Get to Know Jonathan Trentham, the other half of Sherwood Media

I’m thrilled to introduce to you all someone who is very important to me, and who has been foundational to the growth of Sherwood Media for the past 10 years. 

I’m so thankful for an incredibly supporting partner, father, and husband in Jonathan.

Meet my business partner and husband, Jonathan Trentham.

Jonathan joined Sherwood Media full-time in December 2024, but he has been a big part of our story since the beginning, more than ten years ago.

In the office, he manages our books, streamlines our processes, improves the client experience. On set, he sets up lights, runs audio, and takes care of loading gear so I can focus on connecting with my clients.

Whenever details need to get sorted out, Jonathan runs to open a new spreadsheet!

He never asks for attention, so I’m (Elisa) writing this blog article to celebrate his story, and how he has been critical to keeping this business moving forward.

I think one of Jonathan’s biggest strengths is being willing to do whatever is asked of him, no matter how menial or inglorious the task. He also has an incredible ability to learn, problem-solve, and offer solutions that improve systems, processes, and people wherever he is.

Growing up in Franklin, TN, Jonathan learned responsibility and independence starting at 13, when he built a lawn care business that quickly grew to serve the majority of his neighborhood and surrounding properties.

Full of big dreams and ambitions, he attended the University of Tennessee where he planned to study astrophysics. 

Working through college at Chick-Fil-A opened his eyes to other opportunities.

Jonathan worked closely with Eddie Halliday at multiple Chick-Fil-A locations.

“That’s when I began leaning more into growing through time in the workplace and decided I didn’t need to spend a lot of money for a fancy degree when the opportunities were in front of me today.”

After a year of facing disillusionment and soaring debt, Jonathan decided to drop out of college and worked his way up to management at Chick-fil-A.

He’s shared all kinds of stories with me about staying up all night scrubbing chicken grease off of industrial kitchen equipment, juicing thousands of lemons for lemonade, hiring and firing, and frying a LOT of chicken.

While on track to becoming an Operator at Chick-Fil-A, Jonathan felt a clear call to move to Cambodia.

Jonathan contacted a Christian missionary friend in a little village called Kampot and asked if they needed help getting a new program or project off the ground. The timing was miraculous, and he began packing his bags and selling his belongings to join the mission.

He lived and worked in Cambodia for 2 years, where toilets were flushed with buckets of water, showers were always cold, and taking deworming medication was part of your routine.

Jonathan became a part of the Lighthouse Ministries team, serving at an orphanage and starting and English school.

When he thinks back on this time, he said,

“I was going for it. It was a big wild crazy idea and I was wholesale going for it.”

“As a child, my motivation was always to be useful and capitalize on unique strengths and giftings. The idea of doing something crazy like selling everything I own, moving to a third world country because I could really be useful and I believe God asked me to, I got to just trust God and do this thing. It was very enjoyable to take a risk.”

He returned to Knoxville, and his next steps shaped who he is today - after all, that’s is where he met me (a story for another day!)

Our beautiful wedding at the Southern Railway Station in Knoxville, TN.

Jonathan’s desire for growth and learning led him to small business administration. 

If you walked in to Jonathan’s office at his previous admin job, you’d see a small stack of “coffee table” books about Cambodia, a cup of Dr. Pepper (no ice) from Chick-Fil-A, a wall calendar of outer space, and a sign on the door that read, “Director of Miscellaneous” - a title that fits him so well. 

I loved visiting him at work with a squishy baby or two, and seeing how much people appreciated his contributions, and how warm they were to him. He has worked hard to build relationships everywhere he has been, and that has served him well.

I think this is partly because Jonathan is happy to do al the things most people don’t want to deal with - HR, finances, stocking toilet paper, filing paperwork, washing dishes, and building (another) Ikea desk. He was also able to contribute his knowledge and creative problem-solving by working side-by-side with C-level executives.

I’ve always said Jonathan is a great mind to have in a room, because he isn’t afraid of challenging the norm with a creative idea that no one has thought of yet.

Jonathan loved his time working with the team at Eventbooking, now Momentus technologies.

Jonathan is strong in a supporting role, but he’s not afraid to dream.

“Early on in our relationship, we dreamed of a future of using our unique skills and partnering together in business.”

We launched Sherwood Media in January of 2015, and were engaged that same month. Even though Jonathan has had other jobs along the way, he has always believed in the vision God put in my heart for this business.

“There were times when we were not getting business or making sales and it’s hard to not navel gaze and wonder is this going to be a death spiral. When do we jump ship on this thing?”

During difficult seasons when I would want to throw in the towel, Jonathan would remind me of God’s promises for this business, and to simply take the next step forward.

“I’ve not for one day thought that Sherwood would fizzle out and die. I believed from the first day God would build this business and entrust us to steward it. That didn’t mean it had to be our sole income, but I also believe that our mark would be that the business would bless us, and we would bless others with what we do and how we do it.”

Now, ten years later, we have decided to take the leap of full-time entrepreneurship together.

Here’s what our setup looks like today! Jonathan dialing in audio and lights, while I coach the person on camera to tell their story, pitch their idea, or teach their audience.

What seemed like a wandering path, God used Jonathan’s experiences and values to make Sherwood Media what it is today.

“Success isn’t the pot of gold at the end of a rainbow of perfection. It’s daring to dream and putting one foot in front of the other.”

“It’s not a glamorous journey. It’s excruciatingly humbling. It requires digging deep and getting out of bed before your friends because of the volume of things on your plate to do that day. It looks like raising your hand and offering to do the dirty, nasty, unseen work. It means tightening your belt in uncomfortable areas and getting creative and resourceful. It is not an easy journey, and no one who gives up gets there. But those who are relentless, persistent, and hungry will overcome incredible things and they will reach where they want to go.”

I’m so thankful to be partnering with such a determined, hard-working man who has deeply known the vision of Sherwood Media, and me. While you may see my face representing Sherwood Media, I want everyone to know that I wouldn’t be here today without Jonathan working behind the scenes to keep us on track, to keep me encouraged, and to keep our family together.

Jonathan would love for you to connect with him on LinkedIn!