Networking for Entrepreneurs: Making an ass of yourself is a right of passage

Making an ass of myself at TravelCon taught me a priceless lesson about networking.

TravelCon is an annual conference that artfully blends the romance of travel with the practical skills you need to succeed as an entrepreneur in the travel industry.

TravelCon’s founder and driving force is travel blogger, author, and entrepreneur Matthew Kepnes—who is best known by his professional moniker, Nomadic Matt.

Matt traveled the world non-stop for over a decade, writing his blog and running his business from wherever he happened to hang his rucksack.

nomad on fire

I became aware of Nomadic Matt when he appeared on the podcast Entrepreneurs on Fire with John Lee Dumas. Click here to check out my interview with JLD.

At the time, I remember being captivated by the notion that this guy had been out roaming the earth for years generating enough revenue from his blog to fund his travels (and then some!).

Over the years, Matt’s readers grew increasingly interested in more than just his expert travel advice. They wanted to learn about Nomadic Matt, Inc., the business that fuels his enchanting lifestyle.

Simply put, Matt’s loyal fans wanted to know how in the hell he does what he does—so they could do it to.

Several years later, TravelCon was born.

the heart of a traveler

TravelCon’s stated primary goal is to help people learn the skills needed to develop a profitable and sustainable career in the travel industry. It’s a straightforward goal—which I appreciate, but I like to portray TravelCon in a slightly more romantic light.

In my view, the true heart of TravelCon is in teaching passionate travelers to create lifestyles that allow them to travel when they want, where they want, and for as long as they want.

The inaugural TravelCon event went down in 2018 in Austin, Texas. The three-day conference offered dozens of live learning sessions with experts teaching the skills they use to fuel the money-making engines in their businesses.

I left TravelCon 2018 inspired, energized, and with several new goals for the coming year. The most audacious of those goals was to be a speaker at TravelCon 2019 in Boston.

Any why not? I love speaking. I love teaching. And I love TravelCon.

demystifying podcasting

TravelCon 2018 included a session called “How to Start a Travel Podcast” delivered by two of the best travel podcasters in the biz: Chris Christensen from the Amateur Traveler and Travis Sherry from Extra Pack of Peanuts—both of whom I've interviewed on my podcast.

I was already an experienced podcaster, but I attended the session anyway in support of my podcasting brethren who, like me, believe the microphone is far mightier than the sword.

Chris and Travis’ presentation served as a solid primer to the often mystifying world of podcasting.

Moments after the session concluded, a pivotal question popped into my mind: where do we go from here?

an idea hatches

Podcasting has been a game-changer for me, and I am passionate about helping aspiring podcasters get their voices out into the world.

The first TravelCon podcasting session was clearly intended for beginners, and I imagined Matt and his team would want to build on that the following year.

After the 2018 podcasting session, I spoke with several attendees to see what lingering questions they had about starting a podcast. Unsurprisingly, many of their questions were about podcast production—equipment, recording, editing, publishing, etc.

Based on their feedback, I came up with an idea for a hands-on podcasting workshop where attendees could record, edit, and publish a podcast—all within a one-hour conference session.

The wheels were in motion, and I didn't waste any time in pitching my idea to Matt for TravelCon 2019. Looking back, I probably should have wasted some time.

Instead of dazzling Matt with my idea, I laid an egg of epic proportions.

seizing the moment

Matt was very visible throughout the conference. In fact, he seemed to be everywhere. Watching him hustle for three solid days left no doubt that he is wholeheartedly invested in the success of TravelCon.

On the last day of the conference, I skipped one of the afternoon sessions so I could meander peacefully through the sponsor booths while the rest of the attendees were occupied.

I spotted Matt chatting with a woman at one of the tables. A few seconds later, he said goodbye and walked away. Surprisingly, nobody followed him. For the first time in three days, nobody was waiting in the wings for his attention.

Nobody but me.

here's the pitch...

I said hello and introduced myself. In my attempt to not be annoying, I did what seemed like the right thing to do: I got straight to the point.

Matt walked swiftly through the concourse of the conference center. I managed to keep pace with him while akwardly blathering out my podcast workshop idea in what felt like a single breath. He sped up slightly, which compelled me to talk faster. His head swiveled back and forth several times. He appeared to be looking for a lifeline—a friendly face to rescue him from the bitter end of a one-sided conversation.

"I think a podcast workshop would be a great fit for next year,” I gushed as I involuntarily shoved a business card in his hand—something I’d never done to anyone before or since.

“OK, thanks,” he said, turning abruptly back to the business of TravelCon.

sleazing the moment

Matt didn't know me from a hole in the wall, and I'd just assaulted him with a hard pitch mere seconds after meeting him for the first time. And while he was trying to run a conference no less.

It took a moment to process what had just happened. When reality finally hit, it hit like a ton of rotten tomatoes.

I was that sleazy networking guy.

only after an epic failure can the real growth begin.

Discouraged, but not defeated, I remained committed to my goal of speaking at TravelCon 2019. It was starting to feel like a longshot, but it takes more than one awkward conversation to make me throw in the towel.

My last shoestring of hope was dashed when 2019’s initial roster of speakers was announced. It was revealed that podcasting royalty Jordan Harbinger was leading a session called “How to Host a Killer Interview.” Jordan has been podcasting for over a dozen years and has legions of fans.

It was at this point that I accepted my fate and did something I hoped I wouldn’t have to do: I purchased an attendee ticket for TravelCon 2019.

keeping it in the family

Like I mentioned before, TravelCon offers sessions on a rainbow of topics—one of which is family travel blogging.

Thanks to my Family Travel Radio podcast, I am part of a robust network of entrepreneurs and creators who serve the family travel market—writers, bloggers, television hosts, travel advisers, tour operators, etc. Over the past year, I’ve been steadily nurturing relationships with many of these individuals without expecting anything in return.

Even though my podcast puts me firmly in the family travel media space, I hadn't considered myself a great fit to speak on family travel. Being a relative newbie, I often feel like an impostor standing next to my more experienced family travel colleagues.

TravelCon 2019 was less than a month away when I received a call from one of those colleagues. He had been slated to appear on the family travel blogging panel, but a health concern had forced him to cancel.

He asked if I was interested in taking his place.

holy cow!

I jumped at the opportunity and asked him to put in a word for me with Matt, which he promptly did.

The next day I got an email from Matt. I was in. My goal of speaking at TravelCon 2019 became a reality.

The colleague who helped me get the TravelCon gig is part of that network of individuals with whom I’ve been patiently nurturing relationships. In the end, that approach delivered something that an aggressive sales pitch could not.

The failure of my obnoxious pitch taught me a partial lesson about networking and life. The lesson was complete when a friendship I’d built thoughtfully over time ultimately helped me win the day.

the punchline

After writing the initial draft of this post, I revisited Nomadic Matt’s 2015 appearance on Entrepreneurs on Fire.

In the interview, host John Lee Dumas asked Matt to tell the story of his worst entrepreneurial moment. When I heard Matt’s response, all I could do was shake my head and smile. He’d given me the perfect ending to my story.

Here's an abbreviated transcript:

"I got to meet Ramit Sethi from I Will Teach You to be Rich. I’d never met him before … 

"I remember asking him, 'Ramit, I’ve got this new e-book called How to Travel the World on $50 a Day. It’s a small little PDF ... would you put in on your mailing list?'

"Little did I know that you don’t pitch big people the first time you meet them. It’s off-putting."

- Nomadic Matt Kepnes, April 2015

There you have itproof positive that making an ass of yourself is, in fact, a right of passage for entrepreneurs.

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About the author, Aaron Schlein

Aaron's personal mission is to create a freedom-filled life for his family.
His professional mission is to help others do the same.

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