How do you bridge the gap between seller dreams and buyer reality in a lower middle market deal?

The unsung hero: the contingent promissory note.

A thread 🧵 2/ In SBA and LMM deals, the buyer and seller almost never agree on value upfront:
- Seller wants a premium for “potential.”
- Buyer wants protection against downside risk.
- Lender only wants to underwrite predictable cash flows.

Entrepreneurship is hard.

There’s no such thing as an “easy” business.

Anyone telling you otherwise is selling courses.

But some businesses are better than others.

This is a realist’s guide to what actually makes a good business in 2025

And a list of the very best…🧵 1/ First: the internet is full of furus hyping “boring businesses.”

Car washes. Residential cleaning. Vending machines.

Most are garbage: high churn, low margins, operational headaches.

Not businesses you buy to build wealth, they’re jobs in disguise.

Avoid this garage:

"Qualified Small Business Stock" or "QSBS"

The most powerful wealth building tool in business today!

What is it?

Lets find out... a THREAD: Let's start at the beginning.

QSBS means "Qualified Small Business Stock".

It is stock that is issued by a "qualified small business" (QSB).

How does a business qualify as a "qualified small business"?

The following is a super serious 7-step thread on succeeding in corporate America.

Do all of this and you’ll be GUARANTEED to make partner or the C-Suite: I’ve worked for some of the most prestigious law firms and well-known companies in the world…

Disney, Rocket Mortgage, Kirkland & Ellis

The following worked at all of these places…

Looking to buy a business like this one?

Here's a quick guide on where to find one:

(This answers the #1 question I get DM'd)

A thread: 1 - Establish Your Criteria

Start by setting a rough criteria. This will help.

Consider things like size, location, industry, and financials.

What are you good at and what would you enjoy doing?

Working Capital

Arguably the most important (and often overlooked) element when buying a business.

This is a must read and could save your behind!

A THREAD: 1 - What is Working Capital?

The textbook definition (yawn):

The difference b/t a company's current assets and current liabilities.

This difference comprises the financial resources needed to fund the day-to-day operations of a business.

$7 trillion of Baby Boomer businesses will be sold by 2030.

A quick and dirty guide to buying one: Before we dive in, some quick background:

The number of businesses bought and sold since 2018 hasn't materially increased.

And many of the businesses for sale will not and should not sell.

We are seeing a TON of opportunity nonetheless.

If you look hard enough, you will too!

Breaking: Absolutely enormous real estate news today that affects us all. This settlement could reduce realtor commissions by 30% and put massive downward pressure on home prices across the U.S. 🤯🚨

The back of the American residential realtor lobby was just broken.

Watch for digital players like Zillow and others to emerge as the big winners as many (most) realtors are forced out of the profession.

There are bad people in life and you won't recognize them until it's too late.

They don't care about you and are motivated only be greed.

I have these conversations too often.

Here's what I'm getting at:

Sellers intentionally violate non-competes all the time!

More... Here's the bottom line:

No funny business with non-competes and non-solicits.

None!

Terms:
1. FIVE-year duration minimum (yes, it's enforceable!)

2. No cap on damages. You need to be able to recover 100% of your loses... they can kill your business!

3...

$7 trillion of Baby Boomer businesses will be sold by 2030.

But where do I find one (like this one) to buy?

A thread: 1 - Establish Your Criteria

Start by setting a rough criteria. This will help.

Consider things like size, location, industry, and financials.

What are you good at and what would you enjoy doing?

If you’re a professional service provider and you’re not already offloading work to ChatGPT…

… you’re way behind the competition.

A thread 🧵

(As featured in Bloomberg) Here are a few ways that we use ChatGPT in our practice, and how to best capitalize on applications of the technology:

$7 trillion of Baby Boomer businesses will be sold by 2030.

You want to buy one like this?

Start your journey with these basics: $2.6 million in cash flow in beautiful SoCal for a $5.0 million purchase price?

Pretty incredible, right? Well maybe!

The following are the resources you should start with when beginning your search to buy a business...

Academia is becoming a total fraud.

The average tuition at some schools is $50 to $70k, with graduates earning half that amount? Horrible ROI.

Meanwhile, most professors have no actual experience and voice over text books written by other professors with actual no experience. This is the rec center at Texas Tech (this is not a joke)

Starting Saturday, @KHendersonCo and I are going to tell you everything we know about business buying:

• structuring your deal
• finding investors
• SBA lending
• the best service providers
• how to find a business

Completely Free!

But first, help us pick cover art 👇🏻 1

::Head Exploding::

• 81% buyout
• 19% seller rollover (no PG)
• Zero money down
• Option to call seller equity after 12 months at original multiple

Someone smart tell me why every deal shouldn’t be structured this way? Less risk for buyer.

Less risk for lender.

Easier entry point for buyer.

Phased-in 100% buyout.

What am I missing?

Working Capital

Arguably the most important (and often overlooked) element when buying a business.

This is a must read and could save your behind!

A THREAD: 1 - What is Working Capital?

The textbook definition (yawn):

The difference b/t a company's current assets and current liabilities.

This difference comprises the financial resources needed to fund the day-to-day operations of a business.

Lets run this back…

You have a $3 million 🏡 budget

You can live *anywhere* 🌎

(Forget about money; you’re set)

Where you moving?

Comment below 👇🏻 Bonus points for pictures, Zillow listings and/or an explanation.

A $100k investment can buy you between $30k and $83k in passive income as an investor???

Here’s how…

Introducing SBA 7(a) financing 🧵: Yesterday’s post on SMB investments proved very few people know how SBA financing works.

The comments were… funny.

Check it out again then come on back:

https://twitter.com/smb_attorney/status/1650983408858812417

PART THREE! 🚨

Viewed by over 35 million people! 👀

The following is the next installment of:

“Things ChatGPT can do right now that (maybe) you no longer need to pay lawyers for!”

Negotiating a Lease Agreement

[*Please see the disclaimers at the end*] This is the third installment in a series of potential legal use cases for ChatGPT.

Part One can be found below 👇🏻

https://twitter.com/smb_attorney/status/1648302869517312001

How to build wealth as a service provider

Here’s the blueprint: Step 1: Income 💼⌛

Establish a service business in a high-demand niche area and generate service-based cash flow by trading time for money.

Find a profitable niche where your skills are in high demand, and offer top-notch services to your clients.

This will help you secure… twitter.com/i/web/status/1…

The smartest students graduating from the best schools no longer want to go to Wall Street and kill themselves. They want to buy and operate boring, small businesses that print money. Wharton, Harvard and Stanford grads buying cabinet repair and cleaning cos in random U.S. towns. For everyone thinking, “I don’t remember this at Wharton in 1998.”

This book was published in 2017 and changed everything: