Value-First Platform: Data Modeling with AI

📋 Show Notes

Episode Description

Last time, we hit our first major AI limitation live on camera.

Episode 2 of Value-First Platform ended with Claude maxing out its token limit trying to audit the properties of a complex HubSpot portal.

Most content would edit this out, restart with a cleaner demo, or pretend it didn’t happen.

We’re doing the opposite.

Today’s episode starts with exactly this reality:

What do you do when your AI collaborative partner hits a wall?

How do experienced practitioners adapt in real-time?

What strategic opportunities emerge from apparent limitations?

Here’s what’s fascinating about this moment:

Ryan Ginsberg discovered that AI can serve as a neutral moderator, preventing consultant-client friction by making technical decisions feel collaborative rather than imposed.

Rylee Powell identified the “restart multiverse” challenge - every time you restart an AI conversation, you get a different journey. Traditional progress tracking doesn’t work, so what does?

Trisha Merriam recognized the gap between AI implementation theory and her daily reality of “inherently lazy” automation needs that often cost more time than manual work.

The breakthrough insight: These aren’t bugs to solve - they’re features of AI-native collaboration that require completely different approaches to project management, progress measurement, and team coordination.

Today, we demonstrate live how AI-native teams actually handle constraints:

• Rapid synthesis of complex prior work • Real-time strategic pivoting under deadline pressure • Collaborative decision-making about async vs. sync work patterns • Strategic reframing when limitations create new opportunities

This is what collaborative intelligence looks like when it meets real business constraints with real deadlines.

The polished demos end here. The authentic learning begins.

Join us to see how AI-native teams turn limitations into strategic advantages.

#AI #HubSpot #ValueFirst #Platform

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