Chapter 3
Reset Your Destination

What do you stand for?

The months leading up to that fateful day at that rest stop on the New Jersey Turnpike were filled with anxiety. An uneasy feeling in the pit of my stomach I couldn't shake. Even before my rest stop epiphany, I had an innate sense that something needed to change. I couldn't keep going like this.

So I'd sought out a coach to help me take some different steps in life. Emmanuelle Skala, one of the great revenue leaders in startup land, had suggested I reach out to her coach, Jim Rosen.

We got on our first video conference, and Jim came on the screen and we got to chatting. He innocently asked me, “What do you stand for?”

My mind went blank.

“Making money?” I said.

“That's not enough,” he said. “What do you stand for besides making money?”

I didn't have an answer. And that's when the panic started to set in. If I didn't know what I stood for, how could I build something great? What will it be about? Who will it be for? What was I even doing with my life?

It's not enough to stand for “making money.” In fact, it doesn't really answer the question in the first place. Making money is the output of building something wonderful. It's not prescriptive. It's ultimately empty and means nothing.

You make money when you build something that reflects who you are, what you stand for, and your values. All of that needs to come from a place of joy and fulfillment. Money is the natural outcome of that process in regulated capitalism (the most beautiful system in the history of mankind, in my opinion).

So standing for making money wasn't enough. Jim pointed that out for me. But in BRS (before the rest stop) time, it was a puzzling moment for me. What did I stand for?

The Elusive Struggle for Money

I'd suffered through so much cynicism and defeat in the previous 10 years. The culture of my first company, Gerson Lehrman Group (GLG), had been so much about making money in those old days. And the clients we'd served, hedge funds, all had 20‐ and 30‐something millionaires getting huge bonuses for their trades and their investment positions. Twenty‐eight‐year‐olds driving Ferraris around the Hamptons and Connecticut. God, I was jealous.

I'd had a few years back at GLG where they'd written me some very large checks. Like back in 2006 and 2007, I made close to $800,000 after Silver Lake Partners invested over $200 million with us, and I was paid a retention bonus as a key person on the account.

Coming out of GLG, in the midst of a financially costly and emotionally tragic divorce, all that money I'd made had been bled out of me slowly by lawyers and my ex‐wife. All things in life are correlated, and so often there are macro forces beyond our control or reach. While I know now that looking at yourself as a victim does nothing to help, it's impossible to deny that sometimes we are part of something bigger. And at the time, victim was all I could see in myself.

So there I was during the 2008 and 2009 financial crisis with seemingly endless divorce costs, now making $700,000 less at my new company, Axial, and trying to reorient my entire life.

The “lesson” I'd taken from those days was simple: find a way to make money. Money is what matters. Work is a means to an end. And that end is to win the competition against your peers and friends. Win that competition of wealth and expensive watches and nice cars because those are the things that are important in life and especially when someone is trying to take it all from you.

I was completely blinded by this need to make more. To be more.

I'd spent a few months after I was fired from GLG trying to find what appeared to be a linear route from my perspective. Logically, I thought I should go work at a hedge fund where I could do for them internally what GLG did for them externally. I had a few meetings, but the reality was that I had no credible experience as any kind of head of research, and they would've had to teach me far too much to be useful. I wasn't a salesperson per se. I wasn't an investor. I was a service provider. And service providers generally don't get to be the ones who make it big.

So instead, I joined a startup. I learned a lot during my years building Axial, but money was always front and center for me. It was always dominant. I wanted nice things. My girlfriend, who later became my second wife, Camille, wanted nice things. It was a struggle. A grind.

Man, did we grind.

For years, all I could think about was money. I'm sure there are folks out there who understand. I was locked in this struggle. Eking things out. Spending more than I made. Negotiating for late payments on my maintenance to my ex‐wife. Watching the credit card debt bounce around. Looking for shortcuts.

At one point, I'd become so desperate, I fell in with a con man from Germany full of talk and promises. He had contacts. He could sell cheap luxury items directly from retailers in Italy to some of the best e‐commerce platforms in the United States, like Bluefly. Could I find someone to buy luxury handbags from his supplier? I could make 20%, he assured me.

I started networking with other e‐commerce sites like Rue La La. I made the introductions, but as soon as I did, the guy would swoop in, steal the connection, and cut me out. We had a falling out when I accused him of being a fraud, but that was only after he made a couple hundred thousand dollars in sales from my contacts.

But still I couldn't stop. More credit card debt. Getting some kind of payment, but not paying taxes on it. Thinking if I could just make more money, tomorrow would never come.

But it would. I'd always have to pay the bill. Tax day would roll around, and my accountant would tell me I owed the IRS $60,000, and I would break down, knowing I didn't have it. Not at all.

Money clouded my brain for years.

On a trip to Italy years ago, all I could see were dollar signs. Every minute was like we were in an overpriced cab from the airport, watching the meter click. Dinner and drinks: $300. A boat to Capri: $250. Here's a nice little shopping detour in Paris: $500.

Coming home, I was terrified to log into American Express to see the butcher's bill. The bloody butcher's bill.

So, you see, when Jim Rosen asked me in 2017 what I stood for, I thought, “What kind of question is that?” I stood for paying off all the people who wanted something from me. I stood for making money. I stood for anxiety and stress and fear and bills I had to delay.

What else was there to stand for?

What Do I Stand For?

And yet, that's why Jim and I did the exercise.

I hired Jim to help me navigate the treacherous waters that were The Muse and the sense of unease I had. I still ended up getting fired at the rest stop anyway, but Jim and I had already embarked on our journey together. I'd even negotiated Jim's fees as part of my severance package with The Muse.

If I cleared away the doubt and stress and anxiety, I sensed there was something deeper within me than just a desire to make money. We started looking at various attributes and qualities of a human being. I would circle those that resonated with me.

We ranked values against three key elements: foundation, focus, and future.

We started with the Foundation—what were my foundational values? What was important to me? We looked at values such as Honor, Respect, Discipline, and more to establish the foundation that was core to my survival.

From there, we looked at values that helped me Focus on who I was and helped me define my identity in a professional context more clearly.

Finally, we used those values to establish a vision for the Future—a vision for who I wanted to be.

The values most important to me were:

  • Support
  • Helpfulness
  • Loyalty
  • Appreciation
  • Altruism
  • Humor
  • Forgiveness
  • Mentoring

And all of it still centered around a concept of me as an architect of my future. One that valued achievement and impact over the course of a life.

The exercise was time consuming, but it was productive and useful. And at the end, I emerged with the realization that I did indeed stand for more than just making money. Much more.

From this values exercise, we wove together one coherent statement. My own personal mission statement. Something that I ultimately “stood for.”

Simple, right? And maybe obvious, but at the time, it was a bit of an epiphany. One more milestone on my lifelong journey to transcendence.

That mission statement is at the heart of the business I built. In fact, that IS the business I built. That's the whole point of Pavilion.

This statement helped me understand a core fact about myself: I draw strength and energy from helping people. Not just any people, but people I care about. Although, admittedly, I had a general tendency to care about most people I interacted with. But more than that, I feel fulfilled by helping people I respect.

And who I respect above all else are people who combine compassion with a work ethic. The kind of people who have the knowledge and wisdom to put their back into it and work hard, while still bringing compassion to their daily lives. The people who see the world as it is, understanding its trials and tribulations and tragedies, and still retain hope and optimism. People who I liked to think were like me.

Those are special people, and I want to do whatever I can to help those people achieve whatever it is they want to achieve.

And the funny thing was, when I looked behind me, reflecting on everything I'd done the past few years, that's exactly what I was already doing. I was already helping those people.

That's what the New York Revenue Collective was, after all. It was a series of dinners and emails all built around a simple concept—let's help each other. Maybe that could be the thing I stood for. Maybe that could be what drives me.

How to Reset Your Destination

Even just the fact of knowing and identifying what I stood for was a seminal moment for me, and it can be for you, too.

You have to know what you stand for. You don't have to stand for the same things I stand for. But you have to stand for something—something more than making money.

Money is the thing that follows when you pursue what you stand for. Your values are what will trigger the avalanche of money and success if you can find them and slowly, tirelessly work to align your reality with the vision of the world you want to see.

The problem for me in 2017, and the problem when I tried to give this advice to other people, was what you stand for doesn't always immediately translate into professional success. I had no way of knowing what would happen in the future. I didn't think it was possible that a small little networking business might be worth $200 million, or even $1 billion one day.

Unfortunately, that's how most things related to mental discipline and our relationship with the world function. We want everything to be as easy as pressing a button. Just hit it, and—poof! Your life changes instantly.

But that's the thing about playing for the long term and placing faith in something bigger than yourself: you need to trust that your values and ethics will someday lead to something great. It's a leap of faith, of sorts.

Leaps of faith are leaps because they aren't guaranteed. You need to trust that doing the right thing with the right structure will reward you, over time, in the ways that you've hoped. You need to believe it will happen.

But calling it a leap of faith for me isn't exactly fair or accurate. These were decisions made out of necessity and a sort of desperation.

I remember sitting at breakfast with my friend Jonathan Glick about a year later when I decided to pursue Revenue Collective (now Pavilion) full time. I said, “Well, if this doesn't work out, I can always go find another CRO job somewhere.” He smiled at me indulgently, supportively, and said, “We've tried that experiment haven't we?”

I can't sit here and say, “It's a simple formula, my friend! Quit your job. Hire Jim Rosen. Do a values exercise. Soon, you'll be worth millions.”

It's not about instant gratification. In fact, in many ways, it's about the exact opposite of instant gratification. It's about doing something for its own sake and not quitting your job or telling the man to fuck off just because (although that can feel very good).

It's about living a life according to your true principles. The main thing about charting a new destination is that it's a destination built on a different view of the world.

Don't get it twisted. Money still matters in this world. But it's a world inhabited by people willing to help you. Willing to support you. People who are willing to give you their time and not send you a bill the minute you hang up the phone. Doesn't that sound like the world you want to live in? Sometimes what we need is simply affirmation and confirmation that such a world can exist and that it's possible for us all to move toward a different universe.

When I was doing this exercise from my living room in the West Village on a Zoom with Jim Rosen, drawing squiggly lines between words like “Humor” and “Discipline” and “Compassion,” I had no idea this would translate into anything directly. It wasn't about money, and it wasn't about instant reward of any kind or shape.

It was born from the intuition that there was a different way to conduct myself and that in order to get off the hamster wheel, I needed a series of frameworks and ideas that could help shift the trajectory of my life toward something more meaningful. Following the playbook others had set for me wasn't working, and there didn't seem to be an exit ramp.

The New Jersey Turnpike of my career was one gray potholed lane after another with smokestacks in the background. I had no idea that New Jersey was actually a green beautiful place somewhere beyond the periphery of the prescribed path. Once I took the exit ramp, a whole new New Jersey opened up to me.

Foundational Myths

Figuring out what I stood for was important, but putting my values into action meant challenging the foundational myths I thought were core to my being.

What were the myths I told myself? I didn't have any good ideas. I couldn't be a CEO because I didn't know how to code. I wasn't technical.

That meant that despite working on companies for 20 years, and having strong opinions about how to build them, I'd removed a specific, lucrative, and fulfilling possibility for myself immediately. As the CEO of Pavilion, it's clear now how wrong I was.

Why do we tell ourselves such myths?

Fear. Fear is the underpinning of so much of what we believe in life and what we tell ourselves is possible. Fear is about the unknown. Fear is about thinking something might be tragic or terrible or have some horrible outcome.

I was held rigidly in place by fear. Part of it was a lack of experience. Part of it was frivolous spending and a strange relationship with money, living under debt and constantly comparing myself to such an extent that every dollar I had was really about propping up my identity.

On that trip to Italy, Camille and I first visited a friend of her late mother, Marco Musso, in the city of Genoa. We then rented a car and drove down the coast to a beautiful old hotel called La Poste Vecchia, built on ancient Roman ruins. The trip was off to an amazing start. It seemed like one of those trips and one of those places that inspires you. Maybe things would be different.

But then things turned as we continued on to the Amalfi Coast. We were driving down beautiful winding mountain roads into the towns of Sorrento and Positano. This area of the world is supposed to be some of the most beautiful in existence and I was prepared for some kind of transformational, transporting experience.

We arrived at our hotel, and everything immediately started to feel less than perfect. I do have a tendency to find fault, and doubt started creeping in. There were ants on the pillows. I thought, doesn't this place seem a little shabby for $500 per night? It was the most I'd ever spent on a hotel room to that point. Shouldn't it be the most amazing experience?

These types of fancy European‐style places can be toxic if you don't have the right mindset or the right resources. On that trip, I felt like the meter was always running. Every cocktail, every bottle of water pushing me backwards against the wall and creating more and more stress as I tabulated bills and invoices in my head. I spent countless hours counting and recounting the money in my accounts against my credit card debt and sinking deeper and deeper into black darkness.

Fear. Fear wrapped itself around me like an anaconda on that trip. I carried this fear and stress and anxiety with me for years—and still do if I don't force myself to reset. There is still an active sense of dread lurking inside my head. A sense that something is wrong.

For so many years, I didn't understand that dread. Because when it wells up inside you, your brain takes it in and puts words against it. It's all‐consuming. You feel like the choices you make are predetermined by those feelings, so your brain takes dread and fear and spins it into stories. Those stories are arbitrary, but at the time you don't know it.

One story I told myself: I didn't deserve this Italian vacation. Another story: whether I deserved it or not, I couldn't afford it. The dread loved my money anxieties. Fed off of them, always wanting more. I spiraled down, down, down.

The dread led me to visions of the IRS and a feeling of being trapped, tied down, always constrained by earthly limitations, squeezed too tightly.

In fact, the dread loved to take those money fears, remove my personal agency, and then paste them unfairly onto other people.

Other people were the problem. I told myself outside pressures were putting me in a position that forced my back against the wall. With each passing minute, my anxiety would grow and compound—and grow and compound.

These are hard things to “fix.” There actually isn't much fixing of them because there is some kernel of truth to all of them. Of course, your fear and dread know that—that's why they're so powerful.

So maybe my dread would have been lessened if we had never taken a vacation. But maybe I was using all of these stories about vacation and spending as a means of displacing my own insecurities.

Figuring out who you want to be in life is hard. I felt completely trapped in 2017. But the beginnings of my personal and spiritual transformation finally took hold when I decided it was time to take the exit ramp and reset my destination.

Resetting Is a Process, Not an Act

When I was fired for the penultimate time, there was of course fear and trepidation. Those foundational myths were potent. But there was also an awakening, one that unfolded over a period of years once I decided to take control of my life.

From fear or exhaustion or whatever process you want to call it, there was a beginning. That process of resetting can be construed as a lowering of expectations, but that's not how I experienced it.

There was no need involved. Perhaps that was the secret. There was no desperation. The motivation came from a place of energy and enthusiasm and fulfillment, instead of a desperate anxiety to fit myself into other conceptions or definitions.

I wrote down everything I knew and began to imagine my life differently—not as an act of rebellion, but as a complete redefinition.

I looked inward and tried simply to place independence and autonomy at the center and then layer‐in all the work I had done with Jim Rosen on establishing my values. My life's success moved away from a simple definition of net worth to something more modest and much more empowering.

Once you realize you can make money on your own, doing the thing that you love doing, then perhaps that is wealth in and of itself. Wealth is really about the freedom and independence to pursue your passions and your ability to first and foremost prioritize your own time and energy. Those things don't require a certain amount of money, although they do require some of it.

A Sense of Becoming

By December 2017, my consulting business was up and running. After my first consulting gig with LeagueApps, I consulted with a company called Optimove that provided software to retailers. Then, I consulted with a company called WayUp that provided a platform for college graduates to find their first job. It finally seemed that I was headed in the right direction.

But the thing I remember most about that time was taking an entirely different kind of trip with Camille and our beautiful dog, Walter, to California.

We stayed at a house in Laguna Niguel, up the hill from Laguna Beach. I had taken this trip without a steady job, but with the knowledge that I had a pipeline full of consulting clients waiting for me when I returned.

And unlike the trip to Italy the summer before, this felt entirely manageable. And I felt free. For the first time in as long as I can remember, I didn't have anyone to answer to back on the East Coast.

Camille and I would wake up every day and go for a hike in the trails around Laguna. We'd eat a late lunch and go sit on the beach with Walter and film short videos where his fluffy coat would blow in the breeze. We rented a Ford Mustang convertible and Walty would get in and hop into the passenger seat and then we'd drive to pick up some green juice for Camille while she slept, and we'd listen to “Money for Nothing” by the Dire Straits very loud while we basked in the sunshine and the wind in our respective hair and fluffy fur coat.

But the best feeling was simply a soft, warm exhilaration when I realized I was on a path to doing something that truly aligned with what I stood for. It was almost like my sails had caught the solar winds of the universe. My toes dug into the sand in Laguna, on a blanket next to my wife and dog, and I was thinking that the future only contained possibility. That somehow I had wrested my independence and control of my life from others and given it back to myself. I finally had a new destination on the horizon.

Chapter 3 Tactics: Build Your “About You” Deck

When Camille told me to write down everything I knew about building a business, she was intuitive and prescient on a practice that can help change your career and enable your success. Which is a simple thing—document your expertise and the concepts you develop over time.

Keep a Google Doc of notes, strategies, and tactics you have accumulated over time and over the course of your career and your work. Jot down key insights. The document can evolve in any number of ways, but as you grow you'll slowly build your own playbook.

Once you have a batch of notes and ideas and have refined them, this can become part of your brand, resume, and toolkit. When you interview for opportunities, you'll be differentiated because you'll have a ready‐made overview of how you operate and what you put into practice.

Additionally, over the years, I've also compiled an “About Sam” document that I share with incoming employees. This goes into my mood, temperament, how I like to receive feedback, and how I operate. It helps manage expectations appropriately and directly addresses the years of feedback I've received on how I process my emotions.

As much as I'd love to be more consistent as an executive, the reality is that I've always been a bit up and down. But as Anne Juceam told me, self‐awareness is kindness.

If I can prepare people for what it's like to work with me and, as an executive, can outline my beliefs on operations, strategy, and tactics, I can demonstrate that I've been using the years of my career to intentionally lean into key experiences and challenges.

The process of documentation helps clarify your beliefs and practices while also enhancing the perception that you are a student of the game and take the time to develop actual frameworks.

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