From a secluded beach house to an apartment in the heart of a city, Airbnb offers unique getaways for thousands and thousands of people. Shouldn’t you start thinking about investing in Airbnb then? Airbnb investing gives you so much freedom, both financially and time-wise. Learn more about investing in Airbnb, getting licensed, and more in today’s episode as Zeona McIntyre talks one-on-one with her former mentor, Rocco Montana. Rocco is a longtime real estate investor and the co-founder of JROC Properties. Listen to his real estate stories – from his first deals to his biggest mistakes – and learn to never give up when you fail. Remember, you’re only a failure when you quit.

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An Inside Look Into Airbnb Investing With Rocco Montana

Here I am with a great friend of mine, Rocco Montana, who got me started in real estate as an agent and I’m forever grateful. He was my first mentor out of the gate before Craig stole me away. Craig, he’s a bad guy, not such a bad guy. This is a great show and I hope you read all the way to the end. There are lots of nuggets and a big reveal with a very disastrous story.

We talk a lot now about being a real estate investor, real estate agent and Airbnb investing, which is near and dear to my heart. I hope you get some nuggets and that you end up reaching out to Rocco because he is such a wealth of knowledge. Let’s bring him on the show. Rocco Montana, welcome to the show.

Thanks for having me, Z.

Tell us, how did you first hear about financial independence?

I transitioned from the traditional W-2 worker, trading a lot of time for money and leaving my job, which I later learned stands for just over broke. I got into an investment coaching program. I’ve seen these postcards and advertisements, “Come and figure out how to get wealthy in real estate in a weekend and we can have financial freedom.” I was like, “What does all that mean?”

I went to a free Wednesday night class. They had me hook, line and sinker. I paid a couple of hundred bucks for the weekend-long class. The strategies and things I learned about finance were primarily focused on real estate. It’s a real estate investment-focused coaching program. It blew my mind and the opportunities that were out there to earn and to create passive income to offset your daily expenses.

Airbnb Investing: There is no negative or downside to getting licensed. In fact, it’s an advantage to get licensed as you embark on your journey of becoming a real estate investor.


That was the light bulb for financial independence, having to show up at a certain place or a certain time and a coaching program, which some people don’t like. Everybody has their positives and negatives experiences personally, but I had a fantastic experience. It got me started on my entrepreneurial and my real estate investment journey. I’m grateful for that. It was money well spent and it was not inexpensive.

A lot of those guru programs end up being $40,000. They have these like, “You can buy this and you can buy this other course.” I think you’re lucky that this sounds like it was a legitimate program and you didn’t get suckered into something else.

It was a legitimate program and you were pretty on the money for about what it costs. I had convinced someone else, a couple that was no longer associated with, my friends or a professional, to split it. We got into it for about a little over $20,000 for a couple, I find some other couple. I truly felt the only way to fail was to not follow the instructions. It was black and white and clear.

Me being who I am and a human being, I got enough information if it is dangerous. I did a couple of deals that worked and a couple of deals that didn’t in a big way. I don’t regret it. I still lean into those resources in that network. I occasionally pop on their website and use the services that I paid for to get questions answered if I can’t find them in my immediate network.

This couple that you don’t talk to anymore was the split because of the money?

It was a little bit more personal. It’s not a rabbit hole worth going down. They ended up moving out of state. They got involved in some other industries that they were more passionate about. I do know now both still have jobs and my wife and I are both business owners. We’re a lot closer to financial independence than we were when we started with them.

I know you personally and I know that you are a badass real estate agent. You sold us the house that I am sitting in right now before I got my license. You were the person who said, “What the hell are you doing with your life? You should get a license.” Now I have one. Thank you. This is all to you. I’m wondering if you were already an agent at the time that you took this class or that happened later, as you were realizing there’s an opportunity there.

Your audience is primarily investors. I don’t know if it’s just agents but when I took the course, I did not see any negative or downside to getting licensed. As a matter of fact, I thought it was a monster advantage to get licensed as I embarked on this journey of becoming a real estate investor. The other side of the coin is a lot of people are like, “You can’t say this and do that. You have to over disclose.” I’m like, “I’m not lying to anybody. I’m not trying to take advantage of anybody.” Why would I not get the license, share with these people that I’m trying to buy their house for cash or flip and talk about the advantages and disadvantages of going through an investor versus going to the open marketplace.

By the way, because I have my license, which was fairly easy to get, I can give you the best of both worlds. I can buy your house for cash at a discount. It could be quick, easy and painless or you can get the highest and best price with a significant amount of effort to list the house, plus the tools and the data and the MLS access. The realtor association, love them or hate them, can be a great network to get involved with.

There are a lot of rock stars in the realtor associations and there are a lot of other fringe benefits, systems, resources, tools, events and networking. I got licensed. I am involved in this investment coaching course and immediately got my real estate license. I quit my W-2 job, took a month off and went to the physical class because I’m not a good webinar learner. I was licensed within a month of leaving my W-2 job and I was an investor with a license from day one.

I love that because so many people will get overwhelmed or they won’t lean into it, but it seems you were like, “This is it. I’m lighting a fire and I’m going to change my whole life.” I know you’re married. Were you with Jamie at the time?

I don’t even think we were engaged yet. She liquidated the only full 401(k) she had to pay for the real estate investment course. I had convinced her. We are not yet married. She left a conference a day early from her W-2 job to come to be part of the interview that these guru courses to make sure that you qualify. It’s very fancy-sounding. At the end of the day, they want to make sure that you can pay that first bill and show a little bit of initiative.

They’ll definitely take your money, all of them, even the good ones. She dove in and supported me for about a year and a half working a W-2 job while I built our business, one beer and coffee at a time. That’s going to be the name of my book. Don’t steal it. It’s in the works. It’s one of the many things I’m trying to get off the ground and keep things going.

Once that first domino falls, the second one might not be as quick. But once that second one falls, it's off to the races. Click To Tweet

My wife has been super supportive. It took her about a year and a half to convince her to get away from that. I get my paycheck every two weeks and I have my 401(k). We have health insurance. What happens if something goes sideways? Now we are both business owners. We are partners in the investment company and the realty company. She has another partner in a construction business. We’re working on owning the vertical and as far as it comes to at least the real estate investment part.

I’m ready to go into your first deal and talk about that but I do want to highlight something that you brought up a little earlier. You were mentioning how you can buy homes at a discount with a real estate license? There’s the one way where you’re saying, “I’m negotiating with a distressed owner who might be going through a divorce, death, for foreclosure or something like that but the other way is simply because we have a license, we get about 3% off.”

For a lot of people, 3% off might not sound like a lot, but I was looking for a $1 million house. When I did the calculations, that was like $27,000 and some change. It can make a big difference to do your own paperwork, which you would’ve done happily and get to pocket that as equity. There are lots of benefits to having your license.

Quick side note, the log cabin that you see me sitting in is the second home my wife and I bought, which is Airbnb eligible. We can always talk about that and we’ll do that. We will Airbnb the other home that we already have. This house was $650,000, as I had written my 10% second home loan down payment, I also got a $17,000 check back closing because the seller my commission. The seller paid me to buy the house.

Let’s go into that because it’s fun for a moment, $650,000, so $65,000 down and then your closing costs were probably another $12,000 or $13,000.

I think I was $73,000 out of pockets between the earnest money, closing costs and down payment.

How much did you get back?

It’s $17,200.

You’re paying $50,000. It makes it so much sweeter and it makes your return on investments super great. Thank you for sharing that because that is a good whole nugget. We like to have the segment that we call the Thrill Deal. We want to talk about the first deal that made you feel like an investor. Do you have one that sounds appropriate? We can go to that trailer one you want to do. I want to talk about some Airbnb stuff because I know you for Airbnb.

I’m thinking in my head, “What was my actual first deal?” It’s the deal that made me quit my W-2 job. I’m going to go back before the trailer deal. That might have been my second deal. I can remember the numbers and go over some crazy ROI on how we did it. I was selling cars and working at a car dealership. I convinced my wife to spend all this money on this investment coaching program and I still have to keep my W-2 job because why are you ready to take the leap?

I’m doing some of the rudimentary, young investor things. I’m on Craigslist and Facebook Marketplace. I’m joining all the groups, finding out where the networking is and going to Meetups. On one of the groups, it was the investment coaching’s private group, which you get when you pay your $50,000 or whatever. A guy posted, “I’m overwhelmed with deals. My mother-in-law’s selling her house. I want a smooth transaction. Let me know if anybody’s interested, preferably cash offers. I don’t have the bandwidth. I want to help my mother-in-law.”

I reach out to the guy who says, “I’m hands-off. It’s my family. I’m going to put you in touch with my mother-in-law. Do the right thing. We share the same investment coaching. I am going to trust the transfer of trust with that program that you’re going to do the right thing.” I look at the house and I call up the lady. I googled Colorado real estate contracts, I printed it out and filled in the blanks with a pen. Now, we use Google+ or anything.

Was this 1990? What’s happening?

I’m handwriting these contracts and I sent them to the lady. She said, “I had 4 or 5 people reach out to me but you’re the only person that sent me a proper form. I had somebody try to sit me down and negotiate on a napkin.” The professionalism right there was awesome. I was so clueless and I got the property under contract. I reached out to a general contractor I knew and realized I didn’t know enough about estimating repair costs yet. He says, “I’ll buy it. What do you need for it?” I said, “Okay.” I believe I had it under contract at $440,000 and I sold it to him for $456,000.

You wholesaled it.

It was wholesale. I put it under contract. I went into the coaching program and found an assignment of contract form. I went to my general contractor and he walked through it. He could tell I was over my head for the amount of work. He said, “I do this.” I didn’t know he was a guy in my network, previous to my investment career. He says, “I’ll buy it from you. What do you need?” I went back and forth with some roof credit and things like that. We came out to $456,000. I put $16,000 in my pocket and probably in total, including signing at the end to finding the deal to making that first phone call, maybe four hours of work and I quit my W-2 job that week.

I imagine at that time, you were still scrappy and frugal because I know you’re pretty scrappy and frugal now. At $16,000, were you thinking, “This is a runway for me for 4, 5 months or something like that, and by then, I’m going to have something else going on,” or was that not even in the plan?

That was the plan. The plan was with $60,000, I can get by in a couple of months with this and I can focus on the next deal. Truth be told, my next deal didn’t happen for almost a year. I got to give you the whole truth. I can’t tell you it was all sunshine and rainbows from day one.

Airbnb Investing: Long-term tenants and short-term rentals are half the wear and tear and twice the income. They shower, shave, smoke weed, and leave. They don’t clean dishes or fix the couch.


I think there’s something about the first deal as an agent, but also as an investor. As an agent, I experienced this. I spent three months showing people around and not knowing what I was doing. I’m starting to feel a little desperate and then when I did the first deal, it was like, “I can do this.” It was easier. It’s almost like you have to mentally switch something in your mind and go, “This is possible. Now, I’m good to go.”

After that first deal and building my business, one beer and coffee at a time, for 8 to 12 months, I did about a dozen flips over the course of three years or probably 2 or 3 wholesales after that second deal and beyond. Once that first domino fell, the second one wasn’t quite as quick but for me, once that second one went, it was off to the races.

Tell me about the second deal and then I’m going to fast-forward us to the deal that you have that’s near my house that I think you’ve already sold. It’s fun the way you structure that Airbnb deal. I want to make sure that we cover it. Let’s talk about deal number two because it took you a whole year. Were you feeling like you were being a little overly cautious or there wasn’t anything or you didn’t know how to identify a deal when you saw one?

Overly cautious is part of it as much as I’m much more open to risk than my wife is. She’s a lot more conservative than I am in that sense. After doing many deals, you learn the ropes of where you can benefit, where you can be a little loose or where you need to be firm? That first year, I couldn’t make any deal make sense.

In hindsight, it was fear and secondly, it was too much of a buffer, like, “Just in case, I’m going to put in this extra $10,000,” when I probably should have put in an extra $1,000 or, “I’m going to calculate a year the whole time even though our target is 3 or 4 months,” and I could have calculated at six and still had a comfortable buffer.

Fear was a little bit of it but that second deal, I had some cash saved up. We might have used some 0% credit card money, but we bought a trailer house with a partner who was in a different investment coaching program. He’s a much older guy who had a much longer track record than I did, but he was open to working with me. He said, “I found this opportunity. I need some private money.” I said, “I’ll lend the money for the deal.” It was a $16,000 trailer.

I went with this partner, Tony, at the time. We emptied the trailer out, did a deep clean on a Saturday and a Sunday. I’m talking about a 55-year-old man with hundreds of deals under his belt. We’re scrubbing the smoke yellow off of the walls in this trailer house and then we market it for sale for $24,000. He and I split the difference, plus I made 12% as a private lender. The whole process was 60 days. My ROI on that second deal was 42% annualized. If I could repeat that over and over again in the course of twelve months, if we extrapolated the data, it was 42% or 46% were my annualized rate return on the money and time that I put into that deal.

I want to go back to what you’re saying about this 55-year-old guy who’s done hundreds of deals and he is on his hands and knees scrubbing the walls. It’s something that I think is inherent to investors. Most of us are scrappy people and I will say the same about myself. I love to travel, work part-time and be super casual but when it gets to me needing to do something serious like bang-out furnishing an Airbnb, I’ll pull sixteen-hour days. I’m cleaning trash cans with maggots. I’m doing gross-out shit. I will not ask anybody to do something I wouldn’t do myself.

We rented and loaded box trucks at midnight to get staging furniture out for Airbnbs. After my wife’s full-time job at the time and me starting my career as an agent, focusing on that as well. A little tip that I have, if I may share. I’m going to have to coin this term somewhere. Maybe you can experience this. You were a long-time investor before you became an agency. The conduit of opportunity in my experience didn’t from being an investor to being an agent but being an agent, I’m exposed to a lot more opportunities for investments.

Maybe you can attest to that or not as someone that was an investor for a decade before you got licensed or five years before you got licensed. I got licensed and when I leaned into the agent community, there was so much more. In my opinion, a lot of better opportunities to invest than there were without my license or without having that network of other agents.

I have this theory that it has to do with doing something real estate-related all the time. I have a very simple practice. I like the Redfin App and I look at it every day. It sends me listings that are new in the area based on what I’ve been searching. If I’ve been in Hawaii or all over, it sends me random shit, but it sends me enough stuff in Boulder that occasionally I’ll see something and send it to a client.

They’re probably already on a search. They may have seen it, but I cannot tell you how many magical experiences have happened because of that practice. I think it’s simply that I’m dedicated towards doing something every day that’s in real estate. If you’re in real estate as an agent, most likely you’re doing something real estate-related.

The freedom that real estate gives you, financially and time-wise, is unmatched. Click To Tweet

Maybe you’re knocking on doors or talking to people. You’re going to hear about off-market stuff. You are going to hear about stuff early and you’ll know how to recognize a deal because you’re in that market every day. Maybe it’s a combo, but there is something to doing something every day and letting the magic unfold through that. I don’t know how much further it was. Let’s do the timeline. When was this trailer parked deal?

I got my license in September 2016. I joined that coaching program in June or July. I believe it might have been October of 2017 was that second deal.

From there, one to skip a few, what did you do in between before you got this Airbnb property here in Boulder?

In 2017 is about when I started Airbnb’ing property. I had a roommate. My wife moved in with me because she had three roommates and was in this basement apartment. There were two people upstairs and it was outside of town. She wasn’t loving it and it didn’t make sense financially for us to have two different housing payments.

Since I had owned my home, I said, “Why don’t you come in and we’ll split the mortgage? You don’t even have to pay anything as my girlfriend.” I had a roommate in another bedroom that was paying 80% of the mortgage. My wife says, “We’re grownups. We’re getting married, engaged and we’re done with roommates.”

I’m trying to build our business by networking in beers and coffees and my wife’s got a W-2 job that she hates and we stumble upon Airbnb. We start Airbnb’ing the second bedroom instead of having a long-term tenant, which I’m sure you know or have shared with your readers. Everything I have read and in my personal experience that having long term-tenants and having short-term rentals. It’s half the wear and tear and twice the income with the short-term rental.

People show up. They shit, shower, shave. They go to the show and leave. Long-term tenants sit on your couch, smoke weed, watch TV and you’re like, “You’re putting a dent in my couch. Could you do your dishes?” We decided to start doing that. We get to the point where Airbnb’ing both bedrooms and sleeping on our couch.

It’s not very grownup.

Not exactly the intention my wife had but it was lucrative and I was able to convince my wife of the power of real estate, the moves that we could make next and how this will catapult our growth. That overnight success takes ten years that everybody talks about. I didn’t get to the point like you didn’t get to the point of X amount of properties, X amount of clients and X amount of six figures times, however, per year. It started with roommates, sleeping on a couch, maggot-infested trash cans and filling up a truck at midnight to get here. I think that’s an important thing to lean into.

I hope I’m not too far off-topic but for your readers, at least the newcomers or young investors that are young in their career. I’m six years in as a licensed agent and an investor. There are times when I’ll Airbnb all of my front-range properties and go stay in a hotel. It’s fun and a running joke with my wife and some of the close friends but if I go stay at the Westin for $150 and I’ve got 3 or 4 houses rented at $200 a night, I’m still winning.

You get a sweet little staycation.

We had fun. We’d bring the dog. It’s no big deal.

We have some numbers on that property. Can you tell us what you bought it for and all that so we can visualize it?

We’re going to go way back beyond before my investing career. I’ve never paid rent proudly. I bought my condo at twenty in Boulder. It was a foreclosure. I’m from New York and New Jersey. I’ve rounded out the rough edges, but I still got a way to go, I’m sure. I reached out to have as an agent in New Jersey at nineteen years old, and one person got back to me. They were like, “This guy’s not going to buy a condo in Boulder at nineteen years old.” Ben, I will never forget him. He picked me up at the airport. He showed me twenty condos in two days and dropped me off back at the airport on Sunday, Saturday morning to Sunday night.

Airbnb Investing: There’ll be times where you’ll have to Airbnb all of your properties and go stay in a hotel. If you go stay at a hotel for $150 and you’ve got three houses rented for $200 a night, you’re still winning.


I offered $80,000 on this foreclosure that was listed for $115,000. Ben said, “That’s not how it works.” I said, “That’s how it works where I’m from. If you don’t want to write the offer, I’ll find someone that will.” He says, “Okay.” The bank comes back and they go from $116,000 to $114,000. I said, “All right.” I offer them $90,000. He was like, “What are you doing?” I said, “I don’t care. We’ll figure it out. We’ll make it work on this one. We’ll find another one.”

The bank comes back to him and says they’re not going to entertain more offers under $100,000. I said, “Great.” I offer them $100,000. I bought the condo for $102,000 in 2006. I moved in January 2006 and I closed it November 2005. Fast forward to 2021, I got a place in Denver. It was a flip that went a little sideways. My wife fell in love with the house. We were able to afford to keep it and we could Airbnb. Because of the primary residence rules in both Boulder and Denver, we tried to walk the thin line and have one be my wife’s primary and another one be my primary.

Boulder was smart enough to see marriage records because I got married in Boulder County. They said, “Your wife has a rental license in Denver and you have a rental license in Boulder. Therefore, we assume Boulder’s no longer your primary residence. We decline your short-term rental license.” I have a real estate license. I didn’t want to push the limits. I got caught. I sold the property for $325,000.

I took no commission on it. I paid 2.8% to the buyer’s agent because it made more sense for me to defer my capital gains because it was my primary residence. Why would I take $9,000 as income with my brokerage when I can put that into my free and clear capital gains avoidance because it was my primary residence? That was the condo in Boulder.

Let’s go into that a little bit. Are you’re saying it was still your primary residence at this time or not technically? If you were there living there two years of the last five years, you could take at least $250,000 capital gain straight.

As a married couple, it’s up to $500,000. There is no tax on the $225,000 gain.

Do you remember what your mortgage was on that place back when you had your roommate and what your roommate was paying?

When I had the long-term tenant sharing the room, my mortgage was never more than $1,100 plus between $250 and $360 in HOA fees for over fifteen years.

It’s somewhere $1,300 to $1,400.

I was getting $800 a month with one of my first roommates. Towards the end of the long-term roommate situation, we had a roommate paying $1,000 a month.

For people that don’t know, these were basement rooms. You guys had it decorated too. You did a whole renovation of the kitchen. That’s a lot in Boulder to be paying $1,000. I imagine you had it furnished.

For the most part, we kept the dresser, TV and the bed in that room to make life a little bit easier.

You had to redo the kitchen. Do you remember what you spent on that?

This is a little bit of a side note. My property in 2013 flooded not because of the big flood in Boulder but because the unit above mine was vacant and the refrigerator line went. All the water had come through the floor through the wall in my kitchen that was separating my dining and kitchen that gave me the galley kitchen and down into my basement bedrooms. It was all popcorn ceiling. Because my homeowner’s insurance paid for it, I got $50,000 or $60,000 in remodel, plus move in, move out, plus a hotel for two months while the house is getting worked on. My renovation didn’t cost me anything. It’s a $1,000 deductible on the homeowner’s insurance.

You are a lucky guy.

I was very lucky in that situation.

I do think that luck favors the real estate investor. If you get yourself in the right positions, there is a lot of luck that can happen. I’ve experienced a lot. What happened was great. When you went from this $1,000 a month long-term person, what rates were you seeing from these Airbnbs that made you want to rent out both rooms and sleep on a couch?

Walking away from an unfinished product is not an effective solution. Giving up is not the solution. Click To Tweet

Part of it is a necessity. Let’s call a spade a spade, but the other part of it is we probably could have done one. We were Airbnb’ing one-bedroom and we used some resources like AirDNA and things like that. My basement bedroom was the number one private bedroom in Boulder for three years on Airbnb. If you went to AirDNA, that bedroom in that condo was the number one private bedroom with shared common space in Boulder for four years. You might be more analytical than me. I’m a little bit more of a sales guy. I know that, as a whole, that property in the analysis, even with a $1,100 a month mortgage and $300 and change in HOA fees, we were doing between $3,500 and $5,000 a month in Airbnb on that property.

That made sense and that’s also back when you were becoming an agent. That allowed you not to have a deal for a year and have the spaciousness. I want people to realize that because that was true for me too. At the beginning of my Airbnb, I lived between two apartments and stayed wherever wasn’t booked. I had a rolling suitcase and I was living between the two. That was my life for two years.

I still do that.

It’s what you got to do. It’s the hustle. Now you have luxury homes that you go-between. We can all dream but it allowed me to call myself financially independent and freedom to travel. It’s so much good that it outweighs some of that discomfort. I want people to see that because Airbnb changed my life for sure.

We get back to my wife’s family ranch every 45 to 60 days. Sometimes we go back for two days and sometimes we go back for twelve. The Airbnbs are rented or both houses will be rented. All three houses now have been rented here in Colorado’s Front Range. It’s a little bit higher risk. Don’t get me wrong. I know your properties, at least used to be in other states that are a little bit more affordable housing prices. We have three Colorado front-range properties. Higher risk comes higher reward and a higher margin of error when things go sideways. The freedom that we have financially and time-wise, thanks to Airbnb and real estate, is unmatched. I don’t know where else you can get it.

Real estate sales allow you to have this unlimited and uncapped resource for income. It’s as much work as you want to do or as much hustle as you’ve got. You can make $1 million-plus a year if you want to. I think there is not a lot of other jobs out there that do that.

You can make $1 million-plus a year and it doesn’t have to be that high hard. It’s not that much brain damage. I tell everybody, whether it’s your tenants, vendors, clients, buyers, sellers, investors, just care. That’s what I tell my team. Give a shit and you’ll stand out amongst other landlords, agents, investors, vendors or whatever you’re doing.

When you’re passionate, like you and I are, about real estate, financial independence and helping others, primarily being passionate about helping others, especially in the real estate space because we’re both passionate about that as well. You have no choice but to get there if you care about other people and you’re in real estate.

Before we transition to the second part of the show, what would you say is your average cashflow from your three houses? I know it’s seasonal but do you have an idea of what you’re living off of on these homes?

We average it over the year, $10,000 a month in 2021. We are moving from one condo to another. I don’t know if the cost aligns. It’s quite a luxury property yet but we anticipate doing $15,000 a month in Airbnb in 2022.

Is that gross or is that net? Is that your profit?

That’s gross. That doesn’t include mortgages. Our mortgages are about $8,000 a month across all the properties.

$7,000 is still super great, plus you’re selling tons of real estate. Even if you weren’t, that’s enough to be financially independent. Maybe not for you because you got big ass goals.

We’re making lots of investments in our businesses and in our properties. My wife and I talk about it all the time. Once we pay off any of the mistakes that we’ve made, the coaching programs, the few losses that we have taken, which are the minority but they were larger, the minority of deals where we took losses, we could live off of these three houses for the rest of our life. I can stop selling real estate. We could pay off two of the three mortgages and still live a super nice life and never have to work again on three houses.

If people are new to real estate, they don’t necessarily know. Maybe your cashflow is $100, $200 or $300 a month per house. If you’re trying to cover a $75,000 a year income and leave your job, that’s a fuckload of houses. You made so many houses. You’re like, “How am I going to manage all that and everything.” It shows the power of Airbnb that you can do this.

Airbnb Investing: You can make $1 million-plus a year and it doesn’t have to be that hard. You just have to care, whether it’s your tenants, vendors, clients, buyers, sellers, or investors.


For me, it was two properties and they were little ass condos. Now you’re saying three houses, but you could have done it earlier, two with less. It is pretty remarkable how fast you can supercharge that. I wasn’t going to go into this but because you brought it up, I want to hear about one of your fantastic fails. Would you be willing to go into that?

My fantastic fail came in a pair. Up in Fort Collins, which is a great town in Colorado, it’s where Boulder meets Cheyenne, Wyoming. You got a lot of left, a lot of right, a lot of yuppies, cowboys and they all congregate in Fort Collins. We bought two houses one block apart. We saw another, at least one if not two investors that had done maybe half a dozen deals in that neighborhood in the last several years.

We thought we were going to be hotshots and we were going to do these luxury remodels. These were deals 3 and 4. We underestimated, over-trusted and undermanaged. We had a business partner that brought no money to the table. We used some family money, 0% credit cards, hard money and bought this house for $450,000. We put $120,000 into it, so that’s $570. We borrowed 100% of the money at 12%. I believe we had this property for two years to get it down.

I remember a phone call from the general contractor at the time, who we do not use or recommend, where the drywaller blew his shoulder out. I hadn’t been by the property in a week, which is my fault. I undermanaged. I thought the partner that we had up there that didn’t bring any money to the deal was going to be on-site and checking in every day. There’s no work had been done for two weeks.

I called up the contractor and said, “What’s going on?” “He blew his shoulder on. He was in the hospital and couldn’t get to work. We’re at a standstill.” I was like, “This house is costing me $475 a day. What are you missing about needing to be expeditious?” Maybe I could have delivered the message better. It shouldn’t have got to this point where we’re eighteen months in to a 6 or 8-month hold. The budget was going to be $80,000. We’re at $120,000.

At the end of the day, you have to have checks and balances in your real estate investing business. That’s the point I can make. Between the two properties, they sold within a month of each other after holding them both almost for two years and both going 30% or more over budget. We lost almost $250,000 in borrowed money, credit cards and family money. That being said, here’s some advice if it goes sideways in your audience’s business. All of our lenders got paid back in full. All of our partners paid right.

I had lenders renegotiate interest in terms and fees with us because we never ran. I begged and borrowed but I didn’t steal. The begged, borrow and steals are phrases we might be thinking of when I say that. We begged and borrowed and got the jobs done because we knew walking away from an unfinished product was not an effective solution. Giving up was not an effective solution and that’s the point I’m trying to make when things go sideways. We learned a lot, who to partner with, not to partner with, how to vet your partners, what level of trust to give to your vendors, how to have accountability for your vendors and how to run your numbers better?

There was so much learning that happened. How to have a hard conversation? How to go back to the hard and private money lenders and say, “I don’t know if I can pay you this month.” I’m taking out 0% credit cards left and right to finish the paint and drywall so we can get it listed and get it sold. I’m not going anywhere, but I’m asking for you to work with us because I’m showing up telling you, “I’m going to do my best and do right by you. It might not be in the timeline that you want, but I’ll get it done.” My favorite private money and hard money lenders still work and recommend us.

We’ve done another 8 or 10 deals after that where we’ve made money. Everybody got paid back and everything went right side up. We ended up selling those houses. We bought them both for around $450,000. We put about $120,000 in each of them, which puts us at $570,000. Trying to make a sales commission wasn’t happening for me. Thank God I was the listing agent because I had my license, but 3% of the buyer’s agents, two years of hold costs, we sold those properties. I think we sold one for $605,000 and one for $625,000.

That’s a powerful story and I’m glad you were willing to share it but it’s rough for sure.

If you take anything out of it, Zeona is don’t give up, don’t stop. Things are going to happen. Don’t run and hide. Put your best foot forward. Be honest, come from a place of integrity, communicate early and communicate often with your partners, vendors, lenders and you can make it happen.

It’s funny that you brought up hard conversations because you are somebody that I had called before and said, “How do I have these hard conversations?” I call you very often when I need some advice on how to be like a better person do the right thing.

Something is not a failure unless you quit. Click To Tweet

That’s a pretty big compliment.

You’re my go-to guy. I appreciate the candid story because the thing that I like the least about real estate is that people are willing to talk about all their successes. How special and smart they are but they’re not willing to share the times that they failed and that’s part of it. We all have to fail a little bit.

The coaching program I was in emphasized fail forward. They were like, “People are going to make mistakes.” Whether you’re a real estate agent, investor or widget salesman, you’re going to have mess-ups. Get out of the way, move forward, move on and you can get it done. One of my favorite quotes or sentiments that was shared with me at one of the many conferences that I like to visit and they work for me, and not everybody loves it. I got people that call me Ra Ra Rocco in my network because I’m always the one that could pull out a quote by some famous sales guy, like Zig Ziglar, a Grant Cardone thing or a Gary Vee thing or whomever.

I was at a conference and along the same vein as being worried what other people are doing or other people’s successes are having a five-gallon bucket on the shoreline and picking that five-gallon bucket in the ocean. That’s your deal flow or your opportunity and being upset that there’s another guy, a mile down the shoreline with his five-gallon bucket.

What that means to me is whether you think about that in terms of how to get through losses, being jealous of somebody else that’s doing better than you or whatever it might be. There is so much opportunity. As long as you keep filling that bucket and you keep going to that shoreline, there’s much opportunity. It benefits you never to give up and keep moving forward. Things are going to go up and down. Keep moving forward and you’ll get through it.

I’ve got to tell this story before we go into the final four because it is alive right now. This was from an Airbnb guest. We Airbnb our own property here and we do a lot of pets sitting in a lot of travel. On Christmas in 2021, we got a message from our guest who was checking out the next day. She said, “I got to tell you, I slipped and fell on your dishwasher.” I’m like, “What?” That’s a first and she sent me these photos. It must have been open at the time. She slipped and fell. It looked quite painful, but she was fine. A couple of dents in the dishwasher, but it rendered it unusable.

She ended up sending us $600 to pay for the dishwasher. Now we upgraded and got something that was $900, but it’s still pretty awesome that this stuff happens. It’s a hassle. I had to do a lot of shopping around to get the delivery and how we’ve got guys in our house, but it’s one of the upsides of Airbnb.

Sometimes you can turn something that’s negative into a positive, like how you had that raining into your apartment from the upstairs neighbor. It turned into a whole free renovation for you to get rid of that popcorn ceiling that’s a super amazing kitchen. Sometimes those are the failures that are not failures until the end. You realize they’re awesome. Let’s go into our final four. I’ve got four questions for you. I don’t notice this about you but are you a big reader because we’re going to ask you what you’re reading right now, but maybe you’re a listener instead of a reader.

I’m a big fan of 75 Hard if you’ve ever heard of it. This guy, Andy Frisella, created this self-disciplined mental toughest program that also gets confused with a fitness program because it has a fitness section of it, but it requires the reading of a physical book. It got me in the habit of reading physical books. I do like to listen. I did listen to David Goggins, Can’t Hurt Me. Do you want to talk about dealing with adversity and pushing through? That was a fantastic book.


I also got into hunting. The physical book I’m reading is Steven Rinella’s The MeatEater Guide to Wilderness Skills and Survival. I’m reading a book about how to build a shelter in the woods if you get lost. How to find plants that are edible? How to find a small mane, trap them and have food if you need it? The next book is Traction. They’ll be back into the business books that I’ve had many people recommend, which I believe the premise is a lot of tracking.

It’s streamlining your business. I feel that if COVID takes a turn for the worst, I’m going to come to your house. I’m going to come to figure out how to be in the woods together. I got to tell you that at the beginning of COVID, I was like, “Maybe I need to learn how to be a little more self-reliant.” Luckily we haven’t had to do that yet.

Thank goodness but COVID is part of what got me more into hunting and how to live off the land. If shit does hit the fan, there are very few people that are going to make it more than a few weeks.

I hope he comes up with a vegetarian guide because I’m pretty much screwed. I don’t eat meat, so I don’t know what’s going to happen there.

There are a shocking amount of edible plants.

Question number two, what is the best piece of advice you’ve ever received?

Don’t quit. All the mistakes, errors and hard times, it’s not a failure unless you quit. That gets misunderstood by a lot of people too. People don’t want to quit their job to become an entrepreneur or to move into a different field, that’s not quitting. It’s making a transition. If you deal with some adversity and you give up on that task, that would be a little bit more along the lines of the definition of quit in my book.

It’s about how you look at things. For example, in that apartment you had, when the ceiling came raining in, you could have been like, “I knew I should have never bought a property. I’m never doing this again. It’s over. This is terrible.” You listed the next week but you ended up going through the process, getting it fixed, realizing that you had so much more money to do with how you wanted and made it something amazing. It’s the same with this dishwasher. I could have said, “I’m never doing Airbnb again. I’m out $600.” You see how you can make something better. If it’s not ending in a good way, it’s probably not the end yet. I don’t know how that quote goes, but something like that.

I get what you’re saying.

Question number three, what is your why?

I almost feel like it’s cheesy to say but with financial independence, freedom is my why. I like to say freedom because of the freedom to give back to my community, family, to spend time with whom, where and when I want. To be able to be the master of your own universe. My why is to keep going, get through the adversity, try again, take another risk and do another deal. The goal is freedom. Freedom of choice is the biggest thing.

The MeatEater Guide To Wilderness Skills And Survival

I had somebody close to us call me money hungry. I was like, “You’re so missing it.” It’s not about the money-hungry and making more money so that I can have a fancy car, home or nicer clothes. It’s about the freedom that comes with making with that earning potential, wealth and the ability to control your time to have more choices. My why is the freedom to give back, do what I want, when I want and with whom I want.

This is why we get along because freedom is my biggest value too and that’s what set me out on this path. Question number four, if you could go back and do it again, what might you do differently?

I want to say the same answer a lot of people say is to start earlier, if I could go back and do something differently. I was terrified of commission-only and starting a business. I can only imagine with the last several years of being a real estate investor, agent and being self-employed. It’s to start sooner. That’s it. If I could go back and do something different, I would hesitate less.

I’m like, “What was I doing investing in real estate and managing properties this whole time without a license?” I also trust in timing. I’m happy I’m here now. Where can people find out more about you or get in touch?

My business number is my cell phone number. You can always call me at (303) 862-4939. My real estate team is JROC Properties. It’s like a cattle brand. My wife grew up in the cattle ranch and JROC is for Jamie and Rocco. My wife, Jamie and I’m Rocco. It’s been a pleasure. It’s @JROCProperties on all the socials. Feel free to reach out. DM me or call me. I’d love to help if I can help anybody out there.

Thank you so much for your time. A lot of people are going to resonate with your story and it was fun to have you.

Thank you so much for having me, Z. It’s always a pleasure to connect with you.

That was Rocco Montana. I’m waiting for Craig to say, “Z, what’d you think?” What I thought was it was a fun show. I like the whole spectrum. The fantastic fails and the way that it’s ended so well in his life with three properties, how they’re cashflowing $7,000 a month and probably more in the summertime of 2022. It’s inspiring to see what can be done with little resources and even coming back after losing $250,000.

I hope you guys take away some great nuggets and maybe get inspired about Airbnb. If you’re thinking about starting an Airbnb business, you can reach out to Rocco or me. If you’re thinking about becoming a real estate agent, Craig, I, and Rocco all have teams here in Colorado but we can have teams nationwide and we would love to talk to you. Reach out because you could start now and that might be starting sooner than you thought. Thanks so much for reading all the way to the end. If you like the show, please share it around with your friends or leave it a comment or review wherever you are reading. We’ll see you next time.


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About Rocco Montana

Rocco is our team lead and co-founder of JROC Properties. Born and raised in New York/New Jersey, the outdoor lifestyle brought Rocco to Boulder where he lived for 15 years before recently moving to the Wash Park neighborhood of Denver. Rocco purchased his first property in Boulder at 21 years old.

Since then, he has developed a wide array of experience in Real Estate including flipping houses, wholesaling, investing in commercial real estate, and short and long-term rentals. Rocco married a rancher’s daughter from South Dakota whom he loves very much.

Together they enjoy spending time with the family at their nephew’s rodeos and going back to South Dakota for branding or sale days on the ranch. Rocco has practiced a form of martial arts for the past 10 years. He enjoys hiking, biking, snowboarding, camping, climbing, archery, and hunting.