We just launched Planners Perspective – the number one resource for wedding planning education, apparel & office decor.

Jess Aiken


Location: Williamsburg, Virginia

We were just seventeen when I told my now husband about my dream of owning my own wedding planning business. It would be five years later that Tristan would surprise me with a life changing check for $500 to start my business. After a trip to the bank and knowing nothing about owning a business, Wedding Co. of Williamsburg opened it’s doors.

We began this little biz with just two employees, Tristan and I. He was the accountant/HR Director/handy guy/really anything I needed him for. I was the brains of the operation – Marketing Director, Lead Planner, Assistant Planner, really anything I needed to do to keep the business running.

By the fall of 2016, I was making plans to leave my corporate job and to finally live out my dream. May 9, 2017 was my last day of working for someone else. I set some seriously high goals for myself. I hoped to hit six figures and create a wedding planning team within 5 years. Within 10 months I hit my five year goals.

With a lot of passion and a whole lot of luck, I am now living my best life!

  • Virginia Living Magazine Winner 2019-2020
  • Published in Southern Brides Magazine
  • Top Wedding Vendor by the Knot & Wedding Wire 2013-2020

What’s the biggest challenge you’ve ever faced while planning an event and how did you overcome it?

In 2020 we had a couple that decided to move their entire wedding to another state because of COVID. We had 3.5 weeks to scrap the old wedding and secure all new vendors and come up with an entire new design for the new wedding location. It was something I hadn’t experienced before and I didn’t know the venue. I called in all of my top vendors and trusted the venue and the brides in-law’s who were in the area to help us with making the right decisions. It was a huge success!

What are 2 trends in the event planning industry that you’re excited about?

Upgraded Linens (Velvet napkins and velvet chairs). There is something about dreamy linen that just gets me.

Bar & Food Rental Setups. They are so over the top and I’m loving that our couples understand the value of displaying food in such a curated manner.

What are some tips for creating an elegant and memorable event on a tight budget?

Having compromise is key when a couple is on a tight budget. Figuring out where the funds should be allocated, too, is so important. For couples who have a tight budget, we recommend allocating their budget to their highest priority and finding ways to get creative in the categories that aren’t as important to them.

If you had unlimited resources, what would your dream client and event look like?

We would have a tent wedding that utilized a Sperry Tent. The tent would have wood poles and would be adorned with greenery and heavy florals and candlelight. Every food station, bar, and lounge area would be modernized by bringing rentals in. Cascading florals would adorn the ceiling and it would be an experience of a lifetime for the guests.

How important are your relationships with vendors and what are some ways that you successfully cultivate and ensure good rapport?

Vendors are everything to us! We show them our love and support by recommending them continually and sending little gifts throughout the year to show them our appreciation. On wedding days, we thank ALL of the vendors and the village it took to pull off the wedding!

What’s the most exciting thing on the horizon for you personally or professionally?

We just launched Planners Perspective – the number one resource for wedding planning education, apparel & office decor.

What inspired you to launch your own company in the event industry? How long did it take from initially having the idea to setting up and starting to attract a client base?

My passion for people and my knack for attempting to organize everything in my life and others led me to this career path as a senior in high school. I just knew Williamsburg was where I was going to end up in life. I landed my first job in the wedding industry in August of 2006, working for a Williamsburg based wedding planning company. Every chance I could, I came home from College and assisted on weddings. I soon found myself dreaming of the day when I owned my own planning business and was executing dream weddings.

Little did I know this reality was just at my finger tips and somehow my life was going on the exact path I needed to make my dream come true. After graduating from James Madison University in May of 2010 (go dukes!) I packed my bags and relocated back to Williamsburg where it all started. After months of unsuccessful job hunting I finally landed a position at a local event rentals company. Ya’ll, this was honestly by the grace of God and I attribute a lot of my knowledge to this job. I worked for an incredible local who seemed to know every caterer, venue and important person within the community. I established many relationships and learned everything there was to know about tents, tables, chairs and linens!

Within less than a year of working at this company, I received a call from Kingsmill Resort. They were looking for a lead wedding planner for their Resort. When Kingsmill called, I was just twenty-one years old. I had a Bachelors Degree in Communications, an internship and 9 months of real life experience. I had no idea why or how in the world they thought I was qualified for the job, but I am so glad someone on the other end of that phone believed in me. I started my career at Kingsmill in January 2011. The next year was a whirlwind. I met an incredible group of ladies and that year we executed 60+ weddings and brought in over 1 million dollars worth of business.

In July of 2012, I came home to a check for $500 written out to me. The check was from Tristan, who I had been dating since I was seventeen. To my surprise, he had been researching what needed to be done in order for me to open my business. He asked me to take his $500 investment to the bank and match it. With a trip to the bank, 2 checks for $500 and a business name, Wedding Company of Williamsburg was officially opened for business.

For the next six years, I hustled hard trying to balance being a newlywed (yep, Tristan and I got married after 9 years together), a pup pup mom, a full-time job, and trying to grow my business! In May of 2017 I traded in my heels and cute dresses for jeans, oversized t-shirts and slippers and left my corporate job to be a full-time boss lady! When I left I had two goals. Goal #1: To grow my business into a team. Goal #2: Make six figures or more doing what I love. I wrote this down in hopes that I would hit this goal within five years. With a ton of drive, support and a whole lotta luck, I was able to hit my five year goals within 10 months of leaving my corporate job!

Now, Wedding Company of Williamsburg, serves more than 30 couples a year, executing their big day in the Williamsburg, Virginia area and consists of 12 team members.

What’s the first event you can ever remember planning and how did it go?

I planned my first event in high school and it was the after prom. I had no idea what I was doing and I had to learn early on how to manage everyone. It ended up being really successful, but I learned a ton.

What are some things you wished you knew before starting your businesses?

While many days I LOVE what I do and I am so thankful that I get to be a wedding planner as a career, there are days where I find it tough to be a business owner. I have so much passion for wedding planning and I want to help everyone. But as my business grew, so did our fees and services. I can no longer help everyone and that is a really hard thing.

What’s the most surprising or unusual request you have ever received from a client and were you able to fulfill it?

I had a client who had 150 guests and they wanted to offer a carriage ride to every guest from the hotel to the ceremony space in downtown Colonial Williamsburg. We received the quote and it was over $45,000. The client ultimately decided not to do it, but not because of the money, it was because of the timing of it all! It was wild.

Anything else you’d like to comment on while we have you?

Thank you so much for allowing us to be a part of this 🙂

Jess Aiken
Author: Jess Aiken

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