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Hilarious Interview With Leo Resig Founder Of Resignation Media: “Seriously, Don’t Quit Your Day Job”



I love theCHIVE. It’s funny, mostly crude and, “probably the best site in the world.” And it’s just ONE of Resignation Media‘s multiple photo-centric websites run by the Resig bros on the Venice Beach boardwalk. Lucky bastards. We caught up with brother Leo to talk ‘stash bowling, hustlin’ 50 jobs and the mystery of lady-killer Matt Lauer.

How long have you been involved with the internet? What were your first steps?

My first computer was a Commodore 64 where I dominated Tank and Jumpman Jr, but this was my pre-online period in the late 80’s. I have been on the interwebs since I was 14 (1994) when I got my first AOL email, leo51080[at]aol[dot]com, and still remember the hissing and beeping of dial up. I have since abandoned patience all together.





I love that you used the word, “interwebs.” What time do you usually start work each day? Do you have an office or work at home?

My day starts depending on how late I worked or stayed up drinking wine the night before. We have an office that I go to around 9, but I’m usually in front of my computer around 7:30am. I usually start work from my it’s where I get most work done with zero distractions (other than my daily disagreement with my fiancée Tiffany over whether we watch SportsCenter or the Today Show. Why do chicks LOVE Matt Lauer?)





What’s the first thing you do when you leave the office at the end of the day?

Take my dog for a walk and hunt for food. My nights are fairly tame these days. A little too much laptop time before bed.

We want to know about where you spend your day! What’s on your desk right now?

A three foot tall bowling trophy with my recent nickname, Samson, with my high score of 213. I was dubbed Samson that day because I was sporting a 70’s style wig and a fake mustache that kept falling off. The only time I took my mustache off, I left pins standing, mustache on = strikes. My ‘stache was my Samson.





Other than that, I have Macbook Air and a big ass monitor on my adjustable standing desk that gets a lot of downtime. And lots of paper stacks that need filed.

A lot of people have big ideas. What gave you the confidence to actually put your life on hold and realize yours?

I’ve always been an entrepreneur with a lot of ideas, too many. I think everyone has a lot of really good, and bad ideas. It’s a matter of recognizing the bad ones and acting on ONE good idea to start. My brother John still gives me trouble of how many bad ideas I continually spew out.


I’ve started a couple businesses that failed miserably and these are the best mistakes of my life. For me, my confidence came from knowing that I could hustle and make a buck all by myself if I didn’t have a job. Whether it’s sneaking on to golf courses as a teenager and finding golf balls to later sell on a street corner, setting up a vending machine in my fraternity in college, or selling fake celebrity autographs on Ebay (sorry Neil Diamond fans). I’ve had over 50 jobs in my life and I always have had the confidence of knowing I can make money on my own whether through offering a service or selling something.





Yes, I’ve experienced a good amount of success with theCHIVE, but I never thought it would be as big as it is now. Some entrepreneurs fall victim to their over-optimism, and illusions of grandeur are exactly that, illusions until one can experience it. Not to say I’m a pessimist, but optimism and confidence are not one in the same with me, I need results to give me more confidence. Which is why we have bootstrapped the business rather than taking on funding so we could grow at our own pace, adding employees only when it was absolutely necessary and we could afford to do so. I never used to think big and now I do, which is why I have such high aspirations and expectations for, our newest venture connecting men to cool products while entertaining them at the same time.


What advice do you have for other entrepreneurs struggling to get their business off the ground?

Don’t quit your day job. I know that phrase is exhausted and used more tongue-in-cheek, but there’s a lot of truth to it. Out of college, I was working as a server at a wine bar in Chicago and writing screenplays while most of my friends were starting their entry level, crappy corporate jobs. I was doing well enough to live on my own in Chicago waiting tables and I convinced my ego that it’s ok to be a server with a college degree because I was pursuing my dream of filmmaking. Turns out, I hated waiting tables and I wanted freedom to do what I want when I wanted.


Being overly ambitious, I thought I could start my own wedding DVD business full time so I quit my job and set off on my own with no overlap of running the new business and waiting tables, which actually paid the bills. It didn’t have legs and I opened multiple credit cards to fund the business (thanks Robert Rodriguez) and it all went to hell. In about 6 months. I didn’t hedge my bets in the beginning and maintain an income stream while trying to launch a new business with no funding and it bit me in the ass.





When I started theCHIVE in 2008 with my brother John, I was working for an online ad rep firm, full time with salary. I worked on theCHIVE at night for a whole year before quitting my career. I didn’t quit until the profits from theCHIVE were enough to sustain my lifestyle.


3 people you recommend we follow on Twitter, and why?

  1. Mac Faulkner because he is the weirdest, funniest dude I know. Plus he sacrifices sleep thinking of his next great Tweet, like, “I wish my gang colors were more seasonal”
  2. Venice311 because Venice is the most entertaining city in the US and Venice311 is the pulse
  3. Matt Lauer so you can win girls’ hearts
  4. theCHIVE is a must follow because it’s probably the best twitter feed on the internet





Can you share some numbers with us?

Sorry, revenue figures we hold pretty close to our chest because we are privately owned but we’re keeping the lights on for a long while. Traffic wise, we’re happy to share our Google analytics with anyone who asks. theCHIVE started from scratch and now have over 40M visits/month (14M UV’s) and 200M PVs across both online and mobile combined. Tapiture is only 3 months new and is already doing 1.5M UV’s and 25M PV’s. We now have 20 full time employees under our roof in Venice Beach.


And finally, what would you do if the government shut down the Internet?

Make wine.


Photo Credits | |

Author : Holly Hutton

Born in the Big Easy and raised in the Sunshine State, Holly has spent the last five years brunching in the Big Apple and bantering with Big Ben. As a wandering writer, techy-in-training, and avid alliterator, Holly has written everything from educational policy and political news briefs to web content and travel blogs. She is thrilled to be a part of the KS team and working with a community of smart, savvy, entrepreneurs on all things startup!

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