I paid $50k for a lesson I already knew

This is embarrassing to admit.

Last year, I burned through four virtual assistants and blew $50,000 on operations consultants.

The consultants turned a 90-day project into 9+ months of chaos. We were worse off than when we started—halfway migrated to new tools, broken processes, complete disarray.

Here's the kicker: I already knew better.

I literally coach technical business owners on this exact mistake every day. Just in sales instead of ops.

The "Who Not How" Trap

Maybe you’re familiar with Dan Sullivan’s advice in Who Not How: Don't figure out HOW to do something—hire a WHO to handle it.

It's brilliant advice. I recommend it all the time.

But there's a critical piece missing that cost me $50,000 to learn (again).

Here's what happened:

Attempts #1-4: Hire "Hows" I hired affordable VAs to be an extension of me. Clean up automations. Simplify our tech stack. Create SOPs.

First one failed. Must be them. 

Second one failed. Bad luck. 

Third one failed. What are the odds? 

Fourth one failed. For fuck's sake.

Attempt #5: Hire a "Who" "I know this lesson! Dan Sullivan says hire a Who, not a How. I need someone expensive who can just handle this."

Found someone with stellar credentials. They talked a great game (not hard when I didn't know the right questions to ask).

Nine months later? Still broken. Actually worse—now we're halfway migrated to multiple systems.

The Moment I Finally Got It

Banging my head against the wall, I made a decision:

I'd figure it out myself.

Not forever. Not to become an ops expert. Just enough to understand what the hell was actually needed.

And when I finally rolled up my sleeves and dug in, I discovered:

• Massive redundancy in our tech stack

• Using only 20-30% of our tools' capacity

• Processes that contradicted each other

• Overlapping automations that created chaos

But more importantly, after looking under the hood I finally understood:

• What actually needed to be done

• Whether I needed a "Who" or a "How"

• What questions to ask candidates

• What success would actually look like

The Real Sequence That Works

Dan Sullivan isn't wrong. But the complete formula isn't:

Who Not How

It's missing a critical variable: You.

Here's what that means:

You First: Do enough to understand what's needed. You don't master it—just understand it.

Then Who or How: Now you can hire intelligently because you:

• Know what you're hiring for

• Can give clear direction to a "How"

• Can validate expertise in a "Who"

• Can set them up for success

Without that first step? You're just throwing money at a black box and hoping.

Why This Was So Embarrassing

I teach this exact lesson to technical founders and MSPs all the time—just about sales:

They try to hire away sales before understanding it. The pattern is identical:

1. Hire the wrong SDRs → Fail

2. Try a few more times → Fail

3. Outsource to an ‘easy button’ agency → Fail

4. Hire expensive sales rep → Fail

5. Hire sales manager to "figure it all out" → Fail

And what's mortifying is I tell them exactly why this happens:

You can't hire for what you don't understand.

Yet there I was, doing the same thing with ops.

The Uncomfortable Truth

We all want to skip the "You" step.

• Technical founders want to skip learning sales

• Sales folks want to skip learning operations

• Everyone wants to skip whatever feels uncomfortable

But here's what I've learned (twice now, apparently):

You can't delegate what you don't understand.

That's not hiring—that's hoping.

The You Action Plan

If you're stuck on something right now: Stop trying to hire it away. Spend 30-90 days getting a better sense of what you actually need. I’m not talking about ChatGPT’ing your way through things. I’m talking about rolling up your sleeve and doing the thing: making cold calls, experimenting with the tech, learning the platform, or whatever it is.

If you've failed with multiple hires in one area: The problem probably isn't the people. As Peter Drucker famously said, if multiple people fail at the same role, the role is broken. Not the people. And it needs to be redesigned. But you need to understand the role in order to redesign it properly.

If you're thinking about hiring for sales: Can you explain your sales process? Do you know what good looks like? Can you score candidates you’re interviewing beyond gut feeling? Can you train someone? No? Then start there.

This is exactly why our fractional SDR and sales management programs require owner involvement. We could sell you a "done-for-you" solution, but we've seen how that movie ends.

You. Then Who/How.

It's a $50,000 lesson I apparently needed to learn more than once. I’ll call it tuition.

But don't be like me.

Adios,

Ray