Inside CVC: Orchestrating Connection: Why Trust, Gratitude, and Community Drive Better CVC & M&A Decisions

In this episode of Inside CVC, we’re joined by David Homan, author of Orchestrating Connection, for a wide-ranging conversation on why trust, gratitude, and intentional community building are no longer “soft skills,” but strategic advantages in corporate venture capital and M&A.

Drawing from more than a decade of building a global, high-trust network spanning family offices, venture capital, private equity, and corporate leadership, David challenges the transactional mindset that dominates deal-making today. He argues that the biggest failures in CVC and M&A often stem from ignoring relationships—while the biggest wins are unlocked by honoring the chain of connection behind every opportunity.

We explore why leaders who prioritize curiosity and vulnerability make better long-term decisions, how communities function as strategic “current” rather than static structures, and why boards should treat trusted relationships with the same rigor as capital allocation. Along the way, David shares real stories from the worlds of venture investing, corporate strategy, and global leadership that illustrate how connection can de-risk bold bets—and why cutting out the connector often costs more than leaders realize.

This is a conversation for CEOs, board members, CVC leaders, and operators navigating complexity, uncertainty, and transformation—where who you trust may matter more than what you buy.

What You’ll Hear in This Episode

• Why **relationships—not assets—often determine the success or failure of M&A and CVC bets
• How honoring the chain of connection builds trust, access, and long-term advantage
• The difference between transactional capital and community-driven value creation
• Why curiosity and vulnerability are underutilized leadership strengths in boardrooms
• How trusted communities act as a strategic hedge during periods of disruption
• What corporate leaders miss when they prioritize speed over integrity in deal-making
• A simple, practical ritual leaders can use immediately to strengthen trust and influence

Transcript

Steve 0:00

Welcome to Inside CVC, the podcast that brings together leaders in innovation and capital investment to explore the trend shaping the business of corporate venture capital. I'm your host, Steve Schmidt, and together with Philip Willigman, we're speaking with corporate investors, entrepreneurs, and ecosystem builders driving the future of innovation. InsideCVC is brought to you by UPath Advisors, helping corporations and startups unlock sustainable growth through strategic partnerships. To learn more, visit upath.com. That's the letter u, com. And to catch up on all of our episodes, search InsideCVC on your favorite podcast platform or visit upath.com forward slash podcast. In this episode, we explore trust, access, and the role of purposeful community in venture capital, MA, and corporate leadership. Our guest is David Holman, composer, connector, and co-author of Orchestrating Connection: How to Build Purposeful Community in a Tribal World. David has spent more than a decade building and stewarding high trust global communities, spanning family office, venture capital, private equity, and corporate leadership. In this conversation, we discuss why relationships are a strategic asset, how trusted networks de-risk bold decisions, and why leaders who treat connection as infrastructure, not etiquette, consistently outperform. Here's our conversation with David Holman. David, thank you for joining us on Inside CBC. How are you today? I'm doing fantastic. How about you guys? Thank you for taking some time out of your schedule to join us today. Really exciting to have this conversation. You've got a new book out, Orchestrating Connection: How to Build Purposeful Community in a Tribal World. Can you start today with maybe telling us a little bit about the premise of the book and why this theme of chain of connection is such an important topic, particularly when we're talking about venture capital and MA?

David 2:08

Absolutely. I mean, every new author is going to be excited to talk about their book. But I'll say what's exciting about what I wrote with my co-author, Noah Askin, is this is based on 10 years of running a global thriving community, which not only involves a large amount of impact and access, but in that has a considerable threshold into the world of next-gen family office, venture capital, private equity, hedge fund, all these worlds where either those people are looking at who to trust and who to talk to, and everyone else is looking at how to build access or even start the conversation. And what I built very intentionally over the last 10 years was a community with some of the most insane access on the planet. Because I started with this idea that you have to build trust through generosity and gratitude, that you actually have to be a curious and vulnerable person the first time you meet somebody, basically meaning don't be a selfish, you know, the next part of that word. Um, but in that, everything about this was the way that we've regressed in our society into more tribalism. We talk to people who look like us, who think like us, who confirm what we're doing. And yet every innovation on the planet happens through diversity. There's very little that's been created in this world that didn't have an immigrant stamp as part of it, didn't have people of different faiths or genders or ages weighing in on each other, didn't have inspiration that comes from parts of our society that we might think we need to put a handout to, but instead are pulling us up. And so the whole idea of orchestrating connection was that you have to do this with yourself, the self-work to become the best, most elevated version of yourself. And then you have to insist around you that everyone else uphold those same standards. And when you do it right, every corporation, every person, every venture firm, even every family can have a different sense of being a purposeful and intentional community. And that's how to give the tagline, you orchestrate your life.

Philipp 4:13

David, I'm I'm super excited to have you on the show. And uh, of course, also humbled to be part of your network and uh seeing some of the magic which is happening uh in your circles. I spend my career mainly in corporations, if it's big fours as a consultant and some Fortune 500s. And uh when it comes to MA or investing, oftentimes it was a focus on okay, how is it to get a competitive edge? Do we really care so much about the company, the people behind it? We really need that specific asset. I will say in the last uh corporate role I had, there was a culture which uh was heavily uh impacted by a company called Danaha Group. And one of the things I learned there was really you build the connections, right? Any deal you do, a better deal is like if you actually really know the company you might want to invest in or the company you may want to um acquire. And uh it was a very different experience than all the other deals. If it's the acquisition divestitures I've been I've been involved in before, because it was really it started with building trust and realizing, okay, together we can create more than each of us by itself. So, question for you there, you know, you you referenced Visa, you know, obviously uh Visa and other corporate, and we they talk about billions when it comes to budgets or acquisitions. And you typically don't hear people talk about relationships when it comes to the big Fortune 500s, but it's always about the budgets and the billions. So why should corporate leaders and boards, you know, treat building trusted communities with the same seriousness, you know, as as cabinet allocation?

David 5:57

Because if they don't, they're making significant mistakes and not understanding how the world works. I'll give you two examples. Number one, this is how I built my own business in my connection theory part. Um, I was hired years ago to work with family friends. Those friends are Ray Dalio and his children. And I was asked to build a film company for Ray's son Paul and Paul's wife Christina. And one of the first tasks was how do you build a company of integrity when Hollywood wants your money? So I went through my network. I went to my friend Brian, he went to his um business partner, Colin. Colin went to his dad, Howard, and Howard told me the story about going into Hollywood and figuring out uh how to meet the right producer, the right visionaries for um the film world. And you might think I'm on a tangent, but I'm gonna get right back to you with this. Uh, what happened was I finally learned one of the best shining examples of building a film company with integrity based on connections, because Steve Rails, who's the head of the Donica group, also built Indian Paintbrush with Wes Anderson. So Pineapple Express, all of those incredible movies, blockbuster movies, come from that same focus of relationship building in an industry known for dog eats dog. And that incredible visionary billionaire was able to figure that out. And when I presented that to Ray and his trustees and his team, the response was, oh, I could have called Steve. But you had to get all the way around that circle of a chain of connections. And that involved, you know, family offices and a former ambassador for President Clinton, all the way back to what was sitting right in front of this incredible family. Um, and I was able to do that through looking and building trust through every chain. So, lesson one, in some cases, it's sitting right in front of you, but you don't know who to ask because you don't have time to. So, in those positions where industry is competing, and yes, there needs to be competition in a capitalism, it's not just all, you know, kombucha and collaboration. Like what also has to happen endlessly is this understanding that the relationships are the only thing that actually drive real partnerships forward. So that second one, I am hosting a family office event with a couple friends at a really amazing friend's home talking about education and innovation. And the um husband of one of the uh people there, he's a private equity guy. I can't go into his MA deals because this is a story about him, but you've heard of those companies, you've consumed those companies, you know those companies. And he thought my world of like this frufro of relationship building, even though he knew I had a lot of access since I was helping host the event in this home. And I'm not a family office, so when you're constantly invited in, you must be doing something right. And I pushed back because he thought my world was stupid. He didn't, he was like, Well, I have means, I've made great decisions, it's all on me. And I said to him, All right, tell me your top five MA deals. He proudly told me all five right off the bat. He knew them. And I said, Who introduced you to those deals? And he paused and then he named two people. And I said, Are you still in touch with those people? And he said, Yeah, I'm in touch with, and he named the one guy who had been deals number two and five. And then he paused and he's like, Oh shh, shit. And I was like, What? He's like, I'm not in touch with the other one anymore. And I was like, So you're telling me relationships don't matter, and the person who gave you deals one, three, and four that have made you millions and millions upon millions, and you didn't maintain the relationship. What have you lost by not maintaining that or at least expressing gratitude back? And the guy, he started to tear up. A tough man, rich, prominent, realized his failure was in not valuing the relationship first and the transaction second. Not because he could have made more, but he realized he had betrayed that friendship and relationship by making it opportunistic. And if we don't look at it this way, that it is both holistic and strategic, then what we're not seeing is what we're not seeing because we're missing it, because we took the time, especially in the corporate, the venture world, all of this, uh, to see how we maintain and get ahead and ignore the people around us. And when all fails, famous example of Goldman Sachs in the 80s. The most significant quote about relationships was everything else failed failed, but I still had my relationships. Right. I made a few calls and Goldman Sachs became what it is today. So it's it's that's why I say this is asinine. Yeah, like it is sitting in front of people, and when you're in a place of abundance, you don't think you need it. That's not when you need it. So stop looking as if it's something you don't need until you have to make an ask.

Philipp 11:01

And and I I would say, I would say, even thank you for sharing these two stories. Uh, specifically in the world we live in today, and you know, given what's unfolding ahead of us, having real connection will be so much more important to have communities to navigate around some of these developments and shifts, if they are good or bad. You know, let's let's leave that on on the side at the moment. But I feel looking at many corporations, um, especially when they are thinking about working with startups, for example, from a venture perspective, but also when it's about building joint ventures, the the first idea is it's much more transactional, right? It's not about how can we build something together which is truly transforming the industry, truly transforming our organizations together, and have that concept of win-win, which I I grew up with, and and and uh my mentors always said you always make sure that there's a win-win.

Steve 12:03

David, I apply what you said to a corporation, very much its own ecosystem, its own culture, the mass of people bringing their own points of view. And you already touch on it that in most sort of everyday corporations, and it's the business of making money, returns on shareholder value, that is the ultimate goal of the CEO and the C-suite. But you talk very deeply about bringing personal passion and these commitments of vulnerability. So if you're a Fortune 100 CEO, a chief strategy officer, and you're trying to show up and drive and reflect these philosophies that you're articulating and that authenticity. Can you talk about how that might actually de-risk a bold bet in CVC or MA?

David 12:58

Absolutely. So let's go with two of the biggest examples of corporate MA failure, which was the offer to buy Google at under a million dollars and the offer to buy Netflix at what would have been 25,000 percent less than it is now. Now, I wasn't in those rooms, but I have friends who were in those rooms, especially for Netflix and Microsoft. So, in every example of this, we can we leaders often conform around people who back up their vision and opinion. But if you ask anyone for the success in Israeli innovation, ask about the tenth man. It's not an accident, but there always is a contrary opinion. I mean, in Israel, there's many contrary opinions that I've been, you know, a very avid supporter, especially of the art scene there's for years. But in every point of leadership, when you are on this rapid fire of making decisions and guiding something for which you feel a responsibility, all of that is done done from a position of great comfort. Very few corporate CEOs aren't getting paid tens of millions, and if they fail, they go somewhere else because of the one thing that keeps them more valuable than their leadership, who they know. And the top leaders, when you actually understand the circles behind this, just look at, and these are not things I can publicly disclose, but you if you look at people who then publicly back Ted's Audacious Prize projects, you'll look at some of the most phenomenally successful corporate 100 CEOs and major family offices exited in many cases, and it's all based on relationship. So, number one mistake don't spend the time building the relationships, talking with peers, talking with rivals. And more than that, have an openness to see something for which the way you're seeing it isn't the only isn't the only and largest perspective. Because all the biggest bets that have happened from blockbuster video and Netflix on up, all of the innovations that happen within certain companies and certain others, you know, there's a reason that Shrek became a multi-billion dollar beast, and it's because the guy who envisioned this was fired because he wanted a different seat at the table. And so in every case of this, these the biggest failures, Steve are the most obvious, because leaders wanted to have people conform to their perspective. The best leaders, especially in the American market, are celebrated for taking risks, even if those risks don't work. Because my friend Craig, who built Hello Brand toothpaste, he walked into the Colgate Palm all offices, according to him, with an incredible story, and he took his fluoride-free toothpaste and he ate it in front of them and asked if they would eat theirs and they wouldn't. And then after Hello Brand became a massive global brand and target and everywhere else, and I still use this toothpaste today, both because I like it and I'm okay when my kids accidentally eat it. But more than that, then guess who hired him for years? The same company who didn't see his innovation then hired him for his innovation. Now he's making an amazing coffee company with Robert Downey Jr. And he's doing great in life. But this is that example, right, of a major corporation who had somebody in front of them that by partnering to scale could have done great, and then they did great later with him. But what did they miss in between? And why did they why did they miss him?

Steve 16:41

David, so curious. You used the word obvious, and as you were telling the story, it was the word hindsight came to mind in my mind, right? When you said, you know, when you Netflix, et cetera, et cetera. Why don't executives see that in the moment when that opportunity is in front of them?

David 17:01

Why do our parents in their 50s say they will never be like their parents in their 80s and then they become like their parents in their 80s, right? Why why is it that we have this prescribed view of how the world changes and then we change just like that? It is because of two things. If you stay curious, you stay young. If you stay vulnerable, you stay connected. These might be simple and commonplace, but the amount of times I walk into a room, no matter how big the room, and lately, as you guys know, and we took off the recording for this earlier, but I'm saying it anyway, and I talked about my ailing father at 87. The number of people who open up about what they're dealing with with their parents, no matter what tier, very famous, rich, I need to talk to, or just amazing human that's that's also there, we we reach a common ground that then builds trust. And all these leaders are trying to maintain their position because it's really hard to know who to trust. It's really judgmental to be vulnerable. But if you start with curiosity in all of these examples, yeah, some people in hindsight, they could have missed the mark. But the visionaries leading these companies knew their value and they weren't listened to. And in most cases, every story of a founder making millions than billions is of is of being in the right opportunity to be supported, and then being like, this thing sucks, so I'm gonna start sketchers. This thing sucks, so I'm gonna start this. Every example of innovation is somebody trying to fit and add to somebody's vision, and that visionary often going, eh, I think you're wrong. And that's that's the problem in innovation with this view that we shouldn't take as much risk. Because I sit in all these circles now. I hear these crazy private, delicious stories. And what happens if everyone is somebody missed the mark on asking the right question or asking in the world world of Ray Dalio, you know, asking more than that how to triangulate it. Who else could validate these opinions? Why do you think Bridgewater was so successful for all of the stuff around them? Because no decision could be made unless external validation confirmed it, which meant you had to be inherently curious and inherently humble in every decision made, even a rapid fire decision that doesn't accidentally make somebody the world's largest hedge fund.

Philipp 19:37

When we met or we started talking about the reality that you make introductions or I make introductions, and we were both annoyed by the fact that sometimes people come up, don't even come back to say thank you. Just a simple thank you, right? Not even thinking about what else there could be. But can you talk briefly about what does it actually mean if you're cutting out the connector and um just trying to move faster?

David 20:04

Or you think you move faster, but so I've been interweaving in subtly, because this is my whole life's work, the book to this. So when I talk about curiosity and vulnerability, those are both chapters in my book. Uh, diversity, gratitude, generosity are the other five, the other of the full five principles. Everything I've built, Philip, is a system for which the way that people take advantage of the person who makes relationships, if you build your community right, no longer can happen. I am not by happenstance mentioning people I have talked to or have access to. I have gained access to some of the most significant people on this planet through this approach. So it is not just, and I was not born with this. I do not have money. I do not have access that wasn't built through action. So when somebody takes an action to not honor you or me, Steve, to anyone listening, my rule for the last 10 years is you've broken my trust, you're out of my community, or in many cases, you're not even allowed in. I don't, I don't charge membership, I don't take sponsorship, I do events at cost. It's a privilege to be in this because of how you lead with action. But what it means when I find out somebody's crossed one of you is I can go to the people that are part of their circles and go, you know what, Steve? I know you like this person, but I wouldn't leave my kids with them. I don't think they should be on your podcast. And what would you guys do? You cut off that guest that you had made a commitment to because of that trust of me. And so, what happens when we live in a world where we actually draw a line? Not in everything. People are fallible, people make mistakes. I've made many in my life. But in what I'm talking about, Philip, it's this idea of what happens if you do that around where Whether somebody will build a trusted relationship or take advantage of it. And so in the book, the thing that went viral or still goes viral is the risk part, which when I started my community, people thought was stupid and asinine. Visionary people, people I love and trust, said, you can't kick people out. You can't have such a hard line. You shouldn't have such a harsh rule system. And my network growth is insane of high-quality people. I now run a global network with access to 35 countries and 187 cities with events in three countries over 40 to 50 a year by focusing on why one should be honorable and what happens if one does not. So for everything about the book, all those principles, the stories around it, the fact no one realizes I'm a composer, even though I coined the term orchestrated connecting. And you can Google me, ask Alexa, or watch my videos on my homepage. You know, I'm an improviser, I'm a pianist, I'm a classical composer, having done this since I was 12. And the way I try to find the resonance with people also focuses on that disharmony. So everything about the book, everything is you want to do it right, focus on the long game of relationships, and you want to do it wrong, try to work through me or you or Steve or anyone we know. And in my system now, watch what happens. My tech company called SourConnect is now addressing this at scale and will come out of MVP in a few months. My book, which became a bestseller, is about this. My network, people try to buy into. And by asking that, they failed the test because you can't.

Philipp 23:43

Right. So so maybe one last question, like getting back to the book, and then let's let's open up. But based on what you just said, obviously there is um everything is underpinned by trust, right? And trust, you know, is obviously also a new currency. But in order to build trust, right, and also you know, create very effective organizations, um, there are certain patterns or rituals um organizations may may embrace. So based on your work, are there certain yeah, certain tools or rituals you recommend, for example, to boards and leadership teams to really make a move towards embracing connection more?

David 24:27

So when you're in your eco chamber, the C-suite, all the marketing executives, all the product, whatever it might be, you're failing because you're not talking to the rest of your team and you're not talking to the people you're selling to. Now, a lot of people do surveys, they don't necessarily have conversations. Guacamole flavored Doritos did not come from the innovation team at Frito Lay. Like these are every example is sitting here. People talk about this endlessly at every conference I go to. And yes, we gloss over it because these things are put into practice as thought, not action. And so if you want to take an action to understand how your bank relates to the community, don't sponsor a walk and have a table asking people to sign up to be a client of the bank. Have everyone go down. And if you've been doing an annual food drive, make it weekly and then see how many people you touch. And then how many people see you consistently there even when they are not, then they feel they need to be consistently there and then see if they bank with you. Not going to be a surprise. We live in a world now where the currents that happen can destroy a company. I won't get into it because it's a longer story, but there's a major poster company who years ago, uh, their leader came out as anti-a lot of different types of people. And they had to course correct so much they became the shining example of a high-to-hire based on diversity, sexual orientation, and especially gender. And in most cases, when you look at something like that, that company then became one of the most celebrated for pivoting. But if they've been talking to their customers and understanding the values and the demographics of the people they were selling pasta to, would that have happened in the first place? Or would the pivot have been much more gradual but much more intentional? Then we can't sell our penne anymore. We better, we better shift. So every part of this is if you get out to the people you're with, the community you drive home to, the one that you're around when your kids are playing soccer against each other, you literally have to start with community and then head back to corporate. There's I understand that this might seem naive to people, but the most successful connections in my life have come from parent friends of my children. They come from comforting somebody in an event who's crying. They come from standing in line in the bathroom for an event that doesn't have enough toilets and letting the person who looks like they need to behind me go in front of me. And then I meet their friend, and that friend is a famous rock star. So it's just this idea that you do not compromise your values as a corporate if you lead with the human values first. And if you make that central, then competition becomes collaboration, innovation becomes opportunity, and everything we rale or really rail against that doesn't seem like leadership is actually true leadership. Because the most famous people I've met on this planet were talking A-list Hollywood celebrities, over 67 giving pledge billionaires, royalty, active politicians, the ones I considered high integrity, were humble first. They didn't have to prove anything, not because they already achieved it. They were humble when they started. They achieved greatness with others, not in spite of others. And that's why every leadership book, every single one, talks about servant leadership. It doesn't talk about being the top alpha dog overcompensating for receding hair loss and you know a marriage falling apart and how they made billions when their employees were all laid off. So they might have made a lot of money, but they're not the ones we revere.

Steve 28:27

Why don't we close with some advice, right? If if if there's a CEO, a CXO listening to this on a Monday morning and is going into work and wants to apply some of the wonderful advice that you've shared on today's conversation. What's what's the one thing that you would offer that individual as they walk into the office?

David 28:50

I would say spend the first few minutes and call or message a handful, two or three of the people who helped you get there and express gratitude. That's it. Don't make an ask. Just tell them thank you. Watch what happens if you do that every day. Because I have met incredibly, incredibly successful people. And if I need to ask them something, I'll get scheduled in. If I have to say to them, thank you for taking the time to help me with this, they will take the call now. It's strategic and it's valuable and it builds a relationship without an ask. And every CEO spends their time with people wanting to catch up with them when they just won't make an ask. So see who responds with gratitude. Start that chain. People write books about this, it's just a chapter in mine. There's nothing more strategic. Not only does it make you feel better and accepted, but I can promise you, from a decade of studying this, that what will happen from it is a few weeks later, that CEO listening to this calls up their friend Tom, and Tom says, I'm so glad in grad school this happened and so proud of what you're doing. Week, weeks or months later, that same guy will go, you know, I was somehow just thinking about you. And there's this thing we're going in on. It's a new fintech deal. Do you want to bring your company into? And that's not accidental. It's it's strategic, and all you had to do would lead with generosity and gratitude and watch how the cards fall a different way the more and more you do it.

Steve 30:32

Thank you.

David 30:34

Thank you.

Steve 30:36

That's today's episode of Inside CVC. As always, thanks for listening. To hear more episodes, search Inside C V C on your favorite podcast platform or visit uPath.com forward slash podcast.