The most important takeaway from the Adir Shiffman and Sleeping Duck litigation, in which Shiffman lost is that startup founders, investors, and other parties should ensure any agreements they think they have are formalised and legally enforceable. But we didn’t have to wait for a multi-million lawsuit to find out that.

The case did, however, offer a fascinating insight into an area of the early-stage startup investing industry which receives much less media attention and scrutiny than conventional venture capital.

Shiffman is a good example of a “lone-wolf angel”, i.e. an investor who invests alone in startups, with aggressive terms and wants more than equity.

In this case, a relatively modest $100 investment secured Shiffman’s 5% of Sleeping Duck, with an option to purchase a further 5%. He also claimed that the investment gave him a voice in the daily running of the business.

Shiffman currently owns 9.4% of the company (with an option to acquire 10,000 shares). Despite the loss, Shiffman told i>Capital Brief/i> that he a href=”https://www.capitalbrief.com/article/exceptionally-painful-breakdown-shiffman’s-wont change his investing style despite sleeping duck court loss.bfdc6ce1″>doesn’t intend to change Shiffman currently owns 9.4% (with the option to purchase 10,000 additional shares) of the company, but despite his loss, Shiffman told Captial Brief that he does not intend to change his investing strategy.