Ryan Cristelli says he has only one skill. The 43-year-old Seattle native and Ada High alumnus has a talent for storytelling. 

As a seasoned creative director, he has developed content for NASA, The Chickasaw Nation and Under Armour, to name a few — all designed to engage the hearts and minds of humanity. This skill allowed Cristelli to build a nice, comfortable life for himself and his family. In many ways, he was living a dream.

A few years ago, however, a news article would wake him from his earned contentment — leading to sleepless nights and a renewed sense of what it truly meant to love thy neighbor. Becoming increasingly aware that each night becomes a gamble for those who don’t have a roof over their head or a bed to call their own during the unforgiving winter months, Cristelli took a deep dive into the plight of the unhoused community in Oklahoma City.

He found that he couldn’t turn away.

“When you become involved with folks who are experiencing homelessness,” Cristelli says, “you don’t ever view the winter and summer the same way again. You don’t go past an alleyway without looking down a fence line. You look for a gathering of crumpled fabric and ask if that is trash or a human being.”  

More than six years ago, Cristelli created Project Winter Watch — dedicated to outfitting the homeless with the necessary gear to stay alive during Oklahoma’s often brutal winter months. In that time, Cristelli estimates it has helped thousands of women, men and children who live on the streets in Oklahoma City. Those who have no shelter from the ice, snow, wind and rain, or temperatures near or below freezing.   

“What Project Winter Watch can’t do is solve the problem,” Cristelli says. “That’s going to be something bigger. But what Project Winter Watch does is it provides the right gear that meets the cold when it has to. It has to be a zero-rated, compacted, weatherproof sleeping bag that you can boogie out when it’s time to go. Insulated gloves, insulated socks, hand warmers and tarps. It’s triage for maybe another day, a week, another month, another season, until maybe they meet up with that resource that’s going to be that move to permanent housing. Maybe it’s that treatment they need or reuniting with a family member. The cold doesn’t care how they got out there. It takes all the same.”  

A Different Direction

This is not where Cristelli saw his life heading some seven years ago. He had just married his wife, Aley, and he was working for a local creative agency.

But when he started helping out his wife, who started the Pine Pantry, Cristelli started to see a different side of life he had never been privy to or thought much about before. The Pine Pantry is a small pine closet that sits outside local businesses, at which people can drop off food, socks and other items for those in need, who can then come by and pick up what they need. Since Cristelli was often the one who would set up or fix the pantries, it allowed him to connect with those whom they set out to serve.  

“When I would go stain the thing or have to hammer back down a shelf, I would talk to folks,” Cristelli says. “In the course of talking to the folks that are hungry or maybe dealing with any number of issues, I learned that my notions — of what those things are and why those things are — were completely wrong and maybe a bit naïve. I wanted to think that everybody had a place to go. And there was always going to be a roof one way or another. But that wasn’t the truth.”  

Cristelli also found many preconceived stereotypes and beliefs he had formed about people who were homeless disproved.   

“People were battling things I didn’t know they were battling,” he says. “The idea of what mental health starts to look like. What addiction looks like. There is not a one-solution thing. Then I felt very small; I wasn’t up to any of this. I felt very insignificant.”  

Cristelli didn’t know what to do about it, and just kept on living his life as he had always done. But in 2016, he was hit hard with the reality of the dangers of living on the streets. While still helping his wife at the pantry, he read in a news article she sent him that four people in Oklahoma City had died during a February cold stretch.   

“I couldn’t believe that people died because the cold took them from us,” he says. “All that [feeling] of insignificance rushed back.”  

This time Cristelli decided to do something. He interrupted a text thread with his friends. The complaining about college football and lawns was replaced with Cristelli asking if they wanted to donate some money to an idea without a plan.  

“I don’t know what I’m doing. But I have a full tank of gas and $58 in my wallet,” Cristelli remembers texting. “I’m going to run to Academy (Sports). If you guys want to pitch in a few bucks, I’m just going to buy some sleeping bags and figure something out.”  

Cristelli ended up with around $350 from his friends and was able to fill up a shopping cart full of gear. But once he got outside to his car, the realization hit. He had no idea what he was doing or where to even begin.

“I didn’t have any of this knowledge that takes years to acquire about where our unhoused neighbors are. I didn’t know what I was going to do,” Cristelli says. “All of a sudden, I just turned into a pool of emotion and I just headed south. I saw people that I had assumed were in crises or whatever and I handed out those bags. I felt accomplished.”  

However, his accomplishment was doused pretty quickly. He found that he had made the same mistakes many people across the country make when trying to do something good for those they see struggling on the streets.   

“What I would come to find out from that first gift, through six years and handing out thousands and thousands of bags, gloves and socks being given out, is that science has to work behind it,”

Cristelli says. “I was buying these bags ready for -30. But they weren’t water resistant; they’d turn into a bag of concrete when they got wet. A lot of folks have to move rapidly, and a bag that is as round

as a basketball hoop and three or four feet tall — you can’t move with those things. Those touch-points don’t work. It was a hindrance to them. Decent gloves and socks weren’t going to work either.”  

Making It Happen

Instead of letting the wayward attempts dissuade him from helping again, Cristelli wanted to learn more and find out how he could do better. His wife introduced him to outreach programs that had the knowledge and expertise he was seeking.  

“But then I had to get money,” Cristelli says. “I had worked in advertising going on 20 years and I knew there was a bit of science to activating folks. But I didn’t want to play on emotion; I wanted to just tell the truth.”  

So he took his iPhone and began documenting what he saw. After making sure the people were OK with being filmed or exposed, he started doing what he does best. Storytelling.   

“I take their words and turn them around and start making posts about these folks,” Cristelli says. “And it started to change a bit of the narrative around how I thought and talked about our unhoused neighbors. I had friends who were seeing these folks for the first time. They would tell me, ‘I didn’t know. How can I help?’ It just started to work.”  

The kits that Project Winter Watch puts together consist of a sleeping bag, gloves, socks, hand warmers and tarps. Each kit is valued at around $100.  

Cristelli said it’s impossible to tell how many kits are handed out each winter, but conservatively he puts it about several thousand. He estimates that Project Winter Watch has taken in somewhere around $400,000 in donations in the past six years.  

“When things are really cooking, I’m making weekly purchases over $8k, and that does not count the products purchased by our givers,” Cristelli says. “Project Winter Watch is nothing without our givers. I’ve said this many times, and it lives in my deepest fibers: I’m nothing more than caffeine and adjectives without every person that chose to make a gift and protect someone they’ll likely never meet. It’s everything.” 

Project Winter Watch has grown from a bunch of friends donating to a Venmo account (rynosu) to Cristelli becoming the go-to guy for outreach and resource centers, and local hospitals. They need his help. They include collaborations and relationships with Feed His Sheep, The Ice Angels, Sandwiches With Love, Second Chances Thrift Store, Norman Regional Hospital, The Homeless Alliance, VA’s outreach program and the Mental Health Association of Oklahoma. 

This past winter, when a two-week stretch saw temperatures fall to single digits and Oklahoma City had run out of shelter space, Project Winter Watch became a hub of local outreach.   

“It’s an all-points bulletin on social media,” Cristelli says. “You could see that cold snap coming and know it’s going to be the worst in forever. It’s going to do a lot of damage. So here is what we have to do. If you are a resource, an outreach program and going out, let me know. Let’s get you kitted. If you are somebody that is a provider for the project, now is the time. Of all the times, now is the time. Here is the Amazon Wish List and here is the Venmo and Cash App. Every day, three times a day, there would be a row of cars snaked to the front of the storage unit with people from the VA (Veterans Affairs), the mental health association and City Rescue. Cars would pull up, and we ask what they need and then get it to them. You keep that conveyor belt going, then fill up your own car, then go out.”  

According to Cristelli, during those two weeks, UPS and Amazon would have nothing but Project Winter Watch items to deliver. During those two weeks alone, the organization handed out 800 sleeping bags.   

“Part of me froze, broke off and died,” Cristelli says. “It’s just so hard and so scary. I had the luxury of having layers and a home. You go out and you see and you do it again. You don’t understand the fairness in the world. I can’t make a lot of sense of it. You see the fear and hope in the faces of all these amazing people with the outreach programs going hard, all the time.”  

The Work Continues

During the annual Point in Time Count, Oklahoma City registered 1,339 countable people who were experiencing homelessness in 2022. That was down from 1,573 in 2020. The

counters include anyone staying in overnight shelters or transitional housing and living on the streets. However, since the count took place in March instead of its normal time in January, officials at the Homeless Alliance said it does not necessarily mean homelessness is down.  

When Cristelli started, the feeling that was driving him was accomplishment. But after that winter, he said he is now driven by fear.   

“I’m terrified we’re going to lose somebody,” Cristelli says. “But that’s OK. It’s whatever gets you to do it. On a night when I can’t sleep, I will pack up 30 packs, and I go out and meet 30 people and provide all these things. It’s the 31st person I see on the way back that I think about because I don’t have anything. I will go to the storage unit, grab some packs and come back to that same spot and they are gone. That’s all I think about. But it’s the 31st person that gets me going the next day.”  

Cristelli had thoughts about expanding his operation into

the summer, when the dangers are different, but no less deadly as temperatures rise above 100. But the toll his work takes physically, mentally and emotionally during the winter forced him to really think about what he was getting himself into.   

When Aley asked him, “Are you going to be ready to meet the winter doing this?” he had to have an honest conversation.   

“I found out I don’t have it in me,” Cristelli says. “I had to be honest with myself. I just don’t have it in me. What I realized is I’m not built for this. I’m so in awe of the people who are. I will work my guts out in the winter. But I don’t know how to do both.”  

Cristelli is the first to admit that running Project Winter Watch is taxing, draining and stressful. As the winter months get closer each year, he knows that there will be people whom he won’t see because they didn’t make it through the past winter, which he dreads.   

But he also knows he can’t stop. When he talks about the people who have told him they would not be alive if not for the help Project Winter Watch provided, Cristelli gets emotional and tears well up in his eyes.   

“When people tell me those things, I feel grateful,” Cristelli says. “Then I feel activated to keep going and doing these things — because it matters.”  

He plans for the project to continue for as long as he can hold up, because he knows what the work means to those in need and those who choose to give.   

“It’s about shifting the way we see our neighbors. In our very best moments, it’s our selfless giving that is our best,” Cristelli says. “It gives people the opportunity to be who they hope they would be.”