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In the News, "Meet Jessica Heddings"

Canvas Rebel, Conversations with Entrepreneurs, Artists & Creatives

We were lucky to catch up with Jessica Heddings recently and have shared our conversation below.

Jessica, thanks for taking the time to share your stories with us today…

How did you come up with the idea for your business?

I was fortunate enough to grow up in a family business. My grandparents purchased our waterfront property in 1968 and served the community with a small but popular bar, marina, and picnic grove…  Read full story here… Canvas Rebel – In the News

My parents stepped into operation in 1983 and grew the business exponentially in 2000 when they moved the roadside bar to the waterfront turning the family business into a thriving waterfront restaurant. As a youngster, myself and brother could be found helping at “the bar” and when old enough, worked beside Grandmom Laing and my dad to learn all aspects of the business and together launch the family biz to even bigger success.I stepped away from the business to grow my own family and my dad resumed the operation of the restaurant…and then the restaurant industry was rocked with a global shutdown. We were faced with the dilemma to sell or pivot. Many discussions later, yet no clarity of what the future would hold, I started advertising Island View as a waterfront wedding venue. And booked a wedding that would take place in a short 6 months. Then I booked 4 more!! The decision was made that the restaurant would take a back seat and I would focus solely on booking weddings and events. Here’s why I knew this would work for our family business: we have a gorgeous waterfront property, making it easy to sell a waterfront wedding. But most importantly, while our family sold food and drink, our core business was always taking care of people and celebrating them! In our community, there is not a wedding venue like ours. We are not cookie cutter, and our couples are creating a wedding experience that conveys their core values. Instead of being all inclusive or DIY, Island View Waterfront is a mix of everything so that couples can design a day reflective of their unique partnership. I can honestly say I am having so much fun meeting new clients and watching their vision come to life using the natural beauty and surroundings of Island View!

Jessica, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Growing up in the bar business, I used to wash dishes when it was busy, crush beer cans for money, run around the pool table during tournaments, and do my homework by the fireplace with a plate of hot beef, mashed potatoes, and green beans. It was home. It was our family’s business. My actual first paying job was making salads at another neighborhood restaurant, then a golf course as the beverage cart girl (who didn’t sell beer but learned that the golfers would tip well if I ran by their cars to grab their illicit coolers of beer) and then back to the family restaurant as a server and bartender. My parents encouraged myself and my younger brother to try on different jobs and to go to college. Both of which I did; I have the degree and unique resume to go along with it. Ultimately, every job was customer service focused and I honed my skills of knowing what the customer wanted and needed before they did while giving the best experience I possibly can. It wasn’t always easy. I made a ton of mistakes, fought too much with my family, avoided and ran away. Only to come back to the family business “all grown up”, with many lessons learned (and still more), ready to start the next chapter of our family’s business. Now I am raising my kids in the business, and I can’t wait to hear what memories they will make. Whether it is selling food or a waterfront wedding, the number 1 rule is fast and hard; take care of the client like they are the only one you have and treat them like they are family in the best possible way. Our family built our business by getting to know people and letting them see inside of our family business. The food and drink were good but the friendships and connections over the years are what makes our family business stand out.

Have any books or other resources had a big impact on you?

There are so many amazing resources at our fingertips. When I worked for a cruise line, part of the training was a video called “Give ‘Em the Pickle by Bob Farrell – Customer Service Training.” I remember sitting at that table, surrounded by co-workers I had yet to meet, and having my mind blown. It’s so simple yet what separates our business from the rest.

Chick Fil-A may be one of the top fast-food chains ever. And I stumbled upon a book called “Covert Cows and Chick-fil-A” by Steve Robinson. It made me want to have a Chick-fil-A franchise (I don’t) but inspired me to look at our family business differently. Putting the right systems and people in place are the golden ticket. Great read.

Other notable, favorite books that have shaped me:

  • The Tipping Point by Malcolm Gladwell

  • Night by Ellie Wiesel

  • Think and Grow Rich by Napoleon Hill

  • How to Win Friends and Influence People by Dale Carnegie

Do you have multiple revenue streams – if so, can you talk to us about those streams and how you developed them?

The core business is inviting people to share our family’s waterfront property. In order to have multiple streams of income, we are adding different ways to sell the waterfront.

For years, it has been a restaurant. Now we’ve expanded into “real estate.”

We currently rent our property for weddings and private parties (birthdays, showers, life celebrations, etc.). We also have a section of our property that a local, non profit kayak group leases from us. Their members use our property and launch to explore the Chesapeake Bay by kayak.

We also cater small parties but are exploring leasing our kitchen to local food truck vendors as a commissary kitchen.

We have a 7 day/package good liquor license so I am able to sell bar packages or products to clients.

To dive into my brain and learn more about my 5 year plan, I’d love Island View to be a weekend wedding destination. I will turn my family’s home into a place for the couple to stay while they get married at Island View, or rent it out (airbnb style) for travelers who are want to explore the Chesapeake Bay but don’t want to stay in downtown Baltimore (we are approx 20 miles from downtown).

I’m always on the lookout for opportunities to share our property, and connect. If you want to collaborate, pitch me your idea and let’s grow a business!

Contact Info:


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