We were lucky to catch up with Drew Reynolds recently and have shared our conversation below.

Drew, thanks for taking the time to share your stories with us today Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

I was asked by an acquaintance to go to a short term rental presentation in Madison. I didn’t really have any interest in going, but he asked me to go, so I went. What is funny is that the guy that asked me to go didn’t show up. So I sat there by myself and listened to the presentation. And the concept that was presented made absolute sense to me. When I left the presentation I was fairly sure I was going to do it. I did some research and what I found backed up my gut feeling that it would work in this market. So, I called the guy who didnt show up to the presentation and asked him if he wanted to partner up. He said yes.

I signed up for a class/mentorship and spent the next couple weeks learning the basics of the business and getting a framework in place. After that it was time for massive action. I didn’t know for sure that it would work, but I knew that the only way to be 100% sure that I didn’t “miss” the opportunity was to go all-in with action. We ended up getting our first unit within a month, and then another one a few months later. We slowly put a good team in place and now we are over 30 units in Madison and Milwaukee.

The two most important things to move from idea to launch, in my view, is planning and action. You have to plan before you do anything, otherwise you’re obviously going to very likely fail. But you can’t spend years and years thinking and planning, otherwise your going to end up finding a hundred ways why you should keep waiting and pushing off taking action. If you sit around thinking about all the negatives that can happen, then you’re going to talk yourself out of starting the business. There is a line between being careful and doing your due diligence and procrastination So, I did a reasonable amount of research and planning, got some advice, and then took action.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Remotely provided furnished housing for traveling workers, medical professionals, and others who are looking for housing but don’t want to stay in a hotel. Our goal is to have our guests move in and feel like they are at home. People who travel from city to city for a living can spend a lot of time trying to find reliable housing, and it can be stressful process to find a place to stay. If they are traveling every 3 or 4 months, then they have to go through the process of finding housing 3 or 4 times a year. For anyone who has tried to rent a new apartment, they know that it can be a pain and take weeks, if not months, to find a place to live. Our units are all professionally designed, cleaned and maintained to the Remotely standard. We want travelers to know that if they stay in a Remotely apartment or house, that it will be clean, comfortable and safe. They won’t have to rent a place, sight unseen, and cross their fingers that the pictures match the reality.

I get the most gratification when I get a call from someone who we can help. Sometimes they are people who are stuck overpaying for a small hotel room. Other times they are calling from a competitor’s rental and the pictures do not match the reality, and they need to get out of there asap. And if we can get these people out of those situations and into one of our rentals and make them happy, that is a big win.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

There comes a point in your business when you are going to have to stop grinding and hire other people to help you out. Eventually you need to bring people in. There are only 24 hours in a day and you will hit a ceiling where you can’t grow or scale anymore based on the Founder’s work ethic alone. My background is in the trades, so I have a head-down get to work mentality and to do everything on my own. And it has taken a long, long time to break that mentality. The Founder, when they start a business, is going to be doing most of the jobs. And that was the case with us. We were doing a lot of the smaller tasks. It got to the point where all those smaller tasks were taking up the entire week. They were taking time and energy away from the larger, strategic items that need to be addressed in order for the company to continue to grow.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

This was definitely a side hustle at the beginning. For almost three years, I was working on Remotely after my day job, on the weekends, and sometimes even in the early hours of the morning before my day job started at 7am. We eventually brought on another partner, Andriy, who has done a great job overseeing a lot of the operational aspects of the company. He has been invaluable. But it was still a part time hustle for another year even with his help. For the last 6 months before I quit my previous job, I would basically get home from work, grab something to eat, let my dogs out, and then get in the car to go and build the business. It was crazy for a long time.

It got to the point where it was no longer feasible for me to basically work two jobs. It wasn’t good for the business and we were able to budget in my salary to pay for it.

Contact Info:

• Website: www.stay-remotely.com
• Instagram: https://www.instagram.com/stay_remotely/
• Linkedin: https://www.linkedin.com/company/stayremotely

Image Credits
All the photos of the apartments are curtesy of Jose Carvalho and his company Upperview Media