Four Small Business Owners Share The Milestones That Made Them Think, ‘Okay, We’re Really Doing This”

There are a lot of memorable moments when you launch a new business. Most founders probably recall the day they hit ‘publish’ on their official webpage. Or the day they first introduced themselves as business owners in public. Or — the crown jewel — the day someone first paid them for their work!

(At Owning My Own, I keep a photo on my phone of the first piece of mail that came addressed to the company. Granted, it was a postcard from an accounting firm that wanted to do our taxes, but still. It was legal, official, stamp-and-paper mail, baby!)

We wondered what other small business owners marked as their pivotal moments, so we asked a few:


Chris said he can still vividly picture the morning after school let out for summer vacation in 2011. He’d resigned from teaching to work on OneSeed Expeditions full time, and as he was biking across a bridge to his new coworking office, “the sun was coming up in Denver, the ballpark was there, and I was like, ‘This is it. This is what being an entrepreneur is like.’”

He also recalls the day, four months in, when the company earned its first revenue. “I remember taking that check to the bank,” he said. “I was so proud. But it also locked me in. Now I had to do this thing.”

Chris Baker

Founder, OneSeed Expeditions

Amy said she remembers setting a date for the first market and putting it on flyers and online. “You have the parking lot. You have the logo. You have the date,” she remembers thinking. “This is happening. You can’t back out now!”

Amy and Doug Yetman

Owners, Horseshoe Market

Within his first year, Paul found himself on an airplane to Boston. International Data Group, or IDG, had discovered his presentation workshop online and called to see if he would be willing to come and train their employees. It was the first time he’d been paid to travel as a speaker.

Paul Vorreiter

Owner, Reflective Spark

Brian said he clearly remembers, about four months after opening the shop, he got the first phone call from a school asking him to repair their broken band instruments. It was proof that Rocky Mountain Music Repair was starting to build a reputation. Today, they work with all the elementary schools in their town, as well as several high school bands. They’re even starting to get the most coveted work – universities.

Brian and Deanna Stevenson

Owners, Rocky Mountain Music Repair

Do you remember the moment you felt like your business was real? Tell us about it in the comments section. Or respond to the current Question of the Month, and we’ll publish some of our favorite answers in a future article.