Episode 90 : Enlightened Self Interest, Shifting Capital To Conscious Investments - Gary Moon
Gary Moon works and plays at the intersection of capitalism, consciousness and social impact. As Managing Partner, Gary led the formation of Nfluence Partners, a Technology Boutique Investment Bank. Previously Gary ran the Tech, Media & Telecom practice for Headwaters MB which Gary and his partners grew into a top 5 Technology & Boutique by number of transactions before forming Nfluence in 2018. At Nfluence, Gary focuses on managing the firm’s institutional investor network, as well as working with mission-aligned businesses.
In 2018 in partnership with Conscious Capitalism, Gary launched the Mission-Aligned Growth Summit , an annual banking conference, and now a monthly salon series focused at the intersection of conscious business and capital markets. Gary serves on the San Francisco Bay Area board of Build.org, a non-profit teaching entrepreneurship to high school students in under-resourced communities. Gary and his partner Maria have 5 kids between them, ranging in age from 7 to 25. You can most often find them traveling somewhere in the world on various internal and external adventures.
Audio Title: Ep90 - Gary Moon
Duration Transcribed: 1:01:40
Number of Speakers: 2
[00:00:00] Intro: Welcome to the Heroes of Reality Podcast, a podcast about the game of life and the hero's journey we all experience. Let's jump in with our host, Dylan Watkins, as he introduces today's guest.
[00:00:22] Dylan Watkins: Welcome young adventurers. And on today's podcast, I have Gary Moon. He is the Managing Partner for Nfluence Partners. Span out in 2018, Nfluence was originally founded in 2011 as a Technology, Media Telecom, TMT, group and Headwater MB.
Gary and his partners built Headwaters into the top five focused boutique investment banks in 2017. 2018 in partnership with Conscious Capitalism, Gary launched the Mission-Aligned Growth Summit, an annual banking conference, and now a monthly salon series. I believe it was called Jefferson's, focused on the intersection of consciousness, business, and capital market. So without any further ado, I'd like to welcome Gary Moon.
[00:01:06] Gary Moon: Hey, Dylan. Thank you.
[00:01:08] Dylan Watkins: Hey, Gary. Thanks for being on the show. I appreciate you being here today.
[00:01:11] Gary Moon: Yeah, excited to get going.
[00:01:14] Dylan Watkins: Yeah, me too. And, one of the things I think is really interesting is this intersection between investment and consciousness, which it sounds like, oxymoron in some way shapes and forms. But I think there's definitely a ton of merit behind it. But I'd love to kind of get just a little bit of your perspective of what got you to merge these two things together? Could you talk to me a little bit about your journey that led you up to where you're at today?
[00:01:46] Gary Moon: Yeah, yeah, sure. Yeah. So I was originally an entrepreneur and had a good run with my first company straight out of school. That was about a five to six year run, sold the company and then, you know, it was really looking for something that fit my personality a little bit better than, you know, the zero to 10 million. That led me ultimately to investment banking.
And you know, over the last 18 years you do what you do when you're passionate about something, you figure out how to have success. Some grinding, some luck, a whole lot of hard work. And, you know, the investment banking career path is not necessarily one full of the most conscious folks. So it really attracts people who are focused on money, shopper, you deal with money all day, big surprise there, right? A lot of really good people in the industry, don't get me wrong, but it's not exactly what I would call steeped in folks exploring the consciousness domain.
On the personal side, you know, as life does it serves you lessons and it knocks a little louder until you ultimately listen. So after a few pretty hard knocks, I started listening and really began my own consciousness path through meditation, Buddhism, ultimately plant medicines, et cetera. And I just, you know, at some point call it six, seven years ago, going deeper into consciousness on one hand and in an industry that is not very conscious on the other. And frankly, I just didn't really know what to do with that. Other than it didn't really work for me.
Ended up on Necker island with a group of social impact entrepreneurs. And you know, the pieces all came together. A combination of working with some folks who are trying to change the world and watching Richard Branson live his life, which if you've ever hung out with Richard, you can't tell if he's playing, working, families around, friends are around, there's partying happening. And I just looked at that as a model and went, "Oh my God! Like there it is, the fully integrated life." You work on all of it all the time in varying degrees. And that's when it all clicked for me. Well, I guess I'm just going to have to go create what I want.
[00:04:22] Dylan Watkins: Yeah.
[00:04:23] Gary Moon: And have the conversation with my partners and, you know, gratefully 12 of the 15 people on my team came with me to form Nfluence. And that was about three and a half years ago.
[00:04:35] Dylan Watkins: Oh, that's epic. So then you, you had the journey where you figured out the capitalism side of things. You were able to kind of understand and get that space, but realize that there was a gap. And then you saw a model, right?
[00:04:51] Gary Moon: Yeah.
[00:04:51] Dylan Watkins: With Richard Branson of him just, just that fully integrated life of playing full out. And then you realize, okay, if he can do it, I can do it. And so then you're inspired to kind of broadcast that message and then have those pieces line up.
What have been some of the struggles of trying to live that fully integrated life? Because I'm sure it's not all sunshine and rainbows. What have been some of the – what have been what I would call threshold guardians that you've had in order to get this ultimate vision of what you wanted?
[00:05:24] Gary Moon: Well, a big part of the realization was, you know, trying to find companies to work with. You know, so what do we do in our pocket of investment banking is we helped companies sell some mergers and acquisitions. And then we helped companies raise growth capital. And the click was looking for companies who are interested in conscious capitalism or more broadly defined, we call it Mission-Aligned. So companies with a purpose beyond profit. And see how much of our business we could make companies that fit that rough definition, if you will. So today, we're probably about a quarter to a third of our business is there.
[00:06:05] Dylan Watkins: Yeah.
[00:06:06] Gary Moon: And you know, the first piece of that is really when you're in front of a CEO, do they care about what you care about? And, are you the right fit? And so you have to go through this process of really how much do you emphasize the mission orientation based on who's in front of you. Because there are a lot of our clients who, frankly, don't really care about much of that stuff, and that's okay, right? We're – our job is to be really good at what we do, whether it's mission aligned or just pure tech amongst all of our history. But that becomes a tricky definitional challenge because we want to be a larger firm. And so that sort of has some trade-offs along the way, in what companies do you work with.
And then you have to take that message back out into the ecosystem, you know, Google Mission-Aligned investors. Yeah, there's no pitch book for that, right? There's not 500 firms who raise their hand and say, "Yes. Absolutely, we want to focus in this domain." And so, you know, I call it ecosystem building. We do a lot of ecosystem building, carrying the message, showing examples. But you know, sometimes that can be a bit of a grind.
[00:07:26] Dylan Watkins: Yeah. There's a couple things to unpack with that. So let's take this one piece at a time. Looking at that, one of the challenge you have with people that are mission-aligned is they usually have a profitability gap. So it's a very challenging thing that as people try to grow and 10X their business there are sometimes moral conundrums that happen as you try to scale your business.
[00:07:53] Gary Moon: Yeah.
[00:07:53] Dylan Watkins: So how, let's just take this at the first phase of going from struggling startup, which is zero to one, right? Which we could say seed rounds, initial capital. And then converting into what would be the growth capital, which means they've actually have in a – they've have market fit and they're actually able to scale upwards and now they just need capital because they've found a widget for the economy to scale up from. How do they not sacrifice who they are in exchange for that growth market share?
[00:08:26] Gary Moon: Yeah, exactly. That is the question. And even in the, that – it's the first question, there's plenty to unpack within that question. Right?
[00:08:35] Dylan Watkins: I've got more, don't worry. Let's...
[00:08:38] Gary Moon: So, the first, you know, the first piece of that is what game are you playing? Right? Are you playing a venture capital game? That's where I spend a lot of time. So know that, right? And if that is the scale orientation of the business that you want to build, then you have to know what the rules of venture capital are. Right? And what works and what doesn't and why does it work and who's in it and the rest.
The most common thing that I would say though, is the more mission – and this is an overgeneralization, but I meet a lot of mission-oriented CEOs who think it's only the mission that matters. When people ask me, "What makes a good mission-aligned investment?" I say, "Well, it starts by being a good investment." Right? It is at the end of the day, if you're choosing to enter a capital markets game that is about return, then you have to take some of the rules of that game. And whether you call it compromise or, you know, just understanding the rules of the game as you have to reflect it in your own decision making, that's really the first place you have to onboard what you want to do next.
[00:09:53] Dylan Watkins: Yeah. A lot of that is about having impact and if you can't even feed yourself, it's very difficult to have a large scale impact. If you're unable to actually have a Google, if they were completely broke, wouldn't have bicycles on their campuses and yoga mats and all that jazz. So you need to have a profitable company and then choosing what you do with that profit, which is a challenge, which – one thing that I've seen with a lot of mission-aligned people, it's the avoidance of actually understanding how to sell and market and produce a profitable company because it's easier to meditate with Mala beads than it is to actually drive leads through and nurture them out to a development process. So I completely agree with that.
Let me ask you a question. As a company scales, as a culture scales, and you take on more people that culture expands. I have two parts to this question.
[00:10:50] Gary Moon: Yeah.
[00:10:51] Dylan Watkins: Let's do the first part of the question. Do you have any recommendations for people being able to keep their culture at scale? Because when you start to scale in growth companies, then usually the culture drops, and so leaving the area of the actual generating of revenue.
[00:11:06] Gary Moon: Yeah.
[0:11:06] Dylan Watkins: What about the area of culture?
[00:11:09] Gary Moon: I think you have to, you know, as people have a Chief Growth Officer or Chief Revenue Officer, I think you have to have something akin to a Chief Cultural Officer. And the faster you're growing, the more important that becomes. Because the, you know, again, not all cultures are created equal. We're big proponents of, in practice, in our own firm, conscious leadership and conscious cultural development. And those are all about instilling practices along the organization.
And so, as soon as you start to sacrifice time against other objectives, it's easy for us to sit here on a video screen and say, it's much harder when you can't possibly hire enough people fast enough for your business, recognizing that. But if you don't have the infrastructure to scale your culture, as you scale your number of employees, then it becomes very, very easy for that to fall back.
[00:12:08] Dylan Watkins: Yeah, that makes a lot of sense. What do you recommend in terms – so, primarily it's having a Chief Culture Officer that can do that. Have you seen any systems or frameworks or methodologies that help them be able to maintain the pace? And you're right. It's super – it's one thing on either side of the spectrum. Either a super struggling mission-driven company that can't pay its bills saying, "I would never sell out."
And then there's another one that's at the very top that needs to bring on a thousand new engineers. That's just like, "I want a culture fit." But you can't – you know, you don't have enough people applying for the jobs that you need. So, on the growth side of things, are there any systems or frameworks or things that you've seen in place that are – ones that stand out to you as good practices that people can kind of integrate into other companies?
[00:13:00] Gary Moon: Well, the thing we read recently, I'm just looking, it's called An Everyone Culture, which is around deliberatively developmental organization. And they have three different examples in the book of different ways that people have developed systems around the idea that everybody is constantly learning in the organization.
You know, our frame of reference is learning and growth, and which flavor of it is part of the DNA of any particular business. But a lot of people who think this way, hang out in conscious capitalism circles. I'm a big fan of a group called Stagen where I've taken some integral leadership classes, as of many of my entrepreneur friends. We have one of their former guys who leads all of our internal work called Nathaniel Chakin [Phonetic] who, you know, he comes in and puts us on the mat and we practice every week.
[00:14:01] Dylan Watkins: When you say practice on every week, you're talking about difficult conversations. You're talking about work.
[00:14:06] Gary Moon: Yeah.
[00:14:07] Dylan Watkins: Okay.
[00:14:07] Gary Moon: Yeah. We're learning different frameworks. So just as an example, we're, I think we're two years into the work, and right now we're rolling out The Work from Byron Katie across the organization. And so, you know, it's teaching basically everyone in the organization at some level, and that we've been skill building to get to that point along the way. And right now we're just in the early innings of rolling out The Work.
So it, for me, it's really about, do you find that person who's going to lead the initiative that you trust that will help you design and then, you know, turn it over because we're probably running the company. And while culture is important, there are people who are of world class expertise and that who can probably do a much better job than you and I can to implement.
[00:15:03] Dylan Watkins: Yeah. Well, yeah, yeah. And part of that is taking their frameworks, mixing it in with your own culture and innovating new frameworks that you can then integrate across the culture. Okay. That – it makes lot sense. Yeah. Byron Katie is great.
And then in terms of, as this is the Heroes of Reality Podcast, you understand that part of the hero's journey is a part of transformation. It's a part of one part of yourself dying, the ego death, and the rebirth of a new self. And so as companies evolve and they level up at different stages, there is a death and rebirth of the company at different levels. What worked for a company of 10, does not work at a hundred or a thousand. And so the same is true in terms of the leadership potential.
What are your thoughts? And do you have any stories or reflections around leaders that have been able to reinvent themselves as they've been able to scale the organizations, versus replacing a CEO of a company because they maybe have been a good fit at 10, but maybe not a good fit at a thousand? And how do you do you look at those two differences?
[00:16:16] Gary Moon: Yeah, that is a super tricky, super tricky question. Because and we – and we see this all the time in different degrees, because when we start working with a company, especially when we're raising capital, these companies are scaling fairly dramatically. You can see – you can start to see signs when CEOs or founders have topped out. And it's no different between a CEO who's brought in or a founder who started it. At some point, you top out at your skill set for the task in front of you. And that's okay.
The question that I always try to ask myself when we're working with somebody is how coachable, how oriented to learning and growth is this person? Because the more they are open, you know, especially the more they're interested in becoming more self-aware, exploring consciousness domains, the more I believe that, you know, it's not always going to be a straight line, but at least they're going to be, you know, headed in the right direction.
That's not ubiquitously true. I know this is a question a lot of investors ask themselves at various points along the way when maybe things aren't going exactly right. But that's really our lens because it's really – at the end of the day, we coach and advise, and our clients make the final decisions. So it's really hard to work with people who aren't coachable. So, that's a big, big part of our lens.
[00:17:48] Dylan Watkins: That's great. And that's fantastic. And you're right, because that means if they're coachable they can evolve or they're open to evolutions. And the difference between a hero and a villain is a villain is someone who forces their authority on people while heroes inspire others, right? And so, if you came in with the hammer of God and I've seen some investors force out CEOs of the spaces because of that, then, you know, perceived as a villain of the space versus, you know, the inspiration of helping them try to get along.
[00:18:16] Gary Moon: Yeah.
[00:18:16] Dylan Watkins: How do you – when you're say – when someone's coachable, what are some indicators that they are coachable? Are there signs or things that you've seen, or have you seen unusual pivots that someone has been able to go from seemingly uncoachable to coachable? And what's the gap in that?
[00:18:35] Gary Moon: Yeah, that's a good question. You know, we're usually working with, with somebody for a six to 12-month period, at the most. So it's hard to see, you know, that long of an arc for somebody to maybe go from uncoachable to coachable. I would say that, you know, there are degrees of uncoachability. The further the degree away is, you know, we try to stay away.
[00:19:06] Dylan Watkins: Yeah, yeah.
[00:19:08] Gary Moon: But it's, you know, how do they relate to expertise, right? Do they onboard what somebody, who – do they recognize when somebody has more expertise in a domain than they do? Are they threatened by that? Do they have a reactive sense when inputs come in that threaten a story versus where the input itself may or may not actually be anything more than neutral for the business?
You know, since we are in a consciousness-oriented podcast, one of the frames that I look at is, are they operating out of abundance? Are they operating out of scarcity? Are they operating out of fear? Right? And so, the more frequently you see someone's decision making coming from a place of fear, then that's really – or scarcity, that's really, really tricky.
The other major tell is are they out actively seeking people who can level them up? And that's like the easiest indicator of all. I want to seek a coach for this. This is where I'm going. Who do I know? Who do you know that I can work with to build my skills in that? That CEO I want to work with every time.
[00:20:31] Dylan Watkins: Beautiful. Have you ever inspired somebody to go off to the jungles of Peru to take a large amount of plant medicine in hopes to shifting and widening that that degree of coachability? Have you ever seen that as a – because there's, you know, there's daily meditations and journaling and practices and new things. And then there's what we'd call more of a dramatic step forward. That's why I don't know if anybody's ever has been encouraged to go off and do a dramatic shift because it's, you know, almost like a crash diet per se.
[00:21:08] Gary Moon: Yeah.
[00:21:10] Dylan Watkins: I don't know if you've ever seen that. I've just seen – I've seen a lot of people who are trying to figure their stuff out, go off and do things like that and then come back. I don't know if you've ever encouraged that kind of behavior or have seen that amongst your portfolio.
[00:21:22] Gary Moon: Yes. Well, how deep down that rabbit hole do you want to go? So...
[00:21:27] Dylan Watkins: Oh, I'll go deep. We'll go pretty deep. We've had quite a few people on and talking about their journeys through this one, but if you've seen it and one of the challenges is that is the full integration in keeping that. But I don't know if you've actually seen a successful thing. If someone goes, "Okay, I realize I need some work and I can't do it. I can't do it with the – in the short term thing." So they go and expedite the process. That's the...
[00:21:50] Gary Moon: Yeah. So the first thing I would say is I did that myself in 2014, I headed down to Peru for a couple weeks, out of Iquitos, off of a recommendation from an entrepreneur friend and, you know, life changing, for sure.
[00:22:08] Dylan Watkins: Yeah. I was in Iquitos in 2017. I did a two weeks and five sessions of plant medicine.
[00:22:16] Gary Moon: Yup.
[00:22:17] Dylan Watkins: I think it was the Mallorca river.
[00:22:19] Gary Moon: Okay. Yeah.
[00:22:20] Dylan Watkins: But yeah, that was definitely a fundamental. Me and my two other co-founders and...
[00:22:24] Gary Moon: Oh, awesome.
[00:22:25] Dylan Watkins: You know that. That whole thing. So...
[00:22:27] Gary Moon: Yes. Yeah. I went to Temple of the Way of Light, which is a beautiful place and seven ceremonies in two weeks, so...
[00:22:36] Dylan Watkins: Oh. Welcome.
[00:22:37] Gary Moon: Yeah. You know.
[00:22:41] Dylan Watkins: Lots of – yeah, it kind of just rakes through your soul and goes, "Okay, what are you looking? It's going to find something." And then, you know, whatever is the lowest hanging fruit it'll grab and bring out you. So...
[00:22:52] Gary Moon: Yes. Yeah.
[00:22:53] Dylan Watkins: That's beautiful. Well, it's also, it's also great that you you've done it so you understand the value versus trying to have someone do something that they haven't actually done.
[00:23:01] Gary Moon: Yeah.
[00:23:02] Dylan Watkins: So, that's powerful. And it's a powerful tool.
[00:23:06] Gary Moon: It's a powerful tool and I'm going to another retreat center in October for my next journey with a group called One Heart, which is a fantastic group that brings together a lot of entrepreneurs and change makers. It is a one week, three journey, fully wrapped. It's a fantastic organization. So we're going, going deeper with them. But yeah, not only have I recommended it frequently, but I am one of the co-hosts of an organization that we call The Yearn. And we just had our second event in June.
And the idea of the event is we all meet pretty interesting people along our paths. And it's probably the exception that you can – I can meet you Dylan and in five minutes go, "Hey, let's go to Peru and do plant medicine." When I might meet you and go, "Hey, Dylan, that that's like a really interesting conversation. Why don't – I do this event it's called The Yearn and, you know, we call it the gateway event for the conscious curious."
And so, it's 88 people. Half of the group are deep in the consciousness domain. The other half are people are curious. And over the course of two and a half days, we create a super safe container that allows people to explore. There might be some medicine, but very light. Not like, go out into the universe too far. But lots of examples, lots of doorways. We call it, "Choose your own Adventure." What resonates for any given person on their consciousness path.
[00:25:04] Dylan Watkins: Oh man.
[00:25:06] Gary Moon: And it was a huge, huge success. It was our second one. We'll do it at least once a year, if not twice a year. The folks at One Heart are, you know, we're working with them as a place for people to go deeper. There are some other folks in the group where, you know, our goal is to guide people who feel called into deeper learning modalities in the consciousness path. So yes, that's an unequivocal yes. That's what I do in my free time.
[00:25:37] Dylan Watkins: I think that's beautiful, man. I definitely resonate with that. And good move on having a filter selection process. The one thing about plant medicine is it's a shared journey and a very sacred space. And so sometimes when people sign up for the journey and they aren't fully prepared, it can kind of rock everybody's boat.
[00:26:05] Gary Moon: Yeah.
[00:26:06] Dylan Watkins: And so, having that kind of experts meet newbies, kind of an acclimation process, see how they feel about it, see if they want to step through things and then doing it. I think is super powerful. I love finding these micro communities of awesome people that come together. I'm a part of a group, Burning Man group called Pink Heart. And so, we're just – they're heart-centered people and they're part of the Playa and they give water away and they do that kind of stuff, and – as a part of it.
And they're wonderful people, but they have a – it's a natural filter selection process to be a part of that. And so, similar types of paths, successful entrepreneurs that have sought more and have gone through it. It's not specifically dedicated the way yours is, but heart-centered kind of behavior. But I love the, I love the integration because I've definitely been on the journey with some people that you're like, "I' don't know if you're quite ready for this."
[00:27:03] Gary Moon: Yeah.
[00:27:04] Dylan Watkins: Or, you're going to get power leveled and go from like zero to six real quick. So that's amazing. That's a very interesting side hobby you have as a thing. Do you have... could you talk so far about this expansion of the consciousness and growth mindedness? Are there certain values that you have? Ones that are – are there ways that you live by, truth that you have, that you kind of have as like internal, external mantras that you live by?
[00:27:37] Gary Moon: That's a good question. You know, I do, my partner Maria and I, really have centered around certain values in our partnership. You know, I think the biggest orientation is around learning and growth. And just how, you know, back before, the Necker Island experience, I was really puzzled by what to do with this. I knew my domain in the world was to impact consciousness in finance, but I just had no idea how to do that.
And as I've continued to – you know, my net there is just start walking because things have a way of figuring themselves out. So eventually I started walking, and that is just, at the end of the day and everything I do from implementing it culturally within my own firm to, you know, being an advocate for it out in the broader ecosystem at work. To my partnership and our family at home to things like The Yearn out in community, it's really, how can I help impact a learning and growth orientation more broadly in the world.
I think the thing that I'm really tuning into right now, because, you know, I do have challenges like everyone else. I do have a program that gets in my way, like everyone else. And, you know, honestly the last month has been fucking brutal, because my partner and I just really got into some difficult waters, you know, the deeper you drop into the rabbit hole, the more the amygdala starts screaming, going, "Ah!!! what's going on?"
And so it's been really tough. And the thing that is really coming to the forefront now is all of that other stuff is awesome and great and brilliant. But I also really need to take care of myself. I need to do all of that in the world from a place of grounding, from a place of health, from a place of having space. You know, you asked at one point what gets in my way? I'm a red line guy. Like, I will run at the red line constantly until something comes in and I just have a spectacular crash and burn. Right?
And that just doesn't really serve me all the time. You know, it serves a story. And so, what I'm practicing right now is really slowing down, understanding where that story comes from, taking care of myself and getting in a stable base so that I can go out in the world and be more powerful in these other domains that are, you know, really exciting and light me up.
[00:30:50] Dylan Watkins: Yeah, man. I totally, I totally – I feel you on that. Work hard, play hard kind of thing. And one of my recent reflections that I had was around mistaking indulgences as a form of love when really it's a form of scarcity.
[00:31:09] Gary Moon: Yeah.
[00:31:09] Dylan Watkins: And like, thinking like, "Oh, I'm on a diet now. I'm going to go to this vacation so I'm going to indulge and I'm going to indulge like crazy." And it's really the scarcity mindset, just overcompensating for the fact that I didn't have enough food or enough, whatever I want to catch up and makeup. And I mistakenly thought that indulging myself was giving myself love, but really it was the scarcity mindset trying to compensate and overcompensate to a situation.
And so I've been attempting to indulge in moderation. As a form of being able to still give myself that gift without the explosive behavior of redlining, collapsing, just breaking everything down and then just building it back up.
So, how do you maintain your health? What habits, rituals, patterns do you keep to keep you from burning out past that red line?
[00:32:12] Gary Moon: Yeah. So, meditation for sure. I used to meditate fairly regularly on my own. And then I think it was a podcast that Maria and I were listening to and it was a couple that had their – has a morning routine. So she and I meditate together now. So we have a very nice morning ritual when we're together. I meditate when we're apart.
[00:32:41] Dylan Watkins: What's your...
[00:32:42] Gary Moon: No, go ahead.
[00:32:43] Dylan Watkins: On that note, what's your trigger for meditation? Like, is it time sensitive? Is it an event hub? Is it an internal reflection? What's your triggers for the actual meditation?
[00:32:54] Gary Moon: So, you know, broadly, I think different meditations do different things for you and for different people, right? So for me, there's an element of being in silence and winding down the noise. That is the centering of breath. So call it more in the Vipassana domain, where you're just observing. You're coming to center and you're observing what's happening. That, you know, wind down or that silence is an important element for me personally.
More recently, in what Maria and I do together is a little more guided meditation. And so I've been in the more experimenting around with different teachers. I love Insight Timer. Yeah, and I know lots of people have that. Or there's just lots of different teachers and different modalities to explore on that. So sometimes we'll explore, sometimes we'll center on some specific teachers.
And then right now, based on one of the teachers and just experimenting around, I'm actually designing my own daily practice, which takes some bits and pieces of different things that I'm working on and incorporating them into the meditation. So, just as one example, a Metta, which is a loving kindness meditation. That's something that in particular time periods I'll work that in. So 20 minutes of silence, 10 minutes of metta meditation. But I like to just play around with it a little bit based on where I am and what I'm working on.
[00:34:32] Dylan Watkins: So, so a couple things. So it sounds like the, one of the triggers and cues is in the morning, you do it with your partner and then there's the – and you kind of alternate through them depending on the modalities you're currently interested in exploring. I mean and another one is you said, you're currently doing it by yourself. What is the trigger before the meditation for you to do it by yourself?
[00:34:53] Gary Moon: Oh, I have to do it in the morning.
[00:34:56] Dylan Watkins: Oh, okay.
[00:34:57] Gary Moon: Yeah. Like if I don't do it before I start my day, like it, it's just not happening. It's the same thing – it's the same thing with the gym.
[00:35:05] Dylan Watkins: Yeah.
[0:35:05] Gary Moon: Like if I don't exercise before I start work, like I'm just not going to get there. So, my morning block is all about meditation, health, whether that's a walk or a run or a lift, before I ever start my day. Yeah.
[00:35:24] Dylan Watkins: Totally makes sense. Yeah. Yeah. It's the gift you give yourself in the morning, so you can have the capacity for the day so that you go through, otherwise you just – sounds like you're redlined, you got everything blocked out in your schedule and then it's just never going to fit in and then you collapse at the end of the night. And then...
[00:35:38] Gary Moon: Basically, yeah.
[00:35:38] Dylan Watkins: ...rinse and repeat. Yeah. Totally. Okay. So looking at this, there's something that you started. You did a consciousness summit.? Is that correct? Or was I – am I off in that one? Did you, you put together – sounds like you put together some events, but did you put together a consciousness banking summit? Did I get that correct?
[00:36:03] Gary Moon: Conscious Capitalism and Capital Markets is sort of what we call it as the intersection of those two things. And that's, you know, again, out in the – I just need to create it. There isn't what I want in the world so I'll just go create it. That's one of them. We called it the Mission-Aligned Growth Summit. And so again, it's where do you bring capital together with companies who have a purpose?
You know, we did it – we had one big event and then of course we were going to have our second one in April of 2020, so that didn't quite work out. And then, you know, as you can probably tell, I don't like to do things everybody else does. So when we decided to reboot it in COVID, the focus was really what can we do that's original? I don't want people to turn up to yet another Zoom. The original idea was always, this is not a pitch fest. Like we all get pitched at all the time anyway.
So we turned it into Jeffersonian Dinner. And so what a Jeffersonian Dinner is 12 to 15 people. There's only one conversation. And so the way that I like to structure it is there's one or two sparks. So those are the people who hold the topic, but you go around the first and you ask something of a personal question. So we did one on wellness investing. And the first question was really, tell us about something in the last year that has changed your relationship to your internal states.
And so, this is awesome because then you're not, "Hey, I'm Gary and I'm the Managing Partner of Nfluence Partner." in my pitch face. It's like, "Hey Gary, this thing really challenged me. And I love setting the tone and going deep."
[00:38:00] Dylan Watkins: I love it.
[00:38:01] Gary Moon: And so you just get this different texture of people in the meeting because you're learning about them personally. And then the second one is a little more on the topic. Again, this one, like in wellness, tech investing is, what is their orientation and view and different aspects of it? And so then people go around and give a little bit more like, "Here's where I'm thinking about." And those sorts of things.
Virtually, it's fun. It's more juicy when you can do it in person, because then after you go around, everybody sits around and talks for another couple of hours. I'm looking forward, you know, knock on wood, soon that we can host those in person.
[00:38:45] Dylan Watkins: That's awesome. Okay. Couple pieces. One piece, where would you be hosting those in person?
[00:38:51] Gary Moon: Maria and I used to do them in our home.
[00:38:55] Dylan Watkins: What city or state?
[00:38:56] Gary Moon: Oh, San Francisco. Yeah, San Francisco, New York, LA, Boston, Miami. Those are the places that I tend to be. So that's probably where we'll be...
[00:39:06] Dylan Watkins: Can we avoid Boston in January, please? That would be...
[00:39:10] Gary Moon: I will be in a Todos Santos in January, so maybe we can do it there.
[00:39:15] Dylan Watkins: Okay. That sounds better. That sounds better. Yeah, cool. I was in – so I do hackathons like virtually hackathons and I helped organize and judge the MIT Media Lab hackathon.
[00:39:30] Gary Moon: Oh yeah. Awesome.
[00:39:31] Dylan Watkins: Yeah. And it was, my friend who helped put together one over at USC brought me over to do the one over there and I've never been to Boston. And I was there in January being from California my whole life. And I thought it was a good idea to go for my morning run. And I didn't fully understand the concept of what that was like. And I was like, and I did a large run around, I'm like, "I might die. I may not make it back. This is actually dangerous."
[00:40:00] Gary Moon: Yes. Yeah.
[00:40:03] Dylan Watkins: So, just the – that's the burning memory that I have of being in Boston. So when you said that, it's smart people, really cool, really smart people. Cutting edge stuff, and they know how to party and talk a lot of shit. But for the most part, it was really – that was a really cool thing. That's great. That's beautiful.
So let me ask a question with that. A lot of times with having engaged in conversations, one of the things about like having these types of conversations, the one-on-one, we have back and forth and there's an engagement piece.
[00:40:30] Gary Moon: Yeah.
[00:40:31] Dylan Watkins: How do you – the reason why conversations break off in the side tangent is because people feel unengaged in the conversation. Is there any ways that you keep, I mean, whether virtually or in person, how do you keep that engagement going when there's 12 to 15 people? I say something for two minutes and it's going to be 15 people around the table. It's going to be a half an hour before it comes back to me again, I can't say anything else.
Is there anything that you do to keep that level engagement, to have them contribute in some way with maybe not overtalking the person? Is there things that you do around that?
[00:41:03] Gary Moon: Yeah. So the basic ground rule is that there's a single conversation. And depending on – you have to, you know, now I usually know who's in the room, because I invite everyone who's in the room. It's a little trickier virtually to keep things going than it is in person, because in person you can sort of read the room a little bit better. But we really haven't had as much of an issue there. As long as you keep the topic engaging and you remind people that they have three minutes.
If somebody's drowning on for seven minutes, you're going to start having people disengage. So it's how do you tactfully remind somebody that everybody gets an opportunity to contribute into the conversation. Sometimes you'll have some of that natural back and forth, where somebody will ask a question and pick it up and the rest of that. When you have more time, that's a little easier to do.
But for the most part, when you are mindfully inviting people into the room, not just anyone into the room, it's only 12 to 15 people after all. And then keeping the topic interesting. And reminding people that we're not pitching at each other, that this is where, you know, we're bringing our full authentic self into the conversation. Those sorts of cues, generally, it goes pretty well.
[00:42:36] Dylan Watkins: Okay. Just curious, as being someone who hosts events and things, and I've noticed that, like that, that the reason why it starts to break off is that like general distraction, shiny objects whatever's going on. And so it's kind of like, sometimes, especially with highly interesting people, they sometimes like shiny objects. And so it's sometimes a process. So I was just curious about that.
[00:42:59] Gary Moon: Well, and the other thing, you know, Dylan is, there's a reason why I always go first or when we're doing them at home, like either Maria or I would do go first, because you set the tone. If I share something that is, you know, I don't want to over rotate, but more trivial in nature or more surface level in nature, that's going to set the tone. And if I'm listening to somebody drone on, on something that I can hear at any point anywhere, that's less engaging. If you drop deep and then the next person shares deep, the next person shares, like you are engaged.
[00:43:40] Dylan Watkins: Yeah. Yeah.
[00:43:42] Gary Moon: And so that sort of tone, and then those verbal cues of reminding people become really important. And I found them to be just really, really effective.
[00:43:52] Dylan Watkins: Beautiful. Yeah. And I know the intimate dinner parties that with awesome people is magic. It is like, you know, it's funny. I feel myself in two worlds, right? High technology, crazy virtual reality, wild things. But also like getting around people around a fire with cooking meat with music is like, like there's something in that primal sense of having people in that type of environment, sharing food that is like, it is, it's got these tribal reward elements that are fundamentally enriching that you can't get from scrolling on TikTok for a half an hour or whatever insert activity. So...
[00:44:40] Gary Moon: Well and what's the – like, this was a big part, big focus for us at The Yearn is in that table conversation, what's the question? The very nature of the question invites someone to go deep or not. Right? And so it's just creating that space and it's, you know, it's not like it's difficult to have an open invitation.
And the thing that's amazing is, to me, is you don't need a bunch of people who are steeped in exploring consciousness to ask a really deep question and see what happens in almost any room, because people are hungry for connection. Like whatever label you throw it on it, you know, we all talk about it from a consciousness perspective. But people are hungry for connection. And when you ask that question and allow them to show more of who they are, it just creates an environment where, I don't want to say almost anyone. But you would be surprised perhaps at the level of depth that most people are willing to go, as long as they have the example and the invitation.
[00:45:51] Dylan Watkins: Do you have a favorite go-to question? Like, is there something that, or things that you like to, that you can set the frame really well? I mean, I love the like internal wellness question. That one is a gem. Because then you can like have a notepad onto the side. And you know, that's – that's super interesting.
[00:46:11] Gary Moon: So what I would say is I have some friends who are really good at this. Keith Ferrazzi, if you know that name, Never Eat Alone. He's one of the co-hosts of The Yearn. This is his zone of genius for sure.
And then, Maria and I have another friend, uh, Lisa Kalfas [Phonetic] who, this is what she does now is helps open space for people to have deeper conscious conversations and it's just incredibly impactful. So what do I do? I call them.
[00:46:42] Dylan Watkins: Okay.
[00:46:43] Gary Moon: I call them for example...
[00:46:44] Dylan Watkins: Phone a friend. I love it, man. I...
[00:46:46] Gary Moon: Totally.
[00:46:47] Dylan Watkins: I love it. Yeah. One of the reasons I was ask, I just like, oddly enough, I have like the – I had a couple of my really good friends chatting in one group of things and it's all a couple of my favorite people. And I said, "I really want to get you all together. This would be incredible."
[00:47:05] Gary Moon: Yeah.
[00:47:06] Dylan Watkins: And one of them just booked an Airbnb for us to go into Utah in the next two weeks.
[00:47:10] Gary Moon: Awesome.
[00:47:11] Dylan Watkins: And, but they're all like high level dudes. And we're going to get in and just, you know, talk about life and all that stuff. And so, as we're talking about these things, I was just like...
[00:47:21] Gary Moon: Yeah.
[00:47:22] Dylan Watkins: I think I can – we have some good ones, but I do like the phone of friend trick, especially if they're super experts in the space.
[00:47:26] Gary Moon: Yeah. Well, I think if I remember right, one of the ones we used at Yearning Man was, "Tell me something about your life that has made you who you are." Right? And so pick some experience in your life that has impacted who you are. And so, like that's full on. Like, if you invite people into a deeper conversation, there's a lot of interesting stuff can come out of something like that. So...
[00:47:57] Dylan Watkins: That's a good one. I haven't heard that one. Thank for sharing that.
[00:48:01] Gary Moon: Yeah.
[00:48:02] Dylan Watkins: So let's talk – when you talk about getting pitched at and getting pitched at, from people who maybe it's not the right time for them to pitch. It's a little off. How would you tell if there's somebody listening to this, how would they know if it's the right time for them to go out and pitch to people, to knock on the doors, maybe not sand hill road.
[00:48:33] Gary Moon: Yeah.
[00:48:33] Dylan Watkins: But they're going to be going, they're going to be going along the pace. Like, what cues would they have that they're, that they're primed and ready to actually reach out for investment?
[00:48:43] Gary Moon: Yeah. I mean set and setting and context. You know, if you are somewhere and it's about getting to know people then that maybe not be the right context. At the same time, you know, we shouldn't be afraid to talk about interesting things about ourselves. Right? So there's a lot of nuance there.
Do I want to hear that, you know, my company grew X to Y and da, da, da, when I'm at somebody's home in a dinner party? No, not really. I want to get to know who you are, and if I think who you are is pretty interesting and engaging, and I know that you're running an interesting company, oh, then that makes a natural follow up. Where if you're like pitching me all the stats and the this and the that, and this investor and these got, and then it's like, "Oh my God. Seriously. Thank you."
[00:49:36] Dylan Watkins: Where has been the worst place you've been pitched at? Where has been the most uncomfortable setting? You don't have to say any names or anything. Is there anything comes to mind that has been the most egregious that pops to mind?
[00:49:50] Gary Moon: I don't know. I don't really store stuff like that. You know, because I'm just sort of go “whghaaa”. I'm pretty good at setting boundaries and you know, I’m not sure what impression it makes on somebody else. But I probably just pretend like I don't notice and keep moving.
[00:50:09] Dylan Watkins: I just – what flashed in my head was you trying to go to the bathroom and someone just like banging on the door. Okay, well, appreciate you indulging me on that one.
[00:50:19] Gary Moon: Yeah.
[00:50:21] Dylan Watkins: Cool. So, ultimately with like, like with what you're doing with this, because you're making these ecosystems with your – I mean there's – it is. It's a very difficult thing to try to find conscious companies that are in the growth phase that have figured out the deepness of consciousness, but also been able to be highly productive successful businesses that can grow up from there.
[00:50:50] Gary Moon: Yeah.
[00:50:50] Dylan Watkins: And so you're making this ecosystem for this. Ultimately what is your holy grail of creating these ecosystems? What are you ultimately trying to achieve with all of this?
[00:51:03] Gary Moon: Yeah. So I am admittedly an incrementalist for systems change. You know, part of what, you know, there are people who are a little more revolutionary. You know, let me just put it this way, my day job is to get shit done, like, you know. So, I need to go – I need to do it from a frame of being able to get shit done. Right? So if it's just a conversation, then I'm bored and it doesn't matter.
So what do I hope to achieve? I hope every year there are more investors who are exploring what it means to be a conscious business or a purpose-driven business. How do you do that? You get more stories out. You bring investors who are curious similar to The Yearn on the personal side, together with investors who are steeped in it.
You know, one of my favorite examples is Mayfield. Over the course of years, more and more of a pivot. Now, if you look they're fully fledged, we invest in conscious companies. We're a conscious capitalist venture capital firm. Like that stuff doesn't happen overnight. And so, along with Tim Chang, who does awesome work there, and some of his partners in just being a beacon of calling more and more investors and more and more companies to identify in those domains, share their successes, become examples.
And, you know, listen, if every year there's another a hundred million or a billion that starts moving 25% more consciously, 10 years from now – you know, put an accelerator on that, 10 years from now, there's a lot of money moving more consciously. That's really my goal. And at some point, you know, listen, we are in a capital market system. It's not necessarily, I'm not hopeful that the whole thing flips. But I am hopeful that it becomes something where it's the oddity or the exception to be unconscious than it is conscious because things like your full stakeholder ecosystem matter, things like investing alongside your value systems matter. And that's, you know, when I sit down to put the flag in the ground on Nfluence, that's my 30 year arc. So I got a lot of work to do.
[00:53:36] Dylan Watkins: Awesome. Okay. So currently, what do you think is the capital amount percentage that's dedicated in the total investment market? What is that currently at today would you say is it? do you – is there a percentage that you have in mind? Because you talked about one of the metrics for success with this is the, how much capital in investment is dedicated towards consciousness? So what is it – do you have a ballparky guess? And then what do you think?
[00:54:05] Gary Moon: Well, yeah, I want to draw a little bit of a distinction there because there are a lot of things that sort of mush together in some of these definitions. When we call it mission-aligned, we call it companies who are impact, conscious companies, purpose-driven companies. So a lot of things go into a bucket there. And then there are companies who work on consciousness itself. Like this is where the Nichole and the trans tech team is focused on in wellness technology in those. So I want to draw those as separate elements.
[00:54:40] Dylan Watkins: Yeah.
[00:54:41] Gary Moon: You know, there's a lot of headlines that say impact this and that and the other thing. You know, down in the trenches, for me, it's in the hundreds of millions, which is not very much that truly moves with a consciousness lens to it. Like, is this a conscious company doing good and scaling? You know, maybe that's not generous enough and it's in the low billions. But it needs to be a whole lot more than that.
And the other thing I would say is the bulk of the money is early stage. And that's awesome and fantastic. It has to start there. But when you get past a series B, and even at a series B, when you need 30, 40, 50 million and up, yeah, it becomes pretty tricky. That's one of the holes we hope to eventually fill with a fund and move, you know, like Norwest, for example, is a firm where they're investing more consciously. Now, is it a hundred percent across the board every investment? No. Is it three investments this year instead of one last year? Yes. Like that's the incrementalism that I see that when you apply that across the full ecosystem starts to add up to things that become pretty, pretty interesting.
[00:56:06] Dylan Watkins: Yeah. No, absolutely. I like the practical tactical approach you have of like, hey man, I'm not, I'm not going to swallow this whale in one bite. I'm just going to cut off a piece. I'm going to just, I'm just going to – are we making progress? Are we – it's more of the direction, not necessarily the actual, the goal. So are we moving the right direction? And can – you not only support mission-driven companies to do it, but you also want to inspire other investors to go into the conscious capitalism space to get there.
What would you say if there were investors listening to this that are maybe generalist investors or things like that? What would you say to inspire them to want to make one more investment this year into a mission-driven or a – someone that's got a value-based decision making model for a company? Is there anything you would say?
[00:57:03] Gary Moon: Well, the first thing I would say if they're not investing in the area, is these companies actually perform better. Why? In the war on talent, people stay. People want to come. They don't have to – they don't have to have top dollar. And then what's the company working on? Is it working on something that's good in the world, or is it just a company, not just, let's just say for the sake of argument, it's just a company that focuses on conscious culture. It has a thousand employees.
Those thousand employees go home at work. And each of those thousand employees is more conscious, is a better father, is a better husband. Like that's like real impact. And the marginal, you know, difference in investing – a bias for an investing in a company like that versus another company. All things being equal, right? We're still talking about good investments. You're just going to have better performance.
[00:58:11] Dylan Watkins: Yeah. Yeah. So it's kind of that enlightened self-interest kind of thing.
[00:58:16] Gary Moon: Hundred percent.
[00:58:17] Dylan Watkins: Yeah.
[00:58:18] Gary Moon: And then you get to feel good about it too.
[00:58:21] Dylan Watkins: Sleep better at night, knowing you're doing some good in the world.
[00:58:23] Gary Moon: Yeah.
[00:58:24] Dylan Watkins: This has been beautiful. Is there anything else you'd like to let people know about before you tell them how they can get a hold of you?
[00:58:33] Gary Moon: I think we've actually covered the range. The one thing I had in mind was something like The Yearn or, you know, keeping eyes open for communities of people who are, you know, out there trying to change the world a little bit and plugging in.
[00:58:48] Dylan Watkins: How would they find these communities? Right. Being either an investor or a mission-driven, conscious, aware, conscious tech company.
[00:58:55] Gary Moon: Yeah.
[00:58:56] Dylan Watkins: Where would they go to find these people's?
[00:58:59] Gary Moon: Yeah, I think, keep your ears open. I'm an advisor to a group called Second Time Founders. I'm a huge fan of what they're doing. So there is a good – it's, you know, again, shared value system there, learning and growth. You know, you get humbled by your first company most frequently, so maybe you're a little more focused on learning and growth by the second one.
So it's about creating that peer group to enable learning and growth. And there's a pretty good consciousness center of gravity in that, self-awareness in that. So communities like that, even the YPOs and EOs of the world can be pretty good around learning and growth. Maybe not as consciousness-oriented. But they're out there. You just have to listen.
[00:59:49] Dylan Watkins: And you have to be a second time founder to join Second Time Founders? Is that the thought process, you have to successfully have sold the previous company?
[00:59:55] Gary Moon: You don't have to have successfully done anything other than beyond your second company. So...
[01:00:01] Dylan Watkins: Okay. Okay.
[01:00:02] Gary Moon: Plenty of people have a lot of success on the second one, regardless of whether their first one crashed and burned or not.
[01:00:08] Dylan Watkins: Yeah. A lot of lessons learned in that tool belt as you go through. I definitely know that.
[01:00:15] Gary Moon: Pretty good. Yeah.
[01:00:17] Dylan Watkins: That's beautiful. Great. And so, the final question is, if people want to find out more about you, if people want to pitch you in the restroom, if people want to reach out to you, how do they get ahold of you?
[01:00:30] Gary Moon: Yeah, just, Nfluence Partners website. It's an N not an I-N, NfluencePartners.com. You can find me there. I'm on LinkedIn. Not a huge Twitter guy, but I'm Gary – @GaryMoon. So, I'm pretty easy to find. There aren't that many Gary Moons, other than a rock star and a race car driver, which you know, is a little ironic too. So...
[01:01:01] Dylan Watkins: Well, Gary, it's been a pleasure, brother. I really appreciate all you're doing, supporting the communities, man.
[01:01:06] Gary Moon: Likewise.
[01:01:07] Dylan Watkins: It has been wonderful. So...
[01:01:08] Gary Moon: Fantastic. Yeah.
[01:01:09] Dylan Watkins: Yeah. Thank you so much. Have a beautiful day and I will see you in another reality.
[01:01:14] Gary Moon: All right.
[01:01:15] Dylan Watkins: Good night. Take care.
[01:01:15] Gary Moon: Sure.
[01:01:16] Dylan Watkins: Bye now.
[01:01:19] Outro: Thank you for listening to the Heroes of Reality Podcast. Check out HeroesofReality.com for more episodes. While you're there, you can also take the Hero's Quiz to find out what kind of hero you are, or if you have a great story and want to be on the podcast, tell us why your hero's journey will inspire others. Thank you for listening. See you on the other side.
