeup team for Model X Showcase, his show at NYFW.
I became Donny’s left hand Makeup Artist, and led every show out. Now, show producers hire me to recruit and organize Makeup Teams for shows all over the country. When Donny’s clothing brands ,Donny’s Angel and Donny’s Devil began doing well, he decided he wanted to add cosmetics to his collection. Luckily, he knew someone with expertise in makeup! As of recently the two of us have been growing our cosmetic brand, DA Beauty with Jacalyn Rae. I am responsible for the social media presence and quality of products. Together, we have curated a collection of Leaping Bunny Certified, cruelty free products that are made without gluten or sulphates!

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
Growing up, I was taught not to speak up for myself. If I did, I was considered weak. I was taught that I would be more respected if I stayed quiet and didn’t make an impact.
As an adult, I noticed that remaining quiet has done the opposite and made me more vulnerable. Remaining quiet allows people to decide who you are. It allows them to assume based on their experiences. When people have negative mindsets, they perceive negatively so it’s important for people to protect themselves by speaking up.
If a person speaks up but is still perceived negatively, at least they have the peace of mind knowing they were authentic.

Do you have any insights you can share related to maintaining high team morale?
In order to manage a team, you must have difficult conversations that risk people not liking you. I believe it’s important to know that not everyone teammate is going to like you, before getting into a management position.
While not everyone is going to agree with you, there is a way of getting your point across without coming off a certain way. With humor. The team being managed expects there to be difficult conversations at times as no corporation is perfect. Using humor to facilitate these conversations can show the team that the leader has emotional intelligence and control. The leader will also be respected and trusted more if they have a good attitude because staying positive in tough times is difficult but it’s simple when you throw in a joke here and there.
Contact Info:
- Instagram: Jacalynraethemua
- Other: Tik tok: jackkkkkip


