ITF 82 | Medium-Term Real Estate


Many people found the path to financial independence through real estate. Today’s guest has walked on that path from a young age, learning from his family to eventually taking on his own. In this episode, Craig Curelop and Zeona McIntyre sit down with entrepreneur and Airbnb ambassador Jake Cohen. Jake shares his journey in real estate, getting his start in hotels and falling in love with the Airbnb short-term, medium-term model. He takes us across the properties he has, the big rehabs he did, and the investment partnership he has with his mother. Talking about the elephant in the room, Jake also imparts some wisdom on preparing your properties for a potential recession. This conversation is packed with insights on the industry’s current state and how you can navigate it in the future. Don’t miss out!

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From Hotels To Airbnbs: Navigating The Short And Medium-Term Real Estate Model With Jake Cohen

How are you doing, Z?

I am doing good. I’m excited that our guest is talking about Airbnbs because I am in the process of selling a B&B and buying another one. We talk about the recession a little bit and it freaks me out because it is one of those things. What happens if my little plan doesn’t work out? It’s always scary to buy real estate.

What are you going to do if you can’t do Airbnb? What’s your plan B?

I don’t have a plan B. It’s positioned well. This house is located 1.5 hours from Seattle. With the type of guests and the amount of money around there, people will always want to drive to the destination and stay. My whole thought is that if we hit a recession, people may not be flying to Hawaii and those grandiose vacations, but they will drive somewhere cool by the sound and do a kayaking trip and get out in nature. Here’s hoping.

If they don’t have jobs, they don’t have anywhere else to go. They then can go on vacation. We’ll see what happens.

I’ll let you guys all know how it happens.

You’ve got to follow Z’s story, @ZeonaMcIntyre, on Instagram. Speaking of Zeona McIntyre on Instagram, we got a guest, Jake Cohen. Jake is an awesome guest. He has an interesting start getting into a hotel right away and then how that transitions into him falling in love with Airbnb, the short-term and medium-term model. He talks a lot about how you get more out of your property, the big rehabs that he did, and his story through the whole thing. It’s a fun episode. Z, anything you want to say before we bring him on?

We should get him on.

If you’re thinking about becoming a real estate agent like us, you might want to go to Kaplan. That’s where I got my license. I found that they made all this dull information interesting and memorable. If you’re looking at getting your license, see if they have your state. They cover a lot of states but not all of them. If you want to get a little discount, use our code INVEST2. Thanks, guys.

Jake Cohen, welcome to the show. How are you doing?

I’m doing great. Thanks for having me. I’m happy to be here.

It’s good to have you on. I hear you have a fun story to tell us ahead. Why don’t we kick it off from the beginning? When did you first hear about financial independence?

It’s a little hard for me to pinpoint the exact moment when I knew about financial independence because financial independence has somewhat been a part of my life for a long time, although I did not call it financial independence. When I was about ten, I remember my grandpa was explaining price-to-earnings ratios to me on stocks. He gave me a big book and he told me to circle all of the stocks that had priced earnings ratios above ten and those were the ones we were going to look at.

Is your grandfather Warren Buffett?

He’s not Warren Buffett, but he did well investing in stocks. That was my first introduction to what stock is and what a stock can do for you. I found out later in my life that my grandpa did well investing in stock and that’s how they made a lot of their money. As I grew up, my parents house-hacked. In the first house that I lived in, we had a basement apartment. They rented out the basement apartment. We then bought a bed and breakfast. We lived in part of the bed and breakfast. We had guests in the rest of the bed and breakfast.

My whole life was an introduction to FI. When I realized FI was FI, I was probably about 32-ish. I was listening to The BiggerPockets Money Podcast and it was episode 5, 10, or something like that. It was early on. They introduced these guys from ChooseFI. ChooseFI has grown hugely since then. This was the first podcast that they were on at that time. I started listening to their episodes and I took a deep dive. I’ve listened to probably 1,000 FI podcast episodes at this point. I feel well-versed.

You come from an early version of financial savviness in your family. You’re lucky. It’s awesome that you were able to grow up with that and see your parents outside hustling as well. You heard ChooseFI around age 32. Is that when you start taking action for things yourself or have you been investing prior to that?

I invested prior to that. I house-hacked when I was 22. I moved into a hotel and managed the hotel and got free rent by managing the hotel. From there, I bought my first house when I still lived in California. It continued to grow. I didn’t do a whole lot of stock investing at that point because I didn’t have any money. Eventually, when I started to get real jobs and made a little more money, I was able to do some stock investing.

I need to hear about the hotel. How do you move into a hotel and then get free rent? That sounds super interesting.

It’s not quite as weird and crazy as it sounds because my parents owned the hotel. My parents owned a bed and breakfast as I was growing up. When I was graduating from college, they decided they wanted to have two locations. The first location was in Lake Tahoe, that’s where I grew up. The second location was in Palm Springs, California. They bought a 1950s-themed hotel and decided they were going to renovate the hotel, reopen it, do the bed and breakfast thing, and it was going to be great.

The only problem was when they bought the hotel, they found out the manager didn’t want to stay. Suddenly, they were stuck with a hotel 500 miles away from them and no one to run it. “Jake had graduated college.” I said, “Sure, I’ll go down there and manage the hotel.” It was quite an experience. I did a big renovation and went right in and learned from the Hard Knocks because we went right into a recession. It took us about five years to get through the recession and recover. This was in 2008. A little crazy.

I know you a little bit, Jake. Craig doesn’t know that Jake takes on a lot of Airbnbs that need a ton of renovation. He’s the guy that takes on the Airbnb that needs $250,000. He breaks it down and starts all over again. This all makes sense. It’s coming together where I’m like, “This is not your first rodeo.” This is where you slept and breathed. You were raised in that.

I’ll blame my dad for it.

Don't overextend yourself. Click To Tweet

You’re 22 years old, having this massive rehab in front of you. What did you do? Did you hire everything out? How did you find contractors? While many people may not be in your position of doing rehab in a hotel, this could apply to any renovation. Give us some of your tips.

I had a lot of support in that initial part of the renovation. My dad is a handy guy and has the patience of God or something. He’ll sit there with a problem for eight hours and figure it out slowly and methodically. I don’t have that patience. He was a big part of helping me with that renovation. I took over the management of the hotel after the renovation. It was me, my dad, and another guy that worked with us. We started doing this rehab ourselves.

In the first shower that we tried to take out, we got through the first layer of tile that we were demoing, and there was another layer of tile. We demoed the second layer of tile and then there was a third layer of tile. This one shower stall took us two days to demo. This was the first thing we did on the property. We said, “What did we get ourselves into?” We did end up hiring a lot of help throughout the process. We were trying to still run the hotel at the same time. We were doing rehabs on 1 or 2 rooms while we were renting the hotel’s other rooms. It was a mess.

I don’t know if I would do it exactly that way again. We were trying to save a buck and do a lot ourselves. It was great. I learned a ton. It was interesting seeing coming out of a recession and into a stronger market, how important the marketing was, and how important the Internet became. That was at the time when everyone was transitioning into booking online. I signed up for Airbnb in 2012. I had no idea what it was at the time, but I had the hotel at that time. I thought, “This would be interesting.” I never got one booking from it. All of these things are now things that have built the experience that I have now.

I’m curious about the recession as a hotelier. For me, being in short-term rentals, I’m scared of the next recession. Maybe it’ll be minor and it won’t be a big 2008. It feels like it’s been coming. It’s been trying to come for a long time. Do you have any words of wisdom? How are you preparing your properties for a potential recession?

The biggest thing is don’t overextend yourself, which is exactly what we did not do. We overextended ourselves and went straight into that recession. It was difficult. We were worried about losing both of our properties at that time because we had taken out hundreds of thousands of dollars of loans. We were unable to pay them back at that time because the business went in half.

For established businesses, it’s not as big of a deal. We were trying to start over as a new brand with a higher price point, a different product than what we were offering before, and that made it difficult. That being said, going into this next recession, whenever it comes, I agree with you. It seems like it’s coming. Make sure you have lots of reserves. Be ready for anything. Don’t commit yourself to huge projects in the future until you know you have the cash to back them up.

You have a lot of reserves. It’s such good advice. We’re looking at it from that perspective of, “There’s a recession coming.” What about the other perspective of inflation that’s at a 40-year high? Your cash is getting devalued like crazy. What do you recommend people do?

Both invest and hold reserves. Let me play the perfect political card here. You should be a Republican and a Democrat at the same time. It’s difficult to make those calls. I’ll be honest. I am selling a property because of the huge highs that we’re experiencing in our market. I’m also buying a property because there is an opportunity to still invest and do well. I’m doing both. What probably is the perfect situation is maybe to have a HELOC where you can access some funds if you need them, but you’re not paying interest on them right now.

Ultimately, that is good advice, to have a HELOC. It’s been harder and harder to get HELOC, especially on investment properties. It’s fairly easy to get one in your home. On investment properties, it’s tough. Don’t overextend yourself with the loans that you have. If you’ve bought properties in the past several years and you haven’t refinanced them, I guarantee that equity in them. Rather than refinance, pull out every dollar, and make it super efficient, enjoy your cashflow. Rents are going up. Enjoy that cashflow.

That way, if there is a recession, everything tanks. People are still going to need a place to live. They’re still going to need to pay your rent even if rent declines a couple of $100 bucks. Hopefully, this increase brings it back down to where it was when you bought the deal. That way, you’re hedging against the long term. A lot of people lose in a recession. If you can keep yourself from drowning, that’s the goal in a recession, in my eyes.

Jake, I want to take you back after the hotel. You went from this crazy experience that maybe was a little bit traumatic. You then went in and bought your own house. Knowing what you knew, did you buy something that needed a lot of renovation? What was your thought process on that house you got?

Interestingly enough, the first house that I bought did not need a lot of renovation. It’s probably the only property I have bought that did not need a lot of renovation. At that time, I was living in Palm Springs, California. Palm Springs was going into this recession. I was starting to have a little bit of cashflow. I wanted to have a place of my own. I bought this place in Desert Hot Springs, which is barely fifteen minutes from Palm Springs, for $108,000. It was in a country club. It had a golf course. It was nice.

I wasn’t ready to move out of the hotel yet, so I rented it for a year to continue to grow a little bit of my extra cashflow. It worked out great. I moved into that property with a roommate, house-hacking. It turned out well. I thought in my head that maybe if the market continued, I could make a good appreciation play on that. I only sold it for about $135,000. I never made a huge, big cash lump sum on that. Nonetheless, it still went up. It gave me a place to live and it was nice. It did not need a bunch of renovations.

ITF 82 | Medium-Term Real Estate
Medium-Term Real Estate: Make sure you have lots of reserves. Be ready for anything. Don’t commit yourself to huge projects in the future until you have the cash to back them up.


What year did you buy this property?

This would be 2009 when I bought that property.

You brought it the trough. The real estate is tanking. Everyone’s saying, “Don’t buy real estate.” Jake is buying real estate anyway. You sold it for $135,000. What did you say you bought it for?


Do you know what your mortgage payment on that was? Do you remember?

I don’t. It was low. $600, $700 a month. I rented it for $1,200 a month. I did have an HOA payment as well. I want to say I was cashflowing a couple of $100.

Are you living there or not living there at this point?

This was before I moved in there. Once I moved in, I rented one room for $600 and then lived in the other room. It probably was negative a few $100, but I was getting a place to live. It’s still pretty awesome.

It’s still a huge one. This is a different time. You’re making the 1% rule over in Palm Springs, which is pretty amazing. Your cashflowing. If you’re seeing what real estate can do for you, it’s amazing. You sell it for $135,000. You’ve got a couple of years of cashflow. What happens after that?

At that time, I had moved to Denver. It was a different time in Denver for those of you that are reading. In 2012, the houses here were not valued at $1 million everywhere in Denver. There were houses to be had for $100,000 or so. I rented at that point. I was trying to figure out if I was going to be with the girl I was with, who now is my wife. We now have two kids.

The first real estate investment we made together was the property we bought in Denver in the Sunnyside neighborhood. It was a 3-bed, 2-bath house. It’s about 1,200 square feet. We bought that for $365,000. That one is on the market under contract and we are selling it for $795,000. We bought that in 2014.

Was this a rental the entire time or did you ever live there?

We lived there for five years. It was a great first home for us when we had our first child. Our first child started crawling when we realized it was time to move to a bigger house, a bigger yard, a bigger everything because she was moving. We realized we needed more space.

Did you buy this property with a low percent down or did you go with 20%?

The goal in a recession is to keep yourself from drowning. Click To Tweet

We bought it with 20% down. It was a great first property for us to buy together. At the same time, I started investing with my mom in 2014. I can give you a little more background on that, but that was a whole other side of my investing life.

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Before we move into your investments, I want to highlight that this is a perfect example of buying and holding and why that is great. A lot of people reading might be like, “It’s the house that you lived in. What’s interesting about that?” Getting to see what happens over time if you hold on to something and get to enjoy the equity, this place doubled for you. That’s pretty awesome.

One thing I want to add to that is a lot of people, when they want a house hack and whatnot, don’t want to live with people. That’s one of the biggest bits of feedback that I get against house hacking. Jake bought this property in 2014. He bought it with 20% down, but he could have bought it for 5% down or 3% down.

Instead of living there for five years, he could have lived there for one year, had the whole place for him, his wife, and his child, moved on to the next one, and then rented out the first one. That’s another way that you can house hack and build a portfolio. You’re not going to get super rich in one year off the strategy. Jake got $400,000 of equity in four years. That’s a salary for a lot of people.

Small disclaimer, we may not have an appreciation as we’ve had for the past several years in the future, but I sure hope so. That’d be great.

Who knows? We could or we could not. No one knows. The whole thing is you don’t put yourself in a position to be lucky. If you never buy, you’re not going to get lucky.

I love that. Put yourself in a position to be lucky. Well said.

You have an investment side of things and you invest with your mom. Let’s talk a little bit about that dynamic and how that came about. Give us the lowdown.

It’s a little crazy. If you had asked me growing up or during my hotel career who would I be investing with, my mom or my dad, it would have been my dad 100% every time, no questions asked. The funny thing was my dad wanted to keep running the hotels and he did. My mom wanted to get out of the hotels and she did. My mom took a little bit less. We realized that she hadn’t set herself up for a great retirement.

I told my mom that I would work with her and we could invest together. I would do the property management and renovations and she would put up the cash. Our first investment was $135,000 in 2014, a 3-bed, 3-bath townhouse at 17th in Sheridan in Lakewood, right on the edge of Sloan Lake. That place is probably worth $500,000-plus. It’s crazy.

ITF 82 | Medium-Term Real Estate
Medium-Term Real Estate: Rather than refinance, pull out every dollar, and make it super-efficient, just enjoy your cash flow.


I’ve got a house right there.

It’s a good spot. I wouldn’t mind living in that area. It’d be awesome.

Let’s get into that property. What did you buy that house for?

$135,000, 3-bed, 3-bath townhouse. That was another property that did not need a ton of renovation. It did about $5,000 in renovations. I rented the property before we closed escrow. People stayed in that property for three years. I sold the property before they moved out. It was the easiest, best long-term investment property anyone could ever own. I started with rent at $1,400 a month and it grew to $1,650 in year three when we sold it. Our expenses have stayed at about $1,100 a month. It was a nice little cashflow play for us.

Why did you sell it?

We decided we wanted to trade up. The truth is, I thought maybe the market was peaking at that point.

What year was this?

2017. This will be somewhat of a common theme because every time I think the market may be peaking, I try to pull back a little bit, take a little money, and move it to somewhere else. I worry that if I leave all that equity, I’m not going to have access to it if the market changes. We sold it for $308,000 in 2017.

You’re still looking at over double in three years. Put yourself in Jake’s shoes and you’re like, “This thing has doubled in three years.” It feels like it’s the top. Things are going crazy. We don’t have a crystal ball. We can’t see that in the future. In hindsight, this is 2020. I don’t know if that was a horrible decision. You don’t make your money until you sell. You made some money and you pulled out. Where did you put the cash?

We 1031 into a duplex in Steamboat Springs, Colorado. It was a 2-bed, 1-bath on the top and a 1-bed, 1-bath on the bottom. This is where I started my short-term rental career where I got into vacation rentals. I found this place that needed a ton of work. I go after the ones that are the worst and need everything. This one was a mistake in how much it was needed. Nonetheless, I went up there. I found this place and it was $470,000. The market seemed like it was primed for a vacation rental.

I talked to a couple of property managers and they said, “You could do $50,000 to $60,000 a year in revenue with this property.” To me, after taking the money where I was making $1,650 a month, $50,000 to $60,000 a year seemed like a pretty big upgrade from that. I dove in. I did this huge renovation. We spent way too much money. It was about $260,000 that we ended up spending on renovation, which is a little bit of a mistake.

In our first Airbnb property, I wanted to impress. I thought I had to compete with the Four Seasons. I was doing all the highest-end stuff, quartz countertops, and all these things. Meanwhile, it’s a 600-square-foot apartment. Is it going to compete with Four Seasons? Probably not. In our first year, we did $80,000 in revenue. It made money every single year that we owned it. We cashed out of that property in 2021 for $878,000. We got our money back, but we didn’t get a ton of extra money after that big renovation.

Every time you do something, you double it.

If I continue to do that, life will be good.

Put yourself in a position to be lucky. Click To Tweet

You’ll have people giving you money left and right. Jake, you’re talking big dollars here, $60,000. How do you finance that? Is it your mom that’s doing that? Do you have any other outside investors?

We did have some outside investors. It was complicated because we got part of the way through the project and our budget was not nearly $260,000. We were in a situation where you can’t stop halfway through a project. One of the lessons I learned from that project in Palm Springs was that we realized we were getting ourselves into trouble. If you leave it halfway done, you’re not out of trouble.

We kept the foot down on the gas pedal and said, “We’re going to finish this thing. We’re going to get it done as fast as we can. We’re going to start making money. We’re going to start paying things back.” That’s exactly what we did. Luckily, we were able to bail ourselves out of that one. It’s not the way I would do it again. If I went into it now with the knowledge I have, I wouldn’t have gotten myself into that same trouble. That’s how we learn.

Making mistakes is huge. How did your relationship with your mom go through this whole thing? I imagine working with anyone’s mom can be maybe a little frustrating. Maybe they’re a little stubborn or whatever it is. Was there any animosity or anything like that? How did you navigate that relationship?

That was the only project that we worked on together. Since then, we have decided that I will take care of the projects and she will not be part of decision making or anything of that. Our relationship has been significantly better since then. She was supportive, given how everything was going. We were both frustrated with the situation.

Part of it was trying to push to get it done faster than we should have. We were trying to get it ready for high season in Steamboat, which starts in wintertime. We bought this at the beginning of November. We said, “We can do a $250,000 renovation in a month and a half. Sure, no problem.” The reality was we couldn’t and we ended up overpaying for a lot of things trying to push too hard and get things done. It took us till the middle of January to open. It was a lot to do with that timeline.

Still, 2 or 3 months and $250,000. Not to mention it snows like crazy so getting trucks and stuff up to wherever the heck that house was, I’m like, “Good for you.”

It was a challenge. Maybe I wouldn’t do it that way again.

Why don’t you give us a rundown of what your portfolio looks like now? We don’t have enough time to go deep dive into everything. You’ve gotten quite a few after that.

We own a midterm rental in Lakewood. It’s our former primary residence, 4-bed, 3-bath. It’s rented for $5,000 a month. That’s the model of house hacking that you were talking about when we were talking about our Denver property. We lived there for two years. We moved out. Now it’s a great rental for us. We make more than double our mortgage. That mid-term rental market is cool because it’s such an underserved market and it seems like it’s pretty easy to break into. We have that.

We’re selling the place in Denver. We are under contract to purchase a new primary residence in Steamboat Springs. That resident has a one-bedroom caretaker unit. The cool thing is I’ve already had offers from people to rent that one-bedroom apartment. One bedroom and 600 square feet. $2,300 a month is what I have been offered to rent that property. It will be almost half of our mortgage. The other side of the house has 5 bedrooms, 5 bathrooms. We’re somehow cheating the system that someone wants to give us half of our mortgage and we’re going to get 5, 6 of the house essentially.

We have two short-term rental properties, one in Steamboat Springs that is a triplex. It’s a total of 7 beds and 4 baths. That one we paid $645,000 for. We did $300,000 in renovations. We did a refinance in 2021 and pulled all of our money back out. That property did $185,000 in revenue. It’s on pace for about $225,000 in revenue for 2022.

That’s a lot. How many units do you have? How much passive income would you say you get from those units?

It’s a moving target. I transitioned from a job where I was earning a W-2 income as a firefighter. This is the first year that I’m trying to support myself and take money from the properties. I’ve been paying my mom $3,500 a month for the past number of years. She put in $350,000. She earns 10% on that no matter what. Her payment goes first. I’m now at a point where I’m taking $5,000 a month for myself. I have a feeling that we’ll be more comfortable taking more than that. I wanted to make sure that we have enough reserves and that everything is set up well before I take more.

ITF 82 | Medium-Term Real Estate
Medium-Term Real Estate: Every time I think the market may be peaking, I usually try and pull back a little bit, take a little money, and move it somewhere else.


It sounds like these properties that you have probably give you somewhere between $10,000 and $20,000 a month of passive income after expenses are paid. That’s the number for a lot of people, financial independence. If you’ve got 6 or 8 properties and do this medium-term rental stuff, that can get you there much quicker than a long-term rental would.

The point I’m trying to make here is if you are trying to move faster, you’ve got to think creatively. Is it a medium-term rental? Is it rent by the room or Airbnb? Sure, it might be a little bit more labor-intensive. Do you mind trying to find tenants every 3 or 4 months or do you want to work at a W-2 job for the next 40 years? Tell me what’s more work. That’s great.

That’s the situation we came to. We bought a fourplex in between this and have since sold it in Denver. I realized from running that fourplex that long-term rentals were going to make me rich eventually, but I was still probably going to work until I was 60 or 65 to get to that point. By transitioning into the short-term rental market, I was able to accelerate that extremely.

My mom and I started investing in 2014. She put in a total of $350,000. Our equity position is probably close to $2 million. We’re earning somewhere in that $10,000 a month range in passive income. I’m able to make the decision if I want to make that the primary job, I can. If I don’t, I can still go back to my W-2. I’ve been running all these properties while I’ve been at work, having two kids with my wife working as well. It’s all possible. It takes systems to get to that point.

That’s a great segue because I know that you have been working on a course. One thing that I love about short-term rentals is that there are many great systems and automation. Hopefully, the medium-term space is going to get transitioned into sooner or later. Would you like to share a little bit about your course before we wrap up and into the final part of the show?

I’d love to. Over the past couple of years, I started coaching people on their short-term rentals. I created a business with a business partner called Master Vacation Rentals. We started doing free webinars. It transitioned into something where we realized we were teaching the same thing over and over again. We had about six webinars, so we kept teaching the same thing because that’s all that people were asking us.

We turned it into a course and the course can be found at What I tried to do was take my brain, take all of the things that I’ve learned over the past several years of running short-term rentals, and put it into a course. It starts with a video of me, click-by-click, walking you through how I set up my first Airbnb listing. Why are photos important? Why do you have your title this way instead of that way? From there, I go into the different software that I use. Pricing software and automating your emails are important. It’s cost-effective not to do it yourself. I feel bad for anyone that’s not, honestly.

I’m excited about the course. It’s going to be something that can grow. What we’re going to do is we’re going to have some online Q&A sessions for a month where everyone can hop on and ask any additional questions. From there, I’ll build additional modules for the course. Hopefully, eventually, everything is there and you can walk through it yourself, get yourself up and running, be super successful, and leave your W-2 job if you want to.

Coaching is something that is super helpful. It’s investing in yourself. It always accelerates the process. If you know Airbnb is the way to go, check out Jake’s program. Jake, How much is the course?


I bet you’ll make that back by getting it up one month sooner. If he can get you one month sooner, I bet you’ll make more than $450 back. I make a lot of purchases without justification.

It’s not rocket science. Airbnb is something that is figureoutable. How long are you going to spend trying to figure that out and making mistakes? It’s great if you can get a coach, pay a consultant, get the book, do whatever it is, or that course. It’s great that people are out there making things like this. Thanks, Jake, for taking the time. Craig, let’s move into the final part of the show. What do you think?

Let’s do it. Let’s call it The Final Four.

Jake, we’re going to ask you four questions in this final part of the show. Your first question is, what are you reading right now?

You don't make your money until you sell. Click To Tweet

Unfortunately, I don’t read many books like this anymore because I have two small children who run around and do crazy things. I am reading an audible book called Richer, Wiser, Happier by William Green. It’s pretty awesome.

I don’t know that one.

It’s worth checking out.

Jake, what is the best piece of advice you’ve ever received?

I’m going to tell you a short story. This goes about 10 or 12. My dad said, “Do you want to make a little extra money?” I said, “Yeah.” He said, “Okay. Can you go wash my car for me?” I went outside. I sprayed a little water, threw a little soap on the car, and sprayed it off, and I walked back inside about ten minutes later and said, “Dad, your car’s clean. Can I have my $5 now?”

He walked outside with me and he looked at the car and said, “Is this the best work that you could have done?” I had to eat my pride and say, “No, it wasn’t the best work I could have done. I thought I was washing a car. Who cares?” He sat with me and said, “I’m going to teach you how to wash a car the right way.” He started on the top and worked way down. From then on, I realized that anything I was going to do in my life, I should do the right way. I shouldn’t cut corners, even if it’s as simple as washing a car.

That’s why you put quartz countertops in 600 square foot apartments. That’s a great story. Dad is instilling wisdom at such a young age. I love it.

What is your why?

My why are my kids and my wife. It’s getting to spend time with the ones that I love instead of spending all my life grinding until I’m too old to appreciate the time that I have with them. Also, my why is to get to go my own way. I love to follow my passion and it’s hard to do that when you’re working 50-plus hours a week for someone else. It’s been refreshing for me to not go to work and decide each day, “What do I feel like working on today?” Most of the time, I learn a lot, I explore a lot, and it’s been fruitful. It’s been great.

Congrats on quitting your job, by the way. I love hearing about people’s journey when they quit their job.

I’m not 100% quite yet, but it’s close. I’m on a leave of absence.

Last question. If a tomato is a fruit, is ketchup a smoothie?

Yes, 100% true.

Next time you get a burger with ketchup and mustard, you better make sure you want a tomato smoothie and mustard with that.

ITF 82 | Medium-Term Real Estate
Medium-Term Real Estate: I realized that anything I was going to do in my life, I should do it the right way. I shouldn’t cut corners.


Watching my daughter eat ketchup backs that up for me. She likes to slurp the ketchup right down. She doesn’t care about dipping anything in it. It’s a drink to her.

Ketchup and no fries. Jake, where can people find out more about you?

You can find me at It’s probably the easiest way. I am on Facebook and BiggerPockets, trying to answer questions for people in the short-term rental forums. We will connect to our Instagram account. @StepByStepBNB is our handle. Facebook, the same thing, Step By Step BNB. Reach out. We’d love to chat. If you have any questions about our course, we’re always happy to answer them.

Thanks so much for coming on. You’ve instilled some awesome information about big rehabs, Airbnbs, and how to extrapolate a little more from the properties you have so you can get what you want maybe a little bit quicker. Thanks so much for sharing. Z, anything before we kick it off?

No. See you next time.

See you.

That was Jake Cohen. Z, what do you think of Jake?

It was a great story. I liked that he focused on trading up. Trading up is unpopular in real estate. A lot of people want to talk about collecting and buy and hold. I’m also one that likes to trade up. I prefer to have fewer properties that I find are in nicer conditions and nicer places that I want to visit. Everybody has their own path. I love that he does highlight how great his trades ended up being.

Do you know who would hate Jake? Casino. Casinos would hate Jake because what he does is he buys a property and cashes out when he’s ahead. He’s not staying in there to make more. We all know that casinos win. With real estate, it’s not the same way. He has that mindset of like, “I’ve doubled my money in this property. I’m going to trade it up into something bigger.” He’s going to take his winnings and run versus keeping it.

Over time, real estate will likely continue to grow up. If you hold it for the long term, it will continue to increase. There’s no doubt about that. I like the way he thinks about it. He’s intentional with what he buys and sells. Jake’s got an awesome story. He’s about to quit his W-2 job, which means he is 98% to financial independence. Heck to the yeah. I love adding people to that club. Anything else you want to say about Jake, Z?

Not so much about Jake, but if you guys liked the show, please leave us a rating, review, or comment. Share it with your friends and family because we would love to have more folks like you.

Please do that. With that being said, we’ll see you guys all next episode.


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About Jake Cohen

ITF 82 | Medium-Term Real EstateI am an Airbnb Ambassador and have been hosting on Airbnb for 5 years. I have pretty much been through it all, from crooked contractors to not knowing which mattress to buy. I am here to help you succeed. I started Step By Step BNB because when I got into the Short term rental space, I didn’t feel like there were good resources available on how to buy, furnish, and manage a property. I now own 3 Short term rental units in Steamboat Springs, 2 short-term rental units in Gulf Shores, Alabama, and 2 monthly rentals in the greater Denver, CO area.

I currently live in Steamboat Springs, Colorado with my wife and 2 crazy kids and love to be outside enjoying the snow or the trails. I am a systems and lists fanatic. Instead of keeping all my lists and techniques to myself, I am here to guide you to become a SuperHost as well. I look forward to connecting with you as part of our Step By Step BNB hosting course and being your mentor on this exciting journey.