Don’t Change My (User) Behavior

Working in venture capital means all kinds of founders, smart ones and retards alike, pitch me their solution on a daily basis.

It’s funny because I don’t have a business card. I stay home as often as possible. I don’t even make the investment decisions. But I exist near the waterfall, and founders want to get rained on.

Perhaps the worst kind of pitch, though, is when the product requires a change in user behavior.

It goes something like this:

“Everyone is doing ____, and it’s stupid/inefficient/expensive/bad/unhealthy.”


“Yeah. And we’re going to change that.”

There is a fine line between providing a better way to do something, and a new way. Uber? Better way to hail a taxi. Airbnb? Better way to find a place to stay. Dropbox? Better way to store files.

Uber doesn’t ask you to ride on a motorcycle. Airbnb doesn’t tell you to sleep in a tent (although at this point there are certainly tents on the platform). And Dropbox isn’t a network of well-trained carrier pigeons. They’re all just superior forms of the things you already do.

My buddy David used to tell the story of a large college campus, where the best strategy is to let the students’ natural trails serve as the blueprint for paved sidewalks. Let the student shape the path.

The same principles can be adopted in software. What do your users already do, why do they do it that way? How can you inject your solution into their existing workflow, instead of creating a new one?

Zoom, a popular meeting tool, knows that when you want to create a conference call you’re likely in the middle of sending a calendar invite. So instead of requiring users to log into their website to generate a link, they provide a Chrome extension that overlays Zoom in your Google Calendar.


With this simple, 1-day-of-code tool, Zoom users are empowered to use a Google Hangout alternative, while in the midst of creating a Google Calendar invite, every time they need a conference call component to their meetings.

Zoom is Smart. Be like Zoom.

How to do 100s of Pushups Every Day

“The journey of a thousand miles begins with one step.” – Lao Tzu

I’m like most people. I work out, lose 50 pounds, love my new lifestyle, then digress.

Over the past few years I’ve fluctuated from 175 –> 240lbs and back again, thrice. Currently I’m 190 and content.

There are more important things to do with my time than hit the gym, so I compensate by eating lots of salad, generally not snacking, and drinking far, far less than I used to. Maybe one day I’ll start running again, but it’s not a priority right now.

One habit I have picked up, however, is pushups.

You don’t need any special equipment, athletic clothes, or even time.

Every day at 3:30p I hit the roof (or basement, pending SF weather) with several office mates and we do as many pushups as we can in 3 minutes. That’s it.

We started at the end of November, and in my first day I did 48. Nowadays I routinely log 100+, and my personal best is 120 in 3 minutes.

Sometimes I do multiple sets in a day. Just last Friday I logged 100 at 3p, and another hundred at 3:30p. Because when all you’re doing is pushups, you recover quickly.

Inspired by this new habit, over Christmas break I built Pushup Metrics. While it was intended exclusively for my workout team, now it’s striking a chord with people all over the country. In the past 2 weeks alone, several dozen folks have signed up to log their pushups.

Here’s what my personal dashboard looks like:


There’s an addicting quality to micro-tasks with singular metrics like “quantity.” Combined with my adornment of quantified-self, I’ll do just about anything harder, faster, and more competitively when it can be measured with charts and graphs. Maybe you will too.

If you want to geek out and get stronger at the same time, I encourage you to join us.

Protip: create a private team for your friends by logging in or signup up at and the app will do the rest. For inspiration, here’s my office team.


Smell vs Taste

Do you have a favorite dish that doesn’t smell good, but tastes great?

Then you’ve pinned the truth about most things worth having in life.

The difference between successful people and unsuccessful people?

Successful people can hold their nose.

On Taking a Slot

I went to high school with a girl who later attended a prestigious university. Everybody was stoked, “What will she do next?

We haven’t spoken in years, but my understanding is she’s teaching English in a foreign country. What a waste.

Often I wonder who got the rejection letter because the girl I know took their slot. What where their dreams?

Anybody can take a TEFL course for $250 and hop on a plane for an “experience of a lifetime.” But that’s not what our world needs. We’re tired of the adventure-seekers, digital nomads, life-hackers. We need visionaries.

Of course, not everyone is (or wants to be) a visionary. It’s a title reserved for a small group through nothing more than self-section. So while no one can declare you aren’t a visionary, the statement rings true until you prove them wrong.

Two months ago I moved to San Francisco, the tech capital of the world. And it got me thinking…

I’m taking a slot.

It’s disturbing how many talented engineers I meet — from Spain to New Zealand — who aspire to live here. They have the talent, the drive, and they embrace America’s free-market culture. But their visas run out in 2 weeks.

For the next couple years, or however long I live in San Francisco, I’m going to do my best to make it count. I’m not here to make friends, go to brunch, or learn to surf. None of that matters.

To my euro-asia-latin-african peers, know that this California dude is trying to make a difference. That he isn’t interested in rising rents, long walks on the Embarcadero, or weekend Tahoe escapades.

I’m here to make the world a better place through software.

Wish me luck.

What is an A-Player?

It’s complicated to describe the world’s best talent. Are they nice, resilient, charismatic? Any array of character traits is defensible with the right prose, rendering all of it useless.

I’d like to debunk that.

An A-Player is someone who gets called “a machine” behind their back.

That’s it.

You can be a nice machine, smelly machine, noisy machine. You can be a machine that shows up late, leaves early, and hates meetings. It doesn’t matter.

Employers (clients, investors, whatever) love working with machines because they just work. It’s why Grandma loves her iPad.

Machines do things that aren’t really their specialty, or department, or within their job title. And because they’re machines, they do this thing called machine learning. That’s a fancy way to say they improve over time, without any effort from the user.

It’s no surprise A-Players don’t play nice with B-Players. Machines and people don’t get along.