Today, I’m very excited to return to Initialized Capital as a full-time General Partner alongside my longtime friend and collaborator Garry Tan.

Here’s a little history first. Initialized launched in 2011. Before that, Garry and I were having success as angel investors and founders kept telling us we were providing more value than other much better funded investors.

Before long, we’d raised $7 million for our first Initialized fund, which made seed investments into startups like Instacart and Coinbase. We were on to something.

Since then, we have grown to manage more than $250 million, which is invested in companies that are now worth more than $20 billion (including six unicorns, startups that are worth over one billion dollars). We’ve recruited a remarkable team of partners, and built a ton of software to scale all of the traditionally high-touch, and less scalable parts of the venture business to better serve our founders.

We want to be the first check and we want to do the work — we aspire to be the kind of investors we wish we’d had when we were founders. And after more than three years of serving back at Reddit, my first “baby” is in a much better position and has a great team in place.

via Ro Khanna

Thanks, Jimmy!

Been looking forward to saying that for a long time. Click here and then follow me on Reddit, my posts will show up on your frontpage, and you can join the discussion around them (the best part).

I'll be sharing all kinds of never-before-seen Reddit history, as well as present musings, and a glimpse into the future, too.

Our tech community in SF turned out big-time on a very rainy night this weekend to celebrating the third fund of Initialized Capital. They're the reason we get to do this, for that we're grateful.

Lots of people, but I only got a few photos...

This post is sponsored by Chase Ink®

I’m proud that Reddit is the seventh largest website in the U.S. with millions of users worldwide. But it wasn’t always that way.

When we started, my co-founder Steve Huffman and I faced some enormous hurdles on the meandering pathway from the initial idea to an up-and-running business. 

We made it, but it could have been easier if we knew then what we know now.

Whether you are just launching a new business or are a serial entrepreneur, there are best practices for making the journey a bit easier.

Here are three actions that I believe are must-dos to ensure your company survives and thrives.

1. Embrace your culture. There’s a reason why people want to work for your company, and the paycheck isn’t usually #1. Culture is the glue that holds your team together, that drives people to do their best work. 

But if you grow too fast, you can lose control of that culture. For instance, Reddit has strived to never double our headcount in a single year (I know, I know, a nice problem to have). The point is … stay true to what guides your company. Believe me, it’s what draws customers – and employees – to your brand. 

2. Spend smarter. In the early days of a startup, or when the company hits a growth spurt, it’s easy to lose control of expenses. For me, travel expenses have always been a struggle to control. Because our company is global, I’m always on the move. And that can quickly overwhelm the budget. 

Look for ways to save while spending. You may have seen one way I recommend doing it, in this video. I’ve been a Chase customer for a while, and the new Chase Ink Business Preferred Card helps business owners get something back for their spend on certain purchases important to entrepreneurs. Earn 3x points on travel, internet, cable and phone and in other select business categories.  Points you can redeem down the road, for things like … more travel. Ahh, the circle of life. 

3. Protect your biggest asset … you! At the ripe old age of 33, I’ve finally started to take better care of myself. Not so much in the early days at Reddit. I worked all the time, and I loved it. But there is a cost to bear, both physically and mentally. 

Now, I spend more time exercising and being careful about what I’m eating – and I feel more productive and effective when working. I wish I’d started taking care of myself a lot sooner. Don’t make that mistake. 

At the end of the day, we’re in business to make money. That’s a tough proposition even in good times, but it’s even more difficult if you’re not in control of your business culture, your expenses or your health. 

##

Alexis Ohanian, co-founder of Reddit, and other small business owners are finding creative ways to use the rewards points earned on their business credit cards to invest in their business. Learn more about the new Chase Ink Business Preferred^SM Card and its flexible and rich rewards.

Below is a copy of the post I wrote for Reddit yesterday. It was an intended to be an open letter, to encourage other American redditors to share their own or their family's immigration stories. Within 9 hours, this post had a record score of over 90,000 points and over 25,000 comments. Many of these stories were far more eloquent and moving than my own. Please read them here.

After two weeks abroad, I was looking forward to returning to the U.S. this weekend, but as I got off the plane at LAX on Sunday, I wasn't sure what country I was coming back to.

President Trump’s recent executive order is not only potentially unconstitutional, but deeply un-American. We are a nation of immigrants, after all. In the tech world, we often talk about a startup’s “unfair advantage” that allows it to beat competitors. Welcoming immigrants and refugees has been our country's unfair advantage, and coming from an immigrant family has been mine as an entrepreneur.

As many of you know, I am the son of an undocumented immigrant from Germany and the great grandson of refugees who fled the Armenian Genocide.

A little over a century ago, a Turkish soldier decided my great grandfather was too young to kill after cutting down his parents in front of him; instead of turning the sword on the boy, the soldier sent him to an orphanage. Many Armenians, including my great grandmother, found sanctuary in Aleppo, Syria—before the two reconnected and found their way to Ellis Island. Thankfully they weren't retained, rather they found this message:

“Give me your tired, your poor, your huddled masses yearning to breathe free, the wretched refuse of your teeming shore. Send these, the homeless, tempest-tossed to me, I lift my lamp beside the golden door!”

My great grandfather didn’t speak much English, but he worked hard, and was able to get a job at Endicott-Johnson Shoe Company in Binghamton, NY. That was his family's golden door. And though he and my great grandmother had four children, all born in the U.S., immigration continued to reshape their family, generation after generation. The one son they had—my grandfather (here’s his AMA)—volunteered to serve in the Second World War and married a French-Armenian immigrant. And my mother, a native of Hamburg, Germany, decided to leave her friends, family, and education behind after falling in love with my father, who was born in San Francisco.

She got a student visa, came to the U.S. and then worked as an au pair, uprooting her entire life for love in a foreign land. She overstayed her visa. She should have left, but she didn't. After she and my father married, she received a green card, which she kept for over a decade until she became a citizen. I grew up speaking German, but she insisted I focus on my English in order to be successful. She eventually got her citizenship and I’ll never forget her swearing in ceremony.

If you’ve never seen people taking the pledge of allegiance for the first time as U.S. Citizens, it will move you: a room full of people who can really appreciate what I was lucky enough to grow up with, simply by being born in Brooklyn. It thrills me to write reference letters for enterprising founders who are looking to get visas to start their companies here, to create value and jobs for these United States.

My forebears were brave refugees who found a home in this country. I’ve always been proud to live in a country that said yes to these shell-shocked immigrants from a strange land, that created a path for a woman who wanted only to work hard and start a family here.

Without them, there’s no me, and there’s no Reddit. We are Americans. Let’s not forget that we’ve thrived as a nation because we’ve been a beacon for the courageous—the tired, the poor, the tempest-tossed.

Right now, Lady Liberty’s lamp is dimming, which is why it's more important than ever that we speak out and show up to support all those for whom it shines—past, present, and future. I ask you to do this however you see fit, whether it's calling your representative (this works, it's how we defeated SOPA + PIPA), marching in protest, donating to the ACLU, or voting, of course, and not just for Presidential elections.

Our platform, like our country, thrives the more people and communities we have within it. Reddit, Inc. will continue to welcome all citizens of the world to our digital community and our office.

And for all of you American redditors who are immigrants, children of immigrants, or children’s children of immigrants, we invite you to share your family’s story in the comments.

The next big march on Washington could flood the Mall with scientists.

It's an idea spawned on Reddit, where several scientists — concerned about the new president's policies on climate change and other issues, and hyped from the success of the Women's March on Washington — were discussing the best way to respond to what they feared would be an administration hostile to science.

Then someone wrote, “There needs to be a Scientists' March on Washington.”

"100%,” someone replied. Dozens of others agreed.

One participant in the exchange, University of Texas Health Science Center postdoctoral fellow Jonathan Berman, took the conversation to heart. In short order, the march had a Facebook page (whose membership swelled from 200 people on Tuesday night to more than 300,000 by Wednesday evening), a Twitter handle, a website, two co-chairs, Berman and science writer and public health researcher Caroline Weinberg, and a Google formthrough which interested researchers could sign up to help

I recently got a Reddit PM from a reader of Without Their Permission that absolutely made my week and he allowed me to share it.

Getting on the bestseller list is great, but getting an email like this is everything for an author. You write a book because you hope it takes someone away from their life for a few hours to really open up a new way of thinking. In this case, helping them help themselves change their life in a material way for the better.

Ben, your choices are going to pay dividends for you the rest of your life and I'm hoping to hear from you over the years as you keep leveling up. Thank you so much for this note. And thank you for your service.

If you don't like images, here's a copy of the text:

Hey Alexis,

I messaged you on Facebook and I'm not sure you'll get it, so I figured I'd try to reach you here as well to tell you how you've helped me.

A little over two years ago, I was a Marine deployed on the Naval ship USS Bataan. At this point, I had left college at the University of Rhode Island because I just didn't care about learning, I guess I just never had a passion for learning. Anyway, I magically saw Without Their Permission in the ship library and decided to check it out. After reading it I was completely inspired, and began teaching myself Javascript. For once, I loved learning--and it was because of your book. I spent every waking minute immersing myself in Javascript and learning about startups. This eventually led me to begin reapplying to college to continue down the path of education that your book took me on.

I ended up interviewing for a leadership scholarship to Dartmouth College, and they thought my story of becoming passionate about code was compelling enough to award me a full scholarship. I just started school this fall, and I'm loving it.

At a recruiting lunch on Tuesday, I was asked about how I began coding and immediately mentioned reading your book a few years ago. Recalling all of these memories made me want to reach out to you and thank you. I'm not sure what your book was doing in the ship's library, among dry manuals about military tactics and such. All I know is that I'm extremely thankful that you wrote such an inspirational book, and that it happened to be there for me.

Thanks!!!

Ben [Redacted]

HP Presents Reinvent Giving with Alexis Ohanian from Collectively on Vimeo.

Looks like we just leveled up, according to Alexa, to the 7th largest website in the USA.

Thank you for all the upvotes. ⬆️ We've still got a lot more work to do.

I loved seeing this collaboration Reddit did with COSMO. There is such a diverse range of dating- and relationship-themed communities on the Reddit platform and the audiences there made for a great survey crowd.

I shared this story on stage at Web Summit and thought I'd share the screenshot of the original upvote (and downvote). You see, before I designed the now ubiquitous upvote ⬆️ and downvote ⬇️ arrows, we started with "interesting" and "boring."

Thanks again for a wonderful time, Libson!

Met a founder yesterday in Waterloo who had saved this postcard I sent him over 7 years ago. ⬆️ IIRC his girlfriend had ordered him a Reddit shirt, which I of course personally packed and shipped with a note -- and a postcard I designed, signed by the ENTIRE team in SF. Yes, 5 of us.

Here's an excerpt from my book, Without Their Permission, about Hipmunk, which feels particularly relevant given the news of its acquisition by Concur last week.

"It’s really hard to design products by focus groups. A lot of times, people don’t know what they want until you show it to them." -- Steve Jobs

“Adam really wants to call it Suckage, but that won’t fly,” Steve explains to me as we’re discussing the default sort option for our soon-to-launch travel search engine. It’s about halfway through August in 2010, and I’ve only been on the team a week. I’m sleeping on Steve’s sofa while we work in the living room of our friend and hipmunk co-founder and CEO, Adam Goldstein. The idea for the search engine is simple enough: make sure people get the best flight for their dollar, maximizing suck reduction (a scientific term) by ranking flight search results based on criteria beyond price alone, such as number of stops and flight duration. We’re days away from launch, and Steve is browsing through an online thesaurus for various synonyms for pain when he comes across it: agony. 

Agony. We’ll take the agony out of online travel search. 

Words couldn’t express how delighted I was. Adam somewhat randomly picked the name of the site after his girlfriend wisely suggested choosing a misspelling of a cute animal (perfect for an Alexis mascot!), and the name hipmunk (chipmunk without the c) was available at auction for a low price. Though I’d have protested, it could’ve ended up being called BouncePounce, but the concept of “agony”—and taking it out of  travel—was so awesome I don’t think Adam or Steve even realized it at the time. We’d stumbled onto the perfect word for branding our delightful alternative to everything in the travel search market. So while Steve built the ultimate product and Adam hustled all the deals that would let us take off, I’d take advantage of every opportunity to build the hipmunk brand. 

But first, let’s go back a couple of months. Steve first told me about the idea in May via e-mail: 

Basically, we’re doing travel search. . . . It’s not too glamorous, but it’s a huge market and the big players really suck.

Steve never was a salesman, but he certainly could get to the point.

In San Francisco, I got an early demo of the  then-unnamed travel search website. It was a rather unexciting list of search results, just like any other travel search engine you’ve ever used, except this one didn’t have any polish. I wasn’t too impressed. But Steve said they’d been noodling on some different ways to present the data that were going to be infinitely more  user- friendly. I trusted him, but I went back to Brooklyn thinking he and Adam were a long way from that minimum viable product (or as the cool kids say, “MVP”). 

In my mind, searching for flights was already a solved problem. It worked well enough to allow me to sit at my laptop and, if I had enough tabs open, not bother my dad about finding me a good flight to San Francisco. But Adam knew it could be so much better. You see, Adam realized he had a problem booking flights back in college. He ended up memorizing airport codes from AAL to ZRH because the MIT debate team competed all over the globe, and Adam had the unenviable job of booking flights for everyone. He absolutely hated it. It was too hard running all those searches, in all those open tabs of his browser, while deciphering hundreds of search results that confounded him with codeshares and tight connections (or ludicrous layovers). 

If finding a good flight is this hard for an MIT graduate, what about the rest of us? At first, however, Adam had a hard time persuading other people that it could be any different. This is a common problem for entrepreneurs who try to solve problems people don’t realize they have. It’s not  until you present most  people—even me—with a better alternative that they realize how bad things used to be. That’s why it’s important for the founders of any Internet company to build something so damn useful that everyone wonders how they ever lived without it. 

So after Adam graduated, he came to Steve to talk him out of early retirement. Steve, however, was significantly less enthusiastic when he heard the pitch. “I totally agreed that it was a nice company to start because it was close to people’s wallets,” he told me. “But I hated travel. It’s an industry that’s so not startup friendly.”

Soon, however, Steve realized that this hostile market was the perfect reason to try disrupting it with smart innovation— because it was so starved of quality solutions. “No one was thinking about what consumers really want,” Steve said, and soon he and Adam got to work on revolutionizing travel search. 

They applied to Y Combinator and didn’t have any trouble getting accepted, given Steve’s history. Several people have asked me why Steve would do the program a second time around, giving up a chunk of equity again, despite having more experience, connections, and even personal wealth than the first time. But as I tell them—Steve is not a dumbass. He wouldn’t do it if he didn’t think it was worth it. So there he was going through Y Combinator again, the baby-faced graybeard in the room for those weekly dinners (you’ll learn more about this in chapter 5). Another month later I found myself back on the sofa in Steve’s apartment, and he had something new to show me.

Aha! Here was the invention I didn’t realize I couldn’t live without until I saw it. It was beautiful. All the search results in a beautiful visual layout that looked something like train schedules I remembered from European backpacking  trips—and all on one page! No more scrolling through pages of results. You could easily compare flights—the duplicates were automatically hidden, along with flights no human would want to take. Oh, and just because opening multiple browser tabs was a nuisance, Steve and Adam had baked the tabs into the website. You could instantly open a new tab and compare itineraries within seconds and in one window. It was awesome, and it made sense. That’s why you build. Don’t tell me a story, show it to me. 

We had a little less than a week to get ready for the launch, but we still had a long way to go. We didn’t even have a name. Or a cute mascot. An adorable rodent was part of the plan with a name like hipmunk, since we could tell people “chipmunk without the c,” as though that had anything to do with travel search. Admittedly, the first time I heard the name, I thought it was a cool guy with a shaved head in saffron robes. Just to be safe, we also own hipmonk.com but have no plans to expand our business into taking the agony out of tonsure. 

I got to work on the branding. Fun fact: I was looking for font inspiration and grabbed the Redskins font (or at least a very similar font called Pythagoras, as in the brilliant Greek mathematician—he struck me as someone who’d have enjoyed hipmunk). It looked great in lowercase, and to this day it’s the font of hipmunk.

By that time, I’d also put together the first sketches of the hipmunk himself. I was really proud of my  pear- shaped chipmunk. He had buckteeth, sported a fetching aviator scarf and goggles, and pretended to fly by holding his arms outstretched, like wings in a child’s imagination. I sent the first version to my girlfriend, who said it looked like a bear with buckteeth. At least I got the buckteeth right. Please don’t go sharing this story around—I’ve got a reputation to uphold. 

Whenever I’m working on a design, whether it’s a brand or a user experience, I always rely on a small council of trusted friends to turn a fresh eye on the project and give me candid feedback. This has only gotten more valuable as I’ve gotten more successful, given that success seems to naturally have an inverse relationship with the amount of constructive criticism one receives. Just say no to  yes- men. I’m terrified of faltering, so these people are my motivation as much as they’re my inspiration. 

It still needed a slight tilt to give it that perfect touch of mirth and motion. I knew it was done when Steve’s wife walked into the room, saw my monitor, and her immediate reaction was an audible “Aww!”

When I sent the final version to my dad, he told me he liked it but said, “I liked the goggles and scarf better the first time, when I saw it on Rocky the Flying Squirrel.” 

Right. Thanks, Dad. I vaguely remember catching reruns of that cartoon as a child. The similarity was  unintentional—it came from my subconscious—but it just goes to show that we’re all standing on the shoulders of giants (or giant rodents). 

How to Win Deals and Influence Industry Titans 

Totally unlike reddit, hipmunk has zero user-generated content; the value of the site comes from how we display the content provided by airlines and hotels. Back then, we just needed flight information (remember, minimum viable product), but we couldn’t just scrape the data off airlines’ websites (scraping is essentially sending software to “read” and copy content from other websites). Most important, we wanted to get paid every time someone bought a flight that we helped him or her find on hipmunk. 

This was a great lesson: as the saying goes, we wanted to be “near our users’ wallets.” We were far from it with reddit, which made its money primarily through advertising, but we were totally there from launch day at hipmunk, thanks to some incredible hustle from Adam. 

We weren’t taking off unless we had airfares from providers. The data alone was invaluable because it’d make the site functional, but a business deal would also generate revenue from launch day — hipmunk would get a percentage of every ticket booked through us. Every single one of the fares on hipmunk (or on any of our competitors’ sites) is the result of negotiation with a carrier or OTA (online travel agency). 

Those negotiations may take months, or even years, and we simply didn’t have that kind of time. If we were to launch within the Y Combinator time frame (more on this in chapter 5), we had less than three months to build and launch. 

We needed someone to bite, because it would validate our business and help close other potential partners. Social proof in business development is not unlike fundraising for your company (also see chapter 5). It’s a dreadful catch-22 in which no one wants to do business with you unless you’ve already got someone doing business with you. It’s similar to the challenge Steve and I had when we launched reddit with only the two of us as users while trying to encourage a community to form, which is more easily accomplished by making up fake user names than by hiring actors who pretend to be past business relationships. The way to break this particular cycle is with pure hustle, which is just what Adam did. 

It started innocently enough, with phone calls and e-mails. Adam was polite and to the point, but no one responded. When he didn’t get what he wanted, Adam didn’t wait for anyone’s permission. He just got on a plane. No meeting  planned— he just got on a plane from SFO to ORD. He landed in Chicago and stopped by the offices of Orbitz (one of our OTA business development targets), announcing that he had some spare time to meet for a quick cup of coffee. Eventually, someone agreed, and armed with a laptop, he did a quick demo to show off what he and Steve had built. That hustle is what got us the pivotal first deal that let us launch hipmunk as planned. Then, because we had social proof, we took advantage of the same herd mentality that had previously worked against us. We may have been a tiny startup in San Francisco, but what mattered was we had a product that clients (or at least a client) wanted. 

This particular deal was quite fortuitous, as Adam would discover, because we were now presenting a wide range of fare data from scores of airlines. We could approach each of these airlines with an offer to do a deal directly with  them— we’d get a higher commission, and the airline would still be paying less than what they paid Orbitz. Everyone would be happy (well, maybe not Orbitz, but that’s to be determined). So Adam started working his way down the list of domestic airlines, then foreign, then domestic hotels, then foreign, et cetera. Right down the list. And it all started with a plane ride and a cup of coffee. 

An important coffee with Paul Graham changed our lives in chapter 2. There’s another pivotal cup of joe in chapter 5. If nothing else, I hope this book convinces you to go out and drink more coffee.

All Adam’s debate training paid off in the boardrooms of airline and OTA executives. Once he finally got in the door—and he did some impressive things to get there, like scheduling last- minute flights and dropping notes to employees saying that he’d be in town for just a hot minute—he finally got to decision makers at some of the country’s biggest airlines and OTAs. 

Granted, connected investors and networking can help tremendously, but don’t count on it. We have some awesome investors and advisers at hipmunk, but when it came to landing United Airlines, Adam came up empty-handed. So he went back to e-mail. Since we’d launched, we’d gotten a fabulous response from the online community and quickly became darlings of the early adopter crowd. This helped us get press, which encouraged more people to try hipmunk, which they inevitably talked about on social media, which helped us get more press, and the cycle continued. Soon Adam felt like he had enough wind at his back to try a cold e-mail to the United CEO, Jeff Smisek. 

I’ll dig into this more in chapter 5, but note the length and content of the e-mail Adam sent to Jeff: 

Hey. We can lower your distribution costs. Let me know who to talk to.

Adam got a response in fifteen minutes. It contained an introduction to a senior exec, and it all rolled smoothly until a deal was done and hipmunk was partnered with United Airlines, at the time the world’s largest airline.

The deal still took about a year to close, but its origin was that direct e-mail Adam had the audacity to send to the CEO of United Airlines. Hipmunk is a great example of the value of persistence, because travel is such a turbulent industry. One has to be tenacious, because there are always layoffs, mergers, promotions, chaos. The people you build a relationship with could be at another airline or out of the industry before the ink dries. 

But it worked. And knowing this is possible for the ever-changing travel industry gives me hope for almost every other industry. 

On our side we had Adam Goldstein, the MIT whiz kid (damn, I must have said that to every single reporter I pitched hipmunk to) who memorized airport codes and simply would not take no for an answer; an ingenious and beautiful user interface; and an  aww-inspiring mascot. But we would’ve been hosed without partnerships. The first one, like your first first down, is the hardest to get, but once you get it, it gives you the confidence and momentum to get more. 

I can only imagine how many secretaries Adam sweet-talked. And that reminds me— bring chocolates, because winning over the people on the front lines makes a difference. Take care of the people who can take care of you. This tactic has never disappointed me; it’s only pleasantly surprised me.

Sick to His Stomach on Launch Day 

Of course, Steve had already launched a website once before with reddit, but that was when no one was looking. Along with all the advantages that actual experience grants us, we lose the naïveté and blind audacity that being a novice affords us. When you’re a pair of nobodies launching a “social news website” in Medford, Massachusetts, no one (except maybe your mom) has high expectations for you. 

You could fail a thousand times and no one would know, so why are you hesitating to launch? 

Back in 2010, Steve Huffman was already well known as a top developer in the industry, and, as you know from chapter 2, reddit was (and continues to be) a great success, thanks to his work. Would his sophomore effort be a slump? 

That morning, Steve told me he wanted to puke. 

Fortunately, launch didn’t disappoint. What a difference just five years had made. Whereas it took me months to generate any kind of attention for reddit from mainstream media, CNN reached out to us within twenty-four hours of hipmunk’s launch. The launch was spectacular; Steve did not vomit.

Want to Read More? Get a Copy of My Bestseller, Without Their Permission.

Read Rayouf's AMA on r/twoxchromosomes. You'll have to remind yourself that she's just 15 years old. Please share this widely and we'll update when we hear back about our proposal.

Proud to be working with @RayoufAlhumedhi and @jenny8lee on a proposal for the Unicode Technical Committee to add a headscarf emoji, for millions of women across the globe to be represented. She's doing an AMA in the @Reddit community r/twoxchromosomes right now (link in bio) and is easily among the most impressive 15 year olds I've met. Why? Emoji have become such a big part of our communication (historians are going to have fun so much fun with this) that to leave out hundreds of millions of people is glaring. As a white American man I've greatly benefited from the different perspectives I've found on communities like r/islam where people are speaking freely about feeling marginalized. Emoji may not seem like a big deal, but it's one more way for a lot of people to feel acknowledged and represented -- and that's a good thing. ⬆️

A photo posted by Alexis Ohanian (@alexisohanian) on Sep 13, 2016 at 10:39am PDT

A small mattress company (yes, a mattress company) generates over $60,000 monthly from this single organic post in the r/minimalism community. That's the power of authenticity at scale. That's the power of Reddit.

Had a surprising moment on r/MildlyInteresting Reddit today--it seems Snoo ended up on this children's toy.

I got started chatting with Redditors and answering questions about the early days and how that doodle I made while bored my senior year at UVA ended up on a fake plastic credit card.

Here's an excerpt from my book, Without Their Permission that covers how Reddit got started. Since I've already typed it out before, I figured I'd just share it online.

Early Decisions

Once we were accepted into Y Combinator, we got back to studying for finals and enjoying our last weeks of college.

On 4/14/05, Steve Huffman wrote:

Paul said it would be nice to whip up a prototype. We don’t need to make anything work, but a quick page to show what our site might look like could be cool. Do you have any time this weekend?

Steve

To which I responded:

yeah man,

sat afternoon or sunday—all day sunday would work well. i have some ideas, but i’ll need to sit down and sketch some things out with ya.

-alexis

There it is. Were you expecting something more dramatic? Two college seniors just agreeing to get together over their laptops one weekend. That’s how mundane starting what would become the 9th largest website in the USA is. There’s no parting of clouds or springing from foreheads—just deciding to set aside some time on a Sunday to get some work done.

We did start thinking about reddit a bit, although I didn’t come up with the name until a couple of weeks later. I promptly registered it on April 29, just a few days after my twenty-second birthday.

After graduation, Steve and I started working in earnest in a rented apartment in Medford, Massachusetts, a quiet neighborhood outside Cambridge. I’d found the place, which was subleased by some Tufts students, on craigslist; all I knew was that it needed to be on the MBTA Red Line and it had to be cheap. We’d shown up with a month’s worth of clothes (it was already furnished), our laptops, and some sketches in our notebooks, including one of the logo and one of our alien mascot (in truth, I’d created these months before we’d even figured out how the site would work. Priorities!).

Steve and I set out that June to build a website where readers, not editors, would determine the front page of what’s new and interesting by submitting links to be voted on by the community. We had no ambitions to have the president of the United States conduct a real-time interview with millions of people on our site, which he would end up doing—from Charlottesville, no less—seven years later; we just wanted to create a place where anyone at any time could find what was new and interesting online. These could be links to an article, a video, or even a photo of a cat; if users like it, they vote it up (and vote it down if they don’t). Neologisms like upvote and downvote came into existence without any forethought—I just liked the way an up-and-down arrow looked.

The first version of the site used two words a user could click on, interesting and boring. We even debated dropping the “negative vote”—whatever it’d end up being called or looking like—in favor of a binary “I like this!” button, perhaps in the shape of a star. Fortunately, we’d already had a taste for how good it felt to bring a bit of retribution to the submitter of a bad link with a click of the downvote button, so it stayed and I got back to redesigning exactly how those arrows should look—down to the pixel.

We didn’t anticipate how much people would adore getting these upvotes, but we did know that the karma score (your total upvotes minus your total downvotes) would be a great incentive, especially early on, for people to submit. And when you’re trying to build a community from scratch, you need a simple system to encourage participation. The point system was neither novel nor fancy; it just worked. Steve engineered a clever algorithm to keep links rising and falling based on their votes and time, producing constant freshness.

The most pivotal product decision we made seemed much less important at the time but was our first big fight. I really wanted “tags” as a way to categorize content, and Steve insisted we let users launch their own reddits within our network (we’d call them subreddits). Just like WordPress was a blogging platform for online publishing, reddit would be a platform for online communities. It didn’t seem important at the time, but Steve was absolutely right and it’s a damn good thing he won because that decision would ultimately drive reddit’s success where all of our then competitors failed. We combined this simple point system with the ability for anyone to create a forum for an online community to share and discuss links—from NFL fans (r/NFL) to corgi lovers (r/corgi). The resulting network is a black hole of productivity worldwide.

We applied essentially the same model to our commenting system, which as a result generates the best discussions on the Internet. We added that commenting system a few months after we launched and I still remember Steve promising “something awesome” as he dashed off to get started building it—boy, did he deliver. I wish more people copied the reddit commenting system so I wouldn’t have to question my faith in humanity every time I watch a YouTube video and glance at the comments. But we started, as all startups do, with only ourselves as users.

I came up with the name reddit (as in, “I read it on reddit”) while I was in the Alderman Library at UVA one day, but we didn’t settle on it until just a couple of weeks before the launch. It was almost reditt, but fortunately I asked my friend Melissa Goldstein which bastardization made more “sense.” She chose wisely, and I stuck with reddit from then on. Yet it nearly became something else. Thanks, Melissa.

Excerpt from my bestselling book, Without Their Permission: How the 21st Century Will Be Made, Not Managed.

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.

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.

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.

(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.

As you can see, Steve downvoted my first submission (the first ever submission on reddit).

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.

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.

BOOM!

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.

BOOM!

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.

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.

Engage!

Had such a great day visiting the MakeGamesWithUs Summer Academy and then bringing a couple of the students over to FOX for a TV appearance talking about educating this new generation of app developers. So excited to see where they all go from here.