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High Five with Kevin O’Connor of The Ringer

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Checking in with an old friend.

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A few months ago, Kevin O'Connor was hired by Bill Simmons to work on his new website The Ringer. Before that he wrote for CelticsBlog. As the old saying goes, it took Kevin 5 years to become an overnight success. While he is obviously talented, what sets Kevin apart is his tireless work ethic. I thought it would be a fun idea to interview him with the intent of giving aspiring bloggers and writers some tips on how to do this the right way. Oh yeah, and I couldn't resist getting in some Celtics and draft related questions too. Hope you enjoy.

1. I get applications to write for the blog every month. When I got your application way back in 2013, I was impressed with your professional tone, your confidence in yourself, and the all important writing samples that showed me that you were both talented and prepared to put your best foot forward. What advice would you give college students and other young writers as they seek employment in the writing field?

First off, I can’t thank you enough for the opportunity you gave me. I read CelticsBlog for years and never thought I’d see my name on the site. While interning at Comcast SportsNet New England, my good friend Andy pushed me to apply, so I did. Then just a few days later you brought me on. I guess that’s the first step: find a platform or create one for yourself. You need to be known to get noticed. But understand that a “no” doesn’t mean you’re any good. It might just mean you aren’t ready for that stage. Find ways to improve no matter what.

Here are some other general pieces of advice:

  • Make connections, but make them genuine! Networking is very important regardless of the field you go into. Talent matters. Hard work matters. So does getting to know people within your field. If you’re a shy person and find it difficult to meet people, but I believe in most cases shyness is a habit. You can change by revising your behavior.
  • Accept criticism and learn from it. I see a lot of writers say, “Don’t read the comments.” Sure, sometimes it’s a toxic wasteland, but I love the community and there are lessons to be learned at every corner, especially when you’re a young writer.
  • Read more books. This is something I still don’t do enough because it’s hard to find the time. But do know that the most successful people in the world are avid readers. Learn from the example they set.
  • Surround yourself with people who are positive, yet also real with you, and be equally nice to the people you meet. At the same time, never lose sight of who you are. My best friends are all still the same people I was best friends with in high school.
  • Make sacrifices if it feels like something or even someone is keeping you down. It might be something like giving up video games, or not binge-watching a show on Netflix, or it might even mean not going out on a Friday night with your friends. But those sacrifices are rewarding when you’re investing the time into something you truly love.
  • Luck plays a role in everything, but you can also create your own luck. As Bill Belichick once said: “Talent sets the floor, character sets the ceiling.” Always remember that, and be ready for when your opportunities do come.

It feels weird even being asked for advice, but if anyone ever wants to chat they can hit me up on Facebook or Twitter @KevinOConnorNBA. With that said, while I feel proud about where I am at this stage of my career, this is a never-ending learning and growing process. There are much better examples. Look outward at people from different fields and environments. Every word in this piece by Ben Casnocha is important. They might be the most important lessons you ever read.

2. Your draft guide was so well researched and layed out in such a user-friendly format that it became a must-have for NBA fans and media leading up to the draft. What inspired you to put that together and just how much work went into it?

I’ve always enjoyed scouting and making predictions. I embrace and trust the process. While I starting to establish myself as a writer, I thought it would be a great way to do something nobody else was doing for the NBA. Various NFL writers put together their own NFL Draft Guides and I thought I’d do something similar for the NBA. It was an important thing for me personally and professionally. I’m thankful that it was something you allowed me to promote on CelticsBlog, and I hope it’s something the CelticsBlog community enjoyed.

3. Ok, what is Bill Simmons really like to work for? (Or said another way, "How do you like working at The Ringer?")

It’s an amazing experience. It’s beyond anything I ever could’ve imagined and I’m so grateful to have been given the opportunity. My editors Chris Ryan and Danny Chau have helped me improve. They’re truly amazing. The Ringer has so much interesting content besides sports, too, like movies, music, or tech. Juliet Litman’s Bachelor Party Podcasts are my favorite. Shea Serrano’s columns never fail to make me laugh. Jordan Ritter Conn writes the best long form stories on the web. We have a staff full of talented people that all work hard and do so many creative things. It means a lot to be part of this team.

4. True or False: The Celtics need to make a trade between now and the 2017 draft to have any hope of a championship in the next 5 years.

False. They could make one during free-agency, and it’s always possible that turns out to be the best time for a trade anyway. The best order of operations would allow the Celtics to outright sign a player(s) first in free-agency using cap space, and then make a trade. But, let’s be real, the Celtics will take the trade when it’s available. Unless they feel confident they’d be able to sign Gordon Hayward this summer, I still say Carmelo Anthony at a low, bargain price, still provides the Celtics the best of both worlds; I know I’m in the minority, but hear me out.

5. Give us your top three prospects for the Celtics fans should focus on for the rest of the year. (I know, I know, it is hard to narrow it down)

Markelle Fultz and Lonzo Ball are the clear top two prospects, in my opinion, at least at this stage. After that it gets fuzzy. Brad Stevens and Lonzo Ball are basketball wizards. I sometimes wonder if they’re made for each other. Fultz’s two-way versatility is remarkable; he’d be a tremendous fit next to Isaiah Thomas. For the third player, keep tabs on Malik Monk. He can stroke shots from literally anywhere on the court and I think he’s a better playmaker than he gets credit for. However, like Thomas, he’s not a defender or rebounder, so that’s not the best backcourt fit.

Thanks again Kevin and great work on The Ringer. Don’t be a stranger!