Over the last fifteen years, Cave. has been rebuilt more times than I care to admit.

There was V1, which included me and a handful of buddies building and running the agency by the seats of our pants. It was fun, but it wasn’t sustainable.

After their departure came Cave 2.0, which had me thinking I could hire and train talent fresh out of college. This was good, but not great, largely because I vastly underestimated how much of my time training would take.

Then 2023 hit us like a ton of bricks. A lot of our clients in tech lost their funding as interest rates spiked, and marketing budgets were the first to get chopped. We lost clients, had to lay off people, and figure out how to keep the business afloat.

I know it’s fun to talk about profit and growth. But to be honest, we were hanging on by a thread. There I was, 12 years into running a business, wondering if I still had it in me.

Was I any good at this? Should I shut down the business? Or maybe I should get a job?

All of those thoughts ran through my head.

So my then fiancé—and now wife and business partner—Lauren knew we had to do something. We walked over to the equivalent of a park bench and talked about what we were going to do.

Should we quit? What was our best chance for success? How could we get there together?

Over a few hours, we talked through everything. What came out of it was a commitment to building Cave together in a way that focused on systems for content creation, management, and delivery, while providing white-glove support to our clients.

We believed we just had to make it through the storm. If we could do that, we’d be ready to regain speed once the waters calmed.

Around the start of 2024, a few months before we were set to get married, things started to improve. Leads began to come in. We started growing again, not just holding on to our last few clients.

Over the next 18 months, we built our team to 11 people. This time was different.

No juniors.
No generalists.
Just specialists.

It’s not that I have anything against junior employees, but we are not a good training ground. Our clients pay us for a standard of work that I believe only senior people can deliver.

And not only do I believe it, I’ve seen the proof. Since taking this new strategy of hiring specialists, and focusing on systems our business has grown. And perhaps only at the cost of my own ego as I don’t have to run every strategy.

For a long time, I believed I had to lead the charge on every client account to ensure quality. That sounded good on calls, but in reality it came out of insecurity. An insecurity that others on my team might actually be better at my job than I am.

Well, not only were they better, but I also realized that wasn’t my job in the first place. My job (and frankly what I’m best at) is not doing every aspect of the work; it’s finding great people and coordinating their efforts so that every aspect of the work is handled by an expert in that domain.

That one hurt. But after a few months, I realized what I was holding on to was misplaced pride in doing the work, as opposed to making sure the work was excellent.

So now, as we enter 2026, I’m off the rollercoaster. The path is clear. We’re building a boutique social media agency with specialists covering every aspect of the work and delivering world-class social media.

This year, I’m viewing the business more like a hike. It may take longer, and we’ll need breaks along the way, but there’s a clear peak we’re working toward. And we get there one piece of content at a time.

— Jordan

This is part one of the Building The Agency series. In this content series, we will share stories on what it’s actually like to build an agency business.