Jack O'Brien

VP & Editor in Chief, Cracked

THIS CHAT HAPPENED ON October 19, 2015

Discussion

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!
Matt Geller@matthewgellerod · CovalentCareers,Inc.
@jack_obrien What's the best way to qualify if a writer will be good for your team?
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? 😊
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?
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 · PMM @Twitter // Previously @ProductHunt
Given ad block rising prevalence, what does the future of advertising on the web look like?
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?
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?
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.
Melissa Joy Kong@melissajoykong · Content, Product Hunt
How do you think the evolution of journalism—and the platforms through which people consume news now—are changing the way the world thinks and behaves?
Jacqueline von Tesmar@jacqvon · Community at Product Hunt ⚡️
What do you consider to be your best accomplishment?
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.
Corley@corleyh · COO @ Product Hunt
@jack_obrien what scares you?
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!
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.
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
Thanks for joining us Jack! What are your favorite podcasts to listen to?
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
@alexcartaz My favorite podcasts to listen to are This American Life, Radiolab and the other usual suspects for journalistic stuff. For comedy, I love Earwolf and The Doughboys podcast with Nick Wiger and Mike Mitchell is new and incredible.
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
What is the most interesting thing you've learned while creating Cracked's podcast? and what is the most frustrating problem you wish you had an easy solution for?
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
@alexcartaz Difficult question! I have a hard time seeing into the past beyond the most recent episode. The fact that screwdrivers were invented 300 years after screws blew my mind. Probably, the 11 Nations of America episode. Our Editor Kristi Harrison found this book and we interviewed the author and it taught me a lot about US history, and how the demographics break down and influence the things people do to this day. I had no idea that New York City is based on a totally different set of ideals from Boston, for instance. I just lumped them together as East Coast cities, and I've lived in both of them before. http://www.businessinsider.com/a... Also the data from Dataclysm was incredible. Researching that episode was like a week long head-rush. http://www.npr.org/2014/09/06/34...
Ben Tossell@bentossell · newCo
Hey what would the you of 2 years ago think of where you are now?
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
@bentossell Hm. That's an interesting question. First of all I think he'd be psyched to have access to time travel. We'd probably high five each other about that straight away. Two years ago I was just developing the Cracked podcast and I'm pretty happy with where we've taken it, though it is nothing like what I had in mind for it at that time. That version would have been impossible to produce. You can hear something closer to the original version in Episode 1. I think there are some problems he'd be disappointed we haven't solved yet. Renewable energy. The above mentioned ad blocker paradox. But I think he'd be ... encouraged? Sorry. Boring answer. Great question.
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
As a podcaster (for multiple podcasts) and podcast listener, do you have any specific thoughts on what the future of podcasting will look like? a new/different listening experience? in-app purchases on ads? data around listening habits, etc.? what do you most hope to see that doesn't currently exist?
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
@alexcartaz I'd like to see podcasts lead the way for the rest of the web, actually. Ads that are in the same voice as the content, honest about the fact that they are ads, while respecting the intelligence of the listeners. I hope podcasts don't become more like ads elsewhere on the web. I'd like to see the rest of the web become more like podcast ads. I think it's just a much more authentic experience than any other online ad format that I've experienced.
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
What are your goals and vision for Cracked over the next 5-10 years? and unrelated: what is your current favorite animated series? and what movie have you most enjoyed dissecting on the podcast? =)
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
@alexcartaz My goal is to turn Cracked into a great business. My vision is to do it without screwing up the level of trust we've built with our audience. I think it's possible, and I think if we pull it off the way I expect us to, we will be leaders in the industry. I like Bob's Burgers and Archer but I'm way behind on animated series. I need to get caught up before I can vouch for them being my jam more than anything else being made. I love talking about Pulp Fiction. It's so timeless and there are just nesting dolls of brilliant ideas hidden inside of what, on its surface, is a great movie.
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
EDIT: I was answering a question but I'm just going to leave this dangling out here because I like how it looks on its own. Spiders. Spiders scare me. http://www.cracked.com/article_1... http://www.cracked.com/quick-fix... http://www.cracked.com/article_2...
Alex Carter@alexcartaz · Operations @ 60dB. Ex-PH Podcasts 😻
@jack_obrien thanks for taking the time to chat with us today, you're a fascinating person and this was really insightful! =)
Andu POTORAC@andupotorac · Co-founder at Widgetic
@jack_obrien How often do you guys use interactives to tell better stories? Are your articles usually just text + images, or you're investing time into creating engaging experiences / widgets as some of the bigger brands do? (ny times, bloomberg, etc)
Andu POTORAC@andupotorac · Co-founder at Widgetic
@andupotorac Say, from 10 stories how many are just text + images? And is there anything you guys are doing / strategically planning to increase user engagement?
Jack O'Brien@jack_obrien · VP & Editor in Chief, Cracked
Thanks everyone! Great talking with you! Hope to see some of you tonight at our live podcast at UCB Sunset!