Alex Weinstein
On Growth, Product, and Leadership
Arrogance, a fatal flaw

It’s curious to explore reasons for failure. We often discuss lack of vision, poor execution, wrong team as the killer for technology ventures. Allow me to shed some light on my recent favorite: arrogance.

Our field is full of socially awkward, yet really smart people, and many of them see such drastic intellectual superiority over many of their peers that they catch a fatal disease. At some point in high school, they got an A when everyone failed a test. Or, in their big company, they single-handedly saved the day and saved an entire department from slipping. Or they were a young prodigy in academia and wrote a famous paper.

This is when it hit them – dude, I’m really bright. Moreover, I’m so successful that it must be because I’m so much smarter than folks around me. In everything I do, I can only trust my own judgment – because it’s better than that of others.

And this is when they’re dead. Rand Fishkin, the founder of SEOMoz, calls this “the dangerous hubris of the startup world… the original and most serious of the seven deadly sins.”

They’ll be the ones to build a beautiful new gaming system, only to ship it with a controller that’s too large for half of the world to use. Or they’ll build a gorgeous car, and in their wisdom call it something that sounds great to their own ear – but means “it doesn’t go” in Spanish. All of these are the problems of leaders that think that they have the world in the palm of their hand – and they need no one else’s advice.

I stipulate that the cause of death of countless startups is the stubborn certainty of their founders to keep the original course. The reality is, most successful companies changed course drastically since their inception. You have to be flexible to admit a mistake, make a course correction before it’s too late, and vigorously attack the new path.

I’m a big believer that growth happens through what Einstein called a “school of hard knocks.” Through failure and humility, we see our own imperfection, and strive to improve on it. If we think we’re already perfect, the learning stops. The issue is that the others keep learning – and the world keeps evolving. If we keep using the same hammers for the new tasks, we’ll go extinct.

This issue is exacerbated by our talents. There’s a lot of really brilliant arrogant technologists out there. There ingenuity places them into leadership positions – thus putting not just them, but their followers in jeopardy.

Ask yourself, and be really honest – what were some of the mistakes I made in my professional life? What were some of my judgments that ended up being really false? I’ll point to Eric Sink’s Make More Mistakes article as a fantastic inspiration. The guy pours his soul out for the others to learn – it sure is a painful process, but my god, you get to internalize the lesson from those mistakes so well when you put them on paper.

Here’s a couple of my own dumb mistakes.

1. Do the market research before jumping head-first into a venture.

Cocktail Builder, my first entrepreneurial project. Premise is simple: put in the ingredients you have in your bar, it tells you what drinks you can make. Moreover, it says what stuff you can almost make – so that if you were to buy this one extra ingredient, you’d be able to make this cocktail.

Hey, I thought, when building this – I can sell the missing ingredients online, right on the spot! People are really likely to buy at this point! And so I go on and build the entire site. I market it, get pretty good traffic.. And then I start working on adding the monetization capabilities for selling liquor.

And that’s when I realize: you can’t really sell hard liquor online in the US. Ooooops. There goes that idea… and 8+ months of work with it.

2. There will always be people smarter than me. Find them.

Find Touch, my next entrepreneurial venture. My co-founder and I were convinced that we needed to amass a large client base by luring them with a free product offering, before we can follow on with a jobs marketplace that will leverage that client base.

Our first advisor and lawyer – thank you, David Marks – asked a seemingly obvious question: why aren’t you guys going for the real deal right away? Why not create a jobs marketplace immediately, instead of a silly entry offering that’s impossible to monetize? This question saved us months of work and ultimately made us a viable business.

Our second advisor – thank you, John Kueber – kicked us in the butt when we were obsessed with raising money. We spent 6 months agonizing over decks, financial models, introductions to angels.. All while we had basically no product and little traction on the marketplace. John made us drop this nonsense in favor of making the product sing – and in favor of getting some real customers use this product.

This is just the beginning of my list.. At this point, I know that I probably have more wrong hunches than right ones. That said, I do know one thing for sure – if you listen carefully, someone will quietly whisper a thought that never visited your head. You may just find a missing piece of the puzzle, if only you are willing to listen.


In parting, allow me to offer you a story from a friend. He was recently interviewing in a successful technology company for a senior position; he was speaking directly with a division’s vice president. He asked the VP a simple question: do you see the role of your employees as implementors of your vision, as an extension of your own capabilities?

The VP answered “yes, I simply cannot implement all of my vision myself, so I need my team to follow through on it. I frequently have issues where the team doesn’t quite understand the full scope of my intent, so they have trouble implementing it.”

Is it just me, or does that phrase smell like “I’m the smartest ass in town and I know the solution to every problem. I need cogs for my machine to execute my vision.” No matter how brilliant that guy’s vision is, his team is going nowhere. Innovation comes from diversity and from nay-sayers – from passionate, open, and respectful disagreements. Innovation comes from employees that have autonomy, mastery, and purpose as their motivators.