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
Jamie: “In your own words — what does it take to be a successful business owner?”
Greg:
“Grit is the obvious answer. But more than that — it’s commitment. If you’re going to do this, you go all in. Half-assing it isn’t going to cut it. There’s always going to be someone out there who’s committing more than you are. That commitment is what gets you through the hard parts.”
