Carolyn Childers: How a Fortune 500 exec ignited her own startup

Carolyn Childers cut her professional teeth at the best-of-the-best companies, between investment banking and big businesses. But when faced with the challenge of straying from a traditional corporate path to start her own company, founding her business — Chief — became her biggest move yet.


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Carolyn Childers

Carolyn Childers is the co-founder and CEO of Chief, the private network built to drive more women into positions of power and keep them there. She is an experienced leader and operator, having successfully scaled several early-stage businesses including at Handy, Soap.com (Quidsi), Victoria’s Secret, Avon Products, and Deutsche Bank.

Five leadership lessons from a unicorn founder: Carolyn Childers, CEO of Chief

Carolyn reflects on her journey to the top and imparts wisdom about what she wishes she’d known in her early days as a founder.

It’s a common story—a childhood lemonade stand foretells an eventual bite by the entrepreneurial bug, and the rest is history. For Carolyn Childers? “Nope, that wasn't me,” she says with a laugh. It wasn’t until years into her career that she entertained the idea of entrepreneurship. “If I did it all again, I'd wanna get into startups faster,” she says. 

After completing a finance degree, Carolyn set her sights on working for some of America’s biggest corporations—and she landed a gig as an investment banker at Deutsche Bank. She eventually found her way into the startup world years later after meeting connections through her MBA program. Fast forward to the present, and Carolyn Childers is CEO at Chief, a professional network focused on senior executive women. In March 2022, Chief became a unicorn with a valuation of $1.1 billion. More than 20,000 senior executive women are Chief members and another 60,000 are on its waitlist. 

We sat down with Carolyn and she shared lessons including why trusting your team is one of the best things you can do as a leader, the reason you should pay attention to early wins, and a warning for aspiring unicorn founders about what not to do when you raise cash.

There’s no better teacher than autonomy and trust

Carolyn’s first foray into the world of startups was at Quidsi—at the time, a fairly unknown company— now famously nestled under the Amazon umbrella. The co-founders, Vinit Bharara and Marc Lore, had a reputation for succeeding in notoriously difficult markets through intense grit and perseverance. “Marc continues to be an inspiration for me as a leader,” says Carolyn. “I've never worked for somebody who gives so much autonomy to people.”

Carolyn had been tasked with running operations for Soap.com, an arm of the Quidsi business. “I walked into that company with zero qualifications for doing what I was being asked to do,” says Carolyn. “And yet Marc gave me just complete, full reign.” 

Carolyn recalls working through initial inventory buys with Marc before launching the platform. She noticed that in order to have the wide variety of assorted inventory needed for a successful launch, she’d need a hefty budget. But she was concerned it’d slow her down too much to go through the process of securing more dollars. “Marc just pulled out a piece of paper on the spot, drew up a very quick contract between the two of us and named an amount of money. It was millions and millions of dollars,” says Carolyn. “He was like, ‘I trust you, go!’ It was incredibly empowering. His trust drove me to work harder than I’d ever worked before.” 

The biggest learnings come when there is no playbook

It was at Quidsi that Carolyn first started dreaming of building her own business, but she made one more stop along the way before entering the world of entrepreneurship herself. She spent four years heading up operations at Handy, an online household services marketplace for cleaning, installation, and handyperson services. It was a business model that was extremely challenging to make profitable, so Carolyn had her work cut out for her.

“With Quidsi, there was a playbook for how to make an eCommerce business successful. With Handy’s business model, that wasn't the case,” says Carolyn. “There was no gold standard to learn from. I needed to figure out: How do you build and scale a home services organization that is meticulously personalized for every single person?” But this challenging environment proved to be the crucible in which Carolyn developed some of her most important skills as a business person and leader. 

“It was such a big business challenge that I needed to push myself every single day to think through, ‘How do we truly innovate to make this work?’” she says. Navigating this uncharted territory—and eventually drawing her own map—was one of the most important professional experiences Carolyn has ever had. As tough as it felt at the time, Carolyn feels she wouldn’t have become the entrepreneur she is today without it.

If you can’t find it, build it

“Being a senior executive at a startup and being the founder of a startup are two very different things,” says Carolyn. Even though she was beginning to gravitate towards entrepreneurship, Carolyn wasn’t just looking for any old idea.  “It needed to be a mission that I could pour myself into for years and years.”

Two factors sparked the idea for Chief. Firstly, Carolyn was grappling with these questions at a time of great political and social turmoil. The combination of the 2016 election and the #MeToo movement influenced many companies to step forward for the first time and say that they wanted better representation in their senior leadership. And secondly, Carolyn was realizing, “I was not very good at building my network. I decided to go on a personal journey to address this gap.”

“I started to look at other models and other businesses that offered professional networks and support, and didn't find anything that I myself was eager to join,” she says. “So I decided to build it.” But the journey was anything but easy. “That early period was by far the darkest,” says Carolyn. “Because everybody had skepticism.”

Celebrate early wins that give proof of concept 

Today Carolyn is at the helm of a thriving—and growing—business. But, “to this day, I'm still in the paranoid state of like, ‘Is it working?’” she says. That’s why it’s crucial to celebrate the small wins along the way.

Carolyn recalls two early moments that assuaged her anxiety and gave her the powerful sense that she was onto something. In 2018, Chief had just announced its seed funding in a major publication. “We didn’t even have a full live website describing what we did yet. We just had a simple waitlist,” she says. “But we had thousands of people sign up for that waitlist within hours of the press hitting. That was the first time that we really felt like, ‘Okay, there's something here.’” 

Another win came when the Chief team was sending cold outbound emails targeting senior executive women. “Within two hours of us sending this email, a C-level, Fortune 100—probably like Fortune 10—individual signed up and paid.” 

“These moments made me realize, ‘This isn't just something that I feel like I need. This is something that people are really looking for,’” says Carolyn.

Don’t let an influx of cash steal your focus

In March 2022, Chief raised a $100 million Series B, hit a $1.1 billion dollar valuation, and officially became a unicorn. This moment was a triumph, and not just for Carolyn and her co-founder Lindsey Kaplan. “It felt like a celebration for our entire community—all of our members,” she says. “Beyond that, it felt like we showed that investing in women is a good investment.”

Carolyn has advice for other aspiring unicorn founders. “If you have too much capital, it gives you the luxury of being able to ignore things that aren't going well. You can just muscle through them by putting more money into problems. But if you do this, you don't learn what's working or not working for your organization,” she says. “The failures and the hard parts, the things that you didn't know are actually where you learn the most about your business. “

“Whether it's unicorn status, your first Series A, or any time you raise capital, make sure that you are really focused,” says Carolyn. “Just because you have more capital doesn't mean that you should set it on fire.”


Carolyn Childers: There’s something about kind of blowing up the bridge behind you so that you can’t go back. That is both a really good thing to do, but also somewhat unhealthy at the same time. But for me, I don’t think I would ever erase that.

Talia Goldberg: Welcome to Wish I Knew, the show about the revelatory aha moments that founders, CEOs and leaders discover along their own business journeys and why taking risks leads to growth. I’m your host, Talia Goldberg. And on today’s episode we find a new way into the wonderful world of startups with our guest Carolyn Childers.

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About a decade ago when I was in college, I remember that the best and the brightest students all really wanted to go work on Wall Street. Everyone was dressed up in suits for their on campus interviews and recruiting and was vying for jobs at places like Goldman Sachs, JP Morgan, Deutsche Bank, Blackstone, you name it. I was a lone wolf wanting to go into the tech industry and work with startups. But a few years ago when I went back to campus as an alum, I saw that things had totally changed. Many of the students I spoke with were inspired by people like Mark Zuckerberg and other dorm room founders, and they wanted to go work at tech companies like Google or Amazon or Facebook or even do startups of their own and jump in and try their hand at entrepreneurship.

It was a total change from what it was a decade ago, let alone two decades ago when our guest, Carolyn, found herself working at Deutsche Bank. And while that was an interesting time to be in banking, Carolyn was also an outsider for the era as she caught the startup bug. This episode is all about the tenacity and uncertainty that comes with going out on a limb and diving head first into founding a startup. But we’ll learn that from Carolyn herself as we chat with her from her home in Florida. Joined by the next voice you’ll hear, Kent Bennett. Kent and Carolyn have known each other for decades. Kent is also my partner at Bessemer Venture Partners, and as it turns out, he also makes for a really, really great co-host. Fun fact, he was a screenwriter before he was a venture capitalist and he has written a lot of comedy, so I think you’ll laugh too. Here’s Kent.

Kent Bennett: Okay, so Carolyn, tell us your name and what you do.

Carolyn Childers: I am Carolyn Childers. I am the co-founder and CEO at Chief, and Chief is a professional network focused on senior executive women.

Kent Bennett: And you and I have known each other for a long time.

Carolyn Childers: A long time.

Kent Bennett: Well before there was a chief.

Talia Goldberg: It was in 2006 at Harvard Business School where Kent and Carolyn first met.

Kent Bennett: Like many friends, I don’t think we’ve ever sat down and actually just talked linearly about our lives. I am genuinely curious. I’ve never asked you, when you were leaving college, what was on your mind? Did you know that you were headed for startups? Did you have a plan?

Carolyn Childers: I think for me, a lot of people always tell the entrepreneurial story and say, “I was an entrepreneur since I was little with the lemonade stand and the mail route,” or whatever it is. And that wasn’t me actually.

Talia Goldberg: Carolyn found herself in a household of entrepreneurs growing up. Her family had their own business, a travel agency. And as Carolyn grew up and watched that family owned business ebb and flow with the economy, she realized she wanted to go bigger. Literally. She wanted to go the large corporation route. So right from the very beginning and coming out of undergrad at Boston College, Carolyn kept her eye on the prize in wanting to start her career at a big corporate powerhouse. She hit her mark right out of the gate in joining one of the biggest financial firms in the world, Deutsche Bank.

Carolyn Childers: Going into investment banking right out of college just felt like a really good training ground. I didn’t think I wanted to be an investment banker for the rest of my life, but being able to get into a discipline and an organization where you would just learn such good business basics was the plan. I didn’t know where I was going from there, but the entrepreneurial idea was not even in my head.

Talia Goldberg: Carolyn then continued on her career journey as she had always planned with big businesses, moving from three years in investment banking to a whole new industry, cosmetics. She started at Avon in 2004 and along with that move to a new industry came lots of learnings.

Kent Bennett: I find this really interesting. So you had gone to Deutsche Bank, you went to Avon, big old companies, the safety of that big corporation. If you had to do it again, do you still go through the Deutsche Bank of it all? Was that big company experience at all relevant?

Carolyn Childers: I think the Deutsche Bank phase, yes. There’s a level of understanding of the fundamentals of business and how companies are valued and how you think through the financial health of your business. That was a great learning ground.

Talia Goldberg: Carolyn found her stride working at large global scale businesses like Deutsche Bank and Avon. But despite all of her initial corporate successes, her next move was more strategic. She went to get an MBA.

Carolyn Childers: I did not go back to business school for the learning of it. I had done business undergrad, I had worked at investment banking, I learned things there, but the slope of learning was so much less that the second I started, I knew that big companies was not the right place for me. Being at a small startup where the decisions that you’re making just have such big impact and if you’re going to pour your heart and soul into what you do, having it at that scale of impact was just really important to me. I feel like I got a lot of the fundamentals of the learning of business already and I would’ve learned some of the fundamentals of growing and scaling businesses probably better in seat than necessarily in a classroom.

But what I got from it were amazing friends and connections. The reason I ended up going over to startups was because of those connections. I was sad that it was limited to just two years and in some ways wanted to create the ongoing version of that with Chief. But if I did it all again, I’d want to get to startups faster for sure.

Talia Goldberg: So Carolyn decides to take a risk and give startup life a shop for the very first time. She went to a small e-commerce platform named Quidsi. At the time, Quidsi was fairly unknown, but today it’s famously nestled under the Amazon umbrella and includes Soap.com, Diapers.com and other baby household and beauty products. It was then that Carolyn was bit by the startup bug and she joined as head of Soap.com to bring that product to market.

Kent Bennett: So take me back to Soap.com. Mark and Vinny, the founders there have a reputation for a particular sort of challenge that’s kind of take no prisoners, super competitive markets. I’m sure that was a pretty intense environment.

Carolyn Childers: Yeah. Mark is somebody that continues to be an inspiration for me in the way that he leads organizations no matter what industry or what competitive environment he’s in. I’ve never worked for somebody who gives so much autonomy to people. And like I said, I walked into that company with zero qualifications to be doing what I was being asked to do, and yet he gave me just complete full reign. I remember at some point we were working through our initial buys of inventory before we were about to launch and I was like, “If you want me to hit the breadth of assortment that you want me to hit in time for us to launch, I’m going to need to spend a lot of money and not necessarily the minimum buys that we have. I don’t know that we’re going to turn through that in great speed.”

And he just pulled out a piece of paper, did a very quick contract between the two of us of, “I give you,” and it was millions and millions of dollars. Sight unseen. “I trust you. Go.” And that was really empowering. I had never worked at that point as hard as I did in that moment because of the trust that I felt from him. And the thing I took most was the leadership qualities that he really demonstrated and how much that really drove everyone in the organization to truly be their best selves. I knew I wanted to start my own thing at some point.

Kent Bennett: When did you first know that?

Carolyn Childers: At Quidsi for sure. I think that there’s something about your very first foray into startups being something like Quidsi that has this amazing trajectory, great outcome of being acquired by Amazon and you’re like, “This is great.” And yes, there were hard moments, but it was a success story. I hadn’t really seen the true hard parts of startups. I had this kind of glorified idea of what running a startup looked like and knew that I wanted to go in and do it myself. But I also knew that being a senior executive at a startup and being the founder of a startup are two very different things and it needed to be an idea and a mission that I could just pour myself into for years and years. I was just trying to see what ideas I might have to go and start, and there was nothing that was really calling me.

Talia Goldberg: The time wasn’t exactly right for Carolyn to go ahead and dream up her own startup, Chief, at least not yet because she had one more big lesson to learn. And that was at Handy, an online household services marketplace for cleaning installation and general handy person services.

Carolyn Childers: I ended up running operations for them for about four years before finally starting to get the idea of Chief and realizing that that was my moment to go and actually do it myself.

Kent Bennett: So operating in that, let’s just call it an extremely tough operating environment, Handy, really hard business. What did you learn from that? Would you do that again, or do you skip that one if you go through the time machine?

Carolyn Childers: No, I actually think that was probably one of the most important ones because in many ways working at Quidsi and e-commerce, there’s some known fundamentals of what makes a good e-commerce business. How do you make it run? And you have the behemoth of Amazon to look at and say, “Okay, what elements of that do we want to take on? How do we differentiate?” But you’ve seen somebody who has done it and done it with success that there’s a little bit of a playbook there. And with Handy, that wasn’t the case. How do you create a scaled home services organization that is so individualized and personalized for every single person? You have thousands of individual contributors that are performing these services and you’re trying to do it with consistency in a business model that honestly from a P&L perspective, it’s really hard to make work. How do you make it work? How do you make it profitable?

I actually think that it was such a big business challenge and you needed to every single day push yourselves to think through how do we truly innovate to make this work? There was no gold standard out there that you could look at and say like, “Okay, this is what good looks like.” I think Handy was a great learning in business pivots.

Kent Bennett: Innovation.

Carolyn Childers: Innovation. Yeah.

Kent Bennett: So while you were there, you said you began to have the notion of the idea that became Chief, or did you step out first?

Carolyn Childers: There were two things that were happening. So one was the election of 2016 and right after, you had a lot of the Me Too movement and companies were really starting to for the first time step forward and say that they were really wanting to ensure that they had better representation in senior leadership. And I think that was just a wave of a movement that was happening. Then I think for me personally, I tend to just get very heads down in my career and focus on what I’m doing, that I was not somebody that was very good at going and building my network. I was also going on a personal journey of are there organizations that I should join to meet people and find the right group of peers to help me navigate these next phases of leadership?

Those two things were happening at the same time that I started to look at other models and other businesses that created this great professional network and support and didn’t find anything that I myself was eager to join. I decided to build it.

Kent Bennett: Nice.

Carolyn Childers: But I also think that that was by far the darkest period of all of it because everybody has skepticism.

Talia Goldberg: Coming up, as Carolyn starts to crystallize a vision for her own startup, Chief, the road ahead seems longer and longer. And as many first time founders often do, Carolyn starts to question if Chief will even be able to make it at all. More on that after the break.

Carolyn had spent over 15 years helping other companies find success. She learned the basic fundamentals of business from working inside larger corporations. She was now perfectly positioned to bring Chief to life, but she realized the founder’s journey can be lonely. It can be filled with skepticism and sometimes it can be downright defeating. So Carolyn realized that the best way to pull herself out of a very dark time was to see how other people felt about her business idea.

Carolyn Childers: I know some people go into a place as they’re starting something where they’re very secretive about it. And I was the opposite. I wanted to talk to as many people as I could about it and just continue to shape it as I had conversations of what potential members would want. So I wanted to take that time, but you end up in a place where your are waiting for people to get back to you. It was a hard period of time because I wanted to move so much faster than I was able to move.

Kent Bennett: Were you thinking this was a classic startup? I mean the handy story, this wasn’t a cookie cutter SaaS, this is a weird business model that you pursued here. I’m just curious, were you thinking this is a VC backed startup? Were you thinking this is a non-profit? What was the shape of Chief that initially sort of formed in your brain?

Carolyn Childers: There were a lot of people that as I started to talk about it would go into a place of this feels like a non-profit, not a for-profit business. But for me, we live in a capitalist society. I looked at how much companies had made statements about wanting to drive representation, how much they budget for investing in their top talent and thought there is a real business model here where companies should be supporting their female executives as they are making these statements. I don’t see why this can’t become a for-profit big scale business. There’s also 5.5 million women who are VP level and above in the US alone. So as we were focused on senior executive women, that’s a $30 billion market.

Kent Bennett: It’s massive.

Carolyn Childers: It’s huge. So I looked at it and thought I wanted to be really ambitious about the impact that we could have on the world. I thought the best way of realizing that ambition was to go and get VC dollars that really allowed us to think bigger and move faster. One of the first conversations I had around this, I met with a woman VC that I was like, “Oh, that would be somebody great to back this that would have a great story.” And she literally said to me like, “Oh, you’re so talented. Why would you go and waste your talent on this?” And I was like, “Oh god.”

I think actually I reached out to you to be introduced to a few lawyers to talk to. The one you introduced me to we ended up going with. But other intros that I had for lawyers who I would pay to represent us as we were founding the business, they’re all like, “This is not a VC backed business. I can’t in good conscience represent you.” It was a tough, tough moment where you just don’t have the feedback from real consumers yet. And it’s just you in your own mind. That’s the hard place. There’s something about blowing up the bridge behind you so that you can’t go back that is both a really good thing to do, but also somewhat unhealthy at the same time. But finding that right balance for yourself of truly how do you put yourself in a position where you have no choice but to go forward?

Talia Goldberg: It was Carolyn’s second big hurdle of her founding journey, a moment where it might have been easier to simply give up, but it was then that Carolyn found another secret recipe for her business’s success, her co-founder Lindsay Kaplan.

Kent Bennett: When in that journey did you meet Lindsay?

Carolyn Childers: I had probably been working on it for a number of months while starting to have conversations with Lindsay about being a co-founder. I grew up playing team sports my whole life. I love teams. It was a dynamic that I personally wanted and I knew when I was starting Chief that when you say a women’s professional network, unfortunately the image that comes to mind is not one of a big aspirational brand. You often go to a very corporate stodgy feeling.

So it was really important to me as we were building Chief to really invest in a brand in a way that could break through. And Lindsay was at Casper. She was one of the first employees there and a mattress company is also not exactly an aspirational brand, but she had done such good work in really helping to create that brand and was excited to partner with her to do a similar thing here at Chief. Lindsay and I are such different people in the way that we operate. She is much more of the creative brand person and I am more of the like, how do you scale this business operator? And it created just such a great-

Kent Bennett: It’s a good match.

Carolyn Childers: It’s a really good match. So for anybody who is going down the path of thinking about getting a co-founder, try to find somebody who is really different from you that has just a really complimentary skill set. And I’m not going to lie, and Lindsay would say the same, it tested us at the beginning because we work very differently and we had to find our ways of working that allowed for both of those strengths to come forward. But when it did, now it’s a great beautiful partnership that allows for both of those strengths to come forward. The number one thing that a co-founder gives you is just somebody who is in the trenches with you that you can have real authentic conversations with that’s going to go through the hard times with you.

Talia Goldberg: With Lindsay by her side, Carolyn found the energy she needed to get out of a particularly sticky time in her startup journey and she leaned on her co-founder to help position Chief as an emerging brand focused on women.

Kent Bennett: Do you have advice for other founders or regrets yourself about pursuing a business model that was so unique? That created obviously a lot of communication challenges. Or do you think there are real benefits in that?

Carolyn Childers: Yeah, I mean I think that there’s a real challenge that you have as you are fundraising and it should just be something that you recognize as going to be a challenge going into it of trying to educate people on a very new business model. I think the ability for people to say, “Well, we’re going to be the Warby Parker of X category.” Or, “We’re going to be the Uber of home services.” Or whatever it is, there’s just such a benefit that you have of creating that analogy for people for them to be able to put it in a construct. And we didn’t have that. It was really, really difficult then to educate people on that.

I think one of our biggest challenges was, you say that you are for women and automatically people think, “Oh well then that’s half the size of market.” And then you say, “We’re for senior executive women.” And they think, “Oh, well, now you’re slicing it even further.” That was the challenge that we were always faced with was is this a big enough market for venture capital dollars? No matter how many times and how many different ways I would show it is a huge market that is growing.

I would say the second component of that obviously was we were talking with a lot of male VCs and therefore as you were talking about why it’s needed, it doesn’t necessarily tap into a problem that they themselves may have a personal understanding of which then creates that type of hurdle. So it oftentimes would go back to conversations of, “I want to talk to my wife about this. Is it something that she would need or want?” Which they want to talk to potential members of something like this so I can understand that desire. But that was just an additional hurdle for us to get through of we couldn’t talk to a need that the person sitting across from us was familiar with.

Kent Bennett: Yeah. Conversely, did it have any advantages?

Carolyn Childers: I think that there are moments where there’s just huge opportunities for specific types of businesses to come into being. I do think that Chief very much benefited from us launching at a particularly good time for us to be launching something focused on women. So I think the advantage of being focused on women is that there was and is a macro environment and change that was happening that allowed for Chief to create the impact that it’s having now.

Kent Bennett: When did you know it was working? You were in those beta tests. Did you see something there that told you something actually very special was happening? Or did it take a while?

Carolyn Childers: I’d say there were two moments and it was actually pretty quick, but to this day, I’m still in the paranoid state of is it working? But like I said, we were in this really dark moment of not getting feedback and is this going to be something that people want? We officially launched with a… There was just a press piece and a pretty big publication that announced our seed funding and all we had was just a wait list for people to sign up for. There was not even a live full website that was describing what we were. When we had that press hit, we just had thousands of people sign up for that wait list within hours of the press hitting. I think that was the first time that we really felt like, “Okay, there’s something here.”

And simultaneously, we were doing a bunch of cold outbound emails to people that we knew were the right target for what we were building. And within two hours of us sending this out, a C level Fortune 100, probably Fortune 10 individual signed up and paid within two hours. So that combo right there of just like, “Okay, this isn’t just something that I feel like I need and Lindsay feels like she needs. This is actually tapping into something that people are really looking for.”

Kent Bennett: I remember you sharing with me early days some of the data on that cold email outreach you were doing, and the effective payback on your effort was like 12 seconds. It was almost so efficient that it kind of broke my brain if I think about what I wish I knew, I wish I just could’ve smacked myself at that moment. I mean, I think the light was blinking bright green like holy cow, something unbelievable is happening here. But it was almost too good to feel real.

Carolyn Childers: For me, the real question then became, “Okay, once people join and are a member, will they love it?” And that is where all of our attention continues to be. But as we had some of our first groups come in for events, for our core groups, for all of those things, we similarly were just getting phenomenal feedback on it all. We launched in February, 2019 and in June, we started to do our series A because both of those things, the acquisition side and the experience, were running so well that we thought we really should think about how we take this and start to think about next cities. Because we were just in New York City at that time.

Talia Goldberg: By the end of 2019, Chief was expanding to new cities like LA and Chicago. Leases were being signed. Things were moving. But we all know what happened at the beginning of 2020.

Kent Bennett: I just have to imagine your vision of the business at that time was at least in some part about physical spaces and COVID hits. I know you’ve spoken about all your investors reached out immediately and thought, “Holy cow.” How did you feel? Was there a moment where you thought, “Oh, okay, this is over”? We started a clubhouse business and the world can’t leave its house anymore.

Carolyn Childers: Well I think for me, even from the very beginning, I had kind of plotted through where the business was going to and needed to go. The analogy that I was using all the time was the Peloton analogy of they had a studio in New York City, they were doing classes there, and over time you don’t have to go to a studio to experience Peloton. Skip straightforward to the digital membership part of it and knew that that was an evolution that we were going to need to and want to go into as we started to think about some of the other markets. We were not going to be able to put clubhouses in every single market. I just didn’t think that we were going to do that year two.

So in many ways, I think because we had been and had already imagined out where we would go as a business, as the company, it didn’t feel like we had to completely reinvent ourselves. It just felt like we had to shift what our focus of 2020 was. I talked before about the darkest time was pre-launch and how hard that is when you’re not getting feedback. March of 2020 is still the most proud moment that I have of Chief by far. The team stepped forward so much. We didn’t miss a week. There was actually not a single week where we didn’t have services running. I mean, it was a moment of time where people needed something like Chief more than ever of trying to navigate not just what they were going through personally, but professionally and how they could support their teams.

But as we moved everything over to virtual, it also just democratized access in such a robust way that you didn’t have to add in an hour commute into a clubhouse to get the benefits anymore. So engagement just went up so much that we definitely took a little bit of a pause to just make sure everything was running and working well in this virtual environment. But we ended up, we were going to launch two cities in 2020 in a very in person way, and instead we ended up launching four cities in a completely virtual way. So it ended up having a lot of silver linings for us.

Kent Bennett: In the building of Chief, there are all these incredibly stressful, dramatic moments, but you seemed very prepared for most of them. I’m curious, the theme of this podcast is what you wish you knew, what did you not know going into chief that if you had to do it over again, that you would bring that knowledge with you and do something differently, if anything?

Carolyn Childers: I was thinking about this before we jumped on where I was like, “I don’t know that I would want to know some of the things. I don’t know if I would’ve done it if I knew everything.”

Kent Bennett: They would’ve scared you the hell out of there.

Carolyn Childers: So in some ways there’s some benefit to not knowing. I think the thing for me are always the things that I wish I knew always revolve around people and the learnings that you continue to have is you go on a leadership journey yourself of I wish I was further along in that leadership journey.

Kent Bennett: Okay. So you’ve now vaulted into the famed unicorn territory. Congratulations on that.

Carolyn Childers: Thank you.

Kent Bennett: What was your reaction to that valuation just personally?

Carolyn Childers: It felt like a celebration that wasn’t just for me personally, but for our entire community, all of our members that investing in women is a good investment.

Kent Bennett: I mean, give the future unicorn founders advice. What’s the downside of being a unicorn or that you’ve actually seen new challenges emerge just because of that new category?

Carolyn Childers: I think there’s a few things that aren’t necessarily just a unicorn status. I think it is related to any fundraise. When you have greater capital right after fundraising where you feel like the most resource rich, it can really change the way in which you are going through that prioritization and focus. So I think that is the biggest thing that I would give to anyone is just making sure that just because you have more capital doesn’t mean that you should-

Kent Bennett: Set it on fire.

Carolyn Childers: Set it on fire. And it’s somewhat related to the question you asked of what do you wish you knew? And I actually think that the failures and the hard parts, the things that you didn’t know are actually where you learn the most about your business. Where if you have too much capital that you are in some ways able to ignore the things that aren’t going well and kind of muscle through it by just putting more money into the picture, you don’t learn. You don’t what’s working or not working for your organization. That’s just the advice I would give to anybody that’s at a specific stage, whether it’s unicorn status, their first Series A, anytime that you kind of get that influx of capital. It’s to make sure that you really stay true to what’s important and stay focused.

Kent Bennett: Okay. So rapid fire time so our guests can get to know you a little more personally. I have three rapid fire questions for you, not about our time at business school. Are you ready?

Carolyn Childers: I am ready.

Kent Bennett: Okay. Where can we find you on a Sunday night as you’re getting ready for a Monday morning?

Carolyn Childers: On a Sunday night, typically I have a glass of wine in my hand trying to go through my calendar for the rest of the week while watching probably a really guilty pleasure on Bravo.

Kent Bennett: What’s the show?

Carolyn Childers: Oh, name any Bravo show. Any Real Housewives.

Kent Bennett: Okay. Doesn’t matter?

Carolyn Childers: You name it. Yep. It’s on in the background.

Kent Bennett: Got it. That’s great. What is your go to sort of pump yourself up? When you hit a wall, what do you do to reinvigorate yourself?

Carolyn Childers: I am somebody who, like I mentioned, I grew up playing sports. So for me, the ability to just be active is so important. For me, every day I go on a pretty long bike ride every morning, which is some weird form of meditation for me. I listen to podcasts. I get kind of ready for the day. But if it’s not that, it’s hiking or pickle ball or name something, but that’s the thing that keeps me sane.

Kent Bennett: Love it. Pickle ball, sweeping the nation.

Carolyn Childers: Pickle ball.

Kent Bennett: There’s a business.

Carolyn Childers: It is amazing. I love that game.

Kent Bennett: It is pretty good. Okay. Do you have a favorite quote or a personal mantra that you carry with you into your work?

Carolyn Childers: There are many different quotes that I think go through my mind. I think the one that I constantly revert back to is, “Don’t let perfection get in the way of progress.” We just have amazing members and I think we always want to do things that are just the best that they can be when we launch them for our members. But yet that slows us down and just want to make sure that we are constantly innovating and getting things that are good, maybe not perfect but better than where we are, into the world.

Kent Bennett: I buy it. Okay. Last question. On The Wish I Knew podcast, we end each episode with a parting thought for our listeners as they embark on their own personal and professional journeys. So I’ll ask you this question, which I think we’ve covered in some depth, so maybe we’re out of regrets. But looking back at your time as a professional, what do you wish you knew either before it all began or as it was unfolding?

Carolyn Childers: I think there’s a lot of people that have a tendency to get very five year planned focused, and I need to hit this milestone by this date. And for me, I think the thing that made me successful was that I just jumped to the thing that most gave me passion next and ultimately found the right place for myself. The advice that I would give for people is to not get so focused on needing that next promotion, that next thing, but to really focus on the learning and following what makes you excited.

Kent Bennett: I love it. Thank you, Carolyn.

Carolyn Childers: It was fun, Kent.

Talia Goldberg: That’s it for today’s episode of Wish I Knew. You can find and follow the show anywhere you listen to podcasts or at BVP.com/WishIKnew. Special thanks to this week’s guest, Carolyn Childers for telling her story and to Kent Bennett for moderating today’s conversation. Wish I Knew is a podcast by Bessemer Venture Partners. The show was created by our very own Karen Lee and Christine Deakers. I’m your host, Talia Goldberg. Our show is produced by the team at Filia Media. Our lead producer is Molly Getman. Our executive producer is Katie Walsh. We’re engineered by Evan Viola. Our theme music is by Terry Divine-King at Audio Network. Additional music by Blue Dot Sessions.

And remember, don’t overthink the plan. Just follow the idea that gets you most excited. We’ll see you on our next episode.

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