You’ll hear people talk about how ‘easy’ high school or University was.

Or you’ll hear stories from successful entrepreneurs who were ‘too busy with side hustles’ to attend class or study, which is why their grades sucked. Or they had ADHD or dyslexia (who doesn’t these days), to explain their GPA.

I was NOT that guy.

I was the guy who studied HARD and still walked out with a C, D, or F. Now don’t get me wrong, I managed a few A’s, but they were in classes that came naturally to me like English, History, or… PE (a real intellectual combo). Math and Science? Didn’t matter how much studying I did — I was sweating come test time.

Turns out, it’s not because I’m stupid. It’s because I wasn’t thinking like a dumbass (stay with me).

Like the midwit meme, I (the midwit) would white-knuckle my way through studying, especially in math. I’d try to memorize how to do the practice questions instead of learning how to solve the problem. The moment the test had any variance from the practice exam — I was lost. If I’d simplified my approach instead of complicating it, I would’ve been fine.

There’s a joke in the entrepreneurship community that real estate has the highest net worth-to-lowest IQ ratio (to be clear, this is not my joke). Real estate guys get this rep because the entire playbook is: buy a building collecting $X of rent per month, pay a $Y/month mortgage, pocket $Z in profit. Then hold it for decades while the rent pays down the mortgage, and eventually sell it for a big gain or pass it along to the family.

Now, if you reacted to that with “hey, it’s not that simple!” — congratulations, you’re approaching it like a midwit. Because it really is that simple. Executing it is not.

I’ve witnessed this countless times. You meet a wildly successful entrepreneur who, respectfully, seems like a complete dumbass. But that’s exactly the point. They never overcomplicated their way out of a good decision.

A lot of people come to Breakwater to buy a business. Unfortunately, we deal with a lot of midwits. These are the buyers hunting the perfect ‘unicorn’: low CAPEX, a full-time CEO already running the place, and an owner with ‘no other options’ who’ll take $0 down. In the midwit fantasy, the dividend cheques start rolling in month one while they ride off into the sunset of their passive income oasis.

The result? They never find anything that ticks every box, get frustrated, and quit their search without ever buying anything. Meanwhile, the best acquisition entrepreneurs (and that dumbass at the cocktail mixer) don’t overthink it. They buy a cash-flowing business for a fair price, make a few small tweaks, and let it compound for decades.

So the next time something looks ‘too simple,’ remember: while the midwits are busy building spreadsheets to prove it can’t work, some delighted dumbass is already living off it.

new videos on youtube

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that’s of interest, make sure to subscribe

Morgan Tate

M&A Advisor | Building Breakwater M&A | Writing @ morgantate.com

YouTube

idea of the week 💡

Credit: ideabrowser.com

ExitBrain — an AI exit interview that pulls the business out of the owner's head

  • Problem: 70%+ of small businesses listed for sale never sell. the three usual culprits: too much owner dependence, messy financials, unpredictable revenue. a retiring boomer and his son on r/smallbusiness just ran a $374k/yr business through meeting after meeting and still couldn't get it sold. the operating manual was never written down — it lives in one guy's head, and buyers won't pay a premium for a head.

  • Idea: an AI interviewer that asks the owner exactly what a buyer's diligence team would ask, then turns the answers into an interactive playbook a stranger could run the business from. answer the objections and the rejections upfront instead of discovering them in week six of diligence.

  • How it works (wedge): structured voice sessions ask the buyer questions — which ten clients actually matter, what breaks in February, who has the vendor relationships, what happens when you're gone for three weeks. transcripts compile into SOPs, an org map, a client concentration view, and a risk list. a refresh session re-interviews the owner every quarter as staff and pricing drift. start with brokers and exit planners who already have listings that keep dying in diligence.

  • How it makes money: $499 per interview, $99/month to keep the playbook current. real upside is the channel — brokers, M&A advisors, and QoE providers white-labelling it as a pre-listing step, plus the data asset that comes from thousands of owners describing how their businesses actually run.

  • Why it might fail: the people who need it most are the least likely to buy it — owners who won't document anything also won't sit for six hours of interviews. and a playbook doesn't fix messy books or lumpy revenue, so the promise of "add dollars to the offer" is hard to prove. feasibility 7/10 — the tech is straightforward, the behaviour change isn't.

my two cents: this is the deal I see die most often. the business is fine, the owner is the business, and the buyer prices that risk right into the offer. anything that moves knowledge from the owner's head onto paper before a listing goes live is worth real multiple points.

workouts this week

at-home

15-minute AMRAP:

  • 12 push-ups

  • 16 walking lunges

  • 12 backpack (or dumbbell) rows

  • 30-second plank

gym

Strength + conditioning. 4 rounds:

  • Back squat: 6 reps (moderate-heavy)

  • Strict overhead press: 8 reps

  • Pull-ups: 8 reps (band if needed)

  • Row erg: 45 seconds hard

Rest 90 seconds between rounds.

outdoors

  • 10-minute easy jog (warm-up)

  • 4 rounds: 3-minute run (steady-hard), 90-second walk (recover)

  • 5-minute walk (cool-down)

tweet of the week

I built an entire startup around the idea of outworking and outsmarting everyone in the industry… spoiler: it failed.

my plugs

every second counts

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