I started with a Pro Photography Studio, which I sold in 1st year university and switched my major from Film to Accounting/OB.
While working for a few seconds as an Accountant (2nd year) I realised that I could make more money as myself and started an IT consulting shop (in 1988!)
By 1994 I had offices in Toronto, NY, and Mexico City and started selling off the clients.
Many of my clients were in advertising & Marketing so:
I started a Marketing Company (Technology based - database, web, IVR, etc.), which, in 1999 I sold to WPP.
Shortly after I started to build office buildings in Russia - until the Yukos thing hit the fan.
Now I have an Consumer Auto Finance Co.
www.maclease.ca for people with bad credit.
Throughout the whole process I have been involved in several start-ups and various Merchant Banking projects.
My wife is in Real Estate Development with projects all over North America.
My advice to anyone starting or thinking about starting anything:
1) Create a long term biz plan
2) Forcast revenues and expenses out two years
3) Figure out how to operate on half to 10% of your revenue forcast
I have seen more business fail that rely on lots of start up capital than businesses that don't rely much on startup capital - that IS the secret!
If you have a biz idea I'm always happy to be "grey hair" and chat, I don't need the $$ and I'm not an investor (I invest in my own stuff only now), but I've travelled the road a few times and am happy to point out pot holes!