Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

1298: The 5 Levels of Digital Operations That Separate Amateurs from Pros w/ Michael Greenberg

Nov 12, 2025

Michael Greenberg, a serial entrepreneur and founder of Third Brain, dives deep into digital operations and AI readiness. He introduces the flywheel effect, highlighting how it enables sustainable growth over brute-force methods. Michael discusses the five levels of digital maturity crucial for business scaling and defines key differences between AI and automation. He emphasizes the importance of mastering foundational systems before integrating advanced technologies, and shares actionable strategies to help entrepreneurs streamline operations and escape the 7-figure grind.

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ANECDOTE

Entrepreneurship From Family To Exit

Michael grew up in multi-generational entrepreneurial families and started selling imported goods in high school.
He dropped out of college, learned to code, worked as a CTO/consultant, built a podcast agency, and later sold its main unit.

INSIGHT

Foundation Before Fancy Tech

Michael compares building business systems to building a house with an essential foundation.
You must document manual processes before automating or adopting advanced tools like AI.

INSIGHT

Flywheel Drives Scalable Growth

The flywheel separates businesses that stall from those that scale beyond eight figures.
Reaching a unified data layer creates consistency, clarity, and capacity, which drives the digital operations flywheel.

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Tired of feeling like you're brute-forcing your business to the next level? In this episode, serial entrepreneur and digital operations expert Michael Greenberg breaks down the single biggest differentiator between businesses that stall and those that scale to 8-figures and beyond: the flywheel effect. Michael demystifies the buzzwords, offering a clear, step-by-step framework to build a rock-solid operational foundation. He reveals the five levels of digital maturity, the crucial difference between AI and automation, and why you can’t use a “chainsaw” (advanced tech) until you’ve mastered the “axe” (manual processes). This episode is a masterclass in strategic thinking, providing entrepreneurs with a practical roadmap to build a business that gains momentum with every turn, reduces stress, and creates sustainable growth.

💡 What You'll Take Away For YOUR Business

⚙️ The Digital Operations Flywheel: Discover how to build a business that builds leverage with every turn, making future growth easier and more automatic.
🪜 The 5 Levels of AI Readiness: Learn how to assess where your business currently stands—from siloed data to a fully automated system—and what steps to take to level up.
🤖 AI vs. Automation: Understand the critical difference between data automation, AI tools, and AI agents, and why you must master the simple stuff first.
💰 Escaping the 7-Figure Grind: Uncover why brute force only gets you so far and how implementing the "Three Cs" (Consistency, Clarity, Capacity) is the key to breaking through growth plateaus.
🔨 You Can't Use a Chainsaw If You Can't Swing an Axe: Why mastering and documenting your manual processes is the non-negotiable first step before implementing any advanced technology.
🚀 Where to Start Your Systems Journey: Pinpoint the highest-leverage area in your business (hint: it’s probably sales and marketing) to begin building your operational flywheel for the fastest results.
💸 Tech Stack Benchmarks: Get clear benchmarks on what percentage of your budget you should be spending on technology, depending on your business type.

📝 About Michael Greenberg

Michael Greenberg is a serial entrepreneur, author, and the founder of 3rd Brain. Growing up surrounded by multiple generations of entrepreneurs, business is in his DNA. Michael’s journey took him from dropping out of college to attend a coding bootcamp, becoming a CTO at a seed-stage startup, and eventually founding and scaling his own agencies. Through his company, 3rd Brain, he now partners with small businesses to build a foundation of talent, training, and strategy to accelerate their growth using his proprietary Digital Operations Flywheel. His unique perspective bridges the gap between old-school business principles and new-school technology, making him an invaluable guide for any entrepreneur looking to scale intelligently.

🎯 Michael’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Have a bias for action, but ensure you have the data and a clear reason to back up every decision you make."

🔗 Links & Resources