Breaking Up the Boys' Club: Stephanie Cartin on Building the Entreprenista Movement

It is so exciting, everything that is happening with AI, because it is leveling the playing field for so many small business owners to be able to have more resources to be able to grow their business faster, and actually not have to raise capital. Because now you could use a tool that might be 20 to $50 a month, instead of having to raise capital to go hire three team members.

So it really is leveling the playing field, especially when it comes to operations in a business. But I'll share, Leah, where I feel like I truly believe AI cannot replace this, this conversation that we're having right now. Real human connection. So it's like, let these AI tools help you optimize in your business so you have more time to do this, to have these conversations, and to go meet in person and build real relationships.

Hi, everyone. I'm Leah Solivan, and this is Breaking Precedent. Not only did I found TaskRabbit, one of the pioneers of the gig economy, I'm now a venture capitalist backing the next generation of rebels through Precedent VC. In this podcast, we dive deep into the stories of innovators who are pushing societal boundaries, challenging precedents, and setting new ones in their fields.

My guest today wanted to be on the Broadway stage. Instead, she talked her way into hospitality, learned how to sell, and spotted something most people in 2010 still dismissed as a fad: social media. She turned that hunch into Socialfly, one of New York's leading agencies, bootstrapped without ever raising a dollar, sold it, and then built the company she wished had existed for women founders.

She is the co-founder and CEO of EntrepreNista. Let's dive in. Stephanie, thank you so much for joining me here on Breaking Precedent.

Leah, thank you for having me. So excited to chat about all the things.

I know. So many things we have to chat about. You are a precedent breaker, for sure. I wanna start with a little icebreaker for you.

So I read that you walked away from your corporate job, you went all in on Socialfly, which we'll talk about, in a single day, May the 4th, 2012. So tell me, what is the most reckless looking thing you've ever done that turned out to be the smartest thing? Was that it, or was there something else?

I would say that was probably it, but maybe I wouldn't even call it reckless because we did have a plan, and we just had just absolute belief, Courtney and I, in each other that we were going to build something amazing, and I knew we were not gonna let anything stop us.

Now, if you talk to Courtney and have a separate episode with her, she'll tell you she had her backup plans in place, and had planned everything out, and had the what-ifs in place. But I was like, "We're going all in. We're gonna make this happen, and I'm not gonna be employable by anyone else anymore. We're gonna build this business."

Isn't that funny when you realize you're no longer employable by anyone else?

I

know. It's like, it's kinda like, "All right. Let's go. We're doing this," right?

Absolutely.

Yeah. Well, I wanna rewind and start at the beginning because you didn't actually set out to build a tech company. I was enthralled by your passion for musical theater and the stage, and seems like that's something that was a big part of your younger self, something that you studied.

Can you share a little bit about that?

Absolutely. So I grew up in Maryland, and I actually had an older sister who was doing musical theater from an early age, and I watched her going to classes and starting to perform, and I was like, "I wanna do that," and started tagging along and going to classes. And I just loved singing, and dancing, and being on stage, and I think what I loved most about it was really just the reaction you would get from the audience.

And you would perform- Mm ... and it would make everyone so happy. And I loved being able to provide happiness to other people, and I think that is really what motivated me. So I, essentially, was a child actress in Washington, DC, Maryland area performing- That's amazing ... in all of the dinner theaters and summer dinner theaters.

And I was doing professional theater at seven, eight, nine years old- Wow. Wow ... and I would miss school to go do the Wednesday matinees in Annie- Awesome ... in Annie Warbucks, and Sound of Music, and all of the shows, and I just absolutely loved it. And then I saw my sister actually wanted to go to school for musical theater, but she wasn't allowed to, and I realized, okay, I'm probably not gonna be able to- Mm

do this professionally. Mm-hmm. So how can I take- My love of performance and build businesses.

It's an amazing story. So at the time, you were kind of ... Yeah, I guess you were, like, self-aware enough to realize, like, "This maybe isn't something that I will pursue professionally, but how can I take this passion and fold it into what I'm doing?"

A family friend told you about the Cornell Hotel school, and is hospitality something where you feel like you're able to, like, fold in that performance, that stage, making people happy? How did those two things tie together?

Yeah. So we actually went on a family vacation when I was 11 years old, and on this vacation, it rains the entire time we are away, so we had nothing to do really, 'cause it was a beach vacation.

And we saw this sign for Disney Vacation Club. And as a child, I see the Disney logo, and I'm like, "Let's go there. Disney's here." We were in Hilton Head. And we go in for this presentation to learn about Disney Vacation Club, which is a vacation ownership program, and I'm 11 years old, and I'm sitting there, and this man, John, is sharing with my family all about the Disney Vacation Club program.

And I'm watching what he's doing, and I'm watching him explain this program. I'm like, "Okay, we need this. We go on vacation. We spend money." Clearly. "We need to own this." Yes. So my family purchased this. I started growing up, getting to travel- Ah ... to go to nice places that- Mm-hmm ... we would not have been able to go to if we didn't have this.

Mm-hmm. And I just loved going to nice places- Mm ... hotels, Disney. And when you go to a hotel, and especially when you go to Disney, everything is a performance. Mm-hmm. And everything is planned, and you're creating memories and happiness for people. So now, when it was time for me to apply to go to college, I remembered John, who sold my family that vacation ownership package.

Okay. And I called him, and I said, "I wanna do what you do. Where should I go to school?" You

called John

from vac- Called John from 11 years old- Oh my God, that's crazy ... to 18 years old, found him, and our family had stayed in touch. And I said, "I wanna do what you do. Where should I go to school?" Okay. Yep. "I want to help make people happy through hospitality."

And I applied. Wow. I got in, and that is how it all happened.

What a very cool story. And John, wow, was he still working vacation ... at the Disney Vacation Club?

He was working for Marriott at the time, and that's- Yes ... why everything- Mm ... goes back to relationships, right? This relationship- Mm-hmm ... as an 11-year-old that- Yeah

we maintained for years, and then meeting with him again when I'm 18 years old. And then I got into Cornell, and then I needed an internship, and I called John. I'm like, "Can I come intern for you?" And he said yes.

Wow.

And then did an internship- That's incredible ... with Marriott, and then went to work for Marriott full time.

Wow. And it's all about building relationships.

Yeah, it really, really is. That's incredible. So you're in hospitality, you were then at Spa Finder, then you get pulled towards social media. Tell us about that moment where you start to learn about something at the time that was just emerging. Like, most people thought it was a toy, not an actual industry that was being created.

Absolutely. So I was one of the first users of Facebook when it first came out, and this is actually going back to when I was in college. So- Mm-hmm ... I was a sophomore at Cornell, and it was thefacebook.com back then, if you remember that, and the way- I

remember ...

we felt we were so cool. We got access to this platform, and back then, the way we used it at first was we would take pictures, but we would go out at night in college, and then we would physically have to connect the camera to the computer to upload the photos to put them on thefacebook.com.

But I remember thinking, Leah, I was like, "This is going to change everything I'm learning about- Yeah ... in college." I'm a hospitality major- Mm ... with a concentration in sales and marketing, and we're learning the principles of marketing and sales and marketing strategies. I'm like, "This platform is gonna change everything that I'm learning about," but I didn't know exactly quite how back then.

Mm-hmm. It really wasn't until I graduated from Cornell and I started working in the hospitality industry when Facebook and now Twitter had come out back then and started gaining more traction, and I'm like, "Okay, there's really something here. I'm working for this hospitality company. They're opening a spa.

How are they gonna get people to come into this spa? They need to be on Twitter." Yeah. "They need to be on Facebook." And I just started having conversations with people and putting together these- Hmm ... social media strategies really on the side of my full-time job until I realized very quickly this is not an after-work activity.

This could be an actual business.

That's pretty interesting, because it kinda starts out as this fun thing, but then you realize, oh, no, wait, there's an actual business here

If a decade of building TaskRabbit taught me anything, it's this: the everyday stuff never actually stops. There's always a bookshelf to hang, a bed to assemble, a garage you keep meaning to clear out, a run of errands you keep punting to some perfect Saturday that never quite arrives. And we all do the same thing.

We swear we'll get to it, and instead, it just sits there, humming in the back of your mind. You didn't picture your one day off on your hands and knees decoding flat pack instructions, but somehow that's where you ended up, pulled away from the people and projects you actually care about. That's the whole reason I built TaskRabbit.

It connects you with skilled, reliable taskers right in your neighborhood who show up and get it done, often the same day. Furniture assembly, mounting, hauling, home repairs, yard work, all the little jobs that quietly swallow your week. You book in minutes, you pick your tasker, and the whole list lifts off your shoulders so you can keep your home or your business running without adding another thing to your plate.

It's what I send people to the second their to-do list starts calling the shots. I've watched it give people their Saturdays back and a little peace of mind along with them. So stop white-knuckling the chores, hand them off, and go spend that time on what only you can do. Breaking Precedent listeners get $15 off your first task with code Breaking Precedent.

Visit taskrabbit.com or download the mobile app to get started.

.  What do you think

that you saw, and what gave you that insight that, before no one else saw it, no one else did? I mean, you were kind of early to the game here.

I feel like I have this, or I know I have this hidden talent of seeing the future

Do you have a crystal ball?

I, I do. I wish it saw everything. It see- it usually sees the future when it comes to trends and business. Oh, wow. Okay. I just have a foresight to know- Mm ... based on what I'm seeing happening. Mm-hmm.

And then I just have this inkling of what I think is gonna happen, and it's pretty much always happened. So that's been my tell of, like, always listening to myself and my gut and my intuition- Mm ... and just going with it. Now, sometimes I will tell you, and Courtney has this too, like, sometimes we're too early.

We're like, "Okay- Okay ... we know this is coming," and we're able to get there faster because as startup founders, we can move really fast, but the rest of the world hasn't caught up to everything yet. So it'll be like four years later and we're like, "Oh, see now everyone's caught up and is there." Like, we started our podcast in 2018.

Yeah. We knew what was going to happen- Yeah ... and how big podcasts were going to become, and we would really just take action and move.

Yeah, it's pretty amazing. So Stephanie, talk to me about the thread between the stage, the theater, you go into hospitality, and then into business, and you're interested in this new social media thing.

Can you talk to me about how that thread kind of all ties together and kind of spearheaded you forward?

I feel like so much of the success that we've had building our businesses has really come back to, one, the relationships that we've built over the years, but two, the training I had in musical theater growing up really provided me with that foundation for everything in business.

So no matter what you're building, if you're building a business, if you're going to medical school to be a lawyer, you have to be able to present, you have to be able to share, you have to be able to get up in front of people, and really- Mm-hmm ... you have to believe in yourself. Yep. And so much of that you learn from theater, from performing.

So I always share with other moms and dads now, I'm like, "If you can, put your child in musical theater classes just so they can really get that and build that strength when they're young."

Yeah. No, I love that. I'm really into the ballet, specifically ballet. I mean, I love musical theater too, but I grew up as a ballerina, and then I just wrote this article about everything ballet taught me about raising money.

Hmm. Like, for my company, for my fund, because it is that similar approach of you have to be disciplined, you have to be focused, you have to perform under pressure, all these things. So that totally resonates.

And practice, and doing things over and over and over again. Yes. And it's like when you're doing a show, like when I was in Annie, we would do the run for three months, and you're doing the same script and the same thing over and over again, and you have to make people feel like it's the first time you've done the performance.

Yeah. And it's the same thing- Right ... if you're pitching investors, and you have to be excited- Yeah ... every time you're talking about your idea- Right ... or to your team- Yeah ... or you're building something, so- Yeah ... it's all that same muscle.

It's so true. So you've got this kind of social media thing you're exploring on the side.

At what point do you realize, "Okay, there's a business here, and like maybe we should bet everything on it. Maybe we should make the leap"? What is that moment like?

Cory and I spent about 10 months trying to build the business on the side, and we did get some traction early on. We had a few clients and customers, and back then, 2011 and 2012, early days of social media, so we were charging a few hundred dollars a month to these small businesses to help them manage their social media.

But after doing that for 10 months we're like, "Okay, we either just have to go all in or not do it anymore," because it just became too much to be working nights and weekends and our full-time job, and we knew we were not gonna be able to build this into what we were able to do if we were just doing this on the side.

So we said Let's just go all in and try to build it, and we'll see where this goes. But I just believed, I knew that between the opposite skill sets that we both had, the tenacity that we both had, and- Mm-hmm ... I saw where social media was going. I knew this- Yeah ... was not going away. Even though back then, Leah- Mm-hmm

we literally had to pound the pavement, walking around convincing people they needed to use social media for their business. They were like, "This is a fad." Right. "This is not going anywhere." But I just knew-

Yeah. Yeah ...

if we kept going, we could build this. So We said we're gonna take the leap, and we made a whole plan and quit our jobs May 4th of 2012, and never looked back.

What did that morning feel like of May 4th, 2012? Were you terrified, excited? How were you feeling in that moment?

So I was so excited because I knew this was gonna be amazing and this was gonna work. Courtney was a little more terrified. Again, she had her whole backup plan. She was leaving- Yeah ... Amex, so she had a great corporate job at Amex, and she was almost nervous to tell them what she was going to do in case it didn't work.

Mm. I'm like, "This is gonna happen." And I was just so excited because I just wanted to sleep. I didn't wanna be up till midnight trying to work on these- Yeah, right ... fun campaigns. I just wanted to- Yeah ... execute during the day and start to build, so I was ready to go.

I love it. So a social media agency in 2012, a lot of people may think that idea was crazy in 2012.

There was definitely no playbook for it. What did it feel like to be building in a space that had no precedence to copy, and you just had to create your own from scratch?

We learned very early on as we were building that we never wanted to be the smartest people in the room. We wanted to learn from whoever we could learn from.

Mm. People who'd already built businesses. Now, just because people had never built a social media agency before, there is millions of business owners out there. Let's learn from the best people. If you can picture this, Leah, so we quit our jobs on a Friday. We went out and celebrated that weekend, and on Monday we got to work.

We were in my Upper West Side apartment in New York City, and Courtney came over. We had a whole, you know, whiteboard. It wasn't even a whiteboard. It was like those sheets of paper that you can rip off to write out our whole plan, and we were like, "Okay, we should get some interns because it's the summer, and we can probably get some awesome people to help us- Yes

this summer." And then we were like, "Oh, wait, we don't have an office. Where are they going to go?" And this is before remote work and Zoom- Of course ... and how everything is today. So Courtney called her mom, who has also owned businesses for years, and she called her mom 'cause Courtney remembered her mom had a client from years ago who had a printing company in Manhattan who had a lot of office space.

Ooh. And she still had a relationship with Frank. So she calls Frank, and he says, "Tell Courtney and Stephanie to come meet me in my office. I'm happy to help them." So the next day we go to his office, and we say, "Could we have some of your office space so we can bring some interns here?" And he was like, "Wait a second.

How are you gonna get all these clients?" And we're like, "We're gonna pound the pavement. We're gonna go out and just go walk door to door and meet business owners who need social media services." And he said-

Yeah ... "

Let me help you, ladies. Come to my networking group." And that group, we went to that first meeting, set the stage for everything, Leah, that we would accomplish in business over the past 15 years.

That one group- Wow ... we went to that first meeting, and we saw how business was getting done- Mm-hmm ... how people were talking about their business, referring clients to each other, and that business owners really do wanna help people, and that there's enough- Yeah ... business to go around for everyone. So we joined that group that first week in business full time, and it is what led to all of our first clients and customers.

Those speaking engagements led to us meeting our mentor, Carrie Kerpen, who had a social media agency, and she was a few years ahead of us. It led to every single initial connection and conversation that helped us grow to a seven-figure agency, and very quickly.

It's amazing, amazing. And here's my favorite part of your story.

You never raised a dollar of funding. Can we, like, underline, highlight, make that blow up? Because fully bootstrapped, you build this agency. Can you talk a little bit about why getting outside funding was a choice, not just a constraint?

Well, I'll tell you this, Leah. Back then, Courtney and I were in our early and mid-20s.

We were building a service-based business. We didn't even know raising money or going out and getting capital was an option- Yeah ... or a thing. Right. That wasn't even- Yep ... on our radar. Mm-hmm. It really wasn't until a few years in business that we actually saw how so many businesses were getting funded that way.

And typically, with a service-based business, most service-based businesses are not going out and seeking outside capital, right? Mm-hmm. So the only way we knew how to fund the business was through revenue. There's 14 million women-owned businesses. Mm-hmm. The majority of those businesses are not funded by venture capital.

Now, some of them- Mm-hmm ... might be funded by taking out a credit card or a line of credit or an SBA loan, and we've done all of those things. So we've taken on a lot of capital, a lot of debt for ourselves, but we- Yeah ... didn't take on that debt until we knew that when we would take on debt for our own business, it was to fund an investment in the business that was actually gonna help us grow.

Yeah, I have so much respect for that, and I think it's such an incredible, powerful, smart way to build a business. You built an all-woman agency in an industry that doesn't necessarily look like that. What assumptions about who runs an agency or who clients will take seriously did you have to break?

You know what's so interesting, Leah, is that because we didn't really have, like, a model for how any of this was done

Yes

it was actually a great thing, right? Yeah. We kind of just went out and did our own thing, and neither of us had come from the agency world. So we were not- Mm ... coming with years of experience working at a PR agency or a traditional marketing agency. We were just creating what we thought needed to exist.

And then I mentioned our mentor, Carrie Kerpen, who was- Yes ... a few years ahead of us. I don't know if you know Carrie. She's incredible. Mm-hmm. And she was a few years ahead of us in business, and when we got a meeting with Carrie and we met with her for the first time, and we walk into her office. She agrees to meet with us.

She has these glass walls in her agency, and if you know anything about, and you built a, a big company with a lot of people in an office, it is very expensive to have glass- Yeah ... walls in New York City. Yes. Let me tell you. But what we saw from that when we walked into her office was we saw what could actually be possible for us.

And she took us under her wing and showed us when we were going through growth challenges, she literally took out her org chart the first day she met us. She's like, "Here's how you do it." Mm-hmm. And I want you to go meet with our- Wow ... head of HR and hiring, and he's gonna share advice with you. And she showed us very early on there's enough opportunity to go around for everyone, and she started referring clients to us that weren't a right fit for her.

We started doing incredible things for her, and built this incredible mentorship. But, like, now we're j- just a close friendship. Yeah. And she was the role model, really, of who we saw ahead of us. Aside from Carrie, there was no one else really doing what we were doing back then.

Here's something I know in my bones from building TaskRabbit, the back office work will bury you if you let it. Payroll, benefits, compliance, the endless HR paperwork nobody warns you about, and every founder I know falls into it, right? You didn't start a company to run open enrollment or double-check payroll at 11:00 PM, but there you are, pulled off the one thing only you can build.

That's exactly why I love Justworks. They bring payroll, benefits, HR, and compliance together in one place so that whole pile comes off your plate and your team's plate too. It's built for small and growing businesses, which is to say it's built for exactly the founders I spend my days with. Justworks is the one I point founders to when they're making those first hires and the paperwork starts to stack up.

I've watched it hand people back their focus and their weekends. So don't be a hero about the admin. Get it handled and go do the work that actually moves your company forward. Go to justworks.com to learn more. Go build the thing only you can build. 

It's so nice to hear that you can find not just mentors, but someone who's gonna advocate for you, right?

Like, really be a sponsor, and really help clear the path and show the way, especially in an industry that you're creating from scratch. So you went on to sell SocialFly, and from the beginning, was that always the goal? Was that kind of the path that you had in your mind for this business?

The initial goal when we started the business was to basically create jobs for ourselves, that we were building something- Yes

that we could replace our 9:00 to 5:00 income and do something that we were so passionate about and enjoyed doing every day. Mm. That was goal number one when we first started. When we then joined that networking group, it just expanded us so much more to see what was possible and what we could actually build.

And then when we met Carrie about not even two years into starting the agency full-time- Aside from showing us her org chart that day, she said, "You ladies need to read the book Built to Sell." Mm. She is who opened our mind to see that, wow, we were actually building something that could be worth something so much more than just replacing our nine to five income and creating jobs for other people.

We were actually building an asset that could live beyond us, that could be sold, that could be sold to our employees, that there were so many other options out there for us. Mm-hmm. Yep. And this could actually be so much more. So we read that book that day, and then Courtney and I built out a whole plan for how we were going to build this business, not necessarily to sell right away- Yeah

but we wanted to build a sellable asset that if and when something ever happened to us or we decided we didn't wanna run this business anymore, that this business- Mm-hmm ... was worth something- Yeah ... and live and move on without us.

So smart. Well, in 2021, you decided to split the business. You took over EntrepreNista.

Can you tell me a little bit about what you felt like is here that you just couldn't walk away from, that you really wanted to pour yourself into?

Yeah. So when we were building SocialFly, we started getting so many messages and DMs and emails from other women who were starting businesses who really just wanted to go out to coffee and pick our brain, and wanting to hear how we were able to build what we did so quickly, and that's all I wanted to do all day, every day.

But it wasn't scalable, and we still had to run the agency business, and I was still working day to day in the agency, so we started thinking, how can we actually help as many women as possible but do it at scale? So our initial idea to solve this problem was to start our podcast, and EntrepreNista really started as the podcast, really on the side of running the agency, and that was back in 2018.

And then when everything happened with the pandemic in the beginning of 2020, then we're about a year and a half into the podcast, and now we started getting even more messages from our listeners and our followers. Back then we were hearing things like, "I lost my job. I wanna start a business. Can you help?

I need to pivot. Can you help us?" And I'm like, here we were in the middle of the pandemic navigating running the agency, but we had- Yeah ... network at that point and support, and we had built a community of other agency owners that we could workshop with on how to manage everything. But all of these other women reaching out didn't have that.

And that's when Courtney and I knew in that moment at that time in 2020, we were like, "Okay." We always knew EntrepreNista could be so much more from the moment we started the podcast, but because we were- Mm-hmm ... so focused on the agency, we couldn't go all in. Now we were in the middle of the pandemic, we were actually now all working from home.

We closed our physical office at that point. Mm-hmm. And we had all the time in the world now, 'cause we didn't have to commute every day in New York City, so we were like, "All right." We knew we were gonna sell the agency at the point. We had really scaled me out of the day-to-day operations of the business by that point as well.

I was focused on sales and marketing for the agency, but we had a whole team under me doing that. We're like, "Now is the time." We worked with our business coach, and we made a plan of how we could really divide and conquer so Courtney could stay focused on growing the agency and setting the agency up for sale, 'cause we knew we were gonna sell, and I would start building everything out with EntrepreNista to be what it is now today, which is a full media company and our membership community, the EntrepreNista League, because we knew when we sold the agency, Courtney would likely have to do an earn-out, because that's what happens when you sell a service-based business.

Mm-hmm. So the plan was, by the time we sell the agency and she's done with the earn-out, I'll have already built EntrepreNista to be where it needs to be so she can come back- Yeah ... and work full-time in the business, and then can help execute. So- Amazing ... that's the plan that we literally followed to the T.

I love it. And so you mentioned the EntrepreNista League, now over 1,000 members. What was the gap for women founders that you kept hearing that made you say, "I have to go build this"?

Well, I will tell you, Leigh, we now have 4,500 members inside-

Amazing ...

the EntrepreNista League. Amazing. Wow. And we were hearing everything from, "I feel alone."

We've definitely solved the entrepreneur loneliness problem. Basically- Mm. Yeah ... no woman entrepreneur could ever say they're alone anymore, because everyone has that connection and support inside the community. Mm-hmm. Women, as they were scaling their business, did not know who they could connect with or turn to next for the challenges that they were having in their business.

So we realized we needed to really create that path for them so they would have those resources and connection and support as they were scaling and going through different stages in their business. And then the last thing that we continue to hear, and it's something that we experienced, and we learned how to navigate this ourselves, is visibility.

So in order for a business to succeed- Either your business has to be very visible and you need a marketing strategy so everyone knows what your business is so people can buy from you and do business with you, and/or founder, the founder needs to be visible, and you need to do founder-led marketing so people fall in love with the founder and then wanna do business with you.

Mm-hmm. So we learned the art of that very early on as we were building SocialFly, so we would always practice what we would preach for our clients. We would do the same things for ourselves, so we worked on building our personal brand, our business brand, PR, marketing, speaking, all the things, and we were thinking, how do we package this up inside EntrepreNesta to now give our members this visibility platform that they don't have to piecemeal together other places?

So now our members have built-in visibility opportunities for themselves personally and for their business when they join.

It's amazing. Amazing platform. And you took this playbook, and you actually wrote a book. We should talk about this 'cause I'm in the middle of submitting my book right now. It's a whole process, right?

That's so

exciting. Yes.

So Like Love Follow, what did writing it all down in a book do that running the agency couldn't do?

Writing that book really helped with our credibility and visibility in the early days. Mm. So that book- Okay ... we wrote a book about- Wow ... social media in 2015. We are in 2026 right now.

That book- Mm-hmm ... totally outdated, right? There's nothing in there about TikTok and other things. Yeah. But we were able to say, going into new business meetings back then, that we wrote the book on social media. Not a lot of other people could say that. So we had this instant credibility, and I always share with founders, especially founders who wanna write books, there's different reasons to write books.

No matter what your reason is- Mm-hmm ... you need to have a commitment to it because, as you know from writing a book, it takes time, and it takes money, and money is time. And it takes- Mm-hmm ... follow-through and commitment to then market the book and achieve the goal that you want from the book. But for service-based business owners, having a book really can be this credibility piece for you that can lead to- Mm

more business opportunities, and that's how you can really monetize that opportunity. But for others, it might be you have something on your heart that you wanna share with the world, and you wanna get all of that out in writing and be able to make a difference in the world and to share your message.

And that is a reason that a lot of people choose to write books, and even that type of book can still lead to so many opportunities. But as you know- Yeah ... writing a book can be challenging. You need to have a whole plan and process to do it, and we help our members with that, too.

I know. I was gonna say, like, this seems like a really good area to help your members with because I agree.

It does add the credibility. It elevates your voice, your story, whatever it is that you're working on, but it is a tough system to navigate. Yes. It's a very closed system, right? I didn't know anything about it before I started writing my book, and there was a lot to learn. There's a huge learning curve.

There's so many different paths to be able to write a book. Mm-hmm. Back in the day, everyone thinks like, "Oh, traditional publishing. You need to write your book proposal and get it to a traditional publisher, and that's the only route to go." And that's not- Yeah ... the case anymore, and that's a really great way to go if that works for you.

But there's- Yeah ... so many different options out there. We have partners that we work with that have self-publishing platforms. We're working on building something out internally at Entrepreneсса to have different options for our members because- Awesome ... we have seen there's such a need for this right now.

But it's hard to write if you don't have the process to follow, when you don't have all the tools in place, and then the marketing power behind it.

Yeah, absolutely. You have spent over a decade now helping other women build, and I wanna kinda spend our last stretch here on what you see that is still broken for them and where it all goes from here.

So- You've repeated a stat, I've repeated this stat too. Less than 2% of women, female founders ever hit a million dollars in revenue. Less than 2% raise money from venture capitalists. For women of color, it's even less. From where you sit and the experiences you have had, do you feel like it's an access problem, a capital problem, a belief problem?

Is it a combination of all three, or what do you see?

It's all of the above, and while things have definitely gotten better, it's still not perfect, and that's what we've been trying so hard to solve for all of these women, specifically in our EntrepreNesta community, because we knew as we were building SocialFly, like, it took us years to build our agency.

We were not an overnight success. Someone might look at us right now as the co-founders of EntrepreNesta, built two seven-figure businesses, sold businesses. We started from zero. All of us started from zero. Yeah. And it took us just doing the building blocks over and over again, joining this networking group, joining that group, speaking, meeting this person, meeting that person.

We're like, there has to be a better way and a faster path to put everything together so we can empower more women to have the tools and resources and the connection and support that they actually are going to need to grow. And if we went through all of the growing pains, and look, everyone still needs to go through some challenges.

That's how you learn.

Yeah.

But let's just make it a little easier, because it's really hard out there if you don't have that support, so that's why we created the community, to put it all together. But when it comes to fundraising, I was actually just recording a podcast episode with one of our members who is an angel investor, and she was just talking about how right now, usually there's cycles with raising capital, and you're doing this work every day, and- Mm-hmm

it's very challenging to raise capital unless you're an AI company.

It's true.

But there's a lot of alternative forms of capital out there. Yes. Yes. And a lot of it comes down to the education and the access to know that these other- Yeah ... opportunities exist, and that's why having conversations like this and getting this free content out there for women to hear and learn is so important, because someone listening might be like, "Oh, I can actually do a crowdfunding campaign, and this can help- Yes

fund my initial product launch. I don't need to go raise venture capital. My business is- Right ... not a venture scalable business anyways. Right. But that's what we're seeing in the media. But we need to have these conversations to talk about the other alternative access points.

Not every business is built for venture capital, and that is okay.

That is actually so much better in a lot of ways for the founders and entrepreneurs that are building, not to have to get on that venture train, right? And just understanding what are the other opportunities, and like you said, access to capital. What are some creative things that I can do? I think it's really important.

You've been such an advocate of not gatekeeping this knowledge, right? And really sharing this knowledge. Is there a piece of insider knowledge that you wish someone had handed to you at the start? I mean, I know you had incredible mentors. But is there something you wish you had learned faster?

I'll tell you something that I wish I had just known.

Mm-hmm.

Everything will eventually work out. I just believe that, and just having that in my heart, because Courtney and I both professionally, like running our businesses, and personally, have just been through so much. Like, every single rollercoaster and hard up and down, like we've been through it all, and I've always just believed, okay, I just have to share this with everyone so other people don't have to go through this.

But it always does eventually work out, and it's just remembering in that season that really everything is just a season. You just need people around you who can be there for you, who can be that sounding board, who can support you. Because now when things happen, and we had something crazy happen, like totally crazy happen recently, but I knew exactly who to call.

Mm-hmm. And I know that no matter what happens, I have the right person to call who will take my call, who will respond to my text message, and then I know based on what I learn, I'm gonna share it and pay everything forward. So surround yourself with community and know that you are not alone, and it really will all work out

Yeah.

So powerful. You came up just as social media was being born, and now that's happening with AI. AI is doing that to everything. It's changing everything, right? How are you using it inside Entrepreneasta, and what do you think it changes for small women-led businesses?

It is so exciting, everything that is happening with AI, because it is leveling the playing field for so many small business owners to be able to have more resources to be able to grow their business faster and actually not have to raise capital.

Because now you could use a tool that might be 20 to $50 a month instead of having to raise capital to go hire three team members. So it really- Yeah ... is leveling the playing field, especially when it comes to operations in a business. Mm-hmm. We're actually doing a whole AI week at Entrepreneasta next week- Oh, cool

inside the community. So we're partnering with some incredible AI tools, and also members of our community that are experts in AI, so we can really teach our members how to be using these tools, and make sure that you're using them strategically. Because the thing is, there's so many tools out there, there's so many resources.

How do you decide what to use? Where do you invest? What to do? It's so overwhelming if you're not, like, in the day-to-day of AI every single day, and that's why we love to bring in experts to just help break it all down so you don't feel like you have to be spending all day on AI, researching this yourself.

You can have experts- Right ... come in and show you and spend an hour to do that. Yeah. And that's what we do inside the community all the time. But I'll share, Leah, where I feel like I truly believe AI cannot replace this, this conversation that we're having right now. Real human connection, and a few years into all of these tools, I think we're just craving this more than ever.

Personally, like, I go on LinkedIn and I'm on Instagram, and I'm like, "I don't wanna read content that's written by AI tools anymore." Yeah. I just wanna connect with real people and hear real stories- Mm-hmm ... and give people- Yeah ... actual hugs and build meaningful relationships, and I don't think- AI can replace that.

I totally agree. Human empathy, human connection cannot be replaced by AI. And I think it's gonna become, like, as people are building their businesses and building their strategies, it becomes, I think, even more important, how do you emphasize those pieces- Mm-hmm ... that truly are human, right?

Yes, because at the end of the day, I can tell you- Mm-hmm

that every single thing we've accomplished in our businesses, and then for myself personally, like, everything- Mm-hmm ... has been built because of actual, real, human connections and relationships that I've made. Let these AI tools help you optimize in your business so you have more time- Yeah ... to do this, to have these conversations, and to-

Yeah

go meet in person and build real relationships.

Like John from age 11

to age 18, right? And guess what, John now lives 10 minutes from me. And when we were on vacation- Yeah ... and we do a local, we got- Oh, my God ... called a near-cation to the beach. So we were out on John's boat just a week ago. That's amazing.

Amazing. And now my seven-year-old daughter is on a boat with him. Mm-hmm. And I met him when I was 11, so that's what it's all about.

It is. That's incredible. So looking forward, I mean, you have accomplished so much, and you have really set precedents in the industry that others are following as well. Is there a sort of next precedent you have your eye on breaking or setting, or something that you think needs to be done differently?

I truly just want to continue building Entrepreneasta to be the largest community for women entrepreneurs, and I shared this with Courtney actually a few years ago when we started building Entrepreneasta. My goal was that every single bank or institution, if a woman walks into a bank and says, "I want to build a business," that the banker there says, "Are you part of Entrepreneasta?

Do you have your community?"

Mm. Love

it. Love it. That is the first thing when you're building a business, someone says to you, "You need to make sure you're inside community," because I truly would never have been able to build all I have without community and relationships, and everyone deserves that. We don't have to build alone.

We can go so much farther, so much faster when we support each other, when we champion each other, and when we know that we're not alone.

I love it. You have built the community you wish existed. What's the thing that women founders still can't get anywhere that you think should exist, that, I don't know, maybe you'd think about building next?

Well, actually, the business I tell people to build right now is an AI consulting business. I'm not starting any business right now. Yeah. But I give everyone all of my business ideas. Y'all can go execute, and I have the community to support you, and I will champion and help you. But right now, because AI is moving so fast, and there's so many businesses out there right now that don't understand AI or don't have the time to learn it, if you build a consulting business to help business owners learn how to use AI in their business to save time and money, that is the business right now that, where you can make a lot of money fast and help a lot of people.

Absolutely, and will apply literally to everyone. Yes. Every business- Yes ... is gonna need this. Needs it right now. Needs it yesterday.

Yes. Absolutely.

Okay, looking ahead, 20 years from now, when people tell the story of Entrepreneasta, what is the precedent you want them to say that you broke that no one else would at the time?

That no business owner will ever have to build their business alone ever again. And I know 20 years from now, there are now gonna be Entrepreneursta chapters and meetups in every- Mm ... single city every single month, where women can come together and build their businesses together every single day.

Yes, I love it.

It's so exciting. We do need community. We need more connection. Do you see an opportunity right now that maybe no one is moving on yet, but you think is the right time? I mean, given AI, given what's happening in the industry.

I would say it's actual human connection right now, because people- Mm ... are feeling stuck, that they just have to be in all these tools, and they're stuck to their phone- Yeah

all of the time, learning these AI tools, stuck on social media. I actually see some of the biggest opportunities is everything IRL, and- Yeah ... getting people back out in the world. I mean, we've been doing in real life events since we were able to do in real life events in 2021 after the pandemic, and everyone's just craving that real human connection.

So even for consumer brands as well, how can you bring your customers together? How can you get everyone together to really feel part of your brand? It applies in every single industry.

Yeah. Yeah, I love it. All right, last question here. If you could hand the next generation one precedent to break, one rule the whole business world just takes for granted, we still obey without questioning it, what would it be?

Hmm. I would tell my daughter right now that when she is ready to build her business, if she decides to build one, that you can really build anything that you want. If there's a demand for your service or your product, you can figure it out. If people tell you no, you're going to hear no over and over and over again in business.

You have to find the way to get to that yes. So as long as there's that demand that someone wants what you're offering, you can figure out how to build it.

I love it.

Building TaskRabbit taught me one truth I'll never forget. The highest leverage thing you can do as a founder is stop doing the work someone else could do for you. But we all fall into it. You're the one booking the travel, chasing down the receipt, rescheduling that same call for the third time when you should be building.

That's exactly why I love Squared Away. They pair you with a world-class virtual assistant who becomes a true force multiplier for your business and your life. And here's what makes them different. Their assistants are overwhelmingly military spouses, some of the most resilient, adaptable, organized people on this planet.

And in this AI era, they're not just assistants. They're AI managers, the humans in the mix who make your AI integration the best it possibly can be, because AI is only as good as the person directing it. And Squared Away gives you someone who runs the tools and tasks so you can focus on the things that only you can do.

Michelle, the founder, built this company almost a decade ago. She is a precedent breaker herself, and I admire her story so much. This is the solution I recommend to founders in my portfolio when they finally admit they need help. I've watched people get whole days of their week back. Breaking Precedent listeners get 25% off your first month at gosquaredaway.com/breakingprecedent.

Go get your time back

Well, Stephanie, this has been such an incredible conversation. I love all of the work that you're doing. I'm so excited to be able to collaborate with you.

I'm doing so much investing, too, in female founders, in entrepreneurs just getting started. So there's just so much important work, I think, that overlaps and crosses over between our two worlds.

Yes, I'm so excited for all the collaborations ahead, and you'll definitely have to come meet with everyone inside the community, for sure.

I would love that. Thank you. That was Stephanie Cartin, a founder who didn't just build companies. She challenged the assumption that you need permission, a pedigree, or a pile of outside money to start something that lasts. From a Broadway dream, to a hotel sales floor, to a bootstrap agency she sold, and a community of over 4,000 women strong, Stephanie's story is really about one thing: refusing to wait for anyone else's blessing.

She reminds us that some of the most precedent-breaking ideas start on nights and weekends with one person who simply decides to bet on herself. Who said you need venture capital money to build something real? Who decided which founders get taken seriously? And what happens when women stop gatekeeping and start handing each other the playbook?

If you know someone who's rewriting the rules in their own industry, I wanna hear their story. You can send me a note on my website, breakingprecedent.com. Until next time, I'm Leah Solivan.