Oliver Roup’s Blog

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.