Systems vs. Discipline: The Real Breakthrough for Roofing Owners with Jason Todd - Roofer Growth Hacks - Season 4 Episode 2

2025-09-09

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Welcome to Roofer Growth Hacks by RoofingSites.com. In this episode Chris Hunter interviews Jason Todd, founder and CEO of Thinker Ventures. They discuss Jason's entrepreneurial journey, the role of Thinker Ventures in helping businesses grow, and the common challenges faced by small businesses. Jason emphasizes the importance of discipline over systems in business management and shares insights on how to implement effective strategies for growth and exit planning. The conversation also touches on the use of AI in business operations and the significance of reflection and...

Jason emphasizes the importance of discipline over systems in business management and shares insights on how to implement effective strategies for growth and exit planning.

The conversation also touches on the use of AI in business operations and the significance of reflection and outside perspectives in achieving success.

If you’re serious about growing your roofing business and mastering modern website strategy, this episode is for you!

About:

High-growth teams hire Jason Todd to shape business strategy, technology, and communications. With 20+ years of experience, he has founded and exited four companies, written over one million lines of code, advised hundreds of organizations, built brands worth $300M+, and negotiated with billion-dollar corporations.

He helps leaders and teams through:

Business Advising – multi-disciplinary mentoring for faster growth
On-Demand CTO/CIO – expert tech guidance without full-time overhead
Sprints & Short Contracts – 90-day growth and accountability sprints
Advisory Boards – strategic leadership and connections to funding

Todd’s track record spans startups to $1B enterprises—driving systems integration, ecosystem development, brand strategy, and software innovation. He’s also a community builder, having hosted 500+ hours of live streams, podcasts, and startup events.

Find more at www.TheRealJTodd.com

Timestamps:

[00:00 - 00:48] Intro

[00:49 - 01:45] Who is Jason Todd?

[01:46 - 04:20] The Role of Thinker Ventures in Business Growth

[04:21 - 06:31] Common issues: founder cap; discipline + team to scale

[06:32 - 14:53] Lead Handling, Outside Eyes & Pricing Turnaround

[14:54 - 20:17] Systems vs. Disciplines in Business

[20:18 - 23:05] The Role of AI in Business Operations

[23:06 - 29:30] Understanding AI Agents and Their Limitations

[29:31 - 29:47] Sponsor AD

[29:48 - 41:24] Lightning Round (Rapid Fire Questions)