All Episodes

March 4, 2024 • 30 mins
Join us as Brian Head, the visionary force behind Head Start Equity, unveils his transformative trajectory from a sharp investment advisor to a real estate titan with a commanding $400 million portfolio. Our exchange with Brian is a treasury of acumen, as he dissects the intricacies of detecting hidden gems within multifamily properties and articulates why residential real estate is the cornerstone of his investment empire. His two decades of experience serve as a masterclass in navigating the real estate realm's opportunities and challenges, providing a poignant reminder that investing in properties extends far beyond finding a place to call home.
Strap in for a ride through the competitive battleground of real estate auctions and the nuances of seller financing as shared from Brian's frontline experiences. His insights are a wakeup call against the passive income fairytale, advocating for a proactive stance in property management. It's all about the educational hustle and the power of mentorship in this episode, where Brian lays out the roadmap for aligning with a mentor who resonates with your investment aspirations and the transformative impact a mastermind group can have when tackling complex deals. Our conversation is an arsenal of strategies and stories, empowering listeners to shatter the barriers of fear and charge confidently into the entrepreneurial fray, no matter the industry.

Become a supporter of this podcast: https://www.spreaker.com/podcast/night-beat-media-living-the-dream--2752105/support.
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:02):
Welcome to night Beat Media's Living theDream podcast with your host Gregory Tucker,
where we discussed the entrepreneur's journey ofturning a dream into reality, showing you
how to learn, overcome, andacquire strategic action steps. If you're ready
to turn your dream into a reality, then get ready to take action.

(00:25):
Here's your host, Gregory Tucker answeringthat question, and that is if you've
ever wondered what it takes to turnyour dreams into reality, You're in for
treat Today. Our guest, BrianHead, founder of head Start Equity,

(00:47):
is about to unveil the secrets tohis phenomenal success. Now. Brian has
twenty years of experience. Brian isactive and passively invested in two four hundred
and sixty two units across eighteen properties, totally a whopping three hundred and ninety

(01:12):
nine million dollars. He's a financegraduate from UTSA and worked as a licensed
investment advisor for a decade. Buthere's the hook. Brian's journey isn't just

(01:34):
impressive, it's a masterclass. Brian, Welcome to the show. We always
like to ask our guests this importantquestion. Brian, tell us about you?
Yeah, So I currently live inSan Antonio, Texas. So actually
born and raised here. I livedhere all my life. I got married

(01:57):
with two kiddos. I've got afive year old dollar and a twelve year
old daughter. Of course they keepus pretty busy. But yeah, So
I just to kind of give youa real quick rundown of I guess my
career. I just recently so,I guess May of last year. I
left a corporate job with a largefinancial services company here in San Antonio after

(02:20):
nearly twenty five years. So,as you mentioned, I was a financial
advisor and stockbroker for about half ofthat time, and the latter half of
that I was kind of a businessanalyst type role, working with it and
business folks. But during most ofmy career in the corporate world, I
was also investing in real estate onthe side. It was really my passion

(02:44):
the whole time, so I've beendoing that for over twenty years. My
story, the beginning of my storyis kind of similar to a lot of
folks that get in real estate,bought some single family properties, started renting
those out, and then started flippingproperties as well, and then started getting
into the smaller multifamily so duplex triplex. I've also invested a little bit in

(03:06):
Airbnb as well, and then afew years ago is when I got into
the commercial, larger commercial space,investing in the one hundred plus unit apartment
complexes, and so that's when thingskind of really took off, and that
was part of what provided me theopportunity to leave in May of last year
after almost twenty five years at mycorporate job. Okay, now, Brian,

(03:29):
can you elaborate on your investment philosophyand the approach it comes to value
added multifamily properties. Yeah, So, you know, I've always I've always
been of the mindset that it's reallybest to try to if you're going to
invest in real estate, to tryto do it from a value ad standpoint,

(03:52):
So trying to find a bargain kindof going in right. There's an
old adage in real estate that youreally make your money when you buy the
property, So you know, tryingto find that value add opportunity where there's
an opportunity to you know, obviouslyadd value through you know, making renovations
and things like that, and soin the multifamily space, that's that's what

(04:15):
we primarily look for, is youknow, multi family properties where the units
are innning for less than what themarket is in the area, and usually
that's because you know, they're eitheroutdated or they're being poorly managed, or
in most cases it's a combination ofboth. So that's primarily what we look
for in the properties that we investin. And after spending so much time

(04:36):
far as in financial services, whynot transition into commercial real estate? Into
commercial real estate or yeah, well, the multifamily the multi family properties that
we invest in now are considered commercial, but in terms of like are you

(04:57):
talking like office space or some ofthe other types of yeah, yes,
So you know, it was muchmore It was a much more natural transition
to do large multifamily because it's thesame concept as doing single family rentals,
just multiplied by a lot more units, and so it was a much more
natural transition. Also, I tendto, you know, my belief you

(05:20):
know, different real estate investors aregoing to have different beliefs, and I
think there's good investment opportunities and allthe different kind of commercial assets. However,
I will say that I've always beena big believer in residential because people
need a place to live, right, so that that's never going to change.
And specifically, you know, whenit comes to residential there's been a

(05:43):
housing shortage for quite some time now, and so that that helps present some
some opportunities there. Okay, Nowin going into real estate and being in
it as long as you have,what are some of the lessons that you've
learned along the way? Oh boy, there's there's a lot of lessons there.

(06:09):
You know, one thing I don'tI'm not ashamed to admit. You
know, if really, if you'reinvesting for any length of time and in
any particular asset, you're going tolose money, right and and I've had
my you know, I've I've lostmoney in real estate. And one of
the lessons I learned early on was, you know, I was doing really
well flipping single family properties and thenI got into a property that was a

(06:31):
larger property, much more expensive property, thinking, oh, I can you
know, I can replicate the successthat I've done in these smaller properties into
this big, expensive property. Andbottom line is I lost money on the
deal. It took way longer tosell. There was a lot of extenuating
circumstances. It could be a wholeflip. This house episode on TV with

(06:53):
all those stuff that that happened inthat that flip. But there's there's a
lot less buyers when you start higherprice points you get to in real estate
in terms of single family you know, there's there's less buyers out there.
And the timing of it wasn't great, and I probably over improved the property.
You know, even my very firstproperty that I flipped, I way

(07:14):
over improved it. I was waytoo picky. You know, you hear
a lot about you know, whenyou're investing in real estate, you have
to make sure you look at itlike an investment and not a house that
you're going to have to live in. And with the first house that I
flipped, you know, I gotsuper picky. You know, this little
run in the baseboard, you know, and all these different things and just
way way over improved, did waytoo much stuff, got too picky,

(07:35):
and it was really expensive. Andhowever, you know, I did make
a whopping eight hundred dollars on theproperty, but I learned a ton.
It was really the learning and probablyeven more than that, it was proving
to myself that I could do itand taking that first step and getting over
that hurle and getting over that fearof taking that, you know, investing

(07:57):
in that first property and just goingfor it. I didn't even have have
contractors lined up. I didn't knowwho was going to do the work on
the property. I literally talked tothe neighbor after I bought it, and
they said, oh, hey,I've got a general contractor, buddy,
that does work. And so Iended up using them, and you know,
paid too much money for that.Again another learning you know, lesson
that I learned there. But uh, but bottom line is if I hadn't

(08:18):
taken that step, I wouldn't bewhere I am today. And so that
was a huge learning opportunity but alsoallowed me to get over my fear.
Okay, now along this journey,were there any mentors or if you can
go back and find that young Brian, would you would prefer to have a

(08:43):
mentor at that time? And andI and I had, you know,
some my my real estate agent thatI was using at the time. You
know, he kind of served asa as a little bit of a mentor
for me, you know, hekind of he kind of helped nudge me.
You know, I was literally havinga conversation with him on the patio
in the front of this house,and you know, I he looked at
me and he was just like,Brian, you know, you just got

(09:05):
to do it at some point.You know, you've read all these books,
you've done all this education, You'reat a paralysis by analysis standpoint.
You've just got to do it.And so he did help me get over
you know, get over that fearand taking that first step. And you
know, I did lean on himover the years to kind of help help
guide me through some of what Iwas going through and some of the lessons

(09:26):
learned. I think, you know, generally speaking, if you can learn
from other's mistakes, that's some waybetter way to learn than making the mistakes
yourself. You're inevitably going to makemistakes yourself. That's if you're not making
mistakes, you're not taking risks,you're not taking chance, and you're not
going to you know, you're notgoing to excel in life. Right.
But yeah, he definitely helped me, and there have been other mentors along
the way. But yeah, ifsomebody can find a mentor that can that

(09:52):
can help them that they'll they'll kindof help shortcut some of the some of
the experience. So you share withthe of the obstacle that you faced in
how you handled those. Were thereany other milestones along your journey? Yeah,
you know, so in terms ofthe transition from the single family space

(10:18):
to the multifamily the larger type projectsthat I'm doing now. You know,
one of the things we kind ofhad my wife and I had a life
event back in twenty eighteen. Shemy wife, was diagnosed with breast cancer.
Fortunately she is cancer free now,she's doing great. But that life

(10:39):
event really made both of us kindof stop and reflect on life and you
know, what are we doing,Why are we doing what we're doing?
Where do we see ourselves in thenext five, ten, fifteen, twenty
years. And so, you know, we tried to kind of turn a
negative thing into a positive thing.And that was when I decided, you
know, and we decide together thatthese larger multi family projects were going to

(11:03):
help expedite the process a little bit. There's plenty of people that you know,
can do really well and succeed andsingle family properties and scale that that
wasn't for me though I didn't reallywant to. I didn't really want to
go and purchase one hundred you know, single family properties to try to provide
the income that we were looking forand everything, so decided it would be
it would be a better option forscaling purposes to get into the multi family

(11:28):
projects. And so that that lifeevent is kind of what spurred head Start
Equity and kind of started that process. Okay, and that's interesting that you
brought that up, and that iswhat changes in the industry have you noticed

(11:48):
over the years. Yeah, well, it's way more competitive. There are
a lot more people investing in realestate than when I started. I mean,
there was a decent number of peopledoing it when I started, but
this was probably twenty two years ago. And you know, I kind of
a funny story, you know,I had funny but not so funny.

(12:11):
I had a couple of properties thatI did seller financing on to somebody recently,
and I ended up having to basicallythey stopped making their payments. They
hadn't made payments on it for likethree months, and so I had to
foreclose on the property, just likea bank would do. And I went
here in San Antonio, the waythe county does it when they auction off

(12:33):
properties, you literally go to thecourthouse steps and there's the different you know,
trustees for the different properties are outthere and they started talking about the
property. And you know, backwhen I did this, when I started
doing this twenty plus years ago,there would be a handful of people at
this event. At these events rightnow, when I went, it was
crazy because there was booths set up, there was this whole I mean,

(12:54):
there was dozens and dozens of peoplethere and you know, it was just
it was just this whole spectacle.I was just like, this has changed
so much from from when I firststarted. So I think it's gotten a
lot more competitive. There's a lotof different you know, a lot of
people trying to you know, figureout their niches in the in the space,
and so there's a lot of peopleyou know wholesaling meaning trying to get

(13:18):
find a property, find a sellerthat's distressed that needs to sell it,
and then get it under contract andthen try to find a buyer after the
fact. And you know, sothere's just it's way more competitive than than
when I started. There's still waysto succeed and do well. Plenty of
people are doing it, but it'sdefinitely more more competitive than it used to
be. And I know that there'sa lot of especially internet traffic, that

(13:43):
there's a lot, of course isbeing offered far as one real estate because
one unique thing about real estate,and that is you can't make any more
land or any more you know,it is what it is right there.

(14:03):
You can't go out and create anymoreyou can build on it. So that's
been one of the things that reallyI believe that that may have spurred ars
like the New found gold rush.Right there is the actualization or the realization

(14:28):
that hey, real estate, gettingthe property right there, holding on to
it. Now, there's much moreto it than just getting the property and
saying, okay, now I havean ATM. I have the property.
I just put bodies in it,and it's like an ATM. Every time

(14:48):
I go by this time of themonth, it's just going to be spitting
out change. Tell us about that. Rainbows and unicorns. Yeah, it's
uh, it does crack me upwhen when so, first of all,
there are a lot of there's tonsof courses out there. There's so many

(15:11):
that are just just, I don'tknow, ridiculous to me, Like I
theoretically, yes, you know,no money down and all these great all
these things that they tell you,Yeah, theoretically, yes, it's possible.
It is possible, and there areways to do it, and there
are people that are successful with it, but it is, like you said,
there's a lot more to it,and you know it is not you

(15:33):
know, some people like to say, oh, you know, go get
a single family rental house, it'sa passive investment. Well, it's not
a passive investment, you know.And even if you have a property management
company that you hire to manage youfor you, it's still not passive.
You know, they're they're still goingto be coming to you for certain questions
and things like that, and soit's it's not a passive investment and there's
still decisions you'll have to make.But I personally, I've actually never used

(15:58):
a property management company. Always managedmy properties myself. Obviously, not the
apartment buildings, that's not something that'spossibly not feasible, but in the single
family, small multi family space,I've always managed it myself. And you
know that it's not passive. There'sthere there are some good courses out there,
but I think, you know,for me, I think if I

(16:19):
could give people one piece of adviceon trying to get educated in real estate,
whatever avenue you're going down, Iwould I would kind of go back
to what you mentioned about finding amentor and finding one that's local to you,
because I think there's so many ofthese courses out there that are national
and you know, do all thisstuff online and that's great, but I

(16:40):
think you really needed to be ableto sit down with somebody, have coffee
with somebody, and you know,just pick their brain a little bit,
and you know, go with themto go check out a property and get
their thoughts on certain things. Andyou can't do that if it's all virtual.
I mean, I guess technically youcan, but it's not the same.
And so, you know, evenwhen I got into the multi family,
these large multi family I joined alocal mastermind group here in San Antonio,

(17:03):
and that was one of the gamechangers for me in this space because
I was able to get around peopledoing these large, you know, multimillion
dollar deals that you know, beforethat, I always thought, well,
you know, I don't have youknow, a million dollars in cash sitting
around to go put into a property. But then I was able to get
in a room with people that werefiguring out a way to do it,
pulling money together, you know,investors and things like that, and so

(17:26):
I think that's one of the biggestkeys, is finding a mentor that will
will really help you. And Iwould say, I would say that,
you know, people that are seriousabout it interview some different mentors, don't
just jump into the first one youfind, and because they're not all quick
created equal, and you may not, you know, you may not gel

(17:47):
with that particular person, and Ithink that's super important. So yeah,
that would be Yeah, it's it'snot it's not all you know roses,
and you know, there's definitely somechallenges and you know, victions and things
like that. I'm literally, youknow, I've still got some of my
single family properties now too. Diversificationis important to me, so I'm holding
onto some of those as well,and I'm literally going through an eviction process

(18:11):
right now, so those things happen. And I would imagine also that each
area, as far as the regionthat you're in, also has a lot
to do with that. So it'simportant that you know, Okay, I'm
in the southwest or I'm in theeast, then it's good to know far

(18:36):
as what are some of the thenuances I would imagine versus you can't get
it offline right there or just googlingthat sometimes you got to be in the
area in order to really get asincere feel far as for it, Yeah,
for sure, I would totally agreewith that. I think, you

(18:57):
know, that's the whole boots onthe ground theory, right, We're not
really a theory, it's a thing. You know, you want to have
boots on the ground. You wantto have somebody there, local in that
area, somebody that understands in themarket. And you know that's why from
a from an active standpoint, I'venever actually gone outside of Texas to invest
I mean, I've always stuck tothe state. This is what I know.

(19:18):
And yeah, it's it is verydifferent state to state. You know,
some states are more landlord friendly thanothers. Right, Texas is considered
a landlord friendly state. California isnot. You know, it can take
months and months and months and monthsand months. And you know what,
after doing this for a while,one of the things that that does frustrate
me a little bit is and there'sbad landlords out there, don't get me

(19:41):
wrong, but this whole you know, this this whole concept of you know,
slum lords, and there are someof them, but you know,
I think landlords tend to get clumpedinto all together by some people, and
you know the reality of it is, you know, most real estate investors
like myself, right, yes we'relandlords. Yes we're collecting rent from people,
but we have loans we have topay too, and when tenants don't

(20:04):
pay, that hurts us. Andso it's it's you know, I had
during COVID, I had I hada tenant actually call me up and tell
me because you know, they weredoing the they were pausing the evictions and
stuff like that during COVID, whichis fine, but I had a tenant
call me up and say, uh, yeah, I heard I didn't have

(20:26):
to pay my rent. The presidentsaid that we didn't have to pay our
rent. I was like, no, that's not really, it's not really
how this is. This is working. We can't evict right now, but
if you don't pay that, you'rejust setting yourself up for in the future
that's going to happen. So theyjust didn't government didn't want to create that
hardship on people during that time.But you still are supposed to pay.

(20:47):
So it was kind of interesting.But yeah, there are some bad landlords
out there, but there's there's alot of good ones too. Yeah,
that sounded like that was a littlebit of selected hearing. Selective hearing right
there. For it's so so uh. The main things FAR is for someone
who's looking to go into the realestate business, such as yours, or

(21:12):
to take on a journey such asyours. You had mentioned finding a mentor
far someone that's local. So whereare some of the places that a person
would find. Would that be thenational or the regional real estate association or

(21:33):
how would they go about finding aYeah, you could do that, you
know pretty much. Now there areso many different meetups in every city now,
different real estate investing meetups. Youknow, we have we have actually
our own real estate investing meet uphere in San Antonio called Wealth and Whiskey.
Kind of a pretty cool name.Buddy of mine came up with that

(21:55):
name. But but there's so many, there's so many different meetups where you
can meet a lot of interesting peoplewho are doing these types of things.
And I think that's one of yourbest bets is trying to find somebody at
one of those meetups because most ofthem are free, you know, so
you can just go during the weekon an evening and just you know,
try to find some folks that arelike minded, that are willing to help

(22:17):
you. One of the one ofthe biggest challenges, honestly is finding somebody
that is willing to take the timebecause you know, just like any any
industry, any any business, right, everybody is busy. You know,
everybody only has so much time.And you know, time is very valuable.
You know, you can't get itback. So you know, finding

(22:38):
somebody that's willing to work with you, you know, and if you can
find that, and even better ifyou can find it with somebody that you
know isn't going to charge you atarm andal a, you know that that's
great. And and you know,just I think you just got to get
out there and you just got togo to those meetups and you've got to
try to find some folks that thatare willing to help you out. That

(22:59):
is so important right there. Nowanother thing, and that is just as
when you were in the financial servicesbusiness, where continuous education is important because
the uh, the business is constantlychanging. So give us your take on

(23:22):
that right there, or give ussuggestions as far as for this series.
Yeah, I think that you know, books are still a great way to
educate yourself, you know, forme, when you know, kind of
my first the first little seed plannedfor me and investing in general, was

(23:44):
from my economics teacher in high school, where we had to He asked us
to start tracking stocks and in thenewspaper. This is back when there was
no internet, so we were trackingthe stocks in the newspaper. And that
kind of, you know, putthat seed in my mind. And then
when I graduated high school, Ijust went to the library and just started
checking out books and you know,learning everything I could. There were podcasts.
There wasn't the Internet like there isnow, so obviously now there's podcasts.

(24:07):
You know, podcasts are great.It's a great way to learn a
ton, and so podcasts, there'sso much information on the internet. Again,
mentors are a great way. ButI think, you know, for
me, I obviously I stay reallyconnected with what's going on in real estate,

(24:30):
but I'm I like to look ata much bigger picture too, of
what's going on in the economy.I was just you know, I watched
CNBC most days, you know,just to kind of get a pulse on
what's going on, listen to differentpodcasts that have nothing to do with real
estate that are more on the economy, where you know what's going on with
interest rates, and you know,as much as I don't really like politics,
I kind of keep up with someof that as well, just to

(24:51):
stay you know, educated on what'sgoing on because that can that can affect
you know, you know, realestate values, that can affect you know,
policy changes are big, you know, in real estate, especially when
it comes to taxes and stuff likethat, and so I just think it's
important to keep your education diverse anddon't just you know, if you want
to get into real estate, obviouslyyou really need to dig in and go

(25:12):
into that and research that, butdon't limit it to that. Look at
some of these other financial avenues aswell, and keep yourself abreast of what's
going on outside of the real estatemarket and how that can impact real estate.
So, oh, that's a lotright there now, Brian. Brian,
I know you're a very busy man, and I greatly appreciate you're taking

(25:37):
the time to share as far aswith the audience this valuable information because this
could actually be applied far as toa variety of other industries. Now,
before you leave or before we endthis, could you give us some pointers

(26:02):
or what would you like our audienceto unpack. What are some of the
most important things that they should goaway or come away with. Yeah,
I think you kind of Actually youmentioned it with the education piece. I
think education is huge, and that'sone of the reasons why I do what
I do now, is because Iactually love educating folks on real estate.

(26:23):
I could talk about it all day. I just have to, you know,
temper it a little bit because Iactually need to do some work too,
But I could talk real estate allday. So I think education is
important. You know, we alsotouched on fear a little bit earlier,
and I think you know, andagain, like you said, this could
be applied to other avenues as well. But you know, the reality of

(26:45):
its success is on the other sideof fear, right, and so you've
got to be able to get overthat fear. In any avenue of business,
you've got to be able to getpast that. And you know that
that's probably one of the things thatstops most people from from getting very far,
and especially entrepreneurs that that are lookingto because it's a whole different corporate

(27:06):
world is one thing, right,the corporate world, Yes, you have
to work hard, and you haveto do all that and you have to
be creative and things like that,right, but things are more dictated to
you in the corporate world. Rightyou're kind of told, here's the things
you need to do. You know, this is how we're going to evaluate
you and everything. When you're anentrepreneur, it's all on you, like
the buck stops with you. Youyou you know, it's all based on

(27:29):
you know, your success is allbased on what you what you're able to
do, your success of your business. And so I think getting over getting
over fear is is just one ofthe one of the biggest things for people.
And you know it's not and it'snot just jumping in and you know,
haphazardly and not planning. I thinkyou need to You need to plan
and goes back to educating yourself andtrying to set some things up. And

(27:52):
you know, I fear is abig thing. And it obviously helped me
back for a while too, becauseI was in a corporate job for a
long time, but I was kindof I knew I wanted to be an
entrepreneur and I knew that was realestate was what I wanted to do.
But I still stayed in the corporatejob, and some of that was security,
right I had a great job fora great company and it provided the
steady income and that that was great, but you know, it took.

(28:14):
It took finally getting to the pointwhere you know, okay, this is
this is it, this is whatI want to do. And again going
back to life events that that thatreally played a vital role in that as
well. But I think just gettingover the fear is huge. That's that's
probably one of the biggest things.Okay, well, that's great right there,
because our audience is it's a diverseaudience right there. And one of

(28:37):
the things that we're finding out andthat is that there's a lot of entrepreneurs
that are over fifty five that aretheir first time out as far as in
the field right there, because thelandscape is constantly changing, so that those

(28:59):
are some great words of wisdom rightthere. Brian, again, we thank
you far As for taking the timeand sharing with us your journey and how
you turned your dream into a reality. So that way right there, our
audience who are listening and looking atthis podcast, that they'll take those golden

(29:22):
nuggets and apply it to their circumstancesand at the end of the day,
turn their dream into a reality andbe intentional about it. Right there.
Thank you, thanks for listening tonight Beat Media's Living the Dream. If

(29:55):
you enjoyed this podcast, please livea comment or hit follow and subscribe on
our lake so you can stay upto date on new episodes until next time.
When writing the story of your life, be sure you're holding the pen
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

CrimeLess: Hillbilly Heist

CrimeLess: Hillbilly Heist

It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.