The entrepreneur and loss

A few days ago someone I know posted a note saying his father died.

He was unusually blunt in his assessment of the circumstances, and of watching his father suffer through hospital care when all he wanted was to go peacefully. 

Entrepreneurs tend to absorb a great deal of grief. This is true of all humans, but the risk undertaken building a company from scratch leads to a deeper emotional risk than most people are willing to take. 

It’s most frequently expressed by a conflicted relationship with winning and losing. We tend to punish ourselves for loss because we assume internally that we are strong enough to navigate all currents, if not direct or control them. 

A friend who works in / with startups wrote about that dynamic a few months ago… 

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The difference between a poverty and scarcity mindset

A few years ago there was a Forbes post entitled “If I were a poor black kid.”

In it, the author (who is not poor, black, or a kid) imagines some ways disenfranchised children might use technology to get ahead, including via tools like Skype, Google Scholar, and Evernote. You can get a deeper look at his views via comments on this NPR response to the column.

The question that struck me while reading it isn’t whether or not he wants to be helpful (I think he clearly does), it’s that he wrote a piece from the perspective of someone he didn’t understand, whose experience he only casually related to. 

More plainly, he wanted to solve a problem without first understanding the person having it. 

This type of thinking comes up frequently when people talk about poverty who have not themselves experienced its’ paralyzing effects…

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Telling one story a day about the people who use what you create

Building a company from scratch is exhausting. 

Entrepreneurs need various kinds of support to stay afloat —understanding friends and family, tough advisers / mentors, a good reading list to encourage contemplation, these are all important.

But the best source of support is the people actually using what you build. Their stories are the ones that open up your world when you’re thinking too narrowly, and provide inspiration to keep going. While solving a problem for one person typically doesn’t justify a stable small business or a rapidly growing startup, it’s the starting point for everything else. 

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The emotional state of an entrepreneur

Entrepreneurship is largely about belief.

Sometimes that belief is what keeps us going, but it can also lead to dangerous territory — like listening mostly to people who think the same things we do, or shelving deeper feelings for years only to find out later that they are subconsciously undermining our best work. 

A common mantra in the startup ecosystem (besides hustle, scale, and growth) is that you should test your assumptions. There are different approaches to testing, including the well known lean startup method that Eric Ries advocates for. It’s a concept that’s also well covered by Steve Blank, Seth Godin, and an array of designers, technologists and thinkers. 

With the exception of Seth, most of the time the language / framework for testing assumptions is focused on developing & designing a product or learning from customers, and rightfully so. As soon as an idea gets out of your head, into the real world, and beyond a small circle of people… that’s when challenging your assumptions becomes critical. 

But there’s another, slightly different way of thinking about it: you’re testing what you believe to be true, not only about your product but about yourself. 

Nowhere is this more evident than in how we avoid, deal with, process, or even embrace our emotional state in times of turmoil, whether it happens quickly or over a long period of time.

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On the importance of frameworks

I’ve never seen a business plan that looked like a business. 

I’m not sure exactly why this is, but it probably has something to do with the fact that in the early stage of any company there are a lot of variables, and things that seem to mean one thing can easily turn out to mean something else entirely. Sort of a particle / wave duality principle, but for startups.

(A high number of people who sign up for a product trial, for example, might not be a positive sign if none of them stick around once their two weeks is up — possibly indicating that your inbound growth levers need tweaking). 

For many entrepreneurs and startups, frameworks occupy a critical space — the one that arrives after “I have a bunch of ideas” but before “here’s the full plan to take over the world.”

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