Last week I let all of my calls go to voicemail and checked my inbox at a record-low once per day.

That’s how I got myself free to have a series of freak experiences at the largest gathering of startup community leaders on the planet—the UP Summit, presented by UP Global. With more than 500 leaders from 75 countries around the world, I would have been paralyzed by the magnitude if I hadn’t found a 1-2 combo that unlocked the event’s full potential.

1. Go Up


I woke up each day and promptly punched my inner wuss in the face. Rolling out of bed in Vegas is hard enough on it’s own, but when you put yourself out there to learn something or meet someone new, your first instinct is to flinch.

It’s totally rational. As founders and instigators, we’re probably already balancing more projects than is healthy for a human being. The prospect of adding more action items and followups to the ever-growing to-do lists doesn’t get most entrepreneurs giddy. And breaking ground on a conversation with someone new can be a little scary.

Luckily, the UP Summit organizers facilitated in a few of the conference tracks that helped give some conversations a push. And Downtown Las Vegas delivered on its mission to foster connectedness, collisions, and co-learning.

It almost seems counter intuitive.

Sometimes, you just have to get the courage to walk up and ask, “Um… excuse me, sir, but I noticed you’re dressed as a banana. Why is that?”

OK, most times you won’t have an alley-oop approach like that. So, don’t give yourself any more than 2 seconds to think about whether or not you should talk to someone new. Make like an overused advertising slogan and just do it, because it’s the collisions that make the difference in building a community or a business.

Pro Tip: If you’re as exhausted by the “So what do you do?” line of questioning as 99.99% of the world (that’s a true stat I just made up), go for something relevant like the speaker in the previous session or the funky socks that your new friend is rocking.

2. Go Deep

Photo credit: @FrankGruber

There’s no value or meaning to creating small talk or collecting business cards. If you’re going to go up to someone new, go deep.

This one’s tough because every brain cell between our ears screams at us to stay in our happy place—that grotesquely mediocre zone of comfort.

The real happiness can be found in the quality beneath the surface.

At the UP Summit, the leaders in attendance converged upon Vegas from such a variety of cultures that we didn’t have as many how-about-the-weather, or did-you-see-that-game discussions. Without the crutch, we had to lean in (boom, Sheryl Sandberg reference).

up-summit-friendsThe quality-over-quantity theme was threaded through every minute of time with the UP Global crew. Strong relationships sprouted from each event that catered to serendipitous connections. The deepest growth was rooted in scheduled blocks of time that allowed for potential collaboration.

If I hadn’t taken a swing at going up to new people at the UP Summit, I never would have met the dozen new friends from around the world. I wouldn’t have learned about new programs that I’m now planning on bringing back to my hometown. And I wouldn’t have found those new partnerships that will more deeply connect my startup community with what’s happening around the world.

If I hadn’t dared to go deep in my conversations I wouldn’t have learned from the best conversation I’ve ever had about how to grow a successful relationship while running startup. I wouldn’t have a startup friend to visit when I go to the Philippines this summer. And, most importantly, I wouldn’t have learned about what all of the inspiring people in the UP community are building.

So, my question is, why don’t we build intention around creating these kinds of experiences back at home? How can we keep the momentum going by going up and going deep?