Cultivating Talent And A Community: This CEO Runs Her Company With A Lot Of Heart


There is certainly no shortage of talented people out there, but not every talent is heard or seen—enter Cultivated Entertainment. Cultivated Entertainment is a talent service that helps its clients succeed and reach—and perhaps even exceed—their potential in whatever field they may be. Whether a chef, singer, journalist, athlete, or someone of another profession, Cultivated Entertainment takes pride in its conscientiousness in catering to specific, individualized client needs. The Founder and CEO, Jen Proctor, is a people person with a big heart, and she treats each client like family. We asked her to share a bit about her business and why forming a warm, familial environment is so important to her.

1. What inspired you to start Cultivated Entertainment? Was there a sudden A-ha! moment from which the idea was born?

Running my own business was instilled within me very young, whether I knew it or not. My entire life, I’ve watched and learned from my entrepreneurial father. Owning his own business, he had the freedom to make decisions that were aligned with his values, what he believed was best for his clients, and how he wanted his brand to be perceived. And I was fortunate to absorb all of this wisdom throughout my childhood. Up until I formed Cultivated Entertainment, I had worked mostly at large companies. It was incredible experience and I learned a lot, but there came a point where I wanted the freedom to choose the projects I worked on. I wanted to be inspired by the types of projects I was involved with on a daily basis and not just working on them because I “had to.”

2. What makes Cultivated Entertainment different from other talent services?

The number one reason that I attribute my success to is my relationships. I truly believe that we are nothing without trust from others and the incredible relationships we create—personally, creatively, and in business. Each and every client of ours is treated like family. Cultivated Entertainment is not a cookie-cutter company, we customize every project based on the specific needs of the client. We take the time to build and develop relationships with each person that walks through the door. The center of our entire business is talent—whether it’s a TV show, a development project, an event, or a brand—so we work with clients to identify, strategize, and deliver the most effective outcome for their goal.

"There are as few reasons I chose the name. The first being the meaning of the word cultivated, it’s about growth and a particular gravitas that takes care and attention to create. This is exactly what we are all about." Photo courtesy of Stefanie Villers

3. Tell me a little bit about your podcast? What sparked the interest to create Cultivated Conversations? Do you have a favorite episode?

Cultivated Conversations was born out of a WCW (Women Crush Wednesday) post that we started doing on our Cultivated Entertainment Instagram account. Each Wednesday, I would feature a woman I have worked with, know personally, or who inspires me. The feedback we received was incredible. People wanted to hear more, they were inspired. Thus, the podcast was born. Each of my guests has an incredible story to tell and we discuss real life topics in a vulnerable way, usually sitting in my living room, where I love to record. Whether you’re a college student, a business owner, or a stay at home mom, there is something in this podcast that resonates with everyone. We all have our own unique experiences and believe it or not, we all have lessons to learn from each and every person in our lives. I have to say, my favorite episode has to be the first episode. Not because of the guest, as I could never choose a favorite guest—all of these women inspire me—but because it was exhilarating to press record on something I knew had the potential to impact people’s lives. Take a listen and let me know what you think—I love feedback from listeners!

The Cultivated Entertainment team. (Photo courtesy of www.cultivatedent.com)

4. How do you foster close and meaningful relationships with your clients? Why is this so important to your mission/overall success?

I suffered from a lot of loss as a young child and had to grow up very quickly. Because of this, I learned the importance of communication and relationships at a very young age. I would not be the strong, confident, and successful woman that I am today without the people in my life. I always approach relationships from an honest and open perspective, and that is key in building a real connection.

5. How did you come up with the name “Cultivated Entertainment”?

There are as few reasons I chose the name. The first being the meaning of the word cultivated, it’s about growth and a particular gravitas that takes care and attention to create. This is exactly what we are all about. Secondly, my family has been in agriculture for many generations; I grew up driving around the farms with my Dad. I am very lucky to have a close-knit family and I love the fact that our history is a part of my company name.

6. What has been the most rewarding project you have been a part of thus far?

We have been so fortunate to work on an incredible array of inspiring and rewarding projects. While I don’t have one that could be deemed “most rewarding,” projects that are examining our culture today are so important right now. Working with the teams at Sarah Silverman’s “I Love You, America” on Hulu and Aisha Tyler’s “Unapologetic with Aisha Tyler” on AMC, have been great for me personally. Sarah’s show highlights the beliefs, values, similarities, and differences of us as Americans and is intelligent, encouraging, and of course, funny. And Aisha’s show is creating conversations unlike any others out there, with guests like Charlize Theron, Gloria Allred, Laverne Cox, DeRay McKesson, and more, talking about a range of topics from body image and gender discrimination to racial and social injustices. I feel very lucky to be a part of these opportunities to foster conversation and share varying viewpoints during this critical time in our culture.

7. Who is your biggest female role model in the entertainment industry right now? Why?

There are so many women, in entertainment and outside of it, that inspire me. Right now is the most incredible time for women as we’re seeing women of all colors, shapes, sizes, and backgrounds making a difference, pushing boundaries, shattering glass ceilings, and standing firm for what they believe in. I feel so inspired being a woman in this pivotal moment in history.

8. Have you faced any challenges as a woman blazing a trail in the industry? If so, how did you overcome them?

Throughout my career, I approach every opportunity with a positive disposition and upbeat demeanor. In business, these traits can be perceived as a weakness and something to be taken advantage of. Especially when you are a woman. But I have always remained firm in who I am and the way I know I want to conduct myself and never let anyone’s perception sway me to be someone I am not. In relation to that, I always want to take care of everyone and know that I put additional pressure on myself to be a perfectionist. Whether this comes from being a woman, or it’s just the person that I am, it creates an added layer of stress and responsibility in times when it is simply not necessary. I spend a lot of time worrying about everyone else. Admittedly, this is one of my best qualities and biggest curses.

9. Any advice for fellow female entrepreneurs?

Ladies, you so got this! The quickest lesson that I learned as a business owner is that you really have to take it one day at a time. If you work as hard as possible and pour your passion into what you believe in day in and day out, you can hold you head high knowing the results will come. Every single day is a new adventure; there are ups and downs and it is an amazingly wonderful and wild ride that you need to embrace. And for those moments when you feel overwhelmed, stop, take a breath, and focus on one goal right in front of you that you know you can achieve. It can be making one phone call to a prospective client, filing one contract, or answering one email. You’d be amazed as how quickly you can shake off the feelings of dread and refocus that way.

"I feel very lucky to be a part of these opportunities to foster conversation and share varying viewpoints during this critical time in our culture." Photo courtesy of Ashley Streff

10. What’s next for Cultivated Entertainment?

We are expanding to New York this month, which is huge for us. There are so many opportunities out there that we can’t wait to sink our teeth into. So stay tuned!

3 min read

Help! My Friend Is a No Show

Email armchairpsychologist@swaaymedia.com to get the advice you need!

Help! My Friend Is a No Show

Dear Armchair Psychologist,

I have a friend who doesn't reply to my messages about meeting for dinner, etc. Although, last week I ran into her at a local restaurant of mine, it has always been awkward to be friends with her. Should I continue our friendship or discontinue it? We've been friends for a total four years and nothing has changed. I don't feel as comfortable with her as my other close friends, and I don't think I'll ever be able to reach that comfort zone in pure friendship.


Dear Sadsies,

I am sorry to hear you've been neglected by your friend. You may already have the answer to your question, since you're evaluating the non-existing bond between yourself and your friend. However, I'll gladly affirm to you that a friendship that isn't reciprocated is not a good friendship.

I have had a similar situation with a friend whom I'd grown up with but who was also consistently a very negative person, a true Debby Downer. One day, I just had enough of her criticism and vitriol. I stopped making excuses for her and dumped her. It was a great decision and I haven't looked back. With that in mind, it could be possible that something has changed in your friend's life, but it's insignificant if she isn't responding to you. It's time to dump her and spend your energy where it's appreciated. Don't dwell on this friend. History is not enough to create a lasting bond, it only means just that—you and your friend have history—so let her be history!

- The Armchair Psychologist

Need more armchair psychologist in your life? Check out the last installment or emailarmchairpsychologist@swaaymedia.com to get some advice of your own!