Dire Straits and making “gut feel” decisions

Hey everyone,

I killed last month's newsletter at the last minute. Had it written, proofed, scheduled, everything ready to go. Couldn't hit send.

I had written 2,000 words about a real business owner staring at $1,500 in their checking account with bank payments, seller notes, and payroll all due next week. Almost no receivables coming in. No cavalry on the way.

No happy ending. No pivot story. No "and then they implemented EOS and everything turned around" crap. Just the truth about what happens when everything you've built is circling the drain and you're making decisions in the dark with no idea if you'll even be in business two weeks from now.

Most business communities won't show you this. They'll sell you frameworks and funnels and "scale" strategies from consultants who've never missed a payroll in their lives.

What I hope happens is that this person makes their comeback. That by next year I can share the full arc—from the absolute bottom to complete redemption. A business that once caused them panic attacks at 2am turning into something that actually delivers what we're all chasing: financial freedom, purpose, proof that we were capable of the hard thing.

But right now? Right now they're in the shit, they’re moving day to day and it’s a big question mark of whether they will make it out.

And honestly, this is what business ownership actually looks like most of the time.

You make a dozen decisions today that won't be proven smart or stupid for years.

You buy a company knowing it will be hard, convinced you're capable of hard things, but you won't have actual proof of your capability for 24+ months. You hire someone thinking you nailed it, only to discover three months later that all you have is wasted time, money, and a smoking crater where your operations used to be. (But hey! You learned something new and you’re slightly less likely to screw it up next time!)

The same "smart" decision that works for someone else may be stupid for you.

Because your business is different. Your market is different. Your people are different. Your debt stack is different. Your skills are different. What saves one operator could hurt another.

Yes, there are tools and frameworks that help—EOS, Predictive Index, industry-standard CRMs, proven SOPs. Things that thousands of others have tested and work broadly across most companies. All of these exist to help you make better educated guesses given the specific mess that is your business.

But at the end of the day, you're still guessing. Just better educated guessing.

Uncertainty comes with the territory. The good news is it builds like a callus. You get used to operating in the fog.

So for this newsletter, I'm going to share five "gut feel" decisions real operators in our community made, some of which go against conventional business wisdom. Decisions that might be genius or might be financial suicide, but at the time they’re making these decisions the answer isn’t clear. 

I'm not sharing these so you'll copy them (please don't just copy them). I'm sharing them so you understand you're not alone. There are operators out there making unconventional moves, trusting their instincts about their specific businesses, and living with the uncertainty that comes with it.

Let's get into it.

1. Two $4M Commercial Cleaners With Basically No Overseas Talent

On our most recent peer group call, we had two commercial cleaning operators (both doing over $4M annually) discussing their overseas teams.

Or rather, their lack of overseas teams.

One owner had a small bookkeeping setup overseas. The other had zero global talent. Nothing.

At $4M in annual revenue, that's rare compared to the rest of our community. We had the obvious conversation about opportunities to integrate global talent for administrative roles.

But they both had legitimate reasons for staying local that went beyond the usual concerns about culture and team cohesion (though those concerns were real).

There are a couple operations dynamics in commercial cleaning that makes global talent a bit difficult even for roles like customer service or reception.

Here's why: Communication with labor happens at night while crews are cleaning. Coordination with management happens during the day—estimating, scheduling, customer communication, all of it.

Both operators had strong convictions that a customer service person needs to be in the office. The role benefits from in-person presence because of constant impromptu conversations and on-the-spot problem solving. And anyone interacting with cleaners needs to be there in person when they're checking in or out.

2. Towing Operator Offering Health Benefits (In An Industry Where Nobody Does)

One of our members owns a towing company and is (I think) the largest operator in his area offering health insurance.

The statistic is something like 97% of towing companies don't offer health benefits. It's just not common.

He didn't do it to boost employee happiness or retention, at least not directly. He did it because of personal beliefs about healthcare accessibility. It costs him a pile of money every year that he could otherwise pocket.

Paying a ton of money for something no employees expect? And still paying them market wages? Why?

Well here's what happened: It completely solved his recruiting problem.

Other tow truck operators spread the word around town. Now, anytime anyone's looking for a new gig, he's the number one pick. He's getting the best operators because he's the only game in town offering real benefits.

There’s a ton of other soft benefits to this, for example it’s a pretty nice feeling knowing that you’re not being held hostage by your local talent pool.

This was not an expectation he had going into it, and it took over a year for the word to really spread around in his industry. But it was an unconventional decision (for his industry) at the time and today it’s paying off.

3. Manufacturer Who Ripped Out Health Insurance (And Gave Cash Instead)

On the complete opposite side, one of our manufacturers doesn't offer a company healthcare package at all.

Instead, he provides a $425 monthly cash stipend. That's it. Do whatever you want with it.

He does this because:

- It's flexible—some employees get coverage through a spouse, some want the cash bonus, some prefer concierge medicine or group cost-sharing setups. Everyone wants something different.

- He hates the administrative brain damage that comes with group health plans

- He's done chasing employees for enrollment paperwork

- He's tired of fielding questions about networks, co-pays, and coverage decisions he has zero control over

- He doesn't want to deal with annual plan changes and price increases

- He's experienced the nightmare employee-owner-insurer relationship where employees blame their employer for decisions the insurance company made

- He genuinely believes small business group plans often have worse options than individual marketplace plans anyway

Here's the kicker: He acquired this business and actually had to ROLL BACK the healthcare package the previous owner offered.

That's a risky move. But in this case his employees appreciate the flexibility and it's working for him.

If you’re considering doing this, know that results will absolutely vary.

4. 250-Person Manufacturer Who Fired All Three VPs On The Same Day

I spoke recently with a manufacturer running a 250+ employee operation. He had three VPs who'd each been with the company for 3+ years.

When he looked under the hood at how they were actually managing their teams, he saw cultural problems dividing the business.

The problem wasn't that these VPs were toxic and their teams hated them. The problem was subtle. Their teams were absorbing the ethereal energy and mentality of their bosses, and each team's individual culture was getting skewed off track from what the owner was trying to build and it was causing some infighting.

So he fired all three of them. At the exact same time.

Then he took on the work of three executives himself while relentlessly screening replacements for perfect culture fits.

He basically hit the eject button on his entire leadership team. A decision that at the time felt insane. But today he has a company that’s aligned on culture which he is happy with.

5. Construction Operator Pursuing A Wildly Creative JV Deal (That Fell Apart)

One of our members in construction is growing fast and recently approached a very creative deal structure: starting a new entity in a new state, selling roughly 30% equity to one of the major general contractors he worked with to fund startup growth.

There were other criteria that made it much more complicated, but the core structure was extremely rare for the industry. Theoretically, it made sense. He was bringing innovation and creativity to an incredibly boring, traditional industry.

Unfortunately, that deal fell apart (as most do).

But I admire that he tried. I admire that he looked at a commodity business and thought, "what if the fundamental structure was completely different?"

To wrap these stories up, just know that there are others out there making their best guess, living with uncertainty, making big moves, and not knowing if they’re the correct moves often for years to come.

It’s normal

Now I want to shift gears and talk about something related which I discovered at our Atlanta Manufacturing Retreat last week.

The retreat was incredible. We toured two larger manufacturing operations, facilitated discussions for a day and a half, and created space for real relationship building between people who have a lot in common… Things that have nothing to do with their industry.

Here's what I noticed during the retreat:

Over the last few years, I've listened to hundreds of business owners describe their problems and discuss potential solutions (Like those gut feel decisions mentioned above). Over time, I've watched whether those solutions actually worked or not.

It could be a tactic, a SOP, an employee who needed to be fired, a software tool, an advisor who specializes in a specific problem.

At the retreat, I realized a huge amount of the value I bring to our community gets delivered through this accumulated knowledge—this agglomeration of insights, tools, stories, and real outcomes.

Remember those 5 gut-feel decisions I just shared? Anytime a business owner brings up a similar decision they're wrestling with, I have context. I have real data points. I know who's tried what, what worked, what failed, and why.

And that's just 5 decisions. I have hundreds, maybe thousands of these to pull from.

More importantly, I have real answers. In our community, we know who uses what tools, who works with what advisors, who pays for what software. We know all of it, and we can distribute information about what actually works as a shortcut for the operators we work with.

I see two directions this can go:

Direction 1: A business owner comes to us with a question about a problem they're experiencing, and we connect them to resources and real-world examples that resolve it or give them more clarity around it.

Direction 2: We proactively audit our member’s businesses, identify deficiencies they're unaware of, and offer them perspectives or solutions that have already worked for others—making their companies stronger.

So all of that uncertainty I wrote about above? I believe we can make the business owner journey far more visible through connections via our community and our member case studies.

How this actually manifests is still unclear. But I feel very strongly that we're developing a core capability beyond just connecting people. We're connecting their combined knowledge and experience into something greater that helps everyone grow faster and make fewer mistakes.

Because here's what I know for certain: You can't figure this out alone. The decisions are too complex, the stakes are too high, and the feedback loops are too long.

You need other operators who've already made the mistakes you're about to make.

If you want to see if joining a peer group is right for you, reply to this email or apply here

Talk to you next month!

Rand Larsen