Episode Details

In this episode, Jamie Seeker sits down with Greg Gillespie, the Co-Founder of Collectiv — a fast-growing data and AI consulting firm that’s made the Inc. 5000 list three times. Greg shares his journey from being laid off in 2016 to building a 30-person firm helping mid-sized and enterprise businesses operationalize AI, Power BI, and data strategies across their organizations.

But this isn’t a tech-heavy episode — it’s all about what really makes businesses grow sustainably: process, people, and leadership.

Greg opens up about the hard lessons he’s learned from micromanaging, hiring too fast, and what it took to build a values-driven team that could scale smartly. From moving from all-1099 contractors to a W-2 team, to implementing EOS and culture-based hiring practices, he shares a masterclass in business growth through intentional people strategy.

📌 Key Takeaways:

• AI success starts with process — not just tools. You need systems in place before layering in automation.
• Micromanaging is a trap for founders. Greg shares how "Delegate & Elevate" helped him shift his leadership style.
• Hiring for values > hiring for skills. Skills can be taught, but shared values and cultural fit are foundational.
• Invest in employee growth. Greg shares how their internal training paths are built to elevate team members from day one.
• Rapid hiring = real risks. Scaling without systems can cost more in the long run — both financially and culturally.

💬 Memorable Quotes:

🗣️ “I didn’t know how to build a team at first. I did everything myself. I was a micromanager because I felt like I had to be.” – Greg Gillespie

🗣️ “We started with all contractors. It sounded great in theory — but when no one’s bought into the culture, things start slipping.” – Greg Gillespie

🗣️ “If these core values don’t mean something to me, how can I expect anyone else in the company to live them out?” – Greg Gillespie

🗣️ “You don’t realize how much it costs to hire the wrong person — until you do it a few times.” – Greg Gillespie

🗣️ “If you’re gonna do this — build a business — you do it all the way or don’t do it at all. You’ve gotta commit.” – Greg Gillespie

🗣️ “Eventually you plow through that wall and go, ‘Why was that so hard?’ But you only get there if you’re committed.” – Greg Gillespie

🧠 Topics Covered:

• Greg’s entrepreneurial origin story — from layoff to leadership
• Building a business around Microsoft’s Power BI & Fabric
• How EOS and “Delegate & Elevate” transformed his leadership
• Culture-first hiring: mistakes, pivots, and the impact
• HR strategy for scaling smart (especially with AI adoption)
• How to build an AI-literate, change-ready team
• The importance of clarity around values in building a sustainable company

👥 Team Size:

~30 employees + offshore team in South Africa

🛠️ Tools & Frameworks Mentioned:

• EOS (Entrepreneurial Operating System)
• Delegate & Elevate
• Core Values Alignment
• Culture Index
• Microsoft Power BI, Microsoft Fabric, Azure
• Predictive Index

🧭 Where to Find Greg & Collectiv:

🌐 Website: https://gocollectiv.com

🔗 LinkedIn (Greg): linkedin.com/in/greg-g