WIN x West McDonald: The Economics of AI

West McDonald has spent four and a half years teaching managed service providers how to make money on AI.

By his own count, almost none of them are doing it. I checked that against our own data before we sat down to record this episode of WIN. Fox & Crow Instinct tracks roughly 110,000 technology service providers, MSPs, VARs, and office equipment dealers with a managed services practice, across LinkedIn, Facebook, and a rolling 30-day snapshot of every company's own website. I searched three terms: AI workflows, AI policies, and monetizing AI. Fewer than 250 companies turned up under each one.

West, founder of gowest.ai and BizVantage, wasn't surprised.

We've been in this business now officially for four and a half years, and we kind of thought that MSPs would've taken this on like lightning, the way they did once cybersecurity offerings came along.

Here's why that never happened, and what he tells MSPs to do instead.

Listen to the full episode:

The Resale Play That Never Showed Up

MSPs know how to sell a box. Antivirus, backup, cybersecurity: someone builds it, the MSP resells it, bills for it monthly, and moves on. West says that's the model most MSPs assumed AI would follow, and it's the reason so many of them are still standing on the sideline.

He described one conversation with an MSP who told him AI monetization was "too complicated" and "not vertical enough." That MSP's actual plan was to wait for AI-enabled chips from HP and Dell to land in customer hardware, and layer Microsoft Copilot licenses on top.

We think that's the direction we're gonna go, 'cause we can resell those things and then we're in the AI game.

None of it played out that way. The on-device chips never found a job to do, because the AI workloads people use moved to the cloud instead. Copilot can generate revenue, but only after an MSP wades through licensing and implementation work most of them weren't set up to sell.

So no one's gonna get paid to sell ChatGPT, or Claude. However, to be able to incorporate those into customer environments, that's where the money lives.

That's a different sale than the one MSPs are used to making. It isn't a product line. It's a service built on understanding a customer's business well enough to know where AI fits, and West says that discomfort, not the technology itself, is what's kept most MSPs on the sideline.

The Trust MSPs Are Sitting On

While MSPs wait, other players are moving in. Instinct puts the median age of a managed services provider in our database at 16 years. We're also watching two- and three-year-old companies enter the market and present themselves to MSP-sized customers as if they've been established for a decade, competing for the same technology dollars.

West sees the same pattern playing out with the business consultants he partners with, smaller firms doing the kind of work McKinsey does at enterprise scale. For a separate benchmark of how MSPs position AI advisory services publicly, see the Fox & Crow Instinct MSP AI Visibility Report.

All of them have this kind of imposter syndrome. It's like, 'It's not our job to do AI.' But the answer to it is, it absolutely is, because customers are begging for help to figure out how to navigate this.

MSPs are better positioned than almost anyone to answer that call, because AI is, at bottom, a technology, and managing technology is the job description. West likes an old line for this: in the land of the blind, the one-eyed man is king. An MSP willing to spend a little time learning doesn't need to become an AI research lab. It needs to know enough to be the most informed person in the room, which, right now, is a low bar. Matt Tomlinson's WIN conversation explores why MSPs already using AI often hesitate to talk about it publicly.

Start With The Work, Not The Tool

West's advice for where to begin runs against how most MSPs are trained to sell.

Don't think about AI. If you want to know the best way to use AI in your business, start with the work. Find out the areas of your business that you think you need the most help in.

He's watched clients get this backward constantly. One told him they'd already decided to roll out Copilot and just needed help with the permissioning. West pushed back and asked why. The client didn't have an answer beyond "we know we have to do it," and West says that's exactly the wrong place to start. The right starting point looks more like: our document management is a mess, our SharePoint is unsearchable, and our team can't get customers answers fast enough.

The way he gets to that answer with a client isn't technical. It's a single question: tell me about the worst part of your day, and don't worry yet about what the fix looks like. That approach to starting with the buyer's business problem is also at the heart of surfacing business pain in MSP discovery.

It's kind of like being a bartender, where people offload their worries and concerns, and how good you feel after you've done that. And you feel even better when the MSP comes back with a solution to fix that problem.

One of the examples he builds almost daily for clients is an inbox triage assistant for executives buried in email. It runs inside tools the client already pays for, Claude or ChatGPT, takes about three hours to build, and pays back immediately. That's the pattern: find the tedious, recurring thing that's already driving someone crazy, then apply AI to it, not the other way around.

West's second piece of advice is to not be afraid to bring in outside expertise to get started. He credits it to the late father-in-law of his business partner, who spent his career at PricewaterhouseCoopers and whose parting advice to his family was simply, "outsource everything." West applies the same logic to his own blind spots: what looks easy to him after doing it a thousand times isn't easy for someone doing it for the first time, and that gap is exactly what a specialist gets paid to close.

His third recommendation is the one he says MSPs should treat as the actual starting line: AI policies and guidelines. It doesn't require a big technical lift, and it solves a problem that already exists inside every one of their clients' businesses whether anyone's noticed yet or not.

I guarantee you right now some people are using Claude, some people are using ChatGPT, some people are using Codex. This stuff is all happening in client environments, and what they first need to do is lay down an established set of rules.

The Relationship AI Can't Sell

West's own platform, BizVantage, automates the workflow assessments and AI policy documents he used to build by hand over roughly four days per client. What he won't automate is the interview that feeds it.

A client once asked him why the discovery interviews couldn't just be handed to AI. West's answer:

Because you need eight, nine, 10 points of contact in a sales process with a human being for them to trust you and buy from you.

He came back to the same point later, from a different angle:

AI cannot build relationships, and if you're selling, at least that's my belief, you need a relationship before somebody buys from you.

That's the same conclusion I've landed on watching our own sales data. AI is genuinely useful after a discovery call, reviewing the recording against dozens of criteria to show a rep where they dug deep enough and where they didn't. It has no place running the call itself. Customers don't build trust with a chatbot, and MSPs selling AI services are, underneath it, still selling trust.

The MSPs willing to do that work, ask the questions, write the policies, sit with a client's actual pain instead of a vendor roadmap, are the ones who'll own this category before it gets crowded. Everyone else is still waiting for a chip that already missed its moment.

You can hear the full conversation in WIN x West McDonald: The Economics of AI. He works directly with MSPs through gowest.ai and runs AI workflow and policy assessments through BizVantage.

If your MSP needs help building the kind of sales process that turns a discovery conversation into a service customers buy, that's what we do at Fox & Crow Group with our MSP Sales Process training. Book a call to talk through where your MSP stands today.