The Downsides of Large Syndicates

There were some great comments on my post from Sunday titled Being Syndication AgnosticOne of them was from Kevin Vogelsang – he asked the following question:

What are the downsides to syndicating a round of financing for the entrepreneur/startup (assuming the relationship with all investors is a good fit of course)? By syndicating a deal, the entrepreneur gains access to a larger network. This seems to be a big positive. However, there must be downsides (less attention, more interest groups, etc.) Love to hear more on the topic.

While there are plenty of downsides, I’m going to take on five common ones in this post. 

Too Many VC’s on the Board: Most VC’s want a board seat when they invest in a company. At the early stages this is usually manageable (although not necessarily desirable).  However, once a company has raised several rounds of financing and built increasingly large syndicates, this can quickly get out of control.  The largest board of a VC backed company I’ve ever been on was 11 (8 VCs, CEO, founder, one outside director).  It was a completely ineffective board.  Now, the board size problems can be dealt with by a strong CEO and a strong lead investor who will help the CEO organize the board in a manageable way, but it has to be done proactively.

Too Many People in the Room: This is a corollary to “too many VCs on the board.”  If the VC doesn’t get a board seat, they’ll want an observer seat.  In addition, most later stage VCs or strategic investors want observer seats.  Suddenly even though you’ve managed the size of the board effectively, there are a bunch of people in the room.  I’ve been in board meetings with over 20 people in them (I don’t know the exact max, but I’m going to guess it’s around 25 since eventually you run out of chairs.)  Not surprisingly, these tend to be weak or inefficient board meetings with separate “executive committee meetings” where the real board meeting happens, and then another three hour song and dance for the benefit of the 15 other people.

Both of these are a natural result of most investors in private companies wanting to have a seat at the table.  While a reasonable expectation, it’s important for the CEO and founders to set an appropriate tone and expectations with their investors early on so that there’s actually an effective board, investor, and company dynamic as the syndicate gets large.

Misalignment of Interests: With each round of investment and each new investor comes new expectations.  As the syndicate size grows, the chance of interests between parties getting out of alignment increases.  This is especially true when each round has different dynamics beyond price (such different preference structures, protective provisions, voting thresholds by class of stock, and various participation caps.)  When everything is going well this isn’t an issue, but the minute the business goes sideways (or worse) strange things start to happen.  As the situation degenerate, the knives (or flamethrowers) come out.  I’ve been involved in situations that resulted in the destruction of companies that deserved to live another day because the investors around the table (which included me) couldn’t get their collective shit together.

Decision Vacuum: This is a corollary to “misalignment of interests.”  It’s similar to when I lived in a fraternity at MIT and a dozen of us would stand in the hallway trying to figure out where to go out to eat.  This drill could go on for a while, especially if we had a keg of beer (or, er, something else) nearby.  Eventually someone stepped into the decision vacuum and said “I’m going to Mandarin – come with me if you want” (well – that was what I usually said – others had different choices).  Whenever you’ve got at least four VCs sitting around a table, you run the risk of a decision vacuum forming (queue snarky jokes here).  If you are a CEO of a company and you see a decision vacuum developing, grab a bunch of matter and get in the middle of it.

Lame Duck Syndrome: There has been plenty of personnel changes in the “VC business” in the past five years, including plenty of firms that are winding down, have shrunk in size (and let partners go), and have disbanded.  However, they are still investors in your company and some of them still sit on your board.  In some cases they are just hanging around to “protect their investment” although they have no ability or interest in putting additional capital into your company.  Now – some folks in this position are incredibly helpful, but many don’t do much more than show up.  And – the more of them like this around the table, the less fun it can be.

Now, there are plenty of other downsides as well as plenty of advantages of large syndicates.  If you’ve got additional ideas, or stories to share (especially horrifying ones showing the downside), comment away even if you change the names to protect the not so innocent.