5 Life Changing Lessons From Launching a Podcast Conference

As I write this, I am in the middle of building the first podcast conference in Western Canada. We are 74 days away from the event and I have no idea how it’s going to turn out. But for the first time in years, I feel EXCITED, and I can not wait to wake up and get to work. Here is how I accidentally launched a podcast conference, and the unexpected lessons it taught me.

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The Collapse.

Minutes after my TEDx talk in Canmore, I collapsed into my wife’s arms behind a fridge in the backroom kitchen. Weeks of preparation, days of practicing and memorizing all culminated into a 12 minute thing that happened. I didn’t remember what I said, or how – it was a blur.

In my mind, this was the pinnacle of my speaking journey. Even though I’ve been incredibly fortunate to speak at many conferences – sometimes in front of more than a thousand people – this felt different. It was TEDx. It was a big deal, and it was a goal I wrote down in a letter to myself back in 2004.

And now it was over. And with it, everything was over.

By this time, I reached most of the goals a younger version of myself set out to achieve. This talk was the cherry on top.

Now what?

Standing there in the back, away from everyone, this was one of those existential crisis moments I’ve been reliving for the last couple of years while trying to figure out what to do next.

It turns out there are two ways to deal with it: do nothing, or do something — continue the routine and settle into a monotonous comfort, or rekindle that fire within and take a leap into uncharted waters.


Walk the walk.

In 2012, I had the opportunity to speak at an entrepreneurship and marketing conference that featured Gary Vaynerchuk and a bunch of other million-dollar-plus business owners. I made the least amount of money out of everyone by at least a factor of 10, but somehow I ended up on stage.

Just before going on, I hung out with Gary for a little while (you can see the video here). Until then I had a love / hate relationship with the Garyvee brand. He swears a lot on stage, his parents already had a successful business before he started Wine Library, and I didn’t think Crush It was all that great.

I didn’t get what his deal was – until we had a chance to speak and he shared something that stuck with me since.

He wanted to show everyone he could build a successful company from scratch. That he wasn’t just a Mr A-Lot-Of-Twitter-Followers.

And he was doing it. VaynerMedia was about two years old at that time, and it was growing rapidly towards his vision of 200 employees, and $20 Million in revenue.

He talked the talk as a social media and branding personality. Now he was walking the walk as a business owner and investor.

For years, I spoke and wrote about trends, helped companies improve their marketing, and taught students about strategy. I built a business serving great organizations – while putting my own ideas and projects on the back burner.

I talked the talk. Could I walk the walk?

It’s a question that’s been in the back of mind since 2012.


Testing the waters.

Like most marketers and entrepreneur types, I’m a fan of Seth Godin. Not just because of his books and insights, but because of his projects – The Domino Project, AltMBA, Krypton Community College – just to name a few.

I was never attracted to building a large business – it’s why I keep my consultancy small (just me, plus a contractor or two if needed). But I LOVE the idea of project-based entrepreneurship, and I keep a notebook of content and business ideas I’d love to try someday.

A couple of days after Canmore, I felt like a ship without a captain in the middle of an ocean. I could go anywhere, but couldn’t make a decision where. I had a list of ideas I wanted to build eventually, but wasn’t sure which one to tackle first.

I even stopped taking on client work the year before to make room for building these “projects”.

One evening I had a sudden spark of motivation and decided to run a quick and simple test. Would anyone come if I built a podcast conference?

I asked on Facebook, Twitter, and reddit.

What came back was surprisingly positive. It could have been due to timing, supportive friends, or just luck. I don’t know.

But it was enough to make a decision. This will be the first project I dedicate myself to.


It might not work.

Risk is hard. We don’t like to think about it.

We tend to look at risk as an adventurous, desirable thing. It’s what all the entrepreneur porn being peddled on the internet promotes. People instagramming flashy cars, sharing motivational memes, humblebragging about meeting Gary Vaynerchuk backstage, or posting pictures of themselves working in a cozy chair with a cup of coffee on the side of a laptop.

We like to gloss over the fact that every new venture is a risk, and with every risk there are potential downsides. Risk means this MIGHT work, not this WILL work. You own the rewards if it does, and you are left holding the bag if it doesn’t.

And that endless moment, in that space, is everything.

To try something new, you have to let go of the old, familiar, and comfortable. And that becomes much harder with kids, a mortgage, and other responsibilities. The punishment for failure is much higher than before.

And yet – you only get one life to live. So the tension grows between who you are now, and who you would become after taking the leap.

For a long time, I chose to stay inside my comfort zone. And for whatever reason, that changed this year.

This podcast conference is just the first step in a new direction, and the truth is… I don’t know if it will work. This is my first time trying to build an event, and even though I understand the marketing side of things, I have only instinct and some friendly advice to run on in terms of organization, logistics, and event planning. I know the kind of event I would want to go to – and that’s what I’m building.

For the first time in years, I wake up excited, and can’t wait to get to work! I am ready to own the outcome, however it turns out.


All of me.

Over the years, I’ve had a number of different interests ranging from calligraphy, podcasting and black & white photography to random things like restoring straight razors and making furniture from reclaimed wood. These were always side projects and hobbies on top of my regular work that includes marketing, business strategy, curriculum development, teaching, and speaking.

What’s interesting about this particular project, is that it pulls all of those interests, skills and talents together. It feels like an engine firing on all cylinders. It feels like diving into a deep, warm pool of immersive and joyful work.

In 2013 I started focusing on the idea of meaningful work, and finding ways to do more of it. By now I interviewed dozens of entrepreneurs, authors, and thought leaders about doing work that matters, and within those I discovered a common thread.

Their work exists at the intersection of three key elements: values, service, and competency.

Values – They are clear on who they are, and what they stand for. Their values serve as a guidance system for clients, businesses and projects they take on.

Service – Their work benefits many. It is designed to serve a specific audience, solve a problem, and every project adds to their body of work. Their legacy.

Competency – They leverage their unique ability. I found that almost every impactful leader has a different, unique combination of strengths and talents they put on full blast in their projects.

PodSummit has all those elements for me. It aligns with my values of learning and sharing. It serves a passionate group of people sharing their voice with the world. It allows me to fully leverage and test my skills in marketing, building, audio, video, and design. It is all of me.

This is my fire, rekindled. A leap into uncharted waters. And I don’t know if it’s going to work.

But it’s worth trying.

So, what are you holding back from?

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