EPISODE

The Billion Dollar Community Propelling Women To The Top - Carolyn Childers of Chief.com

May 12, 2022·54:00·Sam & Shaan·with Carolyn Childers·Listen·AppleSpotify
0:0027:0054:00
16 moments · 112 paragraphs · synced to the second
SAM

So I have a friend who's part of it and he's an, he runs an agency and I'm pretty sure it's $60,000 a year. So quite expensive. I think it's only 2 events a year that they do. So it's almost, it's basically an events business and they sold for hundreds of millions of dollars recently to, uh, PE, just like, I think a PE company. And then another one is, uh, Aventa. Have you heard of Aventa?

I haven't heard of Aventa.

SAM

Okay. So it's E-V-A-N-T-A. Aventa was sold to Gartner for like $250 million, and it was almost like the same thing, but it was worse because it was advertising driven. The reason why we asked you to come on is because Chief is awesome and we love community-based businesses, and most community-based businesses have horrible business models. And from the outside, it appears as though you have, from the press and whatever I can just read about on the internet, it seems like you've got a really good business model. And that's what I wanted to talk to you about today was that business model, because we've talked a lot about Tiger 21 and, uh, YPO's kind of interesting, but, uh, you guys are like the next kind of person attempting this and it seems like it's working really well. And that's what I wanted to ask about.

Yeah. Awesome. Well, uh, congratulations on, on the podcast and, uh, and was excited to come on and chat because there's been a lot happening for us at the beginning of this year.

SAM

So yeah. And before this, where were you?

Casper? No, that was my co-founder. So, uh, we both have been in kind of the New York City ecosystem for a while. Um, I actually, I started the startup scene at Handy. I launched I launched and ran soap.com, uh, under Marc Lore. Quizzy got acquired by Amazon, then went over to South Korea and worked on Coupang, which is the Amazon of South Korea. And then most recently, right before Chief, I was at Handy running operations for them. Uh, and my co-founder was at Casper. So yeah.

SAM

And when did you decide, when did you go all in full-time on Chief?

I probably went full in 2018 is when I officially left other positions and dedicated myself full-time to this. And it was one of those things that I felt like I had to do the full commit and actually like put everything behind it or else it would just like keep that slow crawl of kind of an idea because Uh, without pulling, putting everything in it, it just, you know, wasn't making the same progress that it really needed to make.

SAM

I do the same thing. And I, that's what I tell people. Uh, what, what's, I think the phrase is, uh, I used to say it was burning your bridges, but it's not, it's burning the ship. So like there is this like conquistador, I forget who his name was, but it was like, uh, where he like landed in America or somewhere like that. And they're like, look, we have to succeed now because I just burned the boat. So like, we ain't going home. And, uh, I guess that's a story. I don't know if that's real or not, but I totally believe that that's the, uh, that's the, the, the way to go about this. And what Chief— what, what, what, how would you describe Chief as it is now?

Yeah. So Chief is really focused on senior executive women. Uh, it's, you know, under the phrase that we hear so often of it gets very lonely at the top. Um, but it gets lonely at the top for women a lot more. Um, and our mission is really to drive more women into positions of leadership and keep them there. And, and by focusing on that kind of senior executive woman, you know, our belief is just getting more of them in true positions of influence, the ripple effect that that could have across all different companies and organizations is, is really where we wanted to go and kind of tackle this first.

SAM

And I kind of call it like a YPO but for VPs, which is Basically like, and this is all from the outside. Obviously I'm not a member, but this is, you basically, it looks like what you get, you pay like some sum of like $5,000 to $8,000 a year-ish and you get, and the company pays for it and you get to meet up with like a core group of like 5 or 10 different women or it's the same women. Um, and then you have like a coach and then you have the ability to like chat with the entire group whenever you want online. And then I imagine you have some type of like programming throughout the month. That you can join as well, right? Is that, is that basically the model?

It's, it's very, very close. Um, so I would, uh, YPO definitely was an inspiration for us for sure. Um, where they only focus on CEOs and presidents. Um, that is their entire focus. And as a result, not surprisingly, it's largely men that are a part of YPO since that is what the makeup of a CEO and president When I think of YPO, I think like old white dudes. It's, it's not far off. Um, and it was just an inspiration for us to say, wouldn't it be great to have an organization like this focused on women? So we're VP level and above. We, we also have a lot of CEOs and presidents who are women that are a part of the organization, but we focus on VP and above. And as you mentioned, probably the heart of what we do is what we call our core groups. It is this group of 10 individuals. We go through a very curated process of finding the right group of 10 to come together. They meet every month. There's an executive coach in the room, and that's called Core for a reason. It is the heart of, of the service that we provide. But around that, we have all sorts of different services and, and, and resources that you can tap into. So we have our own programming that you can attend as much or as little as you would want to. You can tap into the whole network through our community product. We even have clubhouses in 3 cities across the US that you can, that you can use. So lots of things that are kind of around the, around the core experience, but that truly is the heart of what we do.

SAM

What was the original idea? How was it different than how it evolved into, into what it is today? What was the original premise?

I, as we did this last fundraise, it was funny, we pulled out our seed deck of, you know, what we were showing when we were raising. And it didn't change that much, which is kind of phenomenal. You always hear so many stories of, you know, we tried this, we needed to pivot because this wasn't working or that wasn't working. And the heart of what we wanted to do was always very much what it is today. I think the biggest change that we've undergone is most of our services were all happening in person when we launched. That's the reason why we had kind of these physical spaces. We had the clubhouses, we were doing core in person. Um, but with the pandemic, everything moved over to virtual, uh, which has, you know, in some ways been a small silver lining for us in that we've been able to, you know, extend to more cities faster because we don't have to do big buildouts. And it's actually even more powerful and engaging for our members because this truly is like the movie trope of the busy woman. And now instead of having to, you know, trek across a city to get to a clubhouse to get the benefit of Chief, it's now in your pocket wherever you go.

SAM

And at this point, did I see 15,000 members? Is that right?

It's close to 15,000 members, yes.

SAM

Wow. Or maybe it said 30, I forget what the pre— the, you guys, You, whatever you, whatever it's at, 13 or 12, whatever it said recently, because you raised $100 million in funding at a $1.1 billion valuation. So it's like, it's a pretty huge business and you only launched what, 3 years ago? Like launched, uh, live, uh, publicly 3 years ago.

3 years ago.

SAM

Yes. That's crazy, right?

It is. It is. I can remember back when we were launching and we're like, we're gonna have just 100 great members as we launch and we're really excited. And even from the very beginning and the launch that we had, we had thousands of people sign up for a waitlist for Chief. And now, yes, we're close to 15,000 members, but we have a waitlist of close to 60,000, which is kind of incredible. And I think it just really shows how much a community like this is truly needed, um, and the value that it's, that it's really creating for our members.

SAM

So let's say you're at 15,000. Let's just say the average price is $6,000. That's $90 million in revenue. I imagine the truth is like give or take 20% maybe. And I don't know if you say that or not, what it is, but regardless, if it's in that ballpark, it's a pretty substantial business and a, and such a, uh, That's, let's say, $60 to $100 million in recurring revenue in 3 years. That's wild, right?

It is. It is. And I think what's really, what I feel so much privilege of on any given day, when people hear about Chief because it's such a mission-oriented business, um, that's what they think of. They're like, oh, it seems like such a good business, um, but great mission. And I don't think that people realize that it's both like a great mission and a great business. And I think, you know, we live in a capitalist society and being able to have both of those things come together.

SAM

What idiot would say that? You just, you just do the math. Like it, it makes sense. Like this, like if you scale to like $50 million in recurring revenue in 3 years, that's a great company. You're probably a lot higher than that. I mean, what that, uh, do they know how to do math? Do they, can they use a calculator?

I don't know. I've, I've talked to a lot of VCs, so there still needed to be a lot of convincing.

SAM

So when I started The Hustle, um, so The Hustle was my company. We sold it to HubSpot. When I started The Hustle, it was just a, it was basically just a daily email and it was relatively easy compared to what you have started because the person receiving the email had no idea if there was a million people or one people getting it. Like it didn't impact their experience. So then we started Trends, which is like our subscription business. And that had a paid community. And that sucked because I had to make it cool before I thought it was going to be cool. So like I had to like convince my friends to like join and post in it and like make it seem like a, you know, it's like a restaurant that already has customers before you actually know, like if it's any good. When you— so I know these businesses can be tough for that reason. How were you able to get your first, let's say, 10 or even 100 people? Because it's like you're selling them something that isn't real, but it only becomes real when they're sold and bought in and like commit to it.

Yeah. I mean, I think that there, um, was a lot of small tactics that all bubbled up to, you know, uh, a meaningful investment in the brand that allowed for people to understand what we were trying to build and who we were trying to build it for. And I think we were really fortunate in having just some really amazing early members that kind of kept that ball rolling. But it was everything from, you know, one of the things that we did was have a physical space at the onset. And the physical space in some ways was like marketing for us to kind of show a brand that we were trying to develop and really bring that to life. We, that was a conscious decision and investment into the brand. Things like we didn't have a social media presence at all because we felt like, what were we gonna say? How would it be meaningful? And it actually helped to create like this really interesting tightness of people that were in the community versus trying to, you know, shout it out into all of the different social media areas. So there were a lot of things that I think we did And ultimately, like, word of mouth was by far our entire acquisition strategy, which was pretty amazing. I just like became the mouthplay.

SAM

You just emailed like your 10 or 20 closest friends and they probably told a handful of people and you just said like, hey, we're launching this in like 60 days, apply and we'll let you know if this is a good fit.

Yeah, I mean, it was not just our closest friends. We definitely sent some cold emails out to people that we had never met before. And I remember even some early VC conversations where we were showing, you know, here's our first members. And they were like, oh, so are these just all your friends and Lindsay's friends, my co-founder? And we're like, actually, no, that's not the case. It was amazing, a cold email to C-suite executives at Fortune 500 companies and people were excited to join. I think being able to also reference the YPO model, which a lot of people understood, helped to create some of that traction. And even the companies themselves. So our model is one where we, you know, sell directly to her. She then goes and gets it sponsored within her company. And we didn't know how well or how easily that sponsorship would go and companies signed up really quickly. I think for them, they look at, you know, one-on-one executive coaching can be $30,000 for a 6-month engagement. So, uh, relative to that, this was a great way for them to invest in some of their top talent.

SAM

And you got to, like, I, I was, uh, like reading, I think, so you launched, I'm looking at my notes, you launched like around December 2018, within like a month or two, you're, you passed 7 figures in recurring or like a run rate, right? But you had that cash in and then by the end of the year, you're nearing $10 million in revenue. I mean, that's pretty wild.

Yeah. Um, we started to sell at the end of 2018. We didn't officially launch services until 2019, in February of 2019. And we were just in New York City. Um, so we were continuing to add members in New York City until Around, you know, mid-2019, we went and raised our Series A largely to expand into new cities, which at the time was a more capital-intensive way of expanding because we were in person, we had to make investments into clubhouses. And so we were in the midst of those buildouts when the pandemic happened. And that's when we made the full pivot over to virtual. And as we did that, engagement actually went up. Across every, every one of our services. It was a time where something like Chief was needed more than ever. And it allowed us to expand in a much different way.

SAM

How did you know what to tell the coaches? Like what, what to tell them how to run their group or at YPO, they've got facilitators. Uh, I don't know what you call your, uh, folks, but basically like it's, I've, I've done a couple of these things and they're pretty amazing. It's basically like, And some people get insulted when I say this, but it's basically group therapy and it's awesome and it's incredibly necessary. But a good facilitator or therapist like makes or breaks it a little bit.

They do. They do. And we do a lot of vetting to make sure that we have the right coaches that are coming on that act as— we call them guides on our platform. And they're just fabulous. We have close to 400 executive coaches that act as guides for us now. And for us, I think there's, you know, a little bit of a beginning introduction into core that is very similar for all core groups. In the first few sessions, there's, you know, a very prescribed way of bringing the group together, making sure that everybody creates a deep sense of community even within that group. And then from there, a lot of it really is for the coach to decide the right path for that group. Because every group is different of what they need and what they're looking for. So we have created a lot of content, but it's to the coach and the group to really decide which direction they want to take a lot of those conversations. And, you know, a vast majority of those conversations are real-time dependent on what's happening with the people in the room of, you know, somebody is about to go through a massive recon— restructuring within their company. They're going to want to have a little bit more airtime in that session of people helping them work through some of those things. So it's, uh, it's heavily structured and guided, but with a lot of flexibility depending on what is needed for each group.

SAM

So I want to kind of nerd out a little bit on this, on these models, on this business, this community business model. I think it's awesome. And I actually think that like it's with the remote or whatever we are in now, I think it's you're going to see a lot more of these pop up. And I think you're the first of this, like, new age ones. But I want to talk about some old school ones. I want to tell you about my research and you tell me if you've heard about any of these. Have you heard of World 50?

I have.

SAM

Yes. What do you know about World 50? So you're going to know of all the ones that I know plus more. And you're the only person that is able to nerd out with me on this stuff. So that's why I like you.

Yeah. I mean, they're all— what I have, what I have generally found is that most of the communities that existed before now were all very focused on the most senior people for CEOs, like the, you know, uh, and a lot of what I'm guessing you're about to list are all that. They're all that. I think. Yeah.

SAM

No, no, no, no. One isn't. I have one that isn't.

Okay. What's the one that isn't?

SAM

On Deck. A lot of people know what On Deck is. I don't even think On Deck knows what On Deck is. I think they're still trying to figure it out, like their existence or like, you know, their identity., but they are attempting to do something. It, it seems as though they've piv— I have no inside information. This is all just looking at their website. It seems like they're, they're, they're pivoting into kind of what you're doing.

Yeah. I mean, I think, uh, I have deep respect for them as a company. Um, I think a lot of times what you often find is there's this, uh, what, what leads? Does like community lead or does like curriculum and professional development lead? And I think for them—

SAM

It's bad when it's education, I think. I think it's hard. It's hard.

It is. It is. And for us, community has always led. And even, you know, you could extend that to many other paradigms of like, does community lead or does space lead? Like, what is the actual service that you are providing? And for us, we knew that community had to be the thing that always led. And even if you think about some of the, you know, kind of analogies that you could make, like business school as an analogy, like, yes, a lot of people think you're going back for curriculum. I don't think you do. I think you go back for the network and the people. And so for us, that has always been the major thing that we knew we had to focus in on. And I think, you know, for On Deck, I'm not sure that they lead with community as much as they do kind of the programming. Um, and, uh, that I think is kind of the, the difference that I would see there.

SAM

So here's a few of businesses in the space that might like surprise the, the listener. So we talked about World 50. So as I know it, World 50, it's basically, uh, for CMOs, I think just CMOs, right?

Uh, I thought it was broader than CMOs. I thought it was actually more of like CEO, uh, individuals.

SAM

It started as CMOs, but yeah, I think it's expanded beyond that. But basically I think they were sold. So in the, the CMO or whoever it is, and there's like agency owners. So I have a friend who's part of it and he's an, he runs an agency and I'm pretty sure it's $60,000 a year. So quite expensive. I think it's only 2 events a year that they do. So it's almost, it's basically an events business and they sold for hundreds of millions of dollars recently to, uh, PE, just like, I think a PE company. And then another one is, uh, Aventa. Have you heard of Aventa?

I haven't heard of Aventa.

SAM

Okay. So it's E-V-A-N-T-A. Aventa was sold to Gartner for like $250 million. And it was almost like the same thing. But it was worse because it was advertising driven. So the attendees would like log on, like it would be like this chief information officer, which frankly, I don't even— companies that are— I've never worked at a really big company. Like in order to have a chief information officer, you're going to be a pretty huge company. So I don't even entirely know what a chief information officer is, but they would host these like webinars pretty much where like a chief information officer, a bunch of would come and like, you know, do like the group therapy thing and explain, pros and cons and like, you know, how are we supposed to work from remote and do all this? What do you know, whatever. They just complain and improve at one another and all that type of thing. And they would charge like Bank of America or some big sponsor money to be there. And they sold the company to Gartner for like $300 million. It's pretty wild.

Yeah. Yeah.

SAM

Yeah.

I mean, event businesses in general is a type of business model that I didn't really have much familiarity with until Chief, and I would never consider our ourselves an event company. Um, but, uh, it's been pretty interesting to see the opportunities that exist for, for people in that space, for sure.

SAM

So what are the— I used to own an event business and we like did like 7 figures a year on it. And it was a pain in the ass. It was so hard. It's so stressful. It just like, because like there's not many businesses where like, if it rains, you're screwed. Like if it rains 1 day out of 365 days, like you're, you're, you're poor. What opportunities do you see with events?

Well, I mean, I think that there's all sorts of different angles that people have created in that world. And, you know, I think a lot of the content businesses have even started to, you know, try to extend into that a little bit more. But, you know, like Summit Series, I think was just like a really interesting model of what they were trying to create, had a lot of community within it. But You know, again, it was more events-led than I think community-led. So it's been an area that we definitely pay attention to because it feels related, but not in our exact wheelhouse for sure.

SAM

Have you heard of Vistage? Vistage is an interesting one too, right?

Yeah. Yeah. Vistage is basically like YPO. They focus specifically again on that CEO and president profile. Um, I think they're close to like a $200 million business.

SAM

Um, I heard that they're doing $100 million in profit a year. That's what I heard from a relatively trusted source, but I don't have proof of that. Would that, would that surprise you?

Um, I think that If you look at some of those business models, so let's take Vistage or you take YPO, you know, YPO is a nonprofit and yet might be one of the most profitable nonprofits I would imagine because what we have is our biggest expenses, you know, we have these spaces, we invest heavily into our coaches, we do a lot of that stuff. Stuff. For YPO, they actually don't have paid facilitators. They train members to be the facilitators of a lot of those groups. So it's an interesting model to think about. And what a racket. I would imagine that as a part of that, they do pretty well. But I've never seen their financials, so I cannot speak with authority on either of those businesses.

SAM

Wait, YPO you've never seen?

No, no, I've never seen.

SAM

It's public, isn't it? Can't you just log in and because it's a nonprofit?

Yeah. They bucket things in ways that I think makes it pretty difficult to really discern what's underneath each thing. Um, so, uh, not fully able to break that down. So.

SAM

Right. Are you guys, uh, as Chief, um, were you able to run it mostly break even or were you losing a lot in order to get big fast?

Cause.

SAM

It seems like it worked.

I would reframe the latter statement to say we were spending to make the experience as strong as possible. I wouldn't say that we were spending to grow faster. Like I said, most of what we and how we have grown has been through word of mouth. So we haven't had to, you know, continue to just pour money into a marketing cycle. But for us, particularly over the pandemic and everything else, we wanted to make sure that we were really investing in the member experience and continuing to do that. And we're continuing to do that. And that's why we wanted to raise more capital to continue to do that. And, you know, I think about when brands are made and it's in those tough times. And for us, Being able to be there for our members through the pandemic when a lot of them at the very beginning of the pandemic, there were furloughs, there were all of those things. Like how do we invest in that experience over that period of time was really important to us.

SAM

If an employee, if one of your members quits or leaves their job, do you just have a team that will just like holler at their new employer and be like, hey, uh, you know, Ashley was a member of Chief. Her, you know, IBM no longer pays for it. And then you like, you know, somehow like get in with that company a little bit.

Yeah. I mean, I think that is actually one of the other reasons that we wanted to go in and raise this money is that right now it is an A to C to B business, right? Like we develop the relationship with her. She then goes and gets it sponsored. And what we have found is that when she asks, the sponsorship has actually been pretty easy to get.

SAM

Yeah, it's a no-brainer.

But the barrier is her asking. And so us going and actually building more of those relationships directly with the company, it seems like a no-brainer for them to proactively do more of this instead of reactively approve. And so I think that's an opportunity for us to explore to really take that burden off of her to have to go and get that sponsorship. Um, but, uh, you know, we, we definitely, you know, 20% of the workforce changes jobs in any given year. So there's definitely a lot of new relationships for us to help both the companies and the members navigate.

SAM

We are talking about Tiger 21 and it's cool. So Tiger 21 is basically, uh, you know, a community for people who have, I think, above $10 million liquid net worth. And that's cool. That's pretty sexy. You just hang around rich folks all the time. That's great. But it's actually kind of a tough sell, I would imagine, because it's the person paying for it. And when I heard about Chief, um, I was like, oh my gosh, this is like, uh, you know, when I, our company, when I sold, we were only 40 employees. And so we were probably just crossing that threshold where we could afford to send only a couple employees to like things like this. And I was thinking about like my leadership team. I'm like, man, if one of them come, came to me and asking for this, like this would just be like, the easiest of like, yeah, yeah, totally. I would probably make them sign like a deal. It says like, all right, but if you quit within a year, like you owe us like some, you have to reimburse us. But I was like, yeah, this is just an easy sell for Chief. I understand why this company is gonna get so big.

Yeah, yeah. I mean, I think we've definitely heard stories where when there has been like, that the, there's some companies who I think are like, well, you're gonna go in and you're gonna meet new people and that could actually open up new opportunities for you. That you may not otherwise have. And it's actually the exact opposite. What we have found is when a company says no on the sponsorship, it is a really clear signal to a lot of these people that, okay, you're not investing in me, you don't value me. And so that is actually the trigger of somebody thinking about going and leaving and finding other opportunities. And so they will self-sponsor and go and find something versus be sponsored, be happy in the job that they are, and continue to grow as a leader for that company.

SAM

What other, uh, you know, you're focused on your thing, but a lot of times what we do here is we talk about ideas. So things that we may or may not do, but it's interesting based off the intel that I know, what other, uh, niches or opportunities do you like this business model for?

Yeah, I mean, I think that, uh, this business model in particular is one that I think will have a really interesting next few years as people are still working from home and still in this hybrid world, but wanting that community and those connections. And so I think in those, in any area where that feeling of loneliness is, is still really present coming out of the pandemic, I think there's some really interesting opportunities. I think the hard part is the nice, the really nice aspect of Chief is that ultimately it's the company that can sponsor it. And so how do you find those areas and those demographics and those people who need that community, who will crave that community, but have somebody like the company that's willing to make that investment in those people? And that's the one-two punch that I think makes Chief really interesting. And harder to find outside of like the professional sphere. Our software is the worst. Have you heard of HubSpot? See, most CRMs are a cobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot, grow better.

SAM

Yeah, well, I was thinking about this model and I was like, it makes perfect sense for this group because I was like, you know, we have a problem with women not— there's, you know, it's not equal in terms of like the representation. So like, of course I would invest in this in order to help my folks. And in doing so, like whenever you have a group that feels like they're like disrespected or like they don't like how they're being treated, they bond together in a great way. It's like us versus the world. Like, you know, that like mobilizes them. And that type of— every great community is based on that. And I was thinking about like, well, if you just did this for like just anyone, like let's say like, uh, I think there's a company called Venwise. Have you heard of Venwise?

SAM

Yeah. And I, I think it's basically just what you're doing, but for everyone. And I'm like, well, that's— why is that succeeding? And why is Chief succeeding and not Venwise? And it was— or they are probably succeeding, but they're probably no, nowhere as big and impactful as you guys. Um, it's because that, like, this idea of like, it's us versus the world, that type of, you need that in any type of community, I think, to, in order to mobilize one another and to feel bonded.

Yeah. I, Venwise, I think focuses in on, um, senior executives, probably like C-suite executives and high-growth startups. That's like their, their focus. So, um, and. I think a lot of what they do really focuses in on that peer group model solely and doesn't have a lot of the community, the broader community around it. It doesn't have that shared mission. And I would potentially reframe what you said just a tad to say like, I don't know that it's as us versus them as much as like a galvanizing mission that brings you together that just makes you feel really bonded. And it doesn't have to be at somebody else's expense, but it is a feeling of togetherness that is created. And I think that is what, you know, the mission of CHIEF really does allow for is that broader connectedness within the community.

SAM

Yeah, that's what I didn't mean. Like I said, us versus the world, but it's definitely, it's not like we're trying to kick anyone's ass. It's like, You know, not everyone can identify with how we feel. Finally, I'm, I'm amongst my tribe and others don't exactly understand. Uh, yeah. You know, Vistage could be cool. I think Vistage is, I think I, Vistage, I think their whole like shtick is, uh, la, it's, it's kind of like blue collary. So like someone who owns like a moving or plumbing company that does like 10 or 20 million in revenue and, and that person to themselves probably says like, I feel alone. Like, you know, I don't ha, I don't hang out with people like me and I need to find like my people. And so like, it's like that finding your tribe maybe is a little bit better than us versus the world.

Yes, exactly. It is that feeling of, you know, I don't have a group of people that understand my context easily. And finding that, being able to tap into that and to be able to have the confidentiality that goes with some of that too. Because a lot of what happens in these peer groups is, you know, pretty raw, honest, authentic conversations that is, is hard to have with just anyone.

SAM

How are you as a founder able to get intel and insight into your customers and your product? Because I bet you're, you don't go to some of these groups. I mean, you, you don't go, that would, that wouldn't be great to have you, uh, you know, like the big boss and, and a bunch of these groups. So like, how are you able to learn quickly and figure out what's working and what's not?

Yeah, I mean, we do not. It's a confidential space for them to have their conversation. So we're not able to, you know, watch what is happening in each of these sessions. But I think, you know, even going back to what we were just talking about of there being a galvanizing feeling around this mission, our members are just so passionate about this mission that they are not shy. To give us feedback on anything and everything. So, it has truly been kind of an amazing experience to be able to get all of that feedback and be able to create some of this in partnership. And we have some amazing members who have stepped forward and, you know, we have one member who's like, "I'm gonna just run a sub-board services community group within Chief and bring in speakers and help each other find opportunities." So you've just seen such an uprising of both feedback, but also really big interest in stepping forward and helping to create stuff together.

SAM

So for one of our communities, we have like 15,000-ish paying members, sort of like you have, but like not even close to the amount of revenue, but a lot of people. But we, and like the hardest part in terms of like tactics for starting a community is that I found is getting people to participate online. And it's like literally like just the friction. And so a lot of the things that I've done, I've built like so many things, so many— I've built a bunch of different communities on Facebook groups because I have never seen a platform get— or a community platform get as much engagement in terms of, um, people it, people in the group, uh, the ratio of people in the group to the ratio of, uh, people in the group to people who participate in the group. But then a lot of people I've seen, like I've got a couple friends that have huge blogs and they just go, you know, let's just say like one of these blogs is Financial Samurai, financialsamurai.com, personal finance blog. It's awesome. He was like, oh, I'm just going to create a forum on my website, financialsamurai.com/forum. And even though he's got this huge audience, the forum is crickets. And it's because like literally going to that website and posting on a forum is in like, it's like a 0.01% like ratio of people in the community and readers to participating. Whereas Facebook, I've found it to be like, if you have 100 people in the group, like 10 or 20 people will actually participate, which is pretty astounding. Have you been able to crack that code with getting people to log in and go to your website? And making it all happen and participating?

Yeah, yeah, absolutely. So we started early days in a pretty similar tactic, candidly, of where are they already and how do we not create that additional friction of needing to go to our proprietary app, website, et cetera. And so we actually started early days on Slack. And it was amazing to see the amount of interaction that was happening there and how much people were stepping forward to help each other, to connect, to do all sorts of different things. The problem is that Slack is definitely not built for a community of—

SAM

No, man, Slack sucks. I hate it.

You don't even know who you're talking to unless they properly filled out their pro— It's just not the forum. And so we switched over to ours. Our own in 2020. And it has sustained. And I think for us, a lot of it is around, you know, there's these known touchpoints that are going to come up. You're going to, every month, you're going to have a core meeting that's going to pull you into the product in order for you to go and get what you need to get to go and have that conversation. And there's many of those types of things that, you know, there's there's many utilities that exist within the platform that pull you in. And then once you're in, draw you into a lot of the community aspects. So it's been really great to see. And it's everything from, you know, I, I'm looking to hire somebody to I need an employment lawyer, like there's just so much need. And for you to have a vetted network to be able to tap into do that, you can't really do that on a LinkedIn at this point, because if your LinkedIn is like mine. I think I know like, I know like 20% of the people that I'm connected to at this point. And so it's a really valuable utility and resource that we've been really excited about how much people have engaged in it. And it's not just to go on and doom scroll and, you know, look at our content. It's actual utility for them.

SAM

What I'm about to say kind of sounds like a backhanded compliment, but it's not. It's very much a compliment. But basically you guys have created this brand The reason it sounds bad is because I was going to use the word like elitist, but that's not fair. I don't mean like elitist in a bad way. Maybe elite, like just like badasses, you know, like it's, it's like Harvard or something where it's like, it's hard to get into. Uh, there's not much on the internet about it, you guys, because I don't think you have a Twitter or a Facebook or an Instagram. You only have LinkedIn. And so like, there's this thing where it's like, I don't know if you like to admit it, but it's like FOMO where it's like, oh man, like the cool people, the people who I want to be are part of this thing. I wanna be part of it, but I can't, you know, I gotta get accepted. How do you, how do you go about creating a brand like that on purpose? Is this just something that came natural to you? Like how, how do you make this where it's like, so I don't mean you just executed that strategy well.

Yeah. Yeah. I mean, we, we like to think of ourselves as vetted. We are a vetted community. We're not an exclusive community. We're not an elite community, but we are vetted because so many of the people that are members de facto fall into the mentor position or, you know, the manager. And so really, for it to be a beneficial community for her, it has to be vetted for people that are more her peers. And, you know, I think that there is a level of aspirational branding that we wanted to create with Chief because Candidly, if you think about even like 3 years ago as we were building this, if you heard the term a women's professional network, you would not think of something aspirational. It would be like warm white wine, name tags, and pantsuits. Like, that is what would be like in your mind of what a women's professional network was. And so it was really important for us to create something that felt like we were celebrating our members instead of what so often a women's professional network gets created into. And that was why, you know, we talked about that at the beginning of this. That was why we wanted to have a space that felt, that brought that brand to life, that helped to showcase what we meant by that. And the space really allowed that brand to come through. It's why we didn't want to be on a lot of those social networks. So I think my, my co-founder and I were talking about like a social media strategy. We're like, what are we going to do? Just put inspirational quotes out there like every week? Like we've seen that. Like, how do we make this feel different? And so it was very important for us to really create a brand that we thought our members deserved.

SAM

How do you think this story is going to end in terms of like You gonna— is someone gonna buy you? Do you think that like a LinkedIn would buy you? Do you think you want to go public? What do you— what's going to happen 5 or 10 years down the line, you think?

I think that we are excited to keep any and all options open. But at the end of the day, the entire value of this organization is our members. And so, and it's our members are here because they are, they need the value that we create, but they also care deeply about our mission. And so anything that we do, any partner that we, you know, want to talk to, any strategy that we go and enact has to be very much in line with that mission. And I've been very fortunate in going the VC route that we've been able to find the right partners who can come on as those VCs that understand that that leads everything and anything for us.

SAM

Would you want to be CEO of a public company?

It has never been on my bucket list of things that I like craving to do, but I want Chief to be as successful as it ever could possibly be. And I want there to be a great outcome for our members, our team, etc. And That leads more than anything.

SAM

Well, this is awesome. Um, this is, this is really intriguing. You've, you haven't done a ton of podcasts, I think, right?

No, we have, we have our own, The New Rules of Business by Chief, but, uh, I've not been, uh, on many podcasts as a, as a guest.

SAM

Do you think, uh, well, good. And I, I noticed that and that's why I wanted to talk to you. Do you think that, um, You're just so under the radar for, I think, how the, the, uh, there are so many other businesses in the, in our little circle jerk startup world. It's kind of full of stupid hype. And there's so many of them that are, we talk about so much, but they're like kind of bullshit, like not good companies and they're gonna go nowhere. But then you folks are the exact opposite where you're like, seem like you actually have a pretty substantial business. I think it's going to be actually incredibly big. Very few people are talking about you. You know what I mean? And I find that— I kind of think that's actually cool. And I want to know, how do you— how does that make you feel?

I'm right where I want to be. I think that there's actually something really amazing about being under, you know, hyped. I really like kind of making sure that we are focused on the most important thing, which is like building a great business and not like, and even for Lindsay and I, you know, as co-founders, part of the reason why we don't do a lot of publicity and other things is because we are actually trying to showcase our members more than ourselves. Like they're actually a hell of a lot more impressive than either of us are. Um, and so it feels, it feels right for what we are creating, um, to be heads down and focus on building a great business versus, you know, uh, building hype.

SAM

Yeah. Well, it's awesome. Where are you from? Where were you raised?

I, uh, grew up in Ithaca, New York area.

SAM

Okay. So you, so, and where's your co-founder from?

Also upstate New York, but like New York City, upstate New York, like an hour, not my true upstate New York.

SAM

Well, that's badass. I'm, uh, I'm, I'm happy we got to talk. I think it's amazing what you guys have accomplished. You're, you're under the radar, I think. And the reason I wanted to talk to you was I noticed not a lot of people had talked to you and it, I don't know, I feel like maybe, uh, I could like, uh, I take a little bit of pride in like We spotted this winner, not quite early on. You already raised money at a billion-dollar valuation, but like, uh, maybe, maybe, maybe a billion will be considered quite early for how the story ends though. So, uh, uh, I'm really appreciative that you guys, uh, that you decided to come on and give me a, give me a shot.

Yeah, no, I was excited to come on and, and have the conversation. And, um, like I said, I think a lot of people I remember very early days of even just trying to get a lawyer to like help us establish the company and like, yeah, I was talking about wanting to be VC funded and I literally could not get a lawyer to work with me because they were like, this should not be a VC funded business. This is a very nice, you know, lifestyle business. I was like, I can't even get a lawyer. That's stupid. I'm going to pay to do this. So it is nice to be able to you know, celebrate some of these wins and, and for people to know that we have a deep mission, but it is a great business too.

SAM

Lawyers wouldn't talk to you and you're happy that you're able to like celebrate this win?

Yeah. So yeah, I couldn't even pay lawyers to, to represent us. So it's nice to have these wins and be able to, you know, not only show that we're a really mission-oriented business, but we're a great business too.

SAM

And I think that's— first of all, I hate when people say it, when they say, oh, this is a knife light. This is a nice lifestyle business. I hate that for A, they're, they're trying to insult you and be insulting a little bit, and B, they're wrong because lifestyle businesses are like, what, what does that mean? It's a lifestyle business. Oh, like it's just a company that can make like $20 or $30 million a year in profit and I could just own it all. Yeah. Then it is a life. Like, yeah. Like a lifestyle. But what's that mean? Like, like Like, I don't, I don't know, like Mars candy, like a family-owned business that's like the largest company in the world. Yeah, sick lifestyle. So I cannot stand when they say that. I think that's really stupid. But with your, with your business, I do think I'm like, man, I would want to be greedy and own the whole thing. I wouldn't want to raise money. And so is there any— do you think, do you think you'll have regret about raising money or at least about raising as much money as you have? Because The business model is pretty freaking perfect. Like, it's like a pretty efficient, amazing model, I think.

Yeah, I mean, I think that there is a, uh, a definite strategy that businesses like ours could have of going very slowly and using proceeds from the, the business to feed back into the services that you want to create. That's definitely one way that the strategy could go. I think I, I do not think that I would have any regret with the, the way in which we are going, because I think we're impatient of trying to build a really meaningful, powerful network for badass women that, that, that need this. And, you know, at the heart of the mission is like to drive more women into positions of leadership and keep them there. It's over 200 years before we get to gender parity in senior executive positions. And if a little bit of dilution means that we can go and execute on that mission faster, I'm game.

SAM

I understand why people invested. You're very good at your pitch. You have it honed in. You seem like a force to be reckoned with. Congratulations on everything. Uh, I'm happy I got to speak with you. Thank you, uh, for coming on. Do you, do you use social? Is there any, Is there anything that you want to plug? Like your, your, your, I don't even think I saw you using social, did I?

Yeah, I'm not, I'm not as much of a social media person as my co-founder. I'm on LinkedIn, but yeah, I think the thing I would plug is, is our podcast as well, The New Rules of Business by Chief, which we just launched last year. And so people want to check that out, they can see us there.

SAM

How's it going? Podcasts are a pain in the ass to grow, aren't they?

It's fun though. I actually like, I, every single podcast episode, I'm kind of like, this is like a nice little learning experience for me too. You're just talking with like experts in their fields and learning a ton through it that I'm really enjoying it.

SAM

I think it's fun to do. So at The Hustle, when we, so we are acquired by HubSpot, so we don't have advertising anymore, but before we were advertising, but to make money. And when that was the case, it was very tough. It was very hard. And because it was like, all right, how do we get downloads up? How do we get downloads up? For you folks, like maybe because you're not making money directly from it, it's so important to get big or whatever, but it's not like, you know, you're not going to go hungry. Uh, and so yeah, if I was in your position, I would think it's awesome as well.

Yeah, that is true that we are not an advertising-led podcast business.

SAM

I appreciate it. Thank you.

Yeah, thank you. This was fun.