Wantrepreneur to Entrepreneur | Start and Grow Your Own Business 1204: Bought companies, sold companies, & building companies through RELATIONSHIPS in the IT space w/ Darek Hahn
Darek Hahn isn’t your typical tech CEO—he’s a relationship-first entrepreneur who's redefining how businesses experience IT. In this episode, Darek shares his path from watching his mom build a business to leading, acquiring, rebuilding, and launching multiple IT companies. Now at the helm of AffinIT, he’s proving that the secret to lasting client success isn't tech—it's trust.
Whether you're scaling a service business or stepping into leadership for the first time, Darek’s insights on team building, vulnerability, and executive focus are game-changers for founders at any stage.
💡 What You'll Take Away For YOUR Business
- 🎯 Why leading like a “conductor” can transform how your team performs
- 🧠 The surprising difference between being an entrepreneur and being a CEO
- 👥 How to build client relationships so strong they outlast contracts
- 💼 Why emotional intelligence is your business’s greatest asset
- 🧰 How to structure your time as a visionary entrepreneur with traction and discipline
- 🔄 How to turn IT pain points into profitable value-add services
- 🤖 What AI policies you NEED to have in place before it’s too late
📝 About the Guest
Darek Hahn is a relationship-driven CEO with a diverse background in facilities, IT, and startup leadership. He entered the IT space in the early 2000s and went on to lead several startups before spearheading the acquisition of an IT Managed Service Provider in 2016. After rebuilding the company following the loss of a major contract, he successfully led its sale to a cybersecurity firm in 2021. In 2024, Darek launched a new MSP with a clear mission: to restore the human connection often missing in the industry. Today, we’ll dive into how that vision is shaping his latest venture.
🎯 Darek’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"It’s not about you—it’s about the people you surround yourself with."
Key Takeaways:
✔ Success comes from building a high-performing team, not doing it all yourself
✔ Surround yourself with people who challenge and complement your skills
✔ Celebrate and elevate every person’s contribution like you’re conducting an orchestra
📢 Memorable Quotes
- “Your technicians are more important than your CEO—they’re the ones keeping clients.” – Darek Hahn
- “I want to be at your retirement party—and I hope you’ll be at mine.” – Darek Hahn
- “The best leaders aren’t afraid to be vulnerable. That’s how you build trust.” – Darek Hahn
💡 Actionable Takeaways
- ✅ Build a values-first company culture rooted in trust and honesty
- ✅ Schedule structured "executive time" to focus on strategy and self-reflection
- ✅ Implement traction or a business operating system to align your team
- ✅ Create a formal AI policy—your people are already using it, whether you know it or not
- ✅ Don’t just fix tech issues—use them as opportunities to deepen relationships
🔗 Links & Resources