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Rising Stars: Meet Jessica Heddings

Today we’d like to introduce you to Jessica Heddings. 

Hi Jessica, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstories.
My grandfather retired from a local steel mill, Bethlehem Steel, in the late 1960s and wanted to run his own bar. So, in 1968, my grandparents, and their 6 children, became the proud owners of a small bar, hall, marina, and home on the water in Essex, Maryland. They opened the doors to Tom’s Tavern on New Year’s Day of 1969. Fast forward to 1983, when I was just a baby, and my parents jumped in to help my grandmother run Tom’s Tavern (soon to be Island View Inn) after the passing of my grandfather. Living on the same property, my brother and I grew up in the bar business. My resume includes pouring my first draught beer at age 8, crushing beer cans, washing drink glasses behind the bar that I could barely see over, and shooting pool in between tournaments (among many fun adventures and skills we could discuss in person). 

I continued my education by receiving my business degree, specializing in entrepreneurship, and exploring different jobs that could only be described as an adventure; golf courses, restaurants, sales, and finally cruise ships until I jumped back into the family business. By this time, our little neighborhood bar had moved to the waterfront and was operating as Island View Waterfront Cafe, a full-service bar and restaurant. My grandmother and father taught me every job there was to be learned and I can confidently say I am grateful to have these skills now. Though I stepped away for a bit to raise my own kiddos, it gave me time to reflect on the stamina of our small family business celebrating their 53rd anniversary in business this year. And while we served many, many plates of food, our guests (new and old) came back year after year because of the hospitality, connection, and friendship that my family provided. With the trials and tribulations of 2020 and into the foreseeable future, running a restaurant is and will face even more challenges. It feels like it’s time to make changes that will benefit not only our family but the community that we serve. With that being said, I decided (with many of a discussion with the family) to pursue offering our unique property as a venue. While we have had many weddings and affairs over the years, all were in conjunction with a full-time operating restaurant. And I want to be able to build a sustainable business operation while maintaining our core family values; hospitality, connection, friendship, and now, celebration. I am excited to pursue my passion of helping people secure a charming and affordable waterfront venue for their important celebrations. All the while, connecting other small businesses to work with us and these special guests, creating a strong community to build friendship and business for the next 50+ years. I truly hope to form bonds with each guest and they recognize how grateful I/we are for their business and that we are truly invested in them. 

We all face challenges, but looking back would you describe it as a relatively smooth road?
Is this a therapy session?! No, there is no business that can say it has been rainbows and butterflies. And ours has been no exception. Currently, the biggest challenge I am facing is navigating this new portion of our family business. It’s new to all of us and it is a big change and transition from ‘just’ the restaurant business. Though we aren’t a new business, and I have loads of experience, we are new to the venue space/market, so it feels like building a brand-new business from scratch. But so exciting too!! To meet fresh faces and to show them our special property, I’m ready! 

Appreciate you sharing that. What else should we know about what you do?
As a steward of my family property, and a division of the 50 plus year business, I am sharing our one-of-a-kind, waterfront property with the community so that they too can connect and make amazing memories like we have. 

Aside from being able to wear many hats, my special gift from growing up in the “people” business is being able to connect; albeit with the client or other businesses. I truly go above and beyond to find the answers or have genuine conversations with each person I meet. It is more than a sale for me. 

Currently, I am chief Jane of all trades in regards to growing our venue footprint… I am the gal behind the emails, marketing, tours, contracts, and venue representative at the weddings & events on the property. 

My parents hold down the physical property and maintain it (waterfront living isn’t always easy). 

I am incredibly proud to be the 3rd generation to continue the entrepreneurial spirit that my grandparents started. To grow up, and now realize, the hard work and dedication it took my own parents to successfully run a business and raise kids, I am excited to show them what I can do (and potentially pass on to my own kiddos). 

So maybe we end on discussing what matters most to you and why?
I absolutely value freedom and happiness. For myself, for my family, for any person I meet. To operate your own business, well, sometimes it feels harder than if you worked from someone else. But there is freedom in making a business your own and building a business around the life you want to have! And happiness, that’s an inside job. Every day it takes work to not let external factors dictate your happiness. 

In the venue industry, when I set out to invite couples to get married on our property, I want them to have the freedom to design the day of their own. I will give them ideas as to what others have done but I want every guest to be able to have a day that makes them happy. Obviously, we are a business and need to pay the bills, but the price I set was truly to offer a space that can be simple or extravagant based on each couple’s needs and wants. They are free to choose what makes them happy for their wedding day. 

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