(Forewarning- this is very long. Sorry)
Over the past couple of years a lot has changed for me.
“If you’re not growing, you’re dying,” goes the phrase.
My buddy Chris Nikic says we should all strive to be just 1% better than we were yesterday.
Ryan Holiday says, “The Stoics believed it was the little things that added up to wisdom and to virtue. What you read. Who you study under. What you prioritize. How you treated someone. What your routine was like. The training you underwent. What rules you follow. What habits you cultivated. Day to day, practiced over a lifetime, this is what created greatness. This is what led to a good life. All you need are a few small wins a day.”
In one of his most famous letters to Lucilius, Seneca gives a pretty simple prescription for the good life. “Each day,” he wrote, “acquire something that will fortify you against poverty, against death, indeed against other misfortunes, as well and after you have run over many thoughts, select one to be thoroughly digested that day.”
(Sorry, I’ve also been a big stoicism kick the past few years)
George Washington’s favorite saying was “many mickles make a muckle.” It was an old Scottish proverb that illustrates a truth we all know: things add up. Even little ones. Even at the pace of one per day.
The point is, it's in our best interest, as human beings to want to become better today than we were yesterday. And better tomorrow than we are today.
It gives us purpose.
Like most people, (I think), I'd been seeking purpose for a long time in my life. Easily visibly without it, but longingly seeking it.
As well as looking for validation.
For some people, they are able to accomplish that via their profession. Turned out that was not the case with me.
I’ve had a million jobs and enjoyed them all, and still do love what I do, but at the end of the day, I can’t say any one of them “fulfills” me.
Growing up, we didn’t have much but we always had enough. My mother, a woman with a true heart of gold, made it a point to instill in my sisters and I a sense of always remembering to give back. We didn’t have a lot of money, but we could donate our time. Which she showed us by example week after week at our school, at the Church, as a volunteer at bingo night, as head fundraiser for our various sports leagues, and on and on and on it went.
Back then, I never understood her frenetic drive to stay so busy and spend what little free time she had away from working at her nursing job, or driving her three kids from practice to practice, on complete strangers.
But that’s all changed because now I get it.
I can’t say when, or how exactly, it hit me, but I think it was when I was at my lowest point. Around the year 2013.
I was depressed. Sleeping until noon. Not wanting to get out of bed at all. Forcing myself to finally at 2 in the afternoon, abusing alcohol every night. It was bad. And I felt hopeless because it was an endless cycle.
I had suffered a bad breakup, watched my closest friends move away from Chicago, start families, and there I was still living like a jerkoff 20-year-old.
During high school, things weren’t so great around my household so I went out of my way to spend as little time as possible there.
Luckily for me, I met some guys at St. John’s who welcomed me into their families, and who remain some of my best friends to this day.
The Barlow family, Tierney family, and Spadea family all basically christened me their 2nd and 3rd son, and allowed me to spend multiple nights at a time every week over their houses.
Aside from all the incredible family vacations they took me on, and opportunities to visit places I never could have imagined, staying at their houses, I developed actual study habits and discipline to do homework, and I enjoyed actual family meals on a nightly basis. Most importantly, though, I was subconsciously observing how a healthy family dynamic worked, and how important a strong male presence was in the household.
My mom was a Saint. But there was only so much she could do.
Mr. Barlow taught me how to shoot trap. Mr. Tierney taught me how to fix a flat tire. Mr. Spadea taught me how to be an entrepreneur. And endless other things. But not one single lesson or skill they taught me was more important than the importance of believing in myself.
I had gone to a school where I felt everybody was richer, smarter, stronger, faster, tougher, and better than me. I was a minnow in a shark tank.
Without these men instilling confidence in me, through believing in me, I never could have myself.
I took a hard look in the mirror at what I was doing, where I was headed, and thought about what a letdown I was to these people who had shown so much confidence in me, and myself.
I decided I needed to shape up because nobody was coming to save me. I wasn’t a victim. I was one of the luckiest guys around in fact. And I needed to wake the fuck up.
I joined a gym, began attending mass again, finally became open to the idea of seeing a therapist (and did), and looked for ways to become fulfilled.
I’d had a friend Thatcher who volunteered as a mentor through his Church and seemed like he really got a lot from it. I thought to myself, “what better way to help, then to do for a young kid what was done for me?” So I researched and found Big Brothers Big Sisters.
Now I know most people know the name, and the general premise of what they do, I thought I did too.
Thanks to movies like “Role Models” (one of my favorite comedies and films I think are severely underrated), and the TV commercials growing up I figured they’d pair me up with some hilarious kid, we’d hit it off and have all the same interests, and I’d be a great role model to him.
After all, I wasn’t a square. I was a hip DJ, pretty in tune with pop culture, current trends, and definitely current music, and I know where all the best restaurants are.
Boy, was I wrong.
To begin the process you attend an orientation. I visited the Chicago headquarters at 560 W. Lake St and was surprised how packed the room was. Men and women, all ages and colors were there. The young woman who presented to us all gave a general overlay of what Big Brothers Big Sisters’ mission statement is, what their requirements and expectations are, and what makes a good “Big”.
It wasn’t a “come one, come all” thing whatsoever.
Their screening process was very thorough, (for obvious reasons), and they required you to attend several meetings and do your homework.
Throughout the entire process. Not just the beginning. They made this clear numerous times.
They were trying to weed out people who weren’t serious, couldn’t fully commit, or might flake over time.
(I later realized why this is so crucial in the process. Because most of these kids in the program have been abandoned and let down so many times that the last thing Big Brothers Big Sisters wants to do is set a child up with a mentor who is going to do the same.)
After sticking to the syllabus, attending the meetings, and passing my background check, I was ready to be paired up with a “Little”.
Our match support specialist at the time had been in on interviews with me several times and had a general idea of the type of kid I was growing up. I had trouble focusing in school, was a constant disruption and distraction, and was always trying to get a laugh out of my classmates. (Often at the expense of the teacher or other students. I was a pretty awful kid.)
So she suggested pairing me up with somebody whom she described as the same type of “character”.
His name was Tremontae, he went by Tre, and he was “the class clown.”
He was being raised with his little brother by their single mom Valerie way down on the south-south side.
His grades weren’t great, and he wasn’t interested in many things other than getting in trouble in school or being glued to watching videos on his phone.
I instantly began regretting my decision.
I was expecting Ronnie the funny kid or McLovin the LARPer from Role Models.
When we met for our introduction at Tremontae’s grandmother’s house, I was shocked to find out he was my size. I’m 6’2” and he could look me in the eye. And he was so big he could probably kick my ass pretty easily if he wanted to.
He was shy and standoffish at first. My match support specialist and lead-up meetings told me this was likely to happen so I didn’t get worried.
We discussed what he liked- video games, sports video games, Steph Curry, and other kinds of video games.
I asked if he watched or played real basketball or football and he quickly said “no”.
So I thought to myself- “ok, let’s hit an arcade for our first outing”.
We went to the one by the movie theatre in Streeterville and had a blast. He kicked my ass in Timecop, and I kicked his in air hockey.
He was competitive, which was great, and it turned out he really wasn’t that shy.
This was going to be a breeze I thought to myself.
Again, boy, was I wrong.
During the next couple of outings we had I think Tremontae said 10 words total to me.
All one word.
He was constantly buried in his phone. When I could get his attention, he’d look up with a face of pure misery, give me a “yah”, or “nah”, and go back to watching some video on Youtube.
I tried restaurants, bowling, a movie. Nothing could get him off his phone.
He whipped my ass in bowling, and at the arcade he was really good at the pop-a-shot. Which naturally led me to asking him why he didn’t want to play sports for his school or for fun?
He “just didn’t”. So I left the subject be.
I even took him to what ended up being the last Bulls game before the pandemic shut the world down in March 2020.
He was actually really into that.
It turned out he had a zillion takes he couldn’t wait to drop on me, mostly about how trash the Celtics were (his words), and how the best Warriors team from a few years ago could beat the 96 Bulls.
I explained what a spread and the over/under were, and my buddy who works for the team got us out on the court for a picture.
It was a great time.
Then Covid shut the world down and we were only able to communicate via text and facetime for a while.
Like all of our relationships, it became tough to find things to talk about with not being able to live life and all. No sports. No dining, or entertainment. It sucked.
What sucked, even more, was the fact that Tre was forced to take all his classes online.
He went months without seeing his teachers or classmates in person.
He did all his learning through the same iPhone screen he was always glued to anyway.
I was worried his grades would slip but a miraculous thing happened- they actually improved.
It turned out that not being live in person, in front of his classmates, Tre wasn’t able to entertain or distract them. And was thus able to focus better himself.
He began getting all A’s and B’s and his mother was elated. As was I.
She sent me his report cards to prove it.
As soon as MLB lifted their ban on fans in the parks, and allowed minimum capacity I snatched us up a couple of Cubs tickets and took Tre to Wrigley to celebrate his scholastic success.
We even got him a shout out on the video board (thanks Cubs Productions)
And after that, we went to Au Cheval for what I told him was named not just the best burger in Chicago, but the best in the country. (He said it was an 8 out of 10)
Things were back on track and Tre began to come out of his shell.
Instead of just talking about sports, he began actively participating in them. Unbeknownst to me.
He went and tried out for his school’s basketball and football teams. As well as a city team.
I was so happy, and felt a sense of relief, that he’d done this because I know how vital the concept of team sports play in a young person’s life, and all the invaluable things you learn through them.
Unsurprisingly, he was a standout on the football field.
His coach had him playing center and nose guard and surprisingly to me, he loved both.
The only issue he told me was that some games he didn’t get to get on the field because he had to share a helmet with a teammate who was the only person close to his size head.
I quizzed him on this when he told me because I at first didn’t understand.
Turns out, like textbooks, and computers, the schools in Chicago’s poorest neighborhoods also get shafted on sports equipment.
His team barely had enough to go around for a team of kids who mostly all played both ways. Kids had to switch off sharing helmets. A perfect microcosm of Chicago in general.
After searching literally for 2 days all over the internet, and calling sporting goods stores all over the country looking for a youth size XL, or men’s small football helmet, I resorted to social media.
Nobody, and I mean nobody had any inventory at this time, or any clue of when they’d be getting any in. (Thanks Covid)
Luckily for me, an Angel by the name of Jenny, who I’d known since my “Outfit Events” days responded almost immediately. She told me where to meet her and when, and that she’d get Tre situated no questions asked.
We drove outside the city to a storage facility where she was waiting. She not only found and gave Tre a helmet that fit him perfectly, she also made him take pants, and shoulder pads.
(Sidebar - he's going to be pissed I'm telling the world this, but after I posted these tweets Large texted me and asked me what size shoe Tre was and what his address was. The guy when online and bought him the nicest pair of Nike football cleats he could find, and a pair of "house shoes" and shipped them to his house. You want to talk about a sweetheart of a gu? I love that man.)
I was beginning to see Tre not only start to mature, but also build confidence in himself.
And it was a really beautiful thing.
He began to also ask me questions. Lots of them. And often.
In the middle of the day I would get texts from Tre asking if I could teach him about zone defenses (I couldn’t), how to drive a car (I will when he’s 15), and how to invest (I told him he doesn’t want my advice).
On one of our outings, I took him to my friends' restaurant Elleven/Elleven in the West Loop.
He was surprised to see two successful young black men owned it. They gave him a grand tour and Ahmed (far left) drilled Tre with a million questions. Tre handled them all cool as a cucumber. I was amazed. And it turned out Ahmed actually grew up in the same exact housing complex that Tre lives in now. We had an amazing meal and afterward Chef Lamar (middle) (from Food Network fame) gave Tre some tutorials in the kitchen. It was an awesome experience. And an eye-opening one for Tre.
In a somewhat sad/funny way Tre thinks I am “rich rich” and began to ask me every time we hung out if he could come work for me. I told him he was too young. So he said it could be under the table. (Hilarious). And that he really wanted to learn from me.
I've told him my story from when I was his age, and how through hard work, and the help from some really great people, I was able to make a really awesome life for myself. One I never could have imagined back when I was younger. But it took me being determined to outwork others, prove naysayers wrong, and never giving up.
I could tell this one particular conversation we had hit different, and that he was really thinking about what I said to him as I dropped him off at home.
The next day Tre texted me out of nowhere-
“can you help me get into Mount Carmel?”
I was equally shocked and excited.
“Yes of course” I replied. Quickly followed up by, “but why?”
He told me he “wanted a future” and I was immediately sold.
I was getting this kid into Mount Carmel.
(sidebar - one of the reasons I was so happy he had chosen Mount Carmel of all schools is because a while back I was having a discussion with Carl about all the area high schools and the differences between them. Not growing up here, I had no clue what separated a Brother Rice from a Rita from a Loyola from a Mount Carmel. I knew what the difference was between a Holy Name vs. a St. Peter Marian vs. a St. John's vs. a Xaverian. Carl told me that "Mount Carmel is where you send a boy to become a man." And that stuck with me.)
I texted Jenny, again, and asked for her help on what I needed to do to make this happen.
Once again she went out of her way and helped me and Tre’s mom get him scheduled for a makeup entrance exam. I was more nervous than Tre was pre and post-exam.
When I asked him how he thought he did he told me that he didn’t get to all the questions, because he took his time making sure he got the ones he could focus on right.
I told him how proud I was of him regardless of if he passed or not (knowing deep down that even if he didn’t, there was no way I was taking no for an answer)
His score came back and he passed. He was officially accepted to Mount Carmel!
His mom called me in shock, in tears, thanking me.
I told her that it was all Tre’s determination and hard work. And that now we had to get to work on getting him financial aid and looking into some scholarships.
I texted Tre to tell him how proud I was of him and he sent me the most meaningful thing anybody’s ever said to me before.
“Thank you for believing in me.”
So simple. Yet so important.
The power of knowing, truly knowing, that somebody bigger, or older, or you look up really believes in you.
At this stage in life we might laugh it off. Having forgotten just how terrifying and unsure it is navigating the world as a youngster. (And that was 20+ years ago. I can’t even imagine today). But it’s like rocket fuel. Everybody, especially insecure teenagers, need a confidence boost and to know that as weird, or different, or inferior they might feel, we’ve been in their shoes. We made it through and came out the otherside. And we believe in them.
Over the past few months, the CEO of Big Brothers Big Sisters Chicago, Jeremy Foster, has reached out to me after hearing about Tre’s story asking if I’d be willing to use my platform to continue sharing and spreading the word about mentorship.
Of course I will.
Finally in my life I can truly say that I have found something that makes me feel fulfilled and given me a sense of purpose. And that is helping others.
That’s not some bullshit, brochure flap quotable either. I wouldn’t have spent 2,500 words writing this blog if I didn’t truly feel it.
When I began this process a few years ago I thought that it would be a one way street where I would help a young kid who needed it.
Never in my wildest dreams did I imagine that in turn, I’d feel like I’ve finally done something significant in the world.
One of my favorite quotes of all time (I am a big quotes guy) is etched on Jackie Robinson’s tombstone. It reads:
"A life is not important except in the impact it has on other lives"
As I grow older that becomes more and more evident to me as we watch the world get crazier and crazier.
(Now for the sell)
If this story touched you in any way, inspired you to give some of your time and attention to a kid who drastically needs it, or just got you off the fence to volunteer in some way, shape, or form- amazing!
Mentoring isn’t for everybody.
But if you feel like you could help change the life of a young boy or girl, through just a couple hours a day, a couple times a month, than I’m begging you to reach out to the program in your area (LINKS) and find a way to get involved.
Big Brothers Big Sisters offers a mentoring program called site-based mentoring where other Big/Little matches attend if you are not comfortable with the traditional community-based program. You are still matched one-to-one with a Little but in a group setting where you go on group outings and do everything from show up and throw the football around with a group of other “Littles” and “Bigs” to helping out with some homework in an after-school center.
Jeremy told me one time when we met the number of children in the pipeline, waiting for volunteers to step up and mentor them, and it was heartbreaking. These are kids, from families, who want guidance, and positive role models in their life because they know the value of it.
I promise you it will be one of the best decisions you’ve ever made in your life.
I wrote a letter about Tre to the admissions counselor, the head of financial aid, (and the football coach).
For blog purposes, I’ll include it below.
Good afternoon gentlemen-
I am writing this in regards to a young man who applied to Mount Carmel, and was accepted, by the name of Tremontae ——.
I am writing on his behalf because he is determined to become “a Mount Carmel man”, and I am determined to see that he does just that.
Let me tell you a little bit about why you should feel so honored by Tremontae wanting to attend Mount Carmel.
Tremontae came into my life via the Chicago Big Brothers Big Sisters program.
You see, I am his “big brother”, and he is my “little”.
Except that he’s far from little.
I stand 6’2” and 180 lbs and he’s already bigger than I am.
At first, when we were getting to know each other I didn’t know if I’d ever get him to open up to me, or come out of his shell.
For the first time in my life, I found myself feeling “old” and “out of the loop”.
Even though I consider myself pretty dialed in to pop culture and current events through my jobs in the hospitality industry, with Barstool Sports, and with the Chicago Cubs.
Boy was I wrong.
Since meeting Tremontae I’ve managed to learn, through him, all about the metaverse, online gaming, tik tok, and what kids are listening to these days.
And we finally managed to find something we can both relate to and are passionate about. Playing sports.
Last year was really tough for kids everywhere. Trying to juggle learning remotely, maintaining friendships remotely, and still just “being a kid” were all extremely hard.
But I watched Tremontae handle it with zero complaints.
That’s one of the many things I truly admire about him.
For a kid who has a million things he could complain to me about, he never has.
He’s one of the most upbeat, positive, and “glass-half-full” people I have ever met.
He’s taken everything in stride and somehow managed to improve his grades and actually excel in his studies during these trying times.
He’s also become motivated to not only try out for his school and a local traveling basketball team, but also an area football team. (Something I never thought he would do a few years ago.)
Every time we spend time together he finds a new way to impress me. Be it by his genuine kindness, a curiosity of the world he’s unfamiliar with, or his hilarious sense of humor.
From what I’ve seen he’s very good at making his friends laugh and encouraging them to be their best selves, (Something I think we should all strive to do on a daily basis), as well as pushing himself to become better every day.
That’s part of the reason I was so moved, and proud, and humbled when he came to me and asked me if I could help him find a way to get into Mount Carmel.
Initially, I was taken aback by the request. I asked him why he wanted to go there and he said because he knew that it would open doors to him that he’d only find at Mount Carmel. (Again, this is a 14-year-old kid).
Throughout our talks over the years, I told him about how attending a Jesuit High School back in Massachusetts before coming to Chicago to attend Loyola completely changed my life. And I owed everything I have accomplished in my life to the doors that education opened for me and opportunities it afforded me.
Now here he was reciting his desire to do the same back to me.
Through the help of a longtime friend Jenny Czerwonka, I was able to line up an entry exam make-up date for him, get him and his mother the necessary financial aid documents, and get him to the exam.
He has never once felt or shown a sense of inferiority, or self-doubt. Being a teenager from a single-parent home myself, and being crippled with those feelings at his age, this is also something I truly admire about Tremontae.
He’s also a very hard worker for his age.
He had asked me repeatedly to hire him at one of my restaurants because he wants to work, learn the business, and make some money for himself. (I plan to give him a job when it’s legal).
In case you haven’t got the sense already through this letter, Tremontae is a really special person. And a genuinely good one.
His friendship has been eye-opening and has enriched my life. And it is a top priority to do the same for him.
This is why I’m requesting that you grant Tremontae an in-person interview so you can see for yourselves just how special a person he is, and catch a glimpse at his potential.
A potential that I know can and will be realized through a Mount Carmel education.
His mother's financial aid package was only $3000, resulting in a balance of $10,000 due in order for him to attend. That's totally out of the question for her considering she lives in public housing, and raises Tremontae and his little brother on her own salary as a city crossing guard.
I agreed to pay his registration fees and to buy his books for him, and I will obviously chip in what I can in order to make this happen.
But I am asking that you consider reviewing his application and possibly reconsider his award amount.
I promise you you will not regret helping Tremontae become a Mount Carmel man.
And I will contribute in any and every way I possibly can be it through helping to fundraise, or simply help give back.
If there is anything I can do or any questions I can answer, please don’t hesitate to contact me.
I thank you for your time and consideration.
For anybody who has ANY questions whatsoever about the program, feel free to reach out to me on social media or at email@example.com
For those in Chicago, Big Brothers Big Sisters is actually hosting their annual "Big Bash" on May 7th. It's an awesome event. You can get tickets or donate here -