recapping SXSW 2019

In learning, stories, upside by Jay Clouse

Last week I flew to Austin, Texas, for my fourth SXSW Festival. If you’ve never been to South-By before, it’s described on their website as “The South by Southwest® (SXSW®) Conference & Festivals celebrate the convergence of the interactive, film, and music industries.”

All things considered, it’s one of my favorite events. For a few days, Austin becomes a center of gravity for people in all kinds of creative walks of life — entrepreneurs, musicians, educators, researchers, and so on.

If you were to turn to the person to your right and start a conversation, you’d be constantly surprised by how interesting that conversation became.

The festival itself has hundreds (thousands?) of official events, and they are matched by a slew of unofficial events as well. If you planned out your entire day, you’d still miss 99% of what is available to you.

So between the people and the content, it can create unbelievable FOMO if you let yourself fall prey to it. It was easy for me to constantly feel like I should be doing more.

Doing more meant being around more people, all the time. And for an introvert, that can get pretty exhausting pretty quickly.

A lot of my SXSW strategy was to maximize for collisions and hold space for serendipity. After one event, I ran into the author who wrote about our podcast in Fortune. At the same time, I ran into a former podcast guest.

One afternoon, while I was just looking to find a lunch spot, I came across the Linkedin pop up where I met up with the producer of my last course on freelancing.

It reminded me of a piece I wrote last year about Tony Hsieh’s viewpoint on collisions.

I think you can create your own luck. The key is to meet as many people as you can and really get to know them. If you’re in an environment where you’re always running into people, the chances of one of those collisions being meaningful is maybe 1 in 1,000. But if you do it 100 times more, your odds go up.

My advice is: Meet lots of different people without trying to extract value from them. You don’t need to connect the dots right away. But if you think about each person as a new dot on your canvas, over time, you’ll see the full picture.

I think a major key to doing an event like SXSW well though is intentional planning and coordinating of schedules, which I credit Eric for doing well for us.

We recently onboarded our first major podcast sponsor (more info coming soon) and I told Eric I wanted to invest in some new podcasting equipment.

We came to a compromise by proactively planning a half dozen interviews with companies in Texas, which was as easy as a couple of tweets.

And with just a few emails, between John (Firebrand) and Bryan (Capital Factory) we booked several interviews at a local startup in their conference room.

We interviewed a half dozen founders, including a member of the first ever Techstars cohort, whose exit allowed him to invest in the first ever Techstars fund, which invested in the likes of Uber, Sendgrid, Twilio…we had no idea that he had that kind of background, and he brought us a bottle of wine!

And ALL of that was planned outside of our biggest reason for attending, our panel.

The panel was called “Geography vs. Investing: Does Location Matter?” and was an effort to bring the upside conversation to a national festival stage. With two founders, one in Florida and one from San Francisco, and an investor from New York, we talked about the geographical aspects of receiving startup investment.

And after the panel, Eric spearheaded the organizing of a dinner that night, which with a matter of a few texts and a couple of calls became a pretty large group of people, most of whom did not know each other.

This all took place in the span on just a few days — Saturday through Tuesday.

So what’s my point?

Once again, I was surprised at how easy it was to make plans with people. At events like this, it seems like everyone has the same fear of empty space and wasted time. So when you offer to fill some of that time with something worthwhile, they jump at it.

It was unbelievable how much we squeezed into a pretty small timeframe. Some of it planned, yes, but even the soft plans of meeting up with people happened in pretty short order.

Of course, it was hard to get done just about anything else outside of the madness (one of the benefits to really focusing on the weekend). But, I suspect if we would’ve tried to have an interaction with all the different people we met with at SXSW, it would’ve been stretched out over a matter of weeks instead of a number of days.

And there’s always something that will be special about meeting someone in the flesh. I love video conferencing, but the shortest distance to forming a real bond with someone is still a face to face, in person interaction.


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