006: Rejection, Creation, and Building a Unicorn Company with Suneera Madhani

That's where people get hung up in that fear is that we're expected to go from A to Z. You don't need to go from A to Z, you just need to get to A to B. And then when you're at B, then get from B to C. Yes. Big goals are made up of small steps.

Attention is power and creators harness it better than anyone else, but they're not using that attention to create the biggest impact possible and are vastly under-monetized. Hi, I'm Rachel Rogers. My co-host Nathan Barry and I believe you can be a billion-dollar creator. Sound impossible? Over the last 10 years, we've followed each other on our own quest to build billion-dollar companies. We've studied creators and seen how entrepreneurs build traditional audiences and use them as a launching pad for a massive business. And it got us thinking, if it can happen for them, it can happen for us. And if it can happen for us, then why not you? Billion Dollar Creator is a show teaching creators how to capture attention and turn it into real wealth. We will deep dive into brands, celebrities, and entrepreneurs who have done it before and show you how you can apply it to your business as an everyday creator. Join us weekly as we learn from both the wild successes and the missed opportunities, the grand gestures and the integral mistakes, and through that, help you become an expert at building your audience on your journey as a billion-dollar creator.

It's good to be here in Nashville with you all. One thing If you've listened to the podcast at all, we talk about Taylor Swift quite a bit.

And also Beyoncé.

And Beyoncé, which, you know, shout out to Taylor Swift for putting the NFL on the map this week. It's good that they're finally getting some of the attention that, you know, they've hoped for for years. In all seriousness, that's wild. Just the Taylor Swift effect, even on something so popular as the NFL, like blows me away.

Yes, exactly. We actually happen to be in her neighborhood.

Yeah, her apartment is the next building over. And we're hosting a mastermind in the room and Alyssa on our team comes in and is like, I know why you chose this hotel. And I'm like, what do you mean why? And she's like, that's Taylor Swift's apartment, which I did not choose it for that reason. It's just a happy coincidence.

Just a happy coincidence. Just, you know, happens to be a unicorn, right? Causing money to be spent wherever she goes. Yes. Money to be spent, money to be made wherever she goes.

Yes. So speaking of unicorns, our guest tonight is someone who has built a unicorn company. Has done all kinds of incredible things. And so Rachel, I'm gonna let you introduce our guest.

Yeah, so Sunira Madhani is a friend of mine. I met her last year at South by Southwest. We were on a panel together and we just hung out all day long. You know, it's like we met for breakfast and then we just followed each other around all day. She is just a dope creator and had an idea working at a company, and she'll tell a little bit about her story, and decided to bet on herself and just accidentally not so much accidentally, built a billion-dollar business, which she recently exited. And now she's deciding on what she's going to do next. She is all about women's empowerment. She is all about showing that people of color, women of color can build billion-dollar businesses. And so, one of the things that she's doing right now is being very visible, doing a lot of media because she wants to make sure she knows how important it is that her story is out there so that, you know, people like us can see it and say, okay, I can do this too. We can have billion-dollar businesses. And that's why we do this podcast, because we want you to dream bigger. We want you to see that there's so much opportunity out there for you, and you don't have to choose the smallest thing. You can do the biggest thing if you want to. So I'm so delighted to welcome Sunira, who has her two children here. She's a mom of two that built a billion-dollar business. Amazing. So y'all are going to hear that story in just a moment. Welcome, Sunira.

So, Sanera, you built a company to an amazing level. Like, someone who's not in payments or tech might not understand these numbers, but you're processing $40 billion in payments, which is absolutely insane. We want to— like, are there— why don't you throw out—

90,000 customers as well. Can you imagine? 90,000 customers. That is a lot of people to have a responsibility to, to deliver for. So scaling something like that is pretty spectacular.

Yeah, will you throw out a few more stats? What are some of the things that you did at Stacks Payments that just to help people understand the scale of it before you exited?

Oh my God, if I have to sum, it was the craziest whirlwind over the last, it took 10 years by the way. So one, I want to say that all of those stats and all of those numbers, it did not happen overnight, right? It took 10 years. And I, what I will tell you that I have felt every day of those 10 years, right? It goes by really fast. And I think most successful founders will probably tell you that, that you look back and you're like, man, that happened so fast. But when you look back, you did feel every single day of those days. And so, it did take 10 years, but I am so, so proud of what took place. And so, yeah, so I started the business in 2014 and scaled it from just an idea that was rejected by every bank, every processor, every, you know, fintech wasn't even a word. Payments was something that I was just part of. I was in the industry. I saw a need. I was selling terminals out of the trunk of my Volkswagen Beetle. Like, I literally from the ground up started this business and scaled it to just record-breaking heights. I mean, we were the fastest growing fintechs in America over the last like 5 years, uh, and took it from absolutely nothing to exiting at over a billion, actually exiting at over a billion, to get raised over $500 million in venture capital. $40 billion in payments just processed this last year from an idea that didn't even exist. And so, 90,000 customers, over 5— almost 500 employees nationwide, multiple offices, all the things, very exhausting, but super wonderful. And I'm so grateful now to kind of be on the other side and to share. Truly, I'm here to share what it took to get to unicorn status.

So let's start back where you began. So you're selling payment terminals out of the trunk of your car.

Yes.

Tell us what that was like. How did you get to selling payment terminals? You worked in this industry?

Yeah. So I graduated with a degree in finance and marketing from University of Florida. So I'm a Gator. And thank you. Yeah, I, I actually did not want to become an entrepreneur. So I think there is like a Forbes article somewhere that says like reluctant entrepreneur built billion-dollar business. Like I was a reluctant entrepreneur. You see, I grew up in an immigrant household, so I grew up with a family of entrepreneurs, but entrepreneurship was out of necessity, not because it was sexy. Okay? So, when you grow up when entrepreneurship is a need, you view it differently. And so, I saw the struggles that my parents had firsthand in, you know, growing their businesses and scaling their businesses. And the reason why my parents became small business owners was because that was the only way to the American dream. There was no other way for them to succeed, you know, without an education. They were— both of them were in education. They came here from Karachi, Pakistan separately. They met in Chicago. I was born in Chicago. I grew up in Dallas, you know, proud Cowboys fan, by the way. And so grew up in this amazing household. It's like one of the most, like the thing that I will always say that has, if I look back at why I'm successful, it's because of the values that we had as a family. And one of the things that we had, and now I know, and we talk a lot about, which is like the abundance mindset, right? So we talk a lot about the abundance mindset. We naturally had that as like an immigrant family. Like did not matter what we had, whatever we had was more than enough, right? And it was the best. Like we had the best vacations, we had the best meals, we had the best celebrations, and it took a village. So I was always used to having one, a million people in our home, a million people at the dinner table, but it took everyone to succeed. And so I didn't grow up with that and I'm so grateful for that because I didn't grow up around it. And now I look back at it and I don't, I didn't have any scarcity mindset around me. It wasn't about self anything. It was about community. It was about the togetherness and the building and those family values. And so that is important for me to share how I grew up. I also grew up working in my parents' small businesses. So we had a convenience store and then another convenience store, and then we had like a chicken franchise and a marketing firm. My father was a serial entrepreneur by the definition and successful in his own way, but also a very like bored entrepreneur. So he would start something and then we would go to the next thing. And so my brother and I went to 10 different schools in 12 years. That is a lot of schools. And so I'm used to, and that's why I can, I can make friends with anybody so quickly, so easily. And I'm also grateful for those experiences, but it was hard. And so I was a kid that was always new, always trying to find a seat at the table. And now when you hear these things about me, Rachel will be like, oh my God, she knows this. And this stuff like totally makes sense in my friends because I always fought to belong somewhere. And I ended up going to school at UF because that was like the scholarship that I I had, and I ended up going to UF, and it was, you know, this amazing opportunity. I went to college. I was the first person in my family to earn a degree, and that is— it was a big milestone for our family, and that was the American dream for my parents was that we become educated so that we never have to work with the sacrifices that they had to work. And so I wanted that corporate job. I wanted that stability. I wanted that 401(k). I wanted the things that I did not grow up around seeing, so I was a reluctant entrepreneur. But all of the things that were just in my DNA, right? Naturally, I'm a problem solver and I cannot sit back and see things that take place and not want to fix them, whether it's on my paycheck or not. Okay? And so that's how the payment industry, like, was. I got, you know, I got a corporate position. I had multiple corporate positions. And then my third job out of school, I was working for a payments company. It was a super large payments company and it was credit card processing and I was Sold this dream that ended up becoming this nightmare. And I'm so grateful for having a real sales job. Let's call that. I was like hesitating to say it was a real sales job. It's different getting rejected over the phone or online than you have to show up to a business in person and be rejected to your face.

First of all, one of the best things that can ever happen to you is that you are rejected repeatedly.

Yes.

Because then you are like, oh look, I didn't die. And then, then you get comfortable asking for what you want and what you need. You know, so I love that. I think we need to put ourselves in positions to be rejected a whole lot more often so that we can understand like, okay, this ain't the end of the world and be more like Sunira and just strike up conversations and ask for the sale and get up in there, you know.

So hard. I remember sitting there and I would have to like look myself in the mirror and say, all I need is one yes today. Yes. Right. And like, I get to eat lunch when I get that yes. So I would go hungry if I didn't, and I knew once I got the yes, I could eat my lunch.

First of all, can we talk about this for a minute? Because I play games like this with myself.

Do you?

Do you do this too, Nathan Barry? Is this the mark of a successful—

Not with food.

These are like war games. You're taking that very seriously.

But I think it's— I don't know, there's something about gamifying it, right? Like, oh, after I get— when I hit this, I'm going to reward myself with that. You know, it's fun. So I don't know, maybe not with food.

But I guess it is. I guess that is like what's important to you. I mean, food is very important to me. I am a Pakistani. Food is very important to me. I think about the next meal. I do. I think I want to eat really good. I want to eat really well. So that—

listen, that motivated— it's about what motivates you, right?

It was just about the fact that I knew I had to get the one yes, and I knew that I was going to get the nos. And it's hard. So I show up in person. I learned the credit card processing industry, but I was paying attention. Right? So it's paying attention to the customer. And I think people are not paying attention to their customers. I think we think we're paying attention to our customers. You're not actually paying attention to your customers. So I was paying attention to the customer and I heard all of the things that I was getting rejected for. They were burnt out, fees were really crazy. They couldn't understand what they're like, what this was. And like all, they had no support, but also I paid attention to where the puck was going. So the industry was very commoditized. It's just like, who can offer better service or better rates, right? So pricing, better pricing and better service. That is not the industry you want to be in. If you are in a position where you're having to undercut pricing or you're having to like, I have better service, you're not going to be a billion-dollar business, right? Because there's going to be the next person who's going to offer better service and better pricing than you. Okay. But what I— where I saw the puck going is that we are becoming more and more cashless as a society. Those transactions that are flowing going through that terminal that I was selling. I was focused on selling those terminals. Like, what about the data that's actually going through those terminals? What do we do with the data that's in that box? Like that literal black box, what are we going to do with that? And so I worked in the industry for a couple years and I was really frustrated. And one snowstorm in Texas, Texas does have snowstorms, Dallas does have snowstorms. I was stuck in a snowstorm. I was visiting my grandma and I legit that week, binge-watched season 1 of Shark Tank. So it did happen. This is over a decade ago. This is like 11, 12 years ago now. And I binge-watched this whole season. And I think there was something in there I saw that is so important. You can't be what you can't see. You cannot be. And I saw entrepreneurs and like they're asking for money, they're asking for investment. I had no exposure to that. I did not have any exposure to that. And I saw, and all these businesses, none of them were, I didn't know what the term SaaS was. I didn't know the term software. It was just like, product-based businesses that were getting up and pitching. But I, one, I can look back and I can like put the pieces together. And I saw people asking for money for their business. Two, at that same time I was rerouting my subscription boxes because I was a subscription junkie. Okay. So in every which way. So like, it was like, this is, I'm going to age myself, uh, Birchbox ladies, Birchbox, BarkBox, right? Like all of the, all of the boxes. Okay. I was— They all got you. Yeah. I was obsessed with these boxes and I was like making sure I'd be home to like receive my packages. And that was it. That's when like the aha moment happened. And I was like, why isn't there a subscription-based credit card processor? Like there's all the subscription-based like movement happening or it's about to happen. Industry's moving this way. Who's supporting one subscription-based businesses? Who's supporting like all of my, my customers are complaining about pricing, all like all this stuff. What if we had a flat fee subscription? Like we do our, our like Spotify or Netflix wasn't even like, I think we were selling like CDs. I don't know. But whatever. What if it was a subscription in the payment industry? And I did what every young entrepreneur does is you go to Google, right? You're like, okay, here you go. Like, there's got to be something out there. And there wasn't. And I had two options. I was like, okay, what? I can either hold that idea or what can I do with it? So I decided to— my superpower And Rachel can— I can get into the room with anybody. That is my superpower. I, that is my super— I can, I'm one degree away and maybe it's like how I think about it. I'm one degree away from anyone I want to be in the room with.

That's an abundance mindset.

It is. Just a quick brag on you. That includes the vice president because you were—

That also includes the president too. But the vice president is way cooler. But to be clear, you were at the vice president's Yeah, recently she just invited me over to her house for dinner. It was amazing.

So just to— when Sunira talks about that mindset and how she channels it, right, it goes all the way to the top.

It clearly works.

So she's on to something.

It is. But you've got to— you do belong. Like, you do belong in the room. Whatever room it is, your voice matters. It does. And when you start believing that it matters and you feel passionate about something that you want to advocate for, like the seas will part.

Mm, I love that.

Mm, mm, mm. Okay.

Just preaching up here today.

Oh, I'm so happy. I'm so happy to be here. I'm so happy. And I am here because I want to be here. I want all of you to know I'm so happy to be here. Thank you so much, Nathan and Rachel, for having me. I'm so excited to be here with you all because this mission that they have is real and we're going to change the game and why all of you should be building $1.2 billion businesses. Okay. So when I went to headquarters, so I decided to switch my flight, went to headquarters, said, I'm going to go make a meeting with the CEO. I got into the room with the CEO. So I got the meeting, did it. Little Senero, who's 25 years old, young, not, you know, anybody important in the company. I get the meeting and you know, when you're young and you work for like this big company, you're like, you imagine what headquarters is going to be like, right? You're like, oh my God, everyone's going to wear like fancy suits and you're going to walk in and everyone's going to like, I don't know, be drinking like protein shakes. I don't know what I had. Everyone's gonna be like on their laptops and there's gonna be board meetings, a lot of cool stuff.

It wasn't?

No, I get to headquarters and it was like nothing like I had like imagined my company to be. Yes. And the first thing I remember is that there was nobody that looked like me at the company, at headquarters, at like the main, like the thing I looked up to so much. There was nobody that looked like me. There was no women. And the women that were working there were all in the support department or were secretaries or were in the marketing department. There's nothing wrong with any of that, but I wanted to be in the C-suite. That's where I saw myself when I was working for that company. And I got into that boardroom and I'm super overachiever. So I'm a Virgo, by the way, and I'm not just like, I'm like that explains everything. It does everything, everything. My whole life is like, I will tell you all the therapy right here. You'll understand me in like 5 seconds. So I'm super Virgo, super Type A, older sibling, all the things. I am like in charge and when I do shit, I do it well. So I gave the best presentation of my life for this business plan for my company on the, the, like the subscription-based model that's going to disrupt our industry.

So you're pitching this to your job where you work?

My job. I, I did not want to, I didn't even think for a second for myself that this was going to be me to do it. I just thought this was going to help my company. And that I'm going to get to be the one who helps create this and I'll get to lead a department, I'll get to have a team underneath me. And I thought this was going to be my step up in my corporate journey. And I give the best presentation of my life. And y'all, I get laughed out of that room.

Wow.

Little girl, your ideas are too, like, they're strange. This would never work. You want us to invest in technology? We want to give away our pricing? It's been done like this. You don't know. I don't know, I'm inexperienced. You don't know. This is not how it works. This is not how it's going to be done because this is how we make money in this industry. So I get back on that plane.

First of all, how often do people love to say, well, it's never been done that way before, and it's like, yes, that's why I'm about to do it. Duh, you know, but it's so true. It's like, oh, because people always tell you it's a bad idea because it's not common. And that's why it's a good idea. So you can't let other people's fears or projections stop you from doing what you want to do.

So I literally left that room so defeated, but I had two options. And I knew I had to quit that job. I get home and by coincidence that Sunday that I fly home, it happened to be family dinner. My brother was there from San Francisco. We're all around the dinner table and my dad He looks to me and he goes, "Sunny," which is like my family name, my nickname, "Why don't you just go do it?" And the first, me, "Dad, where do I go find Mr. Visa? How do you go start a platform? Like, I don't have any experience in building technology. Like, how do I go build a network?" And he said, "You'll figure it out. You're a problem solver. So if you want to go solve it, you'll figure out the solution." You have it. And I have it tattooed here on my arm. And it's— he was right. I did have it. That's my superpower. I solve shit. I know how to solve. I don't— I didn't know what, what it was, how the sausage was going to be made. But I knew that if I actually put my brain to it, I could go get to the next step. And I didn't need to go from A to Z. I just needed to go to A to B and then from B to C. And I think that's where people get hung up in that fear. Is that we're expected to go from A to Z. You don't need to go from A to Z. You just need to get to A to B. And then when you're at B, then get from B to C. Yes. Big goals are made up of small steps. Right?

So true.

And so that was the journey. And from there, we started the company and went from that first year from not knowing Mr. Visa to partnering with every major card network. I became a mother, built the business as I continued to scale. And if I can do it, I kid you not, you can do it too.

That's amazing. One thing that I want to dig in on is I think a move of playing chess, not checkers. And that's when the industry is all very standardized. For anyone who doesn't know the credit card processing industry, there's standard rates. And so for the most part, you pay like Stripe would be 2.9% plus $0.30 per transaction. It's what everybody does. PayPal has their own model, etc. And so I can imagine when you come in and say like, hey, let's throw all of that out and let's let the merchant— we'll charge a flat fee, you know, $100 a month or whatever it ends up being. And then you can just pay as a merchant, you can just pay the interchange fees, what Visa and MasterCard and others charge. So it's basically like, I mean, you basically brought wholesale pricing. And so I understand why the other, like, You know, the, the bosses in the relatively boring office, they're like, we absolutely hate this idea.

Never say it again out loud.

Please do not tell anyone this because it's going to disrupt their entire industry and they're not willing to take that risk.

Yes.

And so I think it's so important. Often there's just this one insight that shifts it and thinks about the business in a totally different way. And so I'm curious, as you launched this, was it a huge uphill battle because You're showing up, you know, later to Mr. Visa and others and saying, this is our model. Now they still make their cuts. They probably don't care, but I'm curious how that went. If people like, did you get laughed out of more rooms?

As did people not believe you? Cause I think as a customer, I'd be like, really?

It sounds too good to be true.

What's the catch?

I think there was a, there's a lot of that in there. I think that for anything really novel and the word disruption, what is the word disruption? What is that word disruption? What is the word disruption, Nathan? What does it mean to you?

Taking some of the status quo and upending it.

Completely flipping it on its head, right? It's disruptive. So when things are disruptive, people don't like change.

Yes, they really don't.

People don't like change. They are resistant to change. We are all resistant to change, right? That is why we are so fearful in even starting a business, launching a business. It's change.

Changing your business, trying something new. Pivoting.

Yes. Yes, change is hard, but right, in order for you to succeed, you must evolve and you must change and you must disrupt, right? At any stage. And so disruption, I think, is what people are most afraid of. And most any sort of disruption that occurs at any industry, it doesn't matter what you're disrupting, right? You're going to get the naysayers. And I think what Rachel, what you said, you've got to get used to that level of getting rejected. And I was unfortunately, unfortunately, it's not a, it's not fair and it's not a great thing to be proud of to say that I'm, I was constantly rejected. Right. And still, even at this point, and I'm happy to talk about where I feel like still, as after all the things that we've done, you know, still there's a space where, you know, minority founders still have to prove, like prove themselves in a different way.

Oh, don't get me started.

No, I think we should. I think we should get started. We should get started.

Because it's that proving thing, like, oh, you know, well, prove that you can do this. Okay, I'm gonna go do that. Do it. Check. Well, now prove you can do this other thing. Okay, did that. Check. Now prove you can— It's like this endless, well, we don't know if we trust you. We're not sure. We just have doubts. It's like all of this language that's really racially charged. And, you know, if it's not race, it's about gender.

Right.

It's just kind of like we can't believe something so profitable is coming out of this package.

No, it is very difficult. Change is very difficult. So, yes, so much uphill battle. Like, I will say that the reason for our success and for like why, if you look back and like the biggest myth, like I could demystify for any, any entrepreneur ever, like if somebody asked me like, what is my biggest lesson? And going back to this checkers thing, it's like I wish somebody positioned it like I was playing chess, not checkers. But I would say the biggest lesson that I learned is that it doesn't get easier. You just get better.

Yes.

Okay. You just get better at tackling the fucking problem, tackling the fucking solution. And you know, and you know what's coming, right? So you, that experience and is that notch in your belt and that notch in your belt is worth so much in gold because now I look back and I'm like, okay, I'm about to go start. So we exited and I'm happy to talk about what's next, all the things. And if I do this again, which I will, right? If I do it again, I'm already like 7 years into the game. What took me that first 7 years for Sal and I to go figure out? And so yes, to your question, Nathan, a lot of rejection, but it almost becomes comical also at a certain point.

Yes, you do get to a point where you laugh it off, where you talk shit about it, where you're like, y'all, let me tell y'all this story. You know what I mean?

And I dare you to tell a woman she can't do something.

Exactly right.

One thing, you have this entire background as a creator as well, and we'll get into the dichotomy between CEO and creator and that balance. But before we do that, I'm just thinking about as a creator, we often have both the luxury and the crutch of staying behind the camera, behind the computer. And sometimes in a way we get rejected a lot. Because the thing that we put out there maybe didn't get the views that we wanted or the attention. On the other hand, it's a good way to think about it. Yeah. But on the other hand, you can hide behind it and avoid rejection, right? If I'm putting out a blog post that then ties into the thing I want you to subscribe to, and then I'm selling my products on the back end of that and people just hit the back button, like you don't actually learn much from that rejection. You're not out there selling. And so one thing that I think a lot of creators should do is seek out more of that rejection, have conversations with customers, you know, even if it's a lower priced product, try to sell it on a call so you can understand that feedback. Because otherwise, like the back button from a visitor on your website is a rejection, but you don't learn anything from it.

Right. You don't learn how to do it better.

I love that, Nathan. I think that that might be one of the Achilles heels for creators because now in today's world, we can stand behind a computer. And anyone can reject us, hate on us, send the shade, whatever the things are, or not view or not watch or not subscribe or whatever we measure success as, as creators. But I think that the real, like, if I think what we were talking about in the back room of how creators can go build the next $100 million business or billion-dollar business, it's not about the blog or it's not about the post. It's not about the creation of the content. It's about what is the business behind it. And in order for you to build a business, you still have to connect with your customer. And so behind like the digital screen, there is only so much, no matter how engaged, air quotes, you are, your audience is like, how fucking engaged are you really with your audience? Right? When was the last time you actually went through like, and actually did customer discovery calls or built the product with your customer? And so I do think what you're saying on like the value of of that customer and that true customer feedback of getting on a sales call and maybe not even on a sales call, maybe it's just about connecting with the customer without even an ask to get that feedback or that feed forward, not even the feedback, right? The feed forward on what you're building, what you're doing, what you're launching, what that product is, build it with them, right? And not from the lens of just behind the screen or the mobile or the computer screen. And I think a lot of what's happening in the world today, It's scary. Like I, as a mother, I'm afraid of what like the transactional nature of the world has become. And one of the biggest, like there's like, there's two things I like, the freedom of time. Time is the biggest currency that we have. And that's the one that I value top of the most. Right. But I would say like freedom of dollar is like freedom of time is important. Freedom of dollar is also important, but that, but it's also freedom of the, like of not giving a fuck in their relationships. Right? Like I think really, and I do think that having like meaningful, meaningful interactions with people is one of the reasons why I've been like the relationships, right? Getting in the room with people, I said, is my superpower. I didn't get that by just sitting behind a screen. My businesses weren't built by being just a creator. That happened later. My businesses were built with true meaningful interactions with humans. And so in order for me to have the freedom of time, and then freedom of impact and the freedom of no fucks given is because I had those relationships and I was able to call on my customers, call on the vendors, call on the partners, call on the friends, call on the support, call on that village that I was first alluding to. And those relationships cannot be built just behind a screen. And I will say we met behind a screen, right? We met virtually. So Rachel and I actually met just digitally online.

Yes.

I don't know how, like we connected. And obviously what she was doing at Hello7 was very similar to my mission at CEO School. We're empowering women. Woman of color, all the things. We got connected and it was great and we became friends online, but it didn't— like, that was one level of it, but it didn't click until we became friends in real life.

Yes, exactly. That's why I'm so big on events. And so what you're saying is exactly what we're doing here with this podcast, right? We didn't wait until we were 5 years and had a huge audience to do events. We were like, we're just gonna launch with live episodes. And then we get real-time feedback, right, on what we're building from the listeners, right? So I think that's something that should definitely be built into whatever you're creating. I love live in-person opportunity to interact because you just get so much more information. I remember I used to do retreats early on in my coaching business and I'd spend a week in a house with like 10 of my clients. That data was so valuable. It's like I had content for the rest of the year to write about. I knew them I knew what they were buying, what they were paying attention to, what they were cranky about, right? Like all of the things you get to know them so well through these interactions. So I agree with you. And that's one of the superpowers is the more you pay attention to your customer, the more you can serve them better, the more likely you're going to get that sale and that repeat sale again and again.

So I think to wrap up that what we're saying is no matter what type of business you're in as a creator, building a non-creator-focused business, any of that, get out from behind the screen.

Yes.

Go talk to people to think, did I get rejected today? How many opportunities did I even have to get rejected today? Something that I think about when I was building ConvertKit a lot of the time was I was sending emails that were scary. Like you hit send and you like feel that like, yeah, like, is this, I don't know. And then you refresh the inbox. They didn't reply. You're like waiting to get rejected. And I realized, yeah, that's good.

That's a good feeling.

It doesn't feel good, but it's a good feeling.

You're in the arena, right? Like, you're in a position where you could get rejected, which means you're also in a position where you could potentially get a good feeling.

That means because you're doing something uncomfortable, right? And that means you're stretching, you're stretching beyond the par. So if you do not feel it in your gut, that means that you are not stretching to the next level.

Yes.

Okay, so if you are playing at this level and you are comfortable, you are going to stay here your whole fucking life. So if you want to play at this next level, that level to press that send button, Nathan Barry, is scary. Yeah. And that is a good feeling, right? We have to get comfortable getting uncomfortable, right? Because if we're not uncomfortable and we don't hit that send, right, we're not going to move up to that next level by playing at this level ever.

Something the president of my company at Hello7, Brittany Martin, she always points out, and she said that the feeling of fear and the feeling of being excited, it's the same in your body. It's the same physical reaction. So you can choose to interpret it as, I'm terrified, this is horrible, or you can choose to interpret it as, I'm excited because something's going to happen one way or another. Or at least maybe they'll ignore it, but hopefully something happens. Even a rejection is good because like now somebody else out there knows what you're trying to do.

When the great thing about a rejection is, socially speaking, people have to give a reason why.

Yes.

And right.

You can't just say like, no. Like if I say, hey, will you buy this thing? You can't just like— or they're not allowed to just get up and like awkwardly look at you and walk out of the room. Like socially, that's not allowed. And so they have to say like, oh, you know, I would love to buy it from you, but here's this, you know, whatever reason. It's too much work to switch to your product. Right? I'm sure you heard that a lot in the payments industry. And so then you're like, aha, it's not a no. It's changed from a no, but, and you're saying like, okay, what if we did the whole switch for you for free? You know, what if? And so you can, when you actually get to a rejection, then you can often just keep going until it turns into a yes.

Yes, exactly. One question I want to ask you is about raising capital and your experience with that. Was that a positive experience for you? Was that an absolute nightmare?

She's laughing already.

How many conversations did you have to have to get that first check?

We're going to be here for a while. I mean, come on, y'all. The best way to raise capital, okay, is if you are a white man. Straight white man, to be fair. Straight white man. And then it's a lot easier for you to raise capital. But no, all jokes aside, it is fucking a nightmare to raise venture capital as a woman in business. It is so— like, it is not even beyond difficult. First, I want to say, let's just first not forget even pulling out any other piece of it. Just as a woman, and we're leaving out an entire fucking sex, like 50%, 51% of the planet. It's 2.3% of venture capital still. I think it was 2021 stats still less than went, went to women founders.

I wanna like connect for you why that is so important.

Oh my God.

They, we're talking about billions upon billions of dollars that are poured into the economy every year to support certain ideas and to make sure certain ideas happen. Right. And so that means that certain other ideas never happen. Right. So if there's no people of color who are able to do that, and if no, if there are no women who are getting that money, then the like people of color's perspective, women's perspective is completely left outta that conversation. And those ideas never get to happen because if you have a big idea that requires a lot of capital, it's like you can't get that check. So it's really challenging. And of course, there are all kinds of things that are coming up now where there are now women venture capitalists and Black women venture capitalists and, you know, people like Sunira and myself and Nathan Barry, right, where we build companies and then we reinvest in other companies. And so like now there's more people like us. It's still such a tiny, tiny, tiny, tiny thing.

No, the gap, it is a real, it's a big problem. There's a lot of conversation about it. And I really do like the one thing that I'm not a, I hate using the word anger, right? Frustration and emotion. I think honestly it's great. We are all humans. We have those emotions, but I really don't try to con— like there's not a lot of things that truly rile me up. This, this is a real problem in how fast technology has grown, how fast, like everything has moved into this amazing direction, but we are really held back like as women. And it is very— this— I am a mother of two daughters today, and it's going to take 300 years, 300 years before— I'm not even talking about color yet, y'all. I'm just talking about our gender. For women to have equality in terms of opportunity. We don't need to have physical— I don't need to like lift as much as you and take— like, I don't need physical equality. I want mental Equality. I want opportunity. I want the same opportunities to be CEO, to have the position, to create our world.

To create. That's what this venture capital is doing is allowing new businesses to come. Like Uber is now a part of our life, right? That wouldn't have never happened without capital first, right? So like these ideas get to create the world of the future and we are not participating in that. That is a huge fucking problem.

Huge. And it is important and there's a lot of conversation. We all feel like, wow, there's this great movement for women in business and we're having the conversations, but the statistics are not moving fast enough. They're just not.

They're barely moving.

They are barely moving. And so it is important not to bring light, but it's actually what needs to change. I've done a lot of research on this over the last 3 years, and this is how CEO School was created. I mean, I got really frustrated in 2020 during the pandemic. I read an article in Forbes that read less than 2% of female founders ever hit a million in revenue. No, right? That was like, that was it for me. I read this and I'm like, why is this like, this is a major, major problem. And in order for us, and I was speaking on a lot of stages, we were venture-backed, all the things, and it was not easy. And I'm happy to share so many, so many, I have scars on my back on how we got there. We willed our way there. So it was not going to take no, I was going to figure it out because we're problem solvers, right? So you can find, just don't give up that, that it's hard to not give up. The world is different for us. It is different for— and I think you just accept what that is. And it's an unfortunate truth, might not be the advice that you want to hear, but I want to be honest with you. Accept the fact that the world is different for you. Okay? But show up anyway. Right? Show up with a passion that you know that that person is— there is still that— there is a judgment there. There is. And whether it was— I don't believe that it was intentional. There was parts of it that— there is this unbiased racism, consciousness, sexism, ageism, all of it that exists, all of it, right? And so you are, the cards are stacked against you. And I think knowing when you like play the game, right? So if you know you're playing the game, you're playing this game. If you know the cards are stacked against you, you just have to, you have to be so good that they can't ignore you, right? You have to be even better. And that is what I have found, that men are given investment for their potential. Mm-hmm. While women are given investment for what they've done. Prove it. Okay.

Yes.

And so I had a business, I didn't raise capital out of the gate, right? So I had to prove myself, right? So I didn't get the investment right out of the gate. We were rejected countless times. I built a business and we had $5 million worth of payments going through our rails. Like we had built our platform, we had built our MVP, we had customers.

Meanwhile, they're writing checks for people who've done none of this yet.

They just kind of slide down. None of it, right? They wear a hoodie and a sweatshirt and they're like, here's my idea. Invest in us.

But that's why, that's exactly why we created this podcast. That's exactly why we're having this conversation. And that's, that, this is the thing to get you motivated, right? To say, I can go bigger. There's more that I can do. And when I do it, I will be example to all of these people who are watching me do it. And I make it more possible for the next woman behind me, the next person of color, right? So that these conversations are very, very important to just sow that seed so that you can start to believe that, yes, you can do it.

But you can. And for this, that's where the rejection comes in, right? I, you know, you just have to get that one.

Yes.

Right. So you'll find a way. And that, that's all it was. It was, it's a numbers game. Everything is a numbers game. So it's like, how can I show up? And I'm not going to go build those connections behind my computer screen either. So if you expect to go raise, oh yeah, like here's the stat. It sucks. We're not, you know, they're not investing in women-owned businesses and less than, it's like decibels for minority-owned businesses regardless of gender, by the way. Huge fucking problem. And it's not going to change fast enough. It's not. So what are we going to do? How are we going to be solutions to the problem? Okay. We can sit here and bitch about the problem, but how are you going to be the solution to the problem? You're going to go figure it out. And so we cannot do it behind the screen. And that's where I was out every place that I could. I was at every venture conference. I was at every stage. I was pitching at every place that would give me a mic to say, I want to talk about my business. Right. And I want to get the message out. And it did not matter what the outcome was. I was there with pride. I was there, you know, happy to sign one customer up in every room that I was in. And so I do think that there is that resiliency that if you do have, that level of true grit. And people don't like to hear this. And I know like this is where, Rachel, I'm getting canceled out of the world because I know people don't like to grind and hustle and work.

Well, there's a point at which you have to.

But you do have to.

You don't get anything started by sitting on your ass. You know what I mean? You got to get moving.

Hard work is the shortcut. Shortcut. No, it's not. It's hard work. It is fucking hard work. And we had to show up and we had to grind and we had to be better than everyone. And our like KPIs had to be textbook perfect. But guess what? I knew what I needed it to look like. So I knew what the end result needed to be. Right? And I think that's where you play the game smart and you're like, this is what you study. You study your industry, you study your competitors, you study who is getting funded. Who is funding those competitors, right? And you find a way to get in the room, but then you find a way to be better than anything they've ever seen. And you're not going to be better, again, like I said, because of the idea of I'm going to be better and I'm going to provide this thing and I'm going to be blah, blah, blah, blah, blah. They're not going to trust you. They're just not because you didn't go to Harvard. Okay. I didn't go to, I didn't go to CEO school. I don't have an MBA. I don't have a rich dad. I didn't have the network. I didn't have the connection. I did not I did not have shit, but my business stood for itself. My revenue stood for itself. My sales stood for itself. My customers stood for itself.

Well, see, this is the thing that you're pointing out is that all of that sort of being underestimated creates a chip on your shoulder, which is very powerful. And that chip on my shoulder is why I have an 8-figure business because I just was like, watch me, you know, just indignant about it, you know. So believed it for myself, and that irritation, right, like being underestimated fueled me to get up at 5 AM, go do the thing. And I like what you say about it's a numbers game, right? Like it's all a numbers game building the audience, right? If I show up every day, then I'm going to see more people will see my stuff. I'll build a bigger audience. If I show up twice a day, then more people will see my stuff 2x, right? And then I can build an audience even faster. So just playing with the numbers in your business a little bit and seeing like, where do I need to double up my efforts so that I can double up the return that I want? Like, I want to make 2 times as much as I'm making. I want to double my revenue. Great. What are you going to do differently? It doesn't mean you have to double your efforts. It just means like, what's, what's the opportunity where you can see more coming from your efforts, right? And see more happening. So I want to jump to exiting your business. Let's talk about that.

So what do you want to know?

What was that? What was that journey like deciding that you were done? Or, you know, I'm sure you wrung your hands about it because that's a hard thing to do, to walk away from your baby after many years of building. So what was that like for you?

So for those that don't know, I officially exited, like, left my business as CEO February of this year. So it's very recent and it's a very hard thing to decide. So over the last decade, I've only had one thing, right? Heads down. You feel my passion, obsessed with what I do. Love what I do, and I'm out to prove it. I'm here. And one of the things that, you know, I'm ambitious. I'm so— I'm always raising the bar for myself, right? And I think most incredible successful entrepreneurs like you that are in the room, you're like, here's the bar, and then you start to climb it. And before you even get to the level, you're like, okay, here's the new bar, right? And then you start to climb it, and then you're like, here's the new So you don't even allow yourself to actually achieve the bar. You're constantly raising the bar and it doesn't stop. And it's not a bad thing. That's hunger. That's what I said is so good. It's so good to be hungry. It is great to be hungry. The ones that are hungry are going to win. If you're not hungry, you're complacent, you're comfortable, you're not growing. So I did find the most incredible investors that believed in me, that believed in our business. It took a little bit to get there. But once they got there, they got it and they were 100% in on the mission and were there to fuel and to mentor and to guide and grow. And I remember the one Christmas I sent these McCallan's bottles and I changed the label and I said age to 100 million. And I thought it was so clever for those girls. I was like, we'll open it at 100 million. But I look back and I'm like, I capped myself, right? I capped myself. And it's honestly because I did not know that like I could keep going, right? Like I did not know what was achievable. And every day I showed up for a job that was harder than the one I had yesterday. Every day I showed up for something and I showed up. And I know you can feel that, Nathan, right? At where you are in your business, the hardest times. I remember that. And you're showing up every day for a job that was harder. The next milestone was 100. And I hope you don't cap that, right? Like, and I remember like once we surpassed that Series C, it was like 200-something million was our valuation and we did a private equity recapitalization of the business. So I ended up, there's different ways to exit your business and we're not going to go into all the details right now, but it is really important for you to think about your exit in mind. And I find that most often entrepreneurs start a business without an exit in mind, or they say they want to sell their business for like a bajillion dollars and they don't know how they're going to get there. Right? So it is important for you to not just like throw something out to say, oh, I'm going to build this too. $100 million or $1 billion? What is your actual path for your business? That means you understand your industry, you understand your competitors, who has sold in your space, how have they sold, who have they sold to? Is it a strategic buyer that's going to acquire your, your company? Are you going to take it public? Are you going to go IPO? Are you going to sell it to a private equity? Right? There are multiple ways. Are you going to merge it and then be part of a larger organization?

Selling your business is a whole art and it's something I think that people need to study. And think about, you know, as something that you might do in the future, even if you don't want to do it right now, eventually you'll be done or eventually you'll be ready to move on in some way. And so thinking through what, what could that look like is an important part of the journey as an entrepreneur.

Huge. And I really encourage every creator to think about that now. Right. And it's like you're building that business, but what does that exit— how long are you going to show up online for or on your blog for? What happens after? We have to view our business as an asset.

Yes.

Right? It is an asset outside of you. Right? And right now it's okay if your name is tied to the business, but what happens when you get tired and you don't want to show up anymore? What happens to all of that value that you created as an asset? That just dissipates? That's not how real businesses work. Right? So if you were to get a real, a restaurant or an e-commerce store, any sort of business that's a tangible business, software, whatever the business service is, Your business is an asset. So even as a creator, think about your business as an asset and think about what the exit in mind in your end and whatever your niche is, whatever your specialty is, who are the, like what's already been done is important. I'm not saying you have to go do that, but at least gives you a space to say, what are the benchmarks? So as I was scaling across that point where it was a couple hundred million and we did our Series C funding, we had a private equity come in and they bought majority of the business, which meant that all of our previous investors were bought out. We had a huge, it's called a recapitalization on the business. As founders, we got to take some chips off the table, which was amazing. We got to finally make some wealth out of that, all of the equity, that sweat equity that we had put in. And the business was valued at, I think it was like $250 million at the time. But what was interesting is that I was still tied to the business. So everybody else was given 100% of their exit equity, our investors and our employees that had it. Like, we had made 30 millionaires on our team. Like, it was the most amazing, most beautiful— I will— 2020, it was during COVID too. And people told me not to go to market. And by the way, when somebody tells me don't do something, I definitely go do it. So I took my business to market. And you don't want to go against— like, there's so much I can— and we should probably do more later, Rachel, on like what the exit strategy is. But I got stuck back into the business. I loved my business. I had no problem doing it because I still had this vigor and this passion. I'm 7 years into my business and I got to take some chips off the table, but I was expected to roll 70% of my personal equity back into the business and go make more money for our new investors, which I did. And I 4x'd their investment and went from the $200 million to the billion. However, yeah, thank you, thank you. I'll take the round of applause. However, what I, at this next turn, I knew that if I was going to stay into the business, that I was going to keep getting stuck into the business as a CEO and as the founder. And there's nothing wrong with that. I just, I was 10 years into it. And as a founder and as like, I'm a visionary, I'm a builder. And there comes to the point where you build and we had crossed $100 million in revenue as a company, as a SaaS company. Like there's a lot of like the CEO that we need is definitely I could do the job, okay? So, because I learned how to do the job, but it wasn't making me happy to optimize processes every day, to optimize our P&L every day.

It's not as fun.

It's not because I wasn't innovating. I wasn't building. I wasn't disrupting.

A super successful business is usually a boring one.

Yes. So, you know.

And entrepreneurs are not good at being bored.

No. And so at that point we're a decade into the business and people call me crazy for leaving and I was incentivized at every step to continue to stay and the company is going to be amazing. Built it. It was hard walking away and making that decision. And it happened when last year we did our Series D funding and we did another round of financing to scale the company, grow further, and we surpassed a billion in value. And I literally thought getting to that point, you kind of want to reach for it, you reach for it. How many more times do I keep raising that bar? I raised it and it was at a billion and we did it. We fucking did it. We hit a billion. Crossed $100 million, did the things, and that celebration lasted that week. Everybody wrote about it. It was on, I was, you know, did the press tour, was on every major public, did all the things. So exciting, so whatever. And when it was done, I was the loneliest I'd ever felt in my life. And I felt so empty. It's like, what happens when you actually achieve the goal you set out to do? What happens when you actually land on the moon? What else do I do? Set a new one, right? But I wanted to, I took the time. So I took a sabbatical with my family and I just took time. Like finally it was the first real vacation that I took. And I realized that like I didn't want to go and I got the new board plan and it just wasn't, I didn't want to go hit another number. And I knew I did what I needed to do for my company. And now it's time for me to go focus on the things that like, it's time to build something again or to take the time off. And I thought I was to take the time off and retire and then I traveled the world and I did the things and I hung out with my kids 24/7 and it was amazing. Then I'm like, okay, I got to get back to work. And so now it's working on chapter 2, but it was a very hard journey, but I feel the happiest that I've ever been now today. And finally being like, I did it and it's done and it's going to be great.

There's a joke that I've heard in Silicon Valley of if you've invested from venture capitalists, if you've invested in a company, and the founder starts posting on Twitter, you can just go ahead and write off the investment. It didn't go anywhere, right? Because the idea is that a content-focused CEO is going to then care more about their image or something like that than they do about building the business, which I think is— maybe there are cases that it's true. We could prove anything with a few random examples, but I think the inverse is true so often where the profile that a content creator is able to get is so much bigger than what a company, what a logo can do as a brand.

Yes.

And so I'm really curious about your experience of building an audience and that community, you know, first on Instagram and then on the podcast while running the company and how you balance those two things.

I will be very honest, right? Like we talked, I've not shared this. It was never viewed as an asset. It wasn't. It was always viewed as a distraction.

By your investors?

By everyone. By everyone. It was always viewed as a distraction. I never felt that what I was doing to go drive an audience, to go build customers. So like my audience, a little bit about my journey on like online. I started sharing, I think my first, my Instagram handle was Mom Boss. So I like, I think I still have #MomBoss trademarked by the way, if anybody wants it. And you know, Rachel, like when you become a new mom and then you're a business owner, you're like, your whole world is like trying to figure out the two balances, right? It is. It's like, it becomes like this huge thing because you're like, do I go build my business? Do I go become a mom? The world says I can't do both. And it's really hard. And I went through that and I was sharing my journey online of being both. And I was like, I deserve to have it all. I can be a great be a great mom and be a great CEO. So I was like sharing just like, I think this is when Instagram stories came out and that's how kind of how I, and I love the natural element of stories and I'm a great storyteller and it was so, it was so easy for me to do that. So I was sharing online of like dropping like Mila off to school and then heading to like, you know, Atlanta for a board meeting or whatever. And so this audience was growing and it was truly like women entrepreneurs and I was connecting with them digitally through Instagram. So fun. I actually got to keynote at Meta on Monday and it was so great to like to just literally the offices are so freaking cool. Like everything is Grammable.

I saw it on your stories.

I was, I was geeking out. I was geeking out. It was so fun. But that is how the online journey started for me was on that platform, was on Instagram.

And also you're saying that you were just talking about something that was going on for you. Yeah. Like talking about being a mom and being a business owner?

It was easy. It wasn't— I had no intention to go build like this audience, to go build whatever. It was like so fun. And then I definitely started getting a lot of the mommy blogger, like started getting things to like share and whatever. And it just didn't feel authentic for me. I was like, I'm not trying to go down a— I wasn't. And there's nothing wrong with that. It just was not what I was trying to do.

You mean like brand deals, like promoting products?

Like brand deals with like products and like all the— and I tried a few. Like there's definitely like, if you like scroll all the way back, like decades of—

Oh, I tried a few too and I was like, this is absolutely a waste of my time.

So it wasn't going to be what I wanted to do.

I mean, you can definitely make a living doing it. It's just that wasn't my thing.

So, and it wasn't what my— I had no purpose in that. Right. So, and I wasn't a full-time influencer in that. I was just sharing just hardship of like being a mom, raising capital, doing the things. And from there I had this, like when live came out, it was the audience grew from being like this mom boss audience to just women entrepreneurs who were resonating with me. And I was just showing up online. And in 2020, during the pandemic, probably had an audience. It was a small audience of like maybe 35,000, like quite sizable, but just in my own little corner of the internet, had this audience. And I had switched. So you do the mom thing for like new moms. Like we're like super into it in the beginning. Then we're like so over it 3 years later. So I like literally went from Mom Boss to Senera Madani real quick. I was like, yeah, love you kids, but I have an identity outside of you. Yes. And you go through that journey. Moms out here can relate to what I'm saying. So I went from Mom Boss to just Senera Madani. And I was still post— it was all about just female entrepreneurship. And during COVID or during— before COVID happened. So showing up for these Instagram Lives and women would come, female entrepreneurs would come and they would just ask me and it probably was like $12 to $20 million in revenue. And I was very transparent about like, oh, here's— and I probably had raised Series A, maybe I was raising Series B, and we were so like a growing company, but I was just a couple of years ahead of like what was, you know, just sharing my journey. And Instagram Live was how women were showing up. And I'm like, why are people coming here and like asking me like business questions? Like all these different types of every industry imaginable, service-based industry, product-based companies, brick-and-mortar businesses, physicians were coming to this live. And then during the pandemic, when real COVID hit, so 2020 and like March, everything shuts down. That Wednesday was my Instagram Live for like Wind Down Wednesday and like business talks with Sinara. I had over 1,000 women. And for my audience that were like, maybe like 40 people showed up to a Live, there was 1,000 women there that night. And they were asking me about, Sinara, what are you doing for remote work? What are you doing with the PPP loan? What's happening? How do you, how long do you think this COVID is going to last? Right? Like it was right. And I was like, I don't know.

2 weeks?

Like, let's prepare for the worst, a month.

Is that really funny or really not funny? I can't tell which.

I think it's both, and I think that's why we're all kind of like crying hysterically laughing. 3 years later, here we are. So it wasn't, I don't know, but I knew in that moment there was no place, like, there was no place for us to go. No, like as women, you're showing up to my corner of the internet to ask me about PPP loans. Like I'm doing it with you, girlfriend. Like we're doing it together and we got to go find the resources. And I knew then, like I didn't go to CEO school and that was it. So I pulled up my mic and I could not do the live. So I did a live every single night. I was trying to find resources. I had other people come join the live. I am not a social media expert, or I thought I was not a social media expert. And I pulled up and that is how CEO School was born and the podcast was born. And we just celebrated a million downloads. Yeah, you guys all have to subscribe to the show. It is amazing. And it was literally that week of that frustration and, and during the pandemic when I thought I had free time. And here we are 3 years later and every single week I've had a show and it has been a labor of love, but it's been all about consistency, right? I've shown up every single week. And you asked me the question, Nathan, of like, what, what happened? Like, what were the investors thinking? What was everyone thinking? What was interesting is like my intention was to go support women in business and also my audience, like the customers who could become our customers at Stacks could be women in business, right? They're like, they are our ideal clients as well. And so I thought like, what a great win. And I was also like, I know I've never had like sponsorship for the show. Our only sponsor has been HubSpot, which is like one of like a tool that I love and I use, but I've never had like ads on the show or sponsors on the show. Like I've truly felt like I wanted to have this platform to be, to bring in as much knowledge. Like I feel like education is what I bring to the table that is all about scaling your business. That's what I do best. That's what I'm bringing. And that's how like this, like I never put ads into it and it just organically grew. But the end result, I was like, great. I can also support the women through Stacks. So I always had Stacks ads running, like to be like, sign up for our solution, which makes makes complete sense, but it made even our, like everyone uncomfortable because it was like, well, you know, CEOs don't show up on social media, right? CEOs don't share what's happening on their, in their private lives.

They want you to work like 18-hour days and have no time for anything else.

No. And they don't want other people to see that, right? So if investors see that I'm doing something else, is she distracted? Right? So the word distracted is what would come up in these conversations. I remember feeling so exhausted. Tossed it, always fighting to say, like, look at the impact that this has had. Like, I cannot give this up. Like, who's going to support these women? There are not a lot of examples that are— who's doing this that's actually building like this type of business that we can— and I saw the tangible results of that. So I was going to fight for it, but man, it was so hard. So, so, so hard. So I had to work every single Saturday is when I would record it. And I had to do all of it even though it was my own company. Me. I had to make sure everything was perfectly fucking checked off the box, done the things, do the things. And I will tell you, I look back at that journey, Nathan, and I'm like, well, like if Jack Dorsey can fucking run Twitter and Square, right? And like, it's not Elon Musk can run all of these fucking companies and do like, do all the things. When women do one, like it's already so fucking hard for you to accept that I can go do this. But if I can excel at multiple things, Why is that a problem? But it is. It makes people uncomfortable. And I definitely had to go battle with even people that I loved. Like I had to go battle why this was important. And I'm so proud, so, so proud that I did not give up. And I built CEO School as while I was building Stacks still.

It was your side hustle.

It was my side hustle. And it was, it was my side hustle. And we have a small team. We have a team of 7. It's not so big, It's a 7-figure business and it's not a business that's like generating anything back. It's a great business and it's going to scale and all the things, but it's for impact. And we have a foundation and we have, you know, so many women that go through our programming and our curriculum. And we see like the statistics on that 2%, our women that come through CEO School, 47% of the women that go through CEO School scale beyond the million-dollar mark. Okay. So I know what I'm doing. What we're doing is working. And I know this is my way of, this is how we're going to change the statistics, the statistics. But it hasn't been easy, but I'm very, very, very proud of not fucking giving up.

So I love that. So you've had a huge journey related to like the amount of money you have. And I imagine your relationship to money has changed. Backstage, we were talking like, we should talk about money on this. And you're like, Yes. Like, I love talking about money. One thing I'm curious about is how— well, let's start here. What's something that you're still cheap about despite having private jet level money?

Definitely taking the jet. I was saying, like, hurts my— like, every time I see the money go out, it definitely hurts a little bit every time.

So I got a whole education at South by last year about private jets from Sunera.

Yeah, it's the greatest thing that you— time. You have to value time over dollars.

Yes, but I'm still too cheap to do it. So you're not? I'll just take my Diamond status on Delta. But I do it sometimes, like if I really need to, if it's really hard to get to a place or something like that.

But I will convert you. This whole week I was like, I did the Delta Diamond thing all week. All week I was in New York, I was in San Francisco. I'm exhausted and I spent way too many hours in the air and without a lot of my food, not with my family.

You can't beat it in terms of time. You cannot.

So there is, I would say that it depends on what you value as money. So first, okay, the value, there's different kinds of currencies. And I think that we all think about currency one dimensionally. Okay. It's not the tangible dollar. That's one value of it. It's a very important, money is energy. Okay. So we have to value currency differently. So my level of currency I would say time is my highest level of currency. So for me, hands down, I divide, I do everything into $10 tasks and $1,000 tasks. That's how simple I make it. Whether it's now worth $10,000 an hour or it's now like whatever it is, I just start to simplify it. Every single aspect of my life, I say, is that a $10 task or is that a $1,000 task? And if it's a $10 task, then somebody else has to do it. And if it's a $1,000 task, which is my value of my time, right? Or now it should be $10,000, whatever it is now. But I still go back to that. Then that means that that is my, my worth on my hour, that I need to make sure that that hour is measured in dollars. Okay. So if I am not, you know, if I'm spending that time doing something like else, am I making that $1,000 an hour or $10,000 an hour? Now, whatever the hourly rate is.

And the thing that I want to know specifically about that too is when you create a business, you create an economy. Economy, right? So you have a team, you have customers, you have agencies that you hire, you know, there's so much that is happening around the business that you can provide value for. So you want to value your time so that you can contribute at the highest level to that microeconomy that you've created with—

agree. And this, but this goes even beyond your business. I see mothers all the time, right, not delegate things out that are $10 tasks. For me, even without a business, $1,000 task for me is spending quality time with my children. When I get home from work, I want to spend time with them. And for me, a $1,000 task could be cooking with my kids, right? Although I could delegate that out, for me, that is a $1,000 task to be with my family, to be present with my family.

And it's my priority to never cook for my family.

And that's your $10 task. Right.

So like for you, it's private jets. For me, it's Chefs, like I will never live without a chef.

Exactly, exactly. So whatever, whatever, but it doesn't apply. I want to be clear here. It's not about having a billion-dollar business. We all, no matter where we are in our world today, we need to change our relationship to money today. I do not care what level of income you are at. You are not valuing your currencies. Okay, so the number one currency is time. Whatever time looks like for you, I'm not going to determine what that time looks like for you. For you, but you have to determine what are those $1,000 tasks and what are those $10 tasks. Number 1, my relationship to money luckily has always been with that mindset of time is my currency. And then I would say another currency is relationships. And I never viewed relationships as a currency. And one of my earliest mentors, she told me, people collect things, right, in their lives and their journeys. She's like, I collect relationships. And I was like, that is so profound beyond like, I'd never heard of this. And she's like, I want you to think about, and it's probably one of the best pieces of advice I was ever given. And I love to pass this on to every single person in the room, collect relationships. Not, you don't need anything from them. You don't, there's no ask, but build real meaningful relationships. And that is going to be a currency to you over time. And you don't know it yet, but that is an asset. Asset, right? That is a valuable asset. So it's time, it's people, and then there is a tangible factor to the dollar. Dollar has value and freedom of dollar allows you to have the freedom of time, right? So it is important for you to have that freedom of dollar. And so yeah, I still want to know what you're cheap about. So what am I cheap about?

I am cheap about— I'm—

and so what I will say, I'm a value seeker. So like the thing that I am like cheap about is is even when it comes to spending money, I'm all about like, I still will make sure that we are getting the best bang for our bucks. I'm all about spending money, but I always, I'm a value-driven human and I wanna make sure that my value, like that I'm getting the value. So as long as I'm getting the value, I'll spend all the money.

Yeah.

But I wanna make sure I—

You don't wanna overpay for anything.

I do not wanna ever overpay.

And everyone wants you to overpay when it's like public knowledge that you have money.

I'm on social consistently every week for 3 months and I guess it's not for me.

Yeah, I don't have a million followers yet, so I guess I'll quit.

Yeah, so all of these things, it takes a lot of time and it takes a level of execution that's beyond what most people are willing to do. And so I just encourage you to look at, okay, am I going to show up? This is within my control. The one thing that I can fully control is how I show up. Am I going to bring that billion-dollar execution? To what I'm doing. So thank you so much for joining us tonight.

Thank you.

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