From Boutique Roots to STR Heights

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In this podcast, Mark Simpson hosts Jake Cohen from Steamboat Springs, Colorado, at STR WealthCon 2024 in Nashville. Jake discusses his property management journey, starting with managing boutique hotels in California, then shifting to long-term rentals, and finally to short-term rentals. He now manages multiple properties and oversees revenue management for 45 units across the U.S. 

Jake emphasizes the importance of data and revenue management in maximizing rental income, despite his reliance on Airbnb and lacking direct booking sites. He shares his success in outperforming the market and the support he's received from industry mentors like Bill Faye and Stacy St. John.

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A special episode

[00:00:00] Mark: Welcome to the Boostly podcast. This is a special recording from STR WealthCon 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 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.

[00:00:22] Jake: Thanks for having me, Mark. Excited to be here. Uh, I live in Steamboat Springs, Colorado. Have. Did I say my name? Hello. My name is Jake Cohen. Uh, I'm a host in Steamboat Springs, Colorado. I live there with my wife and two little kids, three and five years old. Uh, we own three units in Steamboat, co-host three more there, a duplex in Gulf Shores, Alabama, and a midterm rental in Denver.

[00:00:53] I also do revenue management for 45 units across the United States.

How Jake got started

[00:00:58] Mark: Wow. So as a heck of a portfolio, how did you get started? Where was property number one?

[00:01:03] Jake: well, uh, it's a long and winding road, um, but I Started backwards. Most people are getting into boutique hotels now. I Lived on-site at a bed and breakfast from the time.

[00:01:16] I was 10 years old when I graduated college at 22, my parents had bought a second Boutique hotel in Palm Springs, California. Uh, 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, moved to Denver and, uh, got into some longterm rentals and realized, man, I do not like dealing with long-term rental tenants.

[00:01:50] These were very. Low price, not fun, long-term rentals. And, uh, I 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.

[00:02:10] I'll send you a check every month. So, we started with long-term rentals and then pivoted into short-term rentals, which was a much better fit for our background in hospitality. And, uh, we bought a duplex in Steamboat Springs and then a triplex, uh, about a year after that. And, man, we just kept growing.

[00:02:31] And, uh, I put her from her few hundred thousand dollars invested. She now has a two-million-dollar equity position. She gets paid 4, 500 a month. And, uh, it retired me from my W2 as well. So, pretty cool.

[00:02:44] Mark: That's an amazing story. So we share a very similar background. I grew up in a bed and breakfast. Really?

[00:02:50] In Scarborough. Uh, I would think I was four when they knocked down a barn and turned it into a bed and breakfast, with four bedrooms. And, uh, yeah, it's a heck of a story.

The one piece of advice

[00:03:02] 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 from them?

[00:03:20] Jake: It's a great question. Um, you know, honestly, what I've been diving into now is the numbers, the data, the revenue management stuff. I've been working with clients all across the country, and I've been so surprised at how much of a difference. Tweaking some numbers can make it into your portfolio.

[00:03:42] So, um, I would say I'm behind on a lot of things. I don't have a direct booking site. I still get 99 per cent of my bookings through Airbnb. Uh, I'm not sending emails to my past guests. I'm doing all the things wrong, but I am good at revenue management. And because of that, um, I will be 99 per cent of the market in the areas that I host.

[00:04:05] And, um, it has made those inefficiencies in other places not seem like that big of a deal. So, uh, my, my advice would find what you're good at in your short-term rental. Be 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.

[00:04:28] And that's where I'm at now is I'm realizing I'm gonna focus on the revenue management. But I'm bringing on a team now to help me with communications building out a site and doing all those things. So, uh, very exciting place to be where I can finally say, I don't have to do all this myself.

[00:04:45] Mark: Nice. So we are at a short-term rental conference in Nashville.

Who helped educate you on this journey?

[00:04:49] There are many speakers, thousands of people here. Who have you followed online has helped educate you in this journey? Are there any special speakers here, special people that you want to give shout-outs to who's helped you along your journey?

[00:05:04] Jake: I'm one of those people that consumes everything. So I love all of the speakers here.

[00:05:08] I have enjoyed all of the information that I've received. Um, I am Bill Faye's mastermind and Bill has been an amazing mentor to me. Um, helped me see the bigger vision of where am I going and how 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.

[00:05:29] 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 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 are so many people who do everything else well.

[00:05:52] So love bill for that. Um, other people that I'd like to shout out to, um, I think, uh, what Stacy St. John has done with her stuff has been phenomenal. Um, I started working with her and recorded, uh, a revenue management session for her course and, uh, the energy in her group. So I've had the pleasure of working with several people in her group now and, uh, I mean, these ladies are phenomenal.

[00:06:19] They are so much fun. So gone out with a couple of them while we're here in Nashville and 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 same thing.

[00:06:40] And we all love the same stuff. And. great. So, uh, those are the two I would shout out to.

[00:06:46] Mark: Amazing. So let's talk about your tech stack. So right now you said you're on Airbnb. What other channels are you on?

[00:06:53] Jake: That's it?

[00:06:54] Mark: Just Airbnb. What's the property management software tool that you use?

[00:06:58] Jake: Hospitable.

[00:06:59] Mark: And do you have any dynamic pricing that you use?

[00:07:02] Cause you do revenue management. What's your, what's your one of choice?

[00:07:05] Jake: Yeah, I use price labs. Um, I have subscriptions to, A lot of pricing stuff, so I have key data, I have playing around with wheelhouse behind the scenes, I have, um, Um, Intellihost, RankBreeze, all of these things that help with pricing, I'm very, very into, um, but I've lagged on some of the other stuff.

[00:07:27] Mark: That's okay, so, do you use, um, 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 shoutouts to all of those.

2024 plans

[00:07:40] And then the final question, as we like to wrap up behind the host, is what is your plan for 2024?

[00:07:45] 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?

[00:07:52] Jake: Absolutely. Well, I'm super excited that I'm podcasting this year. Uh, price your STR. So look forward to giving you more insights on your pricing. And, uh, I hope to grow my, clients from 45 listings to 200 in my revenue management business in the next 12 months.

[00:08:14] Um, bringing on a number two in the business, uh, in about a month. So I'm excited to help her grow and learn the revenue management side of things. For my properties, um, I have, uh, Really three main properties, and I am trying to pivot them a little bit from where they are. So, I own a place in Gulf Shores, which is doing great, phenomenal revenue.

[00:08:40] However, it's tier four, and I've decided, really, I only want four properties. That is my goal. Four properties that do 250k to 500k of revenue each. So, I'm going to pivot that property from, uh, Uh, the tier four and sell it and buy a beachfront property. I'm not 100 per cent sure if it's going to be there or if it may be in another destination.

[00:09:04] Um, I have a triplex in Steamboat Springs, uh, that I've been operating as three separate units, but the more I've done the research, the more I realized that a seven-bedroom home if I can combine the units, it's going to be way more beneficial. Uh, it's a unicorn in the market as opposed to one of thousands.

[00:09:27] So I'm looking forward to making that transition, um, moving towards that single-family home model. Uh, I think it will increase revenue by 100 to 150 K a year for that one property. And then I want to sell my former, um, primary residence in Denver, Colorado. It's a midterm rental. It's been a good investment for us.

[00:09:48] It has equity. It's not worth my time anymore. I'm making a couple hundred bucks a month on it and it's time time to move on.

[00:09:55] Mark: Nice. So you're gonna 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 it is, of all the verticals that you're doing, where's the best social media, email, how can they get hold of you?

[00:10:07] Jake: Yeah. Um, my website is step-by-step. B and B dot com. Um, I do have a Facebook group called price your STR. Um, so if you're looking for great free information on revenue management, uh, I try and do a long two-hour ish session once a month where we get, we all get on Zoom, people can ask questions.

[00:10:31] We dive into a topic there. Um, you can also email me Jake at step. Step B and B dot com. Uh, would love, love to connect with more people. Um, that's one of my favourite things about being here at these conferences I get to see people that I only see either on Zoom or on Facebook and I get to meet them,and ghug them

[00:10:56] Shake their hand. It's awesome.

[00:10:57] Mark: Nice. Jake. Absolute pleasure. Thank you very much. All the best. Have a great year. Thank you for tuning into the Boostly podcast. Uh, we show up every single week to give hosts the tools, the tactics of training and the confidence to go and increase their direct bookings.

[00:11:13] Uh, we will be back. in a couple of days'days 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.

[00:11:28] Thank you very much. And we'll be back soon.