Grabbing a seat on a rocket ship


Why I joined HotelTonight

Last week I started a new role as a Marketing Manager at HotelTonight, a white-hot startup based in the heart of San Francisco. After some time apart from startups, I feel like I have been released back into my natural habitat.

Back in April, a blog post I wrote entitled Rate-of-learning: the most valuable startup compensation ignited the largest response of any post I’ve written, in part because it validated the rationale for joining startups and because it aligned with real experiences of those in the startup community.

The key takeaway? The single most important reason to work at a startup is not salary or stock options but the chance to learn at an incredibly fast rate and generate compounding interest on those learnings over time.

Ironically, I wrote this post nearly a year and half removed from working at a startup—the last one I’d worked for, ThisLife, was acquired by Shutterfly at the end of 2012. I hadn’t realized it at the time but the piece was one part love note to startups and another part subconscious resignation letter.

Launching a new brand at a public company with financial resources and massive distribution channels at your disposal is a dramatically different experience than hustling to drive growth on a shoestring startup budget. But part of what working at a non-startup taught me is why I love startups so much in the first place: their abhorrance of bureaucracy, their aversion to mediocrity and a direct connection with the customer that comes from having proved nothing and being paranoid about getting your ass kicked.

This is why startups are able to win despite having fewer resources—and why it was time for me to put my money where my mouth was and hunt down the kind high rate-of-learning role I had advocated others to do in my post. To grab a seat on a rocket ship and never look back.


Download HotelTonight here

After talking with startups of varying size and scale, I was and am most supercharged about HotelTonight. An emerging powerhouse in the on-demand economy, HT makes the hotel experience sexy by letting consumers book a room on their smartphone in 10 seconds or less. Hotels love HT because of its focus on last-minute hotel reservations (which don’t cannibalize future bookings) and consumers love it because they get great deals on amazing rooms—making spontaneous weekend trips or last minute accommodations a cinch. At the highest level, I think there is something magical about a company with an incredibly simple, customer-facing front-end that is powered by a sophisticated logistics engine on the backend to make the magic happen.

Throughout the interview process—an adventure in itself — HotelTonight had all the attributes of a company with escape velocity growth. Three in particular sealed the deal for me:


Every company talks about the importance of culture—but talk is cheap. Culture is when you have a two hour interview late on a Friday afternoon right before Outside Lands and everyone still looks excited to be at work. Culture is when employees meet up with you for drinks during their off-hours to help you prepare for your new role. Culture is when you have an open work-from-home/time-off policy and everyone comes into the office anyway to be part of the action.

Walking into the HotelTonight lobby, you immediately see the words Build. Question. Respect. emblazoned on the wall. Usually these types of mottos are pretty meaningless because either A) they don’t line up with reality or B) they are just a series of cliches that fail to differentiate your culture from any other. But these words popped off the wall and became real for me as I connected with the company.


The HotelTonight office bar. Every employee puts a bottle on the shelf. Mine is the Fireball.

Build means thateveryone in the company is a builder, no matter their role. No matter if you’re in marketing or finance (i.e. not an engineer)—you find your own way to build the company, improve the product and make customers happy. The builder mentality is contagious; once it’s got a hold of you, it’s hard to be a part of any company where builders are scarce.

Good questions are a way to make sure you are building the right things. Should I be spending my time on X? Should the team be spending their time on Y? Is there a better way to do Z? Questioning helps you identify the things that matter and eliminate the things that don’t.

Questions demonstrate respect not only for your coworkers who are joining you on the mission, but the customers and the partners you are there to serve. Fuse all three values together, and you have an organization that’s laser focused on building the right things well. Many companies attempt this, but fall short on one dimension or another, and only the rocket ships are able reach the outer limits of space.


HotelTonight CEO Sam Shank gave a talk at SXSW Las Vegas about design being the ultimate differentiator in mobile commerce. In a world where the marketplace has shifted from offline to online, and from web to mobile, the stakes for design have increased exponentially as thousands of square feet of retail space are sucked into the 1136 X 640 pixel screen of the smartphone. A halfway decent design may be tablestakes for launching any new business on mobile—but great versus not-so-great design is the differentiator that allows consumers to sort the winners from the losers quickly and decisively, using their thumbs and powerful pocket computers to vote yes or no on your company’s existence.

Great design, however, can only be born out of great cultures because design is not a commodity, but rather a value, cultivated and sustained over time. You can see the value of great design not just in the craftmanship of the product a company ships but in the place where that product is built. Pick any company with a beautiful app. What you’ll see when you walk into their office is a space where aesthetic matters, filled with people who care about getting the details right. HotelTonight is that kind of place.


Inside HotelTonight headquarters in San Francisco


Paul Graham talks about “building something people want,” which despite sounding simple is insanely hard to do. Most startups never get lift off in this respect; they push their product into the market, but the market is unmoved. Over the last few weeks, I’ve told a dozen people about HotelTonight and nearly all of them downloaded the app and several have either booked or will book a room soon. Getting people over the hump of installing the app was my anecdotal test for determining how much product-market fit the product has, and in this case the readings on my PMF meter were off the charts.

As a marketer, I’m only at my best when I’m delivering something people actually want. A lot of marketing is removing barriers that keep people from adopting a product worth loving. Sometimes you’ll hear talk about “growth hacking” as a vehicle for taking rocket ships to the moon, but it’s a fantasy if the underlying product isn’t solid because they eventually run out of gas. When you have true product-market fit, the market will pull value out of your company as fast as you can build it because they genuinely want more. And that is the only fuel you need for the trip.

We choose to go to the moon, not because it is easy, but because it is hard.


As a mobile-only company, taking the hospitality market by storm is no small undertaking. Competitors dump millions into acquiring customers on the web and many of these tactics don’t work with a mobile app. Despite these headwinds, HotelTonight is riding a gigantic, cresting wave because consumers are mobile. Like the Great One, Wayne Gretzky, HotelTonight is “skating to where the puck is going to be, not where it’s been”.

I believe the HotelTonight rocket ship will go to the moon, remake the hospitality industry, and become the number one most loved hotel app in the world—and I can’t wait to be a part of that journey. To the ThisLife team at Shutterfly, I have enjoyed working with all of you and am rooting for you to win. To the HT team, thanks for welcoming me aboard and making me feel at home already. And to everyone who is seeking out a high rate-of-learning, take the risk to find the rocket ship that will get you there, not because it is easy but because it is hard. And it matters. Because when you hop on a rocket ship, it becomes a launch pad for everything else you will ever do.

Special thanks to Tammy Han from First Round Capital for putting me in touch with HotelTonight and helping make this happen.

Want to get hooked up on HotelTonight? Use my code KYLET for a $25 credit towards your first booking. You can download the app here.

↗ Popular posts: Rate-of-learning: the most valuable startup compensation • Uber may be the greatest company of our generation • Rise of the full-stack marketerMarket first, code later 

Rate-of-learning: the most valuable startup compensation


The frothiness of today’s environment in Silicon Valley makes it easy to get sucked into a warped sense of reality. Valuations are high, capital is cheap, housing prices are skyrocketing, and RSUs are flowing like wine.

Talk of another “bubble” is rebuffed, even by those who were scarred by the Dot-com collapse of 2000. Some argue we’ve exited the installation phase of technology—which was still sputtering along at the dawn of the new millennium—and have entered what Carlota Perez calls the ‘deployment phase’ of technology. In this phase, startups move “up the stack”, switching from building core infrastructure (i.e. interstate highways) to applications that go on top of it (i.e. Teslas).

Undoubtedly, changes in technology over the last 15 years have been breathtaking. The cost of bringing new products to market has dropped exponentially, and companies that hit product/market fit can build value incredibly fast through escape-velocity, engines of growth—going from worth nothing to worth billions, seemingly overnight. Unparalleled access to capital has led to an arms race for talent, with top tech companies stockpiling software engineers like ballistic missiles for the Tech Wars of the future.


Naval on exponentially increasing startup leverage

One risk of living in this Guilded Age of Tech is the temptation to view your own career and compensation through a disproportionately financial lens—much as a growing company would.

Companies are built on 5 to 10 year time horizons, so navigating the feast-or-famine fundraising environment and tracking jaw-dropping economic headlines across the globe are functions of survival. But when it comes to evaluating your own compensation and growth, focusing on the financial dimension seems problematic because it’s too short-sighted.

Since the time horizon for your career is long, the most valuable startup compensation you can acquire isn’t a competitive salary, a chunk of stock or a Yoga-laiden benefits package. If you look at the expected rate-of-return for each of these and benchmark them against the market, they aren’t dramatically different from what you could get working at the stereotypical big company. In fact, they are worse on average—with one exception:

The most valuable compensation for working at a startup as opposed to a “normal job” is a dramatically higher rate-of-learning (ROL).

Your rate-of-learning is a better proxy for how successful you will be than your current salary or stock compensation because it’s a leading rather than lagging indicator. Abandoning the cubicle at your normal job to throw yourself head-first into a startup is a fiery accelerant for growth, changing your career trajectory by orders of magnitude through a substantially increased rate-of-learning. To explain why, let’s define ROL:

Definition: Rate-of-learning is the velocity at which you are aggregating new insights and deploying them in ways that build value.

In physics, velocity is measured along two vectors: speed and magnitude. In this case, the pace at which you are uncovering new insights (speed) has a direct relationship with the leverage you accumulate deploying these new insights (magnitude). Whether this process of aggregating and deploying insights is in the form of writing code or driving growth, scaling this steep learning curve is the forging process that turns you into a badass full-stack developer or full-stack marketer with a high market value—not getting paid a large salary to sit in meetings all day.

There are three reasons why I believe rate-of-learning is your most valuable personal asset class:

Compounding interest on learning. You may have noticed in the graph above that the line representing startup rate-of-learning is exponential while that of a normal job is linear. While this is more conceptual than anything else, it illustrates an important point: if you reach a fast enough rate-0f-learning you start generating compounding interest on those learnings.

Let’s use a real life example. Imagine you’re a growth marketer at a startup and uncover a new way to drive sign-ups by aggressively retargeting people who have visited your blog organically. You deploy the retargeting campaign and it works, so next, you find a way to generate more quality blog content by syndicating posts from experts in your space so you can attract even more eyeballs. Having successfully widened the top of your funnel, you switch gears and figure out how to dramatically increase conversion by personalizing sign-up page copy and background images based upon location data you’re pulling off a visitor’s IP address. This leads to another insight about a series of fields that can be moved out of the sign-up form and into the onboarding flow to reduce friction. The cumulative effect? You increase sign-ups by 20%.


In a startup, this series of experiments can happen over the course of a few days. In the alternative universe of a normal company you might be waiting a week for a small retargeting budget or approval from your manager. Therefore the valuable insights that should theoretically follow your initial insight may never come. If you extend this slow rate-of-learning over months or years, the opportunity cost of missed insights is massive.

Learning equals leverage. People think having “fuck you” money is leverage, but in reality, a high rate-of-learning gives you more leverage than money does. If I were to give you a choice between wiring $10,000 to your checking account or an opportunity to uncover 50 powerful insights that could land you an awesome job at Airbnb or Dropbox, which would you take?


Another way to think about rate-of-learning dividends: the present value of money is low, especially when interest rates are at 0%, because you can’t generate as much compounding interest on money as you can on your learnings. So if you have a choice between getting paid $50K at a startup or $100K at a dying company, your future self will thank you for taking half the pay in exchange for a 3-5X ROL. A high rate-of-learning is the most bankable asset you can have in the startup world because it’s the vehicle by which longterm value is created, both within yourself and for your startup.

Learning is an end to itself. The interesting thing about highly successful people is that most of them they don’t stop working once they’ve “made it”. They continue climbing the learning curve long after the millions from big exits have been wired to their bank accounts. Why? After years in high rate-of-learning roles, they discover that learning was an end in itself.

Though it may seem like money is spilling all over the streets in Silicon Valley, don’t get distracted by shiny objects. Play the long game. Put yourself in a position to maximize your rate-of-learning, even—and especially—if it makes you a little uncomfortable. The long game is hard, but rewarding, because you’ll know you had the strength to make the steeper climb.


Uber may be the greatest company of our generation


This weekend my wife and I had friends visiting from Merced, a small town in the Central Valley about two hours east of San Francisco. It was a perfect weekend that combined the best of everything the Bay Area has to offer— cloudless and spectacular 68° weather, a long hike off Skyline Boulevard down to Half Moon Bay and some amazing Greek food in Los Altos.

On Saturday night we decided to go out for drinks and a nice dinner in San Carlos and, naturally, my first thought was to fire up my Uber app and get the evening’s transportation dialed in (I’ve vowed when possible to never take a traditional cab again). “Have you guys heard of Uber?” I asked as I was making Moscow mules for our guests. “What’s Uber?” they replied. I immediately shifted into VC-pitch mode, explaining how Uber may be the coolest thing to come out of Silicon Valley in a decade and how it will transform how people and things are moved on-demand, with just the push of a button. They immediately got it.

As I hit the “set pick up location” button for our trip, we marveled at the simultaneous simplicity and intricacy of the app, watching in real-time as our driver, Fadi, made a left turn in his black Chevy Suburban off the 101 freeway and hopped on the 92 towards our house. Then I said “you guys realize this is just the beginning for Uber, right?” I described the company’s crazy growth trajectory from having just one driver in San Francisco back in 2009 to now processing tens of thousands of rides per week in cities all over the United States and in countries all over the world, while growing at roughly 20 percent month-over-month. This statement sparked an entire conversation about all the pain points Uber could solve and how great it is that we get to “live in the future”.


We talked about a future where unreliable public transportation that gets shut down by strikes is disrupted by a more cost effective and human alternative (Uber’s fare splitting feature actually makes it cheaper to take Uber X than BART in many cases). We talked about a future where physical goods can be transported from point A to point B with just a few taps, as a network of drivers (or drones) bid in real-time to deliver your package in a matter of hours, making next-day delivery outmoded. We talked about a future where self-driving cars take the wheel, moving people and things with increased safety and efficiency, and your Uber driver transforms into an Uber concierge, focused on the critical human aspects of these transportation transactions. This was a future we all wanted to live in.

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Unbundling Silicon Valley

And spawning Valleys all over the world


Last week, a late-night Twitter conversation with Marc Andreesen and Dave McClure got me thinking about the future of Silicon Valley in a different way.


The perennial “future-of-the-Valley” debate isn’t a new one. Nor is it surprising that a community preoccupied with building the future is curious about how the entrepreneurial world map will be redrawn in years to come. Will the Bay Area remain the mecca of modern tech entrepreneurship? Or will replica Silicon Valleys sprout up in cities like Singapore, Moscow and Tel Aviv that eventually reach parity? In short, will the future of the Valley be a story of continued consolidation or one of global diffusion?

I’ve always been in the camp that’s long on Silicon Valley—not just as a physical space for entrepreneurs but a mental one that values putting big dents in the universe. The ecosystem here is both complex and self-reinforcing, and each component—the Stanfords, Googles, Wilson Sonsinis, weather and natural beauty—would individually be so difficult to replicate that copying the entire package would be nearly impossible, akin to building a man-made Mount Everest in the desert and convincing the best climbers in the world to abandon the original and come scale Ever-esque.


I still believe this about the Valley. But Marc’s 140-character stream of thoughts has me thinking the entire premise of the debate may be wrong—and far too binary for what the future might actually look like. The Silicon-Valley-versus-the-world argument smacks of the mercantilist rhetoric of the 16th century that viewed global wealth as a zero-sum game—that Silicon Valley’s loss would be some other ecosystem’s gain and visa versa. Instead, Silicon Valley’s biggest export may be a model and culture of entrepreneurship routed across the globe, pollinating pockets of specialization that emerge and contribute new value to a much larger ecosystem. These geographic outposts would apply the Valley’s startup model to new domains where they are uniquely positioned to build a longterm, sustainable comparative advantage.

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Market first, code later

How the full-stack marketer breaks the rules to get started


Most startup projects fail because they never even get off the ground. Ideas stay in the brainstorming phase on the back of napkins and never make it to the actually-talking-to-prospective-customers phase, which is the critical moment when a startup takes its first breaths of life.

There are usually a litany of excuses that go along with the premature death of a startup idea: I don’t have a technical cofounder so how will I build my product? How will I have time to work on this with work or school? What if someone just steals my idea? Nonsense.

Let’s get a few things straight.

• You don’t need a technical cofounder to start talking to prospective customers about your idea. In fact, what good is someone who talks to computers and writes code all day going to be in talking to people.Talking to people is your job; get used to it.

• There is never a “good time” to start working on your startup. You can wait for things to ease up at work or to be done with school and before you know it you’re married with kids, sitting in a cubicle talking to your coworkers about how you once had this great idea. Lame.

• No one cares about your idea. Literally no one, except maybe you, cares about your idea.Your belief that someone is going to steal your idea is an illusion based upon the bias of your own perspective. Besides, ideas are completely worthless. Execution is what matters.

Running a startup is kinda like climbing without a rope.

Since your first ideas will probably suck anyway, use them as a vehicle for learning how to execute. Climbing the steep learning curve of modern, digital entrepreneurship is what’s going to turn you into a full-stack marketer that’s a force to be reckoned with. The further you climb, the more skills you acquire for dealing with challenging situations and traversing uncharted territory. And the failure you’ll encounter along the way will innoculate you against the idea that failure signals finality; failure is just table stakes for getting into the game.

The only way to learn to climb is to start. There is no other way.

So cut the rope.

The full-stack marketer doesn’t wait for anyone’s permission to get started. There isn’t time for that. So he breaks certain rules to put himself into a position where his startup can take shape and grow. Here are four rules you should get comfortable with breaking if you want to convert your ideas into realities.

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Pivots, perseverance & insights

How entrepreneurs “drill” their way to success


The most precious asset any entrepreneur has is time.

Because time is constantly slipping away, one of the most basic entrepreneurial dilemmas is knowing when to pivot and when to persevere. When to take flight and when to keep fighting.

Like an oil prospector in search of his first strike, an entrepreneur traverses the dangerous terrain of rapidly shifting markets to find elusive black gold. You never know whether you’re meters away from hitting the lucrative depths of product-market fit or whether you should pack up your rig and find another spot to set up camp.

Great companies, however, aren’t built on pivots or perseverance, but on insights. Mark Zuckerberg’s decision to build Facebook wasn’t based on a conscious decision to pivot or persevere but instead on a core insight into a human behavior that could be ported to the Internet. Similarly, an oil prospector chooses when to keep drilling and when to give up based upon the insights and clues he collects along the way: that rock formation looks suspect, these deposits look promising, that river seems to have moved.

For entrepeneurs, there is more than one way to identify a promising spot to drill so you can start sifting through the mud to unearth these gems of insightfulness. And no one heuristic is necessarily better than another in the way that no one philosophical theory is demonstrably better than another—because they’re just models of thinking.

One way to start drilling is to identify an acute and widespread pain point, one that you’ve experienced personally or have seen others struggle with, and try to solve it. Think of Instagram making photos on your phone not look like shit. Another is to look for a large, validated market and find a better way to serve it. Think of how Amazon plans to restructure the logistics industry with theirdelivery drones. Yet another is to target a large incumbent business and use new technology to dislodge their hold on the market. Think of how Netflix murdered Blockbuster (RIP).

Even when you use one of these frameworks as a starting point, it remains incredibly hard to build something people actually want. The soul-crushing aspect of entrepreneurship is that you may never find black gold at all. And since our time is finite, you can only place a finite number of bets. The good news is that as you pivot and persevere in your entrepreneurial drilling, the insights you collect along the way go into an insight bank you can draw from to make smarter subsequent bets, increasing your odds of eventually uncovering something worthwhile.

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The Age of Context

Turning real-world locations into personal sensors


When I was a kid, I remember reading books that depicted the future. Everything was taken care of for you by technology and no one had to work very hard because robots subsidized human productivity.

That second part turned out to be total bullshit, but in the waning months of 2013 it’s starting to feel like we do in fact live in the future. What I mean is that technology is starting to do more and more of the heavy lifting for us, which is ironic given that modern-day humans work more hours for less pay than their 20th century predecessors.

But we can’t really complain. Gold miners in the 1840s couldn’t push a button on their smart phones and have a horse drawn carriage pull up minutes later. Italian merchants in Renaissance markets couldn’t exchange gold bullion instantly with tiny plastic squares. File storage for Alexander the Great meant building a 100,000 square foot stone library in Alexandria to house hundreds of thousands of scrolls.

We work like dogs but live better than the Kings of England or Pharoahs of Egypt ever could have imagined.

At the push of the button we can get almost anything we want.

And things are just getting started. Over the next few years, I predict we will finally unlock the Minority Report-style world we were promised by Hollywood and science fiction. In this new world, you won’t even have to push a button to get what you want. You won’t even have to take out your phone. Our powerful pocket computers (and hopefully less-douchey looking Google Glasses) will be able to predict what you will want purely based upon context.

Real world sensors will be deeply embedded in everything around us, giving us information where and when it matters most. And we will be able to tap into this network throughout the day as our smart phones communicate—on our behalf—with the nodes and other devices within it. As we interact with these sensors and push updates to them, our feedback will percolate throughout the entire network, like ripples in a vast digital pond.

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The Goliath Syndrome

Why big companies get slayed by startups


It’s a paradoxical yet persistant truth in Silicon Valley that innovation is almost exclusively a biproduct of small, scrappy startups, not large public corporations.

It may seem counterintuitive that disruption and headcount would have an opposite relationship. You would think that amassing an army of thousands of employees would give you more leverage in this digital Game of Thrones, but business parks across North America are strewn with the carcasses of megacorporations that have been killed off or irrevocably maimed because they thought the clock would never run out on them (Kodak, Blockbuster, AOL, Motorola, RIM, Sun, Sony).

There are some obvious exceptions (Apple), but as a general rule bureaucratic inertia at large companies gets channeled into a death grip on the status quo, not big bets for the future.

Like the power law of distribution, innovation in the technology space follows a sort of inverted 80-20 rule (also known as the Pareto Principle) where the top 20 percent of startups like Square, Uber and Dropbox generate 80 percent of the innovation and the largest 20 percent of corporations like Samsung, Yahoo and HP mount 80 percent of the obstruction to that innovation through activities masquerading as progress, like patent lawsuits, government lobbying and acqui-hiring youthful competitors.

These are textbook symptoms of The Goliath Syndrome—when big companies become blind to their own vulnerability because they view their size as an asset instead of what is truly is: a liability.

But why is this the case? Why can’t more big companies defy bureaucratic gravity and institutionalize the process of innovation the way startups are naturally able to do? Apple practically stands alone as an exception to this rule—a huge company that behaves like a paranoid startup, pivoting from personal computers to MP3 players to phones to tablets as if they were a few guys in a garage about to run out of money, cannibalizing their own profits in the process.

It doesn’t make logical sense. You have companies with billions on their balance sheet that can’t innovate worth shit while teams with a dozen hackers, designers and engineers and almost zero money are able to turn entire industries on their head. The list is long: Napster → music industry, Uber → taxi industry, Square → payments industry, Dropbox → file storage industry, Makerbot → 3D printing industry, Kickstarter → funding industry, Netflix → movie rental industry, Tesla → auto industry etc. And this list could go on for the rest of the post. You also have “startups” in the financial sector like 500Startups and AngelList that are dismantling the traditional venture capital and fundraising industries, riding an historic tidal wave that is shifting power away from investors towards entrepreneurs.

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Rise of the full-stack marketer

A shifting consensus around what a “seller” founder looks like


It is often said that there is an engineering bias in Silicon Valley, but in reality, it’s a bias towards doers over talkers, of execution over ideas.

This is why you’ll frequently here the refrain that MBAs make bad startup founders, because MBAs are oriented towards administration and management (talking) over designing, programming and growth hacking (doing).

That doesn’t, however, mean that engineers always make the best startup founders either. While it’s next to impossible to imagine a great founding team that doesn’t have at least one engineer, increasingly, it’s becoming just as hard to imagine a great founding team that is comprised solely of engineers.

You can visualize the requisite skill set for a founding team as a pendulum that swings over time depending on the macro-circumstances. Twenty years ago, the technical costs of building a product were so enormous, that it made sense to stack your team with engineers and figure out your business later after you’d raised your $20 million A round; to load up on business guys prematurely would have been putting the cart before the horse. When Silicon Valley got overheated in the late 90s, VCs were writing checks for business plans with no product, so all the business guys wanted to start companies too—and we all know how that worked out.


Over the last decade however, the cost of building a product has asymptotically drifted towards zero. Your main cost is time and the certainty that comes with a steady paycheck. With the ascendancy of the full-stack developer, you can switch between web, mobile and native without necessarily having to switch people. With technical costs going down, one of the biggest challenges a modern-day founding team will face isn’t getting the product built—although that is and always will be hard—it’s getting distribution once you’ve built a minimum viable product, nailing the killer user experience and putting your product into the hands of real people quickly.

Maybe this explains why the greatest founding teams of all time have almost always included a builder and a seller.

Think Jobs and Wozniak, Allen and Gates, Ellison and Lane, Hewlett and Packard, Larry and Sergei, Yang and Filo, Omidyar and Skoll. -@Naval

Naval Ravikant’s post from four years ago remains the single most clear articulation of why the best founding teams require a builder and a seller, and why two founders is the magic number. But if two is the magic number (and I think it is), then what do these two ideal founders look like in 2013? What attributes do Founder A and Founder B have that make their odds of success higher than average?

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In entrepreneurship, impatience is a virtue

Impatience turns wantrepreneurs into hackers, designers and programmers that focus on execution instead of just ideas


It is often said that patience is a virtue. And sometimes it is.

The best time for patience is when you don’t have control. If you’re waiting in line at the DMV to renew your license or stuck in rush-hour traffic on the 101, no amount of impatience is going to change things for the better. In these cases, impatience is counterproductive because the stress-induced cortisol shooting through your veins will inevitably grind you down and make it harder to fight the battles that actually matter. It’s better to keep your powder dry.

In the world of entrepreneurship and startups, these same rules don’t apply. When you’re building a startup, there are a lot of things you don’t have control over: timing, the market, your competitors, the macro-economy. These forces are so powerful that they can overwhelm great products and great teams like a giant wave that capsizes a tiny boat. Building a company (at the risk of mixing too many metaphors) is like a game of three-dimensional chess that never really ends - and you’re constantly dancing on the edge of glory and failure. The only thing you have control over is yourself, and in this persistant battle to create something from nothing, impatience is your friend.

Typically you will hear people talk about “drive” as an essential ingredient to building great products and great companies. But in an entrepreneurial context, drive is really just the ability to convert impatience into action. The first time I was ever exposed to “code” was about ten years ago when I was editing my MySpace profile with one of those glittery HTML generators. I became so impatient with how shitty my profile looked that I started manipulating the code directly to get the result I wanted and Googling things like “How to link an image” so I could write simple things like <a href=”image.jpg”>link</a>. A few years later I started my first little company, a T-shirt business that made politically-oriented t-shirts and bumper stickers. I had poll-tested my first batch of t-shirt sketches with my fellow high-schoolers and when it came time to actually make the designs I didn’t want to hire a designer because I was too impatient, so I played around in Photoshop for hours until I felt happy enough to take the files to the printer.

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Don’t tread on me

The ascendancy of libertarianism in Silicon Valley


The average American looks to the West and assumes that Northern California is populated by roving packs of Prius-driving, weed-farming, granola-eating, deodorant-despising, left-wing Marxists.

For certain pockets of the Bay Area—Berkeley comes to mind—this is probably a fairly accurate description. But when it comes to Silicon Valley and the tech community more broadly, the political sentiment here is not so easily put into a left-right, Republican-Democrat box.

In fact, over the last few years, I’ve seen something much different happening here—a rising tide of libertarianism in a community that is increasingly taking on the mantle of ethical capitalism, free-markets, civil liberties, limited government and personal responsibility.

Silicon Valley’s political reawakening and realignment away from the two major parties towards a philosophy of economic liberty and social tolerance has come not a moment too soon, at a time when crony capitalism is at an all time high (Solyndra), faith in government is at an all time low (11% Congressional approval rating), the economy is in a sluggish state of perpetual malaise (2% GDP growth) and civil liberties are being eliminated at the stroke of politicians’ pens (NSA Prism).

Last year, when Congressional Democrats and Republicans alike moved to quietly push through SOPA legislation that would give the federal government power to regulate and censor the Internet, an army of Silicon Valley-ites of every political affiliation and background imaginable came out of the woodwork to take it down, protesting what was widely seen as a blatant overreach of power by the government.

Petitions spread across the Internet like wildfire. Tech companies blacked out their logos to raise awareness. Anti-SOPA Tweets were fired off from iPhones in coffee shops from the rolling hills of San Francisco to the steamy streets of Austin to the bustling avenues of New York City. Practically in real-time, as Congress prepared to vote on legislation which was essentially a done-deal, you saw nervous politicians start to back peddle—switching their votes from yes to no.

In a matter of days, the SOPA bill which was supposed to sail through Congress went down in flames as an activated citizenry took to the streets, both literally and virtually, in a deafening demonstration that surely had the Founding Fathers cheering from their graves. It seemed that, for once, the government was fearing the wrath of the people who had elected them to serve the country and protect the Constitution.

“When the people fear the government there is tyranny, when the government fears the people there is liberty.” — Thomas Jefferson

If you think the blowback against SOPA was a one-off event, a momentary blip of techie civic activism, you’re wrong. From the proliferation of groups in Silicon Valley supporting the restoration of the 4th Amendment in the wake of the NSA Prism scandal to widespread support for foreign-born immigrants and entrepreneurswho want to work and start companies here, Silicon Valley is becoming a mecca of digitally-engaged advocates for increased liberty.

Senator Rand Paul writing “Give me liberty” on the wall at Facebook HQ when he was courting Silicon Valley entrepreneurs back in June.

Is this because people here are more tech savvy or because the entrepreneurial ecosystem here is so naturally aligned with the concept of individual liberty? I would argue that while it’s probably some combination of the two, the culture in the Valley makes it a unique breeding ground and clearing house for libertarian ideas unlike any other enclave of the country.

An anti-bailout culture. An important pillar of Silicon Valley culture is its unique attitude towards failure. Unlike the “too big to fail” culture of Wall Street or the perpetual blame game in Washington, D.C., entrepreneurs in Silicon Valley are encouraged to own their failures, to wear them as a badge of honor. This cultural difference between Wall Street and Silicon Valley has massive ramifications at scale. After the mortgage crisis of 2008, Wall Street received a massive bailout from the taxpayers. When the tech bubble burst in 2001, there was no bailout; tech entrepreneurs took their ass-kicking, regrouped and began taking smarter risks.

An anti-overregulation culture. The tech community has come out strongly against a stupid wave of new SEC regulations designed to make it harder for startups to raise money and for smaller investors to invest. The new laws would closely monitor how startups publicly solicit funds and put more stringent diligence into place for verifying accredited investors (who must have an annual income of at least $200K per year or have a net worth of over $1 million). As if Sarbanes-Oxley hasn’t screwed things up enough, the SEC believes that making itharder for startups and investors to collaborate is somehow a good idea.

An anti-patent trolling culture. While some of the biggest corporations in Silicon Valley are among the worst perpetrators of patent trolling around, many of the biggest advocates against patent trolls are in tech. Marc Andreesen, Ron Conway and Mark Cuban for example have been vocal in their opposition to patent trolling. Mark Cuban has been quoted saying, “I would like to see software patents completely eliminated, or if not eliminated have a five-year max shelf life” lamenting that “dumbass patents are crushing small businesses”.

A pro-free speech culture. Part of the opposition to SOPA/PIPA was rooted in the fact that the Valley has a very pro-free speech culture. The idea that some bureaucrat 3,000 miles away could have the authority to shut down a private citizen’s LOL Cats blog because it “violated” the Stop Online Piracy Act was something that offended people’s belief in the first amendment. This isn’t surprising; the Internet itself epitomizes the idea that the free flow of ideas should be facilitated and protected as much as possible.

A pro-immigration culture. This Valley was in large measure built by immigrants from Asia, India and Eastern Europe. Many of the biggest tech companies of the last few decades were founded by immigrants (Google, eBay, Yahoo) and over 50% of the top startups in the U.S. were founded by immigrants. That’s why it’s so backasswards that we make it incredibly hard for foreign-born entrepreneurs who come here, get degrees from Stanford and start companies, to actually stay here, create jobs and help grow the economy.

A pro-capitalist culture. At the end of the day, there is no place where the creative destruction of the capitalist system is more on display than in the Valley. It’s Adam Smith on steroids. Thousands of startups emerge every year, many of which fail and some of which succeed and put dying companies out of their misery. We are living in the midst of a Silicon Valley gold rush where software is “eating the world” and transforming our lives. The velocity at which new products and services are being created and outmoded ones are being destroyed is unprecedented, and probably rivals the Industrial Revolution.

Now, am I saying that 80% of Silicon Valley is going to vote for Rand Paul in the next Presidential Election? No—that probably won’t happen. But I am saying that Silicon Valley has a chance to decouple itself from both major political parties and establish a new American political philosophy based upon liberty and technological progress that decries the authoritarian leanings of both major political parties.

And as the political lines in the United States get redrawn into a battle between authoritarianism and libertarianism, Kings and rebels, incumbents and startups—Silicon Valley has an opportunity to become a stronghold for liberty and lead a Second American Revolution.


Our new office decorations at Shutterfly
  • iPhone 4
  • Aperture: f/2.8
  • Exposure: 1/24th
  • Focal length: 3mm

Our new office decorations at Shutterfly

In entrepreneurship, impatience is a virtue


Impatience turns wantrepreneurs into hackers, designers and programmers that focus on execution instead of just ideas

It is often said that patience is a virtue. And sometimes it is.

The best time for patience is when you don’t have control. If you’re waiting in line at the DMV to renew your license or stuck in rush-hour traffic on the 101, no amount of impatience is going to change things for the better. In these cases, impatience is counterproductive because the stress-induced cortisol shooting through your veins will inevitably grind you down and make it harder to fight the battles that actually matter. It’s better to keep your powder dry.

In the world of entrepreneurship and startups, these same rules don’t apply. When you’re building a startup, there are a lot of things you don’t have control over: timing, the market, your competitors, the macro-economy. These forces are so powerful that they can overwhelm great products and great teams like a giant wave that capsizes a tiny boat. At the risk of mixing too many metaphors, building a company is like a game of three-dimensional chess that never really ends - and you’re constantly dancing on the edge of glory and failure. The only thing you have control over is yourself, and in this persistant battle to create something from nothing, impatience is your friend.

Typically you will hear people talk about “drive” as an essential ingredient to building great products and great companies. But in an entrepreneurial context, drive is really just the ability to convert impatience into action. The first time I was ever exposed to “code” was about ten years ago when I was editing my MySpace profile with one of those glittery HTML generators. I became so impatient with how shitty my profile looked that I started manipulating the code directly to get the result I wanted and Googling things like “How to make an image tag” so I could write simple things like <a href=”image.jpg”>link</a>. A few years later I started my first little company, a T-shirt business that made politically-oriented (read: right wing) t-shirts and bumper stickers. I had poll-tested my first batch of t-shirt sketches with my fellow high-schoolers and when it came time to actually make the designs I didn’t want to hire a designer because I knew I would becomeimpatient, so I played around in Photoshop for hours until I felt happy enough to take the files to the printer.


My first business -

The difference between an entrepreneur and a wantrepreneur is that entrepreneurs use impatience as a vehicle for making progress; it’s the fuel in the tank that keeps the trip going. The roadblocks and hurdles that stop nontrepreneurs in their tracks just become the next milestone in the journey. Need to build a proto-type but aren’t very good at programming? Wireframes and photoshop are your friend and can get potential users closer to a real product than a sixty-page business plan ever will. Don’t have a “technical cofounder”? That sucks. There are so many free resources out there to start learning to code (like Stanford’s video lectures on Objective-C and Xcode) that the barriers to entry are practically non-existent.

For wantrepreneurs, impatience is usually greeted with a range of excuses that masquerade as progress (business plans, schwag, going to conferences) all of which obfuscate and abstract from the core task had hand - learning how to build a great product. When you are pouring your energy into things that are on the periphery of what actually matters, progress becomes nothing more than an illusion. This observation comes from experience because I’ve been on the wantrepreneur side of the ledger many times before. Instead of digging deep and learning to program, I’ve procrastinated and tried to fill the void with building pitch decks in Powerpoint that just fall flat. It was just a little over a year ago I finally took the plunge and started learning to build iOS apps in Xcode and I still have so much to learn. The internal struggle between being a wantrepreneur and entrepreneur isn’t a battle that ends, it’s a battle that I fight myself on an almost daily basis.


Finally learning to program in Xcode

Impatience is a virtue because when it can be converted into action. The biproduct of this type of action, of knocking down obstacles over and over again, creates a specific kind of momentum that is incredibly important for building companies. It’s not the false kind of confidence rooted in ideas and words but the kind of confidence you can only acquire through execution, anchored by the humility of having tried and failed over and over and over again. Even though I’ve designed and launched a handful of products, I still don’t consider myself a designer or an expert in user experience. Even though I’ve been programming here and there on the web and for iOS for several years, I am the furthest thing from a software engineer. Even though I’ve shipped products that have acquired thousands and thousands of users (Gunman got over 1M users), I’m no growth hacker either. I’m just an impatient son-of-a-bitch that learned how to design, program and growth hack products out of necessity, in the pursuit of trying to build something people want. If I do my job right, I’ll be able to find realdesigners and hackers to join the cause - but they better be impatient too.