Boutique Business Advisory

Clarity for operators who've outgrown generic advice.

Stillwater Advisory works with a small number of founders and operators — providing direct, experience-based guidance on growth, operations, and technology strategy, including how AI fits practically into your business and leadership approach.

Schedule an Exploratory Call How I Work

20+ Years Operating

Multi‑Site IT Services Background

Max 10 Engagements — by design

"The most valuable conversation I'd had in years — and it was the first call."

IT Services Founder — Pacific Northwest

What I Do

Focused help where it matters most.

Advisory engagements are tailored, not templated. Depending on where you are, we may work across strategy, operations, or growth — or just one of them.

Strategy & Direction

Evaluating new markets, service lines, or business models. Building a decision framework when the path forward isn't clear — including where AI fits into your business strategy and how to adopt it without distraction or overhype.

Growth & Scaling

Moving from founder-led sales to a repeatable growth engine. Building the team structure and processes that let you step back. Navigating the transition from $1M to $10M and beyond.

Operations & Teams

Diagnosing what's creating drag in the business. Org design, compensation structures, and accountability systems that work at your scale. Getting out of the daily firefighting mode for good.

Mastermind & Peer Group

All active clients are invited to participate in a facilitated peer group — a small, private forum where operators at similar stages share context, pressure-test decisions, and hold each other accountable. Structured, not a casual networking call.

Who It's For

A limited practice for a specific kind of operator.

Stillwater isn't for everyone — intentionally. This model only works when there's a genuine fit on both sides.

Founders and owner-operators in technology, professional services, or adjacent businesses — IT services operators are especially well-served
At any stage — validating an idea, building your first team, or scaling past $10M. Revenue isn't the filter; mindset is
You've hit a ceiling and aren't sure if it's a strategy problem, a people problem, or both
You want a direct conversation, not a framework presentation or a consulting deck
You want a sounding board who has actually done what you're trying to do

Not the right fit if you're looking for...

A large team of generalist consultants
Implementation support or project execution
An execution partner or implementation team — this is advisory, not delivery
A guaranteed outcome or a silver bullet

How It Works

Simple, by design.

No intake forms, no lengthy questionnaires. Just a direct conversation to see if there's a fit.

Exploratory Conversation

We start with a 30-minute call. No commitment, no set agenda. I want to understand where you are, what isn't working, and what you're trying to build. You'll leave with at least one useful insight regardless of whether we move forward.

Engagement Structure

If there's a fit, we agree on scope and cadence — typically a mix of regular calls and asynchronous communication. Engagements are built around your current priorities, not a pre-set curriculum. All active clients are also invited into the peer mastermind: a small, facilitated group where members share context, pressure-test decisions, and hold each other accountable.

Ongoing Access

Active clients have direct access when something comes up — a decision to make, a conversation to prepare for, or a read on a situation that needs an outside perspective. The goal is to be useful in real time, not just on scheduled calls.

About

Domain Expertise

MSP Operations Hosting Pricing Strategy Team Building Multi-Site Mgmt Customer Retention Service Design AI Strategy Fractional CIO/CTO

Practice Size

Maximum 10 engagements
Selective — group fit matters

Available Via

Referral or Direct Inquiry

Expert Networks

GLG · AlphaSights
Guidepoint · Third Bridge

An operator's perspective, not a consultant's.

I've spent over two decades building and operating IT services companies — including two that I built and successfully exited. That means I've lived through the things most advisors only study: managing teams across locations, navigating difficult customer relationships, making hard calls on services that weren't working, and figuring out how to grow without losing what made the company good in the first place.

Along the way I've dealt with the full arc — including businesses that didn't make it. Those experiences taught me more than the exits did. Hiring the wrong people and fixing it. Pricing that killed margin. Services that sounded good but didn't scale. Leadership structures that worked at $2M and broke at $8M. I've made the expensive mistakes so the people I work with don't have to.

What's different about this advisory relationship is that I'm not speaking from the rearview mirror. I'm actively running companies right now — which means the instincts, frameworks, and hard-won lessons I bring into every conversation are being tested in live conditions today, not recalled from memory. When the market shifts or a new challenge emerges, I'm inside it alongside you.

At some point I realized the most valuable thing I could offer wasn't another deliverable or a polished report — it was a direct conversation with someone who actually had relevant context. Stillwater is that. A small, quiet practice for a small number of operators who want that kind of relationship.

I work with clients through expert networks and by direct referral. If you found your way here, you probably came through one of those channels. If you're not sure whether this is a fit, the easiest thing to do is reach out — the initial call is always free and there's no obligation.

Get in Touch

Start with a conversation.

Schedule an exploratory call

Reach out directly. I respond to every inquiry personally, typically within one business day.

David@stillwatersvcs.info

Stillwater Advisory Services is a Wyoming LLC. All inquiries are handled confidentially.

"Most of the operators I work with had been looking for this kind of conversation for a while. They didn't need more information — they needed someone who had seen what they were going through from the inside."

Engagements are intentionally limited to maintain quality. If there isn't capacity right now, I'll let you know and keep you in mind as things open up.