Would We Actually Buy This Business? Our Honest Take on 6 Industries
First, Alex and Ian share how to get paid when customers sit on your invoices. Then Will, Alex, and Ian say whether they'd put money into six industries they see from the inside, and what would need to be true.
The Short Answer
Of the six industries, power washing got the clearest yes, as long as you add a second service to cover the slow season. A med spa that charges well, sells well, and keeps clients was also a yes. Cash-pay physical therapy, niche SEO and AI search agencies, and higher-end home building were yes only under specific conditions. A bookkeeping and tax firm on its own was the clearest no, because AI is pushing bookkeeping prices down and tax work is seasonal. The episode opens with collections: ask for money up front, make paying easy, call people, reward early payment, and escalate when invoices go 60 days late.
Why Unpaid Invoices Turn Into a Cash Crisis
Alex has seen the same problem with a lot of owners lately. You won the bid, did the work, and paid your crew, your materials, and your overhead. Then the customer doesn't pay. He compares it to sprinting the length of the field and getting stopped at the two-yard line.
It snowballs from there. Because you're not getting paid, you start stretching your own vendors. Now you're the one frustrating people. You're acting like a bank, collecting from some people so you can pay others, and eventually you reach for a maxed-out line of credit or a merchant cash advance. Ian adds another trap: owners take on more jobs as fast as they can to cover the gap and stop watching the margin on what they bid.
Alex asks owners in this spot one question: if all the money in your 60-plus-day receivables bucket were in your account right now, how would you feel? Almost everyone says they'd be fine. In construction and the trades it can be seasonal, with spring work billed in mid to late summer, but higher interest rates have made it worse across the board.
How to Get Paid Faster
Alex thinks of it as a totem pole of people waiting to get paid. Your job is to not be at the bottom. Here's what the team recommends, roughly in order.
1. Get as much as you can up front
Prevention beats collection. Ask for a deposit, even 50% down, or payment at the time of service. Many owners assume they'll lose the job if they ask. Often they've never actually asked.
2. Make it easy to pay you
Send a pay link instead of mailing an invoice. If you bill the same amount every month, put it on auto-pay through ACH or a card on file. Most payment processors and accounting software can do it. When a customer has to decide to pay every month, some of them won't.
3. Automate reminders, then pick up the phone
Email and text sequences help, but one email in an inbox of thousands is easy to ignore. Ian's rule is to assume ignorance, not malice. Maybe their card was declined and they don't know. A friendly call often gets an apology and a payment the same day.
4. Get face to face
It's easy to say "we're working on it" to an email. It's much harder to say "I can't pay you" to someone sitting across from you. If a big customer owes you money and has never met you, fix that.
5. Reward early payment
Alex once had a supplier that offered 2% off for paying by the 9th of the month. That bill was his biggest, and it was always the first one he paid. A 2% to 5% discount can be far cheaper than carrying the gap on a line of credit at something like 12%.
6. Escalate when you need to
If someone is 30 to 60 days late, a polite email from the office isn't enough. Move collections to someone with a salesperson's demeanor, or do it yourself. Go pick up the check in person, or better, get them on ACH. Some contractors pre-lien larger projects, and there are services that send an intent-to-send-to-collections notice. Talk to your attorney about what applies in your state.
One client was owed about $200,000 on bigger contracts right before Christmas, and nobody was really collecting. They put their best salesperson on the phones with a commission on anything collected. All of it came in within a week.
For more ways to free up cash, see our free 9 Cash Flow Levers workshop.
Why Owners Avoid Asking for Money
Most owners already know they should call. Ian says the real block is usually internal. Asking for money feels icky, especially for owners who see themselves as caregivers and don't want anyone upset with them. And the longer an invoice sits, the more awkward it feels, like an email you didn't answer for three weeks.
He flips it this way: when you don't ask, you're quietly deciding the other person can't handle it. Treat them as capable. If they say they can't pay $40,000 today, ask what they can handle today. It's the same skill as sales: you're just working out an agreement to move forward. And deliver bad news early. If insurance denied past visits, tell the patient now, not ten visits later.
"Always assume ignorance, not malice."
Ian Hogan, co-owner of CEO Finance AcademyAlex also suggests borrowing from other industries. A pool cleaning and maintenance owner collected a card before each scheduled visit, then billed after the work. Nobody owed him money, which was nearly unheard of in his industry. You can tell customers "this is how we do it," explain why, and most will go along.
Would We Buy It? 6 Industries Rated
Next, the hosts played a game. Imagine you could buy into the business and step in as an operator, even without years of experience in that industry. Would you buy into this kind of business? These are generalities from what we've seen inside client financials, not expert verdicts. Great and terrible versions of every industry exist.
| Industry | Our take | What would need to be true |
|---|---|---|
| Bookkeeping and tax firm | Lean no | AI will likely push bookkeeping prices down, and tax prep crams the work into a few months. Alex would only consider it paired with higher-value advisory work. Ian would look hard at the team, client retention, and relationships. |
| Med spa | Yes | Charges well, sells well, keeps clients, and isn't dependent on the owner doing every treatment. Ian sees most of the ones we work with carrying a wait list. |
| Power washing | Hard yes | Ideally two crews and trucks, plus a second service like holiday lights or snow plowing to cover winter. Cheap to start. |
| SEO and AI search agency | Yes, with a niche | Depends on who it serves. Serving businesses AI won't easily replace, like medical or professional services, was the preference. Will notes ad platforms are already automating a lot of the work. |
| Physical, occupational, or speech therapy | Only if cash pay | Insurance reimbursements keep dropping. Alex wants PT visits around $175 or more, recurring services like classes or fitness, and enough therapists that the owner doesn't treat. State rules on scope matter too. |
| Residential home building | Split | Alex and Ian would consider a higher-end builder with capital for spec homes, WIP reporting, a strong admin, and good subs. Ian worries about waiting six to twelve months to get paid. Will leans no because of the overhead. |
Opinions from the episode, not investment advice. Do your own due diligence with your CPA and attorney before buying any business.
What the Good Ones Have in Common
Across the six, the same few things kept deciding the answer.
It doesn't depend on the owner
In smaller med spas and therapy clinics, the owner is often the best practitioner. Ian looks for at least a couple of people who can deliver 80% of what the owner can.
It can charge well
The med spas that do well price high and focus on the client experience. Cash-pay therapy only works at a rate that lets you pay therapists more than a hospital would.
Revenue is steady and sticky
Retention, recurring services, and a plan for the slow season showed up in almost every yes. So did getting paid on a predictable schedule.
The human part is hard to automate
Work that's pure "one plus one equals two" is the easiest for AI to cheapen. Relationships and trust are what both Alex and Ian expect to hold their value.
If you're looking at a business to buy, or getting yours ready for a buyer, see what makes a business sellable.
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Book a Free Intro Call Watch the free 9 Cash Flow Levers workshopFrequently Asked Questions
Start by assuming they forgot or didn't know, and reach out kindly by phone, not just email. Make paying easy with a pay link or auto-pay. If invoices pass 30 to 60 days, move collections to someone with a salesperson's demeanor or handle it yourself, and consider picking up the check in person. Ask your attorney about stronger options like liens.
It's worth running the math. On the show, Alex pointed out that a 2% to 5% early-pay discount can cost far less than covering cash gaps with a line of credit at around 12%. He always paid one supplier first because it offered 2% off for paying by the 9th of the month. Check that the discount fits inside your margins.
In this episode, the hosts favored businesses that can charge well, keep customers, earn steady or recurring revenue, and run without the owner doing all the work. Power washing and well-run med spas got the strongest yes. Treat that as a starting point and do your own due diligence with your CPA and attorney.
The hosts leaned no on a firm that only does bookkeeping and tax prep. They expect AI to push bookkeeping prices down, and tax prep packs most of the work into a few months a year. A firm that pairs bookkeeping with higher-value advisory work, has strong client retention, and serves businesses of a meaningful size was more appealing.
It can be. The hosts said yes to med spas that price well, focus on client experience, sell well, and keep clients coming back. Many they've seen have a wait list. The main risk is owner dependence, since the owner is often the best practitioner. Look for other providers who can deliver most of what the owner does.
The hosts would only consider mostly cash-pay clinics. Insurance reimbursements keep falling, which makes it hard to pay therapists competitively. Alex wants PT visits around $175 or more, some recurring services like classes, and enough therapists that the owner doesn't have to treat. State rules on scope of practice also matter.