Suneera Madhani: Why Most Founders Fail—7 Things You Must Do to Succeed

Suneera Madhani: Why Most Founders Fail—7 Things You Must Do to Succeed

March 26, 2025 1h 26m

What habits do you think lead to success?

How do you handle setbacks or failures?

Today, Jay Shetty sits down with Suneera Madhani, a visionary entrepreneur who defied the odds to build a billion-dollar business. As the founder of Stax Payments and CEO of Worth AI, Suneera opens up about her remarkable journey—from being the daughter of Pakistani immigrants and the first in her family to attend college, to becoming a trailblazer in the fintech industry. Her story is a powerful testament to resilience, innovation, and breaking barriers in a world where women are often underrepresented in leadership roles.

In this insightful conversation, Jay and Suneera dive into the mindset shifts necessary to scale a business, from overcoming self-doubt to making tough leadership calls. Suneera shares her game-changing “Do, Delegate, Delete” framework—a powerful time management strategy that has helped her balance the demands of entrepreneurship and motherhood. Jay emphasizes the value of living with intention, drawing parallels between Suneera’s disciplined approach and his own experiences with self-awareness, productivity, and personal growth.

Together, they discuss the unique challenges women face in business, especially in male-dominated industries like fintech. Suneera opens up about the gender disparities in venture capital funding and leadership, sharing eye-opening statistics that highlight the struggles many female entrepreneurs face. More importantly, she offers practical strategies for women to break through these barriers—building strong networks, seeking mentorship, and how to step into executive roles with confidence.

In this interview, you'll learn:

How to Turn Rejection Into Opportunity

How to Effectively Manage Time as an Entrepreneur

How to Scale a Business to the Next Level

How to Balance Entrepreneurship and Family Life

How to Build a Strong and Supportive Network

How to Succeed as a Woman in a Male-Dominated Industry

How to Shift Your Mindset for Long-Term Success

No matter where you are in your journey—whether you're launching a business, chasing a passion, or facing life’s challenges—remember that success isn't just about hitting a milestone. It's about staying aligned with your purpose and pushing forward with intention.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

02:46 Highly-Caffeinated Time Hacker

03:46 The Best Time Management Strategy

07:35 How to Delegate Time & Tasks Effectively

11:05 How It All Started

16:42 Collaboration to Solve Hard Problems 

19:46 The Risk of Playing It Safe 

25:50 How to Set Empowering Goals

30:15 Build Your Network

37:19 Don’t Lose Yourself in the Process

41:37 Building a Business with Family

50:21 Find Your Niche to Build a Product That Lasts

55:19 Mindset Shift to Build a Successful Business

01:01:24 The Darkest Day for an Entrepreneur

01:08:41 The Importance of Self Reflection  

01:12:16 A Supportive Partner is Key

01:20:21 Suneera on Final Five  

Episode Resources:

Suneera Madhani | Website

Suneera Madhani | LinkedIn

Suneera Madhani | Instagram 

The CEO School

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Full Transcript

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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. Hey everyone, welcome back to On Purpose, the place you come to listen, learn and grow.
you know that On Purpose is the home of deep, profound, powerful conversations with humans who've lived extraordinary lives, achieved phenomenal things, but at the heart of it, have a deep purpose. They also have the ability to open their hearts, open their minds, to share the true failures, the lessons that they've had on their journey.
Today's guest is someone that I'm so excited to introduce to you. She's had truly a breathtaking journey and it's one that's gonna inspire you and help you learn how you too can build an amazing business, understand what it feels like to manage and balance family life through it all and at the same time, go and pursue more even after success.
I'm speaking about the one and only Sunira Madani, a true trailblazer in business world. Sunira is the CEO and co-founder of fintech startup Worth AI.
Sunira previously founded Stacks Payments, where she took an idea and built it first into the private startup with $140 million in recurring revenue and then into a business valued at over a billion dollars. Suneera is also the founder of the CEO School podcast and the founder of the CEO School company.
If you haven't subscribed, make sure you do because both of them empower women to scale their businesses and change the landscape of the traditional business world. Suneira is the daughter of Pakistani immigrants and the first person in her family to attend college as well.
Please welcome to the show, Sanira Madani. Sanira, it is such a joy to have you here.
Your journey is truly remarkable and I'm so glad that we get to share it here with the On Purpose community. Jay, thank you so much for having me.
I'm so grateful to be here. I'm so excited to just carry this amazing conversation that we've already been having.
We're like, turn the cameras on. It's time.
I know. I felt like, I was like, we're probably going to have to put some of that in.
But I want to start with this. And it's probably nothing to do with what I said we were just about to talk about.
But 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 eight-year-old daughter and a five-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 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 $10 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 10, that's a $10 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 tasks 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 of weeks I'll do a time audit.
I love this already. Yeah, I do a time audit because 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 and 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 because 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 have all the time in the world. I have all the time in the world.
I have 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, And 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. 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 busy or is it full? 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, 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 as 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 the rule of three for everything. I can't remember more than 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 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 gonna get done that are gonna be towards the goals that are gonna 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.
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 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, all 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.
I love 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 four in the morning, wake up kind of guy. Every morning he'd wake us up and he'd say, Sonny, that's 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. My brothers and I's biggest champions.
And so you carry that level of like responsibility. 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 gender.
Like I was just the eldest kid. And so that meant that I got to do everything first.
I never felt my gender until I went into the workforce. Wow.
That's, yeah. Not even in college.
In college, like, you know, I went to, I went to University of Florida. We had like three championships 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 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.
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 overlove 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

Let's go. 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, we 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, Sonny, 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. And 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 was like, and if you don't, in six months, you'll get your MBA.
That was it. That was, it was as easy as that.
Amazing. I want to unpack so many things.
So now you've given me enough stuff to just grapple with. I loved what you said about the idea that you can't overlove 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 there and 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 taking place about money or about business or about family, we were solving problems together.
So my parents would always ask our perspective. That is something that I do feel is very interesting.

Just as a child, I try to do that with my daughters at the dinner table now is to ask them what they think.

So thinking about solutions versus 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 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 I'm going to go ahead and 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.

Then when they would come out and do 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 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.

And it's important to see,

like you can see both sides of your parents. Things weren't perfect.
I look back and I think about mostly the positive, 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. 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. So I'm imagining that you were making a decent amount of money working at a 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 I'm not making the money anymore, life changes. Walk me 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 ask myself, would I do it again? 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. 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 the risky decisions today.
And I know we're going to talk more and this journey is 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 you do have to 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.
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.
I even think about parenting. Oh my God, now if I knew all the things that I knew 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 because 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, 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 like, 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 my car.
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'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, because 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 it, 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 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. I love, love meeting.
And I get an opportunity with everything that I do with a 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 kid's school. Somebody wasn't solving something for their industry.
There is 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 empathetic part, the nurturing part, the problem-solving part of women. And women actually end up becoming the most successful investments for venture capitalists.
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 women at the top across the world on a global standpoint.
So it is important because women build with purpose. And I think that that's what you have to stay you have to stay grounded.
And it's 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 we're, 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.
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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.
Like 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, masterclasses, 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 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 in the workforce, you know, since the 1940s, 50s, since post-World War. Like the business world has not been designed for women in mine.
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 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 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 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 were 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 were. 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 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 got investors, was venture-backed. It's not anyone's fault.
It's just I was the first portfolio company that was founded. That was a female-founded portfolio company.
And I arrived to this conference, and every CEO walking

in through the door stopped me and 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 the event manager until one of the LPs was like, I'm welcoming our newest portfolio CEO, Sidera, and 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? I think that's the third piece of advice is it took me so long to get comfortable with fully 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 many stories of how I would show up. I called myself a man in a skirt.
So 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 and leading the way that as Sanira, that came later for me. And it came through confidence, right? It came through like doing it and finding 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 do it anyway, show up in the rooms and show up as you.
You don't have to be a man in a skirt. Be exactly how you are.
And I think that the world is, I think it's changing, Jay. So I think it's getting better.
The statistics aren't there. And I've got thoughts on why the stats aren't there.
And it's because we're not holding institutions accountable. There is an accountability component.
Shit does not change unless you hold somebody accountable to it. So venture capitalists, where is the 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 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 behavior, as well as so many things.
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'm really curious to see how we're going to do that in my generation.
I want my daughter's generations. I want my kids to 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. 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 heard when I was in England, I heard the 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. 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 and they'd be like, wait, how's your name? Steve. She's like, Oh, they go.
I go by Steve. Cause 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. Just being honest.
Yeah, no, and 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 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 me to get that, land that customer, to 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, every one of my investors, mentors, they're all probably rolling their eyes laughing at. Typical scenario conversation is how they can be better for us too.
I'm like, okay, next time instead. And so the next year at that conference, my wonderful investors, and they're so incredible.
So it was not their intention to make me feel left out. And it was a golf tournament on the second day.
Of course, it's a golf tournament on the second day. And so they set me up at 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 because I've got my kids to go like to get home to.
But I want to be invited to that. Like, I want to just be part of the thing.
I don't want to have this like curated extra experience. And so I'd always invite them.
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, it didn't say anything. And so I do think that that's where I was, 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.
I know 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 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 fintech space is different.
But I do think that we can co-create a more beautiful experience for all. Running your own business means wearing a lot of hats.
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Let Pandora Jewellery remind you that love starts with you. 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.
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, 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 backend. 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.
I mean, we have the same DNA, right? Like there's like same value system. 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 craziness, the family stuff. They're really your, you know, the other half of you in a different way in the 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 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 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 and 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 were 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 and even though I was started 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 business is going to fail?

We're going to have success.

We're going to fail.

I didn't know what was going to be the outcome, but family is forever.

Like, I didn't want 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 two years older.
So older sister, I like that. I love that.
So that was the deal. And actually this company now, we're building again together.
And this time he has 2% more to make life fair. 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. And so every decision that you make and whether that's with your friend or with your spouse or whoever you're doing a business partner that you're doing business with, if you guys are coming at it from this same equitable lens, then you know that there's that extra level of trust because there isn't any other gain or benefit for Sal or for myself.
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, it's 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 that 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 not just having the end in mind. We actually never signed a contract.
So that's actually, I'm giving the advice. I never took 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 are 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 nonstop. 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, a 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's like a third party there that's been super helpful and just building upon that communication.

So trust is super important.

And that communication, 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 relationships, it's resentment.

We don't talk about it. We're not addressing it.
We're not finding 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 hard 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. That's her world.
That's what she's dedicated her life to. She's a nutritionist.
She's a dietician. 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 journey for the morning and a journey for the evening and a journey 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 nine, 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 talk to a lot of

people about. And I think you've nailed it.
And we kind of touched on it in our previous

conversation 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. It's not sexy.
Yeah. I call it unsexy money 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 consumed.
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 with. And I always be like, no one's ever heard of these companies and there are founders here 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 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 many ways. We have to stop doing things for the gram.
We have to, it is our mentality of building companies, products, services, that if it's not this, then 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 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 the spirit of solving for problems.
It's not for show. Success will come if you just let go of that 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 because 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've 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 and 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 day, there's another mountain and there's another mountain.
So you've got to love that challenge. That's what entrepreneurship is.
It's not, I didn't build a billion dollars. 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 exit, right? It's like, here I'm back again and building again.

It's because I see the problem

and I know we can solve it.

Okay, I have two questions for the guys out there.

Do you want to have nice, healthy skin?

And would you rather not spend a ton of time getting it?

So for the like 99% of guys who said yes to both questions,

Dove Men Plus Carebody and Face Scrub is the ultimate hack for effortless skincare. And when I say hack, I mean it.
It really makes getting better looking skin as simple as possible. The new Dove Men Plus Care Scrub literally exfoliates, cleanses and moisturizes in one step.
That's it. It's the definition of a hack and you can feel good about using it.
We're talking about natural essential oils. It's vegan and parabens and sulfates free.
Plus it's totally designed for men's skin. But the main thing is that it works and it's easy.
Your skin will look and feel better. And in case you missed it before, you don't have to work hard to make it happen.
Yep, just hack your grooming routine and add the Dovemen Plus Care Scrub into your shower. The jewelry you wear is so personal.
It's like a little piece of your story you carry with you every day. That's why I love Pandora.
Their designs feel so thoughtful from charms that remind you of the moments that matter most to pieces you can have engraved with something truly meaningful. My favorite pieces are the ones that feel like they're just made for me.
Whether it's a sparkling diamond, a vibrant pop of color, or a charm that holds a memory, it's more than jewelry. It's a way to express who you are and celebrate your journey in the most beautiful way.
Shop Pandora today, in-store or online at pandora.net. Every day is a chance to be love.
Let Pandora Jewelry remind you that love starts with you. You've probably been hearing about AI everywhere, and we all need to be mindful of the tools we trust in this new chapter of technology.
Claude is the, if you know, you know, AI assistant that just feels different. While other AIs often sound like robots, Claude is being created with special research that informs its character, meaning that Claude just gets it when it comes to empathy and emotional intelligence.
That's why millions of people are turning to Claude. For parenting tips.
Dating advice. Mindful habits like journaling, budgeting.
And so much more. Claude has been thoughtfully crafted by Anthropic.
And its team of researchers. Whose mission is to design the most capable.
And secure systems systems that place people at the center. You can try Claude for free today at claude.com.
That's C-L-A-U-D-E.com. Yeah, 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, a hundred 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 a hundred.
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 a hundred, a hundred 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 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 get new technology.
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, or the hundred 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 seven years to unlock that next.
And then I'm going to go to small businesses. So 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 being over-prepared over all the things so that I could be the best CEO that I could be.
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 meets me and my brother.
We're one team. We're one team, one dream.
Like 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. 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 $100 million mark. And when I started the company, the name of the company was Fat Merchant, by the way, because I was 25.
It was fun and we were disrupting the industry. But I knew Fat Merchant was a $100 million company.
Stacks 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 to 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'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 was so tired of hearing my entire career scenario, 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, 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 playbook.

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 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 I'm listening to you now and I'm thinking there's probably at least like, I reckon you have a minimum of a hundred 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 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 mentioned mentioned, I was chasing something that I didn't know that I wanted.
And so it was like, boom, we did, it was 220 million, I think was the 2020 valuation and exit where we cashed 70% out of the company. So whoever owns shares, everybody made money.
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 was 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 think women can relate to this.

Like my OB was my doctor for like, because I was having babies in between and Faisal

and I were planning a family and that was it.

So for five 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.

You have to like do these insurance, 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 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, you're, you're from essential, like you dream of like being in front of like the Black Rocks and the KKRs.
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 close the Series D, bring in other minority investors.
We were a hundred 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 revenue and we closed around 1.1 billion, everything I'd ever dreamed of.

The whole, 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 mayors,

like everything's there,

all of this excitement around this milestone,

around this series,

either on this valuation and around this exit.

And when the party was over, it happened so fast. Like it was like two weeks of all of this and then I was back to work and I went to my next board meeting and I 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 have no goal.
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 we had this big plan laid out for the next transaction or maybe going to IPO. We had three acquisitions at that time.
And as a student of learning, I get really excited about just learning. I'm like, I want to do something that I haven't done.
And going public was something 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 was like, I have to, this is not for me anymore. And that 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've spent my entire adulthood building this. My work was my worth.
It was my only identity. And it was so hard to shed what was next.
And so that was it. That was the toughest moment.
It was the hardest decision. I had many people think that that was 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 Stacks.
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 come off. I've got the podcast.
I love meeting amazing women and supporting female founders. But if I turn that into work, it would lose its magic.
And so after a couple months, and this is where serial entrepreneurship 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 happened. And we got the team back together.
And we're going to go do it again because I'm 37 years old. And what else am I going to do with my life? And so I'm going to go build.
But this time, I think I get to build with more confidence. I get to build with a different network.
I get to build without having 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 Scenera 2.0. Okay, I have two questions for the guys out there.
Do you want to have nice, healthy skin? And would you rather not spend a ton of time getting it? So for the like 99% of guys who said yes to both questions, Dove Men Plus Care Body and Face Scrub is the ultimate hack for effortless skincare. And when I say hack, I mean it.
It really makes getting better looking skin as simple as possible. The new Dove Men Plus Care Scrub literally exfoliates, cleanses and moisturizes in one step.
That's it. It's the definition of a hack and you can feel good about using it.
We're talking about natural essential oils. It's vegan and parabens and sulfates free.
Plus, it's totally designed for men's skin. But the main thing is that it works and it's easy.
Your skin will look and feel better, and in case you missed it before, you don't have to work hard to make it happen. Yep, just hack your grooming routine and add the Dove Men Plus Care Scrub into your shower.
The jewelry you wear is so personal. It's like a little piece of your story you carry with you every day.
That's why I love Pandora. Their designs feel so thoughtful, from charms that remind you of the moments that matter most to pieces you can have engraved with something truly meaningful.
My favorite pieces are the ones that feel like they're just made for me. Whether it's a sparkling diamond, a vibrant pop of color, or a charm that holds a memory, it's more than jewelry.
It's a way to express who you are and celebrate your journey in the most beautiful way. Shop Pandora today, in-store or online at pandora.net.
Every day is a chance to be love. Let Pandora jewelry remind you that love starts with you.
You've probably been hearing about AI everywhere, and we all need to be mindful of the tools we trust in this new chapter of technology. Claude is the, if you know, you know, AI assistant that just feels different.
While other AIs often sound like robots, Claude is being created with special research that informs its character,

meaning that Claude just gets it

when it comes to empathy and emotional intelligence.

That's why millions of people are turning to Claude

for parenting tips, dating advice,

mindful habits like journaling, budgeting,

and so much more.

Claude has been thoughtfully crafted by Anthropic and its team of researchers whose mission is to design the most capable and secure systems that place people at the center. You can try Claude for free today at claude.com.
That's C-L-A-U-D-E dot com. Yeah, that's what I was going to say that is that scenario 2.9 now like that's the i mean it's been 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 have all the time in the world now because 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. I'm like, everything is like, I'm the healthiest I've literally been since before I had kids.
And it feels amazing. And I feel so great inside and have this amazing energy in a different way, and I prioritize myself and my workouts.
It used to feel like a chore, and now it's like I never thought I would be that girl that loves to work out. And I have different—I love to walk, and I love being in nature.
I've 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 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.
If you ask any of my friends, my energy is just in a different energy. 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 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, it's because 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've got to put in the work and it's hard 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 we said so many mistakes so many things I want to do over on that 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 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. So 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 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 it's one of those unfair questions with the unfair pressure 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 were like, I think we're really trying to do this right and raise great humans 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 were two things that were the two priorities that made sure that both things stayed on track, what would they 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 Faisal and then we're like chopped liver like everybody loves it it's everybody loves Raymond but our house is everybody loves like Faisal 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, 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.

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 feels emasculating because they have so much success or that they're maybe earning more money or have more accolades. And I do think that 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 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.
It's 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 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, they get to pick their activities. And so every week we sit down and we just were 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, 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 Ernst & Young,

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 knew our path would coincide backstage.
The girls were with me. 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 pickup, 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 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-offs, 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 bullshit.
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 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 stay.
And it's not perfect. We've had our moments through 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 don't have date nights 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't 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. why I love going into the office so Faze likes to work from home we can't work in like because he's always cooking he's always distracting me like he's he lives on Kronos time like he's 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 go into the office because 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.
Cynera, 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, which are the fast five. So you have to answer every question in one word to one sentence maximum.
So Suneer and 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 because it's been the underestimation, like the underestimation of like, that you can't, right? Or not now. And why not now? Why not me? Nice.
Question number three, what's your freedom formula? You know, freedom of dollar 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.
Question number four, how do you avoid being lonely at the top? You surround yourself with real friends. You surround yourself with people who also feel just as lonely or in their fields.
And you don't have, you have a small circle, but you have a meaningful circle. And fifth and final question we ask is 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 for your own self, just do it with love. Like do it with extra, extra, extra, extra, extra love.
Because if we just love on each other, if we love on ourselves, I do think that the world would just, it would be perfect. Oh, Sunira, 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 started talking and I got to meet Faisal 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 Sunira on social media, subscribe to our podcast, watch out for what's next with their journey with Worth AI. And Sunira, I'm truly grateful to call 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 Suneera 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. Sanira, 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 what they're going to be like. And I've been a true, like I've always looked, the amount of podcasts that I've listened to the amount of daily J's I've heard in my, you know, in my career, I was almost afraid when I met you.
And 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 if not better, you are 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, Sonara. Thank you.
If you love this episode, you'll enjoy my conversation with Megan Trainor on breaking generational trauma and how to be confident from the inside out. My therapist told me stand in the mirror naked for five 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.
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