Mastering the Real Estate Game: Brian Head's Journey to a $400 Million Property Empire

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Welcome to night Beat Media's Living the
Dream podcast with your host Gregory Tucker,

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where we discussed the entrepreneur's journey of
turning a dream into reality, showing you

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how to learn, overcome, and
acquire strategic action steps. If you're ready

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to turn your dream into a reality, then get ready to take action.

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Here's your host, Gregory Tucker answering
that question, and that is if you've

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ever wondered what it takes to turn
your dreams into reality, You're in for

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treat Today. Our guest, Brian
Head, founder of head Start Equity,

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is about to unveil the secrets to
his phenomenal success. Now. Brian has

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twenty years of experience. Brian is
active and passively invested in two four hundred

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and sixty two units across eighteen properties, totally a whopping three hundred and ninety

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nine million dollars. He's a finance
graduate from UTSA and worked as a licensed

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investment advisor for a decade. But
here's the hook. Brian's journey isn't just

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impressive, it's a masterclass. Brian, Welcome to the show. We always

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like to ask our guests this important
question. Brian, tell us about you?

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Yeah, So I currently live in
San Antonio, Texas. So actually

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born and raised here. I lived
here all my life. I got married

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with two kiddos. I've got a
five year old dollar and a twelve year

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old daughter. Of course they keep
us pretty busy. But yeah, So

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I just to kind of give you
a real quick rundown of I guess my

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career. I just recently so,
I guess May of last year. I

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left a corporate job with a large
financial services company here in San Antonio after

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nearly twenty five years. So,
as you mentioned, I was a financial

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advisor and stockbroker for about half of
that time, and the latter half of

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that I was kind of a business
analyst type role, working with it and

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business folks. But during most of
my career in the corporate world, I

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was also investing in real estate on
the side. It was really my passion

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the whole time, so I've been
doing that for over twenty years. My

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story, the beginning of my story
is kind of similar to a lot of

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folks that get in real estate,
bought some single family properties, started renting

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those out, and then started flipping
properties as well, and then started getting

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into the smaller multifamily so duplex triplex. I've also invested a little bit in

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Airbnb as well, and then a
few years ago is when I got into

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the commercial, larger commercial space,
investing in the one hundred plus unit apartment

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complexes, and so that's when things
kind of really took off, and that

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was part of what provided me the
opportunity to leave in May of last year

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after almost twenty five years at my
corporate job. Okay, now, Brian,

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can you elaborate on your investment philosophy
and the approach it comes to value

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added multifamily properties. Yeah, So, you know, I've always I've always

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been of the mindset that it's really
best to try to if you're going to

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invest in real estate, to try
to do it from a value ad standpoint,

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So trying to find a bargain kind
of going in right. There's an

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old adage in real estate that you
really make your money when you buy the

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property, So you know, trying
to find that value add opportunity where there's

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an opportunity to you know, obviously
add value through you know, making renovations

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and things like that, and so
in the multifamily space, that's that's what

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we primarily look for, is you
know, multi family properties where the units

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are innning for less than what the
market is in the area, and usually

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that's because you know, they're either
outdated or they're being poorly managed, or

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in most cases it's a combination of
both. So that's primarily what we look

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for in the properties that we invest
in. And after spending so much time

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far as in financial services, why
not transition into commercial real estate? Into

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commercial real estate or yeah, well, the multifamily the multi family properties that

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we invest in now are considered commercial, but in terms of like are you

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talking like office space or some of
the other types of yeah, yes,

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So you know, it was much
more It was a much more natural transition

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to do large multifamily because it's the
same concept as doing single family rentals,

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just multiplied by a lot more units, and so it was a much more

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natural transition. Also, I tend
to, you know, my belief you

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know, different real estate investors are
going to have different beliefs, and I

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think there's good investment opportunities and all
the different kind of commercial assets. However,

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I will say that I've always been
a big believer in residential because people

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need a place to live, right, so that that's never going to change.

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And specifically, you know, when
it comes to residential there's been a

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housing shortage for quite some time now, and so that that helps present some

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some opportunities there. Okay, Now
in going into real estate and being in

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it as long as you have,
what are some of the lessons that you've

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learned along the way? Oh boy, there's there's a lot of lessons there.

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You know, one thing I don't
I'm not ashamed to admit. You

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know, if really, if you're
investing for any length of time and in

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any particular asset, you're going to
lose money, right and and I've had

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my you know, I've I've lost
money in real estate. And one of

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the lessons I learned early on was, you know, I was doing really

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well flipping single family properties and then
I got into a property that was a

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larger property, much more expensive property, thinking, oh, I can you

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know, I can replicate the success
that I've done in these smaller properties into

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this big, expensive property. And
bottom line is I lost money on the

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deal. It took way longer to
sell. There was a lot of extenuating

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circumstances. It could be a whole
flip. This house episode on TV with

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all those stuff that that happened in
that that flip. But there's there's a

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lot less buyers when you start higher
price points you get to in real estate

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in terms of single family you know, there's there's less buyers out there.

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And the timing of it wasn't great, and I probably over improved the property.

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You know, even my very first
property that I flipped, I way

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over improved it. I was way
too picky. You know, you hear

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a lot about you know, when
you're investing in real estate, you have

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to make sure you look at it
like an investment and not a house that

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you're going to have to live in. And with the first house that I

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flipped, you know, I got
super picky. You know, this little

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run in the baseboard, you know, and all these different things and just

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way way over improved, did way
too much stuff, got too picky,

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and it was really expensive. And
however, you know, I did make

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a whopping eight hundred dollars on the
property, but I learned a ton.

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It was really the learning and probably
even more than that, it was proving

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to myself that I could do it
and taking that first step and getting over

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that hurle and getting over that fear
of taking that, you know, investing

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in that first property and just going
for it. I didn't even have have

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contractors lined up. I didn't know
who was going to do the work on

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the property. I literally talked to
the neighbor after I bought it, and

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they said, oh, hey,
I've got a general contractor, buddy,

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that does work. And so I
ended up using them, and you know,

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paid too much money for that.
Again another learning you know, lesson

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that I learned there. But uh, but bottom line is if I hadn't

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taken that step, I wouldn't be
where I am today. And so that

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was a huge learning opportunity but also
allowed me to get over my fear.

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Okay, now along this journey,
were there any mentors or if you can

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go back and find that young Brian, would you would prefer to have a

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mentor at that time? And and
I and I had, you know,

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some my my real estate agent that
I was using at the time. You

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know, he kind of served as
a as a little bit of a mentor

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for me, you know, he
kind of he kind of helped nudge me.

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You know, I was literally having
a conversation with him on the patio

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in the front of this house,
and you know, I he looked at

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me and he was just like,
Brian, you know, you just got

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to do it at some point.
You know, you've read all these books,

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you've done all this education, You're
at a paralysis by analysis standpoint.

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You've just got to do it.
And so he did help me get over

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you know, get over that fear
and taking that first step. And you

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know, I did lean on him
over the years to kind of help help

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guide me through some of what I
was going through and some of the lessons

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learned. I think, you know, generally speaking, if you can learn

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from other's mistakes, that's some way
better way to learn than making the mistakes

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yourself. You're inevitably going to make
mistakes yourself. That's if you're not making

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mistakes, you're not taking risks,
you're not taking chance, and you're not

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going to you know, you're not
going to excel in life. Right.

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But yeah, he definitely helped me, and there have been other mentors along

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the way. But yeah, if
somebody can find a mentor that can that

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can help them that they'll they'll kind
of help shortcut some of the some of

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the experience. So you share with
the of the obstacle that you faced in

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how you handled those. Were there
any other milestones along your journey? Yeah,

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you know, so in terms of
the transition from the single family space

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to the multifamily the larger type projects
that I'm doing now. You know,

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one of the things we kind of
had my wife and I had a life

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event back in twenty eighteen. She
my wife, was diagnosed with breast cancer.

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Fortunately she is cancer free now,
she's doing great. But that life

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event really made both of us kind
of stop and reflect on life and you

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know, what are we doing,
Why are we doing what we're doing?

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Where do we see ourselves in the
next five, ten, fifteen, twenty

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years. And so, you know, we tried to kind of turn a

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negative thing into a positive thing.
And that was when I decided, you

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know, and we decide together that
these larger multi family projects were going to

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help expedite the process a little bit. There's plenty of people that you know,

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can do really well and succeed and
single family properties and scale that that

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wasn't for me though I didn't really
want to. I didn't really want to

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go and purchase one hundred you know, single family properties to try to provide

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the income that we were looking for
and everything, so decided it would be

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it would be a better option for
scaling purposes to get into the multi family

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projects. And so that that life
event is kind of what spurred head Start

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Equity and kind of started that process. Okay, and that's interesting that you

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brought that up, and that is
what changes in the industry have you noticed

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over the years. Yeah, well, it's way more competitive. There are

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a lot more people investing in real
estate than when I started. I mean,

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there was a decent number of people
doing it when I started, but

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this was probably twenty two years ago. And you know, I kind of

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a funny story, you know,
I had funny but not so funny.

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I had a couple of properties that
I did seller financing on to somebody recently,

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and I ended up having to basically
they stopped making their payments. They

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hadn't made payments on it for like
three months, and so I had to

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foreclose on the property, just like
a bank would do. And I went

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here in San Antonio, the way
the county does it when they auction off

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properties, you literally go to the
courthouse steps and there's the different you know,

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trustees for the different properties are out
there and they started talking about the

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property. And you know, back
when I did this, when I started

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doing this twenty plus years ago,
there would be a handful of people at

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this event. At these events right
now, when I went, it was

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crazy because there was booths set up, there was this whole I mean,

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there was dozens and dozens of people
there and you know, it was just

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it was just this whole spectacle.
I was just like, this has changed

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so much from from when I first
started. So I think it's gotten a

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lot more competitive. There's a lot
of different you know, a lot of

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people trying to you know, figure
out their niches in the in the space,

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and so there's a lot of people
you know wholesaling meaning trying to get

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find a property, find a seller
that's distressed that needs to sell it,

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and then get it under contract and
then try to find a buyer after the

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fact. And you know, so
there's just it's way more competitive than than

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when I started. There's still ways
to succeed and do well. Plenty of

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people are doing it, but it's
definitely more more competitive than it used to

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be. And I know that there's
a lot of especially internet traffic, that

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there's a lot, of course is
being offered far as one real estate because

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one unique thing about real estate,
and that is you can't make any more

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land or any more you know,
it is what it is right there.

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You can't go out and create anymore
you can build on it. So that's

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been one of the things that really
I believe that that may have spurred ars

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like the New found gold rush.
Right there is the actualization or the realization

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that hey, real estate, getting
the property right there, holding on to

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it. Now, there's much more
to it than just getting the property and

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saying, okay, now I have
an ATM. I have the property.

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I just put bodies in it,
and it's like an ATM. Every time

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I go by this time of the
month, it's just going to be spitting

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out change. Tell us about that. Rainbows and unicorns. Yeah, it's

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uh, it does crack me up
when when so, first of all,

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there are a lot of there's tons
of courses out there. There's so many

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that are just just, I don't
know, ridiculous to me, Like I

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theoretically, yes, you know,
no money down and all these great all

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these things that they tell you,
Yeah, theoretically, yes, it's possible.

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It is possible, and there are
ways to do it, and there

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are people that are successful with it, but it is, like you said,

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there's a lot more to it,
and you know it is not you

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know, some people like to say, oh, you know, go get

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a single family rental house, it's
a passive investment. Well, it's not

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a passive investment, you know.
And even if you have a property management

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company that you hire to manage you
for you, it's still not passive.

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You know, they're they're still going
to be coming to you for certain questions

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and things like that, and so
it's it's not a passive investment and there's

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still decisions you'll have to make.
But I personally, I've actually never used

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a property management company. Always managed
my properties myself. Obviously, not the

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apartment buildings, that's not something that's
possibly not feasible, but in the single

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family, small multi family space,
I've always managed it myself. And you

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know that it's not passive. There's
there there are some good courses out there,

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but I think, you know,
for me, I think if I

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could give people one piece of advice
on trying to get educated in real estate,

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whatever avenue you're going down, I
would I would kind of go back

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to what you mentioned about finding a
mentor and finding one that's local to you,

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because I think there's so many of
these courses out there that are national

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and you know, do all this
stuff online and that's great, but I

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think you really needed to be able
to sit down with somebody, have coffee

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with somebody, and you know,
just pick their brain a little bit,

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and you know, go with them
to go check out a property and get

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their thoughts on certain things. And
you can't do that if it's all virtual.

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I mean, I guess technically you
can, but it's not the same.

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And so, you know, even
when I got into the multi family,

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these large multi family I joined a
local mastermind group here in San Antonio,

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and that was one of the game
changers for me in this space because

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I was able to get around people
doing these large, you know, multimillion

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dollar deals that you know, before
that, I always thought, well,

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you know, I don't have you
know, a million dollars in cash sitting

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around to go put into a property. But then I was able to get

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in a room with people that were
figuring out a way to do it,

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pulling money together, you know,
investors and things like that, and so

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I think that's one of the biggest
keys, is finding a mentor that will

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will really help you. And I
would say, I would say that,

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you know, people that are serious
about it interview some different mentors, don't

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just jump into the first one you
find, and because they're not all quick

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created equal, and you may not, you know, you may not gel

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with that particular person, and I
think that's super important. So yeah,

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that would be Yeah, it's it's
not it's not all you know roses,

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and you know, there's definitely some
challenges and you know, victions and things

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like that. I'm literally, you
know, I've still got some of my

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single family properties now too. Diversification
is important to me, so I'm holding

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onto some of those as well,
and I'm literally going through an eviction process

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right now, so those things happen. And I would imagine also that each

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area, as far as the region
that you're in, also has a lot

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to do with that. So it's
important that you know, Okay, I'm

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in the southwest or I'm in the
east, then it's good to know far

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as what are some of the the
nuances I would imagine versus you can't get

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it offline right there or just googling
that sometimes you got to be in the

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area in order to really get a
sincere feel far as for it, Yeah,

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for sure, I would totally agree
with that. I think, you

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know, that's the whole boots on
the ground theory, right, We're not

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really a theory, it's a thing. You know, you want to have

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boots on the ground. You want
to have somebody there, local in that

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area, somebody that understands in the
market. And you know that's why from

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a from an active standpoint, I've
never actually gone outside of Texas to invest

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I mean, I've always stuck to
the state. This is what I know.

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And yeah, it's it is very
different state to state. You know,

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some states are more landlord friendly than
others. Right, Texas is considered

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a landlord friendly state. California is
not. You know, it can take

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months and months and months and months
and months. And you know what,

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after doing this for a while,
one of the things that that does frustrate

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me a little bit is and there's
bad landlords out there, don't get me

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wrong, but this whole you know, this this whole concept of you know,

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slum lords, and there are some
of them, but you know,

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I think landlords tend to get clumped
into all together by some people, and

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you know the reality of it is, you know, most real estate investors

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like myself, right, yes we're
landlords. Yes we're collecting rent from people,

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but we have loans we have to
pay too, and when tenants don't

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pay, that hurts us. And
so it's it's you know, I had

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during COVID, I had I had
a tenant actually call me up and tell

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me because you know, they were
doing the they were pausing the evictions and

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stuff like that during COVID, which
is fine, but I had a tenant

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call me up and say, uh, yeah, I heard I didn't have

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to pay my rent. The president
said that we didn't have to pay our

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rent. I was like, no, that's not really, it's not really

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how this is. This is working. We can't evict right now, but

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if you don't pay that, you're
just setting yourself up for in the future

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that's going to happen. So they
just didn't government didn't want to create that

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hardship on people during that time.
But you still are supposed to pay.

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So it was kind of interesting.
But yeah, there are some bad landlords

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out there, but there's there's a
lot of good ones too. Yeah,

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that sounded like that was a little
bit of selected hearing. Selective hearing right

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there. For it's so so uh. The main things FAR is for someone

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who's looking to go into the real
estate business, such as yours, or

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to take on a journey such as
yours. You had mentioned finding a mentor

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far someone that's local. So where
are some of the places that a person

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would find. Would that be the
national or the regional real estate association or

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how would they go about finding a
Yeah, you could do that, you

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know pretty much. Now there are
so many different meetups in every city now,

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different real estate investing meetups. You
know, we have we have actually

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our own real estate investing meet up
here in San Antonio called Wealth and Whiskey.

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Kind of a pretty cool name.
Buddy of mine came up with that

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name. But but there's so many, there's so many different meetups where you

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can meet a lot of interesting people
who are doing these types of things.

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And I think that's one of your
best bets is trying to find somebody at

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one of those meetups because most of
them are free, you know, so

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you can just go during the week
on an evening and just you know,

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try to find some folks that are
like minded, that are willing to help

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you. One of the one of
the biggest challenges, honestly is finding somebody

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that is willing to take the time
because you know, just like any any

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industry, any any business, right, everybody is busy. You know,

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everybody only has so much time.
And you know, time is very valuable.

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You know, you can't get it
back. So you know, finding

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somebody that's willing to work with you, you know, and if you can

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find that, and even better if
you can find it with somebody that you

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know isn't going to charge you at
arm andal a, you know that that's

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great. And and you know,
just I think you just got to get

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out there and you just got to
go to those meetups and you've got to

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try to find some folks that that
are willing to help you out. That

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is so important right there. Now
another thing, and that is just as

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when you were in the financial services
business, where continuous education is important because

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the uh, the business is constantly
changing. So give us your take on

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that right there, or give us
suggestions as far as for this series.

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Yeah, I think that you know, books are still a great way to

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educate yourself, you know, for
me, when you know, kind of

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my first the first little seed planned
for me and investing in general, was

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from my economics teacher in high school, where we had to He asked us

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to start tracking stocks and in the
newspaper. This is back when there was

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no internet, so we were tracking
the stocks in the newspaper. And that

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kind of, you know, put
that seed in my mind. And then

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when I graduated high school, I
just went to the library and just started

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checking out books and you know,
learning everything I could. There were podcasts.

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There wasn't the Internet like there is
now, so obviously now there's podcasts.

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You know, podcasts are great.
It's a great way to learn a

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ton, and so podcasts, there's
so much information on the internet. Again,

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mentors are a great way. But
I think, you know, for

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me, I obviously I stay really
connected with what's going on in real estate,

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but I'm I like to look at
a much bigger picture too, of

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what's going on in the economy.
I was just you know, I watched

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CNBC most days, you know,
just to kind of get a pulse on

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what's going on, listen to different
podcasts that have nothing to do with real

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estate that are more on the economy, where you know what's going on with

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interest rates, and you know,
as much as I don't really like politics,

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I kind of keep up with some
of that as well, just to

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stay you know, educated on what's
going on because that can that can affect

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you know, you know, real
estate values, that can affect you know,

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policy changes are big, you know, in real estate, especially when

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it comes to taxes and stuff like
that, and so I just think it's

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important to keep your education diverse and
don't just you know, if you want

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to get into real estate, obviously
you really need to dig in and go

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into that and research that, but
don't limit it to that. Look at

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some of these other financial avenues as
well, and keep yourself abreast of what's

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going on outside of the real estate
market and how that can impact real estate.

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So, oh, that's a lot
right there now, Brian. Brian,

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I know you're a very busy man, and I greatly appreciate you're taking

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the time to share as far as
with the audience this valuable information because this

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could actually be applied far as to
a variety of other industries. Now,

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before you leave or before we end
this, could you give us some pointers

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00:26:02.000 --> 00:26:04.920
or what would you like our audience
to unpack. What are some of the

347
00:26:06.000 --> 00:26:14.319
most important things that they should go
away or come away with. Yeah,

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I think you kind of Actually you
mentioned it with the education piece. I

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think education is huge, and that's
one of the reasons why I do what

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I do now, is because I
actually love educating folks on real estate.

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I could talk about it all day. I just have to, you know,

352
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temper it a little bit because I
actually need to do some work too,

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But I could talk real estate all
day. So I think education is

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important. You know, we also
touched on fear a little bit earlier,

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and I think you know, and
again, like you said, this could

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be applied to other avenues as well. But you know, the reality of

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its success is on the other side
of fear, right, and so you've

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got to be able to get over
that fear. In any avenue of business,

359
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you've got to be able to get
past that. And you know that

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that's probably one of the things that
stops most people from from getting very far,

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and especially entrepreneurs that that are looking
to because it's a whole different corporate

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world is one thing, right,
the corporate world, Yes, you have

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to work hard, and you have
to do all that and you have to

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be creative and things like that,
right, but things are more dictated to

365
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you in the corporate world. Right
you're kind of told, here's the things

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you need to do. You know, this is how we're going to evaluate

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you and everything. When you're an
entrepreneur, it's all on you, like

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00:27:25.799 --> 00:27:29.200
the buck stops with you. You
you you know, it's all based on

369
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you know, your success is all
based on what you what you're able to

370
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do, your success of your business. And so I think getting over getting

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over fear is is just one of
the one of the biggest things for people.

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And you know it's not and it's
not just jumping in and you know,

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haphazardly and not planning. I think
you need to You need to plan

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and goes back to educating yourself and
trying to set some things up. And

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you know, I fear is a
big thing. And it obviously helped me

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back for a while too, because
I was in a corporate job for a

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long time, but I was kind
of I knew I wanted to be an

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entrepreneur and I knew that was real
estate was what I wanted to do.

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But I still stayed in the corporate
job, and some of that was security,

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right I had a great job for
a great company and it provided the

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steady income and that that was great, but you know, it took.

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It took finally getting to the point
where you know, okay, this is

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this is it, this is what
I want to do. And again going

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back to life events that that that
really played a vital role in that as

385
00:28:22.960 --> 00:28:26.640
well. But I think just getting
over the fear is huge. That's that's

386
00:28:26.680 --> 00:28:32.440
probably one of the biggest things.
Okay, well, that's great right there,

387
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because our audience is it's a diverse
audience right there. And one of

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the things that we're finding out and
that is that there's a lot of entrepreneurs

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that are over fifty five that are
their first time out as far as in

390
00:28:51.680 --> 00:28:59.039
the field right there, because the
landscape is constantly changing, so that those

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are some great words of wisdom right
there. Brian, again, we thank

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00:29:03.799 --> 00:29:08.839
you far As for taking the time
and sharing with us your journey and how

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00:29:08.880 --> 00:29:14.839
you turned your dream into a reality. So that way right there, our

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00:29:14.960 --> 00:29:22.000
audience who are listening and looking at
this podcast, that they'll take those golden

395
00:29:22.079 --> 00:29:27.240
nuggets and apply it to their circumstances
and at the end of the day,

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00:29:27.960 --> 00:29:37.000
turn their dream into a reality and
be intentional about it. Right there.

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00:29:37.400 --> 00:29:55.640
Thank you, thanks for listening to
night Beat Media's Living the Dream. If

398
00:29:55.680 --> 00:30:00.240
you enjoyed this podcast, please live
a comment or hit follow and subscribe on

399
00:30:00.279 --> 00:30:03.839
our lake so you can stay up
to date on new episodes until next time.

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00:30:04.279 --> 00:30:08.440
When writing the story of your life, be sure you're holding the pen