← Real Estate Pros
Real Estate Pros · November 21, 2025 · 29 min listen

How a $1,000 PPC Test Turned Into an $18,000 Wholesale Deal for Eli Goodman (Chicagoland Cash Buyer)

Show summary

In this conversation, Eli Goodman shares his journey in real estate, emphasizing the importance of market focus, the challenges faced in partnerships, and the resilience required to succeed. He discusses the struggles of starting out, the lessons learned from failures, and the need for tailored strategies in real estate. Eli also highlights the significance of understanding personal goals and adapting approaches based on individual circumstances.

Key takeaways

  • A $1,000 investment in a Google Ads setup service generated a contract within a week that turned into an $18,000 assignment fee on a house the seller listed at $90,000.
  • When his own cash buyers list passed on a deal, Eli JV'd it to another investor (Fernando Angelucci) who found a buyer within a day who showed up with a $5,000 earnest money check.
  • Early lead generation attempts included mailers (little result) and Facebook ads (worked well until Apple's iOS update hurt ad performance), before settling on Google PPC as his long-term main lead source.
  • A bad partnership structure (Eli handling business/buyers, partner handling real estate operations and sellers) fell apart after about a year because the partner stopped following up on leads; Eli left with only the Google ad account and had to relearn negotiation and seller conversations by working on commission for a fix-and-flip company for six months.
  • Going full-time in February 2020 meant starting with about $7-8,000 in savings and a 0% APR credit card, living with parents to keep expenses at zero, and surviving deal to deal through the first year or two, compounded by COVID hitting a month after he launched.
  • Even after finding a dedicated PPC agency that improved lead quality, Eli nearly quit three months in due to unrelated setbacks stacking up at once: a raccoon break-in at a rental, a six-month vacancy, and a car repair bill, before a contract came through and business rebuilt over the following months.
  • Choosing a real estate strategy should be based on personal goals, time versus cash position: time-rich/cash-poor people should consider building a wholesaling business, while cash-heavy/time-poor professionals may be better off buying a couple of BRRRR or 25%-down rental deals per year instead of treating wholesaling as another trade-time-for-money job.

In this episode

  1. 00:00From $1,000 PPC test to near quitting
  2. 02:13Intro: Eli Goodman, Chicagoland cash buyer and wholesaler
  3. 02:42From personal training to a failed first partnership
  4. 04:37Day-to-day in the early years: learning comps and running numbers
  5. 06:58Testing mailers, Facebook ads, JV deals, and the $1,000 Google Ads bet
  6. 09:28The first deal: $18,000 assignment fee on a $90,000 house
  7. 11:03Finding a buyer: cold calling the buyers list and JVing with Fernando Angelucci
  8. 12:10Partnership falls apart, Eli leaves with nothing but a Google ad account
  9. 14:50Going solo in 2020: COVID hits, living deal to deal
  10. 17:09Fumbling through Facebook ads, iOS update, cold calling, then finding a real PPC partner
  11. 22:03Advice: match your real estate strategy to your goals, time, and cash position

About the guest

Eli Goodman is a cash buyer, wholesaler, licensed agent, and former flipper based in the Chicagoland market, now focused on wholesaling. He got into real estate in 2018 after years of doing personal training, went full-time in wholesaling in late 2019/early 2020, and has relied primarily on Google Pay-Per-Click as his lead source for years. He runs a Facebook group with about 20,000 members focused on the Chicago market and hosts a monthly investor meetup in Chicago.

Listen to the audio

“I get my check we had to split it with him and then I had to split the rest with my partner. I look at it and I go, hey, we spent a thousand dollars on Google ads... That's a two thousand dollar investment with an eighteen thousand dollar ROI. I'm about to be rich.”

Eli Goodman

“I have no backup option. I didn't get a college degree. So if this fails, I don't even know what I would do.”

Eli Goodman

“You've got time on one side, money on the other. If you're cash heavy and time poor, then use that cash to buy back your time. But if you have a lot of time, use that time to get some cash to buy your time back.”

Eli Goodman
wholesalingChicagoland marketGoogle PPC adsFacebook adslead generationJV dealsreal estate partnershipscash buyersBRRRR

Questions answered in this episode

How did Eli Goodman get his first wholesale deal?

He and his first business partner spent $1,000 on a service that set up a Google Ads account for them (found through an online webinar pitch). About a week after the ads went live, they got a contract on a house the seller wanted $90,000 for, which they wholesaled for an $18,000 assignment fee, split with a JV partner and his business partner.

How did Eli Goodman find a buyer for his first wholesale deal when his buyers list fell through?

His own cash buyers list passed on the deal, so he JV'd it out to another investor, Fernando Angelucci, who doesn't normally do single-family deals. Angelucci sent a buyer out the next day who showed up with a $5,000 earnest money check, and the deal closed a few weeks later.

What lead generation methods has Eli Goodman used for wholesaling in Chicago?

He tried mailers (didn't get much), Facebook ads (worked well until the iOS update hurt performance), cold calling, and Google Pay-Per-Click (PPC), which has been his main lead source for years. He eventually hired a dedicated PPC agency about two years before this recording after finding them through a YouTube video, which improved lead quality and consistency.

What happened when Eli Goodman's first real estate partnership ended?

He and his first partner worked together for about a year starting in mid-2018, generating leads through Google Ads, but the partner stopped following up on leads and making offers. Eli left the partnership with only the Google ad account and no real estate negotiation or selling skills, so he went to work for a fix-and-flip company for six months on commission to learn the business before going out on his own in 2020.

Should someone with a full-time job get into wholesaling or buy rental properties instead?

Eli says there's no one-size-fits-all answer: sit down and figure out your actual goals before picking a strategy. If you have time but not much cash, use that time to build a wholesaling business; if you're cash-heavy and time-poor (like a high-earning professional), you may be better off buying a couple of BRRRR deals a year or putting 25% down on rentals rather than treating wholesaling as just another trade-time-for-money job.

How tough was it for Eli Goodman to go full-time in real estate wholesaling?

He saved three to four thousand dollars, got a 0% APR credit card for another $4,000, and started full-time in February 2020, right before COVID hit. He lived with his parents for the first year and a half with no expenses, and the first year or two were 'living wholesale deal to wholesale deal' while he fine-tuned his Google Ads approach.

Resources and links

Full transcript

Eli Goodman (00:00)

so it was a couple of years of just fumbling around because I got into the PPC, uh, Google ads, uh, that was doing very well, but it slowly started like not, it got worse and worse as competition. I feel like I kind of got into the Google ads at the early onset before is really as famous as it is now. Um, and so we started testing, I started testing Facebook ads that went really well. So I moved into Facebook ads, but then the iOS update came out and just destroyed our Facebook ads,

was like this close to quitting. And all of sudden I get a contract and slowly but surely built back up over a couple months. And ever since then it’s been just really well.

Dylan Silver (02:13)

Hey folks, welcome back to the show. Today’s guest, Eli Goodman, is a cash buyer in Illinois in the Chicagoland market, wholesaler, licensed agent, ⁓ flipper, now focused on wholesaling. ⁓ Eli, welcome to the show.

Eli Goodman (02:30)

Hey Dylan, thanks for having me.

Dylan Silver (02:33)

It’s great to have you on here. I always like to start off at the top of these shows by asking guests how they got into real estate.

Eli Goodman (02:42)

Yeah, it was definitely not on purpose kind of stumbled into it. I was at the time I was doing personal training and I was just burnt out of waking up at 5 30 a.m. For canceled appointments running all over the city all day and basically just realizing that I was trading time for dollars, which was great when you were 20 years old. I was making decent money, but I realized that that was not going to be my future. At the time a friend of mine, he was interested in becoming a real estate agent.

And he would be on YouTube all day just learning how to be a real estate agent, preparing for his test. And one day he sees someone with a Lambo and a check in front of Chase Bank, buys a course, quits his job, gets a sports car and goes broke. And I thought it would be a good idea to get started in this as well. So I said, hey, I’ve got some business experience running my personal training thing. How about I use that money I have, that experience I have on the business operation of it while you do the real estate operation? As I’m sure most

of you guessed that did not go well. We went for about eight months, got our first deal and I ended up leaving him and working for a fixin flipper for about six months I’d say. Did a couple deals with him and then at the end of 2019 I said I’m just gonna take the jump and hope that it works. Quit personal training and went full-time and been doing that for the last I guess six years now.

Dylan Silver (04:07)

So you got in 2019 wholesale at that point in time was tremendous. ⁓ From what I understand, I was not in at that point. I got in around 2023. Walk me through what the day to day was like at that point in time, the kind of deals that you were coming across and then also just what the market was like and what the landscape was like in the wholesale space.

Eli Goodman (04:37)

Yeah, I mean, I can’t really answer to a lot of that because at the time I was really just learning like, what is this real estate thing? Like, how do I comp?

I knew nothing. So that was really my main focus is like learning how to come learning how to run repairs and making offers and that was my day to day I’d wake up I do my clients I’d have some odds and end jobs ⁓ just to make as much money as possible because all my money would come in

as soon as it’s come in go into the business and just go into marketing and just get burnt up right dollar in dollar out ⁓ so that was a lot of my day just wake up try to find ways to make money put that money into the business

some time working on the business and learning the day-to-day and then when I went to work for that flipper I was cold calling I was visiting sellers and just trying to figure this thing out for those first couple of years.

Dylan Silver (06:17)

So first couple years you mentioned really getting the foundation of the business, understanding how to comp, understanding lead flow, how leads come, but you’re also seeing, you’ll hit a lick, especially wholesale assignments, right? But then you have to sometimes make that money last at the same point in time. You either have to put in massive effort and time in order to generate some of these leads or you have to pay for leads, right?

After those first couple years you’re starting to roll, what was the scaling of the business like and did you identify a niche that was a good lead source for you?

Eli Goodman (06:58)

Yeah. So when we first started, we were really just figuring out, know, I was figuring out what is this thing and on his, and then as well as on the business operation side, how are we going to generate consistent leads? Right. So we said, okay, let’s do what everyone’s doing. The mailers did a couple mailers didn’t really get anything. Tried Facebook ads, doing JV deals. And one day we get this, someone sends my partner this email and it’s about, it’s one of those scammy

webinars where there’s no face and

They just spent an hour slow pitching you something and at the end they say give us $1,000 and we’ll set up your Google Ads account and we decided we have nothing to lose. Let’s just do it. We put that we give them a thousand bucks a week later. We have our first contract and we close $18,000. We had to JB with someone that my partner split with me. So I was just about breaking even at that point.

So that was really what we’re doing, trying to figure that out. And then when I went to work with this other guy, the same thing, our first two deals, we did one auction deal and then the other two were from, I think they were from Google, whether that was organic search or a paid lead. And when in 2020, when I went full time, I said, that’s what I’m gonna do. I’m gonna go into Google pay per click. And I’ve been up and down with Google for a while, but I’ve settled as of now that’s been my lead source that I’ve been using for years. My main lead source.

Dylan Silver (08:20)

So when

you’re, I wanna walk through that $1,000 ⁓ course or service that ended up being really fruitful, right? So you said, hey, let’s put $1,000 into this. At that point in time, did you…

know or have familiarity with you know other flippers wholesalers are buying leads and that hey this might be something that we should do and were you looking at pay-per-click versus other lead sources as well or were you somewhat sold out hey we need to get into google ads

Eli Goodman (08:56)

No, we were literally just throwing money at whatever came across us until we figured out what could get us good leads. So it was just, we hear Facebook ads, we put money into Facebook ads, just giving everything a shot until we figured it out.

Dylan Silver (09:03)

And so.

I want to walk through that first deal, right? So you mentioned $18,000 assignment fee, right? That first deal, Google ad services, someone called in, texted in, emailed in, how’d they get ahold of you?

Eli Goodman (09:28)

⁓ I don’t remember at the time I was not managing leads. My guess would be they either, you know, they went to our website, made a phone call or submitted a form and my partner kind of handled it. ⁓

We kind of knew at the time that it was a good deal or he knew at the time because he was good friends with like one of the top brokers in the city. So he called him and the guy was like, yeah, that asking price of the seller, seller wanted 90,000. He said 90,000, that’s a deal. You just had to negotiate your assignment fee now. So he was spent all night. He literally stayed up all night before his appointment, just preparing for that appointment,

comps, repair estimates, negotiation tactics, everything. ⁓

And so yeah, we were just working that one lead.

Dylan Silver (10:48)

And the buy side, so you acquired it, you had to disposition it at that point in time. Did you have investors lined up for that deal? Did you have to blast it out to a network that you had? How did you find someone quickly to purchase the deal?

Eli Goodman (11:03)

Yeah, so while I was running around doing personal training and hard jobs to make money, learning about real estate, trying to generate leads, building out our social media, we were also going to networking events and meeting with cash buyers. So we get this great deal on our contract and we go great, easy $17,000 or $18,000 spread. All we gotta do is call our buyer’s list and sell it to someone. Call our buyer’s list, none of them want it, they send a couple people over, none of them want it.

And

we end up jv-ing with I’m not sure if you know Fernando in Galuchi He doesn’t do single family But at the time we gave him a call and he sent someone out there the next day and they showed up With a $5,000 earnest money check and we closed a few weeks later

Dylan Silver (11:48)

Wow, wow, so that was ⁓ the first deal, right? After that first deal then, did you start basically pouring money into that Google Ads lead source and was it, you mentioned it was up and down. How did you fine tune it over time to have some consistency there?

Eli Goodman (12:10)

Yeah, so I mean as soon as I got my check we had to split it with him and then I to split the rest with my partner I look at it and I go hey we spent a thousand dollars on Google ads. We spent a thousand dollars for these guys to set it up That’s a two thousand dollar investment with an eighteen thousand dollar ROI. I’m about to be rich. All right, that’s my thought So I just put all of it into Google ads. I say let’s go all in let’s just put as much money as we can pump out these leads and I’ll focus on getting those buyers because I’m looking at this and I go

man, we just lost 50 % of our revenue. We can’t keep doing this. So I’m gonna focus on this buyer’s list while my partner can focus on the sellers. And let’s just do this. If a $1,000 investment grants us $18,000, let’s put 5,000 into it.

Unfortunately, my partner did not have that same mentality. He was just not focused on the business and we would generate leads and he just was not following up with them, not making offers, which is when I then had to leave and I left the company and all I took with me was a Google ad that left him everything. And now I have a problem because I don’t know everything. can’t talk to sellers, I can’t negotiate, I have nothing. So I went to go work for this fix and flip and I said, okay, let me just put this business on the backend. Let me learn the real estate business and then once I have

more cash saved up. ⁓ Let me, let me, once I have cash saved up, once I know this business, let me start again or let me integrate with him, whatever that looks like, but I just need some time to learn this business.

Dylan Silver (13:40)

What time period was that? Sounds like maybe 2022, 2023 timeframe, somewhere around there.

Eli Goodman (13:47)

So I started with him a July of 2018 we came up with this idea out of July right around July 4th we worked together until about June of 2019 and Then so we were together for about a year when I went to work for that fixin flipper June July time And I worked with that flipper until December so six months of full-time the six months until I went full-time for him

Dylan Silver (14:05)

Okay.

Okay, so actually it was a pretty substantial learning curve. It could have been years, you know, but you can then sit down into a couple months with the partner, ⁓ learn, ⁓ you know, lead acquisition. And then you say, okay, I really got to understand the foundations, how to negotiate, how to do a lot of these ⁓ pivotal ⁓ parts of the deal in order to be able to take it from the cradle to the grave.

So now you’ve worked for the flipper, now you’re on your own effectively. ⁓ What was it like first couple months, first year on your own?

Eli Goodman (14:50)

Absolutely terrible. So I get, I had 2019, I go or 2020, I save up a couple thousand dollars. Cause right. I had sunk all my money into this business.

Then I went to work for this fit fixing flipper and I’m a hundred percent on commission. So if I don’t close a deal, I don’t make any money. So for that six months, I had some money from personal training, but I was just saving up that money. And then I go, okay, I’m gonna start this business. I got three, $4,000. I’m gonna get a 0 % APR credit card.

I got another $4,000 for one year and I’m just going to put into Google ads.

So I get started right around mid February 2020 and COVID happens a month and I end up moving out of my parents house. So the first year and a half I’m still living with my parents. I got no expenses. I move out of my parents house and COVID hits. And while a lot of people listening in hindsight may say, has said that was a great time to be in real estate. It was actually both good and bad because

In the beginning of COVID, everyone thought, rightfully so, that we’re about to have a market correction and it’s a terrible don’t buy. ⁓ A lot of sellers just, everyone was just kind of frozen in place and that happened, but I still got my first deal. And for the first year or two, was just kind of like figuring it out, fine tuning things and just living wholesale deal to wholesale deal really.

Dylan Silver (16:56)

I’ve been there. I know exactly what that’s like. The rush is great, but then you got to find the next one. ⁓ Did you have a pivot after that? How did you stabilize after that period of time?

Eli Goodman (17:09)

Um,

so it was a couple of years of just fumbling around because I got into the PPC, uh, Google ads, uh, that was doing very well, but it slowly started like not, it got worse and worse as competition. I feel like I kind of got into the Google ads at the early onset before is really as famous as it is now. Um, and so we started testing, I started testing Facebook ads that went really well. So I moved into Facebook ads, but then the iOS update came out and just destroyed our Facebook ads, tried some

some cold calling, so I sprinted around a little bit. And then about two years ago, I was on YouTube and I saw some guy who runs a PPC ⁓ company and he posted some video, some random video about YouTube, about real estate and I watched it and I just went down this rabbit hole, watched all his videos, booked a call and hired them to run my PPC campaigns. And right away I could tell that something was different here. I could tell the lead quality was better, more consistent.

you

know, I was just kind of running Google Ads without any knowledge of it. I was just kind of like this guy, I paid this guy a couple years ago, a thousand bucks. They set up my Google Ad campaign, just run the ads, do it how I want to. But they were there to kind of tweak me through it of like, hey, we need to tweak these ads, we need to upgrade your campaigns, upgrade your website, website speeds, all these different things. And right away I could tell things were different. But I also got started with them at a terrible time where I had a number of rentals that went wrong.

There was like a raccoon that broke into one of my rentals. One of my rentals was vacant for six months. My car hit something and I needed to repair my car a couple grand. And even though they were doing really well, it still took me three months and I was like this close to quitting. And all of sudden I get a contract and slowly but surely built back up over a couple months. And ever since then it’s been just really well.

Dylan Silver (19:06)

I think it’s beneficial for our audience to hear the full spectrum of this because when we talk about, you know, early partnerships not working out, then pouring money into ads and then not having the system and then finding the right people, but then, you know, things outside of real estate happen, it just becomes difficult. It’s nice to hear the whole perspective, the kind of unfiltered truth, because it is a long haul. Like if you…

take a look at any one of those steps, you probably could have stopped and said, hey, I’m gonna go do something else. But each step of the way you had faith and you stayed in it the long haul. Was there something, you know, even during those tough times that was keeping you in it? Did you just have internal belief that it would work out or you just love real estate? ⁓ What was the idea? Hey, I’m gonna keep through this.

Eli Goodman (19:56)

That’s a good question. ⁓ I think in the beginning, those first year or two when I was still part time, ⁓ there was just something in me that wanted to get into this real estate thing and I saw a way of making a lot of money. I would say right now there’s going to be, you know, there’s a lot going on right now because there’s, you know, there’s a lot going on too right now that’s making it tough. ⁓ And a lot of it is just like, I have to, I have no backup option. Like I didn’t get a college degree.

So if this fails, I don’t even know what I would do. So that’s gonna be part of it. But there’s another thing at this point where I look at it and I go, okay, I’ve been through these ups and downs a couple times. I know what to do. It’s still tough, but I know that I can just ride this out.

Dylan Silver (20:43)

I mean that perspective is really ⁓ nice to hear. Because there’s a lot of folks who look at this and say, okay, well didn’t do it in two months, three months, six months, and I can’t find my first deal, and they kind of throw in the towel. But this is not a three, six month, or nine month type of game. I know people in the multifamily side who have massive portfolios, but haven’t successfully closed a deal in…

more than a year because they’re so selective at what they’re looking at. So oftentimes in the single family space we tend to say, hey, let’s just get something undercut, let’s just do it, let’s just do it, let’s just do it. But also too, you can lose money that way as well. So I think hearing your perspective is beneficial to folks who may just be starting out. I do wanna ask ⁓ your feedback on that front for folks who may be starting out or may have a job. ⁓

They may work for the city, they may work for the government, whatever it is, teacher, you know, and they’re thinking, well, how do I get started in real estate? You know, I’ve heard mailers, I’ve heard pay per click, you I don’t know if I can do this part time, I don’t know if I should go rentals. Do you have any feedback for folks who may be on that side of the game, just getting started and trying to figure out where to jump in at?

Eli Goodman (22:03)

As far as like what part of real estate to jump in at? Yeah, that’s an interesting question and there’s really no specific answer. Each person has to sit down and ask, you know, what they truly want. Like, you have to sit down with yourself in a quiet room and a pen and paper with your spouse or family or friends or whoever that person is that really knows you and ask yourselves questions because…

If you’re a doctor and you’re making hundreds of thousands of dollars a year and you say, hate this, I want to get into real estate, wholesaling is probably not the solution for you. You’re just trading a high paying job for a potentially higher paying job. But wholesaling is a job at the end of the day until you can really build this out, then it can become a business. But that’s tough. ⁓

And maybe you’re just better off, you know, working for a couple years and using that money to buy some multifamily and just kind of scaling from there. So you have to ask yourself, like, what are your goals and where do you fit in? Like maybe you’re a doctor and you go, I want to start a big wholesaling business. Like I will sit down and put my face to the grindstone and just grind it out. Then go for it. But similarly, if you’re, you know, maybe like a small, you know, you’re an accountant, you like your job, it brings you stability, but you want to plan for retirement.

you’re better off buying a couple houses per year, whether that’s a BRRR investment, buying, rehabbing, and refinancing, maybe that’s just putting 25 % down. ⁓ But don’t get caught up in the gold, chasing the gold and the silver, because again, you just have to decide what you want and what fits it. You’ve got time on one side, money on the other. If you’re cash heavy and time poor, then use that cash to buy back your time. But if you have a lot of time, use that time to get some cash to buy your time back.

Dylan Silver (23:51)

Well, I appreciate the feedback. I think, you know, a lot of folks will say, you’ve got to go wholesaling, you’ve got to go multifamily and, you to be able to tailor it to you, you mentioned, you know, if you’re a doctor, wholesaling is just going to be exchanging your time for money as well, potentially. It is no one size fits all solution, but I do believe that there is a spot in real estate

for everybody, whether you wanna go higher risk, lower risk, higher time commitment, lower time commitment. ⁓ We are coming up on time here though, Eli. Where can folks go to learn more about what you have going on, ⁓ as well as maybe ⁓ discuss a deal that they may have in the Chicagoland area?

Eli Goodman (24:35)

Yeah, so I have a Facebook group. We got about 20,000 people in that. That’s a great way to kind of find out what’s going on in the Chicago market if you’re just looking to poke around. Otherwise, my Instagram’s great. It’s ⁓ ELIG_OG. That’s where I’m just posting different stuff I’m doing, ⁓ posting deals I have. If you have a JV deal, that’s a great place to DM me. ⁓

I’m just posting a lot of stuff there. ⁓ And then I got a monthly meetup. We’re taking some time off because my partner’s having a baby, my sister’s having a baby, and I’m getting married. But we meet first Tuesday of the month in Chicago. ⁓ You can find out more about that. Same thing, Facebook group, IG, or illinoisbestwholesaledeals.com forward slash meetup. So there’s really a lot of ways to get a hold of me. If you really want to get a hold of me, I’m pretty responsive.

Dylan Silver (25:24)

Eli, thank you so much for coming on the show here today.

More from Real Estate Pros

All episodes →
The Investor Fuel Mastermind

Doing deals every month? Do them with people who do more.

Quarterly in-person masterminds, monthly boards and a community of serious real estate operators. Membership is by application.

Learn About Investor Fuel