Monday, October 20, 2014

Ditch The Swagger

Once upon a time, swagger was considered a negative.  Think of the phrase, "swaggering bully." Now, however, swagger has become a quality that many view as a major positive, and try to adopt for themselves.

Swagger-philia has proliferated across numerous industries and fields.  No longer just the province of entertainers and professional athletes, now even software developers call themselves "rock stars" and swagger about, accompanied by "hustlers" who brag loudly about being "ballers."

Is this a good thing? A bad thing? My gut says bad, but it's worth a closer examination.

First, we have to define swagger.  Is it simply confidence? I think swagger requires confidence, but it's certainly possible to be "quietly confident" without swaggering about.  If you're not sure what I'm talking about, consider two of Denzel Washington's iconic roles.  In "Training Day," Washington's character *is* a swaggering bully (albeit a mesmerizing, charismatic one).  In "The Equalizer," Washington plays a stone-cold badass who humbly works at a home improvement store.

Confidence isn't swagger.

Okay, so perhaps we should take a look at swagger from a different angle.  What  does it feel like to have swagger? I think the key here is that swagger is like an addictive drug.  When you swagger about, you feel cool, badass, superior, invincible, name it.  It feels great.  But why? I would argue that it's because swagger is both completely self-centered and detached from reality.  Swagger gives you permission to focus on self-aggrandizement, and to ignore reality.  Joe Namath guaranteed a victory in Superbowl III; the reason we  revere his boast is that his team actually delivered.  99% of such guarantees go unredeemed.

So if swagger makes you feel good, focus on yourself, and ignore reality, it's essentially the cocaine of attitude.  A lot of fun until you crash.

And make no mistake, swagger usually leads to a crash.  Even Michael Jordan crashed when he returned to the NBA with the Washington Wizards.  Manic activity and ignoring the evidence might feel good in the short run, but it generally leads to feeling bad in the long run.

The amazing thing is that those with true swagger can crash time after time and never concede one iota to reality.  The NBA's Nick Young had the swagger to nickname himself "Swaggy P," and amazingly, even made it stick.  Despite being, objectively, a below average player (in his best season, he didn't even hit 45% of his shots), his propensity to take and make (a low percentage of) circus shots continues to win him fans.  This despite many of those same shot attempts ending up on YouTube, like his failed attempt at a 360 degree layup which sailed directly into the stands.  Of course, Nick is also a multi-millionaire who is in a romantic relationship with multi-millionaire, sex symbol, and #1 recording artist Iggy Azalea, so perhaps he is the one having the last laugh.

But for every Swaggy P, there are a million playground loudmouths, writing verbal checks their game can't cash.  And that's the problem.

Swagger is so outlandish and mesmerizing (remember Denzel in "Training Day") and feels so good (just ask any former SNL star/cocaine addict) that many people flock to its practitioners and imitate them.  But the lucky few swaggerers who can actually back it up are like the lucky few athletes or entertainers who hit it big.  Yes, the outliers have an amazing outcome, but the median outcome looks an awful lot like failure.

Swagger doesn't age well; even the swaggering playboy eventually runs out of young women witn daddy issues and low self-esteem.  Would you rather be Hugh Hefner or Nelson Mandela? (If you answered Hef, you should be ashamed of youself.)

Building quiet confidence based on the evidence and your experience with reality doesn't feel like doing blow, and doesn't sound good on a reality TV soundbite, but for the vast majority of people, it's a better path to a happy, productive life than the swaggerer's way.

Tuesday, October 14, 2014

Drivetime Consulting: Amr Shady

I just completed my first Drivetime Consulting engagement yesterday.  Amr Shady reached out to me via email yesterday afternoon, and we set up a call for my drive home last night.

The call was exactly what I was hoping for; Amr is a successful entrepreneur and all-around interesting guy, and he wanted my feedback on a new product that he's building, for which I would be a natural customer.  I was able to give him some very concrete feedback, and we also discussed some of his other activities, such as his involvement with Endeavor.

Hopefully, I'll be able to get more involved with Endeavor in the future, and we've made plans to meet up when he comes to San Francisco!

Saturday, October 11, 2014

Why Reading Literature is Valuable

I was listening to the New York Times Book Review podcast (one of the little ways I stay connected to the literary world) when I heard a debate about the value of literature.  As is often the case with literary folk, the debaters were conflicted and ambiguous, pointing out the contradiction between arguing for literature's inherent value, and the frequent argument that reading literature prepares one for the world.

I've never been particularly good at angst--one of the main reasons I always struggled to write literary fiction (and to get dates with my fellow writers at Stanford, most of whom seemed to prefer darker, more brooding suitors).  To me, it's actually fairly easy to come up with a taxonomy of why reading literature is valuable:

1) Entertainment.  People pay money to be entertained; people find literature entertaining.  Ergo, literature provides entertainment value.  Beyond the simple power of page-turning, literature can also make you feel emotions that you wouldn't normally encounter in your everyday life.

2) Cultural fluency.  Reading the canon grants access to a broadly shared set of ideas and experiences.  In other words, reading literature provides cultural fluency.  Eric Cartman of South Park can say, "Captain Ahab has to get his whale," and we understand why.

3) Reading ability.  Literature tends to be a far denser read than, say, TechCrunch posts.  It acts as a training program that enhances both your reading speed and your ability to glean meaning from text.

4) Ideas.  Literature grants you access to other lives and minds.  Not only does it expose you to new ideas, those ideas can serve as models for your own decision-making.  I often use principles I learned from literature and history to make better decisions.

5) Authority.  When you seek to persuade others, citing classical sources seems to have a far greater impact than, say, children's cartoons.  Rightly or wrongly, the judgment of history grants literature authority that you can leverage for your own purposes.  (Though I'll note that I'm always a sucker for any argument that is based on DuckTales)

6) Branding.  Even today, reading literature is considered a key part of being learned.  If you don't know Shakespeare, Twain, and Austen, you won't be taken seriously as an intellectual.

Of course, I would argue that entertainment is the fundamental value.  If you don't find literature entertaining, you'll end up like the millions of American high school students who can't remember much about The Great Gatsby...and were born too early to simply watch the Leonardo DiCaprio movie.

Wednesday, October 08, 2014

The Writing Feedback Loop

Like many things in life, the feedback loop on writing is long and uncertain. When I write a post, I don't know if it will quietly sink beneath the waves, get a reaction or two, or spark a week-long furor. Sometimes, the shortest and least effort-filled posts draw the best.

As a result, only people who love to write stick with it; the extrinsic rewards are too uncertain. You have to rely on intrinsic motivation.

(originally appeared as a comment on Hunter Walk's blog)

Monday, October 06, 2014

Drivetime Consulting

For years, I've been saying that I ought to set up a drivetime consultancy.  I'm in the car for 20-30 minute chunks each day, and I'd rather be talking with people than listening to the radio.

What's held me back is the work involved.  I figured I would need to build a fancy scheduling system, and I just never seemed to have enough time.

To heck with that.  If I can tell entrepreneurs to get gritty and make things happen, I should be willing to do the same.

Therefore, I'm announcing the Chris Yeh Drivetime Consultancy.  Anyone who wants to buy a 20-minute chunk of my time for drivetime consulting (either 8:30 AM or 5:30 PM Pacific, Monday through Friday) can simply send me $100 via PayPal.  I signed up for PayPal so long ago that my PayPal address is actually my old business school email:

Once you send me the money, follow up with me via email (that same business school email still works, amazingly enough) to schedule your call in the next week or two.

If this MVP works, maybe I'll go ahead and build that fancy scheduling system.  And while $100 for 20-30 minutes may sound steep, it's a pretty hefty discount over my rate of $10/minute (I'm willing to discount for people who save me from the vagaries of drivetime radio).

Sunday, October 05, 2014

Economic Growth and the Rise of Religion

An intriguing thought, trigger by this Atlantic article, "A Cost-Benefit Analysis of Being Jewish":

What is religion is now a luxury good?

Consider the following: Marx called religion the opiate of the masses.  During an era in which life was brutish, nasty, and short, focusing one's attention on a glorious afterlife made a lot of sense.

But as standards of living rose, the influence of religion waned in the developed world.  Rather than worshiping in temples, people worshiped at the altar of the vast entertainment complex (including sports and the arts).

All this makes sense if religion is an "Inferior Good" (an economic term, not a value judgment) where demand decreases as income increases.  In the 20th Century, Jewishness behaved like an inferior good; higher incomes and education were strongly correlated with Reform Judaism.

But perhaps religion is both an inferior *and* a luxury good.  As standards of living rise higher and higher (for example, even the poor now carry connected supercomputers in their pockets), the ability of religion to provide unique experiences makes it increasingly attractive to well-off consumers.

One might even consider things like Burning Man or TED as evidence of this theory; these secular events show a lot of religious characteristics, such as community and ritual.

Rather than viewing religion as a relic of the past, we might be wiser to see it as a once and future pillar of the human experience.

Friday, October 03, 2014

Gaming The System Doesn't Work, And Everyone Has Worries

One of the exciting things about Paul Graham handing over the reins of Y Combinator to Sam Altman is the fact that it gives Paul more time to write.

Paul has long been one of my writing inspirations, and his concise yet conversational style has always struck me a near-perfect fit for his topics.

I'm delighted to report that Paul's latest essay is one of his best.  For the most part, I'll simply quote some key passages, but I will add a few additional thoughts here and there.
"Gaming the system may continue to work if you go to work for a big company. Depending on how broken the company is, you can succeed by sucking up to the right people, giving the impression of productivity, and so on. But that doesn't work with startups. There is no boss to trick, only users, and all users care about is whether your product does what they want. Startups are as impersonal as physics. You have to make something people want, and you prosper only to the extent you do.

The dangerous thing is, faking does work to some degree on investors. If you're super good at sounding like you know what you're talking about, you can fool investors for at least one and perhaps even two rounds of funding. But it's not in your interest to. The company is ultimately doomed. All you're doing is wasting your own time riding it down.

So stop looking for the trick. There are tricks in startups, as there are in any domain, but they are an order of magnitude less important than solving the real problem. A founder who knows nothing about fundraising but has made something users love will have an easier time raising money than one who knows every trick in the book but has a flat usage graph. And more importantly, the founder who has made something users love is the one who will go on to succeed after raising the money."
Growing up, I was always a game the system kind of guy.  Offer me a game, and I'll try to figure out the best way to exploit the rules.  There's a reason why I'm the king of board game night.

When I started my first company, I did the same thing.  I quickly assembled all the markers of success, from my own academic credentials to my successful co-founder, and used my verbal agility and emotional intelligence to raise millions of dollars (in two rounds of funding, just like Paul wrote!) while I was still a b-school student.

The only problem was, nobody really wanted my product.  The sinking realization hit me when our receptionist, a young, recent graduate, asked me to show her the product.  She tried it out, then simply said, "That's *so* not worth it."  And she was right.  Everything after that was simply finding a way to get as much money back to investors as we could.

By the end, I felt trapped, but I also felt an obligation to get as much money as I could for the investors who had placed their faith in me.  I've had a lot more success since then as both entrepreneur and investor, and a lot of it comes from having learned a painful, expensive lesson my first time out.

P.S. Gaming the system is still a lot of fun...when you know that you're playing a game.  Feel free to challenge me!
"Larry Page may seem to have an enviable life, but there are aspects of it that are unenviable. Basically at 25 he started running as fast as he could and it must seem to him that he hasn't stopped to catch his breath since. Every day new shit happens in the Google empire that only the CEO can deal with, and he, as CEO, has to deal with it. If he goes on vacation for even a week, a whole week's backlog of shit accumulates. And he has to bear this uncomplainingly, partly because as the company's daddy he can never show fear or weakness, and partly because billionaires get less than zero sympathy if they talk about having difficult lives. Which has the strange side effect that the difficulty of being a successful startup founder is concealed from almost everyone except those who've done it.

Y Combinator has now funded several companies that can be called big successes, and in every single case the founders say the same thing. It never gets any easier. The nature of the problems change. You're worrying about construction delays at your London office instead of the broken air conditioner in your studio apartment. But the total volume of worry never decreases; if anything it increases."
There have been times in my life when I had enough so that I never worried about money.  There have been other times when I had so little that I constantly worried about money.  But the one constant is that I always had plenty of worries, regardless of the state of my bank account.  (The other fact is that it's not a constant linear progression from poor to rich--entrepreneurship is far more of a rollercoaster, with multiple steps forward and back, at least for most of us)

I have friends who have vastly more money than I do, and I have friends who have vastly less money than I do.  We all have worries.  And as Paul notes, one of the interesting things is that those who have a lot of money get very little sympathy, probably because most people would trade lives with them in an instant (something of which those very successful folks are well aware).

In fact, I've joked that I should set up show as a "First World Problems Counselor," and charge money to lend a sympathetic and understanding ear to Silicon Valley's 1-percenters.  Everyone has problems, and everyone deserves sympathy, no matter how enviable their overall situation.

So if you keep thinking to yourself that you'll finally stop worrying when you become "successful," I've got bad news for you.  No matter how "successful" you become, you'll never stop worrying.  The only way to stop worrying is to learn to stop worrying, regardless of your life circumstances.

The Manic Side of Entrepreneurship

One of my long-term projects is to write a book about the psychology of entrepreneurship.  One of the issues I want to write about is what I call the manic side of entrepreneurship.

Entrepreneurs are innately optimistic; otherwise, they wouldn't jump into a field of endeavor that has a 90%+ failure rate.  I can assure you that every company I've started or invested in, I've felt had a better than average chance of succeeding...and despite that certainty, plenty of them have failed.

HBS professor Howard Stevenson famously defined entrepreneurship as, "The pursuit of opportunity without regard to resources currently controlled."  And therein lies the wonder and danger of entrepreneurship.

Being willing to pursue a goal whose achievement depends on resources beyond your current control is a massive leap of faith.  Yet it is precisely this leap of faith which helps change the world.  In the words of George Bernard Shaw, "The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man."

Entrepreneurs are unreasonable.  They start sprinting as fast as they can, convinced they'll figure out how to fly before they run out of runway.

I'm not going to argue against optimism or risk-taking; these are essential ingredients for success.  What I am going to warn you about is the danger of manic overcommitment.

One entrepreneur whom I work with has an issue with chronic overcommitment.  The instant he has things under control, he starts taking on more commitments.  I joke that like the late Warren Harding, he simply can't say no (I bear more than a passing resemblance to the former President myself, having someone contrived to be a startup executive, venture investor, social entrepreneurship mentor, and author, all at the same time).  He sometimes dreams of the day when he'll be so successful, that he won't have to worry about how to meet all his commitments.

Well, I hate to break it to him, but that day will never come.  Not because he won't be successful (he almost certainly will), but because an entrepreneur's ability to make commitments will always exceed his or her ability to deliver on them comfortably.

Tony Hsieh is an enormous success.  While still in his twenties, he founded LinkExchange and became fabulously wealthy.  Then, he somehow exceeded that wild success when he founded Zappos.  As his third act, he plowed $350 million of his own money into turning Las Vegas into a startup hub.

While he's been able to generate enormous change, he also overcommitted, and recently stepped down as head of Project Downtown, and laid off 30% of his staff.  Even someone as rich and successful as Tony saw his ambitions outstrip his resources.

The manic side of entrepreneurship has its uses, but by making yourself aware of it, and taking steps to avoid overcommitment, you can tap its wild energy without plunging yourself into the depression that seems to be its unavoidable doppleganger.

What Entrepreneurs Should Do Differently To Stay Married

I recently dove into Jay Goltz's New York Times post, How To Be An Entrepreneur, and Stay Married.  I thought it was an insightful piece, but to me, it was missing the most important part: What entrepreneurs should do differently to stay married.

Having recently celebrated my 16th anniversary (and the 18th consecutive year in my career of not selling a company and becoming a billionaire), I thought I'd share some of my perspectives and strategies for staying married.

1) Make family the most important priority, and mean it.

Any of my entrepreneurs who has asked me what to do about family issues knows my consistent refrain: Family is always more important.

Note that this doesn't mean that family is the #1 place where you spend your time; entrepreneurship is time-consuming, and building a company requires sacrifice.  But no matter who you are or what your company does, you should never put your family's health and happiness at risk.

I have made plenty of decisions in my career that reduced my current income, and as a result, we don't live a lavish lifestyle.  But we've never been in danger of ending up on the streets.

And if a health emergency arises, drop everything else.  You'll never regret that decision, and you might regret the alternative for the rest of your life.

2) Spend time with your spouse every day, no matter how mundane the activity.

I don't care how busy you are, you can certainly set aside 30 minutes to do something with your spouse.

This doesn't have to mean a "date night" (though that helps).  Even chatting and watching television together at the end of a long day helps maintain the health of your marriage.

My wife and I often watch some of Conan O'Brian's late night show.  It's not really that funny much of the time.  But it is a ritual that helps end the day on a together note.

3) Take actual vacations.

There's something special about vacationing somewhere new.  Seeing new sights and learning new things helps renew our zest for life.  This is especially true when you vacation with your kids.

We've taken the kids on vacations all over this country, and every time we travel together, it helps build the happy memories to sustain us through the everyday grind of the endless setbacks of entrepreneurship.

This doesn't mean you have to go off the grid; even on vacation, I'm checking emails and taking occasional calls (activities that my wife doesn't relish, but tolerates).  But when you're actually doing something as a family, it means really being present.

Sadly, entrepreneurship is very stressful on a marriage.  But if you actually take steps to protect your relationship, my experience is that strong marriages can survive and thrive despite the stress.

Sunday, September 28, 2014

Hard Choices Are An Opportunity

I'm a big podcast listener because I like to multi-task while I'm cooking and washing dishes (something I do a lot on weekends, since that's when I prepare our family's food for the week).  Today, I listened to a fascinating TED Talk by philosopher Ruth Chang.

It's worth listening to the entire talk, but for the impatient, I wanted to relate the key insight that I took from it.

Chang's talk is called, "How to make hard choices."  Her point is that hard choices are often hard because they aren't quantifiable.  Indeed, deciding whether to become a lawyer or philosopher (the very choice Chang faced when she was in college) is difficult precisely because the options are almost impossible to compare, and thus are "roughly on a par."

Chang's insight is that hard choices are actually an opportunity.  If you can't use reason to logic your way to a "right" answer, a hard choice gives you the opportunity to say something about yourself.  Choosing law school says something very different about you than philosophy grad school (though I would argue that depressed prosperity and angst-ridden poverty are both rather unattractive options!).

I've faced plenty of hard choices in my life, and will no doubt continue to encounter them as the years roll by.  But thanks to Chang's talk, I'll be able to frame the process of making those choices in a way that empowers me to choose my own identity, rather than paralyzing me with trepidation about the future.