I found myself planning a series of flights for Hacker Paradise, flying from Tel Aviv –> New York –> San Francisco –> Tokyo –> Tel Aviv with a few days of flexibility for when to take each flight. I spent about half an hour on Skyscanner and Google Flights, and couldn’t find flights for less than about $3,000. Which is a lot. At roughly the same time, Vlad from Flystein reached out and offered to help Hacker Paradise participants book flights. So I tried the service out.</strong></p>

    Flystein Homepage

    What’s Flystein?

    Glad you asked. Flystein, it turns out, is what a value travel agent looks like in the “digital age”. Instead of making money by taking a percentage of your booking fare from airlines, Flystein helps you find the cheapest possible fare online that meets your needs and then charges a flat fee for doing so. You then book the flights yourselves, via links & booking instructions Flystein provides.

    Taking money for providing value. Who knew.

    How did it go?

    I gave Flystein my itinerary and neurotic set of flight cost preferences.

    My flight itinerary

    A day later, they came back with flights totalling $1934. A ~$1,150 difference between a “reasonably competent” online flight shopper like me and a bona fide flight expert.

    Proposed Routes

    How did things get so much cheaper?

    Throwaway Ticketing. My Tel Aviv to New York flight includes a roundtrip flight back to Copenhagen in February. I’m probably not going to take it, but who knows. Also, who cares – it was $200 or so cheaper than the equivalent one-way flight. I would have never known to check.

    Hidden City Ticketing. My San Francisco to Tokyo flight included a day-long layover in Tokyo and then continued on to Hong Kong. I, however, never made it on the connecting flight. One day, Hong Kong, one day.

    The Economist has a good write-up of the hows and whys and economics of flight hacks. The point is, you can save a considerable amount of money on flights if you know what to look for and are willing to dedicate the time required. Or you can use Flystein.

    How was booking?

    Mostly fine. One of my flight legs was expired by the time I looked (you have to book quickly) and I ended up calling British Airways, only to be told that I needed to pay thousands of dollars more.

    So I let Flystein know. After cursing about British Airways for a bit, Vlad found a flight that worked perfectly only a few minutes later. The new flight cost a whole $20 more.

    The whole booking episode could have been avoided if I had the ability to go full “travel agent” and just given Flystein permission to book on my behalf. It turns out there are legal reasons why doing so is not trivial, but they’re on it.

    Was it worth it?

    Flystein saved me over $1,000. Research fees for a trip like mine cost <$100 (a simpler flight starts at $49). So, yes. 90%+ of the savings for near 0% of the frustration in finding & booking flights. Value….but what if they don’t find anything? Fair question.

    It’s possible you’ve already found the cheapest rate you’re going to get. Flystein has a beat-my-price option where you only get charged if Flystein actually saves you more than their fees.

    Flystein. Use it when booking flights of non-trivial complexity (international flights over $500). It’s a thing.

    Published: August 01 2014

    I’m putting Estonia on hold - still excited to go there, and hoping to do so in April or May, once it warms up again.

    In the meanwhile, I’m heading to Costa Rica to help facilitate Hacker Paradise a 12-week digital retreat. The location has all the benefits of nomadism (cheap, beautiful location with delicious food and friendly people) while bringing together a small community of hackers working on individual learning, contracting or their own companies.

    Here’s how it happened: Casey Rosengren, a Penn classmate and fellow Penn Hackathon organizer, was doing the whole travel-and-freelance thing and did some work for a boutique hotel that was down to give Casey the entire place for a couple of months, leading to the creation of Hacker Paradise. I saw one of Casey’s posts about the place, and offered to come help.

    In short: I’ll be hacking by the pool in Costa Rica until November if you need me.


    PS. Care to join, either for the whole 12 weeks or for a shorter trip? We’re keeping a couple of spots open.

    Published: July 03 2014

    TL;DR: My US work visa runs out in a month, so I’m leaving for about a year to go travel. I start on August 2014.

    …actually, that’s it.


    • Wait, you’re not American? I’m an Israeli citizen born in Ukraine. I came to the US for my undergraduate degree. I kind of sound American because I went to the American International School for elementary through high school in Israel.

    • So what’s the story with the visas? I was able to stay in the US on my F-1 (student) visa for two a half years after graduation through OPT and STEM. This year, I applied for an H1-B visa with a sponsor - there were 172k people for 85k slots. There was a lottery, and I didn’t make it. Could have been worse.

    • Well, that sucks. Anything I can do to help? It’s fine, really. Thanks for your concern! I’ve been meaning to travel for a while, so the timing works out. If you’d like to help,
      • Recommend particular cities that you think would be great places to live for 2 months
      • If you know any good companies that do remote work, I might be interested
      • …actually, if you have the space and aren’t planning to move for a year, I wouldn’t mind storing a bit of stuff in your basement
    • What’s the plan? Largely TBD, but the tentative plan is to live in six different locations for about two months each.

    The first stop is Tallinn, the capital of Estonia. Why? Wired swears by it, and my further research confirms Tallinn should be an interesting place. I don’t know if I want to work on my own ideas or contract remotely yet - time will tell. Plans are still up in the air for the next destination, but I am hoping to get a couple of months of skiing in over January & February.

    • That sounds fun! Can I come visit? Absolutely. My plan is, rent prices permitting, to have a guest bedroom in every place I’ll be living in.

    • …so, are you coming back? I certainly plan to. I love it here.

    • Our immigration policies are ridiculous! That’s not a question. Also, politics is hard! If you want to help, consider supporting fwd.us or one of many other immigration reform groups.

    • Let’s hang out before you leave! Totes. Email me and let’s try to find a time and a place.

    Published: February 04 2014

    I helped organize HackCon, a conference for student hackathon organizers, this past weekend in NY.

    I gave a talk about Hackonomics, trying to quantify the financial benefit for hackathon sponsors and figuring out what the future looks like. I then annotated the slides - on Medium, for a change.

    The writing style here is a lot more like the talk I gave - more stream-of-consciosness than well-organized. Different, but not necessarily worse. Hopefully.