Step into the extraordinary life of Ryan Vaughn, a former aspiring NBA player turned tech CEO, as he unfolds his transformative journey with Matt Edmundson. From basketball courts to tech innovation and the power of meditation, explore how Ryan reshaped his identity and leadership style.

In this captivating episode, Matt Edmundson converses with Ryan Vaughn of Inside Out Leadership, exploring Ryan's unique life story. From pursuing NBA dreams to leading a tech company, Ryan's narrative is a compelling tale of self-discovery, confronting fears, and embracing change. Join us as we delve into the pivotal moments of his life, including an extended sabbatical that redefined his approach to life and leadership.

Key Takeaways:

1. The Power of Transition: Ryan Vaughn's journey from an aspiring basketball player to a tech founder highlights the fluidity of life paths. His story emphasizes the importance of embracing change and finding new passions, showing how our dreams and goals can evolve over time.

2. Embracing Vulnerability in Leadership: Ryan's experience underlines the significance of vulnerability and authenticity in leadership. His battles with imposter syndrome and the realization that showing vulnerability can be a strength provide valuable insights into the essence of modern leadership.

3. The Role of Self-Reflection: Ryan's 18-month sabbatical, dedicated to meditation and introspection, illustrates the transformative power of self-reflection. This period was crucial in helping him confront personal fears and beliefs, significantly impacting his relationships and professional life, and offering a compelling testament to the value of dedicating time for inner growth.

And I think that was, that was, uh, um, a pretty critical sort of shift and

in that whole space, uh, in the, the willingness to be Ryan as opposed to Ryan,

the CEO or Ryan, the basketball player, any of that stuff was where, um, where

vulnerability came from because it was in letting go of the person that I wanted

people to think I was, or the person that I wanted to become and just being.

Me, here, who's nervous or scared or happy or excited or whatever, um, being

willing to bring that, um, just opened up everything else that happened since.

So we've continued to build companies, um, continue to support people and

be as useful as I can, but it comes from a really different place now.

to

and welcome back to Push To Be More.

I'm your host Matt Edmundson, and we are about to dive into

another deep exploration of what truly fuels the journey of life.

Now joining me today, I have an exciting guest, Ryan Vaughn

from inside out leadership.

We're going to be diving into his life experience, the hurdles he has had

to push through, the way he recharges his batteries, and his spirit, and

what steps He's taking to be more.

Oh yes, we're going to get into all of that now.

Don't forget, you can find all of the detailed show notes and complete

transcript of our conversation on our website pushtobemore.

com and whilst you're there, if you haven't done so already, of course,

sign up to the newsletter and each week we'll zip all of the shows, insights,

links and goodies direct to your inbox.

Absolutely.

Free.

Oh yes.

Now this episode is brought to you by aurion Media, the champions

of meaningful conversations and creators of powerful podcasts.

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Now.

Let's meet Ryan Vaughan, CEO of Inside Out Leadership.

Now, if you've ever imagined a basketball playing future NBA aspirant turned

tech founder who's had more life chapters than your favourite binge

worthy series, well, that's Ryan.

Yes, hailing from Michigan, Ryan's journey is the stuff of legends.

Uh, chapter one, it's all about hoops, dreams and tattoos.

Chapter two, a wild ride that, uh, veered close to the edge with

drinks, jail time and near misses.

We're gonna get into all of this.

By chapter three, after a sobering wake up call, he dove headfirst into

the tech world, creating the ESPN.

com.

Com for high schools and scaling it to heights.

Even he didn't foresee.

But of course, as they say, with great power comes great self-reflection.

So what happens when the hotshot c e o steps off the rocket ship?

Well, Ryan did what most of us only dream of.

He paused, breathe, meditated with monks, dance with psychedelics,

and searched for Ryan.

Just Ryan.

No titles, no pretense, just pure unfiltered authenticity.

The results.

A renaissance man reborn, now guiding CEOs and founders to find their Ryan moments

through his venture Inside Out Leadership.

His message, letting go can be the most empowering thing.

So for those tired of keeping up appearances and hungry for

genuine, authentic leadership, apparently Ryan, you're the man.

Great to have you on the show.

Thanks for joining us.

How are we doing today?

I'm doing fantastic and I feel like I want to give an honorary mic drop

for everything that you just did.

That was, that was divine.

Divine, it's, um, it's one of the things that we've started doing, uh, if you're

a regular listener to the show will know this, we've started taking the

bios of, uh, guests coming on the show and we just have some fun with them.

And why not?

I quite enjoyed that one.

That was quite a good one actually,

It was great, yeah, I don't think I could have told it any better.

Well, there you go, what can I say, well done to the team, big shout

out to the team for doing that.

Uh, and so, uh, you hail from Michigan, are you in fact

in Michigan right now, sir?

Yeah, I'm in this beautiful, it's actually new to us, but it's a 19th

century house in the middle of a historic district in Grand Rapids.

So, yeah, beautiful day, excited to be here.

Just at the turn of the school season, sort of segwaying into a quiet

house for the first time in three

yeah, yeah, yeah, it's funny because here in the UK, uh, school

has, um, started back recently.

And what has happened is the weather has got really good, so all the kids have

gone back to school and there's like this mini heatwave and they're all moaning,

why is the weather so good, now we're back at school, but I'm enjoying it,

I'm not going to lie, it's nice having a bit of peace and quiet, it's good fun.

So right, let's open up with the question.

I do like to ask all of my guests, uh, so we're pushing boundaries here with

the help of aurion Media, or paving the way for passionate leaders to

amplify their reach through podcasting.

So let's imagine you're about to hit the record button on

your very own podcast show.

If you could pull up a chair for anyone, past or present, who's left

an indelible mark on your journey, who would you want on the other

side of the microphone and why?

Um, so I don't have a podcast, I've been on a few podcasts, but

I haven't been the interviewer.

And so this is a, this is a new thing for me to, uh, explore.

Um, my, my instinct, my first instinct is I would love to interview.

Actually, okay, I have two answers for this.

My first instinct is I would love to interview this guy named Michael Singer.

Michael Singer, most people probably know him.

He wrote the book called The Untethered Soul.

Okay.

But in addition to that, he has one of the most fascinating stories, cross

sections of inner work, sort of deep self reflection, and tremendous business

success, I think, that I've ever seen.

He wrote this other book that I've read.

And this is the reason I probably wouldn't choose him because he wrote a book about

his experience, which I think is the coolest thing, but, um, it's called the

Surrender Experiment and, uh, he journals his, his, an autobiography of how he

started as this monk in the woods, uh, and then just through this, this one decision

that he made, which was to just surrender to what the universe was interested in him

doing and do the best work that he could.

That led him through a crazy series of events to eventually

managing two public companies.

Uh, taking two companies public and then getting investigated by the FBI

and just all sorts of crazy shit.

So...

I would love to have that conversation, but he has told his story, so I

don't think if I had one choice, I don't think he'd be the guy.

The person that I think would be the guy, uh, or the, or the

person, uh, is, uh, Lao Tzu.

Uh, Lao Tzu is the author of the Dao De Qing.

Which is, um, probably the most influential book that I've read.

Um, and it took me a decade.

I first read it when I was 21 or so, and I was just in the process of getting sober.

Um, and I was recommended it by my sponsor in, uh, in AA, and he was like, you

should read this book, this Tao Te Ching.

And it made no friggin sense to me at all.

Um, uh, the, the book, it's, it's, um, it's poetry ish, poetry lite, um, and

it, and it speaks in ways that Your brain, I've learned, needs to evolve

to a certain level before you start to understand what they're talking about.

Um, and it's one of the most brilliant books that I've read.

Uh, there's debate whether Lao Tzu is a real person or if he was like an

amalgamation, kind of like a Banksy, uh, over in your guy's neck of the woods.

But, um, you know, back, uh, 3, 000 years ago, 4, 000 years ago when

The Doubted Chain was written, I would love to interview whoever

it was that came up with that.

That book, um, and just talk philosophy.

I think that would be the most interesting and amazing sort of

channeling from one person to the other that I could come up with.

So, I mean, two fascinating guests on the show.

There's obviously a connection between the two of them.

Um, and, uh, we're going to get into why maybe those two a little bit, because I'm

curious if we fast forward, if we rewind, uh, back to the start of your journey

and I'd asked you the same question, they, I'm guessing, would not have been

your first choices to be on your list.

Mm

No, I mean, at, at various points in my journey, I'm sure I would have, I would

have pegged other people because that's.

That's what my mind was at, that's where, where my attention was being paid, right?

Um, I imagine when I was a young kid it probably would have been,

you know, Michael Jordan or Wilt Chamberlain or something like that.

Um, but, uh, but yeah, I mean I think that's, that's, I think

that's a normal part of growth.

Um, and, and.

Where I sit now, that's very much, um, it's that level of depth of

conversation that I'd like to have.

I've sort of gone through the process of chasing as much as I can and trying

to accomplish as much as I can and that would, there's people that have

that conversation and I've had a great deal of those conversations, but but

I think if I had one shot, I'd want something that's very, very meaningful

and has the potential to change me.

So what does, what does a meaningful conversation look like for you then?

Hmm, um, so I went through Well, and I'm, I know we're gonna talk about

my, my, my story a little bit, but just to give a, a little sense of it.

So I was a c e O for, uh, 15 years, uh, a tech c e o.

And in that period of time, uh, I was so careful about.

The image that I had, the CEO that I was perceived to be, like I had this

idea of who the perfect CEO would be for my investors, who the perfect CEO

would be for my employees, who the perfect CEO would be for podcasts that

I was going to be on, for the media, all these different things, right?

And.

Um, and I was very manicured, uh, about making sure that I was, I was going to

be this person, you know, it's going to be the best possible version of, of, um,

what was expected for each of these roles.

And as a result, um, very long and involved story short, one of the things

that happens is I lost myself in that process and really got caught up in

trying to be all these, you know, trying to meet all the expectations

of all these different people.

And it took, uh, a lot of work and a lot of pain.

To get to the point where I was willing to open up, um, and I was willing to just be

vulnerable about the fact that, you know, like everybody else, I don't know what

the hell I'm doing, um, I'm making it up and, and trying as best as I can, like,

like anybody else, despite the fact that I had this idea that I should have all the

answers for my investors and I should have all the answers for my employees, when

I started, when I was finally willing to open up and be vulnerable and be honest

about what was true for me, It opened up a space for whoever it was I was

talking to, to do the same and to have conversations that, um, almost immediately

went from, you know, they slowed down in cadence, and I can feel myself

slowing down as I'm talking about this.

They went from a level of depth of sort of, you know, playful banter

and things like that into something that was more, more meaningful and

more, um, sort of, there's a different listening that's present then.

When people are really listening to you and, um, and then that creates

a space for them to share the same.

So, if I had, uh, uh, if I had my podcast, I'd want to have

those types of conversations.

hmm.

Well, please do a podcast because I would find that absolutely fascinating,

um, in terms of how you would do that.

So one of the things that's always intrigued me about podcasting,

Ryan, is the stuff that we get to talk to, certainly on this show and

some of the other shows that I do.

Um, we have to get into the...

What we call here in the UK, uh, the nitty gritty quite quickly.

Um, otherwise it's just boring for the listener, right?

You've, you've got to, and so what happens is the guest comes on the show and they

come with this sort of understanding, at least the best guests do.

The ones that, that aren't vulnerable, that don't sort of share their story.

Um, They're not, they're not the best guests.

The best guests always come on and they, they get into it pretty quick,

quicker than you would if you were down in the pub, for example, you

know, there'd be a lot of small talk about football or whatever.

Um, you can't do that with a podcast.

You've got to get straight into it.

So the conversations you have are genuinely unbelievable.

When you think about, really, this is the first time, well, this is

the second time we've met, right?

So we talked half an hour for the first time, you shared your story, we're

going to get into it a little bit.

In a space of whatever that is, like 60 minutes to 90 minutes that

we've technically known each other and talked, you get in some pretty,

pretty deep stuff with people.

Um, and they always, always make the best shows.

And so I'm kind of curious.

Um, when you talk about what you use words like vulnerable, which

in my head is very connected.

I think the first time I'd really heard that in the context of

business was the TED talk by Renee Brown, um, uh, which was fantastic.

Um, so you've used words like manicured, getting lost in all of this, you kind of

lost yourself that there needed to be an air, an air, sort of air of vulnerability.

But at the same time you said that process was pretty painful, um, just, just lead

us, give us a snapshot, uh, of the story that, where this was all discovered.

So Thank you.

Thank you.

I have, I think my life has been, in one lens on it, is like a study of identity.

Mm hmm,

and identity has, has, uh, the way that I'm orienting to identity at any given

time has been a, has kind of played a chief role in how life has gone, how

I've showed up, and everything else.

And certainly has a lot to do with, um, with how I've, I've landed at least

for now where I am and, and, uh, um, the vulnerability that I bring, uh,

to, to life and to work and to all the other aspects of, of, of my life.

Um, the first time, I don't think I realized this at the time, but when I

was young, uh, the way that I oriented to identity was I would have this

very clear idea of who I wanted to be.

And as you sort of, uh, uh, alluded to earlier, that was an NBA player.

So I had this vision of future NBA player and that future vision was

so powerful for me that it sort of, uh, compelled me to change whatever

I had to in the present to serve.

That future vision.

I was going to become that future NBA player, right?

So, very much oriented, my identity is very much oriented

towards this future thing.

Um, and I found that that's a really powerful way of

catalyzing, uh, motion for me.

And I think, uh, for, for, uh, in general.

Um, and so I'm pretty much practicing basketball five

hours a day, all this stuff.

Uh, I got, I'm wearing long sleeves today, but I got tattoos because,

uh, you know, if you're gonna go play in the league, that's what you do.

just all these, all these, uh, all these interesting things, um,

that really fit with this idea of this is who I'm going to become.

And, and that lasted as, as long as my temperament would allow it to last.

I ended up, I was a, uh, a cocky little shit and I got in a fight

with the coach when I was, uh, uh, an 18 year old kid and quit the team.

And all of a sudden, uh, this.

This, not only like the investment of 15 years of my life into something

that I was really passionate about, but my identity, who I was, wasn't,

I was no longer allowed to be that because I'd quit the team, right?

And going from very clear, I am going to be this and everything

makes sense to that's gone.

I don't know who I am, was incredibly disorienting.

Um, and the first time I interacted with that feeling of like, um, you know, I

was going this direction, now I'm not, and I don't have a, have a, an answer for

that, uh, I got really angry as a result.

And so, um, that's when I went through a four or five year period

where I was, I, I, I lightly call it when I got a case of the fuck it's.

Um, I just like drank as much as I could, did all the drugs that I could

find and really was pretty convinced that I was going to try to break

through to the other side or die trying and, um, and that was a dark time

yeah, no

me a while to, to, to dig my way out.

Um, but eventually I, I, uh, I dug my way out and, and part

of that was getting sober.

That was, uh, probably the big catalyst to that.

Um, but then even immediately after that.

Uh, identity was the, another big question.

Okay, now I'm dry, right?

I'm not killing myself, but who am I?

And just like the first time I looked around and the thing I saw, um, you

know, the first time it was like NBA players is the coolest thing that I could

be, but now it's just 2000 and 2006.

Uh, so now it was, uh, tech founders.

So, you know, Zuckerberg's doing his thing.

Jack Dorsey's doing his thing.

And I look around and like, that's, you know, everybody will

really admire me if I do that.

hmm, mm

and so, uh, so that's what I did.

So I, I began the process of, of starting companies and I started three of them,

uh, four of them now, but three of them in that sort of phase, um, the first

two were progressively larger learning experiences and then the third one scaled

and the next one was pretty successful.

Um, but that 15 year period as a CEO right there was again, very much in the

sense of like who I am is this future hotshot tech CEO, like unicorn leader.

And, and I need to live into that and, and all of my efforts all the time were

like, how do I, um, how do I, how do I become this as, as best as I can?

And again, catalyzed a hell of a lot of motion, but it leads to this, I

learned this, um, well two things.

One, a feeling of, a pretty strong feeling of imposter syndrome because

you're, you're, um, the expectation of who people think you are and think you

need to be, at least your expectation of that, is really different from who

you think, who you think you are and how you understand yourself to be.

That was my experience.

The other thing is it's really brittle, um, because if anything doesn't go

that way, if, uh, if you quit the basketball team or, uh, in the case of

when I was a, uh, a startup founder, uh, I, uh, went to my board and I was

like, I want to roll up these companies and they were like, that's awesome.

We want to do it.

We want to fund it.

And we want to hire a CEO who's done that.

So again, I was sort of confronted with, oh man.

Now, this image that I have of myself, this, this identity,

I can't do that anymore.

Um, and, and coming from that sort of future oriented place, again, you

know, that identity is gone and, and then the question is, well, now what?

So, um, the second time in my life, uh, and this is, this is, I don't know, five

years ago or so, um, I was confronted with, uh, with, Uh, not, you know, not

knowing who I was and not having a, um, a clear answer for like, I'm Ryan, the

guy who's building this and here's how it's awesome and all that and having this

really polished, like, like podcast intro sort of a, uh, sort of a vibe, right?

And And I think that was, um, the pivotal decision that I made, and certainly one

that I'm glad that I did, was in that second time that I had been confronted

with that liminal space of not having an answer to who I was and what I was

doing, um, first time I reacted to it and got mad, the second time I got curious.

And I remember, um, I remember talking to my wife about it, and I told her at that

time I was going to take a sabbatical.

And she's like...

You can't do that.

You just brought in this new CEO, you're going to get fired.

And I was like, I'm, I'm going to take a sabbatical.

It was supposed to be two months, it ended up being 18 months.

So it was a, longer one.

Um, but when I, when I told her, I was like, I have been.

Running my ass off my whole life, and I've always thought that I was running

after something that's super valuable.

That's going to make me feel amazing when I finally get it.

And I've gotten it so many times.

I've gotten so many gold stars, raised all the money, you know, eventually

sold the company to all this stuff.

And And it still hasn't changed anything, still hasn't changed the way that I

feel, so, and yet here I am, even on, on, like, having just transitioned away

from the CEO role and doing strategy and other things, still running my ass off.

I can't figure out, if I'm not running towards something, the only thing

I can think of is I must be running away from something, and um, so, the

only thing I can think of to do is to stop running and let it catch up.

right,

And that, that was my sabbatical in a nutshell, um, was, was

confronting some stuff around that.

And it was the most challenging thing that I've done, um, along

with getting sober probably.

And uh, and also one of the most remarkable things that I've done,

cause at the end of all of that, despite all sorts of instincts that

had me want to create another company, which is the easy instinct to do, um,

or, or any number of other things.

Um, I allowed myself to get comfortable through practice in just being Ryan and

not having a, a thing that I'm doing, not having a, you know, Ryan, the guy who's

building the next blah, blah, blah, or Ryan, the future of this, but just really

centering and settling into, um, just me.

And that was this crazy, radical notion, uh, and it was incredibly like, you know,

when you're on sabbatical, the first thing everybody asks you is, well, what's next?

What are you doing?

What's, you know, what's coming?

Um, there's all sorts of opportunities to practice just being like, I

don't know, um, I'm working here.

I'm doing some things over here.

I'm really interested in.

I'm interested in leadership development and racial equity work.

And, um, I'm, you know, I'm building things in each of those spaces, but, um,

for the first time, none of it defined me.

And I think that was, that was, uh, um, a pretty critical sort of shift and

in that whole space, uh, in the, the willingness to be Ryan as opposed to Ryan,

the CEO or Ryan, the basketball player, any of that stuff was where, um, where

vulnerability came from because it was in letting go of the person that I wanted

people to think I was, or the person that I wanted to become and just being.

Me, here, who's nervous or scared or happy or excited or whatever, um, being

willing to bring that, um, just opened up everything else that happened since.

So we've continued to build companies, um, continue to support people and

be as useful as I can, but it comes from a really different place now.

That's fascinating.

Uh, and if you don't mind, I'd love to dig into this a little bit.

Um,

Yeah.

you use, you use this phrase, stop running and let it catch up.

Um,

Yep.

and I think intuitively I know what that means, um, but I'm curious,

what did that look like for you?

What, 'cause it's a phrase which I get, and I, I intuitively understand what it

means, but what did stop, stop running?

What, what was that?

What did that look like?

Mm-hmm.

Um, so for me, um, and I think that, that, that I've, I've worked with some people

that have a similar sort of dynamic, but for high achievers, we'll say those people

who are always moving, which of, of which I, I, uh, I've always been one of those.

Um, my experience is that when you stop moving, it can be pretty uncomfortable.

Um, there's reasons that we continue to run.

There's reasons that we continue to create all the time.

Most of the time, those are unexamined reasons.

Um, it's just like, well, I run because I want to make a big impact.

I want to make a dent in the universe, or however we've heard that, right?

But, but, um, for me, for a long time, whenever I would, you know, I

would sit still, I would get antsy.

And I'd start thinking about what's the next thing I'm going

to do, and things like this.

Um, so when it, when it came time to like stop running and let it catch up, a

lot of what I did, I had been meditating for 10 years prior to that a little bit.

Um, but one of the things that I wanted to do really intentionally was to stop

creating, stop all of the motion that I had been engaged in for so long.

Um, you know, both stuff that I felt was really positive and stuff that I

felt was less so, uh, just stop all of the things that gave me a sense of.

Um, the progress and the chase and all that stuff that I had been doing, the

way that I did that was I just happened to have a Zen master that lives like 10

minutes or 10 minutes, like 30 minutes from my house, which didn't realize at

the time, but, but did during that period.

And so I traveled down there and worked with him, um, really got,

uh, really sort of like dove into the, my meditative practice and was,

was practicing for a couple hours a day for, for quite some time.

Um, and what I found was, was when I could still myself enough, the parts of myself

that I, that it was possible for me to, to make still, um, what I would find is

all of the things that were moving behind the scenes that caused me to be in motion.

All this time.

So when I got still, I saw, um, you know, the sort of base belief that I wasn't good

enough and I needed to prove it somehow.

Um, I needed to go out and do the next amazing thing.

Otherwise, you know, otherwise something was like inherently wrong with me.

Um, I saw a lot of discomfort with, uh, with conflict.

I saw a lot of discomfort with, um, you know, my own sort

of, how would I phrase this?

Like there was some tension between.

What I had been told a good leader was, or what I'd read a good

leader was, or all the different inputs that I had, I had taken in.

Um, and what I felt was true for

hmm,

Um, and all of that came up.

So it was like all of these things that were there all the time, but

just, I would just work through them.

I would just bust my ass.

And, and that was my sort of like coping mechanism.

When I stopped moving and sat in place, all that stuff came up and it was just an

opportunity to look at it a different way.

Um, instead of trying to run away from it through achievement or through drugs

or through alcohol or anything else, or exercise even, um, I got a chance to, to,

and really made the conscious decision to just sit with it and just feel it.

Um, and believe it or not, what I found is that if even with a, with

a doozy, like I'm not good enough, like that sort of a, a base level

hmm, mm hmm, mm

Um, when you sit with it and you don't run from it and you really just feel the

texture of that belief, not necessarily in like a moral good bad sort of a way,

but more of a, uh, an aesthetic way,

mm hmm.

Not good enough feels heat in my stomach.

Not good enough feels tightness behind my eyes, and there's a story running

in my head that's really unpleasant.

We can break it down to that level of phenomenology.

Um, it's just, it's sensations and you can be with it just like anything else.

And you can establish a different relationship.

I learned, um, with some of the demons that, that, uh, had been

driving me for a long time.

Um, and I think it's that integration or equilibrium that I was able to

develop with, um, the things that were like frightened me for so long.

Um, that's what I mean by like letting it catch up and seeing where that went.

And is that, um, something then that you did, I mean, you, you talked about

visiting the, you know, the chap down the road, um, but sitting with it and

understanding your relationship with the feelings of, of, um, Of how you

felt in relation to, say, not feeling good enough, you know, the heat in your

stomach, the tension behind your eyes.

Did you work through that by yourself?

Is that something that you got, uh, if you don't mind me asking, you

know, counselling to help you through, um, is that something you did, uh,

sort of debated with your wife?

I, I'm, what, I appreciate this is a bit of a, you know, a, a, a strange, no,

a,

strangely strange.

on.

no, yeah, it's, it's a, it's a journey, man.

It's not, there's not an, there's not an answer to that.

There's so many answers and I just want to pause also and just, just, I don't

think he's probably listening to this, but if Sokuzan is listening to this to

be called the chap down the road, I think it's just the coolest that he would,

sure,

this grumpy old Zen master.

And, uh, and if he heard that, he would be, I think, I think he'd crack up.

Um, so, so he played a role, um, I'm, I, uh, have been an

avid reader my whole life.

So, uh, so all sorts of teachers through, through books, um, there's a, one of

my inspirations to, to get into the work that I'm doing now, uh, is a guy

named Jerry Colonna, who is an executive coach out of, uh, Boulder, I think.

And he wrote a book that, uh, was sort of the right book at the right time.

Um, Michael Singer, um, anyway, a whole bunch of different, uh, different,

uh, uh, inspirations in that way.

But then I also, uh, began working with a coach, um, it was a, a coach named Carl

Bacciolari who, um, was sort of brought this really cool balance of, uh, business

wisdom and Taoism, which was a nice, nice sort of compliment for me at the time.

Um, I had, uh, uh, mentors, um, there's a, uh, Uh, mentor of mine, he had started

a software company and scaled it and it's a, I don't know, a hundred million dollar

software company, something like that.

Um, and he had always been a business mentor, but I knew that he had gone

on a sabbatical just before I did.

And so I was like, I ought to talk to this guy.

And he had a really similar story, very different details.

But the, but the, um, the idea of like, I have Exhausted business success.

And I don't want to do this.

And I don't know what I want to do and how this all like, I don't know

what's next, but this isn't it.

And I'm going to stop and I'm going to see what happens.

Um, so he had just really, uh, he was a really inspiration.

He's an inspiration to me and continues to be.

Um, and then I worked with, uh, I probably worked with four or five therapists at

this point, too, each with its, with their own, um, perspectives, their

own tool sets, uh, and each playing their own role in, in my journey.

Um, and I'm not, you know, I don't know that I have, uh, uh, I'm not advocating

for one direction or, or another, but my experience is that when you, um, when

you're open to it, when you're looking, uh, you tend to find, uh, The right

person for you, and you have a sense, at least I had a sense of like, right

now, this is the right path to go, and I'm gonna explore it, and then at some

point that'll be that, and I'll go to the

mm hmm, yeah.

Give myself the freedom to do that, I think is important.

It's interesting how that works, you know, where, um, I was saying this to

my wife the other day that years ago, uh, when we started having kids, I

realised, Ryan, that I knew nothing.

about first aid, right?

So if something happened to my kids, I was not the man to be able

to deal with that situation, right?

I would,

You get scared of blood too?

I'm not scared of blood.

I just, I just didn't know what I was supposed to do, right?

That's more the, more the issue.

And so I joined the Red Cross.

I joined the British Red Cross.

They had an office on the opposite side of the, the park to where I was.

And one thing led to another and I ended up.

Uh, working on the ambulances for a while with the British Red Cross,

which was all kinds of crazy and all kinds of fun and all kinds of cool.

And so I'd gone from wanting to know a little bit of first aid

to, you know, all, all kinds of crazy stuff that we got up to.

But anyway, I'll say that for another day.

One of the fascinating things to me at the time was,

Crew,

uh, there was this season when I was with the Red Cross where I would

regularly call my wife and say.

Listen babe, I, I'm gonna be late, I'm just waiting for the ambulance,

it's not, I just want you to know it's not me, I'm okay, it's somebody...

You know, else.

So, um, I came across road traffic accidents.

I came across, uh, people that had serious falls.

I mean, just in the, I was, I was cycling my bike down the river and an old lady

had fallen down some steps and cracked her head open and, uh, and it, and

you get involved in these situations and it was, it happened so often.

Uh, it became a sort of standing joke and then one thing led to another and I

eventually left the Red Cross, um, that season of my life, for want of a better

expression, had come to an end and, um, I was sort of, I sort of moved on from that.

What fascinated me was when I stopped doing the Red Cross, when I

stopped doing all the training and the constant assessments for being,

uh, you know, on the ambulance.

I stopped coming across really all these incidents, they just, every now

and again, you know, I see something or I'll get involved in something,

um, so from going from something once a week to something once every

four or five years, it's fascinating.

And so there's this really interesting play at work, which is when, I

don't know how it works, but somehow when you're prepared for something,

when you're open for something.

You sort of, it's sort of, you seem to be positioned in places where that's

actually quite useful, do you know what I mean, and, uh, and it sounds

like when you were letting these things catch up, um, a similar sort of

thing, that some of the books you were reading were the right books at the

right time, because you were in this sort of place to sort of read that,

and it's, that's always intrigued me.

Yeah, you know, it's like when you, when you buy a new car and then you see

that same Volkswagen everywhere, where you never used to see it before, right?

And now it's there.

There's a, um, I think there's a, uh, the term that I've heard used for it

is the reticular activating system.

It's the part of your brain that sort of...

Chooses what to see and what to filter out.

And I think that plays a large role in, in this process.

And it feels, I mean, it's sort of from a subjective perspective, it can

feel really serendipitous, um, when all that stuff is, is, is happening.

So, um, I mean, if you open to that, it, for me, the experience was super joyous.

It was really fun

and Hmm.

funny how those two things go together, uh, you know, um, how is your, if, if

I can delve a little bit into this, I'm, I'm curious, there seems to have

been like a, an, you know, quite an incredible personal journey that,

you know, took a few years for you to go and you're still going on it, you

know, life's still a journey, isn't it?

But it sounds like you're quite a different person.

to the person your wife first married, and I'm kind of intrigued how she's responded

to this whole journey of life for you.

And, um, when, uh, when I work with clients now and anybody going on their

own sort of transformational journey, and I work with quite a few of those

people, oftentimes, Um, founders that are just exited their companies and now are,

are in that sort of liminal space and are figuring out or all sorts of other,

like, um, external circumstances as well.

But personal transformation, uh, I think you're hitting on

something that's really true.

It changes people.

Um, you know, I think, uh, it, it brings people closer to a truth in them, but we

don't start out very close to that truth.

We start out trying to educate.

You know, it's a, to do our best, um, our best job to win the game

of society, however we define that.

If we're a doctor, we win that game.

If we're a lawyer, we win that game, whatever.

Um, and the transformational process is one of coming back to yourself,

that, that you've been this whole time, but you sort of lost your way.

And that occurs like a really big change for people.

Um, and.

It is a huge challenge on relationships.

Um, I've worked with clients where that needed to change relationships.

They needed to, to, um, once they sort of got in touch with themselves,

they had to make some shifts.

Um, in my case, uh, I have a lovely and awesome wife that did some

amazing things along the way and is, um, somehow, uh, gracious enough

and big enough to hold all versions.

Uh, which has just been, I mean, I'm super fortunate that that's the case, but.

I actually met her, Laura, uh, prior to even getting sober.

So we met in college.

I was a, um, you know, this, like this party all the time, you know, doing

all sorts of debauchery all the time kind of guy, um, but very entertaining,

very, very social, uh, and We had been dating, I'm going to say, six

months or so, uh, by the time I got my second DUI and ended up in jail.

Um, and I remember looking at her through the glass and going like, well,

there's no way this goes anywhere, right?

This is a, this is, you know, there's only one, there's only one ending

to this and this relationship.

And that felt really, really bad because I really, really cared for her.

And then, for some reason, and I still don't know why, she decided

she was going to stay with me.

And, um, and...

And grew and changed herself along with me and gave me the space to kind

of go on my own sobriety journey.

Um, so by the time this happened, you know, 10 years, 15 years later, uh, she's

like, well, okay, I've done this before.

Uh, I know what this, what this looks like.

And I don't know, I remember her saying this when I was going through it.

She's like, I have, I mean, I'm scared cause I don't know what's going, what it's

going to look like at the end, but also.

I have no illusions that this is not going to happen.

Mmm.

So it's just a matter of like, it's going to happen.

I'll support you however that works.

And then at the end of it, um, you know, we'll see what we see.

And, um, and as a, I mean, I think that approach worked really well.

Um, and I think we've, we've become closer each step of that

process, the more I've sort of.

I've been willing to be open, be willing to be, um, vulnerable and, and trans,

it's not even really transparent.

It's not, there's, it's not a matter of sharing or not sharing things, but it's

like, um, opening to, to another person, I think the closer that we've gotten.

So, um, for in our case, it's been very much, uh, um, we've been growing together.

Wow.

That's not always the case.

no, no, no, kudos to Laura for doing that because that, um,

like

think that's a her, that's not a me.

yeah, yeah.

It's um, my wife often tells me that I'm not the man that she married.

Um, in a, in a, in a similar sort of way, you know, a

transformational, yeah, yeah, yeah.

Absolutely.

And that's the way it should be.

I mean, I, geez, uh, I was not great.

I mean, I was okay, but I, you know, I, I, I think I'm a better person now.

Um, I'm a, I'm a more aware person now, which is interesting.

And, uh, it fascinates me.

You, you, you use the word identity a lot.

And I think I was listening to a conversation with Kerry Newhoff and

Tim Keller, I was listening to an interview with them and Tim Keller was

talking about how, um, identity was the crisis of this age, you know, um,

in the, in the light of social media.

And I thought it was a fascinating conversation.

And I'm aware that my daughter, who is...

Thanks for

she just started sixth form, uh, beautiful girl sees around three or

four thousand images a day, which are not authentic, which are not

true, all trying to tell her to be something, which I, it's just not her.

And how you, how you deal with that, whether it's in the business environment,

whether that's in social media or whatever that is, how you face up to that,

um, and continue to deal with that, I think is one of the challenges that we.

We all have to deal with, and I think it's probably the challenge

of our time in a lot of ways, um, and so I, it's a fascinating, it's,

are you working with that with her?

Like, what do you do?

My kids are five and seven, so I'm not quite to the Instagram level yet.

it comes down to conversation at the end of the day, it's like, um, I remember,

uh, we had, a few years ago I owned a beauty company, and I sold it two years

ago, exited that business, And we had a salon, we had a beauty salon, and

I remember saying to the therapist, I want you to get every single photograph,

every single image, whether it's on the wall, whether it's in a magazine, whether

it's in some sales list or whatever it is, let's get them all on the table.

other

And I said, I challenged the girls, I said, I want you to take away every

single photo that's been photoshopped

being said,

and doctored in some way, uh, and leave only the authentic photos left.

Well, they, they didn't leave a single image on the table.

Um, and this was really interesting and so I'm like, well, let's throw it all

in the bin because it's not true, is it?

And they're like, well, what are we going to put up there?

What are we going to put out there?

And do you know what we did?

We went and bought, and this is fascinating to go through with your

daughter, we bought, um, a book, a photo book done by Time Magazine.

I think it was by Time.

Cause they do all these sort of photos, or maybe it was National Geographic,

National Geographic, not Time, uh, photos of women from all different

parts of the world, different tribes, different, you know, skin colors,

different dress, everything was different.

Um.

And we just started taking those pictures out of the books and putting those

on the wall and we left those books out rather than the beauty magazines.

And the feedback from clients, we didn't tell them what we were doing, was just,

people were saying, there's just, I don't know, they're just, the salon

just feels lighter somehow, a little bit less oppressive and I wouldn't

change the paint or anything, it was just all we changed was the images.

And so, it's a long answered question, uh, long answer to your question, Ryan.

I It's conversation, it's like, this is what, this is, I think you used

the phrase manicured earlier on, I'm trying to get Zoe to understand that

Instagram is very, very manicured, um, but what does real life look like?

And so, me, when, if I do Instagram, not just doing the manicured stuff, or, um,

you know, showing, yes, we see that photo, but let's look at what they really look

like in that, do you know what I mean?

And, and, and having those conversations, because I think my daughter, She's had

no choice really I suppose, but I think she wants to have them, I think she

wants to, I think she wants somebody and

Yeah.

Yeah.

think, I might get into trouble for saying this but I think actually this

is a significant role of dads is to say to their daughters this is not real, and

actually you as you are is enough, um, and you, and you have to, Protect them.

Protect is a wrong phrase.

I'm gonna get into trouble for some of the words that I'm using because

I've not really thought about how to say this before, but, um, but I think

you have to draw that out of them.

Do you know what I mean?

And nurture them, and maybe nurture is a better word, uh, and have

those conversations with them.

I think that's right, and I don't know who the hell is going to get

you in trouble for saying that.

That seems like that makes all the sense in the world.

Yeah, it's, it's, it's one of those, isn't it?

It's, um, dad's relationships with their daughter.

Do you have a daughter?

two sons.

Two sons.

Very different how you talk to sons.

I mean, in a lot of ways, you know, sons have the same issues, right, around

identity, but I think their identity, I have two sons, one who is 22, one who is

19, both who are now men that I'm, I mean, I've always been proud of them, but I'm

very proud of the men that they've become.

Um, and my relationship with my sons is very different to the

relationship with my daughter.

Um, because the relationship with my son is.

I show them the same photos and go, you can never actually be the guy that

creates that photo because chances are it was created by a man if we're real.

Do you know what I mean?

And, and so, yeah, fascinating.

The whole thing is fascinating.

Anyway,

it's uh, oh, go ahead,

no, no, you crack on.

yeah, I was gonna, I was gonna add one other sort of element that I

see to this, uh, or I'm wondering, it seems like there's There's maybe

two levels of growth that happen, like there's the level of, or maybe

increased understanding or awareness.

The first level I think you're talking about, which is just that the things

that we're comparing ourselves to and the things, particularly young people, that

they are fed all the time aren't real.

They're manicured, they're steered, they oftentimes have a purpose, they

oftentimes have like an agenda that comes with them and, um, You know, uh,

uh, learning to see through that and let go of the things that are, are not

real and just dwell in what's real.

I think that's, that's, that's a critical part and I'm, I'm, I don't know if I

can say I'm looking forward to the point when my boys get there, but I'm, I'm

You know, definitely aware of it and, um, and, uh, we'll take that seriously.

I think the, the second part, the second sort of, uh, awareness or,

or, or unlearning almost is this process of, it's not only like, what

are we comparing ourselves to, but it's the idea of comparing ourselves.

It's the idea of...

yeah,

My worth and my value is in is in comparison to all these people and I

am here versus here and Whether it's real or not and I think the there's

a later stage of Conversation, you know with a young person which is

just around you're owning your own or you're running your own rights.

This

yeah,

Um, there is no real comparison, uh, whether it's, you know, whether it's,

uh, Photoshopped or if it's just, uh, you know, uh, a picture taken.

So, um, I think that's just such a fascinating journey and I have so

much more, um, Dadding to do that I'm so excited about, but it's cool

to hear from, from folks who have, uh, who've, who've gone through

the, you know, the dad journey for, for decades longer than I have.

So nice work.

Oh, and it's honestly one of the most rewarding things, best decisions I've

ever made in life, get married and have kids, right, and um, I've been married

25 years, my kids are just awesome, we all get on super well, and I'm very,

very grateful, and you're right, this whole comparison thing, comparison

is a joy thief, is what I say in the

I've heard that.

and it's How do you deal with a world?

How do you be a man in a world dealing with, dealing with the fact

that every way you turn, they're going to compare you to something?

, right?

So you're gonna get compared to your classmates.

That's how the grading system at school works, right?

You're gonna get compared to the guy on the running track because he

finished first, you, then it finished.

Third you mean and all.

So in a world which constantly grade you in a world that wants to constantly

compare you to something to judge your worth, because we don't have a

better way of doing it, um, salaries, you know how much we get paid, right?

It's a men talk about their salaries in the pub, not because.

They're grateful, necessarily, but because they want to compare their

salary to their mate's salary.

It's crazy, you know what I mean?

And it's fascinating, isn't it?

And how do you, how do you be a man in a world that wants to constantly

compare you and not get bogged down in that comparison in your own mind?

Because everything's telling you you're not good enough.

And how do you deal with that?

And again, that comes down to this whole conversation around identity, doesn't it?

Mm hmm.

Yeah, I think it's, um, what's, what's, uh, there's this wonderful book, uh,

and I don't remember who wrote it, but it's called, um, it's a Japanese

author and, uh, the, it's sort of a, an analysis of Alfred Adler's work.

Alfred Adler was a psychologist back in the turn of the 19th century with,

um, Jung and, and Freud and Adler.

Adler's like the, the third one.

Um, and the book is called The Freedom to be Disliked.

And I think that's, to me, is, um, kind of hints at the essence of what it means

to not be compared or to go the opposite direction is like you, um, in order

to be free of that process, it really does take A willingness to be disliked,

uh, by somebody, um, either that, if you're not willing to be disliked,

then you're playing the game to win somebody's game that they've created.

Like, whether that's the game of, you know, a race, or that's the game of

popularity, or it's the game of, you know, you're, you're going to the bar and

who's got the biggest whatever, right?

Um, and all of these games already exist.

And so if you, if you want freedom from that to run your

own race, it, it requires.

It requires something.

It's not an easy thing.

It requires being willing to be disliked.

and I think that's, uh, that's not to be underestimated and it takes

a certain amount of something.

Maturity in my case, um, but, but, you know, maybe moxie, uh, for, for people

to, um, to be willing to step off.

moxie is a great word, moxie is a great word.

I

love

for me to put it on myself, so I said moxie for someone else,

but yeah, maybe moxie, who knows.

moxie is a great word, it's interesting isn't it, because as you're talking

I'm reminded of the word grace, you know, the grace, the whole concept of

grace, the unmerited, the undeserved favour, for me is perhaps the most

freeing revelation of life, you know, it's not about what you do or don't do.

Uh, in a lot of ways and, and.

And once you, it's a lesson, I was, I was writing about this this morning,

it's a lesson that I just have to keep continually learning, uh, because you,

you quite quickly fall back into this trap of, I need to earn, I need to earn,

I need to do something, I need to do something, I need to be, be, be, be.

Anna, Sam Guth,

And it's, um, the, the, what, um, my good friend, uh, Cesar

Kalinowski calls the do to be lie.

I've got to do to be, uh, rather than just be, and then do.

You know, it's, uh, it's, we've got it screwed up somehow.

Fascinating.

Fascinating.

I think

Right,

and

all the ways that matter, in all the ways that matter, I think,

um, grace is much more powerful than anything we can do anyway.

So we gotta learn that.

And you gotta, you gotta be reminded.

'cause it's easy to forget.

'cause we don't live in a grace world.

We live in a doing world.

Um, but every once in a while you get that glimpse.

You do.

And it's wonderful.

And it's beautiful.

And it's lovely.

And I wish I could do it more often.

And again, hence my language, I wish I could do it more often.

So you catch yourself in these situations, don't you?

Uh, which is quite fascinating.

Um, but Ryan, listen, I'm aware of time.

I'm, I'm, I'm taking up a lot of your time here.

Um, so I'm gonna, I'm gonna do, we're going to close with the question

box because it would be rude not to.

Um, and

Let's do it.

Yeah.

We can't miss that.

Yeah, yeah,

Can't miss that.

So I'm going to flick through the questions.

You're going to tell me when to stop.

And that's the question we're going to ask.

Stop.

Okay.

This is, you stopped here.

I just want to point that

Yep.

Yep.

Are they all the same question, by the way?

Are

Uh, no, no, no, they're all very different.

Okay.

Yeah, sleight of hand going on behind, no, no, not at all.

Is there anything you regret doing, or not doing, should I say, due to fear?

Yeah.

Mmm.

No.

Um, if the question was, is there anything I would do differently were I not scared?

Sure.

Um, but I don't really, I find that, like, if, it's hard for me to regret something

because all of this made me who I am and got me where I am, so it's hard for me

to think, like, I want to change this.

Um, but would I do things differently next time?

For sure.

I think one thing that, the first thing that pops to mind is, um, uh, I

would, um, I would own my power in the boardroom much more than, than I did.

And I think that, Um, part and parcel to that process of wanting to be the perfect

CEO for these people and these people and these people was being really clued into

what my board members thought of me and trying to, trying to sort of serve that.

Um, and that's, in my opinion and experience, not a great place

for the CEO to be optimizing.

Um, CEO needs to optimize for, for building the best company that they can.

And sometimes the board is, is, you know, uh, a good check for that.

And sometimes.

It could be all sorts of different things, but what they're not is...

The market.

Um, and so, uh, so I think that some of my fear, uh, showed up for

sure in the boardroom around as I unpacked it around some dad stuff.

Um, you know, uh, my parents got divorced and my dad left when I was, uh, 16.

Um, he didn't leave leave, but he kind of like slowly worked

his way out of the picture.

Um, and when I, you know, 20 years later, I'm in the boardroom and I

got this really alpha angry investor who's doing his alpha angry thing.

It's not a big leap to see my dad within that, um, and, and I found myself

wanting to please this guy, wanting to like, have the right answer, and, um,

and absolutely would handle it totally differently now, but, um, but, uh, it's

an interesting, it's an interesting thing to explore the way that fear has,

Shifted outcomes, uh, in my life and, um, and like any, any sort of fear, like

when you're aware of it, then you have a choice, um, but before you're aware of it,

you're just kind of a puppet on a string.

yeah, yeah.

No,

How about, how about, hold on, no, hold on a second.

How about you?

Now, I was, I was thinking as, as, as I read the question, I thought,

how would I answer this question?

And I think...

Um, again, I think it defends, how do you define your relationship with regret?

Because it's, you know, I, I don't, I don't wish to be anywhere different

than where I am today in a lot of ways.

Um,

I

at Like You, I would have, the thing which I think fear has stopped me doing,

which I probably should have done sooner and more often was confront things that

needed to be confronting, confronted rather than just letting them drift past.

And that came.

down to something in me,

Hand,

stopping me doing that, which in reality I should have done.

And I think I'm, I'm hoping that I'm getting better at

that, um, as I'm getting older.

Um, but I can see it in my kids sometimes.

You can see them not want, they're not saying something or

they're not confronting something.

Uh, and to encourage them to go, no, come on, let, do you know what I mean?

Let's bring that out, I think would be.

Um, not in every situation, obviously, but I think I, I, if I could go back and

do things differently, a lot of it would be, I would have spoken up at this point.

I find that, um, I work with a lot of men and I find that we all have

interesting relationships with anger.

Um, and, and anger is this emotion that, that wants us to stop something.

It's like this needs to end, whatever this is.

Um, but it's never as quite as simple as that, or at least it takes a lot

of work for it to be that simple.

So I empathize.

Yeah, yeah.

Ryan, listen, I feel like we could talk for hours, man.

We should go down the

This was fun.

I enjoyed it.

Yeah, yeah, I

enjoyed this.

It was great,

it was great.

If people want to reach out to you, if they want to connect with you, um,

maybe got some questions for you, want to find out more about what you're doing

with the company and all that sort of stuff, what's the best way to do that?

Yeah.

Easiest way is on our website.

It's leadinsideout.io, l e a d, inside out.

I'll spell out io.

Um, and then you can subscribe to our newsletter.

That's probably the easiest way to stay in touch.

And, um, we publish, or I publish, I, I do all the writing, uh, uh, once every

two weeks and anytime anybody responds, it gives me an opportunity to like,

Dive into the discussion with them.

So, um, I, I'd love to hear from people and, uh, we can talk

philosophy, we can talk leadership, we can talk vulnerability, whatever

it is that the, um, you know, that, uh, that's the, the topic du jour.

Uh, it's a, a cool mechanism for that.

I love that.

The topic du jour.

Very good.

Throw in a bit of French at the end.

Why not?

Uh...

Well, I was looking for what's the French word for weak, but

I don't know what that word is.

So, okay.

Yeah.

Fair enough.

Fair enough.

Absolutely, we will of course link to Ryan's info in the show notes

which you can get along for free with the transcript at pushtobemore.

com and they'll be coming to your inbox if you sign up to the newsletter.

Well Ryan, listen, so many good things there, I really enjoyed the conversation,

genuinely, you don't get to talk like that so, that often and it's, it's,

it's really enjoyable, thoroughly.

Thoroughly enjoyable.

Um, so yes, thank you.

Thanks for coming on the show, man.

Really appreciate it.

Thanks, Matt.

Good to be with

Awesome.

Well, a huge thanks for, uh, Ryan coming on the show.

Also, again, a huge thanks for the show sponsor, aurion Media.

For all you change makers out there contemplating

podcasting as your new vehicle.

Maybe you can have some great conversations just like this

one that I had with Ryan.

Check out orian media.com.

Now remember, keep pushing, uh, and don't forget to follow the show

wherever you get your podcast from because we've got some more seriously

amazing conversations lined up.

And I don't want you to miss any of them.

And in case no one has told you yet today, let me be the first.

You are awesome.

Yes, you are.

Created awesome.

It's just a burden you have to bear.

Ryan has to bear it, I've got to bear it, you've got to bear it as well.

Now, Push To Be More is brought to life by Aurean Media.

All the information's on the website.

Big shout out to the team that makes this show possible, Sadaf Beynon

and Tanya Hutsuliak, and also thanks Josh for the incredible theme.

Music.

That's it from me.

That's it from Ryan.

Thank you so much for joining us.

Have a fantastic week wherever you are in the world.

I'll see you next time.

Bye for now.