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Dear Boundless Families:

Everyone arrived safely to the tail-end of a downpour that doused the fire ban. Hallelujah. While its early in the game, I do have some observations about both groups. 

Let me start by introducing you to two of the more interesting trip leaders in our fleet. While you would be proud to have your daughters marry either of them, they are unusually unusual.

Tony Rupoli – English Course Director and Principal, who protested yesterday, “Just when I was out, they bring me back in “

A mixed Italian (his mama is Caucasian), Tony insists he is not white. He struggles with his genetic duplicity like a 21st century Spock. The white man inside likes shooting pesky groundhogs like Yosemiti Sam on steroids,  and he’s addicted to trash TV. Tony is first to laugh at his own boorish humour, and it leaves his companions rather befuddled at how he can pull off his uncanny charisma. But watch his Italian artistry at teaching teens, and the high standards of character Tony holds himself and his students to, and you will want him to live long and prosper.

I asked Tony to come clean on the big secret. “What book did you choose?”  

His imposing 6 foot 6 frame postured aggressively, ” You killed my father, prepare to die!” I knew right away his students are going to have quite the ride studying the Princess Bride. I am told they are a loud bunch. What is it with our english classes this year? Second one in a row where you need to stuff earwax. They are playing at what Tony refers to as “english icebreakers” this afternoon, with strange sounding exercises like “Shakespeare Hip Hop”. All 16 of our english students are in for quite a ride in Tony Town.

Tyler McCartney – Trip Leader Outdoor Program

If there was a Donald Trump of Boundless, it would be Ty.

Never one to shrivel from an attack, Tyler hits back hard. He’ll not hesitate to get into a parking lot screaming match with the Executive Director, protecting his turf with vehemence. He’ll soon need to do some Trumpish comb-over for his abundant testosterone is ravaging his scalp.

But that’s where the similarity to the Republican ends.

His sincerity endears kids to his cause, and he gives voice to the sentiments of the group with a deft understanding of what teens need. Tyler has a sense of humility that make students and his colleagues fall for him hard. He takes it on the chin for someone else’s benefit. And so Tyler is a combination of puppy dog and barracuda – hopefully just what the outdoor crew needs. They have started their river training by being baptized into 24 degree Madawaska river class 2 rapid madness. The bus ride up was quiet, and then half way started to pick up steam. Upon arrival, the kids started moving dining table seats so they could have conversations with one another. One teacher remarked, “how odd, that openness started so early”

Its been a good day 1 so far. if you don’t hear from us in the next 3-4 days, it means your child is rocking this place. Here’s to hoping your phones don’t ring!

I’ll update you guys again in a few days when I’ll have a lot more to gossip with you about.


Steven Gottlieb