My First Acquisition Started With a Question I Posted in This Community

When I started The Whisper Group, it was just me. No Maggie. No team. No one.

Here's the part I don't always lead with: I had no idea how to build the systems a company actually needs. I'd built my first company, Likeable, back in 2007, and I'm a vision person, not a systems person. I'm almost allergic to order. My whole business lived in my head.

So I went to my friend and fellow Entreprenista, Katie Dunn, who is a master of her CRM and her systems, and asked her to show me how she did it. She pulled up Monday.com, walked me through it, and I remember looking at it and thinking, I can never do this.

One Community Question Changed My Business

So I did the most Entreprenista thing possible. I posted in the community: “Is anyone good at ops?”

Caitlyn Wells replied within moments.

Here's what still amazes me. Caitlyn had joined Entreprenista only weeks earlier, in July of 2024. She was brand new, just starting to engage and meet people. Another member, Ingrid, saw my post and nudged her toward it. Two women, both new to the same community, found each other because one of us asked a question and the other was paying attention.

I got on the phone with her and, I'll just say it, she was amazing. She ran an audit of where my processes actually stood and told me exactly what to fix. I hired her on the spot for fractional work. For the first stretch, it was me and Caitlyn against the world.

Then Maggie came on as my co-founder and loved Caitlyn as much as I did. Molly joined. As the business grew, Caitlyn grew right along with it, and somewhere in there the four of us stopped being a founder and her contractor and became a team.

How Caitlyn Built a Business Worth Acquiring

The moment I understood what Caitlyn had really built came when she went out on maternity leave with her second baby. I panicked. How do I run this without my operator? And then she stepped back, and her team kept everything running, flawlessly, on the systems she'd built. Nothing broke. Her whole goal, as she says, was to work herself out of a job. She calls messy operations a silent killer, the thing draining revenue and opportunity from businesses that look just fine on the outside. I was watching my own clients lose deals over exactly that. Caitlyn had solved it, and she'd built a real business doing it.

So we brought Upwell Strategies into The Whisper Group, and Caitlyn became our COO. And the part of the story worth telling is why she said yes.

She didn't sell because she had to. She told me she did it from a place of empowerment, not panic. And when she described making the decision, she didn't talk about the number. She said: “I don't ever want these three women to not be in my life.” She stayed for Maggie, Molly, and me. For the relationships.

That is the whole thing, right there.

Why Community Became My Highest-Return Investment

And it isn't only Caitlyn. I found Fatima Teos, my head of marketing, through Entreprenista too. Molly McCartan, my Managing Partner, is someone I reconnected with in this same community. The people who make my company run, and the company I now own, all trace back to the same place.

We talk about community like it's “networking,” a nice-to-have. It isn't. It has been the single highest-return investment I've made in this business. It gave me my operator, my marketing lead, my Managing Partner, and my first acquisition, all from one question I almost talked myself out of asking.

So thank you, Courtney and Stephanie, for building something that creates actual financial impact for the women inside it. That is rare, and it is the entire point.

If you take one thing from my story, let it be this: the best hire, the best partner, or the best acquisition of your life might be one post away. Ask the question.

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