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Community Highlights: Meet Derek McMonagle of The STR Manager

Today we’d like to introduce you to Derek McMonagle.

Hi Derek, so excited to have you with us today. What can you tell us about your story?
First off, I am thankful to get to share my story with the Voyage Phoenix audience for a second time. It is always a very humbling experience to share my business and my passion with others. So, I got started in the property management space about 4 years ago. I was unemployed, living on my buddy’s couch in downtown Phoenix, studying to become an NBA agent. Little did I know, the Good Lord above had a different plan in store for me.

After months of not hearing back from the NBAPA and FIBA after submitting my application, I received a cold email from a woman named Brittany Miller, who was the Director of Business Development for an Airbnb management company called Makomi. Honestly, I thought the email was spam, or at least it was too good to be true. She mentioned that she had viewed my resume and my sales credentials on LinkedIn and was looking to grow her sales team.

I had mentioned that I no longer lived in Pittsburgh, so it may not be a good fit, and that’s when she mentioned that I would be able to work remotely, and then I thought it was too good to be true. After a couple of phone calls and interviews with her and the CEO, Jesse Gross, I joined the Makomi sales team, and got my start in the Airbnb industry with an awesome start-up company! We managed 300+ Airbnb properties throughout New York and the East coast, and things were going amazing!

March of 2020 rolls around, and the CEO calls for a team meeting on Monday, March 16th. What we thought was just a typical team hype-up meeting turned into the company shutting down that day. Effective immediately, I was out of a dream job and didn’t know where to turn. This was my first time being part of an amazing company, and then that amazing company shut its doors abruptly due to a worldwide pandemic.

I spent the next 6 months depressed, overwhelmed, and severely broke. I had ZERO income coming in and had to figure out something quick. I ended up taking advantage of a free session I received from the company for their career coach, and figured, “Why Not.” Little did I know, that conversation changed everything for me and was the motivation I needed to get back into entrepreneurship.

So, after being unemployed, depressed, and having no sense of direction, I had my motivation, and disciplined mindset back, and created The STR Manager, LLC, my own Airbnb property management company in December 2020. Granted, this wasn’t the best time to start a business, according to some because COVID was still running rapidly, but I trusted in God’s plan for my life and was obedient to Him calling me back to entrepreneurship. In year 1, we made a whopping ZERO dollars in business; yes, ZERO. I didn’t bring on one property!

I was about a month away from shutting the doors because I had no money, no plan, and I was mentally defeated, but I still had the Good Lord on my side, and I just kept hearing in prayer, “Persevere a little longer.” Little did I know, persevering for just a couple more weeks, gave me the breakthrough I needed. I brought on my first property, and then my second, and then my third, and then my fourth, and the momentum was rolling. I was managing the homes, guest communications, actually cleaning all the properties, doing the landscaping, and everything in between!

I was so excited, but I also had to make a living, so I had to do every aspect of the management side of things just to survive and break even until I grew more! It was the biggest blessing in disguise, and fast forward 3 years later to today, we now manage 30+ listings in 3 different states. We entered Arizona, Texas, and Florida, and have team members in all 3 states, as well as expanded into a partnership with an awesome company that helps us handle our back-end business operations!

We all face challenges, but looking back would you describe it as a relatively smooth road?
Not! Everything but smooth, but that’s the fun part! Granted, the world of entrepreneurship can be stressful, but the reward to run your own company while blessing others with employment opportunities, and giving people the chance to achieve their dreams is well worth the stress.

We take on bumps and bruises along the way, especially financially, and from a scalability standpoint, but my faith is what keeps me grounded and humbled along the way. Without the Good Lord on my side, I wouldn’t be able to do what I do!

Alright, so let’s switch gears a bit and talk business. What should we know?
The STR Manager is a locally owned and operated full-service Airbnb and short-term rental property management company that is built on faith, honesty, and integrity. We help you get your hands off with your property as your personal Airbnb concierge and handle everything from start to finish!

We handle everything from start to finish. From initial photography and listing creation to managing guest communications, pricing changes, vendor management of our cleaners and service team members, claims assistance, and much more! We are hands-on, so you can be hands-off and just watch the money roll in!

What allows us to stand out is our motto of property management built on faith, honesty, and integrity. We lead with faith at the forefront, and a lot of people are turned off by that, and that’s okay. We aren’t the management company for everyone, but we are meant for those that value a strong faith and moral groundwork, as well as honorable values.

We don’t just focus on our bottom line; we focus on our client and guest experience, and will always put that first, and ensure our clients have a Disney-world experience when they come to The STR Manager!

Can you talk to us about how you think about risk?
Absolutely. I’ve taken risks with this company since I opened the doors. From betting every dollar I had in the bank on myself and The STR Manager, to missing vacations, holidays, birthday parties, and everything in between. Some people will say in the long run that I have too much of a reckless attitude towards risk, but what I share with others is that I don’t make decisions on my own.

Everything I do in my personal and professional life comes from discernment with Christ. I confirm every single decision with Him in my business and my personal life. Every risk, every opportunity, is run by the Man upstairs! I believe to be a successful entrepreneur, you have to have a pretty solid relationship with risk.

Now, as I say this, there may be people that think starting a company and betting the house on everything and putting yourself in a sticky financial situation is a stupid risk, and I’m not going to disagree, but I realized that I work best when my back is against the wall, and when only Plan A exists and going back to discernment with Christ, He always leads the charge on those decisions. He is always going to reveal a powerful blessing and lesson through that hardship.

So, all in all, I encourage you to take risks. I encourage you to go all in on yourself. Because at the end of the day, that job will always be there. The opportunity to work for yourself and build a faith-driven dream from the Lord is a once-in-a-lifetime opportunity and I’m going to cash in on it. I can always get a safe job and make a 6 figure salary with my skillset.

That doesn’t push me to be the savage servant the Lord made me to be though, and there’s nothing wrong with a 9-5, but as a 26-year-old, with a mentality to serve, and become the best version of himself, I am following the Lord in my business, and allowing Christ to be my CEO and lead our company to success, and ultimately on the path to Heaven. So, take risks, small, and big, and assess your risk tolerance. Don’t just follow my approach. Pray on it, discern what you should do, and then make it happen.

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