McKay Thomas

What Humanity Does Next

By McKay Thomas

When I was first designing and building at in 2006, 1 in 100 websites I actually used impressed me. In fact, I had a bookmark list back then of websites that really blew me away and that list was very, very short.

I designed on the side as well during that period and back then good design on the web was so rare that nearly every client of mine could scarcely believe what I had created for them when I would walk them through a pitch. And, deep inside, I knew I barely even compared to the web’s and the world’s greats. But that just goes to show how far we’ve come.

Now I’m rarely not impressed by most sites I visit. Pages are basically well laid out. Content is written for humans, for the most part. Photos are clear and hi-res and most are edited fairly well. Menus are standardized and orderly. Lists are easy to follow, videos easy to play, and everything is easy to share (really) anywhere!

All this was not true in 2006. Really any of it. In fact the opposite was universally true with rare, rare exceptions. By 2010, and this is anecdotal, but feels about right, we were to the point where 1 in 15 websites were getting there. At this point, though, the web was going through a weird mobile-morphization. Things started to take a few steps back. In the old days where only a few great designers knew how to execute a web strategy, now most designers had some web experience and could help put together a fairly thoughtful strategy. But mobile crippled it. Roadmaps couldn’t adjust in time and designers once again were experimenting with things that they had no exposure in.

Now flash forward to today and things have begun to settle down again for the web, and (now) mobile, world. Today as I go through my phone’s apps and navigate the 100 or so websites that cross my way each week, I’m struck by how easy and fast and beautiful everything is again. Almost everything is designed for retina displays and PC widths and mobile widths. Menus are standardized, videos are easy to play and everything is easy to share and save.

Tonight, to actually draw a point to this collection of personal observations, I’m wondering where we, as a human race, and more specifically as a clan of design thinkers and creators, apply our problem solving spirits to next. Where do we go from here? Of course there is always a new website or app or experience, but we have precedent now. A lot of it. And there will always be an envelope to push, but is there a medium we have left to explore? A place we can go next that will let us unleash our design thinking in new and unexplored ways?

Maybe the next great frontier for our great band of revolutionaries should be business. If you are glazing your eyes over, may that be a sign to you of an under-explored world of design thinking. Distribution, partnerships, business models and product married together in well sized markets and populations are the untamed jungles of our economy.

As a designer turned entrepreneur (of several years now) let me give you my personal witness of the vast and exciting opportunities that await the truly brave and creative that venture below the pixel to the business itself. Listen to it next time it calls for you. Because, indeed, it is calling.

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University of The Possible

By McKay Thomas

Twenty Thirteen was a university of the possible for me. It wrapped up the way you wrap up lunch with an old friend. Awkwardly. You both loved it, but neither knows how to say goodbye.

Twenty Twelve delivered me, cold and wet, on to the streets of San Francisco. The ensuing hours and days took my brightest dreams and darkest fears and smacked me in the face with them.

I started a company from an idea and raised a couple million dollars to build it. I recruited a top flight team, built an app, and now have thousands of people using it every week.

I traveled to seven different countries this year. I meditated with Hindus in India. I snake-charmed with thieves in Morocco. I rowed through the canals in Amsterdam. I ate Jewish desserts till I was silly in Melbourne and cuddled as the sun set in Baja.

I found a new home in San Francisco from São Paulo this year. Making California my home for the second time after 26 long years. I found myself here in the way I needed to, but wasn’t sure I could. I think many people come to SF looking for something, but never find their feet and I was fortunate enough to find mine.

My son started walking. My daughter started school. My wife and I lost a combined 43 pounds. We fell in love all over again as we continue to define what makes a successful marriage.

My kids were kidnapped. The car was stolen with them inside and I called 911, where they asked me to describe my son and my daughter to them, creating a new low in my life. They were found 40 minutes later and returned to us within two hours. Short. But terrifying.

Three employees of my company quit this year. They all left for reasons, but most days I don’t want to confront those reasons. The company and the team today works well and I’m glad things turned out the way they did. But it hurts watching someone walk away.

Soaring highs. Plunging depths.

It’s the human experience. Deciding in a leaping moment that no one else will decide your fate. You might get fired. Your kids might get taken. Your team may abandon you. But the whole earth is still yours for the taking. It may all burn to the ground tomorrow, but today you have a world to change, because you can. You really can. And 2014 will be my year for doing just that.

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Manifesto For 2014

By McKay Thomas

The city breathes. It inhales with hissing busses, dripping coffee, and the foreign tongues of conference attendees. It exhales with the crisp, cool air blocked by coat collars and scarves.

You feel it in the vibrations of the stairs you climb at the MUNI station on Market. Your feet scratching like sand paper on every step, while your messenger bag waves and taps on your back in perfect rhythm.

It breathes in chatter and rumor. In free wifi, found hope and shattered dreams. It breathes.

Many try to find meaning it all of it. Between the bankers on 2nd, the shoppers on 4th and the dope dealers on 6th, there seems to be a kind of direction to it all. A free-mindedness that seems to unite everyone in a common chorus that things could be better. And if not better, different. It shows itself in every coffee house and Michelin-star lunch spot.

You sit down with an old friend and within seconds the table is set with words like, “I had an idea,” and, “wouldn’t things work better if…” Throughout the 60 minutes a grand design is laid bare. Golden forks and four spoons. Crystal and china. Watches are glanced at and as fast as it was built, busboys come and remove the dreams to the sound of clinking glass and metal. Ready for the next lunch-hour dreamer.

You catch your breath, but the city exhales without you. Another path for another day.

The sound of soles on the sidewalk are barely audible through the sound of the city. Trolly bells ring a few blocks down. A street performer has turned barrels in to drums. The office is just around the corner, when the fog breaks and the sun warms your face.

Why not me? Why not today? The city seems to grab at you. Pulling you. Throwing you against the bricks as it has for thousands of others before. The words written and spoken by others echo down the alleys of the surrounding streets. The streets you know well and walk often. Failure. Doubt. Fear. Bills. Husbands. Kids.


It’s too much. You force another breath and decide to move on. But what if you knew that everyone in the city was right along with you. What if the voices of dissent were voices of envy. What if every aspiring sneaker that ever touched down from SFO grabbed your shoulder and whispered in the breathless voice that accompanies every would-be entrepreneur, “We’re right behind you!” What if you knew the nights wouldn’t be as long as you thought, nor the debt as heavy as you anticipated.

If you listen to the city close enough you can hear those voices now. Both the risen and the fallen are with you in spirit and though you may not win the day, you will have been in the arena.

And the heart that feels as if it will leap right out of your chest and the breath you can not catch are all signs that you are alive! And today, more than every day before it, is for living.

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Baby Weight

By McKay Thomas

So much was right about my last startup, They say so much in business is luck and after Baby I’m inclined to believe them. We had the right business at the right time with a team that knew how to roll with the punches. We ended up hiring 200 people within our first 12 months. But that isn’t the whole story.

What is discussed far less frequently, both in regards to Baby and any startup success story of any size, are the details that were a part of that growth. The fear, the emotions, the broken relationships. Mostly ignored with statements like “Startups are hard,” or “It was a challenging period for us.”

However, what no one really talks about is the screaming matches that happen between founders.  The back-stabbing. The secret meetings that end up getting someone kicked out of the company. The facial ticks that develop, the weight that is gained by the tens, and the achey jaw from being overly clinched. When someone says “Startups are hard,” this is what is being referred to. The physical and emotional abuse founders and early followers put themselves through in the name of money, power, pressure and prestige.

After I left and moved back from São Paulo to San Francisco (Go Niners!), I had some things to sort out. I had to get my life back to normal. This is no easy stroll. Again, when we use euphemisms like “sort some things out,” what we really mean is that there is bitterness to ease, facial ticks to relax, weight to lose, and memories that need to be left alone. 

My therapy of choice is entrepreneurship. Within 24 hours of leaving Baby I had already begun laying the footwork for my next business, First Opinion. The process for building my team has been much more deliberate than in previous businesses. Everyone had to be easy going. Everyone had to be the best at what they did. Everyone had to be a true member of a collective team. Sounds easy enough, but I assure you it isn’t and the consequences of hiring the wrong person couldn’t be more dramatic or damaging.

The reason this all comes up today is I just weighed myself in this morning at 197.6. That’s still much higher than it should be, but it’s also where I was before I started My Baby weight. So much about Baby was right, and that is sticking with me. But those things that were wrong are slowly falling off. It feels good. Startups are hard, but there is a way through it.

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Press check for @firstopinion’s handmade letterpress thank you card for our earliest beta users. Thanks everyone! It’s been the most rewarding journey with you.  (at Dependable Letterpress)

Press check for @firstopinion’s handmade letterpress thank you card for our earliest beta users. Thanks everyone! It’s been the most rewarding journey with you. (at Dependable Letterpress)

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Stretching Is Learning

By McKay Thomas

One of the original team members was in San Francisco today and in telling him the story of how First Opinion got started he said something that struck me as an inalienable truth: you can’t learn by doing something your already know.

So, by taking the inverse of that, you learn by doing something new. By stretching yourself. As he shared his little piece of wisdom with me, I remembered a video I shot on the flight as I was leaving my last startup for my current startup.

I pulled it out this afternoon and felt like it highlighted exactly how I was feeling at the time. Stretched. Alone. Scared. No next steps, but at the same time 500 next steps. I had no idea if I was doing the right thing or not. No idea if it would be worth the sacrifices I and my dear wife were making.

Although there are no endings to this story, First Opinion is gearing up for it’s next step. Launch.

Stay tuned…

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The Things We do To Change The World

By McKay Thomas

I read a great post by Mark Suster a few weeks ago about always asking for what you really want. Just today I had to buy an iPhone case at the mall and when I was told they were $20 and up, I found the one I wanted and asked to pay $10. And I ended up paying $10 with almost no hassle.

There are more important things than phone cases, though, and that’s precisely the point. Several months ago when First Opinion was just three of us in a corner in someone else’s office, I was trying to recruit someone to help with the training of our doctors abroad. After meeting with several people of several disciplines, it felt like there was no one that would ever pick up their life and move to a foreign country for an extended period of time for such a young company.

That said, I had the perfect person in mind. He was a user himself, with his wife. He had a young family, which I love. He was very senior and experienced and, most importantly, impassioned about First Opinion. I came in to the office one day, having thought about my options, and decided I was going to ask. Why not?! What could I lose? I sent him, Rick, a text asking if we could have a call that day and we set up a time. The call was very direct, not unlike asking to pay half price on an iPhone case.

"Rick, thanks for making the time!"

"Sure, no problem."

"I had an idea I wanted to run by you in regards to how you might be able to get involved with First Opinion."

“Oh yeah?”

"We’re building out an international doctor network and I’m looking for someone who can be my eyes and ears and help move things forward abroad, initially in India. After getting to know you and spending some time with you the other day, I think I would regret not exploring what it would look like to have you and your family move there and be a full-time part of this little movement of ours."

"That’s crazy." He said, then he laughed, and that’s when I knew that it might be possible.

I responded, “I’ve moved internationally before with a wife and a young baby, and I’m telling you, those memories are amongst the most vivid and formative of my life.”

We hung up not long after that. I went back to my corner and told my team I had just asked Rick and Josi to move to India. They both thought I was crazy. “They’ll never go,” one of my team members told me. But, not 24 hours later, Rick had accepted that it was something he and his wife wanted to do and we had begun hammering out the details. I just asked.

However, their enthusiasm and sense of adventure have reminded me, once more, of grander purposes. Beyond the code and financial models, the business and the politics of the startup, there are insanis praedonum, latin for crazy pirates. And these insanis praedonum can’t be stopped. They roam the planet in search of the things their mother told them not to touch and teachers told them were foolish. Where books and movies require fiction to tell the tales of extreme adventurers, insanis praedonum need no such literary license. And though gold may be the excuse they share with others, it is the unconquerable human spirit that actually drives them, these insanis praedonum. 

To Rick and Josi and their young one, I wish you safe travels. You’ve sold nearly everything you own, packed up the rest and, with your 4 month old baby boy en tow, are moving to a country that people describe as another planet. To you who are clearly insanis praedonum, I solute you. There is no telling where any of this will end up, but there is no doubt in my mind that what you will find, what all of us will find that embark on the strange and compelling journey of insanis praedonum, will change you forever.

Go get ‘em, crazy pirates. Hedge no bets and change this world for the better.

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Debunking Business

By McKay Thomas

What is business? I think it could be classically defined as the exchange of value. In the movies when the top secret weapon is exchanged for someone’s beloved pet, the classic line, “pleasure doing business with you,” is typically exchanged.


It has become the pursuit of my generation. Maybe all generations before mine, as well, but it feels as if there has been a shift. A shift from pursuit, possibly, to obsession. On the coattails of scientists like Niccola Tesla, inventors like Steve Jobs, and engineers like Mark Zuckerberg, my generation has slipped the generational bonds of mere employment for the game of business.

We left college for it. We left home for it. We left our moms and our dads for it. We left jobs and the life we were promised for it. We have paid a high price for it and now treat it as a kind of religion. And what have we received in return? What was the exchange of value? And is it what we feel we were promised?

Business, to me, has been a taker. It has taken my childhood, or what was left of it, and bashed me over the head with it. It has taken family from me. It has taken more days and nights than I can count along with much of my peace of mind.

I fear that in the pursuit, the obsession, of business, my generation will lose what we took this journey to secure: a better life.

It doesn’t have to be this bleak. And maybe it really isn’t. It’s been a hard day today. A hard day in business. Truly hard days take something that is hard to get back, but that’s what the English language is for. That’s what family is for. That what’s sunny days and green grass are for. That’s what a cool breeze and rushing water is for. What prayer is for. To get us through all the hell that business throws our way.

My generation may lose personally more than it may gain collectively, but at least we’ll be a part of something. A movement. And as long as there are bad days, at least there will always be parks and wives and kids and movies and a good day of tech news to get us through it.

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Four years ago {tomorrow} McKay and I tied the knot. Four years. 

It feels like a lifetime ago, and yet it feels like we’re babies still. Babies with babies. 

In four years we’ve lived in two countries, three states, four cities, a basement, a high-rise, a house that we bought, and an apartment twice the price of the aforementioned mortgage payment.

We’ve had two kids, three startups and too many adventures to count.

Between the two of us we’ve Instagramed 2,225 photos, been to seven countries and spent truckloads of money on sushi.

It’s been a pretty eventful four years! Moving and living abroad {oh, and then moving back to the states to start a brand new business} has really brought us together. And although we are just starting out on this marriage journey, it feels as if we’re old, seasoned friends. 

I love you, McKay. Happy Anniversary!

{can’t get enough Thomas Anniversary love? Click here for years three, two and one}

A wonderful anniversary post from my wonderful wife. I’m in love.

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Startups Are Like Friends

By McKay Thomas

Sometimes you love them. You can’t get enough of them. You wake up Monday morning and can’t believe how lucky you are to have them.

Sometimes you hate them. They take and they take and they take until you feel like you have nothing more to give.

Sometimes they make you laugh. Sometimes there’re tears. Sometimes they give you facial ticks and sometimes they give you money.

Sometimes you make new ones. And sometimes they die.

There are many ways for startups to die. Acquisitions, no matter the price (aQuantive for $6.2B), acqui-hires, too much money (ahem, color), too little money. But most of the time it’s because, to quote Chris Dixon:

The default state of the world is to stay the way it is, which means the default state of a startup is failure.

My mind is whirling this evening around this subject as Mick, a friend of mine and fellow entrepreneur (although a more successful one), is turning off a product he and his world-class team have been building for the last year and a half.

Now the team is nowhere near wrapped up, but their product, Undrip, is. Undrip has been for me a place I go when my Twitter and Facebook feeds  are boring and overly noisy. They developed an algorithm that sifted through my feeds and helped me discover, truly, the best of my web. Not just the web at large, but the web that I wanted to know. My little corner of the web. And Undrip made my little corner that much more cozy and familiar.

I opened up my cozy little corner today, the Undrip app, and I was shown a message that I knew was coming, but was not ready for, the message saying that the team was shutting the app down to work on a new and exciting project.

But, again, I say that startups are like friends and when they die it hurts. My cozy corner is once again the noisy circus is was before. And maybe I’m partially to blame. Maybe I could have used the app more. Maybe I could have told more of my friends about it. Maybe I… well, I guess none of that matters now.

What matters most is that my dear friends at the Undrip office, and all would be world-changers, can hear me say thanks! Thanks for making my life that much easier, if only for a while. Thanks for caring. Thanks for the long hours and the weekends. Thanks for the sweat and the blood, yes, the blood, for who would doubt the wounds these startups inflict.

There are, probably, too many startups out there. Heck, I’m one of them. But tonight there’s one too few in my heart.

So, guys, girls, entrepreneurs, would-be world-changers, I think I speak for everyone when I say I can’t wait to see what is coming next! Knowing you, it’ll blow us all away.

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The more I think about it and the more I see it and experience it, the mote I’m convinced that mobile devices are converging around one device. Laptops are becoming more like tablets, and at the same time tablets are becoming more like phones. Phones are getting larger, but I’m feeling more and more that the phone will be the device that will see the most activity long term. (at Caltrain)

The more I think about it and the more I see it and experience it, the mote I’m convinced that mobile devices are converging around one device. Laptops are becoming more like tablets, and at the same time tablets are becoming more like phones. Phones are getting larger, but I’m feeling more and more that the phone will be the device that will see the most activity long term. (at Caltrain)

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Google is shutting Google Reader down. I’m going to miss it so much. I’ve starred nearly 1000 articles as favorites that I’ll never be able to really have now. Hurts. In fact I just saved another one this morning. Old habit I guess.  (at Startup Graveyard)

Google is shutting Google Reader down. I’m going to miss it so much. I’ve starred nearly 1000 articles as favorites that I’ll never be able to really have now. Hurts. In fact I just saved another one this morning. Old habit I guess. (at Startup Graveyard)

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Where To Draw The Line: What Is A PC?

By McKay Thomas

Over the last couple years we have seen lots of people weigh in on whether tablets should be counted as PCs. However, we’ve seen a slow shift towards research firms adding tablets together to demonstrate PC marketshare.

What was one 10” tablet, the iPad, became lots of tablets of many sizes from many manufacturers. Flash forward to the last few weeks and we’ve been hearing rumors of a larger iPhone. Although Samsung has had lots of larger phones, Apple introducing a product in the category would be very legitimizing for the form factor, which leaves me asking: what is a tablet? And what should we count for marketshare?

Is a tablet defined by a diagonal screen measurement? That is about the only think I can find different between the iPad and the iPhone. A larger iPhone may only not count towards PC marketshare only because Apple will call it an iPhone Something rather than an iPad Something.

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There are many satisfactions to being involved with product and software development. There are also many dissatisfactions. The universe is determined to ship as little code as possible. As many engineers and developers and designers will attest to, shipping comes far too rarely.

However, when you’ve experienced a few shutdown projects, a few shuttered startups, and a few failed features, then the sweetness is all the more sweet when all the elements combine for a big launch. A day like today.

My faux-founder, Otavio and I set out to create the greatest product and technology team in Brazil. It was April last year when we started getting our first few yeses from team members. It grew from two to five, to 15, to now over 25. The goal was always quite simple: change the way people shop online. Make it faster. Make it trustworthy. Make it so easy that they stop shopping anywhere else. And that’s when industries start shifting. A brilliant product can get a rival CEO fired. Can get an entire board of direction reshuffled. That was the goal and today we took the first step towards that with the launch of our new web store. The new

I say we, but in reality the team did many of the final preparations without me. I left my day-to-day responsibilities at the company I co-founded in December. I ache in a certain way as I see this product launch as I am just beginning development on a new product at a new startup. I’ve written many times on how heartbreaking it is to leave something that demanded so much of your soul, even if it is what you know is the right thing to do.

I miss the team now and hope they can hear me across continents as I shout from the rooftops,”I’m so proud of you guys! You’ve done it! You shipped! And the tides in the industries we will disrupt have begun changing. I can feel it all the way from up here. You inspire me with your dedication and your product accumen. I miss you and am full, full, full with satisfaction in this, your victory.”

Parabéns meus amigos! Parabéns.

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I’m naked now. In a very metaphorical sense, but it’s true. Through the crazy emotional journey of fundraising, I’d slowly started putting on someone else’s clothes. Someone from the establishment, someone with old ideas and blinders, someone who wears parachute shirts and shoes I can quite describe other than uncomfortable.

I was listening to the questions of all those around me and was being consumed by them. I was letting others doubts about my business and my very future wear me. An outfit I’m not used to.

Then I had a call with the usability expert on my team. She’s met face to face with dozens and dozens of our users over the past month and as a result has deep understanding of the business. She had slowly watched me changed my clothes. Looking back, I could feel it too, but it wasn’t as obvious to me.

"That’s the wrong question, McKay." Stacy said. "We’re not selling information. You can get that anywhere." She went on to describe a doctrine that will no doubt guide this business over the next phase of its life. And maybe forever. The Stacy Doctrine.

As I heard it I felt the strange outfit begin to fall off and I began to feel exposed. Naked. I was once again fighting an industry worth billions with a vision I had relayed to Stacy but had somehow forgotten. I am not here to ask other people’s questions. I’m here to build something for my users. I’m here to make something and make it so well that my users will feel compelled to say, “Boy! This makes things so much easier.”

Not 3 hours later I came across this article in Fortune about the chairman of Samsung.

"In the late 1960s Samsung officially entered the electronics business. In the early years the company was known for cheap televisions and air conditioners. That all changed in 1995, when its chairman, Kun-Hee Lee, paid a momentous visit to the company’s plant in Gumi, a factory town in south-central Korea. Legend has it that Lee had sent out the company’s newest mobile phones as New Year’s presents and was horrified when word came back that they didn’t work. Later, at Gumi, he made a giant heap of the factory’s entire inventory and had it set on fire."

May we take the precedent of whatever it is our lives have been about until now and make a big heap of it. May we douse it with the fuel of shock and discouragement and pain and skepticism and light it up. Watch it burn. It doesn’t matter what you’ve made up till now if isn’t what you want it to be. If it doesn’t work or doesn’t inspire.

Screw other people’s questions. Go build something. That’s the Stacy Doctrine. And may we ever live by it.

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