Making AI Work in Business (Without the Buzzwords)
Everyone is talking about AI — automation, ChatGPT, digital transformation. But very few business owners can actually explain what it really takes to make AI work inside a company. That’s exactly why we invited Greg Gillespie, Co-Founder and Principal at Collectiv, onto Business Owners Tell All: What It Takes.
Collectiv is a Dallas–Fort Worth–based data analytics and AI enablement firm that has landed on the Inc. 5000 list three times, helping mid-size and enterprise organizations build data foundations that fuel real, scalable AI adoption. Greg’s journey from a 2016 layoff to leading a 30‑person AI consulting company is filled with lessons on leadership, process, hiring, and what it truly takes to grow.
This episode isn’t just about technology.
It’s about people, process, and the grit required to build something great.
From Layoff to Leadership: Greg’s Entrepreneurial Beginning
Greg’s entrepreneurial spark started early — long before data engineering and AI. His father encouraged him to explore entrepreneurship through small jobs like mowing lawns and doing odd tasks for neighbors. That foundation of independence and problem‑solving stayed with him through adulthood.
In 2016, he was unexpectedly laid off. Instead of job hunting, he took it as a sign.
“I said, are you gonna do this thing or not, Greg? You’ve gotta commit and give it everything.”
After discovering Microsoft Power BI, he launched his first consulting company. It wasn’t easy, but the momentum eventually led to co-founding Collectiv in 2019 — and the rollercoaster of growth hasn’t slowed down since.
Building a Team for Real AI Adoption
Greg didn’t master team-building overnight.
At first, he did what most founders do: everything himself.
“I was the individual that basically did everything. I was micromanaging — that’s what happens when you wear all the hats.”
Collectiv initially operated with all 1099 contractors, imagining a scalable, flexible model. But reality set in quickly:
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Contractors weren’t bought into culture
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Projects slipped
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Communication wasn’t consistent
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There was no true team alignment
The idea looked great on paper — but without shared values, things fell apart.
Greg and his co-founder shifted to W‑2 employees, focusing heavily on culture, core values, and long-term growth. This shift changed everything.
Hiring for Culture, Training for Skill
One of the biggest mistakes Collectiv corrected?
Hiring purely for technical skills.
“We weren’t looking at culture fit — we were only looking at whether they could do the technical work.”
After implementing EOS and rebuilding their core values, Greg realized something crucial:
Culture can’t be an afterthought.
It has to be the strategy.
The team began hiring based on:
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Shared values
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Communication style
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Growth mindset
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Role alignment using tools like Culture Index
And skills?
Those can be taught.
The result has been a team that works better together, communicates proactively, and stays aligned with the mission of helping companies build AI-powered operations.
Developing AI‑Literate Employees
Greg also highlights how important training and upskilling are for long-term success — especially in fast-moving industries like AI and data.
New hires are paired with managers who:
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Map out career paths
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Create tailored training plans
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Expose team members to the right projects
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Build confidence in both technical and consulting skills
Collectiv doesn’t just build strong consultants — they build AI‑literate leaders.
The True Cost of the Wrong Hire
One of the strongest themes in the episode is how expensive bad hiring decisions are — financially, emotionally, and culturally.
“You don’t realize how much it costs to hire the wrong person — until you do it a few times.”
Rapid growth caused Collectiv to hire quickly, and sometimes too quickly. Greg reminds listeners that smart hiring should be slow, intentional, and deeply tied to values.
This is where many businesses fail.
This is also where Collectiv grew.
Scaling Smart: Balancing Contractors & Full-Time Staff
Today, Collectiv operates with a hybrid model:
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~30 full-time employees
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Offshore team in South Africa
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Trusted contractors for peak cycles
The difference now is strategy.
Contractors are used purposefully — not to compensate for unclear hiring processes.
This balance keeps the company flexible during intense periods while preserving culture and quality.
What It Takes to Be a Successful Business Owner
At the end of every episode, we ask our guests what it really takes to sit in the entrepreneur’s seat. Greg doesn’t hesitate:
“Grit is the obvious answer. But commitment — that’s what separates people. You go all in, or you don’t do it at all.”
He explains how commitment pulled him through setbacks, hiring mistakes, walls he kept hitting, and moments of self-doubt.
“Eventually you plow through that wall and think, ‘Why was that so hard?’ But you only get there if you’re committed.”
This is the heartbeat of the episode — and the show.
Where to Find Greg & Collectiv
🌐 Website: https://gocollectiv.com
🔗 LinkedIn: Greg Gillespie
📺 YouTube: @gocollectiv
If you’re attending FabCon, Collectiv will have a booth — be sure to stop by.
Final Thoughts
This conversation with Greg Gillespie is a powerful reminder that making AI work in business isn’t about the tools — it’s about the people using them and the processes supporting them.
Whether you’re scaling a startup, hiring your first team, or navigating the complexities of digital transformation, Greg’s insights make one thing clear:
AI doesn’t transform companies.
People do.
