We tell stories about entrepreneurs who take big risks because risk is sexy. People who take risks, the implication goes, are fearless. It makes for a great story. A hero overcoming odds.

But if you’re anything like me, big risks sound scary. Today I run Site Builder Report, a one-person niche business that makes ~$40,000 / month. But five years ago, I was working my first job and saddled with student loans. I wanted to quit the job and start a business— but that just felt too risky. 

So here’s what I did instead.

1.Cutting Back on My Full-Time Job

My first job was Digital Media Co-ordinator for Union Gospel Mission. And though it was great, I constantly daydreamed about starting a business. 

Unfortunately I had a monstrous student loan— and quitting was just too risky. I needed to get creative.

So I came up with a solution: I asked my manager if I could work three days a week instead of five. I promised to keep the same responsibilities— I'd just complete those responsibilities in 3 days rather than 5. 

To sweeten the deal, I also said I’d take 3/5's of my pay. My job paid ~$44,000 CAD and I believed I could scrape by with less. 

My manager deserves a lot of credit. Though he may have been skeptical, he was supportive. He promised to talk to HR and see what he could do. 

It wasn't far-fetched to imagine getting my work done in 3 days. My job had plateaued after I completed some ambitious projects in my first year and I was confident that I could stay on top of everything if I stayed focussed. 

A few days later my manager got back to me and said we could give it a try. Boom. 

2. Starting My First Business

So I found a co-working space and started my business. 

Early morning at the co-working space. Though I definitely did not have the money at the time, I will never regret getting a co-working space. I’ve always found working out of my bedroom to be demotivating.

The business I started was bad. It was called Bright Contractor. It was a website builder for contractors. (The year before I had built a successful website for my brother's concrete business and thought I could scale that service up.)

Though Bright Contractor was a bad idea, the days spent building it were great. I would wake up early, extremely excited, bike to my co-working space and happily hack away all day.

Occasionally, a cranky person at my job would be upset that they couldn't get a hold of me on my days away (“What!? He doesn’t work Tuesdays?!”). But in those cases I would— using discretion— let them call me. The arrangement went smoothly otherwise.

An early build of Bright Contractor.

3. Pivoting Into a Profitable Business

After a few months I launched Bright Contractor. Unfortunately no one signed up for it. 

I tried everything to make sales: I designed free mockups. I read sales books. I would randomly asked contractors what they thought of my idea (most suggested it was a tough market— they were right). 

Nothing worked. So I decided to shut down Bright Contractor. 

I was frustrated because I thought Bright Contractor was a good idea— it was just overshadowed by corporate website builders like GoDaddy and 1&1 who could out-market and out-promote me. 

I concluded that in the world of website builders, it wasn’t the best product that won, it was the most well-known product. That conclusion proved valuable: it lead me to my next business idea: Site Builder Report.  

Instead of building yet another website builder, I would help people choose the right website builder by doing reviews of every website builder I could find. I realized the market didn't need another website builder— it needed an air-traffic controller.

In time Site Builder Report became a nice, profitable niche— and most importantly, a ticket to quitting my job permanently. 

4. Don’t make starting your business an all-or-nothing gamble.

Would I have started Site Builder Report if I had quit my job fully? 

I’m not so sure. I would have been desperate for Bright Contractor to succeed— it would have been my only source of income. I would have been walking without a wire. It’s hard to make a decision to pivot when you don’t have money for rent. 

I was able to pivot into Site Builder Report because I had a secure, consistent income from my job. My life didn’t depend on Bright Contractor succeeding. Sure, I didn’t have a lot of money, but I wasn’t without options. I didn’t need to bet the farm. 

We tell stories about entrepreneurs who take big risks because risk is sexy. People who take risks, the implication goes, are fearless. It makes for a great story. Mark Zuckerberg got up and moved to Palo Alto to build Facebook for a summer— but we forget that he also had enough money to put $85,000 into Facebook that summer between him and his parents. 

If you read Indie Hackers you're probably sharp enough to be skeptical of sexy cover stories about death-defying entrepreneurs. I’m guessing you're bright enough to see through the myth-making. 

So here’s an alternative: play the slow-game. Life is a longer than we think. Take a small step today and let it grow exponentially over time. 

Don’t make starting your business an all-or-nothing gamble.

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