Rap Genius founders Mahbod Moghadam, Tom Lehman, and Ilan Zechory are having one hell of a year. Rap Genius—a Wikipedia-esque website that allows contributors to interpret rap lyrics—is not only gaining users like crazy, but it also raised $15 million this fall from Silicon Valley powerhouses Marc Andreessen and Ben Horowitz. Their vision is to move the site's model beyond just rap music, letting people critique and annotate everything from classic literature to acts of Congress. It's an ambitious project for sure, but the former college pals have the energy (and sense of humor) needed to tackle it. We caught up with the trio to chat about sleep routines, workspaces, and of course, tunes.
Names: Mahbod Moghadam, Tom Lehman, Ilan Zechory
Occupation: Mahbod: Co-founder, Rap Genius; Tom: Co-Founder, Rap Genius; Ilan: Earth Mother of Rap Genius, occasional hypnotherapist
Location: New York, NY
Current computers: Mahbod: Lenovo; Tom: 15" MacBook Pro Retina with maxed out everything; Ilan: MacBook Air with external monitor
Current mobile devices: Mahbod: Droid (don't judge me!); Tom: Second black iPhone 5. I tried switching for a white version after dropping the first one in an Art Basel porta potty, but no dice!; Ilan: iPhone 5
What's apps/tools/software can't you live without?
Mahbod: Twitter is my life!
Tom: Number one is definitely Boomerang for Gmail—once you have this it's game over. No one can keep up with you. They'll always wonder, "How does he stay up on everything?!" Rapportive is also pretty key, especially for screening job candidates since online identity is so much more important than your resume. Jing and Dropbox for easy screenshots are a must. SizeUp is de riguer if you often look at a bunch of different terminal or TextMate windows simultaneously. The best pen is the Pilot G2 07 and the best notebook is the unlined Muji. Also, the holy trinity of command line keyboard shortcuts: ctrl+a, ctrl+e, and ctrl+k.
Ilan: Boomerang for Gmail, Jing for screenshots, and ClipMenu so I can access more than one thing on my clipboard. Also, I drink a TON of water (2+ gallons a day) because Mahbod tells me to.
Pictured above: Tom's desktop. Expanded version here.
What's your best time-saving trick / life hack?
Mahbod: The key is to only steal or nibble grapes or cashews from Whole Foods and never buy them!
Tom: Killing your commute by living at the office is probably the biggest one. Not following sports saves a bunch of time but it makes you a weirdo. I used to have a script that would automatically reserve me the coveted 7:15 PM squash court right as it came available, but it broke. Also, don't worry about organizing your iPhone—just keep the home screen trill and search for everything else (NO FOLDERS!).
Ilan: I never check the weather.
What's your favorite to-do list manager?
Mahbod: I'm a big fan of Trello (hello!).
Tom: I've tried everything, but the truth is you just gotta be 'bout that life, grinding 24/7, 365. Keep everything in your head. It sucks, but life happens too fast to write stuff down—and especially to re-prioritize the stuff you've already written. I do keep a Muji pad left of my keyboard to write things down really quick, but it always ends up covered in doodles.
Ilan: I'm still waiting for something that works well with email. I'll fux wit Trello or WorkFlowy from time to time, but I end up dropping them. So much work comes out of email, and I don't want to write everything down that I don't take care of immediately. I end up on the inbox zero treadmill (with Boomerang), which sucks from a mental health perspective, but I haven't found a better way to get everything done. Important things I just try to remember.
Besides your phone and computer, what gadget can't you live without?
Mahbod: My RZA headphones. Way better than Beats by Dre.
Tom: I like my All-Ett wallet (AKA the world's thinnest wallet).
Ilan: I'm feeling this little cube timer for naps.
What's your workspace like?
Mahbod: I sleep by my desk so it's an easy commute!
Tom: Computer-wise, the MacBook Pro is hooked up to two 27" Thunderbolt monitors. Lefty has a 2x2 arrangement of TextMate windows (sometimes I'll make it 2x1 if I need to look at something big) and righty has three terminal windows open, two of which run the Rails server and the Rails console. I do my browsing, testing, and chatting on the right monitor.
Ilan: My office reflects my role as Earth Mother of Rap Genius: big comfy chair, blankets, slippers, some books, a foam roller. Our friend Max Kotelchuck builds the Rap Genius furniture (out of wood!), which is all very minimal and beautiful.
Pictured above: Ilan's workspace. Photo by Maia Harms.
What do you listen to while you work?
Mahbod: Mainly Killa Cam, a lot of Beach House, I love Grizzly Bear, [and] Gucci Mane is nice to work to.
Tom: Silence! Or whatever Mahbod posts on my Facebook. I also like the second best song a lot. And of course the first best when I'm feeling emotional.
Ilan: "It Feels So Good," by Sonique.
What's your sleep routine like?
Mahbod: I sleep any time I don't have caffeine jetting through my veins, but it's pretty rando. Not at all tied to the rise and fall of the sun.
Tom: I'm generally a 3:00 AM-10:30 AM kind of guy, but if I do happen to wake up early—and especially if I go to the gym first thing—I make sure to tell everyone about it. I use my phone as an alarm, but I always put it on "do not disturb" mode which I love. Ilan says I should stop checking Hacker News and Twitter on my phone the instant I wake up, but I just love it—a true guilty pleasure!
Ilan: Checking your phone right when you wake up is poisonous! It's like feeding a newborn baby Diet Coke. I own the URL to wakeupcheckphone.com and I'm going to build some sort of mobile shaming site one day. As long as I get enough sleep over the course of a week, I don't care how it's distributed.
What everyday thing are you better at than anyone else?
Mahbod: I'm a really good tweeter and I have healing hands [for] massage.
Tom: I'm good at getting rid of old clothes. The secret is to think a lot about death.
Ilan: I have a pretty solid "WTF are you talking about, WTF are you doing, get away from me" face. Always have.
What's the best advice you've ever received?
Mahbod: The homie Justin Kan told me that traction is the only thing that matters. If millions of people are using your product then you've changed the face of humanity.
Tom: "Mail in your 83(b) right now!" - Paul Graham, Jessica Livingston, and Kirsty Nathoo; "As long as you're on the side of parks, you're on the side of angels. You can't lose." - Robert Moses
Ilan: You must work for your own salvation!
Pictured above: Tom's workspace.
Anything else you want to share?
Mahbod: Don't eat sugar—it's poison!
Tom: Come work at Rap Genius—if you're a bomb programmer, we'll cake you up! Whatever number you're thinking of right now...it's higher.
Ilan: You're all gonna die eventually.
Note: You can connect with Rap Genius on Twitter @RapGenius.
Top image by Maia Harms.
The How I Work series asks heroes, experts, brilliant, and flat-out productive people to share their shortcuts, workspaces, routines, and more. Every Wednesday we'll feature a new guest and the gadgets, apps, tips, and tricks that keep them going. Have someone you'd kill to see featured, or questions you think we should ask? Email Tessa.