A Boostly podcast special recorded at STR Wealth Con 2024 in Nashville. Mark Simpson interviews Jake Cohen, a host from Steamboat Springs, Colorado, about his hospitality background (managed a 12-unit boutique hotel), pivot from long-term to short-term rentals to help his mother retire, current portfolio (multiple Steamboat units, Gulf Shores duplex, Denver midterm) and revenue-management work (45 listings currently). Jake emphasizes focusing on strengths (revenue management), uses Airbnb and tools like Hospitable and PriceLabs, and plans to launch the 'PriceYourSTR' podcast and grow his revenue-management clients from 45 to 200 within 12 months. He also plans property portfolio changes (combine triplex into a 7-bed single home, sell a tier‑4 Gulf Shores unit and seek beachfront), and shared contact info (stepbystepbnb.com, Facebook group PriceYourSTR, jake@stepbystepbnb.com).
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Welcome to the Boostly podcast. This is a Special recording from STR Wealth Con 2024 in Nashville. We are doing a Behind the Host special and with me we've got a special guest who is a host in the USA and we're going to find out all about his story. So can you please introduce yourself, Let everybody know who you are, where you are and where your properties are and we'll go from there.
Thanks for having me Mark. Excited to be here. I live in Steamboat Springs, Colorado. Have. Did I say my name? Hello, my name is Jake Cohen. I'm a host in Steamboat Springs, Colorado. Live there with my wife and my two little kids, 3 and 5 years old. We own three units in Steamboat, co host three more there and a duplex in Gulf Shores, Alabama and a midterm rental in Denver. And and I also do revenue management for 45 units across the United States.
Wow. So it was a heck of a portfolio. How did you get started? Where was property number one?
Well, it's a long and winding road, but I actually started backwards. Most people are getting into boutique hotels now. I lived on site at a bed and breakfast from the time I was 10 years old. When I graduated college at 22, my parents had bought a second boutique hotel in Palm Springs, California. From 22 to 27 I managed a 12 unit 1950s theme boutique hotel. Learned all about hospitality, served on a bunch of hospitality boards and stuff like that. And then I said oh, I need to get out of here. Move to Denver and got into some long term rentals and realized man, I do not like dealing with Long Term Rental 10 tenants. These were very low price, not fun long term rentals. And I actually decided that I wanted to help my mom with her retirement. She made kind of a bad deal with my dad during their divorce. She didn't have enough money to live on. So I said hey mom, invest a couple hundred thousand dollars with me, I'll do all the work, I'll send you a check every month. So we, we started with the long term rentals and, and then pivoted into short term rentals which was a much better fit for our background in hospitality. And we bought a duplex in Steamboat Springs and then a triplex about a year after that and man, we just kept growing. And I put her from her few hundred thousand dollars invested, she now has a $2 million equity position. She gets paid $4,500 a month and it retired me for my W2 as well, so. So pretty cool.
That's an amazing story. So we share A very similar background. I grew up in a bed and breakfast, really in, in Scarborough. I think I was four when they knocked down a barn and turned it into a bed and breakfast. Four bedroom. And yeah, it's a heck of a story. So you are many years into your journey now, you've grown the portfolio and I assume it is continuing to grow. What is that one piece of advice you would wish you had received when you were just getting started? That property number one, what's that one piece of advice you wish you had received by them?
It's a great question. You know, honestly, what I've been really diving into now is the numbers, the data, the revenue management stuff. And I've been working with clients all across the country and I've been so surprised and amazed at how much of a difference tweaking some numbers can make in your portfolio. So I would say I'm behind on a lot of things. I don't have a direct booking site. I still get 99% of my bookings through Airbnb. I'm not sending emails to my past guests. I'm doing all the things wrong. But I am really good at revenue management and because of that, I beat 99% of the market in the areas that I host and it has made those inefficiencies in other places not really seem like that big of a deal. So my, my advice would be really find what you're good at in your short term rental, be really good at that. And whatever you're not good at, find other people to help you with that so that you can continue to grow. And that's where I'm at now is I'm realizing I'm going to focus on the revenue management. But I'm bringing on a team now to help me with communications and building out a site and doing all those things. So very exciting place to be where I can finally say I don't have to do all this myself.
Nice. So we are at Short Term Rental conference in Nashville. There are many speakers, thousands of people here who have you followed online that has helped educate you in this journey. Is there any special speakers here, special people that you want to give shout outs to that's helped you along your journey?
I'm one of those people that consumes everything, so I love all of the speakers here. I have enjoyed all of the information that I've received. I am in Bill Fay's mastermind and Bill has been an amazing mentor to me. Really helped me see the bigger vision and where am I going and how Do I continue to move forward in this industry? I felt like I was by myself in a closet doing my thing, not talking to anybody. All my friends were firefighters. I was a firefighter for seven years and I was this guy doing stuff that no one else was doing. And I didn't have friends in this industry. And since I've joined the Mastermind, I've been part of some of these events. It's been incredible just having that camaraderie and realizing I don't have to do everything myself because there's so many people that do everything else well. So love Bill for that. Other people that I'd like to give a shout out to. I think what Stacy St. John has done with her stuff has been phenomenal. I started working with her and recorded a revenue management session for her course and the energy in her group. So I've. I've had the pleasure of working with a number of people in her group now. And I mean, these ladies are phenomenal. They are so much fun. So gone out with a couple of them while we're here in Nashville and really enjoyed that. So I think these niches that we have are so cool because instead of feeling like, oh, I'm all by myself because I'm doing something different, it's actually I'm all by myself with 500 other people that are doing the exact same thing. And we all love the same stuff and been great. So those are the two I would shout out to.
Amazing. So let's talk about your tech stack. So right now you said you're on Airbnb. What other channels are you on?
That's it.
Just Airbnb. What's the property management software tool that you use?
Hospitable.
And do you have any dynamic pricing you use? Because obviously you do revenue management. What's your. What's your one of choice?
Yeah, I use price labs. I have subscriptions to a lot of pricing stuff. So yeah, I have key data. I have playing around with Wheelhouse behind the scenes. I have intellihost, rankbreeze, all of these things that help with pricing I'm very, very into. But I've lagged behind on some of the other stuff.
That's okay. So do you use any operations software behind the scenes? Any other tech stack that you've got or is those are the main ones?
No, those are the main ones.
Nice. So special shout outs to all of those. And then the final question as we like to wrap up on behind the Host, is what is your plan for 2024? The next 12 months, if we were to sit here in this same booth, 12 months on, where would you like the business to be if you could wave a magic wand?
Absolutely. Well, I'm super excited that I'm hoping to launch a podcast this year, price your str. So look forward to giving you more insights on your pricing. And I hope to grow my clients from 45 listings to 200 in my revenue management business in the next 12 months, bringing on a number two in the business in about a month. So I'm really excited to help her grow and learn the revenue management side of things for my properties. I have really three main properties and I am trying to pivot them little bit from where they are. So I own a place in Gulf Shores which is doing great, phenomenal revenue. However, it's tier four and I've decided really I only want four properties. That is my goal. Four properties that do 250 to 500k of revenue each. So I'm going to pivot that property from the tier 4 and sell it and buy a beach front property. Not 100% sure if it's going to be there or it may be in another destination. I have a triplex in Steamboat Springs that I've been operating as three separate units. But the more I've done research, the more I realize that a seven bedroom home, if I can combine the units together is going to be way more beneficial. It's a unicorn in the market as opposed to one of thousands in the market. So I'm looking forward to making that transition, moving towards that single family home model. I think it will increase revenue by 100 to 150k a year for that one property. And then I want to sell my former primary residence in Denver, Colorado. It's a midterm rental. It's been a good investment for us, it has equity, but it's not worth my time anymore. I'm making a couple hundred bucks a month on it and it's to time, time, time to move on.
Nice. So you'll have a busy 12 months ahead by the sounds of it. So if anybody wants to reach out to you for your help and guidance, whatever. Of all the verticals that you're doing, where's the best social media email? How can they get hold of you?
Yeah, definitely. My website is step by stepbnb.com I do have a Facebook group called PriceYourSTR. So if you're looking for great free information on revenue management, I try and do a long 2 hour ish session once a month where we get, we all get on Zoom. People can ask questions. We dive into a topic there. You can also email me jake@stepbystepbnb.com Would love, would love to connect with more people. That's one of my favorite things about being here at these conferences is I get to see people that I only see either on Zoom or on Facebook and I get to actually meet them, give them a hug, shake their hand. It's awesome.
Nice, Jake, absolute pleasure. Thank you very much. All the best. Have a great year. And thank you for tuning in to the Boost Leap podcast. We show up every single week to give host the tools, the tactics of training and the confidence to go and increase their direct bookings. We will be back in a couple of days time with our next episode, but until then, go follow all the channels, do the YouTube, the podcast, the downloads. We just passed 1.5 million downloads in the last 12 months. So thank you for being a part of that. From the SDI Wealth Conference, my name is Mark Simpson. Thank you very much. And we'll be back soon.
