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Push the Boulder or Catch the Water

Jun 13, 2026

•

5 min read

Push the Boulder or Catch the Water

Sense the Awareness, Sensei

Matthew Kee
Matthew Kee
Two Types of Investor Conviction

Jun 6, 2026

•

6 min read

Two Types of Investor Conviction

Why investors on the cap table do not change the underlying startup opportunity

Matthew Kee
Matthew Kee
Why We Passed on This Startup (Episode 15)

May 30, 2026

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8 min read

Why We Passed on This Startup (Episode 15)

A retro of why we *didn't* invest

Matthew Kee
Matthew Kee
Starting from Fundraising ZERO

May 23, 2026

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7 min read

Starting from Fundraising ZERO

Separate the Acclaim from the Aim

Matthew Kee
Matthew Kee
How to Neutralize Your Competition

May 16, 2026

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7 min read

How to Neutralize Your Competition

The Power of a Check-Mate Move

Matthew Kee
Matthew Kee
What The Insecure CEO Didn't Know

May 9, 2026

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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

•

10 min read

When Products Win But Startups Don't

A Displaced Actor is a Bad Actor

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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