Magic Tricks

Back in my junior year of college, I switched my major from Cinema Studies to Economics. I was sitting in the office of my favorite professor and adviser, a man who had his Economics degree from Harvard. I was asking about post-graduate options.

"I was thinking about maybe getting an MBA one day. Do Oberlin graduates stand a chance of getting into the Harvard MBA program?"

My adviser smiled in a good-humored way. "Honestly George, I don't know how anyone gets into the Harvard MBA program. I think you have to be magic to pull it off."

When I heard those words, my heart sank, but I took the advice to heart. Seven years and two startups later, I still vividly remember that conversation because it crystallized my understanding of how to pull off a seemingly impossible accomplishment: it's a magic trick.

Getting into the Harvard MBA program might embody a magic trick for most people, but magic tricks encompass anything that appears to be impossible on the surface. Retiring at the age of 30, traveling full time while working remotely, being a C-level executive at a Fortune 500 company, or knowing people of repute. All of these accomplishments work to confound explanation and increase the perceived importance of the speaker. After all, only 1 in a million spend our evenings rubbing shoulders with A-list celebrities and our days on the cover of a business magazine. It's unique, it's interesting, and it defies simple explanation.

But it's a mistake to write off such accomplishments as impossible. It's an even bigger mistake to write them off as unimportant or shallow.

I've learned the hard way that when you are an entrepreneur, it is extremely important to quickly impress people you meet. When all you have is a one-month-old company and a smile, people write you off unless you can quickly portray success. Maybe you didn't go to Harvard or MIT, but the more magic tricks you have under your belt, the more investors, customers, and peers will assume you can accomplish your next audacious goal. This is the first step in actually living your life like you want.

Which bring me to choosing magic tricks. I've used common examples above, but your achievements will be most impressive if they are your own. Maybe you want to start a nonprofit mentoring program and positively impact 1,000,000 kids. Maybe you want to make the next greatest search engine. Maybe you want to replace Netflix and bring the world a decent selection of on-demand movies. You need to define what you want to achieve, and then do it. The coolest thing about magic tricks is that they are cumulative: the more you've already done, the more people will believe you can accomplish the next one.

After all, if you've already started the first commercial space program or played basketball with president Obama, or even been accepted to YCombinator on stage, then you can probably do whatever you want.

It's Sad to See Your Startup Turn into a Business

This post was originally published on 2/1/2013.

When I founded Skritter in 2008 with Nick and Scott, we called it a startup. We raised three rounds of funding, hired developers to help scale our team, and attended startup summits, venture capital panels, and meetups filled with aspiring entrepreneurs working on the next big thing. As with all young startups seeking capital, our business plan growth model had us making 30M in profit in 3-5 years as we took the language learning world by storm.

Four and a half years later, Skritter has become a viable, successful, growing company. We have three employees in addition to the founding team, and have provided employment for twice that many along the way. We've proven that our business model generates profit, that it adds value to customer's lives, and that we can achieve product-market fit.

But somewhere along the line, Skritter stopped being a startup and became a business. And while I am deeply proud of our achievements, the change makes me sad.

When you run a startup, you dream big, you think in terms of conquering entire new markets, challenging entrenched competitors, and changing the world in a big way. You work hard, play harder, and forge lifelong relationships with your co-founders.

Businesses, by comparison, are more modest and mundane. Businesses tend to know whom their customers are, they have a good sense of what makes money and what doesn't, and they don't make a habit of re-investing every penny to try and shoot the moon with a new product. Businesses are like middle aged fathers who just want things to run smoothly without too much fuss. Startups are their star-struck sons spouting poetry to their lovers in moonlit gardens.

Startups are just more exciting, vibrant, and entertaining.

But they also have this frustrating tendency to fizzle out, fail, or explode catastrophically. Founders lose their shirts, relationships are ruined, investors are burned, and once stable, gainfully employed founders end up in their parent's basements applying for jobs to cover their credit card debt.

I'm proud of what Nick, Scott, and I have built at Skritter. I'm proud we achieved the dream of building a profitable company. But if you've ever been there for the startup part, the irrational giddiness you get from building something new, you'll know instinctively what I mean when I say it's sad to see your startup turn into a business.

Why You Can't Admit Personal Mistakes on the Internet

My uncle is an entrepreneur-turned-corporate executive and has achieved considerable career success in his life, which is just to say that he's imposing and has a track record of getting what he wants.

One summer between my junior and senior years of college he hired me to help landscape his lawn. Several weeks after I had started, I made a small mistake.

"Oh, sorry about that, I'll just --"

"George, never say you're sorry" he said.

"Sure, I just meant that --"

"I know what you meant, but never say sorry, it makes you appear weak. Instead of saying you're sorry, fix the problem." He paused for a moment, looking at me, and then went back inside.

His advice ran so counter to what I had been taught that it stuck in my memory. I had always been taught to admit mistakes and correct them, but here he was suggesting I skip the first step. I'm still not sure I agree with it completely, but like every good over-generalization it has a nugget of truth: admitting a personal blunder to someone who has no empathy for you is ill-advised. That summer was all about me becoming employable, so I'm pretty sure my uncle meant that I would appear weak to a boss or employer, but the rule holds doubly-true for internet readers.

In the past, I have been tempted to write blogs about my goof-ups. I have almost always decided not to write such posts, not for want of subject material, but because they don't have any upside for me or my company. In the best case, people will think I'm humble, in the worst case they will think I'm incompetent. Simply put, I'm not willing to risk being labeled the latter for the former. And neither should you.

Self-aware people admit failure to get constructive criticism and seek catharsis. You aren't likely to get either if you bare your soul to the anonymous masses on the internet by first saying "I'm sorry."

Now You Are a Geek: Saying Goodbye to Wave

This was originally published on 2/2/2012.

Google Wave closed write access several days ago. This had been on my radar for some time, but as a heavy user and advocate of the service, it's difficult to see it go.

Seeing a pet project die is a right of passage for a career technologist. It's not just that it's a coming of age event, it's an important part of becoming better at building and improving ideas.

When I was young, I didn't think about technology or specific projects as transitory. I had such a short period of reference that everything was effectively permanent. I used Altavista for search because that was the only search engine that had ever existed and I played Descent 2 because it was the best game. I spent a lot of time playing games, trying operating systems, and installing utilities without thinking much about the people behind those monoliths of time and effort.

When you don't have an ownership stake in what you consume, it's easy to remain agnostic about games, operating systems, programming languages, server platforms, SDKs, editors, project management styles, deployment techniques,  and a hundred other topics about which technologists care deeply.  As I transitioned from being a consumer of web technology to a producer, I began forming opinions about the tech that surrounded me.

I love Google App Engine, dislike AWS, love Python, hate Java, dislike Windows, but think Mac OSX is for snobs, snub Firefox for Chrome, love Winamp, hate iTunes, loath antivirus software, prefer Google hangouts to Skype, and a hundred other subjective preferences. For having so many pet technologies, I have seen remarkably few get abandoned. Among those that I have lost, Wave has been the most important.

I was enamored with Wave because of the ideals and dreams of the people who invented it. I don't know much about the creators of Winamp [1] but I could put a face to the Wave development team and I wanted them to dethrone email, destroy chat programs, and better organize all web communication.

The fact that it failed makes me more of a real geek. I invested heavily in Wave and will now pay the price [2]. But in going away, Wave has also taught me some valuable lessons. I've learned that even well-funded projects die, technology doesn't often win out against established behaviors, and evangelism can only go so far.

The pace of innovation in web technology is accelerating and there is a tendency to avoid investing in any platform, but I think that it is the mark of a mature and invested hacker to have a small cemetery of pet technologies to grieve for. Don't hang on and be that backwards guy who wants to implement everything in Pascal, but remember what you've lost and use it to build better products in the future.

[1] This is because I wasn't old enough when Winamp was disruptive and being talked about, I have heard anecdotes that suggest it is quite an interesting story.

[2] Endless exporting and unsorted data migrations await. There is a strong temptation to accept the data loss and start over on another platform, but there is data in Wave that I simply cannot afford to lose.