July 5, 2025 • 12 mins
Robby Butler is Managing Director and head of capital markets at Y Street Capital, our development company. On today's show we are talking about attacking complexity and simplifying business processes. To connect with Robby, he can be found on LinkedIn at https://www.linkedin.com/in/robby-butler/ or at Y Street Capital.
-------------
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:02):
Welcome to the Real Estate Espresso podcast, your morning
shot of what's new in the world of real estate investing.
I'm your host, Victor Minash. This is the WEEKEND edition
where we interview notable people from the world of real
estate investing. Today is no exception.
We have a great guest all the way from Saint Louis.
Welcome to the show, my good friend Robbie Butler.
It's great to be here. Well, Robbie, great to have you
here. You're part of our the Y St.
(00:23):
Capital team, you're director ofour capital markets team, and
you're the lead integrator in our company.
And very excited to have this conversation because we've been
going through a lot of work within within the company to
really streamline our systems, our processes.
And you've been at the center ofa lot of that.
And I think there's a lot of value that our listeners can get
(00:44):
from that. But maybe before we dive into
those details, perhaps give justa short back story and how you
got to this point. Sure.
In context for this conversation, I'll talk about
some of my own, let's call it organizational experience.
I always found myself getting into the nitty gritty.
I look even back at my college days and I, I had a student
(01:07):
government leadership role. And what I was so intent on
doing was pulling the threads tofigure out why are these things
relevant and moving into my professional experience.
I with with my nonprofit fundraising roles that I had
right out of college. Again, I saw it's not enough
just to raise the money, we haveto know what happens afterwards.
(01:28):
So in that context, I was sitting in a sales role, but to
just hand it off to the members of the nonprofit was not enough
in my entrepreneurial experience.
Same concept I knew can't just go out and drive business, can't
do more real estate deals. We have to know what are we
delivering to our investors? What are we delivering in a
really clear manner that accomplishes what they came here
(01:50):
for. So always that systems thinking
has been a part of of my journeyand I found it a little annoying
when trying to focus only on theproduction side.
But if you're just producing andburning money, burning
employees, burning cash, you're wasting your time.
And so in Y Street, over my timewith Y St.
Capital, stepping into the integrated role and taking on
(02:10):
managing director as a title, I,it was very natural for me to
engage with these core processes, these core systems,
and to understand what are the threads in our business and how
do we make it as simple as possible.
And so that's what we're talkingabout today.
This is something that's talked about.
There's acronyms like KISS, Keepit Simple, Stupid complexity is
(02:31):
the enemy of progress. There's all kinds of different
quotes from various luminaries throughout the years, and it's
really driven as we've been going through our
entrepreneurial journey as a company, it's driven a real
focus on simplification of systems and process within our
organization. And occasionally we bump into
(02:53):
these things and we discover, man, this is more complicated
than it needs to be. Talk a little bit about how
that's being attacked within thecompany.
Sure, you need to understand themajor components of every of
every activity. The curse of an engineer is to
optimize something that shouldn't exist at all.
(03:15):
Again, one other you know, I don't know who says that, but
it's a luminary quote that someone is perfecting something
that shouldn't really exist at all.
And we've found that we have so many quality procedures, but
they sometimes add extra steps. They add components that have
encumbered us. And we are a fairly complicated
organization because we're pursuing very complicated deals.
(03:36):
So when we back way, way up, what is complicated?
Real estate development is complicated.
It is why you can have such highreturn profiles.
It's why so many people are terrified of it.
When I hear someone say, well, development is so risky, I go
no, you just don't understand the necessary components you
have to accomplish on the way toa successful development.
(03:58):
However, that doesn't make it any easier.
By definition is complicated because it is not simple.
But Jim Rohn has the incredible line that if it is easy, it is
something you can do. Therefore, if it is hard, it is
something you cannot do. Real estate development you can
do, so it is easy. However, it's not always simple,
(04:22):
but it can be done. And unless you hit the true
wall, which we've now learned after decades of, of real estate
development among the partners in this company, that there are
certain things you'd never want to hit.
There are, but there are third rails you don't want to touch.
That means you can accomplish itand you can simplify it.
And that's what we're working on.
So long explanation here. One example is we're in multiple
(04:45):
states, we have different jurisdictions across all of our
projects. So there's different processes
that every single project gets inserted into.
So we know this is going to be aself storage asset, but what we
may not have done before is the exact county's specific
requirements. And so we have to vet those out.
We have to flesh those out. It also means that a lender that
(05:07):
we're working with perhaps we'vedone deals with that lender
before, has to understand the complex structure that because
of our multiple counties, multiple states, multiple
countries, they have to be able to see through all of that.
And so this is a complicated issue.
Simplifying it has started to look like a very long PowerPoint
that has every single corporate structure.
So at any point they can refer to the entire PowerPoint and go.
(05:30):
I'm trying to understand this entity that controls this aspect
of the project as opposed to separate entity, separate
control structure. Same project, but they can find
it in the same document. We also have a point person
who's responsible for explainingthat every single time.
This is 1 simple example of applying some simplicity to
something that is inherently complex.
(05:52):
Well, at the end of the day, forexample, if you're presenting a
project to a lender and it's gotto go to loan committee and so
on and, and the underwriter for the, for the loan can't
understand the corporate structure, then it's just not
going to get over the finish line.
So you know, that that's an example where we've had to
expand more energy than we wouldhave ever wanted, explaining
(06:14):
what has turned out to be not through any desire to be
complex, a corporate structure that is just not as
straightforward. It, it takes a little bit of
reading to truly internalize it.I mean, it's easy for us because
we live it every day. But for the loans officer that's
underwriting that particular loan, they go, oh wow, I haven't
(06:35):
seen that before. So it it's really understanding
where that may be unnecessary complexity comes into play.
Another method that we've used to, to break down the, the
complexity is to look at, like Isaid earlier, what are the most
core processes in the entire company that all have to run no
(06:57):
matter what. We have basically 7 core
processes. And there, if anyone's familiar
with the entrepreneurial operating system, you have
sales, you have operations and you have finance and each of
those has two or three core processes.
And if they're not running, nothing works.
So if you have a new idea, for example, if we said we want to
(07:19):
grow our property management relationships, that's a
beneficial relationship for us to have.
But is it truly core? Because we're developers, we
have a few excellent property management relationships.
Do we really have to drive for more?
Because it requires a new process, it requires someone to
be accountable for it. So through some discipline,
(07:40):
cutting away those things that are not essential, it's not
essential for us to go meet another Gray star.
It's not essential for us to go meet another nationwide property
management group. So it's a process that's not
core to the core things we do asa company.
And so it's best to gently remove it or to say we will come
back to this 90 days later to decide whether it really needs
(08:02):
to be a part of our company's work.
Getting those core processes clear has also been a a bit of a
joyful effort because it helps us to say we can say no to this
new initiative because it doesn't fit what's truly core to
this company. Let's talk a little bit about
organization chart because you know, at the end of the day, if
something's not getting done, the very first question I ask is
(08:22):
well, who's responsible for it? And if you can't find that
individual, then it's usually not a surprise that it's not
getting done. The accountability chart for the
company is, is one of those coretools that really identifies
who's on 1st and, and who owns that particular deliverable.
And if there's gaps, then that'swhat you got to go fix.
And sometimes the answer is nobody.
(08:44):
Sometimes the answer is everybody, which is the same as
nobody. Sometimes it's the person at the
top of the house that's the sameas nobody.
So finding the right accountability on the chart is
also one of those pieces, makingsure that we don't have too many
dotted lines or the OR lack of clarity or ambiguity and
accountability. One of the core features of
(09:06):
building an accountability chart, it's also what makes it a
fair, a fairly challenging experience for any organization
to do is to look at what would be ideal.
Ignoring all people, ignoring all history of the company or of
the industry or of the asset class or whatever and saying we
are looking for principle here. In principle, what is best for
(09:30):
us. And, and then engineering that
following the accountability line, saying this is what we
would do in the ideal. And then looking at, OK, now how
do we populate that ideal structure?
That's the, I would say the mostchallenging part because you are
attached to your history, you'reattached to your educational
experience, the things that you have brought you to this stage.
(09:52):
And you think that that should instill itself upon building out
the accountability chart. But to say, no, we want what's
ideal and we want to pursue the ideal no matter what.
And then we look back and go, well, this is how we could get
there as fast as possible and this is how we can accomplish
the next 6 or 12 months based onwhat we've got.
That's the real lesson, always going all right, what's the
(10:14):
ideal then? Reverse engineer that.
Well, and then of course, you also have to look at, especially
in organizations that aren't large, that don't have the
luxury of moving people around at at will or hiring at will,
sometimes the skill set that youhave within the organization is
not a perfect match to what might be that ideal.
So you you want to play to people's strengths.
(10:36):
You don't want to give somebody responsibility for something
that they're really terrible at because that's a recipe for
failure. And you say, well, you were
accountable for that. You didn't deliver.
Well, yeah, but they weren't setup for success either.
So you got to be a little bit pragmatic about it as well.
And the ideal is also finding that perfect match between the
skills for the person who's actually tasked with the job,
with the work that needs to be done.
(10:57):
Business is a great game, and learning to play this specific
game is one of the fun ones. How do you pursue the ideal
without shipwrecking along the way or causing issues that are
irreparable in the organization?There's a story I absolutely
love, which actually comes from Guy Raz's book, How I Built
(11:17):
This. Great business lessons all woven
through that book. And he talks about the founder
of 1800 got junk. I don't remember the revenue
they were doing on an annual basis, but they had 18 or 20
employees. They were successful.
And yet he realized all in a blinding flash of the obvious,
he built a company that was throwing trash away.
And what he wanted to build was a company that gave people their
(11:38):
freedom back by taking away things that didn't belong in
their freedom, that that freeingthem of the things they didn't
want so that they could pursue freedom.
And he wiped his entire organization clean, fired
everyone, started all new. It was him and 10 trucks.
No one else worked there. And he started all over again.
And 1800 Got Junk is a successful business once again,
(12:00):
but he had to go through that very painful experience of
firing everyone to get at his actual vision.
And ideally you get there without needing to trim away
everything along the way. Love it, Robbie, If folks want
to connect, if they want to learn more about what's going on
at Y St. Capital, what's the best way?
Always follow me on LinkedIn. Love talking there, love meeting
people there, and love sharing what we're learning as an
(12:21):
organization. And for Y St.
Capital, find us@ystcapital.com or this podcast.
Awesome. Well, Robbie, happy 4th of July.
Have a great weekend. And for the listeners at home,
definitely connect with Robbie Butler in our team at Wide St.
Capital Links will be in the show notes.
And in the meantime, have an awesome rest of your weekend.
Go make some great things happenand we'll talk to you again
(12:43):
tomorrow.
Welcome to the Real Estate Espresso podcast, your morning
shot of what's new in the world of real estate investing.
I'm your host, Victor Minash. This is the WEEKEND edition
where we interview notable people from the world of real
estate investing. Today is no exception.
We have a great guest all the way from Saint Louis.
Welcome to the show, my good friend Robbie Butler.
It's great to be here. Well, Robbie, great to have you
here. You're part of our the Y St.
(00:23):
Capital team, you're director ofour capital markets team, and
you're the lead integrator in our company.
And very excited to have this conversation because we've been
going through a lot of work within within the company to
really streamline our systems, our processes.
And you've been at the center ofa lot of that.
And I think there's a lot of value that our listeners can get
(00:44):
from that. But maybe before we dive into
those details, perhaps give justa short back story and how you
got to this point. Sure.
In context for this conversation, I'll talk about
some of my own, let's call it organizational experience.
I always found myself getting into the nitty gritty.
I look even back at my college days and I, I had a student
(01:07):
government leadership role. And what I was so intent on
doing was pulling the threads tofigure out why are these things
relevant and moving into my professional experience.
I with with my nonprofit fundraising roles that I had
right out of college. Again, I saw it's not enough
just to raise the money, we haveto know what happens afterwards.
(01:28):
So in that context, I was sitting in a sales role, but to
just hand it off to the members of the nonprofit was not enough
in my entrepreneurial experience.
Same concept I knew can't just go out and drive business, can't
do more real estate deals. We have to know what are we
delivering to our investors? What are we delivering in a
really clear manner that accomplishes what they came here
(01:50):
for. So always that systems thinking
has been a part of of my journeyand I found it a little annoying
when trying to focus only on theproduction side.
But if you're just producing andburning money, burning
employees, burning cash, you're wasting your time.
And so in Y Street, over my timewith Y St.
Capital, stepping into the integrated role and taking on
(02:10):
managing director as a title, I,it was very natural for me to
engage with these core processes, these core systems,
and to understand what are the threads in our business and how
do we make it as simple as possible.
And so that's what we're talkingabout today.
This is something that's talked about.
There's acronyms like KISS, Keepit Simple, Stupid complexity is
(02:31):
the enemy of progress. There's all kinds of different
quotes from various luminaries throughout the years, and it's
really driven as we've been going through our
entrepreneurial journey as a company, it's driven a real
focus on simplification of systems and process within our
organization. And occasionally we bump into
(02:53):
these things and we discover, man, this is more complicated
than it needs to be. Talk a little bit about how
that's being attacked within thecompany.
Sure, you need to understand themajor components of every of
every activity. The curse of an engineer is to
optimize something that shouldn't exist at all.
(03:15):
Again, one other you know, I don't know who says that, but
it's a luminary quote that someone is perfecting something
that shouldn't really exist at all.
And we've found that we have so many quality procedures, but
they sometimes add extra steps. They add components that have
encumbered us. And we are a fairly complicated
organization because we're pursuing very complicated deals.
(03:36):
So when we back way, way up, what is complicated?
Real estate development is complicated.
It is why you can have such highreturn profiles.
It's why so many people are terrified of it.
When I hear someone say, well, development is so risky, I go
no, you just don't understand the necessary components you
have to accomplish on the way toa successful development.
(03:58):
However, that doesn't make it any easier.
By definition is complicated because it is not simple.
But Jim Rohn has the incredible line that if it is easy, it is
something you can do. Therefore, if it is hard, it is
something you cannot do. Real estate development you can
do, so it is easy. However, it's not always simple,
(04:22):
but it can be done. And unless you hit the true
wall, which we've now learned after decades of, of real estate
development among the partners in this company, that there are
certain things you'd never want to hit.
There are, but there are third rails you don't want to touch.
That means you can accomplish itand you can simplify it.
And that's what we're working on.
So long explanation here. One example is we're in multiple
(04:45):
states, we have different jurisdictions across all of our
projects. So there's different processes
that every single project gets inserted into.
So we know this is going to be aself storage asset, but what we
may not have done before is the exact county's specific
requirements. And so we have to vet those out.
We have to flesh those out. It also means that a lender that
(05:07):
we're working with perhaps we'vedone deals with that lender
before, has to understand the complex structure that because
of our multiple counties, multiple states, multiple
countries, they have to be able to see through all of that.
And so this is a complicated issue.
Simplifying it has started to look like a very long PowerPoint
that has every single corporate structure.
So at any point they can refer to the entire PowerPoint and go.
(05:30):
I'm trying to understand this entity that controls this aspect
of the project as opposed to separate entity, separate
control structure. Same project, but they can find
it in the same document. We also have a point person
who's responsible for explainingthat every single time.
This is 1 simple example of applying some simplicity to
something that is inherently complex.
(05:52):
Well, at the end of the day, forexample, if you're presenting a
project to a lender and it's gotto go to loan committee and so
on and, and the underwriter for the, for the loan can't
understand the corporate structure, then it's just not
going to get over the finish line.
So you know, that that's an example where we've had to
expand more energy than we wouldhave ever wanted, explaining
(06:14):
what has turned out to be not through any desire to be
complex, a corporate structure that is just not as
straightforward. It, it takes a little bit of
reading to truly internalize it.I mean, it's easy for us because
we live it every day. But for the loans officer that's
underwriting that particular loan, they go, oh wow, I haven't
(06:35):
seen that before. So it it's really understanding
where that may be unnecessary complexity comes into play.
Another method that we've used to, to break down the, the
complexity is to look at, like Isaid earlier, what are the most
core processes in the entire company that all have to run no
(06:57):
matter what. We have basically 7 core
processes. And there, if anyone's familiar
with the entrepreneurial operating system, you have
sales, you have operations and you have finance and each of
those has two or three core processes.
And if they're not running, nothing works.
So if you have a new idea, for example, if we said we want to
(07:19):
grow our property management relationships, that's a
beneficial relationship for us to have.
But is it truly core? Because we're developers, we
have a few excellent property management relationships.
Do we really have to drive for more?
Because it requires a new process, it requires someone to
be accountable for it. So through some discipline,
(07:40):
cutting away those things that are not essential, it's not
essential for us to go meet another Gray star.
It's not essential for us to go meet another nationwide property
management group. So it's a process that's not
core to the core things we do asa company.
And so it's best to gently remove it or to say we will come
back to this 90 days later to decide whether it really needs
(08:02):
to be a part of our company's work.
Getting those core processes clear has also been a a bit of a
joyful effort because it helps us to say we can say no to this
new initiative because it doesn't fit what's truly core to
this company. Let's talk a little bit about
organization chart because you know, at the end of the day, if
something's not getting done, the very first question I ask is
(08:22):
well, who's responsible for it? And if you can't find that
individual, then it's usually not a surprise that it's not
getting done. The accountability chart for the
company is, is one of those coretools that really identifies
who's on 1st and, and who owns that particular deliverable.
And if there's gaps, then that'swhat you got to go fix.
And sometimes the answer is nobody.
(08:44):
Sometimes the answer is everybody, which is the same as
nobody. Sometimes it's the person at the
top of the house that's the sameas nobody.
So finding the right accountability on the chart is
also one of those pieces, makingsure that we don't have too many
dotted lines or the OR lack of clarity or ambiguity and
accountability. One of the core features of
(09:06):
building an accountability chart, it's also what makes it a
fair, a fairly challenging experience for any organization
to do is to look at what would be ideal.
Ignoring all people, ignoring all history of the company or of
the industry or of the asset class or whatever and saying we
are looking for principle here. In principle, what is best for
(09:30):
us. And, and then engineering that
following the accountability line, saying this is what we
would do in the ideal. And then looking at, OK, now how
do we populate that ideal structure?
That's the, I would say the mostchallenging part because you are
attached to your history, you'reattached to your educational
experience, the things that you have brought you to this stage.
(09:52):
And you think that that should instill itself upon building out
the accountability chart. But to say, no, we want what's
ideal and we want to pursue the ideal no matter what.
And then we look back and go, well, this is how we could get
there as fast as possible and this is how we can accomplish
the next 6 or 12 months based onwhat we've got.
That's the real lesson, always going all right, what's the
(10:14):
ideal then? Reverse engineer that.
Well, and then of course, you also have to look at, especially
in organizations that aren't large, that don't have the
luxury of moving people around at at will or hiring at will,
sometimes the skill set that youhave within the organization is
not a perfect match to what might be that ideal.
So you you want to play to people's strengths.
(10:36):
You don't want to give somebody responsibility for something
that they're really terrible at because that's a recipe for
failure. And you say, well, you were
accountable for that. You didn't deliver.
Well, yeah, but they weren't setup for success either.
So you got to be a little bit pragmatic about it as well.
And the ideal is also finding that perfect match between the
skills for the person who's actually tasked with the job,
with the work that needs to be done.
(10:57):
Business is a great game, and learning to play this specific
game is one of the fun ones. How do you pursue the ideal
without shipwrecking along the way or causing issues that are
irreparable in the organization?There's a story I absolutely
love, which actually comes from Guy Raz's book, How I Built
(11:17):
This. Great business lessons all woven
through that book. And he talks about the founder
of 1800 got junk. I don't remember the revenue
they were doing on an annual basis, but they had 18 or 20
employees. They were successful.
And yet he realized all in a blinding flash of the obvious,
he built a company that was throwing trash away.
And what he wanted to build was a company that gave people their
(11:38):
freedom back by taking away things that didn't belong in
their freedom, that that freeingthem of the things they didn't
want so that they could pursue freedom.
And he wiped his entire organization clean, fired
everyone, started all new. It was him and 10 trucks.
No one else worked there. And he started all over again.
And 1800 Got Junk is a successful business once again,
(12:00):
but he had to go through that very painful experience of
firing everyone to get at his actual vision.
And ideally you get there without needing to trim away
everything along the way. Love it, Robbie, If folks want
to connect, if they want to learn more about what's going on
at Y St. Capital, what's the best way?
Always follow me on LinkedIn. Love talking there, love meeting
people there, and love sharing what we're learning as an
(12:21):
organization. And for Y St.
Capital, find us@ystcapital.com or this podcast.
Awesome. Well, Robbie, happy 4th of July.
Have a great weekend. And for the listeners at home,
definitely connect with Robbie Butler in our team at Wide St.
Capital Links will be in the show notes.
And in the meantime, have an awesome rest of your weekend.
Go make some great things happenand we'll talk to you again
(12:43):
tomorrow.
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