Changing the format here a bit.

Going from writing —> documenting.

Was feeling the pressure of coming up with “worthy” ideas to talk about. And while that may be a useful exercise for someone trying to build an audience, that is not my goal.

After talking to a friend last night (hi Louis), I realized my goal is to just capture the nothingness that happens day to day.

When (not if) this business (or businesses) is successful and I am rich, I’ll remember the big moments, but I likely won’t remember the small one. Yet, the big moments wouldn’t be possible without the forgettable moments.

Everything is a part of the journey.

I’ve also changed the title from The Unsexy Business to Should Be Easy.

Should Be Easy is an inside joke I have with my business partner. We always say that new projects we take on “should be easy”.

They never are.

Thought it was suiting for this venture too.

Anyways, here’s a few thoughts from this week.

“You work too much.”

I’ve heard that from my mom many times this year.

She’s probably right.

It’s the offseason (landscaping in Ontario = March —> December) and I’m still working 10-12 hour days regularly.

The offseason is supposed to be a time to take your foot off the gas and relax. And while we have been physically relaxing, we’re certainly not working any less.

I kind of like it, though.

Working hard feels good. And until recently, I can’t say I’ve worked very hard. Like, truly hard.

It’s nice to know what your capable of. And it’s nice to move the standard too.

Working 14 hours used to ruin me, but now, it doesn’t bother me all that much. Not sure if that’s a good thing or not.

Anyways, the goal this offseason is to build out our systems as much as possible in order to allow us to dedicate all of our time to marketing and sales.

Logistically, that means writing a ton of documents (thank you, Google Drive).

We are constantly asking ourselves a couple questions.

1. What went wrong last season? Why?

2. How can we solve it?

3. What needs to happen for us to not work in field?

Right now, we are building out all the resources necessary to make sure our crew leads (the guys who run the trucks and crews for us) are set up for success.

I think we are making solid progress, but I am worried about the implementation of these documents.

Will half of them even see the light of day?

Is this just busy work to make us feel productive?

What actually moves the needle?

I’m not sure we know the answer to that. I guess you never do.

I’ll let you know in a few months.

On repeat this week

Forever - Big L (ft. Mac Miller & Pale Jay)

There’s a handful of rap songs that make me feel like a little kid again. This is one of them.

I can’t quite put my finger on what it is. I think it has something to do with the instrumental. 90’s drums + piano perhaps? Think Heard ‘Em Say by Kayne

Anyways, I can’t say I know much about Big L, but I do love Mac Miller. This is obviously an old verse of his and based on the intro, it’s clear that Big L was one of Mac’s heroes growing up.

It made me happy this song was on this album.

I’m sure Mac would have loved that.

Until next time, try not to take life too seriously.

Talk soon,

Devin

This is my career progression over the past 5 years:

corporate —> labourer —> solo entrepreneur —> buying into a larger business

Nothing fancy, right? But, I’ve noticed a pattern recently.

No matter where I am in my life, what I’ve accomplished or learned, I can’t seem to shake the feeling that I don’t belong.

Let me walk you through the imposter syndrome I’ve faced at every transition point.

Transition #1 (corporate —> labourer)

In 2023 I quit my corporate sales job (because the thought of even one more cold call made me want to jump off the side of my office building) and decided to landscape in a family friends business.

We built patios & fences, chopped down trees, cut grass, etc. All that jazz. It was textbook masculine work.

Despite that, I kept feeling like I wasn’t “manly” enough to be doing this. I felt like any time someone looked at me, they knew I was a fraud. Just some boy trying to convince himself he was a man.

On top of that, it wasn’t even my business. I was just a labourer.

But not for long.

Transition #2 (labourer —> solo entrepreneur)

Later that year. I started my own landscaping company. I wouldn’t be just an employee anymore, I would own the whole thing.

I knocked doors to get my first customers. I fulfilled work. I even hired an employee by the end of the year. I was, by definition, an entrepreneur.

But when people asked what I did I would tell them, “Oh, I just run a landscaping company”.

"Just”

That was the word that always killed me.

All of my friends, friends of friends, friends of friends of friends have super impressive, high paying careers.

Investment banking. Private equity. Corporate real estate. Lawyers.

All the careers your mom is really excited to tell her friends about. The sexy jobs.

But despite actually running a business. Turning complete strangers into recurring customers. Creating money from seemingly no where. I was embarrassed to call myself a business owner because, let’s face it, owning a company that cuts grass isn’t that impressive.

“It’s just landscaping”

And of course revenue could always be higher.

Transition #3 (solo entrepreneur —> buying into a larger business)

So, I decided to make a jump.

Earlier this year (2025), I bought into my friends property maintenance company.

It was a major jump in both operations and revenue.

Probably 6-7x what I was doing myself.

First and foremost, it’s an awesome partnership. I can see myself being business partners with him for the rest of my life. And I’m excited about work every day.

But, this also solved my status insecurity.

If the industry I work in isn’t going to impress people, maybe the money can.

I wouldn’t have to tell people I “just” own a landscaping company because we also happen to make a bunch of money (not true btw, but it seems true on the surface).

And it worked!

When people now ask me what I do, I tell them I own a landscaping company with a business partner.

No “just” in sight.

And if they’d ask about revenue, they were always impressed when I told them.

Problem solved, right?

Not really. Because there’s a new problem.

It wasn’t my business.

I mean on paper it is, but I didn’t start it.

Sure, I helped grow it significantly but it already existed before I got there, so in my mind, I did the easy part.

I used to hope that people wouldn’t ask what I did for work. Then that they wouldn’t ask about my revenue.

Now I hope people won’t ask how I got here.

It seems like no matter where I land, I feel like I don’t belong there yet.

I don’t know if that’s insecurity, ambition, or just the cost of moving faster than your self-image can keep up.

I’m still figuring it out (as you can see).

There’s an idea I’ve been sitting with lately:

Identity lags reality by 1-2 years

That feels uncomfortably true right now.

Personally, I still feel like I’m in 2023, pushing lawn mowers for someone else, trying to convincing myself I’m allowed to be here.

I don’t know if that means anything needs to change.

And if it does, I have no clue how to change it.

On repeat this week

Chain Gang - Sam Cooke

I’ve been binging Fallout recently and the soundtrack is absolutely phenomenal.

It’s all late 50’s, early 60’s stuff.

This song has been stuck in my head all week.

I can’t stop doing the little grunts from the chorus unprompted.

Until next time, try not to take life too seriously.

Talk soon,

Devin

Growth sucks ass.

Sorry, growth sucks cash. Typo…

In 2025, our landscaping company, if I can say so myself, grew a good amount.

Revenue was up about 50%. Net profits increased around 35%.

On paper, that’s a great year.

And as the year comes to an end, we’ve sat down to plan what growth looks like in 2026.

And what we mostly discovered is that growth means spending a shit ton of money.

What do we spend money on?

Emergency fund.
Equipment.
Marketing.
Spring rush carrying costs.
Truck wraps (someone tell me why are they $5K per truck???).

How much do we spend? Pretty much everything.

It’s weird. You work all year. 50, 60, 80 hour weeks. You lay 20 yards of mulch in the blistering heat, do 4 quotes, invoice, run payroll, then can’t sleep because you’re worried about some customer leaving you a 1 star review for stepping on her Hostas.

For all this work, you expect, at least subconsciously, some kind of payout.

And you get your payout. It’s just not cash. It’s your truck thats out delivering service. Or the Facebook ads that just landed you 5 new customers. Or the emergency fund thats tucked away incase you can’t make payroll.

It exists, but it doesn’t feel like it exists.

It’s funny. I’ve always said I’m okay with delayed gratification, but when I’m faced with the actually decision, take cash now or reinvest so the business can grow, it’s not the no-brainer I thought it was going to be.

It’s easy to say you want growth. It’s hard to actually live with what growth requires.

Lately, the tradeoff feels like this:

I can feel rich. Or I can build something that will actually make me rich.

The uncomfy part is deciding what the business needs right now.

Is the business meant to pay us today? Or is it meant to make us wealthy later?

Do I want a high paying job? Or do I want to own something that cash flows without me there?

That’s the decision we’re sitting with.

It’s not exciting.

But it’s honest.

On repeat this week

Martha My Dear - The Beatles

For years, I’ve said that if I could play any song on piano, it would be this one.

One of my New Year’s resolutions is to play piano for 30 minutes a day. I started early this year, and I’ve spent the last week learning this song. I’ve made more progress than I expected.

Paul (McCartney, but we’re on a first name basis) has a gift for writing riffs that feel impossible and then singing melodies on top of them that have no business being sung on top of them.

Check it out.

Until next time, try not to take life too seriously.

Talk soon,

Devin