Rethinking What It Really Takes to Start a Business

People often assume it takes a huge amount of money, time, or expertise to start a business—but it really doesn’t. One of the best books I’ve ever read is The $100 Startup by Chris Guillebeau. The premise is simple and the title says it all: starting a business can be so straightforward that you can do it for less than a hundred dollars. It sounds like a gimmick at first, and I would have thought the same—until I tried it myself and actually succeeded.

The Challenge That Sparked Everything

Two years out of college, I heard about this book on a podcast and challenged myself to finish it by the end of the month. Once I put it down, I gave myself another challenge: start a business for under a hundred dollars, and if I couldn’t make back the money within 30 days, I’d walk away from the idea entirely.

Finding the Right Idea

So I started brainstorming, and that’s when the idea of a curb address-painting business came to me. It seemed simple, straightforward, and in a city like San Diego, there was a clear need for it. Once the idea hit, I dove right in. I came up with a brand name, built a basic website, set up a Google profile, created social media pages, and printed out flyers that I dropped around my neighborhood.

The First Request That Changed Everything

About five days later, I got my first service request through the website—and I was honestly shocked. First, because I couldn’t believe someone actually found me and booked me, and second, because I suddenly realized I had never painted a curb in my life.

I immediately watched a handful of YouTube videos, ran to the store to grab the basic supplies, and headed to her house just a few minutes away. I can’t pretend I did an amazing job, and I don’t think she thought I did either—but she was incredibly kind and handed me $30.

Why That First $30 Mattered More Than Any Paycheck

Sure, I had earned $30 before at regular jobs, but these $30 felt different. They meant more to me than any paycheck I’d ever received. This was money I earned by creating something from scratch, taking a chance, and proving to myself that I could build something of my own.