Inside the 90™ Episode #51 - The 3-Part AI Strategy for Entrepreneurs with Josh Heller of Crushable
Inside The 90
114 views
In this episode of Inside the 90, Jami and Andrew are joined by special guest Josh Heller of Crushable to tackle one of the most common questions facing growing businesses right now — how do you actually build an AI strategy? Josh walks through Crushable's tried-and-true framework of identity, operations, and leverage, explaining why most companies skip straight to the fun stuff and pay for it later. The conversation covers the dangers of moving too fast, the rise of custom software over legacy SaaS, and why the companies that can tell the AI story clearly are the ones who will win. Packed with real use cases from the room, this one is equal parts practical and energizing.
Key Topics
Why most companies skip identity and jump straight to leverage — and why that backfires.
The Crushable framework: identity, operations, and leverage explained.
Growth mindset vs. optimization mindset when approaching AI adoption.
The Incumbent's Dilemma: why past success can become a liability in an AI-first world.
The rise of custom software and why off-the-shelf SaaS is being reimagined.
Pace awareness: how to move fast enough without creating tech debt and chaos.
Real use cases from the room: proposals, estimating, admissions workflows, and more.
Key Chapters
0:00 - Welcome and guest intro: Josh Heller and Crushable.
3:00 - What Andrew is hearing inside 20 businesses about AI right now.
6:30 - The identity, operations, leverage framework explained.
11:00 - What AI identity actually means for your team and your culture.
15:30 - Growth architect vs. optimizer: the two mindsets around AI investment.
19:00 - Starting with finance: why the CFO is the best first win for AI projects.
23:00 - The Incumbent's Dilemma: when what got you here could kill you next.
27:30 - Custom software, the death of SaaS support, and tighter feedback cycles.
33:00 - Real use cases: Wonderbrand proposals, Diane the AI agent, and admissions workflows.
40:00 - The handoff problem and how AI is finally bridging it.
45:00 - Pace awareness: hitting the hydration station before you burn out.
50:00 - Key takeaways: pace, identity anchored to core values, and coloring outside the lines.
Mentions & Credits
Josh Heller - LinkedIn: joshgheller
Crushable - https://crushable.ai
Lovable - https://lovable.dev
Whisperflow - https://whisperflow.app
Salesforce - https://www.salesforce.com
Flywheel - https://www.flywheelgvl.com
EOS Worldwide - https://www.eosworldwide.com
Wonder - https://www.workwithwonder.com
Inside the 90™ Episode #51 - The 3-Part AI Strategy for Entrepreneurs with Josh Heller of Crushable
Inside The 90
114 views
In this episode of Inside the 90, Jami and Andrew are joined by special guest Josh Heller of Crushable to tackle one of the most common questions facing growing businesses right now — how do you actually build an AI strategy? Josh walks through Crushable's tried-and-true framework of identity, operations, and leverage, explaining why most companies skip straight to the fun stuff and pay for it later. The conversation covers the dangers of moving too fast, the rise of custom software over legacy SaaS, and why the companies that can tell the AI story clearly are the ones who will win. Packed with real use cases from the room, this one is equal parts practical and energizing.
Key Topics
Why most companies skip identity and jump straight to leverage — and why that backfires.
The Crushable framework: identity, operations, and leverage explained.
Growth mindset vs. optimization mindset when approaching AI adoption.
The Incumbent's Dilemma: why past success can become a liability in an AI-first world.
The rise of custom software and why off-the-shelf SaaS is being reimagined.
Pace awareness: how to move fast enough without creating tech debt and chaos.
Real use cases from the room: proposals, estimating, admissions workflows, and more.
Key Chapters
0:00 - Welcome and guest intro: Josh Heller and Crushable.
3:00 - What Andrew is hearing inside 20 businesses about AI right now.
6:30 - The identity, operations, leverage framework explained.
11:00 - What AI identity actually means for your team and your culture.
15:30 - Growth architect vs. optimizer: the two mindsets around AI investment.
19:00 - Starting with finance: why the CFO is the best first win for AI projects.
23:00 - The Incumbent's Dilemma: when what got you here could kill you next.
27:30 - Custom software, the death of SaaS support, and tighter feedback cycles.
33:00 - Real use cases: Wonderbrand proposals, Diane the AI agent, and admissions workflows.
40:00 - The handoff problem and how AI is finally bridging it.
45:00 - Pace awareness: hitting the hydration station before you burn out.
50:00 - Key takeaways: pace, identity anchored to core values, and coloring outside the lines.
Mentions & Credits
Josh Heller - LinkedIn: joshgheller
Crushable - https://crushable.ai
Lovable - https://lovable.dev
Whisperflow - https://whisperflow.app
Salesforce - https://www.salesforce.com
Flywheel - https://www.flywheelgvl.com
EOS Worldwide - https://www.eosworldwide.com
Wonder - https://www.workwithwonder.com