Going From 0 to 10 Deals per Month (and quitting his job) in 18 Months


– Hey guys, this is
Jaren with Retipster.com and I wanted to go
ahead and take some time to introduce you to a fellow Chicago based land
investor Willie Goldberg. Willie’s been doing land for
about a year and a half now and he’s averaging about 10 deals a month. Which I think is ridiculous. I personally want to grow
my business to that point. So when he reached out to me and he told me what he was up to I was like dude I have to get you at least on like some kind of a YouTube video or something
so Willie welcome man and how are you doing today? – Hey Jaren, I’m doing well. Thanks for having me. – Yeah man, it’s not very common that you run into other young people that are doing this business and when you were telling me that you’ve grown kind of your passive income to like $12,000 a month roughly. I hope you’re cool with
me sharing numbers. Are you cool with my sharing numbers? – Yeah, all good, totally good. – Okay, yeah. I mean when you told
me that I was like dude that’s the dream, what the
heck, how did he do this. So tell us a little bit
about your background man. Like how did you get exposed to land? You know, and then take us
from there to your first deal. – Sure, so I guess I grew up in the north suburbs of Chicago so a
born and raised Chicago guy. And always been a competitive guy. I played football and
wrestling in high school. Played football for a couple of years when I was, I went to Pomona
College out in California. And I started getting into finance and that’s kind of where I thought I was going to go with my career. So that’s kind of where I started and I started a couple years
out in investment banking. I jumped around in a couple cities. I was in Charlotte,
Boston, and then Chicago. So I was in investment banking working pretty bad hours and after a couple years I knew that that’s not the route
that I wanted to go in. So while I was in my second year I started to listen to podcasts and hear people talk
about investing in land. I was interested originally
in wholesaling houses but it was really challenging to do. Especially when I had
a pretty demanding job. And so I listened to podcasts, I heard about land, so I
decided to take a leap. Sent out a mailer and yeah,
that’s how I got started and it’s been a good journey so far. – Man, I feel you on wholesaling. Coming from working at Simple
Wholesaling in Indianapolis I think it’s like the second best real estate business out there but land is just better. You just can’t get around it. Like it’s just easier. Not trying to be biased here, but like the reason why I did it myself because I could have personally been like a wholesaler in Indianapolis but I was like dude, land is
much much much much better. So I’m with you. I’m totally in love with this business. So tell me a little bit
about your first deal. What was it like when you sent out that direct mail campaign? Did you have it going to
a prerecorded voicemail or did it go to like a live phone? How did you set that up? – So when I originally started I started by sending out postcards. I thought that would
yield the best response and I think I was correct by that. I had a delinquent tax list. I didn’t have it go
directly to my voicemail, I tried to take as many calls as I could. Obviously when I’m at my
desk I couldn’t do it. I was pretty nervous speaking
to sellers for the first time. Didn’t really know how the process worked and was pretty uncomfortable
and awkward on the phone. And yes my first deal, it
was out in Yavapai County. It was in Arizona. I haven’t sent out a mailer there since. That one just happened
to be the first place and I talked to the seller. I actually never communicated
with them on the phone it was all communicated through email on this particular deal. So I guess the deal was actually previously bought for over $50,000. I studied it and knew nothing about land, I was just super super conservative. I was like the best I can do is $3,000. So I bought it and somehow
they agreed and accepted that. Looking back I definitely
got a screaming deal. I could have sold it for quite a bit more but bought it for three sold it for I think it was eight five. And yeah, I sold that on Craigslist and definitely a good first
deal to get out of the gate. – I remember the first
time I answered a call. I had everything go to
a prerecorded voicemail and I remember I was sitting in the car and my wife straight up
was holding back laughter. She’s like dude you sound so nervous. – (laughs) – You sound so ridiculous. But I remember within the first batch I talked to this guy he had a
property in southern Indiana and he lived somewhere in
the north tip of the state. And I just remember that
feeling of like dang this guy is literally
selling me a $20,000 property for like three grand or like five grand, whatever the number was, I forget. I think it was around 6,500 or something. But whatever it was like whoa, you know. Like I just sent out postcards, he called me wanting to sell his property, and it just changed, I don’t know. I am obviously a kid in a candy shop when it comes to this stuff.
– (laughs) – So tell me about how many deals were you doing when you first got started? Did you have like this epic plan of like one day I’m going to have $12,000 in passive cash flow and like I’m going to do ten deals a month. Or was it just kind of like
I’m just trying this out and trial and error and just kind of throwing things at the wall
and seeing what sticks. – Yeah, so I definitely
did not have that plan. I didn’t even offer owner
financing at the beginning. So I would say during the beginning I was not doing that many deals. I ended up doing just
over 50 my first year. – Nice. – So April and March
of the following year. When I first started it
was definitely super slow but I did that first deal
and then I think there was a two month period where
I didn’t do anything. I was buying a whole bunch of properties trying to figure out what
markets to invest in. Find my niche. There was definitely a building period. – Yeah. – But I kind of just leaned in and I think that’s really
what was important for me is just kind of leaning
into some of the discomfort and having inventory properties, just keep continue buying and just know in my mind
that they will sell. So I just kept buying. A bunch of different areas. Some were selling, some weren’t. And just kept leaning in, leaning in and just kept buying properties. And towards, so November
was a big month for me. I think I had like six or seven and then just at the end of my first year that month I had, I think I had 10 or 11 or something like that,
definitely built up the learning curve and then it started really to take off from there. – That’s awesome man. In November what was the tipping point? Or what was like the key thing that really changed the game for
you in order to do more volume? Was it owner financing, or? – Yeah, so owner financing was definitely a tipping point for me. When I started to get a lot of sales. – Yeah. – That was in March. I think November just
happened to be a good month. I was starting to get the systems in place and learning where to
market and how to market. Talk to people on the
phone and be persuasive. But March is really when the tipping point for my business was. When I started offering owner financing and I started getting a ton more sales. There were so many more buyers out there and cash flow started coming in. But yeah so I just started
building up my portfolio notes and yeah so I never looked back since I first started
offering owner financing. I definitely don’t regret it. – So I have a couple
questions related to that. First, what is your typical
like acquisition cost? – Yeah when I started it was probably between 1,000 and 2,000 was
what I was trying to go for. I had some that were a little bit bigger. As I’ve obviously progressed
my deals have gotten larger. Today I’m still buying the ones
that are in that price range but I’ve also started first buying into or buying properties that are five, 10, 15 thousand dollar acquisition prices and trying to get a good mix of that. So there’s property on my website for all different types of
price points and buyers. – So when you first got started how much money did you have set aside for you know, ongoing marketing
and acquisition price? Like did you say okay I want to spend like x amount of
dollars per month on marketing and I want to try to buy
like two to three deals starting off at this price. How did you set all that up? – So when I started I had bit of money saved up from my previous jobs. So I actually probably had
more than you definitely need. I put 50 grand into a
different checking account. Which I had made it for acquisitions and marketing and the like. So I really wanted to just go all in. And so I started sending out
mailers and using those funds. It took me a while to build up to around 50,000 in inventory but over time I just kept buying and investing and building up my inventory so. – That’s really cool. So you didn’t get into any loans or private lenders or partners or any of that, you built this thing from good ole sweat equity. – Yeah, from the beginning it was just savings I had built up from my jobs. – That’s awesome man. That’s really awesome. So in the beginning or at the point as you started progressing
when you developed a system, what did you have to track or figure out to be like okay if I want to do you know, five deals a month or ten deals a month I need to spend x amount in marketing. Or you know, did you, how did you kind of reverse engineer how much
you needed to be putting out in terms of marketing and
do you always put it out and then consistently and
just buy and buy and buy and then just wait for things to sell off? Or do you kind of do a big campaign and then buy a bunch of property and then shut off marketing and then you know, turn it on and off? What’s your approach there? – Yeah so in the beginning I was more of the on and off approach. I would just send out a mailer and then buy some properties. And in some cases I had some
pretty successful mailers to buy a bunch of properties and then learn how to market and sell and then once I get a couple of those sold send out another one. Obviously since then I’ve
developed a good system where I don’t have to do
everything in my business anymore I have virtual assistants
who’ve been pretty vital in my growth and I also quit
my job in June of this year. So I’ve had a lot more time
to commit to consistency and building systems and focusing on just yeah making everything a
little bit more smooth. What I try to do is I try to
buy three properties a week. If I buy three properties a week I imagine I’ll sell
three properties a week, maybe not this week but going forward. So I think that’s really
what my key metric is that I’m trying to accomplish is buy three properties a week and I have reverse engineered that and have been sending out
between four and five thousand units of mail a month and that’s been over the past few months. I think I’m going to
slow it down a little bit but I’m having some good
response now so, yeah. – Do you just do postcards or do you do blind offers and yellow letters? Have you mixed them all or are you just always doing postcards? – So I just do offers now. So I just letterprinting.net. They’re pretty cheap, I
think they’re 53 cents. I use a one page offer letter just to try to maximize the
cost of sending out mail. So I use that and they’re
super helpful to me. – What percentage of quote
unquote market value, that’s super relative in land, but like are you doing
20 cents on the dollar, 30 cents on the dollar, what are you doing as your kind of blanket approach? – Generally speaking I just look at the lowest edge line of
property and divide that by two. And it’s been a bit more competitive but I don’t see any problem
acquiring property at that. So it’s probably like five,
fifteen, twenty percent. – No yeah, no that makes sense. That’s perfect. So I want to go back to
you quitting your job. How the heck did that feel? – It was great. It was awesome. So I went on a road trip right before. I had no intention of quitting my job, I was just having a road trip with a buddy and we went to Montana and we have a friend who has a place over there so we were just hanging out. And it was a lot of time
to just think about life, think about my job, and on the ride back we were just talking about it and I just kept thinking about
it and I knew it was time. I had the cash flow, I
had the income coming in that it didn’t really make
sense to have a job anymore. And so when I got back in my
chair on the following workday I was just like alright
I think this is it. I’m going to call it quits and yeah so that’s how it went down. – That’s awesome man. Nah, that’s super cool. I think that for a lot of people that’s kind of the dream is that moment where they’re able to like step out and kind of be their own man, you know. – Yeah. – So let’s talk about
building up cash flow and owner financing. One of my biggest questions in the way you’re approaching the land business if you’re doing a lot of owner financing, how many deals would you say are owner financing versus cash right now? – So I’d say two thirds owner
financing, one third cash. So maybe three to four a month in cash and I guess six to seven
in owner financing. – So I’m assuming you’re also like holding a percentage of the note too. Like you’re not getting what
you have in the property out in the down payment or anything, right? – Correct. So I’m holding note and the
down payment is usually just a couple hundred bucks
to make it affordable. So I’m not getting the down
payment out right away. – So do you have to
make a certain amount of money in cash per month in order
to keep the marketing going and to do 4,500 units,
like that’s probably a couple thousand dollars
a month in marketing. So like do you just take the cash and just put that toward marketing and then just live off your cash flow? How do you structure kind of the balance? Because if you just
kept selling everything owner financing like eventually right you’re holding notes, like
you have all these notes and you’re making money every month but you don’t have any more to buy, right? – Yeah. I guess cash flow is a little bit of a challenge in the business. It’s not my goal, it’s not
what I’m really gunning for. So I guess it’s like I said, I started with about 50k
in that checking account and that amount has gone up a little bit so cash flow is still a little positive, not a lot but.
– Yeah. – What I’m really trying to do is just build a portfolio of assets and that’s really what
I’ve been striving to do. So I started with about
50k in the bank, no assets, and then over time I’ve built up to combined with receivables
and lands that are currently marketed a little over 600,000. So if find not having the best cash flow but just building a portfolio
of assets that are performing. So I still have enough capital in the bank to where I can continue
to buy three a week and I’ve been selling
about three or so a week. So assuming that cap keeps happening I think capital will stay about the same or go up a little bit it depends on how big the acquisitions I keep going for but I’m trying to manage that. It’s just kind of a balancing act. – No that makes a lot of sense though because the approach is
just totally different. The goal with your land business isn’t for it to be a cash cow it’s to literally be a
passive income stream. It’s a lifestyle based business, right. So that makes a lot of sense. So you take a lump of
cash that you saved up and then you use that to
get as much owner financing situations as possible and then you just build that monthly cash
flow up and up and up and as long as you’re
maintaining roughly that balance so that you can still buy the amount that you’re wanting to buy per month then you’re able to just
grow that infinitely. So that makes a lot of sense. – Yeah. – So what would you say is the most challenging thing
about the land business? – The most challenging is
for me is just a mental game. To be honest it’s once
you buy a new property and you’re sitting
there, it’s not selling, it’s been a couple of months, you find out something about the property you didn’t know before hand. I had a lean come up on
one of my properties, a $5,000 lean. – Oh man. – I had sold the property and then I get a mail from some law firm suggesting that there’s
a lean I’ve got to pay. And I reach out to the seller, he’s not responding, not responding. I call him 100 times, not responding. And stuff like that. You just have a lot of money
of your own capital invested and I think that’s what really
stops people in their tracks. I guess people who don’t start they don’t want to spend
the money on the mail, they don’t want to spend
the money buying properties, they’re not as confident. In my mind it’s a mental game. I think that the business
itself is pretty easy. I mean, you just buying a
better valued asset yourself and you’re selling it for more but it’s still under what
the market’s trading for. So I would say the mental
game is challenging. You’ve just got to play
it the best you can. – So when it comes to
selling off properties because that’s really the biggest challenge in land is dispositions. When you can move inventory, that’s the name of the game, right. What’s some of your top one to three tips on moving properties
that are hard to sell? – So yeah it’s really more
of a marketing business than I mean, it’s half
marketing half real estate. What I do, what’s been
pretty instrumental for me is building a email list and
marketing to that email list and building a buyer base and just building a connection
with that community. So I have my property posted, I don’t have it posted anywhere special, so Facebook, Craigslist, Lands of America, Rural Vacant Land, and Land Flip. And then Zillow so like six places, like nothing uncommon
with all those places. But what I do differently, and also my main page of my website collects an email before
anyone can see a property, I think that’s pretty
– That’s cool. – It just adds up over time. But whenever I have a phone call or a text or any sort of conversation with anyone I make sure
to ask them for an email. I collect probably close
to 30 to 35 emails a week and just add that to my database. Sending out weekly emails and just marketing
emails just letting them, people know what’s on the market. I think video has been
instrumental in helping to sell. So I create videos of my properties, send update videos to my buyers. – That’s awesome man. What do you do on getting
video when you’re out of state? Because you live here in Chicago or in the Chicago area
right, in the suburbs, and then you’re doing a lot of stuff out in like California,
Arizona, and New Mexico, right. So how do you get videos
for your properties? – So I just use Google Earth and use like software online to just show
overviews of the property. I try to use street view whenever possible and just try to give as many
details about the property. And I think a lot of
it’s not even about the, well I think a lot of
it is about the asset and like showing them here it is, here’s the market, it’s undervalued. I think a lot of it is
just so your audience can get to know and trust you because when I get people on the phone I refer to myself as
Willie G from wglands.com and when I get someone on the phone they’re like oh it’s
Willie G, oh that’s cool. They think it’s like interesting that I was the one creating the video but I’m also the one answering the phone. So they already know who I am and they think I’m more legitimate. It gives me a lot of credibility. So I think that is really
meaningful and beneficial. – One final question for you
before we wrap this thing up. What do you think has been the one single most impactful
thing in you land business? To go from just doing
one deal here to there to where you are today where you’re doing about ten deals plus a month. – As simple as it is I’ll tell you the persistence and hard work, just not giving up and
figuring things out. Just don’t give up on any deal, don’t give up on the business and keep focused and yeah
just figuring things out. When the answer’s not
right in front of you just staying with it and
making sure you get the answer and never giving up on a lead,
on a phone call, or anything. So I think just keeping at it and I mean the business is
proven to work over time if you stay at the business for a long enough period
of time you’re going to do well just playing the
numbers game and not giving up. – Alright I’m going to
press in there for a minute because on these interviews a lot you know, you hear just
gold just like you shared. But a lot of the times
what people walk away with is like okay I don’t need to give up but like when you’re in the trenches right and they’re not coming off of a super motivating
conversation like this one it’s really hard not to give up. You know what I mean?
– Yeah. – Like especially this land business. It’s really lonely sometimes. Like you’re just, it’s kind of you and your computer and you’re like dude half the world
doesn’t even understand what the heck I’m doing and
they think that I’m like crazy. In those moments, what
do you do personally when you want to quite and you want to just throw in the towel. Like a deal backed out or like
a seller stopped paying you when they’re supposed to pay you. All that stuff. What is your practice for not giving up? – So I would say I need to be in the right mindset at all times. The more obsessed you are with it the more you’re likely to not give up and you’re going to be
in the right mindset. But I think just surrounding myself with people who are
positive and encouraging. Yeah, just taking a step back and just surrounding
yourself by positive thoughts and talking with people who are in similar situations is kind of the best way that I go about it. Being an entrepreneur anyway you need to be in the right mindset. You’re not going to just one day become an entrepreneur, you need to first change your mindset and understand there are going to be ups and downs and it’s not just a little thing it’s really a process that takes time. – Well hey man, how can
people best connect with you? Like if I were to drop a link, do you have email or do you want me to send people to go join your buyers list? – So they can email me, [email protected], that’s
Walter George l a n d s .com. Or they can go on
Facebook, Willie Goldberg. You can find me on there. – Sweet, I’ll have all the links in the description box below. Yeah man well this has been great man. I really appreciate your time and it was really inspiring
to hear your story. – Thank you, thank you. I really appreciate it. – Until next time, later. – Sounds good, thanks Jaren.


  1. Great questions, Jaren. Just as I wondered about something, you would ask that question. Great answers from Willie, also. Clear overview of how he got started and progressed until today. Thanks, guys.

  2. Awesome video! Willie is a real inspiration! I appreciate everything the REtipster team has been sharing. The content keeps me focused and helps answer many of my questions.!

  3. Isn't there land finance businesses that will buy the deeds? I mean, why would I owner finance and hold the deed when a I can take a little loss on profit but get payed instantly and never worry about rent to own buyers failing to make a payment? It seems like a no brainer to flip the land ASAP even If I don't get full land value, just flip it and move on with the cash. I understand some people have bad credit but those people should be paying the full price that you payed for the land as their down payment because they're HIGH risk buyers.


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