#475 Cooper Simson - Portfolio Manager at Martell Ventures

Update: 2025-11-25

Description

AI used to feel like a “someday” technology. Now it’s a power tool founders can use this weekend to build real products, validate ideas, and even qualify leads while they sleep. In this episode, I’m joined by Cooper Simson of Martell Ventures to talk about the real front lines of AI: shutting down a profitable AI startup, spotting bad ideas in a hype cycle, and using AI to build, sell, and iterate faster—without getting lost in the noise.

Topics we cover:

When AI actually “caught fire” and why development is becoming commoditized
How Cooper turned grant writing into an AI startup (and why he shut it down even though it was working)
Practical signals it might be time to wind down your product or pivot
The difference between product validation and true product–market fit
What Martell Ventures looks for in founders (domain expertise + speed of action)
Common AI founder mistakes: copycat products, no defensibility, and one-and-done tools
Why so many founders struggle with sales (and how to sell problems, not features)
How to use AI to 10x your output: system prompts, voice-to-text tools, and AI lead qualifiers
A simple 2-step playbook to go from idea → customer conversations → weekend MVP
Cooper’s own “just get started” moment building a Shopify sales-tax tool for his fiancée’s business

Chapters:

0:00 – Introduction

1:30 – Cooper’s first AI startup: grant-writing software in the “GPT 1.0” days

5:30 – Knowing when to shut down a ‘working’ business (government risk, sunk cost, AI catching up)

10:10 – Rapid Fire Q1: The Post-It note he’d give the next generation (“Just go sell”)

11:35 – Rapid Fire Q2: Mantra when things get hard (glass-half-full & keep the sail up)

12:30 – Rapid Fire Q3: Priorities when everything feels urgent (Eisenhower Matrix in real life)

14:15 – Rapid Fire Q4: Staying motivated when the wins are slow to come

16:10 – Rapid Fire Q5: Cooper’s next Just Get Started moment (Shopify sales-tax tool for his fiancée)

20:45 – What makes an AI idea worth building vs “because we can build it”

24:00 – Common founder mistakes: copycat AI, no defensibility, one-time-use tools & ignoring churn

29:15 – Why founders struggle with sales (and how to sell the problem, not the product)