Jack O'Brien
VP & Editor in Chief, Cracked
Discussion
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
Hi everyone, my name is Jack and I’m the founder and Editor in Chief of Cracked. Over the course of the past 9 years (4 decades, Internet time) I’ve gone from writing and editing the majority of the content on the site to heading up an editorial team of over 20 full time creatives. I also host two Earwolf podcasts, and am the co-VP of Cracked’s business. These days, my main focus is inventing new types of Cracked content, and building a native advertising strategy that is in step with the future of online content, and the high standard of quality our audience expects from our brand. Ask me anything that isn’t my social security number!
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Matt Geller
@matthewgellerod · CovalentCareers,Inc.
@jack_obrien What's the best way to qualify if a writer will be good for your team?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@matthewgellerod We tend to look for people who can write funny, and have good editorial instincts. It's a really rare mixture of skills, and once we find them, we make them work incredibly hard, and see how they deal with feedback (that can be pretty brutal). If they're still around after that point, they're probably on our team right now.
Ryan Hoover
@rrhoover · Founder, Product Hunt
Jack! What article on Cracked are you most proud of and why? 😊
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@rrhoover Either this one that I wrote with forum member Elford Alley three years ago: http://www.cracked.com/article_1... The response has been really nice, and it seems like we reached a lot of people; or this one that I wrote with David Wong / Jason Pargin http://www.cracked.com/article_2...
As for articles that aren't by me, I'm really proud of the Personal Experience section of the site that Robert Evans created a few years back, and that has continued to grow in really interesting ways ever since. http://www.cracked.com/personal-...
Erik Torenberg
@eriktorenberg · Former Product Hunt
Often times writers/journalists have hard time becoming managers. How did you make the transition and what is your advice to others?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@eriktorenberg Definitely made the transition very slowly while giving myself room to make a lot of mistakes. Otherwise, brutal honesty, and always trusting my editorial instincts and the instincts of the people I hired. There's this thing called delegating that just means you let other people who are smarter than you do the work instead, and that's been extremely useful too.
Andrew Ettinger
@andrewett · Product Marketing, Twitter (ex-PH)
Given ad block rising prevalence, what does the future of advertising on the web look like?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@andrewmettinger I think the future is in providing honest, straight forward marketing that respects the audiences intelligence. The reason ad block is so popular is because a lot of ads these days are designed to make it difficult to enjoy sites. I don't think there is a future of advertising on the web until publishers aren't forced to sacrifice user experience in order to make money. Obviously easier said than done but I think there are ways to do it. It's a worthy mission statement anyways.
Emily Hodgins
@ems_hodge · Community and Marketing, Product Hunt
What living person would you most love to interview?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@ems_hodge Probably Errol Morris. I'm reading an incredible book by him right now called Wilderness of Error and he just seems to have such a lively, engaging sense of the truth. I'd love to talk to him about some of the mysteries I'm working on for my Howl podcast Good Question.
Melissa Joy Kong
@melissajoykong · Content, Product Hunt
I love some of the topic selections for the Cracked podcast. I was just listening to the one about the genealogy of fear. How do you choose the podcast topics? And is there a specific episode that struck a chord with people in a way that surprised you?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@melissajoykong The podcast topics grow out of the editorial pitch docs and conversations we're having in editorial meetings for the most part. Every week we read through 300+ pages of pitches from our online writer's workshop as well as interviews conducted by our PE team. We then spend 3-6 hours of the week discussing those pitches, what we find interesting about them, what direction we'd like to see them taken. So as an editorial team we're ingesting a lot of inspiration, and we're already doing a lot of digesting it behind closed doors. I will then usually choose a topic, or someone on the team will pitch a subject that seems really intriguing to me, and we're off to the races. But for the most part, it's making public the types of conversations that were taking place already as part of our editorial process.
Jacqueline von Tesmar
@jacqvon · Community, Product Hunt ✌️😻
What do you consider to be your best accomplishment?
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@jacqvon Building the editorial team that we have in place at Cracked. We haven't had a creative leave the team since the very early days of the site. I obviously can't take credit for all of the hiring decisions. Once you hire the right people they find the other good people for you, but I'm really proud of the culture we've built. That or beating my dad in one on one when I was in seventh grade.
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@corleyh Spiders. Spiders scare me. http://www.cracked.com/article_1...
http://www.cracked.com/quick-fix...
http://www.cracked.com/article_2...
Harry Stebbings
@harrystebbings · Podcast Host @ The Twenty Minute VC
Hi Jack,
Thanks so much for joining us today. My question is where do you feel the future of journalism lies? Is it in the long form more traditional style or are the links of buzzed presenting an alternative method of content! Love to hear your thoughts!
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Jack O'Brien
@jack_obrien · VP & Editor in Chief, Cracked
@harrystebbings I think they both serve a purpose. When I started the site, the conventional wisdom was that you had to keep word count down because people on the Internet didn't read. We now run 5-6K word articles on a regular basis. Some of our longest articles are some of our most popular. So I think there will always be a place for long form journalism, as long as you don't waste people's time. That's the one thing the Internet doesn't forgive, and rightly so.