Path to $100M: How Chad Anselmo Is Building a Multi-Trade Business Through Acquisition and Operational Discipline

Most subcontractors grow the way they were taught: carefully, one project at a time, protecting cash flow because that cash flow is also the owner’s paycheck. Chad Anselmo is doing something different.

After three exits in fintech, he went looking for a boring, durable industry, ranked 72 of them across six to eight factors, and landed on the trades. In 2023 he founded LionShield Holdings. In 2024 he bought a plumbing company, nearly tripled its revenue, and built four more subcontractor firms around it. In this Path to $100M conversation with Billd CEO Chris Doyle, Chad breaks down the operational decisions that move a trade business from a few million in revenue toward $100M. The throughline is not a growth hack. It is discipline about capital, hiring, quality, and what you choose to let go of.

Why owners cap their own growth

Ask Chad what actually changed at the companies he acquired, and he goes straight to the owner’s relationship with cash.

When you’re growing companies extremely fast, working capital becomes a problem, and a lot of owners just don’t want to deal with that. So they say, ‘I’ll grow as usual. I’ll manage the cash flow more than I’ll manage to growth.’

It is a rational instinct when the business is your whole net worth and your entire income. Telling an owner to double growth usually means telling them to skip a dividend, and most owners cannot make that trade. LionShield can, because it spreads the balance sheet and cash flow across a portfolio of companies. If one company is growing faster than the others and hits a working-capital wall, the parent funds it internally and gets paid back as the work materializes. The lesson for a single-company owner is not to copy the portfolio structure. It is to recognize that managing to cash flow instead of to growth is a choice, and often the thing quietly capping the business.

Growth by acquisition, and by building from scratch

LionShield’s growth is deliberately two-sided: acquire, then build. Chad’s companies sit in adjacent trades on purpose, like vertical and horizontal plumbing, so they can share resources and take both sides of a job a GC would otherwise have to contract twice. But he is disciplined about when to buy versus build.

I could buy a $20 million company and pay $12 million for it, or I could start from scratch and get to $20 million in two or three years. So why would I pay $12 million for two or three years?

The exception is when the acquisition comes with something you cannot build quickly. “There are things we’ve acquired where we said, ‘There’s an economic moat here,’ therefore we’re going to acquire the economic moat.” Build for speed and cost; buy for the moat.

The infrastructure you grow into

One of Chad’s core frameworks is that the overhead required at $100M cannot exist at $5M or $25M, and the art is knowing what to over-invest in early and what to bootstrap. He thinks in three buckets: people, process, and platform, and he sequences them.

Optimize for cash flow first, get it to a point where you’re comfortable, then focus on your processes. Once your processes are set, you can really start to drive the people aspect of it.

The one thing he would scale ahead of the curve is people: leaders who can grow with the business. You do not need a maintenance yard at $3M, and you will not have a full management team until $50M or $60M. But the right people compound, so hire them before the org chart says you can.

Your first-round draft pick is the estimator

When Chad is asked which position is his number one draft pick, he does not hesitate.

Estimator. You estimate a project wrong, it doesn’t matter what else you do.

It is also one of the hardest hires, which is why so many contractors grow their own estimators out of the field. Someone who has installed the work for a few years, is sharp on a computer, and can read the first few pages of special instructions that make or break a project is worth more than almost any other seat. Chad’s own horror story makes the point: on one school project his team missed nearly every wall, ran pneumatic chippers across a 15,000-square-foot concrete pad for two weeks to move the pipe, and lost more than half a million dollars on the job.

The three things to a successful project are a good estimator, a good foreman, and a good GC. If you’re losing big money, all three of those stool legs came off.

Build quality that scales instead of throttling growth

Most owners assume growth and quality trade off against each other. Chad’s answer is to hire for quality rather than slow down for it. About a year and a half ago, LionShield put quality-control people in each region to walk projects and catch problems before they get expensive.

Don’t let the throttle of quality take down your growth. Just hire a person who focuses on quality.

The economics are stark. A toilet two inches out of ADA compliance costs about $300 to fix before the walls go up, and about $15,000 after. Catch five or six of those a year and the QC hire has paid for itself many times over. The role works because those people, often journeymen-in-waiting, read every spec with fresh eyes that a foreman staring at the same job for months no longer has.

Keep your best people by being the steady option

Every senior foreman Chad has, he says, has left at some point, and most have come back. The reason they return is not pay. It is reliability.

You need good people with good product, good delivery schedules, and good communication. And $3 an hour doesn’t buy that.

The pitch to the field is the same one he makes to owners he acquires: this is a place where payroll is always on time, the material shows up, and you can build a career. It is a competitive advantage that has nothing to do with being the highest bidder.

Treat capital as insurance, not a crutch

Chad’s advice on financing is to build the banking relationship before you need it. Be transparent, bring two-to-three-year projections, and walk a line of credit up over time rather than expecting the full number on day one.

Do we use it that often? Hardly ever. But it’s there for a rainy day. Heaven forbid one of our businesses lands a data center project and needs $4 million of material tomorrow. We have the ability to go tap it.

That is the mindset that separates growth-minded operators from reactive ones: capital arranged in advance, accessible fast and repayable quickly, turns a sudden $4M material order from a crisis into a Tuesday. It is also the exact gap Billd built its products to close for subcontractors who do not have a portfolio balance sheet to lean on: fast, flexible working capital that lets you say yes to the next project without draining the cash you need for payroll.

Advice for owners in the messy middle

For owners somewhere between $5M and $50M, still holding most of the work themselves, Chad’s advice is about letting go.

Find something you can delegate almost 100%, trust it, and free yourself up to do other things. Losing a little bit of control actually frees you up to do bigger and better things. It doesn’t restrict your business.

He also did the unglamorous work of earning credibility in a trade he did not come from. When LionShield bought the plumbing company, Chad enrolled in plumbing school for six months so he could sit in a meeting and understand an offset, a takeoff, or a wall that did not come up. “I wanted fundamental knowledge so my knowledge gap did not hinder the ability to talk with the owner or the performer.”

If you are going to sell, choose the buyer carefully

Because so much capital is chasing the trades right now, Chad closes with a warning for owners weighing an exit. A higher multiple is not the whole story.

Think of the worst-case scenario, apply it times ten, and ask, ‘Do I want to be with this person through that process?’ There are PE guys who will offer you a turn or two more, but if you miss a number for two quarters, they can become your worst nightmare.

His own operating philosophy is the opposite of a faceless roll-up. “I always say, ‘I’m going to leave the name on the front door so people don’t walk out the back door.’” For an owner who spent decades building a name, that is often worth more than an extra turn of EBITDA.

The takeaway

Chad Anselmo’s path to $100M is not built on a single move. It is built on refusing to let cash-flow fear cap growth, hiring the estimator like a franchise quarterback, catching quality problems while they are still cheap, keeping the best people by being dependable, and arranging capital before the moment you need it. None of it is flashy. All of it compounds.