Full Transcript

Jason Kirby: Hi everyone, welcome back to Fundraising Demystified. Today we have Kerry Kerpen on the show with us. Welcome to the show Kerry.

Carrie: Thank you so much, Jason. I'm excited to be here.

Jason Kirby: Excited to have you come on and share your story. You are a successful exited founder that had the joy of selling the company for over eight figures. And I want to hear your story—what was unique to you and what the story was. But before we dive into the specifics, just tell a little bit about what Likeable Media was and why you ended up selling the company.

Carrie: Yeah, so Likeable was one of the very first social media agencies. My husband and I launched it in 2007 when there were no social media agencies. As a result, we scaled pretty quickly. It wasn't figuring out product–market fit; it was like we opened our doors and were instantly inundated. That was both exciting and scary. Neither of us had ever run an agency before.

But we did and we scaled pretty quickly and there we were. In 2013, my husband wanted to launch a tech business and raise funds for that. We separated the two businesses—we incubated it through Likeable Media and then spun it off as a separate company that my husband left to raise funds for. I stayed and ran Likeable Media. In 2013, things were quite different than in 2007.

In 2007, nobody did social media. In 2013, everybody did social media. In 2007, we had no money because we were just starting out. In 2013, we had no money because we were so busy staffing to service all of the Fortune 500 clients we won and had delayed payment terms. It was really hard to get profitable. Also in 2013, Dave was no longer the leader and face; I was now the sole founder left.

I was surrounded by founders in digital media who were loud, extroverted, and male. I was none of those things. So in 2013, I set forth a plan to build a company that would eventually become a sellable asset—focused on profitability, steady growth, being about more than just the founders, diversifying revenue—and took it forward in that way. I was intentional, and then brought it through to exit in 2021.

Jason Kirby: What sparked that? What gave you the motivation to think like that and structure the business as an asset to sell?

Carrie: A few things. First, when we launched the tech company, we knew we weren’t going to make money from that for a while—we’d put our heart, soul, and fundraising into it—and we needed a source of income. Becoming profitable was table stakes. For building a sellable asset, I was inspired by John Warrillow’s Built to Sell, a parable about a PR agency founder who learns his business isn’t worth much because it’s built entirely around him, lacks focus, and has no predictable revenue. I was lit up when I read that and asked, how could I build a company to one day be sellable? It didn’t go exactly as planned, but it guided my direction.

Jason Kirby: Incredible to have that spark. When it came to packaging it up, what were the KPIs and drivers you thought were important, and how did you decide they mattered for your business?

Carrie: It came from learning what made the business interesting and special. In my next act, I launched an exit-readiness advisory for women-owned businesses, based on what I discovered mattered in my own exit. For revenue, I use RED: Recurring, Expected, Diversified. Can I forecast revenue? Do clients repeat? Is revenue diversified enough that if one product becomes irrelevant, the business is still solid?

Agencies are valued on an EBITDA multiple, so profitability was non-negotiable. We built systems to understand pricing and deliverables. I made the business bigger than myself—extracting me from being the driving force. Another key differentiator was defining and proving our “secret sauce,” not just marketing speak. Income and profit get all the attention, but differentiation you can prove is critical for success.

Jason Kirby: When did you decide that 2021 was the best time to sell, given you’d been thinking about it for years?

Carrie: I encourage founders to always be ready to sell—so you can pull the trigger when the moment comes. The market was very good then, though I didn’t realize how good until later. But it wasn’t just the market. I knew Likeable wasn’t my life’s work; it had a limited runway for me. I also wanted enough energy to deliver during an earn-out, which is common in services. I didn’t want to be dead inside—I wanted to be valuable to the acquirer and capture the earn-out.

I also felt tech would be crucial to social’s future and wanted to align with someone stronger there. Finally, social media requires constant reinvention. I’d done it well multiple times, but didn’t want to shoulder the next reinvention’s risk alone. And our revenue and EBITDA were at a point where we could extract a minimum of eight figures—enough to create security and space for what came next.

Jason Kirby: You coined the “exit gap.” Tell us what that is.

Carrie: The exit gap is a depressing stat but needs context: women-only founding teams capture about 0.8% of exit value—less than a penny of every M&A dollar. That’s shocking, but context matters. Women receive far less venture funding, and many women start lifestyle businesses designed for flexibility, not fundraising. Exit isn’t on the radar; think interior design firms run until kids are grown, then closed or handed to an employee.

Lifestyle businesses, when built properly, can be life-changing assets. Whether you’re building a behemoth or a local services firm, your time and effort should have value at exit. That’s how we close the exit gap—by building sellable assets at all scales.

Jason Kirby: I read in one of your reports that women-owned certification can be a net negative at sale. Can you explain?

Carrie: It’s a double bind. Women-owned businesses are encouraged to get certified (MWBE) to access government or supplier diversity contracts. But upon acquisition, you usually lose that certification because the buyer isn’t women-owned. Acquirers discount revenue they believe is tied to the certification. Many founders get certified because they’re told it’s good, but unless you actively pursue and maintain government work, you might not see real benefit—yet still be penalized at exit. I recommend not renewing certification about two years before selling, if it’s not materially driving revenue.

Jason Kirby: What steps should female founders take if they’re starting to think about an exit?

Carrie: First, get a valuation to know where you stand. Then envision what you want your exit to be. Look at typical multiples in your industry and work backward: if you’re worth X today and want Y, what EBITDA or revenue do you need, and what steps get you there? Assess beyond dollars: is revenue RED? Do you have a clear differentiator? Strong systems and processes for transferability? A capable team instead of key-person risk?

My WHISPER framework covers seven areas: your Why (target and purpose), How (multiples and likely acquirers), Income (RED), Secret Sauce (differentiation), Profit, Executive team/Ecosystem, and your Roar—how you present confidently in diligence, often in rooms full of men picking apart your business.

Jason Kirby: What mistakes do you see founders make during this journey?

Carrie: While building: not sticking to a strategic plan with quarterly and annual priorities. You can succeed flying by the seat of your pants—but you risk being forced to sell when you’re not ready. At exit: unfamiliar terms (working capital, non-competes, etc.) can sink a deal. Many founders fear looking uninformed and brush past details they don’t understand. That’s tragic—those details can make or break an acquisition.

Jason Kirby: It helps to have advisors—ideally before you’re in a live process—who know you and the business.

Carrie: And not just advisors who are only incentivized to close. M&A advisors and i-banks want your deal to close. So do you—but you also don’t want to get screwed. Have a great deal team, and also trusted peers you can gut-check with who’ve been through it.

Jason Kirby: What’s your take on the current M&A market?

Carrie: I think it’s going to pick up. 2021 was the wild west—money flowing, cheap borrowing. Then a screeching halt, multiples down—the one thing you can’t control. Build a sellable, profitable business so you can wait out markets. If you can’t wait, you can’t control conditions. As rates come down and recession fears fade, activity should rise. I’m optimistic for 2025.

Jason Kirby: Any sector or structure trends you expect?

Carrie: Gradual multiple recovery as buyer competition returns. In agencies: large-scale consolidation (e.g., holding-company mergers) pushes independents to be more acquisitive to compete. Expect more PE and independent roll-ups as borrowing loosens. Also, many owners are unsure how to adapt to AI, so more businesses will come to market—spurring activity, though possibly tempering price in some niches.

Jason Kirby: Legacy customer lists can be highly acquirable assets, especially if the acquirer can cross-sell AI-powered offers.

Carrie: Exactly. A large portion of my acquisition value was strong, long-tenured, name-brand clients. Acquirers wanted those logos and relationships, then could deliver bigger, faster, cheaper via technology.

Jason Kirby: Walk us through your sale process for Likeable Media.

Carrie: In late 2020, during our annual personal retreat, we revisited “Is it time?” Dave introduced me to a woman M&A advisor he respected. I interviewed others but chose her for domain expertise (agencies), personal fit, and fees. We created a SIM and went to market, including prior inbound acquirers and her own targets, especially in tech. We received five LOIs (it was 2021 and we had a strong, profitable, sticky book with a NYC studio).

I initially signed an all-cash-upfront LOI from an independent agency forming a collective. Too good to be true—diligence surfaced issues (e.g., contract tenors) and they couldn’t do all cash. I returned to a tech acquirer, 10Pearls, whose founder I respected. We re-engaged, negotiated terms, and moved quickly. We signed with the advisor in December and closed on April 1. Fast for a deal of that size. If I’d taken more time, I might have eked out more cash, but fit mattered more, and I believed in their trajectory.

Jason Kirby: Any final advice for female founders at the early or pivot stage aiming for a bigger outcome?

Carrie: Dream big and execute. Don’t fear risk—women’s risks are often calculated and smart. And remember at the deal table: they’re lucky to acquire you. Shift from “I hope they’ll buy me” to “they’d be fortunate to.” Know your value throughout diligence and bet on yourself.

Jason Kirby: Beautifully said. Thanks for joining us!

Carrie: Thanks Jason, and thanks to all your listeners.