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A Love Letter to DSW: Conferencing, Reimagined (Part Six of Six)

Friday: Showtime


It’s the day of my presentation and 2 things happen that I feared most. I forgot to eat and I had technical difficulties with the damn slideshow.


The day starts off with sleeping in. I’d moved from the pool house to Castle’s cavernous loft in a desolate but developing section of town (as evidenced by the joggers hustling strollers down the sidewalk).


Without even getting off the couch, I make the mistake of opening my laptop to take a peek at my slideshow. 3 hours and 150 edits later, panic starts to set in. I realize I haven’t eaten, Castle’s house, though filled with carnival paraphernalia, mannequins, taxidermy, and ironic, vintage tchotchkes glued across every inch of the wall, still doesn’t have a morsel of food in the fridge. She microwaves me a bowl of noodles just before she exits the building. It doesn’t quell the hunger. I’m running out of time, and perseverating over my presentation, playing through jokes, trying different openers, wondering if my memes will catch a laugh. I’m worried, mostly because I’m physically starving, but it’s easy to mis-translate the panic as something deeper and worth obsessing over.


After walking in circles around her loft for a few minutes – gathering my keys, printing a backup of the presentation, finding my laptop, etc., checking my pockets for keys, checking the laptop for the presentation, etc. I dig into my DSW tote and find bean and egg burrito from a couple of days before. Has it gone bad?


So now I’m driving down the street, eating a cold, doughy burrito and trying not to heave. Thank god there’s a parking space right in front. I hop out, check the time. I’m so NOT me right now, which is the worst thing possible for a presentation. This is where I make my most important decision of the day.


I get back into the car, roll the windows up, push the seat back, and meditate for 10 minutes. Eventually – probably around minute 8 – the voices in my head chill the fuck out. I’m breathing. It’s me. My second most important decision is choosing to not worry anymore. Days of preparation, 15 years of experience, a desire to help, a selfless love of the people … these are the things that make for a badass presentation.


With newfound peace and stillness, I walk in the door and find an empty front desk. The stage looks enormous, the bleachers and folding chairs, vacant and formidable. Showtime in 20 minutes.


Some dude tells me there’s another desk on the other side of the building where someone can help me. That wouldn’t be a problem if I wasn’t standing in a giant (modernized) industrial warehouse.


“You got a golf cart?” I jest. He offers to walk me over, which takes a solid 5 minutes at a quick gait. A woman greets me warmly, gives me a bottle of water, and we walk back to the stage. Another 5 minutes. People are trickling in as we hook up my laptop.


Time for problem number two: technical difficulties.


The most important part of the presentation are my résumé samples. That’s what everyone wants to see – how I can solve their problems on paper. But the links in my slideshow aren’t working. The memes look great, but no résumés.


No résumés? That’s like a lion tamer showing up without his lion. Not good, but the clock is ticking and the chairs are filling up. Eff it.


Brian’s smiling face makes it all better. He hops up onto the stage and says he’s going to introduce me in a few minutes and that Castle is held up somewhere. He can’t figure out the link problem with PowerPoint either. It’s showtime.


Brian’s intro is stellar – it’s not about my credentials, my umpteen years in the business, my Silicon Valley heritage… rather, it’s about my laugh. “Next to me, Cliff might have the best laugh of anyone at this conference.”


It makes me laugh, which makes him laugh which makes me laugh again. Snickers in the audience. The stage is set. I take the mic from Brian and briefly wonder how deep his genius goes. Then I turn to the audience, about 200 or so people, not many empty seats in the house. It’s on.


Perhaps counterintuitively, presenters feed on validation. We’re the experts up here and yet we’re often looking to the audience to tell us how we’re doing. Musicians are this way too: relying on their crowd to source energy, gauge success, and dictate the direction they go in.


“Presenter Validation” shows up in several ways:


1) Laughter & Smiles

2) Notetaking

3) Handraising

4) Personal Disclosure

5) Not Leaving


I remember the Denver Startup Week Presenter tenets of not giving a fuck, cussing openly and unapologetically, being an expert, and being myself. It helps to have plenty of familiar faces in the crowd: people I’d met in prior days of the conference, Castle’s friends, and (since the 20-minute mark) Castle herself, who gives me plenty of laughter and smiles from the sidelines.


About midway through the presentation, in front of the backdrop of my bulleted resume strategies, I look out into the crowd and recognize I’m checking all the boxes.


It doesn’t matter that I can’t access my resumes through the PowerPoint. Fuck the technical difficulties. I ditch the PowerPoint and open up a folder on desktop. The jokes come easy from my side, the hand-raising and questions rise out of the audience and land at my feet like loaves of bread.


People stay the duration and beyond. 20 or so people hang afterward to get questions answered and 50 more leave business cards before sneaking a wave out the door: my fellow entrepreneurs and creatives full of that thing we crave and relentlessly pursue: inspiration.


The week dug itself into me and I just gave something back. I done good.


Lessons Learned:

If you can find a way to be yourself and be an expert at the same time, you can’t lose.



Friday Night


When I walk into Castle’s loft, buzzed on my post-prezi high, I find her laying in bed with one of her besties. They’re exhausted and elated. Content and clothed, down to the shoes and jewelry.


“Who wants a whiskey?” I shout triumphantly, walking into the galley kitchen.


As I hand over the tumblers, I ask Castle what we’re doing tonight.


“Drag Queen Panel,” she says. And then more dramatically: “Building a Bankable Brand as a Diva.”


“Of course,” I reply.


Most conferences end with a tour of the city or a hotel-sponsored party under bright lights and beige walls.


Not Denver Startup Week.


The final event is a lineup of local drag queens, including special appearances from Sue Casa of San Francisco fame and Chad Michaels, winner of Ru Paul’s Drag Race All-stars and unbeknownst to us at the time, Yvie Oddly, this year’s Ru Paul’s Drag Race winner.


The queens don’t disappoint. They’re catty, articulate, sultry, and serious about their brands. I learn that lots of queens are philanthropists – they have causes – even though the money’s not so good on the runway.


After the panel, Castle comes out and drags me into the VIP section, where we eat nachos and drink stiff drinks. The highlights of the drag shows to follow are a lip sync to a TLC medley with full dance numbers and, of course, Sue Casa doing her famed “Hollaback Girl” with poopy bananas.


2 hours later, a huge dance party breaks out, with food trucks outside where you can mingle with the drag queens. I eat. I dance like mad. With the smoke machines going, the lights, and the pulsating crowd, it’s easy to forget I’m at a conference – a conference, I know, I won’t soon forget.


Denver Startup Week: designed to enlighten.

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