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When you look at the books, you are looking for the monthly burn. Focus on the last 3-6 months. Anything prior to that is just about meaningless. You want to know who (what firms) led each funding round and who is on the board from each. Success is driven by the team and and burn rate. Market size matters very little to most start-ups once you determine there is a market. Good board members (people that have helped take companies to great liquidity events) are critical, as are the other leaders.
Ask to see the books. Look at the pipeline and the receivables and ask questions about both
Good advice above - but IME - @ the end of the day, ask yourself if you are comfortable with the company cratering in 6mo regardless of your diligence & the strength of the management team/board? I went to a well-funded startup years ago. There were warning signs and the doors closed 1 year in - but I would do it again in a heartbeat just for that experience.
I might be one year away from being “ok” if it cratered in 6 months...guess I’ll have to wait...:(