I am currently in a high risk, potentially high reward situation with a start-up. I love the technologies and the creative nature of the work I am doing with start-up X. I know you are looking for additional employees right now, but since you are growing quickly I suspect that you will be looking again in 6 months and maybe again a year from now. I would love to sit down with you once every 3 or 4 months over a cup of coffee and share some of what I am learning and hear about how things are going with your consulting agency. If things start to fall apart at the start-up or it becomes clear that transitioning to a FT employee is not really going to happen we can talk about whether you folks have an opportunity at that time.

And, by the way can you give me a list of the 3 or 4 biggest gaps in my skill-set? One's that if I spent some effort learning would make me even more valuable to your company at some point in the future?

I suspect that this would make you stand-out to the consulting agency and may help you hedge your bets on a risky venture.

1) What is the funding situation like - specifically, how much capital is available, is any of it tied to contingencies (i.e. hitting a sales number), what are your plans for getting more if it runs out/is there investor interest in giving you more? 2) When do you expect to be cash-flow positive? (incoming cash >= expenses) 3) What's your burn rate? More specifically, given the current rate of cash burn, when is drop dead? 4) When do you anticipate being able to make a decision on whether to bring me on full time if I join you as a contract-to-hire worker? 5) What's the duration of the contract and what are the renewal options if we don't go full time hire?

Three basic criteria to score-

- The Work: is it intellectually challenging? Can you see yourself doing it everyday? Will it stretch you professionally?

- The People: Are they decent, smart, trustworthy? Will they help you up your game? Can you help them?

- Compensation: Beyond the dollars (include perks, benefits, options, bonuses). On asking about comp, simple - "what's your budget range for this position?"

Check Payscale for a quick benchmark >http://www.payscale.com/research/US/Job=Software_Engineer_%2...

- Your long term goals: Do you want a lot of different experiences quickly? Do you want a single place you will work at for years (however unlikely that is these days)? Will these opportunities help, hinder, or have no impact on your ultimate goals?

My final advice:

Sit down and actually write this stuff down. Don't just attempt to intuit the answer, but actually write down the things you want and need. Write down how you think the opportunities will impact your list. If you use that to feed your decision, it will make your choice easier and lead to a lower probability of regret later on.