Tree Trimming Profits!

10/6/23

Howdy!

In 2019 I was building a startup with Jason (yes, that Jason). In the beginning, it was not going well and we were running out of cash, fast. We kept pivoting ideas and just couldn't find traction.

During that same time, Jason's brother Mike was starting a tree trimming business. His brother knew nothing about business, but he sure was a smooth talker, and could sell an oil change to a Tesla owner.

Jason started looping me in to help with marketing. Man, what a great business this was! We'd generate leads and at the end of the day Jason would text, "Mike closed 4 of our leads today for $7k! At 60% margins!"

Over and over we kept telling ourselves "What are we doing wasting our time with this startup...we need to start cutting down trees!"

We were only half joking.

‍As a recovering domain name addict, I started shopping around, just in case I might want to start a tree business one day. FastTreeCare.com was open for $10, so I bought it. What a strong name! I might name my next son that, actually...

So all you fellow domain name addicts out there, let me tell you, there is hope for you and that domain you keep renewing.

Our startup soon found traction and the tree biz idea was pushed to the back burner, but Mike kept running with it. He's still running it today, actually!‍

4 years later I happened to own a startup incubator/venture studio that has thousands of bright young applicants, hungry and eager to start a business, but without funding or tools.

One of the incubator applicants was James. James was about to graduate from Bowling Green and had a management trainee job waiting for him at Amazon, but he didn't want to take it. He wanted to work for himself. Once you taste that life, there's no going back.

How would you bet he made money in college? By flipping and fixing phones! We obviously became fast friends.

Being active on Twitter, and thinking back to those days of helping Mike launch his tree biz, I penned up this thread on how to start a tree biz, and half a million people ended up reading it.

‍The flame became reignited, but I still didn't have the bandwidth to execute. Tons of people DMed me to partner on it, but it never felt right. But hey, maybe James would take a crack at it!

I told James that if he were to move to Dallas after graduation, I'd give him a truck, a big chunk of equity and $3k/month to start this business. I'd pay for his gas and all the funding the business needed, including (and especially) marketing costs. All he needed to pay for was rent, basically.

In addition, I'd be his playbook, his treasure map and his mentor. I'd show and tell him exactly how to start a successful tree trimming business and promised him that he'd be successful as long as he followed my instructions.‍

BUT, I wasn't going to be there with him in the truck every day. He'd be out there on his own.

We'd meet regularly and talk daily, but this was going to be his baby.

‍James saw this as an asymmetric bet. He'd be making half as much than he would be at Amazon, but would be working for himself and could potentially build a big, profitable business, and fast.

‍He was in.

Before committing, I flew him out to Dallas for tacos and he stayed in our guest bedroom to make sure we were a good fit for each other.

Like a glove, baby! Can you tell his dad played football for USC?

A couple months later he'd found an apartment and was driving all over the metroplex. Here are the key points to this whole business model: