What Earning $60K in a Summer at the Age of 21 Taught Me About Entrepreneurship

My idea of entrepreneurship had always been a romantic one.

I associated it with prestige, with intelligence, with control.

The reality, as I learned when I started my first business, was that entrepreneurship was also 99 percent toil and 1 percent glamor. It was getting up before the sun and hearing a lot of "No's" so that I could get to the people who would say, "Yes". But with a lot of effort, I made enough money in one summer at the age of 21, than I ever thought possible. I've been bitten by the entrepreneurial bug ever since. Here are the lessons I learned.

Lesson One: Use your weaknesses as your strengths.

Up until starting my business, I had never in my life painted a house. So you can
imagine that becoming a residential painting contractor who was young and a student seemed like a hurdle I couldn't overcome. I was convinced that I'd have trouble closing a sale. But then I was given the great advice that my perceived weakness was actually my strength. Most of my competition was made up of lifelong contractors, and as a result, hiring a student was a feel-good novelty. Soon thereafter, giving my pitch and closing sales became much easier. I embraced the fact that some people were more than happy to have us paint a room or even the entire exterior of their house because we were students. In fact, my biggest deal ever came as a direct result of someone wanting to "give back" and he bought some of our most expensive options just so that he could help us earn an income.

Lesson Two: Get comfortable with the grind.

While the majority of our painting happened in the summer, the lion's share of our
marketing had to happen much earlier, starting even as early as January. At the time I had zero dollars to spend. So getting the word out required that I go door-to-door; bundled-up against the cold, Canadian winter in my boots and mittens, asking homeowners if they were considering painting their houses once the snow melted. It was ridiculous, and people often told me so. But without fail, 20 people out of 100 would say yes to a free estimate, and then about a quarter of those would go on to hire us. It was hard, being out there for hours, day after day. But eventually, I gave into the grind. Having people turn me away hurt less and less and I started to think of it as the price I paid to get the results I wanted. I leaned into the grind.

Lesson Three: Systems and people change everything.

There was a point in running the business where I had enough experience delivering on projects to see patterns emerge. I could anticipate how much work each job was going to be, how much paint was required, and who on my team would be interested in taking on more responsibility. These patterns started to nag at me until I took advantage of them to create systems. I learned that I could order larger quantities of white glossy paint all at once (instead of on a case by case basis) because every job needed it and that way I could get a discount. I realized that a few of my painters wanted and could take on more responsibility and even lead a team of three or four other painters through a job so long as I briefed them. Slowly, I spent less and less time at each job site, and by the end of the summer, I showed up only to drop off cold drinks and treats and do spot checks. The amount of work being done didn't change, but the way the work was getting done changed drastically. It was then that I understood what it meant to create a business that could run outside of myself.

Now, in my late 20s, I'm learning to run a whole different kind of business that is based in technology and providing marketing services. With it comes new challenges and a lot of hard work, but patterns are emerging and progress is happening.   

So if you're an entrepreneur, I welcome you to reflect on the lessons you might already know about business and ask yourself if you're truly putting them into practice. And if you're considering entrepreneurship, I welcome you to embrace the grind and your weaknesses so that you can get to a point where you can create something bigger than yourself.