The conversation highlights how successful founders build systems to connect teams and eliminate inefficiencies, yet often struggle with fragmented wealth management. Creative Planning addresses this by unifying tax, estate, and investment expertise under one integrated team. Similarly, Pega merges AI power with enterprise control to help businesses scale confidently. Rich Roll shares his journey from law to sobriety and a rural life in Hawaii, which led to creating a podcast that prioritizes authenticity over algorithms. His network stands out by using long-term, relationship-driven 360 brand partnerships—focused on mutual value rather than transactional CPMs—ensuring deeper audience trust and loyalty. The emphasis is on integrity: living in alignment with one’s values, being emotionally present, and resisting the pressure of algorithmic content. Ultimately, the narrative underscores that sustainable success comes not from chasing scale or virality, but from authenticity, personal growth, and building meaningful, trustworthy connections across business and personal life.
The very best founders I know are brilliant at building systems.
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A tax accountant here and a state attorney there, a wealth manager who doesn't talk to
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Learn more at creativeplanning.com slash masters of scale.
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I'm excited to talk to you.
I think this is going to be a little bit of a different kind of conversation than I'm
used to having.
The idea of somebody starting their own business was like a foreign language.
It's been really an amazing experience and a crash course in entrepreneurship.
To garner people's attention, you're best served by trafficking and contrarianism and
platforming people with maybe not so great ideas.
As somebody who is trying to operate from a place of integrity, it creates a conundrum.
What happened in your life that you found yourself on that farm in Hawaii?
What made you think about putting a first podcast out?
A lot happened.
Welcome to Masters of Scale.
I'm Jeff Berman, your host, and I am sitting in the Los Angeles area in the iconic studios
of the iconic Rich Roll.
Rich, welcome to Masters of Scale.
Thank you for having me, Jeff.
This has been a long time in the making, and I'm excited to talk to you.
I think this is going to be a little bit of a different.
It's a different kind of conversation than I'm used to having when I guest on podcasts.
Why is it going to be different?
Well, most of my appearances tend to be in the wellness arena, by and large.
I mean, it's called Masters of Scale.
It's a business podcast.
It might be the first quote-unquote business podcast that I've ever been on, so I'm curious
to hear what you're going to ask me.
Let's start with this.
When you started, could you have imagined getting to 1,000 episodes?
No way.
When I started, it was late 2012, and I still didn't know anybody personally other than
myself who was a listener of podcasts, and I would create these playlists because I would
go out all day on my bike, and it became like this parasocial friendship that I began to
develop with certain podcast hosts, and I had been so positively impacted by what I
had experienced.
Back then, it was. It was a completely different thing.
It was almost embarrassing to say you had a podcast, but when I figured out how to get
a show up on iTunes and record an episode, I was doing it for fun.
My wife and I, we were living at that time on an organic farm on the north shore of Kauai
in the Hawaiian Islands, and I was starting to get island fever, and I wanted a creative
project, and it was just a fun thing to try, not knowing whether I would ever publish
a second episode.
It was really just a fun thing to try, try out.
We're sitting here in a gorgeous studio complex.
You've got staff, you've got infrastructure, and you're building out a network, which I
want to get into.
What are the biggest differences between those early days and now for you when you sit in
the host chair and you engage these conversations?
The intention remains the same, sitting across from somebody who inspires me in any number
of different ways.
And trying to engage in a conversation with them where I am creating an environment to
get the best out of that person.
I'm not a journalist.
I'm not here to challenge people necessarily.
I'm here to highlight the people that I think are worthy of attention.
And that has been, from day one, consistent through all of the 1,000 episodes.
I have a lot of affection for those early days where the stakes were very low.
And it could be very loose and free and fun.
I am a grateful beneficiary of the fact that this medium has become so mainstream and so
popular.
Today, because our information and entertainment landscape is so algorithmically driven, if
you want to garner people's attention, you're best served by trafficking in contrarianism
and extremism.
You can't do anything about it unless you have the courage to try to do it.
And that's why I'm here to talk to you today to talk about some of the things that we've
learned in the last few years that we've been able to do in the last couple of years.
I'm here to talk about some of the things that we've learned in the last couple of years
that we've been able to do in the last couple of years.
And I'm here to talk about a lot of the things that we've learned in the last couple of years
that we've been able to do in the last couple of years that we've been able to do in the last
couple of years, and I'm here to talk about some of the things that we've learned in
the last couple of years that we've been able to do in the last couple of years that we've
been able to do in the last couple of years.
How are you balancing maintaining your integrity while differentiating your episode from all
the others and not chasing the algorithm and the outrage machine for the clips?
Yeah, I try not to think about the algorithm at all.
I know a lot of people who reverse engineer their podcasts and their questions are very
specific to elicit a response so they can create a clip that will go viral.
I don't think it serves the show or the audience for me to think that way, but that means I
have to be.
I'm at peace with the fact that I'm not creating something that is going to necessarily travel
as far as it could if I would make those decisions.
I think that every host brings something different, and I think my strength is trying to connect
with the guest on an emotional level.
I do a lot of preparation.
I go into every interview very prepared.
But like an athlete, like, you then set the preparation aside and you have to be present
for the experience, because if you're caught up in your head, then you're not actually
going to be able to perform.
So I try to engage it more like a dinner party conversation.
You don't prepare for a dinner party.
I don't know.
Maybe some people do.
Maybe some people who listen to Masters of Scale think that way.
I don't think that way.
I try to be as present as possible, and I have in my mind a direction of where I want
to take it and things that I want to know about, but I also have to let go and allow
it to be what it wants to be.
Like I'm trying to create an environment, an intimate environment where people drop
their guard and feel comfortable sharing.
And I can't expect them to open up and be vulnerable with me if I am not willing to
do that myself.
So I try to lead with some of that to create that environment.
If we go backwards to somewhere between episodes one and 1,000, was there a moment,
like an inflection point, where a guest came on the show and they had the opportunity to
add that transformational experience, able to use it to launch forward, where something
clicked for you and you said, "Oh, this is different.
This is going to work in a different way than I ever imagined"?
Yeah.
I never would have imagined that would be a plausible trajectory for anybody, but I've
had that experience multiple times.
I mean, I was the first person to have David Goggins on a podcast, and maybe that was the
first kind of truly viral experience that I had.
It was pretty early on, as I recall.
David is somebody that I had known.
I had known not directly but indirectly because of my involvement in the ultra-endurance community.
Like everybody in the ultra-running community knew who David was long before everybody else
knew who David was.
I had been chasing him to come on the podcast for quite a while.
He wasn't interested, and then eventually he was.
And he happened to be in LA, and I went to his hotel, and we sat on the floor of this
hotel room.
This was before video, you know, and recorded this audio conversation.
It went nuts.
Not that I'm taking responsibility for his trajectory or his career in any way.
He's a very gifted orator and obviously an extremely inspirational figure.
But I'm proud of the fact that, like, I found him first, kind of, you know?
But then there's also people who are complete unknowns.
I found a guy called Josh Lajani who was living in the rural bayou of southern Louisiana with
a very heavy Cajun drawl who had been extremely obese.
And had come from, you know, a community of people that didn't have a relationship with
eating healthy.
Beautiful people, but just disconnected from, you know, the kind of things that I think
about and talk about.
And he took it upon himself to figure out how to lose the weight and reinvented his
life and became a runner.
And like, he's so endearing.
And that episode really made an impact on the audience that then made an impact on him.
And he would go on to be on the cover of, like, World of Warcraft.
Yeah.
You know, like, Runner's World magazine and, like, he's done all these cool and interesting
things since.
And so those experiences mean the most to me.
I mean, it's super fun to go to Arnold Schwarzenegger's office and have him pull out the Excalibur
sword and, like, I mean, it's a life highlight.
Like, who gets to do that?
that. But when people ask me, like, who's your favorite guest? I don't really have a good answer.
We were joking before we turned the microphones on. You said perhaps it's masters of modest scale.
Yeah. And at the same time, you've built quite a show with quite a following and, you know,
super well monetized. And to your point, the space has evolved dramatically. And at the same time,
you're building more. You're building out a network. Why?
Good question. I mean, first, I would say that
I've never considered myself a business person or an entrepreneur. I was raised in a very
traditional family in Washington, D.C. I was raised to be a safety seeker, you know, to kind
of pick the traditional career path. So foreign that I didn't know what it was. I didn't know what it was. When I went to Stanford, this is, you know, the beginning of like this massive tech boom. I was
completely oblivious to what was going on. Everyone was taking computer science classes and I was
reading literature and completely disinterested. I didn't set out to be an entrepreneur or a
business person. The idea for the network grew out of noticing there were a lot of really good
voices out there that weren't operating their podcast optimally.
And weren't being remunerated in a way that I thought was fair. And since I'd been in this for
a long time and made all the mistakes and had been at this network for a while and that network for a
while and had bad experiences at all of them, had decided we're going to be independent. And over
many years, we built up a team with infrastructure where we were able to handle brand relationships
in a really favorable way. But the infrastructure was such that we were in a position to be able to
scale it. And I would get calls from podcasters who'd been doing it for a while and had built up
significant audiences, but they were just baffled about how to monetize their show
because the options were either, well, I negotiate my own deals or I'm going to have to hire somebody
and then manage a business. But the podcast is one thing of many that they're doing.
They don't want to run a small business. So the only option left was to sign up at one of these
networks.
Where they're a line item on a spreadsheet and they're going to get lousy CPMs and they're going
to have to do ad reads for companies they don't believe in. And they're not going to have very
much agency over the kind of brand landscape that they're dealing with. None of those were good
options. We'd figured out a different way to go to CMOs directly and work out complex annual deals.
And we had been really successful at that. So my idea was, let's make this available
to. Yeah, that's a great idea.
Let's make this available to a few select voices that I think are worthy of this offering because
they're trying to put something out there and we're in a position to be able to not only help
them, but help them get paid what I think they should be getting paid. And that's how it began.
And it's been really an amazing experience and a crash course in entrepreneurship. I still
am not involved in the super day-to-day. I'm more like the person who helps find the right
podcasters to bring into the network.
And you're sitting in this studio that we constructed, 10,000 square foot studio. There's a 60-seat movie
theater. We have six studios here. And we work with podcasters that aren't just in Los Angeles. They're
all over the place. All of our hosts are people who I share a sensibility with. They're doing
something different than me, but I think complimentary. And they're trying to do it against
the incentives of the algorithm. And we're trying to find a way to reward them for that rather than
them being punished for that.
There must be thousands, if not millions, of podcasters who would want to be part of
your network. You've got 10 or so. How do you decide, how can you tell when someone
is not just the right talent, but it's the right format for the network?
I would say we're still figuring that out. Intuitively, I know if somebody's going
to be a fit. I think it's about finding the right person who understands the value proposition
first and foremost. And those tend to be people who have been podcasting for a while. So they've
had the negative experiences or they had the frustrations of trying to do it on their own.
And they're the ones who are so grateful to have the support. And they understand the
work behind the scenes that goes into trying to make sure that all of these pieces fit.
When you have somebody who's new, sometimes there's expectations and entitlements that
are out of balance with reality.
So we've had some fits and starts that haven't worked out and we've learned along the way.
So we're not in a hurry. We're not trying to enlist hundreds of hosts. We're trying
to be very boutique and hands-on right now. But we just made a big hire. And this year,
we are going to start trying to scale up a little bit more.
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Hey, listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may
be missing half the show because every Friday we release a second Rapid Response exclusively
in the Rapid Response feed.
The guests and topics are just as compelling and timely, from Ford CEO to NASA's administrator,
to the lessons learned.
Lessons from the Devil Wears Prada.
It takes about 10 seconds to find.
Just search Rapid Response wherever you listen to podcasts and hit follow to make sure you
never miss an episode.
I hope to see you there.
Humans will never be more intelligent than AI.
There's going to be two types of companies.
Those are great at AI and those that went out of business because they weren't.
How do we build a future that is human-centered?
I'm Rana El-Khayoubi.
And on my podcast, Pioneers of AI, we answer that question and so many more.
As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works
for everyone.
Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes
of the AI that's transforming our lives.
Find Pioneers of AI wherever you tune in.
It strikes me, listening to you talk about this, Rich, that you're a pioneer.
You're taking multiple approaches that run very much counter to the moment.
You're not chasing the algorithm.
You are really producing an integrity.
You're not chasing scale for the sake of scale.
You're being very intentional about who you bring onto the network, which, what shows.
So much of media broadly and podcasting specifically is driven by CPM, cost per thousand impressions.
It's really transactional with maybe month to month or quarter to quarter.
You're doing year-long sponsorship deals or multi-year sponsorship deals.
More in the vein of the NFL or the NBA than how media is typically bought and sold.
What is it about you that helps you see how to do things different from the way the rest
of the industry seems to be going?
Well, first of all, I want to make sure everybody understands it's not just me.
I have partners in this business who understand business better than me.
One of those partners is Jonathan Retzek, who runs RXR Sports in New York City.
Everything change media is basically a joint venture with RXR.
I was represented by them as a client and they would handle my speaking engagements
and brand relationships outside of the podcast.
Then they took on handling the podcast.
So they come from a sports management perspective, not an advertising perspective.
And those things are very different.
And so together, we have come up with some interesting. Interesting and innovative ways to work with brands that are very different from the typical
way it's done in podcasting.
To your point, CPM, size of audience, like, okay, you have this many people in your audience.
That means we'll give you this CPM and you'll get paid that.
And it is extremely transactional.
You just do the read and you move on and you never think about it again.
What happens is there isn't brand fit with the host often.
And so a lot of that direct marketing doesn't work.
Which means there's a lot of churn, the advertisers back out.
And then the show has to always be like onboarding new and new advertisers because the life cycle
is very short.
What we've done is much more like how a manager or an agent would think about representation
for a professional athlete.
Sure, we do some ads, it's just the ad rate.
That's fine.
But many of our partnerships are what we call 360 deals.
That's what we're doing.
The podcast ad buy is just one portion of a larger deal, more like an ambassador deal.
deal. So for example, I have a few brand partnerships where they agree that they're
going to run this many ads over the course of a year on the show, but also I'm committed to doing
this many travel days for them and appearances and speaking fees and events, et cetera,
or photo shoots or whatnot. And those are exclusive categories. So if I'm representing
one brand in that category, I can't represent, you know, I can't do anything with a competitor
brand. So it comes with a larger degree of investment of time. But what happens is that
you end up with a real relationship that's meaningful. The audience knows it's meaningful
and it converts much more significantly for the brand. Like our philosophy and our approach
is to always be thinking ahead around what the brand needs. I think there's a lot of
creators in the digital space and podcasters.
Who have a sense of entitlement. Like my audience is this size. You should pay me this much money.
Instead, we're like, how can we help this brand? Like, what is the problem that this brand is
having that we can solve? And trying to solve it in advance of them realizing they even have it,
because that way you become an indispensable brand partner. There's no churn. And the
relationship, it's a two-way street. And I think too many creators in the digital space don't
respect that.
Or don't think about that. They're just thinking about what is this brand going to give me
where it should be the other way around. They should be thinking about
how they're uniquely positioned to serve that brand.
I appreciate that your legion of fans are probably pretty familiar with your personal story.
I'd like to just spend a minute on how we ended up here. You and I both went to law school. I'm
barely still a lawyer. You're not practicing. What happened in your life that you found yourself on
that farm in Hawaii thinking about?
Putting a first podcast up?
A lot happened. I was raised pretty traditionally in a very education-first,
achievement-oriented household. And so I was sort of indoctrinated into
this philosophy of life that happiness is a product of climbing the corporate ladder and
crafting a safe and secure career for yourself where you were well-paid and you could be
a respected member of society. So I was pretty good at playing that game. But things started to
crack pretty early in that I developed an affinity for alcohol that took me down some dark alleyways
and was essentially a functioning alcoholic for maybe 10 years and a really bad alcoholic for
five years.
Ultimately, I got sober at 31. But it really broke me. I ended up in a treatment center in Oregon
where I spent 100 days and was introduced to new tools for living. And I think that was the first
time that I began to question what I was doing with my life because I never really had before.
I was just on the track, you know?
How did you end up there? How did you end up in the business?
I started drinking in college, and it was a pretty, you know, party permissive environment,
work hard, play hard. But from the get-go, it was pretty noticeable that I had a different
relationship with alcohol than everyone else. Like, I was the last guy to leave the party.
If the keg was tapped out, I was the guy looking for the half empties.
I was the guy who ended up doing something stupid that everyone wanted to joke about the next day.
And that's all fun and games when you're 21 years old.
Then I moved to New York City, and I was learning how to become a professional alcoholic there,
because that is the best place to do that. And I had a great time. Like, I was somebody who
was living my life in dissonance with my spirit, but I was unaware of that. I was just going along
my way, but something was wrong, you know? And that relationship with alcohol,
continued to deepen and worsen. And the consequences for my behavior started to get
more and more significant, to the point where I was living a double life,
thinking no one knew what I was doing. But of course, they do. I ended up getting in trouble
with the law. I ended up, you know, having difficulty holding down a job. I got two DUIs
in a period of about six or eight weeks. Shortly after I moved to Los Angeles, I was facing jail
time.
And I was on the precipice of getting fired from my law firm job. And my parents finally said,
we can't talk to you anymore. Like, we're here for you if and when you're ready to get help,
but you have a big problem. And we're not available to be, like, codependent in this
situation any longer. I didn't have one singular rock-bottom moment, but I did have a marriage that
went sideways and ended on the hook. And I was like, I don't know what to do. I don't know what
to do. Honeymoon. Like, I had a series of, like, you know, pretty traumatic events for me, you know,
in my privileged, privileged life that ultimately made me realize, like, I can't keep living this
way, but I don't know how to live. And finally was so broken that I was willing to raise my hand
and ask for help. And that's how I ended up in a treatment center.
What happened in the 100 days there?
Well, the first thing that happened was that I was honest about what I was doing
for the first time with someone else. I started sharing stories and things that I was doing.
And I remember a counselor, my counselor pulled me aside and said, you know, you, like, you have
a case of alcoholism that we typically only see in veteran drink, like people who are in their 60s
who've been doing this for a long time. And I was 31 at the time. And he said, people like you die.
Don't get it. It's not going to work out for you. And I was able to hear that. And, you know, in my
mind, I was doing a spin dry. Like, I was, you know, yeah, this was bad, but like, I got things
to do. I got to get back to my law firm job. But when they said you should stick around, I was like,
I'll do it. I never want to come back here again. Like, I have an opportunity to completely wipe the slate
clean and figure some things out about myself, uh, so that I don't have to come back here again.
And it was the recognition that my best thinking, like I'm thinking I'm the smart guy, you know,
I've got in all these schools, I can do all these things. My best thinking landed me in what is
ostensibly, you know, an asylum for the temporary temporarily is insane, you know, and, and that was
very humbling, you know, so I got humbled and I was able to not only, you know, I was able to
not only ask for help, but, but receive it. Interestingly, as a lawyer, maybe you'll be
interested in this. You might want to cut it out because it's kind of an aside, but I don't think
I've ever told this story on a podcast. Exclusive, exclusive first, first time I'm telling this.
Before I went to that treatment center, I had been looking for another job and I'd interviewed
at a couple of law firms and Akin Gump was opening an office in Los Angeles. And I interviewed with
Akin Gump and they gave me an offer. And then I went to, I went to rehab after they gave me the
offer and I had told him that I was going to go there. So I'm in treatment, you know, I'd been
there like long enough that I had a clear mind. And I said to my counselor, I was like, listen,
you know, I got, I got this problem. Like I, I, I got a job offer from this other law firm and I
told them that I was going, they don't know that I'm in this treatment center. Like what should I do?
And they said, well, you got to call and tell them, you know? And so that was just terrifying.
Like, of course they're going to rescind the job offer. So I had the counselor sit with me while I
picked up the phone and like called them and I said, I know you offered me this job, but here's
the situation. And, uh, and the guy, it was David Allen, a lawyer named David Allen. He goes, uh,
I'm going to have to get back to you. I said, okay. They get back to me and miraculously they're like,
you still have a job here. And I was like, wow. Okay. But we're assigning you to this partner
who's also in the program. And so I did a call with him and then they said, well, we need you
to get working on this case right now. We know you're in treatment, but we need to, we're going
to ship you all these files and these documents, you know, and you got to start working. We need
you to get going on this. And my counselor was like, no way. This is not part of the protocol.
And so I had to call them and say, I'm sorry, but I can't, I can't do that. Um, I've got to get this
sobriety thing sorted out. And so the job went away then, but it was a sliding door moment.
You know, I could have ended up as a lawyer. I was in DC recently and I was riding a bike around
and I rode by the Aiken Gump office and I was like, oh my God, like I could have been like
living a completely different life. But I was introduced to these new tools for living and
these spiritual principles. And, uh, I returned to Los Angeles and just, you know, I was like,
I just made sobriety my number one priority.
I returned to the law firm
where I was working, but really my job was creating a solid foundation of sobriety. And
I immersed myself in the recovery community of Los Angeles. I'm struck by how out of integrity
you were at the time and how much integrity is central to your life and your work now.
How did you continue on the journey to integrity and leave the law and end up on that organic farm
in Hawaii? It took a very long time. I think if you Google me, it might sound like I got sober
and then I started running ultra marathons and I had a podcast. It was not like that at all.
I went back and worked at that law firm. I committed myself to, I knew I couldn't stay
there. I knew emerging from treatment, I knew like this law firm life is not for me. I've been
jamming a square peg into a round hole forever. I don't even know who I am. I've just been living
my life reactively based upon appropriate.
And I need to figure out who I am, who I want to be, what's important to me. These were questions
I never asked myself until I got sober. And I didn't have immediate solutions to those programs
and I needed to pay the bills. So I stayed at this law firm for a while. Ultimately, I left
because I just couldn't, I was like, I couldn't even type a confirmation letter anymore. Like
some might say it was burnout, but I think it was really just, I'm so out of integrity being here.
Not that I'm not a law firm, but I'm so out of integrity being here. I'm so out of integrity
being here. And I said, it's, there's anything wrong with being a lawyer in a law firm. It just,
it wasn't, it wasn't what I was supposed to be doing. And I knew that to my core.
I was on the precipice of turning 40 and I had a health scare and that kind of collided with
this existential crisis that I was having. And I had an experience not unlike hitting bottom
with alcoholism where I realized I needed to make some lifestyle changes. And that really
kind of accelerated the trajectory of, of rethinking my relationship with,
with career and profession.
As I understand it, you committed to an Ultraman competition before you started training. Do I
have that right?
Not quite that. Yeah. I mean, I, I had started exercising again because I changed my diet and
I felt revitalized. You know, I'd been basically eating fast food and Chinese food in the law firm
and had gained a bunch of weight. I started taking care of myself and I had this resurgence of energy
and, you know, I went back to the pool and my wife got me a bike for my birthday and I started a
little bit of running and, you know, I'm 40 now. So what do you do when you're 40? You're like,
I'm going to do an Ironman. You know, this is like the most trite, you know, kind of cliche
thing possible. But I was enjoying just feeling connected to my body again. I had been a swimmer
at Stanford. I, you know, I'm a lifelong athlete and I had really disconnected from that part of
myself. So I was sort of recapturing that.
Just for the joy of it. But then like, oh, like I like this, like maybe I will do an Ironman.
And I'd done a little short race here and there. I didn't realize all the Ironmans like sell out a
year in advance. And I came across an article about this race called Ultraman, which is a
double Ironman three-day race. And something about it spoke to me. It felt more like a spiritual
odyssey than a competition. And really that's what I was, I was on a spiritual odyssey seeking
answers that I didn't, you know, I was asking people, I was asking people, I was asking people
questions that I didn't have answers to yet. And endurance, like training for endurance events
really was a way of like processing all of that. And this race kind of represented a way of going
deeper into that exploration. And so, yeah, I signed up for Ultraman before I know I've still,
to this day, I've never done an Ironman. I just went like right to the super long stuff.
Curious, Rich, as you sit here, you know, 15 or so years into this podcast journey,
building this business and showing up in the world, how you do for so many people,
how do you stay in integrity? It's a lot of work. It's a lot of work. No, it's, it doesn't come
naturally. I learned early in recovery, there's, there's an aphorism in, in AA, which is you can't
transmit something you haven't got. And I think about that a lot. Like there's a lot of people
pontificating on the internet. They're trying to transmit something that they don't actually have.
And that's why it falls flat because the resonance of your voice is a function of how
fully you're living it yourself. And integrity for me means that I'm living my life in alignment,
mentally, spiritually, physically, and interpersonally. How are my relationships?
How am I feeling about the decisions that I'm making? Am I taking care of myself? Am I taking
care of the people that I, that I care about? Like,
integrity is multifaceted. And I think on a, on any given day, I'm probably out of, you know,
you can't be in perfect integrity or alignment with everything simultaneously. But from a global
perspective, like, are you in the right place doing what you're supposed to be doing? And that's
really a function of your relationship with your intuition. And I think a lot of people mistake
what they want to do with their intuition because they, they're not integrated. Like they're,
they're, they're too disconnected.
Connected from one aspect of themselves, either their body or their mind or their spirit to
differentiate what they want from what their intuition, their heart intelligence is telling
them. And that connection doesn't always come naturally. And the modern world is always trying
to distract us from it or erode it or incentivize us to act in opposition to it. So, you know,
it's something you're always toggling, I suppose.
But it's important to me, you know, and I think there's a lot of charlatans out there who are,
are very much out of alignment in their, and they have large profiles and they wield a tremendous
amount of influence. But I think, I believe in people and I, I think people's antennas are,
are getting more and more finely honed to who's worthy of their attention and who isn't.
And I think as we mature into this complex media environment,
we all live in, there's a need for people you can trust, people who are operating from a place
of integrity, who might not be the biggest, but are the people that when you really want to know
what to pay attention to, what not to pay attention to, who's telling you the truth and who isn't,
like that becomes a very valuable thing. And I think that's something I'm always thinking about.
To me, that's the ultimate commodity and it can be so easily squandered. I think people,
you know, trade their trust and their integrity for pennies on the dollar all the time. And I don't
understand it. Like I'm, I play the long game, you know, and that means maybe you're not the
shiniest object, but over the long haul, I know that when I'm scrolling online, I'm looking for
the person that I can trust. Even if my dopamine is getting hijacked by somebody I don't trust.
What a perfect place to wrap, Rich. Thanks for being on Masters of Scale.
Thank you. Appreciate it.
Loved having you.
Thanks again to Rich Roll for joining us.
And for having us at his stunning studio. Rich, I got to tell you, he's really something.
You've probably listened to him. You've probably seen him. Being in a room with him is a whole
different experience. That energy that you feel coming through your speakers or coming through
your screen is like 10x in person. And seeing now how he's scaling, how he's putting to work
everything that he's learned after more than a thousand podcast episodes, as he builds a whole
new network of creators, it's really something.
Rich is an inspiring example of what it means to truly make integrity a priority in your brand.
If anyone I've interviewed for this show is living in integrity,
it's Rich Roll. I'm Jeff Berman. Thank you for listening.
Masters of Scale is a Wait What original. Our executive producer is Eve Troh. Senior
supervising producer is Trisha Bobita. Associate producer is Masha Makatanina. Video editor is
MG Frederick. Senior talent executive is Stephanie Stern. Mixing and mastering by the audio boys
themselves, Aaron Bessinelli and Brian Pugh, with original music by the remarkable Ryan Holiday.
Visit mastersofscale.com to find the transcript for this episode and to subscribe to our newsletter
and be sure to subscribe to our YouTube channel.
Thank you.
Podcast Summary
Key Points:
Founders succeed by building cohesive, systemized teams that eliminate bottlenecks and single points of failure.
Most founders lack integrated financial planning, leading to fragmented wealth management across disconnected professionals.
Creative Planning offers a unified team approach with tax, estate, and investment specialists coordinated by a dedicated wealth manager.
Pega combines powerful AI with enterprise-grade governance to deliver scalable, transparent, and controllable AI solutions.
Rich Roll’s podcast network prioritizes integrity over algorithms, using long-term, relationship-based 360 partnerships instead of transactional ad models.
The network values authenticity, selecting hosts with deep personal and professional alignment to its mission.
Integrity in business and personal life is rooted in self-awareness, sobriety, and living in alignment with one’s values.
Success in media and entrepreneurship requires trust, emotional presence, and a long-term vision beyond short-term trends.
Summary:
The conversation highlights how successful founders build systems to connect teams and eliminate inefficiencies, yet often struggle with fragmented wealth management. Creative Planning addresses this by unifying tax, estate, and investment expertise under one integrated team. Similarly, Pega merges AI power with enterprise control to help businesses scale confidently.
Rich Roll shares his journey from law to sobriety and a rural life in Hawaii, which led to creating a podcast that prioritizes authenticity over algorithms. His network stands out by using long-term, relationship-driven 360 brand partnerships—focused on mutual value rather than transactional CPMs—ensuring deeper audience trust and loyalty. The emphasis is on integrity: living in alignment with one’s values, being emotionally present, and resisting the pressure of algorithmic content.
Ultimately, the narrative underscores that sustainable success comes not from chasing scale or virality, but from authenticity, personal growth, and building meaningful, trustworthy connections across business and personal life.
FAQs
Creative Planning offers an integrated team of tax professionals, estate planners, and investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and ensures all aspects work together seamlessly.
Pega combines powerful AI with governance, transparency, and control to enable enterprises to scale AI faster and more confidently, without the uncertainty or risk of uncontrolled AI implementation.
Rich Roll prioritizes authenticity and emotional connection over algorithmic appeal, focusing on building deep, meaningful relationships with guests and audiences that foster trust and long-term impact.
The network offers long-term, 360-degree brand partnerships instead of short-term ad deals, focusing on real, meaningful relationships with creators and brands to ensure mutual value and sustainability.
Hosts are chosen based on their alignment with the network’s values, experience in podcasting, and understanding of the challenges of monetization and brand representation in a transactional media landscape.
Integrity is central to Rich Roll’s life and work; he believes in living in alignment with one’s values across mind, body, and relationships, and that authenticity resonates more deeply with audiences than performative content.
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