UNLOCK Financial FREEDOM & Stop Wasting Your TIME | CEO Suneera Madhani

I think it starts with don't just do, know where you want to go. So, if you. know where you want to go and this can. be for your company, this can be for. your personal goals, this can be for a. hobby or an athletic goal you have, whatever it is, you have to define what. that end goal looks like so that you can. work backwards. And I'm a huge believer. in the rule of three for everything. I. can't remember more than three things, like everything is about threes for me. It's not just about getting everything. done, it's what are the three most. important things that I'm going to get.

done that are going to be towards the. goals that are going to get me there. The number one health and wellness. podcast. Jay Shetty. Jay Shetty. The. one, the only Jay Shetty. You are a self-proclaimed. highly caffeinated time hacker. And I. was like, my team and everyone was like, we want to be that. Tell us what that. means. Oh, I've gotten so much more calm in the. last several several years, but I'm. definitely highly caffeinated, that's. for sure. I think productivity is.

something I've naturally just had to get. better at as a CEO and especially as a. working mother, I have an 8-year-old. daughter and a 5-year-old daughter. I've. been building companies since I was 25. years old and had kids along the way and. so honestly time is our most precious. commodity and especially when you're a. busy mom running business, you have to. be really mindful of that. And so I feel. like I've found every which way to time. hack and I do think that I've I've a.

productivity expert, for sure. Okay, so. we're going to need all of those tips. and tools today. For sure, I think. there's a lot of our audience that. really wants to know how to use their. time more wisely, understand how to be. more productive and effective, but I. want to start off by Actually, let's. just dive into that. Let's talk about. that. Like, what did you used to believe. time management was and now having been. so effective for this many years, what. have you now come to the conclusion that. what time management actually is. Freedom of dollar is what we all start.

to chase, right? And there's nothing. wrong with that. There's absolutely. nothing wrong with wanting financial. success for yourself, for your family. And so freedom of dollar is something. that when I started my journey, that was. one component of building the business. But really it became about freedom of. time. Even if you you have that level of. success with freedom of dollar, we still. all have the same amount of time. And so. it really is about that freedom of time. and being able to enjoy the journey. along the way. I want to be able to do. what I call the thousand dollar tasks, not the ten dollar task. And for me, a.

thousand dollar task is when I get home, I want to cook with my family. Can I. outsource that? Absolutely. But that to. me is not a thousand dollar task. That's. a ten That's a ten dollar task for some. others, but for me spending time with my. family is like the number one most. important place where I'm trying to keep. my time freedom. It's really, really. important that I think about tasks in. that way. It's something I really. encourage. I mentor so many women in. business and we have a lot of. responsibility. Like there is this extra.

layer of responsibility. I'm not saying. I mean I have such an incredible. partner, such an incredible husband and. we co-parent, we do all the things. But. as a working mom, there's just that. extra layer of a million things that. have to get done. As a CEO, everyone. wants a piece of your time. How you. spend your time is it's everything. And. so really thinking about what are your. thousand dollar task and just focusing. on those and everything else, finding a. way to either delegate it or delete it.

Do we even like actually have to do it? I have this process of like do, delegate, delete. So every couple weeks. I'll do a time audit. I love this already by the way. Yeah, I do a time audit cuz your seasons. are changing. Like what you're doing. right now, travel's insane, whatever. else it is, do a time audit. So we do a. time audit and I take a look at how am I. actually spending my time? Is it And I'm. intentional about my time. How do I want. to spend my time? And so if I see, you know, certain. habits and certain things that I'm like, okay, no, this has to come off our. plate. This can be delegated off. Am I. spending too much time in one area? This.

can apply to anyone at any point is to. do a time audit and to take control back. of it. And it's also important, I think, when you ask the question of like, how. do I view time now? I used to have this. mantra that I used to say every day cuz. things are so crazy busy and running two. companies, the podcast, the kids, all. the stuff. Every morning I'd wake up, Jay and I'd say, I've all the time in. the world. I've all the time in the. world. I've all the time in the world. But I didn't. And I didn't believe it. inside because I didn't have all the.

time in the world. And now a lot has. shifted where I actually do believe. I have all the time in the world. And. that just comes with presence. That just. means that wherever I'm going to be and. I learned how to be really present in. everything that I was in, I was in with. such intention. that I did have all the time in the. world. I think that those are some ways. that have really shifted my perspective. about time, but I do think it's the most. important commodity that we have. It's. the biggest gift that you can give. yourself, to everyone around you. And I.

think the world is changing so fast, we're such an on demand everything, everything is so speedy, everything. coming at us from social media to life, to work, everyone's life. There's not. It's not a CEO's life that's busy. Every. single person that's probably listening. feels exactly that feeling. It's so. busy, but is it Is it busy or is it. full? Right? And that's the shift. I was. busy before and I learned how to make my. life going from busy to intentionally.

full with purpose. When you're coming up. with criteria for do, delegate, delete, how do you decide? Because I find that. often, especially in the beginning, and. I'm sure it was the same for you, and. we'll get to that in a second, but. there's a feeling like I have to do. everything and I probably have to. because I can't afford to delegate. You. may not have a team in the beginning. So. when you start growing or when you start. building, how do you find the ability to. decide, okay, this is what I'm still. going to do, this is what I delegate,

and this is what I delete because often. founders and startup owners or anyone. will say to me, I think everything's. important. How do I decide what's. important to do with my time? It's one understanding where you want to. go. So I think it starts with don't just. do, know where you want to go. So if you. know where you want to go, and this can. be for your company, this can be for. your personal goals, this can be for a. hobby or an athletic goal you have, whatever it is, you have to define what. that end goal looks like so that you can. work backwards. And I think that is an.

important part of even in business, especially at startups, you want to do. all the things, but you just can't. So. it's really deciding what are the three. things? And I'm a huge believer in this. in the rule of three for everything. I. can't remember more than three things. Like everything is about threes for me. And so it's three goals for let's say. it's for the quarter, for the year. How. do we work backwards that that's the. goal? And then everything else is a. delete, it's a no. And every day I look. and I I plan my needle movers is like in.

business is, you know, a very common. term, but it's not just about getting. everything done, it's what are the three. most important things that I'm going to. get done that are going to be towards. the goals that are going to get me. there. And so you have to start getting. really comfortable with saying no. You. have to start getting comfortable with. you not being the one to do it. And even. if you don't have a team, even if you. don't have the resources, it starts with. you, right? You are the core nucleus of. your company, of your life, of the.

things. That DNA then breeds into the. next your first hire that you're going. to do, and the next hire that you're. going to do. And the job of a CEO is. helping everyone prioritize. Mhm. Like. that's my job every day. My job is not. to do the rowing. So, I think about, you. know, in rowing club or like the. coxswain that's at the front of the. boat, his or her job is not actually to row, it's to give direction, to cheer. everyone on, to make sure that we're. going in the right direction. He or. she's not actually the one rowing. And.

so, your job is just to keep everyone. rowing in the same direction and. prioritizing. And that's probably the. hardest job as well is what is priority, what you asked. But if you don't know it. and if you're not in line with it, then. your team's not going to be in line with. it. Your life is not going to be in line. with it. And this is something that I've. realized that falls into like the CEO. part and the life part. Always both. It's the same. The thing that really hit. me because I've been thinking a lot. about this is the needle moving part. Because often what we think of.

delegation or roles as, we also think, "Oh, someone else will take care of all. the little stuff. I'll do the big. stuff." And actually, you're then. deprioritizing that person because you. also want them to be doing needle moving. things. And you may be doing bigger, larger, more long-term needle moving. things, but you don't want to be like, "Oh, I'm going to hand off all the. little things to someone else to deal. with." Because those little things may. actually become a distraction to you and. that individual. So, anyway, I want to. go back to when you start thinking about. building this billion-dollar empire. And.

did you know. the day you started Stacks that you. wanted it to be a billion-dollar. business? I didn't know I could go build. a million-dollar business, let alone a. billion-dollar one. hearing that. That's great. I had no idea. I was. 26 years old, no money in my bank. account. I was working for a financial. services company. I was the first person. in my family to graduate college. I grew. up in the most incredible, incredible. household. I was getting my MBA without. even knowing it. So, my parents were.

immigrants. They came from Karachi, Pakistan. I was born in Chicago, so I. was first generation here. We moved to. Texas. I went to 10 different schools in. 12 years, which is an insane part of my. story. But, it was the pursuit of the. American dream. And for my parents, it. was about allowing us an opportunity to. be anything we wanted to be, to get an. education. That is 100% every Indian, you know, Pakistani culture, like. education is so important. So, I was a. really great student. I'm the firstborn, eldest daughter, all the things. And I.

loved my childhood. Like, I loved, you. know, see my parents work really hard. Everything wasn't perfect, but we had. the best family values. Like, I was. surrounded by so much. confidence around me. My dad would wake. me and my brother up every morning, and. he was this like loud energy, like 4:00. in the morning wake up kind of guy. Every morning he'd wake us up and he'd. say, "Sunny." That's my my nickname. He'd say, "You have it." Like, that is.

what I grew up around every single day. somebody telling you that you have it, and it was the most annoying thing. They're just our biggest champions. Me. and my brothers and I's biggest. champions. And so, you carry that level of like. responsibility. You want to You want to. succeed. You want to do well. And growing up in also a Muslim. household, like, I didn't feel at all. like my my gender. Like, I was just the. eldest kid. And so, that meant that I. got I got to do everything first. Like, I never felt my gender until I went into. the workforce.

Wow, that's yeah. And not even in. college. In college, like, you know, I. went to I went to University of Florida. We had like three ships in my four years. of college. I studied abroad. I did all. of these amazing cool things. And then I. get into the workforce, and I saw that. there were no women in at any of the. companies that I worked for. I worked. for three different companies, and the. only women that I saw working in the. organizations were in either customer. support or in admin roles. There was. nobody in technology. There was nobody. in anything else besides supporting.

roles. And that was the first time that I was. like, I'm different. There for the first. time I noticed my difference. And I think it was that confidence, I. never had that negative self-talk. And. the self-talk actually started to get. created at that point in my early 20s. But I never had that going into it. And. so, I feel super grateful. And I think. that's how I try to parent as well, is. you can't over love a kid. Like that's. where the confidence comes from, especially for young girls. Because in a.

world like today, no one is telling. them. And then their negative self-talk, because of how the world looks, because. of the inequities that are plainly. there, we start to form those conversations in. our own head. And so, I'm so grateful. that I had super cheerleaders that I. didn't even know that I was rolling my. eyes at, that really carried me through, where I was like, no, I am different, and I do have it, and I can see things. differently. So, I was that bad. employee. I would challenge the status.

quo. And then, I had this really amazing. idea to go start a subscription-based. processing system. And I took it back to. my male bosses. And I was pretty much laughed out of the. room. Like it was, you know, little. girl, great ideas, but this is not going to work. And so, I. came back home, and I flew back from. Houston to with family dinners. That was. always something that always were around. food and family. And my dad looks to me, and you know, so disappointed in the how.

the conversation went. And he said, Sunny, he goes, why don't you just go. start the company? And I said, Dad, where do I go find Mr. Visa? How? I'm 25. Like where do I go build a. fintech? I don't have I don't know. He. said, you'll figure it out. And so, that's exactly what I did. And I moved. back into my parents' house. And he's. like, and if you don't, in 6 months. you'll get your MBA. Like that was it. That was it. It was as. easy as that. For me, spending time with. my family is like the number one most. important place where I'm trying to keep.

my time freedom. As a working mom, there's just that extra layer of a. million things that have to get done. How you spend your time is it's. everything. Everyone's life is busy. Every single person that's probably. listening feels exactly that feeling. It's so busy, but is it is it busy or is. it full? I loved what you said about the. idea that you can't overload someone. Like that's beautiful to hear and I. always feel that my mom's love was like.

that for me. I always grew up believing. I was lovable. My mom's love shielded me. from so much of the other pain and. stress and everything else I saw. happening around me. And a lot of what you just said about. women I see to be so true today because. I've seen research and studies that show. that if a man sees a job specification. and can do less than half of it, he'll. still apply. And if a woman sees. something and even if she can do 80% of. it, she won't apply because she can't do.

the 20% remaining. And so even when I. talk to my male friends today and I know. a lot of their wives and partners and. girlfriends and whatever else it may be, they all find that so many women are. scared to go out and then start a. company. They're scared to take that. risk. They're fearful that they can't or. they're waiting till they have. everything like all their ducks in a row. before they give themselves an. opportunity. How did early on in your. life your dad saying this repetitive. statement to you, how did that not.

become a pressure and how did it feel. empowering? Because I feel that. sometimes if you're told you've got it, you can do this, a lot of people see. that as pressure and then they feel they. can't live up to it. What was different. about the parenting aspect of that? Because I think a lot of parents. listening may take a lot from what your. dad did, right? I was always brought in. on all the conversations. I think. something that my parents did, we had. struggles and we had challenges and we. had to move and we had to various. businesses, but we were always at the. dinner table having the hard.

conversations. You know, if there were. hard things that were to, you know, taking place about money or about. business or about family, we were. solving problems together. So, my my. parents would always ask our. perspective. That is something that I I. do feel is very interesting. Just as a. child, I try to do that with my my. daughters at the dinner table now is to. ask them like what they think. So, thinking about solutions versus, you. know, how they would think about solving. it. So, I feel like I was really. involved in hearing my voice felt heard.

and I think that's important because as. women, I do feel like we're, you know, our voice isn't heard. And so, I grew up. in a place where my voice was not just. heard, it was really valued and my. perspective was valued. And just like so. many memories that I can think of. I had. such an amazing amazing childhood and I. know a lot of people don't have that. On. my 17th birthday, this is really crazy. So, we went to Atlantic City for a. Bollywood concert. It was like a Shah. Rukh Khan concert that when they would. come out and do the the shows, we went. to Atlantic City for this concert and,

you know, there was a casino. I'm not even of legal age to drink. gamble and my dad takes me to the. blackjack table, okay? And he was an. avid like he definitely had not the best. habits as well. Um and it's and it's. important to see like you you can see. both sides of your parents. Things. weren't perfect. I look back and I think. about mostly the positives, but sitting. at this blackjack table, so I'm all. dressed up to go to this concert. I'm. sitting next to him. My parents were. also really young. They had me when they. were like 20. And so, people are. probably assuming I'm like his. girlfriend or something and, you know,

but I'm sitting at the blackjack table. next to him and he hands me a pile of. chips and he's like, "Bet.". And in my head, I'm like, "Oh, how much. is this? Like, am I going to lose the. money? You know, what's the value?" And. his response, he goes, "Just feel it.". He's like, "If you feel like you're. going to win, bet more. If you feel like. you're not going to win, pull back." My. ability to now take risks and listen to. my gut and not worry about, you know, like scared money doesn't make money, as. well. Right? So, my ability to be able.

to say, "Okay, I feel. like I'm going to win. I feel like look. at looking at the hands or learning. blackjack." And I was great at math, and. I can get this concept. That was one of. my like a core memory that I can think. of, but I was always involved in the. conversation. I feel like it was more. tactical with action, not just being. told that you should go do this. I. definitely feel very blessed that I that. I did have that. And now my mom lives. literally across the street from me. She's like one rock away, and we get to. she gets to raise my kids with me, so.

it's wonderful. It's amazing. When you. when you go from pitching your idea to. all of your bosses, and they kind of. look at you like, "This is going to. fail. This isn't going to work." And. then obviously your dad gives you that. encouraging statement. You said that you. moved back home then. Yeah. So, I'm. imagining that you were making a decent. amount of money working at financial. services firm. And when you choose to start a company, I'm guessing you took a massive pay hit. And I assume you were living out, and. then you moved back home. Now, the.

reason why I'm pinpointing that moment. is because I think those golden. handcuffs that so many of us tie around. ourselves with the safe corporate job, and when you've got a great degree, and. you finally get that job you've been. waiting to get for like 18 years of your. life, and everyone respects you for it. It looks good on your LinkedIn and your. resume. I found so many people struggle at that. point to say, "Well, I'm willing to take. less money. I'm willing to downgrade my. lifestyle. I'm willing to postpone and.

delay the gratification of having nice. things." Because chances are if I live. with my parents, and and I'm not making. the money anymore, life changes. Walk. Walk through deeply that decision, because I think for so many of our. community listening and so many people. that I mentor, coach, speak to, this. seems to be one of the most pivotal. moments of their life that were you. willing to go two steps backwards in. order to go five steps forward, and so. many of us are so scared to go two steps. backwards because we've got so used to a.

certain level of lifestyle. So, walk us through that key decision. point. I actually asked myself, would I. do it again? Mhm. And I think that it. also depends on. like it's the risk-taking ability, right? It takes courage to take risk. One of my favorite most favorite books. that I've recently read is Die with. Zero. Mhm. It is such an incredible. book. It's this crazy concept of just. taking risks, and you have your golden. years of your life. Like we should be. spending our money, doing our things in.

our prime. And that makes complete. sense. And the risk tolerance that you. can take also changes with your age. Would I take these risks if I had two. daughters at home? And maybe if I was a. sole breadwinner, or where I don't know. And so, I can look back and say, I. didn't have much to lose. And it was a. level of risk. I had a steady job. I was. on a career path. I could have totally. miserably failed. I think you have to. think about not what is the risk in. doing it. I think you have to think.

about what is the risk in not doing it, right? So, what is the risk if you don't. do the thing? And that's kind of how I. try to make those the risky decisions. today. And I'm I know we're going to. talk more in this journey. It's going to. come full circle in 10 years. I left my. company at the most record high of the. company. But the risk of me staying. was a detriment to my health and my. burnout and my all the things that I had. left to go accomplish. And so, it's. really about the risk of not doing the.

action. But at that time, I think it was. I was young, and I could, and um you do. have to take take a step back, and I. would say I think social media does a. horrible job of showing us success. There's so much saturation of success. There's not enough failures that are. being shown. It's not enough It is hard. to build a business. You know, less than. 2% of female founders ever even break a. million in revenue. That is the most. insane statistic. Men are eight times.

more likely to achieve that. Venture. capital, right? I'm going to go build a. fintech. Less than Currently, 2023, less than 3%. of capital goes to women founders. Less. than 1% It's in the decimals goes to. minority founders. What was I even. thinking trying to go raise capital out. of Orlando, Florida? Not even Silicon. Valley, right? And so, I think there's a. naivete when you're young, and I think. it's beautiful. I think that it's the. most amazing thing. Like, I even think. about parenting. Like, oh my god, now if.

I knew all the things that I knew, right, when we were young and doing the. things, I think that having a little bit. of not knowing what's on the other side. is actually really beautiful, too. Like, embrace that. Now that I know I'm. building second time again, and I'm. building from experience, which means I. can catapult faster and do things. differently, but I also know what's. ahead. I loved when I didn't know what. was coming. So, I didn't know that I. could go build that billion-dollar. business, and all I did was focus on. putting one step one foot in front of.

the other every day. I showed up for a. job. I always say this, that was harder. than the one I had yesterday. Every day. I had a job that was hard cuz the. company was growing. Something else was. happening. That's a pretty cool place to. be in from a young growth perspective. So, if you enjoy that, then. entrepreneurship is for you because it. doesn't get easier. You get better, but it doesn't get. easier. I actually think what you said. makes a lot of sense that. at that time there was a sense of you.

didn't have the pressure. of the success story that social media. puts around you. And so now it's like. everyone thinks to themselves, I have to. build a million-dollar, billion-dollar. business. And as soon as you say that, it's so hard because it's such a long. journey to get there that it's such an. overwhelming mountain. And it's almost. like you're standing at the base of a. mountain and it looks so high and you're. just like, how am I ever going to get to. the top? And I remember the same like.

when we launched our podcast, I didn't. have a number of downloads I was trying. to reach or I didn't have a number of. followers that I was like, oh this would. be success. It was like, this is what I. love, this is the stories I want to. tell, this is how we want to serve our. community, this is the experience we. want to build and that's how we started. And then of course everything got more. strategic as we developed and we learned. more and everything, but I didn't have. that pressure on day one and I think if. I did, I may never have put out a video, I would never have put out a piece of. content because. it was going to be years or months or.

days until you actually reached this. false goal you set yourself. So, when. you're starting out, how do you set. goals that are empowering and not. debilitating? Because I see a lot of. founders setting very debilitating. goals. I think the goals have to be in. line with why are you doing what you're. doing? I think that the numerical. success will come from it. But if that's what you're defining as. your goals up front, you're not going to.

That's That's where the mountain gets. really high. Versus if you're really. just showing up to go serve the five. audience members that you were like, hey. I just want to do this podcast and I. just whoever listens listens, like this. is what I want to do. When I first. started the business, I knew that there. was a gap in what I was what we were. doing. I literally sold the first 100. customers out of the trunk of my car. This is when like payment terminals were. like a real thing and I would carry them. in that my car. I'd I'd go around. shopping plazas. It was just a. completely different I had to go meet my.

customers where they were at. And every. day my goal was, I just want one person. to say yes. That was it. That's a great. goal. That that's it. And so if and I knew. what I wanted to serve small business, I. had such a passion, I knew what I could. help them with. And so it's really. important to stay focused on that. And. it's hard. Like I really that empathy. comes from a place because I find myself. in that now cuz I think social media. makes it really really difficult. We see. living in this comparison culture, living in it's hard not to when you see. you see and it's nice. It's also nice to.

see success because you're like, "Hey, that's possible for me." There's an. amazing truth in that and you should. have I have my I make my vision board. every year, right? And if I'm not going. to have big visions and big goals like I. I do believe in the power of dreaming. big. But you have to stay rooted in showing. up for that one person or that one. customer and building your product and. solution set to really serve. I think. that that's where most of the most. successful companies come from and.

that's why I love women in business. Like I love love meeting and I get an. opportunity with everything that I do. with the podcast and CEO school to just. meet and mentor so many women. I never. meet a woman who's just started the. business or a business for the sake of. it. Every woman I meet is building a. business because somebody wasn't solving. something for their kids school. Some. somebody wasn't solving something for. their industry. There is a a technology. that they see this world in a different.

way that no one's solving for. There's a. greater purpose and she's the last one. She's so exhausted from nobody solving. it. She's like, "Screw it. I got to do. it. I got to do it." And that's. literally how women are starting. businesses. We're not first to raise our. hands to say, "Oh yeah, entrepreneurship. is where we're at." We're solving real. problems because we really care and I. think that's the the empathetic part, the nurturing part, the problem-solving. part of women and women actually end up. becoming the most successful investments.

for venture capitalist. Women actually. end up becoming. the most incredible leaders in. organizations. I do think that the world. would look very, very different in the. environment that we are in today if we. had more more women at the top across. the world on a global standpoint. So it. is important because women build with. purpose and and I think that that's what. you have to you have to stay grounded. and if nothing's going to take you there. because when you talk about those goals, Jay, as soon as you start to reach if.

it's just the goal, before you even get. to the goal, you're raising the goal. again. Before you get to the next goal, you're raising that goal again. You have. to check yourself in that and I fell. into that trap. So once we started to. get the success and we started to grow. the business, our first year we did 5. million in payments through our. ecosystem. Within year five, we did 5. billion. It was real, it was hard, it. was fast. We were scaling, we were. growing and then I just became a product. of living in this.

fintech boys club. and defining success on everyone else's. terms and I stopped checking in with. what I actually want. I stopped checking. in with what my customers really wanted. I stopped checking in. I was just. building because now there was this. playbook of this tech playbook. This is. how we this is series A, B, C. Here's. what's next. Here's how it's all about. value. It's all about this. It's about. acquisitions. And I definitely have a lot of lessons. from building in that way that I had to. really check myself when we reached the.

top. Don't just do, know where you want. to go. Whatever it is, you have to. define what that end goal looks like so. that you can work backwards. Social. media does a horrible job of showing us. success. There's not enough failures. that are being shown. I think you have. to think about not what is the risk in. doing it. I think you have to think. about what is the risk in not doing it. The statistics you mentioned a couple of. moments ago about the number of female. founders, funding going to female.

founders, those are so alarming. and they're not even close to being. good. No. Like they're they're so far behind. What. was some of the blocks and the barriers. you saw for women that you had to learn. to navigate. And how would you encourage. women who are in that space right now. because it can get so easy to get. discouraged. It's so easy to become. bitter. It's so easy to become. completely disempowered. And by the way, all of that would be extremely valid.

based on the statistics you just shared. What did you learn that if you were. like, here are three lessons, master. classes, moments of navigation that I. learned that helped me play the game and. figure it out as opposed to give up on. the game and quit because it was too. hard. What would you say were the. biggest three things that you were like, these three things taught me how to play. the game and I had to learn to navigate. these in order to win in this world? I. would say the first thing is to build. your network. Like that is the number. one thing. I think what has made the. boys club so successful is it is they.

they do business on the golf courses and. through relationships and through this. college and they went to this school and. there is a network. There is a boys club. network. We haven't had an opportunity. to build a network. We've only been on. the workforce, you know, since the. 1940s, 50s, since post World War. Like. the business world has not been designed. for women in mind. And so it is. important to start building that network. immediately. And so get out of the. screen, get into the room. So that's.

like the number one first piece of. advice that I have for every woman. building everywhere. is build your network. And the boys club. isn't bad, right? And so you find the. right supporters, Find the right allies. And so, I had the most incredible I had. two male co-founders, my brother and my. other brother. And so, we built. alongside and I had the most amazing. mentors, male mentors that had been. there, done that. And so, I do think. that you have to find the right men.

around you for support as well. So, seek. allies and ask for help. point. Because the world isn't one or the. other. People do want to help. And I. think as women, this goes back to like the number two is. that we carry all of the burden. We. carry all of this extra mental pressure. We carry all of this self-talk, the. doubt. And again, all valid, but we. never we're the last to ask for help. We're always pouring into everyone. I. see this from my own mother. I see this. me as a mother. I have to remind myself. that I need to be poured into as well.

We're just that's how our DNA is. This. is how we've been physically designed. and built from our primitive years and. days, you know, from the stone ages. That's what our jobs were. Nurturers. We're We're part of But we were part of. the village, right? We didn't have to do. it alone. In this world, why do we feel. like we have to do it alone? And so, get. comfortable with asking for help. So, getting those allies super super. important. Third piece of advice that I. have for female founders is to do it.

anyway. Like go for it anyway. And so, there's going to be a lot of noise. There's going to be a lot of people that. are going to doubt you. Every time you're going to step into a. room, there's going to be somebody and. I've experienced this in every room that. I've been been in. I can name countless. stories of the misogyny, of the sexism, of the racism, and even the ageism, right? Like even being young, you're. doubted. I can think of my first CEO. conference when I did got investors.

with, you know, venture-backed, you. know, and it's not anyone's fault. It's. just I I first portfolio company that. was founded like that was a female. founded portfolio company and I arrived. to this conference and every CEO walking. in through the door. stopped me and be like was like, "Hey, where's the event? Hey, where do I get. my name badge? Hey, where do I get" They. just assumed that I was like the event. manager. Until, you know, one of the LPs. was like, "And welcoming our newest. portfolio CEO, Sadiqa." And then their. faces, right? And so just ignore it as.

best as you can. and you just have to keep showing up in. those rooms and. be authentically you, right? Like I. think that's if I would like that's the. third piece of advice is it took me so. long to get comfortable with. fully it showing up as myself and I mean. it's not my fault. I had to put on a lot. of armor. I was one of the only women in. the boys club and there's so so many. stories of how I would show up. I called. myself a man in a skirt. It's like how I. would dress. I could not eat another.

steak at a steakhouse. Like it was like. I was doing all the things to fit in and. that's natural. That's human tendency. You want to be part of the club. So I'm. not going to disrupt the norm. But you know, I think that where the. change really happened for me was. standing up to my board and to the team. and being comfortable in leading the way. that as Sadiqa. that came later for me and it came. through confidence, right? Came through. like doing it and finding the cur like. the courage to be confident in my own. ability. But I wish I found that sooner.

So my third piece of advice is to just. to do it anyway, show up in the rooms. and show up as you. You don't have to be. a man in a skirt. Like be exactly how. you are and I think that the world is is. I think it's changing, Jay. So I think. it is it's getting better. The. statistics aren't there and I've got. thoughts on why the stats aren't there. and it speaks It's because we're not. holding institutions accountable. There. is an accountability component. does not change unless you hold somebody. accountable to it. So venture. capitalist, you know, where is is.

funding going? Why aren't we mandating. that at least percentages of these funds. go towards women-owned businesses, lending, banking. That's exactly why. we're building Worth again. I did not. want to go be a serial entrepreneur. I. am exhausted of building businesses. But. there isn't an equitable landscape and. we have to hold institutions accountable. as well. And so, I'm trying to do that. by standard by standardizing the. business credit score and holding. institutions accountable for equitable. lending and for an equitable financial.

ecosystem, but I think that those things. have to change as well as our consumer. beha- as well as so many things. Like. there's so many things that have to. change and I do believe that the. dialogue is happening, which is. important. That's where it starts, but. action comes from doing. And so, that's going to be the next big. step and I I'm really curious to see how. we're going to do that in, you know, in. my generation. I want my my daughters'. generations. I want my kids to I have. two daughters for them to grow up in a. world that they can be and do and.

right now they have no concept just like. I did, right? And so, I'm raising them. in the same way and they're so strong. and so independent and so cool and so. different and. all the things and I hope that that. continues. Like they can always continue. to be themselves and have that positive. dialogue not just from me as a parent, but from their own from their own self. because the world hopefully looks. different for them. Yeah, no, great. great advice and you reminded me of a. story I had when I was in England. I.

heard this speaker. talking about and I may get the date. wrong, but I think she built a big tech. company in the '80s in England. She. talked about how. when she started out, she used to call. other CEOs and she'd pretend to be her. own assistant. Yeah. And she'd say, "I'm setting up a. meeting for Steve Shirley." Her name was. Stephanie Shirley. And she'd be like, "Hey, I'm calling on behalf of Steve. Shirley. Steve Shirley would love to. come and meet you. The person would book. in the appointment and then she'd turn.

up as a woman. They would be like wait, how's your name Steve? She's like oh, they go I go by Steve cuz I'm Stephanie. And her name became Steve Shirley. because that's what she was known as. And that's what it took. And now I'm. hoping times are changing and things are. shifting, of course drastically since. then, but still that feeling of women. feeling like I have to go to a. steakhouse, maybe I have to hang out. here. We're hoping culture's changing, but if we're completely honest, if you. didn't do those things, would you be. successful today? I don't know. And.

yeah, no, it's it's such a valid point. This is a conversation we're having with. friends last night at dinner. You know, a friend asked, what would I. look back and do different? And so many. things is what I want to say, right? Hindsight's 20/20, but the truth is. nothing, right? Because it it took me to. the next step and it took me to the next. room and it took me to the next table. and the next conversation. And it made. whatever decisions I made allowed me to. for for me to get that, land that. customer. It's me to land that. partnership and that investor and I do.

think that it is important not to lose. yourself though. And so although I was showing up at the. steakhouse and at the things like I. would invite my counterparts to come. like to see it from a different lens and. I'm always like every one of like my. investors, mentors, like they're all. probably rolling their eyes laughing at. like this is like typical scenario. conversation is like how they can be. better for us too. Like okay, next time. instead instead of the next year at that. conference, uh my wonderful investor and they're so. incredible. So that was not their. intention to make me feel left out with.

and it was a golf tournament with on the. second day. Of course it's a golf. tournament on the second day. And so they set me up in a spa. appointment, which was so sweet of them. But I'm not here to go to the spa. I'm. here to network with other CEOs and get. business done, right? And so I ended up. just riding the golf carts, right? And I. ended up riding the golf carts and we. had such a great time and like by the. end of it, you know, next year they're. like, "What should we do different?" And. I'm like, "Nothing. Just invite me to. the golf course." Right? And maybe I'm. not going to golf, and maybe I may leave. early from a dinner, maybe I won't stay.

overnight at a conference cuz I've got. my kids to go like to get home to, but I want to be invited to the like I. want to just be part of the thing. I. don't want to have this like curated. extra experience. Since I'd always. invite them, like they would invite me. back into that conversation of what they. could do better. But I don't think if I. voiced it, they wouldn't have known. If. I just went to the spa, didn't say. anything, right? And so I do think that. that's where I was, you know, the early. parts of having your voice heard is. important. You can't make change if.

you're not going to express those ideas. So you have to get comfortable, and it's. hard. it's so much easier said. It takes. courage to do that, but I think if you. do it in a way that's kind, and if you. do it in a way that's loving, and if you. do it in a way that's empathetic, and. it's not belittling, and it's not oh, you made me feel. It's not you language. It's I'm really excited for this, and I. see a lot of good in people. And even. though I faced a lot of the things that. I faced, I knew that very very few times.

where I felt that I was malicious or. intentional, but most of the time it. wasn't. They just don't know. They they. just don't know. And so I think if you. invite people into a proactive. conversation, a co-created conversation, that change can happen that way. And. that's how I was able to navigate the. boys club once, doing it again. I mean, fine, it still hasn't the like the the. fintech space is it's different, but I. do think that uh we can co-create a more.

beautiful experience for all. Yeah, no, thank you for being so honest as well, because I think it's. like you said, it's been 10 years, and. it still hasn't changed drastically. It's changed a little bit, but your. ability to deal with it positively and. proactively has helped you move along. And one of the things you did, and you. said to me like you built your business. with family. Yeah. And that's rare I. feel as well in this day and age. I feel. like there were companies like a century. ago which were family built, family. owned, they passed it down through. generations. Family built businesses are.

more rare now, and I've even had a lot. of friends and family members that I. know that have built things with their. friends, investments, companies, and at. some point there's a break off, there's. a breakdown in communication, there's. potentially distance that's created, and. I think people can sometimes be quite. naive and trusting when they go into. family-based or friend-based businesses. And at some point the friendship kind of. changes because of money, the family. falls out over money. Generally money.

seems to be this force that has the. power to break some of the deepest. bonds. As someone who's built a successful. relationship with their family and built. a business at the same time, what three. warnings or cautions. or clarifications would you put into. place for anyone listening right now. thinking, "I'm starting this with my. friend, I'm super excited. We love each. other, we don't need anything. Contracts, forget it." Or someone with. their family is just like, "I Of course. I trust my family." What would you be. three things you'd lay out for them to.

say, "Here's how to get it right, and. here's what we did." It's definitely. very rare. So I and I've seen it with my. own friends firsthand of what you're. saying is so true because you go into it. with that level of trust, that. excitement. With my brother, when he. came into the He came into the business. a year after, almost a year after. He. was supporting me on a back end, and. then when things really started taking. like taking off, I needed help, I needed. to grow, and he was an expert in. different things. And I think advice. number one is don't just partner up for. the sake of partnering up. We definitely.

had so much trust. Me, we have the same. DNA, right? Like there's like same value. system, every like there's nobody in my. life that has gone through almost every. life experience with me than my brother. Like that's such a cool bond as siblings. that you get to have, right? They really. understand all of the the craziness, the. family stuff. They They're really your, you know, the other half of you in a. different way in your primary part of. your growing up. So we had so much. trust. Everything that made me great.

made him great. Everything that, you. know, would be things that maybe messed. us up messed him up, right? So we had. this true bond. But he was different in. his skill set. I had really strong. strength in people and brand and. marketing and just the ability to. inspire and get talent and drive. He was. so great at sales and operations and. that was the skill set that I needed. And so I think advice number one is. stay in your lanes. So I think where.

what happens is like when you're, you. know, in each other's lanes, that's. where it becomes tough. So having clear. roles and responsibilities and then. that's where the trust component comes. in because if you really trust each. other, then you have to let them. run it the way that they would run it. And they have to trust you in running. that lane the way that I would like that. you're going to run it. And so I think. that that's number one is to divide and. conquer. Number two, you brought up. money. Money is it's tough, right? And so in it. that is truly what has I've seen broken.

families and relationships and. one thing that, you know, when Sal came. on board I could have maybe offered a. different equity stake or when we're. like trying to figure out how we're. going to do this. and we it was 50/50. It wasn't even a. question. And even though I was start. like started the company first, whatever. it was, but I knew that I never wanted money to. be our relationship is the most. important thing. And so I never wanted.

to build like what if the the business. is going to fail? We're going to have. success, we're going to fail, we're. going to I didn't know what what was. going to be the outcome, but family is. forever. Like I didn't to ruin that. And. so, to avoid not letting money come in. the way. And I know this isn't practical for many. people. But, that was the reason why it was. 50/50. I got 2% more because I'm 2 years. older. So, older sister rule like that. I love it. So, that was the deal. And. actually, this company now we're we're. building again together. And this time. he has 2% more to make life fair.

Um yeah, so but we came from a place and. what that allowed, it wasn't about me. feeling great or him feeling great. We. both came from a sense of partnership. Mhm. And so, every decision that you. make and whether that's with your friend. or with your spouse or whoever you're. doing a a business partner that you're. doing business with, if you guys are coming at it from the. same equitable. lens, then you know that like there's. that extra level of trust because there. isn't any other gain or benefit for Sal. or for myself. There we're always coming.

at it for the same outcome. And I know. that's not perfect for all kinds of. businesses, but it's all about value, right? Where there's not that disconnect. is when someone doesn't feel their. value. And so, really sitting down and. understanding the value component of it. is super critical. And then, just advice. that it is important to talk about what. happens if it doesn't go well, right? So, to have Have that conversation. conversation and to have things in place. to say if it doesn't go well, here's how. we're going to solve through it. But, I.

think it's it's not just having the end. in mind. We actually never signed a like. a contract. So, that's actually I'm. giving the advice, I never take the. advice. And I will say, what did get us through. it is any business partnership business. is personal. Like, period. It's a relationship. I mean, you were. the guru of relationship advice. Like, it is you have to nurture this. relationship. You have to spend time in. this relationship. It's a relation you. have to ensure that the other person is. feeling seen, heard, valued. And you've.

got to ensure that there's strong. communication in the relationship. So, Sal and I we're siblings. We fight more. than any like it is non-stop. Like I. disagree with him a hundred times a day. A hundred times a day. But we also make. up very quickly because the way that I. talk to my brother there's probably. nobody in the world I could ever talk. to. That is like it's just how siblings. work. But we have great level of. communication and we got an incredible. coach to support us. We had almost like.

a therapist, business therapist. Because. that's what this is. It's a. relationship. And so I think it's never. too early. So if you do have a. partnership to have a third party that. you can communicate just like couples. therapy. Right? That you can go to and. you're like we're both committed to. making this work, but it's so annoying. when she does this or it's so annoying. when he does that. And so it's not. coming from a lens of. me against him and that there is like a. third party there. That's been super. helpful and just building upon that. communication. So trust is super. important. And that and that.

communication it's where it goes wrong. is when you start brushing it under the. rug. Right? When you're like that's. where resentment forms. Where. relationships fail, business. relationships, personal relations it's. resentment. We don't talk about it. We're not addressing it. We're not co-. we're not fighting a solution for it. And then the next time it happens you're. like oh remember that last time that. that happened? Remember that So like all. of this triangulation, that negative. conversation. I'm a huge believer. I'm like always heart on my sleeve.

Always. And so that's what's worked just. be honest and have those conversations. and if you need help then get that third. person involved. But that's been what's. worked really well for us. I think. there's something to be said for. relationships where you already have a. deep understanding of each other. When. Radhi and I started Juni together which. is our tea company. it was so much about leaning into each. other's strengths and trusting each. other with what we knew. So I know that. Radhi deeply understands flavor profile. She really understands ingredients. She. knows what's good for people's health.

She's that's her world. Like that's. that's what she's dedicated her life to. She's a nutritionist. She's a dietitian. She has a background in that. And so I. can trust her with that. And then I love. storytelling. I love symbolism. I love. aesthetics. Like that's that's my world. And I love the idea of how something can. become a part of someone's routine. And. you know, we have a drink for the. morning and a drink for the evening and. a drink for midday pick me up. And I. understand how people need to use. products in order to feel better.

And when there's that trust and that. understanding, now it's like, okay, we. don't need to tread on each other's. toes. But we'd been together for. probably like. 9, 10 years when we started something. together. So there's such a deep. understanding. Whereas if we started it. in year one, chances are it would have. been a lot more difficult. And so I. think if you are building something with. someone you know, if you know them well. enough, it's more likely to be effective. as opposed to like, oh, we just hit it. off and we kind of got some chemistry. And then, you know, you don't really. know them well enough. But I wanted to.

ask you something. Something that I want. to pivot slightly. because I think it's something that I. talked to a lot of people about. And I think you've nailed it. And we we. kind of touched on it in our previous. conversation before before we started. recording. You built a business in what. is a background product. Right? In the. sense of it's not consumer-facing. directly. It's not something that. everyone would come across. Yeah, it's I call it unsexy money. And. it really And it's And I think it's the. coolest type of money.

There's a lot of pressure these days. where everyone thinks, I have to have a. social media following. I have to build. a brand that's known online. I need a. viral brand if it's going to make money. It has to be consumer Like we put this. weird pressure. And I always think about. like I used to work at Accenture. And I. used to think about the amount of things. that Accenture acquired, things that. Accenture worked on. And I'd always be. like, no one's ever heard of these. companies. And there are founders here. who are winning massively. And I feel. like this generation might be missing. out on the businesses that solve real. problems that affect millions of people.

behind the scenes, that the opportunity. to scale really, really fast because. we're too busy trying to grow an online. following. And so, walk us through that. understanding of how you encourage. founders to find their niche and build. their product and think about what. they're doing because today it's been. like, "Oh, well, if my brand hasn't had. a viral video yet, it probably won't. become big." So, so walk us through that. a little bit. It's done so much good, but it's ruined us, right? Like it's. ruined us in so so many ways. We have to. stop doing things for the gram. We have.

to It is It is our mentality of building. companies, products, services that if. it's not this and it's not that. And I. also think that it's important for us to. have a social presence and to utilize. all these tools that we have. So, there's so much good that can come from. it, but it doesn't have to be all of it. And so, I do think it's important. There's so much opportunity out there. Most entrepreneurs that I know of. personally that have been really. successful came from a corporate. position that like saw something and.

then they wanted to go tackle this one. unique problem. And these unsexy. businesses are solving the most complex. problems for us. So, we did $40 billion. in payments through this ecosystem that. I almost didn't start. If I didn't build. it, we we solved huge problems in this. It was so unsexy. Card present versus. card not present. So, Stripe was focused. on digital transactions, Square was. focused on in-person transactions. Guess. what? There was nobody bridging the gap. for like dentist offices that needed. both in-person and online transactions.

Boom! There was the opportunity that. nobody saw in building that tech. And. it's not about I didn't have the. background. I wasn't a coder. I wasn't. an engineer, but I could see where the. world was going. And I think that's what. entrepreneurship is. It's this spirit of. solving for problems. It's not for show. Success will come if you just like let. go of that. And you can also have a. social following and build a great band. and have the podcast and do the things. to go reach more people, but you can.

solve if you just focus on solving the. problem and seeing it uniquely. And if. it's one of you, you're really like it's. resonating with you cuz you're like I am. that person. I I'm always finding like. you're in the shower and you're like. this should be better. This could be. better, right? You're you're always. finding the next thing. But ideas don't make you an. entrepreneur. Execution does. Right? Everybody has ideas. It's really. about execution. And that's the thing. I. feel like that's the thing that I saw. maybe in like Sal and I growing up was.

like you got to put in the work. Even. after everything that I have, I show up. every single day and I work. I put my. head down at night and I ask myself did. I like give my 110? I work so hard. still. And it's just part of and yes, I work. smart too. So it's not that I'm not just. grinding my way. I'm being intentional, but hard work is a huge part of it. because there's no such thing as a. billion-dollar idea. It's a. billion-dollar execution. And to. execute, it's every single day. You just. got to keep showing up. And like that.

mountain, the mountain's going to be. there and then you're going to climb it. and guess what? You're going to get to. the top and you're going to climb this. thing the next the next day, there's. another mountain and there's another. mountain. So you've got to love that. that challenge. That's what. entrepreneurship is. It's not I didn't. build a billion-dollar It took me 12. years to build that business, 10 years. to exit that business. It didn't happen. overnight. It happened because I just. kept showing up. It wasn't this magic. formula. People ask like, what was the. secret to the billion-dollar success? I. didn't give up. Like I just somehow kept.

showing up. I can name every founders. like every journey where we almost. didn't make payroll. I had to put my. mortgage on the line. We had to do We. didn't get the investors. We lost the. customers, but you just keep going. And. so you have to find that why to really. power you through. And for me, it was I. just love to solve really big problems. And that's why even after I exit, right? It's like here I'm back again in in. building again, it's because I see I see. the problem. and I know we can solve it. Yeah, I I. think you're the right person to ask. this question to because you talked.

about working hard and working smart, but what was the mindset shift in. building a million-dollar business, 100. million, and then getting to a billion? Like, what changed? Because I think. there may be people listening who've. like built the million and they're like, "I want to get to 10 or 100. I don't. know what's What do I need to do. differently?" Because I think at every. level. there's a different mindset, a different. type of work that's required. And often. we don't talk about that enough, and so. you keep doing the same thing again and. again expecting a different result. As.

Einstein said, is insanity. What was. different? What did you find that you. had to up-level to go from one to 100, 100 to a billion? You're brilliant. because everything has to change. It's. completely different. Going from your. zero to six figures, you know, getting. that validation of your It's a. completely different journey from zero. to six. From six to seven, it's a. completely different journey and. everything breaks and it's supposed to. break. Going from seven to eight figures. in revenue, it's going to break again. Your systems are going to break, people.

are going to break. It's going to break. because it's supposed to. Once you get, you know, you get things right or you. you think you get these things right, if. you're doing what you've set out to do, which is go get more customers, go get. more revenue, there's pressure on that. system. And then you've got to. recalibrate. You've got to recalibrate. the tools, you've got to recalibrate the. next level of scale. And so, it is. supposed to break. But the one thing. that's not different, if I look back, so. we had to change our mentality on. growth, we had to, you know, get new. technology. It's scale is it's not.

simple, but if I were to boil it down, it comes to three things. It's people, process, and profit. You've got to scale. your people, you've got to scale your. process, and you've got to scale your. profit. Most companies that go beyond. that market validation of million in. revenue and you're trying to get to the. you know, or the 100 million in value, they have multiple lines of revenue. And. so you're thinking outside of the box. So once we were acquiring small. businesses, we've shifted to an. enterprise strategy. Now I'm building. again, we're selling directly to the. banks, we're going directly to. enterprise first because that was the. one-to-many that I It took me 7 years to.

unlock that next, and then I'm going to. go to small businesses to you have to be. able to tap into that scale of people, process, and profit. But the one thing. that I would say stayed exactly the. same, and it was so important for me, I. wanted to be the one to see the company. through to exit. And I worked so hard at. being overprepared, over all the things. so that I could be the best CEO that I. could be. Like I put so much. intentionality behind working really. hard to be the best leader that I could. And the thing that carried me through.

that was exactly the same was our values. in the company. I think we hired the. right people, we fired the right people, and those decisions are hard, and our. culture was really built on the value. system. I mean, I have one team tattooed. here on my arm. It comes from that that. means me and my brother. We're one team. We're We're one team, one dream. Like. that's That's how it's been since we. grew up. That's what I wanted our team. environment to be like. And so building. that culture, the DNA value system, and.

those core values, those don't change. Those evolve, but that needs to stay. grounded and the same as you're scaling. Then you just shift into Those are just. like It's just the next playbook. Mhm. It's a different heart at the next. level, but you can solve it. And you can. find people to solve it. And then at. that next stage, we had amazing leaders. at the you know, 100 million-dollar. mark. And when I started the company, the name of the company was Fat. Merchant, by the way. Cuz I was 25, you.

know, it was. It was fine and we were disrupting the. industry, but I knew Fat Merchant was a. $100 million company. Stocks was a billion dollar company. And. I had to get comfortable even though it. was my to make those pivots, to make. those changes. And so you've got to see. where it's going and you've got to be. willing to just throw it away and just. start again at that, you know, to bring. in we had to bring in new leaders. That's hard, change is hard for. organizations. And so you you've got to go build and to. be willing to willing to change. It's.

supposed to break, so get comfortable. with it breaking and you just get. better. It doesn't get easier, but you. get better. But as long as everybody. that's coming in through that door has. that same that that value principle and. that's something that I think it's the. most important thing. I I was so tired. of hearing my entire career Sonia, you. take things too personally. Oh, wow. And. I do because it is personal. It's the most personal thing. I spend. I had this company before I even had my. children. It's my first baby. All right, like I give that much energy and love.

even for for work, right? Those that are. in the workforce, like you spend more. time at work than you do anywhere else. It is personal. You don't leave yourself. at the door before you show up on Zoom. Or you shouldn't be expected to. And I. think that we can create and I have this. vision of a world in, you know, a. working world where we do bring the. human first. And we've we had the most. tremendous. leadership and people and it's been so. amazing to be able to build again with.

that same value principle and it's just. come it's the first component of it. And. who like you are the company you keep, literally. You are the company you keep. And so that DNA is the most important, so don't change that. Has to be. reflective of your value system. And. then the rest is just a byproduct. I really appreciate your highlighting of. just. how many challenges there are to solve. and how it's actually normal for things. to break every time you upgrade and up.

level. And by the way, this includes the. team that's working, too. Like, I look. at I couldn't do anything without my. team. It just wouldn't be possible. And. the people, process, profit point is is. so brilliantly laid out for anyone who's. listening right now. Like, I think those. three things are so pivotal in an. organization. And people being able to. constantly solve after a break, that. resilience and grit that's required by. the whole team, not just by the leader, by the whole team.

That's so pivotal. And I was going to. ask you because the. I'm listening to you now and I'm. thinking there's probably at least like. I'm reckon I reckon you have a minimum. of 100 stories a year of things going. wrong. And I was going to ask you, what. was your darkest day as an entrepreneur? Like, what was the toughest day that you. remember where and and. how did it feel and how did you deal. with it? Surprisingly, my toughest days. were actually after I achieved the. billion-dollar value. I sold the company.

twice, which is also very of an. interesting journey. And I did the. things that I wanted to do for my team. So, I carried that my team with me. We. made record-breaking success for our. investors, for our team, all the things. And then the next year we like I got. distracted. As I had mentioned, like I. was chasing something that I didn't know. that I wanted. And so, it was like, "Boom, we did you know, it was 220. million." I think was the the 2020. valuation and exit where we cashed 70%. out of the company. So, whoever owns.

shares, like everybody made money. It. was And it wasn't just about the. financial. It was meaningful in a sense. of like. when you get to exit something, when you. get to like take it to completion, it. feels so good. Like, it was just. incredible. And then got heads down because it was. now what's next? It's let's let's keep. growing. Let's get it to the billion. Let's IPO. Let's go, you know, do what's. next. And I got heads down again in 18. months just building and grinding and. building and grinding. The only things. in my life were my company and my. family. Like that is all all it was. My.

health was deteriorating. I was at the. worst worst health. and I actually had never gone to a. doctor because I I think women can. relate to this. Like my OB was my doctor. for like cuz I was having babies in. between and Faisal and I were, you know, planning a family and that was it. So. for 5 years my only doctor was my OB and. I had to go to the doctor because. it's like not the most prideful thing I. can say, but we had to get like key man. life insurance before our series D. You.

have to like do these insur- which which. means that like I had to be tested if I. was healthy and what my insurance policy. as a CEO was. So I went to the doctor. because I was required to for work and I. got my report card back, which was my. health report. And I was quite literally like a. 57-year-old man. Like I actually became. the pale, male, stale CEO. Like I. literally became him. And my health was my cholesterol, my. cortisol, everything was like I didn't even know. Like I had no clue.

And you know, I had lost my father the. year before and it was just hard. It was. like what am I what am I doing this for? And we had our series D coming up and. it's brutal. Like going through some of. these fundraising like with big bankers. and investment bankers. I was on the. road. I had to do 40 plus fireside chats. with the most incredible, you know, large private equities that like in. finance you like, you know, you have. your your from a central like you dream. of like being in front of like the. Blackrocks and the KKR's and like it was.

so fun and exhilarating in a different. way, but it was hard. I was on the road. and. we accomplished what we set out to do. was to go, you know, close the series D, bring in other minority investors. We. were 100 plus million in revenue and so. it wasn't even a fictitious value. It. wasn't a value based on like, oh, here's. this tech value multiple. We had a. hundred plus million in in revenue and. we closed the round 1.1 billion. Everything I'd ever dreamed of. The. whole we're in we're an Orlando-based. company, which is a huge deal. We're the.

first unicorn out of Orlando, out of. Florida. Like so many big moments. We. had the community it was a big milestone. to celebrate. So, we had this huge the. mayor's like everything's there. All of. this excitement around this milestone, around this series A, around this. valuation and around this exit. And when. the party was over, it happened so fast. Like it was like 2 weeks of all of this. and then it was back to work and I went. to my next board meeting and it was. like, here, here's the next now it's 2. billion. And it was the first time that I was.

like, do I actually want to go do it. again? Like and I felt the most emptiest. I had ever, the loneliest I had ever. felt. And it's because what happens when you. aim for the moon, but you actually land? I've no goal. And I did everything that. I wanted to do. And so, I did what most. typical tech founders do is I took a. sabbatical, took my family to Europe and. it was really just to spend time with. myself and to really ask myself the hard. questions of what is it that I want to. do next? And then, you know, we had this.

big plan laid out for the next. transaction or maybe going to, you know, IPO. We had three acquisitions at that. time and. as like a student of learning, like I. get really excited about just learning. I'm like, oh, I want to do something. that I haven't done. And going public that was just like on. the, you know, on the checklist. But I came back and decided that I was. going to leave my job. I said I was. like, I have to this is not for me. anymore. And then I was And also the organization. was quite large. You know, as you can. tell I'm a people person. My love.

language is quality time. And so, it was. just time for me to hand over to another. team that was going to take it from that. billion to two or to the next milestone. and to the next level. That was when the. transition really began and I spent my. entire like adulthood to fight like. building this. My work was my worth. It. was my only identity. And it was so hard to shed. like what was next. And so, that was it. That was like the toughest moment. It.

was the hardest decision. I had many people think that that was. like the craziest thing to leave at that. time. I left a lot of equity on the. table. I'm still a huge I love this. company. I'm a big shareholder. It's. always going to be part of my story. I'm. always going to be the founder of. Stocks. But I had more I wanted to do. And impact was an important part of it. and taking care of myself and. getting to know myself and I lost a. decade. And I wouldn't change it like we talked. about. I wouldn't go back and change it.

It's like it's literally given us the. most incredible life. It's given me all. of these opportunities. I would do it over again every single. day. But now I just want to be a lot more. intentional. And I get to come from a. place of where I get to build again and. it's not about freedom of dollar. anymore. It's about freedom of impact. And I get to use my time and my. resources and my connections and the. network and to go build something. incredible. And I thought maybe I'd. retire right after, right? So I was. like, "Okay, maybe I'm going to you. know, come off. I've got the podcast. I.

love meeting amazing women and. supporting female founders.". But when if I turn that into work, it would lose its magic. And so, after a couple months and this is where. serial entrepreneurship like kicks in. and now I get it. You get the next idea. and then you can't eat, breathe, sleep, think about it in the shower and. that's how it that's how it happened and. we got the team back together and we're. going to go we're going to go do it. again because I'm 37 years old and like. what else am I going to do with my life?

And so I'm going to I mean I go build. But this time I think I get to build. with more confidence. I get to build. with a different network. Mhm. I get to build without having the. the the dollar in mind or having that. pressure. And I get to take a different kind of. risk. And I'm really excited about the. scenario 2.0. Yeah, that's what I was. going to say is that is that scenario. 2.0 now? Like that's the I mean, it's. been a it's been such an amazing journey. of just getting to know myself and. finding time to really think about.

what's important and I was telling you. that mantra in the beginning of I've all. the time in the world. And I'm so busy. it's back again. I've got all the. million things, but I really do believe. I've all the time in the world now. Cuz. I get to choose it with all the things I. get to fill it with all the things that. I love. I took on my health head on. I'm. proud to report that my health is. incredible. Like I'm like everything is. like I'm the healthiest I've literally. been since like before I had kids and it. feels amazing and I feel so great inside. and I have this amazing energy in a.

different way and I, you know, prioritize myself and my workouts and it. used to feel like a chore and now it's. like I never thought I would be that. that girl that like loves to workout. And I mean, and I have different like I. love to walk and I love being in nature. I found I've always been a spiritual. person, but I lost that part of me. because it's hard to make the time, right? It's hard to add all the things. and I've really given that like a big. part a big bucket in my life. And I've really filled that bucket and.

found ways to just go deep and be in. peace and I'm so much more calmer now. Like if you ask any of my friends like. my energy is just in a different energy. I'm so grateful. You know, I was talking. to Faisal on the way here and it's like. we think that everything's happening to. us, right? It's so hard. It's so hard. But when hard things happen, you have to. trust that it's happening for us and I. really do understand that now. I think a. lot of spiritual.

teachers will, you know, share that that. you have to trust. You have to trust in. that there is a better plan. And I finally get it. And now when I pray or when I look deep. and I ask and I'm like, I want this or I. want to think about that or allow me. these opportunities or something better. So when things don't happen exactly the. way it's because the timing isn't right. because there's something better and you. just have to trust in the power of the. universe and I really do I really do. believe that when you're in that. frequency and it sounds like so woo, but.

I I get it and I feel really grateful. that I was able to take the time. to put in the work and you got to put in. the work. And it it's hard to to look. deep and check your ego. What check, you. know, how you're actually living your. life in action and is that really. aligning and I can look back and I also. cuz I had so many mistakes, so many. things I want to do over on that I I. don't I won't change, but I think growth is a big part of the. journey and I don't know what my. destination is going to be. I think this.

time around I'm not going to just build. a billion-dollar business. I'm probably. going to build I don't know something. even greater, but I'm not capping it. It's to just uncap it. And I'm really excited about that. That's so beautiful to hear and. it's so wonderful that you were able to. take lessons from the last 10 years and. shift and make changes and use this. transition period to. have a more transformational journey now. because. yeah, you can get so lost and broken by.

something that it's hard to do it again. And I think a big part of that from what. I've learned from you and private. conversations has been your relationship. with Faze. You've been with him since. you guys were 20. Yes. And and your. children as well and you know, I find. like women get asked this question more. than anyone. It's like, how do you do it. all, right? Like and and and it's one of. those unfair questions with the unfair. pressure. that that falls on women and I wanted to. ask you though for your relationship. and your relationship with your. children, how you were telling me this.

earlier, you're like think we're really. trying to do this right and raise great. humans and and everything else. What. have been the two most critical pieces. of being in love since you were 20 while. you build this 37 today. and having two children five and eight. That's during all of this, right? Like. this is all happening we haven't even. like that's all happening. And was it perfectly balanced? What did. balance look like? And and if you had to say here are two.

things that were the two priorities that. made sure that both things stayed on. track, what would that be? I'm so. grateful for. my husband and my partner and you know, we met so young and we built our lives. together and so I'm like super he's also. an entrepreneur. We're both like. different personality types but also. just he's the most incredible loving. human. You know, we have a joke in our. family that it's like everybody meets. Sal, my brother and it's like everybody. loves Sal. And Sal always goes and then. they meet my sister and then everybody. loves Sanira and then they meet Fayzal.

and then we're like chop liver. Like. everybody loves it it's everybody loves. Raymond but our house is everybody loves. like Fayzal. So we've got a house that's. just full and it's filled with so much. love. And I think it goes back to the same. things of communication and you know, I. think we in the in the beginning we. talked about productivity and we just. communicate really well. We're a team. The value system is of a team and never. in our like we've always had to you. know, one person's been in the driver's. seat or one person's been you know, in.

the back we've always been side by side. even if our careers are taking us in. different paths. Like I do feel like. I've had that support system in my home. life with him and. that is something that I'm so grateful. for to have a partner that is not. intimidated by the success or not. intimidated by like he's my biggest. cheerleader. He's my biggest biggest. fan. And it's that level of confidence. I do. think that I've been very fortunate to. have strong men in my life. I've never had men that, you know, I've.

had all strong male models who treat. women with like just the most amazing. things that we are. And I feel like that. has been a huge part of where I don't. see the world in that way. Like I I feel. empowered because my home feels. empowered. I know so many women that. they have to. mask their success at home or on a date. I have so many friends that are. struggling in dating life and they're so. successful, they're so incredible. And. when they show up, they have to it it.

feels emasculating because they have so. much success or that they're, you know, maybe earning more money or have more. accolades and. I do think that, you know, it takes. strong men to be with strong women. And. there are strong men in this world. I've been fortunate for that. And the. advice that I have on how we've been. able to co-partner and co-parent and do. the things is is building a home with. love and honesty and trust and. spending time together. That. productivity, like every Sunday we have. this meeting. So we have like my my.

whole life has been CEO life that I like. put into our our systems at home. But we. have a Sunday meeting, we call it Sunday. zoom out. And so my schedule is really. busy. I have to travel a lot for work. I'm speaking at conferences. He's got. his businesses. We're like two ships. sometimes in the night. And then we've. got our kids, we've got our girls. They're our number one priority. And each other. Like as a family unit, we're a priority. And so on Sundays, we. sit down. And now Mila is old enough, she's actually like she takes notes for. us. And so the kids are involved and. it's like here's the schedules for the.

week. And here's what, you know, mom's. up to and here's what's what dad's up. to. And, you know, their schedules are. crazy. They've got tennis and soccer and. piano and they're super overachievers. with a full schedule as well. By their. choosing, by the way. So by their. choosing, uh they get to pick their. activities and. so every week we sit down and we just. we're like, "Okay, here's what's. happening." And so that in and of. itself, that transparency, it's not like. mom has to go to work. We're so excited. because mom is going to LA to go do do.

be on this podcast. And then I'll show. them a clip of the podcast and they're. like, "Oh, that's so cool." Many times. like with if I have like so much travel, the kids go with me. They have been on, you know, every stage. They've gotten to. meet the most incredible They got to. meet Simone Biles at the uh Ernst &. Young the the Strategic Growth Forum. I. was speaking at Strategic Growth Forum. and, you know, I knew she was going to. be there. I brought the kids and I I. knew our path would coincide backstage. The girls were with me. Like we just try. to incorporate the kids into everything.

as best as we can and it's not perfect. parenting, right? They're going to miss. school. They're going to do the things, but involve them. And so on Sundays we. sit down as a family and we're excited. for each other. That takes the pressure. off of like, it's not about the. schedule. It's about what are our wins. for this week as a family. And then we. prioritize, okay, so if this is what's. happening and this is what's happening, then we go into like the tacticality of. it, right? Who's doing pick up? Who's. doing drop off? And I do want to make. sure, you know, the women in the. audience especially here, I do have help.

because. that is it's impossible. It is. impossible. The weight of the the things. that we have to do, ask for help. Whatever you can delegate off, even if. it's the laundry, even if it's And if. you don't have the resources, ask a. friend. Ask for help. Trade share. Do. the things, but help is a big part of. how it all works. And so I've got my mom. and we've got support and just because I. have support doesn't mean that Faisal. and I aren't the ones that are like the. nucleus of it, right? Like we fight over.

drop off. We fight over it. And so we. just divide and conquer and the kids are. involved and there really isn't perfect. balance. I think that's what it's a. myth, you know, myth balance is. There isn't It's integration. And so we've just learned to integrate, we've made our lives out of it, we. travel so much, we make it fun. That's. what how we do. And then every week we. prioritize time together for just him. and I. And that's how we've been able to. really say And there's And it's not. perfect. We've had our moments through. our days over the years like hard. moments through the years. And every.

time we have hard moments, it's because. we've deprioritized ourselves. We've. deprioritized our relationship. And then. when we we don't have date nights or or. just even a walk, right? Where it's just. one-on-one time and we're not. connecting, then we're annoyed at each. other and we're bitter. And then. everything else falls into place. So, that Sunday meeting is super super. critical for our family. And you can. have it all. Like you can I was so tired. of hearing that you can have it all. We. often hear that. And many successful. people say you can't have it all.

I want to have it all. But I want to. define what all looks like. So, for me. it's that going back to the threes. I've. got three buckets. That's it. So, it's. my family, it's my work, right? And now. it's still building this company, and. it's impact, right? It's It's It's the. work that I get to do with women in. business. And I think that that's And. that might change, right? So, your. buckets might evolve, but those are the. buckets that I'm filling. And it's not. perfect on a day-to-day. So, when I'm. here and I'm here for work, I'm fully present here. And I know. everything is taken care of. And when.

I'm home, I'm fully home. And that's why. I love going into the office. So, Faze. likes to work from home. We can't work. in flight cuz he's always cook He's. always distracting me. Like he's He's. always on Chronos' time. He definitely. has all the time in the world. And he's. just so chill. We're like so opposite. And so we work separate. Like I I go. into the office cuz I like to go in. I. like to get my stuff done. But then when. I'm home, I'm home. And everything is. like it's all for them. So, I spend We. spend quality time. And I think that's. what it is. I think it's truly that, you.

know, living in the now and living in. the present and just enjoying. We can enjoy the journey today. We don't. have to wait for the milestone. We don't. have to wait for when we have this house. or when we have this or when we have. that. People waste away their lives. chasing. Waste it all away. You have it in front. of you. Sinera, it's been such a joy. talking to you today and hearing about. the incredible journey you've been on. and I'm so excited to be your friend now. and watch the next phase and get to know. you more through this part. And we end.

every On Purpose episode with a final. five. Oh my goodness. Which are the fast five. So you have to. answer every question in one word to one. sentence maximum. Okay. So Sinera Madani, these are your. fast five, final five. So the first. question is what is the best advice. you've ever heard or received? Everything isn't as good as it seems and. everything isn't as bad as it seems. Oh, that's great advice. All right, question number two. What is the worst. advice you've ever heard or received? I. think the worst advice I've ever. received is it's honestly been the best.

advice in some way cuz it's been the. underestimate like the underestimation. of like that you can't. Right? Or not. now. And why not now? Why not me? Nice. Uh. question number three, what's your freedom formula? You know, freedom of dollars is. important. You've got to be able to have. financial freedom. It doesn't mean that. you've got to have all the money in the. bank, but financial freedom is important. so you can feel secure. But it's freedom. of time. Like that's what we're living. for. And if you can get that freedom of. time, then hopefully you can focus on. impact. So it's freedom of impact. So.

it's freedom of dollar, freedom of time, and freedom of impact. I love that. Uh. question number four, how do you avoid. being lonely at the top? You surround yourself with with real. friends. You surround yourself with. people who also feel just as lonely or. in their fields and. you you don't have you have a small. circle, but you have a meaningful. circle. And fifth and final question we. ask this to every guest who's ever been. on the show. If you could create one law. that everyone in the world had to. follow, what would it be? The one law.

that I would like the world needs to be. led with kindness. So, before you say. anything shitty or nasty or something's. about to come out of your mouth, like or. even in your own for your own self, just. do it with love. Like do it with extra. extra extra extra extra love cuz if we. just love on each other, if we love on. ourselves, I do think that the world. would just it would be perfect. Uh. Sinera, I love your energy. Ever since. the moment we met, we met last year at. the Baby to Baby Gala. And we just hit it off and start talking.

and I got to meet Faysal as well and so. us three were hanging out and every time. I meet you I fall more in love with your. energy and aura and I'm just so grateful. for what you're doing for entrepreneurs. all over the world and I hope everyone. who's been listening and watching. follow Sinera on social media, subscribe. to our podcast, watch out for what's. next with their journey with Worth Ai, and Sinera, I'm truly grateful to call. you a friend and I'm really really happy. that you came and trusted us to be on On. Purpose. And I hope everyone who's been. listening and watching share your. insights, the things you're going to.

try, the nuggets of wisdom that Sinera. shared that resonated with you. Share. them on stories, on TikTok, on. Instagram. I'm always looking out to see. what really connected with your heart. and your mind. And I think there were so. many amazing insights that came out of. today. Sinera, thank you so much. Thank. you, Jay. The feeling is so mutual. You're incredible. For those that Of. course your audience knows this, but. it's hard to meet your heroes because. you don't know like what they're going. to be like and I've been a true like. I've always like the amount of podcasts.

that I've listened to, the amount of. Daily Jays I've heard in my you know in. my career, I was almost afraid when I. met you and I I told you this. I didn't. know you know what it was going to be. like, but you were the same as what I. would have imagined but in if not. better. You were just so incredible and. I wish you so much success and the world. is rooting for you because we need more. people like you rooting for us. Thank. you. Thank you so much, Sinera. Thank. you. If you love this episode, you'll. enjoy my conversation with Meghan.

Trainor on breaking generational trauma. and how to be confident from the inside. out. My therapist told me stand in the mirror. naked for 5 minutes. It was already. tough for me to love my body, but after. the C-section scar with all the stretch. marks, now I'm looking at myself like. I've been hacked. But day three when I. did it, I was like, "You know what? Her. thighs are cute.".