Juventas Fugit –

Last year I set out some goals for 2011, and while I didn’t accomplish everything, I’m pretty pleased with the results. To recap, I set out to gain a better understanding of mathematics (fail), to drastically improve my handwriting (fail), to learn how to code (success!), to improve my understanding of learning & the education system (success!), to write more (success!), to drink more water (partial success), and to eat healthier (partial success).  

This year I’m going to keep it simple and focused:

• Learn Javascript. I’ve managed to the learn the basics of coding (mainly through Java), while reconnecting with my HTML/CSS roots. Given my love for the web, and recent developments in Javascript (Node.js, MongoDB, Google’s V8 Engine, jQuery, CoffeeScript, etc), this is the language I really want to master.
• Launch an app. It may be small, or it may be one of the larger projects I’ve been working on in the education space, but either way I want to take something from concept to users on my own.
• Sketch regularly. I’m giving up on my handwriting for now, but I really want to get back into drawing.
• Gain a better understanding of mathematics. I’m trying this one again, this time with a more focused approach. I want to learn at least the history of mathematics, which will hopefully give me better bearings on where to look to improve my core understanding of the subject. (Why are we not taught this in school??)
• Exercise daily. Anything will do. Regularity is the key.
• Eat healthier. Less junk food, less carbs, and more protein and veggies.

I’ve had the privilege of working in venture capital for the past few years, starting at a very young age with little mentorship in the beginning. As a result I made a ton of mistakes – and learned a great deal making them.  Below are a few of the more important lessons I wish someone had told me on my first day:

1. Don’t be a generalist (focus on a space you care about).  Don’t be afraid to limit the scope of what you’re willing to spend time looking at. I’ve actually found that the more specific I was about my area of interest, the more deal-flow I would see in a given space (e.g. education). The logic is simple: when I see a good deal, I want to send it to friends. But when every one of the 100 VCs I know has told me to send them stuff I like in ‘mobile,’ who do I send it to? I can’t send it to all of them, so I end up sending it to (a) the guy I saw last week that’s top of mind, and (b) the person who told me they’re super passionate about that specific space.  There are plenty of startups in spaces you care about – focus on those. 
2. Say no quickly. Early on I had this misguided notion that every deal we were sent we had to deeply examine, and I would therefore spend far too much time researching and sorting each out in my mind. Just because something looks like a good deal doesn’t mean it should be pursued.   If you aren’t really passionate about the space – or haven’t taken the time to truly understand it on your own –, don’t waste an entrepreneurs time with weeks or months of due diligence. They have a business to run.  I try to say no in the first meeting (or even before that) to most of the stuff we’re sent, while pointing them in the right direction and providing a few thoughts if I know something about the space.  I’ve found that the best entrepreneurs will come back and try to prove you wrong (and tenacity is a very good sign).
3. Make sure you can really add value. If you can’t add value (beyond recruiting) on an ongoing basis, you won’t stay relevant to the team and will be out of the loop – even if you’re on the board. (Side lesson: the most important decisions are made before and after board meetings). Stay a part of the conversation and in the know by making sure that you’re constantly engaged with the team and helping out. This is another reason why it’s important to be specific in your investment screening – if you care about the space you will have an easier time staying actively involved.
4. Invest in teams with an ‘unfair advantage.’ Because of simple web languages, an abundance of APIs, and open-source content, it’s easier than ever to build a web product quickly.  The teams you want to invest in are those who have an ‘unfair advantage’ in two areas: (1) in their deep understanding of the space – the competitors, partners, and customers –, having lived/worked in it for years, and (2) in their *proven* ability to build beautiful products people love. A deep understanding of the space provides them with not only the knowledge to navigate it but the right relationships to sell into it. This understanding, combined with an ability to craft great products, makes for a huge competitive advantage. It’s easy to build a product, but difficult to build one that the right people will care about enough to pay for.
5. Invest in (technical) novelty. I don’t believe venture capital dollars should go to companies that are building a ‘me too’ concept for a different geographic region or demographic (see the Founders Fund Manifesto for more on this). Invest in big ideas that will really pave a new path and radically change the world in a positive way, and in technology that took more than a weekend to build.  There’s no problem with simplicity, but generally it takes a while to get an idea right for a specific space. It’s not about the pure technical complexity of a product, but rather the fact that the team has slaved away on it long enough to know exactly what features and technology is required to solve the core of the pain-point for their target demographic. In most cases there’s a pretty strong correlation between the time it took to build the product and how long before you see serious competition.
6. Don’t be pressured into closing fast. It always takes a few in person get-togethers for people to show their true colors. Make sure you have enough time to really get to know the entrepreneur (see this post by Mark Suster), and to do your homework. Generally there’s no way that you’re going to have time to properly reference check and diligence a person and concept if the deal is closing in a week. I make this clear to entrepreneurs upfront, and its one reason why I frequently say no fast.
7. Involve your partners early and often. I’m a pretty independent person, and in the beginning I lost a few great opportunities because I worked alone and tried to present my partners with a pretty package at the end, only to be met with a lack of excitement or confusion.  Don’t expect your partners to jump the moment you show them a deal. Make sure they ‘get it’ early and often, and don’t assume they’ve read the due diligence and understand the intricacies. Most importantly, figure out what your partners are looking for. Ask what they need to see for it to be a rockstar in their eyes.
8. Manage Entrepreneurs’ Expectations. All too often my excitement would translate into mixed communication with an entrepreneur, and a misguided notion that it was a done deal. Make sure they’re aware that it’s a partnership decision, and that you speak for yourself, not others.
9. Make sure your vision of the product is the same as the entrepreneurs. And that they have a strong vision to begin with. Coming from the entrepreneurship world, I tend to have a very ‘big vision’ way of looking at things, and sometimes get caught up in my own ideas for where something can go. Make sure you’re not projecting your vision onto their startup, and that you’re on the same page.
10. Don’t screw entrepreneurs. Keep deals simple, and give founder friendly terms. (It will come back to bite you – trust me).

I’ve officially joined the Enterproid team this week, and I could not be more excited. I’ve worked closely with the founders over the past year since our investment, and have just been blown away. The technology is impressive, and the guys are among the brightest I’ve ever worked with. (Comcast, Qualcomm, & Google Ventures agree.)

While I’m moving back to the light side, I will remain a partner of BOLDstart Ventures (so please keep sending opportunities my way!), continuing to work with Eliot and Ed, who have both been awesome mentors for the past few years. I’m totally committed to continuing to actively support our entrepreneurs – I am, as always, still happy to hop on a call or meet up at any time to help out. Several of the projects I will be working on for Enterproid will be highly relevant to other mobile startups (more on this soon), and should enable me to provide a lot more of that elusive venture capital ‘value-add’ to the companies we work with.

Those who know me well know that I love to build, and that since putting my last startup project on hold to join the venture world I’ve been eager to get my hands dirty again. I strongly believe that to be a great venture capitalist you need to deeply understand what it’s like to work at and start a venture yourself. I’m hoping that Enterproid will be the first of several opportunities to make myself a better investor, and a better entrepreneur.

For the past nine months I’ve spent most of my time in Oxford, researching social policy and the Internet’s impact on access to higher education. While I’ve technically been working at Penny Black and BOLDstart full time as well, I’ve spent most of my time disconnected; reading, thinking, and wandering through the countryside.  Here are a few of the more important takeaways:

1. There’s no such thing as a generalist. At least not a useful one. Many people who go into consulting or similar fields believe they can study a bunch of different businesses and solve any problem once they have the right set of tools.  While I’m sure they can help bring clarity to many problems, there’s nothing like immersing oneself in a space – enough to intimately understand all of the players, issues, and interests. In the startup world this kind of experience gives entrepreneurs a big leg up against others with a similar idea, and it’s for this reason that venture firms put so much weight on a team’s domain knowledge.
2. Detach completely for quality thought. I took for granted the importance of having time/space to think clearly, and didn’t realize how hard this is to do in New York. You get used to being bombarded every few minutes with emails, texts, phone calls, meetings, and other distractions.  Living in a big city affects your clarity of thought. Being antisocial every once in a while – perferably in a beautiful place –, and taking the time to think, digest, and reflect, leads to amazing results. Simply reacting all the time to the social stimulus around us makes for dull (and stressed) people.
3. Diversity of people = diversity of thought. 99% of the people I hung out with in Oxford did not know what an API was, had not integrated Rapportive into Gmail (yet), and were slightly offended when I told them that Klout could predict how influential they are online. Generally we think of diversity as people of the opposite view, but the best diversity is people who are not even on the same plane of thought. Innovation happens between, not within disciplines, and it’s important to expose yourself to that every so often.

I frequently take up issue with the costs of higher education and the general worthlessness of many degrees. But if for whatever reason you are fortunate enough to have the opportunity to do a one year independent study program, it can be an incredible and valuable experience. If you do have the opportunity, don’t go straight out of undergrad, find a program that lets you explore before diving in, in a beautiful place, and in an environment where you’ll be forced to surround yourself with people much smarter and very different from yourself.

There’s no reason why 30 students should sit in a classroom and be lectured on the same thing at the same time at the same pace when everyone learns differently. There’s no reason why the tens of thousands of algebra classes are each being reinvented right now across the country by teachers of variable skill levels. There’s no reason why college students should go into hundreds of thousands of dollars of debt for courses and a diploma that may not take them where they want to go. And there’s no reason why teachers should waste time conveying materials that can easily be found online, when instead they could be inspiring students to be curious, discover themselves, and apply what they learn.

Despite how huge the education market is (estimated at $750b in the US alone), many VCs are afraid to invest in ed-tech because there was a lot of ‘road kill’ in the space after the dot-com bust. But much has changed in the past decade: the addressable market has expanded dramatically (10x more people are online, have 10x as fast connections, and are connected at least 10x as much), and we’ve recently seen a proliferation of internet-enabled mobile devices, data storage and processing innovations, and the spread of open source content that have brought about great efficiencies in content distribution, consumption, and production.

The importance of the Internet in changing education is more relevant than ever: we continue to move from a manufacturing-based economy to a knowledge-based economy at a rapid pace, yet our school system is still stuck in the Industrial Revolution. 

There are a great diversity of opportunities to innovate in the education realm. On the learning side, we need to create new ways to make it:

1. Fun. All physics lessons should be as fun as Angry Birds.
2. Ubiquitous. I should be able learn anywhere and everywhere, taking full courses on my iPhone or any other device.
3. Adaptive / Customized. Machines should learn how I learn and teach in a way that works best for me.  

And on the accreditation side we need to find ways to get people credit (/certified) for practical skills they enjoy in a much faster, cheaper, and more accessible way than is provided by the accreditation bodies who hold a monopoly on the education system today.

I’m not arguing that we should try to overhaul the current system and force schools to adopt new technology and ideas, but rather that if we create compelling learning and teaching products outside of the school system we can push change from the outside, in.

Some Inspiration:

• Fred Wilson and Brad Burnham on hacking education (especially the comments)
• Khan Academy (watch the videos!)
• Sir Ken Robinson & Jane McGonigal’s TED talks
• A Mathematician’s Lament (PDF)
• Turning Learning Right Side Up
• And many others (ask me!)

I hope this is obvious: forcing students to answer a series of questions under the clock is probably the stupidest way to test proficiency in a subject area. The ultimate goal of teaching is not fact memorization, it’s application. Exams under intense time pressure are useless: they are not at all a representation of the depth/breadth of a person’s knowledge in a subject area, nor how capable they are in applying it.  And worse, they encourage short-term memorization of information that becomes useless a month after the test. How much information do you remember from the last exam you took?

I admit that there are some professions where memorization-based, timed exams are more relevant – such as emergency medicine –, where the need to recall random facts under time pressure is actually a skill in and of itself. Though I would argue that even this skill will soon change as on-demand medical data is more easily accessible.

Thanks to the Internet and the relatively powerful mobile devices we now carry around, we have moved from having a ‘local’ to a ‘networked’ brain, where data is now able to be stored and accessed not just from our own head, but from society’s collective mind. These devices have literally become an extension of our brains: they help us navigate complex terrain, recall detailed information from years ago, and give us access to billions of pages of data covering almost every subject thinkable.

This model is obviously not without costs in terms of human independence, but we have always been social creatures, and this is simply the evolution of that capability to communicate and work together. Given this incredible new model then, how we use that information becomes so much more important. Exams should be structured to reflect this, and focus on data-rich application and creativity.

A month ago I bought a Kindle, and after a week of use I brought it back with me to Oxford, leaving my iPad in New York. It was a great decision.  For the longest time I had dismissed the Kindle as silly, calling it a ’segue technology’ – a device that would just be around until the iPad or some other multi-function tablet squashed it.  Who needs another media consumption device? I was totally wrong. 

What I had forgotten – living in the tech world and spending every free moment on email, Twitter, and blogs – was that reading a book is a very special and unique experience. It’s immersive, demanding complete attention, and involves opening your mind and letting yourself be transported to a different place, or a different way of thinking. This requires a device that disappears entirely as you start to use it: it has to be light enough that you forget you’re holding it, be large enough that you can immerse yourself in a page without it being unwieldy, and be easily readable in your favorite spaces – under a tree, on a beach, or in front of a fireplace.  

It also has to be free of distractions. The iPhone is great for short-form communication, skimming tweets, checking Facebook, listening to music, and watching online video on the go, among other things. These functions all happen to co-exist very nicely in one device: you’ll read a tweet with a link takes you to a web page with an interesting video that you then want to email to a friend or broadcast.

But reading a good book – and really absorbing the knowledge or story – is a totally different experience. If you find the right book and environment, it’s truly magical. It deserves a device focused solely on making that experience incredible.

The information age has fundamentally changed the job requirements of a teacher. A vast majority of the world’s basic knowledge is now ubiquitous – stored and easily accessible online from almost every computer and billions of mobile devices. Why, then, are we still forcing students to buy expensive textbooks and hiring teachers to lecture on subjects whose content is largely available from a quick Google search?

Before the 15th century, only a small subset of people on the planet had access to society’s accumulated knowledge. In the past 500 years, while the accessibility of knowledge has advanced dramatically, teaching methods have largely remained the same. Imagine the standard high school algebra class: the same set of materials is being taught in every school across the country by hundreds of thousands of teachers of varying competency. Yet a quick Google search reveals enormous amounts of free online materials on the subject that anyone can use to learn from right now on their own. So why do we still employ thousands of teachers to convey those exact same materials to students?

Rather than have restless students sit in a lecture and be instructed on a subject, we should teach them how to discover the subject themselves, and let them be free to explore. Teachers (sherpas?) should point students towards online resources like Khan Academy, and students should be left to explore different areas that interest them on their own with some basic guidance as to the minimum required competency of the subject they must achieve.  The teacher would act more as a mentor and guide, working with individual students on conceptual issues that arise in their learning, and ensuring they find the best resources on the subject along the way.

I hated school – and was a terrible student throughout most of it –, yet I love to learn. This doesn’t make sense. Teachers should not teach – they should inspire their students to learn, instilling curiosity and holding their hand through the discovery process.

While angel investors and early-stage venture capitalists invest pre-revenue or sometimes even pre-product, university admissions officers are the true early-stage investors: they invest pre-idea! When you think about it, it’s actually striking how similar admissions officers are to VCs: they invest in people, they (the university) hope for large returns in the future (by way of donations), it’s an expensive investment on both sides, and a stamp of approval and access to the network of a cream of the crop ‘investor’ is highly valuable.

As much as I bash universities for not providing the right educational experience for students and allowing enough room for experimentation – most of my learning definitely happened outside of the classroom –, there is no denying that my Harvard diploma has opened doors that would have been a lot harder to maneuver into without. That stamp of approval – similar to an investment from Kleiner or Sequoia – has made it a lot easier for people to have faith in me at a young age.  And of course, my peer-group at the universities I’ve attended has also been a huge factor in my success. 

Are universities paying enough attention to who they hire as admissions officers? Probably not: it’s not exactly the most prestigious and sought-after employment position, and I’m sure it does not pay anywhere near what a venture firm pays. As a result, the people they hire are not anything like the world-changing rock stars they should aspire to admit. A similar argument can, should, and has been made for teachers, but this seems like a much easier issue for universities to fix - an issue that directly affects their top line.

When I say ‘fix,’ I mean universities should hire admissions offers good enough to identify passion, creativity, tenacity, and a big vision, without simply relying on easily-gamed, non-representative indicators like GPAs, standardized test scores, club memberships, and application essays. Wake up, Harvard - you’re hiring poor investors and it’s going to hurt when you’re the last one in the room to figure that out.