Do Cool Sh*t (27 page)

4. What is the best life advice you can give to help someone else do cool shit?

First, take a moment and make sure that you are coming from a starting place of kindness. Then speak your truth! It will be scary. But run toward it. Try to do so fearlessly, or despite your fear. Because your truth, the thing that lights a fire inside of you, is a huge part of who you are. If you dull it, or dim it down, to try to make others comfortable, you will just make yourself small and lessen your chances of being effective. The best way to elevate others is to elevate yourself. So be big. Be bold. Speak it, shout it, from rooftops and the peaks of mountains. Love your fire. Breathe it into other people. And you will inspire them to do the same. Then we all get bigger and better.

5. What was the moment in your life that made you realize that you could stray from the norm and do cool shit on your own?

When I started to realize that my voice mattered. I started to use social media to have conversations about causes that inspire me, music that gets me dancing, style that knocks my socks off, and the responses I started getting blew me away! I realized that my authenticity—my nerdfests and freak-outs and passionate diatribes—mattered to the people that matter to me. And that changed the game for good.

GRAHAM HILL—FOUNDER OF
TREEHUGGER
AND LIFEEDITED

I met Graham Hill when I was twenty-three years old. I would like to say that Graham was the person who introduced me to the world of entrepreneurship and made it seem possible. I met him standing in line to get into a party in 2003. Graham founded an awesome blog called TreeHugger.com and he sold it to Discovery Channel a few years later. He started another design concept called LifeEdited, which brings smart design to small spaces.

We had a blast that night at the party, and he invited me to brunch the next day in Chinatown at a place called DimSum Go Go. (I’ll never forget it because it was at this brunch that I met Anne Maffei and Upendra Shardanand. Both Anne and Upes were go-getter entrepreneurs, and they really took me under their wings and invited me to so many different events and parties over the next few years and introduced me to other people doing awesome stuff. It was with their guidance, inspiration, and blessings that I was able to open my first business. Thank you guys so much!)

1. What does “doing cool shit” mean to you?

From a business perspective, it would mean acting as a catalyst to bring beautiful, useful, world-changing things into the world. Creating things that matter and that resonate with people . . .

2. What cool shit are you up to now? And what cool shit are you planning in the future?

I’m building a movement around less stuff and less space. I believe that we can apply design, technology, and behavior change to create fulfilling, compelling lives that allow us to live within our means financially and environmentally, and that simplifying our lives will give us a little more time, a little more ease, and perhaps a little more happiness. My company, LifeEdited, is focused on working with developers to build large buildings composed of small spaces paired with sharing systems and heavy on community. We are also looking to create small-space enabling housewares and furniture.

3. What was the most important lesson you’ve learned about doing cool shit in business?

At the end of the day, it’s all about the product. Sure, you can help things along with marketing blah blah blah but it’s pretty much about the product. Make some good shit!

4. What is the best life advice you can give to help someone else do cool shit?

Find some shit you love. Focus in that area. And notice that entrepreneurs aren’t that special, they just figure it out and keep moving the ball forward.

5. What was the moment in your life that made you realize that you could stray from the norm and do cool shit on your own?

Don’t think I had that moment . . . just realized at some point that that was what I was doing.

ADAM RICH—FOUNDER OF
THRILLIST

Adam Rich is part of the Summit community as well. The world just keeps getting smaller and smaller. I brought some pizzas over to his office, and he gave me a tour of his impressive, growing workplace, and as we walked the floors, I could really see a sense of great pride in what he has accomplished thus far.

1. What does “doing cool shit” mean to you?

On the most basic level “doing cool shit” means putting energy in. It’s the opposite of coasting along and following a groove. No matter what the “shit” in question is, if it’s going to be “cool,” it’s got to feel exciting and fresh. Doing something others haven’t requires an investment in thought, bravery, and effort and represents a basic way you interface with the world at large: Do you accept what you see around you and accept it as immutable, or do you perceive it as a starting point? Honestly, I don’t think the scale of the endeavor is really that important. It’s a binary characteristic: either you put energy in, or you don’t.

2. What cool shit are you up to now? And what cool shit are you planning in the future?

Right now we are rethinking what we do at
Thrillist
. After putting out a men’s lifestyle e-mail for the last seven-plus years, we’re right now going through a really exciting period of unsentimentally reassessing everything we do. Seven years is an eternity in media, so as nerve-racking as it’s been to call into question everything we know about our company, it’s actually brought me closer back to the excitement I felt starting the company in the first place. I’ve realized that over these seven years, the evolving and refining we’ve done had turned our start-up into the exact kind of legitimate machine that inspires entrepreneurs to ask what they can do to push things further. I’m just excited that—in this instance—that entrepreneur can be me.

3. What was the most important lesson you’ve learned about doing cool shit in business?

To be transparent and treat people with respect.

4. What is the best life advice you can give to help someone else do cool shit?

Go for it. After conferences and panels, I talk to so many would-be entrepreneurs who don’t have a website or anything concrete to show for their ambitions. My personal experience is that no matter how long you agonize over getting your initial offering perfectly right, once it’s out there, you’re showing it around, using it in the real world, you’re going to find flaws and need to revise. Knowing that you can’t ace it right off the bat, it’s really just a question of grabbing your balls and jumping in with the best you can do. You either have a business or you don’t, and not having a business is a surefire way to not have a successful business.

5. What was the moment in your life that made you realize that you could stray from the norm and do cool shit on your own?

I honestly don’t think there was ever a point when the music swelled and I realized “I can do this!” Starting
Thrillist
was extremely stressful and scary, and it was only through years of working hard for incremental successes that I felt confident that it would all pan out. No matter how great you think your idea is, if you’re not in there every day with your sleeves rolled up, it really doesn’t matter.

I will say that—right before launch—I harassed and pestered every single person I knew and badgered them to sign up for our newsletter. Most were people I thought it would serve: young mostly guys living in NYC eager to feel like they were spending their time and money wisely in a city where you never have enough of either. My pitch was a personal one, since I created
Thrillist
because I felt the same way. What we sought—and still seek—to do is cut through the clutter, and with a trusted voice offer our readers a clear-eyed recommendation of some new thing they should check out. The tagline was “Here’s the move.” We sent our very first newsletter out to six hundred people.

CAPT. ZACHARY ISCOL—FOUNDER OF HIREPURPOSE

I met Zach in college at Uris Library. I remember we were both student athletes and were cramming for a test. We dated during our sophomore year and transitioned to best friends ever since. His family is like my second family and has been instrumental in so many of my life decisions.

When we graduated, Zach became a captain in the Marine Corps and served during the Iraq War. He earned a bronze star, and he had far too many close calls, but was somehow spared. He produced a documentary film called
The Western Front
with my sister Rads about the war in the Middle East and has since founded the company Hirepurpose to help veterans get jobs when they leave active duty, since he found that the government and military didn’t properly help the veterans transition to civilian lives.

1. What does “doing cool shit” mean to you?

To me, doing cool shit means challenging the system and figuring out a better way of doing something. You can’t be afraid of criticism, ridicule, or failure. Think about Magellan setting out to circumnavigate the world. Most people probably thought he was nuts because he was challenging popularly accepted truths. It is easy to look back and think, “Wow, all those people back then were crazy. How silly to think the world could be flat.” But how often do we do the same thing today when faced with new technologies or ways of doing business? But those crazy ideas change the world. It isn’t about making money or becoming successful, it is about challenging the status quo and striking out on your own in order to create something, do something that’s never been done before, make meaningful change, and leave your mark.

2. What cool shit are you up to? And what cool shit are you planning in the future?

I served in the Marines and did a number of combat deployments overseas. In my last job in the service, I had the opportunity to help build and run the recruiting, screening, assessment, and selection program for US Marine Corps Special Operations. Essentially, that’s how we find and select the right marines for special operations. After I got out, I started helping a few of my former marines find jobs and quickly realized that the entire online employment industry was built on a preindustrial technology—the résumé. Even the most technologically advanced job sites use powerful software applications to attempt to match key words in résumés with key words in a job description. For veterans, this is especially challenging because their military skills do not translate well to civilian jobs. So over the course of eight months, we took part of the methodology we used to screen and select marines for Special Operations and used it to build a sophisticated online platform (hirepurpose.com) to match top veterans with great jobs and internships. Unlike other military job sites, we dig deeper than just the résumé and introduce veterans to companies through employment testing that measures soft skills and behavioral strengths and personal profiles that enable veterans to better tell their stories to potential employers. Eventually, I’d like to use this to help everyone, not just military veterans, find meaningful employment that suits their interests, motivations, and strengths.

3. What was the most important lesson you’ve learned about doing cool shit in business?

Don’t be afraid of failure. There is no such thing. You can only fail if you fail to learn from setbacks. If you’re open and honest to it, failing is the best teacher and the only way to challenge assumptions that stand in the way of better products and, ultimately, success. But you also have to be willing to really lay it all out there and work your ass off. Otherwise you’re just going to fail because you’re lazy.

4. What is the best life advice you can give to help someone else do cool shit?

Don’t be afraid to try new things. To be alive today and live in the developed world means you have more freedom of choice than at any point in history. Even one generation ago, your chosen profession remained your career for life. Take advantage of the fact that that’s no longer the case. If you’re not happy, try something else on for size until you are. Time is the most precious commodity.

5. What was the moment in your life that made you realize that you could stray from the norm and do cool shit on your own?

I was never the fastest kid, and I was never the smartest kid. That meant I didn’t have much choice. If I was going to be successful, I was going to have to invent my own game.

DAN ROLLMAN—FOUNDER OF RECORDSETTER

I met Dan Rollman at my friend Nazli’s party. He was by far the tallest guy in the room at six feet seven inches. I met him while he was helping my sister build a dresser in our new apartment. It took them seven hours to build the dresser. Dan founded RecordSetter after he was inspired by the Burning Man camp Playa Book of Records, where the camp would give out badges to anyone who set a random record about anything. With that whimsical idea, he thought to himself, “Why not create the Wikipedia of World Records?” and the idea grew from there. I love it and I am proud to say that I hold three world records on RecordSetter
.com.

1. What does “doing cool shit” mean to you?

“Cool shit” happens when you find the courage to follow your gut and then execute to the best of your abilities.

2. What cool shit are you up to? And what cool shit are you planning in the future?

Right now, I’m focused primarily on RecordSetter, a Burning Man–inspired media company that invites anyone, anywhere to set any world record they want. I also work on the National Day of Unplugging, a project designed to get people offline for one day a year. In my spare time, I make handwritten T-shirts (snerko.com).

The future is TBD, but possible “cool shit” projects include an Internet-free coffee shop, a line of Russian doll envelopes, a sport that combines miniature golf and bowling, and the World’s Largest Menorah.

3. What was the most important lesson you’ve learned about doing cool shit in business?