It's been a wild ride ever since that 2013 World Series.
All I've ever wanted to do was this job. I started my own Red Sox blog when I was 16 years old on New Years Day, 2006. SoxSpace is what it was called. From that day forward, I stopped caring about school. I didn't need it. Not in my mind, at least. I knew what my calling was. After some health complications my junior and senior year, my GPA was unsalvageable, so I mailed it in for the rest of my high school tenure and was actually laughed at by guidance counselors when I told them that I wanted to go to a state school. I didn't actually want to go; it was more that I was being forced to get my degree by my parents. Nevertheless, I was told that it was community college or bust by my high school. For as much as that sucks to hear, they weren't wrong.
So, I went. Didn't give a fuck there, either. I was focused on getting better every single day at writing. I'd be at house parties with my laptop, banging out Red Sox blogs while a beer pong tourney was going on a foot away. I mean, I still had my fun, don't get me wrong. But I also knew the opportunity that I had in front of me. By my second full year of blogging, my site had built up a community that was north of 100,000 Red Sox fans. The theme here, as you'll notice, is that I've gotten lucky quite a bit throughout my journey, and I was very, very lucky that I started blogging right before the Red Sox won the 2007 World Series. That luck continued the following year when they made it to a seventh game of the ALCS.
Like I said, I was a shitty student. I'll own that. But despite my lack of efforts in the classroom, I still maintained good relationships with my teachers. When I was 18, I wrote my first book called One Fan's Story: If This Hat Could Talk, which was essentially the story of the Boston Red Sox through all of my firsthand experiences. I didn't really learn grammar or sentence structure until after I had written the book. My junior year English teacher at Saugus High, Jane Osgood, volunteered to edit the book for me.
When it was done, I sent her the file of the entire book, expecting her to edit it and send it back all corrected, and she was like, "Oh no. That's not how this is gonna go down." She printed off the entire 430-page manuscript and corrected it in red pen like it was a final paper, twenty pages at a time. Every Wednesday, I would go back to Saugus High and, during her free class, she would sit next to me and go over every single mistake that I made so that I learned what I did wrong and how to do it correctly moving forward. I don't think she understands that she basically taught me how to write throughout that entire experience and I'll forever be thankful for that.
I wrote for eight years without ever seeing a dime. I didn't care. I was doing what I loved. Writing was my passion and it gave me an avenue to connect with Red Sox fans all over the world. It was and continues to be such a rewarding experience. The first paid gig I ever had was for the 2012 season with the New England Baseball Journal. They adopted SoxSpace as their Red Sox blog and had me writing two columns a month in their magazine. I got paid $300 a week to blog full time in addition to the two columns. Early on, we didn't see eye to eye because I wanted to do my thing and my "thing" wasn't exactly what they had envisioned. It happens.
If you recall, that 2012 season was an absolute nightmare. The Red Sox were a disaster on and off the field. They finished in last place, and TMZ-like stories were all the rage that season. I hated it. I was like, if this is what it's gonna be like, then I'm not really sure this is what I want to do anymore. I want to talk about baseball, not John Lackey's divorce drama and Bobby Valentine being a dickhead. That, on top of the differences with my employer, made for a miserable first-year experience doing this for a job.
After the season, we mutually decided to go our separate ways. Being completely honest, that season and my experience professionally really damaged my passion for writing. I tried not to get too discouraged, though. A friend of mine by the name of Brett Rudy offered to help me out by putting together a list of just about every news outlet that covered the Red Sox. I'd say there were about 40-something outlets on the list. We put together customized PowerPoint resumes that were specifically tailored to each one of them, and we sent them out to every outlet to say this is who I am, this is what I've done, and this is what I can do for you.
I got two responses. One of them was a pass, and the other was a, "We'll let you know if anything opens up." Of course, I never heard back from the one "maybe" that I got, and all of that rejection became the biggest reason why I have such a big chip on my shoulder. It's also why I have such an undying loyalty to Dave Portnoy and Barstool Sports. Anybody could've had me, and he was the only one that took a chance on me. This had been my dream for so long, and that was me shooting my shot and air-balling it. I was embarrassed and depressed.
You also have to understand that, back then, openly being a fan of the team that you're covering wasn't really a career option at the time. Sure, Bill Simmons existed, but he was an outlier. Sure, Barstool existed and Dave was doing just fine, but the company that exists now is not even close to the company that existed back then. If I really wanted to "make it", I knew that in all likelihood, I would have to get a job somewhere that would make me tuck my fandom away for the sake of the position, and that was never something that I was willing to do, either. I was never willing to sacrifice who I was for a paycheck, and I never understood why being a fan of the team was perceived as a bad thing in this industry. I would rather hear genuine thoughts from someone who actually cares than from someone who is paid to tell me about something that they don't actually care about.
After failing to get a job with the mass resume approach, I thought it was time to focus my energy elsewhere. One of my mentors at the time was a Marine, who now owns and operates Yawkey Way Report, a magazine sold outside of Fenway Park before each game. After feeling like I had failed at making my dream of covering the Red Sox come true, I had decided that I was going to join the Marines. It's a funny story now that I've shared on Barstool Radio a couple of times, that the Red Sox were so bad that I'd rather be in the line of fire than in Boston watching that team. But that was a really dark time for me.
Behind my parents' backs, I took the written test and met with Marine recruiters to explore all of my options. If I couldn't be a Red Sox writer, then I, at least, wanted to do something that my parents could still say that they were proud of me for doing. The last thing I wanted to do was finish my degree and work a nine to five job that I hated. After my mother found out about what I had been up to, she wrote me a heartfelt, handwritten letter that begged me not to go. She encouraged me not to give up my dream of writing and that it was going to happen for me some day.
That's when Jen Royle came along and said that she was starting up a Boston sports blog called SportsReel Boston, and was interested in having me join the writing team. It was unpaid, but I didn't care. She didn't have a quota for posts. She just wanted to give me a place to write, and I was free to write whatever I wanted, whenever I wanted. So, that's what I did. That 2013 season breathed new life into my passion and my career. During the 2013 World Series, I was getting TV opportunities every day with NECN. When the Red Sox finally won it all, I wrote the best blog that I've ever written in my life, detailing that entire 2013 season and what that team meant to the city of Boston. I post it every year on the anniversary. Because of everything that happened that year, I'll never be able to top that blog, and I am more than fine with that.
The following year is when I rebooted SoxSpace and brought on a team of writers for the first time. They ranged from actual writers to Red Sox fans that I had been following on Twitter, whose tweets I had enjoyed and thought they'd make a great transition to blogging. It worked. That year, I graduated from Endicott and was ready to make another run at doing this for a living. In May of that 2014 season, I was part of the pregame ceremony at Fenway Park for Red Sox Nation Day. My girlfriend at the time went down to field level to take pictures of me during the ceremony, and the NESN cameras captured video of her that they later showed during the game broadcast. Humble brag, but she's a dime, and the Barstool guys started getting tweets from Stoolies with screenshots of her face from the NESN broadcast, saying, "Send out the smoke patrol."
Feitelberg ended up blogging a picture of her, and then he got some tweets from people being like, "Yo, that's Carrabis' girlfriend." He ended up following me on Twitter, saw that I was a Red Sox blogger, and we started to talk Barstool. I've been a Stoolie since 2007. I started talking to Dave Portnoy around 2008. When I was running SoxSpace, I would hit him up for advice on how much to charge for banner ads based on the traffic that I was getting. I kept a relatively PG-13 blog back then, so whenever I came across a story that I thought was more up Barstool's alley, I'd send it to him. We just always kept in touch until I met him at the 2011 New England Sports Blog Awards.
Portnoy hosted the event, and awards were given out for Best Red Sox, Bruins, Patriots and Celtics blogs. The way that it worked was that out of those four winners, the audience in attendance voted for Best Overall New England Sports Blog. I won Best Red Sox Blog and was stunned when I ended up winning Best Overall New England Sports Blog, as it was voted on by my peers who were chasing the same dream. When I went up there to accept the award, I said, "The only reason why I won Best Overall New England Sports Blog was because Barstool wasn't nominated," and I'll never forget Dave's face. He was surprised, obviously, that it was my moment, but that I gave it to Barstool. How could I not?
When I started talking to Feitelberg about becoming Barstool's Red Sox guy, it was not something that came together immediately. The process took months before Dave ever got in the loop. First and foremost, I didn't want to leave the SoxSpace team I had just built high and dry. I wanted to at least finish out the season with them. Second being that I wanted to finish college, so I did that, too. After the 2014 season, Dave said that he hadn't considered me for the role because he thought I was happy doing SoxSpace. I was, but how could I ever turn down joining Barstool?
And I don't think he meant it as a slight, but I'll never forget what Dave said when we got to a point where me joining Barstool was becoming a reality. "I'll give it a shot," he said. Oh, you'll give it a shot? You're leaving the door open for this experiment to become a failure? Okay. I started part-time making $500 a month, while maintaining a nine to five at an SEO firm. I remember some part-time guys complaining about the part-time money and that it discouraged them from writing as much as possible, but I took my part-time role and embraced it as if I were a full-time writer. If the option is there for me to write as much as I want, then I'm going to write as much as I want. That means every single day. After I got the job in November of 2014, I wrote every offseason story, every in-season story, every regular season game, and by the start of the 2016 season, I was full-time.
Almost three years later, and he still can't say my name right. Keep that chip on my shoulder, Dave.
If anybody takes anything from this story, I hope it's to never give up. I almost did, and it quite literally would've been my biggest regret and the worst mistake of my entire life. I get asked all the time how I ended up with a job at Barstool, and there's no one answer to that question. My degree was in business and had nothing to do with how I got here. College was always a backup plan for me. I'm still both glad and proud that I got my degree, but I didn't need it. When I'm asked how to create a path to Barstool, I tell everyone to create their own opportunities. Start your own blog. Start your own podcast. Write every single day. Find your own voice and perfect it. Get comfortable speaking into a mic and being on camera. Nobody is going to hand those opportunities to you, so you have to create them for yourself.
I did, and now I'm about to cover the Boston Red Sox being in the World Series for the first time as an employee of Barstool Sports, the hottest media company in the world. On the road to this World Series, Section 10, a podcast that we started in Pete Blackburn's mom's basement back in spring training of 2015, was putting on live shows that had bars outside of Fenway Park at capacity five hours before first pitch. That podcast spawned another podcast, Starting 9, where I get to break down all of Major League Baseball with Animal from The Muppets, who also threw the nineteenth perfect game in baseball history. I could've never dreamt that it would get to this point.
I've waited my whole life for this. I've basically dedicated my entire adult life to this. I hope that whoever reads this takes some inspiration to chase their own dreams, even if it isn't a job like this. I used to get shit all the time from people telling me that I was "obsessed". My favorite quote is that "obsessed" is just a word that the lazy use to describe the dedicated. Sometimes, it takes obsession to get to where you want to be in life, and I'm exactly where I want to be.
For this all to come full circle, I would not be here today without the 2013 Boston Red Sox winning the World Series and reigniting my fire five years ago. My life would be so different without that team. And I most certainly wouldn't be here today without Dave Portnoy taking a chance on me, everyone who has supported me since day one, and those who have joined my journey along the way. Now, here we are, five years later, and I'm enjoying the best year of my life with the Red Sox right back in the World Series for the first time since that fairytale October. Four more wins to write the next chapter.