Meet The Dad Who Made $250K Profit with Dirt in 12 Months

In this conversation, Dylan walks Clay through how he went from sending blind offers on direct mail to closing development deals worth $300-400K net — including a 22-acre subdivision he closed on seller financing, a rezoning project he personally drove around with the landowner, and a survey hack deal where he split off 30 acres from someone's homestead. 

He also breaks down why he focuses exclusively on Wisconsin, how local relationships with landowners, realtors, and title companies have become his biggest competitive advantage, and why he'd go all in on cold calling if he had to start over today.

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Transcript

all while working at W2 and having those family responsibilities
most important so
I'm a husband and a father of uh
3 3 kiddos under 5 years old
land investing has allowed me the freedom and flexibility to
to pour into my family I did about 15 flips in my first 12 months
gross profit right around the 250 k range
and that's where my business really took off
I quit my W2 actually
in December of 2025 scale into a
building a team going after some big development deals
as opposed to just me flying by the seat of my pants
today
I'm sitting down in the Landman podcast with Mister Wisconsin himself
if they had a Mister Olympia or a Miss Universe in Wisconsin
it would be this man a former private coaching student of mine and a
a land investor that a lot of people can learn a lot from
so I'm super excited to Jan with uh
Dylan Roosh today what's going on brother
yeah I'm
I'm good Clay
thanks so much for having me
yeah like you mentioned
it was great I've been working with you one on one uh
for a little over a year and excited to talk about that experience and
and kind of where my land business is at today
so who is Dylan Rouge
give us the uh
the background on you yeah
so I I better start with what's most important
so I'm a husband and a father of uh
three three kiddos under five years old
so that's primary and
and really
land investing has allowed me the freedom and flexibility to
to pour into my family and have more time and
freedom and flexibility for my family
um I started land investing in December of 2023
and had some great early success
I did about 15 flips in my first 12 months
gross profit right around the 250 k range
all while working at W2 and having those family responsibilities and
and then about December of 2024
about a year into my business
is when you and I got connected
and we worked together for 12+ months from there and
and that's where my business really took off
you helped me scale into a
building a team going after some big development deals
so much so that I quit my W2 actually
in December of 2025
so I'm just a couple months removed from the W2 life
and now I'm I was expecting to show up with a
with a a sweater or a
you know a sweatshirt and a
and a T-shirt you know
you're no longer in the W2 world
yeah no it's
it's been great it just allows you
like I said more time for family
but also like
I have this walking pad treadmill underneath my desk
I'm getting my steps I'm working out
um just
all those things help so much
leaving the W2 and going full time as an entrepreneur
so it's been a blast so far dude
so what got you like
what originally attracted you to land investing of
of all things yeah
for me we had
my wife and I had a few Airbnb short term rentals that we had
I think we had two or three at the time
and those were really successful here in Wisconsin
and we early on
I thought oh
I need to continue to generate capital
in order to keep funding buying rental properties
and so that was my plan early on
to get to use land investing to get kind of those capital pops
to then fund rental real estate
and then as I got into land investing and building a business
I'm just like
why would I even invest in short term rentals or rentals at all
if I can just build a business that um
can scale and and make way more than a short term rental can
so that's where it all started
and I dove in I was part of the App Key community um
and it's it's been a blast
I eat sleep
breathe all things land investing
and I could talk about it all day
so it's something I'm passionate about too
dude that's super cool
I I
it's interesting like
a lot of people come to it for different backgrounds and um
you know I
I like the fact that you're like hey
I wanted to get active income
one of the things that mistakes that I made
Dylan and I know you know this
out of our many conversations is like
I actually went for the now I was working for someone
and then I went to the act at the passive income right
which is
it's really hard to scale that unless you raise a lot of capital
um and so did you buy those Airbnbs with your own money
or did you did you raise capital to buy them
like how did you
how did you get those going
yeah we
we bootstrapped it so um
we house hacked so the first uh
place that we bought was a duplex and uh
I got my wife on board to
to house hack and then um
turn the other unit into an Airbnb
so it was super successful
and she kind of saw the writing on the wall like hey
we can make this work and then um
our next property we lived in it for 12 months
got that owner occupied financing
moved out and then turned that into an STR
so I totally agree with you
like I think everyone was kind of sold this dream of passive income
and I think that's kind of a fallacy
and um
and I think you'd agree
where I'd rather go after massive income as opposed to passive income
where you build a business and something that can really scale
um that's what really clicked for me
probably a few years ago now
and there's no turning back
yeah man
yeah that's the
I had the experience with the Airbnb too right
which was wasn't a good one right
obviously yours was
was a lot better so when you were
but like
before we worked together
Dylan in general
like what
what was your kind of world like
I know we got some really interesting successes
which I'm super proud of you and
and uh
just admire what we're gonna talk about today
like did it all yourself
it was really impressive but like
where were you in your first year versus
like now
like how do you think differently
how do you operate differently and
and but originally
kind of what was your
where you were in in the land world
yeah so when I
when I first started out again
I was still working at W2
so I thought direct mail was kind of the best uh
marketing channel to use and it's still viable today
um but I was just sending out blind offers
and they were some of them
some of them were sticking
and just building great relationships with land owners again
I'm based in Wisconsin so really
all my marketing targets Wisconsin
and that's been a blast to kind of go after the
the local market there that first year
I did roughly I would say
12 to 15 deals about 250 k gross profit
really going after those flips
um but as I started to work
with you and started to come across more
just leads with different opportunities
that's when I really got into the minor subdivides
the major subdivides the rezones
the entitlements and all that stuff
so um
and I was doing it all myself before
whereas now as we sit here today in early March 2026
filming this um
I have a kind of half time US based uh
sales slash lead manager who's been great
as well as a uh
VA that's uh
working for me full time kind of in an operations role
so I feel much more like an entrepreneur
and much more like a business owner
as opposed to just me flying by the seat of my pants
and trying to keep up with leads
type of thing dude that
that's a huge um shift
it was interesting before I got on
on this call we were placing an offer on like 120 acres
and I was on the call with this
with this broker and he was from Tennessee right
and I got a Yankee accent man
cause I'm a freaking Yankee
you know what I mean I'm a Yankee
we all are Yankees and I want to kind of hear your thoughts
this is a little bit off the
you know the
you know the regular conversation
but Wisconsinite and you and I
I'm I'm pushing this cause we talked about this a lot
but
what's the benefit of being a Wisconsinite and focusing on Wisconsin
or being it you know
a Tennessee and focusing on Tennessee
yeah yeah
great question so
I mean the beauty of land investing is you can do it anywhere um
and we've all proven that
you've proven that with your business
but I think land is getting more local
and you and Justin have talked about this a lot on
on your other podcast where um
developing those local relationships with brokers
with realtors with different title companies um
helps a ton and my two biggest development deals
my first one um
I was on the back of an ATV with the land owner
and we were driving around the land
and I was literally arms around him basically
and straddling him and he was showing me the land
it was super cool I know it sounds weird but um
great experience and we got to know each other better that way
best experience I had last year
yeah yeah
right right
um but
but that stuff matters
and then my development deal that I closed on today um
that's and 22 acres into seven lots
I drove around in the guy's truck
and he showed me the land
and you're able to shake people's hand and build the trust that way
and uh yeah
there's been so many times where I'm on the phone with people
and they're talking about yeah
I got these offers from people out in North Carolina
or name the state um
but you're the only one in Wisconsin that I've talked to
and they kind of give you the benefit of the doubt
usually I know the area that their
their land is in so that builds trust and
and uh yeah
I think land is just getting more local
and especially with these development projects
it helps a ton to for me to attend these rezone meetings myself
to attend the planning meetings
build relationships with town clerks and the plan commission
and stuff like that um
is so important to be local
I gotta ask you a question about that
so as you know
one of the things that I've been talking about a lot lately was um
you know you gotta
you gotta kiss a lot of frogs to find the prince
you know what I mean and so at the beginning of your business
you kiss a lot of frogs you you
you test a lot of different markets
and local people hear local
it's like I gotta be in the backyard
well local could be an understanding or relationships or family
or people in a specific area right
you could try you could be from Wisconsin
maybe not with a Wisconsin accent
but Wisconsin and focus on Pennsylvania right
or you can be Delaware and focus on New Jersey right
these types of things you get
those are expertise so my question for you is
if you say hey
land is local and the next wave
this is a just a personal question right um
do you think that your accent
your background
gives you a exceptional competitive advantage over someone
even maybe with better sales skills
I'm not saying you have bad sales skills
I'm just saying what
when we're weighing out valuable traits
do you think it truly gives you a big advantage
honestly I think it does
it does um
just being able to drive up two hours north if I have to
in order to to walk a property that I'm not so sure about
and just Wisconsin people
like Wisconsin people a lot of times people don't leave the state
so they'd rather sell to someone that's got gonna be local
that can drive up to their property
shake their hand and who has kind of been in the area before
so I think it matters a ton
but to your point earlier too
like you don't have to be from the state
as long as you maybe focus on
maybe one or two areas within your business
so that you know
you have a perk tester that you can call out of the blue
that you need a perk test done in a week or two
or a surveyor I mean
name the contractor
if you're local and you're kind of specializing in one area
I would consider that
almost the same as being local to the given state
I like that what the way I think about it is like
cause you go through these stages right
and for those at a who are listening
like they know about the land ladder
which is beginner Hustler operator
when you get to the operator stage as a CEO
your job you know
one of the things that when we were working together
I was like wow man
you just do more deals right
you just do more deals and
you know you learn and you continue to mature and
and as a CEO actually
the biggest thing that you can do is create magnets of opportunity
once you once you get like
you know you did 2:50
and then you doubled or tripled
and then all of a sudden it's like
how do I double or triple again
it might not be the same formula
it might not be the same formula
and so at that level it's like
how do I think more strategically as a CEO
so when you think about like
over the last year right um
what do you think were the biggest shifts that you made
that took your game from dude
I'm doing 2:50 to I got a development deal on my desk
I've doubled my business I'm now full time in this business
like what were those shifts
maybe two or three shifts that you really made
yeah I
the first one that jumps off the bat tune
I don't think it's talked about enough on different land podcast and
um in different coaching programs
is just the access to cheaper capital
um so
I spent my first year
maybe giving up more of a profit split than I had to
because I was just getting started
I was building the track record
and now if you fast forward to early March 2026
I have more capital partners than I do deals
to be honest so that's a big thing
so when you're first getting started
a lot of times you're doing those 50 50 profit splits
which are great sometimes you have to do them if you don't have the
that access to capital but right now
I'm getting a much smaller
still a great return for my investors
they're getting their money back a lot of times in two
three four months
um so I'd say that's the biggest lever that um
a beginning land investor can pull
is just getting your story out there
showing your track record
and getting access to cheaper capital
and then I think that the other main driver would be
just seeing deals from a different lens
that those first 12 months in land business
I was just like okay
I have to offer 40 k if something's worth 70 k or 80 k now
because I have access to cheaper capital
and also I have the development experience
and different surveyors
that I can count on to maybe do a minor CSM pretty easily
and I know different zoning regulations
in various counties and townships
um that's been the biggest thing so really the
as you know the flips kind of keep the lights on in the business
and then those bigger deals are what really moves the needle
from a wealth generation standpoint
absolutely man
um that's a good one
so cheaper capital is huge
what are a couple other insights that you have
love that yeah um
cheaper capital going after bigger deals
and yeah just
just more more marketing
to be honest um
when I first started out I was doing a lot of direct mail
and as you know that can get pricey
you don't get as many leads
but as I got more experienced in the land investing space
I would rather have more at bats with a marketing channel
and for me more at bats came from cold calling
so I love using cold calling services as my outbound marketing channel
I still sprinkle in some direct mail when I have to
but I would much rather have a
a ton of leads that I can work
and kind of use my knowledge and expertise
from a zoning a subdivide standpoint
potentially pay 80 to 120% of market value if I can
then go and do a subdivide
do an entitlement with some of those deals and
and really all
all my big deals have come from cold calling as a marketing channel
so that's something that I um
started doing in year two
and especially in working with you Clay
and building up my my CRM
and using follow up boss to really keep things organized
so I'd say that was probably the
the next biggest lever to pull is just more consistent marketing
more volume marketing and just more at bats
I remember when we were we
we connected and you started to create these
additional opportunities in your business
I love this I
I wanna really highlight this
um so before we were working together
there was a um
hey I'm just gonna flip a deal
then I remember I'm gonna add double closing then
and I'm gonna become the broker
right that those were these evolve
so talk about your evolution
and you're talking about local
how can I if I'm not local
get the same type of local advantage
whether it's exit strategy or other things that
that that you and I talked a lot about
like how do I do that if I'm in the Bronx
and I'm trying to do this in a different state
yeah honestly
it's probably just picking up the dang phone and calling more brokers
and talking to title companies and testing out title companies
seeing which one you like best and uh
just building more connections
um maybe just little things like thanking a
a soil tester who does a great job and
and following up like
you can build those connections and be local to an extent
obviously you're not local physically um
but you can kind of be one on one
with someone in terms of just having that relationship
and just treating people the right way
uh
so people like doing business with people that they enjoy working with
um so even if you're not local
I think you can still use that to your advantage and just uh
build relationships and network with people
how about exit strategies
any thoughts on
how do you create additional exit strategies in your business
like you have with the brokerage
and I wanna talk about the brokerage here in a second
but how have you done that
yeah yeah
so um
I guess if you back up a couple years
I did get my real estate license
so with cold calling you get a ton of leads that come through
and what I found in my business is that there's
as you know so many people that want market value for their land
or maybe 150% of market value
so I was just like and I'm letting a lot of these leads go by
that maybe want that hundred to 150% of market value
and I'm really good at selling my own land
and turning my own deals super quickly
and kind of keeping that cash conversion cycle going
where I'm just like gosh
I have my real estate license
I can go pitch this lead on me listing their property
so um
my goal for 2026 is to do $50,000 in listing agent commissions
I think we're blowing that out of the water already
so there's been times where my USB sales lady knows that hey
we're not gonna be able to take this down from a business standpoint
but I'm gonna pitch him on us
on you listing it Dylan
and just today I talked with a guy
who probably has half a million dollars worth of land
that I'm likely gonna list for him
and maybe make 4% commission
and I think that's about 15 to 20 thousand dollars
from a commission standpoint
and that's I mean that's just as good as a buy for 15 k
sell for 30 k with no risk involved um
with me being the broker so um
yeah I would definitely recommend that
for anyone who's maybe interested on being local
and potentially getting their real estate license
again you have to disclose all that with all of your marketing and
and be transparent about that
but it's pretty easy once you kind of get it dialed in
love that dude I love stacking the opportunities that you have
so I wanna talk about the Wisconsin only pit the the the
I'm focusing on the state
I'm gonna be this guy um
if I wanted to do that how would I go about doing that
if I'm doing what I'm currently doing
maybe I'm an investor
I'm a beginner investor and I'm trying to figure out dude
how do I actually add these additional brokerage
double closing all this additional revenue streams to my
my income how
how would I do that and focus on a specific state
what would be your step by step instructions
yeah I think first of all
I'd use different tools like land portal
land stats I mean
there's so many tools out there now to
to focus on the best counties with the best sell through rate
maybe the highest price per acre
there's so many different tools that you can use
I would start there and then hop on Zillow
or have your VA
kind of scrape some of the best land agents that are out there
and build relationships with them
so you may have leads that come in that
maybe you can't do anything from a business standpoint
but maybe you could turn those leads to a broker that can
then go and list it
maybe you can make a commission off of that type of thing
and build a relationship that way
um so that's what I would recommend
that probably be a step one
is just building relationship with brokers
and using them to your advantage
love that that's a great
that's a great thing so um you're
you're reflecting I wanna talk a little bit about some deals right
some deals on that you're doing lately
let's talk about some deals man
what's some what's the big stuff
that's exciting that you're kind of opening up right now
yeah so really excited about just where my business is going
um I have a 10 lot subdivision
I bought 45 acres it was actually on market
so I got the lead lead came in before I put it on
on market and then kind of right when I started working with you Clay
I got it under contract and I got under contract in January
I didn't close on it till August of 2025
and then the plat finally got approved in December of 2025
so um
definitely a long process that included a
a rezone it included some back and forth
and some tabling of the decision from the town
so got to work through that whole process
got it plotted out with a civil engineer and a surveyor
um so such a learning experience there
but then as we sit here in early March 2026
of those 10 lots I've already sold through seven of those
and then in the next two months
I'll be putting in a 500 linear foot road
which should cost about 150 k um
so that'll be again
another learning experience
I've never put in a road before
but long story short I think that's
that's trending to be a 300,000 dollar net deal
when it's all said and done
um the other kicker is that I bought that on seller financing
so I bought it over 4 years at four and a half percent
I pay three payments on the anniversary of the closing date
so that'd be August of 2026
August of 2027 August of 2028
so that allowed me to kind of presell these lots
and kind of take revenue
before having to then pay the seller back initially
so that's been a just a huge deal for me
that's kind of the one that prompted me leaving my W2
and I still have three lots left
and I think they'll sell quickly as well
so when you when you're putting those
the hundred fifty thousand dollars
tell us about the road construction
that's that's really interesting
and like why do you need the road construction
is there
is there a reason why you need it specifically for the sub divide
why couldn't you just sub divide off a road
yeah so that was part of the back and forth with the township
um it's on a county road
so they limited access points
so
in order to kind of maximize and get highest and best use of the land
I had to put in the road basically a 500 linear foot all the sack
to then gain about four lots um
out of that entire development
whereas if I did not put the road in
then I'd probably be stuck at four or five lots
and then the numbers just didn't make sense when you look at um
the purchase price plus the cost of the road
so it's all about just maximizing um
your net revenue cause that's really all that matters
at the end of it the town actually wanted me to put more lots in
but as I ran the numbers that would have increased road costs
increased risk so I had to push back a little bit
and luckily settled on the
the 10 lots and it was kind of a sweet spot um
for that given county and
and they've sold through incredibly well
Roach Road that's what they call it haha
I should have I should have uh maybe
maybe next development it won't be the last
that's for sure that's right dude
Dylan Way Ruth Road
I love it I love it man
so so what is the deal that you're most proud of
is it that deal yeah
that would probably be one
um there's just a lot of back and forth with Township
it was my first one um
and then going back to being local
like it's super rewarding
I mean I'm an hour south of that development project
it's super rewarding to do something in your home state
where you're taking a 45 acre egg parcel
and turning it into 10 home sites for families to then enjoy
so that one is super rewarding
something I'm super proud of and
and then I just closed on the buy side of another big development
buying 22 acres of a 128 acre parcel
and that one was interesting too
because I looked at the future land use plan
basically the comprehensive plan for that particular area
and I saw that that 22 acre chunk was uh
deemed residential in the 2035 or 2050 land use plan
so that's why I targeted that from
from the uh
the previous owner and uh
got the rezone all approved from egg to residential
that was a whole process where your your
in the in those town meetings
and it's kind of you versus everyone else
but you kind of have to know
know the zoning ordinances
you have to treat people the right way
and those are always a lot of fun
and then went through the entire preliminary plat process
and that's all approved so that'll be uh
seven lots that I'll be I'll be creating uh
no road will need to be created from that
which is great and I think that could be
it's penciling out right now as a 400 k a net profit deal
but again you never know until it's all said and done
um you know
pipeline profit can be fleeting
but uh
what the comps are showing me
and kind of the early interest in that project I
I do think it'll be a 300
4 hundred k net project when it's all said and done
do you think that'll exit this year
it could it could
I think the final plat will likely be approved in about
may or June of 2026 to sell through seven lots
that might be tough in the back half of 2026
but it certainly could happen
I'm trying to undercut the market a little bit
from a pricing standpoint
it's a great area it's an expensive area
and that's another one
play that I'm buying on seller financing as well
so I have five years to sell through that
I'm only putting 20% down uh
so your cash on cash return is just insane um
if you can pitch seller financing
so that's another tool in my tool belt
tool belt that I'll plan on using going forward
and I would suggest that um
for any new land investor
to at least bring up the idea of buying and seller financing
to help the seller from a tax standpoint
you never know what they're gonna say
they can always say no
and then you just move forward and underrate the deal accordingly
do you have a a standard pitch for your seller financing
usually I talk about the taxes
so I say like hey
Mister Seller um
this is gonna be a 460,000 dollar purchase price
do you want to pay capital gains on that in the
the 2026 or 2025 tax year
and usually that answer is no
and that's when you can talk them through seller financing
and how they can kind of spread their gains over
over a couple of tax years and
and the reality is
that a lot of these land sellers are usually age 60+
where they're starting to think about Social Security
and thinking about retirement
and wanting those stable paychecks each month
or each year as opposed to one big lump sum
so um
that's kind of my standard pitch
is kind of talking about taxes
and I've gotten turned down on seller financing a lot too
um
then you just underwrite based on your financing and what you can do
yeah um
so let's talk about where you are right now man
so what's something that is exciting for you right now in your world
I would say first and foremost right now is uh
here in Q1 of 2026 I'm really starting to build out a team
I got an awesome uh
operations lead slash VA from the Philippines
uh Lois
she's been great um
just has taken so many tasks off my plate
and then like I mentioned
I have the the US based uh
sales lady on my team
who's just hitting the phones hard and doing a great job
and I could see in the future where she potentially goes full time
if she wants to um
as I really start to scale the business
but yeah
I'm just excited about these development opportunities
there's another deal that I've did a survey hack on where um
basically surveying off someone's homestead and kind of their
their home tract
and then purchasing 30 acres and splicing up that 30 acres
so just land is such a blue ocean
that just gets me excited each and every day
to put the puzzle pieces together of a particular parcel
so um
what are you working on right now that you want help from the audience
or you know
there's all I've quite a few people that listen to the pod and
and the YouTube channel so what
what's something that you'd like to put out there in the world
uh for the world to to
to bring back to you yeah
on mine always looking for capital Partners
you can never have too many
so I'd say that's that's one thing
and I would say if people have deals in Wisconsin
feel free to to send them my way
I'd be happy to to underwrite them for
for that particular investor
I'd be happy to list those for the
for the investor and then um
kind of give comps based on a land investors mindset
not like the typical realtor that might give you say like hey
let's list it at 150 k when it's probably only worth 100
hundred k um
so I'll give you kind of that straightforward advice
so I'm happy to list stuff in Wisconsin for people
and then um
yeah if you have JV opportunities
or different development opportunities you want me to take a look at
I'm happy to be a resource to you and
and happy to help other land investors along the way
yeah if you guys got something in Wisconsin
we'll put Dylan's contact information below uh
he's definitely a guy that
to reach out to uh
and you know it it's been
it was always a pleasure to
to work with with you and
and I know that someone works with you in
in Wisconsin you're gonna be high integrity
make sure that they're taking care of man
I know that that about you
so um
I wanna open up and say what advice
knowing what you know right now
in 2026 what advice would you give a new and inspiring land investor
oh man
that's a great question I
I feel like
I talk to so many new land investors that are big on texting
and texting certainly works
I have so many buddies that kill it with texting and clay
I believe you do too
and I just feel like everyone does that
and these landowners are getting so many texts
whereas I love cold calling as a marketing channel
I'm able to see the transcript from the cold caller with the lead
and I kind of know a lot about the land
before I even had me
or my lead manager have that initial call with the lead
um so I think that's so important
and um
I just like to kind of zig when others zag
and if everyone else is doing texting or mailing
maybe I stick with cold calling
so I would say people like
hey give that a shot
it's a great marketing channel
the return on ad spend is there
um so I think if I had to start all over
I'd probably go all in on cold calling
from a marketing channel standpoint
love it thank you for being a part of the Lamb Lamb and podcast
it's always great to have you on
any last thoughts about anything that you want to put out there
um before we hop off and
and seal the show um
we'll make sure to get all your stuff in the uh
in the comments and everything like that
the the Wisconsin Landman
hahaha perfect
hey I
I like that tagline yeah
I think my final thought would just be for any
you're a land investor or maybe someone who's been in the game for 6
12 months has continued to network with other land investors
I'm part of a pod of
of land investors where we've met weekly for two years now
I feel like and it's been such a resource
there's so many UPS and downs within land investing um
so if you can kind of share those UPS and downs
share those wins and losses with people that are close to you
and people that you trust
it goes a long way in sticking with it in this business
so that's kind of the advice that I would give
uh yeah
feel free to reach out if I can help with anything
especially in the state of Wisconsin
I'd be happy to uh
feel free to DM me on Instagram
I think my tag is uh
d R U s C H5
so d R U s C H5 feel free to DM me and I'd be happy to help
alright guys we'll see you on the next episode