The Work Series | Rethinking the Field: Austin Ilsley on Ai Painting’s Shift to the Sub Model

About the Episode

Not every business decision gets to be a careful, strategic choice. Sometimes the numbers force your hand – and you either adapt or go under.

That’s where Austin Ilsley found himself heading into 2024. Co-owner of Ai Painting Plus in Columbia, Missouri alongside his wife Lacie, Austin had spent years building a W2 field team – investing in culture, leadership development, and the kind of benefits that could compete with larger employers. Then the financial reality caught up. In this episode of Out of the Hourglass, Austin traces Ai Painting’s path from a full W2 model to a predominantly subcontractor workforce, and shares the honest lessons from a transition that’s now producing record net profit.

When the Numbers Said Something Has to Change

Ai Painting Plus was growing.  Austin and Lacie had assembled a team of W2 field employees, including newly promoted leaders being developed for bigger roles. However, the growth was outpacing the infrastructure that could support it.

“We rushed a lot of those people into the positions that we had them in, particularly in leadership,” Austin explains. “They just didn’t have the competency to really fulfill that role. And it caused some financial issues.”

The financial pressure hit hard, and a values matrix exercise helped them identify who was and wasn’t the right fit. They cut over half the team. With overhead no longer covered, the sub model – which they’d been using in a limited way – became the clear path forward.

The Culture That Came at Too High a Price

One of the harder truths Austin shares is that the culture they were trying to build was part of what put them in a difficult position. Ai Painting wanted to be a workplace that rivaled larger employers – benefits, retirement plans, PTO that would make their team proud to be there.

“We wanted to be the avant garde thought leader in the industry that’s gonna find a way to be able to provide the benefits and the insurance for the employees and the retirement plans,” Austin explains. “We just could not afford that kind of overhead.”

Once those expectations were set, walking them back wasn’t an option. “If we were to go back,” Austin says, “the result probably would have been the same. If we took away all those benefits, the same people we let go probably would have saw themselves out anyways.”

As Austin puts it plainly: “If there’s no company, there’s no where to go anyway.”

Letting Go of Control, and Finding It Somewhere New

For Austin and his leadership team, one of the hardest parts of moving to the sub model wasn’t operational, it was psychological.

“We were afraid of the change. We were afraid of that drastic change and leaning completely into something that was so unfamiliar.” The fear of losing control over quality and customer experience was real. What Austin discovered was that the control hadn’t disappeared, it had simply moved.

“It’s not that we actually lost control,” he says. “We just had to figure out a different way to gain that control is all it was.”

Under the W2 model, project managers were frequently pulled into crew dynamics – fielding personnel issues, covering for team members. With the sub model, that changed. Each project manager now has one point of contact per job: the sub crew leader.

“I talk to one leader. I don’t have to worry about X, Y, Z person on your crew not showing up on time, because that’s totally your job, built in accountability, you as the sub. Now I get to focus on the customer.”

What It Takes to Build a Strong Sub Relationship

One of the most practical threads in this conversation is how Austin and his team think about vetting and onboarding subcontractors. His answer comes down to one word. “Trust. That’s bottom line.”

Trust shows up in specific, observable behaviors: showing up for walkthroughs, being transparent about scheduling conflicts, communicating proactively when something goes wrong. Austin also credits advice from another painting business owner for reshaping how they think about sub relationships entirely, treat sub crews the same way you’d treat your own employees. Bring them into your culture.

“They’re part of our team, they’re part of our culture,” Austin says. “We onboarded them and brought into our family the same way we would have…W2 employees.”

Sub crew names now appear in Google reviews alongside the project managers – a sign, Austin says, that they’ve gotten the culture piece right.

The Financial Picture – and What’s Next

Austin is transparent about the tradeoffs. Gross margins have compressed slightly , attracting quality sub crews requires paying competitively. But volume tells a different story at the bottom line.

“Net profit wise, we’re gonna have a record year.”

He also acknowledges real limitations. Institutional work and prevailing wage jobs are harder to pursue with a sub-based workforce, opportunities he’s thinking about recapturing by slowly rebuilding some in-house capacity over time.

As Austin puts it: “There’s no silver bullet. Like this is not a silver bullet to all the problems, but it’s been a benefit for my problems.”

That honesty – grounded, unsentimental, and hard-won, is exactly what makes this conversation worth your time.