The Hidden Skill Behind Every Successful Founder | Lindsay Kaplan

So many people say cold emails do not work.

Yeah, not necessarily. It's funny. Before Chief was anything. We did it the hard way. We cold emailed as many incredible women as we could, we guessed people's email addresses, and those cold emails resulted in our first 200 members.

You raise hundreds of millions of dollars in venture capital funding, you have thousands of members everywhere. This is a people's game,right?

Yes. Human beings are craving more connection, especially for new founders. Relationship building is so important. So many people just spend all their time working on the pitch itself, but it's really about.

Lindsay Kaplan is the community mastermind building one of the most influential female executive networks on the planet. And now she's revealing the secrets of relationship building.

And why no founder succeeds without it.

It almost sounds like there's nothing between a cold email and a warm intro, and there is. Putting a lot of effort and time into building those relationships can have a real big effect. So I had been advising so many early-stage founders that having a co-founder is important, and you need people who are not incentivized to just say yes to you.

Being a co-founder is like being in a healthy relationship. There needs to be disagreement. As we are moving into a world where so much technology has replaced the feeling of talking to someone, AI has become an incredible tool for building connections.

But what AI can never do is replicate that in-person experience. It's not at all a relationship. It is a tool. The real question is how much time are people willing to invest into these real connections? And the biggest challenge is.

Lindsay, welcome to the podcast show. It's great to have you here.

Thanks so much for inviting me on.

So wow, Chief, you guys, what a big brand you've created, really, in the period of six years. You've raised hundreds of millions of dollars in venture capital funding. You have thousands of members everywhere. Wow, what a journey. But let's go back to the early days.

What is Chief, and what was that kind of founding moment when you decided to build the largest network of women-based execs in big companies?

Well, thank you so much for the question. So Chief is, at its core, a women's executive network. But what we found early on, as my co-founder and I got together, is that women's executive networks were out there, but there was none that we necessarily felt compelled to join.

There were a lot of women's networking groups that filled such an important need for women across their entire career arc. Once you got to the executive level, there were so many women that got there, that made it to the top.

But I know one thing you probably.

To become mentors and to be on the speaking circuit. And so who's mentoring the mentors? Where can we create a community of women that are at this level of leadership, where they really want to join, where they find that it's a safe, confidential space that gives them the ability to coach one another, learn from each other, and be in a place where they feel like they truly belong?

So that's what we set out to build when we launched Chief.

I love it. You know, I love these membership-based type platforms. But the hardest part always is finding those first 1,000, 2,000 members who aren't family or friends. How did you go around finding those first initial 1,000 members, and how organic was that?

Such a great question, because when we were pitching VCs, I remember somebody said to us, "Allright, so you're going to get 100, 200 of your friends, and then what?" And my co-founder and I cracked up because we were like, we were like, "Sir, we do not have 200 friends who can join Chief.

We have like three." So that wasn't really a factor for us. We did not have that strong network. We did not already have a pre-populated list of people who were going to join. We did it the hard way.

We sent out cold emails. We guessed people's email addresses,right? Like we'd stick in first initial, last name at bigcorporation.com, and we cold emailed as many incredible women as we could and were really clear about what we were building and why we wanted them to join.

And those cold emails resulted in our first 200 members that joined Chief pre-launch before Chief was anything. And it really showed an incredible product-market fit that people were willing to join before they could even see or feel a real product based off of the promise we were offering, which was this community.

So those 200 women joined sight unseen first, and from there, word of mouth. They invited a lot of their peers, and it quickly took off. And we were not on social media, so we had a very small LinkedIn presence.

And originally, we had said, "We're not going to do Instagram. We're not going to be on Facebook. We want this to truly grow like a secret society and not pump ads into the universe. We want people to find it, to talk about it, and to make this thing feel as special as we know it can be."

I love that. You know, so many people say cold emails do not work. Well, they do. I cold emailed you,right?

They sure do. Yeah.

And here we are.

It's funny. I think, you know, it almost sounds like there's nothing between a cold email and a warm intro. And there is. And that's you doing the work to try to make the cold email as lukewarm as possible.

So doing the research, stalking people on LinkedIn, and putting a lot of effort and time into the relationship building, even on your side of it. So many people just spend all their time working on the pitch itself, but it's really about the process and making sure that you can work through building those relationships to get it from cold to temperate.

Exactlyright. Where were you guys? So 200 kind of preregistered members. What was the starting point? Did you have everything kind of ironed out? This is what the membership is going to be all about? Or was it just like every founder does, just kind of hack it away and see what happens?

We had a very clear idea of what we wanted to build pre-launch. And looking back at that seed duck, not a lot has changed in what our original vision was. And so to me, it is a lesson in absolutely take feedback, hear what investors are telling you.

But if you have conviction and you have a deep belief in your product and what the market wants from your product, keep going.

And this is the great thing about membership,right? We're kind of in this loneliness epidemic where so many people want to meet each other. And for the audience listening, what's amazing about Chief is it's actually only six years old, 2019,right?

How do you decide which city to launch in? Or were you just, let's just email everyone in the US and kind of see what happens? Were you very tactical around that?

So we were. My co-founder and I, we are based in New York City, and we have a real New York City bias, that New York City is, as New Yorkers, the center of the universe. So we started here, focused all of our time, attention, energy in New York City, and had a lot of demand elsewhere.

So we followed that demand to other cities in the US, and that helped determine where we were going to launch next.

You know, it's amazing launching in so many cities, but also as you launch in new cities, this is a people's game,right? People complain, people want more things out of the membership, but keeping that brand image is so important in the early days.

As you scale to multiple cities, how did you maintain the Chief kind of like amazing membership experience versus just, you know, just trying it?

So I think it's twofold. The first is member feedback. User feedback is so important. And so I do look at the experience as something that always needs to adapt and evolve as we hear member experience, but it has to adapt and evolve as a complete, fully formed brand and experience.

So you can't just adapt it in one market because one market wants, you know, more of this, less of that. For us, it was really important to maintain a very, very strong foundational brand. And so using that input, using that feedback, but making sure that it's affecting a whole and it's not getting disparate and disjointed, because a little bit of disjointedness can have a real big effect as you're trying to operate a growing business.

So you guys are scaling fast, even in the first few years, but I imagine there are so many challenges happening. Take us back to 2019, 2020. We're here in New Yorkright now. What are some of those hardest challenges which are happening?

Well, I think COVID was everybody's hardest challenge in 2020. We had launched early 2019. We were picking up speed. We were a fully in-person experience. And so 2020, we were signing leases in other cities, very big leases on in-person locations.

And obviously, we had to pivot to go fully digital. So that was the biggest challenge. And we not only rose to the occasion, and I don't want to take that credit, that is purely the work of a growing startup team that all were working their butts off to make sure we could bring every single facet of membership from in-person to digital in every single different way, whether that's launching a chat application, putting everything on Zoom, moving the entire member directory, everything had to get moved, launching an entire content arm.

All of that movement was due to an incredibly hardworking, dedicated team. So I want to give the team credit for making those moves. But obviously, although it was such a huge challenge, it changed the trajectory of the business because we were now moving from, you know, in-person to online.

We had the ability to move faster and to connect more people, and the demand grew. So we, as you mentioned, people felt like they needed more community. They needed more connection. People were home, going out of their minds, more stressed than ever with their jobs.

And we're talking about executive women who not only are trying to do their jobs really well, but caring for their own teams, doing caregiving in their own homes. And so this cohort of users needed more connection than ever.

And so we were able to rise to the occasion, and that really helped

take the business that we were growing, I think, at a pretty fast clip and accelerate it beyond what we had anticipated as we went in from, obviously, 2019 and beyond.

What's also crazy, like this whole COVID, you know, event which happened, it feels yesterday, but it was five years ago already, which is crazy,right? But it kind of felt like in that moment, that's when community life really comes together and it really matters,right?

But we didn't see any of this coming. You look at all these event online conferencing platforms, which very quickly emerged. The hospitality sector died basically overnight, already struggled. How quickly did you have to adapt? Because this is the kind of business model where you probably have to adapt within weeks.

Oh, it was days. I mean, I distinctly remember. So I was actually on maternity leave. I had my second child in January, and I was set to come back to the office, wanted to take some time off, was set to come back March 13th, and I never came back.

And I distinctly remember my co-founder and I writing that email about, you know, the pandemic. We assumed we would be all of us working remote, testing Zoom for a week or two, had no idea that this would just absolutely, you know, rip apart the modern workplace.

So we made those changes and launched those new digital products within days and in some cases, hours.

Crazy. So much of this journey is shared with a great team, but also a great co-founder,right? I kind of feel like being a founder, you have great days, you have good days, you have okay days, bad days, and shit days,right?

And all of that comes from having a really good co-founder. You and your co-founder, Caroline, you go back quite a few years,right? How did you both meet? And what is the art of having a great co-founder relationship?

So Caroline and I actually met at a shitty women's networking event, which is ironic given what we started. It was one of those events where you were kind of trapped at a table and there was a speaker and a few people dominated the conversation.

And she and I met at coat check and just kind of introduced ourselves, said hi, picked up our coats. And the New York startup scene is huge, but when you become an executive woman in the New York startup scene, there's not that many.

And there certainly wasn't at this point. I think when we met, it was like 2016, 2017. So Caroline actually had the idea, the business concept around Chief. And as she was thinking about co-founders, somebody mentioned my name, and she was like, "Ah, I know Lindsay.

I remember her." So as she was thinking about, Caroline's an incredible operator. I mean, she is just the real deal, phenomenal CEO. She was thinking about bringing on somebody as a co-founder that could really support more of the brand storytelling, creative aspect of what we were building.

And so when somebody mentioned my name, she shot me an email. And I remember getting coffee with her and just being so drawn to what she was building. And to answer your question more specifically about the dynamic, Caroline and I quickly realized two things.

One was that we had very similar values. We both come from middle-class homes in upstate New York, both came to New York with grit. I wouldn't say a chip on our shoulder, but the grit and the drive to define success on our own terms.

And that's a very similar set of values that motivated us. And yet our skill sets were wildly different. So Caroline, as I mentioned, an insane operator. She went to Harvard Business School. She can financially model her way into anything.

She's just such a genius. And I was an English major that has a half-written novel. So, you know, don't show me a financial model, show me a story, allow me to build a brand. And so we took those two very different skill sets.

And again, that foundation of our values created a really important

partnership, but also friendship. And I was literally just at Caroline's this morning. So she moved four blocks away from me. We see each other, I would say, once a week for coffee. We're both still on the board of Chief and care deeply about the business that we've built and co-founded together.

And again, my advice as you're thinking about bringing on a co-founder is find somebody that has a different set of skills, but somebody that you share a deep set of values with.

It's almost the founders who go and build a company. They're careful of who they build this with, but they almost feel they don't do enough stress testing. Can they really have disagreements with each other, or are they just going to agree on everything?

So if you can't disagree, then it's going to be hard to build a big company now.

Yeah. I mean, lucky for us, I have no problem disagreeing. So that worked out well. Being a co-founder is like being in a healthy relationship. There needs to be disagreement. You cannot have one person constantly agreeing with the other.

You need there to be that healthy dynamic of pushing and pulling. And, you know, when you are the CEO, people are incentivized to say yes to you. And as co-founder, I was not incentivized to say yes to the CEO.

I was incentivized to work with her to build the most powerful business we could. And so, again, I think having a co-founder is important. Unless you've done it a few times, especially for new founders, go find somebody to build this with.

It is a lonely, lonely process, and you need people who are not incentivized to just say yes to you.

Totally, totally agree. And, you know, when you see so many great founders out there who are solo founders, I'm always amazed just how they've done it because it's really hard. You get punched in the face multiple times a day, and would you much rather do that by yourself or do it alone?

Super important.

Yeah. Not necessarily always getting punched together, but like someone's nose bleeding, you know, you have somebody else to help clean it up, to use your analogy. Great to have a co-founder.

Exactly. Okay. So fast forward a few years. You guys, three years later, you raise $100 million, become a unicorn in such a short period of time. This is quite unusual, especially for membership-based platforms, because normally it's very consumer-led, but it's also very enterprise-led,right?

What do you think were some of those early characteristics that led you to believe that you found product-market fit and there was really something here to grow and scale?

Well, again, I think that initial traction we saw, we wanted to double down on. So we knew that growing this membership with extremely

high-caliber executive women was a real unlock. It was important for us to make sure that we kept this, it's called Chief for a reason, but we kept this executive cohort. And although there was always a waitlist of people who were in earlier stages in their career, we wanted to make sure we were really protecting that customer because they were joining to be amongst their peers.

They weren't joining to mentor. They weren't joining to be a part of something that was for all women. There are amazing, amazing groups out there across the spectrum in every country that cater to all women in business. We wanted to make sure we were differentiated, and we saw the numbers that showed that there was a market to build this and do it successfully.

You also launched Physical Spaces, which I found super interesting, especially like as COVID was beginning,right? What was the decision to launch Physical Spaces on top of the membership platform?

Yeah. So again, early on, it was an in-person experience. And so we signed a lot of those leases pre-COVID. Great time to sign giant real estate leases, you know, November 2019. But what it allowed us to do as COVID, you know, COVID didn't end, and COVID is still around.

And there was no beginning and end of the pandemic. You know, there was a bit of a like things are back, then they're not back. People are into work. It was a real slow,

slow build back into in-person. And so we had those spaces that we had signed leases on, and it allowed us to build this hybrid experience that our members really wanted and that people today still really want. People want the flexibility of working from home.

They love Zoom. I mean, Ollie, you and I are on different sides of the globe. It's amazing we can have this conversation and do it so effectively. And yet nothing can really replicate that in-person experience you get when you are around people who get you.

It's not something we can replicate with Zoom. And so we were really fortunate that we had built out this hybrid experience and were able to double down on it as COVID started to slow down.

There's something so special about these community-centered businesses. There's another good company called TimeLeft. Have you heard of them?

I have not.

So TimeLeft, they basically put strangers together. 150,000 strangers every month go to these events.

Wow.

And I went to two of these in Bangkok, and the connection you just make with people in person is so much different,right? Doesn't matter if you're here in Bangkok, New York, where you are, wherever you are in the world, there's so much, there's just something so special about meeting people in person,right?

We couldn't do it for four years, but now we can. And these membership-based platforms, you know, take AI. AI aside, I actually think the ones which are going to do really well are consumer enterprise community type of businesses which are solving loneliness and helping us grow.

Well, I think, you know, AI has become an incredible tool for speed, for building connections. What AI can never do is replicate that in-person experience. You can't. And so there is actually more of a need as we come, you know, into this world where there's more ability for you to fake a conversation with a robot than ever.

Lord knows I've had too many conversations daily with ChatGPT just to get its opinion, to fact-check things. It's not a relationship. It's not at all a relationship. It is a tool. It is a tool that for many people can mask the feeling of talking to someone, but it is not a relationship.

It is not a real connection. And so I so believe people will not only need that, but there will be a deeper appreciation, a deeper value put on these in-person connections experiences. I think, you know, as we are moving into a world where so much technology has replaced that, I think the real question is how much time are people willing to invest into these real connections?

And we've seen this with Chief. We've seen that although people deeply value the in-person, a lot of their time needs to be spent online because there's so much productivity is up, because so many demands are on people to be working harder and longer than ever.

So the real question for me is time and how we can weigh the amount of time that people can devote to building these real in-person connections.

That's super interesting. What I also find amazing is you had 60,000 people on your waiting list at the peak. It may have even been more,right?

I believe that number sounds, yes, it fluctuated a lot. There were definitely tens of thousands of people on the waitlist. And again, it showed that there was such a demand for this. And a lot of that waitlist was executive women, but so many were other women in business who wanted to become a chief, who so aspired to be a part of the community, not only for what the product and the experience delivered, but for what the brand and the mission stood for.

And, you know, it was amazing to grow something that women aspired to be, that they wanted to grow up and become a chief and to join Chief was, you know, real recognition that it wasn't just building an experience, but it was truly a movement.

I love that. And also, you know, as these types of businesses evolve, so does the member experience. How has the member experience changed from when you launched in 2019 to where we are today in '25?

Yeah. So I know that Chief just launched new tracks. So Chief wanted to make sure that as obviously as the workplace is changing, women's careers are also. And so new tracks have been launched to make sure that women who are solopreneurs, who are multi-hyphenates, who are, you know, in different stages of their executive level careers can also partake in Chief and make sure that they're getting a more personalized experience depending on where they are in their career today.

Exactly. I think that's really cool. I mean, also, like, if you think of the Chief brand, there are so many cool things you could do,right? Imagine if there was a Chief like emerging managers, maybe there's something out there.

There are just so many, like, different avenues you could go down,right?

Yes. There is just a, there is just so much that women want to accomplish, and there are so many experiences we know we can deliver them to make sure that their needs are met.

When a founder has been running a company for a long time, they, at some point, they realize they may be no longer the best person to run the company for the next five, ten years and so on. And you decided to actually step down from Chief not so long ago.

What was that realization you decided you wanted to make this move and move on to bigger and, you know, more exciting opportunities?

Well, I think it was a combination of factors that I assume a lot of founders feel familiar with. The first is just feeling absolutely exhausted running, playing the same sport, if that makes sense. I don't play sports, but I'm going to make a sports analogy, if that's okay.

I felt like I had been on the field and, like, my knees were bloodied and I had a pain in my back, and I still wanted to move at 100% and win the game. And it's hard to do that when you've been playing for seven years and you've been, you know, just trying to give it your all.

So a part of that is exhaustion, and a part of that is looking over the sidelines and seeing amazing players who have 100% peak energy and knowing that in your heart of hearts, the best person to continue to play and win the game is somebody that isn't bleeding, that is fresh and worked out and ready to come and give it their all.

So thank you for allowing me to use my sports analogy here, but it's not that I didn't want to. It's that I felt like the best move for the company was to bring on somebody who had all of that energy.

And it's natural. I think whether you're a founder or whether you've been an executive or working anywhere for a really long time, you, I wouldn't say you get into a rut, but you don't have that energy. You don't have those fresh ideas that you did early on.

So I thought the best thing for the company was to make sure that somebody who was at the helm, who was captaining the team, if you will, could come in fresh and excited with, you know, the ability to attack this from day one for them.

So part of that was energy levels. Part of it was thinking about who can give the company 100%. And then I think the third factor was also knowing that in my heart of hearts, I love building, I love early stage.

And so as the company moves from, you know, two co-founders to 10 people to 100, to hundreds of people, that's less of a place that I am able to be at my highest potential. And so, you know, a company as a startup turns from something small into something that does over time need to, necessitates being more corporate.

It's just not where I shine. And so all of those factors led me to say, what's best for this company is me continuing to stay on the board, continuing to always be a part of Chief, but to step away from operating day to day.

You know, we mentioned this earlier, and being a founder, it's just so hard,right? You know, we use the sports analogy, getting punched in the face, like, so much,right? Not a lot of founders.

Very good island analogies.

But in a good way,right? I think it's also important to emphasize that so many founders go on this journey of building a company, and I don't think enough founders take enough time to take a step back and actually decide, do they want to do this for the next few years or not, or should they stop and move on to other things?

Yeah. As I advise early, early stage founders, one of the questions I do ask as they hit challenges is, are you sure this is the passionate place that you want to be in for the next five, ten years?

Because it is a huge commitment to become a founder, to give it your all. And if you are not passionate and the work doesn't light you up, it's not giving you intellectual satisfaction to be there every day and solve those problems.

That's not the founder that I want to back as an investor. And I don't think it's the company that that founder should be a part of.

What I love about seeing founders is when they have a diverse cap table. They're made up of operators, founders, and also your traditional investors. So you've been an operator, you've gone from founder, now you've turned a VC at Next Wave NYC,right?

What made you decide to become an investor? And what's getting you excited? Because it is messy out thereright now.

It is messy. I love founders. I love early stage. I love building. I love seeing the potential and the possibility of what somebody could take from an idea into transformation. And so I had been advising so many early stage founders and really wanting to back some of the best and brightest companies that I've come across.

So it was really fortuitous that I could join Next Wave NYC, which is all of us. We are all operators. We're all based in New York. And our charter is to write hopefully first check-in, super early stage, $50,000 checks into these startups.

Our thesis is around AI. And then I also angel invest more consumer side just because my background is more consumer.

What's exciting youright now in this tech ecosystem? We have AI going on. We have consumer going on. What trends are really exciting for youright now?

Yeah. So counterintuitively, I am both excited by AI and I am excited about the IRL experience similar to Chief. There is a real dichotomy of what's happeningright now with human beings. We want things faster, more efficient. AI is the best tool in history to help us 10X the work, to be able to build out processes and technologies faster than ever.

At the same time, as I mentioned before, human beings are craving more connection in response to that efficiency. And so I personally find investing on both sides really fascinating because I think there is so much potential for growth on the side of AI.

And I also think there is so much possibility and so much need and desire for deep consumer brands that understand the emotional aspect of human beings.

You know, I was thinking this earlier and we were chatting about this company, TimeLeft Chief. People want to meet people in person. People are lonely. People, like, there's so much opportunity,right? There's this another company called Hyrox. You may have heard of it.

This kind of, you know, sporting, competing competition. They started seven years ago. I think they're in 80, they do 80 events a year, $140 million in revenue now. They do. It's crazy. And you can do so many cool things around this,right?

I was speaking to a friend last night. She wants to create the TimeLeft experience, but only for girls, 24 to 34 year olds. Like, really cool concept. You could do Chief for, like, emerging managers. People want to meet people, but it's hard,right?

Because there's people at the end of the day.

They do. And again, I think it's balancing. One of the biggest challenges we had at Chief was balancing the desire to meet people and have those connections with the time restraints people have, just knowing that they're working longer and harder than ever and everything that's keeping them home,right?

Like the exhaustion from work, the commutes, the commuting time to actually, like, get somewhere, the pressure to feel like you look good, which is steeper than ever given the rise of plastic surgery, the whole other topic, and just the draws of staying in bed and rotting and being on TikTok.

All of those elements are fighting against that human urge to go out and have in-real-life connections, which is why I'm really bullish on one side and the other.

So you've been the operator, you've been the founder, now you've been an investor. Which side do you prefer the most?

Ah. I'm a multi-hyphenate. I like doing all of it.

I can tell. I can tell.

I am somebody that, you know, I studied creative writing at university. I'm a storyteller, and

I get bored pretty easily. It's why I loved working on Chief. It's one company, but we had so many different products and elements, and there was always a new challenge. It was a very complicated business to run, which I loved.

It just hit every part of me that needed different intellectual stimulation. So I don't want to box myself in. I've really enjoyed exploring VC. I love meeting founders. Can't help. Some, you know, I think one of the reasons founders like having me on their cap table is because you kind of get a de facto advisor.

There are plenty of VCs out there who can give, you know, good advice. There are VCs who just come in with the money, write a check, and don't really need that weekly accountability. I love being able to advise as much as founders want to lean on me because I have all of that experience and all of the learnings that come with being a founder, with being an employee at early stage startups and building something that I think was unexpected that could be so big.

I love that. You know, it's so important for founders to have that diversity on their cap table,right? Especially the former operators turned founders. And there are so many cool VCs who do this, like Next Wave NYC. So if you were to go and build, again, a company tomorrow, what category would you go?

And do you have some ideas you're noodling on now?

I have so many ideas.

When's Lindsay going to launch her next company?

I am constantly noodling. I think for now,

so I left operating about nine, ten months ago, and I still think I need more time before I would go back and start something new. I have really loved meeting all of these founders. Those conversations spark a lot of ideas for me.

So I am noodling, but it is too soon to reveal the noodles.

Time will tell. We're really excited. Hopefully, you're going to do something next. Lindsay, this has been amazing. Thank you so much for your time. What an amazing story. We can't wait to see where Chief goes next. Next Wave NYC for founders, you know, her fundraising.

We're also collaborating at some stage. We're also investing a little bit. So let's definitely do that at some stage.

Very exciting.

And we can't wait to see where you guys go next.

Thank you so much for having me on. What a great conversation.

Thank you.