The Ultimate Entrepreneur's Guide to Work from Anywhere and Travel the USA


The Ultimate Entrepreneur’s Guide to Work from Anywhere and Travel the USA


Have you seen all these bombin’ entrepreneurs traveling all over the country and the world? It’s becoming a trend, and I keep seeing it! Austin and I also traveled a little bit, and worked remotely on while traveling through the Northeast, and then to the West coast.


We traveled to Vermont (Stowe, Shelburne, Burlington), New York (Saratoga Springs, Westchester), Greenwich Connecticut, and Philadelphia. We lived in New York City for almost a year, and then relocating to the West coast. We spent a couple months in Santa Barbara, then traveled up the coast to San Francisco, and permanently relocated to Los Angeles. Before the end of the year, we’ve got our sights on Arizona (the Grand Canyon, Antelope Canyon), Palm Springs, Joshua Tree, and more.


It’s a pretty lucky life. And by “lucky” I mean not lucky at all and totally intentional.


We started first, by letting go of all our leases. We had occupied a cute apartment in Saratoga Springs, NY for $900/month for a one bedroom. We didn’t think this was “cheap” until we started paying $2k+ for housing in NYC and LA. Simpler lives have simpler expenses… like one bedroom apartments around 900 square feet for $900. Tell that to someone in a major city—it’s a bargain. We also had a beautiful office space that we designed together. It was office-heaven.


You don’t have to be majorly successful or super rich, to travel and work from anywhere. You just have to be smart about how you do it, and be willing to live a more minimalist life. In exchange for the minimalism—you’ll get the experience of a lifetime. You’ll receive the experience of traveling and working around the country, or around the world. Alas, here’s your guide to work from anywhere.




Step One: Remove All Yearly Housing Obligations

This isn’t the easiest. If you decide to wait until your lease ends, you could be waiting a while to get going on something you want to do now. However, if you break the lease you could be held to pay the remainder of your monthly payments. It’s best here just to see what options you have.


Take a spin through your lease and understand what the consequences are of breaking your lease early, then decide whether or not it’s worth it. Try to plan leaving as close to when you leave your apartment as possible. We had a lag of 2 months in between when we moved out of our apartment and moved to NYC. Austin’s family let us crash with them for a couple months, but had we planned everything a little better we could have just moved straight to NYC.




Step Two: Reduce Your Possessions

Clutter and “stuff” will hold you back. In preparation for traveling, get rid of as much of your stuff that you can. Trust me, you won’t miss it. If you must hold onto things (furniture, boxes of your “cool stuff” etc.) then get a storage unit. Austin and I moved to NYC, traveled and then moved to the West coast, all with a suitcase and duffle bag each.


I recommend, anything that you can throw out—throw out. Anything that you can give away—give away. Afterwards, find a place to store whatever you have to keep. Use the simple rule – if you don’t think you’ll use the items in the next 6 months, make sure you get rid of them. There’s no point in spending tons of cash on storage unit fees just to revisit in 12 months and realize you’ve burned $1200 and you end up throwing out 90% of the unit anyway. It happens more often than you think.


Get a suitcase that is durable and can deal with some serious wear and tear. I also really like to have a large duffle bag. I find two suitcases would be too much to roll around, but I can sling the duffle over my shoulder and roll the suitcase. Also, make sure you have some sort of backpack/purse/daypack.




Step Three: Give Yourself as Much Support as Possible

We were stepping into some seriously new territory, so we made sure to surround ourselves with support. We travelled all over the Northeast where we had friends. And I had about a half-dozen friends that lived in NYC that helped make the move much easier than it would have been otherwise. They gave lots of tips, and a tremendous amount of emotional support while we were up-rooting our lives.




Step Four: Reduce Overhead Expenses as Much as Possible

I can’t stress this one enough—REDUCE YOUR EXPENSES. Change anything that is costing you cash that doesn’t have to. If you can get it for free, do it. If you can exchange for service, think about it. If you can remove things entirely that are leisure expenses, do it.


Get your expenses as low as possible. There are a couple ways to be successful when moving and traveling (or in general I guess). If you have high expenses, you either have to make significantly more money to compensate, or lower your expenses. I think doing a combination of both are ideal. Start off with lowering your cost of living.


For example, if you love to eat out regularly, see if you can sacrifice this for a few months to have the extra cash reserve.



Step Five: Figure Out Your New Housing Situation

You’ll be looking for shorter-term housing. Airbnb is great for one-two month long stays. When you select to book for a month or more it’s considered long-term. Many hosts will offer the room or home at a reduced monthly rate (I look for the 30% off monthly rates). You can see this in the pricing section on Airbnb. About 10-20% of hosts will get back to you when you contact them for housing. Anytime I am looking for a place to stay, I contact at least 10 people, and up to around 20 if I can. The name of the game here is options.


airbnb and entrepreneur


Pro tip: Don’t select “request to book” because the first person that decides you can stay will just book you and you’re out of options. I select “contact host.” This is where I have a template email that I send out to them explaining where I’m traveling, and for what dates and ask if they have availability. I always say that we’re friendly, not home often, respectful and accommodating. We are all those things—I’ve also found that these are good things to say upfront to build some level of trust that you’re not going to wreak havoc on their home. The Airbnb hosts are letting strangers into their homes, so make it easy for them to say yes, and many of them will.


I’ve also had many situations where we’ve stayed at an Airbnb for a month and loved it, and extended our stay to 6-8 months.


Airbnb is not the only option. You could also sublet.

Craig’s List can be a descent resource depending on the day—I’ve found Airbnb to be more reliable of an option. I say this because they have to be more accountable to you because they’re response rate, and reviews are public. This feeling of accountability means that they usually act more responsibly in getting back to you, and in general (not everyone, I’ve met some crazies but you can totally see it ahead in the reviews).


Aside from Airbnb, I’ve found housing groups on Facebook to be another terrific resource. You’ll find these groups on Facebook for any major city in the US. Search “housing” and the city in Facebook groups and request to join the groups you think you could use. These contacts are more reliable usually than Craig’s List, but keep in mind they don’t have public reviews like Airbnb. Keep communication open, and trust your gut. If you see red flags, it’s probably best to avoid them entirely.

My favorite housing Facebook groups are “Gypsy Housing” in NYC, and “Gypsy Housing West” for LA.




Step Six: Place Your Marketing on Autopilot

When you’re traveling, you’ll want to place your marketing on autopilot. Having opportunities and leads contact you while you’re traveling is way more awesome than having to hunt them down. Start by building up your personal brand, and positioning yourself as an expert. Provide value frequently through social media (Instagram and Snpachat are hot right now), and vlogging/blogging to educate your audience.


Set up email opt-ins on your website to start building your list. Make sure you have a bangin’ website that’s crushing the branding game. Set yourself apart from everyone else by being really clear on your messaging (what you provide and to whom). Don’t be afraid to use your unique personality to set yourself apart from the crowd!


Build your personal brand with intention, and make sure it’s communicating what you offer, and to who quickly. Read this article for all the steps on how to make money as a personal brand starting on day 1 (the action steps and ultimate guide to being an expert).



Step Seven: Step Up Your Social Media Game

Anyone that I know personally that is traveling and working from anywhere successfully—is doing so because of social media. They’ve built sustainable social media followings that provide them with leads, and sales on a regular basis.


My friend Tatianna at My Urban Illumination has a simple system where she gets paid through Paypal for tarot card readings. She has a few different package selections, but overall everything has been set up in a simple, efficient way. She also gets the majority of her sales from social—Instagram and YouTube.


The bulk of our sales at come from our social media followings, blog and email list. We’ve made thousands and thousands of dollars directly from Snapchat, and the same can be said for my Instagram, as well as our email list.We’re consistently building our email lists as a result of social media and blogging too.


Business doesn’t have to be hard. It’s all about getting the right systems in place for yourself to succeed. And one of those systems should be crushing your social media game.




Step Eight: Have Your Money-Making Systems in Place

Make sure you have ways to generate money for yourself online. You can easily accept sales with products you create on Squarespace. You can easily embed a Paypal button on your site and accept sales that way (or through Paypal invoices). You can set up your ebooks on Gumroad. You can sell courses through Thinkific or Teachable. You can accept bigger payments and send invoices from Square. The options are endless.



Step Nine: Get Your Mobile, Entrepreneur Tech-Gear in Place

This is the easier part where you go shopping. Make sure you have the gear you’ll need to succeed. You’ll probably be working frequently from coffee shops too, so download this app: Work Hard Anywhere. It tells you where coffee shops are nearby, and gives you all the essential information like seating, how strong the wifi is, if there are pastries and snacks, parking, and how many outlets are available.


Get a Laptop

I love my Macbook Air (supped up to 500GB SSD, and 8GB Memory). Austin used a Toshiba Chromebook for about a year. It worked for most word-processing and internet-based business. He said it just gets a little slow with 4-5 tabs open on the Internet because it only has 2GB of memory. Now of course, he’s working on a Macbook Air and loves it.


Bring a Back-Up Drive—Actually, Make that 2

Get a hard drive that is just used as a time-machine back-up for the mac. I like to keep this separate and undisterbed. I use my 2TB Time Machine backup from Apple. Then I backup all my photos, videos, design resources and the like on another drive. I also have an additional portable hard drive that I use as additional storage space for working files (also backed up on my photo/video/design hard drive).


Get an External Battery Pack for your Phone

I can’t tell you how many times I’ve run out of phone juice. All the time! My Instagram community management habits can eat up my entire battery in 2-3 hours. Make sure you have an external battery pack for the extra juice. I like the HyperJuice Plug USB battery pack from HyperJuice.


Get an External Battery Pack for Your Computer

Mac batteries are a little harder to come by. HyperJuice has a battery pack that I keep meaning to pick up!


Have Additional Wifi Coverage

Nothing sucks more than being revved up to work, and having shitty wifi coverage. I always make sure I have a backup so when I feel productive I can get done what I’d like. The Karma packs are becoming increasingly popular. They’re a little pricy, but perhaps worth it. You can also tether a wifi connection from a hot spot on your phone.

Invest in a Good Set of Headphones

I can’t even tell you how much headphones contribute to my overall productive-ness. I have a couple sets of headphones. When I’m long-boarding (yes like a skateboard but a bit more stable!) I like to use the Apple earbuds so I can still hear cars around me etc. When I’m working I love my Urban Ears. I’ll be grabbing a set of Beats by Dre soon too, but the Urban Ears are economical and cover a terrific mid-range while being pretty much noise-cancelling.



Step Nine: Network Your Face Off

Find networking groups, socials, meet-ups, events and network your face off! This is a great way to make new business contacts and friends in a new city. Co-working spaces are terrific for meeting other entrepreneurs, grabbing some table space and checking out their events. This is an easy way to surround yourself with like-minded people.


Wework is present in most major cities around the world (for some easy co-working). Do a Google search for the city you’ll be traveling to and see what entrepreneur-spaces are available.



Step Ten: Plan Your Transportation

Transportation is easy in most major cities. Think about whether or not you want a car. Mostly, I’d say you could do without it if you’re going to be in metro areas. Everyone told us that we were going to want a car in Los Angeles, and I have to say that we’ve done incredibly well without it. In fact, I think having the car would for sure be more hassle.


Ways to Get Around

Usually there’s some sort of public transportation to get where you want to go (unless you’re in the middle of east bumble-f*#%).


In New York, I used the subways extensively. In Los Angeles, I use a combination of buses and Ubers/Lyfts. There are usually cheap buses that leave the areas too, like Megabus, Boltbus, Grayhound etc. You can get out-of-town (leave metro areas) pretty easily with Buses and Amtrak. Anytime that I do want more control and want to drive (let’s say up the coast to hit up San Fransisco), I’ll rent a car (costing around $40/day). It’s always worth checking out flights too. I see flights all the time from LAX to SFO and Seattle for around $70. If you just need a car for a couple hours there’s Zip Car in NY (and all over the country, even in LA just not as many), or Skurt (new startup) in LA.



Step Eleven: Choose Your City and Walk Out the Door!

There are tons of cities in the US that are terrific for entrepreneurs and start-ups. Any major metropolitan area will have a diverse crowd of entrepreneurs.


Here are some cities that are known for their startup and entrepreneur hubs:

  • Austin, Texas
  • Chicago, IL
  • Columbus, OH
  • Nashville ,TN
  • Washington, DC
  • New York, NY
  • Los Angeles, CA (Santa Monica, Venice, Marina DelRey)
  • Miami, FL
  • Minneapolis, MN
  • Portland, OR
  • Seattle, WA
  • Salt Lake City, UT
  • San Fransisco, CA
  • San Diego, CA
  • Venice, CA


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I hope you enjoyed the ultimate entrepreneur’s guide to work from anywhere and travel the US!


If you liked this article you’ll enjoy these:

How to Start an Online Business in 14 Steps

How to Make Money as a Personal Brand Starting on Day One (The Action Steps and Ultimate Guide to Being an Expert)

The Ultimate Guide to Generating Free Press (PR)

How to Handle an Uncertain Future as an Entrepreneur

How to Have 1,000 Leads Even Before You Start Your Business

How to Get More Work as a Freelancer


Have more tips to add? Let us know in the comments!