Hey Colin! Sean here. Welcome.
What are you learning in school? Tell us more about yourself, and you don't need to be shy. The more we know about you and your situation, the more we are able to give more applicable advice.
Hope you are getting some business classes.
I'll echo what others have said that its good to learn from successful people.
I started out my business out of necessity, sort of, as I moved to WA state to be with my girlfriend and thought that I'd be able to find more conservation work here, continuing my previous career path. As it happened, I didn't find it in our city (Olympia).
I worked for another tree service for a few months after a big storm. After I had to step away from the big chipper for fear that the three hungover guys charging in with a big top, expecting that by the time they got to the chipper that the space would be clear, would not push me in it, and, oh yeah, a guy almost cut off his thumb, I went my own way.
I started my business with limited tree climbing knowledge (lots of solid trad rock climbing experience and some decent forestry felling experience), under capitalized (aka broke/ on a shoe string), with an Astro van, MS 361, MS 192t, rock climbing gear, and $25 eBay spurs. I was trying to do it all at once, reasonably on the level (WC, GL, Commercial Auto Ins, taxes, etc). A super hard row to hoe.
I made it, but could have learned a lot more working for someone successful, building my experience, and taking on small stuff on the weekends, rather than having to pay my rent, then mortgage based entirely on what money I'd have left over from working for myself.
Some people have worked 3 or 4 days a week for another tree service while getting their own gig going, building their equipment, skills, business experience, and client base.
Its been a tough go, but I've made it, not without some considerable strain on my relationship with my girlfriend, now wife, late nights working, early mornings working, lots of coffee, lots more working, more coffee, taking home less than I should have as I needed to bid jobs where I was sure I would get them in order to make the next insurance/ rent/ payroll/ tax payment.
A year ago, as I felt like I was really hitting my stride with my business (3-4 years in), I started working for a gov't agency. That steady paycheck that covered the mortgage and bills sure was nice. Anything I made with my business was above what I 'needed'. I've been able to keep going with both for the last year. We just had a baby a few weeks back. I've been able to turn over a lot of my business to an employee who has worked for me for over a year, and 6 years before that with another tree service, who has management experience. It has been a good feeling to take some of the burden off my shoulders.
I got a ton of good knowledge from The TreeHouse and TreeBuzz. It has been a lifesaver. ISA has been a good thing, too.
You're in a good place here at the House. As you may have seen, we get off topic often times, frequently into some very good OT information, so keeping up on threads, even when they original posting may or may not be of great interest to you, will often be very, very informative.
People are very supportive and helpful to people who are respectful of others here. Hang out.