When I started out I was kind of retired myself, even though I was only 39. I lost my job as a project manager in the environmental consulting and engineering field and had already built up a fairly healthy financial cushion. My mother was dying of Lou Gehrigs Disease, my dad had been gone for 3 years so she was in my care, I had two young sons (ages 3 and 6) who hardly knew who I was, my wife and I had gotten somewhat distant because I was pretty much consumed with work all of my waking hours...I brought work home every night...reports to review/edit and non-billable work to keep my billability rate up high to get my company profit share rating high. I got a pretty good severance package from my company and was collecting unemployment until I started the business.
I invested 10K as start-up cash and bought a new walk behind mower, trimmer and blower and had a trailer made by a local trailer shop. I already had a truck and landscape tractor for my own use. I cashed out an annuity I had taking monthly payments for 10 years. That allowed me to take it easy at first and put most of what I made back into the business for the first couple of years. My wife hadn't worked since our second kid was born so we got to spend a lot of time together and with our kids. We spent a lot of time recreating on our back acreage and in the river and going to the local attractions. Bascially I semi-retired while I was able to enjoy it with my kids. My wife took a total of 12 years off and is back to work now part time and I'm full time on the business with some seasonal help from the kids. It was really nice to be a young family with me only having to work part time on the business. We didn't get to travel out of state much or do vacations, but we had a lot of fun.
My biggest problem was that my 1985 truck went down on me twice the first season, once for a week to have the top of the motor replaced. I had a tow hitch put on our van to use as a backup. It was a 2002 VW and actually has a 3/4 ton chasis, extra load tires and handled the trailer well as long as I balanced it properly...didn't end up using it but it was available if needed. I mentioned it earlier, but you need to have a spare for just about everything or at least something you can substitute on a short-term basis. Some dealers will have loaner mowers they will let you use. You can get a short-term rental truck from Home Depot or some other source...just don't mention you want to use it as a landscaping vehicle...you're moving furniture
You don't want to be in a situation like I was trying to service your lawns out of a Taurus station wagon with a push mower for a week.