This interview, which was condensed and edited for clarity, was conducted at Portland House of Music on October 25, 2019.

Lindsay, what’s so exciting about your company is that you’re the fifth generation running the business, and that’s a new twist for Like A Boss. Could you start by just telling us about the history of Gifford’s?

It started in the 1800s in Connecticut with my great-great-grandfather and then my great-grandfather who did home milk deliveries and ice cream. They had special batches and recipes that we use today. My grandfather Randall Gifford was born in Maine and went to University of Connecticut where he met my grandmother, Audrey, who is still living today. He would work on the farm after school with her father where he learned the ins and outs of making ice cream and farm life. They married and purchased their first dairy in Connecticut. When home deliveries were becoming a way of the past and grocery stores were becoming the latest thing, they uprooted the family and purchased a dairy in Farmington, Maine. In the ’70s, they purchased Hunt’s Dairy in Skowhegan where our production plant and our home offices are today.

In 1983, they sold the milk portion of Gifford’s to Oakhurst Dairy. We still get all the milk and cream from them for our ice cream. When we transitioned from the third generation to my father and uncle in the fourth generation, they took a risk and said, “We’re going stick to making premium ice cream.” And that’s where we are today.

When did you first start working at Gifford’s?

As soon as I was born. No. Officially, in summers in high school and throughout college I would work in the office. For those of you that know family businesses, you know you do whatever you’re asked, whenever your asked. It doesn’t matter how old you are. There is no slacking.

Did you start full-time at Gifford’s after you graduated from college?

Yes, the day after.

And here you are. How did they get you started on your path to CEO?

I feel like that’s also another difference in family businesses. It’s not as maybe structured, at least ours. You do whatever you have to do, it’s your family, it’s your name. They worked with a consultant and all of my generation were interviewed thoroughly and asked a ton of different questions. When I graduated from college, my title was assistant to the controller. It evolved from there. We had to jump in wherever was needed.

They moved your desk right next to your uncle’s, though, right?

Yes. They didn’t really tell me the reason behind it, but they moved my desk into my Uncle Roger’s office because they wanted me to hear every conversation he had with other family members. And by family members, I mean everybody that worked at Gifford’s.

I would ask questions and he would teach me along the way. We also had a rule that my uncle’s kids never would report to him, and I and my siblings would never report directly to our father.

Then you became the VP of sales and general manager.

My uncle was having what I’ll call a board meeting. They had me taking minutes and at some point, my father very casually said, “You know, my doctor said I’m walking a fine line. I need to slow down. I need to step back away from stress.” This was the first time I was hearing this. And I asked, “What’s the solution?” And they looked at me like, “What do you mean? There is no solution.” I said, “Okay, starting today I am your buffer, anybody that wants to get to you, they have to go through me.” We changed his email so it would go to my email, he didn’t have a company extension anymore, because it went right to my inbox.

Call me crazy, but it’s my dad, so I did what I needed to do.

It seems to have worked out well for you and for Gifford’s. What’s it like to bring non-family members into a leadership position at Gifford’s?

When I was the VP of Sales and Marketing at that time, we were trying to get my father and uncle to slow down a little more. We decided, as a family, to hire a COO who knew ice cream.

Because eating mass quantities doesn’t qualify you as an expert.

No, that takes you only so far. We had to hire someone from outside of Maine. It worked for a couple of years, but there was a cultural difference and we needed to do the best for our family members. We’re looking out for their best interests and their families’ interests. There was a disconnect. After this person was no longer with Gifford’s, we met as a family and with some of our other key folks and said, “Okay, guys, how do you think that went? Do you want that again, or are we going to do this together and figure it out?”

That’s when we decided for me to shift to a different role, General Manager.

Explain each one of the family members that are on your leadership team today and what their role is.

We have me, and my brother, JC who is VP of Sales. My sister Samantha is our marketing manager. My cousin Ryan is quality assurance and safety. Darcy Dow is our VP of Finance. And we have plant manager Joel Violette, who’s been with us for 43 years. And Carl Smith, he’s our maintenance manager. Then we have a general manager also that oversees our five ice cream stands that we own and operate.

When your family sold the milk business to Oakhurst in 1983, you produced 10,000 gallons of ice cream that year.

Yes.

How many do you produce today?

We can produce more than that in a day now. Can you imagine? It reminds me that my father and uncle truly took a huge risk for our family. They had young kids, newborns, and they sold the milk portion, and some people might think, “Oh, well, they took that money.” No, that money got dumped into the business. We needed all the equipment and a bigger freezer for ice cream. I’m proud of them.

In a year, how many gallons do you produce?

This year, it’ll be close to 2.4 million gallons.

I think what everyone wants to talk about is how do new flavors get developed?

In a variety of ways. We have very passionate and loyal customers, and they love to send in different ideas in the mail, over social media or by phone. We also have ingredient suppliers that we work with who present new concepts. Sometimes the name comes before the actual flavor. Dough Your Job was the name before the flavor.

Unfortunately, some flavors get retired. How do you make those tough choices?

That’s when the family dynamics get a little dicey, especially when you have to discontinue your sister’s favorite.

Tell the story about Maine Lobster Tracks, and what you had to do.

I think it was my dad who said, “Okay, we need to do a spinoff on Moose Tracks. Let’s have Maine Lobster Tracks.” So my uncle says, “Alright, Lindsay, your assignment tonight is to go get a lobster and cook it.”

Then they handed over the Pantone color booklet, and I needed to match the cooked lobster to the color, and tell them, so they could tell the ingredient company for the chocolate. I thought they were kidding. I’d never cooked a lobster in my life.

Let’s talk about the Bruins and the Patriots deals because they are both brilliant. How did Power Play Fudge get started?

I had a contact with the Portland Pirates who went on to work for the Bruins. He reached out because they had a change in their existing ice cream company. We had a meeting, and my brother and nephew are big Bruins fans and it all came together quickly. During playoff season, Power Play Fudge was the number one flavor over vanilla.

When the Bruin’s score, Gifford’s name will flash around the arena. The first time I was watching a game on TV and saw that I thought, “Wow, look how far our family has come.” I’m proud of us.

Let’s talk about Dough Your Job which just came out in August.

My brother, my sister, my uncle and I had a retail meeting to talk about what things are working and what needs to shift. We thought, “Oh my goodness, look how well Power Play Fudge is doing. It’s starting to catch on.” My brother said, “Well, why don’t we just reach out to the Patriots? We want to be the number one quart in New England. Maybe this is how we’re going to accomplish that.” So that day, he reached out to the Patriots. From there, it was a quick turnaround. Stressful, but good stress.

Let’s talk a little bit about the core values of the family.

First, honesty. Being open and active listening. I’m still working on that. By being open we mean it’s a different day. Just because we did it 30 years ago, doesn’t mean that we can’t accomplish that this time with a different spin on it.

Love is one of our values. It’s a family business. If somebody’s having a rough time, we want to be there to support them, just as I know that they would be there to support me. There’s passion, pride, quality. Guard quality, that’s a big one, because it’s our family business. Our name is on this package, so we want to make sure that it’s the safest product as well as the best product for our loyal customers.

How do you manage conflict?

Avoid. I do not like conflict whatsoever. I wish I was more direct in certain situations. I always try to think, “Okay, if it was me on the other side of the table, how would I want to be treated or how would I want someone to communicate with me?” I try to be as honest as possible, but sometimes that’s difficult. It’s your family members that you’re working with. You see them more than you see your own kids. Sometimes I don’t do a great job at dealing with conflicts, I will say that is one of my challenges as the CEO.

What keeps you up at night?

Fear of failure and letting people down.

I would say you’re not doing that at all though, so I hope you sleep well. And, you get up super early, right?

I get up between 3:30 and 3:50 am. I get up to Skowhegan around 6:00 am. It’s very quiet. I like to be organized, I like structure, so I can get some of my work done before meetings start.

Before we take audience questions, let’s go with the top five selling flavors.

It changes, but vanilla, chocolate, black raspberry, chocolate chip, frozen yogurt, toasted coconut, and probably Moose Tracks. Sometimes the Power Play Fudge can be in there, or Dough Your Job.

What’s your personal favorite?

It’s three scoops. Orange sherbet, black raspberry, and mint chocolate chip on a homemade waffle cone that we make at our stand that’s dipped in chocolate with rainbows.

Let’s take audience questions.

How do you continue to grow, but also keep your reputation so strong?

Our father always said, “Do what you say you’re going to do, and go above and beyond.” That always goes through our heads. If you say you’re going to get something for somebody tomorrow, well, let’s get it done tonight and send it to them now instead of tomorrow. It’s the respect that you show them, I feel like it will reciprocate. It’s hard work and dedication.

This is our Gifford’s Famous Ice Cream, this is our family. We’re not going to let it fail. And we are grateful to our loyal customers. Without them, we wouldn’t be where we are today.

How do you keep the family relationship and the business relationship separate and good?

At the end of the day, we work together. We all work towards the same goals. It’s just a matter of who’s going to do what in order to accomplish those goals. I don’t think it’s awkward, unless we make it awkward. We got approached by a couple of reality TV shows and we’re like, “Why would they want us? We have no drama.”

Thank you, Lindsay, for being here. We really appreciate your leadership and running such a great Maine company.