Executives, celebrities sleeping on the street

Why would a millionaire or a celebrity choose to sleep on the streets of New York City?

Two words: Homeless youth.

Most of us can't fathom being homeless as adults — but what if you were a teenager?

Executives at the Sleep Out around 1:30am in the Covenant House parking lot.
Mary Stevens | CNBC
Executives at the Sleep Out around 1:30am in the Covenant House parking lot.

The shocking reality is that nearly one in 30 children in America experiences homelessness every year, according to a recent study by the National Center for Family Homelessness.

Covenant House, an organization that helps homeless youth, is holding its fourth annual Sleep Out Executive Edition in New York City, where they invite more than 200 executives to actually sleep on the street for a night to raise money — and awareness. The motto is "We sleep out so others don't have to."

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For the past three years I've written a check to show my support. This year, my friend Tod Monaghan, the VP of Development for Covenant House, convinced me to join them.

"Turney, are you going to man up or what?" he said over the phone before even saying hello.

I knew there was only one answer to that question: "Yes," I said.

This is no joke. We're sleeping on the street. Although it won't be the real thing, they make it as authentic as possible. I'll be given a standard sleeping bag, a cardboard box and a hat.

We each had to raise $5,000, which I just completed this morning. When I worked on Wall Street, I could have done that in about 15 minutes. But today, it seems like a big number. It took me a month.

I have, over the past 30 days, had some hesitation about sleeping on the street for a night. Is it even safe? Regardless if it is or not — I convinced my mother it was. Then I started thinking about the weather elements. But I quickly forgot about all of that after meeting a few of the teens at the crisis center this past Monday. I spent some time with Hanna, who was on the streets at 13. Both her parents were drug addicts and she had no other choice. "I'm three years sober and in college," she said. She had a genuine smile.

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I've had a few situations in my past that left me wondering where I was going to sleep some nights, but nothing like this. All of my past mistakes were self-inflicted, but I always felt like I had a safety net. I can't imagine a world that would be so cruel and leave me with nothing. I mean, these are kids we're talking about. They're just kids.

Beyond raising money and awareness, there are other ways these executives help the homeless youth they meet while doing the Sleep Out.

"Special things happen, particularly at the Executive Edition," Tod said. (Other groups have Sleep Out events, including the Broadway community and young professionals.) "There'll be numerous cases where some of the sleepers, some of the execs, will hire kids on the spot. They'll meet kids, they'll hear from them, and they'll give them an opportunity for employment."

Tonight, the street will be dotted with a lot of Wall Street executives, including a few millionaires and billionaires — and even a few celebrities. Tony winner Audra McDonald and Yankees General Manager Brian Cashman will both be there.

Here is my live blog of the Sleep Out:

Oct. 26 (HIGH: 63 degrees LOW: 53 degrees). I agree to do the Sleep Out. I feel good about following through on my promise. Secretly I want it to snow. I think I have an advantage over the other Wall Streeters and execs – I grew up in Maine, where swimming in a 55 degree ocean and trick-or-treating in two feet of snow is normal. I've got this.

Nov. 6, two weeks before Sleep Out (HIGH: 57 LOW: 48). What have I gotten myself into? Who likes to be cold? Who wants to sleep on the pavement? Fund-raising is tough …

Nov. 10, 10 days to go (HIGH: 61 LOW: 44). Time to get some advice from my friend Dan, a Wall Street executive, who has done the Sleep Out the past two years.

"Did you sleep?" I ask taking a sip of warm coffee.

"Not much my first year," Dan says. "But the second year I slept okay, I have to work the next day so I have to sleep."

"How cold is it?"

"Cold," he says with a giggle. That wasn't the answer I was hoping for.

"Well, are there any tricks I need to know?"

"When we get to orientation, we'll want to sit in the back of the room. So that way when they release us for the night we can get prime real estate near the brick wall," he says. "It blocks some of the wind."

"Got it," I make a mental note to stick by Dan during orientation up until our cardboard boxes and sleeping bags are set up.

"What else do I need to do?"

"Wear lots of layers," he says. "And maybe some ear plugs. It gets loud."

It's going to be a long night, but I'm confident it will be rewarding.

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Nov. 17, three days to go (HIGH: 52 LOW: 40). I drive over to Covenant House to meet with Tod and check out the facility. I meet a few of the teens who are survivors of homelessness, child abuse and parental abandonment. As we toured the crisis center, Tod explained to me that these kids are susceptible to numerous epidemics including human trafficking. It reaffirms my decision to do this. And it reminds me that it's only one night — no matter how cold it gets.

Nov. 18, two days to go (HIGH: 45 LOW: 24). IT'S FREEZING!!! The wind sliced through me on the short walk from my car to the apartment. I have no idea how I'm going to do this. The bright side is, I'm up to 81 percent of my donation goal.

Nov. 20, 10:08am – SLEEP OUT DAY! (39 degrees). I just hit my goal of $5,000, which I'm very happy about. I'm not worried about tonight — it's one night. I heard that I can expect a low of 28 degrees. The only time I think about it is when I get an email or a text wishing me good luck tonight. It seems my friends and family are more concerned than I am. Should I be?

Nov. 20, 8pm (37 degrees). Vigil in Times Square.

Vigil in Times Square before the Covenant House's Sleep Out to benefit homeless youth in November 2014.
Mary Stevens | CNBC
Vigil in Times Square before the Covenant House's Sleep Out to benefit homeless youth in November 2014.
Breakout session. Each group heard from a couple residents and everyone discussed how they felt about the Sleep Out and the cause.
Mary Stevens | CNBC
Breakout session. Each group heard from a couple residents and everyone discussed how they felt about the Sleep Out and the cause.

Nov. 20, 11pm (32 degrees). Just located prime real estate near a brick wall.

Turney's camp site for the night.
Turney Duff | CNBC
Turney's camp site for the night.

Nov. 21, 12:05am (30 degrees). Time to test out my sleeping quarters for the night ...

Testing out the sleeping quarters ...
Turney Duff | CNBC
Testing out the sleeping quarters ...

Nov. 21, 12:45am (30 degrees). It's gotten a little quieter. People are attempting to sleep. It's hard to feel my fingers.

Nov. 21, 12:55am (30 degrees). I'm trying to go to sleep now. Seems like it will be tough. Wide awake. Cold. Cars driving by.

Nov. 21, 1:30am (29 degrees). Fully submerged in my sleeping bag and it sounds like dump trucks are in surround sound on a high-end stereo system it's so loud.

Turney on the left, with two other former Wall Street friends.
Mary Stevens | CNBC
Turney on the left, with two other former Wall Street friends.

Nov. 21, 2:26am (29 degrees). I'm shivering and a bird just sh-- on me. Things are looking up.

Nov. 21, 5:10am (27 degrees). I woke up to a cold snap across my face. My back hurts and I have to decide between peeing my sleeping bag or getting up and facing this cold.

Just before sunrise ...
Turney Duff | CNBC
Just before sunrise ...

Nov. 21, 5:15am (27 degrees). It's a hard to focus my eyes and walk straight.

Nov. 21, 5:30am (27 degrees). I'm up. A cup of coffee is helping. Getting ready for final reflections.

It's been a remarkable experience. Just thinking about others having to deal with homelessness has been very eye-opening and makes me want to sleep out again next year.

This has been a cold dose of reality.

Nov. 21, 6:30am (27 degrees). In the car heading home. Madonna "Into the Groove" blaring.

Reflections from my apartment

Nov. 21, 8am (74 degrees in my apartment). Back home now. My fingers are just thawing out. It was really hard typing last night. So, here are a few final thoughts from the warmth of my apartment.

The first hour was filled with energy and excitement. It wasn't until we were an hour or two into the night and we were left with our own thoughts — that's when things got interesting. It was a time to reflect about our own lives and how lucky we truly are.

As the cold set in, I tried with very little success to type with my gloves on — that didn't work. And I was shocked at how fast my fingers started shaking when I took off my gloves. I couldn't feel my fingers and toes even when I was in my sleeping bag.

I'm not really sure how long I slept. My guess is 45 minutes but it's hard to tell. I was so cold at one point that I felt like someone who was drowning — that moment where you're in and out of consciousness and stuck in lala land. It could have been an hour or 15 minutes — I really don't know.

This morning was a beautiful thing. It was all smiles — no one was complaining. The room was filled with gratitude. People shared their experiences with each other as we sipped out hot coffee. It was a wonderful experience coming together with so many others. The night was a huge success for the Covenant House and everyone who participated left with a gift of gratitude.

250 people signed up for this Sleep Out and raised over $1.6 million. By my estimation, it felt like all 250 showed up — walking from one end of the parking lot to the other was almost impossible without stepping on someones head or feet.

Commentary by Turney Duff, a former trader at the hedge fund Galleon Group. Duff chronicled the spectacular rise and fall of his career on Wall Street in the book, "The Buy Side," and is currently working on his second book, a Wall Street novel. He is also featured on the CNBC show, "The Filthy Rich Guide." Follow him on Twitter @turneyduff.

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