My hardest day as an entrepreneur

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In March of 2019 Alyssa and I had just finished hosting our 3rd RVE Summit in Alabama. We were riding the high of an awesome week with old and new friends and easing back into our typical workdays after a week of craziness.

I checked my email and opened one up from a customer at Campground Booking—our biggest one at the time— who, to put it super mildly, was truly upset and disappointed with our product.

It’s never fun when a customer is upset, but in this specific scenario, I’d poured my heart into helping this person and her team. I’d stayed up for nearly three days straight to help with their initial launch and even flew out to spend time with them in person.

After all of that work, it was heartbreaking to read her message.

I’m not sure if her message was the tipping point or if I was just running on fumes after hosting our conference, but I did something I rarely do:

I broke down and cried.

I felt like a failure.

After spending so much time pouring into something to make someone happy and create this business, it still wasn’t where I wanted it to be. It wasn’t good enough for our biggest customer.

Confronting that viscerally hurt inside.

This may sound dramatic, but at the moment it’s genuinely how it felt.

This was one moment (of several) in building Campground Booking where I wanted to quit and walk away.

Was this worth this pain?

Why was I beating myself up trying to create this new company when I already had a business that was doing well and serving an audience I lovedI could do Summits all year round and be happy and hang out with awesome people.

Is this business that is a huge uphill battle going to be worth it in the end? Or ever?

In the moment, I struggled to answer these questions.

Alyssa, who was sitting next to me while I broke down, wouldn’t have blamed me if I’d simply quit. But like several of the other hard days in entrepreneur-land, she had my back and picked me up when I was down.

And I kept with it.

During other moments like this one, I would pick up the phone and call a buddy who had experience starting a business of their own. I’d vent and complain and they’d hear me and encourage me to stick it out and say that days would get better and this was all part of the process.

I can honestly say that if it wasn’t for having a Rolodex of entrepreneur friends and an amazing wife to pick me up, I 100% would have walked away and quit what eventually turned out to be a very meaningful business opportunity and then acquisition.

The ups and downs of starting Campground Booking weren’t all too dissimilar from the roller coaster we felt when initially hitting the road. Some days were really high—I’m casually watching grizzly bears from the windshield in Alaska! My business is making money while I’m chilling on this beach!—but the lows were really low.

None of our family or friends pursued a nomadic life and until we met other travelers, we felt like we were going at it totally alone.

But once we found a tribe, we could share in the journey together. We could talk about what was going well and what wasn’t with people who understood our lifestyle.

Whether it’s in life, business or travel — I believe that having good people in your corner is what has the power to make all the difference. Having someone to lift you up on the hard days and remind you that tomorrow will be better and that the outcome is worth this brief moment of pain, is what will keep you in the ring long enough to see a big dream take hold.

In thinking about this year’s RV Entrepreneur Summit, Alyssa and I wanted to come up with a theme that embodied this sentiment of community and its importance.

And we landed on the theme of “gather“.

It’s the idea that together we can build more epic stuff than we can alone. The idea that at the end of our lives the work we’ve done will likely be less important to us than the relationships we cultivated along the way.

The idea that gathering with like-minded people who lift us up can make all the difference amid long and strenuous journeys in business, travel, or life. It might sound a bit too soft, but the truth is sheer will is only going to take you so far. You need support to pick you up along the way—I know I did more than once (or more than a hundred times).

And speaking of gathering, I’m excited to bring together and gather a group of amazing people in Colorado this fall at our RV Entrepreneur Summit.

It will be our fifth year hosting this conference and the first time for us to ever do it at our own campground property. This idea of bringing together like minded people—people with common values and passions in life like travel, time in the outdoors, and creating a life where you own your day—is the whole reason I wanted to start a campground to begin with.

And in less than two months, we’ll be able to gather together on our property, boondock, and spend a week talking about RVs and travel and business and all those things that light us up.

I honestly can’t wait.

We released tickets last week and we’re almost sold out with about 15 RV sites left at the moment. If you’ve been thinking about coming, we’d would love to see you here in Montrose, Colorado this September (you don’t need to have an RV to come either, more details on our website).

For more information about our fifth annual RV Entrepreneur Summit, check out our FAQ page here 🙂

Or you can always reply to this email if you have any questions!

One last thing…

I wanted to share this story today because if I’ve learned one thing about running a remote business (I’ve learned a thousand probably but that’s too many for just one email), it’s that you can’t do it alone. You may not have employees or partners or anyone else running your business with you. But you need people in your corner to support you.

Maybe you’re like me and it’s so that you can have someone to vent to when you feel like giving up. Maybe it’s a mentor to give you advice on pricing or taxes or product development. Maybe it’s a spouse to tell you when you’re overreacting and to just get back to work.

But I know you can’t (and don’t have to) do it all alone.

Have a great week and excited to see several of you in person at our RVE Summit in September :).