I think that depends how transparent you are on your business practices. Running anything on a single server is dumb, but if you are one man shop running on EC2

I think that depends how transparent you are on your business practices. Running anything on a single server is dumb, but if you are one man shop running on EC2 and you are clear about that I don't think it's a big deal. Explain what you do, and why it's good. Explain how you've thought about BCP and making sure everything will stay up (essential for a service). Companies routinely hire individual consultants at $2k/day and follow their advice. I don't think that trusting a well respected individual in the industry is so much the problem, as trusting someone who's capability is unknown. If you show the capabilities of you and your systems up front, without BS, then people will take you on for projects that are appropriate to that level of risk. Which may be quite as much as you can handle.