Going to Catholic schools in the inner city, delivering newspapers at 6 a.m., working in a chain of stores my family owned, executing for billionaires, and playing ice hockey deep into adulthood definitely got me addicted to difficult things.

I am exceptionally blessed to have worked for the Pritzker family, in my first serious career at TransUnion, where we went through a decade of acquisitions, scooping up every local credit bureau they could find. Most were family owned and decades old. I learned quickly how people and processes were affected. An unbelievable amount of trust was placed in me. It was my first real career, much different than my first paying jobs as a morning newspaper delivery boy in Philadelphia, and later as a Teamster Union member. Working at my family’s stores was more like a duty to family — calling it a job feels wrong.

I was blessed again to work for BravoSolution, acquired by KKR and merged with Jaggaer. To work for an Italian company out of Milan, and to go country to country working with each local entrepreneur was an incredible experience. Ultimately, it helped bring cohesion to the company’s global service model, improve delivery to clients, and boost the company’s valuation. Ferrari was a customer. They redefined what pressure is when you need to execute for them!

My next significant step was with Simpay Holdings, working for serial entrepreneurs with ice in their veins. Just like at BravoSolution, EOS was critical to success, but so was a ridiculous amount of grit, experience and change management. We got through the pandemic, got funding, and lit the rocket, because scaling was insane. And, it was done well— exceptionally well!

I was behind on my personal goal to relocate to where most of my family, friends and network had migrated over the years (Coastal Delaware), so I stuck it out with Simpay until they were solid, stable, and funded. I started to do remote work, partnering with a friend and using Rocket Ops as our business. It’s just elevates things beyond being a 1099 worker. I successfully relocated to Delaware in 2023.

I did some incredible contract work, mostly as an EOS Integrator and COO. All experiences were good or great, but flipping USA Insulation of New England on its head was the best one, because the odds were stacked against me, so to pull off something amazing in a completely different vertical — home improvement — was incredible and memorable. Breaking sales records in a door-to-door selling environment is a whole different experience than leaning on MRR and ARR!

Along the way, one of the most amazing entrepreneurs I met was Pete S., the brilliant founder of ShowMojo. While I was at Simpay, as we all worked to keep the pandemic from bringing the company to near collapse, I met Pete and did a deep dive into his business, but did not join him, as I needed to see things through at Simpay.

Ultimately, after relocating to Delaware, Pete and I reconnected online, and he eventually shared his decision to sell ShowMojo to private equity. But he had no proven leader within the company; he wanted to exit almost immediately after acquisition, and he wanted things to happen as soon as possible. He said, “You’re my guy.” I just considered that an extraordinary compliment and challenge, and I went for it. I had to be vetted by the PE firm first, of course. Within weeks of me joining, Property Tek (under GSV) acquired ShowMojo, and then a few weeks later, Pete was gone, as he successfully exited.

I wore multiple hats, of course: To Property Tek, I was the CEO, and on level with the other CEOs (all founders) within the holding company. At ShowMojo, I was the GM and Integrator, or the COO and Head of Sales — all depending on what was happening at any given moment. It was an incredible ride that I knew could only last a couple of years, but we beat their numbers, they reorganized the holding company, and all CEOs exited. I think the ultimate compliment was how they loved how we used EOS, and they appreciated that ShowMojo ran like a machine, and how we were meticulous with planning and execution. Impressing some of the most intelligent and accomplished people I’ve ever met was extraordinary.

Recently, I’ve been helping small firms on an ad hoc basis, so I am in pursuit of my next big thing. It will probably be difficult, different, and require tenacity, interesting technological solutions, and teamwork. And it will certainly require some type of operating system to be weaponized, such as EOS. I’ll lead with honesty instead of comfortable lies, and I will hunger for the first planning meeting to get the strategy locked down so we can go make it happen.

Outside of work, I enjoy spending time with my ‘kids’ who are both new homeowners, the neverending challenges and rewards of boating and fishing, and going on interesting adventures with my wife Rebekah and our high-energy Golden Retriever, Ella.