My journey from a freelancer to freelancing platform

My virtual startup was born from a place of pain. I learned that in order to succeed as an entrepreneur, I had to let things get painful–I have to truly feel it when I lose. My journey as an entrepreneur has been all about surviving pain and sacrifice until I achieved freedom. That’s my bottom line; I don’t do it for the money (I haven’t been paid in two years), I do it for the freedom.

Freedom is a core value at Hubstaff. I go to work every day so that myself and more than 30,000 Hubstaff users can work and live as we choose.

This startup origin story explains the beginning of my entrepreneurial journey and is a huge part of our success.

The pain began with cubicles and commutes

I lasted 18 months in my first job. It was in corporate finance, required a 2-hour commute and my cubicle was in a building that looked like all the buildings surrounding it. I was commuting for more than 12 percent of my waking hours to get to a box in a box.

Hubstaff’s journey began in 2002, stuck in Chicago traffic and dreading the drive home. I wasn’t adding any value to the world and that had to change.

Light at the end of the tunnel

I owe my start in entrepreneurship to my dad, who got me a course on how to create my own internet business. I devoured it and began building my business in the golf niche. I started with a book, then moved to DVDs, creating at night while working in a cubicle during the day. Once my business started making US$5k a month, I left the world of cubicles and never looked back.

Once I committed full-time to that business, things changed fast. I went from making US$46,000 at a corporate job to $560,000. We sold more than 30,000 books and 100,000 videos.

The post-cubicle cubicle trap

I created my golf business from my closet with a US$300 eMachines computer. I thought if I could do all that from a studio apartment, I could do so much more with a team of smart people and an office.

Nope.

Getting an office didn’t do anything except add a commute to my day. I was trapped all over again and this time it was my own fault. Essentially I was just trapped in a larger cubicle!

My creative juices fell and competitors were beginning to surface. Ad prices rose by 400 percent and I was learning about the stress of managing people.

Team management is hard

My business was making approximately US$1 million annually, but it also had to support five employees and two partners. I had to make the switch from creator to manager, and it was a new type of pain.

There was a new type of pressure on me; I had to make payroll and manage a team of eight contractors. I wanted to understand what was going on in my teams so I could manage better, so I tried workflow management software, but it was inefficient and didn’t help at all.

Learning about remote management

Hubstaff is born

To be continued