Sticking with the struggling investments

He's right, but I would go further. One of the hardest things to do in the venture business is to stick with a struggling investment.

I woke up thinking about this as I spent yesterday with Josh watching the hapless Jets lose badly to the Dolphins and then heading up to MSG to watch the equally hapless Knicks lose to the Pelicans. It is tempting to stop watching both teams and sell off our seats at MSG for the rest of the year. But we aren't going to do that and we will sit loyally and watch loss after loss at the Garden if that's what comes for the rest of the year. We are fans, even if our team sucks. And they sure do right now.

It is equally tempting to write off a failing investment and stop showing up at board meetings, stop responding to the emails from the founder, and stop thinking about the company. At some point, the company will run out of money, there won't be a reason to put more money into the company, and the investment will fail. Until that happens, as long as the founder is willing to listen to you, I think you have to give your struggling investments your all.

The truth is the investments that are working often don't need that much from an investor. They need more capital, they need recruiting help, and sometimes they need strategy and advice. But the reason they are having success is they are doing the right thing and doing things right. On the other hand, the struggling investment needs a lot of help. And I think the lead investor board member has an obligation to provide that help.

One of the characteristics of USV that I am most proud of is that we stick with our struggling investments. And we have made a lot of them. We have way more of them than our successful ones that are always cited when we are talked about publicly. I think how you treat your struggling investments says more about you than how many billion dollar exits you have had. You need both to be successful in the VC business, of course. The latter metric defines your selection acumen. The former defines your empathy acumen. And when I pick people to work with, I look for the latter. I suspect most people do that.

This is not a new theme. I've written about this here before. But it is an important theme for me and for entrepreneurs and investors. As we headed out last night to MSG Josh said to me, "I am not feeling good about this game". I told him I wasn't either, but all we could do was root them on as hard as we could. We did that. And we will do that again on Thursday when they head out to Brooklyn to play the Nets. We will be there too. That's what fans do and what investors should do too.

(Fred Wilson is a VC and principal of Union Square Ventures.)

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