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Enjoy Every Last Bit of the Upside

Yesterday I listened to a podcast on which Bill Gurley was interviewed. Bill is a partner at Benchmark, a highly regarded West Coast venture capital firm that made early investments in companies like eBay, Uber, Instagram, Zillow, and Snapchat. It’s in the top tier of U.S. venture firms because of its outsize returns to investors.

Bill has been a technology investor for many years. He experienced the dot-com bust and the financial crisis. On the podcast, he shared what he learned from previous downturns: “the best way to protect against the downside is to enjoy every last bit of the upside.” I was surprised. To summarize his explanation, he said that the biggest returns usually come from investments made at the very end of a cycle. If you pull back too early because you’re anticipating a downturn, you’ll miss the best investment opportunities. He didn’t say this, but I assume he thinks that timing a downturn is nearly impossible so people should stay the course until the downturn happens.

Bill is embracing the current reality. He’s accepting his situation and investing accordingly until trends turn and there’s a new reality.

I’ve thought about this and debated with others it over the last day, and I think Bill makes a good argument. Accepting (rather than fighting) a trend positions you to take advantage of whatever opportunities it presents. So what if you don’t like the trend? The trend doesn’t care. If you fight it because you think it’s wrong, you don’t understand it, or you think it will (should) change, you’ll miss out.

This isn’t applicable to everyone or to all situations, but it’s an interesting perspective and food for thought from a wise and experienced investor.

Think of Investors as Partners

I’ve shared my views on the importance of bidirectional relationships, which I believe is one of those good-life principles. But for entrepreneurs, understanding how to approach relationships with investors is imperative.

Don’t view a good investor as a cash machine, but rather as a partner in building your business. Yes, they provide capital and seek a return on it, but they can also add value in a variety of other ways. They can make warm introductions to potential customers or vendors. They can tap their networks to help recruit for key positions. They can help you navigate turbulent times by sharing their experiences and strategizing with your team. A good investor may invest a lot of time as well as money. They aren’t just making an investment in your company—they’re investing in the founder—you—too. Quite reasonably, they are likely to want to get to know you before making an investment. In fact, they like to establish the relationship long before they commit funds.

These ideas may help entrepreneurs approach investor relationships correctly:

  • Pitching – Don’t expect to walk away with a check. Their feedback can be many times more valuable, especially if you’re early stage. Pay close attention to it. And ask questions. Two good ones: “Is there anyone you think I should know?” “Can I help you in any way?”
  • Updates – Send them a clean, succinct monthly update. This will help keep you top of mind. Have a clear ask.
  • Touch base – Periodically reach out to ask them what they’re up to and how they view certain markets. Share some of the things you’re doing that may not make the update. Ask if you can connect them with anyone or help them in any other way.
  • Make connections – If you know someone who could benefit from knowing the investor, or vice versa, make the intro. Both will appreciate it.
  • Share knowledge – If you learn something that you think an investor could benefit from knowing, pass it on.

Approaching relationships with investors correctly can be a game changer. Start developing them early.