how i got here

My PlayStation 3 broke down at the tender age of 15.

I was destroyed and my life was over.

I remember complaining to my dad about my lack of funds to buy a new system.

^“Why don’t you figure out how to make money online?” he says.

Strange words from a parent. That advice was also the greatest gift I have ever received.

Spring Break of 2010 I spent 12 hours a day learning how to build websites.

My plan: rank a blog on Google for people interested in Disney World and sell ads on it.

I had zero interest in Disney World and had never visited.

The blog was a complete failure.

I did learn how to build websites though.

My next scheme was to create a blog for World Of Warcraft and promote affiliate products on it.

I had also never played Warcraft but learned enough about it to rank a few blog posts.

After 3 months of work, I made 2 sales totaling $30 in commissions.

This was massive. I made my first $1 online.

My next goal was to avoid getting a summer job by showing my parents I already had a business.

Unfortunately, my nerdy little Warcraft blog would not cut it.

So I teamed up with my brother Jordan to start something a bit more legitimate.

New scheme: Offer mobile-optimized websites to local businesses.

The smartphone revolution was in full swing. Web traffic was transitioning to mobile.

The problem was that websites looked terrible on smartphones.

This was our opportunity. We would solve this problem and make a fortune doing it.

Our pitch was pretty genius…

We used an online mockup tool to contrast a business’s non-optimized website with a mobile-optimized counterpart.

We would then go door-to-door and sell our solution to every business in our small town of Lindsay, Ontario.

My mom was proud so she snapped a photo before we left the house.

We look normal but inside we were pissing our pants.

We had never sold anything, much less to business owners.

We were used to being customers, not salesmen.

Would we be forever shunned as those slimy teenage salesmen, never allowed to enter these shops again?

We would soon find out.

Our first target was a solar installer about a 10-minute walk from our house.

Our pits were stained on arrival due to the hot August heat.

Hearts pounding, we opened the door and approached the receptionist.

She was cute.

I gave an awkward, nervous pitch rife with stutters and teenage voice cracks.

Her expression turned from confusion to sympathy. She politely asked for our business cards.

We didn’t have any, so I shakily scribbled my name and @hotmail.com address on a ripped piece of paper.

It was a pitiful performance of the highest degree.

Yet, we walked out of there with more confidence than before.

That’s the beauty of going off-script, outside of your comfort bubble.

What you fear is never as bad as you think and this makes you more powerful.

We continued to hit the streets with little success.

Our final stop was a local pizza joint. The owner was a scary Greek man who went off on a 10-minute tirade condemning our lack of business cards.

He did seem interested though…

So we went home, printed some cards, and returned the next day.

We closed him for $300 up-front & $97/m.

It was our first semi-fat stack with a sprinkle of recurring revenue.

We became good friends with the owner and even got free pizza for the rest of high school.

It was the deal that would change our lives forever.

Over the next few years we built a nice-little side business that would pay for our college shenanigans and then some.

Those 4 years would go by in a flash. By the end, we’d both find ourselves in an existential crisis…

Go corporate or continue trying to make it on our own.

Let’s find out next week.

Have a great Thursday 🫡 

Graydon

Cool things I found during my weekly internet stroll.

Super solid IG post with the best tools to work faster and better with AI.

The FDA just cleared a new device that stops bleeding from gunshot wounds in seconds.

I’ve never been to Japan but want to visit now that there’s a Nintendo Museum about to open up.

Served up by Spijker & me.

Gypsy Woman | Stolen Gin, ADLR, Different Hits

Light Up My Dark | Monolink

Live in Iceland for Cercle | Ólafur Arnalds (have probably listened to this 20 over in the last week)