AirWorks Solutions

I told Jennifer I didn’t know how to write a book.

That wasn’t false humility. It was the truth.

I’ve written speeches, social media posts, emails, articles, and more business plans than I can count, but sitting down to write something this personal felt different. Jennifer wasn’t asking me for a testimonial. She wasn’t looking for another success story about marketing or AI. She wanted the real story. The hard parts. What almost stopped me from working with her. What it’s actually like to build alongside her. She wanted the version that usually gets left out.

So I did what I do with most things I don’t know how to do.

I found someone better than me.

I asked Jazmin to interview me instead of staring at a blank page. Jazmin has worked with Jennifer for years, and she’s interviewed me enough times to know when I’m giving the polished answer instead of the honest one. She didn’t let me hide behind the easy version.

By the end of that conversation, I realized something.

The story I thought I was writing wasn’t actually the story.

I thought this was going to be about marketing.

Or AI.

Or websites.

It isn’t.

The truth is, I still get warned about working with Jennifer.

People still pull me aside at conferences. They’ll lower their voice just enough to make it feel like they’re sharing something important and tell me to be careful. Sometimes they say she’s too aggressive. Sometimes they say she has a bad strategy or they point to an unhappy client (who likely wasn’t doing their part to be successful). Sometimes they don’t say her name at all. Or they’ll make a sideways comment on social media or reference “certain people” in our industry, and everyone knows exactly who they’re talking about.

I used to get mad.

Now I laugh.

In some ways, they’re talking about the same Jennifer I know.

She is blunt. She moves fast. Really fast. She doesn’t spend much time softening difficult conversations, and she has very little patience for doing something simply because that’s the way it’s always been done. If your only experience with Jennifer is from across a conference room, through a keynote, or from a handful of social media posts, I can understand why she might come across as cold or even aggressive.

What I know now is that those qualities are the easiest things about her to see.

The harder things to see are also the things that matter most.

I’ve watched Jennifer lose sleep trying to figure out how to help clients whose businesses were struggling. I’ve watched her celebrate AirWorks’ wins as though they were her own. I’ve had late-night phone calls that had nothing to do with growing CI Web Group and everything to do with helping my company. I’ve watched her carry the weight of other people’s businesses in a way that reminds me of how a mom worries about her kids. Fiercely. Constantly. Long after everyone else has gone to bed.

The longer I’ve known Jennifer, the more I’ve realized that what many people experience as intensity is actually investment.

She cares.

Deeply.

I’ve also watched something else happen over and over again.

I’ve watched people publicly question Jennifer’s judgment, criticize her ideas, and dismiss what she was building as unrealistic. I’ve watched people post the kind of sideways comments where nobody says her name, but everybody knows who they’re talking about. I’ve watched people confidently explain why her strategies would never work.

Then I watched the industry catch up.

Months later, sometimes a year later, I’d hear those same ideas repeated from conference stages, in podcasts, by agencies, and across LinkedIn and Facebook as though they’d just been discovered. The very concepts that were once criticized somehow became accepted wisdom.

That’s usually when I smile.

Jennifer wasn’t wrong.

She was early.

It took me a long time to understand the difference.

The funny thing is, if you’d met me when I first met Jennifer, I probably would’ve warned you too.

Not because I thought she was a bad person.

Not because I doubted her intelligence.

Quite the opposite.

I met Jennifer at an E3 event for women in the trades. Like most conferences, people were making small talk, exchanging business cards, and talking about the things conference attendees always talk about. Jennifer wasn’t interested in any of that. She was talking about where our industry was headed and how contractors needed to think differently if they wanted to stay relevant.

I remember walking away from that conversation thinking two completely contradictory things at exactly the same time.

This woman is brilliant.

This woman is completely out of touch.

I know how ridiculous that sounds now.

I wasn’t questioning whether she was smart. If anything, I thought she might be smarter than I could relate to. What she was talking about simply felt so far beyond where I was operating that I couldn’t connect the dots. Kevin and I were focused on building a great company, taking care of our people, raising our kids, and figuring out how to grow one decision at a time. Jennifer was talking about where the industry was going, not where it had been. She wasn’t interested in incremental improvements. She was questioning the assumptions the rest of us hadn’t even realized we were making.

I admired her almost immediately.

I just wasn’t ready to follow her.

That became painfully obvious when AirWorks needed a new SEO strategy and website. I interviewed Jennifer and CI Web Group. I loved the conversation. I thought she was brilliant. Then I hired someone else. Looking back, I don’t think I chose another company because they were better. I chose them because they felt safer.

Jennifer’s approach was different. Not a little different. Fundamentally different. She wasn’t trying to build me a prettier website or make a few adjustments to my SEO strategy. She was asking me to rethink the way I thought about marketing altogether. At the time, that felt like a bigger risk than I was willing to take.

So I hired the company that looked familiar. They built me a beautiful website. It was polished, professional, and looked exactly like I thought a successful contractor’s website should look. It also helped us maintain the status quo.

I’ve thought about that decision more times than I’d like to admit because it taught me something I couldn’t have learned any other way. At the time, I thought I was choosing the responsible option. Looking back, I realize I was choosing the comfortable one. I wanted extraordinary results while making ordinary decisions. I wanted growth without discomfort. I wanted innovation that still felt familiar.

Jennifer wasn’t trying to sell me a website.

She was trying to change the way I thought.

I simply wasn’t ready to let her.

What’s interesting is that even after saying no, Jennifer never really left my orbit. We crossed paths at industry events. I’d listen whenever she spoke. I’d ask her questions. I’d watch what she was building from a distance and quietly wonder if maybe I had missed something the first time around.

I admired Jennifer for years before I was willing to trust her with my business.

There’s a big difference between admiration and trust.

Admiration costs you nothing. Trust asks you to risk something. For me, that risk was AirWorks and I wasn’t ready to make it.

Then something happened that changed everything.

I was talking with another woman in the trades whose opinion I respected deeply. Jennifer’s name came up, and I braced myself for another warning. Instead, she smiled. She told me Jennifer had been incredibly generous with her. Not because she had to be. Not because there was a contract or a business reason to invest her time. She simply described someone who had shown up when she needed help and expected nothing in return. As she talked, I realized I wasn’t hearing another opinion about Jennifer. I was hearing about a completely different person than the one everyone seemed so eager to warn me about.

That conversation stayed with me longer than I expected. It didn’t suddenly convince me Jennifer was right. It didn’t erase every hesitation I had. What it did was force me to ask a question I’d somehow never asked before. Had I actually formed my own opinion of Jennifer, or had I spent years borrowing everyone else’s? The realization was uncomfortable because I like to think of myself as someone who makes independent decisions, yet here I was realizing I’d been carrying around assumptions about a woman I didn’t really know.

So I sent her a text.

I told her someone had been speaking incredibly well of her when she wasn’t in the room. To me, that’s one of the purest measures of a person’s character. It’s easy to impress people when you’re standing in front of them. It’s much harder to earn the kind of respect that gets talked about after you’ve left.

She answered almost immediately.

“I’m so excited about what I’m doing. Let’s change the world together.”

I laughed.

I remember thinking, What in the world does that even mean?

Jennifer told me later that she had been on a golf course when she sent that text, which somehow makes the story even better. There was no carefully crafted follow-up. No sales strategy. No attempt to overcome my objections. It was simply an honest expression of how she saw the world. She believed she was building something meaningful, and she wanted other people to build it with her. At the time, I couldn’t fully understand what she meant. Looking back, I don’t think either of us knew exactly what “changing the world” would look like. We just knew we wanted to build something that mattered.

That text didn’t make me hire Jennifer.

It made me trust her.

There’s a difference.

Trust doesn’t usually arrive all at once. At least it didn’t for me. It came one conversation at a time, one observation at a time, one decision at a time. Somewhere between admiring Jennifer from a distance and working alongside her, I realized I had stopped looking for reasons she might be wrong and started paying attention to why she kept being right.

Working together was nothing like I expected.

I thought I was hiring a marketing company. Instead, I found myself in a relationship that challenged the way I made decisions. Jennifer has a habit of questioning the assumption underneath the problem. She doesn’t just ask what you’re trying to accomplish. She asks why you’ve decided that’s the right way to accomplish it in the first place. If she thinks an idea is wrong, she’ll tell you. If she thinks you’re protecting your comfort instead of your business, she’ll tell you that too.

One of the greatest gifts Jennifer has given me isn’t that she’s always right. She isn’t. It’s that she has no interest in staying attached to an idea simply because it was hers. She’ll argue passionately for what she believes, but the moment the data tells a different story, she pivots without ego. Watching that changed me. She made me understand — this is a thinking game.

Like a lot of entrepreneurs, I used to lead with instinct and defend my decisions until someone proved me wrong. Jennifer taught me something far more valuable. Lead with your instincts because they got you this far. Then collect the data as quickly as you can. If the data confirms your instinct, keep going. If it doesn’t, be willing to change your mind before your pride gets involved.

The data has been rude enough to keep proving her right. And the momentum and head start she now has is incredible.

That data wasn’t just proving Jennifer right… It was teaching me how to become a better leader.

One of the things I’ve come to appreciate most about Jennifer is how remarkably consistent she is. The woman you see on stage is the same woman who will call you on a Tuesday afternoon because she’s been thinking about your business. The woman who confidently challenges the status quo in front of hundreds of people is the same woman who will spend an hour talking through a problem that technically isn’t hers to solve simply because she can’t stop thinking about how to help. Over the years, I’ve realized that consistency is where trust comes from. Not because she’s easy to work with, but because she’s exactly who she says she is. WYSIWYG (pronounced by Jenn as wussy wig) — What you see is what you get.

I also think that’s why so many people misunderstand her.

Most of us have been taught to soften difficult conversations. We wrap criticism in compliments, apologize before offering feedback, and convince ourselves that honesty has to be delivered gently to be received well. Jennifer has never operated that way. If she believes an idea is bad, she’ll tell you it’s bad. If she thinks you’re making a decision that will hurt your business, she isn’t going to smile, nod, and let you figure it out on your own. She’ll challenge it. Sometimes she’ll completely dismantle it.

Looking back, those conversations were never about proving me wrong. They were about protecting my business. That’s a very different motivation, and it took me a while to recognize it.

I remember one conversation after we launched our new Webflow website. I called Jennifer because I didn’t love it. “Jen,” I told her, “I don’t really like it… it could be prettier.” She didn’t argue with me or try to convince me my opinion was wrong. Instead, she asked one simple question.

“Do you want it to be pretty or perform?”

It completely stopped me in my tracks because the answer was obviously that I wanted it to perform. In fact, I loved how it was performing. The site was generating better results than anything we’d had before, yet I was fixated on the fact that it didn’t look the way I expected success to look. That conversation has stayed with me because it was never really about a website. It was about the stories we tell ourselves. How often do we dismiss something that’s working simply because it doesn’t fit the picture we had in our heads? How often do we mistake familiar for better?

Eventually, we made the site prettier too.

That’s another thing people don’t always see about Jennifer. She’s incredibly opinionated, but she isn’t attached to being right for the sake of being right. If something genuinely matters to the client, it matters to her. She’ll fight for the things she believes are important, but she’ll also listen. Some of the best decisions we’ve made together weren’t mine and they weren’t hers. They came from challenging each other until we found something better than either of us would have come up with alone.

Somewhere along the way, Jennifer stopped feeling like my marketing company. She became one of the first people I call when I’m trying to think through a difficult decision. Not because she always has the answer, but because she asks questions that force me to think differently. I’ll go into a conversation convinced I need to solve one problem, and twenty minutes later I’ll realize I’ve been asking the wrong question all along. That’s one of her greatest gifts. She doesn’t just solve problems. She helps people find the problem underneath the problem.

Kevin has watched this relationship evolve almost from the beginning. There have been countless nights where Jennifer and I were still on the phone, texting through an idea or working through a challenge long after most people had called it a day. Eventually I’d crawl into bed, and without even opening his eyes, Kevin would mumble, “Say hi to Jen.”

It makes me laugh every time I think about it because that one sentence says more about our relationship than I probably could. Jennifer didn’t become woven into the fabric of our business because she was our marketing partner. She became woven into it because she cared enough to keep showing up, and I trusted her enough to keep inviting her in.

Jen is not someone I hired. She is someone I build with. My success is her success.