How Gary Pica turned tough love into a lifelong friendship — and made me a better leader in the process

This post marks a pretty special milestone — the 50th TruMethods/Winners Circle Peer Group meeting.

Fifty.

That’s half a century of meetings if you count them in dog years.

I’m one of the handful of people who was there at the very first one — back when the idea of paying to sit in a room full of other business owners and talk about our weaknesses felt… counterintuitive, to put it politely. None of us really knew what we were stepping into — but looking back, it turned out to be one of the smartest decisions I ever made.

And at the centre of it all — the chaos, the breakthroughs, the caffeine-fueled epiphanies — was Gary Pica.

I met Gary years earlier, at a ConnectWise IT Nation event in 2009, back when he was just starting his coaching journey and I was still figuring out what kind of business owner I wanted to be. We hit it off right away — two guys who loved the industry but were both painfully aware of how messy it could be. Gary had this infectious energy and clarity that made you want to follow him straight into whatever wild new idea he was cooking up.  I followed him into way more of those than I care to admit.

Over the years, we grew together — he as a coach, me as a leader. We’d exchange ideas, challenge each other, and occasionally argue like an old married couple (sometimes in front of an audience) about the right way to do things.

(Spoiler: he was almost always right. Almost.)

As my company evolved, Gary noticed something — I was getting pretty good at this stuff. Good enough, in fact, that he started asking me to join him on speaking engagements and TruMethods events, giving me the chance to share what I’d learned firsthand with other owners.

Those experiences were huge for me — not just because it got me started on my journey as a coach who helped others, but because Gary trusted me enough to stand beside him.

Every so often, someone shows up in your life and casually detonates everything you thought you understood about success. For me, that man was Gary.

When I first joined TruMethods in 2009, I thought I was doing alright. I thought I had a good business, great people, modest profits, and enough swagger to believe I’d cracked the code. What I actually had was a full-blown case of Business Owner Delusion — the one where you think you’re indispensable when you’re really just in the way.

Enter Gary — equal parts terrorist, coach, therapist, and human defibrillator.  He said “Well, you have zero profitability, no consistency, and employees walking out the door.  Nice job.”

From day one, he had this unnerving habit of listening to me explain something for five minutes and then saying, “Shut up.  You’re the problem.” No sugar-coating. No PowerPoint. Just truth, delivered with a deadly smirk and the confidence of a man who watched dozens  of other owners make the same mistakes.

And holy shit — he was right.

Gary didn’t just help me fix my business. He rewired how I thought. He made me see that leadership isn’t about control, it’s about clarity. That culture isn’t a nice-to-have — it’s the whole damn engine. And that if your business can’t run without you, you don’t have a business, you have a hostage situation.

Those early meetings were humbling — a mix of therapy, comedy, and business boot camp. Picture a group of type-A entrepreneurs trying to out-vulnerable each other while pretending we weren’t about to cry in front of grown men and women. It was beautiful chaos.

But the real magic was in that room — the people Gary brought together. A collective of brilliant, neurotic, passionate lunatics who wanted to build something meaningful and get their lives back. Over the years, we built more than businesses. We built friendships. We built accountability. We built a safe place to say, “I have no idea what I’m doing,” and still be respected for it.

And through all of it — every win, every loss, every meltdown — Gary was the constant. Manic. Direct. Unapologetically human. A mentor who could challenge you and still make you laugh right after you realized he’d just dismantled your ego.

At some point along the way, the mentorship turned into friendship. The kind where shop talk gives way to real talk — about family, burnout, aging, purpose, and why the hell we still do this to ourselves. Cigars and really expensive Scotch.  Gary became one of those rare people you don’t just respect — you really love.

Nothing bonds you like trauma, and we found out early on that we both lost our brothers far too soon – an event that changed our perspectives on everything we did.  We discovered that we were both huge Billy Joel fans and found ourselves (along with the inimitable Bob Penland) at several shows in Philly singing until we were hoarse.  One of my favourite memories will always be in the lobby of the Westin at 4 in the morning.  Gary was sitting on the piano bench beside me, demanding that I play “Summer, Highland Falls” for the 27^th time.  He kept getting Murray to bring me illicit scotches to ensure that I wouldn’t leave.

So we’ll argue and we’ll compromise
And realize that nothing’s ever changed
For all our mutual experience
Our separate conclusions are the same
Now we are forced to recognize our inhumanity
Our reason coexists with our insanity
And though we choose between reality and madness
It’s either sadness or euphoria

_{Billy Joel – Summer, Highland Falls}

We have been there for each other through our high points, our low points, and the fucked-up parts where I was trying to figure out who the hell I was without a title.  He has dragged me out of places so dark that only we will ever understand.  I literally don’t know what I would have done without him.

When PACE finally hit its stride — becoming one of the Best Places to Work, building a culture I was proud of — I could draw a straight line back to Gary and those early lessons. He didn’t hand me a playbook; he handed me perspective. He didn’t fix my company; he made me face myself.

Even now, years later, when I’ve reinvented myself as a leadership coach, actor, musician, and wedding officiant (because apparently I collect careers like some people collect bobbleheads), I still hear his voice. Every time I start to overthink something or drift back into micromanagement, there he is — equal parts giddy guru and mob boss — saying, “For fuck sakes Shael… stop being stupid.”

We still talk all the time. We still give each other shit. And every time we do, I’m reminded that friendship born from shared purpose is the best kind there is.

So yeah — Gary Pica. Thank you. For the framework, the faith, the brutal honesty, and the laughs. For trusting me enough to grow alongside you. For always – unrelentingly – having my back.  For giving me space to find my own voice as a leader, and later, as a human being.

Here’s to 50 meetings, countless lessons, and one hell of a friendship that grew out of them.

You didn’t just change my business, Gary — you changed me. And I’ll be forever grateful, even if I’ll always follow it up with a smart-ass comment just to keep you humble.  Which – let’s face it – is kind of an impossible goal (see what I did there?)

Here’s to the next 50, my brother.  Let’s go people.