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How to Talk About Your Competition

Jul 8, 2025

•

10 min read

How to Talk About Your Competition

Without sounding like a jerk

CJ Gustafson
CJ Gustafson
Preparing for Google Zero

Jun 24, 2025

•

15 min read

Preparing for Google Zero

How will we find customers when moats for distribution vanish?

CJ Gustafson
CJ Gustafson
How Upwork Optimizes LTV to CAC

Jun 12, 2025

•

3 min read

How Upwork Optimizes LTV to CAC

A Masterclass in Marketplace Economics

CJ Gustafson
CJ Gustafson
Is Product Market Fit Getting Harder to KEEP?

Apr 22, 2025

•

6 min read

Is Product Market Fit Getting Harder to KEEP?

How has AI changed our definitions of escape velocity?

CJ Gustafson
CJ Gustafson
When Churn Is the Model

Apr 15, 2025

•

8 min read

When Churn Is the Model

"Designed to be deleted"

CJ Gustafson
CJ Gustafson
A Deep Dive into TAM Calculation Strategies

Dec 12, 2024

•

2 min read

A Deep Dive into TAM Calculation Strategies

How DDOG, CRWD, and NOW calculate TAM

CJ Gustafson
CJ Gustafson
You have your whole life to write your first record, and only 12 months to write your second.

Oct 29, 2024

•

9 min read

You have your whole life to write your first record, and only 12 months to write your second.

The trials and tribulations of going multi product

CJ Gustafson
CJ Gustafson
Pulling the Future Forward

Oct 6, 2024

•

10 min read

Pulling the Future Forward

10/06/24 Benchmarks for Operators

CJ Gustafson
CJ Gustafson
Your Complete Guide to Customer Segmentation

Sep 26, 2024

•

15 min read

Your Complete Guide to Customer Segmentation

Identifying your best customers to maximize lifetime value

CJ Gustafson
CJ Gustafson
Should You Move to a Non Standard Fiscal Year?

Aug 18, 2024

•

11 min read

Should You Move to a Non Standard Fiscal Year?

8/18/24 Benchmarks for Operators

CJ Gustafson
CJ Gustafson
Burden of Proof: Guilty Until Proven Innocent

Jul 30, 2024

•

6 min read

Burden of Proof: Guilty Until Proven Innocent

And avoiding the Bandwidth Vampires

CJ Gustafson
CJ Gustafson
Going up market

Apr 9, 2024

•

7 min read

Going up market

Lessons from companies who have made the leap from SMB to the Enterprise

CJ Gustafson
CJ Gustafson
Your "TAM" is Why I Have Trust Issues

Feb 20, 2024

•

12 min read

Your "TAM" is Why I Have Trust Issues

The pitfalls of total addressable market analyses, and how to think more critically about market sizing

CJ Gustafson
CJ Gustafson
Winning abroad

May 25, 2023

•

8 min read

Winning abroad

A framework for international expansion

CJ Gustafson
CJ Gustafson
A CFOs checklist for going international

May 2, 2023

•

16 min read

A CFOs checklist for going international

What to investigate before you hit the ground running in a new country

CJ Gustafson
CJ Gustafson
A Total Addressable Market (TAM) Masterclass

Mar 28, 2023

•

17 min read

A Total Addressable Market (TAM) Masterclass

Interviewing Sebastian Duesterhoeft, Partner at Lightspeed Venture Partners

CJ Gustafson
CJ Gustafson
Winner take most(ly)

Jan 19, 2023

•

7 min read

Winner take most(ly)

Being #1 in your market is a bigger deal than you think

CJ Gustafson
CJ Gustafson
What exponential growth feels like

Nov 1, 2022

•

8 min read

What exponential growth feels like

Boy, that escalated quickly...

CJ Gustafson
CJ Gustafson
What's the benefit?

Oct 11, 2022

•

7 min read

What's the benefit?

PEOs, EORs and employee benefit uplifts

CJ Gustafson
CJ Gustafson
Not all revenue is created equal

Jul 26, 2022

•

5 min read

Not all revenue is created equal

A billings bonanza

CJ Gustafson
CJ Gustafson
What Product Market Fit Feels Like

Jul 19, 2022

•

5 min read

What Product Market Fit Feels Like

More than a number, more like a feeling

CJ Gustafson
CJ Gustafson
Swimming up stream to the Enterprise

May 31, 2022

•

7 min read

Swimming up stream to the Enterprise

What to know before making the journey, and how to take your lumps

CJ Gustafson
CJ Gustafson

yo, btw…

none of this is intended to be financial or legal advice. do your own homework. call your mom once a week. and make sure to hydrate.