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The question that exposes every bad deal before you sign
Most buyers spend 90 days on financials. They analyze the P&L. They run the DSCR. They build a model. Then they close and find out the business was the seller. Not the brand. Not the systems. The person. One question tells you everything before you ever open a spreadsheet. "What does your day look like right now?" If they describe a business, you can buy it. If they describe themselves doing 12 things nobody else does, you are buying a job with a price tag on it. I have walked away from four deals this question alone saved me from. Comment "OPERATOR" and I will send you the full seller evaluation framework I use before I ever look at a number.
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The seller call nobody prepares you for.
You find the deal. Numbers work. Seller seems motivated. Then you get on the phone and go blank. Not because you are not smart. Because everyone teaches you how to read a P&L. Nobody teaches you how to read a person. I want to know three things before I ever open a spreadsheet. Why they are selling. What they are walking toward. Whether they can actually let go. The answer to those three questions has saved me from more bad deals than any due diligence checklist ever has. Tomorrow 4pm PST I am going live to walk through exactly how I run that conversation. Real framework. Real examples. Comment "SELLER" and I will send you the link.
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The business was fine. The seller was the problem.
Most buyers do due diligence on the financials. Almost nobody does due diligence on the person handing them the keys. I have watched deals fall apart after close not because the business was broken but because the seller was. Emotionally attached. Quietly resentful. Unwilling to actually leave. The previous owner who keeps showing up. The one who still texts the employees. The one who told his best customer the new owner "doesn't really get it yet." That is not a business problem. That is a people problem. And no LOI protects you from it. Before I go deep on any deal now I want to know three things about the seller. Why are they selling. What they are walking toward. And whether they can actually let go. The answer to those three questions tells me more than two years of bank statements. What red flags have you seen in a seller that made you walk away?
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The 90 days nobody teaches you
$8.29 billion in SBA acquisition loans were funded last year. Nearly 7,000 deals closed. Most of those buyers have never managed someone else's payroll, inherited someone else's vendors, or sat across from a 15-year employee quietly deciding whether to stay or go. The deal gets all the attention. The 90 days after it never does. Here is what those first 90 days actually cost people: A buyer fired the office manager on week two because she "wasn't a culture fit." She was the only person who knew the billing system. Collections dropped 40% in 30 days. A buyer changed the software platform in month one to prove he was modernizing. Three of his best technicians quit. They had been there since the previous owner opened the doors. A buyer renegotiated supplier terms before he understood which vendor relationships were keeping key customers loyal. He saved $800 a month and lost a $200,000 account. None of these people were bad operators. They were moving at acquirer speed instead of operator speed. Your only job in the first 90 days is to understand the machine before you touch it. Learn every name. Understand every relationship. Find out what the previous owner never wrote down. That knowledge is the actual asset you bought. The equipment is just furniture. I kept a list of 10 things I refused to change for 60 days after my first close. That discipline protected the business while I figured out what I actually owned. What would you put on your list?
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Nobody prepares you for Day 1
The wire clears. You own the business. Then you walk in and realize the seller is gone, the employees are staring at you, and you have no idea where the passwords are. I've been there. The deal was done. The celebration lasted about 45 minutes. Then I was standing in a business I technically owned but didn't yet understand. Here's what nobody tells you before close: the first 90 days will test your identity more than your spreadsheet skills. Employees are sizing you up. Customers don't know you. Vendors are waiting to see if you're real. Your job in that window is not to optimize. It is to listen. Learn every name. Touch every part of the operation before you change anything. The fastest way to destroy the value you just paid for is to walk in on day one acting like a new owner instead of a student. I had a handwritten list of 10 things I would not touch for 60 days. That list saved the business. What's the first thing you'd want to know before walking in on day one?
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