The stat that stops every owner I share it with:
75% regret selling their business (Wells Fargo).
And almost never for the reason you’d guess.
After several years of advising owners through exits, I can tell you the regret is rarely about leaving money on the table.
It’s about leaving the version of themselves they built on the table.
The business was the calendar. The identity. The reason the phone rang. The day after closing, all of that goes quiet at once.
The owners who exit well treat the life after the sale with the same rigor they treat the deal.
They plan the next chapter before they sign anything.
They negotiate for time.
They build a life outside the business in the year before the close, not after.
If you’re thinking about an exit in the next 1 to 3 years, the most valuable work you can do this quarter has nothing to do with valuation.
It has to do with what you actually want your first Monday morning to look like.
What would yours be?
#BusinessExit #FractionalCFO
Struggling business, three options: hire expensive management, sell, or back your current manager with AI.
Most owners skip the third. Price it first. If the manager rises, buyers pay more. If not, you decide with evidence, not fatigue.
Before AI touches a customer, make it interview like a hire.
Grade it blind against work your team already finished. The matches get a quick review. The misses write the job description.
Cost: an afternoon and zero live customers.
AI made modeling faster. The new job is review.
Vendors sell the speed. They rarely sell the checking.
The honest math is not hours saved. It is hours moved. Put a named human on the gate before anything ships.
AI after the demo is plumbing, not magic.
My week runs on a morning briefing, written skill files for each job, weekly self-audits, and a human gate on every output.
Write the business down for AI and you have written it down for a buyer too.
Owners call customer relationships a selling point. Buyers price them as a defect.
One question: who approves a price change when the owner is traveling?
If your team looks at you, the discount shows up in the LOI, never by name.
Make your absence boring before you sell.
Every post with my name on it starts as an AI draft. None goes out without me.
Our rules: one assistant per job, rules written down, a human approves anything that leaves, check before publishing, unverified means unpublished.
That is also exit prep.
Credential lapsed. Permits stopped. Standard fix: up to 12 weeks.
Same meeting: Claude on the state's rules, letter drafted and sent. Same-day fix.
AI did not pick the priority or touch the legal matter. Trust stays human.
#AIforSMBs#PracticalAI
A pool owner told me the only fix was another him. He was half right.
More than a dozen decisions hit his phone. Only a handful were judgment. The rest were writeable rules.
Every rule you refuse to write down is a guess. AI raises the price of keeping it in his head.
#AIAdoption #Delegation
A signed LOI starts a clock. One owner spent 19 of 45 exclusivity days hunting paperwork.
Buyer list: 68 items. Four did the damage. The extension handed leverage away for free.
A buyer reads a slow document twice.
#DataRoom#ExitPrep#ExitReadiness
"If you don't pay taxes, nobody's gonna believe you're making any money."
Buyers price what you can prove.
At 3x, every dollar off the books costs about $3 of purchase price.
What would your last three tax returns tell a buyer?
#ExitReadiness#CleanBooks#SMBExit
A client lost the ability to pull permits the day before our meeting.
Standard fix: up to 12 weeks.
Claude + the state's actual rules → a same-day letter that preserved a 60-day window.
AI collapses research-to-action.
Judgment stays human.
#AIforSMBs#PracticalAI #SmallBusinessOperations
Most owners never argue with their forecast.
This one did.
Conservative model said −30%. His actuals said otherwise. We landed on −11%.
Year-end moved from ~$355K to $450K.
If your forecast never loses an argument to your actuals, it is not a forecast. It is a decoration.
#FractionalCFO #FinancialClarity #SMBFinance
The cheapest emergency money my restaurant client could get last week was a credit card at 28%.
The POS one-click advance? About 55% a year.
Convenience is the most expensive feature in small business finance.
Rank every cash source by true annualized cost — before you need it.
#SMBFinance #CashFlow #FractionalCFO
An AI agent found 10 qualified candidates for a hard-to-fill property manager role over one weekend.
It still couldn't make the hire.
Here's what the AI actually did: wrote the job description, sourced candidates who weren't actively looking, built a one-page posting, and drafted the outreach.
Here's what it took humans to do: notice that one word in the job title was attracting the wrong level of candidate. Know which names on the shortlist were worth a call because of the reputation the model can't see. Decide to run the free listings for a weekend before paying for premium job boards.
That's the split I keep seeing across every engagement. AI compresses the work from days to hours. Judgment still decides whether the output is any good.
Owners ask me constantly whether AI will replace their team. Wrong question. The right one: which parts of your operation are volume, and which parts are judgment? Automate the first. Protect the second.
#AIforSMB #FractionalCFO
Buyers don't pay for potential. They pay for proof.
I spent most of June cleaning up a business's books before their tax return. Here's what was hiding in there:
$20,444 sitting in bad debt that was actually a payable. $67,000 of owner loans coded as accounts payable. $210,000 of friendly loans that belonged in equity. Payments on a related party's bank loan are recorded as debt reduction.
None of it changed the profit picture much. Every bit of it would have spooked a buyer.
Here's what owners miss: due diligence is not really an audit of your business. It's an audit of your credibility. When a buyer's accountant finds three misclassifications in the first hour, they stop trusting every number after that. Then the price drops, or the deal dies.
If a sale is anywhere in your five-year plan, the books get cleaned now, not the quarter you list. Clean financials are the cheapest value-add in the entire exit process.
#ExitPlanning #BusinessValuation #SMBFinance
My career was built on:
Financial analysis.
Operations.
Strategy.
Process improvement.
Those skills still matter.
But the game has changed.
Today, leaders need to know:
• How to think with AI
• How to delegate to AI
• How to build AI into workflows
• How to create leverage instead of more work
The professionals who thrive won’t be the ones fighting the technology.
They’ll be the ones amplifying their expertise with it.
The question isn’t whether AI changes your job.
It’s whether you’re willing to change with it.
#ChangeLeadership #Strategy #AI
Most people ask AI for answers.
Last week, I asked mine to tell me everything I was doing wrong.
Not:
❌ “Write me an email.”
❌ “Summarize this call.”
I run my advisory firm on an AI operating system, so I asked it to analyze how I actually use it.
Where was it falling short?
How could I use it better?
Then I sat back and read an honest performance review of my own system.
It flagged things I had stopped noticing:
⚠️ Context I was re-explaining every week.
⚠️ Tasks I was still doing manually that should have been automated months ago.
⚠️ Places where it was guessing because I had never given it the right information up front.
So I asked the obvious next question:
“Okay. How do I fix it?”
And it gave me step-by-step instructions to make the changes inside Cowork.
Not theory.
The actual setup.
Here’s the shift most owners miss:
AI isn’t valuable because of the answers it gives you.
It’s valuable because of the questions you’re willing to ask about your own business.
Most people use AI like a vending machine.
Put in a prompt.
Get out a result.
The owners pulling ahead use it like an advisor that never gets tired of hearing:
“How could this be better?”
Your AI already sees patterns in how you work.
You just have to be willing to ask it to tell you the truth.
👇 So here’s my question for you:
What’s one thing you’ve never thought to ask your AI about your own business?
#AIForBusiness #SmallBusiness #BusinessStrategy #ArtificialIntelligence #Entrepreneur #BusinessOwner #AIAutomation
If a buyer opened your books tomorrow, what would they find?
Clean numbers that tie out, or three versions of the truth and a pile of "I'll explain that one" expenses?
Buyers price risk one of two ways: a lower offer, or a walk. 👇
Comment "data room" and I'll send the free checklist.
#ExitPlanning #BusinessValue #MergersAndAcquisitions