Current: Springdale Industries. Previously exited a commercial service rollup.
Orlando, FL
Joined June 2012
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Don't be afraid to try what you're not qualified to do.
If I only did what I was qualified to do, I'd be pushing a broom somewhere.
-Sacca
Good post. Fully agree.
“We’re going to buy businesses and implement AI.”
Guys, with the exception of maybe a handful of people or firms, I’m not sure many people have a better front-row seat to the small and lower-middle-market acquisition ecosystem than we do.
We take 200+ calls every month from prospective buyers, searchers, independent sponsors, family offices and private equity funds.
And that doesn’t include the orders of magnitude more conversations we see through communities, group chats, conferences and the hundreds of transactions that move through our firm.
Based on our own deal volume and what we see in the market, we believe we’re among the most active law firms serving the lower-middle-market M&A ecosystem in the country.
And I can tell you:
“We’re going to buy businesses and implement AI” is EVERYONE’S thesis right now.
Greg’s piece is thought-provoking, and I think his broader point is right: everyone buying or operating a business should be thinking seriously about how AI can be layered into the company to improve productivity, reduce costs and expand margins.
That is absolutely where things are going.
And damn it, it’s a GOOD thesis.
I say “good,” not “great,” because there is a huge assumption buried inside it:
That you actually get to the part where you can focus on growth and AI implementation.
The acquisition lifecycle usually looks something like:
1. Acquire
2. Stabilize
3. Grow
4. Exit
AI implementation is largely part of Step 3... Growth.
But before you get to Step 3, you have to survive Step 2.
And Step 2 is where things get real.
> You inherit employees you didn’t hire.
> Customers you didn’t acquire.
> Vendors you didn’t negotiate with.
> Processes you didn’t design.
> Technology you didn’t choose.
> Financial statements you didn’t prepare.
> A culture you didn’t create.
And often years of institutional knowledge sitting inside the head of a seller who just got wired a life-changing amount of money and is mentally halfway to the beach.
Meanwhile, the debt payment is due every month.
A lot of acquirers get stuck somewhere between Stabilize and Grow for years.
> They fix people problems.
> They replace customers.
> They rebuild accounting.
> They improve working capital.
> They learn the industry.
They deal with equipment breaking, key employees quitting, sellers behaving strangely, unexpected capex and a thousand other things that never appeared in the CIM.
They put out near CONSTANT fires.
They service the debt.
They hold on for dear life.
They may still create seven figures of wealth...
But they never really reach the clean, optimized growth phase they imagined when they built the model.
That’s why I think assuming you can simply acquire a business and quickly increase EBITDA margins by the magnitude Greg is describing will be wishful thinking in most cases.
Not because he’s wrong about the opportunity.
He isn’t.
AI can absolutely improve margins.
It can reduce administrative labor, improve sales processes, accelerate quoting, enhance customer service, automate workflows and create enormous operating leverage.
Everyone should be thinking about how to use it.
But growth requires stability, management bandwidth, good systems, clean data and capital.
AI is a tool.
It is not a substitute for competent operations.
You still have to buy the right company.
At the right price.
With the right capital structure.
You still have to retain the right people.
Protect the customer base.
Understand working capital.
Manage cash.
Navigate the transition.
And actually operate the thing.
So if you’re considering acquiring a lower-middle-market business, do your homework, hire good advisors and go in with your eyes wide open.
Greg is right that AI creates a massive opportunity for business owners and acquirers.
But the hard part is still getting the business into a position where you can actually capture it.
This is hard as FUCK.
And AI didn’t make that part any easier.
I know an SMB broker that sent his seller a list of the top 3 bidders offers and “accidentally” CCd bidder no.3 (who the seller wanted)
You can replace accidentally with ‘on purpose’
/ no.3 did not win the final auction
Damn. Very sad.
I live in Orlando. I took the Brightline 1x and it was solely out of complete emergency necessity due to air travel issues from Miami. Now, I did enjoy it and thought it was pretty convenient.
Other than that one instance, I have never ever considered taking the Brightline to Miami. This is a general statement but, I have never heard of any Orlando people mention wanting to travel to Miami. Different group, different vibe.
On a weekly basis, people in Orlando bitch about the traffic from Orland to Tampa (and vice versa). I think the Brightline missed big by not going Orlando <> Tampa, and did Orlando <> Miami. If I had to guess, the political easiness and funding was a lot easier by having Orlando + Miami though.
My wife would divorce me if I told her to check our daily planner and delegate tasks to her.
CC the entire fam 🤝!
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Ready to keep everybody on the same page? Join the waitlist or upgrade your existing CC (US only, 18+): labs.google/cc
Only going to get worse, unfortunately.
2023+ has been filled with people hyping up the eta space and using SBA loans. Listening to people that ‘sell shovels’ and collect fees along the way.
I’ve spoken ad nauseam about this (90% leverage, PG’d, first acquisition).
1. Bank isn’t your partner, they are your lender. Who will take the keys.
2. Business, ESPECIALLY SMB, is brutally hard.
I miss when podcasters were normal folk that just so happen to be into niche topics/subjects and their setup was audio only.
Now your favorite podcaster is a celebrity, and it's more about them than the content.
Just finished Michael Ovitz book. Fun read. Great stories. Supremely talented. Complicated guy (aren’t we all).
Another great example of game selection matters.
On Outlook, the most annoying feature (which is saying a lot) is that even after you reply to an email, the reading pane only shows their email and not your reply. If you have a lot of emails, you can't quickly glance and see what the latest email is because it only shows the initial one - not the latest one.
/lifelong google guy, also use superhuman to get out of the outlook ecosystem...but had to get into outlook native today and tried using it. Awful.
