"Just one brilliant, terrible idea"

Why we do what we do. Read this great piece by Ben Evans on VC that applies to founders as much as it applies to investors.
Indeed, all of this applies to entrepreneurs even more than it does to VCs. Just as VCs would like only to do the deals that succeed, so would entrepreneurs. But entrepreneurs only get to do one at a time (normally). So an entrepreneur is committing years of their life to just one brilliant, terrible idea, that probably won't work, but if it does, will be enormous. And around half of those commitments fail - there are lots of risks, and lots of ways that these attempts can fail, without it being anyone's fault. If you take a normal, mature company to zero in a few years, you probably screwed up, but if a startup doesn't make it, generally that's just the risk you took. Pulling a company into reality out of thin air, through sheer force of will, isn't easy. But you're only reading this because of the entrepreneurs who took that bet. This is how invention works.
Take that bet. Create a legacy.

My infamous talk at Howard High school that got me removed from the building by the Principal

14 years ago, I gave the Howard High Class of 2001 Commencement Speech.

This was my chance to say the things I wish I'd known to say back then. Unfortunately, I was told by the Principal that she was embarrassed by my language and told me I would never be invited back. This is the same language I use in most of my talks and in my bestseller, Without Their Permission, so it's how I addressed this room of Juniors and Seniors. Needless to say, I was disappointed when my dad & I were escorted out of the building by order of the Principal. I wanted to stay and take some more selfies with students, but so it goes.

I've since gotten tremendous support via facebook, twitter, instagram and reddit -- including from many of the students and their parents. Thank you. I'm going to keep speaking my mind and you all will go and be amazing, just be true to yourself and give lots of damns about whatever it is you do.

And even though I'm never coming back: Go Lions.

July 11, 2005 - the day we learned about digg

I know I've told this story on stage more than a few times and even wrote about it in my bestseller, Without Their Permission, but sometimes even basic truths needs repeating. Sunlight will always win in the end.

I wrote this email minutes after discovering digg, which was three weeks after we launched reddit. I still have it and revisit it for a laugh from time to time. We were so young. Steve and I had just graduated from UVA a few weeks earlier. This was almost 10 years ago. Wow.

You can tell I was nervous. As soon as I learned about them, I sent this company-wide email out (to Steve) and we took an emergency meeting in the conference room (kitchen) to discuss the venture-backed, celebrity-founded, Silicon Valley startup that would be our chief rival for the next few years: digg.

Fortunately, we'd already launched (back on June 23rd) and Steve & I were building something fundamentally different -- a platform for communities, rather than a single community's democratic frontpage.

I'm so proud of how a little project two naive college kids started grew to become the platform that sets the global agenda, but we have so much more to go and now we have a much larger and more capable team of amazing people with whom to do it!

Onward to the next 10 years.

The Email I Sent Steve That Kicked Off reddit

(You can read more about this in my bestseller, Without Their Permission)

I spent a formative summer after my junior year abroad in Singapore, competing on behalf of UVA at an international Technopreneurship Conference (oh, bless the Singaporeans and their "technopreneurship" conferences).

One of my favorite teachers, Professor Mark White, invited me to go on this all-expenses paid trip. I even turned down an internship at Ogilvy because I like free travel even more than I like unpaid internships in the most expensive city in America.  It was there in Singapore on our first night that I pitched Mark the idea Steve and I had cooked up for our startup.  Mark’s was the first unbiased feedback I'd gotten on the idea (my parents had always been ludicrously supportive of whatever I told them I was up to) and he thought we'd be able to pull it off.

His optimism may've just been a combination of the jetlag and the Singapore Slings, but I was thrilled.

I wrote Steve this email the very next morning.  Here it is in its original form for authenticity. Please forgive all the typos; those keyboards in Singapore aren't QWERTY.  Apparently there's also a button on those keyboards that kept inserting "bro" everywhere -- sorry about that. In fact, imagine a great big [sic] around this whole thing.

hey bro,

i'm in singapore at this technepreneurial seminar, and am basically spending a week learning how to create a tech start-up.i spoke to Mark White (a professor in the comm school, the guy who took me to South Africa, and who recruited me to come here, as well as a generally good guy and technophile) over some drinks last nite, and pitched him on our idea...from his feedback—and let me remind you that he gets pitches every couple of months from students, and was very candid and honest with his thoughts, but basically said it was one of the best he's heard, period.

Not only that, but he wants to be on the board of directors, and already knows some people to hit up for starting capital...

I've got plenty of more details, but I am seriously considering putting off law school for this, but i need you, and we'll both need to be doing this full time for about a year to get it off the ground....but the potential he saw was in the millions my friend...we need to talkseriously.i am coming back the 20th so if we could have lunch around 1pm i could meet you whereever you'd like... let me know.

honestly, this is the kind of thing that could change our lives—and his motivation has really spurred me.but i need you and the same kind of commitment.

Small Empires: Season 2 is HERE

We're back! I'm super proud & excited to share episode one of SEASON TWO of Small Empires. Huge upvote to everyone on the team at The Verge for putting together what I already know will be an amazeballs season. I couldn't do it without you.

Dear viewers, there's still time to revisit all of Season 1 -- I'll be here when you finish.

This Season we're touring North America to revisit some of the best stops from the Without Their Permission bus tour to profile startup communities, one of their startups, and the folks who make them awesome.

First up, Atlanta!

NYRD Radio: For creators, by creators

I've started a podcast & here's a sneakpeak! Not just the people making the next reddit (or similar platform) but the people who will make those platforms awesome (e.g., artisans on etsy, creators on patreon, filmmakers on vhx). The internet enables entrepreneurship on a scale the world has never seen before and we're all writing the blueprint as we go.

Join me for weekly conversations (subscribe on iTunes) with some of the most awesome creators in the game (Episode 1 stars Baratunde Thurston!). We'll talk about how they hacked it to get here and where they're going. Every episode also features Office Hours where I work with an entrepreneur through their challenges -- guests could be a veteran CEO planning a huge product launch or a high school student figuring out how to best launch the crowdfunding campaign for her art.

If you'd like to do on-air office hours with me, click here to sign up. 

This is going to be unlike anything your ears have heard before and -- like everything I'm doing these days -- I hope it scales all the ideas I preach. The future favors the creators.

I want you to be one of the ones who changes the world. Don't worry, I'll take credit for it ;-)

Speaking of which, there's just one week left to apply for the Winter batch of Y Combinator. Do it!

If you're not ready yet, I hope you're tuned in to the free class Y Combinator is teaching at Stanford (How to Start a Startup) and a shoutout to my alma mater (University of Virginia) for a very generous profile on me in the latest alumni magazine.

Similarly, I made the CNBC Next List alongside some awesome entrepreneurs: Elon Musk, Sal Kahn, and Marissa Mayer to name a few.

Time to earn it. I'm headed back to the hustle. Let me know how you like NYRD Radio (leave a review!!) -- it's the only way I know what to improve.

My story: from my first PC to cofounding reddit

The following is an excerpt from my national bestseller, Without Their Permission.

“Yes, I’d like to upgrade my dad’s season tickets. Oh, front row, fifty-yard line, please–the best you have.”
—Me, approximately three minutes after we sold reddit

Halloween has always been one of my favorite holidays, but on October 31, 2006, all the hard work Steve Huffman and I had put into starting reddit (with lots of help from our first hire and good friend, Dr. Christopher Slowe) had quite literally paid off.

The first thing I did after the money showed up in my checking account was to call the Washington Redskins ticket office and upgrade my dad’s tickets to something a bit better than the nosebleed seats we had. I then made a sizable donation to my mom’s favorite charity and got back to handling all the inbound press. It was a blur of a day, but once it ended, I was able to take stock of just how far we’d come in only sixteen months.

When Steve and I looked at each other, there were no cheers of joy, just a shared sigh of relief. We’d pulled off something statistically improbable—just barely—and we knew it. And after everything we’d been through…wow. Grateful, we went and shared a pizza at Mike’s, the same place where we’d been ordering pies since we moved to Somerville, Massachusetts. There, we caught our breath after an entire day of interviews.

For my parents, it was a day when their only child had become a millionaire before he was twenty-four. But they always just wanted me to be happy. Neither one of them really understood the PC they brought into the house not long after my tenth birthday, but they let me do whatever I wanted to it as long as I didn’t break it.

Actually, I almost did break it on several occasions, but then I wound up putting it back together. That computer was my gateway to another world once we got a dial-up Internet connection. I campaigned hard for that 33.6Kbps connection, and when I finally got to hear those now-antiquated sounds of the modem, it seemed like magic to my adolescent brain.

This is actually my cousin BJ’s computer, but if you thought I looked happy playing on his, imagine how excited I was to get one of my own. 

I built my first website on GeoCities. I think it was /siliconvalley/hills/4924 (the WaybackMachine link only goes back to 1999 and by then I’d turned it into a MIDI collection website with some banner ads — I kind of hate myself for making this, but there you go). It was originally my fan page for Quake II (fun-fact: Masters of Doom was the book that made me fall in love with the idea of entrepreneurship). There wasn’t much going on there beyond some photos of rocket launchers and railguns with a few tacky animated flaming skulls. I really liked that game. But at the footer was a counter that showed how many people had viewed the website (I’d later learn that most of those “views” came from me reloading the page).

But at the time: what power! I could build something from my suburban bedroom and millions (okay, well, hundreds) of people all over the world could see just how much I loved a video game. That’s how I got interested in making websites. There was no turning back.

A company called Sidea was my first non-familial-employer (I suspect the real reason my dad wanted a kid was that he needed someone to do all his yard work—and for well below minimum wage, I might add). I later worked a lot of random jobs between high school and college: Pizza Hut cook and waiter (some of the best customer-service experience one can get), deli counter attendant (I was terrible at this and hated smelling like cold cuts after work, despite how much my dog liked it), FedEx warehouse grunt (great exercise, though not very mentally stimulating), and parking booth attendant (get paid to read books? Yes, please! Until the robots replace humans, that is).

But the job with Sidea was one of the most pivotal I ever had–even if the company went bankrupt a year after I started (not my fault!), a victim of the dot-com bubble bursting.

My job was simple: I had to man a booth in the middle of a CompUSA store, armed with a headset microphone and a large computer monitor. I was to demo software and hardware every thirty minutes—regardless of whether or not anyone was listening. Want to give a fourteen-year-old experience in public speaking? Tell him he has to demo random computer products to an entire CompUSA full of people ignoring him.

I can’t tell you how many demos I gave to no one. But I did every one of them as though my boss were watching. In between demos, I killed time browsing the Internet for the latest in Quake II news. For this job I was paid a ludicrous ten dollars per hour. I think I know why Sidea went bust.

But damn if that wasn’t a fabulous way for me to start public speaking. If you’ve experienced the embarrassment of the public speaker’s worst-case scenario (speaking to a roomful of people who are both ignoring you and hating you) before you’ve finished puberty, things are probably going to be okay.

One day I was approached by a man trying to decide between two different mice. I don’t recall the details, but there wasn’t a big difference between them, save the color and maybe another minor feature. I pitched him on his two options with a quip about the bonus “feature” of a different color. He laughed and offered me a job. He handed me his card and said he’d like to hire me for sales. I kept that card in my wallet for years until it finally disintegrated. Fortunately, I scanned it before it did.

Thank you Carlos & Steve. You have no idea how much you did for me. 

I didn’t have the heart to tell the man I was only fourteen. When I told my parents about the offer, they told me to finish high school first. I never called Steve Harper, general sales manager for Stanley Foods, Inc., but I had a hunch I was on the right track. I was always tall for my age, and weighing 260 pounds at the time also helped age me up, as much as being heavy may’ve sucked the rest of the time.

Being the tallest guy in the class and having a name that’s usually given to girls (in fact, I was named after a three-time title-winning boxer, Alexis Argüello) are enough to make a person stand out in school, but make him one of the most overweight as well and you’ve got a recipe for something. It easily could’ve gone the other way—self-loathing and depression—but I cared too much about video games and computers to realize how not cool I was.

Pure swag.

I overcame my weight by making jokes about it before bullies could. Girls were trickier, though. I nearly failed geometry because of a cute girl named Erin, who told me (well, she told my best friend, but so it goes in eighth grade) that I was too fat to go to the dance with.

Like a lot of my not-popular-but-not-pariah peers, we developed personalities and pursued hobbies that interested us, because “just being cute” wasn’t an option.

We tinkered on our computers and spent way too much time playing video games with each other. I started a nonprofit called FreeAsABird.org (I’m really regretting the WaybackMachine) that built free custom websites for small nonprofits that had little or no web presence. I e-mailed all my clients cold, and as far as I know they had no idea I was a teenager. After earning a 4.0 my freshman year, I did as little work as I could but still kept my grades up in high school so I could maximize my time spent gaming and running the competitive gaming teams I managed.

Thank goodness, too. Because that was a long-term investment in myself. Most schoolwork felt awfully irrelevant when compared to work that was actually affecting real people and giving me leadership opportunities (albeit digital ones), nurturing the community management skills that would come in handy later.

Of course, all that time in front of a monitor began to take its toll, as my metabolism wasn’t nearly as fast as my buddies’. Our fast-food binges may’ve done nothing but fuel LAN parties (that’s where lots of people bring their computers over to someone’s house to connect directly to a local area network—for gaming). True story: I’d never attended a party that didn’t have “LAN” in its name until college.

This pattern of eating wasn’t healthy. I got tired of being fat by my junior year of high school and decided to do something about it so I could get in good enough shape to play football before I graduated.

Thanks to regular exercise and the abolition of soda and junk food, I lost fifty-nine pounds. My pediatrician (who was always kind of a jerk) couldn’t believe it when he read it on the chart. And to this day I can’t believe how differently people treat me. To have been the “pear-shaped fat kid” for all those formative years and then join the ranks of the easy-on-the-eyes crowd is like turning on another life cheat code. One random night, I bumped into Erin (remember—from eighth grade?) at a movie theater—she literally didn’t recognize me. It felt great. I may have danced a jig when I got back to my seat to breathlessly tell my friends what had just happened.

There Are Nerds in College

I applied to only one college, the University of Virginia. At the time I didn’t give it much thought, but I can’t help wondering how much different life would’ve been if I hadn’t made that seemingly insignificant decision. I had no contingency plan aside from the local community college, much to my parents’ dismay. I included along with my application a CD-R with my “digital portfolio” on it. It’s rather embarrassing, but I’ve now uploaded it for your viewing pleasure. I’ll wait while you go look.

If you were drinking a cup of coffee at the time, I imagine you did a spit-take. If not, please don’t tell me, as I’d like to preserve the image.

Much to my parents’ relief, I got in to UVA. But that’s not the important part. The decision that defined my experience there and made reddit possible was checking the box for “old dorms” on the housing questionnaire. I didn’t know what this meant at the time; old dorms just sounded cooler than new dorms, which were really suites—I wanted something that looked like the colleges I’d seen in movies.

The day we moved in, I spotted a blond-haired guy playing Gran Turismo on his PlayStation 2 across the hall from my new dorm room. His name was Steve Huffman. I was thrilled because I’d worried that no one played video games in college—that this was something I’d have to leave behind as a relic of my childhood. Steve was much less excited to meet me, because he’d seen my name on the door and thought he was living on a co-ed hall. So I was excited that he played video games; he was bummed that I wasn’t a girl. He got over that, and we became best friends. Picking old dorms and ending up across the hall from Steve was one of the best, albeit most random, things that ever happened to me.

You’ve Got to Be Willing to Disrupt (and Be Disrupted)

My dad has been a travel agent for more than thirty years. I distinctly remember dinner-table conversations around the time the Internet started to disrupt the travel industry. As a high school student with a particular interest in computers and technology, I was especially enthralled with all the buzz around the “dot-com bubble.”

Dad, on the other hand, was watching his commissions from airlines get cut all the way to zero. Travel agents used to make good money from bookings that now were going to OTAs (online travel agencies). Because of this disruptive technology, people were now booking their own flights and hotels, cutting out the middlemen—people like my dad.

Just a few years before, my dad decided to leave his position at a large agency to start his own small travel agency. A first-time entrepreneur, he was now facing a dramatic shift in the way his industry did business—and there was no stopping it. The Internet was changing the fundamental business models for the travel industry.

One night he came home from the office particularly frustrated. He’d just learned from a major airline that they, too, would finally be eliminating travel agent commissions altogether. After years of being gashed by these airlines, my father sent them a fax to articulate just how he felt as his business was being eroded.

“Fuck you.”

He doesn’t remember if he put a cover sheet on that fax, but I like to think he did.

Unlike people in other industries, he couldn’t call his lobbyist on K Street and ask him to get a law passed that would make sure all travel agents get a commission. He had to adapt his business model. And he did. To this day, he continues to operate with a focus on business and first-time travelers (usually boomers taking their first cruise). It’s not an enterprise I’ll be likely to take over, especially given hipmunk, but it’s one he and his employees will, I hope, continue to run for years to come.

But those dinner-table conversations made an impression on me. The Internet was a powerful tool, and I wanted to be sure I knew how to use it. The free market is ruthless. But it has to be. It’s up to us to make the most of it.

We must be opportunistic—when disruptions happen we need to identify the new business models and adapt, as my dad did. Or better, we need to be the ones doing the disrupting.

I knew I wanted to be a disrupter.

Sometimes You Just Have to Stand Up

My commercial law professor at the University of Virginia, Professor Wheeler, one day commented in class on the fact that I always volunteered to be the demo person in front of the class when he needed human props. He said how important it was to show up, to stand up—lauding my effort. I just thought it was fun to be that guy in a class of hungover undergrads. It wasn’t that I thought I might get better grades, but I figured I had two legs, so why the hell not get up and use them?

I’d never expected to give a TED talk, let alone at twenty-six years old, but then again I’d never expected to be in Mysore, India, which is where I was in October of 2009 as an attendee of TEDIndia, one of the yearly TED presentations that the organizers host all around the world.

A month or so before the conference I was included on a massive e-mail blast from Chris Anderson, curator of the TED Conference, that included this attention-grabbing nugget:

It is commonly said that TED attendees are every bit as remarkable as those appearing on stage. It happens to be true. That’s why at every conference we invite you to consider whether you have something to contribute to the program—and possibly later to the wider TED community, through the TED.com site.

So there at my laptop I raised my virtual hand—so to speak—and submitted a pitch for a three-minute talk to TED. These are the palate cleansers in between the more heady and often very emotional eighteen-minute TED talks. I figured I’d better get right to the pitch. Here’s what I wrote:

The tale of Mister Splashy Pants: a lesson for nonprofits on the Internet. How Greenpeace took itself a little less seriously and helped start an Internet meme that actually got the Japanese government to call off that year’s humpback whaling expedition. People manage to sell entire books on the subject of “new media marketing” but I only need three minutes—with the help of this whale—to explain the “secret.”

How could they resist a name like Mister Splashy Pants? Splashy to his friends.

I figured they must’ve been totally floored with awe, because I didn’t hear back for a month. Was this just their way of saying no? I was already in India at this point, so I sent a quick “ping” e-mail to see if I could get a yes or no.

“Congratulations. You did get accepted.”

Hot damn, I had twenty-four hours to write and rehearse a talk people practice for months…

Better turn on some South Park.

Thanks to VPN, I could watch South Park from south India. The episode was called “Whale Whores” (season 13, episode 11), and it satirized the Animal Planet documentary-style reality show called Whale Wars (oh, puns!), which features the Sea Shepherd Conservation Society, an organization that harasses Japanese whalers in an effort to protect marine life.

In the episode, after hordes of Japanese storm the Denver aquarium during Stan’s birthday and slaughter all the dolphins (am I really writing about South Park right now? I love this country), an enraged Stan implores his friends to join him in protecting the dolphins and whales, which the Japanese seem so intent on eradicating.

Stan’s friends are not interested until Stan joins the cast of Whale Wars, at which point Cartman and Kenny pretend to be whale-loving activists in order to milk some of the fame associated with the show. They volunteer, despite admitting earlier that they “don’t give two shits about stupid-ass whales.”

I grabbed a screen capture of Cartman, in a Save the Whales shirt, proclaiming his love of whales; Kenny is beside him, dolphin lover (sic) scrawled on his chest.

That image reminded me of what was then one of the biggest events on reddit—voting for the name for a humpback whale that Greenpeace was tracking. This event has since been eclipsed by other events, such as the “money bomb” donation of over half a million dollars to DonorsChoose.org or fund-raising for three-year-old Lucas Gonzalez, who needed a bone marrow transplant. But the story of Mister Splashy Pants was a special moment in reddit’s development and proved to be a prophetic tale of the power of social media: for an idea to truly become mainstream, it needs to go beyond the early adopters—in this case, whale lovers like Stan—and also include those who want to join the trend.

A lot of people rag on PowerPoint (often rightfully so). But in the right hands, this much-maligned communication tool can actually be incredibly entertaining (and even informative). The problem is, most people don’t understand how to use it, which sets the bar for PowerPoint presentations really low. Here’s my philosophy: lots of big pictures, text, and tons of slides. For my TED talk, I had room for no more than a few words on each slide—and they had to be in 86-point type, minimum. Forty-two slides—a good sign, even though it meant I had only a little more than four seconds for each slide.

There was going to be a giant TED sign on the stage behind me. This could make or break my public speaking career. And I was going to be on the same stage where the brilliant statistician Hans Rosling, using beautiful data, emphatically demonstrated how India ascended to economic superpower status—meanwhile, I was going to talk about a whale named Mister Splashy Pants. No pressure.

I finished before sunrise and took a power nap. When I awoke I began feverishly practicing with my timer. I missed all the morning talks. I was terrified of Chris Anderson, who famously cuts off speakers when they go on too long. As someone who routinely talks more than I should, I didn’t want my talk punctuated by a giant cane pulling me offstage.

I’d later learn that TED does not in fact use a giant cane.

I don’t remember the talk before mine, because I was so busy trying to remember what I was going to say.

Why are my hands shaking?

Chris Anderson introduced me as Alex. I hate being called Alex, but I smiled and took the stage, trying hard not to trip on the way. When you’ve grown up embracing your unisex name (okay, it’s predominantly a woman’s name here in the United States), it’s incredibly vexing to hear someone shorten it to the male version. I’m a dude named Alexis; please call me by my name. Now I was thinking about Alexis Argüello, the three-time world champion boxer my father named me after, and I wondered if he ever had the same issue growing up in Nicaragua—shit, I’m supposed to give a talk right now.

Remember, it can’t go worse than a giant room of CompUSA shoppers actively ignoring you.

That got me started. Get to it, Ohanian.

“There are a lot of ‘Web 2.0 consultants’ [I made air quotes with my fingers] who make a lot of money—in fact, they make their livings on this kind of stuff. I’m going to try and save you all the time and all the money and go through it in the next three minutes, so bear with me.”

I breathlessly shared the story of Greenpeace’s dogged efforts to raise online awareness of their effort to stop Japanese humpback whaling expeditions. They wanted to track one particular whale on its migration and humanize it with a name chosen by their online community. Greenpeace staff chose about twenty very erudite names—like Talei and Kaimana (which means “divine power of the ocean” in a Polynesian language)— and then there was Mister. Splashy. Pants.

I enunciated each word one at a time for full comedic effect. Laughter. They’re not hating this.

Once a reddit user discovered the poll and submitted it to reddit.com, a surge of votes flooded in for this obvious favorite. Who doesn’t want to hear a news anchor say “Mister Splashy Pants”?

Greenpeace wasn’t pleased. They insisted on rerunning the voting process, which only galvanized us. I changed our reddit logo from a smiling whale to a more combative version.

For any scientists reading this:

This time, polls closed with Splashy having an even more commanding lead.

Oh no, I’m running out of time. Please let them be gentle.

Eventually they relented and let the online favorite win (sometimes you just have to let yourself be disrupted, remember), but at this point they’d inadvertently created a brand that excited far more people than just Greenpeace fans—the message had spread far beyond whale lovers. In fact, the Japanese government actually called off the whaling expedition.

Everyone who creates something online has lost control of their message but in the process has gained access to a global audience. Mister Splashy Pants is a story about the democratization of content online—starring a whale—and it demonstrated how little control we have over our brands. It turns out we never had control, only now we realize it. Before the social web, we had little idea of what people actually thought about us—now we know, and when like-minded people band together, they wield a really big stick.

The talk is over. Applause. Even a few “Woo!”s from the crowd.

Nailed it. I’d given a few non-CompUSA talks before then, but once the video of my TED talk hit a million views and was front-paged on reddit, I became a known “public speaker.”  In a brilliant illustration of my argument, the video was submitted to reddit with the following headline: “Nutjob mistakenly allowed to give TED Talk, he rambles for over four minutes before being carried off the stage.”

I have a lecture agent now and get paid more for a speaking gig than I did for an entire year’s work at Pizza Hut. It’s a little bit insane, but then I remember that I’m still getting paid less than Snooki [1], which makes me really question things.

I still get nervous before I get onstage—I just know how to better handle the nerves now. In truth, it really is all about practice. Once you’ve been onstage enough times and make sure you’re always well rehearsed and armed with the feeling that you really know what you’re talking about, it then becomes all about polish. Listen to yourself. I listen (not watch; I want to focus on the words) to every talk I give once afterward to see where the “ums” and “you knows” crept in. I’ll pay attention to jokes that didn’t work and others that worked better than expected—was it the joke or the delivery? Then I put that talk out of mind. Test, analyze, and repeat.

The Internet offers a wealth of great speeches, all freely available with just a few keystrokes. Find your favorite speakers and study them. I notice the way Jon Stewart disarms an interview subject with a joke before hitting him with a knockout punch. President Obama really knows how to hit the Pause button at the right moment for maximum impact. When used well, silence is powerful. And when I learned that Louis C.K.— easily one of the best comics of our generation—trashes all his material every year and starts anew, I knew I needed to keep from getting lazy and recycling entire talks. Louis does it because, he says, “The way to improve is to reject everything you’re doing. You have to create a void by destroying everything; you have to kill it. Or else you’ll tell the same fucking jokes every night.”

Being a stand-up comic is infinitely harder than giving a talk or a speech, so if he can stay that on top of his game, why can’t I?

There Are Much Harder Things in Life Than Being an Entrepreneur

Growing up, I had the words “lives remaining: 0″ written on the wall of my room. If life were a video game, that’s how it’d indicate this is the only chance left.

I’m lucky because I got that lesson when I was twenty-two years old and just a month or so out of college, feeling about as immortal as someone could.

But then everything changed with a phone call.

Why’s Mom calling me? She should be getting ready for her vacation trip to Norway.

She’s crying.

Max, our wonderful mutt, had to be put down.

Because I’m an only child, Max became my mother’s favorite when I left home for college—a position in her heart I could never reclaim. She absolutely adored him, and our family did everything we could to help him fight the Cushing’s disease that had finally taken its toll.

My mother was understandably distraught. I told her I loved her. I understood why she had to do what she did to our beloved dog and, although it didn’t work out that I could be there, I was grateful that she was. She had some more errands to run before meeting up with Dad and heading to the airport. She’d try to get through them the best she could, but I knew it was going to be hard for her to go on vacation.

At least it happened before she got on the plane.

My dog had just died. It was going to be a rough day in Boston. Startup life is extreme enough—every morning one wakes up thinking today’s the day you’re conquering the world—or today’s the day you’re doomed.

I got through that awful morning. I don’t remember what I was doing at the time, but my phone started buzzing again in the late afternoon.

Why’s Dad calling me? He should be at cruising altitude with Mom.

They’re in the hospital.

Howard County General.

On any other night Mom would be working there; she’d been a pharmacy technician there on the night shift for the last seventeen years.

Now she was missing the vacation she and my dad had planned for years.

She’d had a seizure in the dressing room of a department store, and an attentive clerk had called 911.

At least it happened before she got on the plane.

The initial brain scans revealed a tumor. The culprit in her skull was an insidious monster called glioblastoma multiforme. Such an ugly name. They were going to keep her overnight for more tests. She’d likely have surgery soon thereafter. I never should have done the Google search, but I needed to know what my parents would inevitably struggle to tell me.

I bought a ticket for a flight down first thing the next morning, but until then I was stuck in Boston. That night Steve and I tried to get our minds off things and went down to a local bar to watch our favorite team play their archrivals on Monday Night Football. Our Washington Redskins versus the Dallas Cowboys.

It was a really boring game. And we were losing it. So much for even a brief respite from the shittiest day of my life.

By the fourth quarter, there weren’t many TVs with the game still on (we were in Boston, after all). Back in Columbia, Maryland, my dad had already called it a night. He didn’t need any more heartache.

Steve and I had nowhere else to go and needed distraction—any distraction—so we kept watching. It was fourth and fifteen, and we were down 13–0 with less than four minutes left (non–football fans: just know that this means an exceptionally dire situation). Just then, Mark Brunell, a quarterback not known for his arm strength, hurled the ball downfield more than fifty yards to Santana Moss in the end zone.

It was 13–6!

But no one on the field was celebrating—and with good reason. There was hardly any time left, and we were still losing. Even the Cowboys’ mascot was taunting us with a dramatic look at his wrist to remind us that there wasn’t enough time left for our touchdown to matter.

But Steve and I kept cheering. What the hell. They had finally given us something to cheer about. That was our first touchdown of the season! And we’d been drinking, which always helps. We made the extra point, and it was almost a ball game. But that jerk in the Cowboys costume had a point.

Dallas ended up punting quickly, thanks to a stingy Skins defense, and we had the ball again (football novices: that’s our time to go on offense and score points).

First and ten from our own thirty-yard line. One of the commentators, John Madden, couldn’t even finish his run-on sentence before Brunell threw the exact same pass fifty-plus yards down the field right back to Moss, who again beat the coverage.

“And Santana Moss for a touchdown! Wow!” Al Michaels couldn’t believe his eyes as Moss hustled into the end zone.

At this point Steve and I were screaming. We were also the only two people still watching the game, I think.

Suddenly it was 14–13 and we were winning.

Winning? What?

Even when all hope seemed lost—see what happened there—we had to keep hoping, because that was all we had. As much as I wish I could affect the outcome of sporting events from my seat, there’s nothing I can do but cheer at the right times.

But it wasn’t over. Life isn’t a storybook. And what happened next is going to be exceptionally difficult to describe for non–football fans.

The Cowboys weren’t about to be upset so spectacularly in their own house on national TV. They briskly marched down the field, nearing field-goal range as the time kept ticking down. They didn’t need to reach the end zone; they needed to get just thirty-five yards or so from it. As long as they could kick a field goal, they could walk off the field as victors and dash our hopes.

They were that close, but only for a second.

A third-down completion to Patrick Crayton secured a first down and also put the Cowboys in field-goal range. Crayton got a step beyond the marker and then…contact.


You could hear the pop on the television broadcast. Sean Taylor, a lean and hungry safety, delivered a brutal—and legal—tackle that popped the ball loose, resulting in an incomplete pass.


I started yelling. Spilling beer. Probably also spitting a little. It was obnoxious because they kept replaying that hit and I kept yelling BOOM! louder with every replay.

Steve was yelling, too. Everyone else in the bar was hating us. We didn’t give a damn.

Later, I got my hands on the high-def footage of Taylor during and after that hit. He pops up, electrified. That fire. That heart. It’s something awesome when you watch a human—just another carbon-based life-form— doing what he does so well. And loving it.

That hit took all the air out of Cowboys Stadium, from the fans to the field. The Cowboys turned the ball over on downs, and Redskins players poured Gatorade on Coach Gibbs. Not a typical week-two celebration, but we thought it was appropriate.

Steve and I went home singing our fight song, and I had the joy of surprising my dad with the news the next morning. He’d never walked out on a game before and never would again.

I don’t believe in signs, mostly because I don’t think I’m worth all the trouble. But I was inspired.

Sean Taylor saved the day that night, doing what he loved and doing what he was so clearly talented at. It gave me a little bit of happiness on the saddest night of my life and confirmed that it’s never over until it’s over.

So I’d better not give up. And if I can find something I’m good at and love doing, I’m going to put everything I have into it.

Sean Taylor died two years later. He was shot by an intruder while at home with his girlfriend and daughter. He was twenty-four; just a few weeks older than I was at the time.

We often use words like bipolar and all-consuming to describe startup life. Fools compare it to combat, and over drinks even the more reasonable among us still veer into hyperbole about how hard it is to face the day some mornings. I’ve never lain in bed in self-pity, though. Even after that night I didn’t, because I knew back in Maryland my mother and father were dealing with a very different kind of morning. Perspective. My mom, the kindest person on earth, had been told she would die before seeing her grandchildren, and yet the first words out of her mouth when she saw me were “I’msorry.”

That’s the kind of person she was. I knew I’d lived a rather stress-free life until that point, and I knew that that would have to change. I just didn’t think it’d happen all at once. My mom came to this country when she was twenty-three because she was in love with my dad. After a few years of living together while she was still an undocumented alien, they secretly married at City Hall in lower Manhattan, and only later did they have the “public” wedding for their families (surprise, Grandpa!). Eventually the cost of trying to raise a child in New York City (even in the boroughs—Brooklyn and then Queens) proved to be too much, and my parents moved to the suburbs of Maryland, where my dad’s modest income could go much further.

My father had a degree in urban studies and architecture from Antioch College, and my mother wound up getting her GED in 1980, just three years before I was born. She went on to work night shifts as a pharmacy technician, sleeping only a little so she could be present for more of my waking hours.

After all that, my mother—who had supported me my entire life, filled me with confidence, and loved me dearly—was telling me she was sorry she’d inconvenienced me by getting terminal brain cancer because it was something else I’d have to deal with?

Being an entrepreneur was the best decision I could’ve made, because not having a boss gave me the freedom to make my family a priority without compromising my work. I got a lot of use out of that 3G USB stick and laptop. As long as I had those two things, I was in the office, whether it was bedside at Hopkins or in the reddit headquarters in Somerville.

I write this all as a precursor to my story—to hell with chronological order—because as empowering as the Internet is (and boy, is it empowering), we must all still succumb to a common mortality.[2] I would trade anything to have my mom back, but in lieu of that, I can only work to honor her a little bit more every day.

To be reading this book, thinking about how to use this great platform, the Internet, to share your world-changing ideas, ideally from a comfortable seat somewhere, is itself a great luxury. We’re living in a time of unprecedented opportunity across the globe that happens to coincide with a time of tremendous misfortune.

Let’s make the most out of this great hand we’ve been dealt, eh?

More stories from reddit, hipmunk, breadpig and beyond are in the book, available in book-book or e-book form, as well as on audible. Read some reviews on Goodreads (or leave your own!)

  1. This is a cultural reference from the early twenty-first century. Readers in the mid-twenty-first century and beyond will probably know her as President Snooki. I mean no disrespect.
  2. Except for the sentient robots. They’re going to be fine. Don’t shed a tear for them, because they wouldn’t for you—and they can’t; that’d be a lot of needless engineering.

The Next 2 Days Are Very Important for the Open Internet


I'm nervous, but also excited. Mostly excited, but still a bit nervous. The next two days are going to be big.

New Yorkers: Teachout Wu FTW!

If you're a New Yorker, or know one, please vote (or tell them to vote) in today's primary for governor and lieutenant governor -- and vote for Teachout + Wu. I formally endorsed them yesterday at an event where they unveiled their tech policy for New York State. It made me so happy to see people who actually understood these technology issues (as I said, "Wu is an O.G. of the open internet") and cared so deeply about serving New Yorkers.

This is the first time I've ever endorsed a candidate. I'm going to be dancing all the way to the polls today. 

Internet Slowdown Day is tomorrow

There hasn't been an internet-wide protest like this since SOPA/PIPA and the internet needs your help to survive. I published an op-ed on The Verge about this very subject. 

All of your favorite websites are going to be very slow tomorrow to make sure the FCC realizes the fate of the open internet is in their hands as they have a chance to reclassify broadband as Title II (the public utility we all know it to be) and put an end to what John Oliver aptly described as "Cable Company Fuckery."

Please spread the word about Internet Slowdown Day and demand an end to "fast lanes." There's still time left to file a comment with the FCC (here's mine on behalf of Y Combinator!)

SOPA 'em!

Just a couple years ago we were in a similar situation with SOPA/PIPA, but against all odds, we the people prevailed. And we shall again.