Hello friend,
Why you’re getting this: This is my Friends Newsletter; a weekly drop of operator brain goo and frameworks from the chaos of running 75+ businesses. It’s not a VC flex. It’s a “don’t step in that puddle like I did” guide. Unsubscribe if you already know how to spot a great company in 15 minutes.
Here’s what I’m thinking about…
I’ve looked at thousands of businesses.
Bought dozens.
Walked away from hundreds.
And I can usually tell—within 15 minutes—if it’s a yes, no, or “bury this under a rock.”
How?
I use a checklist.
Not a 42-tab model. Not a 90-page deck.
Just a short list of filters that Buffett would probably nod at.
If a business passes these filters, we dig deeper.
If not, I move on; guilt-free.
Because most of what matters shows up fast.
I don’t need a 6-month diligence process to know if:
I just need a good sniff test.
Here’s what I ask myself the moment a new deal hits my inbox:
I don’t want “momentum.”
I want margin.
No profits = no freedom.
Boring is beautiful.
I don’t want hot sauce, I want HVAC.
The less sexy, the better.
If a tech bro would sneer at it, I’m interested.
Not a PowerPoint moat.
A real moat.
If you can clone it in a weekend, I’m out.
The dream is:
Software, memberships, hosting, monitoring, consumables, etc.
One-and-done businesses are fun until they’re not.
I’m not buying a business.
I’m buying a person I can trust.
If the founder is running from burnout and the team is a house of cards?
Pass.
If the operator is sharp, honest, and has taste?
I lean in.
Tiny is not a flipper.
We buy to hold.
If I’d be embarrassed to own it, I won’t buy it.
I have to be okay talking about it at dinner.
I’m lazy.
In the best way.
If I can’t improve it with:
…without showing up to daily standups, it’s a no.
The goal is not to run it.
The goal is to support it.
If someone’s asking 20x EBITDA and calling it “fair because of the vision,” I’m out.
We usually aim for 3x–6x SDE or EBITDA, depending on the growth and moat.
No fantasy math. Just return on invested capital.
If I smell any of these, it’s a no.
Immediately.
If you run a business that:
Email me.
This is literally how we decide whether to start a convo.
Still loving GPT-5 for first-pass financial summaries.
Still using human operators for final calls (for now).
Still saying no 99% of the time.
If you’re building a due diligence checklist for yourself; or thinking about selling; feel free to steal this one.
1. Do you actually decide in 15 minutes?
Yes. But we still run diligence before closing. This just tells us if it’s worth our time.
2. Do you ever get it wrong?
Of course. But fewer than when I used to overthink.
3. What’s the biggest mistake sellers make?
Hiding stuff or overhyping. Just be direct.
4. What do you care about more than valuation?
Trust. I’ve paid more for great operators.
5. Will you buy a startup?
Only if it’s profitable. We’re not gamblers.
6. Do you do earn-outs?
Yes. But only with the right incentives.
7. What about minority stakes?
Rarely. We like control or clear swim lanes.
8. Do you buy agencies?
Sometimes. If they have recurring revenue and strong leadership.
9. Should I pitch you?
Yes. But read this checklist first.
10. What if I want to use this checklist for my own deals?
Please do. That’s why I wrote it.
That’s all for now…
Simple filters. Fast decisions.
It’s not about being right; it’s about knowing when to go deeper.
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