Venture & Business Design at IDEO. Formerly at Lerer Ventures & GroupMe.
Entrepreneurs are often given two pieces of contradictory advice: persistence and flexibility. Have a vision and pursue it through years of people telling you you’re out of your mind. Or, be flexible: look at data, iterate, and change based on the signals you’re getting. There isn’t an actual algorithm. You have an investment thesis about why this project is likely to work and have some outside result, and usually that’s expressed in a set of statements and hypotheses, that if you’re right about, adds up like a logical proof and gives you the output you’re looking for. And you can have varying level of confidence in how these pieces are adding up and supporting your theses.” “The challenge is to follow them both, but know which advice is most appropriate for which situation. You must know how to maintain flexible persistence.

Applied Discovery: Sam Morse

Instructive illustration of the value of behavioral insight in the story of Samuel Morse. (full post here):

Even technical inventions are defined, in many ways, by their non-technical impact on the world, by what they enable for people in their lives. Let’s talk about the telegraph and its inventor — or one of the inventors — Samuel Morse. 
Samuel Morse was actually an artist for the first half of his life, and he painted portraits professionally. He landed this sweet gig in New York painting the famous Revolutionary general Lafayette. Morse was a huge fan, so he got pretty stoked about this, and he wrote letters to his wife back home in Connecticut just beaming with excitement and pride. But she would never read those letters, because back home she had fallen ill, and then later died. The letters from his family explaining the situation hadn’t shown up yet because they had to be delivered on horse, which took like a week to do. So then the dude invents instantaneous cross-country communication.
It’s a great framing of the story — albeit simplistic — because it contextualizes his work against the reason it matters to the world.  It enabled connections between people that weren’t possible before. These days we like to complain about how over-connected we are, how that actually makes us lonely. I think Morse was lonelier.
But, it’s interesting that Morse is our primary association with the invention of the telegraph. Remember that he was a painter for most of his life, not a scientist. His invention depended heavily on the work of the people who came before him and worked with him.  Much of the pioneering thinking behind electromagnetism was already discovered by a slew of other scientists, and even the first telegraph was, in fact, created by someone else — a pair of scientists named Weber and Gauss —not Morse.


One of the reasons Morse’s technology took off where others hadn’t is the insight of morse code. 1774 George-Louis le Sage invented a telegraph that could send complete, written messages. 1774! Samuel Morse wasn’t even alive back then. But this system required dozens of cables, you can see it here, one for every letter in the alphabet, because that’s what he figured was necessary to encode language into an electrical signal.


Morse code, a non-technical discovery I’ll note, meant that communication could be handled exclusively by a single cable. This made the invention significantly simpler and cheaper to implement.
But even though the technology was sound, Morse had a pretty bad “market fit” problem in front of him. Why would anyone use a telegraph where there were no cables… anywhere.
So Morse ends up spending the next years of his life pushing for adoption of his technology. In the process, he ends up burning through all of his money. He goes totally broke trying to petition Congress to install a kind of test cable, a line between Baltimore and Washington D.C. to communicate important political updates. He writes these depressing letters about how his hair is turning gray, and his vision is failing. Death was the only thing he saw in this future at that point.
This was all taking place during the Panic of 1837, the worst recession in the country’s history so far. There wasn’t a lot of optimism around federal funding for a theoretical technology without any proven benefit. Another dream client, right? The bankrupt United States government?


Eventually Morse slowly convinces one congressman at a time, and there’s this critical vote that barely passes, at like 89-82. But it works, and this cable gets constructed. It carries 30 letters per minute — about 14,000 times slower than a 56k modem, but pretty sweet nonetheless. And his standard becomes adopted by all of Europe and eventually he sees it spread into South and Central America. And of course, this technology is the foundation for modern communication, leading to the phone and the television and the internet, and so on.

This second half to Morse’s story is, to me, just as important as the initial invention. We often remember the people who successfully popularized or commercialized an invention more than the person who made the initial breakthrough. You know, we associate Edison with the light bulb, not Joseph Swan. Bell with the telephone, not Elisha Gray.
There are bad reasons for this, like privilege and power. These guys could do some pretty nasty things to take control of these creations. But the ability to take something from the lab and spread it out into the world is important, because that’s when the widespread human impact is actually felt. The human impact, not the technical.


Brian Eno, long-time composer and musician, has a philosophy about music that he sums up as “surrender.” At the moment of surrender, the listener acknowledges that the piece, not themselves, is in control. According to Eno, crossing this threshold is the point at which you’ve created something special.

Surrender is an active choice not to take control. It is an active choice to be part of the flow of something. We enjoy surrender situations.

He takes this theory further to assert that when you consider some of the realms of human experience that we covet most: art, sex, drugs, religion … surrender is the thread that binds them all. We crave when we can ultimately bestow control to some other force. We are, apparently, physically engineered to lose ourselves in something else.

The paradox in this of course is that we worship control. We dignify power and autonomy and those that wield it. And we consistently seek for ourselves a supreme level of authority over our own lives. The paradox is only intensified by our regular dismissal of people and ideas that surrender. Expressions of surrender or submission in every day life are considered forms of weakness.

The products we use seem to dignify this same control ideal. Since listening to Eno’s talk, I’ve found myself categorizing services I use by whether they optimize for control or surrender. Mailbox gives me control over who and when I respond to email. Instagram literally offers filters to control how I view the world I am experiencing. Instapaper lets me control when and what I read in the format of my choosing. IFTTT allows me to control interactions between services that the services themselves have yet to consider. Almost all of the products I use not only afford control, but communicate it as the sole value they offer.

But if the human experiences we delight in most are where we ultimately surrender, then why are products we use so insistent at giving us more control? Why do we seemingly seek a controlled and refined human experience instead of an honest, raw relationship with the world around us?

This is something I’m grappling with, but I have a few theories:

Information has become easier & harder: The increased availability of data and the infrastructure of the internet have done two things. It’s created a wealth of information with which to harness for more varied and dynamic experiences. Maybe these products are resting on the underlying assumption that a textured experience is a better one. The other thing that has happened, due to the same wealth of available information, is that its become harder to derive signal from noise. To accurately tag, store and retrieve data to present back to a user in meaningful ways has become a great and growing technical challenge. I think many of the products we use are, without necessarily knowing it, solving for this problem first and foremost.

We’re overindulged: Expectations have risen for personalization and contextualization:

It seems it’s no longer good enough that content be intelligent and valuable; you need to consider the nuance that dials your message to an audience in their context. Partly in response to the deluge of new information available, there is a growing expectation that its being used. Quantified-self began as a powerful set of tools to harness what we can surface about ourselves to make us better. But something is lost when we discover value in new tools but prioritize it to the point that it strips out the delight and beauty in the product.

There is also an interesting space where the blend of control and surrender can unlock unique potential. In other words, how are surrender experiences made more immersive by providing for an initial form of control. Take Treehouse by Interlude. They’re taking a medium that is entirely passive and surrendering, video, and marrying it with choice to create a more engaging dynamic. If they’re an indication of whats ahead, the future is exciting. Eno talked a bit about this confluence:

A good analogy is surfing … when you watch someone surfing … they take control momentarily. They situate themselves on a wave and then they surrender … they’re carried along by it. And then they take control again. and then they surrender.

Maybe we are in store for more blended experiences like Treehouse. From what I’ve seen though, striking the balance between these extremes without imbuing complexity is a significant challenge.

Eno’s concept of surrender has shifted how I think about product, and its become in many cases a first filter when I try new technologies. For product builders, there might be great hidden value in optimizing for it. It may just be that creating engaging experiences isn’t by granting control, but by taking it away, by allowing people to fully immerse themselves in your product by losing themselves in it. 

Perry Chen on starting Kickstarter:

sometimes a good idea is like an artifact that you find. it’s deep in a cave, lodged in the earth, and you need people to help you pull it out and show the world. yancey stickler and charles adler came down into that cave with me. i showed them what i had found. and they helped me pull it out. 

and that’s really how it feels. like the idea is its own thing, stumbled upon. and that we pulled it out, cleaned it up, and invited people to a party to come see it. it’s always felt this way.

The pathological issue with computer science: why coding can wait

Pathology is defined as “the precise study and diagnosis of disease.” The subject’s name is derived from the Greek word pathos, which means “experience” or “suffering.” Medical students typically take up this course on illness in their first year of medical school. They study the varying afflictions that grieve the human body, and are trained to identify and differentiate what these sufferings might be.

In fact, most of what an early medical student is taught (anatomy, histology, biochemistry) is not the medicine that they will eventually prescribe, but the nature and dynamism of the patient they will encounter. Only after understanding the human body and its intricacies at a detailed level should she conclude a diagnosis and prepare a suitable treatment.

If I can draw a parallel from medical literacy to the technology sector today, my sense is that technologists are delivered a highly reversed set of instruction. If programming holds the potential “tech medicine,” then our community rushes to equip itself before first clarifying what it will be used to address. So its not the subject of computer science itself that I contend with, but more the sequence and relative weight of its given importance.

The value of the discipline feels quite clear to me. The rationale is that to solve problems one needs to have command of the range of potential (technological) solutions. To go out and actually effect change you need a grasp of the complexity of tools needed. Another equally important reason: you need to speak the language of those on your team who are building as well. I’ve learned the hard way on that one.

Part of the importance of programming literacy is the problem-solving mentality it induces, but more importantly, the ability to build and/or understand systems that automate work or make work efficient is increasingly valuable in today’s business climate, where tech touches everything. -Shane Snow, Why You Need To Know Code

I love that. I completely agree, which is why I’ve made strides to learn myself. I’ve taken an intro CS class. I had an informal iOS tutor. Earlier last year, with significant mentorship from a fellow IDEO’r, I was able to build a rough version of a social app in iOS I was curious to test.

But since I’ve grown in the venture and technology space over the past seven years, I’ve heard with increasing intensity, perhaps now to a reckless level, the need to develop a computer science proficiency (“Everyone should learn to code. Especially “business people” should learn to code”).

Yet the underlying and glaring assumption in almost all these calls to action is that you’ve sufficiently diagnosed the problem you’re solving. We tend to assume the entrepreneur has surfaced a resonance within a market around whom she plans to build. But this is not frequently the case.

So might the order of operations here be a bit off? Is it possible that we should be attempting to first learn and understand the techniques to surface such human / user / customer resonance, and then assemble the tools with which to build? The order as it is currently stands may significantly underestimate the subtleties required to create truly innovative products. We see time and time again when a product, not attacking a new problem by any means, breaks into mainstream consumption because of a narrow set of features that users “just get”. The Mailbox app comes first to mind. I’ve come to believe that the founders who go on to grow successful businesses are either innately attune to these needs, arrive at them through a slower, iterative learning process, or in other cases get lucky.

And to be sure, some of this empathic thinking has emerged. As entrepreneurship has flourished, there’s more written for technologists toget out and talk to users. But its still in many cases an afterthought and still not spoken at a volume that many founders hear or in the sequence that may be appropriate. The Google Ventures design team, who borrow some of IDEO’s philosophies for their approach, have one of the best resources on how to do this in a more methodical way.

Software is indeed the backbone of innovation in the digital era. Teams that can harness computer science in powerful ways will continue to transform the world. But please, bring the sociologists and ethnographers into the room. Let’s get better trained in diagnostics to better interpret user needs and then develop the technical skills, by learning or through partnership, to put the desirous solution together. Bring on the pathology.

excerpts from “Thinking, Fast and Slow”

I’ve been reading Daniel Kahneman’s book, “Thinking, Fast and Slow" over the past few weeks. It’s a fascinating read on the way we interpret the world around us and how we believe what we believe. But it’s a long read, chock full of studies and illustrative examples. So many that I find myself fearing that I’m going to lose them almost as soon as I’m done reading them. In an attempt to help remember, I decided to pause from the reading and go back and type out a few of the parts I had initially underlined:

When confronted with a problem … the machinery of intuitive thought does the best it can … When the question is difficult, and a skilled solution is not available intuition still has a shot: an answer may come to mind quickly- but it is not an answer to the original question.  The question that hte executive faced (should I invest in Ford stock?) was difficult, but the answer to an easier and relationed question (do I like Ford cars?) came readily to his mind and determined his choice. This is the essence of intuitive heuristics: when faced with a difficult questions, we often answer an easier one instead, usually without noticing the substitution.


As you become skilled in a task, its demand for energy diminishes. Studies of the brain have shown that the pattern of activity associated with an action changes as skill increases, with fewer brain regions involved. Talent has similar effects, highly intelligent individuals need less effort to solve the same problems, as indicated by both pupil size and brain activity. A general “law of least effort” applies to cognitive as well as physical exertion. The law asserts that if there are several ways of achieving the same goal, people will eventually gravitate to the least demanding course of action. In the economy of action, effort is a cost, and the acquisition of skill is driven by the balance of benefits and costs. Laziness is built deep into our nature.


The psychology of accurate intuition involves no magic … Herbert Simon, who studied chess masters and showed that after thousands of hours of practice they come to see the pieces on the board differently from the reset of us … “The situation has provided a cue; this cue has given the expert access to information stored in memory, and the information provides the answer. Intuition is nothing more and nothing less than recognition.”


Simple common gestures can also unconsciously influence our thoughts and feelings. In one demonstration, people were asked to listen to messages through new headphones. They were told that the purpose of the experiment was to test the quality of the audio equipment and were instructed to move their heads repeatedly to check for any distortions of sound. Half the participants were told to nod their head up and down while others were told to shake it side to side. The messages they heard were radio editorials. Those who nodded tended to accept the message they heard but those who shook their head tended to reject it. Again there was no awareness, just a habitual connection between an attitude of rejection or acceptance and its common physical expression. You can see why the common admonition to “act calm and kind regardless of how you feel” is very good advice; you are likely to be rewarded by actually feeling calm and kind.


A reliable way to make people believe in falsehoods is frequent repetition, because familiarity is not easily distinguished from truth. Markets have always knows this fact. But it was psychologists who discovered that you do not have to repeat the entire statement of a fact or idea to make it appear true. People who were repeatedly exposed to the phrase “the body temperature of a chicken” were more likely to accept as true the statement that “the body temperature of a chicken is 144 degrees” (or any other arbitrary number.)

the stories we tell

Storytelling is the single most valuable founder trait. I believe this. It’s priority as a skill varies by the role in the organization, but it is remarkably under-discussed as a distinct and broadly appreciated proficiency. At it’s best, storytelling is “vision.” At it’s worst, storytelling is hype. Worse still, it’s lying. But there is a significant space within these extremes that captures the magic of translating a founder’s version of the future to those around them.

Magic might actually be the right word for it. The definition of magic is “the power of apparently influencing the course of events by using mysterious or supernatural forces.” The most important word in that sentence is “apparently.” Thatis where the storytelling lives. It is inspiring belief in something that hasn’t presented itself yet. It renders the unseen into a digestible substance.

The way a founder performs storytelling surfaces itself in a few key areas:

team- Early on, every founder is spending the majority of their time relaying their version of the future to potential team members. Inspiring them to help build with her. The best founders will make you question what you thought you knew. It’s like being handed a pair of 3D glasses and realizing that you had previously been watching a different (and less interesting) movie altogether. The most persuasive founders tell enough of the story to draw intrigue, but leave the space necessary for you to feel like you can inform the ending.  This is certainly what brings people on board, but it’s also what keeps teams motivated when the business invariably oscillates between good times and bad.

customers- Some say a genius is someone who takes a complex thing and makes it look simple. I was recently conducting research for a startup I was working with and speaking to one of their potential customers. I was trying to understand what elements of the product were most relevant to his business and how much it should cost. He said to me, “You have to assume I don’t know anything. I need to know why it’s important and how it helps me. Thats it.” The most artful storytelling is one that optimizes for ease of comprehension. It is about making your complex product, one that might not even exist yet, feel immediately useful and intuitive in essence.

investors- I speak to many founders as they are getting ready to raise capital- sometimes it’s help with introductions, crafting the right strategy/amount, or just with their presentation. In either case I almost always end up explaining that the most significant and surprising takeaway I’ve had working in venture is that the ability to secure a (seed) round is almost completely reliant on a founder’s ability to tell the right story. To detail their grand vision.The failed attempts I’ve seen almost always focus on the product in its current form… a plan to take one thing and place it in the hands of as many people as possible. The most successful founders through that process are almost always more concerned with where the current product will take us from where we are today. Those that tell a story about how their product builds a bridge to enter a future where things look much different.

themselves- I think most importantly, storytelling is an ongoing conversation with ourselves. Even the biggest visionary is constantly reminding themselves why they’re doing what they do. Why they’re bothering to push the envelope. Why they’re good enough. One of my most favorite anecdotes:

E. B. White was amused to learn from a farmer friend that many electrified fences don’t have any current running through them. The cows apparently learn to stay away from them, and after that you don’t need the current. “Rise up, cows!” he wrote, “Take your liberty while despots snore!”

We get to decide what we want to believe. There is a narrative that will help us remember that there is actually no current in the fence.

"Invention requires a long-term willingness to be misunderstood. You do something that you genuinely believe in, that you have conviction about, but for a long period of time, well-meaning people may criticize that effort. When you receive criticism from well-meaning people, it pays to ask, ‘Are they right?’ And if they are, you need to adapt what they’re doing. If they’re not right, if you really have conviction that they’re not right, you need to have that long-term willingness to be misunderstood. It’s a key part of invention." - Jeff Bezos

the Innovator’s Paranoia

impulsiveness in the face of steep disruption

Highly successful companies over-emphasize existing customer behaviors and create dependencies on currently lucrative products, and in so doing fail to recognize emerging needs or technological advances before its too late.

An overused rationale, perhaps, but this is nonetheless the regularly identified cause of death for many companies as explained by “The Innovator’s Dilemma.”

Today though, the disruptive climate has intensified. And while it isn’t new to see bold, fresh companies displace uninspired incumbents, it’s happening more often, and much more quickly. Across virtually every industry, from Uber in transportation to Square in payments,larger firms are observing highly disruptive companies ascend into public view at a breakneck pace.

Some credit the now cost-effectiveness of starting a business, or the culture that a few visible successes have infused in the entrepreneurial spirit. Catalyst aside, this accelerated pace has shifted a near reversal of Clay Christensen’s diagnosis. It is no longer inaction that firms are suffering from, its the fear that swift action is necessary to maintain relevance to outpace these more nimble players.

Companies today are essentially turning the innovator’s dilemma into innovator’s paranoia, a distinct yet as acutely paralytic a condition.

This corporate FOMO dynamic is motivating focus and investment in strategies awfully out of line with stated long-term objectives. Such an over-dialed course correction, without proper checks and balances, is potentially leading teams further adrift from eventual viability.

I found a wonderful call-out of this narrow thinking in the latest debates over the optimal strategy for Nintendo. A long-time powerhouse of hardware-software gaming, Nintendo has been urged by many to abandon hardware and focus on iOS, given mobile’s strength of engagement over the last several years. A response fromJohn Gruber, drawing a parallel to Apple in the 90’s as they were facing stiff competition from Microsoft: was common advice then for Apple to do what Microsoft was doing: license their operating system rather than make their own hardware.Microsoft is the most successful company in the industry, therefore Apple should do what Microsoft does and just license software to commodity hardware makers. But if we applied that line of thinking to Apple analysts giving advice to Nintendo today, would not the advice be for Nintendo to stay the course? Apple is the most successful company in the industry, therefore Nintendo should continue doing what Apple does by making its own hardware and software.

Apple succeeded not because it emulated a then-successful strategy, but by digging in their heels and embracing a long-term strategy consistent with their integrated hardware and software competency.

Examples of these detours are numerous, and also seem to arrive in waves. Each cycle presents a solution that proposes to cure a scheduled corporate fall from grace:

  1. Twenty-four months ago, “social” was evidently how businesses needed to reshape their brands. The holy trinity of icons (f, t, t), as it were, was embraced by nearly everyone. And then along with Facebook, Twitter, and Tumblr came Pinterest, and so faith in adding the P icon prevailed. This was happening without much regard to what kind of conversation (short vs long-form? image-based?) with consumers, if any, was most appropriate to engage with consumers.
  2. Around the same time came the “app” phenomenon. Does your digital experience require a controlled environment that leverages GPS and can deliver value in a tightly framed interface? Does a customer’s frequency of use warrant a download? All too many strategies have shifted to mobile without asking those fairly high-level questions.
  3. More recently, companies are seeking saving grace from developing a wearable computing device. From Samsung to Microsoft to Google, each day welcomes a new entrant to the category.
  4. Venture, be it via investment, acquisition, or incubation, is now another high-traffic category. Yahoo has spent billions on almost twenty acquisitions in under a year. As of this month, 7-Eleven has a venture fund. Even traditional venture firms have felt pressure to innovate: just last week, Foundry Group announced a $2.5 million pledge to invest in AngelList’s syndicate program, not more than a week after the platform was announced.

A rapidly shaping landscape has incited maneuvers that are highly inconsistent and uncoordinated. This much feels clear. But the way out of innovator’s paranoia will be through thoughtful and measured experimentation. To be sure, some of the above examples are likely just that. Seeking inspiration through calculated risk-taking may ultimately provide the seeds of clarity for a new way forward. But while strategies must necessarily evolve, companies should not let outside forces dictate their stated long-term vision.

In the end I am not sure which is the lesser of two evils: an adherence to entrenched governing principles or hyper-experimentation in the face of increased activity. I do know, however, that regret from failure is exceedingly heralded as far superior than regret for having not tried. This may just tell us which way things are headed.

On syndicates: are we losing the narrative?

I ran into an old colleague on the street last night. She and I used to work together in the venture capital and private equity fund placement business. Our job was to evaluate fund portfolios, advise on emerging investment strategies, and help raise capital for upcoming financings and fund launches.

We only chatted for a bit, but being one of the sharpest people I’ve worked with, I asked her what she made of all the recent regulation changes around crowd-funding and whether she thought it threatened her business.

She immediately dove into a story from earlier that day- she was speaking with a large institutional investor who explained they don’t have any new capital to allocate in new areas and are taking some time away from the venture capital asset class. My old colleague began explaining to them the latest group she was working with, and by the time the meeting was over, they were debating the size of the allocation and setting up a time to meet the team.

What my old colleague was saying, without actually saying it, is that there will always be a need for stories to be told. For visions to be expressed. And regardless of whether there is an intermediary involved as she is in this case, that narrative can often times make all the difference.

I think whats been forgotten with the latest excitement around AngelList’s innovation is that there is great nuance to these discussions. There is a significant human element. We shouldn’t treat investments, or funds for that matter, as a spec sheet. Particularly as the volume of ideas continues to intensify as it has been, the signal-to-noise ratio is at an all-time low, and we cannot pretend to glean signal as we scroll through an open-syndicates feed. The reality is that gleaning this in person is hard enough as it is.

The innovation community likes to remind itself that ideas are a dime a dozen. That success is about team and vision. Then perhaps to liken the relationship-driven process of funding to a commodity exchange is to undermine what our community heralds as most valuable.

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