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Drew started HoursLogger in 2014. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on HoursLogger?
My entrepreneurial journey started while I was in college. My parents were running a family-owned construction business at the time. Mom was head of the office, Dad was the lead in the field, my sister managed the subcontractors and meetings, and Matt and I worked on the job site.
Me working on the job
All our lives changed when we took a project that went really bad. The project was estimated to take about a year and $1M. It ended up going ~3 years and went well over the budget. We completed the job but it wrecked our family financially.
I felt a personal responsibility to do something about it and started various businesses that didn’t get far. Surfboard beer pong tables, custom shaped whiteboards, and handy-man services for students moving in/out. None of it worked until I put up flyers for tutoring electrical and computer engineering.
I printed flyers at the beginning of the semester and got 1 call at the end of the semester to help someone study for their final. When we finished, he gave me $40 cash and I remember thinking that was the easiest $40 I’ve made ever. At that moment, I knew I was on to something.
I ended up growing the tutoring business to the point where I was charging $50/hr, running group sessions (15-20+ people), and automated many tasks through my website. It was a great playground for business but I didn’t want to tutor forever. That’s when I had the idea to switch to software consulting and started DevCo with Matt.
Once Matt and I got our first real project, we needed to track our time and details so we knew how much to bill and what to put in the line items. It took hours to go through both of our times and sync up on who did what and what was billable.
We took a look at the existing solutions and didn’t like any of the apps we found. Many felt too complex. They had too many features and didn’t feel easy to use. How do I input time? How do I view my time? How do I create the invoice? These were things I thought should be very obvious.
We ended up building our own app that had the bare bones functionality. Even if we never made a sale, we agreed that it would still be good practice to keep it as a side project.
We knew time tracking and invoicing is a really competitive space but there were a few guidelines I used that made me believe HoursLogger was worth pursuing.
- Lots of people need time tracking and invoicing.
- It’s B2B (business to business). If you need HoursLogger, I know you’re making money. Most businesses doing consulting have no problem paying $9/user/month.
- It scales well and is recurring revenue.
- Businesses aren’t likely to change time tracking/billing apps frequently.
- If Matt and I like it, other people may like it.
- It gave us an outlet to learn a ton about tech, marketing, sales, customer support, and more.
After a year of DevCo consulting and working on HoursLogger on and off, we finally made our 1st sale. It was a completely random person on the internet, not a family member or friend. 1 sale turned into 5, then 10, then 20. At that point, we knew the product was working.
Matt and I at a QuickBooks conference promoting HoursLogger