40 posts tagged HB

I started working at Tumblr the day after I graduated in May 2009.  It’s been a remarkable year - I learned more than I did in four years of college, met brilliant and talented people, and was given an incredible opportunity doing business development at one of the hottest startups out there.

I’ve always had a proclivity to stray from the common path.  Whether it was leading bands in high school, managing a digital and print publication throughout college, or running a music marketing and production company, entrepreneurship is in my blood. With a problem-solving idea, a brilliant co-founder, and a whole lot of luck, I’m off to launch my own startup (more news on that end coming soon, but for now visit http://GroupMe.com or go follow our Tumblr or Twitter).

I have a whole lot to be thankful for.  For one, the whole Tumblr team has been wonderfully supportive.  A big thank you to John Maloney who took a random chance on a college grad, showed him the ropes, and mentored me all the way through. Another big thank you to David and Marco who have been nothing but supportive and helpful over the past month.  I’m also indebted to all those who have helped make this possible: my friends, co-workers, new acquaintances, family (who has encouraged and been with me through thick and thin), and Carrie - my better half who keeps me going everyday.

Stay tuned for updates on all things GroupMe - I’ll have a big post on that coming soon. Exciting times to come.

Jeff Bussgang’s recent book Mastering the VC Game is a must read for anyone interested in the startup or venture capital world.  It’s quick, fun, and packed with gems of advice and anecdotes from successful entrepreneurs and VCs.

Bussgang is an entrepreneur turned VC.  He’s seen both sides of the table and the book reflects that.  It’s unbiased and reads truthful.  Bussgang is able to paint an honest picture of what raising capital and investing capital is like for all parties involved.   

I learned a lot about VC that I didn’t know before - the different types of shares and their implications for VCs and companies, pre and post money evaluation mechanisms, protective measures against dilution, and the underlying incentives and driving forces behind VC investments.  

The book is a primer for educating entrepreneurs about what it’s like from the other side and how to approach relationships with investors.  It’s just the right amount academic and sugar coated with stories from Jack Dorsey, Reid Hoffman, Fred Wilson and various other esteemed and successful entrepreneurs and investors.

If you’re at all interested in startups and VC, or you just want to learn a bit more about how this world works, then this is the right book.  

I recently deactivated my old Facebook account and started the service anew.  I’ll report back on my experience shortly, but I wanted to touch on something that I found disturbing: Facebook’s deactivation practices.

I consider myself a relatively tech-savvy person.  I’m capable of using and understanding most online services.  When I deactivated my Facebook account, I assumed I was permanently deleting it.  However, deactivating is much different than deleting.  In fact, it’s difficult to find any page about deleting your account on Facebook. If you don’t know what you’re looking for, you’ll be pointed to the deactivation page - and that’s exactly what Facebook wants. 

I think it’s safe to assume that the average user confuses deactivation with deletion. When deactivating an account, most people are under the impression that it deletes their profile and all the data that goes along with it (pictures, applications, notes, events, etc.).  This is definitely not the case.  This is the message you get after deactivation:

This is the softest deletion I’ve seen from any service, and it’s a piss poor practice.  It’s intentionally misleading and deceptive.  I’d imagine a lot of people get to this point happily thinking they’ve erased whatever trail they left on the service.  This is not the case at all.  To “reactivate” all you need to do is type in your old email address and password (which will be automatically stored in the login bar the next time you go to Facebook’s homepage - you won’t have to type in anything, just press “Enter” and voilá! you’re back to where you left off).

It’s obviously a strategic move on behalf of Facebook.  They don’t want users or user data leaving the service. But this is a shitty practice on their part.  If you actually want to delete your account, you’ll end up scouring through their FAQs.  It’s buried.  The only thing the average user, or even a mildly tech savvy user will intuitively find, is the deactivation page.  It’s easy to access and it’s right where you’d expect it to be.

So what’s my gripe?  Clearly Facebook is deceiving users into deactivating accounts instead of deleting them.  All services should give you a clear and transparent way out - it’s good practice and it establishes trust with users.  For all the contentious privacy issues on Facebook’s plate, they should really think about the way they present deactivation vs. deletion.  For a service I share so many aspects of my life with, the last thing I want is to feel duped.  

This is a story about chess, childhood, growing up, and the things that happen in between.

When I was in the 6th grade I was a competitive chess player.  I’d fly all around the country playing in tournaments.  My life was something straight out of Searching for Bobby Fischer, but a little more intense and a lot more real.  In 1999 I was playing in the national championship tournament.  I started the tournament on Board 5 (equivalent to 5th seed), and drew to a lower rated player in the 4th of 7 seven rounds (he was in the 1400 range and I was in the 16/1700 range at the time, if I remember correctly).  I ended up winning nationals that year with a score of 6.5 out of 7, and the person I drew to in the 4th round tied for second place.

As silly as it may seem, winning nationals has always been one of the proudest achievements of my life.  It’s nice to have something under my belt that no one can take away from me.  Sometimes I think about what would have happened if I hadn’t drawn that match early on in the tournament.  Would I have still won?  Would I have lost?  Would I still be me?  Who knows.  All I know is that I stopped playing competitively shortly thereafter and I was okay with that.  By the time I retired I had played against Hikaru Nakamura, hustled the hustlers in Washington Square Park, met most of my chess idols, and fulfilled my chess dreams.  My chess career peaked at the age of 13.  All things considered, that was probably a good thing.

Fast forward ten years to April 2010.

Several weeks ago I was toying around on LinkedIn and stumbled upon a familiar name: Josh Weinstein.  I scoped out his profile and sure enough it was the same Josh Weinstein I drew to in the 4th round of nationals a decade earlier.  I was pleasantly surprised to learn that Josh had gone on to do some great things himself.  He became the National Speed Chess Champion, the student body president at Princeton, and the founder and CEO of a company I admire called GoodCrush.  He also ended up in the NYC startup scene, and we now work walking distance from one another.

I shot him a note saying, “Pretty sure we played each other at nationals.”  He immediately responded with “Pretty sure you won.”  And that was that.  We got lunch the next day and hit it off.  It was as if the past ten years hadn’t existed and we just finished a marathon series of post-nationals blitz games.  Josh has come a very long way since the 6th grade and it’s great to see him doing so well.

This week Josh and I went over to Shake Shack to grab some lunch.  When we were waiting for food I asked him when we were going to play chess again.  ”e4!” he said. The last game of chess I played in my head was over ten years ago, sitting next to my chess coach at a friend’s Bar Mitzvah.  The way mental chess works is you say your moves out loud and play the entire game in your head.  There is no physical chess board, only an image of it and the pieces in your brain. You either play the all the way through, or the first person to make an illegal move loses (this usually happens before someone is checkmated).  The last time I played, my coach made an illegal move around 15 moves into the game.  I held bragging rights after that.  Damn that felt good.

“e6,” I replied.  Four moves later we were playing a variation of the French Defense. Much to my surprise I could still do it.  My mind was still sharp and my ability to visualize the board was still there. (Unfortunately, my knowledge of openings has completely deteriorated.)  We sat down for lunch a couple moves into the game and postponed it.  

On the way back to work we picked up the game via text message - still no board. The image of the pieces remained fresh in my head.  For the rest of the day we continued to sporadically exchange text messages with our moves - sometimes with 2-3 hour breaks - but we never lost sight of the position.  Finally, walking home from work, I offered Josh a draw.  I was down two pawns entering the endgame (clearly a losing position).  He texted back, “Why the hell would I take a draw?”  I told him to accept it for old time’s sake to which he responded with a big fat “LOL”.  I took that as a polite “yes” and the game was over.* 

Some things stick with you for a lifetime.  It’s nice to sit back and appreciate the way things work out. 

*If you’re interested, I wrote out the game below - it’s not an exciting one by any means, but I’m thrilled that I can still visualize a game of chess.  Josh played white.  I played black.

1. e4, e6 2. d4, d5 3. Nc3, Bb4 4. Nge2, c5 5. ed5,  ed5 6. a3,   Bxc3 7. Nxc3, c4 8. Qf3, Be6 9. Bd2,  Nf6 10. Bg5,  Nbd7 11. 0-0-0,  0-0 12. h3,   a6 13. Bxc4, dc4 14. d5, Bxd5 15. Nxd5, Qa5 16. Bxf6, Nxf6 17. Nf6+, gf6 18. Qxf6, Rad8 19. Kb1,  c3 20. Rxd8, Rxd8 21. Qxc3, Qxc3 22. bc3,  Rd2 23. Rf1 DRAW

For the past two years I’ve had my privacy settings on Facebook set to maximum.  No one sees my photos, no one can comment on my wall, and if we’re not already friends, chances are you won’t be able to find me.  I did this for many reasons, one of which was privacy.

I’ve lost interest in Facebook.  I get no pleasure out of my News Feed.  It’s spammy, uninteresting, and filled with photos and mundane comments from people I’m not really friends with.  Over the past six years I’ve accumulated so many “Friends” I don’t even know who a majority of them are anymore.  

I remember the golden days when it was a quality service - when I actually enjoyed spending time on it, communicating with new and old friends, and sharing photos and updates.  Unfortunately, the satisfaction I used to get from Facebook is long gone. 

I’m going on a mission to see if I can make Facebook meaningful again.  As of yesterday, I began to back up my account with Backupify.  I backed up my photos (there were some gems in there from years past) and my friends (just so I have a list to start from when I restart).  I’m going to completely delete my current account and begin anew, befriending only people I am friends with in real life who I feel comfortable sharing photos, updates, and exchanges.  I’ll set my privacy settings so I’ll be open amongst my real friends, but unavailable to outsiders - aka the way Facebook used to be.

I’m on a mission to see if I can make Facebook work for me again.  I’d like to think it’s possible, but I’m a bit skeptical.  These rather large hiccups with privacy issues are discouraging to say the least.  Either way, I’m open to give it another shot before I turn it off and say good night.  I’ll be documenting the whole experience.  Hopefully it helps myself and others learn a bit more about The Facebook.

I’m putting down The Big Short and moving on to Mastering the VC Game.  I’ve had a difficult time getting into The Big Short so it’s time to move on, but something about leaving a book unfinished makes me uneasy.  Oh well, maybe I’ll get back to it one day.

John Mayer’s recent post and David’s response got me thinking about comments.

Comments are a highly contested subject.  You’ll find some people out there who utterly despise them, and you’ll find others who believe they’re an integral part of the web.  Both arguments have merit.  The issue isn’t whether or not comments are a good or bad, it’s whether they add relevant and meaningful contributions to a topic. 

Let’s take a look at two blogs at opposite ends of the spectrum: AVC and Marco.org. 

AVC is Fred Wilson’s blog. Fred has enabled Disqus on his site, a powerful tool for empowering comments and conversation, and as a result has spawned a community of dedicated readers.  Most of his posts have anywhere from 200-300 comments.  That’s a shit load.  Fred has even argued that the real value of his posts are in the comment section (forgive me, I can’t find the exact link).  If you read through the comments on his blog, you’ll notice that there is seldom any negativity.  Almost all of the conversation is productive and engaging.  Sometimes there’s some name-calling, but overall it’s remarkably civilized and informative.  For Fred’s blog, comments are a positive, value-added service. 

Marco.org is a blog written by my co-worker, Marco Arment, where he waxes poetic on all things Apple, internet, and sometimes politics.  Marco is not a fan of commenting. You need look no further than a couple of his posts to know his thoughts on the matter. Comments are the dregs of the internet.  For proof look at any Youtube comment thread.  They’re negative, vile, and add no value to anything. Marco’s blog does not permit commenting.  It doesn’t even display the Tumblr note count (which isn’t negative by any means - if anything it reinforces the popularity of his posts). Marco’s lack of comments doesn’t preclude the popularity and stickiness of his blog.  In fact, you could argue that it makes it even more attractive.  It’s his own space for his own opinions - not yours - and people clearly like and want that.  (Daring Fireball is another good example of a no-comment medium.)

Fred and Marco provide a perfect example of how comments, or lack thereof, can be both good and bad. They’re both right.  I’m in the camp that comments are a good thing, but they should never be mandatory or forced upon you.  I love the way Tumblr approaches comments (I’m admittedly biased).  We have no built-in commenting system and I don’t see any reason why we ever would have one. John Mayer laid it out succintly:

This is where Tumblr comes in. It’s the future of social networking if your image of the future features intelligent discourse. I love reading other Tumblr users replies, because they’re thoughtful by virtue of the fact that if they’re not, they’ll bring the intellectual property value of their own blog down, and that’s a commodity on Tumblr.

And David’s response was right on point:

After three years at this, I can’t begin to describe the feeling of having this philosophy — the reason Tumblr will never feature a legacy comment system — described so perfectly.

Everyone is entitled to a place where they can share their ideas without criticism.  A space where they can curate, create, and broadcast the things that are representative of who they are.  I believe that Tumblr is the platform for this type of expression and social engagement. 

Like I mentioned before, I’m not a believer that comments are an inherently bad thing. There’s a time and a place for them and they should always be an opt-in feature.  I’ve enabled Disqus on my blog because 1) I think it’s a fantastic application and 2) I enjoy reading people’s comments and conversing with them.  Most of my posts don’t even receive comments, but I always have fun with the ones that do and do my best to respond to everyone’s contribution.  I’d say that 90% of the comments I’ve received thus far have been positive, meaningful, and taught me something fun and new.  

But that’s just me.  There’s no finite answer here - it’s just a matter of opinion. Collaboration, community, and conversation vs. one person’s opinion.   I’m curious to hear what others think about the matter - there’s a big grey area here which begs to be debated.