Many of my clients are concerned about confidentiality when we start working for the first time together. Especially after I ask them for the company financials, cap table, and product development timeline, all essential ingredients for an investor presentation.

Some clients require signing an NDA. Unlike VCs, I sign them if they are capped in time, and do not contain non-competes. But many clients, actually don't bother. Here is why your secrets might be safer with a 1-person freelance organization than a larger company:

• The cost of a data breach is much higher. Even the slightest hint of an ethical issue will put me out of business. For big companies, it is a legal issue that can be dealt with in dollars. But, this is hardly ever going to be an existential issue.
• One person firms are better at controlling information flow than large companies with lots of different departments, with lots of different subcontractors in lots of different locations.
• Good freelancers probably have a 100% full work pipeline, and select work based on the interest or creative challenge rather than a need to fill the empty capacity of a bank of designers waiting for work downstairs. As soon as a prospective client really gets interested (wink, wink) in knowing more about the specifics of the work you did for a competitor, it is a good sign to walk out of the room.
• A free lancer works directly with the client, so the eye-to-eye handshake is a personal contract signed with your consciousness. You are not wondering whether you violate a contract, but whether you are breaking someone's trust.

Image by We are Neo on Flickr