#15: Busting Through The Pink Ceiling with Cindy Eckert
4 Nov 2025 · 61 min
This content was created by Heather Monahan. This content was uploaded by Heather Monahan. This is a podcast episode titled '#15: Busting Through The Pink Ceiling with Cindy Eckert' released in August 2019. The content features Heather Monahan as the host, engaging in a detailed conversation with Cindy Eckert, a self-made serial entrepreneur and advocate for women. The discussion covers topics such as overcoming professional challenges, women's health and sexuality, entrepreneurship, funding for female founders, and empowerment. Heather Monahan shares personal anecdotes and promotes various sponsors throughout the episode. The format is a conversational interview focused on women's empowerment and business success.
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Thank you for listening to this Podcast 1 production available on Apple Podcasts and Podcast 1.
Each week. When you join me here, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Come on this journey with me. Hi and welcome back to Creating Content Confidence. I'm so excited that you are joining with me and I'm so glad you're coming back with me each week. This week has been a crazy one. I actually just got back. I took my son away for the weekend with one of my good friends and her boys and we went on a three day cruise which was interesting, but it was a lot of fun and I'm so glad we did it. But I'm sure like you, anytime you go away, it's amazing to detach and so, so hard to come back to reality. My son's starting middle school this week. I am turning 45 this week. I have so much going on. I'm so far behind with work right now, so things are a little crazy and when I get to feel overwhelmed like this, I really need to take a step back, write down everything I need to do. I love having my to do list and checking things off and when I can't get started, I always, always start with the easiest thing first and I just jump on it to get my momentum and get moving. Taking action fixes everything. So one of the things that I wanted to share with you today, it's kind of funny. I had someone reach out to me last week on LinkedIn telling me how much they loved a certain chapter from my book and I haven't read my own book in a while, which I guess is probably pretty normal. But I had forgotten about this story and the lesson from the story and I really loved it. It resonated with this person that reached out me and I wanted to read it to you. And yes, I do read my book in the audiobook. So if you want me to read to you all the time, you can just buy Confidence Creator on Audible and you got me. Even though so many people told me not to narrate my book, that I should hire a professional, I took that chance and thought I want it to be real and authentic and I think that will be more powerful. And I definitely was right and I'm so proud of it now. So I'll give you the insight here and the actual chapter that this person was talking about. So here we go. It's chapter 12 of my book. It's called Leapfrogging Villains. And you know, I love Talking about the Villains everyone's story has a villain. There are those who support you and those who try to pull you down. You will never be able to root out all the villains in your life, so learning how to leapfrog those villains is essential in becoming successful. I wasn't in corporate America very long before I realized that not everyone was a good person. I was naive and never imagined that people who didn't know me would try to hurt me or hold me back for no good reason. I learned quickly that villains in the real world don't wear witch hats or ride a broom. Some villains are sneaky and fly under the radar. They look like normal people. Some are meek and quiet. Others are affable. But all of them are fake. On some level, you have to keep your eyes open so you can spot those villains. I encountered my first professional villain very early in my career. I had just graduated from college, had no idea what I wanted to do, so I went to work in the wine business as a salesperson. I liked it and I was really good at it. I was doing my job and trying to be the top salesperson in record time. I didn't realize that someone was out to get me. During this time, I heard from friends that Jenny, another salesperson, was badmouthing me to other employees in the company. Aside from a few brief encounters, I didn't even know the woman, so I had no idea why she would have any ill will toward me. It didn't make sense, so I decided just to ignore her. The more you elevate yourself and succeed, the bigger target you become for potential villains. When I became the top salesperson on our team, Jenny became increasingly vocal in her disapproval of me. She was attempting to poison others with stories of why people should not like me. She went so far as to go to leadership and tell them I was a poor representative for the company. Ignoring a villain can be a good first step, but I've learned that most villains need to be sent a much stronger message and be confronted head on. The Wicked Witch needed a bucket of water thrown on her to make her disappear. Ignoring her wasn't enough. When the situation with Jenny escalated, I needed to find my bucket of water. I thought back to a lesson my former boyfriend, Ned. Pause for a moment. That's not his real name, but I did change everybody's name in the book, so bear with me had taught me years earlier. Ned was a police officer who, because of his job, had a habit of preparing for the worst case scenario in every situation. One thing he used to Always warn me about was jogging outside alone. I love to run, but Ned explained how I needed to pay attention to my surroundings so I could react in case of emergency. It was important to run the neighborhoods that were populated and had lots of light. He also warned me about dogs. I thought he was kidding, but he had a point. What do you do if a dog gets loose and chases you down? You have only seconds to react. A lot of people try and run away and get hurt, which is why Ned told me to do the opposite. He said, run at the dog, Yell at the top of your lungs.
It seems crazy, but it made sense.
The idea was that I needed to prove I was the dominant one. A few months later, I found myself in the exact situation when I was out for a run. A rottweiler had broken free from a nearby fence. That dog came barreling at me and looked like it wanted to tear me apart. I wanted to run, but I remembered what Ned had told me. So I started screaming and pointing my finger at the dog while running as fast as I could right at it. This is a true story, by the way. I got within feet of that dog when it suddenly began to whimper and turn back toward the house with its head between its leg. I could not believe it. Once I caught my breath, I nearly fell over. Jenny, my fellow salesperson, posed a much different threat than that dog. But I had to deal with her in a very similar way head on. My opportunity presented itself when she asked for a private meeting with me. I didn't want to take the meeting, but my boss encouraged me to meet with her and get it over with. Up until that point, I had avoided her because the whole thing was so ridiculous and annoying. But keeping my distance was only allowing her to spread more ill will about me. And she was growing in strength. When I walked into that conference room, Jenny was sitting at the head of the table, looking stoic and cold. I sat down across from her, and she proceeded to explain how she felt. There was tension between us. Huh? I didn't feel attention. I just felt annoyed that she was badmouthing me. But I sat there and I heard her out. She went on and on about what it takes to succeed in a man's world. She felt that the way I carried myself was not conducive to making it. I had to ask, what do you mean by that? She told me that the way I dressed was unacceptable and that I was bound to fail if I didn't dress more like her. Now. Jenny was 10 years my senior and had an entirely different look and style than I did. She had a short bob and she wore pants every day. She wasn't someone who had much of a feminine side, or at least she didn't show it at work. I, on the other hand, favored skirts and had long hair and I wore my hair down every day. I very much embraced my femininity and the way I dress gave me a sense of strength and empowerment. It was a key step that helped me build my confidence early on. I wasn't going to give it up because of that woman. I had heard enough. It was time for me to throw my bucket of water. I told her that I was not her. While she may favor pants and short hair, I did not. I like the way I dressed and the way I wore my hair is not a problem for me. It clearly wasn't a problem for anyone else either because I had just been named the number one salesperson in the company. With a very stern look, I asked her, is there anything else? I need to get back to work. That was wasn't an easy conversation for me to have and I was nervous. But she had finally been shut down. Slaying that villain made me feel stronger. A situation that had been uncomfortable for me was finally resolved. From that point on, she backed off and kept her distance from me. Speaking your mind and defending yourself may seem like a simple step, but it's a surprisingly effective one when you're right. Most villains like that are not used to being confronted or called out for being wrong, so doing so puts them in an uncomfortable position. Don't sit around and wait for someone else to do it for you. You are your own best advocate, so it makes sense that you are the most qualified person to slay your villain. Practice what you're going to say. Prepare answers for certain responses. If you stay calm and respectful and speak your mind, the message will be sent loud and clear, just like mine. So if you've got a villain out there and you have been avoiding them like I was, it may be time for you to throw your bucket of water. And keep in mind that story of the Rottweiler. You can't outrun a Rottweiler. The Rottweiler will get you, but you can run them down and show them that you are the dominant one. So enough time for the villains. We're firing them today, no matter who they are or what they look like. And I can't to get into my interview. You're going to really be excited for this, but I have to share one unbelievable find with you before we go There I just became aware of ThirdLove. ThirdLove is an unbelievable company for women. These are the best bras with more sizes than other brands.
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Hey there, Rob Cisternino from Rob is a podcast. And if you're a Big Brother fan, you know the summer is all about one thing. Watching crazy people locked in a house on Big Brother. And we've got episode recaps after every episode with the past house guests talking about all the updates from the game and the gossip from the live feed. Listen to Rob is a podcast exclusively on Apple Podcasts and Podcast one. And if you love the show, why don't you share it or even leave us a rating and review?
Hi. And we are back. Thank you so much for coming back with Me. All right. I say this all the time and I'm so annoyed, but I'm so excited for you to meet my next guest. Cindy Eckert is amazing. Self made serial entrepreneur, vocal advocate for women. Cindy defies convention in her industry, in her companies and in her outcomes. Her work with the Pink Sailing Pinkubator continues to break barriers by investing and mentoring other women. And she's getting them the same outcomes she has. And she sold her companies for. Get this 1.5 billion. That's with a B. First Slate Pharmaceuticals redefined long lasting testosterone treatment for men. Then Sprout Pharmaceuticals, which broke through with the first ever FDA approved drug for low sex drive in.
Get this women.
Oh my gosh, the female Viagra.
That exists. It does exist. Well, there were 26 for men. I thought it was about time that we have one of our own.
Isn't that insane?
It is insane, actually. And it's insane because we had this science, but we weren't paying attention to it because of such a deep societal narrative. Really like we do if something goes wrong for a guy in the bedroom, immediately we think, okay, biological, we'll treat that. Something goes wrong for a woman, we pat her on the shoulder and tell her to take a bubble bath or drink a glass of wine. We completely ignore that.
There's nothing wrong with. There's nothing wrong with a glass of wine or a bubble bath.
Of course there's nothing wrong with it, but it's not going to treat an imbalance of key chemicals in the brain. And that's what happens for 10% of women who lose their interest in having sex.
So for you, you had this background that you were immersed in the medical industry and you just had this epiphany moment one day.
Well, no, there was emerging science. We've learned so much from brain scan studies of conditions that affect the mind. And this desire starts in the brain. And I built this company with one of the male drugs. And, you know, I'm looking at this complete injustice that women who have things going wrong biologically in the bedroom have no treatments of their own. And it just ignited me, I think that injustice of it. And having spent so much time talking to women, you know, sex is. We make it a joke. It's how we deal with it, you know, in our cocktail party conversation or.
Right here, right now.
That's what we do. But the reality is, like, while it's true, nobody will lose their life from not having a sex, they lose their life as they know it. And I spent time talking to women and they were losing their marriages and their relationships, I'm sure their sense of self. And so it really is such a part of the human experience, our sexuality, how we show up, that it got me started and I became a complete crusader here.
It's kind of crazy because you touched on it, that, you know, it's such an uncomfortable topic for so many people and even myself. I was saying to someone today here at the studios, oh, my gosh, I.
Have a sex guest on what am I gonna do?
Because it does make you. It puts me out of my comfort zone. So it's interesting to me. How do you approach that? Because at some point, it must have. Did you ever feel that way?
Oh, are you kidding? I mean, for sure. And it's. I approached it very scientifically. So the geek in me, if you will, was looking at brain scan studies there in black and white. We knew something was going on.
P.S. you don't look like a geek.
Oh, that's so weird. So I show up to raise money. I can remember this time vividly. I'm in the room, like, I get eight minutes to pitch, like, you know, the sea of blue and gray suits of guys. I talk. Open it up. Yep, open it up. The conversation. I want to talk about the first drug ever for women's libido. And literally, it was middle school giggles. Like, the whole room erupted. And it was such an important moment for me because I can remember thinking, oh, my God, where do I go from here? So I reached out to my slides, and I advanced, like, as fast as I could. And then all of a sudden, I get to the brain scans, and I pointed to them very dramatically and, like, went silent so they would feel uncomfortable, too. And I said, I'm just here to talk about the biology of sex in women. Are you looking at what I'm looking at? And they all got quiet. So that's really how I've approached it, is, look, the science has given us the answer. We just need to get out of our own damn ways in terms of all the taboo and everything that we. To this conversation and the opinion.
So what's interesting that I just heard, and I don't know if you even recognize it, first of all, public speaking is one of the biggest fears. I think it is the number one fear people have in the world. Right? So you are in that moment where public speaking, and not only were you being a public speaker in that moment, you're presenting a concept, an idea that's important to you, and you're doing it. You're Standing in front, as a woman, in front of all men, and you're talking about the most taboo topic that there is, 100%. How do you have the confidence to deliver that or how did you in that moment?
Well, somewhere along the way, I shifted from underestimated to unapologetic. And that's so important to me. I mean, I wear pink. I wear blazing hot, besides blazing hot pink in front of this room as well. And that was a lot about a mental shift for me from everybody, you know, saying, oh, how cute, the little pink pill, to really sort of going right for the conversation we needed to be having. So, you know what, people? I talk to female founders about this all the time about confidence. I think that it's less confidence, more competence. I knew my stuff cold. They could ask me anything, and I was going to prepare. We were going to go toe to toe on data, and I was going to win the argument that way. But make no mistake, like, my hands were shaking as I was advancing those slides. Because you're in such an uncomfortable situation. But it's, you know, again, I think it's less confidence, more competence, knowing I'm capable of doing this, and frankly, the willingness to bite back those situations. I think you have to reframe in your brain as an opportunity to surprise people.
Wow, that really is a powerful moment that you were able to surprise them. How did the meeting turn out?
I didn't get any funding in that room.
You didn't?
No, I didn't. I got them to pay attention, and I learned an important lesson that that's how I was going to have to frame the conversation when I went to go speak to others, because they were going to be uncomfortable again, it's just our societal narrative. They were going to be uncomfortable when I brought this up, but it allowed me to start to figure out how to chip away.
And so who did you get the funding from Eventually.
So all this is Incredible. I raised $100 million for this company. It's very expensive drug development, and I did it all from private individuals.
Oh, my gosh, that must have been a lot of work.
Ever wrote me a check, if you can believe this. And why would they? Again, I don't fit the part. I was doing something very unconvent, but thank God it ended up working. Things work out for a reason. And I didn't have a rich uncle in my Rolodex.
Lo and behold, darn it.
So I would tell every single person I met what I was trying to do, and one person would introduce me to Three who'd introduce me to five. And I have now this incredible national network of folks that are really mission aligned with what I'm trying to do. And now in my work in the pink ceiling with female founders or female focused companies, you know, when I get excited about an idea, I show it to them and often raise all their money for them.
I need to introduce you to my very good friend Aman, who's struggling so much with raising funds and dealing with these men and in these presentations. And that's so amazing to me. I happen to be a woman that was fired by another woman, and now I'm sitting with a woman that truly empowers and advances women. How did you get into that?
I think it's your responsibility. You know, I say I walked a mile and there's stilettos. So we know 2% of all funding, 2% goes to female founders. So half the population only has 2% of the good ideas. Ridiculous. And so when I got to a big outcome and my bank account changed, I thought, there's a responsibility to pay it forward. I mean, there really is. Not only to the other female entrepreneurs out there like me, but those who are trying to break through with these products that by conventional standards people will say, oh, that's just niche. Oh, it's niche. It affects half the population. And so it's about helping others get to outcomes like me. I say my mission in the pink ceiling is to make women really rich. And it gets a response. And I say it because I do think we talk a lot about women having a voice or needing a voice. I think women need power and money is power in a way, to sit on the side of the table and make decisions about what you want to see in this world. And I know that when women make money, they pay it forward, they give it back to their community, to other women. And it's by no means am I saying money is what it's all about. I don't know a single successful person who is only in it for the money. It was love of the mission and that's why they got there. But it's an important piece of what I do today.
Wow. So what do you like spending your time or how do you spend your time? Do you gravitate more towards one project than the other?
I think it depends on sort of what's in the queue. So I like to. I work 24 7. It's what I love. My work is my hobby. My hobby is my work. And so right now I spend a lot of time on Sprout and Addy specifically because the company has come back to me. I sold it, then I got it back. So I'm spending a lot of time launching that. And then we have a couple other products coming up before the end of the year that take a lot of my time. So we sort of pace out in terms of when things are launching.
So why would you sell a company and then get it back?
Well, yes, this is a fascinating story. So I sold the business Entrepreneurs dream come true. Here's a big company, they're coming in, they're going to march this across the globe. They're going to make it accessible for women and I get to stay with all of my team and have their resources, if you will, at my disposal. And then it didn't turn out that way. So they bought us and then their business went through its own turmoil and we were the last product in and it really just got lost. They put it on the shelf. They dismantled my whole team. Everybody was gone within three months.
Oh no.
And really kind of the heart and soul of it and of the mission was gone. And so I fought them to get it back and got the product back because we did not fight this hard for women to finally get one on the board for them to not have access to it.
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I N E.com confidence Wow, that is unbelievable. How did you find that drive? Or what was it that drove you? Because I'm sure a lot of people just say, oh, I washed my hands of this, I sold the company, it didn't work out. Why would you take that all back on again after someone else blew it?
You know, it was never about. It was never about the money and it was never about creating a blockbuster drug. It was about women having an option. Take it, don't take it. But by God, you deserve a medical treatment for a medical condition we've known about since the 70s. I think I'm fueled by injustice. You know, when those things just don't make sense, or when there are unwritten rules, if you will, that are holding us back. I think you should break them. And so that was what rips the sheets off every morning and gets me going is that it was about the women that I spoke to. The women who had gone through real struggles, lost relationships over It. I think I felt an obligation to do right by them. And so I came back to get it right for women.
Wow. The stories you must get back from your customers, are they amazing?
They're incredible. And I gotta tell you, from even 2015, when I sold it, to now 2019, the difference in their willingness to talk about it, too, is profound. So if we put up, for example, an ad on Facebook, I'm astonished by how many women are so openly commenting. They're saying, this is me. Thank you for letting me know I'm not alone. And, you know, their brother's following them, their mom, their neighbor, everyone willing to say it. And I think that is the shift. Like, I can feel this is the key inflection point where we move from a sexual revolution that's gone to reproductive rights, and that's questionable, depending on the day, to a conversation about women's satisfaction. You know, if you go to the doctor today and they ask you about sex as a woman, they probably say, are you sexually active? Do you want birth control? Do you want to be tested for STDs? And if they would add one question and say, and are you satisfied? We'd actually open up this conversation forever. We'd remove the stigma, we would remove the giggles, and we'd have a real conversation about a critical component of the human experience.
So how are you going to make that happen?
Oh, I'm working on it.
So we have.
We're talking. We have a campaign right now. It's not about the product at all, but it's called Right to Desire, and it is real women's stories. Clinician experts in the field, there are stories about this, right, if you will, for women to have satisfaction in the bedroom and to claim that they're going to have to be their own advocate in it. But again, this is like a taboo. You know, the big secret that affects so many. I mean, 1 in 10 women are dealing with this. And so it gives, I think, a forum to share stories, to make the information more accessible, to share that with others. And then we work not only directly with patients through the right to desire and women to have more education, but also with the clinical community. That'll take me longer. Getting something in medicine, getting a new practice that we would proactively ask women about their sex life. That might take some time, but it's a worthy cause.
What's interesting is I put myself in the shoes of the women you're talking about when you were just sharing that. And even with my friends, we don't talk about These kinds of things.
I know we're not good to one another that way. And I think we, in an effort to be console our friends, we sort of do the same thing in that we pat them on the shoulder, you know, oh, it's just a phase. Oh, this will pass, go on vacation. And I think that's really not the answer. If somebody's suffering from a brain chemistry imbalance, if it's something outside of their control, where what we should be saying is, you know what, like something may be going on and you should talk to someone about it. And it might be that their best course is therapy and marital counseling and it might be their best courses and medication for it. But if you go back and start sort of harken back to the days of when antidepressants came out, it's really like the evolution of that conversation right where we started to understand there's a brain chemistry issue for some people and they're clinically depressed and they need medication. And so can you imagine back in those days? Today you can't imagine that you would go back and pat somebody on the shoulder and say, oh, life is hard. Suck it up. Like we think that's horrible because of what we know. And so too will the story go for women with this condition.
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I think that breaks down for women. It's the bravery of one that helps, the bravery of two and three and four. And it really. I mean, what an. That's a great story. And I think just to see somebody who you respect being willing to openly discuss something that is otherwise considered taboo makes all the difference in other people's lives. And by no means am I saying that medication is right for everybody, but the conversation is right for everybody.
Sure.
Right.
Knowledge.
Of course, if we're talking about it, we're gonna get to better outcomes, and everybody's gonna feel more permission, if you will, to be honest, in admitting their struggles.
You take on a massive amount when you come out. I mean, this is a really big deal. And because it's a conversation people aren't having, it's even more important.
No question about it is it affects everyone. It affects our. You know, again, like, it's relationships. It's not just that women are suffering in silence from this. Relationships are suffering. Home life, family life is suffering. It is a big, big conversation. My parents tease all the time, and they say, like, could you have not come up with a drug for diabetes?
Could you have cured cancer?
Could you have just done that? And I mean, when they say it, it's so true. Because if I'm not diabetic, I probably have no point of view on this medication. But I gotta promise you, like, everyone has a point of view when it comes to sex. And it has been a fascinating part of this journey of just people's. How strong their belief system is about this. And my belief is, you know, if you don't want it, don't take it. But I would never hold that back from somebody else. And I would never assign my version of normal to somebody else who might be struggling with something completely different in a medical condition.
It's about empowering others 100%. And this is just another way, yet.
Again, to do it for very interesting days.
I can only imagine. I'm sure you've gotten some haters.
Oh, for sure. Oh, of course.
Give me a story about some of your haters.
Well, you know what? I will tell you. So I see this as. And it's not political like people imagine this is political. It's really not a political issue. But I found that very early days, I was in a room full of women who I thought would be like, yeah, you know, you go, finally, we're going to break through with one for women. And I remember telling them what I was about to do. I was going to sell off this company in men that was doing so well and take this on the thing that nobody had been able to do. And if you had taken an aerial shot of that room, the entire room moved away from me, physically moved away, moved away. I said, this is what I'm about to do. And I thought, wow, these are women who I love, who I feel like would be all about. This is empowering for women. And what I found is that for some, it felt like objectification, like there was some kind of imposition of idyllic sexuality on women. And so it was important. It's an important lesson to me because I learned to have that conversation, like, this is not about, like some version of we're on all the time. This is about women who've experienced something. It's medical. We've had this diagnosis forever, and yet they want access to it. But that was a fascinating. I don't. They weren't haters for long, but that it was a really important misunderstanding. And then, you know, I got all sorts of crazy, like, hate mail and stuff as I went along from people who just feel that deeply that women don't need to have more sex.
Do you ever respond to the haters?
No, I don't have time.
You know, totally agree.
Don't have time, don't care.
Right.
And then I think you have to. If you're going to take on something that's unconventional or you're going to, you know, take on a first, you're going to have a lot of arrows in.
Your back or even just shine your authentic light, be your real you. You know, people are going to come for it. They are.
They come for it. And you just see next.
So now that you've been working a lot with helping and guiding women to create their own wealth and monetize their businesses, what do you see as the biggest holdbacks from people making that leap from not succeeding to becoming financially successful?
I really do feel well for women in general. I have a belief that you should always own a piece. Right. So I'm working with entrepreneurs. They've already made that decision. But I talk to women even in kind of classical corporate jobs today, and I say, find a way to get skin in the game. We talk all the time about how you go in and ask for a raise. I'm often asked, what's your advice for that? I said, you know what, don't be worried about like the 3%, 5%, 7% bump. Go in there and figure out how you get a cut, because ownership is going to be your path to freedom. It's going to create more financial freedom for you. And I think it's going to create more freedom to make decisions and follow those things you're truly passionate about. So fundamentally, I believe in ownership and skin in the game. I think for women who are founders, it goes back to my story about underestimation. I talk to them a lot about going into a room and expecting to be underestimated and really flipping that in their mind to be this opportunity, if you will, as opposed to this limitation. And I think if you go in with that expectation, either they'll surprise you because they won't receive you that way, or you'll surprise them because you know your stuff cold.
So when you're advising women to working in corporate America, and frankly, doesn't matter if it's a man or a woman to go into their superior and say, you know, Jim, I'm not here today asking for, for the 5% annual increase you need to cut me in and I need to become a business partner in this company. How realistic do you think that is?
I think that it can take various forms. I don't think in every case it's going to be stock ownership. I think you've got to be very clever about knowing your own data. You've got to show what you contribute to the bottom line, and then you've got to figure out either a bonus structure related to that. And you've got to set it up so that you're really saying, I believe in my own success, and this is what I promise I can deliver. And if I deliver that, I want this, I want this percentage of it. And I think it can be phantom options. I think it can be bonus structures. I think there can be a lot of different ways. It's not really like you're going to walk in and they're going to say, oh, I'm going to make you a 50% partner in the business. But it's creative paths for how you get a piece of what you create. And if you're in a circumstance in my mind where there's no way to participate, why are you staying? Like, why are you creating that value for other people?
Oh, so true.
And create the value. That's why I became an entrepreneur. Why am I, why am I going in and fixing other people's messes and not getting compensated, if you will fairly for that, I'll go make my own mess and then I have to clean it up. But I own it.
But so many people are afraid, myself included, making that leap. My experience in corporate America, which is where I spent the majority of my life, is very well lit. It's very linear. You know, the next person you need to, you know, go to to get that next position, next raise, you know, you can see how much money you can make and it's comfortable because you're not the one taking the ultimate risk that if you fail, you go bankrupt. And so to me, that comfort really is what held me there. It took me getting fired to make that leap. But now I see for all of those years I was building them long term wealth.
You were.
I was not building myself long term value or wealth. Conversely, in the past year and a half, I've lear more than I ever learned in my time in corporate America. I've built so much more value and instead of feeling like at the end of the year. All right, that's a wrap. Now we're onto targets for next year. I'm saying look at everything I built this year. And now it's going to grow exponentially and I'll continue to develop and grow. And passive income is a new realization that I've had. I'm always, I was always chasing down the check each week, the check, the check, the check, the paycheck. Instead, now I've created passive income streams that continue to grow on their own. And you virtually, as long as you're still building your brand and your company, you're building those passive streams.
You're such an extraordinary case study in that though. Can you imagine? I mean, you can say confidently, you'll never look back. So it's really about risk tolerance. Sometimes you're forced out there and then you have to have risk tolerance. And other times, right, you've just, you kind of find it within and you're willing to take the leap. But I don't think you ever look back when you do that. I do say, it's so true. And I started in big corporate and then I moved small. I chased innovation, I went to smaller and smaller companies and then I decided I wanted to do it for myself, create my own band of misfits, if you will. But I think I can remember that mindset early days corporate, where it's so linear and I'm thinking like, oh, there's the ladder, this is the next step. And then this is the next step. And so I do, when I talk to young women who are getting out of school, I always say, like, don't treat your career like a ladder. Treat it like a jungle gym and swing toward those opportunities that are going to stretch you where you're going to learn new things. And certainly I would say swing toward those opportunities where you have skin in the game.
The other thing I would add to that, because when I was a younger woman, I became an equity partner with an owner of radio stations. I didn't see the leverage that I had. I had no idea. I felt lucky, quote, unquote lucky that I got the shot. You know, fast forward three years in a three year period. I was the boots on the ground. I'm the one that moved for the opportunity, ran the operation and took a $25 million property and sold it for 55 million. I got this tiny, tiny piece of the profit and he netted, you know, 20 something million dollars. What I didn't realize I was looking at as, wow, I'm getting to be a partner in something. I get skin in the game. Instead of thinking I'm moving my entire life here. He knows and feels confident in my ability to execute. I've got a ton of leverage here because he was never going to move to run it. He had the capital, but I had the sweat equity and I should have done. In hindsight, what I want to share is think bigger, don't think. You know what, I'll take the small percent and grateful for what you give me. Oh, hell no. I'm the one upheaving my life. I'm the one bringing the real value. You're writing the check to buy the property. But I need to be a fair partner in this operation, no question.
Such a good lesson.
It's a tough one to learn. And every time I see him, I'm like, you owe me $20 million. He's like, no, you signed that deal, my friend, that is a wrap onto the next one.
But you live and learn, right? I sold when I sold my first company. Typically you'll get paid an upfront and then there's a structure to your transaction downstream. Maybe it's royalties or it's earnouts in some capacity. And I wrote this contract and it was governed by classic legal language, a best efforts clause. And then I realized, oh God, your version of best efforts and my version of best efforts a little different. And I was frustrated by it. The whole time I'm like, they're not doing this. I would be doing that. And blah blah blah blah. And then eyes wide open. I sold the second business and that's really why I am in the position I am today. So when I got this check from them, structured transaction. But wait a minute. Very specific performance obligations. You need to spend this much money on education. You need to have this many salespeople calling on doctors and educating them, etc etc and now suddenly when they weren't doing it, I had leverage. And so that is why I sold it for a billion and got it back for nothing.
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Those that deal in specific seldom fail. Those that deal in generality seldom succeed and you learn from that really subjective line and then transitioning that into bullet pointed facts that you could hold them accountable to. Brilliant and so so important in business.
See we get better with with time.
I mean my skin doesn't but My brain absolutely does. I mean, come on. Yeah. Next thing you can invent in the lab, please figure out something for wrinkles while you're at it.
Okay, I'll work on it.
All right, so I want to make sure all of our listeners can find you. Where does everybody find you on social media?
Please follow me at Cindy Pink, CEO.
Cindy, there's one question I didn't ask you that I have to ask before we jet out of here. So in your career, when you look back and in your life, when was the moment that you struggled the most with your confidence?
The moment that I submitted all of my data, I'd met all my endpoints, and the FDA turned me down. I was blindsided. And I got that news. It was a Friday. I just landed, I'd been on a trip, and I got the news at the airport. And I can remember I sat down, and really, I don't think I moved for two hours. And the reason is I had to go in and face the company and say, like, this is it. They completely controlled my fate. And so I just remember going in thinking, I don't have any answer for all of these people who put blood, sweat, and tears in working alongside of me. And I said it. I got to the office, and, you know, we all said it. I think everybody went to a really bad weekend. I went home and took to the bed, cried it out. And the next morning, I remember I got up and I went to my inbox, and I read all the letters from women who'd written me who had this condition saying, thank you for doing this. Thank you for taking this on. And they reminded me why I was doing it in the first place. And I showed up on Monday morning, and I told the company, we're going to dispute the fda.
And that's how you were able to overcome it, is because you went back and disputed it.
I overcame, I think, the moment by just reminding myself what it was all about.
Why were you doing it?
So why?
It always comes down to that, like, what is the heart of this? Why am I doing this? And I think in the moments when you're the most shaken or, you know, the world goes sideways, if you can just return to that, to the purpose of it, you can persevere.
And the important lesson is it's going to go sideways for everybody.
Absolutely.
And it's gonna go sideways a few times, people.
Absolutely. That's right.
So hang on to that. Why? And follow your passion, not the paycheck, because when you follow that, the passion, you are able to get reboot back up and Monday hit the ground running.
That's right.
Oh, you're such an inspiration and I appreciate you so much. Now if people want to find out about pinkubator, where do they go?
So we just online thepinkceiling.com and we have all the information on how to pitch us and be part of the pinkubator is there. My social is indypinkceo and if you want to find out more about the mission that we're on for women to reclaim their right to desire, it's right to to desire.com Cindy, keep up the.
Amazing work you're doing. We appreciate you so much.
Thank you.
I hope you loved meeting Cindy and got some great takeaways just like I did. Before I get into your questions, I want to share an unbelievable opportunity for you. Pluto TV is the leading free streaming television service. Watch over 100 TV channels and thousands of movies on demand, all completely free. Pluto TV never even asks you for a credit card. You don't even need to sign up to watch for free. Pluto TV is the easy and completely legal way to watch your favorite TV shows and hit movies for free. What are you waiting for? Never pay for TV again by downloading Pluto tv. You can download Pluto TV for free on all of your favorite devices today, including your phone, roku, Amazon, Fire TV, Apple TV, smart TVs, PlayStation, anywhere else you stream. I mean, really, do we need any more TVs? It's a little crazy, right? So let's get into a really interesting question that I received. This came into me on DMs through Instagram. Heather. Hey, Heather, I have a question that may benefit your audience.
Ha.
We love that. Loved your Jesse Itzler episode. Guys, if you have not listened to that episode yet, he is amazing. He's such an inspiring and extreme individual and the way he approaches things, it just flipping works. I mean, look how successful the guy is. He's unbelievably successful and he's a complete inspiration. I truly would like you to listen to this episode because in my mind, it's the best episode that I've had on yet on the podcast. So I don't want you to miss it. There's so many unbelievable takeaways. He gets into this whole thing how the majority of people go 95% of the way, but when they're just about to break through and make it that last 5% seems too hard, too scary, too much, and they give up. And. And he's really attributed his success to going that extra 5%. And. And he walks us through some of the different ways he's done that, some of the different situations he's been in. But he brings so much energy to the interview, and it's just. It's impossible not to listen and feel fired up and learn a couple of different tactics and techniques from him that you can apply to your life to help you get ahead, to get to that next level. So please check out that episode. Truly my favorite yet. Such a great interview. He's really powerful, exciting guy. Okay, so back to our question. Loved your Jesse Itzler episode. You mentioned that when you show up as your authentic self, amazing things happen. I couldn't agree more. I recently had a big interview that I went into with so much confidence, but then caught some sudden nerves and was not my authentic self. I was so disappointed. But it was a great lesson in humility. While I think preparation is the key, do you have any recommendations for how to overcome nerves for those big opportunities? So, listen, here's the thing, right? It doesn't matter how confident you are. Of course you can get nervous. I get nervous, Everybody gets nervous. That's really normal. But you don't need it to completely steer you away from who you are. Because the less authentic and real you are, the more nervous you'll become. The less confident you'll be, the less you'll lean into your instinct in, you know, listen to your gut, trust your gut, and respond to questions from a real place that you feel solid and aligned with. So there's a lot of different things that you can do in a situation like this. Of course, number one. Yes. Prep and prepare. I research everybody before I'm going to meet with them. I want to know all that I can know about them. What are some points we have in common? What are some connection points? You know, the more we can visualize ourselves being in a situation, being at an event, being at an interview ahead of time, and allow ourselves to feel more comfortable. Maybe you just drive by the offices so you know where you're going to park. Maybe you talk to somebody that works there. Maybe you talk to someone that knows a person you're interviewing with. The more work and energy you can put into this, the easier you're going to make it on yourself that day. You really want to come up with that vision of you being there, you doing fantastic things, going exactly the way that you hope they would. You know, the more you take yourself through that process and do that work, the stronger, more confident and more calm you'll be in that moment. So that's a really important key step. You need to visualize and see yourself there and do that work, do your homework and practice and prepare all potential questions, all potential challenges. Write them down. Create a list of examples that you can use. People love when you tell stories, real stories about your life, because it's real and it's you, and it's gaining insight into you, whether that be when you're meeting someone for the first time or at an interview. So I would make a list of all those examples of the time that this happened. This is how I learned how to do this. You know, really create and put that effort into going into your mind and saying which stories and examples from my life are great examples to show I'm a strong leader, that I'm creative, that I have great attention to detail, whatever it is. You know, write those different categories out and come up with each one of those different examples and stories from your past, your experience, to showcase you in the best light possible and to bring that real you forward. Another thing I do, and I talk about this a lot, I wear my power color. I have, I usually wear a red. If I'm feeling nervous, you know, I want to look my absolute strongest, my best. And I can see myself in that dress or in that jacket doing amazing because I've done amazing in it before. You know, figure out what that outfit and that look is for you, where you feel your best. Forget everybody else. You know, maybe other people are going to feel their best in jeans, but if you want to wear a suit, then that, you know, you got to be. You don't try to be someone else. That's so, so extremely important. The more you try to be like other people, the more you're going to find yourself in the wrong places. Because if you're dressing for everyone else, then you're going to start, you know, morphing in some way to these other people, which is never going to be your strongest, most talented you when you're trying to be a knockoff of somebody else. So figure out what that outfit is, that color is. I bring lavender with me. Lavender calms me down immediately in any situation. I have my playlist that I use that fires me up. I can visualize myself in other times in my career and my life, stepping on stages when I was nervous and then having it go fantastic. And that song really triggers that for me. So use that song, you know, pair it with certain memories and rehearse it in your mind so that when you're in your car, driving over and you start hearing that track drop, you're like, oh, boy, I am about to walk in to kill it. I know it. I've done this before, I've been here before, and this is going to be great too, you know, so you've got to put that work in. Pair a song, a playlist with that vision and other times in your life where you were nervous and you ended up doing well. Lower expectations on yourself. That's another big one. When I first start out with anything and I'm scared, it doesn't matter if it was. When I got fired and I was starting my own company, I remember saying, if I just sell one book and it reaches one person that really needed that message, I've done my job. I, you know, I really lowered expectations on myself because I was scared to publish it. I. I wasn't an author, you know, I was a sales leader and I was reinventing myself and that was super scary. So, yeah, I felt scared and nervous, and at that time, I felt really confident, but I was still scared. And that's okay. The way that I put it to work for me was I lowered that expectation. I connected with people far, far ahead of me. So I jumped on the phone with my editor when I got scared about publishing my book. He had published 19. So who can you jump on the phone with right before you're going to go to this interview? That's way ahead of you. That can say to you, oh, heck no. You've got this. This is not a big deal. And don't forget how fantastic you are. You know, figure out who that person is, have them on speed dial, ask them for their help ahead of time. Hey, do you mind if I check in with you that day? If I get nervous again, I might need you to help pick me up a little. You know, it's fine to lean on people for support and to lean on people who are much more successful further ahead than you because they're gonna know the right things to say to guide you to get to that next level that you wanna go to. So, I mean, there's so many different things you can do. You can practice gratitude. That will get you calm and centered. Picture three things you're grateful for right now. I'm grateful that I have this amazing opportunity ahead of me today and that I get that chance to walk into it. It. I'm grateful that it's. The sun is shining, it's a beautiful day. I'm grateful that I have so many amazing people in my life that support me and I Can't wait to tell them how fantastic this interview went. Right? Try to start focusing all that we already have so that we don't have. We have to be so consumed with the what if, right? Because at the end of the day, and this is a good thing to remember, if you don't get the interview, if you don't get the speaking opportunity, if you don't end up doing the book, whatever it is, maybe that wasn't the right path for you and this was an opportunity to redirect you to something else. I say that today knowing that, you know, I've been in that spot. When I got fired two years ago, and I was heartbroken and petrified and scared, it didn't feel like that, right? So I get it. It might not feel like it's going the right place and that you're in the right place, but you've just got to live through that uncomfortable for a minute. And it's not going to be easy. And that's okay. If success was easy, everybody would have it. But it's kind of saying to yourself, okay, if I don't try this, if I don't challenge myself to do this, I'm not going to grow, so I'm going to show up. It's not as much about the outcome. If we can let go of that for a minute, let's focus on the steps we're taking. Let's focus on who we're showing up as and when we're showing up as our best self. We are going to be the most powerful, strongest we could ever be instead of showing up as a knockoff of someone else. So if you begin to get nervous, start remembering that the way to overcome those nerves are to go through them as you. And the more you can remind yourself of that and of other times in your life where you've done that, even if it was just baby steps, the stronger it's going to make you walking into this moment. And again, the more you show up as you, the more you're going to show up at the right place or you'll be redirected to a new place, which is the right place for you, instead of showing up as a knockoff of somebody else. So I. It was funny. I had a friend send me this inspirational quote the other day, and I thought it was so cool. And I think of it right now as I'm talking about this. It says, look around you. How many people do you think are settling in their life? Probably a hell of a lot. People settle into okay relationships okay jobs, okay friends, and an okay life.
Life?
Why? Because okay is comfortable. Okay pays the bills, provides a warm bed. Some people are fine with okay, and guess what? That's okay. But okay is not thrilling. It isn't passion, it's not life changing or unforgettable. Okay is not the reason you risk absolutely everything you've got for the smallest chance that something absolutely amazing could happen. I love that I'm so living that even though it is so scary and I'm two years in and I'm still scared all the time because I'm constantly challenging myself to grow. So to this listener that sent me this question, I'm so proud of you that you were scared and nervous and you still went to the interview. Going to the interview is the win, right? Remember, we're not going to focus on the outcome right now. You might not have shown up as your most authentic self in that instance, but that example and the fact that you didn't quit and you did go through it and you did show up, that's the win. And that's going to propel you to the next level next time so you can be your most authentic self. And just don't forget when you really are you people, the right people are going to come to you. When we don't show up as the real us, we're going to attract those wrong people. So, you know, really step into. You lower those expectations. Remember, you're not settling, you're growing. You're going for something new. And that feeling of fear, that's actually a green light. That means go. And actually it truly means go faster because the faster you break through that fear and get to that other side, that's where all that growth exists and that's where all that good is happening. So I'm so excited for you going to that interview. I can't wait to hear about the second one and what power color you rocked and your playlist that you put into place and who you dialed right before you walked in to get you fired back up. And never forget, leave a note on the bottom of your shoes to remind you you can do all things because you absolutely can. I am living proof of this. And the craziest thing is on LinkedIn, it was my two year anniversary this week of creating my company and going to work for myself. Boston Heels. And I've received a ton of DMs. And one of the DMs I received today actually was from the chairman of the company that fired me two years ago. He became ill and stepped down I had worked for him for 14 years and his daughter took his position as CEO. And today I got a note from him saying, congratulations on your two year anniversary. And I. And I found it funny. So I googled the company to see how they were doing. The day that I got fired, two years ago, that stock was trading over $10. And today it's August 12th, that company stock is trading at $3 and change. So, you know, I didn't know any of this was going to happen. Back two years ago. I had no idea what I was going to do. I literally felt petrified. Scared isn't a good enough word. Petrified. Sick to my stomach. Faint. I could. I feel like I could faint. I was dizzy. I had a hard time catching my breath in that window of time. And today to see what's transpired and, you know, the. The success of my book and my speaking career that I didn't even know I'd ever have. I never knew I'd be an author. I never knew I'd have this show. I never knew I'd have Gary Vee or Ryan Sirhan or Lisa Lampanelli or all these amazing guests on my show or that my show would do so well. I didn't know any of these things. I just kept moving forward in that face of fear and, and feeling scared and going anyway and. And that's what brought me to this moment now. So that now, as I continue to grow and challenge myself to move into fear every flipping day. Because if I'm not, I'm not growing. I really am finding ways to get better at it. And again, it's not easy, but I know that it's right. And I'm getting stronger. And you will too. And I'm so grateful you're on this journey with me. If you haven't yet, please rate and review this podcast. It helps me so, so much. You have no idea. And please share with your friends. If you're loving creating confidence, it would mean the world to me. Till next time. I'm gonna see you next week. Week. I'll be creating confidence right along with you.
Thank you.
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