No Longer a Solopreneur

Being a solo founder sounds freeing. You imagine full control, clear vision, and the ability to move fast without slowing down to align with anyone else. The reality is much heavier. Vacations never felt like vacations—I was still checking in on campaigns, assigning tasks from hotel rooms, and holding everything together even while trying to unplug. When big decisions came up, there was no one who truly understood the weight or the context to bounce ideas off. I could lean on friends or advisors, but it was still my call, my responsibility, and my sleepless night if things went sideways.

At DocsBot, our "team" until now has been my son, who I've been mentoring in marketing and entrepreneurship, plus a trusted bench of long-term contract developers and admins. They are all invaluable, but I remained at the center of every decision. Every project eventually funneled through me for approval, prioritization, or execution. If something stalled, it was because I hadn't nudged it forward yet. That kind of bottleneck is brutal when you're trying to build a category-defining product.

That changes now. I'm excited to share that @joshdailey is joining DocsBot as Chief Growth Officer, leaving WP Engine to join the future of customer support. Josh isn't just another hire; he's the person who can share the load, drive results, and own outcomes alongside me.

If you want to read more about the story behind this partnership, check out "From Treehouses to Tech: The Lifelong Friendship Behind DocsBot", a feature in The Repository highlighting how Josh and I went from building treehouses as kids to scaling DocsBot together. The piece dives into our long-running collaboration, the early experiments that paved the way for DocsBot, and why now is the right moment for us to team up again.

Why Josh?

Josh and I have history. We co-founded Infinite Uploads together during COVID (now acquired), where we learned how each other operates under pressure and uncertainty. We shipped product, handled support fires, and navigated growth during the strangest business climate imaginable. We were in the trenches together, and I know I can trust him when things get messy.

This summer he worked part-time with DocsBot, digging deep into the product, the workflows, and the customer journey so we could both be sure this was the right next chapter. He talked with customers, watched onboarding calls, and immersed himself in our roadmap. By the time we started talking seriously about a full-time move, we both already knew he was the right person—it was just a question of timing.

A few weeks ago he and his wife came to visit. We sat on the swing in my backyard and mapped out the details that would make him a true partner in the business: profit share, phantom equity, clear goals, and mutual expectations. We talked through how we'd make decisions, what success looks like at each stage, and how we can keep each other accountable. By the time the sun went down we knew it was time to make it official.

What changes for me

For me, this is both a relief and a turning point. I finally have a trusted partner to lead growth—someone to challenge and run with ideas, carry real weight, and care about the outcome as much as I do. It means I can take a real vacation without packing my laptop out of fear. It means the backlog of marketing experiments, strategic partnerships, and customer education initiatives no longer lives solely in my head.

It also gives me space to return to what I love most: building, strategy, and product. I get to spend more time working closely with our engineers, sweating the details of our AI stack, and shaping the experience that our customers rave about. Having Josh own growth means I can go deeper on the craft of DocsBot without sacrificing the company's momentum.

What changes for DocsBot

For DocsBot, it's the start of a new chapter. Josh is already laying the groundwork for a growth engine that is systematic and scalable: better analytics, sharper positioning, tighter feedback loops between sales, success, and product. He has a knack for telling the story of why DocsBot matters in a way that connects with founders, support leaders, and operations teams alike.

The market for DocsBot is massive. We and our competitors have barely touched it. Today we already have customers ranging from banks in Venezuela and law firms in Saudi Arabia to massive Japanese tech firms and car washes in Texas. Every business needs an AI agent that brings instant, 24/7, multilingual knowledge access for their customers or their team. Our job is to introduce them to what DocsBot can do, and now we have the leadership in place to do it at scale.

I'm energized for this next season. With Josh leading growth, DocsBot is better positioned than ever to serve customers who want reliable AI support that actually understands their business. And on a personal level, I'm grateful to no longer be doing this alone.

Here's to building the future—with a partner.

-Aaron