Carolyn Childers, co-founder of Chief — a professional network for senior executive women — joins Sam to discuss how Chief went from zero to 15,000 members and close to $90M in ARR in three years. They cover how she launched with cold emails, why the company-sponsored model works, what she’s learned from YPO, Tiger 21, and Vistage, and how Chief built an aspirational brand without social media.
Speakers: Sam Parr (host), Carolyn Childers (guest, co-founder of Chief)
Setting the Stage: Community Businesses [00:00:00]
Sam: So I have a friend who’s part of World 50, and he runs an agency. I’m pretty sure it’s $60,000 a year. It’s only two events a year, so it’s basically an events business — and they sold for hundreds of millions of dollars to a PE company recently.
Then there’s Avanta. Have you heard of Avanta?
Carolyn: I haven’t heard of Avanta.
Sam: Spelled E-V-A-N-T-A. It was sold to Gartner for around $250 million. It was almost the same thing — advertising-driven. Chief Information Officers would come together, like group therapy webinars, and large companies like Bank of America would pay to be there. Sold for around $300 million. Pretty wild.
The reason we asked you to come on is because Chief is awesome and we love community-based businesses — but most of them have horrible business models. From the outside, it appears you have a really good one. That’s what I wanted to ask you about today. We’ve talked a lot about Tiger 21 and YPO, and you guys are the next version of this — and it seems like it’s working really well.
Carolyn: Awesome. Well, congratulations on the podcast. And there’s been a lot happening for us at the beginning of this year. Excited to talk about it.
Carolyn’s Background [00:04:00]
Sam: Before Chief, where were you?
Carolyn: I’d been in the New York City ecosystem for a while. I launched and ran Soap.com under Marc Lore at Quidsi, which got acquired by Amazon. Then I went to South Korea and worked on Coupang — the Amazon of South Korea. Most recently, right before Chief, I was at Handy running operations. My co-founder was at Casper.
Sam: And when did you go all-in full-time on Chief?
Carolyn: When I officially left my other positions and dedicated myself full-time. It was one of those things where I felt like I had to make the full commitment or it would just keep crawling. Without putting everything in, it wasn’t making the progress it needed to make.
Sam: I do the same thing. There’s that phrase — burning the boats. There’s this story, I forget who it is, where he landed somewhere and burned the boats: “We have to succeed now because we ain’t going home.” That’s the way to do it.
What Chief Is [00:07:00]
Sam: So describe Chief as it is now.
Carolyn: Chief is really focused on senior executive women. Under the phrase we hear so often — “it gets lonely at the top” — it gets lonely at the top for women a lot more. Our mission is to drive more women into positions of leadership and keep them there. By focusing on senior executive women, our belief is that getting more of them in true positions of influence creates a ripple effect across companies and organizations.
I call it like a “YPO above VP” — you pay somewhere between five and eight thousand dollars a year, the company often pays for it, and you meet up with a core group of five to ten women with the same women regularly, plus a coach. You have the ability to chat with the entire network online, and there’s programming throughout the month you can join.
Sam: That’s basically the model. And I’d add: YPO focuses only on CEOs and presidents. As a result, it’s largely men, since that’s the makeup of who holds those titles.
Carolyn: YPO was definitely an inspiration. We saw the opportunity to build something like this focused on women. We focus on VP and above, and we have a lot of CEOs and presidents who are women as part of the organization. The heart of what we do is what we call core groups — a group of ten individuals who go through a curated process of being brought together. They meet every month with an executive coach. It’s called core for a reason — it is the heart of our service.
Around core we have all sorts of other resources: programming you can attend, a community product, and clubhouses in three cities you can use. But core is truly the heart.
How They Got Started [00:14:00]
Sam: What was the original idea and how did it evolve?
Carolyn: When we did our last fundraise, we pulled out our seed deck. It didn’t change that much — which is kind of phenomenal. The heart of what we wanted to do was always what it is today. The biggest change is that most of our services were happening in person when we launched — that’s why we had clubhouses, why we were doing core in person. With the pandemic, everything moved to virtual.
That’s actually been a silver lining. We’ve been able to extend to more cities faster without major build-outs. And it’s actually more powerful and engaging for our members — the busy woman no longer has to trek across a city to get the benefit of Chief. It’s now in her pocket wherever she goes.
Sam: And you’re at 15,000 members now?
Carolyn: Close to 15,000, yes. We also have a waitlist of close to 60,000. Which shows how much a community like this is truly needed.
Sam: So let’s say 15,000 members at $6,000 average — that’s $90 million in revenue. Let’s say the truth is 20% more or less. Regardless, if it’s in that ballpark, that’s a pretty substantial business — and you launched publicly three years ago.
Carolyn: It is. And I think people hear about Chief because of the mission orientation, and they think, “Oh, great mission, but great business?” They don’t realize it can be both. You know, we live in a capitalist society, and being able to have both together is what we have.
How You Get the First 100 Members [00:21:00]
Sam: When I started The Hustle, it was just a daily email. Relatively easy, because the person receiving it had no idea if a million people were getting it or just one. But when I started Trends — our subscription business with a paid community — that was hard. I had to make it cool before it actually was cool. Like a restaurant that already has customers before you know if it’s any good.
How were you able to get your first 10, even 100 people? You’re selling something that doesn’t exist yet, but it only becomes real once they buy in.
Carolyn: I think there were a lot of small tactics that all bubbled up to a meaningful investment in the brand. We were fortunate to have some amazing early members who kept the ball rolling. One thing we did was have a physical space at the onset — the space was essentially marketing for us. It was a conscious decision to bring the brand to life.
We also didn’t have a social media presence at all. My co-founder and I were like: “What are we going to do, put inspirational quotes out there every week?” We felt that would dilute what we were trying to create. Not having that social presence actually created an interesting tightness — people who were in the community felt inside, versus broadcasting to everyone.
Word of mouth was by far our entire acquisition strategy. It started as cold emails to senior executives at Fortune 500 companies — not just our friends. I remember even early VC conversations where they were like, “Are these just all your friends?” And we were like, “No, these were cold emails to C-suite executives.” People were excited to join.
The YPO model helped, too — a lot of people understood it as a reference point. And the sponsorship model: we sell directly to her, she then goes and gets it sponsored by her company. Companies signed up really quickly. One-on-one executive coaching can be $30,000 for a six-month engagement. Relative to that, this was a great way to invest in top talent.
Sam: You launched around December 2018, and within a month or two you were past seven figures in run rate. By end of the year, you were nearing $10 million. That’s wild.
Carolyn: We started selling late 2018. We didn’t officially launch services until February 2019, and we were just in New York City. We expanded into new cities after our Series A, mostly to build out physical clubhouses — until the pandemic, when we went fully virtual and engagement actually went up across all services.
Navigating Other Community Businesses [00:33:00]
Sam: Have you heard of World 50?
Carolyn: Yes.
Sam: What do you know about it?
Carolyn: Most of the communities that existed before us were very focused on the most senior people — CEOs, presidents. Which is kind of what I was going to guess about your list.
Sam: Most yes, but not one: On Deck. A lot of people know On Deck, though I don’t even think On Deck knows what On Deck is — they’re still trying to figure out their identity. They seem to be pivoting into something closer to what you’re doing.
Carolyn: I have deep respect for them as a company. I think a lot of times you find this question: does community lead, or does curriculum and professional development lead? For them, when it’s education, I think it’s hard. For us, community has always led. Even analogies like business school — a lot of people think you go back for curriculum. I don’t think you do. I think you go back for the network and the people. For On Deck, I’m not sure they lead with community as much as the programming.
Sam: Here’s a few that might surprise the listener. World 50 — for CMOs, I think, or maybe broader, they’ve expanded.
Carolyn: Yeah, I think it started as CMOs but expanded beyond that.
Sam: Then Avanta — sold to Gartner for $250 million. Advertising-driven. CIOs would host these group webinar things where they’d complain and improve with one another. Sold to Gartner for around $300 million. And then Vistage — that’s an interesting one.
Carolyn: Yeah. Vistage focuses specifically on the CEO and president profile. I think they’re close to a $200 million business. I’ve heard they’re doing $100 million in profit a year, from a relatively trusted source, though I can’t verify it.
Sam: Would that surprise you?
Carolyn: If you look at models like Vistage or YPO — YPO is a nonprofit, yet might be one of the most profitable nonprofits. They don’t have paid facilitators — they train members to be the facilitators. So it’s an interesting model in terms of cost structure.
Sam: Tiger 21 — community for people with above $10 million liquid net worth. Very sexy, hanging around rich folks all the time. But it’s actually a tough sell because the person is paying out of pocket. When I think about Chief — when I sold The Hustle we were about 40 employees. We were just crossing the threshold where we could afford to send someone to things like this. If one of my leadership team came to me and asked for Chief, I’d have said yes in a heartbeat. Easy sell.
Carolyn: And the flip side: when a company says no, it’s a really clear signal to the member. You’re not investing in me. You don’t value me. That’s actually the trigger for people thinking about leaving. So the company saying yes keeps great people. Saying no accelerates their exit.
What Other Niches Could This Model Work In? [00:45:00]
Sam: What other niches do you see opportunity in with this business model?
Carolyn: The model will have a really interesting next few years as people are still working from home and in this hybrid world but wanting community and connection. The nice aspect of Chief is that ultimately the company can sponsor it. How do you find the demographics and the people who need community, who will crave it, but have a company willing to make that investment? That one-two punch makes Chief really interesting. It’s harder to find outside the professional sphere.
Sam: I was thinking about this model and it makes sense for your group because you have that “us versus the world” dynamic. A group that feels somewhat disrespected or underrepresented bonds together. That mobilizes them.
Carolyn: I’d slightly reframe: it’s not so much “us versus them” — it’s a galvanizing mission that brings you together. It doesn’t have to be at someone else’s expense. It’s a feeling of togetherness, of finally being amongst your tribe. That’s what the Chief mission really does.
Sam: Right, yeah. “Us versus the world” was the wrong framing. It’s more like: I’m finally amongst people who understand me. Others don’t exactly understand this experience, but within the group, we do.
Carolyn: Exactly. And the confidentiality matters too. A lot of what happens in these peer groups is raw, honest, authentic conversation that’s hard to have with just anyone.
Community Engagement Tactics [00:52:00]
Sam: How do you as a founder get intel into your product? You don’t go to the core groups yourself.
Carolyn: It’s a confidential space, so we can’t watch what happens in sessions. But our members are so passionate about the mission that they’re not shy to give us feedback on anything and everything. It’s been an amazing experience building in partnership. We have one member who said, “I’m going to run a board services community group within Chief, bring in speakers, help each other find opportunities.” You’ve seen this incredible uprising of both feedback and of members wanting to help create things together.
Sam: One of the hardest parts of starting a community is getting people to participate online. I’ve found Facebook Groups have the best ratio of members-to-participants — maybe 10-20% of members actually participate. Whereas a forum on a website can be crickets even if you have a huge audience.
Carolyn: We started early days on Slack and the interaction was amazing. The problem: Slack is definitely not built for a community of our scale. You can’t even tell who you’re talking to unless they’ve filled out their profile properly.
So we switched to our own platform in 2020, and it’s sustained. The key for us: there are known touchpoints that pull you in. You’re going to have your core meeting every month — that pulls you into the product to prepare. And once you’re in, there are utilities that draw you into the community aspects. Members post “I’m looking to hire someone” or “I need an employment lawyer” — you have this vetted network to tap into in ways you can’t on LinkedIn, where honestly I know about 20% of my connections at this point.
Building an Aspirational Brand Without Social Media [00:60:00]
Sam: What I’m about to say sounds like a backhanded compliment but it’s not. You’ve created this brand that — I want to use the word “elite” in the non-pejorative sense. Like Harvard — hard to get into, not much on the internet about it. You don’t have Twitter, Facebook, or Instagram. Just LinkedIn. And there’s this FOMO: the people I want to be like are part of this thing, and I have to be accepted.
Carolyn: We like to think of ourselves as vetted, not exclusive. Because so many of our members are in the mentor position de facto — for the community to be beneficial, it has to be vetted for people who are actually her peers.
There’s also a level of aspirational branding we intentionally created. Three years ago, if you heard “women’s professional network,” you’d think: warm white wine, name tags, and pantsuits. We wanted to create something that felt like we were celebrating our members instead of that stereotype. The space helped bring that brand to life. And the lack of social media presence was intentional — what were we going to do, post inspirational quotes every week? We wanted to feel different.
What’s the Exit? [01:08:00]
Sam: How does this story end? Is someone going to buy you? LinkedIn? Go public?
Carolyn: We’re excited to keep all options open. But at the end of the day, the entire value of this organization is our members. Anything we do — any partner, any strategy — has to be very much in line with that mission. We’ve been very fortunate in going the VC route that we found the right partners who understand that leads everything for us.
Sam: Would you want to be CEO of a public company?
Carolyn: It has never been on my bucket list. I want Chief to be as successful as it could possibly be. I want a great outcome for our members, our team. That leads more than anything.
Sam: You’re very under the radar for how substantial this business is. So many companies in our little startup world are full of stupid hype — not good companies, going nowhere. And then you folks are the exact opposite: a really substantial business that almost nobody’s talking about. How does that make you feel?
Carolyn: I’m right where I want to be. There’s something really amazing about being under-hyped. My co-founder Lindsay and I — part of why we don’t do much publicity is because we’re actually trying to showcase our members more than ourselves. They’re honestly a hell of a lot more impressive than either of us. It feels right for what we’re creating to be heads-down and focused on building a great business versus building hype.
Sam: Well, I’m happy we got to talk. I think I can take a little bit of pride in: we spotted this winner. A billion dollars may turn out to be quite early for how the story ends.
Carolyn: I appreciate that. I remember very early days trying to get a lawyer to help us establish the company. I was talking about wanting to be VC-funded and literally could not get a lawyer to work with me. They were like, “This is a nice lifestyle business.” I couldn’t even pay lawyers to represent us. So it is nice to be able to celebrate these wins and show that we have a deep mission and a great business.
Sam: I cannot stand when people say “lifestyle business.” It’s trying to be an insult. And it’s wrong — because a lifestyle business could be a company that makes $20-30 million a year in profit that you own outright. Like Mars candy — a family-owned business, the largest of its kind. Pretty nice lifestyle.
Carolyn: And the podcast is fun too, by the way. The New Rules of Business by Chief — we just launched it and I’m really enjoying every episode as a learning experience.
Sam: Thanks for coming on. Really appreciate it.
Carolyn: Thank you. It was fun.