How Technology Will Change Entry-Level Higher Education

This guest post originally appeared in Wired

For years, “invest in education” has been a mantra consistently repeated to students and parents worldwide. It is now a phrase that VCs and entrepreneurs know, as technological solutions to some of education’s greatest challenges are gaining attention. As anyone in higher education is aware, the industry faces some intimidating issues, including affordability, accessibility, quality, and the momentum necessary to create system-wide change. Some of the field’s best minds are already hard at work to address tuition and access — and entrepreneurs and investors are also seeing the opportunity to replace traditional media with new technology that better serves today’s students. Ultimately, the investments being made in educational technology will lead to huge benefits down the road for students, their families and the economy.

Disruption in the Classroom

Let’s look outside of education for a moment. Entrepreneurs and the tech community have a reputation for disrupting some of the world’s largest industries in a meaningful way. Take, for example, Elon Musk’s work with Tesla Motors. Where traditional auto manufacturers needed a long time to bring fully electric cars to the market, citing issues with infrastructure and engineering, Musk saw things differently. By leveraging the strengths of an electric car, such as acceleration and handling, he created a fundamentally different and better car that’s a convincing case for investing in the infrastructure needed to support others like it., Similarly, the biotech industry has blown up in the last two decades, redefining healthcare and advancing health-sciences. We’re even beginning to understand the human genome well enough to detect potential health risks before they even exist.

Higher education is no different than the automotive industry or healthcare – our industry has incredible importance and power. With a mix of entrepreneurs and technologists keenly focused on a generation of students that are more socially networked, digitally fluent and tech savvy, education is quickly becoming the next “hot” sector for innovation. 

Back to 101

The tech community is already hard at work disrupting higher education from all sorts of angles. In fact, we’ve been making progress already. It’s been years since classrooms introduced digital platforms like SMART Boards to create more traction in teaching students. More recently, MOOCs such as Coursera have changed the way students attend class by moving entire classrooms into a digital format, expanding access to top professors and subjects. If physical space isn’t a constriction – what other ways can we streamline learning?

Innovation is just beginning within the terrestrial college campus and I think the next opportunity lies in introductory courses. 101 courses are the building blocks upon which college students learn a new subject, discover interests, and set a course of study. They instill foundational learnings that students use to develop expertise in their chosen field. For the investors of the world, the market for the 101 is huge — colleges and universities require students to complete introductory classes to meet graduation requirements, so college-educated students of all majors and in all fields will most likely take a 101 course at some point. That includes the creative writing major with a math requirement, or the science whiz in an English course.

On top of this, 101s are often delivered in a one-size-fits-all approach due to the basic nature of the subject matter presented. Students often must decide for themselves when and how to connect with TAs, professors and advisors to overcome difficult concepts, identify potential further interest and find successful techniques that help them succeed faster. These are the types of issues — essentially shortening the feedback loop — that technology (specifically software) has been solving in the business world for years now. How can we change the way students interact with materials to make them better, faster learners? How do we give students better, consistent feedback on progress? This is where technology can make its impact.

A New Semester in Higher Ed

With the 101, higher education has fertile ground for innovation. There’s a big market, a need for content delivery, and a benefit from higher performance analytics – it’s the classic scenario for technology to bring improvement.

Right now MOOCs are addressing market, content and feedback issues from a classroom format perspective. Adaptive learning tools are tackling studying and information delivery to help students move through material in the best order, testing and delivering the right content and questions along the way. Spaced repetition, in conjunction with high-quality content, will improve fact-based learning. I — and my company, Boundless – believe that students will move away from paying for textbooks, and instead, pay for tools that help them master material. Sooner than we think textbooks will no longer exist and professors will focus on teaching the highest value content, letting students use technology to master basic facts and know where they stand.

As technology continues to filter into higher ed and address some of the challenges at play, I believe that more students will have access to the amazing research and brilliant minds that higher ed has to offer.  I’m hopeful that the technology community will step up and continue to deliver tools and platforms that help students, professors and institutions gain more choice in the cost and accessibility of educational content. Just as college students have to start from the beginning, the technology community should start with the 101 to catalyze further change in higher ed.

Academia 101: Talk about careers and the big picture before the nitty gritty

This is a guest post I wrote on Quartz – original appeared a week ago and is available here


Almost every university student takes 101 classes. Usually, they’re viewed as ways to build foundational skills or complete requirements, rather than gateways to exposing students to interesting career possibilities. The 101 course should be a place where a student experiences the beauty of discovery for the first time—the fact that the cure for cancer could lie in her hands. Often this discovery gets lost in the granular details. It’s time we start thinking about introductory education in universities differently.

According to the New York Times, at Penn State University, 80% of freshmen—even those who have declared a major—said they’re uncertain about their chosen path in college. With the current skills shortage (particularly within engineering), we can’t afford to leave this many students undecided. The 101 class can be used to get more students motivated to pursue engineering, computer science, medicine, genetics—the list goes on and on.

To spark discovery at the 101 level, we need to change the way we teach altogether. Education reformists are trying to disrupt the classroom as we know it in a variety of ways—one method is a “flipped classroom,” where students listen to lectures at home and interactively work on homework in the classroom. A slightly different idea is to switch the order of the curriculum—teaching big ideas first and working down to granular levels of detail at the end of the course.

Let’s take Biology 101 as an example. Most 101 classes start with basic (arguably, uninteresting) concepts and work up to the big ideas. You might never know that you’d be able to clone a wooly mammoth by studying the structure of a cell in intense detail. When you’re learning about the nucleus and mitochondria, you’re often not getting the broader context about why this information matters in the real world. What if we inverted the order of the curriculum, starting with exciting concepts and digging down into detail? Would we have more geneticists? More bioengineers?

At Boundless, we’ve done a lot of research about how 101-level college students use our textbooks. More than 50% of students visiting our open textbooks online look up very specific terms or concepts, and spend most of the time on the site highlighting and quizzing themselves on these concepts to make sure they’ve got them right. Rather than spending time connecting the dots on big-picture concepts, students are researching and being graded on their ability to retain smaller details. They’re immersed in the assembly line model of teaching, which has been done for years and, to some extent, people argue that it’s proven.

But the sheer statistics about how our students rank in math and science skills prove otherwise. According to the President’s Council of Advisors on Science and Technology, “economic forecasts point to a need for producing, over the next decade, approximately 1 million more college graduates in STEM fields than expected under current assumptions.” With American students scoring 23rd in math and 31st in science compared to 65 other top industrialized nations, something must change the way we produce workers in these fields.

Major institutions are coming around to change—Princeton president and molecular biologist Shirley Tilghman spoke out about the need to invert the science curriculum. Salman Khan of Khan Academy has also advocated for change on the K-12 level through a flipped classroom model. But how do we get more universities to adopt the change?

We need to do two big things. First, hook students with 101—don’t be afraid to make broad changes to the way classes are taught. Freshman year is a chance to get students interested in new subjects before majors are declared or set in stone. Second, use technology to make it easier for professors to be flexible. We need more flexible textbooks and adaptive study resources for students that aren’t rigidly tied to a set order or the “way things have always been.”

Math and science provide the answers to some of the world’s most pressing problems. And math and science careers are exceptionally interesting, ubiquitous, and in-demand. It’s a shame that we’re burying those realities in mundane details. Let’s make sure students know why they’re learning what they’re learning, before drilling into the basics. An inverted approach can make learning more exciting and get graduates prepared to compete in the global economy.

Open post

The Simplicity Paradox: Simple > Complex > Simplicity

The Simplicity Paradox: Simple > Complex > Simplicity

“When you start looking at a problem and it seems really simple, you don’t really understand the complexity of the problem. Then you get into the problem, and you see that it’s really complicated, and you come up with all these convoluted solutions. That’s sort of the middle, and that’s where most people stop. But the really great person will keep on going and find the key, the underlying principle of the problem — and come up with an elegant, really beautiful solution that works.” – Steve Jobs.

That’s one of my favorite Steve Jobs quotes. It does a great job in capturing the counter-intuitive nature of how simplicity is harder than complexity.
I’ll go one step further and create the following framework:
Simple > Complex > Simplicity

This framework applies to many facets of life, certainly beyond product development.

Simplicity is elegant. It’s easy to work towards. It’s easy to understand and to sell. But there’s a big difference between simplicity and simple in this case. Once you get over the complexity hump, the solution seems obvious, and seems like it could have been achieved without the work of going through the complexity hump. In practice that’s not the way it works. Truly elegant solutions are the result of fighting through complexity, and are rarely single insights.

Here are a few examples:

The iPhone is perhaps the greatest example of this framework. After the original simple telephone, which let you simply dial and speak, companies went on a feature arms race to continually add new features. Address book, speed dial, calendar, etc. And phones got to be very very complex. And technology companies relished in that complexity and tripped over each other to add features and more complexity. Then the iPhone came along, the result of pushing through the complexity limitation, and ushered in a new era of phones.

In politics we’ve recently seen a similar situation. Romney’s Tax Plan is in the “simple” category. Easy to sell and explain and put into sound bites. But it doesn’t have details because it hasn’t started actually trying to solve the problem. On the next step is Obama, who is so mired in details that he can’t convey a vision for his plan. His terrible performance in the first presidential debate last week showed this. He was trapped in the complexity of the details, trying to explain and resolve real deep challenges to make this all work. Now compare this to the polished arguments of Clinton’s DNC speech, where he accurately portrayed the key issues on both sides, in a simple way that people could understand and relate to.

The same is true in architecture, one of my passions. All architecture started as simple housing and shelter. Then continued to get more complex and decorative. This decorative trend culminated in the Beaux Arts School (literally and figuratively) of architecture. Architects tripped over themselves to add more details and ornamentation the way Samsung and Acer add faceless “specs” to tech products. Then came the modern movement, led by the Bauhaus school, which focused on simplicity. Elegant solutions to challenging problems. And this style and philosophy remains the most elegant in the world. Have you wondered why an Eames chair designed in the 50’s looks more contemporary and futuristic than an Aeron chair designed in the 90’s?

And finally, we see this same trend in the growth of knowledge. Things start as simple: thy sky is blue. Then get complex: because light refracts at that particular wavelength due to the molecular composition of our atmosphere. Then as you really understand things, a new simplicity emerges. The understanding that chemistry, physics, and biology are not separate disciplines, but different ways of looking at the same physical world. As Einstein put it so elegantly: “If you can’t explain it simply, you don’t understand it well enough”.

So whether you’re explaining something, designing something, or building something, keep this in mind. Don’t be naive and think things are simple. Don’t be lazy and let yourself stay in the complex. Work towards simplicity.

The Right Solution to the “E-Book Problem”: Putting Students First

A couple of weeks ago I wrote a guest post on about the future of e-textbooks. Here is the post in its entirety, and you can view it on Forbes here


Textbook publishers are trying to stay relevant in this increasingly open and digital world–but at what cost?

Tom Malek’s recent guest post on this site (“Solving the E-book Problem in Higher Education”) details textbook publisher McGraw-Hill’s new plan to accelerate the adoption of its digital texts by forcing students to buy the e-books for their courses, whether they’d like to or not.

The textbook industry is often called a broken market, as the end consumers do not select the product that they’re ultimately forced to buy. Students are able to choose from a number of options, thankfully, such as used and rental texts, but this compulsory e-book model threatens to make things even worse for them.

Today’s E-Books Don’t Meet Students’ Needs

 Malek is right about one thing—digital is the future of higher education. According to a recent survey conducted by Wakefield Research, the majority of college students (67%) use digital technology every hour. A startling 40% of students can’t stay away from technology for more than 10 minutes at a time.

However, his conclusion about why today’s e-books are failing is wrong. Malek blames the slow uptake of digital texts on students’ ignorance of the benefits of e-books and their reluctance to give up the “familiarity” of print. Studies have shown that more than half of students do still prefer physical textbooks to e-books. Yet if you give those students a chance to interact with a great e-book experience on an iPad,75% of them prefer the digital alternative.

Today’s e-books aren’t the solution to students’ textbook woes because they’re expensive, poorly designed products that students don’t want. Publishers make very high gross margins on traditional textbooks, and since e-books radically reduce the cost of distribution and printing, one would expect prices to drop substantially for digital offerings. Yet thus far, e-books haven’t saved students enough to make switching from print worthwhile. A recent study released by Daytona State College revealed that many students only saved $1 by switching to e-books.

Malek argues that the high-cost of e-books is due to the fact that physical production costs are “only a fraction of what it costs to produce a textbook.” Yet numerous innovative publishers have found ways to produce high-quality texts for far less than their traditional counterparts. Flat World Knowledge, for example, offers cheap print copies of their textbooks and makes them available for free online.

Price aside, the reality is that students have never been offered excellent digital products that cater to the way they best study and learn. A quick glance at traditional publishers’ e-books reveals mostly non-interactive PDF files and “innovative learning platforms” that are little more than multiple-choice questions with a shoddy user experience. Malek and the publishers have chosen to ignore the obvious signal of students’ disdain for current e-book offerings, calling it a mere “problem of perspective.” But rather than improving that perspective, their plan is to drive students even deeper into the textbook trap.

Malek’s Solution: Eliminating Student Choice

This new “model” is a brazen attempt by publishers to further insulate themselves from market pressure. Malek justifies the forced-purchasing model by setting up a false dilemma: the choice between very expensive digital texts and slightly less expensive ones. He avoids the obvious third option—better and significantly cheaper digital learning tools.

It’s not a surprising omission: e-books are a publishers’ dream, as they’re often riddled with restrictive DRM and eliminate the booming secondary market of used and rental texts. Despite this fact, Malek claims that this new forced purchasing model will ultimately help students save money.

Yet by hiding textbook costs in the tuition bill, prices are even MORE likely to increase. According to the US Bureau of Labor Statistics, textbook prices have already risen over 500% over the past 30 years, at 3X the rate of inflation. Only three things have risen faster: tuition, tobacco and hospital stays. Do we really need another excuse to accelerate the rise of textbook prices by bundling them with something that is rising even faster?

Student loan debt has reached new heights in this country—additional mandatory costs are the last thing our college students need. In fact, this forced purchasing policy would increase the total mandatory cost at community colleges by 33%, where textbooks often make up a quarter or more of tuition, fees & supplies.

Is it any wonder that Malek doesn’t mention student sentiment in his discussion of the pilot programs of this new model?

Putting Students First

The best way to solve the “problem” of e-book adoption is creating MORE of a market, not further restricting competition. The future of education lies in building products for students—after all, they’re the ones whom the educational system is meant to serve. Thankfully, countless innovators and educators are putting in the hard work to realize the dream of a more student-centered design approach.

The Open Educational Resources movement has created an enormous library of 100% free content for students and professors alike. Open Content understandably does not compute for traditional publishers, as it can be both cheaper and more effective than traditional alternatives. Wikipedia, for example, often contains the same information (and more) than expensive introductory texts in a given subject.

Education technology companies have seen an unprecedented acceleration of venture investment over the past few years, topping $400MM in 2011 and potentially surpassing that this year.

New initiatives like MIT and Harvard’s edX are promising to distribute high-quality free content to learners around the globe. Companies like Kahn Academy are creating enormous content libraries that integrate deeply with the “super-adaptive” learning tools Malek praises—for $0. At Boundless, we’re committed to replacing textbooks altogether by connecting students with open content in new and exciting ways.

The Future of Educational Content

Desperate attempts to protect antiquated business models are not the answer. The solution is delivering great products for students.

The seeds of this educational revolution are being sown in classrooms, incubators and coffee shops all around the world.

It’s time to give students more choice—not less.

The Consumerization of Education

You don’t have to search far to see the many frustrations with the efficacy or cost of our current educational system. While there are many possible reasons for this, I’d like to focus on particular dynamics of education.
Traditional education products and services are ‘sold’ to key decision makers who then force the decision onto end-users. It’s no surprise then, that the result of this process are products that are inferior in the eyes of end-users. The products may very well meet some checklist that is deemed important to a key decider, but this checklist is usually different from the needs and desires of the end-users, namely, the students. One example is the oft-maligned “standardized tests”, which benefits states and districts looking for singular comparison metrics, yet often fail students by limiting exploration, breadth, and teaching focus.

Slowing Innovation in IT
Another industry that long had similar structural and market dynamics was corporate IT (information technology).
Just ten to fifteen years ago, technological innovation was driven primarily by business needs. New products were sold into businesses and large corporations, and eventually trickled down into the consumers. Whether it was the fax machine, the copy machine, or even early personal computers. The same was true for software.

The problem with that model was that the ‘decider’ was usually a different person than the ultimate ‘end user’. Corporate CIOs would make buying decisions of software and hardware for 50,000 employees, who were then forced to toil in terrible user interfaces and inferior hardware. Innovation suffered.
The Consumerization of IT

Then something changed. Companies began focusing on end-users, and began delivering terrific products, from software like Basecamp from 37Signals, to the biggest tech success of this generation in Apple. 

Apple is leading the biggest disruption in today’s IT world by being a consumer-first company. Apple kept their relationship with the end-user first and foremost, and was able to deliver great products, and ultimately great profits. This wave of innovation would not have happened had the business-first technology leaders continued to dominate. 
Another great outcome of the consumerization of IT and other verticals is the empowerment of the end-user. This new-found decision making and interest in the product can lead to increased productivity, and is evidenced in droves of business users buying and bringing their own iPhones to work, eschewing the corporate issued Blackberry. 

The Consumerization of Education

We are in a similar position in education. Innovation in education has stagnated because market forces don’t reward innovation. Market dynamics put very little power in the hands of students. Students cannot choose much today, other than where to go to school. There is tremendous opportunity to serve the needs of students directly, and use that relationship to drive significant and disruptive innovation. 
Key elements to enable Consumerization 

In order to really drive ‘consumerization’ of any industry or product, two ingredients are necessary:

1) a direct relationship to the end user
2) a desire to build amazing products
I believe strongly in both, which in education means focusing on the student first, and delivering a delightful learning experience, resulting in a more engaged and empowered consumer.
The next great wave of companies and platforms, especially in education, will be built with this ethos.

Returning to blogging – with an education focus

It’s been about a full year since I last blogged. 

That year has been incredible from a personal and professional standpoint. I’ve gotten engaged, started a new company working with a great team and a great group of investors, and even recently gotten a puppy.

This startup, Boundless Learning, was the primary reason for not blogging during that time. Not just from a time perspective, but from a mental energy perspective. All of my mental energy (and most of the physical energy) in that time period has gone towards establishing Boundless, working on everything from high level and long term vision, to immediate concerns like hiring, product roadmaps, content creation, etc. 
One area that has been central to the past year has been education. I’ve always been passionate about education, both my personal education (in and out of school), as well as the education system and what it means for society as a whole. 

Going forward, I’m going to channel my desire to blog more, with my passion and ongoing experience with education and learning. We’ve been learning a ton about the past and present of education, and are working night and day to help define it’s future.
Stay tuned.

Strengths and Weaknesses are Two Sides of the Same Coin

Strengths and Weaknesses: Two Sides of the Same Coin

We often think about strengths and weaknesses in a vacuum, as if they were completely unrelated to each other. We think about building up strengths and eliminating weaknesses.  That’s a bit disingenuous and logically impossible because you end up stuck in the middle, with no real strengths or weaknesses. You end up averaging out strengths and weaknesses, resulting in an unidentifiable and uninteresting mediocre mix of traits. 
Instead, we should be thinking about both the strengths and weaknesses tied to a given trait or characteristic.  Every strength has a corresponding weakness, inherent to the underpinnings of that strength. 

Company size as both a strength and weakness
If you’re a large company, like Google, you can throw dozens of engineers and other resources to try to a problem. That’s a lot of momentum moving in one direction, but that also means it’s harder to get going, harder to change directions, and harder to react to uncertainties or changing environments. On the flip side, if you’re a small company, you may not have a lot of resources, but you can be nimble, make faster decisions, and out-maneuver larger competitors.  
Personal strengths and weaknesses
Personal traits also inherently have strengths and weaknesses. Most of the time, we get feedback throughout our lives about the weaknesses or limitations, and end up focusing on reducing or eliminating those. We don’t realize that we’re also weakening the complementary strength. We end up settling for the lowest common denominator.

I compete in everything I do, big and small, creating competitions out of non-competitive things, keeping score in every game where score is kept. That competitive outlook has helped me in almost everything I’ve done, from succeeding in sports my whole life, to my academic career, to the current startup world I’m in.  But it does have a complementary weakness. Über-competitiveness can be off-putting in certain social situations. But the reality is that it’s not something I can just turn it on and off.  I’m willing to manage and deal with the social awkwardness that may come with being über-competitive.
The power of confidence can create a positive feedback loop of increasing confidence, increasing ambition, and increasing achievement.  But there are also inherent weaknesses of confidence.  The classic is hubris, a self-defeating pride that can lead people to forget their limitations and pursue unattainable and ultimately fatal goals. Another more benign one is that extreme confidence can also occasionally seem arrogant and egotistical, especially in a crowd of non-confident people. 

I don’t give up very easily, will fight to achieve long term goals, and will work hard and summon other strengths (like confidence and competitiveness) to get things done. Like the two traits above, perseverance is so entrenched in my world outlook, that I don’t doubt it will get me through the darkest and most challenging times. But it also comes with a cost, the complement of perseverance is stubbornness. Even the word stubbornness has both positive and negative connotations. It’s important to be aware of both, and to understand the balance, but to realize they go hand in hand.
Managing strengths and weaknesses
Given that strengths and weaknesses are different ways of looking at a particular characteristic, the next step is to think about how to manage or deal with weaknesses.  The goal is not to eliminate or mitigate weaknesses, because that would inherently eliminate or mitigate the corresponding strength. 
Understanding the tradeoffs of each trait is a sign of maturity. Being able to acknowledge weaknesses that are the flip side of a strength is important. Next time you’re thinking about a weakness, think about it’s corresponding strength – somewhere in that weakness is an inherent strength.  Then think about whether it’s worth tempering that strength in order to temper the weakness.  Or even better, how to be aware of both and use it to your advantage. 
This is also highly relevant when building a team for a startup or other endeavor. Don’t worry about mitigating weaknesses, instead focus on finding a team whose strengths work well together, and whose inherent weaknesses balance each other out.

The Secret Power of Confidence

The Secret Power of Confidence and How to Build It

Confidence is one of the most important traits in life. It is imperative for everything from dating and relationships, to startups and business. Most of the conventional wisdom around confidence and self-esteem is trying to find a short cut. But the reality is that you can’t create real confidence by reading a WikiHow article about how to be confident. You can’t create confidence by simply telling yourself that you are special, smart, interesting, or appealing to others, as some confidence “experts” will tell you. All of that is simply addressing the symptoms not the underlying issue.
Real Confidence
The only way to create real confidence is to succeed in something challenging. Everything else is as empty as a participation trophy in elementary school. Real confidence is built upon a solid foundation of achievement, that you can look back on and know is real when things get tough. True confidence is so humble it’s arrogant, and so arrogant it’s humble. 
The Confidence Cycle
Confidence creates a virtuous cycle. It raises ambition, which in turn means you seek out higher goals, which also motivates you to achieve them, which brings you success, which then gives you more confidence that fuels the cycle.
Building Confidence – Seek out challenges
Since the only way to build true confidence is to succeed in something challenging, you need to seek out challenges, and be motivated enough to complete them. This process can start with small goals, to help build the cycle. The challenges do not have to be related to a core strength or long term goal, and are often more challenging and rewarding when they’re outside your core competency. For instance, if you’re an English-major, all-star athlete, learn to build a website.  Conversely, if you’re a techy non-athlete, run a marathon. If you’ve already run a marathon, run an ultra-marathon. If you’re a social butterfly, read the longest book you’ve ever read. It’s not about over-optimizing for the specific challenge, just find one, get started, and continue until you succeed.
The risk of a single source of confidence
Too often a person’s confidence is tied to a specific source, whether it’s their job, their marriage, their alma matter, or their prowess in a particular skill. There are two risks with this single source. First off, it may not imply ability or confidence in other areas. And secondly, if that single source disappears (getting fired from a job, divorce, etc.), you lose all of your confidence and go into a downward spiral. This is one of the biggest challenges of chronic unemployment. People’s confidence is tied to their job, so when they lose it, they are left exposed. 
The Confidence Portfolio
Real, robust confidence is only attained with a diversified and well balanced confidence portfolio. In order to create that, you need to continue pushing yourself with a diverse set of challenges. Make them diverse, then build on successes and let that fuel your rising ambition. The more diverse your sources of confidence, the more stable it is, because you’re creating balance through excellence in multiple things. Psychological research has shown that increased self-complexity, i.e. the different ways of perceiving oneself and one’s strengths, leads to lower levels of depression, stress, and illnesses:
“Subjects higher in self-complexity were less prone to depression, perceived stress, physical symptoms, and occurrence of the flu and other illnesses following high levels of stressful events. These results suggest that vulnerability to stress-related depression and illness is due, in part, to differences in cognitive representations of the self.”
“Self-complexity as a cognitive buffer against stress-related illness and depression.”Patricia Linville, Yale Psychology Professor,
Get out there and challenge yourself. In a follow up post I’ll share some examples of my own diverse set of confidence.

Losing 20 Pounds in 3 Months

Losing 20 pounds in 3 months

Towards the end of this past summer, I had gotten past my comfortable weight, as a result of a fun summer, not working out enough, and enjoying the food and beverage. I was up to 194 pounds, and though I carry it well (on my massive thighs primarily), it’s still pretty robust for my 5’10” frame.
It really pissed me off. And since I don’t believe in moderation, I decided to do something extreme about it, and on August 23, I tweeted the following:

Here I am, 3 months later, having achieved that goal. Looking back, here’s the simple plan and how it worked.
Step 1 – State goal publicly
I’m a big believer in using any means possible to motivate yourself, and committing to something publicly is a great motivator. So I tweeted and posted to Facebook about my goal, told all of my friends, and committed to myself. Not only did this motivate, but it’s also a great way to get other people’s support, especially when you’re turning down food and drink. 

Step 2 – Decrease food consumption
I don’t believe in fad diets. Losing weight is all about a simple equation:
Weight Loss = Calories IN – Calories BURNED (divided by about 3,500, which is the approx number of calories per pound).  
So if you’re running a 500 calorie deficit per day, you’ll lose about a pound a week. Since I was trying to go faster than that, I needed to make sure both factors changed. Reducing food consumption takes discipline, and it reminded me of my days as a lightweight rower. I didn’t skip meals (occasionally breakfast), just reduced what I ate, and ate extremely healthy foods.
Step 3 – Dramatically increase mileage
The second part of the equation is the calories burned. Once I made the goal, I went from running occasionally (5-10 miles a week) to regularly running 30-40 miles per week, every single week. Running 30 miles burns about 4,000-5,000 calories, which is about what I was targeting to lose. 

Step 4 – Profit
Three months later, I’m back at a comfortable 174 pounds, and at a steady point that I can maintain pretty well with some basic working out and healthy eating.  I feel great and look great (according to my girlfriend at least, which is all that counts). Just in time for Costa Rica 😉
Next Goal – Qualifying for Boston Marathon
Now I have to pick a big audacious goal to train for again, so I’ll announce that here. My goal is to qualify for the 2012 Boston Marathon.  For those of you keeping score (and who isn’t), that requires a 3:10 marathon, which is 26 miles at a brisk 7:15 per mile average pace.  The gauntlet has been thrown. 

Fuck Moderation: Balance through Extremes

Fuck Moderation – Balance through Extremes

This was originally written as a guest post on BostInnovation

There is a general conventional wisdom that everything in moderation is good.  As with a lot of conventional wisdom, that’s bullshit.  Everything in moderation leads to a dull, boring, shapeless, unidentifiable mass.  Moderation leads to complacency. Instead of moderation, pursue excellence.
The Importance of Balance
The irony of the conventional wisdom is that it hides a truly important point, which is the need for balance in life. While moderation is insidious, balance is important and beneficial. Balance creates interesting cross-polination, a diversified interest base, and an ability to use one strength to compensate for another when you need to. Balance creates stability and strength. On an individual level, It’s very fulfilling to have a diverse lifestyle, in the spirit the Renaissance man, but moderation is not the way to achieve true balance.How Extremism Creates Stability
In physics, the moment of inertia quantifies the ability of an object to resist rotation. The more weight is out on the extreme of a given object, the higher the moment of inertia, and therefore the more stable it is. The best real world example is a long straight pole. With most of the weight way out on either side, it provides a very stable counter-balance that can be very useful when walking across, say, a tight-rope between the Twin Towers.

Innovation is Extreme
On an entrepreneurial level, all real innovation happens at the edge. There is simply no better way to learn an industry and try to fix a problem than starting a company and devoting all your mental and physical energy to solving or improving some important issue. Startups are extreme by definition, and that’s one of the things that makes them so disruptive. Innovation is extreme. Leave the moderation to large companies looking for 5% annual growth. Even within a startup, balance through extremes is important. For early teams, it may mean finding complementary founders, both of whom are amazing and strong in very different areas, like technology and marketing, for instance.Extreme Abstinence
On the other side of the coin, there are many extremes that can be dangerous. In those cases, I think the best solution is to go extreme in the other direction, by abstaining completely. For example, I don’t gamble or watch TV because I don’t like those extremes.  So I go to the other extreme, by eliminating them completely. It’s not worth watching a single episode of a TV show, and I certainly don’t want to get hooked. In business, what you choose not to do is just as important as what you choose to actually do. It’s much easier to not start a project, or a feature, or a new market, than to do it half-assed.

Focus on 1-3 Extremes at a Time
By definition, being involved in something to the extreme is nearly all-consuming. Therefore, it’s important to focus on only 1-3 areas at a given time. When starting a company, especially in the early stages, it’s difficult to be extreme in much else.  But it’s good to have at least 1 counter-balanace. For me, it was training for an ultra-marathon (50 miles), which I used as an excuse to get me back in shape after 6 months of not working out due to injury. I ramped up my running to 30-40 miles per week, finished the ultra-marathon in just over 10 hours, and had a great time doing it.Vary the Extremes for Diversity
While I enjoy living in extremes, I’ve found it important to vary my involvements over time to create a diverse perspective. I love staying physically fit and active, traveling, understanding different cultures, cooking, starting companies, learning, and much more.  But in order to gain real depth in each of those areas, I had to really focus on each for a period of time.  By choosing to dive in on a few things at a time, you can afford to be extreme.  As you rotate through your various potential interests and projects, you’ll find yourself with a much deeper knowledge base than if you had moderately pursued them all over a longer period.

Choose what you want to do wisely, then do all of those things fully.

Static and Kinetic Friction

Static Friction > Kinetic Friction

I love analogies, especially analogies between life and physics. On a recent run, I was thinking about the parallel between static friction and the forces that keep us from starting things. We all remember the physics experiment from 8th grade, where we put a block of wood or plastic on a ramp, and see how high we can angle the ramp before the block starts moving. In order for the block to start moving, it has to overcome the static friction, which is the frictional force at work at rest, when the surfaces have time to settle and create a sort of frictional bond. Once the block got started, it only has to overcome kinetic friction, the friction against the object when it is motion. Kinetic frication is always lower than static friction. This point is reinforced by the experiment. You need to get to a much higher angle to overcome the static friction, but with a slight nudge at even a much lower ramp angle, the block will keep going.

Life is very similar. The hardest part of any project or activity is starting it. The status quo is comfortable, it’s easy, it’s known. Something new is uncomfortable, hard, unknown, risky. But everyone knows that. What’s easier to forget is that once you start, the resistant forces, while still present, are actually much lower than what kept (or delayed) you from starting.
So whether you’re lying in bed hating the run you said you’d go on, or hemming and hawing about a project you want to kick off, just start it. Trick yourself into starting it if you need. Start small. For example, if you’re having trouble running regularly, just tell yourself you’ll turn around after 5 minutes in the run if you don’t feel like continuing. You’ll likely never actually turn around after 5 minutes, because you’ll be warmed up, and you’ll feel good, but that trick will get you out of bed.

Whatever it takes to overcome the static friction, just do it.

The Lower Right Quadrant

The Lower Right Quadrant

A few months ago I got together in the old YouCastr offices with a big whiteboard, a few pizzas, a few packs of beer, and some entrepreneurial product folks to chat about various concepts (or schemes) and think about web trends in general. 

One of the concepts that emerged, admittedly following some mental lubricant, was the “Lower Right Quadrant”.  Being a former consultant, I love frameworks and 2×2 matrices. So as we were chatting about ridiculously profitable dating sites, and how hard we have all worked to create business that don’t throw off nearly those levels of cash, something hit me. Here is that framework: 

The framework looks at profitability vs. world impact. In the top right are profitable companies that impact the world for the better, like CleanTech (successful ones), and possibly Google (when they’re not being evil). The upper left quadrant are necessary humanitarian efforts that might not be very profitable, either by design (e.g. non-profits, government), or by market conditions (e.g. healthcare). The lower left quadrant is where most companies end up, slightly profitable or unprofitable, with little impact on the world. And finally, the Lower Right Quadrant, is where silly and salacious companies make a ton of money without attracting competition from well-intentioned entrepreneurs looking to make the world a better place.

Interestingly, most startups think they’re in the upper right quadrant, and have audacious goals to change the world and enrich themselves and their investors. But most startups are actually in the lower left quadrant, making incremental products that end up not being very profitable.  
We continued our discussion, thinking about opportunities in the LRQ, ranging from a Swoopo model for dating, to social games, to online pawn shops. One challenge we faced was realizing we weren’t really in the target market for any of the LRQ products we brainstormed, and had to continuously think outside of ourselves (or have a few more beers).  Another challenge is to get excited about something that is not inherently beneficial.  I do actually want to help the world, but there is probably some supply-demand type curve that relates profitability to world-changingness, i.e. the less utilitarian and world-changing the product / company is, the more profitable it has to be to motivate me to continue working on it.

So, before you get all starry eyed about your next big world changing money-printing concept, think LRQ.  And get the shirt in the meantime.

Opportunities in The Mobile Internet

I wrote previously about the four phases of the Internet, and how we’re approaching the Mobile (+ Location) Internet.  As a follow up to that post, I wanted to explore some specific areas and opportunities with this new paradigm.
Solving “Local”

Many companies have tried to solve local, applying technological solutions to the problems facing local business promotion and discovery.  Unfortunately, the local problem has proved to be extremely challenging. This is partly due to the businesses themselves, because they have enough day-to-day issues to worry about and aren’t very tech savvy. But the bigger reason is that selling to local business is very expensive. Even the tech IPO darling OpenTable has spent years and millions of dollars to get to 15,000 restaurants, and still has to fight to make a meager $2.6 million per quarter. The difference in the mobile + location internet age is that there is a potential to crowdsource the local business data (e.g. Yelp and Foursquare), and also make the onboarding process for local businesses much more seamless, potentially as simple as a smartphone app. Results may end up being as simple as geo-coupons, but I think we’ll see much more interesting things that that in this space.

Education, Books and Information
We are in the midst of what I hope will prove to be the most transformative time in education since the advent of the classroom at the start of the industrial revolution. Various new models are emerging in education, but the mobile Internet opens new doors by making an essentially infinite amount of data and information readily available.  As facts become increasingly available (just a quick google search away on your phone), education will shift to focus on concepts, methods, innovation, and synthesis, rather than the fact regurgitation so prevalent in today’s educational models. And of course, the trend will also serve to blow up the concept of a “book”, whether it merges with the Internet as O’Reilly predicts, or simply becomes disaggregated into more focused chapters or articles. Location in this case is less relevant, but mobile computing will permanently alter education and information sharing.
“Hard” Augmented Reality
One of the common threads with mobile based computing is augmented reality.  This phrase usually conjures images of superimposed information or animations on the existing world, whether through the eyes and screen of a smartphone (e.g. Layar), or eventually in more integrated means like retina displays. Google Maps and Streetview are providing the scaffolding for this type of information in the physical world, so you’ll be able to pull up information about a business or a building simply by pointing your phone at it.  Additionally, face recognition technology (e.g. Apple’s rumored acquisition of Polar Rose) will bring that type of functionality to people, perhaps pulling up their contact info and recent status posts when you greet them.

“Soft” Augmented Reality
But in addition to these map and 3D focused augmented reality, there are plenty of applications to improve day to day life that are really “augmented reality” but don’t appear to be.  A great example is Shazam, which lets you find out the name of a song you’re listening to, solving the incredibly annoying problem of not knowing what a song is when you’re listening to it. (I hate to admit it, but I recently tagged a Justin Bieber song.) Many other “soft augmented reality” applications will emerge to make daily life more interesting, fun, and pleasant, without being obtrusive. 
I myself and not a gamer (and I’m not personally addicted to the various game mechanics of today’s location based services), but it would be silly to not talk about the Gaming component of the current internet age. An omnipresent, location aware computer (i.e. smartphone), provides an incredible device to integrate the real world with gaming. It’s the core thesis of SCVNGR. I certainly see mobile + location internet enabling the “gamification” of life, and we’ll see to what extent, hopefully we don’t end up amusing ourselves to death
These are just some of the trends and opportunities emerging with the mobile + location internet. And given that the stakes are higher, the user base bigger, and the technology easier than ever to adopt, there’s little doubt that the winners in this age will be even bigger than those in ages past.

The Four Internet Ages

The Four Internet Ages

Now that I’m between startups, I’ve spent a lot of time thinking about what I want to work on next.  I like thinking in frameworks, which makes it easier to evaluate new opportunities and create my own theses around where technology and business is heading.  My previous analysis on the Product vs Distribution Framework focused on the core traits a company needs to ultimately succeed. This post looks instead at the macro trends of the Internet itself. 
Each phase of the Internet’s growth was enabled by key platforms, and had key successes that were able to level those platforms and other trends to create huge businesses.  Each phase also built on the previous phases, and would not have been possible without the foundation created before it. And because of this improving foundation and growing user base, each phase enables bigger opportunities that can be reached faster than before. 

The diagram below shows the four key phases of the Internet, as the platforms and successes in each, as well as the worldwide desktop and mobile Internet user base. Note that the timeline for each is a general approximation of that trait as the defining leading edge of the web, and there exists considerable overlap in the general use cases and impact of each.

1 – The Early Internet

The first Internet phase saw the early growth of users.  This growth (and perceived future growth) was so explosive that it led to the great Dot-com boom and bust. It was built on the proliferation of the web browser (Netscape and later Internet Explorer), increasing penetration of desktop computers with Internet access, and standardization of web protocols.  In the early days, there were not a lot of users or content, so the most logical way or organizing available content for a limited user base was simply an editorial listing of interesting content, thus the birth and proliferation of portals like Yahoo.
2 – The Searchable Web
The second phase of the Internet saw an explosion of content, which was built on the key enablers of the first age (desktops, browsers, web standards). Once the volume of content exploded beyond the early manageable levels, lists and portals were no longer sufficient to access this content. This led to search becoming the only feasible way to harness the incredibly expanding volume of content. 
Google emerged in this era as the key platform because of it’s simple, powerful, and fast search capabilities. This dominance led to a web that was organized through the principles of PageRank, and created the SEO and SEM industries. It also opened up a new world of long tail e-commerce, where small companies could have a much bigger footprint than ever before, and cheaply reach customers across the world.

3 – The Social Web
The third phase of the web was based on saturation of online penetration among the general population. A true social web can only existing once online penetration begins to saturate the population, reaching 70% adoption or more. Interestingly, most developed countries started reaching this penetration level around 2003-2005, coinciding with the birth and growth of social networks. This is in stark contrast to the Searchable Web, which is valuable to users even with low adoption rates as long as there is enough content to search. 
In this phase, Facebook has emerged as the defacto social platform. This platform has facilitated the creation and growth of two of the fastest companies ever to reach a $1B revenue run rate: Zynga and Groupon.  Both of them used the Facebook platform to grow faster and more cheaply than ever before due to the incredible low friction that social networks have to get new users. Zynga reached 100 million users faster than Facebook itself, mainly because most of the users were ALREADY on FAcebook, making them much easier to acquire.
4 – The Mobile Web
The fourth phase if the one we are just entering, which is being enabled by ubiquitous mobile computers (e.g. smartphones). Inherent to this phase is not just the mobile computer itself, but the fact that they are increasingly always with us, and are location aware (know where we are).  The combination of ever-present mobile computing, plus a rich location layer, seamlessly integrated with the social graph and the searchable web creates enormous opportunities. 
The key platforms in this space have are clearly iPhone and Android, but there is still room for winners on the customer side.  Foursquare appears to be one of the early companies to succeed while specifically leveraging mobile + location, but there will certainly be more. 

What does this mean?
What’s interesting about these trends as I pointed out earlier is that each phase gets progressively bigger than the one before, and leads to faster growth for companies that are well positioned.  You can bet that new companies will emerge will get to $1B in revenue faster than Groupon and Zynga. 

The Product vs Distribution Framework

The Product vs Distribution Framework

In the startup world there is an ongoing debate about the importance of having a very solid product versus having great distribution. A few weeks ago at a dinner hosted by David Skok and Antonio Rodriguez we had a very active and interesting debate about the merits of each. Antonio posed a question about which of the two we would prefer. Since then I’ve continued to think about this issue, and created a framework to help me think about it and evaluate the tradeoffs.  

The Product-Distribution Framework

Given that the product vs distribution debate is not just an either or, I wanted to create a framework to help me think and evaluate the tradeoffs of each, and take into account the strength of each. So I created a simple 2×2 matrix comparing weak and strong product vs weak and strong distribution, using a fun theme of plants to characterize the various types of companies (trust me, it’s much safer for work than the initial images).

The Oak Trees – Great distribution and product feed on each other to build great companies
At the top right are the truly great companies, that have created solid products and achieve successful distribution to reach enough people.  These great companies are household names, including Facebook, Apple, and Google.  There are various paths to get there, but most of these companies have a fanatical devotion to creating a solid product, coupled with a very smart, disciplined, and powerful distribution. Throughout the growth, these two strengths continually feed on each other creating a positive feedback loop. 
Example: Apple in 2010 – Apple is firing on all cylinders, led by Steve Jobs’ literally maniacal focus on creating a perfect product. But it’s easy to forget how strong the Apple marketing engine is, creating hundreds of millions of dollars of free publicity with every product launch. They have also created one of the world’s strongest brands, and use their huge profit margins to build a wildly successful retail distribution channel.
Example: Google – Google is the undisputed search leader with about 70% of the market (and holding strong). Early on they built a fundamentally superior search product, perfected it through continual execution and improvement, and leveraged the strength of the product to grow distribution. Now the two build on each other, with their market share in search enabling them to continue to improve their product through more data and more servers, and that continually improving product keeps people coming back to use their search engine.

The Weeds – Potentially profitable by eventually doomed
At the top left are companies that have created great distribution despite a weak product. Contrary to conventional wisdom, these companies can be very profitable despite the weak product because of various channels to reach customers and user habits.
Example: MySpace – MySpace leveraged huge email lists to spam users and build a large social network. They grew quickly and sold for $580 million, but continual lack of execution on the product led to their downfall and imminent irrelevance.
Example: Microsoft – A monopoly is about as strong a distribution strategy you can have, but even that is not enough to sustain a company that continues to make inferior products. Despite being wildly profitable, their stock has gone nowhere in 10 years, and their lack of product execution has put them in weak positions in the next computing wave (mobile and tablet).
Example: American auto makers – The analogy even applies outside consumer technology, as evident by the downfall of the American automotive industry, which for too long relied on patriotism, customer loyalty, and a saturated dealer network to distribute an inferior product. Eventually it caught up with them, and now even though they are building better products, decades of perception still linger with consumers and they face an uphill battle.  

The Desert Flowers – Potentially great but need some breaks
At the bottom right are companies that have created a truly interesting and innovative product, but have struggled to get it out to the people that care about it. Many companies founded by techies have a strong risk to go down this path, continuing to focus on building the perfect product and not spending enough time getting it out there. And make no mistake, Facebook was not one of these companies in the early days, aggressively crawling online groups to get initial profile pictures and emailing whomever they could.
Example: original Mac-only iPod – Given the rapid success of the iPod franchise, it’s easy to forget that it originally launched exclusively for the Mac as a way to drive Mac sales, and took almost 2 years to sell 1 millions units (vs. 74 days for the original iPad, 28 days for the iPad, and about 1 day for the iPhone 4). It was only when they began offering a PC version and leveraging their iTunes distribution platform that sales began really accelerating.

The Tumbleweeds – Also Rans – Lots of challenges, but could work in certain offline niches
In the lower left quadrant are the companies that don’t have a particular strength in either product or distribution, and are thus left facing many challenges. In certain commodity local businesses with limited competition, this may not be an issue (for example the only dry-cleaner in a neighborhood), but for online businesses this can be a killer.
Examples: Most clones that lack distribution – Clones often try and replicate a successful product but lack many of the soft traits and methodologies that made those products successful in the first place, and thus often create weak imitations. If those are coupled with distribution advantages, they can be profitable, but often they are mired in the bottom left quadrant to hang on and pray.

What this means on a practical level
Coming back to Antonio’s question from that dinner, if I had a choice of having either great distribution or great product, I would choose great distribution, turn that into profitability, and leverage that to build a great product. Practically speaking, however, those choices are rarely presented.  Therefore, when starting a new company, the important point is to clearly understand the tradeoffs as well as the strengths of the early team and company.  Then use that to built a great company, whether it means leveraging distribution to get to a great product, or building a great product and figuring out the distribution. 
And the truly great companies are constantly focused on both, like an oak seed going deep into the ground for a solid foundation (the product), and reaching for the skies to get sun and spread the branches (the distribution).
I’d love to hear other thoughts about this framework as well as other good examples. I’m also planning a follow up post about how to move between areas in the quadrant, and specific industry dynamics. 

Online Groups Suck – Email wins, with limits

I have written before about how email is still the killer app.  There are lots of new dedicated applications to serve specific needs, but often I find myself reverting back to the trusty email.  But one area that I have a love-hate relationship with is the massive email thread.

Email threads have their limitations
This annoyance has recently reached a new high as I have three of these massive email threads going at the same time, one for a local Boston/Cambridge tech geek pickup basketball and soccer, and two for soccer leagues I play on.  We use the email thread to announce game times, check who’s coming or not, coordinate rides, or make jokes. It’s convenient and annoying at the same time. 
Email threads are easy and comfortable
Email threads are great because they require no work or learning to use. It is an invisible “product” (use case really) that relies on a platform people are already using every day (email). You compose an email, fill out the addresses automatically, and hit send. And to reply, it’s one click or keyboard shortcut. No new usernames and passwords, no new places to check out, no new service to learn.
Online groups have too much friction and are not the solution
One common solution to this problem is online groups, but they have continually disappointed me as a replacement for the massive email thread. Yahoo Groups and Google groups are great for lots of collaboration, forums, or development projects, but for a simple email thread, they are terrible.
First off, they require people to register for the group before accessing it. No matter how tech savvy the group is, there will never be 100% participation, and in many cases people have to create new accounts for a new service (and nobody wants to create yet another account that they will soon forget). Second, they require a motivated and dedicated admin to create the group, manage members, and eventually possibly pass the group on to someone else. Third, they require people to either continue receiving all emails (thereby not saving the inbox), or remember yet another website to check out on a regular basis. And finally, they are not stick: I have never participated in an online group discussion that endured past the initial excitement of the first few weeks. 

What’s the solution?
Is there room for a Posterous for online groups and email chain management?  I hope so.

Ariel Day 2010 – Registration Open

Five years ago, while living in Chicago, a friend of mine was making fun of me for planning a full day celebration for my birthday, and cynically suggested to just have a full “Ariel Day”.  I thought it had a nice ring, so I went ahead and did it. 
Since then it’s been a summer tradition. Ariel Day technically is the first Saturday following the 15th of July (my actual birthday). As a point of clarification, Ariel Day is actually separate from my birthday, though every several years they fall on the same day. 

This year the plan is to head out to Georges Island, a great island in the Boston Harbor with a fort to explore, open area to play games, and BBQ pits.  After a few hours there, we’ll head back to my roofdeck for drinks, pizza, great views of the Charles and the sunset.  And for the true fighters,  we’ll head to a club here in Boston (not Felt) for some dancing.
Full details at:, tickets and registration at:

YouCastr – A Post-Mortem

Introduction: Why I’m writing this

There are many post-mortems from failed startups out there, mainly because there are a lot of failed startups, and the people that start them tend to be very introspective and public about their successes and failures. I’m no different.  This post-mortem will serve to get things off my chest, organize my thoughts, get the most out of the experience, and share my experience with others.

I’m also writing this to be able to point to a single, detailed, lengthy answer to the inevitable questions I’ll be getting from friends and colleagues about what happened with YouCastr. Now people can read to their heart’s content. 

As I write about my experiences, people who know startups will see many common themes.  Most of the conclusions here are consistent with Paul Graham’s analysis and understanding of startups, what’s challenging, and why they fail (if you’re planning on starting a company, especially in tech, read every single one of his essays). But no matter how many times you read or hear certain lessons, you have to do it yourself to really understand. Here are my specific and personal experiences to add color to that advice.

A Brief History

YouCastr is Born

The idea for YouCastr was hatched about three and a half years ago, during a car ride down from Jay Peak with my good friend Jeff Dwyer.  Throughout the entire ride we were throwing ideas back and forth about cool companies, fun ideas, and stuff that bothered us.  One in particular stuck with me, which was the idea of bringing Mystery Science Theater 3000 to the modern age, and let anyone provide their own comments.  After exploring this some more, I ended up settling on sports as the logical market. This would mean the commentary would have to be live, because otherwise it would have been just a podcast platform, which was not very interesting technologically.  A couple of days later I shared the idea with my soon to be co-founder Jeff Hebert, and we continued thinking about it.  Within a few months we put together a team of 4, created our initial plans, and began building an alpha version. 

Initial progress

As we were getting off the ground, three of the four founders (including myself) were mainly working on building the actual product, since we couldn’t do much of anything without that. We learned Ruby on Rails, did our own designing, worked nights and weekend on the startup as a complement to our management consulting day-jobs, and clawed our way to our initial alpha and private beta. 

Building the company

We then spent the next three years building the company, quitting our jobs, raising money,  opening our office, hiring people, firing people, going back to bootstrap mode, and finally, pulling the plug.  


Startups are all about pivoting. It’s like a word game where you start with HURT, change one letter at a time, then end with LOVE, with many other four-letter words along the way (btw, you really can do that in 6 moves). In our case, we started as a virtual sports bar where people could chime in audio commentary and ended up as a do-it-yourself pay-per-view video platform.  Seems like a radical change, but each pivot was the equivalent of changing one letter.

Our first pivot was to focus on live audio sports broadcasting of games that weren’t being televised (instead of adding commentary to nationally televised games), in response to what customers were doing. Then we added video broadcasting to that same market, focusing on broadcasting sports that weren’t covered (primarily high school and college).  And finally we expanded beyond sports, mainly by de-emphasizing the sports branding on our platform, and adding a few features more geared towards video producers than to schools and teams. All of these were natural pivots, not jumps.

Shutting Down – The Reasons and Need

1 – Ran out of cash

The single biggest reason we are closing down (a common one) is running out of cash. Despite putting the company in an EXTREMELY lean position, generating revenue, and holding out as long as we could, we didn’t have the cash to keep going. The next few reasons shed more light as to why we chose to shut down instead of finding more cash.

2 – The market was not there

The thesis of our current business model (startups are all about testing theses) was that there was a need for video producers and content owners to make money from their videos, and that they could do that by charging their audience. We found both sides of that equation didn’t really work. I validated this in my conversations with companies with more market reach than us, that had tried similar products (ppv video platform), but pulled the plug because they didn’t see the demand for it. 

Video producers are afraid of charging for content, because they don’t think people will pay. And they’re largely right. Consumers still don’t like paying for stuff, period. We did find some specific industry verticals where the model works (some high schools, some boxing and mixed martial arts events, some exclusive conferences), but not enough to warrant a large market and an independent company.

3 – The team was ready to move on

The core team of 5 of us has already made significant personal, financial, and emotional investment over the past three years. We have had our share of tough breaks, not to mention almost two years without salary.  

4 – No light at the end of the tunnel

Given the industry trends we were seeing, we just didn’t see a light at the end of the tunnel worth surviving for.  This market may get slightly better, but it’s not going to be a big company.  

5 – We need to put a stake in the ground

We’re survivors. We hate giving up, and have tenaciously survived for a long time.  We survived the worst economic environment in generations (during which we also tried to raise money), and knew how not to die.  But it was time to shut down and move on. 

A Retrospective – Why we failed

In most of the following points I say we, but as CEO, many of the mistakes below can be placed directly on my shoulders, which I will take as a valuable experience as I move on.

Didn’t pivot fast enough

We did a pretty good job of pivoting, but we didn’t make the hard choices quickly enough. Our first pivot, towards broadcasting of original sports content, took us 6 months.  We had legacy users and web traffic that we were afraid of losing. We had a brand in one area. We had a story for investors, customers, and the community. All of that made it harder for us to quickly change our focus and apply all resources to the new area, which we knew was the long term future. We iterated our product quickly, but didn’t pivot fast enough

Didn’t love it
We started the company because we liked the idea and wanted to do something entrepreneurial. We weren’t in love with the idea or market we were going after, and weren’t core users of our product. We worked really hard getting it off the ground despite this, but it made it more difficult to sustain the energy and to understand the best product choices.

Made hiring mistakes

Hire slow, fire fast. That’s how the saying goes. We made a mistake when hiring. We hired too early (before product-market fit), and we rushed into it by foolishly setting an internal deadline to make the hiring decision, which drove us to ignore some gut reactions by some of the core team members. Eric Ries has a great overview of how not to make these mistakes in his Lean Hiring Tips post.

Spent too much time raising money

Almost immediately after our private beta we started trying to raise money, and saw many of the typical challenges when raising money for the first time.  This was late 2007 remember, when plenty of Web 2.0 companies were getting funded, and we got caught up in the spirit.  We spent 6 months raising our angel round, and finally closed it after launching our public beta in February 2008.  We raised less than we should have (Chris Dixon notes that the worst thing a seed-stage company can do is raise too little money and only reach part way to a milestone, which is great advice). We spent 3 months getting ready for raising our next round, then 6 months beating our head against a wall trying to raise money during the financial collapse. Finally we regrouped, but had serious short term cash issues that we had to resolve with additional investment from current investors and cutting of costs. We then focused on the product and made some solid progress, with the plan on giving it another go. By the time we got there, though, we realized we didn’t have the metrics we wanted, so pulled back our fundraising efforts and decided to go back to bootstrap mode. 

Never quite figured out customer acquisition

We never seriously figured out customer acquisition, and had trouble growing throughout our various pivots. Customer acquisition is hard and more expensive than most people realize when starting a company. There has been a lot of good analysis, including Andrew Chen’s overview of calculating cost per customer acquisition and David Skok’s warning about how it can be a startup killer, but it takes firsthand experience to understand that. 

Too many founders

We started the company with four co-founders. I believe Dharmesh Shah nailed it in his analysis of the optimal number of co-founders. In our case, the advantage of having 4 co-founders was that had more people and resources willing to work for sweat equity. But it also presented challenges, including slowing down decisions, as everyone naturally wants to chime in with their opinion.  As CEO, a lot of this falls on me, as I should have been stronger in making decisions. I tend to be a consensus builder, but in my next startup I will have to improve my ability to make bold unpopular decisions while still motivating everyone and building consensus after the decision is made.  On the plus side, the entire founding team was incredibly committed through the entire time, and we never had any of the fundamental founder issues that many people complain about become a major problem. 

Counted on big partnerships to close (when they didn’t) and to help more than they did

We initiated some very interesting high level partnership and business development discussions with large companies. We put some hope into these deals, but large companies move much slower than startups, and every deal took much longer than we needed. Marc Andreesen even draws a parallel that going after large partnerships is like chasing Moby Dick

We put too much stock and hope into closing some of these. And for the ones we did close, we expected more results than we got. It’s an interesting dilemma, because partners are often the best acquirers, but the downfalls can even lead people to suggest to NOT partner with big and powerful companies

What I Learned and some of the positives

I’m an optimist by nature, which you have to be to start a company given the odds and challenges. Given that, it’s good to look back and think about the positives of the entire experience. It’s incredibly satisfying to create a revenue-generating company that is flirting with cash-flow positive, especially having started with a crazy idea. The experience of building a company and tasting success was incredible, and though we didn’t quite get over the hump, we have tasted it, and it will only motivate me more to get there again, through all the hardships.

On a personal level, I’ve learned more about business, people, life, and myself over the past three years than I ever have. I have made life-long friends with whom I can share these experiences with. I have come closer to understanding how to reach my limits, which is one of my fundamentals goals in life.  Startups let you try and find those limits  in a way that most jobs wouldn’t, and I’ll keep pushing. And best of all, I have realized that my true passion is entrepreneurship. I have a very addictive personality, and therefore only do things where I am comfortable with the extreme case, like starting companies or running ultra-marathons

We built a great culture, including some great parties for the local tech-scene, competitive ping-pong matches, and late night coding sessions with house music blasting. We converted three lifelong PC people to Mac, all of whom are happier for it.  And most satisfying, we helped kick start two young and promising careers, those of our designer and community manager.

Moving Forward

My long term goal is to continue starting companies.  There’s no question I’m in a better position now to start another company than I was when I first started YouCastr.  It’s almost like thinking back at how much more fun high school would have been had you known what you knew when you graduated back when you started. Practically speaking, though, after having gone almost 2 years without a salary, I’m not in a financial position to bootstrap another company, which is the way I would really want to start a company.  

In the short term I’m working on various projects for my consulting company, Scenario4. We are working with some great people on some fun projects across the tech world.  I am also pursuing several side projects, including the recently launched BooksforBits, a non-profit company designed to help accelerate the transition to ebooks while getting books to communities in need.

It’s an incredibly exciting time in technology. We are on the cusp of the post-pc era, which includes a revolution in the mobile space, and in how we interact with and perceive computers. We are in a world where startups can be more capital efficient than ever before. And most interestingly for me, as a society we are going to be facing challenges unlike any we have ever seen. 

With every ending is a new beginning, and I’m excited about what lies ahead.  

Is Diaspora the next OpenSocial?

Remember about 2 and a half years ago, when the Facebook Platform was still new, and all the talk was about OpenSocial?  It was supposed to be a platform for all the “other” social networks (outside Facebook), where developers could easily create apps for all of them at once. Dave McClure wrote an interesting post about two and a half years ago talking about OpenSocial vs. Facebook Platform (before Connect). OpenSocial all but died, Facebook got stronger. 
Now there is a lot of talk about Diaspora, the “the privacy aware, personally controlled, do-it-all distributed open source social network.” The name is already ambitious and confusing enough.  They have been making some noise, getting some press, including a piece in the New York Times, and have raise over $177k from almost 5000 contributors. Jason Fried argues that they have too much money and no product

But I’d argue that they face much deeper challenges.
Market Adoption
For this to be significant, it has to see Facebook style viral growth. Facebook’s growth curve was a once in a generation thing, I don’t think we’ll see it replicated within the same decade.

Technical Challenges
Authentication has been a challenge online for a long time. Facebook Connect (now Graph) is making great progress on Single Sign on, but it hasn’t been easy, just look at OpenID’s failures.
Users Don’t Care
Most users don’t care about their privacy settings, and won’t care about a more open Facebook. And it’s hard enough to get people to change, even when they do care.

Trading One Master for Another
If Diaspora wins, then we’ll trade one master for another. Maybe with better default privacy settings and visibility, but with a governing body all the same.
Facebook Interoperability
I think it’s fair to say that any effort to create a new social graph will need to rely on Facebook’s existing social information (profile info, etc.) and social graph (friends), and possibly also the photos and other information on there. Forcing people to give all that up will be a challenge.

We’ll see two and a half years from now if Diaspora caught hold, or ended up like OpenSocial.  I’m rooting for a more open Facebook, and maybe Diaspora will help achieve that without ever launching a product. But they’ll have some serious challenges to create a truly viable alternative to Facebook.

Alternatives to an MBA

In my last post I wrote about the only 4 reasons to get an MBA. Now I wanted to follow up with some alternatives. 
Start a Company
The best alternative is to start a company. It will cost about the same (initial investment plus lost salary), but provides a MUCH better first-hand learning, creates a good opportunity to build a network (required for fundraising, finding co-foudners and partners, etc.), and forces you to be self sufficient.  Don’t get an MBA if you want to start a company, JFDI

Get a Masters in Engineering Management
If you know you want to stay on the technical side of management (and have a healthy disregard for MBA types), then get a Master of Engineering Management.  There is a growing number of schools offering the degree (including my alma matter, Dartmouth, and see a full list at Wikipedia). 
Specialize in something you love
The other option that is often looked over, is just to double down and study or do something you really love.  Get a Masters in Fine Art, or History, or anything else. The world needs plenty of specialists, and more often than not, you’ll be able to do much higher quality work if you really love it, and the rest will come (riches, fame, etc.).  

I’m sure there are plenty of others, but these three examples quickly jumped out at me.  

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