i&a: Where did you start? Why did you become an entrepreneur?

Carrie: I didn’t plan to become an entrepreneur. I worked in brand marketing and media sales. My partner proposed and wanted an extravagant wedding. He didn’t mean inviting high school friends. He wanted everyone to attend. We couldn’t afford such a wedding, so we had to be creative. I decided to find a venue that could hold many people and was affordable.

Since I came from media sales, I thought about sponsorships. I considered baseball stadiums in the States, which have promotions during innings. We could have a wedding-themed night at a minor-league baseball park. Instead of t-shirt tosses, 1-800 Flowers could toss bridal bouquets. It would be cute, campy, and fun. We’d get married on the field after the game. Everyone thought I was crazy, but we decided to go for it. Dave and I sold $100,000 in sponsorships to the venue and had the wedding we wanted. We were married in front of 5,000 people. We raised $20,000 for charity and had the most delicious wedding of our dreams.

Everyone had hot dogs and hamburgers, and I married my love. We also had a successful event. But we got a lot of press. It was a sponsored wedding, so it was creative and raised money for charity. It had all the elements. To date, 1-800 Flowers’ largest PR event was ours. We were on ABC World News, CNBC, and The New York Times. Sponsors wanted us to do it again, but we weren’t getting married again. We started a company based on word-of-mouth marketing after deciding against a sponsored divorce. Neither of us had agency experience, but we tried grand opening events and press to get attention. We got married in 2006 and began in early 2007. Facebook expanded beyond colleges in May 2007, prompting us to become a social media agency. We scaled quickly despite our lack of experience.

i&a: You’re no longer just an entrepreneur, you're now a serial entrepreneur. How did you feel about going from one to the other?

Carrie: Dave, my husband, and I launched Likeable together. It worked really well because Dave was a visionary and I was the implementer at the time. I was making everything happen and, you know, women keep it all together. We keep it going. He was the dreamer and the face and all of it. But all of our eggs were in one basket. We both left our jobs. By the time we’d actually launched and gotten some steam I had had a baby and it was scary. And he really wanted to get into tech. And so he said I'll raise funds and start a new business and you're going to run Likeable. It was both exciting and terrifying. You're diversifying your potential, but you're also losing this amazing visionary from this company, Likeable, which was at the time our bread and butter.

When he left in 2013, things were very different. In 2007 nobody was doing social media. 2013 he leaves and everybody's doing social media. He was the leader as like this loud, extroverted male. I was not that at all. And I didn't feel comfortable sharing my story. That was what a lot of social media leaders were doing. It was a really scary time to start out as serial entrepreneurs. That being said, I set out with Likeable. I was going to run that smartly and steadily, protecting the risk. We were going to make it profitable. It's going to be a good culture and we were going to build it to sell. And so that's what I did. We sold it in 2021, 14 years after we started.

I got really comfortable with the idea that I could actually do something again. Dave always had the confidence. He could always do it. He's a born entrepreneur. For me, and I think this is probably innately female, I felt like I had to prove to myself that I could do this and I could sell it. I could build it to be a sellable asset. And only then would I be worthy of being a serial entrepreneur, which is so silly really because I was worthy from the day I started.

i&a: Do you think that's innately female? What key takeaway would you give for that?

Carrie:  Well, my dear friend Reshma Saujani, who is the founder of Girls Who Code, wrote a book called Brave Not Perfect. And she did an amazing TED talk. We teach our boys to be brave and we teach our girls to be perfect. My company will be successful when I built it profitably and when it sells and when everything is great and everyone is happy.

I think men are encouraged to take these risks. I think if we, as women leaders who've done it, who've gotten across some form of proverbial finish line, help encourage other women to take risks. Now they can be smart, calculated risks. I still don't totally shoot from the hip, but if we encourage them to take risks, then we will actually see true reward. I remember throughout my whole journey, I had a lot of what ifs, what if this goes wrong? If I could go back to the me of my twenties and thirties, I would say, imagine all that time you're spending imagining the worst case, spent half of it imagining the best case.

i&a: Walk us through the process of making the decision to sell Likeable.

Carrie: Dave and I always knew that we wanted to build the business to sell. I liked social media, but I wasn't obsessed with social media. I was actually obsessed with building a healthy business. When we built it and he left, we knew we were going to build it to sell.

The decision came after we hit a certain point where the numbers would be good enough, to really be able to extract a value that would be enough for me to feel safe. I wasn’t feeling fulfilled anymore but knew I still had some runway. I wanted to sell before that little nagging feeling became a really loud feeling because I felt it wouldn't be fair to sell the business to an acquirer if I had that nagging feeling, where the candle has just been blown out. I think it's very important to sell when you're not dead inside.

If I have one piece of advice, if you're feeling like get me out tomorrow. I'm done. My first step is always try to get them not to be dead inside first, for one more go. You're just at such a higher advantage, if you're not totally done.

i&a: You didn't need to jump straight into opening up a new business, why did you?

Carrie: I didn’t need to rush. I wish I’d taken more time. I sold and signed a three-year contract with the acquirer. During that time, I evaluated whether to stay and help them build something meaningful. They were great, but I felt unfulfilled. I considered exit planning for women-owned businesses. I researched and found an exit gap.

We’re not exiting as we should due to lack of education. There’s a methodology called the whisper way, with seven factors: why, how, income, secret sauce, profit, executive team, ecosystem, and roar factor. Spelling out WHISPER. I realized I could educate women on how to present during acquisitions, which could generate more money for women, including lifestyle and funded businesses. I decided to test this and discovered a unique opportunity. The business grew rapidly, becoming another full business. I didn’t expect this outcome. I initially planned to consult, but I wondered if I wanted to be a consultant or build something big. I believe I needed a two-month farm stay doing yoga, but I jumped in without that.

i&a: When we talk about how things fill our tank and what gets us excited, was there an opportunity to take a pause or did you feel, if I take my foot off the gas, the car is going to stop?

Carrie: Man, that is such a good question. I think what I would have done was delayed for a little bit and said I don't want to know. Don't tell me about that exit gap. Don't tell me anything. Cause once I saw the opportunity I realized that I couldn't go, I just couldn't go back. The insight is that we're opening businesses at twice the rate of the population. And yet when we exit, we're capturing 0. 8 percent of value. So that was the insight. All of these women are opening businesses. They will not all run them for 25 plus years. They will need to sell them or close them. And if we can help them realize that what they're building now, even if it's a lifestyle business, has value and is a sellable asset, then we've done our job.

i&a: How did you position yourself as the expert in that area?

Carrie: I was known as an expert in the social media space, but like, like an old one. There's all these youngies who know all the TikToks and all of that. I was old. I built Facebook pages. The name was Likable. I had a reputation for two things, being great at social media for enterprise brands and connecting with women in business and telling their stories through podcasting, you know, content creation. I had built this like great network, but most people knew me as a social media expert who also had an interest in advocating for women.

The first thing that I had to do was change what I was known for. I invested in content. I did shoots once a month and I would record like 30 plus micro videos about exit planning and working capital. I created the whole narrative and I pushed myself out of my comfort zone to feel uncomfortable every single day. By posting content every single day and it worked really, really, well, both for driving leads for changing perception and how I'm known. I still hate it actually, it's really tiring and it's really hard, but it really works.

i&a: What tips would you give on tipping you over the edge from dreaming to doing?

Carrie: I think looking first at what it is to dream, it's to find the white space. I saw a white space here in exit planning. There’s a million people talking about exit planning. Exit planning specifically for women owned businesses. There's one to two. Why? Because there's not that many women owned businesses yet that are exiting, right? You have to commit to the white space that you’re going to own. This is my sandbox, what I'm going to do. And then you think about how can I become known for this or build a business around this?

And the thing with content is, there are so many tools that make it easy, you just start producing. You can be writing on LinkedIn. Just start. Start sharing your unique point of view. Start sharing what it is you stand for and what you want to build. Now that's if you're a services business. If you want to build a product, it's a product. Look at what you need to get to the minimum viable product and start figuring out a way to be known for that too. Personal branding is very important either way.

i&a: What’s been the hardest thing you've faced to date?

Carrie: The hardest thing in both businesses, is managing ebbs and flows, but specifically cash flow. Having to manage cash flow can stop you dead in your tracks from being an entrepreneur. It's so scary and so hard. You start a business 'cause you believe in something. I remember so many times when we were about to not make payroll and I would be literally moving like dollars, I gotta cover the AP (accounts payable) or like whatever. That was the scariest point in business. And now, ironically, I'm sort of at that point again, albeit with a lot more security personally. I think it's managing the headspace needed to manage the anxiety of the cash flow.

i&a: What’s it like to work with your husband?

Carrie: Oh my God, it's hard. You want my advice? Okay. The first thing is to designate times for talking about work. The second is different roles. If you have different skill sets and roles. So for me, he was the visionary and I was the implementer. Then when he left, I realized that I really was a visionary and was missing that.

It was an amazing ride because there's no one to trust more than my partner. All the money comes into one house at exit or anywhere else. Like that's amazing, right? There are so many benefits, but the drawbacks can be really hard. He was such an amazing visionary, so amazing. And I never would have stepped into his shoes unless he left. Then I realized, oh shoot, we're both kind of visionaries. So that's why we didn't build the next thing again. He helps, but it would be really hard because our skill sets are too similar. So you want to make sure you’re complimentary.

i&a: What’s been the most surprising thing with your entrepreneurial journey?

Carrie: What you're able to build on your own, like what you're capable of. The most exciting thing on my journey was what I was capable of. When I talk to so many women, what they're capable of, we are capable of creating our own wealth and building these things that are out of nothing. How inspiring is that? Like that is just the coolest thing to discover what we are collectively capable of. It's fantastic. 

i&a:  I want your opinion on this. I’ve read a lot of business books and a lot of them say don't build a business to sell because what if it doesn't sell?

Carrie: Always build a business to sell because if you're building a business to sell you're building a business that is profitable. Profitable and healthy. Why on earth wouldn't you build a business to sell? It doesn't mean you must sell. A sellable business is a profitable business with diversified revenue with a great story and all of it. It's not just about building to sell. It's building a sellable asset. Shifting that perception. You want to make sure it's really a healthy part of your life because if the business isn't making money, you are so much more stressed in general.

i&a: How do you believe being an entrepreneur has impacted your life?

Carrie: It completely changed my life. I was able to raise three children on my own terms. I didn't have somebody telling me what I had to do. I made my own success and I had my own failures and my husband and I were collectively responsible for the direction of the way we wanted to live our lives. Entrepreneurship, it's not for the faint of heart. But it is something that has such good rewards in terms of your freedom. I was always motivated by freedom. I never wanted to be owned by anybody. Wanted to have to ask permission. I was always motivated by freedom. It wasn't really about money for me.

i&a: Is there anything you would have done differently?

Carrie: Taking more risks earlier. I think I ran the business very nervously. Thank God Dave got us off the ground like that because I probably would have been like a squirrel. I probably would have acquired a couple businesses because I didn't realize how easy it actually is.

i&a: What makes you uncomfortable?

Carrie: What makes me uncomfortable? Arrogance. People make me uncomfortable. I think I always had a little bit of a scarcity mindset my entire life. I think even as an entrepreneur I have learned how to take risks. But there's still a discomfort there, which is how I know I need to push forward and do it.

i&a: Where do you see yourself in five years?

Carrie: In five years, I will have built the largest and most robust community for exited female founders. I will have data that shows that the Whisper Group has worked to close the exit gap. And in five years, I will have 10x the size of the company.

i&a: Tell us about your magic sauce and how can people find their own?

Carrie: I think they have to sit in silence. I think for me, my best work, my best ideas always come from when I'm removed from digital devices and removed from technology and just by myself, without the expectations of others. I think in general, women are such people pleasers that we focus on what everyone else wants. And I think to find what you want, it's good to sit in silence. I have an upcoming book, which is out in May called The Whisper Way, which does talk about the methodology of getting to some of those things.

i&a: In the first book, you wrote about finding people and creating a personal advisory board. What is that?

Carrie: Fabhab, your fabulous personal advisory board. I think everybody needs a personal advisory board of people in their lives who they can go to for different issues in their life. Hosting a board meeting like a council of people who are there to advise you because they love you and because they understand different parts of your life. I had advisors who I went to for business things, I had advisors who I went to for fashion things, I had advisors who I went to for parenting things, and I just had like a collection of women that really helped me through. 

i&a: What’s your legacy?

Carrie: Let’s see. My legacy. Carrie was a dedicated wife and mother who was determined to close the exit gap. That's what I would say.  

i&a: What’s inspiring you? What generally sits on your nightstand and in your ears?

Carrie: I'm drawing a lot of inspiration from Mel Robbins’ new book The Let Them Theory. I've been watching all of her stuff. I love her so much. I listened to a lot of podcasts. Build to Sell by John Warrilow. Anything by Katy Kay and Claire Shipman who wrote The Confidence Code.  

i&a: What would you caution people to think about?

Carrie: Making sure you have enough of a cash plan. If you don't have a good plan and you get so anxious and you're stopped by cash, you're not going to do well. Have a plan for six months to survive. 

i&a: What’s your take on work-life balance?

Carrie: Give yourself grace. We're set up with impossible standards. Just alone a workday is typically 9 to 5 but kids are in school from 8 to 3. That should tell you everything you need to know about the fact that this ship is totally broken. Give yourself grace, do the best you can and build the life that you want within the means of what you are able to do. 

i&a: What’s keeping you up at night?

Carrie: I’m sleeping pretty well, but there are so many women who need help, understanding exit planning, and that I'm not going to be able to get to them fast enough.  

i&a: Where can you direct people to for that help?

Carrie: I have a book. It is called The Whisper Way. If you need exit planning services, it’s The Whisper Group. If you are a founder who has already exited and want to join the community, that's also on the website. And of course, you can follow me anywhere at Carrie Kerpen. Also, season three of my podcast, The Exit Whisperer, is coming out this January.

Written by
impact&agency