Digital Nomad-ness: Startup Life in 120 Square Feet.

Originally shared on LinkedIn, A.J. shares his experience working for startups and living on the road.

Digital Nomad-ness: Startup Life in 120 Square Feet.
Summer '21 in a nutshell

(I'm writing this from the dinette of the trailer you see pictured above.) I'm not one to typically publish something like this until I got an email recently that asked:

"What would lead you to accept a job at a startup? What would your main concerns be about working for a new and small employer? What factors should people consider before making a move to a startup?"

Since I started a new job at a small startup in 2021, I thought, here's my soapbox to stand on. So come along for a ride!

It goes without saying that 2020 was a weird year. At the beginning of 2020, I had the opportunity to help open a new office in London while working at unicorn Unfortunately, I landed a week and a half before the UK’s 23 hour a day lockdown hit. As a result, I never had the opportunity to return to the office, or explore weekend trips throughout Europe. Visa extensions, residency, taxation, and no talk of vaccines in sight, brought me back to the US earlier than expected. It seemed like if a news headline wasn't about COVID, it was about the sky-rocketing prices of recreational vehicles and their new owner's aspirations to be the next #vanlife influencer.

Hitting the tarmac back in the US, I thought to myself, if you can't beat 'em, join 'em.

In August of 2020, after years of "professional persistence" (read: nagging), I had finally swayed the previous owner of a 1995 16 foot travel trailer to hand over the keys so I could join the hoards of others that had re-discovered the great outdoors while safely social distancing. For us elder Millenials, 1995 seems like yesterday, but that's 25 years in trailer life. Twenty-five years of light maintenance to get caught up on to feel comfortable towing 3,500 pounds down the highway in search of the next campsite with a strong enough signal to support screen sharing.

Today, I'd like to share with you a few realizations I've had throughout my startup career and attempt at being a #vanlife influencer. First, I joined Outreach as employee #67, leaving five years later as we hit the 1,000 employee mark. Then, I re-joined 2 of the founders of Outreach, Gordon Hempton and Wes Hather as we launch Spot Virtual - bringing virtual offices to the masses, and am excited to take our learnings and build another hypergrowth company!

Realization #1 - Unlimited PTO is only good if you take it. When looking for new jobs in the startup world, it's a staple to see "Unlimited PTO - and we really mean it!" in the job description. I was a part of the onboarding of all new employees at Outreach, and my advice to them on their first day was always consistent: hold yourself accountable for taking PTO. You're an adult; you know what's reasonable. Don't be ashamed for taking the time, but don't abuse it.

The Solutions Consulting team was sick of hearing me talk about how excited I was to get on the road, and couldn't have been more supportive and understanding as I started to plan trips that included long driving days in the trailer.

When I switched over to the team at Spot, Gordon and I talked about my start date. While he was excited to have me on board to help our customers adopt a new platform, he was adamant that I take at least a week to decompress, so sure enough, I took the trailer and hit the road.

If you're joining a startup, my advice to you: never, EVER, leave one role on a Friday, and start the new one on Monday. Be transparent through the entire hiring process that you'll be taking at least a week between roles.

Realization #2 - Things change. Quickly. As Will Smith so eloquently put it in the theme song to The Fresh Prince of Bel-Air, "my life got flipped, turned upside down."

As the days got shorter in 2020, and the holidays quickly approached, I became aware of a dog that had a rough start to life and needed a new home. On January 2nd 2021, I drove north from Seattle to meet her for the first time without hesitation. I was warned she was a bit unpredictable, protective, and needed some training.

What I met was a scared, 1.5-year-old Golden Retriever that needed some love. My routine quickly changed, for the better. I was up earlier, taking lunch, and shutting my computer at a reasonable hour to get outside for a walk.

Joining a startup is a rapid pace that's not for everyone. You're constantly context switching between tasks, brainstorming, and doing anything tossed your way or executing a random idea you had to help the company grow. You won't have the formality and structure of a large company, or in some situations, a computer on your first day.

Experiments at startups don't last for months or years, they last days, maybe weeks, before we've found a way to optimize it. Love him or not, Zuckerberg's quote "Move fast and break stuff" couldn't resonate more.

My advice to you: if you don't proactively manage it, startup life can consume you. Build a routine, be flexible, set boundaries, and stick to them.

The leaders at Spot have been incredibly welcoming of my ideas, product feedback, and letting Sandy crash video calls.

Realization #3 - It's not always pretty. As is all things social media, many #vanlife influencers won't tell you the range of anxieties they have. The morning coffee with a backdrop of mountains is paired with an almost full gray water tank, the campfire s'mores paired with the intoxicating scent of mosquito repellant.

Here's a (short) list of my constant concerns:

  • Is my 6 gallon water heater going to last through this shower?
  • Do I have enough gas to get over this mountain pass? Do I turn back to the station I saw four exits back?
  • What if the camp wifi can't hold a call? Are all three wifi hotspots and cell booster charged?
  • Am I going to lose a tire while going 70 MPH across Interstate 90? (I came close to losing it, but caught it in time!)

If you're thinking about joining a startup, get ready to get your hands dirty. You're going to be hustling hard to get that next customer and tell them how you're different than the competition in the market. You're going to be deep in code to understand why you had a 45-minute outage at your peak user time. You're going to be conducting more interviews of potential candidates than you could have imagined.

My advice to you: Be prepared to ride the wave. There are going to be days that you feel like you're riding on top, and others feeling like you got chewed up and dumped on the beach. But, the good days, shredding the gnar, should outweigh the bad and if they don't, look for ways to improve them.

This is a brief peek into the questions prompted by the email I received, and I'm happy to answer any questions you have. Also, if there's interest I'd be happy to share a second piece around Startup/RV Research, Career/Trip Planning, and a day in the life of living/working for a startup in 120 square feet.

Drop anything in the comments, shoot me an email ( and sign up for your own virtual office today.

PS - we're hiring, so if you're interested in a full tour of the trailer, hearing my next destination, or meeting Sandy, check out our careers page.

#startupjobs #hiring #digitalnomads #digitalnomad