When you were in middle school, one of the assignments in the fall was to tell what you did on your summer vacation.
OK, teacher, herewith.
First, let me explain that my bride Barbara Bry and I go to New York City several times a year. We are classic tourists: museums, theater, Staten Island ferry, Soho etc. And there are always entrepreneurial lessons to be learned.
When the pilot of the airplane comes on to talk to the passengers, 92.37 percent of the time he is not going to tell you something you really want to hear. In April, we were 20 minutes from landing, and the pilot explains that the airport is closed due to bad weather, and we are running out of fuel. And the next stop is Syracuse.
The corollary to this is when your main investor calls just before he is supposed to fund and tells you that his brother-in-law has been hit by a truck, and the money was in his name.
Lesson here – try to be “anti-fragile.” Other plans quickly need to emerge, and even better should be anticipated. (Pack clean underwear in your carry-on.) This is the classic, not all the eggs in one basket and even better, bring some beef jerky in case the basket breaks.
On the next trip, we are invited to a lunch at the “most exclusive club in New York.” Think carefully here Neil, are you trying to hustle him for dough or is he trying to hustle you? If you do not know who the sucker at the table is, it is you. By the way, fancy, shmancy (I had to wear a suit), the fish was overcooked. And yes, I was the one being poached.
A very long time ago, I made a short film that opened in New York. Good reviews, but the investor lost money. I needed to fix things. I called him, and we met at a deli. We had turkey sandwiches, and I apologized. I was deeply embarrassed that I had waited so long to reconnect. Lesson here is simple. He had forgiven and forgotten, and wondered why I had been distant. Shame has no place in entrepreneurship. Tell the truth, press on.
And do not only call people when you want something. Dig wells long before you need water.
On a lark, we go to an auction at Christie’s. One day it’s watches. The other day it’s precious jewels. Yes, it is exactly like you see in the movies. It is theater for the 1 percent. I would not know a Daytona Submariner from a Timex, but it seems lots of people do. Worst case, consider a sun dial.
We get invited to an afternoon startup tech blah blah, sponsored by a big-time law firm. Almost did not get in as it seemed we were past the use-by date.
There were the usual suspects. But one story stands out. We meet two bankers, escapees from First Republic. Barbara and I are starting another little company. We could bank with them, and in addition, and more importantly, we offer to help them establish a beachhead here in the San Diego tech community. We give them our card and ask them to call us.
Crickets. Not a word. The two guys never call us. Lesson here is simple. If you go to these events where you are supposed to network and someone throws you a beach ball, catch it. You never know.
The ultimate irony is that while we are in New York, our little company lands its first two customers. Now we actually need a bank. You’ve got to love arrogance in the service of stupidity.
Finally, know your audience. The speaker on the tech panel was a big shot. The room was filled with startup founders, seeking a pearl or two of “relevant” wisdom. Telling them about his initial public offering was only self-serving. But nice to know he rode it down from 100 to banjo picks.
He talked too long, he dropped big names, he was narcissistic and egomaniacal. I had actually tried to do business with him 13 years ago. I thought he was a jerk then. Opinion remains the same.
The lesson here is simple. Always offer humility and understanding.
Rule No. 813: Sinatra never had to contend with the traffic.
Senturia is a serial entrepreneur who invests in startups. Please email ideas to [email protected]