It sounds like you had a clear goal, and worked diligently to get there. Kudo's!
I am a bit confused about your startup. Were those first two years filled with low sales, unprofitable work, or were you just trying to pay for equipment investment? [yes, I know it was a combination of all of the above, but perhaps you will share some of the details]
In the fall of my last year of college, a classmate and I approached our arboriculture professor, John Ball, about helping us to pick out some basic tree care equipment (climbing gear, small saws, rigging stuff) so that we could make a few bucks on the side while finishing up school and looking for jobs once we graduate. John knew about a city forester who had his own part-time tree service for sale and hooked us up with him. We bought him out and went to work with his older yet reliable bucket truck, full setup of saws and rigging gear and his client list. It cost us something like $10 or $15k at the time (I can't remember for sure).
It kept us busy enough during the school year that we decided to run it full time once we graduated that next spring. That's when reality set in and we had to start repaying school loans on top of paying business expenses and paying ourselves a salary. We just didn't have enough experience in running a business to understand all the expenses associated with a tree service and we were still trying to build a customer base so we could charge what we needed to charge in order to make a living at it. As it was, we were each taking a salary of about $5k that first year after business expenses were paid. Not much to live off of so we each took night jobs at a manufacturing plant and continued to work days doing the tree service thing.
It didn't take working two jobs for long before i decided that the only way we were going to break out and make a go at things was to expand into landscaping. My partner and I each had landscape design degrees as well as arboriculture backgrounds so, to me, it just made sense. After getting a couple of big landscaping jobs under our belts, things took off and we were busy. After two years of the night job thing, I said 'enough' and went back to working full time with the landscaping part of the business while my partner ran the tree service.
Long story short, the landscaping and tree work together got to be more work than my partner had wanted to take on and he left the business. I took it over and bought out a second tree service which gave me more clientel and a bit more equipment to work with. The previous owner was well-connected in the community so I was really buying his name moreso than his equipment. I hired an arborist to run the tree service crew while I still bid the jobs for him and did all the business end of things along with the landscaping.
All this happened in the course of about 3 years. That's how long it took to go from an unknown newcomer in the business to someone with business name recognition within the community. It was a very long 3 years of working 20 hour days with little or no pay to show for it because I put every cent possible back into building the business.
By year 5, things were looking pretty sweet. The tree service was traveling a tri-state area doing residential and utility work and had even gotten in on a huge land reclamation project. The landscaping service was doing a lot of high-end residential work and starting to bring in some serious cash. That's when I made the decision to sell the tree service to my foreman and invest more money into the landscaping company as that's where I saw a real future as the city I was working in was expanding rapidly and had a real need for a
good landscaping company.
The landscaping company did well and I was looking to expand into building a large 16-acre garden center to the point that I had secured part put not all of the funding to do so. The process of securing the rest of the funding drug on for over a year and, eventually, I got burnt out on the idea of owning and operating a garden center and I got tired of the landscaping thing as a whole so I sold the company and went back to school for my masters in landscape architecture with the intention of getting a job teaching at a university.
That didn't quite pan out as planned (good think in hind sight) and now I do tree work part-time along with my full-time job which is a good one. I'd love to do tree work full time but my community is overwhelmed with too many tree services as it is. I'm lucky to make a go at it part time this year with so much competition but I plan on hanging around for a few more years...
There you have it. More history on me than you really wanted.