How to start

Quite a few years ago I found myself in a situation where I wanted to start my own business. I was sick of working at the places I was working at, and I wanted to get out on my own. Problem was… I had no idea what that was. I didn’t have any obvious breakout ideas. The experimental ideas I did have seemed impossible to market, as in, I had no idea how to sell anything. The thought occurred to me to try to raise money to build something, but I didn’t even know where to begin.

It was an awful unmotivating place to be.


My daughter, Addison, turned 3 this week. How on earth have these 3 years gone by?

If you know toddlers at all, you can imagine the types of games we’re playing. Lots and lots of pretend. She’s often “the teacher” and I have to be the student. A baby student. Complete with my weird impression of talking like a small baby.

Addison is also obsessed with her fake groceries and kitchen. She makes me pretend I’m buying those plastic groceries until her “store” is out of stock. Then she becomes the chef, and cooks everything I bought.

She makes a “soup”. Which is just a bowl of random plastic things: fake strawberries, a milk carton, a whole turkey.


She’s a terrible chef.

But that’s the point, isn’t it? There’s no way she can actually be a good chef. She can’t even be an actual chef. She’ll kill herself if I give her real knives or let her use the actual stove.

She has to start somewhere. Anywhere. And pretending to be a chef even with the fakest of tools is somewhere.


The job I had before I struck out on my own was an ecommerce hosting provider for clients who sold downloadable software. Like Shopify but for digital products and with a huge catalog of software sold for their clients.

They had this contest. They wanted to know what would happen if they gave everyone the ability to open up their own “store” with that catalog of software from their clients.

In other words, an affiliate program. You got a commision from any sales your site made.

Out of the box, everyone’s site looked the same. But you could style and brand it however you wanted. You could even set your affiliate commision. Everyone in the company was invited to compete at who could sell the most in a month before they launched this program to the public.

The winner cleaned up. They had this great idea to take the dynamically created pages of their store and convert it to a static site they could further optimize for SEO. If you looked up any of these niche software products in Google that month, it was highly likely, you’d find their store at the top of the list.

I’m sure there’s more than a few people reading this cringing at the contest itself. An affiliate program, really!? Yuck. Those are a race to the bottom.

First, the winner, was just the winner in the first month. What happens when everyone copies their SEO strategy? Then it’s just a bunch of Google spam which Google has gotten better about crushing. Also, the affiliate commissions will race to zero with people trying to undercut each other on the same exact products. Some people will try and take Google Ads out, which might work for one person in the short term, but when everyone starts, they’ll all lose a bunch of money to Google and profit will go to zero.

Yes. Yes. And yes. That’s all true.

But that’s not that much different from making soup out of pretend strawberries, milk and turkey.

Today, that company I worked for doesn’t even run this affiliate program anymore probably because of all those reasons above.

But I learned an incredible amount from that terrible contest. I learned about SEO and how to improve my own search listings. I learned about creating Google ads, keyword research, and split tests. I learned about using copy and pictures to get people interested.

One of my most successful experiments on my affiliate site was creating a banner of someone asking visitors: “PLEASE DON’T BUY ANYTHING HERE”. Sales went up.


My first real business was a company called Inkling. We made it easy for companies to host their own prediction markets which look like stock exchanges, but instead of stock in real companies, it was pseudo-betting on business decisions.

We were late to the market. There were multiple companies already out there that knew this stuff so much better than we did. Not to mention, the best selling book, “The Wisdom of Crowds”, gave our biggest competitor so much free press and publicity.

How could we possibly catch up?

All those things I learned from my fake store sure came in handy. It took awhile, but I got our SEO in order. Eventually we were the top result for the phrase “prediction markets”. Google Ads were no sweat for me to create and optimize. We constantly tweaked our copy to get better at persuasion.

Eventually, I can confidently say, we were the number one company hosting businesses prediction markets.


So many of the strategies I use today to run Highrise, started with running that crappy, pretend store.

Feeling stuck trying to create your own business? Just start. Start anywhere. Pick up some junk in your house and figure out how to sell it. Online or just starting making phone calls. Sign up for some affiliate program and start learning how to craft websites, ads, copy, SEO, whatever. It doesn’t matter.

Do anything. It doesn’t matter if it feels pretty fake. It’s ok to just pretend for awhile.

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You should follow my YouTube channel, where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.