How to pick a winner in life and in venture cap

Picking.

You can pick your fruit at Vons, you can pick your nose (in private) and you can pick which company to invest in. Making a choice is hard. Sometimes, you miss it and leave the ripest avocados in the bin.

A couple of weeks ago, Howard Morgan, one of the most famous venture capitalists, came to town for a fireside chat. Morgan is the founder of First Round Capital. He is 73 and he has done it all (easy to find his background on the web). The topics were wide ranging, but he spent some serious time on two — hiring people and picking investments.

First Round sees 5,000 submissions over the course of a year and by the end of the year they invest in 40. The dilemma Morgan describes is this: “If I could start the year with all 5,000 at the top of the funnel … then, with all of them still available, picking the best ideas and the best teams would be much easier.” But, my dear readers, it doesn’t work that way. You can only see what you see at the time and after you have passed, that deal is gone. It is a VC mantra to almost never come back and reopen a deal. Once it is passed on, to quote my favorite shark, “You’re dead to me.”

Now, think about hiring. The same dynamic is in play. Betty and Bob are available today, but they will not be available in a month. Your dilemma is that you have to pick from what’s available at the time. Sorry, no ripe avocados today. This is classic Tinder. Swipe, gone, oops, she/he looked really interesting, but wait, can I go back? No.

Now, finally let’s bring picking to the only thing that really matters in your life — your partner. So, how do you pick a wife? You can’t keep looking until you are 92, and if you pick at 18 you will only have seen a small slice of the potential pool.

It turns out that Morgan has developed “the Morgan algorithm” for partner picking. He says (with a wry smile) to pass on the first 37 percent of your available pool, and then take the next one that is significantly better than the previous one before. He has been married to his wife Eleanor for 51 years. (Good algorithm, huh?)

There actually is some serious technical brain power devoted to machine learning and picking (dynamic programming, stack overflow, etc.) but the “look back” in time factor is not easily overcome. (I wonder what happened to my first girlfriend in college.)

I know VCs get a lot of picks right, but they also get a lot wrong. Here are some stories. First Round saw Airbnb very early and they passed. Why? Simple, Morgan went home to his wife and said, “Sweetie, would we ever let someone we didn’t know come over and sleep on our couch?” She said she would divorce him on the spot if he did something that crazy. The flaw in his thinking — the Morgans live in a Fifth Avenue penthouse, not in a two-bedroom condo.

So let me share a few more courtesy of some refugees from the Harvard Business School. Flybridge Capital passed on Twitter — “How many people want to tell everyone randomly what they are doing?” OVP missed Visio. X-Star Partners missed on GitHub (they were outbid). Summit Partners passed on Just Eat — currently valued at $5 billion on the FTSE 100.

Tim Draper, a famous VC, passed on Netflix. He wondered why anyone would send DVDs in the mail when streaming was coming in a year or two. (Right thinking, wrong timing). The New York Angels passed on Tote — before it pivoted to become Pinterest.

The point of all this is simple. VCs are standing on the bank fishing in the river, and they get to see what comes by. You are swimming up the river and can always find new fishermen.

As for wives, well I am not going there. The one I have still loves me, and I am not planning to explain the picking algorithm to her. What she doesn’t know can’t hurt me.

Senturia, a serial entrepreneur who invests in early-stage technology companies, writes weekly about entrepreneurship in San Diego. [email protected]