Clay Finck (01:58):

Now, Ryan, it’s been fun connecting with you and reading up on some of your work lately. I’d like to learn more about your story to help us understand why you do what you do today after being an entrepreneur for a number of years.

Clay Finck (02:11):

Could you talk about your story of how you went from being a serial founder, building a marketing platform to now being a coach, helping entrepreneurs realize their full potential?

Ryan Vaughn (02:21):

Yeah, no problem. So I have been in the startup world, in the entrepreneurial world for pretty much my whole life. My first business was an incredibly profitable business selling pogs in second grade on the playground. And that was an awesome business because my parents, my mom would buy the pogs for me and then I’d go sell them and then I’d gamble them back. And I was pretty good. So a lot of times I wouldn’t even have to part with the goods and I’d still end up making money.

Ryan Vaughn (02:48):

I got a sense of like what was possible through business really early. And I went through, I guess, traditional schooling and then just out of college was really interested in getting into sports. So I’d played sports my whole life, everything with a ball. And it’s really, really hard to get a job in sports as a guy just coming out of college, like incredibly hard. And so I failed a bunch of times in trying to get into sports and eventually decided, all right, well, I’ll have to start my own thing in sports because I really want to watch sports and call it work. That was my initial goal.

Ryan Vaughn (03:18):

And so I started a sports’ blog about the Detroit Lions and Detroit Pistons, cause I’m a huge Detroit sports fan and realized really quickly, nobody cared at all about what I had to say about the Lions and the Pistons. So that lasted few, like maybe six months and then that got shut down. But then I found that there was a market opportunity in high school sports. And so there wasn’t the type of coverage and recognition for high school athletes as there was for college and pro. And so I started a blog which kind of became a large blog with about 10 people working with it at one point, covering high school sports.

Ryan Vaughn (03:50):

And it was called West Michigan All Star. And then that went for a period of time and eventually evolved into VNN, we rolled the first business into the second one. I was at VNN for 10 years. At one point it was called Varsity News Network. And then we got sued by a big private equity company for using the word varsity. So we changed it to just VNN and we billed that company as espn.com for high schools.

Ryan Vaughn (04:12):

It was a tech platform that basically was the entire back office for high school athletic departments. And that was my business school. That was all of my sort of learning around the entrepreneurial process and journey. It really kicked into high gear and most of it happened in that period of time through VNN. So early on, I went in, probably about two years or so we went through an accelerator and after the accelerator I was not spending any money. And so I lived on PB and J for a couple years, and then eventually, maybe two years in, closed our first angel round.

Ryan Vaughn (04:42):

At that point we started to kick things into high gear. I was one of the more public CEOs in the tech space in Michigan. And it was a pretty fun time because as Michigan was sort of finding its footing in the startup world, I was at the forefront of that. And I was one of the businesses that just started earlier than other people so I got to ride that wave up. One, the biggest business plan competition at the time in the world raised money from a whole bunch of angels, got into the VC world, raised money from them and was just kind of like every year would ratchet the growth up a little bit higher and a little bit higher.

Ryan Vaughn (05:16):

And eventually we got to the point where we were the largest high school sports communication platform in the country and had a bunch of success. That’s the outside story on the inside there was a lot of tension through that process. And I think a lot of the tension stemmed from the fact that like what made me successful and effective at raising money and recruiting employees and rallying people to my cause was that I really looked like I knew what I was doing. And I really looked like I was up into the right. I was humble bragging on LinkedIn and all this stuff. And I really looked the part and that was effective.

Ryan Vaughn (05:50):

It’s an important part of building an organization is you have to lead, you have to bring people along with you. But the challenge of it was is that inside, I felt completely uncertain about all the stuff that I was doing. And to some degree ambiguity is part of the startup journey, but that was really, really hard for me and going into work all the time, acting as if I had everything under control, when really I was just scared. I was like, “How am I going to hit payroll this time? And what happens if this customer bails on us?” Or whatever the problem de jure was.

Ryan Vaughn (06:20):

And I think for most of my career as a CEO at VNN, who I was for the public was a really different sort of experience from who I was for myself. And that tension was really draining for me between those two things. It was draining, it was isolating, it just took a toll. And what I did as a means of sort of working with that is I found myself sort of numbing myself. Like I would feel scared and I’d feel scared about Runway or anything else. And I would tell myself, “Well, I don’t have time for that. I got work to do.” And so I would kind of shove down that emotion, pocket it for later, and then just continue to bust my hump.

Ryan Vaughn (06:59):

That just has ripple effects, like as I sort of ignored fear and ignored sadness and these other things, I just became just more distant from the rest of life. And so I got really, really laser focused on my organization. Didn’t have time for family. Didn’t have time for friends. Didn’t have time for hobbies, didn’t have time for anything. And I got pretty much like the company was the whole thing for me and you know that was my life. Yeah, so it worked and we grew consistently, but I think that tension was what really sort of started the process for me of like I wonder if this is actually what I should be doing.

Clay Finck (07:32):

The first thing that comes to my mind is early on, how are you able to pay the bills and pay rent and make sure you are able to pay for even your day to day living expenses or even pay some of the employees you had running these blogs and marketing companies early on. Is that one of the bigger struggles you had or is there any other struggles outside of that fear that you hit on there?

Ryan Vaughn (07:55):

Building a business, at least a media business in the early 2000’s was a struggle. It was just a challenge. Advertising was a business model that was changing a lot. You know we were catching the tail end of that and so throughout the process of building VNN, until we got a little bit smarter around how we were monetizing, a lot of it was a struggle. And so we were the type of business and the type of organization that was built on growth. And there’s a lot of economies of scale that went along with it.

Ryan Vaughn (08:20):

And so while some of the early businesses, which were just a media play it struggled to monetize for sure. I think you hit on it, but we believed, and I think was proven out over time that with enough scale other monetization opportunities would open up. And so that’s why we got on the VC bandwagon and started to push pretty heavy on that as well.

Clay Finck (08:40):

So you were running this marketing company, VNN and you were putting so much of your time and energy into the business. Was there a moment you knew that you really needed to take a step away from that and do something different? Or how did that all pan out?

Ryan Vaughn (08:55):

There was a variety of moments. And I think there was probably, I would look at those as like different opportunities I had to step off the treadmill and just a matter of was I ready for it at the time? I think the first time was when we closed our Series B. And I remember just feeling like we just got this money in, it was the culmination of an awful lot of work and hustle and everything else to get to that point. The documents alone are months. So just so much work, kind of all packaged into a, “Cool, we did it,” sort of a sense.

Ryan Vaughn (09:26):

I remember the feeling after that, just being like, “Oh, we just did all this. And I just made all these promises.” But ultimately I remember feeling like I have been chasing gold stars my entire life. And when I make all these commitments to people to go raise money on a series B to then go achieve more gold stars. And I remember just feeling like even if we hit this next milestone, or if we don’t, it’s not really going to make me happy, it’s not going to make a material difference to me it’s just execution. And I think that was an opportunity for me to reevaluate stuff. And that was also a time when I wasn’t ready for it.

Ryan Vaughn (10:00):

At the time I have a hundred odd employees and all sorts of reasons not to actually wrestle with this angst, existential pressure that I feel. And so I just kept going and kept hitting milestones, kept growing the organization and just kind of ignored the voice in the back of my head that was wondering is this really what you want?

Ryan Vaughn (10:20):

That was I think the first one, and I lived in that space, executing and ignoring the feelings that I was having for a couple years. And I probably would’ve gone even farther, honestly, if it weren’t for some outside intervention, which I was fortunate in hindsight, I feel like I was fortunate that someone sort of forced the issue. So I went into a board meeting and I put together an acquisition plan for roll up of these seven other companies. And I was like, “All right, we’re going to do this, this is how it’s all going to work and it’s going to be amazing.”

Ryan Vaughn (10:46):

And the board was like, “This is a great plan, but we also want to find somebody who’s done this before to be the CEO,” and oh, the ego blow that comes with that. And now, I mean, I see that transition enough to know that it’s pretty common, but I certainly didn’t think it was going to happen to me. And it was hard, but I feel like I had a job to do so I saddled up and I went through the recruiting process, brought on a really, really talented CEO to replace me.

Ryan Vaughn (11:08):

And I think even at that point, I was like, Oh, I can be the Chief Strategy Officer, Chief Operations Officer, whatever. But there was this one moment to your question. There was this one moment where we had been working together, me and the new CEO had been working the other for a few months and things were going reasonably well. And we got to a board meeting and it was the meeting where we had to sign the paperwork where I was going to sign over my title and everything else. And I signed the paperwork and it was like I got punched in the gut. And all of a sudden at that moment, it was clear that who I was, had been the CEO of VNN and I couldn’t be that anymore.

Ryan Vaughn (11:42):

And it was that moment that it was all of the stuff that I had been holding back for so long sort of raced at me and I had to reconcile with it. And so that was the beginning of sort of my, a lot of growth work, a lot of inner work to integrate all of these other pieces of myself that I’d been holding at bay for so long.

Ryan Vaughn (11:59):

So for me, that was stepping away for a sabbatical, which is a fantastic thing that I think not enough people get a chance to do. I was fortunate that I could, and that eventually led to me leaving the company and launching a coaching organization.

Clay Finck (12:13):

As you transition from being an entrepreneur at a startup to exiting, it’s like your identity of who you are entirely changes like you were just saying. How can others going through something similar grapple with that and help find their almost new purpose and mission in life?

Ryan Vaughn (12:33):

Yeah, I think it’s a really good question. I think my personal experience, and then also from a macro sense in working with a lot of founders is that early on, I think that the way that we orient to purpose is pretty different from how we do with some experience. You think about it like you come into the world, you graduate school or you start your company, or you’re in that phase where you’re going from, I am being trained, to now I’m in the go, perform.

Ryan Vaughn (12:55):

A lot of the experience of that is like looking at a menu of different options of lives that you could lead. And you’re like, I’m a doctor, I’m going to be a founder or whatever it is I’m going to be. Right? And when you evaluate option A, option B, option C, each one of those options’ comes with a life and comes with sort of purpose that’s attached to it. Comes with all of these questions, kind of already answered a little bit, even if it’s fuzzy.

Ryan Vaughn (13:17):

And so for a founder, when you’re stepping into your first role, a lot of it is like, well, I got to build something massive. I got to make something on myself. I’ve got to leave a dent in the universe, all that sort of stuff. And that’s certainly what drove me for much of my early career. And what I’ve learned happens in working with people, I’ve seen this pattern over and over again is that eventually you get that thing, assuming you have some success, you get a little lucky and so forth, and eventually you have success when you solve the problem you set out to solve, which is that I’m not yet successful.

Ryan Vaughn (13:44):

And then you’re still alive and you got 50 years left to go. And you’re like, now what? And that spot of I thought I knew what life was about. And I went out to go accomplish that and I did it. And now clearly there’s got to be something else, because I don’t feel like I can keep just chasing my tail around this. That’s a really disorienting place. And I actually work with a few founders that are navigating this place and purpose becomes a really big thing for them.

Ryan Vaughn (14:04):

So I think purpose is a really versatile word and a versatile concept. I think in Western society, we tend to think of purpose as a future oriented concept, like a time sometime distant in the future where we’re going to build this big thing and it’s going to be successful for whatever reasons matter to us. And in order to achieve this purpose, we need to subordinate ourselves today and organize everything that we do today, make sacrifices today so that we can invest in achieving this big purpose someday in the future. And you know, it’s a very motivating way of working.

Ryan Vaughn (14:34):

It’s actually hardwired into our brains evolutionarily to value or to sort of feel discontent more than we feel content. That’s part of the reasons why we as a species are so successful, but it means fundamentally that there’s no such thing as enough, as long as the purpose is somewhere in the future, there’s no way of ever achieving it because you just move the goalposts. And we as founders get really good at moving the goalposts and you’re like, “Oh, this thing I’ll be happy when I get this,” and then you get it. You’re like, “Cool, now actually I’ll be happy when I get this next thing.”

Ryan Vaughn (15:02):

So when a founder has, or when anybody I work with founders, that’s what I think about. But when anybody has gone through that process and has sort of exhausted the pursuit, which happens at a particular point, the way that I think about it is that purpose can shift from being future focused, to present focused. And it’s kind of a fundamental rewiring of how to use purpose in your life. And instead of anchoring on this big thing that you want to build someday in the future or you’re building toward, you think about purpose as a type of a life you want to live, a type of a human that you want to be, today, right now.

Ryan Vaughn (15:31):

And then you build towards making that your life as best as you can. So for me around that time, and this is evolving, so it’s continued to evolve today. But at that time, what I really wanted to do is I wanted to live a life being useful to people as much as I could, being in deep conversations with people as much as I could and writing. Because I felt like that was a passion of mine and I wanted to spend time with it.

Ryan Vaughn (15:51):

When I determined the kind of life I wanted to live in the present, then the question was okay, so how do I build toward a life where that’s all I’m doing, where I’m effectively steering my day to day efforts toward that lifestyle where I can live in the present moment as much as is meaningful to me. And I don’t think either of those are right. I may end up anchoring purpose in the future again as well. But right now having a present focus, purpose feels really right to me.

Ryan Vaughn (16:18):

It allows me to do good work for its own sake, not to try to get somewhere, but just because I’m here, I’m a monkey on a spinning rock in the middle of absolutely nowhere. And I have the opportunity to do something creative today. And that’s really how I think about it. When I talk to founders, the process is just really one of being clear on what you want future or present. And then once you’re clear on that, then everything can sort of fall into place, to design toward that end.

Clay Finck (16:46):

Yeah. You mentioned how you’re working more on what feels like more of a creative endeavor. You know, you have a lot more flexibility in that type of work. And I think the struggle for an entrepreneur is like you mentioned, you receive funding for your company. I would think that many entrepreneurs, they have this revenue target or gross profit target, whatever they need to hit for their business. So it’s almost like they might want to go down one path, but they’re always driven by this target that drifts them away from what they really want to do. So I think that’s a really big challenge for entrepreneurs.

Ryan Vaughn (17:19):

Yeah. I mean, I think particularly in the venture world, when you raise venture capital, you’re on a ride and getting off that ride is really, really hard. Because in order to make any sort of progress, you’re making commitments to all sorts of different people. And so the more commitments that you’re making, you’re sort of weave yourself a track that dictates your next period of time. And I don’t think that’s a bad thing.

Ryan Vaughn (17:40):

I think if you’re up to something, if you’re up to building something that’s meaningful, that makes difference, however you define making a difference, that happens through making commitments to people. You’re playing pretty small if you’re not making commitments to people, I think that’s a pretty important part of the creative process is making those commitments, but it does limit your flexibility. And so what I find is that there are for myself and then I also see this in other founders as well. There are these natural break points, which don’t happen that often.

Ryan Vaughn (18:07):

So it’s important to look at them and to take advantage of them when they do, but they do happen. You are between businesses, you sell a business, you hit profitability. There are these times where it’s like I have an option now to change, and nothing says that you have to. But I think that we set the course for our lives when we’re pretty young and we don’t know a lot. And as we continue to evolve as human beings, I find it really, really useful to examine our lives and our experiences and those moments to make an educated choice around where we want to go.

Ryan Vaughn (18:39):

That’s a hard thing to do when you’re full speed ahead on your company. And so that’s why I mentioned sabbaticals earlier. I think that like intentionally doing nothing for a period of time is just so profoundly useful to people. Even if it’s like, I’m going to take a week off and I’m going to sit in my house and I’m not going to do anything for that week. For me, it was like two months that I took off. And I think that’s a really, really meaningful amount of time as well, because what happens there is we are all running so fast, we’re all chasing whatever it is that we’re interested in attaining.

Ryan Vaughn (19:09):

What happens when you stop is all of the reasons that you were running start to tell you to keep running again and you get to see like turns out I am terrified of being left behind by my peers. And I am scared of not mattering. All these different things that drive us. We get to see when we stop because it’s the stuff that starts playing in our head and you get to see these are the things that are motivating me. These are the things that are causing me to make the decisions that I’m making. And if you stop for any period of time it’s hard to avoid those things. They just show up.

Ryan Vaughn (19:39):

So it’s not like you had to do any work, but the opportunity there is when you see the things that are driving you, you get to evaluate do I really want to live a life that is the response of feeling fear that I’m not going to be good enough. Is that really what I want to dictate this one wild and precious life that I get.

Ryan Vaughn (19:54):

And for me it wasn’t, that wasn’t a reason that I found worthwhile enough and stopping for that period of time, enabled me to see that and choose more consciously.

Clay Finck (20:04):

What was your definition of success when you started your company in 2010 and how has that changed over time? And what’s your definition of success today?

Ryan Vaughn (20:15):

I think this plays into the purpose question, right? I think when I first jumped into the startup world, success for me was like building a unicorn business and exiting and making money. And I was on that track for a period of time. Honestly, the business that we built could still get there. I’m not on that day to day involved with the organization anymore. But I think I was on that path until I couldn’t convince myself anymore that if I get money from a unicorn sale that’s actually going to make me happy.

Ryan Vaughn (20:43):

There was a point where somewhere in that messy process of moving on where I couldn’t convince myself of that anymore, I couldn’t convince myself that the pot of gold at the end of the rainbow is really a real pot of gold. And so again now, like as I think about success for myself, it’s really present focus. And after spending so long, especially in the work world, so much of my energy spent on being the perfect CEO or being a great CEO, whatever I thought that meant, you know when you hear that, what I hear is being the person that I thought other people wanted me to be, because that’s how I was going to be a good CEO.

Ryan Vaughn (21:16):

It was like what would Steve Jobs do? I’m going to do that. What would so and so? Right and doing that for number of years, eventually it got to the point where it was really hard to figure out who I was amidst all of the different roles I was trying to play. And so for me, success today is really anchored around being myself, just full out. And so the way that I organized this now is put a decent amount of work into like a really functionally useful, present tense definition of success so that I can use it anytime.

Ryan Vaughn (21:45):

And so for me, it’s three words, it’s soften, which I can feel in myself. I can actually do it. I can soften my belly. I can sort of let any tension in my body kind of relax. You can give it a shot too, if you want to, the second word is open. And so this is a process of opening to the moment to whatever it is that life is asking of me right now. And sometimes that’s bust my hump in building an accelerator right now, sometimes it’s that.

Ryan Vaughn (22:12):

Sometimes it’s go to go walk outside in the sunshine, 75 degrees right now. Like I plan to do that today. And then the third word is full self-expression and that’s really, as I think about a life well lived for myself, it’s less about accolades. It’s less about leaving a dent in the universe. It’s more about, I believe there’s a story that only I can tell because of my unique life circumstances and experiences and personality. I just want to make sure I tell it.

Ryan Vaughn (22:37):

That’s really how I think about success today is in learning what’s on the inside of myself and then doing my best to express that in the world.

Clay Finck (22:45):

I really like that. In your writings, you’ve touched a bit about mental health and trying to take care of yourself while you’re trying to accomplish all of these amazing feats. What have you found over the years to be most helpful in supporting your mental health?

Ryan Vaughn (22:59):

I think that’s a really good question and a valuable one. And I know that I’m grateful that that’s becoming a bit more a part of the zeitgeist now, and I think there’s probably 101 answers or there are probably 101 answers to that question. And generally speaking, I could find a case to support most of them.

Ryan Vaughn (23:15):

What I actually, I think for me, what resonates more than mental health is mental growth and that’s a pretty fundamental shift for me. And so when I work with clients and how I think about it for myself, my own self care, a lot of it’s organized around mental growth. And if you study any of the last a hundred years of developmental psychology, what you find is that there is a process that human beings go through as their consciousness evolves, as their mind evolves.

Ryan Vaughn (23:42):

And whether you’re taking sort of Bob Kegan out of Harvard has an Adult Development Theory, Spiral Dynamics is another one. Ken Wilber has Integral Theory. Well, any of these processes what they say is that human beings, their inner state evolves in a predictable way over time. And it evolves based on moving progressively more from the world of subject to the world of object. So if you think about it, like when you’re born everything, the minute an infant is born, everything is all one thing.

Ryan Vaughn (24:11):

There’re no distinctions between anything. It’s all just, something is all they really can do. Right? And then pretty soon they get a sense of mom is different than me. So now I can see there’s an object out there and now I can interact with that object. And as a human evolves, they start to develop a sense of like, oh, there’s a spoon, that’s an object that I can do something with. And, oh, there’s a soccer ball or whatever. And more and more like the world becomes more and more full of objects that I can interact with.

Ryan Vaughn (24:38):

And that mostly is the childhood development process. For adults, the development process functions similarly, meaning that you’re moving things from the world of subject to the world of object, but it’s moving bits of your personality from the world of subject to the world of object. And this is ultimately when I think about the work that I do and the practices that are important, it’s all around facilitating that process, helping somebody move from what Kegan would call the socially authored mind, where you get your sense of identity from the roles that you play in the groups that you’re a part of. That’s mostly where maybe young adults are. It’s like, I’m a Democrat. I am a Christian. I am a finance person or whatever.

Ryan Vaughn (25:18):

These are all these external groups that I’m internalizing and making part of myself, part of my subject. And the first step in that development process is moving from the socially authored mind, which I just described to the self authored mind, which is when you start to see that, actually I’m not a Democrat. That’s just a thing that exists separately from me that I mistook for myself. And now that I see it separately, I can decide which parts that I like, which parts that I don’t like, and I can work with it more consciously.

Ryan Vaughn (25:46):

So it involves process, that’s probably the shortest crash course in terms of adult development. But when I think about how a human being can orient to helping their mind work at its best, it’s all about facilitating that process. So I have found for myself and then working with a hundred plus founders through various stages of this process that you can kind of pick and choose the model that you want. You can use leadership development, you can use adult development, you can use ego development, you can even use spiritual development.

Ryan Vaughn (26:14):

Actually spiritual development is probably the one that has worked the best for the most people because it’s been around for thousands of years, but it’s all this adult development process, moving things from subject to object and realizing that you are not that. So when I think about the things that work to help people to do that process well, it’s things like meditation. Meditation is a really useful tool, not just to help you be calm, although some people use it for that, but ultimately to learn first and foremost, that you are not your thoughts, your thoughts exist separately from you. They are object and therefore you can work with them differently.

Ryan Vaughn (26:49):

There’s a practice that I use and I work with founders a lot on called Morning Pages, which is a journaling process that you do every morning. You write three pages about whatever, and you can even write three pages that just says, I don’t know what to write about for three pages if you want to, the key is you got to fill the three pages. And in doing that, that again creates space for the processing to happen, where you can process all the different things that you know that you’re doing as you’re building your organization.

Ryan Vaughn (27:12):

A couple more practices that I think are super useful. One, I think of as having a learning focus. So instead of just being like, I’m going to go build a business, it’s like well in order to be a good leader, I need to learn to delegate as an example, and then being really intentional about that’s what I’m learning right now. I’m going to do a deep dive into delegation, become good at that and then move to the next thing.

Ryan Vaughn (27:33):

So there’s probably a handful of other ones that I could riff off of, but ultimately I think the reframe and the frame that I think is so useful is to think about self care as mental growth, every bit as much as mental health.

Clay Finck (27:47):

Ray Dalio, whose book is sitting right behind me like you pointed out, he’s been pretty vocal about meditation and how transformative and crucial it has been for him over the years. I believe he’s done meditation for decades, most of his life. Could you talk more about the meditation practice you do and how that has maybe evolved over the years?

Ryan Vaughn (28:09):

You mentioned Ray Dalio, I think he’s a good example. He’s been vocal about it, but it’s way more than just him. And I think other vocal people are Mark Benioff, the founder of Salesforce, he’s kind of crass about it. He uses curse words when he talks about how awesome meditation is. Jack Dorsey I mean, if you think about the leaders in the tech world and in the business world, I bet you it’s got to be 75% plus are pretty devout meditators. So for me, I started 12 years ago or so. And at the time I was messing around with some of the apps with Calm and Headspace and these types of things and ultimately it was like, I am constantly anxious. How do I solve that?

Ryan Vaughn (28:44):

That was how I thought about meditation and I think that some meditation can do that. Some meditation is just designed to help you get calm, but ultimately meditation is a form of exercise. And so depending on the type of meditation that you do, you’re exercising different muscles and while there’re some types of meditation which are good for focusing, there’s a variety that can help you to focus really well. And that’s a useful skill to have.

Ryan Vaughn (29:07):

There’s a variety that can help you to develop equanimity, sort of calm under pressure by sensing in to your feelings and sort of letting them, experiencing them as opposed to resisting them. And then there’s a type of meditation that’s geared around learning how your mind works so you can work with it differently. And ultimately, as my practice has evolved, I’ve found one type of meditation that I think is just incredibly useful for leaders. And this meditation is called Shikantaza.

Ryan Vaughn (29:34):

It’s the type of really stripped down Japanese Zen. And it’s so, so simple and so challenging, but it’s simple enough that I can give you all the instructions on how to do Shikantaza right here on this podcast. The instructions are sit down and most of the time they have you have your eyes open and just kind of stare a little bit in front of you, but you sit down and you hold everything still, everything that you can possibly hold still, hold still and then watch what moves. And that’s the instructions for Shikantaza.

Ryan Vaughn (29:57):

And what you find really quickly is that there’s a lot of stuff that I can’t stop moving. It’s just going to move. I don’t have any control over it. And at that moment, you start to realize how you react to all of those things that are moving. Like my thoughts are moving and well, wait, I thought I was supposed to be Zen and not thinking about anything when I’m meditating. And then you realize not only do I not control my thoughts, but now I’m having a reaction to those thoughts, which is like, you should be meditating, which I also don’t control.

Ryan Vaughn (30:23):

That reaction just happened without my control. And now I’m thinking I’m reacting and now I shouldn’t be doing that. So now I’m going to react again over and over and over, you get a sense of like just how much of everything that exists in our head happens independently of us. And that starts to A, develop a distance so that you’re not identified so strongly with everything that you think, and you can sort of develop that equanimity, but it also gives you the ability to see patterns in the way that you think. And that really is just such a useful tool for leaders, for investors, anybody that’s making important decisions. Understanding the thought patterns that underlie those decisions and making conscious decisions about which ones work for you well, and which ones don’t work for you.

Ryan Vaughn (31:07):

I can’t think of anything that’s more important for somebody that’s a professional decision maker. And like you talk about Dalio. That’s a perfect example, like the principles that he’s put out and the big model that he developed, a lot of that has to do with let’s think consciously about how we made these decisions and then make conscious choices about whether we should make those decisions the same way again.

Ryan Vaughn (31:26):

Shikantaza is a fantastic tool. It’s hard, it’s challenging and it takes some coaching, but it’s a very, very useful tool to train your mind to think the way that you want it to think, as opposed to just the way that it generally works out of the box.

Clay Finck (31:39):

75% of founders are devout meditators. That’s an incredible stat. It seems like meditation is one of the most underrated and underappreciated practices and routines available. And I’ll be honest, I’ve been on and off with meditation throughout the years myself. Related to meditation and mental health a lot of these practices are done in the mornings. So I’m curious if you stick to a specific morning routine and if so, what that might look like?

Ryan Vaughn (32:08):

Yeah, I do meditation. I do journaling. I do exercise, self-reflection and I have a learning goal and I sort of have another couple practices, but on a daily basis, I think about it that way. But one of the big challenges that people have when they’re implementing practices like this is, I don’t have enough time. Right? That’s always the challenge. Probably every founder I work with is like, “Yeah, right. I can dedicate a half hour or an hour in the morning to just taking care of myself and helping myself approach the day correctly. No way. I don’t have time for that.”

Ryan Vaughn (32:35):

And there’s this really interesting story that I find myself telling a lot. There was an interviewer that was interviewing the Dalai Lama and the Dalai Lama meditates for five hours a day. Something crazy, even to me is that’s quite something, but the interviewer asked him, “You’re running a country, the whole country of Tibet. Plus you’re doing all this peace work all across the world. You’re doing all these things. How on earth do you find time to spend five hours meditating?”

Ryan Vaughn (32:57):

And the Dalai Lama was like, “You know what? You’re right. Actually, I didn’t realize all of the stuff that I’m doing. I’m doing so much. I better meditate six hours.” And that always has stuck with me because ultimately it has much less to do with how much stuff you get done and much more to do with choosing the right things to do and doing them well, especially as your organization grows. And so I think that if you run into the problem or they run into the challenge of, “I don’t have enough time to do this,” in my view you’re not too busy to do it. You’re just prioritizing wrong.

Ryan Vaughn (33:25):

And if you were to look at it consciously and really reckon with the fact that you’re not going to get everything done that you want to get done and start to make some tough choices about what’s actually the smartest thing to spend your time on today, practices are the point of highest leverage. It’s the way that you sharpen your thought every day. So it’s not a thing that I think can be skimped on.

Clay Finck (33:44):

That is a very profound insight. Just that idea of sharpening your mind and taking that time to really think about what are the most important things you should be working on, especially for entrepreneurs, whose time is extremely valuable. And it’s critical that their limited amount of time during the day is spent well.

Clay Finck (34:03):

Transitioning to chat more about working with entrepreneurs. What are some of the biggest mistakes you see other entrepreneurs making that need to be addressed? You’ve lived in many of these people’s shoes and probably are able to spot some of the same red flags that you’ve been through. So I’m curious if you see any recurring themes in who you work with.

Ryan Vaughn (34:22):

Yeah, there’s a lot, honestly, the process of building an organization is so personally challenging that people end up going through a lot of challenges that are knowable. I think for founders and leaders, there is one moment that everybody learns at some point when they realize that all of the dysfunction that they’re seeing in their company is actually their personality being mirrored back to them. And that is just such a jarring thing for most people.

Ryan Vaughn (34:49):

Because this comes back to this adult development process of moving things from subject to object. Most leaders, when they first start, they look at their organization as a thing that they should be managing and you know, to manage an organization, you put values on the wall, you develop a really good purpose and you put all this scaffolding in place to help your organization grow.

Ryan Vaughn (35:07):

And so many leaders, I think, think they’re doing the right things. They check all the right boxes relative to company operating system, values and OKRs and whatever. And then it just doesn’t work. And their company doesn’t do what they think they ought to be doing instead of executing flawlessly on their plan. They’re always late to meetings and everybody’s missing deadlines. Nobody’s communicating well, everybody’s mad, whatever the symptoms are. And that can be so frustrating.

Ryan Vaughn (35:33):

I think it probably is for damn near everybody that goes through it. And it’s not until you start to look at, as a leader, your own personality and your own behaviors as a model for the rest of your organization to follow that things start to open up. And there’s just been so many examples for myself it’s easier to talk about me than my clients because of my clients are all confidential.

Ryan Vaughn (35:54):

But in my own case, we scaled our organization from 15 to 75 people in nine months and everybody hated each other afterwards. And I couldn’t figure out why in the hell everybody hated each other. It seemed like everything was going well. But as I started to work with my coach around my own stuff, what I realized is that when there were challenges, my process was I would say, “All right, don’t care about the challenges, I got work to do.” So even if I’m mad about it or upset, I would shove the emotion down and get back to it.

Ryan Vaughn (36:21):

I talked about that earlier and coach says something like, “Okay, so how does that remind you of your organization?” And as I started to look at my organization through that lens, I started to see so many of my employees who, when somebody wouldn’t do, they’d mess up somehow. Another employee what they would do is they would say, “Well, this person messed up, but I don’t have time for that. I’m just going to do the job and then forget it, we have work to do, we got to keep moving.”

Ryan Vaughn (36:43):

But then they would hold on to that resentment of the other person and just wouldn’t talk about it because that’s what I did. And you have all these employees getting stuff done and resenting the heck out of other people for all the littlest things that they’re not talking about. And pretty soon it just led to this crazy blow up. And I was so frustrated about it. I remember at the time being like, “Why is everybody so mad all the time? It’s crazy.”

Ryan Vaughn (37:01):

And when I finally realized like, oh that’s because they’re just doing what I do. That enabled me to work consciously on how I dealt with problems and talking about not only well there’s a problem. I got to go. But really like, okay, what is this? How is it impacting people? And how can we help everybody feel complete about this? That’s what ultimately helped our organization to stop resenting internally the way that they did.

Ryan Vaughn (37:25):

So for any leader, I think there’s this weird “Aha” moment where you realize that your biggest point of leverage for managing your organization is the way that you show up as a human and not various tools like OKRs or values or anything else. And I think that’s an eye-opening process that everybody goes through and it’s something definitely to look for.

Clay Finck (37:46):

Like you mentioned, being a good leader is obviously something that’s very important in building an organization. How can entrepreneurs and business leaders develop their leadership skills outside of simply just hiring a coach?

Ryan Vaughn (38:01):

Before we talked about these four parallel worlds of adult development, ego development, leadership development, and spiritual development. All of those are give or take the same process. They emphasize different parts and they use way different language. But the process of developing as a leader is developing as a human, a more complete human that can see more of themselves as object, can work with more of themselves and lead better.

Ryan Vaughn (38:22):

And so there’s lots of different ways of skinning that cat. You can dive in any one of those individual ways, but whatever you choose, I think the other thing that I think a lot of people get wrong as it relates to the approach is it’s easy to approach leadership development as like a thing to figure out. It’s like, I got to figure out how to be a leader and I got to find the answer of whatever that is. And that’s not how human development works.

Ryan Vaughn (38:46):

It’s not a cognitive thing. It’s not a… I’m going to learn some sort of bit of information that’s going to change everything for me. That’s not how it works. It’s practice. It’s determining what you want to develop a skill in or develop a competency in and then practicing it over and over and over and over again and tools like meditation and journaling and declaring a learning focus and things like this can all be useful.

Ryan Vaughn (39:06):

Therapy can be useful on the journey, but ultimately I think it needs to be approached as a process of constant practice and then choosing your practice is based on the type of result that you’d like to see. I think that’s just a huge part of it.

Clay Finck (39:21):

What does an effective leader look like to you? I’m really curious about this, because this concept of leadership almost fascinates me. It’s almost like this abstract sort of idea of being a quality leader. And you mentioned Jim Collins, his book, Good to Great in one of your writings and you talk about what it takes to be a Level 5 Leader.

Clay Finck (39:40):

I’m curious what are some things or some qualities that screams like yes, this person’s an effective leader and is capable of leading a great organization.

Ryan Vaughn (39:52):

To me also, that’s squishy in that I think it depends on who you’re asking. What makes a good leader. Jim Collins has a fantastic model. I really liked his and sort of paraphrase using my words. The Level 5 Leadership, Level 4 Leadership is a conscious leader. Somebody who sees their personality and their stuff as object and they can work with it so that if they’re not getting the results that they want by being bullheaded and kind of creating reality distortion fields, they can change.

Ryan Vaughn (40:16):

That’s the key distinction that a level four leader would allow you to do. And that’s what all the mental growth that I described does. But level five in Jim Collins’s world it adds something that’s I think pretty important. It adds what I think of as a transcendent purpose, like a clarity around this is what my life is about. And I believe in this so strongly that I’m willing to subordinate my own needs and my own interests to achieve this thing, to cause this thing to exist.

Ryan Vaughn (40:44):

And that’s a pretty small group of people who not only have the consciousness and the capacity to change themselves to suit the results that they want, but also are lit up by something to that degree. And I think in Jim Collins’ work, he describes a lot of people have to have some sort of a brush with mortality to finally anchor on something that’s like, I get a sense of I’m going to die, hard stop. It’s going to happen. And I will not be able to get everything done. Matter of fact, I’ll get less than 1% of everything done. And so within that context, what is the one thing that I want this all to be about?

Ryan Vaughn (41:17):

And for the people that have that, the people that are clear on this is what I’m working for. And it comes from that deep place of understanding that this is it, that I think makes a really, really compelling leader. So that Jim Collins’ model, I think there’s a lot to be said for that. For myself, the way that I think about leadership is rather than… you know for a long time, I was trying to be a, what I called a successful and certain leader, somebody who had his shit together. Knew where he was going, had all the answers and could tell you all the stuff and I got to the end of that and I realized it was lacking.

Ryan Vaughn (41:48):

It can get you a certain amount, but you know, it doesn’t go any farther than that. And so for me today, the way I orient towards leadership is this unique combination of vulnerable and committed. I think that nexus of those two words just really sums it up in like a chef’s kiss sort of way, for me. Vulnerable in that you’re willing to own what you know, what you don’t know, your fears, your hopes, your dreams, all this stuff is like all on the table in a fair game, because by you being vulnerable in that way, you give the people you’re leading the opportunity to do that as well.

Ryan Vaughn (42:20):

That’s ultimately what engages people’s hearts and gets them to want to jump through walls, proverbially for you, so vulnerable to give your people the ability to be vulnerable too, but then also committed meaning I don’t know what I’m doing. I’m nervous about it. I’m excited about it. I have all these jumbles of emotions, but regardless of all of that, I’m moving forward because this matters that much.

Ryan Vaughn (42:39):

I think to embody both the realness of the vulnerability with the steadfast commitment of yeah, this is uncertain, we’re doing it anyway, because it matters, I think is a really, really compelling place to come from for people. That’s my definition and you know, I think it really depends on the person, how they want to orient towards what makes them a successful leader.

Clay Finck (42:57):

It’s funny, you mentioned the idea of having to grapple with your own mortality. I recently interviewed Eric Balchunas who wrote a book called The Bogle Effect. It was all about John Bogle and building his company, Vanguard. Now Vanguard today has over 7 trillion dollars in assets under management. And John Bogle, I believe he was in his early 30s, he had a heart attack and he was diagnosed with this really rare heart condition.

Clay Finck (43:22):

And I asked Eric why was Bogle able to build this company that no other company was able to build? And it was just this crazy incentive structure where all the profits are just go all straight to the investors and they just lower their fees. You know they really have a completely different objective than all the other companies.

Clay Finck (43:39):

I asked Eric how is he able to do this? And he was like, “I think he grappled with that idea of eventually he’s going to pass away. And he has this rare heart condition. He doesn’t know when he will pass.” And you know, he really just had a purpose driven life and oftentimes with successful people, I’m always curious if there’s one or two books that are must reads for listeners. You know, I interviewed Eric to talk about his book. Are there any books that have had just a profound impact on you?

Ryan Vaughn (44:07):

Yeah. It’s funny as you were describing your conversation with Eric and Vanguard, there was a book that was popping in my head around like, oh, there’s this world of like reckoning with I’m going to die. And so therefore what… there’s a recent book that I read that I really loved called Four Thousand Weeks and the subtitle’s Time Management for Mortals and it really sort of deconstructs all of popular time management stuff, which is all around like how to get more stuff done.

Ryan Vaughn (44:31):

And it basically starts with the stance that all of our efforts of trying to get more stuff done are just a failure to reckon with the fact that we never will get everything done. And the sooner that you can just settle with, yep, I’m not going to do most things. Then you can start to do the hard work of choosing the things that you really want to do. So I think that’s a really, really profoundly good book.

Ryan Vaughn (44:52):

I think for me, the books that have made the biggest impact on me are probably mostly in the world of spiritual development. I’ve really, really liked some of Ron Bass’s stuff. I really, really liked [inaudible 00:45:06] has a lot of really good things as well. And this again is like the spiritual development side of adult development. Yeah, there’s a variety in that world.

Ryan Vaughn (45:12):

I think in the business world, I wrote a post a while ago called Books that Changed my Business. And there are a few now that I think about it that I included in there. So one was David Brooks, The Second Mountain. David Brooks is a New York Times columnist, but a lot of it has to do with this process of going from the achieving mountain, which is your first chapter of life to what’s next.

Ryan Vaughn (45:31):

The Meaning Revolution by Reid Hoffman is another really good example of that. And then Reboot by Jerry Colonna is a great one. That was a kind of right book at the right time for me and was part of what led me to coaching. But I think the one that I’m most excited to talk about is this book called The Artist’s Way.

Ryan Vaughn (45:48):

And I take the stance that entrepreneurs are artists that work at scale. And so being able to channel creativity and hone it and nurture it is a really important capacity for leaders. And The Artist’s Way is the best tool set that I’ve found to cause that for people.

Clay Finck (46:05):

Fantastic. Thank you for sharing. Ryan, I really appreciate you coming onto the show. Before I let you go and we close out the episode. I wanted to give you the opportunity to give a hand off to the audience, to where they can get connected with you, how they can reach out. If they’d like to.

Ryan Vaughn (46:21):

All of my stuff is on my website, leadinsideout.io. The organization is called Inside-Out Leadership. So the website is leadinsideout.io. I’m on Twitter and LinkedIn at Ryan H Vaughn and if you want to stay in touch, I’m not currently accepting new clients, we’re all booked.

Ryan Vaughn (46:38):

But a great thing to do is subscribe to the newsletter that I publish once every other week. And a lot of it just has to do with this conversation around how to evolve as a human being and as a leader and as a professional. Built for VCs, built for entrepreneurs and kind of everywhere in between.

Clay Finck (46:53):

Awesome. Thank you so much, Ryan. I really appreciate it.

Ryan Vaughn (46:56):

Thanks Clay.

Clay Finck (46:57):

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Clay Finck (47:05):

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Clay Finck (47:12):

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Clay Finck (47:22):

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Clay Finck (47:31):

And with that, we’ll see you again next time.

Outro (47:34):

Thank you for listening to TIP. Make sure to subscribe to We Study Billionaires by the Investor’s Podcast Network. Every Wednesday, we teach you about Bitcoin and every Saturday we study billionaires and the financial markets. To access our show notes, transcripts, or courses, go to the investorspodcast.com. This show is for entertainment purposes only. Before making any decision, consultant a professional. This show is copyrighted by the Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.