#drinkport | “Terroir & Merroir with The Lady Oyster”

Do you ever scroll social media and come across interesting people doing really interesting things? That's how I discovered Virginia Shaffer.

Maybe it was the Instagram algorithm working overtime, maybe it was fate, or maybe a mix of both. Either way, I reached out and she agreed to chat with me. So, who is she?

Her business, Lady Oyster Tours & Tastings, is making Maine seafood experiential through intimate oyster tastings, sea farm tours, and coastal adventures. And spoiler alert, she happens to be obsessed with Port wine. Who knew?

She's my first female guest and she's set the bar high. She's chock-full of business insight and advice for anyone thinking about quitting their full-time job to pursue their own venture. And she's brimming with passion for what she does. Pull up a seat and let's #drinkport with Virginia.

Watch and read highlights from our conversation below (edited for clarity).

Q: If you could invite anyone — living or dead — to a dinner party, who would you choose?

A: I've been asked this question before, but I always feel like I change the answer all the time, just depending on where I am in life. The one person who I think would really resonate with me right now — who I would love to pick her brain — is Rachel Carson. She's was a marine biologist in the early 20th century to mid 20th century. She was a prolific writer as well, and a poet.

She had this wonderful duality of science and art. She came from a science background and conducted so much research and put so much effort into environmental activism. Then she was able to translate it for the masses in such a powerful way through her stories, through “Silent Spring.”

She is also one of the most incredible people to have ever walked this planet when it comes to being an advocate for ocean health. I don't think we would have oysters the way that we do today without her and the work she did with banning some pesticides like DDT.

But I want to break a rule because I want to also invite another guest, which is my grandmother. We lost her years ago to dementia, but she was also this woman with that duality of science and art. Growing up, she was a chemist and an incredible teacher. People from Harvard would come to watch her teach chemistry. And then in her later life, became an incredible painter. I just think the two of them would have so much in common and a lot to talk about at a dinner party.

Q: What inspired you to start The Lady Oyster? Tell us about its evolution.

A: It started as a passion project. I started writing about oysters, which was about eight years ago, because I was missing something. There was this disconnect between a food I really loved and anything I knew about it.

I went searching on my own. I didn’t want to monetize anything — this was simply a project. I just wanted to write and be creative and learn.

Because I was so willing to learn, people invited me into their world on mudflats and skiffs and I thought, ‘Why am I the only person who gets to access this?’ And, ‘What could I do to help people make those connections for themselves?’ So it was just an honest passion project that kind of moved into my love for entertaining and hosting, and the beauty of that and the joy in it.

Q: Describe these oyster experiences.

A: We call ourselves a gastronomic culinary tour company. We want people to experience oysters at the source. We want to pull back the curtain a bit on seafood and understand it a little more deeply and create some more connections with Maine. We do that in a couple of different ways.

We have experiences that are sensory — so sensory dining, guided oyster tastings with different wines that we select to pair with them. So that's about an hour-and-a-half event of purely just coming to the coast and enjoying oysters and learning so much about them. We also have oyster farm tours. So we take people out on the water and get them on a float. They learn how to cull oysters and shuck them — that's a more interactive, immersive experience that we offer as a tour company.

And then the last is retreats. We do a few retreats each year that offer a full immersion program. It's also known as seafood summer camp to a lot of people, which is just awesome. We cook three meals a day. We do seafood cooking classes and get them out on the water to meet farmers. We build this incredible culinary experience for people who really want to more deeply understand seafood in Maine.

Q: Prior to building The Lady Oyster, you had a career in sales in the tourism industry. How did you decide to quit your full-time job?

A: How much time do you have Rebecca?

Everybody's path to wherever they want to be is going to look different. I will say that it took me a long time to mentally prepare for a change. I think it’s so easy to be like, ‘I just quit my job and I started this bakery,’ but that's just not real.

I got into corporate sales over 10 years ago. I was in marketing before that for a few years. I got into sales because I didn't want anyone to dictate what my value was — I wanted to make my own income and set that standard for myself.

I came from a family where money at times was financially scarce. There were lots of insecurities around money in my past, and so I think when I started this side blogging project (which was really just to disconnect from work a little bit and give myself space mentally), I started to realize that the only goals I had really set for myself in my career were income-driven goals. A lot of that value that I had for myself was tied to being financially independent and creating wealth that I never really had before.

I had to go through a mindset shift of what my value was in this world and what I could bring to it, versus how much money I could make. And I think that's really where a lot of people have to start — it’s decoupling what you have to offer with how much money that will make you.

When I realized I really needed to change and move out of sales was when I was getting burnt out. I loved oysters and wanted to figure out what to do with that love, but I didn't know what that looked like.

I think a lot of us work in our own minds a lot and we only have our inner voice to listen to and that's not always a confident voice. So therapy is a wonderful thing. Really understanding what our fears are about change is a really good step toward overcoming them.

And my fears were finances. It was like, 'How am I going to do this if I don't have the money to do that?’ And so my therapist, who was a really great life coach as well, was just like, ‘Let's tackle finance then.’

This is an area that I don't really enjoy. I'm not an accountant. These are areas that are very difficult for me. So we started making a plan and that was how much money I was going to save every month; what that number looked like; how I was going to build that; and how I was going to invest here to make a little more extra money.

Then when we were ready, I was ready and set up to take take time off and sort of break out and figure out what the next step was. I had built a significant nest egg that was ready for me. I had re-budgeted everything — I colored my hair less, got my nails done less, and just sort of consolidated all of my bills and made that pot last me a certain amount of time.

I will say, when you make the first big change in your life, all of the other ones are so much easier.

Q: What's the best advice you could give someone who is in between pursuing their passion venture full-time and wanting to leave their full time job?

A: The first thing I'd probably say is stop being so hard on yourself. I think we go it alone a lot when we are in between — we feel sort of like we're living double lives a little bit when we have a passion project and we're still working in a full-time career. Those things are very hard to hold inside all the time and work through.

Giving yourself a little bit of grace in all of those decision-makings is really important. And then the next piece of advice is to really seek some support. I kind of grew up very independent and it has always been very difficult for me to ask for help when I've needed it. But there are some incredible ways of seeking support out there where people can help you make those changes and make them less scary.

Lastly, I would say there are some just basic, money management things that are super important at this time in your life, when you're going through this change. The more that you can overcome it and feel confident about it, the better you’ll be.

Q: You’ve said that you're ‘obsessed’ with Port wine. How did you discover it? Tell me about your journey into Port wine.

A: Port holds this special place in my heart because when I was 19, I had never traveled out of the country. I did an exchange program in Spain, which was a pretty immersive experience. All of my classes were in Spanish. I wasn't doing super well and I was pretty isolated, but I had one fellow American friend who was also in the program and he was going to Portugal for Easter break. And I was like, I need to get out; I need to do something.

He had this plan to go from Oporto to Coimbra to Lisbon. I joined his trip. We started in Oporto. This was my first kind of loner trip, getting out and backpacking like I had always wanted to and dreamed of doing. We ended up at Sandeman, at their wine cellar in Oporto. And I couldn't tell you if it was a great wine cellar or not because I just had no frame of reference at 19. I was just like, ‘This is amazing.’

Port was just so different from what I had drank before. It was something really novel. You couple that with some travel and learning when you're young — that it all creates such a powerful memory.

My favorite moment with Port was when we were in Coimbra and we had stumbled across this little basement bar and you're just like tucked in with all these little locals in this tiny hole. There were a couple of guys playing Fado in the corner. We ordered Port and I just remember sitting there and being like, ‘Wow, where the heck am I?' This is the most amazing thing that's ever happened to me.’ So I think Port just is tied so closely to memory and discovery that it's now just a part of who I am.