Stay SaaSy

No Pain, No Gain

One of the biggest mistakes is shielding people from the pain they need to learn.

Sep 15 • 

Stay SaaSy

29

2

Episode 3: AI Hottakes

Aye, I don't know what you expected?

Sep 4 • 

Stay SaaSy

1

2

29:13

August 2025

You Know What To Do

One of the most consistent observations I’ve had in my time in startups, scale-ups, and public companies is that smart people with context on a tricky…

Aug 22 • 

Stay SaaSy

28

1

Episode 2: Rapidly Roadmapping

A lightning round on a thunderous topic.

Aug 18 • 

Stay SaaSy

1

11:13

You Have Too Many Metrics

What's in a measure?

Aug 4 • 

Stay SaaSy

29

2

July 2025

Episode 1: Winning From Third Place

THE PODCAST IS HERE!

Jul 25 • 

Stay SaaSy

7

3

21:28

Naming Software Teams

What's in a name?

Jul 7 • 

Stay SaaSy

18

June 2025

We Tried That

Past results are not indicative of future results.

Jun 26 • 

Stay SaaSy

19

Your Manager Is Not Your Best Friend

As people become managers, it’s quite common for their team members to want to commiserate with them.

Jun 3 • 

Stay SaaSy

29

May 2025

AI Makes Bad Managers

Know where AI is a crutch and where it's an abstraction.

May 27 • 

Stay SaaSy

16

3

Setting Startup Policies

One of your most important activities as an executive, especially at a startup, is to set policies: Sets of guardrails or rules for how company systems…

May 6 • 

Stay SaaSy

10

April 2025

Leading From The Front

Don't look back.

Apr 21 • 

Stay SaaSy

21

1