“Do you know where we are?” asked Milo.

“Certainly,” he replied, “we’re right here on this very spot. Besides, being lost is never a matter of not knowing where you are; it's a matter of not knowing where you aren't – and I don’t care at all about where I’m not."

Breaking Rules

I’ve always enjoyed breaking rules. 

I received poor grades throughout most of my early schooling, not because I couldn’t do the assignments, but because I didn’t really care. And this disregard for the authoritarian nature of school affected my extracurricular activates as well: in eighth grade I vividly remember being suspended (and almost arrested) for climbing on the roof of the school building with some friends one night – during a school board meeting. And in ninth or tenth grade I believe I became the first student in my high school to get kicked out of prayer indefinitely. The list goes on.

In retrospect, despite all the hair-pulling, yelling, and fighting with my parents, teachers, and others, it was all well worthwhile. Pushing boundaries, often pretty successfully, gave me a perspective and confidence that most other kids my age didn’t have.

Since high school, my disdain for rules and authority has taken an interesting turn: it has evolved into a profound appreciation.  It’s not that I respect authority any more than I used to – much to the contrary –, but I’ve come to realize that having a deep understanding of rules makes breaking them so much more enjoyable.  In graphic design, understanding how to construct a grid, and subsequently break it, is both deeply satisfying and generally creates a much greater communicative effect.  In writing, closely following. And then breaking. Grammatical rules can lead to a beautiful amplification of your point.

So be obedient and learn the rules. If for no other reason than to better break them.

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Don’t Go To Business School

I strongly believe that today, business school – even at the best institutions – is a complete waste of time and money for anyone with a bit of self-motivation. It’s not that the material is totally useless – though it has changed little in the past 100 years and is now largely available for free online –, but relative to the significant cost it’s just not worth it.

Here are some of the common arguments for business school:

  • It’s a great networking opportunity. Yes, if you attend a prestigious business school you will meet and bond with lots of other people interested in business who managed to get high scores on their entrance exams. Sweet! But there are plenty of other great ways to meet amazing people (who didn’t just pass a test and write a good essay). They include: joining a group / club or similar in an area that you’re interested in, going to local events, cold-emailing / tweeting / messaging people you admire to ask if you can take them out for a coffee, etc. I don’t believe the GMAT – or any standardized test for that matter – is at all a good indicator of intelligence or future probability of success. And it is definitely not an indicator that someone will be fun to hang out with.  A majority of the most incredible people I’ve met have come from just being involved with the startup community.
  • I want to learn from the best professors. Read their books. Most of the professors at these schools – especially the best ones – have published their insights long ago. Ever heard of The Innovator’s Dilemma by Clayton Christensen? How about anything by Michael Porter? Google any famous b-school professor and you’ll find most everything you need. 
  • I want to learn finance, excel, [fill in the blank]. Read a book, use Investopedia, or some other online resource. It’s much cheaper, you can go at your own pace, and most of the classes in business school will just have you read them anyway.
  • The ‘case method’ teaches you about tons of businesses in a short period of time. I’m sorry, but reading and discussing a situation is no where close to actually learning about these situations, businesses, and industries, and how to make decisions in a constantly-shifting, pressure-filled environment.  The only way to do that is by actually doing it. If you want exposure to a lot of different business models or sectors, start or join a company that will give you that level of exposure. Also, do you really think that a former CEO, when being interviewed for a b-school case, is going to tell the interviewer the real reason he made the decision to sell the company was because he was cheating on his wife and he wanted to bury the returns offshore before the divorce?
  • It’s a signal for my current / future employer. Why not try to accomplish something that actually proves you’re intelligent / competent / hard-working, etc?  If you’re in sales, show how amazing you are by selling!  If you’re an engineer or designer, make something beautiful and post it online for all to see.  Putting an ‘MBA’ on your resume is a poor replacement for accomplishment.
  • I want to change jobs. This is the most acceptable reason in my mind, but do you really need to spend that kind of money for a certificate and a job fair? Why not spend the time learning about the space, attending local events you care about, and reaching out to people at companies you’re interested to grab a coffee and chat. If they’re not interested in you, try making yourself interesting by learning everything you can about the space and publishing your thoughts on what you’ve learned online (in a blog, on Twitter, on Facebook, etc).
  • I want to learn from / work with bright people (my classmates). This, I respect.If you’re not already at a company where this is possible, consider changing jobs. There are many incredible startups hiring right now. If you think a masters program is the best / easiest way to do this though, consider doing a program where a) you’re learning real skills, and b) you’re collaborating with people very different from yourself, who really bring unique / new ideas to the table.  If I ever do another degree, it will probably be at a design school where I get to actually make stuff and learn things from others that I can’t simply by reading an article online or in conversation with a friend.
  • It’s free (my company is paying for it / I have a scholarship). If you have a scholarship with no strings attached, great. But be sure to consider whether this is the best way to spend the next year or two of your life. If your company is paying, there are generally pretty significant strings attached (a commitment to work for them for the next few years).  Be careful about this.  It may sound great, but I think the gain is tiny relative to what you’re giving up in personal freedom.
  • It’s fun! I can think of many better ways to spend that kind of money on a fun experience. Why not travel? Or pay someone incredible to apprentice under them for some period of time? 

To be clear, I’m not stating that business school is inherently evil, I just think people should be more aware of what they’re getting for the time and money spent. And I think there are definitely better ways to spend both.

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Goals for 2012

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.

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Lessons Learned in VC

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).

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Act II: Enterpoid

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.

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Juventas Fugit  is designed and written by Justin Wohlstadter, who, when not writing in the third person, can be found in a coffee shop talking about startups, thinking about the future of education, and generally procrastinating something important.

  • Passions: startups that positively affect the world, education innovation, good design, learning, and meeting those with an equally insatiable curiosity.
  • Play: director of product design at Enterproid and partner at BOLDstart Ventures.
  • Previously: built the early-stage venture arm of Penny Black. And many other crazy, less successful ventures involving fire extinguishers, measuring philanthropic impact, and creative spaces.
  • Pedantry: most of the important stuff I taught myself or learned from friends, but I’m fortunate to have (barely received) degrees from Harvard and Oxford. At Oxford I wrote my dissertation on how internet innovation will disrupt access to higher education.
  • Procrastination: can be found on Twitter, Linkedin, AngelList and other web spaces, and be reached via email at my first name at this domain.
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