My friend owns and operates two locations of his company. They are apparently doing so well, he's opening a third and looking for people who'd like to invest.

I need to k ow how to know if it's a good idea knowing my financial standing and the company's. Buddy sent a detailed .pdf with a ton of information but most goes over my head.

What's the first step in finding someone to walk me through this? (Prefer it not be my buddy)

He's offering equity in the company. Something I'm interested in.

Find someone who this does not go over their head and pay them. Questions I'd ask:
What's the investing structure?
When do you get paid back and how?
What is the historical P&L of each location and will the additional location be able to perform as well and reach its investment objectives?
How does the expected return compare with simply investing in the stock market?
If he fails will you miss the money and will the friendship recover?

Most important question:
1. Do I trust my buddy as a competent and successful professional that will achieve the stated goals? Some people are great drinking buddies / FFL friends but maybe not the best financial investment.

Just review the corporate bylaws and any existing or pro-forma financial statements (which might be in that pdf he gave you). If this is his 3rd and the other two are doing fine, it's probably a good investment. Understand how much $ gets you what % of the company and try to make a value judgement.

I know of one Montessori school that sold for $5MM a few years ago. Given the right location and leadership, it can be a great opportunity.