How founders should think about choosing a business structure, weighing liability, taxes, and the ability to raise money against the company's actual goals.

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How founders should think about choosing a business structure, weighing liability, taxes, and the ability to raise money against the company's actual goals.
THE MOST POPULAR ENTITY ON THE PLAYGROUND
We are taught in the most basic business law courses about the various types of entities available to individuals endeavoring to become the boss of their own slice of the American pie. It is law school 101. Much of the focus centers around corporations and partnerships, there is mention of the limited liability company (LLC), the professional limited liability company (PLLC) and the sole proprietorship. Yet in practice, outside of the classroom, one entity reigns supreme: LLC. Many of our clients sit down already convinced that the LLC is for them. Some may not even understand why, but this popular business entity has taken over the small business playground. Here’s why.
CD's for Questions #1: S-Corps vs LLC's
Question: Any reason to incorporate as an S-Corp rather than LLC (in NY)? Other than cost of publication? Tweeted out by: @jasongelman.
CD Saved: Think About Life, "Family." For the whole "CD's for Questions" explanation, see here.
[First things first: if a startup will be seeking VC financing, they should know that prior to closing that financing, the startup will have to be a c-corporation. VC's will not invest in pass-through entities, like LLC's and s-corps. Delaware law makes it easy from a corporate perspective to convert these NY entities into a Delaware c-corp (the state preferred by VC's). Plenty of startups initially form their entity as a pass through, take the benefit of the losses on their personal income taxes and then convert prior to a VC financing. However, depending on the business, there may be adverse accounting ramifications to a conversion.]
I generally favor LLC's because of their flexibility. As products of the 90's, LLC's tend to have less corporate formalities than corporations: internal governance and economic understanding among the members tends to be more the result of contract law, set down in the entity's operating agreement.
As a result of its recent vintage, there are some uncertainties with respect to the LLC form. For instance, how much in the way of fiduciary duties can a NY LLC contract away? These issues are still being litigated; legal blogs are atwitter with recent Delaware case law on this issue.
On NY's LLC publication requirement, depending on the circumstances, I may advise startups not to comply. More detail can be found here.
S-Corps tend to be more rigid and limiting. For instance, there can be only one class of shares in an s-corp. An investor cannot be issued equity with any economic or control preferences as compared to another shareholder. The number of shareholders in an s-corp is capped at 100. No foreign shareholders are permitted. And only individuals can own shares of an s-corp.
The one advantage I've found with an s-corp is a potential savings in the self employment tax. For a good description of how it works, see here. But I know other accountants who are not comfortable with the trick.
Again, I generally favor LLC's, but I've seen other skilled advisors go the s-corp route.
Think About Life, "Family." I discovered Think About Life on an online blog and since then have caught them live around half a dozen times. Each time is a better dance party than the last. You can cancel your gym membership. "Family" is their sophomore release; this CD is from the Canadian pressing on Alien8 from May 2009. Standout track: "Havin' My Baby."
@jasongelman: Sweet tunes are coming to you! Wife Safdie sends her gratitude.