Crashing the gate

“Can I see your ID, sir?”

“Are you fking serious?”

That’s how my day started at the “Copy Legends Lock-in” event Tuesday in Orlando. 

The “lock-in” was a one-day, invite-only mastermind hosted by Todd Brown, fulfilling a longtime dream of his to gather around a table with what he considers the “absolute royalty of Direct Marketing” and essentially braindump our best stuff. 

Apparently, no mortal hotel conference room could safely hold all this brainpower, so Todd rented a massive luxury home in a gated community for the occasion. 

Start time was 9:00 am. 

At 8:56 I’m being held for questioning at the security gate, with Chris Haddad in the passenger’s seat. 

Some visual context in case you’re not familiar with Haddad (one of the world’s best copywriters who’s made millions selling sex advice online), he’s a little… extravagant. 

His audacious handlebar mustache, leather newsboy cap, spiked jewelry, and perpetually open shirt give off vibes somewhere between “kinda pervy” and “armed drug lord” depending on your level of social sophistication.

Also, readers of this series will recall that I drive a 2001 Ford Crown Victoria, affectionately known as “The Blake.”

Blake can be temperamental, randomly deciding that he only wants the A/C to work on one fan speed, or that certain windows need to stay in the up or down position. 

Blakes current joke is that all windows work just fine – except the driver’s. It’s been stuck closed for months now. Which is amusing, until you need to speak to someone outside of the car. 

So, with Haddad riding shotgun and already busting my nuts about the two wrong turns I made getting us out of the sprawling hotel complex (I am ALWAYS lost in Orlando!)… 

I pull up to the security gate of a posh residential community where somewhere inside, industry “royalty” is gathering, and the “officer” in the booth, (my guess, a retired NYC cop) is not taking his job lightly.

So, amidst the Benzes and Land Rovers in line for the entrance gate to McMansionland, rolls up myself and Haddad in a throwback police cruiser, looking like B-story characters from The Wire. 

With the window stuck shut, I’m forced to open the door all the way open to have a chat with “Officer Tony.”

“How’s it going?” I say, trying to sound casual. “We’re part of the Copy Legends event.”

Tony stares blankly. 

“Uh… Todd Brown’s thing. It’s in here somewhere.”

“What’s the address?” asks Tony deadpan.

I can’t remember the address, so I say a combination of numbers and a street name that sounds vaguely like what I remember typing into Google Maps 15 minutes earlier…

“1…5…8 Morningside.. Lane?” I mutter, my voice trailing off in confusion like a Jeopardy contestant desperate to beat the buzzer.

“There is no Morningside Lane here,” says Tony bluntly. 

Haddad is doing his best to stay chill and suggests I can get the address from, “ya know, the fucking MAP” on my phone that’s been talking me through the directions up to this point.

I realize NOW how practical that would have been, but with Tony breathing down my neck and a growing line of super-annoyed investment bankers and their fashion catalog families piling up behind me, I panic and start scrolling through my email to find the message Todd’s team had sent me with the address.

Chris is almost as annoyed with me as Tony, but he’s too busy savoring the awkward irony of two members of “royalty” facing denial of entrance for appearing anything but. 

I finally find the right address and repeat it to Tony, whose silent reply indicates that while there IS such an address beyond this gate, he still doesn’t trust that I belong inside.

“Can I see your ID, sir,” Tony says flatly in the way cops do when exerting their power over you. A tone that says, “we both know this isn’t necessary, but refusing will only make things worse for you.”

“Are you fucking serious?” I shoot back without really meaning to. Situations where I’m faced with an authority overreach trigger my worst possible reactions. (Must be a product of my royal upbringing.)

Luckily Officer Tony has heard it all before in his previous gig as an actual cop, and with more privileged vacationers lining up behind me, he doesn’t have time for the “step out of the vehicle” escalation, as much as I can tell he would enjoy that.

He runs my ID into the computer and gets some form of confirmation that I’m more idiot than criminal, and reluctantly waives me through. 

Haddad and I spent the rest of the drive riffing and roasting each other over who had Tony more suspicious and which one of us would survive longer in prison. 

Friggin hilarious!

Of course, the mastermind was incredible, and I have many takeaways to share from it… 

But, this story felt more appropriate for our Sunday chats because it reminded me that it’s usually not the “tips, tricks, and insights” you hear from successful people that lead to the biggest “A-ha!” moments…

Sometimes just trying to get through a security gate is the most revealing clue of all.