Kyle Kesterson

Heath’s biggest business mistake…EVER.

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*ding*

New group message with Wes, Heath, & Alyssa

Wes W: Just landed and heading to baggage pick up. Where you at?

Alyssa P: We’re in Maine…?

Wes W: haha you’re funny

Heath P:

I looked up through our windshield and saw Heath staring at his phone. Heath was pacing on a phone call fifty yards away, but I can say with 95% certainty that he muttered an expletive, followed by a quick “I’ll call you back.”

My stomach dropped. I knew exactly what had happened before I even knew what happened.

I took a deep breath, saved the video I was editing, and ejected the hard drive before sliding them into my backpack. Walking back to the bedroom, I unzipped our empty suitcases. I pulled them out of our storage bays this morning to pack for tomorrow’s early morning flight to Denver.

Heath had been hard at work on our biggest client project ever, helping to plan Winnebago’s first virtual product launch for three brand new RVs. A crew of a dozen people were all flying into Denver and we coordinated our arrival times so we could caravan together out to Buena Vista and location scout before the team dinner.

And Heath booked our flights for the wrong day.

Wes and his crew were all at the airport, expecting us to already be there waiting with the rental cars to pick them up and drive three hours out to Buena Vista to location scout for a week of filming.

We were 2,000 miles away.

“I screwed up,” Heath kept saying pacing back and forth in the RV. “I even said on the call yesterday, see y’all on Tuesday night, but our flights are booked for Wednesday! I can’t believe I did this. I can’t believe I did this!”

Heath called the airline while I quickly packed our bags. If we hurried, we could take a 2 o’clock flight to Chicago, and then hop on the next flight to Denver. If we made those flights, we would arrive at the Denver airport at midnight and roll into the Super 8 in Buena Vista at 3:00 AM—that would be 5:00 AM eastern—and be up and ready to shoot by 7:30.

We would miss scouting locations this afternoon and the all-hands prep meeting this evening, but we could start bright and early tomorrow, fueled by caffeine and mountain air.

This. was. a. disaster.

(And the reason why Heath refuses to book our travel now.)

This wasn’t our first big mistake as entrepreneurs. We’d made plenty. Shooting a video with the mic muted. Accidentally deleting footage. Forgetting to charge the camera batteries.

But missing a flight out to shoot for your biggest client project ever really takes the cake.

Running your own business is hard.

It’s stressful.

And there will be so many times where you make a mistake that feels unfixable—like being 2,000 miles away from a film shoot you’re supposed to be directing.

Learning how to deal with your failures in business is only part of being an entrepreneur.

Like when Heath had to own up to Winnebago and say “I’m sorry I missed last night’s meetings. I booked our flights for the wrong day.”

Which was greeted with a chuckle and a kind “But you made it.

Start a Work-from-Anywhere Business Course

Today we’re launching the course so many of you have been asking for: a 30-day training on how to start a business you can run from your RV.


I typed them up in the Notes app on my phone…When Heath and I started thinking about this course, we were driving to Alabama for our 2019 RVE Summit (so this course has been in progress for over a year and a half 😬) We talked for hours about our biggest business lessons and questions we wished we had the answers to sooner.

Added more to the list throughout the year as I worked on outlining lessons…

And included them all the final version of the Work-from-Anywhere course.

For every big question and hurdle we found to starting a new venture, this course has lessons, guidance, and templates to solve your business problems before you even have them.

Problems like:

I don’t have a single business idea.

SAME. Business ideas? Not my thing. This is why we have a documented process for figuring out how to develop and validate profitable ideas.

No one is going to hire me or buy from me.

We share half a dozen strategies that have worked for us to find customers for multiple businesses, plus a case study from our friend Kim who scored her dream job: freelance writing about wine.

I’m terrible at selling.

Learn how to craft your elevator pitch (don’t worry, you’ll see that Heath is bad at this too) so you can confidently share why you and your business are awesome.

How do I wow my customers so they buy from me again?

I’m 99% sure I’ve made thousands from a particular client because I sent her a bottle of champagne once. (Plus a handful of other strategies for overdelivering to your clients so they keep coming back!)

For the love of chocolate, how do I legally file a business without an address?

We found an easy solution for you, I promise.

Plus we’ll guide you through all of the other really confusing and annoyingly bureaucratic parts of starting a business, like how to set up a business bank account or how to write a binding scope of work for your first client.

Download templates for contracts, scopes of work, and business plans as part of the course

Don’t do this alone.

This year, we missed out on doing one of our favorite things in the world: chatting in person with RV entrepreneurs about their business ideas at our annual RVE Summit.

Darn you, COVID!

Getting to make new friends and share a meal while talking about marketing strategies and business tactics lights. us. UP.

It’s the work we love to do because it doesn’t really feel like work. It’s fun. And there’s usually dessert. Win-win.

Which is why as part of the course, we wanted to include the option of one-on-one coaching calls with us as well as group coaching calls with fellow students.

We work better together.

In coaching calls, you can get feedback on our ideas, get advice on specific problems, and be supported by an amazing community of RV entrepreneurs who get it.

*Access to coaching calls will be limited to 15 students.

Step-by-Step Guide to Starting a Business

Heath and I have been running multiple businesses for years from the beaches of New Zealand to the Colorado mountains to wineries in the Finger Lakes and everywhere in between.

Getting started is the hardest part. Finding that perfect business idea. Figuring out how to get people to pay you to do what you love. Taking the show on the road.

It took us years to feel like we weren’t just faking it till we could make it.

We’ve distilled lessons in this course into a 30-day format to keep you from getting stuck on any one piece of starting your business. You don’t have to take perfect action, you just need to move forward.

Why We Created This Course

We didn’t create this course because we consider ourselves experts in running a remote business.

Since 2014 we’ve made a lot of mistakes like the one above (some equally embarrassing and some more costly).

The purpose of putting together this course is to compile some of the biggest lessons we’ve learned while building our business on the road. Our hope is to help others start their business faster by avoiding some of what we’ve learned the hard way (aka through awkward conversations with clients and last minute booked flights).

We also didn’t want to make this an exorbitantly priced business course, as it’s really catered to those who are just getting started or ramping up their remote business (and you should put that money to use on the biz). The Start a Work-from-Anywhere course is $30 for 30 days of lessons (or $98 for the course + two coaching calls, one group, and another 1-on-1).

Start a Work-from-Anywhere Business closes this Friday, October 9th at 11:59 pm.

Learn how you can launch a mobile business.

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