Bothsides of the Table


Posted on Jul 29, 2015 | 0 comments


To most people it smells. People are afraid of it. It’s like cancer or divorce. When you have it you find you who your true friends are because they’re the ones who double down on helping, on being available, on listening, on understanding. Most people run from failure or disease because they’re hard to handle. Hard to know how to deal with. Awkward.

But I am attracted to those who have had severe set-backs in life because it tells you something about the mettle of the person with whom you’re dealing. It reminds me of a famous quote in one of my favorite novel’s “Damage” by Josephine Hart

“Damaged people are dangerous. They know they can survive.”

And more than anything I love survivors. I love people who have been put to the test – whether by market forces or even by their own stupid mistakes – and come back stronger. But markets don’t generally love failure. It reminds me of the old saying on the topic

“Success has many fathers, failure is an orphan.”

And yet we entrepreneurs who will sign up for the journey accept that failure is a possibility and the true entrepreneurs know that they must stick with the ship even if it’s sinking. Survivors find a way to get through it even though many jumped overboard for the first life raft.

There are many people who I call “wantrepreneurs” because I know that they truly “want” to be entrepreneurs but the failure aspect is too strong. It’s my hypothesis of why so many founding teams have 3-4 founders. There is safety in numbers of saying, “we all decided to do this together” and I believe it’s because failing alone seams unbearable.

But I’ve been thinking a lot about failure in the past year or so.

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The hardest thing about starting a company is that from day one you emerge as this completely vulnerable entity trying its hardest to project success, power, trajectory and inevitability while you secretly know that you’re one knock-out blow from extinction.

Think about it: You start with nearly no money, you bring on some co-founders and if they quit it could completely derail your mission, you talk to journalists who if they decide to be cranky can ruin your reputation, you pitch investors who can change your outcomes by giving you cash that enables more forward progress but if they withhold it you can starve. While all of this is going on you are trying to get customers to use your product, enterprises to sign contracts that don’t leave you with unlimited liabilities and landlords to take you in with limited deposits or guarantees.

In a word – you are truly vulnerable.

Understanding your vulnerability and understanding the power of those with whom you must do business is a very important part of figuring out as a startup how to fit into the broader ecosystem and the art of statecraft is tremendously important in knowing when and how to project power in sales, recruiting, negotiations, fund raising, etc.

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Yesterday I saw two biopic films: “Amy” about the life of Jazz sensation Amy Winehouse who died of alcohol poisoning at the age of 27 and “Montage of Heck” about the life of Kurt Cobain, the grunge-rock generational voice who died of an overdose of heroin and valium at the age of … 27.

It was a heavy day, for sure. Both films were must watches for artistry. They interweave off-stage lives and conversations with amazing musical performances and they both have amazing editing and cinematography.

They are essentially the same story. Each had childhoods with some degree of parental neglect and each suffered from and was diagnosed at a young age with depression. In both cases they turned to hard-core drugs to escape reality – Cobain to heroin and Winehouse to heroin and crack cocaine.

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I noticed this post today from Ezra Galston titled “Dear Brad, Fred & Mark: How The Hell Do You Do It?

The premise is that either I have some magical solutions that allow me to produce a lot of content or I’m super human.


tl;dr version courtesy of Tuvia Elbaum which made me laugh so I’m adding it after the fact. As you can see Tuvia asked me this June 25th. I answered. I get asked all the time. I have the same answer. I sit down to get things done. And I finish.

.@msuster and here’s the shorter version for those who don’t have time 😄

— Tuvia Elbaum (@Tuviae) July 14, 2015


BTW – if anybody at Twitter reads this you need to fix your “embed Tweet” code because as you’ll see from above it doesn’t properly embed when you have a quoted Tweet.

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If you follow the Twittersphere you may have noticed several people weighing in on this recent piece by Mike Isaac of the NY Times, asking “How Many Angels is Too Many?

I found myself nodding through all of it with quotes like,

“Seed investing is the status symbol of Silicon Valley,” said Sam Altman

I myself coined the term ENIFA (everyone now is a fucking angel) in 2011 but it didn’t stick as well as the term Unicorn did. Ah, well. I was trying to cheekily suggest that it was the new status symbol. Sam is more succinct and well-stated than I and I’m guessing ENIFA wouldn’t make the NYT.

One of my favorite entrepreneur-Twitterer weighed in,

“You want to keep tapping into their collective intelligence so you keep saying ‘Thank you for the feedback’ and they keep sending it,” Ms. Morrill said.

“But then you are sitting there alone at 3 a.m.

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