EP. 14 / The Knot Co-founder Carley Roney on building a billion-dollar company while raising her kids
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Carley Roney – Co-founder of The Knot on building a billion-dollar wedding business as a working mom, mom guilt, our society’s obsession with work and how it treats pregnant women.
Wondering how to balance raising kids and growing your business as a working mom? Or on the other end - do you have a gap in your resume and are worried that will disqualify you from some jobs? Wondering how to be present with your kids and disconnect from work?
In this episode, Carley Roney, co-founder of the Knot, shares her experience with starting her own business and trying to fundraise while pregnant. The Knot was valued at over a billion dollars! She shares her lessons learned - everything from her lowest point in business to being able to retire before she was 50 years old (and how she feels conflicted about that because of our society’s glorification of work!)
Carley shares how society needs to change the expectations it puts on women. She gives insight into why working moms actually get more done and are more efficient. She also shares why you should be proud of that gap in your resume and how to make it work to your advantage.
Carley tells us her story about working with her husband (which she doesn’t recommend), prioritizing what is important in her life, and how she is working to change our society’s relationship to work.
If you are a mom and are feeling that guilt for also working, then this episode is for you.
LISTEN BELOW! And don’t forget to ‘follow’ and leave a rating & review!
In this conversation with Carley you will learn:
Learn about how she built The Knot with her husband and took it public with a toddler
Learn about our society’s stigma around being pregnant in the workspace
Understand how to deal with a gap in your resume
Discover the pros and cons of being a mom and an entrepreneur
Consider how small or big you want your business to be
Takeaways from Carley Roney:
Being a digital pioneer
“Every person you talked to, you had to start at the very beginning. We really had to convince a lot of people that the internet was going to be a big thing.
The stigma around being pregnant in the workspace
“As a society, we look at pregnant people and we're like, you are about to be irrelevant.”
On when is the right time to start a business
“There's no right time to do anything. I tell everyone that there is no right time to have a baby, no right time to start a business. You just sometimes have to seize opportunities as they come to you.”
On how big to build your business
“You either need to have a big business or a small business cuz everything in between is torture.”
Experiencing mom guilt
“Not feeling guilty is actually one of the few gifts you can give yourself. It doesn't make it any better for your children. If you feel guilty, in fact, children can sense your own anxiety and guilt and then they feed off of that.”
Dealing with a gap in your resume
“Put it on your resume proudly, but make sure it says ‘up to date on this’ or ‘member of this,’ or make sure that it shows that you're not jumping back in fresh.”
The pros and cons of being a mom and an entrepreneur
“The pros of being a mom and an entrepreneur are that you have complete and total flexibility.
Advice for working moms
“Put your phone on, do not disturb. From like 6:30 to 8:30, I do not exist to anyone else in the world except these little humans.”
On early retirement after being a successful entrepreneur
“Well, I never say I'm retired because it's like shameful to me. Um, I don't know why. I mean, this is so funny and it's been such a struggle….I retired before I was 50.”
Meet Carley Roney
As a female founder of an early Internet company in NY's Silicon Alley -- and one of the few to see that company through from the harrowing start-up years to the growth years and a successful IPO -- Carley has a unique perspective on what it takes to make a solid, sustainable, exciting company. Her company created growth for so many small businesses by injecting creativity, a fresh voice, and technology into the world of wedding planning. (She is still amazed that 90% of American couples consult the service and brand that was created from scratch.)
Carley is passionate about helping other entrepreneurs -- particularly women -- be successful and so she travels the country sharing her tips, her mistakes, and her understanding of what moves millennial customers. She also works to do good on a greater scale, for example helping turn out the vote, raising money for promising candidates, or supporting social justice organizations in Brooklyn, NY.
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Check out the organizations that Carley works with:
Rent the Runway Brooklyn Community Foundation Power of Two Courier Newsroom
FULL EPISODE TRANSCRIPT
Kim Rittberg (00:03):
She co-founded the knot.com a billion dollar company and took it public. When she had a toddler digital pioneer, Carley Roney is here.
Carley Roney (00:12):
So I love hiring, working moms. Why? Cuz we all got in
Kim Rittberg (00:15):
There and we got [inaudible] done. Carley has amazing perspective and she's bringing it all, growing a business. How our identity is tied to our job title, the pros and cons of running your own company. And so much more.
Kim Rittberg (00:30):
Leave your lanyard and swipe card at the dorm. Welcome to mom's exit interview, a podcast for mom's seeking fulfillment and contentment outside the traditional nine to five, whether you're considering taking the leap or you're already mid-air, this podcast is for you. You'll meet moms, poor consultants, entrepreneurs stay at home moms with side hustles and part-time workers across various industries and levels. Plus every episode will have experts with tips so you can turn your inspiration into action. I'm Kim Rittberg. I was a Netflix executive and former head of video at us weekly and I'm a mom of two. I quit the corporate world and I've never looked back, but I'm still on this journey. So join me. We don't need a boss to give us permission or a promotion to lead the lives we want. First off, thank you for your comments and notes and please keep them coming. I'm gonna use your questions to ask our experts. And at the end of the show, I'll be reading out a note and please follow the show and leave a review and a five star rating that helps people find it.
Kim Rittberg (01:46):
That's what it sounded like when you went online. When our guest started her company, this was 1996. Yes. You had to use a dial up modem. You could actually hear it dialing it. Wasn't just like turn on your phone and hop on the internet. And many people got this type of alert when they got mail. You've got mail. This sets the scene for how much of a pioneer Carley Roney is. She launched a billion dollar company, the knot all while giving birth to three kids, you've most likely used the knot or the nest or the bump. All of which she co-founded because 90% of American couples use it. Carley is amazing. She's inspirational. And truly, she's a really lovely person in this in depth conversation. We talk about taking her company public. When her child was a toddler, Carley will share the lessons she's learned. She gives advice about whether or not entrepreneurs should take funding, our unhealthy relationship to work and why she felt ashamed to say she retired before age 50, which in my mind is total life goals. Carley also talks about being pregnant in the workplace, experiencing mom guilt and has tips on how to deal with a gap in your resume and how to reenter the workforce. After a break
Kim Rittberg (03:01):
You've had such an amazing career.
Carley Roney (03:03):
Ah, it's been an incredible rollercoaster ride. I really love to talk about it. I'm also really glad that it's largely over. Um, but yeah, no, we founded it as like four kids just out of college in a, you know, loft in Soho and ended up with like 1400 people around the world and a billion dollar evaluation. Ultimately when we, we sold it. And so it's a, it's a huge success story. And I'm like incredibly grateful not only to have had the opportunity, but to my co-founders and all of my team. I mean, it was really, it's, it's a, a story of a lifetime and it also is incredibly excruciating
Kim Rittberg (03:43):
<laugh> <laugh> yeah. And that's why you're here, cuz you're gonna talk about all the excruciating stuff.
Carley Roney (03:48):
Yeah, yeah, yeah, no, it's really present still here, like five years, you know, out of it. I still can feel every second of it. So I'm happy to talk about it. It's part of my therapy. It's just cheaper than actually going to therapy, which I do by
Kim Rittberg (04:00):
The way, when you say, oh, there are things that you still think about and still haunt you. What are the things that are still in your mind from running the knot?
Carley Roney (04:08):
Um, the, just the constant panic that it was all gonna fall apart. I think the, um, that, that feeling is palpable. I think every entrepreneur out there knows it, the idea that there's like so much resting on your every action, every move and um, between that. And then I have like, I have a couple of like real hardcore memories of super low points is as well as some incredibly high points. But I think that just that feeling of those 20 years of this sort of like panic of disappointing an entire team and your investors and all of that, that, that pressure just stays with you as a feeling
Kim Rittberg (04:53):
I wanted to ask Carley about the high points and the low points of being an entrepreneur.
Carley Roney (04:58):
My true lowest point in my entire career was, um, I, you know, we had this growing company, we were on our way to going public. We're only like two years old. At this point, we are just gotten funding to launch our gift registry. And I made an incredibly terrible decision in the middle of this to also renovate my apartment because I had a baby, um, solution is to also go live with your in-laws in Westchester and commute two hours a day. I'm just setting the scene there of all the bad choices that led to this point. <laugh>. So, um, the, also I had this newborn and she never slept. And the only way she slept was that if you've nursed her. So I basically like nurse kid, she never took a bottle. And so my day was basically trying to find ways to either, you know, nurse this child and do all the work and I'm nursing and writing customer service emails.
Carley Roney (05:54):
And it was 2 45 in the morning and I had to be up at six to drive into the city. And I like, I just can feel like leaning over, keeping my leg up, trying to make sure that she didn't like not latch while I'm writing this email and be like, what is my life about how did I get here? And then like just calm down and keep writing. And that moment, I just, I don't even know how that was the situation. I don't know if I could have done it any differently, but I really thought that I was gonna break at that moment. That was the lowest point in my career cut to
Kim Rittberg (06:28):
<laugh>
Carley Roney (06:28):
Literally four months later, I think, um, you know, being flown to Chicago to be on Oprah, to have Oprah say, you know, after we planned this incredible show with her to have her say America, if you're planning a wedding head to the knot, like just being, realizing that this one moment that you worked for that someone trusted you to plan the show with her and that she Oprah the queen of the, like marketers of the world that the queen maker king maker would say that. And it was just such an extraordinary high, um, and you know, going public the same year, that was incredible rollercoaster. So really, really lows and incredible highs. And so
Kim Rittberg (07:11):
You found the night in 96? Yeah. 96, right? This is tickle me. Elmo is big <laugh> Clinton. It was the second term. And you launched on AOL and there weren't even online ads. Yeah. So, you know, it's easy to say, oh, you launched the knot cuz now everyone uses it. And it's like saying like, oh, I went on Google. Okay. Well, whatever. Um, but it was really, so you were, you're a, a digital pioneer really,
Carley Roney (07:36):
You know, it's hard to remember that there was no internet. Um, now that all of our lives is on the internet and we really had to convince a lot of people that the internet was going to be a big thing. That was the hardest part I think about this is that you're going to this very traditional industry. That's like mom and pops and you know, not the most cutting edge, um, business people and convince them that the internet was going to change their, their lives and businesses and the entire industry, every person you talked to, you had to start at the very beginning <laugh> as I said, with this, like there's this thing called the internet, it's gonna be huge. Um, and so it was a long way before we could really get any significant traction. Um, and you had to kind of really stick with and believe in your vision. But we had a great team of four people. Uh, two of my friends from film school and my husband, we had all actually met at film school. And so we all believed in like producing and doing whatever it took to get everything done. And we could all wear a lot of different hats and had a lot of stamina and um, could live on rice and beans. So it did, we could make our like first million dollars we got from AOL go go pretty far for a long time, you
Kim Rittberg (08:43):
Know, million dollars of rice and beans. I mean, you're eating for like 30 years.
Carley Roney (08:46):
Exactly. I'm
Kim Rittberg (08:48):
Like, I'm not great at math. <laugh> that's maybe a hundred years. I don't know. So remind our listeners, how you and your husband met and how the
Carley Roney (08:54):
Origin of thenot David and I, my husband and I, or co-founders at thenot with two other friends, all from film school, I was in grad school and we had like a production company making like CD Rams, cuz that was the hot digital, um, thing of the day. And really couldn't stand on the work for hire like constantly pitching new business. And we're like, we should found something. We had just gotten married. And um, we were talking to these two other friends of ours, who we wanted to form this business with. And they were like, Hey, what about weddings? And I was like, oh no, excuse my French. But I was like, no, oh my God, I just got married. It is a terrible industry. It's so backwards. It's ugly. It's like not innovative at all. Let's pick something else. And the guy was like, um, did you hear everything you just said?
Carley Roney (09:39):
That means it's like the world's biggest opportunity, right? It's a completely backwards industry that needs revolutionizing. I was like a anti bride. Um, and it seemed almost, you know, shameful to actually start a business in. And then I thought, oh wait a second. There's other anti brides in the world. What if we did something really cool? And that's how I came up as we can call it the knot, we can be very sort of like anti tradition. And so the four of us did it. We got funding from AOL who was looking for content partners for their brand new partner, you know, brand new platform where they put content. And we, you know, we got the money and I think because we were so different, so alternative people thought it was like fun and edgy. And of course that chat rooms were filled with brides, discussing every detail of their wedding, you know, thereby saving their relationships with their friends because were tired of hearing them.
Carley Roney (10:31):
And we just really like hit the perfect thing, like an obsession online of early adopters, who, who then found each other, spent hours and hours, um, discussing it. And we were then slowly but surely because we aggregated this incredible audience. We were able to convince advertisers who were like new to the internet. In fact, we were the first company who thought of advertising on AOL as a way to finance our company. So we were like, we're gonna need some advertisers. And um, I, I feel ashamed about that now. I'm sorry I invented advertising on the internet cause it's kind of like what's made it such a success pool <laugh> but anyway, um, it was a great way to build a business. I mean, I almost got divorced like three times. I was gonna say, right this whole time you're working with your husband. Yes. I need to hear more.
Carley Roney (11:19):
And having babies, everyone wants to know about what it's like to work with your husband. It's awful and amazing. It's really both of those things at the exact same time. What's amazing about it is you never have to like explain to your boss. I mean, he ultimately was elevated to be CEO. We, you know, co-founded it together. But I was obviously going to be the editor in chief spokesperson, but at the end of the day, he's my boss. And what happens in this situation inevitably is as the big boss, he doesn't wanna be seen as favoring the person he's married to. So if he is like extra hard on you just to show that he's not gonna favor you. And then as the, you know, the employee, you're like, no, I'm your wife. So I deserve special attention like or special like, and that never, it just doesn't work.
Carley Roney (12:10):
Right. So, um, I also felt like I could share every opinion I had of everything he did, which is never a good idea. Right. Cuz you weren't treating him like a boss. So exactly. He was trying to treat you in a different way and you also weren't treating him like a boss. Exactly. Like it, it really is a bad idea and we tell everyone don't do this. Like if you have any other option as someone to found a company with do it. But the upside of it is that you're, they always understand what's going on in your life. You don't have to explain. You don't have to be like, I wish you were in a better mood when you got home. Like they're also as anxious about what just happened at the office. Um, and you know, but the ultimate downside is also that you really wanna come home and bitch about your boss <laugh> and there they are like asleep in bed next to you.
Carley Roney (12:51):
It's really not fun. So you need to find friends to bitch too. It's just adds an extra level of, of tension, but we made it and now we've been married for 28 years and are super happy to be, um, you know, retired work, husband and wife. So, um, talk to me about fundraising when pregnant, um, yeah. Fundraising when pregnant, um, doing anything when pregnant, you know, the, the, as a society, we look at pregnant people and we're like, you are about to be irrelevant. You're losing your mind. You're losing your time. You're gonna become obsessed. But though we've come so far in the back of everyone's mind, like, is she gonna be one of those people who quits afterwards? She says, she's not, but, or, you know, there's always that, that questioning in the background. So when you're you're pregnant a you just literally try to hide it.
Carley Roney (13:42):
I mean, I made a point like, and the flip side of that, I made a point to hire pregnant people, right? Like make a show of hiring pregnant people talk about it. Thing. Like here's one, she's actually giving birth in three months, but I think this is great. Cause we're gonna have three months to get her started. She's gonna go on her maternity leave. And then she'll, you know, she'll be able to come back with a, you know, you, you have to work around the reality that women are the only people growing the next generation of humans to consume everyone else's products. So this is a part of our work world too. And we just have to figure out how to find more ways to build that into the models that make women be able to be successful in the workplace. The real problem is we also need to change our cultural, our society's expectations of women.
Carley Roney (14:28):
I mean, it infuriates me, um, the bars, just so incredibly high and so many different aspects of our life. In addition, I'm sorry, this is, you know, my soapbox, like in addition, you wanna be a really, really good mom, not just a good mom, but like an extra good mom and all this information is available to you to read about how you can be perfect at all these things. But the math doesn't work out the hours aren't in the day. So what do we now start to say that you don't have to do as a woman? Like, you know what, one of the things I was like, you know what, I am not the content lead or whatever, the founder of a nail Polish company. So by the way, you will not find me having manicure. <laugh> judge me. I don't have another 20 min you know, another half an hour to sit and do that. Like, what are the other things do we does our hair always have to be perfect? Do we like, are there aspects of that and all the way, can our houses just look kind of like a shit show most of the time, isn't that okay with everyone? How we can't juggle all the balls? So what balls are we gonna collectively decide? We can drop.
Kim Rittberg (15:31):
I was totally typical, New York, 110% hustler. Not just because of New York, but like my dad was an immigrant. He was a business person. My mom was a creative worked full time. That just seemed normal. You go into the work world, you work really hard. You try to be the best at whatever it is you're doing. And then I had a baby and I was by the way, five months pregnant. Yeah. And I totally tried to hide it. I had the, had the, you know, resume holder in front of my belly and my boss, a man, he hired me and I called him before I accepted it. I was like, I do wanna let you know, I'm pregnant. He said, great. I'm a dad. No problem. And he like was such an amazing boss. The second time when we were acquired, I was pregnant with my second. I fully hid that. Cuz I was like, yeah, seven months pregnant. And my mat leave was cut from six weeks to three weeks. And so three weeks
Carley Roney (16:20):
Mat leave. Mm-hmm
Kim Rittberg (16:21):
<affirmative> come on. Could you imagine going to work with that mesh underwear where your look body's falling out like Ugh, three weeks, no way. So anyway, um, I think that I had an inflection point in my life when I had my second child and I said, Hmm, like you're a real like CEO. So I was, I got the, I was lucky enough to have the opportunity to build a business within a business. So I didn't have to take the financial risk and I didn't get the financial reward, but I got to run an 18 person unit. Right. I got to learn how to be a boss. I realized I could do something. I, you know, you work really, really hard. The loyalty isn't necessarily mutual in terms of like what you get and what you give. Is there another way to do this? I'm not saying everybody should quit their job. I'm just saying like, can we, as parents, as working parents as society, can we rethink our relationship to work our relationship, to what we want holistically. I'd love to know your thoughts about leaning out versus leaning in part-time work. Like your children are now older,
Carley Roney (17:21):
Mean there's no right time to do anything. I tell everyone that no right time to have a baby. No right time to start a business. Like you just sometimes have to seize opportunities as they come to you. I do think a couple of things need to be cleared to people. You know, one is when you're young work really, really, really hard because actually, even though you think all these other parts of your life need a little bit more balance, particularly right now, I, I actually think that's the time you wanna like super dive in, give it all you've got, you know, feel what it feels like to get as far as you can, because effort really is a part of a game right. In, in the workplace. So, you know, lay your foundation and groundwork there, make your contacts go to all of the events, go out there because it is true that when you have a child, your priorities change and they should change.
Carley Roney (18:14):
And there's nothing that you should be ashamed of about that. You need to split your time and devote it to your children, even with great childcare. And you know, I had the benefit of, um, my mother-in-law, um, Jane who took care of my children. So I basically had free, you know, childcare, which is what every working woman should have to make it easier. But you need to devote time to your children. Why? Because you have a very, you have a very unique, um, relationship with them. That is essential. Don't let anyone tell you otherwise, babysitters are great. Grandmothers are great, but you need to have that time, um, to do that. So think of investing early and then defend your time with your family relentlessly. When you have a child and work in, in a workplace, demand it, defend it, defend it from your own anxieties about like, I don't know, people are gonna be like, oh, she's not really giving it her all like, oh, she's so devoted.
Carley Roney (19:11):
Yes, yes. You're devoted to your children leave when they, when you know, you can leave demand more flexible work time. Um, and, and companies create some shared jobs. If you, a lot of women in your company, if you know, you have a workforce, that's going to have a lot of children create, figure out how to create shared jobs. So two people could go for maybe two years or so to be sharing certain jobs in the workplace. Yeah. Is it an additional hit to you? Cause you have to pay two sets of, um, benefits to them. Okay. But try to come up with solutions. These are really talented women that are gonna leave the workforce because it is unfair. It's cruel. And I think it is true. Also, there are so many opportunities to be a, uh, a consultant to work from the outside to be a freelance work.
Carley Roney (19:58):
If you have the ability to have someone else in your house, or you could go onto the marketplace and buy your insurance, like to have health insurance pull back during that period, because there are also now a, there are great opportunities. There's so many businesses who actually not only because of COVID are willing to have people who are not nearby, but also don't want a full-time employee to do a particular job. They'd prefer to only be paying someone for halftime, particularly growing companies that don't, you know, growing companies that need to bring on a lot of people to solve problems and want. Also, if you've been out of the workforce for a while, raising your family, which is something you should be incredibly proud of because it's very important. There are all these incredible platforms now from like second shift or things like that, where you now can go in list your skills and services, and don't be ashamed that you took time off, keep it in your resume. You know, there's really no time your children don't need you. I kept waiting for the time where I'm like, no, no it's gonna be okay. Just like around this next corner, I have a 24 year old. Sometimes she's like more, you know, time consuming and needs more of my like, you know, mental attention and emotional support and physical support than she did when she was two. So there isn't really any time where your kids aren't going to need you, but you do have more, um, more time cuz they're in school.
Kim Rittberg (21:18):
Like, but I like what you said, listen, everything is pros and cons. It's not like the perfect time to lean in yeah. Is ex age. But you know, do you think you do feel like children when they're little or need you more than when they're older or
Carley Roney (21:33):
No? I think actually like in the end of the day they need you in middle school. The very most right before, they're about to like kick you out of their lives is when, and that's actually interestingly that's when a lot of people then go back to work cuz of the little, the little ones are the babies obviously need you. And while you're working, you can give your children very, you know, devoted time. You just have to really separate yourself. I mean, I can't say that I was good at that. I was terrible. I had, so it was always like in my head, I can, I sometimes imagine what my kids looking at my face. Then there was like half of my brain that was like, [inaudible] can I solve that problem? What I couldn't really? And I, I would like to have devoted myself absolutely fully while I was there. That is my big, you know, lesson out to everyone else. Like shut it off. When you walk in the door, it will be there tomorrow.
Kim Rittberg (22:23):
So that would your biggest sort of regret or advice to working moms would be when you're with your kids. Yes.
Carley Roney (22:29):
A hundred percent shut off your brain from that other part of your life, don't answer the like you can answer the call after we all worked. When our kids went to bed and be clear with people around you, like really set it up, put your phone on, do not disturb. Now these things are possible, right? You can just say Nope. From like six 30 to eight 30, I do not exist to anyone else in the world. Except these little humans, I'm a hundred percent devoted to these humans. It will feel so much better after. I mean, I try to put my kids to bed, you know, every single night even was by the hair, my chinny chin, chin, like running in the door to do it. But, um, so that would be my, that, that is my big piece of advice. Just please try to make a real strong separation there, which is harder when people are working in the home. And the other one is I think we really need to do something about stress. I think that the amount of stress that women trying to juggle all the balls then go home and that stress is just so toxic for all of us.
Kim Rittberg (23:29):
I thought something you said about guilt that I thought was very resonant. Mm.
Carley Roney (23:34):
Yeah. I think that's the, um, I always feel like not feeling guilty is actually one of the few gifts you can give yourself. Like it doesn't make it any better for your children. If you feel guilty, in fact, children can sense your own anxiety and guilt. And then they feed off of that. That is something, just give that up be when you're there, you're there be there as much as possible and never waste another second. Cheating yourself again. It's like letting it Rob you twice. Right? You didn't get the opportunity. And then you also felt bad about it. There's literally no point. Just let it go. Devote yourself fully when you're there and then work your ass off at work. My favorite were working moms. I loved hiring working moms. Why? Cuz we all got in there and we got [inaudible] done. Nobody wanted to sit and like chit chat about like latest TV shows. We were like P every meeting. It was like, yes, small talk. Anyway, let's go. You know, we just, we knew we were there and we wanted to do great things and we just wanted to do them really efficiently.
Kim Rittberg (24:37):
I think it's really funny when that there is a bias against working moms. I'm like, have you ever worked with a working mom? They're the most efficient because they're so conscious of their time. I remember I interviewed someone for a job and later they were like, you were so intense. I'm like I had to hire seven people in three weeks. Yeah. And I was nursing a baby three times a day in my office with the blinds close. Of course I didn't have time for chit-chat a person comes into your office on their resume a five year gap and says, mom, would you hire them? And what would you think
Carley Roney (25:10):
A hundred percent would hire them? I mean, I really feel like it's important for us to start to be very transparent. Like we can't hide motherhood. We've literally been basically asked to hide motherhood. That's whatever, since the seventies, definitely through the eighties, like let's just pretend that we don't have babies. We just drop them and we keep moving. Um, and I, so I think it's really important for us to start acknowledging that proudly and also to not,
Carley Roney (25:42):
I, I, like I was say before, you also have to be up on your game. You can't be like I'm motherhood and I'm trying to get, I'm trying to get back in. And so I'm thinking about, maybe I should, like, if you're gonna go back into the workforce, figure out where you are, figure out what your skills are, bone up on, whatever has happened since you were gone and keep some of your, you know, go and reignite all of your contacts. Like it's not gonna be just given to you. We still want, you know, ambitious, um, hardworking people in our positions and companies like we, we wanna win at whatever we're trying to do. So, but I don't think that going and being a mom, you know, should disqualify anyone in any way from jumping back in as long as they're willing to like get back in the game. And part of that is, um, is more there's, there's more acknowledgement and opportunity and openness and even like platforms, right? That help you now stay up to date on your, or to, you know, on your, whatever your, your line of, um, expertise is. I think that that's much easier. Now you can get the newsletter from whatever your, um, follow on Twitter, all the people, and you can know what's going on in your industry, um, very easily.
Kim Rittberg (26:55):
So you feel like in invest in that, I guess it's on ramping process, like know that if you're out for five years, no problem. Put it on your resume proudly, but make sure it says up to date on this or member of this, or make sure that it shows that you are you're you're not jumping back in like fresh. How do you prioritize your life? Like when you think about this is how I want my life to be. Mm
Carley Roney (27:19):
I've never been a person who thought very far ahead, halfway through, I thought like, okay, wait a minute. I'm gonna be working this hard for the rest of my life. If I don't start to think about what I want to do. Like after I was in the, for, after we were in there for 10 years, like in that era, a lot of people founded companies, flipped them. We hid you already taken to public. We'd stayed with it. Then, then after a while I looked at myself, I'm like, we're gonna be here when we're 60, if we don't watch out, like, do we wanna run this company for 40 years? No. Wait. Um, so we made a plan to like that the 20 year mark, we should be, you know, cycling ourselves out like a, this is a company that is about the vision of young people getting married. You don't need like 60 year olds helping that like young people should be help doing that. And we were like out of the life stage, you know, we were like, maybe we should start, you know, creating a divorce site and a where to put your elders site. You know, it's like not as sexy as weddings and pregnancy.
Kim Rittberg (28:18):
<laugh> the, not the nest, the bump, the elders, the wheelchairs,
Carley Roney (28:21):
The no, and the crypt for the things we came up with and to choose to live another life was a really big undertaking and very emotional and challenging. I'm so glad I did it, but it was like really difficult for a couple of years to a let go. My 20 year mark coincided with the rise of Hillary Clinton's campaign, um, to be president. And so I was like, this is something I can sink my teeth into. What could change the world for working women was a woman in the chief, chief, chief, uh, CEO role. And so I was able to kind of transition to, to working on her campaign for a year and a half, which was really exciting and devastating as we all know. Um, but that to start and it made me start to think, you have to kind of think ahead a little bit more and not just be operating.
Carley Roney (29:11):
Um, and it made me think about like, okay, that was my daughter was also, um, graduating from high school that year. And I wanted to spend that last time with her. And now as my, you know, middle child's graduating from high school, I've shifted my life a little bit. Like I actually just kind of wanna be around when he is there because you know, kids only talk to you for a little hours of the day and you kind of, it's not like they're gonna talk when you want them to talk. They're gonna talk cause you happen to be there when they are frustrated or they're going to sleep. And so, you know, you, you can kind of plan your life better when you understand what you want. And I really want a good connection with my kids as much as I want them also to fly from the nest very fully.
Carley Roney (29:50):
And so that's something I prioritize. I really wanna be like inspiring and working with and creating like platforms and education that help women build great companies. Yes. But also just have like successful careers that they feel comfortable with. So like I make time every week to make sure that I can get on the phone with entrepreneurs to talk to them. I just talked to a woman yesterday who has a, um, an actual bridal shop in, uh, in San Francisco. And she was like, should I be expanding? Should I get F you know, should I franchise my business? And it's really actually, I like to get back and say, no, actually keep your business very small. There's nothing. You either need to have a big business or a small business cuz everything in between is torture. <laugh> right. It's very, very, you really don't have much control over your life as you are in that area where you don't have a huge infrastructure to support you.
Carley Roney (30:44):
And so I really liked discussing that with her, what her dream, what her dreams were her vision like do you just wanna make money and have a great and build a great, beautiful business that can support you and a couple of great employees or do you really want the stress of building it beyond that, that you're flying from city to city, like make choices. You don't have to do just what the magazine articles or whatever the blog posts say is the exciting new journey of X, Y, Z business person we're glorify this constant growth and change. Well, that's really built oftentimes around gain for investors, right? Is it really gain for you? You have to decide if you want that. Is it worth the extra a hundred thousand dollars you may be able to make at what expense? I think making those choices around, um, you know, I've I around how you wanna spend your time and what the financial payoff is.
Carley Roney (31:40):
And I know this is like a luxury to be able to talk to speak that way. But if you have the luxury to make some choices about your life, maybe you can be more, you know, generous of your life and then actually kind of spread that spread that love to a few people around you be really, really good to the people that you employ in your own lives. Give them paid time off, tell them not to come in. You know, if their child is ever sick and make up for some of that. And some of the extra space you've been able to earn in your own life, we have to kind of spread any, um, less stress that we can earn in our own lives with the people around us who simply don't have any, any choice.
Kim Rittberg (32:18):
Do I think that our society sort of glorifies fives work slash overwork? Yes. And the hustle. And I think I never really thought about it until I had a family and thought about what are the trade offs I'm making? What do you think about our society's relationship to work?
Carley Roney (32:38):
I think it's, I think it's unhealthy and I am a poster child for everything. That's that's wrong with it. Like I absolutely believe that I was a better person because I worked harder than anyone else. I mean, I say a better person, but like, that was the way I managed my own insecurity with, as a human being, I was like, well, at least I work harder. Like it was a way I quelled any whatever anxiety I had and it's, it's actually kind of sick too. Right? Like I have anxiety here working that you work more to call your anxiety like, well, this is perfect for who, oh, the business you work for.
Kim Rittberg (33:17):
So a lot of the listeners on this podcast and women I know are building their own businesses, I guess I would love to hear, how do you think about the pros and cons of being an entrepreneur and specifically a mom and an entrepreneur?
Carley Roney (33:31):
The pros of being a mom and an entrepreneur are that you have complete and total flexibility, theoretically <laugh> the cons are that you have complete and total flexibility, meaning you think you have control of your life and yes, you don't have the stress that your, you can, you know, you can scale your business up or down or your goals up or down based on how much you can handle in your life. But that's only if you don't take on investors,
Kim Rittberg (34:05):
Right. Would you say to someone be careful about how big you wanna grow?
Carley Roney (34:10):
Yeah. I think that if I would stay as much as you can self financ or through, uh, friends and family financing, um, more age of financing, because as soon as you have outside investors who wanna return, you lose increasing control of your because you have to produce for them. That's what the promise is. They're giving you money so you can give them more money back. You really should think hard, whether you want venture capital or not. Venture capitalists are not bad people. They just have a very specific business model. And that includes massive returns for them, for their risk. And you should find somewhere, get a loan loans, have a very lower, much lower expectations of returns and much longer timeframes, like think about all the different financing options and think about if you actually even wanna take on debt of any kind to grow your business.
Kim Rittberg (35:00):
I'd love your take on identity. When you, when you meet people now, how do you introduce yourself?
Carley Roney (35:05):
Oh, it's the worst? It's the worst. It was so easy. It's so easy. When you have like a job title, that's easy for everyone to understand, or you're the founder of this and that. And now I always debate, like, do I have to say like, oh, I spent, I often say like I spent 20 years building an internet company and now I, because I don't wanna be so tied to what I did in the past, but I want credit for it that people don't think like, oh, you're just like a nonprofit board person. Like, I, I really enjoy what I do now, which is a combination of use my, you know, my, my 20 years of, of internet expertise, helping, you know, young businesses and entrepreneurs and, and big companies. But I also really like the other side of it, which is sitting on nonprofit boards and in investing in democracy, like all three of those things I like.
Carley Roney (35:57):
And, but it isn't as easy to introduce. And it makes me a little squeamish sometimes I'm like, do I just leave out? And people will be like, wait, you can't leave out. You're 20 years founding these incredibly like powerful longstanding companies. That's, that's why you have the other opportunities. Right. But, um, but I think it's because we, we, once you said, we glorify, you know, work above all else in our society and you wanna have like a really sexy title and work for a really sexy company. And if your job is hard to explain, you feel a little embarrassed. And so I think we just all need to get over it. Or maybe it's New York also where we all ask each other, like, so what do you do?
Kim Rittberg (36:37):
That's literally, that's always the first question
Carley Roney (36:40):
That that's only New York, by the way. Yeah. What do you do? I'm like,
Kim Rittberg (36:45):
But by the way, I also, I, I feel like, yes, I think that we glorify overwork, but I also think, especially cuz this generation of women are very educated and we, we do wanna spend, we're gonna spend time working. Right? Absolutely. You're gonna spend some the best, right. You're gonna spend work. You're gonna spend some of that, its working hours. So of course we wanna do something that a we're excited about. Right? Maybe we take pride in, we wanna do it. Well, I do think that like, as we are in different stages of our lives, I do think that we need to question, who am I doing this for? Am I doing this so that someone else thinks I'm cool or that I have a fancy business card or I want that, but I also want this, how can I make those fit a little bit better together? So it's tricky cuz I'm saying, oh everyone overworked. Well I, for sure overworked for 15 years, I don't any regrets about it. No, I actually thought, especially when I only had one kid, it was a lot easier to work. Super hard. My second kid, he is mama's boy, like he's going mommy. I think I'm falling in love with you.
Carley Roney (37:44):
<laugh>
Kim Rittberg (37:44):
I was like, sweetie,
Carley Roney (37:45):
Sweet. Don't worry. Wait until he's 17.
Kim Rittberg (37:47):
You launched thenot it's usually successful. You go public, make some good money, you know? And then you're there for 20 years and you retire. What are your feelings around retirement?
Carley Roney (37:57):
Well, I never say I'm retired cuz it's like shameful to me. Um, I don't know why. I mean, I, this is so funny and it's been such a struggle. Like my kids are like, what do I put? They're filling out college application. Do I put your like retired? And I'm like, no, no, no, not retire. I guess I'm retired. It our, I mean, I, I retired before I was 50. It seems like the world thinks I'm just like not ambitious enough. I should have started another company already. Like it, it is embarrassing, um, to be retired and I'm always like, I'm I retired. And then I say, I retired from the not and, but I blah, blah, blah, blah, blah, blah, blah, blah, blah. I sit on the boards of rent the runway. I work with female founders. I, um, you know, I angel invest I'm on the board of two nonprofits.
Carley Roney (38:45):
I, you know, I, I feel this anxiety about feeling, making sure people think like it's not that I'm not ambitious. It's that I made enough money that I don't have to be building more value for my family. I can take care of my family and my extended family with the money I have. So why would I go do more work when I could use my skills for something that is not a full-time job? Listen, I'm talking myself through it. I feel like I have to rationalize the choices I've made, which is completely untrue. I'm so unbelievably happy that we made this choice. I could literally be still working at the not I had this opportunity. We leaped off and did it. We found great people to replace us and I really enjoy what I get to do. Now. I love being able to do this, to share my knowledge.
Carley Roney (39:34):
I'm using it for like real good in the world. That feels fantastic to have changed from building value and equity for my public company, shareholders, to be doing it right now to build equity in Brooklyn or to help. I, I work as a partisan called courier newsroom to build local newsrooms around the country to help educate Americans, um, everyday Americans on what you know, what politics really means and how it affects their lives. Like these are things that I feel a tremendous sense of purpose. I get paid for a few of them. I don't even, I don't even need the money. I mean, I sounds silly, but like I would use it to, you know, take care of my parents, but I feel like we should, in some ways go back to the fifties, but for everyone, for the, for men and women, all families like the goal should be to retire as early as you can.
Carley Roney (40:27):
And we don't have the same pension system. Like people aren't really getting to do that, but that's part of why. And part of why people are working so hard is to build any equity or value for themselves that they can. But, but this should be the goal. People should be able to lessen their work later in life. Not, not work at all. We all love, I loved work. That's part of my problem is that I love to work. And, but to be able to like lessen our workload, to be able to do things that are, to have more time with friends or travel more with family or, um, or your children like that, shouldn't be the goal we should be building towards that. And it shouldn't be a source of embarrassment. You hear I'm lecturing myself here. No,
Kim Rittberg (41:07):
It's, it is amazing to me. I'm like you are wildly successful, worked super hard. Everything you ha you, you worked for and deserve everything you have, but it's, it's kind of, I think it helps other people see, well, if someone like you also feels identity is so tied up where you have nothing to prove, you have nothing to prove you've done it. You're wild success and you have a great life, you know? So I think it helps other people here. How do you prioritize your life right now? What's most important to you right now in this phase?
Carley Roney (41:34):
Um, my kids <laugh> are number one, sorry, David <laugh>
Carley Roney (41:42):
Every mother in the world thinks that she's like the kids and you and you husband. Um, um, oh, how do I prioritize? Like my kids are really important to me. Increasingly my health is important to me. I was like, who cares about your health? You're fine. And now I really think you have to, we have to do more work taking care of ourselves. And um, and democracy is really, really important to me. I think that we all need to. And that's part of what also happens if everyone's working so hard, like mending the mind, Manning the store, what's it called? Tending the store of like this world we all live in. It's really important to me. I want, I want us to be able to figure out how to save our planet. I want us to be able to, um, have, you know, civic participation and voting rights for all these things are really important to me. Um, and I really actually also love being with women who are doing things that are interesting and important in this world. My time with my friends or my colleagues or sitting and talking about the ways we can like change culture or change the world, or just learn more about these different aspects of life's like constantly being curious and having people in my life that keep me curious. That's that's sort of another key foundation and priority
Kim Rittberg (42:59):
Focusing on your health. I don't see you being like the type of person who's eating, like deep fried Oreos. Are you not? I, you seem healthy.
Carley Roney (43:06):
<laugh> I'm I'm super healthy. I, yeah, I'm super healthy. I, um, I think that like I came late in life to a realization of how toxic stresses for you. Yeah.
Kim Rittberg (43:17):
Got it. Oh, health big picture. See I health I'm like, oh, cookies. Like for me, health is cookies, mental health,
Carley Roney (43:23):
Right? Yeah. Mental health. Like how really toxic I'm on the Bo I'm on the board of a, um, organization called power of two. That, that is about toxic stress and infants. And so just trying to learn, I'm a high, as you can tell in this interview, I am not a low key person. And so just like trying to learn how to be like a little bit more low key and not make everything feel life and death. Um, that's my, um, 2022 goal. <laugh>,
Kim Rittberg (43:48):
That's probably where we get along.
Carley Roney (43:50):
I know. Yeah. You're really helpful.
Kim Rittberg (43:53):
I find that as I'm coming to growing the business or other thoughts, sometimes my mind's wandering. I'm finding it hard to not say this is enough. Actually what I'm doing is what I want to be doing. I wanted to slow down. I want to take my son to swim class once a week. I want to be able to take my daughter from school and just have a walk with her and feel present. And so maybe it's a uniquely New York thing, but I don't think it is. I think slowing down has been something that I personally have struggled with. So I'd love. Are there other things that have played a significant role in your path?
Carley Roney (44:29):
You know, something that I, an article I read in the New York times this week that really had had deep meaning to me was about ambivalence, was about that. We're constantly also like judging ourselves with the things we're unable to do. Like, I guess I don't have enough willpower to do that, or I, I don't make strong choices for myself or whatever, but reading this article, it talked about the idea and I, this really spoke to me that actually it's deep ambivalence, that we can see both sides that slowing down. Like I really enjoy my work and I know what the outcome is here and I'm very comfortable in this zone. And I also know that I wanna slow down more and I, but that would be really hard work for me cuz it's not comfortable. And so, uh, I'm just ambivalent and that ambivalence is actually what keeps us because both choices make sense to us.
Carley Roney (45:21):
And in so many areas of our life, like I'd be like, it made sense to me to be working in the middle of the night, writing that customer service email. Cause I really wanted that done and I really wanted to be great. And it also was so painful because I was like really, really tired and I really wanted to sleep. And so I look at it now and it was like, that was the part that was tortuous of it. But I, I couldn't make a different choice. I'm saying ambivalent about it. And so as we are trying to make these choices for stuff, I think sometimes it's great to just to be like, you know what both options mean a lot to me. That's why I can't make this change in my life because I'm actually ambivalent because I understand the payoff here. It's comfortable to me and this other road, I don't understand the payoff.
Carley Roney (46:02):
So that's why I keep doing what I don't really wanna be doing. It's just that it's easier. Cause I understand it. And so I think almost like really being, being smart for yourself, like what are the, what are the benefits of both of these choices and being more literal and just taking a second to be like, is that really what I want? Or I think just to have a certain level of consciousness on, on both hands one to understand all these different motivating factors and really just give yourself a second. Sometimes it's not, not easy or obvious always to make great choices, but also, you know, things are not as life and death as we think they are. You're never sure what decision is gonna be the decision that's gonna make or break anything in your career or your startup, but it is seldom true that that one individual thing will make or break anything. So maybe if you're just more clear about your values, like I'm gonna do my very best given my circumstances every day, but those circumstances also need to include what you want your life to be like set those parameters for yourself. Do as much as you can inside of that, I
Kim Rittberg (47:15):
Feel like this is like the most amazing conversation. Are you happy?
Carley Roney (47:18):
I'm so happy. It's so nice to be so happy. Uh, and that's a very good question. I don't think we worry enough about whether people are happy. We assume that there's like happiness built into life. Um, and it really isn't. I think a lot of life is, um, ups and downs. I'm trying to teach my kids that, that like there are downs, but guess what? There are also ups afterwards. I'm, I'm happy with the way my life is today and what I have done and what I have I've built. I've also just set this incredible run, being like an early advisor to rent the runway, such an extraordinary company. Who's gonna change the world and help save our planet. What a great life I have an incredible apartment. I have really good friends. Um, and I get to work with interesting people that I choose whether I wanted to work with or not. And that honestly, it's kind of like the level of control you have over your life is very, it's comforting to wake up in the morning and to know like, oh, I get to make almost all my own choices today. I see.
Kim Rittberg (48:23):
I think you're right. I think control and choice is what so many women, people, people in general, but this podcast about women <laugh> yeah. Um, control and choice control, choice and freedom. I think those three words are things that come up so much. So it's, it's great to be able to appreciate that you have them. I ask Carly for her predictions on what will happen in the workforce with so many moms leaving their jobs and looking for more flexibility.
Carley Roney (48:48):
I, what I think is fantastic is that companies are going to be forced to find new models for women to work or people to work in general. But in particular women, they can't find anyone to work for them. The power has shifted. Um, the government has an opportunity to play a role in this, but I think that the innovation just the openness, because they will be forced to right. Um, because nobody has it because unemployment is so unbelievably low
Kim Rittberg (49:16):
And you're right. And I also think, you know, the, the, the, I don't wanna say younger, but the, the, the employees with less experience, they're demanding more too. So I feel like if, if working parents are demanding more and the new generation of workers are demanding more right, that forces companies to change, they can't say, I'll just replace you with this other person
Carley Roney (49:33):
COVID and what this pandemic has done to reset so many things about our society. And it'll be very interesting. If you have to compete for talent, you have to have more compelling offerings. Companies need to be being judged by more than their shareholder value. They need to be judged by their employee happiness.
Kim Rittberg (49:55):
So more, I talk to moms, I realize like we are judging ourselves and we are letting other people judge us. And the truth is why, why would we feel ashamed that we're interested in doing part-time work? Why would we feel ashamed that we are interested in maybe working 80% or 75% when our kids are
Carley Roney (50:09):
Little, the enemy, shouldn't be yourself, the enemy. And I, I say this with some reticence, but like, because it's like highfalutin, but the enemy is really the way we have embraced capitalism. And I'm not, anti-capitalism don't get me wrong. But like the hustle benefits companies, it doesn't benefit culture and families. Right? So all of that thing, and there's nothing wrong with it, but the balance is off. So that's, if you could be like, oh, the enemy is that my thinking this way and working harder and feeling bad about myself and wanting to give more to the workplace, actually benefits industry more than it benefits me. And is I'm the only one who's gonna fight for my family, right? Or for myself industry and the economy and cowboy will always want more from me. Right. They'll want me to work more and want me to buy more. And the only person who can fight for like the quiet time, doing nothing, just the intimate, quiet time that doesn't serve anybody is you. And I felt like that, like understanding the war better and to know exactly the same way about breastfeeding. Nobody wants you to breastfeed cuz it benefits nobody. Right. But women have to fight. Right. So remember who you're fighting against, you're not, nobody is, you should not feel ashamed. And that anyone who, um, has that in their mind think about who's benefiting from that thought in your mind, it's not, you
Kim Rittberg (51:41):
That's so poignant. This was a great conversation. I mean, I'm, this is so great. Thank you so much.
Kim Rittberg (51:48):
While Carly has left the knot, she's committed to advising other female founders she's on the board of rent the runway, and she's involved in several organizations to help make the world better. Like the courier newsroom, which helps build local newsrooms around the country. The power of two NYC, a non-profit that coaches, parents living in vulnerable communities to provide their babies with the best care possible. And the Brooklyn community foundation, which is dedicated to Brooklyn's charitable community and works in partnership with generous donors and community leaders to invest in racial justice and community led change. All of those organizations will be linked out in the show notes and you should absolutely check that out.
Kim Rittberg (52:30):
When you send in your comments or your questions, we'll be asking them to the experts and we'll be reading them out on air. This one is from Adriana, Keith Adriana. Thank you so much. She wrote a review. It says I'm loving listening to this podcast. Loving is all caps. Thank you. I quit my career to find something that made me happier a few years ago, and this podcast resonates with me so deeply. I love the inspiration and practical tips for guests spring worth a listen, Adriana. Thank you. Thank you, Bravo to you. It is really hard and scary to meet the huge change. So good for you. And I'm so excited. Thank you. Thank you for listening. And at the end of every show, we have a real mom moment, something funny or embarrassing or whatever you wanna share. So send them in and we'll be reading them out. This one is from me.
Keith Adriana (53:17):
So I got a call from camp. The head of camp says, your son says you didn't pack him lunch. I'm like, what are you talking about? We packed him lunch, some contacts. My son has always been under 10th percentile. So in height and weight, very small. And we pack him lunch the whole year. We give him like a normal or robust lunch that he never finishes. So she says you didn't pack him lunch. I said, we definitely packed him lunch. She turns to him, oh, he says he finished this whole lunch for snack. And he's still hungry. I'm like, this has literally never happened before. So she says, can I give him a granola bar? I said, don't worry. He has no allergies. Give him a granola bar. I'm like, what is going on? My tiny son who has no appetite is like saying I didn't pack him lunch the next day, my phone rings.
Keith Adriana (53:59):
So the camp again, your son says you're to impact him lunch. Now I'm like losing my mind. I'm like, I definitely packed him lunch. Um, did he eat his whole lunch again for snack? She says, yeah, he ate his whole lunch for snack. Um, can I, I said, yes, you can give him a GRA bar. I'm like totally confused. We gave him like a full lunch, bigger than any normal lunch he's ever eaten. So turns out our friends whose kids are also at camp, they packed their kids like a really junky lunch, Lunchables and Oreos and Gatorade, like a delicious snack, like from my childhood, like a delicious, like snacky lunch. And so turns out my son just really wanted that kind of lunch and ate his whole lunch. I think, I don't know. Maybe it was like, maybe it was like to teach me a lesson. Anyway, it was really embarrassing and I was very upset about it.
Kim Rittberg (54:58):
Thank you so much for listening. We wanna hear from you tell us what topics you want us to cover and what questions you have for upcoming shows and experts. We will read everyone and we will use them. You can find us everywhere. Go to kimrittberg.com, scroll down to find the contact button, or you can DM me on Instagram at Kim Rittberg, or you can leave your feedback right inside your review in the podcast app. Please follow the show in apple, Spotify, or wherever you listen and leave review in a five star rating. And don't forget to share it with people who will find it valuable. It's truly meant to be a resource. And this is mom's exit interview. I'm your host and executive producer, Kim Berg. The show is produced by Henry street media. John Horowitz is our editor and Aliza. Friedlander is our producer in publicist.