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Sam’s Newsletter

Writing and essays from @gerstenzang

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The Emotional Cost of Finding Product-Market Fit

It takes a lot to take the leap and start a company. And knowing when to pivot is the single hardest problem in startups.

Breakfast with Jim: notes from the founder of Costco

We discussed Costco's beginning, how it built its brand, competition with Amazon, and how to operate

The Role of the Critic

There’s a popular Silicon Valley view that a founder or company should not be criticized.

Summoning the Courage to Focus

Focus is *the* key lever of strategy but it’s so often misunderstood, and even more frequently ignored.

How Boulton & Watt is structured

Most incubators are structured in a holdco + fund model, which beyond being significant work to administer, has a number of trade-offs.

Startup Operating Principles

After three and a half years, this is a compliment of sorts to Operating well – what I learned at Stripe.

Hiring before playbooks

[Ed.

How many businesses-in-a-box are there?

Every category has a transition point from when the ‘easy’ things get done to when the hard ones remain.

Steel threads: the single most important product market fit technique that I use (that no has heard of)

I learned about the engineering concept of ‘steel threads’ about ten years ago from a colleague who had come from Microsoft.

Option A vs Option B

So much of being a founder is staring down two options and neither looks particularly good.