I'd been convening people for years. Even in my personal life, I'd always been the one organizing Guys Weekend every summer where we'd all go rent a house in the woods for a long weekend and hang out and laugh and grill and drink and play cards.

Gathering others and facilitating discussions became a superpower of mine. The awkward silences and grasping for conversation that usually accompanies networking events make my skin crawl. I hated the mindless chitchat that never really seemed to serve a purpose. Traditional networking always felt like you were just collecting a list of names for clout. I wanted to find points of true connection with others. To see where I could help them out or help them solve a challenge.

That is what still fuels me to this day. Helping others succeed is core to my being. It is my reason for being.

The Origins of Generosity

I don't remember when I first struck upon the idea that doing something for someone else and not needing anything in return felt so good. At some point between my time at Axial and when the business of Pavilion fully emerged, I had hit on this very simple concept.

Perhaps it's because it's such a challenge—like trying to unlock a very specific kind of puzzle piece. Maybe it was from my years spent at Gerson Lehrman Group, an expert networking company that was effectively about matchmaking. Maybe it was my Jewish roots—perhaps some part of my DNA was a yenta in Poland trying to find exactly the right combination between a man and a woman.

But for whatever reason, I started to discover how much I liked doing things for other people. And specifically, as I think about it, not just doing things, but connecting them to specific people. And I especially liked it when I didn't need anything in return nor want anything in return.

There was a certain power, a certain liberation, in only issuing IOUs into the universe. There was a freedom, an exhilarating freedom, in not keeping score. It somehow gave me power and confidence and enthusiasm. Because I was willing to “leave money on the table.”

Specifically, I loved, and still love, matchmaking. It's like a puzzle. Who are just the right two people who can be put together with sufficient context to yield something useful. The thrill is in understanding that you don't necessarily need to make a perfect match. The universe, mutual energy, people's interest and willingness in pursuing something novel and exciting, that will be the plaster of paris and Silly Putty that sticks the relationship together.

So it needn't be perfect. And, in fact, it becomes more beautiful when it's not something you expected at all. You introduce someone in food technology to a marketer, and pretty soon they're starting a company together. You introduce someone you worked with years ago to someone else that seems like a fit for their personality, and pretty soon, one of them has a new job.

It's a legitimate thrill.

And, again, it's even more thrilling when you don't ask for anything.

That's because everyone asks for something.

Be Big, Don't Be Small

Everyone asks for something. Everyone.

Everyone is common. Being common is so common. Someone does something for you, they immediately have their hand out. “Lemme hold something.” Someone makes an introduction for you, let's talk referral fee. Someone wants your help hiring for a position, gimme that placement fee. Someone wants to share an idea, sign that NDA, there's only one of these beautiful ideas, and I can't risk you stealing it.

That's small.

There's a scene in Fargo where Steve Buscemi's character Carl Showalter decided not to park in the parking garage. He was only there for a few minutes but the parking attendant insists on making sure he pays. The sign said nonrefundable. Buscemi says, “These are the limits of your life, pal.”

And it's a joke, because if anyone is trapped it's Carl Showalter. But the phrase has always stuck with me.

People who chisel you. People who needle you on every last point. People who put in a nondisparagement clause but don't make it mutual. People who need you to ask to make everything reciprocal in a boilerplate agreement. These people are small people.

Big people understand the great arithmetic of the universe. Big people understand that fullness and vision and expansiveness all comes back to you in the end. Generous people tip 40%, even 50% sometimes. They understand that there are ripples to surprising people on the upside. There are ripples in the universe that spread across the energy fabric of humanity when you do good things and do them out of sheer joy, do them because the joy itself is the very real compensation. And, to be candid, a slightly less noble emotion, the pride. The pride in not asking. The feeling of completeness you get when you don't need anything from anyone else. You do it for the abundance.

That's the beauty and the power of generosity. It fills you up. It's a belief system. It's a belief system in a place that you already are.

My friends and I first started getting together for dinners at a sushi place around the corner from where I worked at Axial. We'd stay in touch between dinners over email with everyone on the CC: line. Eventually, I created a Google Group and gave it a name—the New York Revenue Collective.

Long before my rest stop realization, I brought together this collective of people who all believed that we could achieve more by helping one another. At the time, the average tenure of a chief revenue officer (CRO) was 18 months. My friends and I were in high‐growth, high‐stress roles, and the only way for us to get through it was together.

I facilitated the dinners and the emails, moderating the conversation to ensure everyone was gaining real value from our gatherings. It became a place where we could ask questions in confidence, talk about the tough challenges of our roles, and bounce ideas off each other.

You see, the more senior your role, the fewer peers you have within your organization. It can often be a lonely place, without colleagues who understand the decisions you need to make and the weight placed on your shoulders. The New York Revenue Collective became the outlet we all needed. And it was built on the simple premises of mutual support and kindness. What I call “give to get.” A new kind of community powered by generosity.

I began charging dues for Revenue Collective on January 1, 2018, and I sold a sponsorship to Salesloft for $10,000.

All of a sudden, I had a real business. The germination of a business, yes, but a business nonetheless. One I had started myself and that was built on the characteristics that I valued. Alongside my growing consulting business, I was stepping into the career I had always wanted. And I was building this business, building this community in a new way.

Building a New Kind of Community

It was a strange moment. Most communities were, and still are, free. But I decided to test a hypothesis—people will pay if there was enough value in it for them. The Revenue Collective initially charged just $50 a month. Not a lot, but enough to see if there was something worthwhile there. Out of the 22 people in the New York Revenue Collective, 20 decided to pay—the first being my good friend Michael Manne, currently the CRO of Ocrolus.

As I found out in my work with my coach, Jim Rosen, I stood for helping people I care about and respect to achieve their goals. So, the New York Revenue Collective was predicated on a simple idea: I would do as much as I could to help people in their careers. I would help them find jobs. I would share compensation information with them. I would bring in experts and teachers. And I would create a sense of community.

But I never wanted to create a community just for its own sake. I wanted a community built on values that taught people that being generous and helpful could pay dividends over the long term.

We established simple ground rules—no spamming or direct solicitation. The flip side was you had to be courteous and responsive to your fellow Members. We believed in a world of “give to get,” where before asking for a favor, you first tried to do someone else a favor.

By this point, I was sick of business being cutthroat. I knew we could all win if we supported each other. So I made this a foundational aspect of my community. In exchange for your dues, we all will do everything in our power to help you. It might not seem like it, but this is actually radically different to how most communities are structured.

The Problem with Most Communities

Because most communities are free, the only way to make money from them is to sell sponsorships, essentially selling access to the community to other people. Inevitably that means that Members of the community become the product. And that product is predicated on size—you need as many email addresses as possible to sell to sponsors for the community to be effective. Which means you need to lower your entrance criteria, letting more and more people into the community. The end result is inevitably noise.

And underneath that noise there are two fundamentally broken assumptions—that the community itself wasn't worth paying for directly and that people should be exploited for the act of convening.

We challenged both of those assumptions in the New York Revenue Collective, and still do today in Pavilion.

That's not to say that growing membership is a bad thing for a community. It's my dream that one day there will be hundreds of thousands, maybe even millions, of Pavilion Members around the world who operate on a shared set of values.

But because we accept money from our Members, we are beholden to them. Our incentives as a business are completely aligned with our Members, our customers. It is regulated capitalism at its finest. We only make money if people value what we do. If we stop providing value to our Members, they stop paying us. It's honestly kind of beautiful in its simplicity.

The reason I took the sponsorship money from Salesloft, and the reason we accepted $25 million in funding from Elephant Ventures in 2021, was so that I could build bigger and more valuable programs for the Members. In 2018, I used the dues and sponsorship money to build the New York Revenue Collective into a truly valuable community, not just a dinner club for venting. That capital allowed us to bring in speakers, to make more connections, and ultimately get people the resources they needed to keep climbing that corporate ladder.

In 2021, we were operating at a profit. We didn't need the investment, but our goal that year was to bring as much value to the membership as possible.

We heard time and time again from our community Members that you don't learn how to be an executive in school. So we used that money to build out learning programs that did teach people how to be successful executives. We used that money to build the structures needed for a global community to scale and continue providing value.

Bloating your membership for the sake of selling sponsorships is a pitfall of short‐term, transactional thinking. It's not sustainable, and in the end your community becomes diluted. The reason people joined the community in the first place becomes less important than meeting the demands of your sponsors or advertisers.

You end up monetizing every other aspect of the community to maintain its status as free. But it's not free. That membership comes at the expense of your personal data. Your clout. Your right to live a life free of spam and ads. You become a lead. Fish in a barrel for headhunters. You become the product.

The free community business model is inherently flawed. But, it's not the only problem with most communities.

So many communities do not know what they stand for. They don't know why they exist. Think about the professional communities you and colleagues belong to. What do they stand for? What is their mission?

So many communities articulate abstractions because they're not quite sure. They'll say things like “we exist to elevate the profession of sales.” Okay. What does that actually mean?

Elevate the profession, how? Elevate it, why? What this signals to me is a group of people got together and thought they should form a group, and didn't think about much else. It ties right back to the short‐term thinking of making a community free. Both are short‐term answers to a problem, not a long‐term solution.

At Pavilion, we exist to help our Members achieve their professional potential. Our goal is broad enough that it doesn't limit what we can do for our Members, but actionable enough to tell people why they should join. If you have career goals, if you think you haven't reached your potential in the workplace, we can help you. How we help takes myriad forms, but you know that when you join Pavilion, we will do everything in our power to make your career aspirations possible.

If you join a community whose mission is to “elevate the profession,” how does that help you? Will you be better at your job if the industry was more respected? Does being respected mean you operate on a set of core values? Does this community exist to give back to its Members?

When I was at Axial between 2010 and 2015, I had access to a community platform run by First Round Capital, who invested in us. People would share articles and they would help each other and answer questions.

When I was fired from Axial, I was barred from everything. Logged out and locked out of every account I had, including the community platform. That community only existed to help employees of First Round Capital companies, and I was no longer one of them.

Not only had I lost my job, but I lost many of the connections and mentorship that would have helped me grow into a stronger leader. They tossed me out because I was no longer of use to them.

What it comes down to is this: that community did not serve its Members. It served investors and CEOs. The actual day‐to‐day Members meant little to them. They could be easily replaced.

Every community I had been a part of, up until Revenue Collective and Pavilion, was too scared to build something that didn't ultimately serve investors or didn't ultimately serve CEOs. From the beginning, Pavilion was built by operators. We wanted to build a safe place for them to talk about the challenges of their roles, where they didn't need to worry about what they said getting back to the C‐suite.

For most of our existence, we didn't even let CEOs join. Beginning in 2021, we started building curated cohorts of CEOs, letting in limited numbers at a time and building a new part of the community. This initiative was led by several existing Members who had been promoted to C‐level roles.

But overwhelmingly, our membership continues to be operators, and they continue to drive how we operate. With the majority of our funding coming from these kinds of Members, we will continue to do what they ask us to.

The secret to building a community, or a business, really is simple. Listen to what people want and give it to them. Give it to them because you genuinely want to help them. When you love and serve your customers generously, the growth possibilities are endless.

Love for Customers: The Missing Piece of the Equation

The notion of truly loving and respecting your customers took hold of me while I was working for a company that did the exact opposite.

Technologically, the company had everything going for it. But they came to believe that they were smarter than the customer, going as far as to have open disdain for customers.

Unit economics are crucial in judging the performance of a business, but retaining those customers is just as important. Customers talk, and negative experiences tend to have more power than positive ones. If your organization has a reputation of being hard to work with, that is not a notion easily overcome.

The truth is that great products are built by people who love their customers. If you put generosity at the heart of your business and truly listen to your customers, you'll probably end up building something meaningful and compelling to them. And you'll be a company they actually want to do business with.

Listening to your customers is so often overlooked in business. We have a tendency to overcomplicate and think we know best. But our customers know best. They will tell you what they need. All you have to do is listen, and then act on the things that are within your control.

This is why we end every week at Pavilion with Member success stories. They help the team remember who we are here for and motivate them to go into the next week serving the people who make our company possible. Without our Members, there would be no Pavilion.

We created learning and training opportunities because our Members told us they needed them. We formed small councils within Pavilion because our Members told us they wanted more intimate interactions and connections. We created a group dedicated to helping Members find their next opportunity when they lost jobs due to the pandemic. None of these initiatives were my idea. They all came from our membership, who pay us dues to make it happen.

Of course you need to be strategic with your business and decide which feedback to act on. But if you ever feel unsure about your direction, listen to your customers with an open mind. They'll tell you where to go.

Generosity Can Be a Competitive Advantage

What this all comes down to is that a business built on generosity will bring back everything (and more) that it puts out into the universe.

When I said Pavilion was founded on “give to get,” this is why. Generosity and giving before you get is not simple altruism. It is a sound business philosophy that can change your relationship to those around you and help you accumulate influence and power.

We have been taught in business and in life not to leave anything on the table. To never split the difference. To always get more out of an interaction than you give.

I'm here to tell you that this is ultimately a destructive and short‐sighted way to live. Inevitably, someone will come along who is more cutthroat, more reckless, and more willing to squeeze out every last drop. Then what will you be left with? A string of pissed off acquaintances who will do nothing to help you get back on your feet? A list of regrets? Maybe some money?

I used to live in that scarcity mindset. That if I didn't take, someone else would. By the time I was standing on the beach in California, after I'd had that epiphany on the New Jersey Turnpike, I could see how wrong I was. It was only when I gave to others that I truly started to gain.

And it's not about being selfless or that I'm less greedy. What it is about is being okay without instant gratification. It's about knowing that what you do now will pay back in dividends in the future. It's about being long‐term greedy.

Being generous doesn't mean you don't want power or wealth or notoriety. Being generous is a long‐term competitive advantage that will build all of those things over time.

Generous people accumulate power because, by consistently looking to help other people, you become, de facto, someone who can help other people. Being someone who can help other people is powerful and soon, simply through the act of serving others honestly and without expectation, more and more people come to you for assistance, and they will come back to you with a variety of opportunities. The results compound.

So many short‐term thinkers only see the table in front of them. But there's a bigger table with more money if you think about your life and your career in the long term.

If I had tried to turn the Pavilion into a recruiting firm or if I had tried to start an investment fund right out of the gate, I wouldn't be anywhere close to where I am now.

The Pavilion business model is a much, much bigger idea than starting an executive search firm. It's an idea powered by generosity, loving our Members, and bringing them value. That idea took us to a $100 million valuation, and will take us as far as we want to go.

Generosity can take you where you want to go, too.

Putting Generosity into Practice

So how do you put generosity at the center of your business?

Look for ways to help people every day.

Introduce a colleague to someone else in your network. Look over a friend's résumé. Recommend a book or a program you know will help someone further their career. Offer advice on a difficult work situation. Make connections. And ask for nothing in return.

We charged a flat fee. Most communities will tell you there's a playbook to monetization. You start a job board and charge for it. You sell sponsorships. You start a recruiting business and charge for it.

Pavilion is able to fundamentally differentiate itself by not doing those things. Instead, we charge one flat fee and try to pour as much value as we can into it. The price you join at is the price you pay as long as you want to remain a Member. We still have original Members paying $50 a year.

We believed and continue to believe in the fundamental long‐term value of customers that come back again and again because they know they'll be treated fairly and with kindness, and we are happy to create much more value than we ever capture in the form of dollars.

This long‐term focus—putting trust and generosity into the core of what we do—creates a far more powerful beacon for those in desperate search of like‐minded travelers, rather than nickel and diming them for each and every service we provide.

Members trust us because they know we're working for them. My peers trusted me because I led with generosity and didn't ask for anything in return. And when I needed their support, they were thrilled to lend it to me. At the time I had no idea if or when I would need to cash in, but when I did, the generosity came back to me tenfold.

Make generosity your competitive advantage. Believe in the long term. Believe in a world where others are also living by the same lessons. Accept the fact that it won't be everyone, but also accept that there will be enough positive energy created by your generosity that you'll achieve what you want to achieve and you'll do so with a full heart.

When you build something on a set of core values, fuel it with generosity, and practice sound business strategies for long‐term growth, you'll be able to capitalize on more opportunities than most.

Chapter 4 Tactics: Find Someone to Help

I don't like networking. I don't like happy hours. I do like helping people. So many times people ask me in career conversations what the key is to career advancement. I typically say the same thing, “Look for someone to help.”

Helping can take a lot of forms, but the easiest way to help is to connect people based on mutual interests. And not mutual interests in the sense that they both like rock music. But mutual interests in that one person has a need and one person has a capability.

This typically manifests itself into job placement. Someone looking for a great VP of marketing coupled with someone who is a great marketer. By cataloging discussions either intentionally through a notebook or document or just by remembering, you can find ways to create matches between people.

Do this consistently over time and do not ask for a finder's fee or any kind of money. Just focus on accumulating the experience of making useful connections and then differentiate yourself by not seeking immediate reward for your efforts.

And don't worry that you're not getting paid to foster this assistance. You are getting paid. You are getting paid based on the increase to your reputation, the increase to your visibility, and the cumulative likelihood that over time people will remember your assistance and contributions and will find some way to return the favor.