From Surface to Substance: The Power of Authenticity in Connection

While many of us compartmentalize work and personal matters, we often underestimate the benefits that come with dropping the formality in our professional networking. Tapping into interpersonal skills that we usually reserve for more casual connections yields relationships of much greater substance and longevity. 

Let’s start with the big idea: What does “Orchestrated Connecting” mean to you, and how is it different from traditional networking or relationship-building?

Relationship Value is the most important currency on the planet, yet we often don’t value it and how we convene and bring people together is the primary way we build those relationships and increase our relational value.  

I’ve rarely been to an event where the people I was supposed to meet were curated for me. Nor do I meet a net-positive amount of people each time I drag myself out for event after event after conference. My most positive experiences are meeting people waiting in line for the bathroom rather than the person timidly waiting at the bar, or the alpha extravert who shakes my hand warmly and tries to see through me. 

Orchestrated Gatherings–the model on which the book is based–are different, as is the entire systems thinking around community design. Infusing intention, purpose, and action into a community that builds trust was the goal. We wanted to do it differently with the people who deeply understand the importance and process are at the TOP of their game with genuine connection. A decade in, I can safely say Orchestrated is a network of trust having engendered tens of thousands of ripples of relationships, all backed by action.

Your new book, Orchestrating Connection, was co-authored with sociologist Noah Askin. What inspired that collaboration, and how did the mix of practitioner and academic perspectives shape the book’s core thesis?

Noah and I met through a ripple of connections.  His “Covid office hours” built him a new network by being open to anyone taking a 15-min Friday slot, and our mutual friend Jamil (his former student) thought we both saw the world differently. Jamil made the intro. We both did see the world differently.

Noah asked to interview 50 of the Orchestrated Community.  He met powerful, amazing people who first offered to help and get to know him and inspired us both that there was something “there” that transcended the events or purpose-driven network I’d built for 5 years (at that time). 

I come from academia on my father’s side, and am an avid reader of history, psychology, and any book on connection/relationships, but what I’d built was done systematically and instinctively, since connection is a living, breathing, ever-changing thing. Noah brought a lifetime of practice and a decade-plus of network research into this work, infusing together for a greater outcome than we could have accomplished on our own.

Our goal was to build out the playbook based on the real-life experiences from my work, and to define in full what makes this approach useful, practical, and inspiring for all.

You’ve said that we live in a “tribal world”—a phrase that can feel both urgent and ominous. How does your work aim to counteract the polarization and fragmentation that come with tribalism?

From our viewpoint, while “tribes” are not necessarily bad historically, any time you see someone as the “other,” society has failed you, and you have failed society. So the fragmentation in our world that tries to return to the past, to what “was” our community, is a false thesis, as we argue that ONLY purposeful community and the self-work that goes along with it, can make our society stronger again and less polarized.  

While we do not specifically address the current political situation or ongoing wars and conflicts, we work to demonstrate that our key principles of curiosity, vulnerability, diversity, generosity and gratitude can be combined to create a culture that reduces that tribalism, because you can choose to curate your life and the community around you, towards a greater purpose than your own wants or desires.  

In a time when online platforms claim to ‘connect’ us more than ever, many people feel more isolated. What’s the missing ingredient in these digital interactions—and how do you help people rediscover real connection?

Real connection is a combination of vulnerability and curiosity, backed by actions that express generosity and gratitude.  Whether virtual or in person, we crave understanding, love, and, more than anything, to be heard and seen. Yet it is often so terrifying to think of being rejected.  It is easier to hide than to be courageous enough to own your value and to constantly examine who you are and how you show up in this world. 

At a recent event, I asked the attendees which of the 5 senses they would give up if they could live past 100 in full health, without that one sense. Everyone justified what they would give up, but no one would give up touch. Not a single person. 

The digital world is an incredible tool to expand our consciousness and world, but it is not the solution. The solution is to be more intentional and purposeful and to give and give and build a community around you that has your back when you need it most.

The gatherings you organize are described as high-trust, high-impact, and intentionally curated. Can you walk us through what happens at an Orchestrated Connecting event that doesn’t happen at a typical networking dinner or industry mixer?

As I mentioned previously, I hate nearly all events. Events are re-mixers, designed for extroverts. A truly intentional event should begin with what you came for, to meet the handful of people you ideally should dig deeper with and get to know.  This is why Orchestrated Gatherings start with small groups, 100% on time (you cannot be late) with deep diving questions that have nothing to do with your net-worth, your job, or your family–but instead your soul.  Strangers find themselves bonding, being heard, seen, and appreciated, and trust is established often so instantly you forget how hard that actually is to achieve.

After small groups, I will speak about the importance of relationship value and many of the principles in the book, and then give 2-3 people the opportunity to speak about their impact. This is called the Impact Ask.  5 minutes for your passions, how those can be amplified, and then the type of relationships we need to move those passions forward. 

By demonstrating that it is OK to ask for what you need, in a proper context, you can create an event that already acts like community even when 70-80% of the people are strangers before they step forward into the room.

Then we leave the final hour or 2-3 hours (I am a morning person so sometimes I leave before half the room does) for open connection–unrushed, intentional, and sought after to meet one more person for you and to meet several more for the people you’ve bonded with.

You’re known for connecting people who otherwise might never meet—across industries, generations, and even ideologies. What do you look for in the kinds of relationships that are most likely to create a lasting impact?

The most impactful relationships come because of deep listening, not just to what someone says, but what they are not saying.  And when you master this, as I hope I have, you don’t introduce people because of a shared interest, you introduce them because their ASKS match each other. They complement each other.  

My community is extremely diverse, very powerful, and represents access other people would dream of, or be willing to trying to pay for, but you cannot access it without being an “action-oriented, natural giver, that I would leave my kids with.”  By establishing a code based on positive action, every introduction is valuable, whether it be for General David Petraeus, WNBA Star Candace Parker, mental health champion Amanda Beausoleil, or a friend whose ask is so private I can’t disclose who without making sure the other people is ready to support.

The book makes a case for community as a kind of ‘social operating system.’ What are the foundational rules or rituals that make a community not just function, but thrive?

A systemic community is only strong when you have every single person within the community dedicated to elevating themselves and others, for whatever purpose you prescribe. It is not something you can just pay to be in and stay in:, you have to have community where the primary core is about action, generosity, and holistic reciprocity.

In our book, we make clear that in addition to the five core principles to build the culture of each community, that the element of RISK is essential. Community is only functional when it is clear how and why you belong and when your actions could result in your removal. While that may seem harsh to many, just look at any community for which the rules are transparent and enforced, whether it be Burning Man or the Orchestrated Community. And then look at those for which the rules are bent or modified depending on “who” broke them.

To thrive, everyone has to act in a way that enhances and amplifies each other, without a transaction expectation in return from those you help. You have to trust and be trusted.

Many high-achieving individuals struggle to build authentic relationships because so much of their world is transactional. How do you help people shift from transactional to transformational connection?

The goal is not to avoid transaction and have a bunch of friends. I am not naive in the fact I have built a network with insane access to sports, Hollywood, billionaires, CEOs, and on and on. But whenever I ask of these friends, the intention is to build things that allow you to maintain relational value even when transaction occurs. 

Perhaps this is best served by example: I once challenged a very (curse word here) private equity person I was stuck at a dinner with, who directly challenged my world of connection and putting relationship value first. I asked him about his top 5 deals. He proudly bragged about all of them. And then I asked him who introduced him to those top deals. 

He paused. 

And then he shared that it was just two people who brought him his top 5 deals ever.

I asked him if he was still in touch with those people, and he paused again and said, “oh my god, only one of the two.” He realized he had cut himself off from the top-performing “connector” for his work, having focused on the immediate transaction and not the longer-term relationship that brought 100x the value.

With the book’s release and the movement it aims to spark, what do you hope changes—at the individual, organizational, or even global level—as people embrace this new framework for connection?

Noah and I would love, humbly, to not just put “author” on our LinkedIn Profiles. Everyone who has read the book so far, and those who have experienced my Orchestrated Community, never sees relationships the same again. We have “named” what was unspoken or unwritten, revealing a code and a playbook that, in our loftiest vision, becomes a new way to see community, with intention and purpose and drives more people to hold themselves and those around them accountable in a world where what you say and promise and what you do does not seem to matter.  

We believe that these actions do matter, and that we can re-shift the balances of power through purposeful, intentional community. 

At Worth, we often ask: What does worth beyond wealth look like to you? How do you define a meaningful and impactful life?

I have spent most of my career around the wealthiest and most powerful people in the world. From working directly with Ray Dalio, and having interacted along with ith over 67 Giving Pledge Families, to having 7 people each with one degree to Kevin Bacon, or apologizing to Asser Malik and his wife Malala because I took a week to get back to them, I have studied power, fame, and ultra-wealth live and in person.   

None of these people, or their most trusted allies, are in my community because of those characteristics. They are there because their actions give them purpose, and that intention elevates others.

Ray Dalio, among others, has given out a HUGE amount of his wealth while living and continues to do so. I admire this beyond even what my words can convey. The family is purposeful, intentional, and generous, along with being clear about what they can help with, and what they can’t. I learned more working with this family in two years than I did in the ten years prior.

Worth is your community. It is who you can call in the middle of the night. Who checks in when you’ve fallen down, not when you’re at the top? It is that subtle shift in a friendship from what you can get out of it, to just being with someone and feeling like that little kid in you never went away, and they are seen. Heard. Valued.