Stay SaaSy

Defensive Driving For Your Career

Quick update: We’ve also launched a small section of merch if you want to Stay SaaSy all day!

Sep 22 • Stay SaaSy

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August 2026

Book the Meeting Before You Need It

Bring order to your operations.

Aug 17 • Stay SaaSy

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The Same Side of the Table

You've got to be on the same side of the table as your team.

Aug 13 • Stay SaaSy

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The Big Management Lie: Overpromising

Everyone knows that lying to your team is bad.

Aug 5 • Stay SaaSy

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July 2026

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…

Jul 28 • Stay SaaSy

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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.

Jul 16 • Stay SaaSy

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June 2026

Riding Technology Waves

Technology businesses are heavily influenced by waves of technology change, like the rise of the internet or AI.

Jun 23 • Stay SaaSy

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Don't Stack Weaknesses

Org charts with stacked weaknesses end in disrepair.

Jun 17 • Stay SaaSy

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What It's Like To IPO

What It’s Like to IPO

Jun 5 • Stay SaaSy

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April 2026

High Amplitude Disagreeableness

True startup people are one of the most important advantages that many tech companies have.

Apr 16 • Stay SaaSy

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March 2026