All Episodes

May 16, 2025 12 mins

Send us a text

Ever wonder how to build substantial real estate wealth while keeping your day job? Meet Cole, a full-time airline pilot, part-time military helicopter pilot, and real estate investor who's built a $5.5 million portfolio spanning 63 units—all without quitting his aviation career.

Cole's journey began humbly washing dishes as a teenager, using minimum wage earnings to fund his passion for flying. His first real estate purchase was a modest $100,000 HUD foreclosure bought with just $3,000 down. That single property became the foundation for his multi-million dollar portfolio. Unlike many real estate personalities advocating for immediate large-scale investments, Cole shares a refreshingly practical approach focused on gradual growth and strategic positioning.

One of his key insights is the critical importance of your first few deals. While experienced investors can weather unexpected expenses, newcomers need particular caution to avoid burnout. Cole also reveals practical hacks like obtaining a real estate license to earn commissions on purchases and save when selling. For busy professionals juggling careers with real estate aspirations, his time-efficient approach to property analysis—completing evaluations in under 20 minutes by focusing only on fundamental value drivers—provides a realistic framework for success.

What makes Cole's perspective valuable is his commitment to authenticity over hype. He's building a community for real operators rather than selling courses or promoting get-rich-quick schemes. Whether you're contemplating your first property purchase or looking to scale while maintaining your career, his journey demonstrates how disciplined investing and patient positioning can transform modest beginnings into significant wealth. Ready to see how your first $100,000 property might change everything? Join Cole as he documents his continuing real estate journey.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hey, my name is Cole.
I'm a part-time real estateinvestor in Milwaukee, wisconsin
.
I'm a full-time legacy airlinepilot and a part-time helicopter
pilot, so I'm juggling a lot ofthings.
But this is my attempt attrying to talk about real estate
in kind of a way that maybewould be beneficial to people
that are just getting their footin the door, looking at real
estate from the outside andsaying, man, I would love to get
into that, but I don.
I started as a dishwasher atthe open hearth and worked my

(00:23):
way from there.
So we built into 63 units.
I've got partners.
I'm the majority partner butwe've got some minority partners
.
It's about 5.5 million or so,plus or minus a little bit, for
total asset value Not thebiggest portfolio out there by
far but I'm trying to get aheadof it and say, document where
I've been and then catch up topresent day and then go from
there with what we're doingtoday.

(00:45):
Just this morning I toured asingle family house with my
buddy and stuff like that Ithink would be awesome to talk
about to somebody who might belooking at the real estate
market, saying I'd love to getinto that or find a way to get
my foot in the door.
This is hopefully going tobring a lot of value to those
people and for absolutely zerodollars.
So we'll see what happens.
So, basically, backgroundstarted as a dishwasher at a

(01:06):
place called the Open Hearth.
It was a lovely restaurant.
I never actually ate their food, but I worked there as a
dishwasher for about a year, 14to 15.
And then 15, I upgraded and Igot picked up at Five Guys
Burgers and Fries, flippedburgers there and hung out there
for a while.
Awesome people I met someawesome characters out there,
really had a blast consideringwhat it was, and then I moved on

(01:27):
from there.
But during that period of time,while I was in high school, I
was using that money to pay forflight lessons.
So it was costing me, I think,maybe $130, $140 an hour for one
hour of flight training and inreturn I was giving them all my
hard-earned dollars at Five Guysor previous to that, the open
hearth, and I was making $7.25an hour or whatever.

(01:47):
From that point forward got tonear the end of high school and
I was like man, I want to fly, Ilove flying, it's awesome, but
it is freaking expensive.
So I was like I need to figureout a way to offload that cost
and move it somewhere else.
And I moved that onto theshoulders of the military
somewhere else.
And I moved that onto theshoulders of the military.
Uncle Sam was looking for somepilots and it just so happened
that I was looking to be a pilot.

(02:08):
So we found an agreement thereand they sent me off to flight
school.
I had about a year wait afterhigh school to actually make it
to flight school, so I graduatedslightly early, like about a
semester early from high school,and I ended up working at the
post office.
So I was slinging mail in theinner city of Milwaukee, getting
harassed by people and justhaving a blast.
So I was slinging mail in theinner city of Milwaukee, getting

(02:28):
harassed by people and justhaving a blast.
So I was delivering mail untilI went to flight school.
Go to flight school, graduateflight school, come home and
that's my first taste of gettingmy foot in the door with the
real estate stuff.
I had gotten my real estatelicense to operate as a realtor
in Wisconsin but I have to tellyou I absolutely hate sales.
So I am not the realtor thatyou would want.
It has that same used carsalesman vibe to me and I just

(02:52):
really hate that.
So I do it for friends andfamily and primarily for myself.
Fun fact, kind of a hack forsome of you who are looking at
trying to get into investmentproperties get your real estate
license and if you buy your ownproperty you get paid a
commission and vice versa, ifyou go to sell a property you
can do it for $0 commission.
So if you're trying to savesome money and make a deal just
a little bit sweeter, that's oneway to do it.
It's only a couple percent, two, three, four percent, but two,

(03:13):
three, four percent does add up,especially when you're starting
out and you don't have a lot.
So that's something I alwayssuggest to people because it
costs money and you have to takea test and you have to study
and everything.
But if that's going to be thebarrier that stops you from
getting into real estate, thenyou're probably not a good fit
for it anyways, because there'sgoing to be a lot more kicks in
the teeth than taking a test andtrying to study for it if you
really want to dive into therental property world.

(03:34):
So first, property as a HUD homeforeclosure online I think it's
called like hudhomestoreorg orsomething like that.
It's government foreclosuresbasically, and what a government
foreclosure is, at least in thecase of this house, was a FHA
loan that somebody defaulted onand then the government ended up
with it back in their hands.
So FHA loans are kind ofgovernment-backed loans,

(03:54):
whatever.
And I went and toured thishouse and it was a little scary
because I'd never really been inlike a really beat-up house
like that.
But I kind of took some peoplethat I trusted with me one of my
friends' dads and him, and thenmy parents.
Some people had good feedback,some people didn't, and I
decided to roll the dice.
So the initial property was$100,000, single family three

(04:15):
bed, one and a half bath, put$3,000 down.
I was a first time home buyerand got all the credits and all
this stuff.
So this is 2017.
And then, rolling forward fromthere, that single family was
the catalyst for everything.
It's a hundred thousand dollarhouse, basically nothing, but it
rolled into five plus milliondollars and a lot more coming
down the pipeline here of realestate.

(04:36):
And it all started with thatone house.
So if I was to say anything toanybody is it may seem like a
small deal.
Your first deal is like man,this is nothing.
There's such bigger players outthere but it's.
It really could be thedifference of me doing
everything or doing nothing.
So take it seriously and Ialways tell people like your
first five deals, that's whereyour money is truly made,

(04:56):
because I can weather and peoplebigger than me, way bigger than
me, can weather the storm of abad deal.
Right, you get a bad duplex,for example, I bought and it was
like $40,000 I was notexpecting to spend and we were
able to weather that storm.
But if this is your first dealand you get hit with that bill,
that could be the thing thatputs a bad taste in your mouth
for real estate and also kind ofends your career before it even

(05:19):
began.
So just think about that andsay, hey, you know what I'm
going to, maybe I'll pass on acouple of deals.
I really want to find basicallythe perfect deal or as close to
perfect as reasonably you canget.
So something to think about.
I just saw a video Grant Cardoneput out where he's I wouldn't
even start with a single family,I'd start with a hundred units.
You know I'm going to go.
You know go big and 10, x andthis and that, and it's like man
, if you're, if you're theaverage person listening to this

(05:44):
, I'm from a.
You know I'm from the Midwest,like if you're an average
Midwestern, you know you don'tworry about the money, just find
the deal.
You find the deal Like youdon't know anybody that has any
money either.
So it's like what do you do?
So I'm going to try to totallyflip that on its head and I'm
going totally practical thingsyou can do to try to save money,
try to make money, try to getyour first property, and then
we'll just kind of go from there, preach about what I haven't

(06:05):
done.
So hopefully that will bringsome value to those of you who
end up watching this video andthe future videos to come.
And if you're just listening toaudio, I'm going to try to do
my best to kind of make themcoalesce and not really do too
much for the visuals.
That way the audio listenersaren't losing out on too much.

(06:27):
But if I end up doing one orthe other, please let me know.
And same with the video.
I'm not a videographer or aphotographer.
So if you see something that'segregious, please help me and
I'll help you by you helping me,I guess, and making better
videos.
I'm going to talk a lot abouttrying to manage real estate,
whether that means buying,selling, actually managing the
properties, whatever it may be,and doing a full-time job.

(06:49):
My full-time career at theairlines and flying for the
military takes up a lot of time.
Sometimes it kind of ebbs andflows.
I've had a couple of days herewhere I didn't have a lot going
on, but then some weeks I'm likeevery day I'm either flying in
the jet or I'm in the helicopterand that takes a lot of my
brain power.
So it's like how can youcontinue to build a portfolio
but also keep your job?
Because a lot of people theanswer they want to hear is, oh,

(07:11):
just quit your job and just goall in on real estate and hey,
that works for a percentage ofthe population, but it's not a
cure-all for everybody.
And in my case, for me to leavewhere I'm at now is really
challenging and it's something Ithink about a lot, but it's
just not quite where it needs tobe to be able to really
consider that.
But even back when I was makingno money, I mean, I was flying
for a regional airline and we'regetting paid like $30 per

(07:34):
flight hour as a first officerand like that sounds like a lot
30 bucks an hour, especially in2018, 19 timeframe but at the
airlines you're only gettingpaid for the hours you fly on an
average trip.
You're not flying 24 hours aday.
You're not even flying sixhours a day, maybe.
So it was a really, reallychallenging time, but I was
finding ways to make it work.
And even back then, when Ididn't have money, I got that

(07:56):
first house.
It took me almost two years toactually fix it up and make it
nice and then I rolled thatmoney that I had maybe 50 grand
with another 20 grand from afriend of mine that I took on as
a partner and he rolled thedice on me and we bought an
eight unit and then we ended upselling that eight unit down the
road and, clear to check, thatwas almost 300 grand.
So just because you're notmaking a lot of money doesn't
mean you don't have the abilityto go and enforce that equity

(08:17):
somewhere within the market andfind an arbitrage somewhere,
because they're everywhere.
You just have to either havethe knowledge to know how to
find them and or spend enoughtime in the market that
eventually, something just fallsin your lap, which it does
happen like that sometimes, buta lot of it has to do with
putting yourself in the position.
The reason I got that deal isbecause I got my real estate
license back when I was justgraduating high school.
I was saving up money workingat the post office slinging mail

(08:39):
, and I was flying helicoptersat night because I didn't have
enough hours to go get a realflying job.
So I was doing that kind ofstuff to put myself in the
position for that opportunity.
But those things didn't makethe opportunity happen, if that
makes sense.
I just was available and readywhen it did come.
So that's the one thing thatyou can do is try to put
yourself in the best position towin when that time comes.

(09:00):
It's not going to be maybetomorrow, it may not even be six
months from now, but if youdon't have all your ducks in a
row when that opportunity comesand you have to pass on it, it
hurts down the road when you seewhat that could have been and
you're just on the sidelinesjust watching.
Is real deals?
People talk all thesehypothetical numbers and a lot

(09:21):
of people are using things thatI really don't think are
important into looking intodeals and people are
overanalyzing deals.
They're showing people how todo all this paralysis by
analysis, type, deal making andto me, I can get in and out of a
property in probably fiveminutes and have a pretty good
idea of exactly what I need plusor minus a couple thousand
dollars maybe and I know whatthe market value is.

(09:43):
I can do all this stuff.
I can do an analysis on aproperty in 15, 20 minutes
easily and I think that thoseskills it's not even a skill
really, it's just knowing how tolook past the BS and not get
hung up on it and just look atthe things that really matter.
So I'm going to be doing a lotof shorts and a lot of TikToks,
probably of those kind of dealday by day deals.
But I do plan on doing somelonger form content of stuff

(10:04):
that I've bought and what I sawon those properties and how it
played out wins and losses.
I've had some losses for sure,and I'm going to do the same
thing with deals that I'mlooking at.
Today, like literally today, Iwent and looked at a deal at 930
this morning with my buddy.
They wanted, I think theywanted 80.
I offered 70.
They came back at 76 and Iended up offering 74.
So we'll see if I get it, butthat deal would be an

(10:24):
interesting one to talk aboutand I think that people that
haven't bought a deal would findsome value in that.
I hope to bring on guests atsome point too.
I don't want to do it until Ihave an established audience and
people that actually want tosee that, because I know for a
long time I'm probably lookingat years of single digit views
on these videos and I understandthat's just the name of the
game and I may not even beproviding that great of content.

(10:45):
I'm going to reserve the guestsuntil I have something
established and I prove tomyself that I can stick to this,
because otherwise I thinkyou're putting the cart before
the horse, and I'm a big one ofmy big things is not doing that.
So I really try not to, and I'min that case.
I'm just going to wait for now,but we have a lot of content
that we can talk about justmyself.
So that's the plan.
I'm really looking forward toit.

(11:05):
That's generally.
The idea is basically justbringing what's real, what's
going on, and trying to bringvalue to people that are either
looking at real estate as anoption, are currently in the
market and building some sort ofcommunity around that I'd love
to really bring together likereal operators.
I don't really want to beinvolved with the course selling
and the gurus and the this andthe that, like, I'm just going
to be real.

(11:25):
Some of it's going to be goodcontent that some of it's
probably going to be bad, butI'm just going to give you
what's going on for me, for real, and we're going to build a
community from there.
That's the plan.
Really appreciate anybodythat's taking the time to watch
this and put themselves throughthe agony of listening to this.
Right now, I've got a lot oflearning to do, especially on
the YouTube side.
The last YouTube video I everuploaded was like 2012.

(11:45):
So I'm way out of the loopright now.
I'm an old, 29 year old, soforgive me, but if you have any
feedback of any kind, you haveany interest in leaving a
comment, please, please, leave acomment and I will totally get
back to you.
We'll talk in the comments andthen we'll go from there.
Really appreciate everythingthat.
Advertise With Us

Popular Podcasts

Are You A Charlotte?

Are You A Charlotte?

In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.

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

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

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

Connect

© 2025 iHeartMedia, Inc.