Carrie Kerpen: CEO of The Whisper Group

Episode 636

In this episode of The Kara Goldin Show, we’re joined by Carrie Kerpen, the dynamic Founder and CEO of The Whisper Group. Carrie shares her journey from building and scaling Likeable Media—a women-led digital agency named one of the best places to work in NYC—to successfully selling it to a major tech firm. Now, through The Whisper Group, she’s tackling "The Exit Gap" and empowering women entrepreneurs to scale their businesses, sell successfully, and achieve life-changing outcomes.
Carrie dives into the challenges female founders face when preparing for exits, the lessons she learned during her own, and how The Whisper Group is creating a roadmap for women to build scalable and sellable businesses. She also shares a sneak peek into her upcoming book, The Whisper Way, and her strategies for helping women build generational wealth.
If you’re a founder, entrepreneur, or simply curious about what it takes to build, scale, and exit a successful business, this episode is packed with insights and inspiration. Tune in now on The Kara Goldin Show!

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Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. All right, welcome back to the Kara Goldin show. So excited to have my next guest here. We have a powerhouse joining us, Carrie Kerpen, who is the founder and CEO of the Whisper group. And I’ve known Kara for a while. She is an amazing, amazing entrepreneur who is flipping the script for women entrepreneurs, helping them scale their businesses and cash out on terms that actually reflect their worth. And I absolutely love the fact that she is an entrepreneur, and she’s come from an incredible business that she sold, called likable media, if you’re familiar with that, and if you’re not familiar with that, we’re going to get into that. She’s on a mission to close the exit gap, as I mentioned. So the Whisper group, we’re going to hear all about that, and we’re also going to hear all about her upcoming book called The Whisper way. So I’m very, very excited to have you here with us today. Carrie, thank you for joining us.

Carrie Kerpen 1:48
Thank you, Kara. I’m so excited to be here. Super, super

Kara Goldin 1:52
excited. So what’s the big problem The Whisper group is solving for female founders, and why did you feel you were the one to take this on? Whoo,

Carrie Kerpen 2:03
okay, so when I bootstrapped and sold one of the world’s first social media agencies, I started it in 2007 when there were no social media agencies, and I scaled it and sold it in 2021 I realized a few different things. First of all, there were so few women I could speak to who had done it before me like I was. I went looking for support and help, and I just felt utterly alone. And then I actually went through it. I had a good transaction. I went to a good acquire like it was all good, and yet I was fascinated with the fact that I really did not have the type of support that I felt I needed. And so I started looking into whether or not I was alone in that experience. And I discovered that not only are we capturing way less, we capture point 8% of M and A activity of dollars at exit point, 8% as compared to men. So for every dollar spent on M and A acquiring businesses, we’re capturing less than a penny. So that was the first insight, right. The second insight was that over 75% of entrepreneurs, regardless of gender, experience profound regret in their first year post exit. So we were making less and we were equally unhappy. And so I decided that I wanted to really help close that exit gap, and for women in particular, Kara it’s not just like some of us are raising funds and building these huge businesses, but so many of us are starting lifestyle businesses that we don’t even realize. We don’t even think like, oh, this is actually a sellable asset. We could take this lifestyle business and turn it into a life changing asset with a few smart tweaks, like I built an agency. It’s essentially a lifestyle business, but you’re able to create it as an asset. And so my goal was to really build something that provided women with education and support throughout their exit process, whether it’s early stage or when they’re actually ready to sell and help connect them with other women who have been in their shoes. And so that’s how the Whisper group was born.

Kara Goldin 4:17
I love it. So did you feel like people were because wouldn’t you sell a company? We’ll get into likable media. Everyone wants to know, how did you do it, right? Yeah, did you feel like people were coming to you aspiring, maybe, to also sell their company? But asking you some of the lessons that you’ve learned, I’m sure so that. I mean, there’s so many signs probably, as you, you know, just discuss where you felt like there’s things that people want to know what you do right, what did you do wrong? Maybe in many ways, they they want the roadmap, but they also want to they, maybe they want to mentor right, that that comes with it too, but they don’t actually, when. You’re selling a company. You don’t necessarily, I guess mentor is not necessarily the word right that you’re gonna look for, but that’s kind of what you’re looking for.

Carrie Kerpen 5:09
Yeah, you’re looking for support. See, here’s the thing, when I was growing likable, people ask me all the time how I did this. One of the things was I was growing it. I started it with my husband with $10,000 in the bank. Okay? We had no money, and we came from no money. And it was the type of thing where the benefit about a services business is you don’t have to invest in a lot of inventory. It’s just you’re selling your brains, and then you hire more people who have more brains, and you expand and contract as revenue grows and contracts, okay? And so as we were growing, I would get so many people coming to me about, oh, you know, are you interested in selling? When would you be interested in selling? Like, pe investment bankers, all these people. And they would come to me and then be like, Yeah, you know, I’m doing okay. I’m working, you know, I’m four years in. I got 5 million in revenue. And they would look at me and they’d be like, Yeah, okay, come back to me when you’re over 10 and you’re 30% margin. And I felt a small b dismissed and like I could never do that. So what did I do? I started doing it on my own, slowly and steadily, to get to where I needed to go. But I never wanted to call someone like that. I never wanted to talk to somebody who is financially incentivized. I should get to a big number so they get a big cut. That’s how I felt. And I was like, No, I’m gonna get to a number that works for me in my life and what I want with my goals and what we do at the Whisper group and mentorship is that as women who have built and sold these businesses, we’ve all been through that type of experience, and so we’re not incentivized by a percentage of your exit. We’re incentivized by experienced shares and helping you get across the finish line. And to me, that’s what I think is going to change the game. There’s a lot of biased help out there, but there’s not a lot of unbiased help. And for me, I wanted to build something that wasn’t based on, okay, you pay me every month until you exit, and I’ll make it last forever and ever. And I didn’t want something where you give me a cut of this exit and now I’m going to be incentivized to get you to take this deal that might not be the most beneficial to you. I wanted to see the whole person, and that’s what I found resonated so much with women in my space, like just looking at it like I want to match you. If you’re an agency, I want to match you with me. I’m going to help you. I’ve been through it. I’m going to show you how I did it. I’m going to help you do it too. You’re a CPG company, I want the exact same thing. So it’s just by somebody who’s been in your shoes. And I think that’s that, that’s what really felt like. It was my life’s work over time, you know, as I as I started thinking about what I wanted and building it, and I was like, shit, like, this is really something that’s different. And I think, you know, we as a collective, which is, we’re a collective of exited female founders, we’re uniquely suited to do this work, and so I’m so excited about it. I focused on, like, really making sure that I was credentialed and in a space where I was able to help work on exits. And then I focused on building that network and helping train them, to get them to be as well.

Kara Goldin 8:20
What’s the single biggest reason women owned businesses struggle to scale or exit compared to maybe male led businesses? Again, this is one girl’s opinion here. But what have you seen that you think women owned businesses could do better.

Carrie Kerpen 8:42
Okay, so first I have a whole report on why, which is, if you go to close the exit gap.com you can download it as great, and it gives you a whole, a whole breakdown. The first reason that the stat is so alarming is based on the same thing that we’ve struggled with forever, which is fundraising. So if you’re looking at huge exits, huge exits. Mostly that’s because people raise a lot of money and then sell for a lot of money. And if women are raising 2% of capital, they’re raising less capital. Therefore they’re ultimately selling for less because there’s fewer of them. However, I think the exit gap and why we’re selling for less exists for a different reason than that. We’re starting businesses at twice the rate of the population. We are opening businesses left and right. We are energized. We are going we’re taking it into our own hands. We’re leaving the workforce, but when it comes to actually knowing how and having a network and having a thought process that will help you build that as a sellable asset, somebody who’s like, I’m gonna start an interior design firm so I could be home with my kids. I’m just gonna, like, do Interior Design. They’re not thinking about building that as something that’s sellable. And yet it absolutely is. And so once it’s like being a consultant versus being an agency, when I started, I could have been a. Social media consultant, no, we positioned ourselves as being one of the very first and premier social media agencies out there. It was positioning, and it was the gumption to believe that we could be bigger than we were that allowed us to build and grow to sell. So I think so much of it comes first is the reality of capital, and then second is the self limiting belief and not believing that we can take some of these smaller businesses and turn them into something of substance. I mean, you can use them to run your life. I mean, listen, I love a lifestyle business. I think they’re the best, but you can use that lifestyle business and then, with a few tweaks, when you’re ready for a change, turn it into a real life changing asset.

Kara Goldin 10:40
Yeah, yeah, it’s so true. I always am surprised when I talk to entrepreneurs and who have raised capital or think that they need to raise capital and and they aren’t really thinking about some sort of exit along the way. I’m like, there has to be I mean, well, the second

Carrie Kerpen 11:00
you taking capital, you have to think about an exit. Right, right in you for funsies. Like, it’s not like, Yay, here you go. Here’s some money. Go be a good girl. Like, right? Want an exit?

Kara Goldin 11:11
No, it’s, it’s absolutely true, and I think that it’s, it’s always been a little bit surprising to me, and some you know naivety around it as well. So your frame framework for getting businesses exit ready, I think is awesome, because often, you know, you’re sitting here dealing with a P and L, you know, operating your company and trying to, you know, continue to grow, continue to be profitable or more profitable along the way, but what are the top three things every founder really needs to lock down on before thinking about selling?

Carrie Kerpen 11:51
Okay, so I’m gonna give you the seven tenants, and I’ll tell you which three are most important. So when we started the Whisper group, whisper stands for each letter represents one of the seven tenants needed to create a highly sellable business. The first is understanding your why. What do you want to sell for, and why did you pick that number? Why are you doing all of this in the first place? Like, getting really clear number, not rooted in ego, not rooted in randomness, or what the other bro down the street did, like, what do you want for your life? Understanding why is going to help you be a much better negotiator. Understanding how the market how the market works, who the potential acquirers are, who the players are networking, understanding all of it, what the multiples would be for your business. Essential. So those two things are like at the upfront. Then there’s income, which is, of course, one of the top three. We want to make sure that your revenue is I like to say we, you know, we like revenue in black, yes, but I like my revenue to be red, recurring, expected and diversified. I want to be able to forecast with ease. I want to know that it’s happening again and again and again. And I want to know that it’s diversified enough that if one thing, if shit hit the fan for one thing, I would be okay. So income, keeping your income red is the most one of the top three. The second is, if we’re going for why, how income secret sauce, understanding what your differentiator is, what your story is, how it works, your profit really, really important. You know, a lot of these companies that raise funds think they’re building unicorns that don’t necessarily need to be profitable. I focus on profit with just about everybody all the time. Those days I think are over. And so I would say focus on having good business fundamentals with with both income and profit, then your executive team, or your ecosystem really focusing on making sure that you have a good team, that the business isn’t totally reliant on you, and that you could be gone and it would be okay. Nobody wants to buy a business to just buy you. And if they do, you’re not going to want to go there. And then, if you are a solopreneur and looking at being sellable, you might want to look at your ecosystem like is the business transferable? And I think that’s a really important piece. Is building something that’s a transferable business. You can go to an acquirer with these and then the last piece is your roar factor is having the confidence to withstand going into these rooms, which are almost always full of men defending your business as it is completely torn apart during these process of acquisition. You have to make sure that you’re psychologically ready. So it’s your why, your how, your income, your secret sauce, your profit, your exec team or ecosystem, and your roar factor. And the most important, you will be evaluated on your income and your profit, for sure, but if you are really able to articulate your secret sauce, that is what will take your multiple to the next level

Kara Goldin 14:40
you were involved in a founder led company that was sold, and then you stayed on with the acquisition for three years. Do you find that that’s something that is most likely? And I guess, how do founders mentally. Prepare themselves for that? Oh,

Carrie Kerpen 15:02
okay. I think it depends by vertical and it depends on size of business. For me, when you work in the agency space, you have contracts that are usually a year they’re a year long, 12 month contract. So there’s really, you’re buying the people and you’re buying the contracts. So if you’re a smart acquirer, you’re not going to buy that business that is founder led, that is, you know, has these contracts and not require somebody to stay. Now for me, in my circumstance, I sold that agency because I felt that social media was changing which it was, and that technology was moving faster than I could and that AI was going to be a big thing. And so I set out to sell to a tech company. So there was for me. I looked at it like I wanted to stay and see what it was like. What would it be like if I worked for a technology company? What would it be like if I was part of this bigger thing, and so that my values and readiness were aligned. However, what I found, like most entrepreneurs, is that it is extremely, extremely difficult to go from being your own boss and running the show to working for somebody, and that cultural shift was very hard, even though my acquire were was great. I had it really wasn’t about them. It was about feeling like I was a free bird, and then suddenly I was caged. And that is a feeling that you must prepare for if you are part of an earn out. This is why people are so afraid of earn outs. Now I will say, or a contract, I will say, for me, I completed it. I did it well. I hit every target like it was a pleasant, relatively pleasant experience, but I couldn’t. I still, as an entrepreneur, felt like a caged bird, and so you just must prepare that, you know, more often than not, it’s not a good experience. For me, it was okay, you know, but I think it more often than not, it’s tough, and even when it’s good, it’s hard. So just knowing that like it’s temporary, I guess, unless, I mean, there are people, I think, who go on to have long careers with places, but I just don’t think it’s very typical.

Kara Goldin 17:24
Yeah, definitely. So many founders think that the end game is just about the numbers, right? And you talked about the growth and the EBITDA on Yes, you have to have all of that. But how much of a successful exit is tied to storytelling and how the buyer sees the business as well, and your ability to actually sell the business and the vision right? How important is that, in most sales? Incredibly, incredibly

Carrie Kerpen 17:58
important. It’s the third of this like you have to have the income and the profit the business has to make sense. Nobody wants sense. Nobody wants to buy a dud. But what the business wants, what an acquirer wants, is the potential of what that business can do. So it’s not just the story of who you were and how great you the founder are. It’s the story of how great you will be together and what is additive to that business, like, here’s this amazing brand, and here’s how we add to your portfolio. Here’s how we 10x what you ever thought this could be. They’re buying the potential of growth. And so for me, it was you guys do tech. We do social media. Imagine if you use tech to infuse into our social media offerings. You’ll be able to charge more cross sell. You know, all of our clients will work together. It’s going to make so much sense. That was the story. So the storytelling is very important, but it also must shift, because we as founders are used to telling our origin story. We’re used to telling our own growth story. Now, when you’re selling you’re going to tell a new story, which is how we, and what we’ve built, can add 10x to you, and that’s the story that they want to hear. They want to be dazzled by you, yes, but they really want to be dazzled by what they can do additively to their organization. So you’re telling the potential of their story. And that’s why it was of my three, it’s income, profit and secret sauce are the most important. Yeah,

Kara Goldin 19:31
I feel like it’s also understanding the other side of the table, right? That’s a negotiation, I mean, and that’s right. And if you don’t have the ability to do that. I think that that is such a big asset to have in that room. Yeah,

Carrie Kerpen 19:48
you have to put yourself in their shoes, because on your mind, see, like, usually it’s about 80% of a business owner’s net worth is tied up in their business, almost always. So large portion. Net worth. So you’re there, and you’re like, I put my heart and soul into this. This is my life’s work. I want me, me, me, me, me, and you’re terrified because it’s 80% of your net worth. It’s a big freaking deal. You don’t want to mess it up biggest transaction of your lifetime. And so if you stay in that space, you come almost from a space of scarcity, where, if you come into the space of these what will these guys get by getting us? And how can I tell this story in their shoes? That is when you really win and when you really like the multiples almost matter so much less. Otherwise, it’s just an asset sale off of income and profit. I mean, that’s like, you know, I could do a valuation on anybody’s business today and tell you exactly on income and profit, what you’re worth, but it’s not actually what you’re worth. What you’re worth is whatever they’re willing to pay, and what they’re willing to pay depends on what they think they can do with that business. And it’s up to you to tell that story and help convince them why that is the right space. So

Kara Goldin 21:03
we hear a lot about COVID time and and I think there were many people that found that COVID really put their business on hold, or, you know, there were definitely a downturn for some and then, you know, as people started to recover, there’s still that spot in their balance sheet, right? That is, that is ultimately kind of a whole, what do you tell founders where they’re just, you know, they’re trying to get it back on track, but, but, you know, it’s, it’s going slower. Do they just throw in the towel, or is there? Is there hope for people that where their businesses were kind of turned upside down? Well,

Carrie Kerpen 21:49
I think the answers are individual based on the businesses themselves, but I would say absolutely there’s hope. You want to look at the trends right. Acquirers do not care too much about the blip on the radar from 2020 to 21 if 2223 24 were great, like they don’t care. They understand everybody went through that experience, and sometimes there’s debt associated with it, and there’s all kinds of stuff associated with it. They understand that moment in time. But what they’re looking for is the upward trend, right? And if you are COVID, changed the way it’s not just COVID, it’s AI, it’s all of it. Our the way we do business is changing, and what an acquirer wants to see is that you can change with that if you can’t, and if you don’t think your business can, can you sell your business? Yes. Will you sell it at a premium? No, not unless we find the story that is so unique and interesting that it just can’t be denied. You know, it’s, it’s really, it’s really about, if you can show that there will be growth and if they buy it, you know, I recommend being really real about it, but if they, if they buy it, then you’re in great shape. If you, if you can’t tell the story of what happened after COVID and you’re still clawing, maybe it’s worth looking at doing business a little bit differently.

Kara Goldin 23:14
Yeah, definitely. So burn it down and rebuild strategy is, is something that we’ve all heard about, that some founders use to get their business exit ready. And so, does it work, or is it just hype? Oh,

Carrie Kerpen 23:32
that’s, that’s like, I feel like that’s like, gross speak like, come on, you have a history of your business. Like, you can iterate. I’m always about iterating. Getting exit ready is see to me, I work a lot of times with clients who are, like, five years pre exit, and they just want to get exit ready. What does it mean? And what it means is to put great business fundamentals in place, get a great story together, and in the end, you end up making a lot more money by making your business healthy. I think to me, to me, it’s all about creating health and better. When a business is exit ready, truly, typically, their founders are less stressed because they’ve created a business that could survive on its own. So when people come to me to sell, they are almost always in a space of, oh my gosh, I’m totally done, and that’s the worst time to sell, the best time to think about this is like to really get in a good space where you are. You’ve extracted yourself mostly from the business you it’s healthy. It’s running on its own. That’s when it’s truly exit ready, not burning it all to the ground

Kara Goldin 24:38
bankers or or going directly to your your dream, um, buyer that you think should buy your company. Bankers

Carrie Kerpen 24:49
aren’t gonna like this, so I Okay. I like going direct however a banker will, if a banker can truly show you that they are going to get you way. More than you could ever expect to afford that fee. Go for it. I mean, bankers are very, very talented. I’m not. You know, this is not to take away from them. That being said, the amount of anxiety that rests with founders around who they should hire to sell their business is immense. And I think it’s, it’s the some the fees vary. You could literally have a broker out of a truck, of the trunk of their car, saying, Okay, I’ll sell your business. You could have an giant investment banker, minimum million dollar fee. Like it, just it. The space is so vast, and that’s why, for me, I was like, one of our products that we have is called the exit whisper. It’s literally behind the scenes advising when you’re interviewing bankers and brokers and this one and that one, or how to do it on your own. Like for me, I just think it’s very important that whatever you choose, you have support from somebody who’s experienced it more, maybe even more than one, to help guide you through. So it depends on the situation, circumstance, revenue, size, potential of exit, what types of with bankers you want to look at what types of transactions they’ve done, if they’ve done one similar to yours, what their fee structure is, and then how you feel when you’re around them. And like, it’s really important, because you’re spending a lot of time, and it’s like, this is the most important transaction of your life. You want to not feel the ick every time you’re like talking of anger, depending

Kara Goldin 26:28
on the size of the company, I guess. But how, how important are boards in the sale process?

Carrie Kerpen 26:37
Depends on the size of the company. I mean, I think, I mean, depends on what you have your board controlling rights are. It depends on all of it you want to make sure. I think, I think who you choose and have on your board is like one of the most important decisions you’ll ever make, and a big opportunity for greatness or for misstep.

Kara Goldin 27:00
Definitely, totally agree. So you have an upcoming book coming out, the Whisper way. So excited. This is your second book, and it’ll be out May 2025, can you give us a little glimpse as to what we’re gonna get to see and and read about

Carrie Kerpen 27:18
Yes, so Okay, so it’s the Whisper way, the secret formula for female entrepreneurs to create life changing wealth. And this book, Kara, is so different from anything I’ve ever done. So it’s, it’s a parable. So it starts with this woman. This the only one who’s based on anyone is me, who has this retreat with seven different female founders, each of whom struggle with one of the challenges within whisper like one can’t identify her, why her? How this one’s income is screwed up. This one doesn’t understand their differentiator, and they workshop them. It’s like the best business beach read. And then it has an implementation guide for founders to be able to make sure that they get exit ready. And then it has some real life stories from women that we know who are fabulous, who’ve exited in a big way. And it’s really exciting. It was my first time writing any form of fiction, and I think it’s, it’s just I really, I love it. I hope that everyone loves it. I can’t wait for people to read it. I am. It’s really this business and this book, and all of it is really something that I felt called to do, which I never felt with likable, like I loved likable. It was great, but I never felt called to do. It was something that Dave and I sort of stumbled into early social media, and we were like, Oh my gosh, this is a great land grab. Let’s go. This is now that I’ve had an exit, I was able to basically afford myself the time to say, I want to work on something that bills me. And that’s what this is, and this book is, and I hope everybody reads it the Whisper. You can go to the Whisper way.com for that.

Kara Goldin 28:54
Love it so. Carrie, thank you so much for joining us today and sharing your incredible journey and wisdom your work and empowering women entrepreneurs and closing the exit gap is so so needed and so awesome. And for everyone listening, be sure to check out Carrie’s upcoming book, The Whisper way, and learn more about the Whisper group as well. We’ll have all the info in the show notes, but thanks for tuning in, and remember, every business journey starts with a bold step forward. See you next time. Thanks Carrie. Bye. Thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast, just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling. Book undaunted, where I share more about my journey, including founding and building. Hint we are here every Monday, Wednesday and Friday. Thanks for listening, and goodbye for now. You.

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