Thinking About Thinking

Don’t Teach Kids To Play Music, Teach Them To Love Music

Posted in Philosophy, Pop Culture by larrycheng on July 29, 2009

My favorite part of the TEDx Boston event yesterday was the themelet on music.  There were three musical performances all involving the younger generation topped off by the Youth Orchestra of the Americas (YOA) led by Benjamin Zander.  I don’t think it’s humanly possible to love classical music more than Benjamin Zander – he’s infectious.

Benjamin Zander’s presentation of music made me think about my own personal musical journey.  As a child, music came quite easily for me – both the piano and the violin.  Once my parents saw that I had some proficiency in music, they sacrificed a lot of time and money to get me great teaching and equipment.  I practiced a fair amount and learned to play a number of the great works by Beethoven, Bach, Mozart, Chopin, etc.  And, at a young age, I even started competing.  Despite my improving capabilities, there was one major flaw in the whole program.  I never really fell in love with music – and that would ultimately be the limiting factor. 

There was a brief moment in my short music career where I could have really fallen for music.  For a few weeks, I got to take a break from classical music and had the chance to try my hand at jazz piano.  What’s unique about jazz is in its truest form, it’s about improvisation.  You don’t play jazz off of sheet music – it comes from within yourself.  I learned that for me, playing the notes on a page of sheet music was not playing music at all.  Ironically, it wasn’t until I threw away the notes, that I really started to feel like I was playing music.  Playing other people’s music was all well and good, but I had the best time making my own.  I always wondered if my brief flirtation with jazz had lasted longer, if I would have ultimately come to love music. 

I have always carried a broader lesson with me from this experience: it’s one thing to be good at something – it’s entirely another thing to be good at something and to also love it.  Anyone know a good jazz teacher? 

Missionary CEOs v. Mercenary CEOs

Posted in Philosophy, Venture Capital by larrycheng on July 27, 2009

I have always had an affinity for a particular “type” of CEO.  I never really bothered to try and define this “type” – I just knew it when I saw it.  Until last year, in an board meeting, Jeff Bezos articulated the framework that captured my sentiments better than I could myself.  He called it: “missionary CEOs v. mercenary CEOs”.  If I had to oversimplify this framework I’d say that missionary CEOs are principally about the mission and mercenary CEOs are principally about the money.  If you met the CEOs of my portfolio companies, you’d find one missionary after another.  Watching Jeff Bezos’ recent video to Zappos reminded me of this nugget of wisdom and reminded me that Jeff is perhaps the perfect example of a missionary CEO.

Jeff’s wisdom notwithstanding, I do not believe that he coined this framework.  After some research, I think he probably heard it from one of his venture investors – John Doerr of Kleiner Perkins who adapted it from The Monk and the Riddle, by Randy Comisar.  Here is John Doerr speaking at Stanford in 2005 articulating how Kleiner views the difference between missionary CEOs and mercenary CEOs.

Over this past year, I have come to appreciate why you invest in missionary CEOs.  Despite one of the most challenging economic times in a century, all of my CEOs exhibited incredible leadership, drive, and passion through thick and thin.  In the darkest moments of this past year, they all demonstrated unwavering commitment and enthusiasm that carried their companies through.  While I don’t know what the future holds for these companies or for the economy, I do know that I am very proud to be associated with each and every one of my CEOs.  They are all great leaders and even better people – worthy of being called missionary CEOs.

[Another piece of wisdom from Jeff Bezos:  How Can We Double Down?]

The Most Innovative and Impactful (Emerging) Charities

Posted in Pop Culture by larrycheng on July 21, 2009

Every day I meet for-profit companies that are trying to change the world by solving really big problems with groundbreaking innovations.  Today I asked my twitter friends which non-profits or charities are following suit.  Just like my day job, I am especially interested in charities that may be emerging or somewhat under the radar.  Following is a running list of what I heard (and who referred it).  In alphabetical order:

  1. ACCESS– helping Boston youth achieve higher education.
  2. Acumen Fund – building businesses to solve poverty. (brandonhaskins)
  3. Alley Cat Allies – improving the lives of cats.
  4. CharityWater – bringing clean water to developing nations. (brandonhaskins)
  5. CommonImpact – building stronger communities. (fyietc)
  6. – funding projects for teachers. (BrettTopche)
  7. Facing History – link the past to moral choices today. (bussgang)
  8. Generations Inc – intergenerational outreach.
  9. Global Poverty Project – helping those in extreme poverty. (robtrotter)
  10. Green Light Fund – helping urban families in Boston.  (Polachi_Co)
  11. Idealist – global clearinghouse of nonprofit resources. (fyietc)
  12. Jumpstart – building vital skills in children.
  13. Kiva – loans that change lives.  (Danielmsullivan)
  14. Mass Mentoring – youth mentoring in Massachussetts.
  15. MobileActive – using mobile phones for social good. (fyietc)
  16. – helping low-income households with emergencies.
  17. NetSquared – remixing the web for social change. (fyietc)
  18. Oaktree Foundation – youth-run development organization. (robtrotter)
  19. Pratham USA – imagine India where every child can read.
  20. Restavek Freedom – putting an end to child slavery in Haiti.
  21. RootCause – supporting social innovators. (fyietc)
  22. Servings – bringing meals to the critically ill and homebound. (LyndonMouton)
  23. SocialActions – open source database of social actions. (fyietc)
  24. Teach for America – national teacher corps. (aseidman)
  25. Ushahidi – crowdsourcing crisis management (justindavey)
  26. WorldChanging – environmental media organization. (fyietc)
  27. Year Up – empowering urban talent.

(If anyone has other ideas, please leave a comment or tweet me and I will update the list.)

What Happens To Copyright?

Posted in Pop Culture, Technology by larrycheng on July 20, 2009

I have been thinking a bit lately about the tension between copyright law and the proliferation of self-publishing online.  How do you protect your copyright when any work can be copied or transcribed within a second of its unveiling and published around the world by any average Joe with a cell phone and a twitter account?  It’s a question I’ve been asking without clear answers so far (but would love to hear your thoughts).

Check out what the US Copyright Office says copyright law protects: “original works of authorship including literary, dramatic, musical, and artistic works, such as poetry, novels, movies, songs, computer software, and architecture.”  Stop and think about the level of technology disruption and subsequent business model innovation in some of the areas listed – music, movies, books, software, etc.  If you want to find industries rich with innovation – you could just pick the industries that the US Copyright Office is trying to protect and go from there.

I wonder what copyright law will look like and how it will be used 10–20 years from now.  Right now, each industry and each author has to decide how they will react to technologies that are seemingly threatening their core asset.  It seems there are two broad options – (1) try to protect your work under copyright law as you always have or (2) embrace technology and adjust your model.  History seems to suggest that banking on #1 is an uphill battle because you’re on the wrong side of technology innovation – just ask the RIAA (Recording Industry Association of America).  Option #2 requires vision and courage to change your industry by leaving old models behind.

Another way to put decision matrix for authors is: do you want to own the content or do you want to own the community?  If you want to own the content, you protect it with all your might.  If you want to own the community, you may need to put your content out there and let people around the world engage with it (a great example of this in education is MIT Open Courseware).  Both are legitimate options.  But, one possible ironic consequence of pursuing the second option is that by giving away or opening up your content, you may end up inheriting more valuable content which is the feedback and engagement of the broader community.  In effect, you might just give up one asset to create one that is far more valuable.

Bob – The 93-Year Old National Sprint Champion

Posted in Pop Culture by larrycheng on July 19, 2009

Today, I ran in the New England Masters Track and Field Championships in Cranston, RI.  It was really fulfilling to get back out and compete in a track meet.  Despite doing pretty well myself, the clear highlight of the event for me was watching Bob run.  Bob ran the 100M, 200M, 400M and 800M races.  Bob is not your average runner – he is 93–years old and is a national champion in several sprint events for the 90+ age bracket.  Here is a video of Bob finishing the final stretch of the 800M race (immediately after which he lined up for the 200M).  Bob, you are my hero.

The Learning Test

Posted in Philosophy, Pop Culture by larrycheng on July 16, 2009

I have found that there’s a simple test for whether you are learning in your career.  Look back 3–5 years from today and ask yourself if you could have been substantially more effective at your past job in your present form.  If you look back a few years and feel like in comparison to who you are today, you had little idea of what you were doing and would have done things a lot differently given what you now know, that’s a telltale sign of learning and growth. 

I have been in the venture business 11 years now, and whenever I look back even a few years, I feel like I was pretty clueless.  Now, it’s not to say that I was actually clueless (though perhaps some of my partners or CEOs would disagree!), but  the differential is just a testament to the slope of the learning curve that takes place every day, month, and year in this business.  I was sharing this with Mitch Free, founder and CEO,, and he said that he feels that way in all the important things in life.  After thinking about that, I have to agree. 

I used to think that looking back and feeling like you’ve made so many mistakes is not such a great thing.  Now I’ve come to believe that the thing to really be worried about is looking back a few years and being impressed with your past self.  If that were to happen, it probably means your learning has stalled altogether. 


Prosper Marketplace: Changing The World

Posted in Venture Capital by larrycheng on July 13, 2009

It is with great pride that I congratulate Prosper Marketplace on successfully completing their SEC registration process pioneering the first true auction marketplace for person-to-person lending (Prosper’s blog post). 

At the highest level, I believe this ushers in a fundamentally new model for auctioning all kinds of securities that will lead to tremendous innovation in the 21st century.  For Prosper, it is great to be back in business after a long quiet period working with the SEC (when we stopped lending).  Before the quiet period, we were growing at a torrid pace having enabled $178 million in loans to transact between millions of individuals in the United States.  Needless to say, we are excited to be back in business and back to the aid of consumers during this difficult financial time.  I would like to thank the SEC for working closely with Prosper and embracing innovation as regulators.

I am personally pleased to see Prosper back up and running because my Prosper portfolio was my top performing asset in 2008.  While economists agree that virtually every asset class excluding gold declined materially in 2008 – stocks, bonds, real estate, etc. – they missed one asset class: person-to-person lending.  I leant to Americans, and they paid me back reliably even during the downturn.  It seems every other day I get an email from Prosper saying those magic words: “One of your notes is paid in full”.  And now it gets even better.  Thanks to the SEC’s blessing, Prosper has now enabled lenders to re-sell existing notes to other buyers through a secondary market giving instant liquidity.  It’s a beautiful thing.

Finally, I would like to thank the Prosper management team and in particular Chris Larsen, founder and CEO.  When we invested in Prosper before the company launched, we thought Prosper had the potential to change the world.  We also knew we were trying to do something so audacious and so big, that there would be ups and downs along the way.  We have certainly had ups.  We have had some downs.  But, today, we are one big step closer to changing the world.  Congratulations.