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What The Insecure CEO Didn't Know

May 9, 2026

•

5 min read

What The Insecure CEO Didn't Know

A framework for sorting now, later, or never

Matthew Kee
Matthew Kee
Reframing TAM to FAM

May 2, 2026

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4 min read

Reframing TAM to FAM

The Market Size that Really Matters

Matthew Kee
Matthew Kee
When Optimism is Alarming

Apr 25, 2026

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8 min read

When Optimism is Alarming

A story of how optimism can cloud execution and dissuade investors

Matthew Kee
Matthew Kee
Why VC Acts Like Tinder

Apr 18, 2026

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7 min read

Why VC Acts Like Tinder

Explaining the Quick-Look Pass

Matthew Kee
Matthew Kee
The Tale of Two Fundraising Founders

Apr 11, 2026

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10 min read

The Tale of Two Fundraising Founders

Why Creating Optionality is a Critical Ingredient in Fundraising

Matthew Kee
Matthew Kee
What Buying Cycles Can Tell You

Apr 4, 2026

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8 min read

What Buying Cycles Can Tell You

A Dynamic that Determines Your Go-to-Market

Matthew Kee
Matthew Kee
When Products Win But Startups Don't

Mar 28, 2026

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10 min read

When Products Win But Startups Don't

A Displaced Actor is a Bad Actor

Matthew Kee
Matthew Kee
The Power of the Small Ask

Mar 21, 2026

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11 min read

The Power of the Small Ask

The Low-Risk and Low-Commitment Offer

Matthew Kee
Matthew Kee
Why We Passed on This Startup (Episode 14)

Mar 14, 2026

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10 min read

Why We Passed on This Startup (Episode 14)

A retro of why we *didn't* invest..

Matthew Kee
Matthew Kee
When Traction Isn’t Quite There

Mar 7, 2026

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11 min read

When Traction Isn’t Quite There

How to Fundraise in the Hardest Moments...

Matthew Kee
Matthew Kee
How Investors Pick Startup Meetings

Feb 28, 2026

•

17 min read

How Investors Pick Startup Meetings

and What You Can Do About It...

Matthew Kee
Matthew Kee
The Poison in Your Pipeline

Feb 21, 2026

•

9 min read

The Poison in Your Pipeline

Maybe speaking > selling

Matthew Kee
Matthew Kee
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Tundra Angels' Angle

Tundra Angels' Angle

Insider tactics as a startup investor that I wish I would have known 10 years ago as a founder.

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