How I Built This Podcast with Guy Raz: Advice Line with Angie Hicks

Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds. Advice Line with Angie Hicks features Weston Table Founder and CEO, Dianne O'Connor, who is wondering how and when to bring on new leadership to help her grow her e-commerce home goods business. Listen to the episode on Wondery, Apple Podcasts, and Spotify, or read the transcript:

GUY RAZ: Welcome back to the Advice Line on How I Built This. I'm Guy Raz, and my guest today is Angie Hicks. She's the co-founder of Angi. It's a brand you turn to for all of your home improvement and maintenance help. What do you say, Angie? Should we take another call?

ANGIE HICKS: Great.

GUY RAZ: Welcome to the Advice Line on How I Built This with me and Angie Hicks. Please tell us your name, where you're calling from, and just a little bit about your business.

DIANNE O'CONNOR: Well, hello, Guy. Hi, Angie. I'm Dianne O'Connor. I'm the founder and CEO of Weston Table. We are a Boston-based e-commerce platform that is seeking to change the way that people open their wallet and shop online. And we have decided that we want this marketplace to be the go-to place for living, giving, and entertaining.

GUY RAZ: All right, and you sell sort of home goods, right? Furnishings and even some furniture?

DIANNE O'CONNOR: We sell very little furniture, to be honest with you. We sell mostly tabletop, entertaining things that you need — you know, things that make your house a home, beautiful artwork. A ton of vintage items from around the world. A lot of American and women-produced goods.

GUY RAZ: Oh, cool. All right, so it's called Weston Table. You're in Weston, Massachusetts?

DIANNE O'CONNOR: Yes, I am.

GUY RAZ: I see. Okay, that makes perfect sense now. All right, from what I understand, you launched this in 2020. Were you in home goods and sort of home decor before you started this e-commerce business?

DIANNE O'CONNOR: No way. I was raising five children a couple years ago. Full of dogs.

GUY RAZ: Awesome. So you had been raising your kids and you jumped back into sort of the outside workforce?

DIANNE O'CONNOR: I did. I was working for a big investment advisor for many years before I had children. Then I stopped working altogether to have these five kids. Then they started going off to college and I was somebody who had a lot of energy. I said I'm going to put everything I've learned being a parent to work doing a business.

GUY RAZ: Wow, I just want to say I love that so much. And if you listen to the show, you know how much I love founders who are over 45, over 50 — which is to say, Cynthia Tice started Lily's Chocolate, sold it for $425 million ten years later — because people think founders are like 22, 23, and it's not true. Most first-time founders average ages 39, 40. You started this business when you were in your 50s.

DIANNE O'CONNOR: It's awesome, and everybody listening should know it is never too late. It's never too late, but it just means I need to get there faster, so I'm well on my way.

GUY RAZ: Got to get there faster? It's okay. All right, good. But you have that — you're coming with all this experience as a parent. I mean, managing a household, you know, talk about real-world experience, that's no joke.

DIANNE O'CONNOR: It is. I started with, you know, myself and then another employee, and now I'm up to 10 or 11 full-time employees plus offshore teams.

GUY RAZ: That's pretty exciting. So you started this in 2020, and now how have you done this all online, direct to consumer? It's remarkable.

DIANNE O'CONNOR: Well, I think we are meeting a place in the market where people are responding to. During COVID, people were stuck in their homes, and they basically had their husbands and children, and Amazon as their best friends. And I loved Amazon, and I still love Amazon, but I got to thinking about it. All the things I missed on the outside world — and what I really missed was that beautiful window shopping experience, that sort of casualness of just, you know, making your house a home by going out into the world and finding things that speak to you and your travels and your life. And I wanted to take my artistic talent and turn it into a website.

GUY RAZ: All right, so before we bring in Angie, what is the question you brought for us today?

DIANNE O'CONNOR: Well, I guess, Angie, I'm super curious. There came a point when you decided that you guys, in order to enter some of these bigger places, needed to take on investors. I'm a national brand already. How do you make that decision to give some of the control — or do I even have to give some of that control to someone else — to really skyrocket this into the next level?

GUY RAZ: All right, Angie, first of all, thoughts or questions for Dianne?

ANGIE HICKS: I need to spend more time finding ways to entertain people and that's really difficult when I'm CFO, CEO, HR. And finding a way that I could focus on what I'm really good at, and give up the things I'm not good at — and by finding a partner or an investor that would take this journey along with me — like you said, you have to be careful about who you pick. But is it necessary? You know, like, when's the right time?

GUY RAZ: Yeah. Dianne, do you mind giving us a sense of what your revenue is right now?

DIANNE O'CONNOR: Just five million.

GUY RAZ: Wow. Okay. So you've really scaled this quickly, which is awesome. Are you talking about — I mean, in your perfect world, would you want to have a CEO and that would free you up to kind of focus on the creative side and the things that maybe you enjoy doing more?

DIANNE O'CONNOR: 100%.

ANGIE HICKS: Yeah, yeah. And I think that's important to know — like knowing what you're good at, knowing what you want to do. I mean, you commented that you came out of finance. Like, I know it's easy for you to do the books, but it's not necessary for you to do the books. You need to be able to read them, understand them. And I have no concern that you're going to be able to do that. No one's pulling anything over on you. But just because you can doesn't mean you should. So, you know, finding people that can kind of take some of those tasks off of your plate — that just allows you to do things. My best example is I used to buy all of our media because I could, not because it was like, you know, I kind of found it fun or whatever. I was getting ready to have my second child and my second child was born in the spring when I would buy all the media. And, you know, I was going to take a whopping six weeks off with my new one. And so I had to give someone else that job. And, you know, that break — being forced to make that decision was one of the best things that happened. We got better rates because she just wanted to make sure she kind of knocked it out of the park. And I didn't buy media anymore, which meant I could spend my time doing things that were more valuable to the organization.

ANGIE HICKS: The cool thing is, is I think we're at a space right now where if we brought someone in and they wanted to be a partner — and I mean a true partner, an investor partner, somebody who's willing to put what I've put into the business and do that as an equal — kind of exciting to me. I have people in my family saying, no, no, no, keep it as a family business. And I'm like, yeah, but you don't have to run it. So, you know, you don't have a say right now because you're not doing the heavy lifting here.

GUY RAZ: I think that it's an interesting — I mean, they're interesting arguments on both sides, right? Like, we did an episode with Mike Sinyard, who started Specialized Bikes. And it was really, you know, he ran it for a long time. And then he was encouraged to bring in professionals. And that did not work out well at all. It almost tanked the company. This is a cautionary tale, and he went back and retook it over, and now, you know, he went back to running it. But we have plenty of examples where people brought on others, operators who had different skill sets, and really were able to realize the vision. And realize the vision in the project. I mean, we had this story with Kava. Kava is now a national food brand. The three original founders were Greek American buddies who had a restaurant. And eventually, you know, many years into the business, when they were kind of small scale, they found somebody who wanted to join them. And he helped scale that business into a national brand. And it's been a phenomenal partnership for all of them.

DIANNE O'CONNOR: That's exciting to think that that's the direction that we're headed in. And watching Angie start at the very bottom in a hundred square foot — I don't know — office space. And I think, yeah, you know, I've got about a hundred square feet here. There is definitely excitement for the future, but finding the partner I think is definitely it.

GUY RAZ: It sounds, Angie, to me that you found a partner right off the bat.

ANGIE HICKS: I did. I did. So I had my co-founder and then he eventually joined as the CEO about three years after we started. So, you know, I had an easier path on that journey because I had an advisor that was, you know, wanting to step in, so that worked out perfectly and kind of let him kind of take that kind of scale and let me focus on the things that I enjoyed focusing on. So it was a good balance. You know, one thing you might also think about is you're kind of talking about these interviews. I mean, if you're looking for a CEO, maybe, you know, like you could go out looking for a CEO or you could go out looking for a Chief Operating Officer, and finding someone that can kind of come in and then, you know, kind of work their way into the business. And then, you know, maybe, in a couple of years, they take that CEO seat as you guys develop comfort around that as well.

GUY RAZ: Indeed. Dianne O'Connor, the company, the brand is called Weston Table. Congrats on your success. Good luck. It sounds like you are well on your way to scaling this thing.

DIANNE O'CONNOR: Well, when I am scaled, I hope you have me back as a guest again.

GUY RAZ: I hope so, too.

DIANNE O'CONNOR: Thank you so much, Angie. I am a big fan.

ANGIE HICKS: Thank you. Thank you, Dianne. Best of luck.

DIANNE O'CONNOR: Thank you. Take it easy. Bye, Guy.

GUY RAZ: Thank you. Bye.