Miha Matlievski
Founder, Fail Coach
Serial entrepreneur. Four-time business failure. Rebuilt from $5M in debt. Now helping founders build companies that don't destroy them.
The short version
Miha started his first business at 16 in Slovenia. By his early 30s, he had built a portfolio of companies worth $15 million across real estate, hospitality, and services.
Then 2009 happened. The financial crisis hit. Four businesses failed simultaneously. He went from $15 million in assets to $5 million in debt.
It took years to rebuild. He had to relearn everything — not just about business, but about himself. What actually mattered. How to lead without burning out. How to build something sustainable.
That experience — the failure and the recovery — is the foundation of everything he teaches today.
The full story
Growing up in Slovenia, Miha didn't have a blueprint for entrepreneurship. He just knew he wanted to build things. His first business, started in high school, wasn't glamorous — but it taught him that he could create something from nothing.
Through his 20s, he built aggressively. Real estate. Hospitality. Professional services. Each business fed the next. By 2008, on paper, he was successful. Multiple companies. Millions in revenue. A growing team.
He was also working constantly. Every decision flowed through him. The businesses couldn't function without his presence. He thought that was just what success required.
Then the 2008 financial crisis arrived. Credit markets froze. Real estate collapsed. Customers vanished. Within months, all four of his businesses were in freefall.
The $15 million portfolio became $5 million in debt. Everything he had built was gone.
What followed was the hardest period of his life. Not just financially — though that was brutal — but psychologically. He had to confront everything he'd gotten wrong. The way he'd built his businesses. The way he'd treated his health, his relationships, himself.
The recovery wasn't quick. It took years. But in that process, Miha learned what actually creates sustainable success. Not the hustle culture nonsense. Not the “grind until you die” mentality. Real leadership. Real systems. Real resilience.
Today, Miha works with founders to help them build what he couldn't build the first time: companies that grow without destroying the people who create them.
“Miha in Your Pocket”
Most coaching relationships are structured around scheduled calls. A check-in every week or two. But business doesn't work on a schedule.
The crisis happens on Tuesday afternoon. The difficult conversation needs to happen tomorrow. The decision that will define your quarter is due by end of day.
That's why Miha works differently. “Miha in Your Pocket” means ongoing access — when you need it, not when the calendar says so. Voice notes, messages, quick calls when something is urgent.
It's like having a trusted advisor who's been through it all, available when the real challenges hit.
Beyond Fail Coach
Outside of client work, Miha shares what he's learned through various channels:
- Brain Dump Podcast — Conversations with founders about the real challenges of building companies. Listen here →
- LinkedIn — Regular posts on leadership, failure, and building sustainable businesses. Connect here →
- Speaking — Miha speaks at events about failure, resilience, and entrepreneurship. Contact us if you'd like to discuss.
Want to work together?
If you're a founder dealing with the challenges I've described, let's talk.