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What if the “safe” choice—a steady paycheck, a traditional career path, playing small—was actually holding you back from building the business you’ve always dreamed of?
In today’s episode, I sat down with Carrie Kerpen—entrepreneur, author, and founder of the Whisper Group—who built and sold an eight-figure company and now helps women transform their businesses into valuable, sellable assets. We get into how financial fear and freedom shaped her entrepreneurial journey, why most of us never feel “ready” to start, and the key shifts you can make to build a business that not only survives but thrives. If you’ve ever wondered how to create a business that lasts, this conversation is your blueprint.
Key takeaways:
Freedom is the ultimate motivator.
Carrie shares that entrepreneurship gave her the power to control her time, her income, and her destiny. For her, building a business wasn’t just about money—it was about never being trapped in a system where someone else could decide her future. This perspective reframes business ownership as a pathway to long-term autonomy.
You will never feel ready—start anyway.
Carrie emphasizes that “ready” isn’t an emotion; it’s a decision. Even after pulling off bold, unconventional projects (like her wedding that became a $100K sponsorship event), she still struggled with self-doubt. Her story proves that successful businesses aren’t built by waiting for certainty, but by acting in spite of fear.
Treat your business like an asset, not a hobby.
One of Carrie’s central lessons is that too many women view their companies as side hustles or temporary endeavors rather than assets with transferable value. Shifting your mindset to see your business as an asset unlocks opportunities for scalability, stability, and eventual sale—even if you never plan to sell.
Sustainable growth requires “RED” revenue.
Carrie explains that lasting businesses keep their revenue Recurring, Expected, and Diversified. This model not only builds predictability but also creates resilience, allowing businesses to weather challenges and maintain value over time.
Closing the exit gap for women founders.
Women entrepreneurs are exiting their companies at far lower rates and for less money than men. Carrie’s mission now is to help women close this “exit gap” by educating them on building sellable businesses, avoiding burnout sales, and planning for exits on their terms. This is how women create businesses that not only last but also deliver lasting wealth.
Loneliness and risk are part of the journey—but support makes it survivable.
Carrie opens up about the isolation of entrepreneurship, especially for women who often lack the networks men rely on. She urges founders to seek mentorship, peer support, and advisory boards—because building a lasting business isn’t about doing it alone.
Notable quotes
“You’re not risk-averse, you just don’t trust yourself.”
“The second you realize you can be your own boss is the moment you realize that you are free.”
“I love money and I love to make a fuckton of money, and my whole mission at my company now is to close the exit gap.”
Episode at-a-glance
≫ 03:00 – Money, Risk, and Gender
≫ 08:45 – The Leap to Entrepreneurship
≫ 14:15 – Starting & Growing a Business
≫ 21:15 – Risk, Anxiety, and Trust
≫ 31:35 – Building Businesses as Assets
≫ 38:45 – Burnout, Scaling, and Revenue
≫ 43:30 – Mistakes & Taking Risks
≫ 45:45 – Support & Loneliness
≫ 49:55 – The Exit Gap
Carrie’s Links:
Website: https://www.wearethewhispergroup.com/
Book: https://www.wearethewhispergroup.com/the-whisper-way-book
Instagram: https://www.instagram.com/carriekerpen/?hl=en
Find out how much your business is worth: http://whispercalculator.com
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Meet Carrie
Carrie Kerpen is the founder and CEO of The Whisper Group, the #1 Exit Readiness Advisory Practice for Women-Owned Businesses. Prior to launching The Whisper Group, Carrie started, and scaled Likeable Media, a women-led digital agency, which was named the 6th Best Place To Work in New York City. After successfully navigating the sale of Likeable to a 1200-person technology firm, 10Pearls, in 2021 Carrie researched The Exit Gap, producing an annual report on the disparities in exit values of female-led companies . She went on to build The Whisper Collective, the only community dedicated exclusively to exited female founders. She is the author of WORK IT: Secrets For Success From The Boldest Women In Business and THE WHISPER WAY: The Secret Formula For Women Entrepreneurs To Scale and Sell For Life-Changing Money (May 2025), as well as the host of The Exit Whisperer, a podcast featuring exited female founders. Carrie is also a Certified Exit Planning Advisor (CEPA), and lives in Port Washington, New York with her husband, her three children, and her dog Homer.
Transcript:
Tori Dunlap:
What if the very thing you thought was keeping you safe, the steady job and paycheck, the low-risk choices, the idea that playing small is the smart thing, is actually the thing that’s holding you back? If you’ve ever dreamt about building something of your own, but you’re stuck in fear, this episode is for you.
In today’s episode, I’m talking with author, entrepreneur, and founder Carrie Kerpen of the Whisper Group.
Carrie Kerpen:
The second you realize you can be your own boss is the moment you realize that you are free.
Tori Dunlap:
After building and selling an eight-figure business, Carrie has made it her mission to help women see their businesses as not hobbies but assets.
Carrie Kerpen:
The difference between a successful entrepreneur and an unsuccessful entrepreneur is time and commitment to that act.
Tori Dunlap:
In this conversation, Carrie shares about how financial anxiety shaped her path to entrepreneurship, why she believes freedom is the ultimate motivator and how women can start scale and even sell their businesses without waiting until they feel ready. Because ready is not an emotion, it’s a decision.
Carrie Kerpen:
I love money and I love to make a fuckton of money, and my whole mission at my company now is to close the exit gap which exists, which is that when women are selling their businesses, they sell them for less.
Tori Dunlap:
We also talk about identity risk and the importance of building companies that work for your life instead of trapping you in them. If you’ve ever wondered if you’re cut out to start your own business, Carrie’s story is proof that you don’t need to wait for permission, you just need to start. Let’s get into it. But first a word from our sponsors.
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If you want more info, you can go to Herfirst$100K/business-bootcamp to get signed up. This is the first and last time we’re doing this for at least the next year, and if you have always dreamt of being your own boss, of running your own life, of doing impact-driven work, then this is a no-brainer for you. See you there.
Carrie, what about business ownership do you think is the most powerful for women?
Carrie Kerpen:
Oh, it’s freedom. It’s freedom. It’s power. I feel like the second you realize you can be your own boss is the moment you realize that you are free. I mean, I’m completely and totally motivated by freedom and by nobody ever trapping me into something, and I think business ownership was the first time I ever learned how to really feel free.
Tori Dunlap:
What did that freedom look like in practice for you? How was that different than working a nine to five or working for somebody else?
Carrie Kerpen:
Okay, so I think that everything I did in the early part of my career was fear-based. I truly think I lived in fear of getting fired, in fear of not being good at my job, in fear of ultimately not having money I think was my… Financial fear was the biggest piece of the equation for me, and once I realized, I think it started when I realized that I knew how to sell. Once I realized I could ask someone for money and they could give it to me, that was when I first got into sales. I was like, “Oh, I have some freedom here. I can control my own destiny.”
And then the moment that I worked for myself was the moment that I knew that I could have real control of my time. I mean, I didn’t start a business until I had young kids, and so for me it was like, “Holy shit, you mean I don’t have to drive this hour and a half commute to rush home to give my daughter a bath?” It was just, the minute I realized that, there was no going back, which of course leads to a whole other set of challenges because you want to make the business successful, you want to make money, you want to do all of that. But I think really for me, so much of my freedom, it’s so funny, was rooted in that sort of fear. I didn’t want to work for somebody else. I didn’t want someone to be able to fire me or change my destiny in any way. I wanted that control over that destiny.
Tori Dunlap:
Yeah, I mean, we were talking before you hopped on about money memories, and you just mentioned in that response of so much of that fear was financial-based. So can you talk about was there an incident in your childhood? Was there something that happened that kind of exhausted that fear with money or made it more dramatic?
Carrie Kerpen:
Okay, so this is really interesting. I’ve been studying my obsession around financial anxiety for decades now. I grew up in a middle-class house, very middle-class. My parents had the philosophy that you do what you love, you don’t really care about money and you value security. So in other words, they took jobs working for the government. My father at first had a very successful law practice and then said, “No, I actually would prefer to be a judge.” They valued pensions. Really, really into low risk. One of my very first memories was when… Okay, so I’m going to date myself for your young audience, but in 1987 when the stock market crashed, I was a little girl and I remember being fueled by that fear and being like, “Mommy, daddy, did something happen here? Are we okay? Are we safe?”
And they looked at me and were like, “Oh, don’t worry. We don’t invest in that. We don’t invest.” So it was always like, “Do what you love. Don’t take any risks, be safe.” And it’s better to be safe and have low desires. Just keep your expectations low and just find something you really like and don’t really take risks. And so for me, I was taught that very early on, and so it was only when really working for somebody felt intolerable, which is probably why I didn’t do it until I had kids. When I had kids, it felt intolerable. I couldn’t do it anymore. I just felt like there was no way on earth I would be able to make that happen.
Tori Dunlap:
Carrie, do you have a brother?
Carrie Kerpen:
Yeah, I do.
Tori Dunlap:
Was your brother taught something different?
Carrie Kerpen:
Okay, that is a fascinating question. My brother and I have completely different views on how we were raised. That is amazing. Oh my God, no one’s ever asked me that.
Tori Dunlap:
Well, because what you just said was the feeling I think that… As soon as we put gender on it becomes very clear what’s happening because boys get taught to take risks. They get taught to try again. They’re allowed to try again. But for girls and for women, it’s, “Pick the safe option, be perfect, don’t want or desire anything.” And I think it’s extremely interesting that, but in addition that you didn’t have a want or at least not a desire that you acted upon until it was a selfless desire. Until it was, “I’m going to do it for the health and the happiness of my children. Not necessarily even for me, but because I know I can be a better mom to them if I’m home.”
Carrie Kerpen:
A hundred percent. And it’s funny, I think they had the same philosophies with my brother, but I don’t think it impacted him in the same way. For instance, when he went to state college, because that’s what my parents… That’s where you were. And said, okay, he was going to law school, he got a full ride to St. John’s or he also got into Cornell Law and my parents were like, “You take the full ride to St. John’s because it’s the safe option and it’ll be safe, it’ll be fine.” And my brother was like, “Actually, I’m going to go try and get into big law and therefore it’s going to be a return on investment for me to go to Cornell.” And he went. I never would’ve been able to do that. I would’ve been like, “I can’t do this.” Until it was for my daughters. I think that was for me, the big turning point.
Tori Dunlap:
Can you walk us through in more detail if there is a story or a moment you said, “Okay, I’m not doing this commute anymore,” but what was that path to entrepreneurship? What was the moment where you’re like, “Okay, I’ve thought about doing this before, but I cannot not do it now.”?
Carrie Kerpen:
Okay, so two things happened that really gave me the confidence to take the leap, and it was like a combination of an event that gave me confidence and an intolerance for timing. So the intolerance for timing was I worked over an hour and a half away and I was getting home too late for my daughter. But the story behind that is that when I gave birth to Charlotte, my first daughter, I had her on my own. I was in the process, when I met my now husband when she was around one. And Tori, when I tell you he wanted a larger than life wedding, I don’t mean he wanted his friends from high school. I mean if he were on this thing, he’d be like, “Hey everyone, I really want you to come watch me get married.” This big personality. Okay?
I am risk averse. I had a starter marriage with a wedding that my parents paid for and I felt like I took a risk and it failed. It was the idea that I would have to figure that out or pay for it now when I have a child, us figuring out. Impossible. And so my first thought was that I wanted him to have what he wanted and I wanted me to have what I wanted. And so out of my mouth came the following. “Dave, we both love baseball. I have an idea. Let’s pitch the minor league affiliate of the New York Mets. Okay? We’re going to buy out their night for sponsorships at six grand. We’re going to resell in sponsors into the game, and that’ll all be wedding themed.” Okay? So we’re going to pitch, like David’s Bridal will have a cute dress thing, and instead of Pepsi tossing T-shirts into the audience, 1-800-FLOWERS will toss bridal bouquets and it’ll be cute and campy and fun, and we can raise money for charity and get press and it’s going to be fricking amazing.
Okay? I don’t know how that came out of my mouth, I don’t, but it did. And the second it came out of my mouth, I was like, “I can’t take that back, what I just said,” because his face. And I was like, “Oh shit, now I have to execute this.” But we did. We raised a hundred thousand dollars in sponsorship. We were married in front of 5,000 people at the Brooklyn Cyclones, and we raised over $20,000 for the National MS Society, and we got all of this press everywhere, everywhere, you name it, national, international press. ABC World News tonight, NBC on the Money. Everywhere. It was a sponsored wedding that was done right. So they picked it up and then all the sponsors came to us and we’re like, “You know what? You guys were so amazing. You could do this. Do it again. Come up with something.”
And so it was moment, even in that moment, even when they looked at me and said, “Do this.” I didn’t feel ready. It was only when I was driving home and I was stuck in traffic. When I tell the fairy tale of the story, the fairy tale is, “They said, ‘Do it again.’ We couldn’t get married again. So we decided to start a company based on word of mouth marketing, and that was in 2007. And then social media opened to the public and boom, we were the first social media agency.” That’s the fairy tale. The real story is I’m driving. I still didn’t have the confidence. I’m driving home in my car hysterically crying that once again, my daughter’s now stepfather has to give her her bath at night. And I didn’t want it. I wanted to be the person to do it. And so for me, it was intolerable. So it was a mix of, “If I pulled that off, enough, you could shut up with your imposter syndrome nonsense and just go do it and take the leap.” And that’s what I did.
Tori Dunlap:
I want everybody to go back about five minutes and listen to that again, because the thing that you said that was so impactful that I cannot say enough on this show is that you will never ever feel ready. You will never feel ready. Whether that is in starting a business, whether that is in negotiating your salary, whether that’s in feeling worthy of opportunities, you will never, ever, ever feel a hundred percent ready. And again, I can say from two successful business women on this show, I have never felt ready and you’ve never felt ready, and you just have to do it.
Carrie Kerpen:
Never.
Tori Dunlap:
You just have to do it anyway. So I would love to spend a couple questions speaking to the wantrepreneurs out there, the people who are like, “I want to do this.” So first of all, what do they get wrong about starting a business? What do wantrepreneurs get wrong about starting?
Carrie’s story about turning to her wedding into a sponsored event that raised $20,000 for charity and then launching her agency is honestly one of the wildest origin stories I’ve ever heard. When we come back, Carrie and I dive into what wantrepreneurs get wrong about starting a business and why certainty is the biggest myth holding women back. Stay tuned.
Carrie Kerpen:
Oh, my gosh. I think that the first thing is that it’s too hard to start. It’s funny, whenever I talk to somebody about how they started their business, and a lot of times I worked in the services space, so I built an agency, an agency based on people. Whenever I talked to somebody who worked in the product space, who built a business that sold big product or something like this, I always say, “How did you figure it out?” And they say to me every single time? “Google. I Googled until I figured out how to find a manufacturing plant. I looked.” We are all the same. So I think the biggest thing for an wantrepreneur is that we have this belief that you have to be a certain something or somebody to start, but look at-
Tori Dunlap:
You have to have a degree. You have to have connections.
Carrie Kerpen:
You have to have a degree. You have to have a this. Yeah. I mean, if you look at the confidence code by Katty Kay and Claire Shipman, every piece of data is there about this. We don’t take the leap unless we are certain. And so the biggest thing I think for us is to sort of abandon that need for certainty. It really, really, really holds us back. That and our own just inner judge, like, “Who do you think you are?” Think about it. I had pulled off something that was pretty impossible, and I still wouldn’t have started unless I got the push that I had to do this or I was going to implode. It’s unbelievable. Unbelievable.
Tori Dunlap:
Well, that word certainty too is so interesting because to someone who isn’t an entrepreneur, certainty feels like a nine to five. Certainty feels like a twice a week paycheck and hopefully health insurance and a 401k or a pension, right?
Carrie Kerpen:
Yep.
Tori Dunlap:
And every time I got a new job that seemed to promise certainty, it was nothing but uncertainty. Between bosses I didn’t respect or who didn’t like me or didn’t want to see me succeed to, I never experienced layoffs, but I have so many friends who did, or I worked at startups where there was always some turmoil of someone getting let go or something happening. And it was like, I just think that so many women, again, because we are told to pick the secure certain thing, the only certain thing to me is me.
I know-
Carrie Kerpen:
That’s correct.
Tori Dunlap:
… that I’m going to show up and I’m going to do my best work and I can rely on me. I can’t necessarily rely on everybody else, and especially a job that has… I am the lowest of the low on the totem pole of responsibility. So if you’re looking for certainty, being in an environment where you know you’re worth more, but keep telling yourself, “No, it’s not the right time.” You are basking in uncertainty.
Carrie Kerpen:
You bet. And now more than ever. Whether you are early in your career or you are midway through your career and making a good amount, you better bet that companies are looking at how to make you a little more expendable all the time. The further up you go in a way, the less certain you are. So no matter what, it’s always a good idea to think about what you would do if you were on your own and how you could do it, and then just take a leap if you can. If you can.
Tori Dunlap:
Yeah. Well, and again, with government jobs, I’m not going to spend too much on politics here, but we are seeing how many government jobs get slashed. That felt like the secure, smart thing, right?
Carrie Kerpen:
Yeah. My dad passed away about 15 years ago, and I always think, “What would he think about this?” That is, like, all you thought was ever secure is now totally upended. Like, wow, I wonder how he would approach that feeling of security and safety now. It’s wild. Wild.
Tori Dunlap:
I think one of the things that holds people back from starting a business that you’ve already briefly touched on is the belief that, “I need to have certain credentials or a certain amount of money.” Or, “Oh, I have kids so I don’t have time.” Or, “I work a busy schedule already, so I don’t have time.” What sort of those other limiting beliefs are we telling ourselves that are actually not true at all?
Carrie Kerpen:
Yeah, I think the concept of what we have time for is really, really important because we make time for what we feel intrinsically is important. And when we don’t make time to living out our fullest potential from a career perspective with entrepreneurship, we are simply reinforcing for ourselves that we’re not important. It’s really like, “Okay, you don’t have time. You’re not making the time because you are telling yourself that you are not important enough to do that.” And again, that does come from a place of… There is a place of privilege there. This is not for when you’re really paycheck to paycheck and in that situation. It’s a very, very challenging thing.
But at the same time, I think another piece that’s really important is just, I always look at this. I just had a friend the other day who was laid off for the second time, and I said, “What you do is so amazing. You could consult, these people don’t want to pay these six figure salaries, but lots and lots of companies would pay you to come in to set up their infrastructure.” And she was just so filled with fear. And at one point I looked at her and I said, “Let me ask you something. What are your other options right now? Your other options are to go look for another job and go through this again. Bet on yourself and make that time for yourself if you can.” It’s a very loving act, I think to start a business. It’s an act of self-love.
Tori Dunlap:
One thing I’ve talked about online is that I’m not special, and I don’t mean that in a derogatory way, like criticizing myself. Again, I think it’s easy to look at you or I, and even in this conversation, again, your brain, dear listener, probably right now is going, “Okay, but they have something I don’t.” Again, privilege.
Carrie Kerpen:
So true. Yeah.
Tori Dunlap:
Maybe. But I am not special. I didn’t even study technically the thing that I’m doing now, I don’t have a rich uncle. I am not special. I don’t have a confidence gene that I was born with that you don’t have. There’s nothing I have that you don’t, except that I started before I was ready, done was better than perfect, and I just decided, “You know what? We’re just going to launch this thing and I’ll figure it out as I go.” That was it.
Carrie Kerpen:
And you probably removed judgment from yourself.
Tori Dunlap:
I had to. I had to.
Carrie Kerpen:
I think it’s so much… We sit and judge ourselves in a way that is so damaging. If I look at every aspect of my business, I say, “Oh, that’s not good enough. That’s not,”… It’s totally self-defeating in every single way and so I totally agree with you.
Tori Dunlap:
It’s also identity-driven. It’s identity-driven too, because you can fail and men for the most part just go, “Oh, I failed,” or, “That didn’t work out.” But women internalize it. We go, “I am a failure. I failed, so therefore I am a failure.” As opposed to, “That didn’t work out. What did I learn? We’re going to keep moving.”
Carrie Kerpen:
Yeah, you’re exactly right. Identity being tied to what we do is a whole thing. So I sold a business that I ran for 14 years. I was Carrie, the CEO of Likeable. I got married on a baseball field and started this business, and here we are. And then all of a sudden I sold it and I was like, “Who the fuck am I? Who am I now? I have to be a whole new person.” And so the idea that we attach ourselves to who we are in any given moment to what we do, that our worth is tied up in what we do is a whole other ball game. I mean, that’s… Forget it.
Tori Dunlap:
I think before we transition to talking about the sale of that business and all of that, in your book you talk about walking people through finding their secret sauce. And again, this is where you have to discover why you uniquely are set out to do this particular thing. So what are two specific things our listeners can do today to start uncovering what their secret sauce is?
Carrie Kerpen:
If they already have a business or when they’re figuring out to start their business? I can answer that.
Tori Dunlap:
Figuring out to start the business. Let’s do that first.
Carrie Kerpen:
Figuring out to start. When you are doing something professionally, where do you feel at your best and like it’s effortless? Where do you feel like you’re in the zone? What is that moment? That’s the internal, where do you feel? And then think about really what do people tell you you’re also great at, which is external validation, which typically I tend to avoid external validation, but I do think it’s good to see what people notice on the positive, what you’re really good at and see how well that matches up with what gives you joy, what gives you that spirit, what gives you that boost. And then the last thing that I would say, I actually, when we talk about confidence and we talk about competence, what we need to do, I always go for the MVC, which is the minimum viable competence. After I sold my business and I was like, “Okay, I’m going to start a new career.” I was like, “Okay, I’m going to go into helping women build sellable businesses.” And I was like, “Okay, I did it myself. Do I really feel confident enough to have other people do it?” And I’m like, “Yeah, yeah, but I’d like a little tiny bit more than me, so what should I do?”
So I got certified as an exit planning advisor and I was like, “Okay.” In that moment, it validated what I already knew. I did a very small… I walked into the class and I was like, “I know all this shit.” And then I felt so much better. I was like, “Oh my God, look, I’m validated by this experience.” So I look for what is the minimum viable competence you need to be able to take that leap because competence is a good thing. It’s good to have competence, but it’s way, way more important for us right now to focus on the confidence to just take that leap. So I like to pair up minimum viable competence with just really where you are in your zone of genius.
Tori Dunlap:
My last question for you, for folks who want to be business owners, you mentioned in this conversation that you’re risk averse, which I know is something a lot of people who want to be entrepreneurs resonate with.
Carrie Kerpen:
Yes.
Tori Dunlap:
Because I think typically we see that entrepreneurs are comfortable with risk or we interpret that they’re comfortable with risk. How do you work through that trepidation you feel?
Carrie Kerpen:
I feel it and I do it anyway, and I journal the shit out of it. I mean, Tori, it doesn’t go away. I really want to be clear for anyone who is struggling with that financial anxiety or risk aversion. So I built up that business. It was extremely profitable. It was an eight figure business that I sold for eight figures. The anxiety or the risk aversion, it doesn’t go away. And the reason is that it is rooted in a lot of your childhood shit and a lot of things that go… Well, feelings about money are almost never truly financial, almost never.
Tori Dunlap:
Nope. Almost never.
Carrie Kerpen:
I mean, you know this, you know this. And it’s crazy. And I think for me, a lot of the times, I always think… I’ve done a lot of thinking on this of where some of my stuff comes from and it’s risk aversion. And it’s also from the time that I was young, I was very, very generous always. I always loved to buy people things and do things and da, da, da. And I think that some of my fear around money and listen to this, how fucked up this is. Hopefully your listeners can get so deep, is that if I don’t have money, I can’t be as generous as I want to be. If I can’t be as generous as I want to be, what happens? People might not like me, and that is where my money shit comes from. That is truly, truly crazy making stuff.
Tori Dunlap:
No, but that’s almost every woman listening to this show right now.
Carrie Kerpen:
It is. It’s absolutely insane. And so the point being it doesn’t go away, it just shifts and morphs. You learn to take more risks, but you always have it within you. So just know it.
Tori Dunlap:
I just wrote down, “You’re not risk-adverse, you just don’t trust yourself.”
Carrie Kerpen:
That’s right. That’s right. It’s so funny that you just said that because I think last night I wrote this in my… I was doing this journaling program thing that I’ve been working on, and I wrote, “The opposite of anxiety is trust.” I just wrote that down. All of that anxiety that I can feel sometimes, if I just trust whether it’s… First of all, believe in myself, believe in all the things. It’s true. It’s a real antidote. I mean, trust is it.
Tori Dunlap:
So if you’re running a business, I think something that starts to happen as you keep going is that a lot of business owners start feeling disconnected from their why. Can you share an example of what that might look like? And then how do we reconnect to why we’re doing this?
Carrie Kerpen:
Yeah. So I think why is the single most important question that we’re going to ask when we’re looking at our businesses and what we’re doing and how. With my own why when we started… So as I mentioned after the wedding, “Do it again.” Yay. We start a word of mouth company, becomes a social media agency. It starts growing really, really quickly. One of the first social media agencies in existence, Fortune 500 companies calling us. We have no business working with Fortune 500 companies. We were babies and trying to figure it out. So we’re growing this company, starts to become really big. Dave, my husband, is like, “You know what? I want to launch a tech company. I want to go take more risks.”
I was like, “Okay, go try this and I will focus on how to make this little agency profitable and give us some money.” We were operating… This is the other thing that people don’t realize. When you’re growing a business quickly and you work with things like Fortune 500s, they take a very long time to pay. You have to hire staff, you have to do all the things, and it was not like massively cash producing yet. And so in that moment, my why became survive, right? As we learned how to grow, and as I focused on, I was very focused on how to make that thing profitable and how to grow it to sell and all that, I realized that I was disconnected from that business. It just wasn’t what was fueling my soul. It didn’t feel aligned with who I was. And so in being disconnected from that, I immediately said, “Oh crap, I need to sell this business. I need to get out.”
And what I realized in that process was that I was kind of trapped. I had built this business and it was big and it ended up providing a very healthy income for our family. And I was sitting there and the prospect of selling it was so scary, but I needed a way to be able to get out. And when I was looking at my why, it was like, “If I sold it, what would I do? If I’m so misaligned, who am I and where am I going?” And it wasn’t until I got really clear about what I wanted to do next that I was able to successfully sell the business.
It’s very hard when you own a business, you start a business, you think you’re so excited, you build it, then you’re done with it, then you’re like, “What the heck do I do with it?” And it was just really malaligned or sometimes we set out with big dreams, “I want to make a fuckton of money,” this, that, the other. But if you can’t articulate to me why, then something’s off. Why? How much and why? And getting through and really to the reason behind the number and where you want to get to. That’s another area that I work with founders on a lot.
Tori Dunlap:
I want to touch on something you just said, which is, “My why was I just need to make money or I wanted to make a fuckton of money.” Again, I can hear the listener’s brains going, “My why if I’m a business owner has to be some sort of moral good.” It has to be I’m saving puppies from the shelter. I am donating 98% of my profits to cancer research. I hope if you’ve listened to this show enough, you know that, quote, make a fuckton of money is a great reason to have… That’s a why. That’s why enough. You don’t have to apologize for it. But how do we run businesses that both feel values-aligned while we’re also like, “Yeah, I want this to be fucking huge.”?
When we come back from a word with our sponsors, we’ll dig into the loneliness of entrepreneurship, why women don’t always take the same risks as men, and what kind of support makes the difference between burning out and building something that lasts. We appreciate you listening to the ads as they allow us to do this show for free for you.
Carrie Kerpen:
So make no mistake, I love money and I love to make a fuckton of money.
Tori Dunlap:
No shit.
Carrie Kerpen:
And my whole mission at my company now is to close the exit gap which exists, which is that when women are selling their businesses, they sell them for less. But my whole mission in life is to make women more money. One thing that is really, really important is when you’re building a business that it has solid business fundamentals, that when you’re looking at the profit, you’re basing it in a space that’s real for the business and building real goals that help you get to where you are. So for me, it’s about, “Okay, I want to make a fuckton of money because I want to be able to not be tied to anyone.” We talked about freedom in that way. I would very much like to get to a point, and I’m unapologetic about it, that I’m at fuck you money.
The question is how much money is fuck you money? And that number by the way, is different for everybody. It’s different based on where you live, if you have kids and extra family in your life that are dependent upon you, what your lifestyle is. So for me, what I like to do with founders is get really clear on what they want and sort of really being able to articulate why they want it, not because they need to apologize, really because I want them to have and get exactly what they want and then plan backwards to get there. I think about, I set out that vision for what I wanted to do, and then I went for it and planned backwards to get there, and that’s sort of how I was able to do it.
Tori Dunlap:
Well, in the same theme or the same vein as that, you’ve said that we need to stop thinking of our companies as lifestyle businesses. I would also lump like, “Oh, it’s just a hobby,” into that. You said we need to start thinking of them as assets.
Carrie Kerpen:
Yes.
Tori Dunlap:
What does that unlock for us when it stops being a lifestyle company or a hobby and starts being an asset?
Carrie Kerpen:
Yes. So first of all, my relationship with the word lifestyle business is complicated because I think every business is technically a lifestyle business.
Tori Dunlap:
Lifestyle business, yeah.
Carrie Kerpen:
You’re just choosing your damn lifestyle. That’s it. But I think that if you’re looking at the way we look at our businesses, when we look at, there was a study done that looked at businesses that were sold over a 10-year period. 1% were female founded. And the reason that is, is not that we’re starting businesses less, we’re actually starting businesses at twice the rate of the population growth. We are starting businesses, but we truly don’t think of them, many of us, as anything other than hobbies or something to get us through child-rearing years or a side hustle or a whatever the heck it is. And we’re not looking at them as assets.
Now for me, I look at every business whether or not I want to sell it, I don’t give a damn if you ever want to sell a business. I look at every single business as an asset, which means you’re building this thing. If it is something that could be transferred to somebody else, it has value beyond what it’s making you today. And every single business. I don’t care if you are a coach or a solopreneur or baking cookies or wherever you are. Every single business can be transferable. And when I look at businesses that you build and I look at how businesses are valued, it changes the whole way you run something. So in other words, if you run a business that’s $500,000 a year and off of that business, you make a hundred thousand dollars a year, right? You bring it home. If you transfer that business, you’ll be paid a multiple of that a hundred thousand dollars without having to work all of the years it would take to do that.
And when this number gets bigger, your multiple gets exponentially bigger. So when we have a shift, even if you never want to sell it, even if you think I’m batshit. If you build it so that you can sell it, then when you get that moment of either, “Oh shit, I really don’t like doing this anymore.” Or, God forbid something happens to you or your family and you need a change, or you get a divorce or you have something where this needs to be sold, you are able to do it. And that for me, it’s all about… My key motivator is definitely freedom because it’s about making sure that women have the freedom to get out when they need to. It’s about making sure that they don’t have anyone controlling them. And sometimes when you leave work and you start a business, it feels like the business controls you. And so it’s all freedom all the time.
Tori Dunlap:
Carrie, how do we determine the difference between I want to sell my business and burnout?
Carrie Kerpen:
I mean, ideally, almost always when you’re crying and you want to sell your business, it’s burnout. Everyone who calls me is like, “I’m done. I want to sell my business.” And that’s okay. It’s okay. It’s just not ideal.
Tori Dunlap:
I love this business, and dear listeners, I can tell you fully transparently, I have had the, in a literal closet crying moments of like, “I’m fucking done.” Now was I done? No, but-
Carrie Kerpen:
I felt that way.
Tori Dunlap:
Right.
Carrie Kerpen:
So you have to be able to evaluate what is a moment and what feels more like a movement. There’s two ways that I like to know if you’re really ready to be done versus just being burned out. One is you’re on an up and you’re like, “You know what? This business is beautiful and it could go to a new home.” It could in a space of calm, of really being in that space. And the other one is just you’ve extracted the value that you feel… Like a lot of people are able to extract the monetary value that they need from the business, and then they want to find it a good home. Those are great. If you are burned out and want to sell, there’s no shame in that. It’s just really good to get it to a space. That’s why I like to think about making a business sellable before you ever think about wanting to sell it.
Tori Dunlap:
Okay, so what are the first signs that a business is ready to move from scrappy and stable to scalable and sellable?
Carrie Kerpen:
Okay, so scalable is an interesting word because I’m very big on bootstrap businesses that just steadily build and don’t need massive capital infusions to give up your equity and blah, blah, blah. It’s not my bag. So for me, I think it’s once you have product market fit, you have a monetization model, you know how much you make off of what you sell, you have a good idea of that profit margin, etc. And you feel good and then you’re ready to test stuff. You get it to a space where enough people have tested this and you’ve learned and you get it to a space where it’s making some money and then you think, “Okay, am I ready to take some of that money?” And this is hard to do because we’re A, raising scarcity and B, we like money, so we’re going to take some of that money and bet on it.
So let’s say you’ve started a consulting business and you are loving it or an interior design business, you’re loving it, you’re great, make good living, your cost is right, it’s all good. And now you want it to be bigger. Maybe you want to invest in ads, maybe you want to bring on a partner. It could be a million things you want to do. Once you have an understanding of the profit, you take that risk and test. And the biggest thing that I have learned is just don’t be afraid to fail. So lots of tests fail. I mean, I’ve tested a million things in both businesses and they failed, and then some have been huge wins and you just don’t know until you try.
Tori Dunlap:
You talk about that not all revenue is created equal, and I could not agree more with that.
Carrie Kerpen:
Yes.
Tori Dunlap:
So what should listeners look for in their revenue to know that it’s healthy and scalable versus it’s revenue that’s keeping them trapped?
Carrie Kerpen:
Okay, I wish I had a glass of wine with me because I would explain it. So I talk about, I have an analogy in the book that talks about keeping your revenue red. So normally we like to be in the black, not red, but red means that your revenue is recurring. So whether it’s retainer base, subscription base, any of those things, or you have customers that repeat and you understand that. So recurring, expected, you’re able to forecast with relative ease where you’re going to be and like, “Okay, we know generally,” it doesn’t have to be exact, but it should be, “We have a good idea, recurring, expected.”
And then the last piece is diversified. So you don’t want to put all your eggs in one basket. You don’t want to put all your eggs in one sponsor, one client, one anything really, one product. You want to make sure that you have an ability to really diversify that acts as a safety net. So I always say, “Keep your income red. Recurring, expected and diversified.”
Tori Dunlap:
That makes me feel really good because I’m doing all of those things.
Carrie Kerpen:
I know you are. I know you are. I’m so proud of you.
Tori Dunlap:
It’s also something that the forecasting bit, again, if you are someone who wants to start a business or in the early stages of business ownership, you’re like, “What do you mean forecasting?”
Carrie Kerpen:
You don’t know it. You can’t do that.
Tori Dunlap:
I’m telling you that you can get to a point I know with pretty darn close accuracy what the business is going to make. We’re recording this July 2025. I could tell you what it’s going to do in December of this year. I could tell you January. I could tell you July of next year. And I only know that because I’ve been in business now a couple of years, and I understand if there’s seasonality, I understand if we’re promo-ing things. July is also a unique thing because we always do a birthday sale because it was my birthday last week, so that’s predictable. So those are the things that, again, if you are a newbie business owner or somebody who wants to be a business owner, you’re going, “Well, I can’t do forecasting. I can’t determine what’s going to happen a year from now, so I can’t be a business owner.” No, this is the kind of thing that you learn while running the business. And I would say 98% of the shit that I know is because I learned it while running the business.
Carrie Kerpen:
Absolutely. And my other thing that I say all the time, so very interesting because I launched this… I’ve been in this business, which is the Whisper Group for a year, and the thing that I keep saying is that my biggest lesson from this, because I built totally from scratch again, as long as you think it’s going to take you, it takes longer. Even if you’re a fast-growing business, it takes a while. You’ve got to test and learn. You’ve got to play. You’ve got to do all of that and just don’t beat the crap out of yourself when you are not able to forecast immediately. Don’t beat yourself up if you have one big client in the beginning. If that’s what helps you start, it’s great.
Tori Dunlap:
What is the most common mistake that you see women make in trying to grow and then eventually exit their business?
Carrie Kerpen:
Well, the biggest mistake I see in exit… I’ll go backwards. The biggest mistake in exit is selling when you are totally burnt out and depressed and on a low. You want to be able to go out before you need to, it’s just like a credit line. I don’t know if we talk about this on the show, but apply for a credit line when you don’t need one, not when you need one. Because when you need one, it’s harder to get, I have a whole story with that, but you want to sell when you’re on the up, when you’re feeling good, your value will be exponentially better. So waiting too long.
And the biggest mistake when growing their businesses, I think for women, it’s not taking enough risk. I know for me it was. I mean, when I look at what I would’ve done differently with Likable, I would’ve bought a couple of small agencies. I could have done amazing things if I did that. And by the way, when you buy some of these businesses, you don’t even have to put that much cash down. Why was I afraid to do that? Why was I so afraid? But I was. I definitely was. Wouldn’t have gone on my radar.
Tori Dunlap:
I think acquisition is one that’s really interesting. I don’t want to spend too much time talking about it.
Carrie Kerpen:
Yeah. Totally.
Tori Dunlap:
I think that you and I should talk offline because it’s something that I’ve been considering seriously over the past year or two. But I think that it’s those sorts of things where, again, it’s so easy to play small and just be like, “Okay, I’m just going to focus on what I’m doing and focus on trying to scale the thing.” And it’s like, “Yeah, sometimes risk does look like, ‘Are there other businesses I can buy or reinvest in? Is there something else I can be doing that, again, requires maybe more money than I thought I could negotiate with?'” How do we get to the point where we feel like, “Yes, this business is worth investing in. I’m worth investing in. I am worth making this work, even if it does cost money, even if it does mean I fail publicly, even if it does mean that my ego’s bruised time and time again.” How do we get to that point?
Carrie Kerpen:
Okay, so one of the reasons that I built my next business was exactly this. I built the Whisper Group based on everything that I wished I had. So things I wished I had. I wish I had somebody who had done what I did similar, but had taken risks and shown me that it was possible. When I was selling, I wish I had someone who had sold their business… I was looking for women who had sold their businesses, who had taken it across the finish line. And so what I would say is that with these things, it is so important to find someone who has done this before. Find somebody who will advise you when you’re ready to take some of those risks in any capacity. We have it at the Whisper Group on growth, but there are many, many ways you can do this. The Fourth Effect helps you form advisory boards. All women. Great, brilliant, brilliant companies do this.
You need to have the difference between, you’re talking about real growth now, do you invest? When I look at you and say, “Oh my God, what you’ve done is amazing. How far you could go,” I want you talking to people who have built some real big shit, because you have built really something special and different and huge. I need people who, if you’re going to take risks, I want you to have really good insight from people who’ve done that on an even bigger scale if possible. So I do that all the time with agencies that are thinking… I’m helping all of these women acquire, all these women marketing agencies acquire other women owned marketing agencies, which are a win-win for everyone and help them grow. It’s like a healing experience for me because it’s everything I wish I did but didn’t because I didn’t have that support. So I think support wherever you get it is critical from people who’ve done it before.
Tori Dunlap:
That brings me to something didn’t expect to talk to you about, but-
Carrie Kerpen:
I’m ready.
Tori Dunlap:
… the loneliness of entrepreneurship at every stage. The, “I want to start this and my parents don’t support it,” or, “My husband doesn’t support it,” or, “My high school friends make fun of me posting on social media,” which by the way, get fucking new friends, but-
Carrie Kerpen:
A hundred percent.
Tori Dunlap:
… as someone who has grown a business that continues to do well, there is the phrase though, “The higher you climb,” what is it? I don’t know. “The higher you climb, the less people you have to talk to.” I don’t know.
Carrie Kerpen:
That’s right.
Tori Dunlap:
I don’t know what the actual phrase is.
Carrie Kerpen:
The thinner the air. Yeah.
Tori Dunlap:
Yes, thank you. The old phrase, “The higher you climb, the less people you have to talk to.” But I think every aspect or every stage of starting, running, growing, exiting, a business can feel extremely lonely, especially if you’re a woman, especially I think if you’re a woman of color where you’re like, “Who else has done this? Who else will talk to me about it?” Because marginally, you just have a smaller sample size of people who can talk to you.
Carrie Kerpen:
And the network. The network.
Tori Dunlap:
Right.
Carrie Kerpen:
The thing is, men have these conversations on the golf course all the time.
Tori Dunlap:
All the time.
Carrie Kerpen:
All the time. So who do we go to talk to? I mean, I had fallen into this business with Dave, and it was great, and then he went to build something else, and then there I am at a table surrounded by men on the largest transaction in my lifetime, and I literally was like, “I don’t know if I have anyone to go to.” And I never felt more alone in my life, and I had a lot of paid professional support there.
And so for me, it’s about people who get entrepreneurship and it’s providing access to those networks of people that you don’t realize. It is unfathomable to me what… Of course, men have done this successfully forever. Of course, 99% of the dollars that exit go to men. And same thing with VC and everything else. It’s like, they have access to things that we haven’t. And yet, this is the biggest time in history that women are starting businesses. We are saying fuck it. We really are. Because it’s intolerable. Because it’s truly intolerable. And so if we just had those networks, what might we be able to do? It’s really lonely. I get it.
Tori Dunlap:
What would an exiting founder say to someone who is just starting their business?
Carrie Kerpen:
Oh, my God. They would say, “Stick with it.” They would say, “I know that it takes time.” They would say, “I’m proud of you.” They would say, “I’m proud of you, and just keep going.” I always talk about this, Tori, the difference between a successful entrepreneur and an unsuccessful entrepreneur is really time and commitment to that act. If you stick with it and are in it, you’ll iterate. You’ll find it, you’ll get there. It’s really about the commitment to the act of having this business. That business might morph, it might change, etc., but sticking with it and having the fortitude to do it just so hard, it’s lonely and you’re making money out of thin air. You’re making it up as you go. It’s really hard. So the beginning, it’s just sticking it out. If you can make it and you can produce income and get there, you can make it the first five years, you’re going to be good. Those first five years are really, really hard. It’s hard.
Tori Dunlap:
Yeah. Okay. I can’t let you go without talking the exit gap, because it’s less than 1% of all exits are female led. You said that, and when women do exit, they earn significantly less. I’m not going to ask you why do you think this gap exists? Clearly sexism and lack of resources and all of that, but are there concrete ways we can close it?
Carrie Kerpen:
Yeah, yeah. There are. Actually, there’s some really promising recent data about female founders being focused on exit readiness. So I think, I mean, yes, it’s sexism. Yes, it’s the patriarchy. It’s all the things, but it’s also that we start businesses that are more primarily bootstrapped, and so we don’t realize that it’s an option. This is all about education. If we realize and we recognize that these businesses, these lifestyle businesses can become life-changing assets, you can run that lifestyle business, you can make your money, you can raise your family on your own schedule without any push. You don’t need to be pushing because you don’t have investors. You’re doing it at your own pace, and when you’re done, you can then extract some value for your hard work.
I mean, I don’t think people know it, but the data recently, what I saw is from a Wells Fargo report, I think, and I will actually send this to you for show notes, but it talked about that women are more focused on exit readiness than ever before, and that’s what I like to see. I mean, I really try and measure… I’m trying to do the exit gap study as often as I can because I just compile all that data. But I just saw that, and that warmed my heart a little because I think it’s really a lot of it on closing the gap, you’re never really going to close the gap. You’re not going to close the gap on amount.
If fundraising is still at 2% for FEMA, then these giant behemoths… But I don’t care so much about the giants. I mean, good for them. It’s amazing. I don’t care about the big funded behemoths. I care about the woman who is starting up with no capital and figuring it out and getting through and building, whether it’s a professional services business or starting a media company or doing any of those things. I think all of those women can get educated, and I think you’ll see a mass boom on those types of exits.
Tori Dunlap:
The exit gap is real. Women are still exiting at far lower rates and for far less money than men. So when we come back, Carrie shares practical tips that every business owner can take to make their company more valuable, even if you’re nowhere near selling. She also talks me through a personal pain point I deal with when running Her First $100K, plus the one piece of advice she wishes she could go back and give herself in 2007.
I wouldn’t be surprised to hear too, that one of the reasons women are exiting at the rate men are is the ownership we have over the business of the, “This is our baby,” or I think that, again, so many women, especially I think all the time, “Could I exit from this business?” And I know you’re going to tell me yes, but one, just the emotional of how do I give up, not control in a control freak way, but how do-
Carrie Kerpen:
No, control. Yep.
Tori Dunlap:
… I not make decisions about this business anymore? How do I step away and have separation? But also too, I think people are largely here at HFK for me, people listen to Financial Feminist for me, and if somebody else hosts this show, I don’t think it works the same way. I think a lot of women are building, yes, lifestyle, but lifestyle or influencery type businesses where the trust is built with that one person. Prove me wrong.
Carrie Kerpen:
Okay. Okay. Well, I have two answers for you, Tori. I have two different answers for you there. So what you’re talking about is how do you build an exit build business? How do you sell a business when you’re a personality? Which is, you are a media personality, of course you are. And you have built a business that, from what I’ve seen and would hope to see, goes far beyond just your personality because you have systems and all of the things that you do and have and da, da, da. But you are correct that people still want you.
When I talk to someone like you, or I’m giving someone like you advice, first of all, I would pair you with somebody who really has been in your shoes, but in your case you have sort of two options. One, you could say, “Fuck this. I’m going way beyond. I’m bringing in other personalities under me, and I’m having a full-on media company.” Which you can. A hundred percent. It requires investment, requires thinking. A lot of stuff like that, or-
Tori Dunlap:
We’ve tried.
Carrie Kerpen:
Yeah, sometimes it works, sometimes it doesn’t. But just because you tried that once might mean that you not-
Tori Dunlap:
We didn’t try it well.
Carrie Kerpen:
… it doesn’t work. Right.
Tori Dunlap:
I would do it differently now if we were really investing in that again. Yep.
Carrie Kerpen:
Two, you separate and spin off some of the systems mechanisms and any schools or things that you have, you build out some things that are sort of like, they’re connected, but they’re separate from you, the person. That’s another area. Third is you run it as you have it now. You make a ton of money, and when you sell, which you can do, somebody’s going to have to pay you a fuckton for you to do it. Now the idea is you extract so much that you then don’t care. You want to be in the space where you have taken out so much that you don’t care if you sell it. And that is when you will sell it for a lot.
Tori Dunlap:
I’m not going to say who it is, but I have a good friend who sold their name and stays on as brand director.
Carrie Kerpen:
Yep, brand director. Great. And if they pay you enough, sounds great. And sometimes when I sold, I worked for the acquirers for three years and sometimes they were good, acquirers, but sometimes they would say some stuff to me where I was like, “Wrong.” They would say, “Okay, you’re going to go in this direction.” I’d be like, “Wrong.”
Tori Dunlap:
“No.”
Carrie Kerpen:
“Wrong.” And then I would say, “They paid me a lot of money for them to be wrong. It’s fine.” They earned that right.
Tori Dunlap:
Less practically… You just give me a great practical answer, which I appreciate. From the mindset point and whether I’m using me as a Guinea pig, I’m not going anywhere, anybody for a while. So let’s reassure. If somebody comes in and they’re like, “We’re going to do this.” How do I not go, “Sorry, that’s not going to work. That’s not going to work, and I need to do it,” and boom, boom, boom, boom. How do you not do that?
Carrie Kerpen:
Well, that’s the reason that a lot of people don’t stay on. I mean, entrepreneurs are entrepreneurs and they just are not happy often after they sell in terms of working for somebody else. It’s very hard to do. So you need to find an acquirer. See, the idea is you get the business and you get your own personal finances in a place that when you sell, you get to choose what you want, choose your own adventure. And for me, that’s my biggest wish. I actually talk about this all the time. So I used to talk about, one of my quotes on my website was like, “I want women to have as much money as possible,” or something very generic, which I do. But I changed it actually to be that, “I want happy, healthy exits,” because the reality is if you have a happy, healthy exit, the money comes.
The money’s a part of it, but I want people not selling their souls to people who will take over and shit all over their stuff. The other thing you said though, before, which is my business, it wasn’t really about you, but you’re saying women think about this. “My business is my baby.” That is all about the identity part that we talked about earlier. It’s that our identity is tied up in these businesses and you got to divorce that. It’s like a part of who you are, but it is not the entirety of who you are. It’s not.
Tori Dunlap:
What is one thing a business owner could do this week to make their company more valuable, even if they’re nowhere near selling it?
Carrie Kerpen:
You want something tiny and practical?
Tori Dunlap:
Give me tiny and practical and big and exciting.
Carrie Kerpen:
Okay. One thing that you could do to make your business… This actually still works for your audience, go through your freaking business credit cards and your subscriptions. You talk about that. I think you work with Rocket Money, but go through, look at all the itemized things there and just get rid of shit you don’t need. So when you sell, you’re worth multiple of your profit usually. So think about, let’s say you’re worth eight times, every dollar you save could be eight on a payout. So really focus on your profit. That is the most practical.
The biggest one I could say to be more exit ready is, oh, think about who would acquire you and go to coffee with them or virtual coffee. Just start conversations early. Who’s someone in your space that you admire? Who would you love? Just hang out, say hi. Stay on each other’s radar so that 10 years down the line when you’re ready to do this, you have a relationship with them. I should have done that. I should have sold to Hello Sunshine. I did not. I didn’t even think it would be possible. I would’ve been a good acquisition for them and I never thought it was possible.
Tori Dunlap:
It would’ve been a good acquisition for them.
Carrie Kerpen:
I know, and I should have called them, but instead I just-
Tori Dunlap:
Oh, great acquisition.
Carrie Kerpen:
I know. I know.
Tori Dunlap:
Yeah. And it’s also too, even if you never sell or if you never sell to them, it gets you in the mindset of thinking long-term about the business, which is your job as CEO is to start thinking. You’re not going to have everything. You’re not going to foresee everything. But I have a general idea of where I’d like us to be in three years. I have a general idea of that.
Carrie Kerpen:
Exactly.
Tori Dunlap:
And so you start figuring that out through conversations. Okay. My last question, if you could go back and whisper, pun intended, something in your own ear circa 2007 with 10K in the bank and a dream, what would that be?
Carrie Kerpen:
Okay. I would whisper in my ear the same thing I have said over and over to myself as someone who has struggled with anxiety and all of it, which is, “Carrie, worry is a misuse of the imagination. Just one step at a time. Go forward.” When I look at myself, I think, really, “In there is a brilliant mind. I know it.” I know what I’m able to do and all of that big beautiful brain energy being spent on worrying, it’s just a misuse of my time. And if I could say it early… I learned it later. Actually learned it when my dad was sick and I carried it through in business and it just, worry is… You can’t worry about things you can’t control. The only thing you do is focus on what you can control and focus on believing in yourself more than anyone else. I mean, you got to count on yourself.
Tori Dunlap:
I love it. If you’re watching on YouTube, my light just went out, which means apparently we’re done.
Carrie Kerpen:
We’re done.
Tori Dunlap:
It’s just like, “I’m done.”
Carrie Kerpen:
The light’s done listening.
Tori Dunlap:
The podcast episode is over.
Carrie Kerpen:
That’s it. It’s over. Time to go.
Tori Dunlap:
Carrie, where can people find more about you?
Carrie Kerpen:
Okay, you can find more about me. Let’s see. Wearethewhispergroup.com. On there, there’s a quiz that you can take to see how much your business is worth today. That’s a really good one. That’s whispercalculator.com. And on social, Carrie Kerpen. Yeah, if you go to whispercalculator.com, you can legit enter in your stuff, Tori, and you can see how much it’s worth.
Tori Dunlap:
I’m doing it right now.
Carrie Kerpen:
Do it right now.
Tori Dunlap:
I’m doing it right now.
Carrie Kerpen:
Whispercalculator.com. And please follow me, Carrie Kerpen. Social media is so hard, Tori, you do such a good job. And I’ve been posting every day for year-
Tori Dunlap:
No, I don’t think so. I don’t think so.
Carrie Kerpen:
No, it’s horrible. And then you know-
Tori Dunlap:
That’s awful.
Carrie Kerpen:
… when you said get new friends? You know when you said that about if people are making fun of you about your social media?
Tori Dunlap:
Yeah.
Carrie Kerpen:
When I first started posting early, I decided I was going to post every day. All this stuff, I would see sends and I was like, “I know who’s sending this. My little bitches in the playgrounds, they’re definitely sending this because there’s nobody following me,” in the beginning. So whatever, I just didn’t care. I basically sent a text to everyone I knew like, “Hey, I am going to spam your social media for a while and follow me. If you don’t like it. Bye.”
Tori Dunlap:
I love it.
Carrie Kerpen:
Bye.
Tori Dunlap:
That’s so good. Thank you. This was so helpful. I love it.
Carrie Kerpen:
You got it. You got it.
Tori Dunlap:
Thank you so much to Carrie for joining us. You can get her book The Whisper Way wherever you get your books. Thank you as always for being here, Financial Feminists. Thank you for supporting feminist media. Please don’t forget to subscribe. Listen to our incredible almost 200… No, we’re at almost 300 episodes of our back catalog. And if you love the show, easiest way to support it is by sharing it with somebody you love. Thank you for being here. We’ll talk to you soon. Bye.
Thank you for listening to Financial Feminist a Her First $100K podcast. For more information about Financial Feminist, Her First $100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and video engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Sasha Bonar, Rae Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Meghan Walker, and Jess Hawks. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
