Stay SaaSy

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

13

2

The Big Management Lie: Overpromising

Everyone knows that lying to your team is bad.

Aug 5 • Stay SaaSy

25

1

2

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

33

3

4

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

21

3

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

9

1

Don't Stack Weaknesses

Org charts with stacked weaknesses end in disrepair.

Jun 17 • Stay SaaSy

22

3

What It's Like To IPO

What It’s Like to IPO

Jun 5 • Stay SaaSy

16

April 2026

High Amplitude Disagreeableness

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

Apr 16 • Stay SaaSy

28

4

5

March 2026

January 2026

The Most Important Teams in Tech

The most important teams in a B2B software company are engineering and sales.

Jan 16 • Stay SaaSy

24

1

1

December 2025