The Good Angel Investor (Part 2): After the Closing

By: Paul A. Jones 

In Part 1 of this post, I focused on issues entrepreneurs and angels should think about as a seed deal comes together. Today, I want to focus on how angels can engage with entrepreneurs after the money changes hands.

Foremost among post-closing advice for angel investors is this: never forget that as an angel investor, you are a coach, not an athlete. Many angel investors have been successful entrepreneurs themselves and one of the “value adds” that these angels can bring to a startup is the benefit of their own entrepreneurial and management experience. But good angels understand that their role is to give counsel, not orders. Few things make for a more unhappy and usually dysfunctional angel/entrepreneur relationship than an angel who thinks he is, or should be, making decisions rather than offering advice and counsel.

Good angels also remember that the business plan they invested in will likely change quite a bit, and often within months, or even weeks, of the closing date; “Pivoting” is the nature of the high impact startup beast. If you are skittish about major changes in direction based on less than complete information, high impact angel investing is probably not for you. Once in a deal, your thoughts and perspectives on pivots should be shared with the entrepreneur, but always with the caveat that that the entrepreneur should make the call.

Expanding on the pivoting theme, angel investors in early stage high impact startups should remember that mistakes will be made, most likely quite a number of them, as a startup matures. In more traditional businesses, the first thing that happens when a mistake is discovered is usually a search for someone to blame. Later on, after the appropriate parties are duly punished and steps are taken to reduce the risk of future mistakes, the focus shifts to correcting the mistake.

At high impact startups, mistakes are thought of more as learning opportunities than career killers. Entrepreneurs that don’t make mistakes are likely not sufficiently pushing the envelope, and entrepreneurs who don’t promptly learn from mistakes and move on seldom find much success. The angel investor’s role in all of this is to hold entrepreneurs accountable for mistakes, that is for timely recognizing and learning/recovering from those mistakes. Angels who take the more traditional approach of assessing blame and punishing the malfeasors simply waste resources, undermine entrepreneurial confidence, and discourage prompt recognition of mistakes going forward.

Taking a “let’s learn from this and move on” approach to entrepreneurial mistakes is important, but so is establishing a culture of accountability. Being supportive, even entrepreneur-friendly, does not imply passivity. Particularly for angels who are on the Board of Directors, being pro-active about regularly asking the hard questions about the business is a critical part of the job.  Think of it like this: as an active angel investor, it is your job to make sure that when the entrepreneur starts pitching new investors for the A round, she doesn’t get any questions you have not already asked. If she does, she should hold you accountable.

Finally, good angels understand that as the company grows, their role will decline, in most cases precipitously. Typically, the arrival of a solid lead investor for the A round marks the beginning of the end for the angel as a key member of the entrepreneur’s cabinet. Angels that want to stay as close to an entrepreneur as possible are wise to recognize this rather than fight it. Even angels that still have a lot to contribute are best served by moving off center stage, if only because that is ground the downstream investors understandably consider their own.


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