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

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!


Why Whiskey Should No Longer Be Categorized As “A Man’s Drink”

I walk into a room full of men and I know exactly what they're thinking: "What does she know about whisky?"

I know this because many men have asked me that same question from the moment I started my career in spirits a decade ago.

In a male-dominated industry, I realized early on that I would always have to work harder than my male counterparts to prove my credibility, ability and knowledge in order to earn the trust of leadership stakeholders, coworkers, vendors and even consumers of our products. I am no stranger to hard work and appreciate that everyone needs to prove their worth when starting any career or role. What struck me however, was how the recognition and opportunities seemed to differ between genders. Women usually had to prove themselves before they were accepted and promoted ("do the work first and earn it"), whereas men often were more easily accepted and promoted on future potential. It seemed like their credibility was automatically and immediately assumed. Regardless of the challenges and adversity I faced, my focus was on proving my worth within the industry, and I know many other women were doing the same.

Thankfully, the industry has advanced in the last few years since those first uncomfortable meetings. The rooms I walk into are no longer filled with just men, and perceptions are starting to change significantly. There are more women than ever before making, educating, selling, marketing and conceptualizing whiskies and spirits of all kinds. Times are changing for the better and it's benefitting the industry overall, which is exciting to see.

For me, starting a career in the spirits business was a happy accident. Before spirits, I had worked in the hospitality industry and on the creative agency side. That background just happened to be what a spirits company was looking for at the time and thus began my journey in the industry. I was lucky that my gender did not play a deciding role in the hiring process, as I know that might not have been the case for everyone at that time.

Now, ten plus years later, I am fortunate to work for and lead one of the most renowned and prestigious Whisky brands in the world.. What was once an accident now feels like my destiny. The talent and skill that goes into the whisky-making process is what inspired me to come back and live and breathe those brands as if they were my own. It gave me a deep understanding and appreciation of an industry that although quite large, still has an incredible amount of handmade qualities and a specific and meticulous craft I have not seen in any other industry before. Of course, my journey has not been without challenges, but those obstacles have only continued to light my passion for the industry.

The good news is, we're on the right track. When you look at how many females hold roles in the spirits industry today compared to what it looked like 15 years ago, there has been a significant increase in both the number of women working and the types of roles women are hired for. From whisky makers and distillers to brand ambassadors and brand marketers, we're seeing more women in positions of influence and more spirits companies willing to stand up and provide a platform for women to make an impact. Many would likely be surprised to learn that one of our team's Whisky Makers is a woman. They might even be more surprised to learn that women, with a heightened sense of smell compared to our male counterparts, might actually be a better fit for the role! We're nowhere near equality, but the numbers are certainly improving.

It was recently reported by the Distilled Spirits Council that women today represent a large percentage of whisky drinkers and that has helped drive U.S. sales of distilled spirits to a record high in 2017. Today, women represent about 37% of the whisky drinkers in the United States, which is a large increase compared to the 1990s when a mere 15% of whisky drinkers were women. As for what's causing this change? I believe it's a mix of the acceptance of women to hold roles within the spirits industry partnered with thoughtful programs and initiatives to engage with female consumers.

While whisky was previously known for being a man's drink, reserved for after-dinner cigars behind closed doors, it is now out in the open and accessible for women to learn about and enjoy too.

What was once subculture is now becoming the norm and women are really breaking through and grabbing coveted roles in the spirits business. That said, it's up to the industry as a whole to continue to push it forward. When you work for a company that values diversity, you're afforded the opportunity to be who you are and let that benefit your business. Working under the model that the best brand initiatives come from passionate groups of people with diverse backgrounds, we are able to offer different points of view and challenge our full team to bring their best work forward, which in turn creates better experiences for our audience. We must continue to diversify the industry and break against the status quo if we really want to continue evolving.

While we've made great strides as an industry, there is still a lot of work to be done. To make a change and finally achieve gender equality in the workplace, both men and women need to stand behind the cause as we are better collectively as a balanced industry. We have proved that we have the ability to not only meet the bar, but to also raise it - now we just need everyone else to catch up.