The Story Behind Her Success Podcast—In the spotlight: Dianne O'Connor

Our founder, Dianne O'Connor, had the privilege of interviewing with Boston's beloved radio voice, Candy O'Terry, on The Story Behind Her Success. When asked what advice she would give to a young woman with a dream or a goal that seems insurmountable, Dianne says: “Take the risk. Listen to your heart.” Listen to the full podcast here and read the transcript:

ANNOUNCER: Welcome to The Story Behind Her Success with Candy O’Terry, presented by Boston Women in Media and Entertainment. Sponsored by TechHelp Boston.

CANDY O'TERRY: Thank you for the stories, because they just keep on coming. The one you're about to hear intrigued me the minute I heard it. But before I tell you about it, do me a favor and just take a look around your house. What are the items that mean the most to you? I'm gonna guess they're the things that are part of your story. An heirloom from your grandmother, a piece of pottery made by your child's loving hands, a cozy quilt that's stitched with love by your best friend. In the spotlight, a woman who sees retail marketing in a completely different way. Her brand is called Weston Table, and it's based on her less but better philosophy, a new nostalgia that integrates the past, the present, the future, featuring the inspired work of small artisans from around the world. Launched online in 2014, and now with a flagship store in the sweet little town of Weston, Massachusetts, Weston Table is a place where beauty, function, and life values all come together.

Every item has a story, and the hope is you are drawn to it with intention because it has meaning for you, because your heart wants it. Dianne O'Connor, welcome to The Story Behind Her Success.

DIANNE O'CONNOR: Thank you, Candy. I'm so delighted to be here today.

CANDY O'TERRY: We met online at The Print Shop, and I just knew that you would be perfect for our show. So here we go. First, we're gonna play Candy O's Lightning Round, which is lots of fun. I'm gonna ask you five questions. I just need five short answers. Are you ready?

DIANNE O'CONNOR: I am ready.

CANDY O'TERRY: Best gift you have ever received?

DIANNE O'CONNOR: A pair of earrings on my wedding day from my husband.

CANDY O'TERRY: Favorite holiday?

DIANNE O'CONNOR: Thanksgiving.

CANDY O'TERRY: Preferred communication, text or voicemail?

DIANNE O'CONNOR: I would say text.

CANDY O'TERRY: You have traveled the world. Most beautiful, stunning place you have ever been?

DIANNE O'CONNOR: The Gap of Dunloe in Ireland.

CANDY O'TERRY: Mantra or favorite expression?

DIANNE O'CONNOR: The new nostalgia.

CANDY O'TERRY: All right. There's a quick glimpse into your personality. Now let's dive into the rest of your story. You got your start as an international investment advisory professional. Tell me about that chapter in your life.

DIANNE O'CONNOR: I moved to Boston from Texas in 1989. It was at a time when the mutual fund industry was booming in Boston, and there were jobs galore. It was kind of like the market today, where unemployment is below 4%. And there were a lot of different jobs out there, and I happened to be bilingual, and so I started looking for a job where I would be able to speak Spanish in my career, and I landed a job at Wellington Management Company.

CANDY O'TERRY: So you traveled the world across five continents while raising five children. How did you do that?

DIANNE O'CONNOR: I have a great husband, who is the best Sherpa. He is a magician with managing car seats and strollers and babies and moms that are a little overwhelmed.

CANDY O'TERRY: We learn something from every job we have. What did you learn from being in the investment world that you brought with you to the creation of Weston Table?

DIANNE O'CONNOR: I was really fortunate to work with some of the brightest people in the world. I had the opportunity to listen a lot, being a young person who was just getting my feet wet in a career that I didn't know very much about. I had a lot of mentors that were really terrific people, who were interesting outside of their work, who really held my hand and showed me the way to handle board meetings — tough people, mostly men, very few women in the investment advisory business. More today, I think.

CANDY O'TERRY: How did you make sure your voice was heard back then in a room full of guys?

DIANNE O'CONNOR: I'm not sure it always was heard. I kind of listened and learned and waited my turn, and now I have my turn.

CANDY O'TERRY: Take me back to your original idea of what you call a less but better philosophy.

DIANNE O'CONNOR: As I was getting started in trying to come up with a business concept where I could be creative, I was looking around at my five children, I was looking around at their friends, and I realized that the Millennials were really onto something. They wanted experience-based everything. And I said, "How is that different from the way that I have approached in the past and how I might like to approach in the future, the way I think about buying?" The '80s, when I came right out of college, was a time when more was better. Excess was better. The Material Girl was everywhere. It came to me to think about how they were gonna spend their money, and if I wanted to be successful, I needed to tap into some of the good ideas that they were bringing to the table.

CANDY O'TERRY: You know, you were just talking about when you started thinking about your business plan. The thing about entrepreneurs is you're successful if you take the time to write it down and figure it out. We all have ideas swimming around in our heads, but it's the successful entrepreneurs who do something about it. Take me back to those early days. You're creating ideas about conscious consumerism, inspired living. How did it all come out of your head and onto the piece of paper or onto that computer laptop?

DIANNE O'CONNOR: The inspiration came from looking around and seeing really beautiful people and really beautiful environments, and realizing that my best times were not out at restaurants with people. They were in people's homes. They were in people's lives, sharing the story, travel stories, journeys to the far corners of the earth, getting into the nitty-gritty, and you can only do that when you have an intimacy with others in friendships and communities. I took the idea and I said, "Look, what is the best that I've seen, and what do I really love, and how do I like to entertain, and how do people feel, and how do I make them feel like they are the most important person in the world when they're in my home?"

CANDY O'TERRY: Small artisans, ethically produced items. How did you find these people? You must have had to create an entire network.

DIANNE O'CONNOR: We have a depth and breadth of a network that's second to none, but I would say that, Candy, to be truthful, I just don't sleep. I sleep about four and a half to five hours a night, and that is it, and I work seven days a week.

CANDY O'TERRY: Where did that work ethic come from?

DIANNE O'CONNOR: Truth be told, I'm a farmer's daughter, and I grew up in Big Sky Country on a sheep ranch. I just all my life have been getting up before dawn.

CANDY O'TERRY: So let's get into that just a little bit. Big Sky Country. We're talking about Montana. Paint us a picture of your childhood.

DIANNE O'CONNOR: Oh, goodness. Boy, I'm gonna have to color outside the lines here, Candy, a little bit. I grew up poor. I grew up below the threshold for middle-class income. My parents, unfortunately, I lost when I was very young, and we ended up, my sister and I, moving in with my grandparents, being raised by people who were too old to raise us. So when I was in high school, my dream was to go to a better school, to get off of the Indian reservation school, to get off of the sort of life. I sort of saw something out there that I wanted, and I didn't know quite how to get it, but I found somebody to take me in, and I spent four years in Missoula, which is a slightly bigger town.

CANDY O'TERRY: This is a fascinating story. You telling me that you were raised on an Indian reservation?

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DIANNE O'CONNOR: Yes, my great-grandmother is Blackfeet Indian, and my great-grandfather was a stagecoach driver who stole a Boston stagecoach, and when he got to Montana, he said he was not turning around and taking it back. It was just too tough. He set up roots there, and back in the day, there was a lot of land to be taken, so they just settled down, and the Blackfeet Indian Reservation was formed, and we got kind of squished onto it.

CANDY O'TERRY: You mentioned that you found someone to take you in. That takes a lot of courage, doesn't it?

DIANNE O'CONNOR: It does, but those are the best people in life. I learned that sometimes you just have to open the door, whether you really want to, whether it's an inconvenience for you — pay it forward, you have to open the door.

CANDY O'TERRY: You go to college in Texas. Tell me about your college experience.

DIANNE O'CONNOR: My freshman roommate was Miss Nassau Bay. She was a really brilliant girl. She was a beauty pageant girl that grew up in Texas with the nice painted fingernails and—

CANDY O'TERRY: And you're a farmer's daughter.

DIANNE O'CONNOR: ...and I'm a farmer's daughter, and I arrived in Texas with a couple of pairs of Levi's 501 jeans and some T-shirts and hair that hadn't been cut in many, many years. She gave me a little makeover. I let her cut my hair. She took me home to her Houston family.

CANDY O'TERRY: You've had a lot of different chapters in your life, haven't you?

DIANNE O'CONNOR: I have.

CANDY O'TERRY: How did you stay strong during these tough times?

DIANNE O'CONNOR: Good people around me. I have a great husband I've been married to for 25 years. I have a wonderful, deep network of friends, and I also think that there are some people that just come out of the womb kicking and screaming, and they're not gonna let anything get in their way, and I'm one of those people.

CANDY O'TERRY: Let's go back to Weston Table. Walk me through this beautiful flagship store.

DIANNE O'CONNOR: I think the most impressive thing in the store, as you walk in, there is a giant wall of 100 years of oyster plates. They are all collected from the Old World. We have political, social, and cultural stories to tell about many of those different plates. Then you might wander in, and you will notice up a little higher than most women's eye level these interesting shaped fire extinguishers. They are made in Belgium, and a gentleman solicits designs, and the best ones win, and he puts them on these really fun fire extinguishers for the kitchen. Instead of wondering if the one you've had in the garage for 20 years is functioning, you have this gorgeous conversation starter piece in your home. We have this spectacular new way to grill in your backyard that is mobile. It's in three pieces, but the thing that distinguishes it is this giant 38-inch round cast iron and steel ore cooking surface that's circular, so people can stand around it and grill together. It was actually based on a gentleman from the Netherlands who was traveling through Far East Asia, and he was fascinated with the street cooking, and he really enjoyed how the men there were bent down and cooking lots and lots of people's meals. And he said, "How can I make this a Western European comfortable way of cooking, because there's so much to it?" And he came up with this grill that you stand around instead of crouch around. It's super fun.

CANDY O'TERRY: Every three months, the store is transformed. Can you tell us why?

DIANNE O'CONNOR: The store is small, but I also think that when you are trying to cater to a very difficult retail market, we don't want to be the kind of company that changes every season to offer a lot of different items that have little meaning for your home. Rather, we would like to focus on teaching people how to entertain, give in a thoughtful and creative way. And in order to do that, we have to inspire people, and if they see the same old, same old thing over and over again, they won't be very inspired for very long.

CANDY O'TERRY: You also have curated gift boxes, 100% flax linen bags. What is your message about giving gifts with purpose?

DIANNE O'CONNOR: Giving thoughtfully, I think, is something we all need to get a do-over on. The world that we live in today is instant gratification — I'm in a hurry, I don't have time, a gift card, cash. We can all pretty much consistently say that the most important things, the things we hold dearest in our lives, are the things that have meaning. And it doesn't matter how big or how small they are, but it's associated with a memory. And it's really hard to associate a memory with a gift card or cash. You can't remember who gave you what cash. I remember who gave me many, many of my wedding gifts.

CANDY O'TERRY: You know, I always think to myself, if my house were on fire, after I made sure all my loved ones were safe, I would probably grab my pictures off the wall, my children's little pinch pots, their pottery collection, and items that have been made with love can't be replaced. Do you agree with that?

DIANNE O'CONNOR: Completely, 100%.

CANDY O'TERRY: You also have a bridal registry.

DIANNE O'CONNOR: We have what we think is one of the most beautiful bridal registries and experiences in the entire country. We offer the opportunity for brides to come into our store with their grooms. We treat them to an over-the-top experience where we bring out options, and we talk them through what it means to register for heirloom gifts. We give them the opportunity to really encourage them to register for something fantastic that they think will just change the way that they entertain, will become kind of their personal mark on entertaining with their friends and family.

CANDY O'TERRY: So the whole thing started out in 2014 with online shopping for Weston Table. Westontable.com is the website, and your Instagram handle is @weston_table, if people wanna follow you on Instagram. Who was your role model when you were growing up?

DIANNE O'CONNOR: My goodness, I have so many, Candy, but the person who made the most difference in my life was an English teacher in high school, and she recognized something in me — just a special person who gave me a piece of paper that at the time I had no idea what this piece of paper was. But she said, "You have to take this exam, and it's on Saturday, and you need to take it." And I looked at it and I said, "You know what? That's great, but I can't afford the $12 for the exam." And she said, "Here's another piece of paper. Sign this and you don't have to pay the $12, but you need to show up for this exam." I showed up. Little did I know at the time that there was no pressure. I had no idea what I was doing, but I just took this exam, and I did really, really well, and it happened to be the PSAT, and it was my ticket into college for four years of paid school.

CANDY O'TERRY: A life-changer.

DIANNE O'CONNOR: It was a life-changer. She was a life-changer. Mrs. Gruba, she was a little Emily Dickinson sort of character.

CANDY O'TERRY: Wow. Tell me a little bit about your five children and how motherhood changed you.

DIANNE O'CONNOR: There is no better job on this planet than being a mother. I love my job now, but I love it most because I took the time to really enjoy my children. And for 17 years, I left the professional workforce and I focused on my children, and I sorta thought about it as a detour. And that detour taught me a lot about how to manage people and how to really negotiate difficult situations. I have three boys and two girls. I have a college hockey player, two college tennis players, a college-bound wrestler, and a rower.

CANDY O'TERRY: Wow. Sports all over the place in your house.

DIANNE O'CONNOR: Yeah, sports keep kids out of trouble, and it also teaches them some valuable business skills along the way.

CANDY O'TERRY: What is mother love?

DIANNE O'CONNOR: Sometimes don't say anything, just listen.

CANDY O'TERRY: What do you say to someone who's listening to this show who has an idea floating around in their head? Maybe they don't have the resources, but they have the dream to create something. What do you say?

DIANNE O'CONNOR: Take the risk. Risk everything, because at the end of the day, it's gonna work out. It always does work out.

CANDY O'TERRY: When I was preparing for our time together, I had to brainstorm about why we buy certain things. "Because our heart wants it," is what I said. Does that resonate for you?

DIANNE O'CONNOR: It totally does. We have to listen to what our heart wants for real, and not just think we want it, but know we want it, and know why we want it. And be able to say, "Look, this is my value system. Every purchase I make is going to fit into that value system, or I'm not gonna make it."

CANDY O'TERRY: What's the best advice you've ever received in your life, and can you pass it along?

DIANNE O'CONNOR: The best advice I've ever received has come from my husband. He said, "You just need to believe in yourself. You have the toolkit. Use it."

CANDY O'TERRY: At the end of the day then, Dianne O'Connor, what matters most to you?

DIANNE O'CONNOR: My family.

CANDY O'TERRY: What do you wish you knew when you first got started?

DIANNE O'CONNOR: I actually think of it as a journey. I think I learned along the way what I was supposed to know at that point in my life, and it's all good. It just keeps getting better and better.

CANDY O'TERRY: People measure success in different ways at different chapters in their lives. At this chapter in your life then, what does success mean to you?

DIANNE O'CONNOR: I have raised five beautiful children, one that did not arrive in the usual way. They are all on their way to living their own lives and building their own dreams. I now have time to cultivate and work on my own personal passions, and I have the support of all of them behind me.

CANDY O'TERRY: I wanna say thank you so much for sharing your story today, an inspiring one, about your past, your present, your future, and the success of Weston Table. I wanna wish you all the best. Thank you so much.

DIANNE O'CONNOR: You're the best, Candy. Thank you.

ANNOUNCER: Thanks for listening to The Story Behind Her Success with Candy Ottery. This is a series with one goal in mind: to shine the spotlight on women doing great things with their lives. We hope these weekly stories will motivate and inspire you. If you'd like to suggest someone for Candy to interview, she'd love to hear about it. Connect with her anytime on Facebook, Twitter, and her website, candyottery.com. That's C-A-N-D-Y-O-T-T-E-R-R-Y.com. You'll find all of these links in the show notes.