Get to Know the Owner of the Grand Outlook
Question: Mike, we’re thrilled to be sitting down with you. Welcome to Anguilla! Tell me a little about yourself.
Answer: I’m Mike Downing, married to my beautiful, wonderful wife Denise (whom I’ve known since kindergarten). We have two boys, a 14-year-old son, Danny “Fuller,” and Patrick, who is 16. As a family, we’re on the road constantly with both of our boys who play hockey. And when I’m not with the family, I’m behind my grill. We have a little carriage house in Cleveland, an outdoor house that’s my mancave. I used to host a show called Garage Cookin’ online, and it’s known for the backdrop… filled with beer cans I’ve been collecting since 1976. I’ve had a love of all things BBQ since cooking with my dad, and traveled the south learning variations of my sauce and recipes, until perfecting my own.
Question: You’re from Cleveland, Ohio. What brought you to the Caribbean?
Answer: Traveling is in my soul. Whenever I could get away or save enough, I was always up for the adventure. All through my 20s and 30s, I traveled the world. Europe, North America, UK, Scandinavia, Africa, throughout the Caribbean and remember thinking, it’s a place I wanted to hang my hat one day.
Question: Tell us more about your career.
Answer: In my late teens, the only thing I knew how to do was build. I started small, really tough work, and have probably hung and taped millions of sheets of drywall and millions of miles of walls. I plowed snow for 25 years and in that time, got my real estate development license, using my construction knowledge, and then would lease out the buildings I built.
Question: So, how does a carpenter get into the luxury vacation rental business?
Answer: Denise and I sold a few properties and needed to do some planning for the future to generate income, and decided to invest in Anguilla.
We were looking at the Caribbean and our criteria were pretty simple—is it safe, is the weather good, are the beaches nice, what’s the potential for rentals? What’s there to do? And when we found Anguilla, the choice practically made itself. We loved the island because it’s unlike any place we’ve ever been. You feel secluded, safe, and simply peaceful. But it’s the people that really sold us, they are incredible.
And the Grand Outlook simply felt like home to us; it’s at the second-highest point on the island. Wait until you’re here! With outdoor balconies extending from every bedroom, every Anguillan sunrise and sunset can (and should!) be watched.
Question: What made you buy the house?
Answer: The previous owners of the Grand Outlook built and designed it beautifully. They did everything right—they positioned it in the right spot, all the bedrooms have an amazing view, every bedroom has a private veranda. As someone in construction, I couldn’t have done it any better. My hat is off to them and the vision that they had—in my mind it’s absolutely perfect.
The first time I sat and looked at the pool, into the ocean, I remember thinking I’ve never seen a shade of blue like this. You can’t imagine this shade of blue until you’ve been there. It’s just blue squared.
Question: Okay, so you’re headed back soon. What are you most excited about?
Answer: I’m having a Jeep shipped over, and can’t wait to explore the island. We’re going to explore every nook, to see the island… but really to check out all the food. I have a goal to eat at every restaurant!