Oliver Roup’s Blog

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.

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.

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.

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.

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

Today, I did something crazy.
I announced that I’m leaving my job, a job that I really like and that others would kill to have, a job with a great team on a project I enjoy and helped start, a job for which I am well compensated and at a company that is probably unmatched in its ability to take on these kinds of hard problems. Who would do such a thing?

Even if every step of a path feels good, it’s important to pause every once in a while and look at where it leads and understand if that’s really where you want to be headed. Much as I love my job day-to-day, I look forward five or ten years and I think that there are some things I’d like to do in my life that my current path is not equipping me for. So, scary as it is, I’m stepping off this path and choosing a new one, even if the destination of the new path is much less clear than the old one and there are no guarantees that I’ll be happier with where it leads.
I’m taking six months off to travel and see the world and then in the fall I’m moving to Boston where I’ll be attending Harvard Business School to get an MBA. There are plenty of people telling me I’m crazy and they absolutely have a point. But I’ve thought about this long and hard and I believe in both following your dream and putting your money where your mouth is so I’ve decided to do both.

I’m trying to say my goodbyes privately, but if I miss you somehow, let me say it here. It’s been an amazing five years in Seattle and four years at Microsoft.  I lived in Seattle from the ages of 26-31 - some pretty critical years as far as figuring out who you are and what you want out of life and the people I’ve spent time with have changed me profoundly. I’ve grown to love this city in a way that I never suspected I would; so much so that I certainly wouldn’t rule out moving back here if the circumstances are right. So not goodbye then, but à bientôt.