Three years ago my business partner and I bought a landscaping company in Austin doing multi-seven-figure revenue with high six figures of SDE, and grew it over 20% in our first year. Six months after closing, we bought a second outdoor living business up in North Dallas, a little bigger than the first. Both are now shut down, and I'm preparing to file personal bankruptcy. I told the whole story on Acquiring Minds with Will Smith last week (episode 476, "How 1 SBA Loan Brought Down 2 Businesses"). I found my business partner through a post on Searchfunder, so it makes sense that I share this here too, especially for anyone looking at landscaping, outdoor living, or anything construction adjacent. The short version of what happened: shortly after closing Dallas, a large commission liability surfaced that we hadn't accounted for in the deal. The seller and we read that obligation very differently (and he disagreed with the validity of it), the relationship broke down, and the disagreement went into a legal process that ate well into six figures in fees without ever reaching a resolution. Dallas revenue fell sharply in the months that followed, several key employees left (after starting a competing business), and by the time we understood the full picture the business wasn't viable anymore. It went into bankruptcy. The two companies were cross-collateralized, with Austin guaranteeing the Dallas loan, so our Austin business was suddenly facing the prospect of carrying two SBA loans instead of one. The math didn't work, and rather than run a good business into the ground trying, we wound Austin down. Here's what I'd tell my past self. Some of it will sound obvious. I'm adamant that it doesn't hurt to hear these things more than once. 1. Talk to key employees before you close Our Dallas seller preferred we not talk to employees before close, and I understand why. It's a real risk for a seller. If employees find out the business is for sale and leave, and then the deal falls through, he's left holding a weaker company. But not talking to them is a huge risk on the buyer's side too. One conversation with the top revenue producer during diligence would have surfaced the commission question before we wired a dollar. The transaction is a risk to both parties, and both should share that risk to the extent possible. Push for the conversations, offer to structure them in a way the seller can live with, and if you truly can't get them, be honest with yourself about what you're accepting. Whatever you can't verify before closing, you own after closing. 2. A surprise liability reprices the whole deal A six figure hit to earnings sounds bad on its own. Run it through the multiple you paid and it gets worse, because now you've overpaid by several times that amount, and that's before a dollar of legal fees. Our escrow would have covered a small fraction of the exposure, but we didn't even get that as there was a legal battle. Do that multiplication early in diligence and you'll understand what's actually at stake in every question you ask. 3. In construction deals, WIP is where the problems can hide The dispute traced back to work in progress, which is the messiest part of any construction acquisition. The purchase terms let the seller keep a small percentage of WIP, and each side understood that differently. We believed it covered certain obligations (i.e., commissions). The other side read it another way. One ambiguous line item cascaded into everything that followed. If you're buying anything construction adjacent, nail the WIP schedule down job by job: who owns it, who collects, who pays what, in writing, with names, amounts, and uses attached. 4. Being right on paper is not a strategy We believed we had strong claims and solid contractual protections. It didn't matter the way we expected it to. Mediation, then arbitration, then the run-up to discovery consumed time and money the business needed to survive, and none of it ever came back. Legal remedies are slow and expensive, and they only pay off if you can afford to see them through. That's why the person you're buying from deserves as much diligence as the P&L. 5. Don't chain your businesses together Austin guaranteed the Dallas loan and the businesses were cross-collateralized. When Dallas failed, its debt service was set to land on a business that was growing and improving its margins, and no amount of growth was going to cover both loans. The structure we chose meant one struggling acquisition took a healthy one down with it. If you're doing a mini roll up, keep the entities as separate as your lenders will allow, at least until everything is truly in steady state. I couldn't tell you what efficiency the cross-collateralization bought us, but it wasn't worth this. 6. There was no reason to rush deal two We bought Dallas six months into owning Austin because we thought opportunities like it were rare. They aren't. Once you own one business, brokers return your calls and deal flow starts finding you. We were still operating with a searcher's scarcity mindset after we had already become owners. Another year of seasoning in Austin would have changed everything. 7. Change management is the actual work The Austin seller ran his business out of manila folders. He had custom stickers printed for them, with checkboxes for whether the plants were ordered and the permit was pulled. I used to joke that in 20 years he probably killed more trees than he planted. The thing is, the process was good. It was just analog. In Dallas we came in with a new CRM and new tech, we relaxed the 7am stand-up meetings, and when my partner had to step back for family reasons, we hired a new leader without involving the team in the decision. Each move was defensible on its own. Together, and fast, they told a long tenured team that everything they knew was changing, delivered by owners they'd barely met, one of them remote. I also learned that digitizing a process that already works returns far less than actually restructuring how the work flows. And neither matters if you lose the people first. 8. Understand your personal downside before you sign the PG I researched this before I bought anything, and it's a big part of why I can write this calmly. In Texas, homestead protection means the bank can't touch my primary residence. Retirement accounts are protected. You keep one vehicle per licensed driver in the household. There's also an exemption for personal possessions, and I remember walking through my house trying to add up what I owned and realizing the fridge was probably the most valuable thing in it. TVs are three hundred bucks now. What I'm actually paying is about seven years of damaged credit. These protections make my life easier, but in no way good. Fact check the details with your own attorney, because exemptions vary a lot by state. Most searchers sign a personal guarantee without ever mapping what enforcement would actually look like where they live. Do that math before you sign, not after. 9. Holding grudges is useless For a while I replayed what everyone else did or didn't do, and there was even a stretch where I wondered if I was the common denominator, if the problem was me. Neither of those was useful. What actually helped was treating all of it as things I did: deals I signed, structures I agreed to, conversations I skipped. Those I can learn from, and learning from them is what gave me a path forward instead of a list of people to be angry at. I don't regret buying these businesses and I don't wish I could go back. I just think my next pursuit will be better because of this one. The offer: I don't want this to read as a warning against ETA, and not every decision we made was a mistake. Bidding out vendors we'd bought from for a decade found real savings. Replacing the old skid steers we were constantly repairing cost less than the repairs did. Spending money to save money sounds obvious and never feels obvious in the moment. So here's my offer. If you're searching in landscaping, outdoor living, or home services, or you're under LOI and want a second set of eyes, I'm opening my calendar. No fee. I can walk you through the diligence questions I wish I'd asked, the WIP mess, and the traps in the first 90 days. I paid an expensive tuition for this education and I'd rather someone get it for free. Full disclosure: I'm also building a software product for landscaping operators. It grew out of the pain points I kept hitting while actually running the business, and started as a tool I built for ourselves, with AI and no developer background, that replaced four separate SaaS subscriptions and cut mid five figures a year in spend. It's early and I'm not selling anything yet (and have since moved on from vibe coding to real development). I'm happy to talk about this side too: why I strongly believe there's no good tool out there for this vertical, why nothing on the market is making the right use of AI, and why AI won't solve everything for you either. If you operate in this space, I'd love to show it to you and get your feedback. DM me or leave a comment if you'd like to chat! redacted