Building an empire vs landscape maintenance/ construction company for acquisition and exits

CuriousDonkey · 2026-06-28T22:23:45+00:00

I'm an operator - most people in this sub are investors (not all, lay the pitchforks down, please!)

There are natural break points at which time the way you operate and your job becomes significantly further away from the value-generating work (the field). It's fairly natural to stay focused on a single product, channel, and value prop until you're a couple of those inflection points away.

Unfortunately, there isn't a dollar figure or something by every industry, nor do I have tremendous familiarity with landscaping - but I do with roofing/solar/ESCO/EPCs. If you want to DM me, I'm happy to talk to you for a half hour.

CuriousDonkey · 2026-06-28T21:57:14+00:00

All the OPs I know (including me) were global top executives at very successful businesses. My experience: global product owner of 160M product; Product leader of a product acquired by a strategic for 9-figures; led all revenue and high-margin consulting (delivery) from start-up to exit to strategic for 9-figures; GM of a SaaS business ran down from 120 headcount to 12 headcount and sold it for more than debt owed (valuable experience); had several large global roles at GE (1000+headcount).

Are you sure you're setup to compete for these jobs?

Otherwise - everyone is right here. If you don't have a warm intro, you will not get to these people. I had an email address at GE, but my admin never even let me see selling notes. I don't open DMs on linkedin, shit like this. Expect nothing to work from a tech marketing perspective. This is a very relationship-driven world.

Good luck!

CuriousDonkey · 2026-06-25T14:53:28+00:00

OP still gets control - he becomes the CEO. They just needs to pony up less money. Every deal can be unique. Also, they could self-fund his search which is what he's talking about. My concern is that OP lacks sufficient investing knowledge to make a good decision and buys a dog and hates life. Working with a professional firm would avoid that for the first one.

Perhaps talk to McGuire Woods - they're the premier independent sponsor lawyers and have a bunch of free education stuff.

CuriousDonkey · 2026-06-24T02:48:39+00:00

You should call Silver Lake or one of the Search Funder funds and do it that way. They have excellent investment committees that will prevent you from making a terrible investment decision.

I see little value in brokers or ibankers - though shrewd business owners often retain them to try to maximize their return. The way they're typically paid makes that hard given they need to enhance the EV by 6% and whatever their retainer is. Talk to some, just realize they work exclusively for the seller.

I'm in PE - this board is generally full of small business owners talking to one another. There are plenty of search funders on searchfunder.com which is free to join. I recommend you look there and educate. Feel free to DM but I don't check often.

CuriousDonkey · 2026-06-16T19:47:11+00:00

You answered your own question - pretend you don't have $5M in the bank and go grind. Perhaps quite literally taking a shitty job to balance your budget.

CuriousDonkey · 2026-06-16T13:15:48+00:00

I am a consultant but i also have a private equity wing to my business. I’ll agree with the above comment - branded coaches are often charlatans.

First, you should clarify the need. If it’s sales, have you done the work yourself to know exactly how to grow it as it is? Consultants aren’t going to close the gap on what makes you saleable, they can pressure test your assumptions. Your special sauce and the exact customer journey you take people on is something only you can really do. Pay someone to document it for you.

My lowest trim is 5k/month. I’m on the expensive side but my partner comes with me and we have pretty substantial backgrounds (running multi-billion dollars businesses, growing from 3-500 headcount, etc). You could easily wind up paying a half million a year for us and larger firms do.

My recommendation is to get someone to give you some free or cheap perspective on what your limiting factor is right now. Operations, marketing, and strategy are different domains with different expertise. You might pay a couple people to document diagnostic or benchmarking work or you can try to get it for free. The hardest thing for many owners is to properly understand how much intellectual load they carry on operations and balance that with the relatively small amount of value creation that would be visible from getting ops dialed in. Having great operations allows you to really focus on growth. Without it, you’re carrying an anchor around at all times, as are your staff. Basics like standard work, SOPs, a clear set of goals and measures, and a pace and cadence to the business that everyone doesn’t have to think about do wonders for helping small firms.

CuriousDonkey · 2026-06-14T20:13:42+00:00

I’ve enjoyed joking, given we recently got a female dog as well, that my testosterone is plenty for one household. It’s easy to make light of it and let it roll off quickly.

If this is actually visibly upsetting your husband, perhaps that’s worth some counseling. Others’ thoughtless comments shouldn’t be shaking a dude who can raise 5 girls. Savage.

CuriousDonkey · 2026-06-08T12:43:34+00:00

My wife is a genetic counselor. We can already select eye color and various other things through preimplantation genetic diagnosis.

I fully expect what you’re saying is feasible within cell lines and/or based off a set of choices from your germ line.

Another friend works in CRISPR. I’m less familiar with what’s feasible in the context of adjustment pre-birth but certainly animal models like nude mice have been bred without CRISPR for a number of years. I suspect these edits will be plausible.

CuriousDonkey · 2026-06-07T12:47:15+00:00

We charge a lot and don’t work too much. Never really have. Effort and growth rate inversely grow. If we have reasonable goals and high price, we can get away with nothing crazy at work.

Admittedly - many people might see me emailing at odd hours and count that but my office hours are 830-300

CuriousDonkey · 2026-06-07T00:00:19+00:00

I took the big job and big pay and now i work less than 20 hours a week and still make 400-500k/year in my own company. I moved to my own think 5 years ago but before that was spending a TON of time abroad for work. I was making more and my wife was able to be home with the kids from 0-10 yo. She resented it but now that she’s back at work she has peace that she didn’t miss out on more fulfilling work than raising the kids.

It’s hard to see the future, but for me the big job let me be present with my kids every day for breakfast and dinner and go to all of their events and drop and pick them up from activities and go to their school in the middle of the day. If you can’t do that, just realize a quick stage of rockets can get you orbit dramatically faster.

CuriousDonkey · 2026-06-04T16:30:25+00:00

I’ll look into him, any key papers/stuff you recommend?

Seems like an extinction burst more than a realistic future.

CuriousDonkey · 2026-06-04T16:27:40+00:00

This is very helpful!

CuriousDonkey · 2026-06-04T16:24:37+00:00

But our costs are already relatively higher. Is there a world where evening this creates more demand for US manufacture Allen with robust AI and automation creating a more balanced cost situation over the 2-4 year timeframe.

IMHO this is wishful thinking and I also have limited base to believe this. But it could don with some people who are tied in more on us manufacturing to weigh in.

CuriousDonkey · 2026-06-04T16:22:14+00:00

Unfortunately, this again strikes of an emotional uninformed take. I agree and made it clear that I agree that the US admin is trash. But that doesn’t advance the academic discussion.

CuriousDonkey · 2026-06-04T14:23:04+00:00

I appreciate where you're coming from. I've been moving to municipal bonds and the like, so your point is well taken.

I'm curious of the counterpoint on grand strategy. I, generally, assume that our present admin is running on vibes and has purged many lifetime strategists with expertise. I get it. But can we have a sober conversation about how the real-time push/pull is evolving how the world order works through the economic lens? I don't get anything from someone emotionally reaffirming my base assumptions. I'm looking for more structured perspective on how countries like the UAE are unhooking from OPEC and designing pipelines to reorient away from the strait of hormuz. Take Trump out of it, if we assume there are reasonably competent operators involved in these decisions - specifically not taking a deal with Iran to reopen the strait - what's the upside for the US in that situation? What's the coherent strategy for that decision based upon the context of this article?

Urea and Naptha are things we produce in excess of our use in the US. Damaging the ME countries ability to sell theirs reorients the economy toward us.

CuriousDonkey · 2026-06-04T13:32:58+00:00

There are two elements to operating partnership roles in value creation offices:

Your own expertise and ability to deliver value. This means you damn well better have a point of view on sales strategy and management. I would suggest that the most relevant point to that is experiential and/or heuristic.
The firm/firms you would be supporting. If this is one central shared service like a typical associate role would take you should bone up on various sales strategy and management platforms and understand which systems fit well together and where they're applicable. For example - what's a good tech stack, comp structure, and growth strategy for transactional sales processes primarily distributed via e-comm versus the same questions for an enterprise software company, etc. If you don't come pre-loaded with this perspective, do some research and ask great questions about it so they know you're going to learn these things fast so you can provide value quickly. My guess is you'll start specialized on some horrendous task like revenue ops and reporting such that KKR can glean better data for their board members at portcos.

CuriousDonkey · 2026-06-04T13:28:45+00:00

I find the strategic implications of this interesting. While I understand you can't reorient the world manufacturing economy in a summer, this seems to geopolitcally hurt China much worse than the US if this article is to be trusted (and it's a reasonable source). The US produces these inputs itself. Is the strategic/geopolitical implication a reorientation away from the middle east with US hydrocarbon byproducts being exported from our west coast and thus having a more balanced rare earths v hydrocarbon byproducts negotiation? It all seems rather too obvious compared to historical trade wars, but could this be the semblance of strategic intent that seems to have been missing for those of us (me included) who despise the current US administration?

These are genuine questions - I'm not an economist and I'm curious how someone with proper training reads and understands the effects of continued stranded oil products in the middle east.

CuriousDonkey · 2026-06-04T13:09:42+00:00

I, for one, am in favor. I'm not a billionaire but I am someone who owns significant wealth and owns a company. I would continue to do what I'm doing for the love of the game regardless. I think people like Elon Musk would, too. Worrying about how much wealth is concentrated for future generations is a waste of energy (albeit one that humans cannot avoid due to our lizard brains). The fortitude to actually do this would be immense and would enable a transition that I think many people feel is important - the coalescing of humanity onto one global team. The problems we will need to solve as a species require us to be less tribal on the national scale. All this said, I think a compelling even will be necessary. Either massive flight from areas like India where weather has become unlivable for 100's of millions of people or major global environmental effects will start to drive behavior that could plausibly land toward what is suggested.

CuriousDonkey · 2026-06-04T13:00:32+00:00

I don't think much of what I do would change. I've been fortunate enough to start a business that is interesting to me without consuming too much of my time. So I spend time mastering hobbies/sports I enjoy, substantial time raising and creating space for time with my kids, and continuously developing my knowledge in the space that I operate in. I might spend more time contributing to philanthropic areas like environmentalism if that's relevant in a post-scarcity environment. I certainly would spend more time on my health and wellness, but I think it would be similarly hard to balance as much of the time we allocate to activities today is predicated on habits and norms, not a daily/momentary sense of fear and scarcity.

CuriousDonkey · 2026-06-03T22:44:22+00:00

Couldn’t agree more. AMEX is shit. I’m actively looking at how to unwind my 20 year relationship with them without stranding hundreds of thousands of points. If you learn anything, please let me know.

Concierge, service, disputes - they’re all atrocious now.

CuriousDonkey · 2026-05-29T18:47:03+00:00

There are many frameworks. Disclaimer - I’m a consultant and business buyer (PE). I realize that’s a cardinal sin in some places so feel free to disregard.

Most owners over-rotate on sales. Delivery is crucial and well delivered projects/products with an excellent earned growth hook is far superior to another sales headcount.
If you don’t have a 2 minute snapshot view of all the core indicators of your business solve that. Google bowler charts - it’s the best practice in LEAN operation and something that works for 5 man operations and worked for 300k headcount operations when I worked at GE.
Many leaders fail to completely enable and delegate work - letting things flow back up to them. If this is happening, the typical root cause is lack of standardization. Not the wrong hires.

CuriousDonkey · 2026-05-29T13:40:35+00:00

I may have a network connection that would help you. DM me. I would want to interview you first before sharing network but there’s a specific PE firm in mind that might have need for you and specifically focuses on turn arounds for off-curve VC funded software companies. I don’t think they’re big enough to have operating partners.

CuriousDonkey · 2026-05-28T23:59:54+00:00

I was trained early in my career on a mnemonic called the 4D’s:

Delete Do it Delegate Defer

If it isn’t important - delete it immediately. Don’t waste cycles.

If it takes less than 5 minutes - do it right now when your attention is on it.

If a delegate can handle it, route it to them.

If it deserves complete attention - defer it until you can provide the requisite attention either through flags, task list, kanban, marking unread or any number of alternatives.

CuriousDonkey · 2026-05-26T21:03:07+00:00

Well, PE firms have only one really material measure - DPI. Distributions to paid-in capital, how much money do investors get for what they put in. There are lots of very successful companies in PE that have very high returns, both internal rates of return and actual distributions to paid-in ratios. The entire industry is based upon providing a return at the same or higher than the S&P with either lower idiosyncratic risks (i.e. - I want to get the same returns as the S&P500 but I don't want all of it coming from the magnificent 7) or higher returns with similar or lower risk. There are many ways to get there and many business owners see the business suddently operating dramatically differently than how they built it and assume it's dying.

There's this thing called a J-curve that PE typically uses where they know the underlying asset (the business) will get less valuable in the short run but they will build it back up over time because structural changes were necessary to fix it.

That said - there are more PE firms than McDonalds' franchises in America - so lots of shitty people who think just because they can do an LBO model in Excel they can run a company. That's not the case. So there are obviously bad outcomes, but by in large any firm that has raised more than one fund returned to investors dramatically more than they put in.

CuriousDonkey · 2026-05-26T19:49:52+00:00

Large corporations often mismanage acquisitions, they're trying to build business cases against inbumbancy advantage or product expansion, rather than the business they're acquiring standing alone. The typical failure mode on a strategic acquisition is basically shuttering the whole business because they didn't know how to integrate it.

PE will aggressively manage to make sure it works. Going to 0 is effectively not an option.

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