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Stay SaaSy

Writing about scaling enterprise SaaS product and engineering teams from $0 to IPO and beyond.

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Substack
PricingOnly free issuesPublishesWeekly
Issues193Founded3 years agoLast Issue2 days ago
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Latest Issues

The Same Side of the Table

Imagine that you’re in a board room, locked in an intense negotiation. Maybe you’re selling your company, maybe you’re signing an NFL contract, maybe you’re fighting a legal case. During a negotiation, there’s a lot of meaning to what side...

2 days ago
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The Big Management Lie: Overpromising

Everyone knows that lying to your team is bad. Only a complete sociopath would argue that lying to your team is a positive, happy activity. But there’s a particular form of lying that many of the most experienced, compassionate, and honorab...

10 days ago
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1

The Best Prioritization Is No Prioritization

In the course of conversations with startups that I’ve invested in, that I advise, or that I simply encounter, it’s very common to get into discussions about prioritization.

Some common situations that I hear about all the time:

  • We do...
18 days ago
33
3

What I'd Tell My Team About Competition

A lot of people simply don’t understand the degree to which competition matters in B2B software, and what competing effectively feels like. Competition is simply the art of increasing your win-rate when you and a competitor vie for the same...

a month ago
21

Riding Technology Waves

Technology businesses are heavily influenced by waves of technology change, like the rise of the internet or AI. Knowing how to adjust strategy for these changes is one of the most important skills to develop.

As technology has advanced, t...

2 months ago
9

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