Darin Pierson

@smblawgroup Spot on. Nothing hurts more than “oh yeah and you also owe me $500k in working capital” 3 months into LOI. 😆

Most failed small business deals die because the hard conversations got pushed there. Here's the pattern_ A buyer spots a material issue early, something like working capital, which is really just an indirect fight over purchase price. But they don't want to look too aggressive or too technical in front of a non-technical seller, so they kick the can down the road and figure they'll deal with it later. Later is the worst time to deal with it, mow it's a live negotiation with a signed LOI and momentum on the line. Surface the big disagreements early, even pre-LOI, and the back half of the deal turns into diligence and paperwork instead of a fight. @Sam_Rosati and @KHendersonCo get into it on this week's Main Street Deals. Listen on YouTube: youtu.be/PSvpbhIUEXQ?si… Spotify: open.spotify.com/episode/55Frcd… Apple Podcasts: podcasts.apple.com/us/podcast/how…

@CPATaxTeam Now that’s a team. No chance they are being replaced with AI!

I told my team I wanted them all rowing in the same direction. Amazing results!

@jakedemi posted this to LinkedIn. Great graphic on how complex your income side of accounting is

@Josh_streimer @CPATaxTeam Fair. I just think AI can do more with clean data vs trying to clean up data.

@CPATaxTeam @darinpierson Oof I’m gonna say wrong, on this hot take. The average small business owner doesn’t know the right question to ask, let alone have the desire to learn or do the leg work consistently. AI is a done for you tool when you understand how to use and automate it.

Hot Take: For small business I think AI is a better CFO than accountant right now.

@KurtisHanni Garbage in garbage out. Yes AI can ask what it needs to do cleanup, but that exercise is way harder than “build me a dashboard w/insights” from clean data.

@darinpierson I think this is reasonable, in that it can give you they options… but you still have to feed it the right info. Most feed it junk and get junk back, then make that decision with confidence.

@CPATaxTeam True! I just think AI isn't great at getting the data clean and accurate. Once you have a set of clean accurate financials, then the CFO stuff AI can do...pulling out insights, etc.

@darinpierson Probably true. Most accountants are horrible CFOs. They can knock out financials to perfection but lack the ability to strategize and guide the client.

@TrentBizBroker Make sure to not pay NIIT on the cap gain from an active business. Seen that too many times - and it can be a material number

Selling your business? Plan tax strategy early—before and after the LOI—to avoid surprises at closing 👇 Full discussion: youtu.be/SSQXqXbZUjc Free course: skool.com/business-acqui… #BusinessSale #TaxStrategy

@EndresenHeather So so tricky. I've personally seen very competent buyers get burned by this post-close.

The trickiest part about making offers on businesses? Working capital. It's part of the price, but you'll be relatively blind to any specifics at the time the LOI is negotiated. A buyer doesn't yet have enough (or any) info on the cash conversion cycle in the early stages of a deal. They simply don't know how much permanent working capital they'll need. Unless buyer can see balance sheets, agings, WIP reports and inventory info up front, the best practice is to keep the LOI vague and ask for a "normalized level of working capital". Avoid being overly specific about working capital until after you can do financial diligence.

@joshthacker DM'd you!

@darinpierson Oh we should trade notes then!

I had 2 acquisitions fall apart while I was searching for a business to buy. Wrong deals. The bottleneck was my own process: 14 browser tabs, a spreadsheet that quietly went stale, a sales CRM doing a job it was never built for. So I built Searcher OS, the operating system I wish I'd had: searcheros.ai (Credit to @sbabmarks who steered me to ~$1.25M SDE back in 2023. Good advice ages well.)

@joshthacker haha! both actually. Not sure what is harder - currently in startup mode

@darinpierson Losing two deals or grinding in a startup lol?

@AlanPetersonSBA I feel like the market has been tough for years....

For searchers who keep hearing “the market is tough right now”: It is. The ones who are getting it done have a tight process, a real lender relationship, and they’re looking at volume instead of perfection. Tough market usually just means you have to be better at the basics than the average person scrolling and hoping.

@SBA_Ray It did seem like every bank was starting a new SBA division in 2021-2023. Not sure if that fits in here

1/ I've got a different take on this chart. Yes, from 1996 to 2026 SBA lending is less concentrated at the top. But there's much more to the story. 🧵

@SMB_Attorney Yeah - no need to “prove your worth” as an intermediary/advisor by stirring the pot. Should be making it easier!

The best transactions are just one good person selling to another good person who want to get a fair deal done without intermediaries who fuck it up.

@CPATaxTeam @RichardCrainCPA This has been a fascinating Twitter debate this past week :)

@RichardCrainCPA why is everyone so obsessed about OOO responses? If I'm out of the country, I'm turning mine on. It's a courtesy to the sender to know that I won't be responding any time soon and my team will reach out to them quickly.

This guy has 400k+ followers. How? Why? If you follow him, defend your intelligence.

@CoFoundersNik Haha lesson learned Nik

Told my kids I’d pay them 5 cents for every branch they gathered They’ve gathered over 2,500 branches in about an hour ($250) Now I’m struggling to decide which lesson to teach them: A) A deal is a deal Or B) Life isn’t fair What do you think?

@RDriscollCPA Submitted!

If you're serious about joining me, complete this form: cognitoforms.com/TheCollaborati…

@LoganGrafTax Try expiring every day!! 😭

Love it when my local credit union's bank feed expires every month. I'm too lazy to switch banks 😭 (I have personal accounts connected to budgeting app)

@SMB_Attorney It totally depends on if they are buying stock in a C corporation or different type of tax entity. If you are selling a partnership or S Corp, the difference between a stock and an asset deal are pretty minimal as a seller - assuming most of the value is blue sky.

What should the net price differential be for structuring a transaction as an equity purchase vs asset purchase? Many experienced acquirers require a discounted purchase price if the seller or business requires an equity structure. What's your take?