Vol. 2: Designing a Healthy, Blended and Productive Lifestyle

We sat down with SaaS problem solver, early stage advisor and fellow Destination Seeker, Will Stevenson, to learn more about his perspective on thriving in the new world of remote work and flexible lifestyles. The world has changed, but we’re built for change if we open up and embrace it.

Live, from anywhere.

So, we’ve had the pleasure of hosting you in a couple of our Destination Homes. Where have you stayed and what led to those events?

I’ve stayed at a D. Alexander Emerald Coast home (Wadleigh) and in the Smoky Mountains. I work from home and our girls are home schooled. With the current events, it makes it really hard to eat, sleep, work, learn, play - all in the same place.

We’ve discovered D. Alexander and we couldn’t be more thankful. It’s been a way for us to escape our day-to-day, while staying safe and limiting our risk with beautiful drivable destinations.

Was there anything you were looking for in particular in a destination market? What about in the home?

The market had to be drivable from Cincinnati. The home had to be unique and above anything, sparkling clean. That’s exactly what we got in both markets.

Work, from anywhere.

Tell us a little bit about you and your entrepreneurial journey…What are you working on now and how did you land where you are today?

I’ve worked with early-stage software companies for the past decade and have been fortunate enough to be a part of a few acquisitions. For the past couple of years I’ve been consulting on customer experience for other early-stage companies. Along the way, I noticed commonalities across these companies (including my past companies)… The new customer onboarding process was less than exceptional. I’ve recently co-founded and launched Onboard.io - a software that helps companies onboard new customers faster and more efficiently.

Inspiring, so why do you do what you do… what makes you tick?

What has always made me tick is solving difficult problems. Which is one of the many reasons I respect D. Alexander so much. A very difficult problem right now is - how do you travel and retreat during a pandemic, safely? From everything I’ve seen, the company [D. Alexander] has solved that challenge to a large degree by aligning customers with drivable locations (or as you would say, from Point-A-to-Point B) while providing a product (or Home) that’s designed and equipped for living and distancing from the world.


The “future of work” is here.

And how do you prioritize work along these journeys? How do you think about that fitting into your lifestyle and what are the most notable changes that you see?

I’m sure many of the entrepreneurs reading this know what I mean when I say “I’m always on”. I might be eating dinner with the family, but I get a message and need to jump to a quiet place to make a call. It’s a little bit of a juggling act, but finding homes with one extra bedroom and fast Wifi always helps.

Do you plan work around your trip or work around your trip?

I’m a big fan of is integrating work and life. Rather than saying “after 5:00 p.m. I’m off the clock”, I’d rather just realize that some days I’m going to take a call at 7:00 p.m. and some days I’m going to go on a family adventure at 3:00 p.m. To me, it’s less about specific times off and more about consistent time off.

So, more on the work front, other business pros can learn from your insight… what do you look for, what makes a home optimal for work?

I mentioned them before but I always look for an extra bedroom that I can work from when needed. The best feature about the home we stayed in on the Emerald Coast was the “community pool”. I put that in quotes because the pool was amazing and there were rarely more than a couple of people at it - so it was a way for me to get out and enjoy the weather and work poolside.

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Play, from anywhere.

Tell us about traveling with your family - how do they embrace getting away and aligning with your work routine?

I have three girls that love to travel. I would actually say I work better on the road. My girls aren’t as familiar with the house that we’re staying in, so I can hide from them better :). Just kidding - they always find me, but as long as I promise them we can explore they’ll let me take my calls when needed.

A new environment helps keep them busy that’s for sure. My wife is amazing and holds us all together (thanks Jess, xoxo) and my kids have been accustomed to work, live, play being one-in-the-same. Your homes [D. Alexander] are clearly optimized for families like us, which helps me dial in work time, and let loose on family time all in one clean swoop.

Are long stays common for you and your group/family?

Not before COVID, but it opened our schedules since we’re able to “work from anywhere”, “learn from anywhere”, and “live from anywhere”.

How do you see households prioritizing getaways differently going forward?

I think drivability will become a great priority to reduce exposure, single family homes will make people feel more comfortable, and markets that are “secondary” will be sought out (fewer people, more space, but close enough to necessities).


Merging Health and Play

2020 has been a crazy year - has your focus on health and wellness changed as a result of being hunkered down at home for long durations, change in schedules, etc.?

Like a lot of people, I’m not sure if my perception of health and wellness has changed, but my focus and being very intentional about health and wellness has changed.

I’ve noticed - as a society - we’re talking a lot about masks and staying out of large group setting - which I absolutely agree with, but another piece to health and wellness is the proactive measures - eating well (cooking at home), spending time with your family, letting the sun hit your face, de-stressing by walking next to the ocean or through the forest. Just like the reactive measures we are taking are important, so are the proactive measures.


Closing Thoughts

So, what makes D. Alexander special?

The special touches - from the welcome basket, to the baby gates, to the easy check-in/check-out process, to the throw blankets. The best part of D. Alexander is every detail has been thought of - for me - most companies miss these details or ignore them. These details are what makes D. Alexander homes feel like… well.. Home. Comfortable.

You can tell that the company really takes ownership of the quality of the homes and providing value. They’re beautifully designed and thoughtfully furnished, not to mention spotless.

What about D. Alexander did you value the most? What would keep you coming back? Do you plan to come again?

I know what I’m going to get every single time - beautifully designed, high quality, very clean, unique homes, in great destinations.

Final thoughts or words of wisdom to yourself 10 years from now, or the version of you 10 years ago…  if there is one piece of advice that you’d leave others with on the topic of work-life-balance in a remote world, what would it be?

Give your children amazing experiences.