Why Every New Entrepreneur Should Travel More

By Sean Ogle •  Updated: 05/31/16 •  7 min read

You want to know an insider’s secret for growing a business quickly?

Travel more.

It seems counterintuitive, right? For years I’ve been espousing on the fact that you can maintain a business while on the road, but it’s difficult to grow a business on the road.

While generally I believe that to be true, today I’m going to show you why strategic, regular travel can be one of the fastest ways to grow a business.

Let’s hop in the Delorean for a second back, to January of 2010.

In January of 2010, I took a leap and I moved to Thailand.

During that time, I was traveling around the country and meeting all sorts of incredible people, who were doing interesting things.

Those were the people who formed the basis for my initial (and sustained) success as an entrepreneur. Because you know what?

As cliche as it sounds, it really is all about who you know.

Don’t believe me?

Have you ever noticed how a couple times a year all of a sudden many of the blogs you read, and many of the emails lists you’re on are all promoting the same thing?

There’s a reason for that.

It’s because so many of them are friends.

One of the biggest reasons I promote products like the Paradise Pack is because I like Jason and Travis, the dudes behind it. Both have traveled to Portland, met me in person, and formed that relationship.

Something changes once you meet someone in person. When you can shake their hand, have a beer, and in many cases, create a shared memory or story – it takes things to a different level.

All of a sudden, they’re more likely to help you out, promote your stuff, or make an introduction to someone else.

Because of my time in Thailand I got to know Dan Andrews, Adam Baker, Matt Kepnes, Jodi Ettenberg, Derek Johanson the list goes on.

All of those people have allowed me to grow Location Rebel in one way or another.

Travel More: But Make it the Right Kind of Travel

Not all travel is created equal though.

Obviously taking a solo backpacking trip through the wilderness probably won’t do much to help you build relationships.

Lately, most of my travel has been golf related as I continue my quest to play the top 100 courses in the US and the world. Because of this, I’ve met and built relationships with tons of influential people in the golf world.

Just this past weekend, I played golf with two editors from Golf Digest, and met with the owners of my favorite golf apparel brand.

The 9th hole at Machrie Links Golf Club on Islay

Machrie Links in Scotland might be one of the most remote places I’ve visited in my quest to travel more.

Because I continue to build those relationships, Breaking Eighty has been getting more and more recognition, and making more money in the process.

haven’t been doing as much travel specifically for Location Rebel, and I feel it. Relationships I’d like to build and I would like to make, haven’t been coming quite as quickly because I haven’t been prioritizing them.

Take a look at some of your favorite lifestyle entrepreneurs. Even if they’re brands aren’t based around travel, my guess is more than a handful of times a year they are going to conferences, traveling to entrepreneurial hubs, and getting to know people in real life.

There’s a reason that all too often your favorite bloggers or business owners are blowing up your Facebook or Instagram feed with photos of them hanging out…together!

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So How Can You Strategically Plan to Travel More?

Ok, so it’s clear: More travel –> More Connections –> More Opportunities –> More Success

But if you haven’t been in that mindset, or you aren’t someone who usually travels, how do you start planning for something like that?

Here are a few things to consider that should help you not only book more tickets, but make the most of your time when you do go.

1) What are the Two Biggest Events of the Year for Your Crowd?

You don’t need to be at everything, but it makes sense to attend to at least a handful of conferences each year.

For years I would attend the World Domination Summit in Portland and SXSW in Austin.

Now I’m branching out to more marketing oriented events. But the fact remains, with every single event I’ve ever been to – I’ve met at least one or two people that have had a significant effect on my business.

It’s never about meeting everybody, it’s about those handful of people you really connect with that will be great relationships moving forward.

I met Nick Reese and Andy Drish at SxSW years ago, and each of them have had a dramatic impact on what Location Rebel has become.

So decide what the two biggest events are for you and your goals and put them on the calendar. Are you a writer? Go to Writers Digest. Lifestyle entrepreneur? DCBKK. Social media expert? SocialPro. Professional blogger? New Media Expo.

2) Why Would Knowing Certain People Make a Difference in Your Life?

Sometimes in order to make the leap and be willing to spend the time and money to travel, you have to have a deeper understanding of why it would be important.

To help with that, answer these questions:

3) What are you going to say?

I’ve recently learned that I’m a natural ambivert.

Meaning, in the right social situations where I’m comfortable, I can appear very extroverted. However, my natural tendency often leans towards being more introverted and shy.

For instance if I’m at a conference where I don’t know anyone, I get really awkward. That’s why thinking this step through before you go to events is so important.

If you have a general game plan for how to introduce yourself, strike up a conversation, and generally just be useful and interesting, you’ll have a much better chance of getting more out of the relationships you’re hoping to build.

I always try and find some commonality as quickly as I can. The work stuff doesn’t matter, rapport does.

So pay attention to everything being said, and look for any bit of personal information you can espouse elaborate on and get excited about.

For instance anytime someone mentions they golf, have lived in Thailand, or like Islay scotch? Game over. Things like that are really easy for me to talk about – so it helps strengthen the relationship quickly.

4) Sign up for a Credit Card

“I can’t afford to travel.”

How many times have we all heard this? First off, most people can afford to travel – it’s just about priorities. This post from Chris Guillebeau I still find to be extraordinarily true.

But if you want some help, frankly, leveraging travel bonuses from credit cards are a great way to make things quite a bit cheaper.

A free round trip plane ticket anywhere in the world, all for signing up for a credit card? No brainer.

Of course this is assuming you can be responsible with it and pay it off in full every month.

Check out One Mile at a Time for some of the latest and best deals.

5) Take a Leap

Bottom line is, if you don’t make it a priority and just buy a ticket, it can be really easy just to stay in the same old routine. That routine where you’re not meeting the people and having the experiences that can help a new business take off or an old business grow even more.

Every day I see entrepreneurs reaping the benefits of building new relationships, and every day I’m thankful for the ones I’ve built.

So, think about where you can go that will have the greatest benefit for you personally. Book the ticket, take a leap, travel more, and enjoy the memories you’ll make regardless of the outcome.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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7 comments on "Why Every New Entrepreneur Should Travel More"

  1. I couldn’t agree more Sean. I’ve been only a travel writing kick recently and just got back from Paris. Traveling is a no brainer! Fun, exciting, educational, a business expense, and great new material for entrepreneurs and bloggers.

    There’s a great big world out there to see! I need to brush up on my Mandarin too. 🙂



  2. Thanks Sean

    I needed that. I’ve felt that traveling wouldn’t be right at the moment because I first need to fix my monthly income. This is BS. Thanks for the reminder.

  3. Thanks for listing some of the events to go to. I’ll look into them and see which ones will suit me best.

  4. Moe says:

    Thanks Sean! I’ve been pushing my help to travel more and this just give me more motivation to travel more.

  5. This is so important because many people will put off traveling like they put off doing their laundry or in the name of progress. The real progress comes from getting out of your shell and surrounding yourself with the lifestyle you want to live.
    Great post, Sean! I’d love to know, what events are on your calendar in the coming months?


  6. Corey Tat says:

    Hey Sean,

    This is a kickass article! I haven’t travelled in almost a decade and your journey really gave me the motivation to try this laptop lifestyle entrepreneurship.

    I’m in the health and fitness industry and I love what I do but my business requires me to be there all the time.

    Reading articles like this makes me work and grind so much harder in my spare time. I want to eventually transition into being able to travel to asia and work anywhere in the world.

    You’re amazing dude. Thanks for the article!

  7. guy says:

    this is so true, not only is travel fun but you can learn so much while doing it, you only get one life and need to make the most of it!

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