Midd Moment, Ep. 10 with Roy Heffernan ’78

Intro:                           We define brand as knowing who you are and acting like it. Knowing who you are and acting like it, not when it’s comfortable, not when you want to, always. And we know who we are. And so the question is, are we acting like it?

LP:                               My guest today is Roy Heffernan, Class of ’78. Roy is current partner-owner and the former COO of Life is Good, an apparel company known for its culture of optimism. Listeners may recognize their classic T-shirt design, a cheerful stick figure named Jake declaring the namesake phrase, “Life is good.” I am so pleased to have Roy with me today, in town for the Hall of Fame induction ceremony and dinner this weekend. Welcome, Roy.

RH:                               Thanks for having me. Great to be back.

LP:                               Roy, we know you have a really tight connection with Middlebury and when you’re here on campus, you know people, you know current students, you know recent grads who’ve just come back, you know professors, you know admin folks, faculty from many years ago that you go see. Tell us a little bit about that type of connection. What keeps bringing you back to campus and how has being on a Middlebury journey with Middlebury given you a sense of excitement and purpose?

RH:                               First of all, Life is Good has 10 superpowers and the beauty of these superpowers is that we, all of us, have access to them. You can grab on to these and use them. One of them is gratitude. And I am so grateful to have experienced four amazing years here, but the rest of my life with Middlebury people that are my best friends. My very best people other than my family are Panthers. I had a heart attack on my birthday in 2014 and all my buddies were there for me. And I keep getting fed by students too. Izzy Hartnett is on the soccer team, she was an intern for Life is Good this past year and she’s just a terrific kid. It just feeds me. There’s a selfishness, there’s also a gratitude level that I really want to continue to find ways to, at least in small ways, to balance the scale of value.

LP:                               Can you give us a picture of College Roy Heffernan?

RH:                               Beyond studying, which did not come particularly easy for me, I was involved with football and lacrosse in very meaningful and powerful ways that continue today. I also was a head waiter—back in the day students actually ran Proctor Hall and I had breakfast because that was the only time I could fit it in between studying and sports.

LP:                               How did College Roy imagine his own future?

RH:                               I’d like to say there was real clarity on all that, but there wasn’t. I took a run at teaching and coaching for three years and then decided that I was a pretty decent coach, but I was a lousy teacher, so I decided to take another path and I made my way in the business world starting three years out.

LP:                               Just knowing you a little bit, I would probably want to disagree that you’re a lousy teacher, but tell me a little more about that experience.

RH:                               Part of what I’ve learned is that I am my best self in a team environment, and teaching, while there are team elements to teaching, certainly, you team with your students, you team with your cohorts that are also on the academic side, I found teaching to be pretty singular focused.

LP:                               And a little isolating maybe.

RH:                               Yeah, yeah, and I didn’t know that at the time so much, but it’s pretty clear to me now why I wasn’t a good teacher because I was not setting myself up for success.

LP:                               Yeah. If I may make a slight edit and this, you could tell me if I’m being fair or not. I would say you’re a fantastic teacher. You just don’t think the classroom is where your teaching occurs. Would you say that was fair?

RH:                               I hope that’s right.

LP:                               COO, first of all, is not chief operating officer, it is chief operating optimist.

RH:                               The role of chief operating optimist was just layered in on top of the very foundation by which Bert and John built the company starting in 1994. But it really didn’t start then. It started with their mom, my aunt, my dad’s older sister, her name was Joan. We lost her about three or four years ago.

LP:                               I’m sorry.

RH:                               Great long life, and she was able to bring to the brothers, I’ll call Bert and John the brothers, and their four siblings, a real peace and a real new energy and a change in the whole atmosphere and dynamic around the dinner table every night when she asked the question, “Tell me something good that happened today.” She was able to create an environment that was just really supportive and most importantly, around this word of optimism, empowered. She empowered her kids to understand that they’re in charge of their disposition and when they choose an optimistic point of view or an optimistic perspective, that they are empowered and they are choosing a path that will allow them to be most successful.

LP:                               Did it evolve naturally or what was the moment where you’re all sitting around the table saying, that’s what I want this to be?

RH:                               I think Bert had in his mind that I would be president/CEO. It never happened. I’m a fairly powerful person. Bert fills the room. He walks into the room and it is filled.

LP:                               And you don’t want to compete with that.

RH:                               I had no intention of competing with that. No intention. And nor would it have been positive for the brand.

LP:                               Yeah. Did you care?

RH:                               For a little while, but no. No. Being president/CEO wasn’t necessary to fulfill my career or something or, no. Actually, what was more important is that I become an owner and within a year when I started with the brothers, I became an owner.

LP:                               Tell me the difference in your mind between being an owner and being president and CEO. And the question is not a function of business titles, the question is a deeper one, which…is defining success for every person is so important. And when you do that well with yourself, you’re good. Life is good. Tell me a little more about what the difference is for you.

RH:                               Well, being an owner of Life is Good just automatically put me into the top tier of everything that had to do with the brand. A CEO can get fired. I wasn’t concerned about being fired, but there’s nothing that necessarily necessitates that the brothers would keep you on. I suppose I could lose my space as an owner, but I don’t know how. And I really felt like becoming a minority owner—by the way, Bert and John still have majority ownership, but there are six of us, four of us are minority owners, and the privilege to have that kind of relationship in a brand that stands for what Life is Good brand stands for, is the fulfillment of my career. A CEO position would not have been. Ownership is.

LP:                               Tell me a little bit more about how you would respond to the cynic that says, “Oh, come on. You’re all about your brand, are you kidding? You kind of sold out to the message of your own company” or something along those lines. That’s not me talking, but I do think that voice is there and I’d love to hear you talk a little bit more about that.

RH:                               Yeah, I have lots to say about this. In a very non-MBA definition, we define brand as knowing who you are and acting like it. Knowing who you are and acting like it, not when it’s comfortable. Not when you want to, always. And we know who we are. And so the question is, are we acting like it? I think companies need guardrails. And one of our guardrails is our mission statement, which I think is one of the best mission statements ever. And I feel that way because I don’t have to take a card out of my pocket to tell you what our mission statement is. It’s six words and it’s to spread the power of optimism. And it isn’t to spread optimism because then that’s about me, it’s to spread the power of optimism and then it’s about the receiver of the message. We need to know who we are and act like it. And part of that is our mission. So if you’re doing something as a Life is Good employee that is something other than spreading the power of optimism, stop because you’re not doing the right thing.

LP:                               Yeah, yeah, yeah. That’s great. And it is a kind of, it is a great guardrail, not just for financial statements or for company culture writ large, but for every day.

RH:                               Day to day.

LP:                               Day-to-day work. Let’s talk a little bit about optimism. And it’s kind of related to that was my second hard question. You’ve already spoken a lot and very eloquently about the role of optimism in your family and the company. I am married to a pessimist and we have this very creative dialogue. And one of the things that some people experience optimism as being is lying. Because pessimists always tell the truth. That’s why prophets, biblical prophets were as good as they are, because it’s always going to screw up. We know that. That’s easy.

RH:                               Pretty safe.

LP:                               Right. The optimist retort to the pessimist is, it’s too easy to be a pessimist because you know it’s always going to screw up. But if you’re an optimist, you’re going to be creative around what’s possible. And that I think is important to remind people of, because we live in this world of suspicion around optimism and it’s been, it’s not good sometimes. Why don’t you tell us about that? Why are you lying and saying that it’s only good? When does optimism become a false, either false hope or a false way of seeing the world? And particularly when it’s bad and you need to acknowledge that it’s bad.

RH:                               Yeah. We are rational optimists. Now we have a relatively new graphic that is on our tees, but also on some of our other products and it reads, “Life is Not Easy. Life is Not Perfect. Life is Good.”

LP:                               Yeah, that’s great.

RH:                               We believe that at our very core. We believe that and so do the people that are our biggest fans, because many of them are going through the most difficult times that you can imagine, and they latch onto Life is Good. It was so important in relatively early in the growth of our brand when Bert and John really didn’t know the power that they could harness with Life is Good, but guess who did know? Our customers knew because they would tell us, “Hey, we just buried our father in his Life is Good tee.” “Oh really? Well what do I do with that?” says a business owner.

And then we had little Lindsey Beggin who was 10 years old and she was in Children’s Hospital and she had a Life as Good beanie on her head. And she got interviewed by the Boston Globe and the interviewer said, “Are you aware of your cancer prognosis?” She said, “Yes, I have a year to live.” And he said to her, “Why are you wearing a Life is Good hat?” And this little gem said, “Because before I was sick, I didn’t appreciate it. Now I appreciate every day and life is good.”

LP:                               Wow.

RH:                               The point is that there’s this: our customers told us how powerful our brand could be and so then it’s up to us to say, “Okay, how do we harness that? And how do we live even though life is not easy, life is not perfect, but life is good?” And the opposite, notwithstanding your wonderful husband, we like to say, “Don’t bother being a pessimist. It won’t work anyway.”

LP:                               That’s good. I like that. I really like that.

I know you’ve been a MiddCORE mentor and one of the hardest things for students starting in that program are thinking about creating something new in the world and putting it out there. They don’t know sometimes where to start. They don’t know how to take all the advice they’ve been given and apply it to their particular idea. Tell me a little bit about A, your own creative process and B, how your work at MiddCORE, which is all about the creative process, has translated your own experience.

RH:                               Yeah. If you sit down with a four- or five-year-old and you tell them to draw and you put some crayons in front of them, they draw. They don’t say, “Hmm, I’m not a good artist.” If you do that with an adult, after they’ve been told by many, many people that they’re not artists in one way or another, they close down. They don’t live their life with their arms wide open. So I’m not an artist and I’m not a musician as much as I’d like to be and I appreciate music. But what I found is I’m really creative and you know where I’m creative? I’m creative on the ops side, on the operation side. It takes great creativity to come up with the right solutions to move your company around certain challenges and pitfalls that they have. I guess the first and primary most important answer to your question is that everybody’s creative. Everybody’s creative. It just, you just have to find how you best manifest that for yourself and for the people around you.

LP:                               I like the way you’re phrasing the story of creativity because it is about not what you know you’re good at. Of course, that’s part of it, but it’s what you’re fundamentally curious about. At some point you figured out that you’re curious about ops and operations and that’s such a wonderful thing to know.

There’s so much more we can talk about, but I usually end with, what’s your question? What’s the one question that you’ll always ask and you’ll never know the answer to but you’ll never get tired of asking? I don’t know if you have any thoughts on that.

RH:                               I’ve worked really hard to understand my essence and that would be defined as when I show up as my very best self. And in order to do that, you have to also understand the opposite of that, what I call bad Roy.

LP:                               Evil twin Skippy is what I call it.

RH:                               Yeah. And I know bad Roy pretty darn well, I’ll tell you that. My question is personal and moves quickly beyond that because I want to continue to understand fully when I am in my essence, how I set myself up for success relative to that so good Roy shows up always. We’re fallible so it won’t be always, but mostly always. And then I want to dedicate my life to helping others to be in their essence. What I do is I leverage my mantra as often as I can and my mantra in life is to leave every communication with the person receiving the communication bigger, not smaller.

LP:                               That’s great.

RH:                               And if I can do that and help them to be in their essence, then that’s what I want to do. The question is, how do I do that with the limited number of years I have left?

LP:                               Roy, this has been a fantastic conversation. I just want to thank you for coming in today.

RH:                               I always love being with you.

LP:                               You achieved your goal of making the person that you’re with always feel better and bigger and thank you for that.

RH:                               Thank you.

Erin Davis:                    Hi. This is Erin Davis, producer of the show. Midd Moment is produced by myself and Juliet Louini, Class of ‘18.5, with help from Chris Spencer. For more conversations like this, subscribe to Midd Moment on Apple podcasts or wherever you get your podcasts. Thank you for listening.