Why I went to Business School

People never stopped asking me why I went to business school. I was too old, too senior and in the wrong career track. “What jobs do you think it will help you get?” they would ask. When framed that way, there was no good answer.

There are a number of reasons:

  • Even though I was succeeding at Microsoft, I knew I had to leave. I looked ten years down the road and didn’t like what I saw: VP of something not so interesting; products I was no longer proud of; master political infighter. There were and are signs of life (Bing!) but it seemed like a long grey road ahead. But leaving for “nothing” seemed unpalatable. Leaving for Harvard was somehow easier to talk myself into.
  • I had spent 4 years heads-down on a media battle that I could now see Microsoft was going to lose and lose badly. The XBOX Live Video Marketplace is a big success in four years otherwise spent trying to make water run up hill. I’d spent too much time on politics – begging the Windows Media Player team to support some feature or another (and them lobbying me).  I’d given up a lot of personal stuff to work so hard for those four years (and there’d been payoffs career-wise) but I wanted to surface, to have fun, to interact with the world, to live.
  • My father had been dying for 5 years. I applied and was accepted before he died but it was obvious where things were going.  I felt like I needed some air – some time and space to get away and come to grips with things. Business school felt arguably more additive than surfing in Thailand for a year.
  • I felt like I knew a lot about a very narrow slice of the world. I could specify software for media really well and I was a good manager. But I just had a sense that there’s so much more out there – and on this Harvard does a great job of exposing you. I spent 2 years learning and talking about airlines and food processing companies, about factories, about sports management, about consulting companies, about politics and about finance. I also made friends from crazy places, out of the way amazing places: Brazil, Belarus, Zaire, rural China, Sweden. I feel like I know a thing or two about macroeconomics and finance and accounting and about a million other things. On this front, Harvard delivered brilliantly.
  • I wanted to be inspired by the people around me again. There was a time when Microsoft hired the brilliant and fiery college kids, the savant programmers, the ambitious drivers. Occasionally they still do (and I’d like to think I hired a few of them) but for the most part, those days are gone. There are still some of those people around but for the most part they are rich, they reflect on past glory and they leave early enough to catch their daughter’s softball game. (Which is a perfectly rational thing if that’s where you are – it’s just that I am not.) Every time someone talked about how comprehensive the healthcare plan was as a reason for staying, I felt like an idiot.
  • If I’m being honest with myself, I thought school might offer opportunities romantically. Whether it did or not, I did not capitalize on them. For the answers to that one, look within.

All things considered, I wouldn’t change a thing (except maybe the huge bill.)


Minsk Wedding

I just got back from a friend’s wedding in Minsk. There were a bunch of awesome sounding weddings this season and I usually make a point of going to all the weddings I’m invited to, but given my new career situation (which I’ll be ready to talk about soon) I’ve unfortunately needed to conserve both the time and money. There’s always an exception to the rule though and my friends Paul and Jenia’s wedding in Minsk was somthing I just couldn’t miss. Highlights:

  • Yes you really can consume an entire bottle of vodka on your own and not die. You just want to.
  • There is a cured meat there that is basically just the fatty part of the bacon with all the meat part cut away. Amazing.
  • Belarussian nightclubs. Wow. We went three nights in a row.
  • The “purchase of the bride” – a Belarussian tradition where the groom and friends must convince the bride’s friends to let her go with bribes of chocolates, singing, champagne and cash. We had stacks of 10 ruble notes (worth about 1/3 of a penny.)
  • Simultaneous English / Russian / Belarussian translation of the speeches at the wedding so everybody could understand. It certainly makes for short speeches.
  • There were 17 nationalities represented at the wedding. (And that doesn’t include cheating ones like “Texas”) An amazing, awesome group of folks.
  • The younger sister of the bride (who speaks both Belarussian and English) gave a very different speech in Belarussian that her family could understand than she gave to the invited English speaking guests. I won’t reproduce it here but it was classic.
  • Belarussian singing / dancing / cover-band. You really haven’t heard Guns ‘ N ‘ Roses until you’ve heard the Belarussian cover.
  • Being beaten by birch branches in the Sauna the day after the wedding. Really the whole sauna experience which involved ice cold water, scalding sauna, absolutely ridiculous hats and of course – more cured meats.
  • Going to see Swan Lake the day after the wedding at the Belarussian Ballet. (Yes mom, I really went to the Ballet!)
  • And of course – the absolutely amazing and cool friends I met there. The only thing I find sad about weddings is at the end knowing that this group of people will probably never assemble again. As I was leaving I had the urge to tell people, “See you at the Christening.”

Summer in San Francisco

Some times are so great, you can tell that they are among the best times of your life even while you’re having them. For me, this summer was one of those times. I spent the summer living in San Francisco, doing exactly what I’d hoped: working in VC, reading business plans, meeting with entrepreneurs, doing due diligence and generally learning the business. I also managed to find quite a bit of time to reconnect with old friends, work out in the mornings, ride my motorcycle into the hills and do a little traveling.

I’m now back at school for one last stretch of classes, but like MacArthur in the Pacific, I shall return!

San Francisco Bound

Today I’m heading out to San Francisco for the summer. I’m going to be working for a VC fund. I’ve already done some work with them and I’m super excited. They’re super smart, have a great track-record and seem like a ton of fun.

I’m also pretty excited to move back to San Francisco. I haven’t lived there since Dec. 2001, so this is kind of a homecoming for me. I think there’s a very good likelihood that I’ll be moving to SF permanently when school is finished in a year, so this is an auspicious start. I’ll be living in the apt. of an old friend from Echo Networks. I haven’t seen it yet, but it sounds awesome and the few photos I’ve seen look great as well. I’ve also shipped my motorcycle (an 1989 Honda Hawk GT 650 in case you’re wondering) down from storage in Seattle.

So if you’re in SF this summer or plan to be there or would like to plan to be there, please drop me a line. I’d love to catch up with old friends.

“We are the ones we’ve been waiting for”

If you haven’t seen them, you really must check out the two videos that will.i.am (of the Black Eyed Peas) created about Barack Obama. They both make the hair stand up on the back of my neck.

Doesn’t some part of you still believe that there are special moments in the world? Special people who catalyze and give a voice to a feeling that has been quietly building for years? When Kennedy pointed at the moon, when MLK stood on the steps of the Lincoln memorial, when Reagan talked about morning in America – didn’t these people shift the world around them just a little bit? Didn’t the right speech at the right time change you and how you saw the world? We all have our own: words, written and spoken that for some private reason moved us.

Today is the day where it could be made real. Today could be the day where we know this is really happening. Barack Obama did not grow up in the sixties. He was not shaped by Vietnam or Watergate. He did not come out of the same cohort of boomers that have run our country for so long. Those who scoff, who say that his difference is exaggerated do not understand how differently the world will see us if this man, this bi-racial man with an African father is the man we pick to be our president. How inherently different his perspective has to be. Louder than any policy this would say to the world that we have changed. We know we have made mistakes over the last 8 years (and longer) and there are more we will make but we have changed.

If you need evidence of his leadership, look to the way he has run his campaign – without turnover, without dirty laundry aired in public; just quiet competence. When did we become a nation that looked to time served? Inexperience did not stop Bill Gates or Steve Jobs or Marc Andreesen.

To those who say that this is all just foolishness, that this optimism is just naiveté, that this will all be dashed on the rocks of bitterness and hardball, that what we really need is someone adept with a switchblade and a bank of favors (and there are many I respect who think so) I say maybe you’re right. Maybe tomorrow I’ll know you’re right. But today – like Fox Mulder – I want to believe.


There was a blizzard in Boston yesterday and cabs were impossible to find. A friend of mine was trying to get across town to meet me and a few others at a bar, but he couldn’t find a cab. So he walked down the street to a pizza place and ordered a pizza for delivery to the address of the bar. When the pizza was ready, he asked the driver if for a 50% tip, the driver would let him ride with him to where the pizza was going. The driver said no problem and everyone made out happy; even me, who got some pizza out of the deal…


Those of you who haven’t talked to me in a while may not know that I’m currently at business school, going to class, doing homework, eating in a cafeteria and all the other things that students do.

Because I came to business school later than most, I get asked constantly if it is “worth it”. A few thoughts on that:

I don’t want to beat the odds. I want to turn the odds in my favor. Great success always encompasses an element of chance, but when you consider people like VCs and entrepreneurs who have been repeatedly successful across many events normally considered “chancy” you have to consider the idea that there are certain things those people do to change the odds in their favor.

Viewed within the next 3 years, business school undoubtedly leaves me worse off than I would have been without it; but if we’re all going to have 40 year careers, is a 2 years and $200k-ish investment in a key set of skills, a network and a credential a rational investment? I’d argue yes. Am I learning? Absolutely and a lot. Am I meeting interesting people? Interesting does not begin to cover it. Am I having fun? Definitely. Does this degree directly open up new, more lucrative careers than I had access to before? Unclear; But that’s not what I’m looking for.

Subjects like finance, marketing and accounting, are all pretty fascinating to me. (Yes, seriously, accounting! The mechanics of GAAP is not so interesting but the managerial accounting material is really cool.) More importantly, I think having those skills will make the ventures I undertake more likely to succeed. Of course the world is full examples of people who have succeeded without the formal training I’m paying for, but in my mind if success is to be a repeatable event rather than a random land of the dice, deep knowledge of those disciplines is extremely helpful.

Is it ultimately worth it? Time will tell.

Getting back to it

A blog that is 5 months stale is embarrassing. Better not to have a blog than to leave it stale. Despite the best entreaties of my parents I’ve never been a great diary keeper – my old justification was that I was too busy living things to write them down. Somehow that argument gets older as I do. With this, I try again.
In case you’re wondering if I ever made it out of Gili Trawangan, I did. I went on to Malaysia, Malawi, Zambia, Dubai, Russia, Estonia and England before coming back to the US and driving from Seattle to Boston. The photos from my various travels are posted here. Needless to say it was an amazing, life changing experience.

I’ve been asked many times what the highlight of my trip was. This may seem mundane to some but I’d have to say it was the 12 days I spent on the beach in Thailand. My daily itinerary was wake, relax, eat, 2hr yoga, beach, 1 hr massage, nap, dinner, party, sleep. 12x in a row.

There was a great group of 6 of us hanging out together and we rented motorcycles and drove all over the island, finding random beaches, bars and restaurants. Eating barbecue on the beach by flickering candlelight with just your friends and nobody else in sight is something you must experience.

All my other vacations and even the rest of my travels have been about doing stuff – sightseeing, meeting people, perhaps partying. The time in Thailand, the knowledge that I could stay as long as I wanted and thought that I had 4 months of travel still in front of me allowed me to unwind in a way that I’ve never experienced before.

Leaving town…

It’s amazing how much work it is to sort out and shutdown your life in a city. Packing, shipping, change of address, goodbyes, etc… Especially if you’re planning on being out of the country for a few months, there’s a lot of crazy stuff to do. A few things I discovered in my preparation:

  • Remote Control Mail is a company that you can have your mail sent to and they will scan it, PDF it and let you read it on the web. It takes a while to get set up (You need to send a notarized permission slip to the US Postal Service) but once it’s going, it’s very cool. The interface is a little crude and not tuned for low bandwidth connections but still it’s a great service. This is a business I looked at starting at one point so I’m glad somebody is making a go of it. Now they just need to get indexed by Google (but only for you…)
  • Onebag.com is really marvelous about telling you how to pack light for a long trip. In particular the MEI Voyageur bag they recommend is fantastic. It’s sort of a pain to get (You have to call the guy who makes them) but it’s really fantastic. Being able to carry everything you have on your back easily makes a big big difference to how you travel.
  • A stick of body glide is a great investment. If youre in 120 degree heat and 100% humidity and walking carrying 40lbs or so, skin in some sensitive places can start to get a little tender.
  • Moleskin notebooks are perfect for sticking in your pocket and writing down addresses, people’s names, thoughts that occur to you etc… If you’re in a place you don’t speak the language you can often show a taxi driver a written address and he will take you where you need to go.
  • Make sure that your guidebooks are recent. I have a 2004 Let’s Go (whoops) and things have changed a little.
  • I brought black leather shoes “in case I want to go somewhere nice” and right now that feels about as likely as going to the moon.
  • Do not, under any circumstances, lose your ATM card. Seriously.

Goodbye to Seattle

On March 10th, the day after my last day at Microsoft, I threw a party to celebrate all the good times I’ve had and people I’ve met over five great years in Seattle.
I’ve still got a lot more to say about Seattle, Microsoft, the last 5 years and the next 25 but for now I just wanted to get the photo album out there. As usual, the photos don’t really do the party justice. I was too busy having fun to take many photos.
To everyone who made it, thanks for coming! Take care and I hope to see you soon.

Goodbye to Seattle