From Broke to Debt-Free in Italy: How Learning Sales Changed My Life

Ten years ago, I was broke, completely flat broke. We were buried in debt, living on credit cards, and I couldn’t even make a $240 car payment.

Fast forward to today: I live in Italy with my wife and our three kids. We’re debt-free, and we bought our house in cash. None of this happened by accident. It happened because I learned to sell, specifically, software sales.

This isn’t a victory lap. It’s a roadmap for anyone who wants to turn their finances and their future around.

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Ministry Dreams, Family Business Reality

I always wanted to make an impact. I even earned a degree in Greek and Hebrew because I planned to become a pastor. But after graduating in 2009 at the height of the financial crisis, nothing was hiring.

My dad and grandfather were both successful in insurance and invited me to join. I learned persuasion, confidence, and how to serve customers so they return year after year. But I hated sales. I was terrified to pick up the phone, even to call customers who had known our family for decades.

Chasing Passion (and Hitting a Wall)

I followed my passion into video production and photography. I took out a loan, bought the gear, built a portfolio, and even worked behind the scenes on sets (yes, real sets with real names). I loved the craft. But skills don’t equal income if you can’t sell.

We lived frugally, tiny apartment, beans and rice, but the debt kept growing. I’ll never forget selling our minivan back to the dealership because I couldn’t make the $240 payment. That moment wrecked me. I felt like I had failed my wife, my kids, myself, and my business.

The Hard Truth: Marketing ≠ Sales

I believed great marketing would carry customers all the way to purchase so I wouldn’t have to be uncomfortable asking for money. But marketing creates attention; it doesn’t close deals. The truth was simple and hard: I needed to get good at sales.

So I got serious. I devoured books and podcasts and asked a simple question: If I’m going to do this, what’s the best path? I Googled, “Who makes the most money in tech sales?” The answer jumped off the screen: large enterprise sellers at cybersecurity companies. For someone making nothing, the potential was mind blowing and clarifying.

I told my wife, “I’m going to become a large enterprise account executive at a cybersecurity company.”

Car-Lot Bootcamp

There was just one problem: I had no real sales experience. So I put $1,000 I didn’t have on a credit card for a sales program and started where I could, selling cars.

I knew nothing about cars. But day after day, I faced rejection, learned negotiation, wrote my goals, studied, and worked the craft. It built resilience and confidence.

That got me into my first software sales role in Austin as an inside seller. I learned product, tech, and B2B sales. Then I was fired after a year. Painful, but pivotal.

Breaking into Cybersecurity and More Setbacks

That firing pushed me toward my goal: I joined CrowdStrike and finally broke into cybersecurity. I helped open the Austin office and got hooked.

But hitting a milestone doesn’t mean the journey smooths out. After CrowdStrike, I joined two startups back to back and was laid off twice in one year as companies struggled to survive. It was brutal and demoralizing. I questioned whether I was even cut out for sales.

Axonius and the Ascent

Those hard lessons set up my next chapter: Axonius. When I joined, it was a small, scrappy team with huge potential. Over five years I grew from AE to Large Enterprise AE, then Manager, then Director of Global Business Development and Inside Sales. I helped scale teams, build playbooks, and grow alongside one of the fastest growing cybersecurity startups.

During that time, I earned multiple six figures, we paid off every dollar of debt, maxed our 401(k)s, invested, and gave generously. We even built our dream home outside Austin with solar and backup batteries.

Freedom, Impact, and a New Life

The biggest reward wasn’t the money, it was the freedom and impact. In 2024, we sold nearly everything and moved our family to Italy. Now we spend our days exploring Europe, meeting new people, working in the garden, and living life on our terms.

What I Want You to Hear

Sales isn’t about quota or being a slick closer from TV. It’s a vehicle for freedom, leadership, and impact.

I started out hating sales. I was terrified of rejection (still am sometimes). But through grit, perseverance, and coachability, sales became the very thing that transformed my life.

If it can do that for a kid from South Texas who once wanted to be a pastor, it can do the same for you, no matter your background.

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