Steven Alessandro

The most expensive education in landscaping is trial and error — here is how to skip it

There is a process and a system for everything in this business
HOA management Commercial properties Pricing and estimating
All of it has a right way to do it

But most operators learn that by making expensive mistakes first

I know because I made them for years

Pricing alone — I cannot count how many jobs I priced incorrectly over the course of my career
You learn yeah
But you learn it by losing money
And that is a slow and painful way to build a business

When I developed the Devon Creek system I went back through every mistake I ever made and asked myself one question
If I started this business tomorrow what would the pitfalls be
What would I look for
What would I need to know on day one that took me decades to figure out

I built all of that into Devon Creek so that franchisees start where I finished
Not where I started

30 years of lessons
Follow along and get them for free

Commercial clients do not fire you because the grass was long — they fire you because the experience was wrong

This is the thing most landscaping operators do not understand when they make the move to commercial

Residential is about the lawn
Commercial is about the experience

When you are managing a hotel property or a commercial building the person you answer to — the property manager or the engineer — is not thinking about your mowing pattern
They are thinking about what their guests see when they pull into the property
They are thinking about first impressions
Line of sight
Focal points

You drive onto any commercial property and your eye goes somewhere immediately
Left right — straight to the things that stand out
Weeds sticking out of a bush
A cigarette butt on the walkway near the entrance
Something growing where it should not be
Interior plants that look tired the moment the lobby door opens

Every single one of those things is a failure point
Every stage of the guest experience is something the landscaper either got right or got wrong

And here is the thing — the manager does not call you and say the grass was long
They call you and say this property does not look the way it is supposed to look
And if you get enough of those calls you lose the account

Commercial clients think about experience
Not grass
Once you understand that everything about how you manage the property changes

Follow if you want to learn how to think like a commercial landscaper — not just a lawn guy

Just left an HOA board meeting — here is what they told me that most landscapers will never hear

Most landscaping companies walk in thinking the board cares about price
They do not

Here is what actually matters to an HOA board

Communication — are you proactively telling them what is happening on their property or are they hearing about it from residents first

Resident complaints — every single complaint that makes it to the board is a mark against you and most landscapers have zero system to prevent them

Reliability — are you showing up exactly when you committed to showing up every single time

Proactive problem solving — are you identifying issues and bringing solutions before the board even knows there is a problem

Price is almost never the reason landscape companies lose HOA contracts
They lose them because they dropped the ball on one or all four of these things

Fix the four and the price conversation changes completely

Just left an HOA board meeting — here is what they told me that most landscapers will never hear

Most operators walk into an HOA relationship thinking the board cares about price
It is the number one assumption in this industry
And it is almost always wrong

Here is what HOA boards actually care about

Communication
Are you proactively reaching out to tell them what is happening on their property
Or are they finding out about problems from residents before they hear from you
The landscaper who communicates first always has the advantage

Resident complaints
Every complaint that reaches the board is a direct strike against your contract
Most landscapers have no system to prevent resident complaints from escalating
The ones who do keep accounts for years

Reliability
Are you showing up exactly when you committed to showing up
Every time without exception without having to be chased
Reliability is the foundation everything else is built on

Proactive problem solving
Are you flagging irrigation issues drainage problems dead plant material or safety hazards before the board knows they exist
Or are you waiting to be told
The landscapers who bring solutions before the board brings problems are the ones who never lose contracts

Price is almost never the reason a landscape company loses an HOA contract
They lose it because they failed at one or all four of these things

Fix the four and price becomes a conversation not a dealbreaker

Most landscapers treat an HOA like 80 houses — that is exactly why they lose the contract

I have been landscaping for 35 years
I got my first HOA when I was 18 and never looked back

But here is what took me a long time to figure out

An HOA is not 80 independent accounts
You have to treat the entire property as one consistent operation

The problem is every resident only cares about their lot
What is right in front of their door
And if you ignore one resident while you are focused on the bigger picture
That resident is going to make it their mission to get you off that contract

The solution is systems
Consistency across the entire property while still making every individual feel like their space matters

That is hard to do
It took me a really long time to figure it out
Now I am sharing it

Follow if you want to learn how to actually manage HOA accounts the right way

Every Sunday night I do one thing that sets my entire week up for success

I look at every property on our schedule
I review the notes from last week
I identify the three biggest priorities for Monday morning

By the time the Morning Rally starts I already know exactly where the problems are and exactly how we are going to solve them

Most landscaping owners show up Monday morning and spend the first two hours reacting to whatever hits them first
I show up already three steps ahead because I did the work Sunday night

Preparation is not optional
It is the job

Try it this week...
You will feel the difference by Tuesday

Stop saying you want to make money

Start thinking about building a business

Build a real business and the money will come — chase the money first and you will be spinning your wheels forever

Amazon did not turn a profit for nine years
Nine
Imagine if Bezos quit in year eight
None of us would know his name

When year one feels heavy that is not a problem
That is the job

Tomorrow morning just get up
One foot on the floor
Make your bed — first win of the day
Get to the gym
Walk outside
Think about what you are grateful for
Do all of this before the phone takes over your life

Think only about the next 18 hours
Schedule your day in minutes not hours
Do the hardest thing first
No complaining
Ever

The freedom you are looking for shows up later
After the systems are built
After the right people are in place
Right now your job is to grind

It is what you do when nobody is watching that makes all the difference

Your landscaping work could be perfect and you will still lose the account. Here is why.

Communication. Or the complete lack of it.

Property managers do not fire landscapers because the grass looked bad. They fire them because nobody called back. Nobody sent an update. Nobody flagged the issue before the resident complained about it at the board meeting. The landscaper showed up, did the work, and disappeared. No communication. No documentation. No relationship.

At Devon Creek every single client gets pre-service notifications before we arrive, property service reports after every visit, and landscape quality audits that track the condition of the property over time. We do not wait for a client to call us with a problem. We find it first and we address it before it becomes their headache.

The bar in this industry is on the floor. Raise it. Follow for more.

I missed things I can never get back. Here is what I did about it.

I will not lie to you. There were years where I did not get the balance right. Where work ate everything. Early mornings, late nights, weekends. The business was growing and I kept telling myself that the sacrifice was temporary. That once things stabilized I would slow down. That once the next milestone was hit I would have more time.

It was not temporary. It was just how I was choosing to run things.

Building Devon Creek the right way, with real documented systems, with a team that is trained and accountable and does not need me in the middle of every decision, that is what finally gave me my time back. Not more revenue. Not more trucks or more accounts. Systems. Structure. People who know what to do and how to do it without me standing over them.

Here is the thing nobody says out loud when they are grinding to build something. The whole point of building a business is to build a life. A better life. More time. More presence. More freedom to actually be where you want to be. If the business owns you instead of you owning the business, you did it wrong. I did it wrong for a long time. Then I made a decision to fix it and built the systems that made fixing it possible.

Build the systems. Get your life back. It is possible. I am proof.

Want your property to look like a resort — here is the secret nobody talks about

Seasonal color rotation Four times a year we swap out the flower displays on a property so it always looks fresh always looks intentional never looks neglected or stale

Spring brings tulips and pansies Summer transitions to petunias and impatiens Fall comes in with mums and ornamental kale Each rotation designed to feel seasonal and intentional not just functional

It is a relatively small line item in a landscape budget that delivers an outsized impact on how a property is perceived Your residents notice it Your customers notice it Your HOA board notices it And the property manager who brought you in looks like they made a brilliant decision every single time someone comments on how good the property looks

This is what separates a landscape contractor from a true landscape partner

Which season is your favorite for color Let me know in the comments

Most landscapers go broke in winter — we make more money

Here is the advantage of commercial and HOA work that almost nobody talks about — snow contracts

Residential operators park their trucks from November to March Their crews scatter Revenue drops to zero And every spring they start over from scratch trying to rebuild the team they lost

Our commercial clients need snow management Curb to curb before residents wake up before the first employee arrives before the first retail customer pulls in Twelve months of revenue from the same accounts Same clients Same crews working year round no gaps no scramble

And here is what that does for your retention — when you can offer year round work your best crew members do not have to leave in the fall They stay They develop They show up in the spring ready to go

You want to keep your best guys Give them year round work Commercial and HOA contracts make that possible