A week of Puerto Rico highlights

In April 2019 I invited a few close friends to Puerto Rico for my birthday. I figured 5-10 would show up. Instead several brought friends and we ended up having a 51 person week long party / unconference / exploration of Puerto Rico.

There were wild horses, bioluminescent bays, giant telescopes, and discussions that made me feel lucky to have such weird and wonderful friends. It was also astonishingly easy to put together, which shows how ready Puerto Rico is for more tourists.

If you’re looking for a very fun vacation that supports many local entrepreneurs and Puerto Rico’s ongoing recovery, follow the itinerary below.

Wednesday in Old San Juan: paella, piano, and dancing

Old San Juan is one of the oldest settlements in the Americas, with buildings dating back to the 16th century. It feels more European than anywhere else I’ve been in the ‘new world’.

Most of these photos are by Daniel Gaspersz, Tammie Kim, Matthew Brown, and Lena Xiao, but I’m afraid I don’t remember which are which. Thanks to all of them!

We rented a 200 year old house constructed by rum baron, now owned by my friend Jon. He rents it on Airbnb here.

We watched sun set from the highest point in Old San Juan: the roof of the Gallery Inn, a fabulous boutique hotel full of art and parrots (there are five: an African Grey, two macaws, and two cockatoos). The hotel is a labor of love created by the 80-something Jan D’Esopo, a gifted painter.

We hired Jorge Morales, the chef from Cafe Poesia, an arts-focused cafe in Old San Juan, to make paella live. If you don’t want to hire him for an event, you can enjoy his paella of the week at Cafe Poesia every Friday at lunchtime.

We ended the night at my favorite one-two punch in Old San Juan: the Cannon Club at the Gallery Inn and La Factoria.

Cannon Club is a gathering place of colorful people, parrots (the same ones from the hotel above) and pianos. Gifted artists often show up unannounced to play live; Alicia Keys and Yo-Yo Ma were both here earlier this year.

La Factoria is a James Beard Award-winning cocktail bar that is actually a labyrinthine collection of 6 bars accessed speakeasy-style through unmarked doors. From the cocktail bar you pass through to a wine bar, a salsa/dancing space that often has live music, a dungeon-like disco with an even more dungeon-like cocktail bar in the very back, and another bar I don’t want to describe in too much detail because it’s more fun to bring people there in person. Since this was my actual birthday, someone was nice enough to arrange a cake and buy me way too many shots.

Thursday: beach day in San Juan / exploring art and nightlife in Santurce

Early risers spent the morning visiting El Morro, a monumental fort built by the Spanish over the 16th-19th centuries at the edge of Old San Juan.

We spent the afternoon at Ocean Park beach, surely one the of the best beaches in the world. A few friends bonded with the local kitesurfing crew while most of the rest of us played volleyball.

By late afternoon we migrated to Calle Cerra in the Santurce neighborhood, a mecca for local art where many of the buildings are covered in murals.

We started with dinner at El Patio de Sole, a restaurant that looks like the inside of a well-curated thrift store. It serves good old fashioned Puerto Rican comfort food.

We visited my friend Shipwreck’s studio, sadly now closed while he works on finding a new live/work space. This was the first, though certainly not the last, time Sean somehow ended up shirtless.

Thursday nights on Calle Cerra usually see a number of gallery openings and live bomba y plena music at Esquina el Watusi, a favorite local bar.

There was much dancing on the street. For no good reason, a number of us decided to wear cheetah print.

The most energetic of the group ended up at El Local. After Hurricane Maria, this alt bar became a soup kitchen and shelter for many in the neighborhood. When we went it was the weekly LGBTQI night, complete with fire dancing performances.

Friday: Space telescopes + ancient petroglyphs

We had a leisurely morning before taking a bus to Arecibo Observatory. It was until 2014 the largest space telescope in the world (now the Chinese have built a bigger one).

The telescope is in a crater in the middle of a mountain range. We had to turn off our cell phones so as to not interfere with the telescope *talking with space*. The accompanying museum had fun interactive exhibits explaining the telescope’s importance to our space program.

Next we headed to the nearby Cueva del Indio, a spectacular beach/rock formation where there the Taino native Americans carved petroglyphs into the cave walls about a thousand years ago.

You have to climb down a bit to see the petroglyphs. I was too distracted by the scenery so missed them. Good thing I live here and can go back..

A few people got their drone one.

And watched the sun set while eating freshly caught seafood from the nearby Salitre Meson Costero.

Saturday: to the (other) island!

Off the eastern coast of Puerto Rico lies the perfect tropical island of Vieques. Once used as a military training site, the island is turning into an eco-tourism paradise powered almost entirely by renewable energy. We took a bus from San Juan to Ceiba where we caught the ferry over.

When I say perfect tropical island, I mean pristine turquoise water, palm trees, and… wild horses!

And foals.

Some people stayed in hotels and Airbnbs, but the majority of the group camped on Sun Bay Beach, which had showers and toilets (though BYO toilet paper).

We worked with the excellent Banquetealo to have food catered to the beach.

We rented jeeps and golf carts to get around. Esperanza is the main town on the side of the island with the bioluminescent bay, which was our target for the evening.

What? You didn’t know the brightest bioluminescent bay in the world is in Puerto Rico? A place where you put your hand in the water and millions of microscopic organisms fluoresce so your hand is covered in blue sparkles? Unfortunately its’ basically impossible to capture on camera so instead I’ll share pictures of our campsite.

It’s easiest to appreciate the bioluminescence under a new moon so it’s as dark as possible. Which means we also got to appreciate the stars!

Sunday: back to San Juan and beyond

Some of us made it to sunrise. Others did not.

Then it was back to San Juan via ferry and bus (some people flew – there are 15 min flights into SJU and Isla Grande, a smaller municipal airport in San Juan). We finished the weekend with a low key barbecue at a friend’s house.

For transport, I worked with chartercoachpr.com who were excellent. We hired Abe’s Bio Bay Tours on Vieques to visit Mosquito Bay. Banquetealo helped cater our dinner on Vieques. Other than a few dinner reservations, we figured out everything else along the way. I couldn’t have pulled this together without everyone stepping up to figure out the many tiny things that needed doing, and owe a huge thanks to everyone who came and made the experience so perfect. But even if you don’t have my friends with you, Puerto Rico has its own magic: come and see for yourself.

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An ode to my ‘iPhone mini’

Every time I check my phone, I get looks. People make fun of me. I get it: I have an old phone.

The iPhone SE, to be precise. I picked up this beauty after dropping my iPhone 6 in the toilet at Kara Swisher’s holiday party in 2016. Yes, the closest contact I’ve had with tech’s most revered journalist is when she gave me a bag of rice to try and save my phone.

The Apple Store was out of the sleek new iPhone 6S thanks to the holiday rush, so I had to buy an SE.

For those who don’t remember the hazy days of 2016, the SE is the same shape as the iPhone 5. Its 4″ screen is at least 25% smaller than any major smartphone today.

iPhone XS Max vs iPhone SE

It’s a testament to how quickly phone fashion changes that this phone looks so outdated. Or maybe not, since it looks like the iPhone 5, which Apple introduced in 2012.

I’m the CEO of a company that makes a mobile app (download Hitlist!), and friends have gone so far as to say it’s unprofessional for me to walk around with a phone that looks like it could be – gasp! – 7 years old.

Let them have their criticism.

Here are the reasons I love my tiny old iPhone:

  1. It’s small. I can hold it in one hand and reach anywhere on the screen. I can sit with it in the front pocket of my pants and not feel like it’s going to snap. It is the second lightest iPhone ever made (a mere gram more than the iPhone 5).
  2. It has a paltry amount of storage, 16 GB. Essentially enough to keep mail, calendar, maps, Whatsapp/Messenger, Uber/Lyft, and Spotify going. I can’t even download Facebook and Instagram because those apps are so damn big. This means it’s less distracting. Everyone’s talking about reducing their screen time, then spending $1k on a phone designed to make you want to use it all the time. Instead of relying on self control or system-controlled time limits, buy a small phone you don’t want to stare at for hours on end.
  3. I’m more productive with this phone. Unless you’re a social media influencer, very little serious work happens on a phone. What needs to be done on the go – checking and quickly responding to emails, taking conference calls – this phone can handle. Anything beyond that is usually 50%+ faster to do on a laptop. I’m not tempted to try and work more on my phone, so I do more faster when I get back to my laptop. (If you’ve found great ways to be productive on your Mega Phone, would love to hear how in the comments).
  4. Because I’m on the phone less and don’t have data-hungry apps I save money on data. I switched from my $80+ a month T mobile plan to Google Fi and rarely exceed $40/month now.

Pretty much the only thing I wish for is a better camera. The built in one is serviceable but I do drool a bit when I see what the Pixel 3’s night vision can do. If I’m dreaming –

Here’s a complete list of things I actually want in a phone:

  • Small size (4” screen or smaller)
  • Rubberized exterior, or something equally durable, so I don’t need a case
  • Amazing camera
  • Long battery life
  • Waterproof
  • Basic health tracking (step counter)
  • headphone jack

And I’d happily compromise on screen & processing quality: as long as it works for emails, navigation, and messaging I’m good. I don’t actually want to play games or watch streaming movies.

In conclusion

For now, when my iPhone mini croaks – which it doesn’t seem likely to anytime soon – I’m more likely to buy a refurbished SE on eBay (current price: $79.99) than to buy anything that’s in the market right now.

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I’ve moved to Puerto Rico!

What the title says!

I don’t know how long I’ll stay, because everything about this place is new to me. I visited for the first time in January and made the decision to move in February. But I am more excited about Puerto Rico than any place I’ve been in years and could envision building a long-term home here. Here are some of the reasons why.

First, a quick note about the basics: as the CEO of a distributed team at Hitlist, my priority is to live in a place where there is reliable internet, easy-to-navigate bureaucracy, excellent travel connections, and quality of life. To the first three: I get minimum 25mbps internet up and down most places, my coworking space scans/forwards my mail as needed, and there are flights to 47 destinations in 15 countries from an airport that is 15 minutes away from the city center. As for quality of life:

  • Puerto Rico is full of smart weirdos. It’s got a reputation as a haven for crypto bros, and a few outlandish ones give the place a bad rap. In the majority of cases, though, people who are really into crypto/blockchain technology are also radical thinkers who I find quite enjoyable, and some of the leaders in the field are here. Beyond that,
  • It’s diverse. Puerto Rico is a melting pot of Latin, African, native American, European, and Asian influence. I’ve not encountered a single unfriendly person, and social circles tend to feature a mix of ages, colors, backgrounds, and professions – something I sorely missed in San Francisco. People even have children here! No one I socialized with in SF had children (except for Avi, if you’re reading this, hi!)
  • Art is everywhere. Every shop, office, and home is filled with art. Not the kind that you get from IKEA or Society6, but things that individual people make. In my first two weeks I met more artists creating amazing stuff (including emerging art with VR/AR and electronic music) than I met in three years in San Francisco. As a bonus, the art that’s being created here is not primarily geared towards being destroyed at Burning Man every year.
  • It’s warm, but not too warm. It’s consistently in the 70s-80s year round (I’ve been told the summer humidity is tough; I don’t tend to mind that but will have to report back after I’ve experienced it).
  • I get to practice my Spanish, though I don’t strictly need to since most people speak English. Charlemagne said ‘to learn another language is to have another soul’ and since at least one of my souls is going to hell it would be useful to have a backup.
  • It’s affordable. You can rent a basic apartment on/near the beach for $500-600/month. You can bike everywhere you probably want to go, or rent a car for $30/day if you want to explore the island.
  • People take wellness seriously, and are pushing the boundaries of conventional medicine. Social life is highly physical: volleyball, acroyoga, salsa dancing, hiking, beach tennis, and climbing are part of a normal week. I’ve been learning to juggle (a skill I never knew I wanted, but am enjoying) at a weekly ‘circus jam’ in a 500 year old former army barracks. There are a lot of people working thoughtfully on ‘nature’s medicine’ (read: natural alternatives to pharmaceuticals, including marijuana, mushrooms, ayahuasca, etc) both legally and semi-legally. Puerto Rico’s status as a territory but not a state leads to some grey areas that are useful as scientists attempt to do studies to determine what the health benefits really are (or are not). I’m bullish on that sector as the US healthcare system gets closer to breaking and societal acceptance of alternative medicine shoots up. Puerto Rico is already the ~5th largest hub for pharma R&D worldwide so there’s a lot of infrastructure in place to scale new ideas.
  • The food! Ripe mangoes and avocados fall from trees. It’s easy to eat organic and local. I’ve lost ten pounds without thinking about it.
  • The nature! If surfing perfect turquoise waves isn’t your thing, you can hike lush jungles to hidden waterfalls, swim in bays full of bioluminescent plankton (the brightest in the world), and/or snorkel over colorful tropical reefs.
  • This is a unique inflection point in PR’s history. Something like $30bn of federal aid has been earmarked for reconstructing Puerto Rico post hurricanes Irma and Maria. The island needs smart, innovative people to bid on the massive contracts that are coming up, in pretty much every sector – urban revitalisation, healthcare, infrastructure, etc. There are already some savvy early movers here and I think many more will come as the extent of opportunity here becomes better known.

All in all, it feels on the ‘fringe’ in a good way, like Istanbul did when I moved there in 2009. Then you have all the conveniences of still being in the US: no telecoms roaming, no additional charges on shipping or moving money (after many years of living abroad, being able to order things off Amazon Prime really is a joy). Plus there are 12 direct flights to NYC a day – I can leave here in the morning and be at a lunch meeting in Manhattan if need be.

It’ll be interesting to revisit this in a few years and see how well some of my first impressions weather. But for now, I’ll leave you with this image of my new machete and me.

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How to travel with no luggage (2019)

For the last four years, I’ve been gradually whittling away at my possessions to the point I carry almost everything I need at all times. I can walk out of the door of wherever I’m living with just my purse and no idea when I’ll be back.

I’m hardly the only digital nomad living out of a backpack. In fact, there’s an entire subreddit dedicated to the art of this particular kind of travel. But I haven’t met many ‘onebag’ers who are also

  1. Trying to look formal/put together enough for business meetings as opposed to extended leisure/adventure travel
  2. Women

So here’s my VERY detailed breakdown of everything I need for extended travel – or to keep looking put together every day.

This isn’t just for travelers. Living with less can be good for the environment and good for your mental health. In my case, it’s helped me concentrate on what makes me happy: building a company, spending time with friends and family, and investing in the communities that have helped me live this life.

(Disclosure: I put in some Amazon affiliate links and received some items for free, noted where appropriate).

Apparel, in roughly descending order of how often I wear it:

  • Uniqlo airism seamless top ($14.90) – I wear this pretty much every day as a base layer. I used to swear by an Everlane silk cami but last year I switched to a Uniqlo synthetic which is slightly more durable in workouts.
  • skirt – I like to bike, so I go with a pleated skirt for mobility. Make sure it has pockets! The one I’m currently wearing I picked up from a Zara in Beirut in 2010 for about $20.
  • boots – for dressy occasions, poor weather, or anytime I want to look more put together. I like ones with a bit of a heel but still comfortable enough to wear all day. If I know I’m traveling to only warm weather destinations, I’ll swap these out for a pair of sandals I can dress up / down. My current pair are Charles Davids I bought at Community Thrift in San Francisco for $6.50.
  • Ex Officio underwear (x2, $18 each) is the traveler’s staple because they’re easy to wash and quick to dry. I usually carry 2+ extra pairs of various brands because I don’t love the cut of Ex Officio and I don’t want to have to do laundry every other day.
  • bra – one regular bra is enough. Currently into the Chantelle Merci plunge bra ($60).
  • tights (x2, £8) – extra warmth for little space. I bought these from Marks & Spencer four years ago and have never had to replace them despite wearing probably 50x each, so it seems insane to buy any other brand. 
  • ROAV folding sunglasses ($165, though the company sent me a pair for free) – anyone who’s hung out with me outside in the last 3 years has probably experienced me unveiling my ROAV sunglasses and trying to convince them to buy their own pair. They weigh almost nothing, collapse to the size of 3 credit cards, protect your eyes effectively with polarized lenses, and look stylish to boot. They’re also incredibly durable: they’ve survived a volleyball to the face (without damaging my face) and two Burning Mans. These are my favorite thing I own.
  • leggings – for workouts and colder days (layered over tights if need be). I’m currently wearing a pair from American Apparel I found at Community Thrift ($3) that have a nice sheen to them, sort of like faux leather, but they’re pretty flimsy and I’m excited to try out the Ever Brand Sweatflow leggings ($60), which have pockets (yay) and promise to go five days of continuous wear before they need to be washed (I’m skeptical but have ordered a pair to try them out).
  • Uniqlo sports bra ($19.90) – is super lightweight so is comfortable to wear for long plane rides. If I’m doing something that will have me bouncing around a lot I double up with my bikini top.
  • bikini – I LOVE Athleta’s sadly discontinued cross strap bikini top (bought on eBay for $40) because I can go for a run or dive off a cliff without worrying about things popping out, while still feeling cute and minimizing tan lines. If I’m doing a light impact workout like yoga I’ll wear this instead of my sports bra. The bikini bottoms can be used as an extra pair of underwear in a pinch. J Crew makes really durable and flatteringly-cut bikini bottoms so I usually just buy a new one when they go on sale.
  • Nike free flyknit 4.0 sneakers (bought on eBay for $60) – I used to wear Cole Haan Misha suede oxfords ($100) which I preferred for their street-to-boardroom versatility. I figured it was fine to work out in them because Olympians before the 1980s pretty much wore rubber slippers to run marathons, so how bad could it be to run in unsupportive leather shoes? Then I sprained my ankle for the sixth time (first wearing the Cole Haans) and my doctor politely insisted I wear more supportive shoes. Definitely on the hunt for something with more street style that will keep my ankles from rolling over, but the flyknits are good for workouts for now.
  • scarf/coverup – ideally big enough to wear as a dress, use as a blanket, sarong/towel on the beach – 4×6 ft works well for me. A silk/linen/wool blend is excellent for transcending multiple use cases. I bought a swatch of poly blend fabric I liked on 9th St in LA’s fashion district ($13) but wish I’d sprung for silk/wool.
  • wool socks – I’ve worn the same pair of icebreaker merino wool socks ($16) for a week straight and I’m not ashamed of it. No smells, no athlete’s foot. I’ve heard people say Darn Tough is even better so I’ll likely switch to that brand when this pair wears out. I usually get by with just one pair of ankle length socks but will bring an extra pair of longer ones if I’ll be in cold weather for extended periods. 
  • merino wool long sleeve – if you hang it up overnight will smell fresh as a daisy in the morning. I’m currently wearing the Patagonia Capilene midweight (found at Goodwill on 23rd St in Manhattan for $2) but I’d like to replace it with something a bit more ‘office casual’ with the same performance characteristics if I can find it. 
  • custom made leather jacket from Bilgili Leather in the Grand Bazaar, Istanbul ($165) – this thing is beaten to a mostly pulp after eight years of heavy wear, but it adapts to many styles, doesn’t pick up smells, and has lots of handy pockets. I’d like to replace it with something a bit lighter and a bit more formal looking.
  • Uniqlo lightweight packable hooded jacket ($5.90)- for rain, but also as a good extra layer when it’s really cold.
  • Columbia Heavenly synthetic down vest ($19 from Headwall Sports in Jackson, WY, amazing source for second hand outdoor gear)
Fur goes with everything, including John Deere, my ROAV sunglasses, and my beloved leather jacket.
  • fur headband ($8.99) – faux if you feel strongly, but nothing matches warmth/weight/style like fur.
  • gloves – I have a super cheap knit pair for now but am on the hunt for something more high quality and durable. Have heard good things about the Icebreaker merino glove liners ($25) worn as a standalone for not toooo freezing temperatures. 


I decant most toiletries into MUJI 12ml PE Cylinder with snap top containers, and paint the container tops with nail polish to be able to tell them apart. I also split toiletries into two categories: my overnight bag and a smaller mesh pouch I carry with me all the time. There are a few ‘swing’ items that will make it into my day kit based on weather/time of month.

  • overnight bag ($3): a PVC pouch I got on amazon that’s tooled to look like ostrich leather, so I can use it as an extra small clutch for going out.
  • tooth powder – a vial the size of a regular tube of travel size toothpaste will last you months (though may raise eyebrows as it looks like about $2k worth of cocaine). I’ve been using Eco-dent ($6.25) but recently sampled Lush’s ‘Tooth Fairy’ ($9.95) and will switch to that when this one runs out because it tastes much better. 
  • Lush ‘No Doubt’ dry shampoo/body powder – ($8.95) for keeping hair fresh but also for sprinkling inside clothes if you are forced to go longer than expected between showers or washing clothes. 
  • razor head (no handle) – I briefly traveled with a straight razor because I like that it entails less plastic waste but TSA does not like those razor blades. Now I travel with one or two disposable razor heads.
  • q tips, band aids, sanitizing wipes, sewing kit, safety pins, all held in the plastic baggie the MUJI rubber bands ($2.30) came in
  • tweezers, nail clippers, eye drops
  • Doctor Plotka’s mouthwatcher folding toothbrush ($8.49 for a set of 2)
  • OPI mini nail lacquer ($15.95 for a set of 4)
  • Public Goods mini lip balm ($1.25)
  • Drugs – I store these in a mini Altoid container
    • antibiotic – if you might be traveling in places where food poisoning is likely, it’s standard to ask your doctor for a antibiotic prescription. I’ve got cipro, which is a broad spectrum antibiotic; reports vary about whether it’s safe and it’s best to consult a doctor about what makes the most sense for you. I try not to take antibiotics but if something isn’t getting better with a day or two of rest a course of these usually cures what ails me. 
    • ibuprofen or any standard painkiller
  • sweet breath ultra concentrated breath mints – these really belong in my everyday kit but the bottles are so tiny I tend to just keep a few of them in various pockets.
  • (optional, not pictured) castile soap – can be used as shampoo, body wash, and laundry detergent. This usually isn’t necessary because I’m either staying at a hotel that provides shampoo/conditioner/body wash; or more likely staying with friends who will have this anyway. If for some reason I am somewhere that doesn’t provide this, I can pick up something at any local drug store. 

Essentials that can be slipped into the clutch or my regular bag:

  • argan oil ($22 for 2) – all purpose moisturizer for face, body, and hair. Trader Joe’s has a good one that I decant into one of the MUJI tubes.
  • reef-friendly sunscreen ($14.44) – I use sunscreen sparingly, because I believe the risk of melanoma is lower than the risk inherent in spreading a bunch of chemicals on my body every day, but will use this on my face if I know I’ll be getting a lot of exposure.
  • Lipstick (can also be used as blush), mascara, eye liner – I have had the same mascara and eye liner for 15 years which should indicate how often I use them, and how useless my advice on brands would be.
  • Lush Aromaco deodorant ($6.95)- all natural, free of aluminum, lasts for months, and actually works, which is more than you can say of most natural deodorants.
  • Mason Pearson pocket hair brush ($105, received as a gift) – I’ve had the same Mason Pearson pocket brush for 20 (!) years and while I wish it were a little smaller, there’s nothing that treats my hair so well.

‘Swing’ items I’ll include depending on plans/time of month:

  • Intimina collapsible menstrual cup ($28.54) – if you haven’t already gotten on the menstrual cup train, ladies, this is the way to go.
  • Condoms – not pictured but Lelo Hex ($19.90/12) earn rave reviews from my male friends.
  • ROAV sunglasses (already mentioned in apparel)
  • lens cleaning cloth
  • small perfume sampler
  • USB-3 to lightning adapter
  • crossbody clutch/fanny pack – big enough to throw kindle, keys, phone, and an extra layer for if it gets chilly, useful for days when you don’t want to carry around the whole bag. I found this one from a street vendor in NYC for $20.


  • Pixelbook ($849.95) – replaced my Macbook and I haven’t looked back. Portability, the ability to switch it into a tablet, two USB-C outlets, and affordability for the specs. 
  • iPhone SE ($399) and Google Pixel (refurb on eBay for $249) – as an app developer I need to have both an iPhone and Android for testing. It’s also useful to have a backup in case one gets stolen, dropped in a toilet, or runs out of battery – just move the SIM card over.
  • kindle ($129.99) – I use Libby to check books out from the library.
  • headphones ($18.99) – I prefer wired earbuds to wireless because 1. I don’t want another thing to charge and 2. I would probably lose one if they weren’t wired together and 3. I like to be able to plug into in-seat entertainment on airlines and 4. they work as semi effective earplugs if I want to block out noise. 
  • light ($15.99) – a small flashlight comes in handy more often than you might imagine. I clip this to the outside of my purse. 
  • Kikkerland universal power adapter ($9.70) is about a third of the size of every other adapter I’ve seen and does everything you need it to. 
  • USB stick – feels a bit ancient but it comes in handy more often than you’d imagine. 
  • port adapters – carry fewer cords when you have adapters to make all of them do what you need. I have a long and short usb-c to usb-c cord, then adapters to make those plug into traditional usb, micro usb, and lightning. 


  • lock ($14.99) – for trips to the gym, locking things at the beach, etc. 
  • stationary + stamps – I like sending thank you notes if I stay at a friend’s house or go to dinner. I also try and send a postcard every day since I find they tend to spark joy. 
  • Space pen ($16.99)- takes up little space and writes upside down, underwater, and in zero gravity, in case that’s ever relevant. 
  • checks – it is INCREDIBLE that the US banking system is so backward, but I find checks are sometimes still the cheapest way to move money. 
  • currency – I try not to carry much cash since you can do pretty much everything by card, but if I have leftover currency at the end of an international trip I keep it in case I end up back in that country in the future, or if I meet a friend that’s heading that direction. 
  • passport – I carry this with me at all times – you never know when an opportunity for adventure will arise, and it’s also useful to have a backup ID on hand. 
  • credit cards – I do most of my spending on a Chase Sapphire Preferred card which has excellent travel rewards, no foreign transaction fees, and a reasonable annual fee ($95). The best card for you is highly subjective, I suggest checking out Nerdwallet to help you evaluate the best fit based on your own spending habits. 
  • debit cards, transit cards, AAA card, health insurance card – since I pass through London, Los Angeles, DC, New York, San Francisco, and Boston with some frequency, I have public transit cards for all of them
  • driver’s license
  • earplugs, extra earbud pads
  • water bottle
  • matches
  • Alaska bear silk eyeshade ($7.99)
  • Hitlist tote bag (priceless) – for picking up groceries or using as overflow if I don’t have time to pack methodically.
  • Travel compression packing cube ($16.99) – all my clothes fit in the smallest one.
  • Drawstring sack ($9.88) – to separate dirty laundry, take to the gym/beach.
  • Cote & Ciel Moselle backpack ($485, received as a gift) – the one bag that fits ALL of the above. I’ve worn this for 7 years and get a lot of compliments, though my ex also referred to it as my ‘deflated couch cushion’, so there’s no accounting for taste. This isn’t the most ergonomic but looks like a fashionable purse and meets every carry on bag restriction.
Traveling outfit – everything else is in the purse.

A few last notes for those who are working on getting to the ‘one bag’ lifestyle:

  • I have a duffel bag with more winter clothes; hiking boots; ski, biking, and boxing gear; camping essentials; a ballgown; and essential documents (birth certificate, company incorporation docs, etc) that lives wherever I am currently spending the most time. I generally ship it to wherever I’m going to need it rather than carrying on the plane.
  • My parents will fairly point out that I still have a closet full of clothes at their house. To be fair on my side, I know my mom raids it and she would never let me throw out my prom dress or marching band T-shirt anyway.
  • I try to get clothes I can wear for a long time between washes, and don’t think that should be considered gross. Washing clothes takes a tremendous amount of energy, releases microplastics into the water supply, and destroys the clothes themselves. Wool, silk, leather, and linen last forever and don’t pick up smells. Darker clothes and patterns are less likely to pick up stains. I wash my underwear after every wear and the leggings after 1-2 wears, but very seldom wash the rest of the things in my bag.
  • If you ever find yourself lacking something you really need, thrift stores are a great source.

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Forming an Advisory Board that’s not horrible

In my last monthly company update for Hitlist, I asked for advice on how to form an advisory board. Here’s a distillation of the feedback I got.


  1. Not too early. “Advisory boards are super helpful (and cheap) if done right, and an expensive (in equity) waste of time if done wrong.” – Josh Elwell, a partner at ValueStream Labs, a FinTech accelerator. “Asking someone to become a formal advisor in the early stage of your company’s growth might be overkill. You can gain many of the same benefits through lunches or phone calls every couple of months – something most can commit to.” – Kerrie MacPherson, Principal, Financial Services Office at Ernst & Young (h/t to Betsy Mikel of Women 2.0 for pointing me towards her post).
  2. If you’ve raised an angel/seed round without a lead investor. “The problem and the challenge with not having the board after the Seed round is that there is no outside, non-executive perspective on the company. There is no higher level accountability for CEO, there is no regular milestones, and no regular check-ups… great boards help keep the business healthy and help accelerate it” – Alex Iskold, managing director of TechStars New York (h/t to Brittany Laughlin of USV for pointing me towards his post).


Via Chris Thorpe, director of engineering at EMC:

  • Advisory board members are people who can either make introductions to key people (former travel executives, for example) or solve hard problems but you don’t need them full time.
  • Ideally look for people who have been on “real” boards and/or have been CEOs or C_Os of companies that you admire.
  • I see executives hire “big names” to advisory boards and it looks good on your website but if they never read your emails or make intros then it’s just marketing. So you should reference check people.

Via Tim Peek of Peek Disruption:

  • While it’s important to have people in your industry on the board, I also believe that diversity of thought and experience is even more important for a disruptive player like Hitlist. So, I’d look for people in “adjacent” industries — areas of business that share some attributes with the travel industry but also are different or perhaps already experiencing what you hope to create in travel. What other industries have followed a trajectory similar to the one you hope to create in travel? Look for people from there to advise you.
  • Culture. I do think culture is the major differentiator for businesses in this century. In my experience too many startups are solely focused on execution (makes sense – there is a lot to do, not much time, and not many people to do it) and culture grows unnoticed. They end up with cultures that ultimately are unsustainable — I believe this is why so many startups don’t survive or have a deep “sophomore slump” and can’t come up with an effective 2.0 product or strategy once they are off the ground. So, what businesses have cultures which are successful and which you want to emulate — get those folks on your board.
  • A leadership advisor specifically for you. Someone you believe can take your leadership to the next level, support you in finding solutions to tough questions, and help you keep your head above the rising tide of daily business to focus on the big questions and direction.

Again from Josh Elwell:

  • Try to get at least one person who is “friends” with lots of people you want to know (investors, partners, customers, etc). Warm introductions are valuable, but that person pushing on “friends” from behind the scenes is even better at getting things done quickly.
  • Try to get at least one person with a “big” exit who fully understands the strategic process of getting a business sold (the second part is critical, because lots of entrepreneurs were lucky, not strategic). I get the best advice from people like that because they think about the end goal and how little decisions made now can help later.
  • Those might be the same person.
  • Relevant industry experience is nice, but I find that people with it aren’t as helpful as I had initially expected if they don’t have 1 and 2 (apart from just using their names for credibility).
  • I have an advisor who used to be a senior level management consultant. He is super helpful with lots of stuff even though he doesn’t have 1, 2 or 3. He always asks the right questions, cleans up all our pitch decks with ease, and is just generally a great person to get rapid feedback on new ideas.

Again from Alex Iskold:

  • Include 2-4 people plus the founders.
  • Recruit one or two of your top angels + other experienced operators/mentors.


  1. Commit to talking to each board member every 4-6 weeks and meeting with the whole board every 2-3 months. People can dial in if necessary, but in person is ideal.
  2. “Don’t be afraid to swap folks out if it turns out to not be a fit.” – Iskold
  3. Set clear expectations for commitment. “Board members will only rise to the level of performance articulated to them and expected of them, so as a board, it is important to clarify expectations with potential new members from the beginning.” – Sarah Najarian and Caroline Page of Robin Hood (h/t to Betsy Mikel of Women 2.0 for pointing me to their post)

More from Thorpe:

  • Grant up to 2 years for your advisory board’s stock grants (typically 10–25 basis points, in my experience, depending on their contribution and experience), but then have it renew by mutual agreement every quarter and vesting happens quarterly. If someone isn’t helping you or they get busy, then you simply don’t renew them for the next quarter.
  • Building the right culture around your board is paramount and it’s one of the things that’s really hard to do when you’ve never done it before. In my opinion for a new CEO, it’s ideal to have a friendly “chair” who can help you manage the rest of the board. This is ideally a former CEO who shares your cultural values, is busy with other things, and doesn’t want your job.
  • Practice building your communication skills with them, talking about issues, presenting company strategy, cash flow, income, creating a plan and showing your progress against the plan (and how the plan evolves over time – it’s a startup, not a public Fortune 500 company). Make a habit of calling your board members in advance of your meetings and making sure they understand what’s going to happen and that you have a chance to answer their questions and address their concerns.
  • At some point investors will want to take a board seat or have formal board meetings. That’s why it’s important to have already established strong relationships and board culture that work well for your company, so that your existing board members can keep meetings in line with that culture. Culture helps prevent unproductive habits like board members ordering you about what to do, regularly showing up late, talking directly to your employees, or going “off the ranch” to others outside your company. A good maxim is “eyes on, hands off” (or “fingers out”). And you kind of need to see people in action for a while before you know. Do they support you as CEO in the board meeting and prepare you ahead of time with their issues? Do they seek to support you when bad things happen, or do they surprise you in the middle of a board meeting with a hostile question? Do they work through you, not around you? Do they ask you hard questions that make you defend your decisions and understand your assumptions better, even if you don’t change your mind? Do they respect your deep understanding of the landscape more than their own brilliant insight from 30,000 feet? Etc.
  • Board meetings can turn into a lot of work, so try very hard to limit the amount of work to just the amount needed to keep you accountable and get strategic and tactical advice. I’ve seen a lot of startups spend way too much time preparing detailed analyses and predictions on the basis of data that are too limited or early stage to be of much predictive power. Understand what you can reasonably know and not know, and what you can reasonably predict from that knowledge. Don’t be afraid to say “this is the best we can say given what we know today, and we’ll update it as we learn more.”

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How we got to 200,000 users with no marketing spend

First thing I need to say: there is no single thing that will get your app to 200,000 downloads with no marketing spend. It takes a versatile team, a ton of work, and more than a bit of luck.

But in Hitlist’s year-or-so of existence, we’ve managed to gain over 200,000 ‘free’ users from the most valuable channels of all: word of mouth and earned media. We’ve never paid for an install, we barely touch our social channels, and we haven’t used any conventional ‘growth hacking’ tactics.

However, there’s one thing Hitlist has done that I haven’t seen elsewhere, and it’s been such a huge boost that I wanted to share it and hopefully inspire others to do the same.

What’s our one silver bullet?

Hitlist has a tiny core team, but we’ve been able to leverage hundreds more through a simple device: consistent, concise update emails. I send one a month, called ‘The best update ever from Hitlist‘, to a list that now numbers in the hundreds.

It wouldn’t be an exaggeration to say that the support we’ve gotten from the people on the mailing list has saved us over $100k that we might have spent on marketing, PR, hotels, conference fees, and countless other goods and services that have helped get us to this point. Here’s a small sampling of things that people on our email list have helped us achieve:

  • App Store feature in 40+ countries that resulted in nearly 100k downloads
  • temporary housing in New York, San Francisco, Zagreb, Berlin, and London
  • features in the New York Times, TechCrunch, The Next Web, and… a major Greek blog that drove nearly 10k downloads
  • >$500k in investment

Here’s what I try and include in every update:

  • Last month’s focus, and how you did. As Mark Suster once put so well, investors invest in lines not dots. Your readers are investors, in a sense: they’re dedicating time to reading your email, and you may be hoping that at some point they’ll invest something else (money or expertise or references). Give people a sense of your arc, and show that you consistently deliver on the goals you set for yourself – or if you don’t meet them, explain why and explain why you will next time.
  • This month’s focus, and an ask: let people know where you’re going and if they can help. They’re already reading your email, so chances are they like you and might like to contribute if they can. Give them an opportunity. If you don’t ask, you never know what’s out there. (If you haven’t seen Amanda Palmer’s ‘Art of Asking’ TED talk and have 13:40 minutes, watch it now, or read this great summary from Maria Popova). Make it specific: not ‘we’re looking for marketing help’ but ‘we’re looking for a senior marketer who has experience optimizing social channels for customer acquisition at a consumer-facing startup’ (know anyone?)
  • Something they don’t get elsewhere: you’re asking a lot of your readers, and some of them will understandably be thinking (in Noah Kagan‘s words), what have you done for me lately? Try and include something educational or access to something cool. Remember that not all of your supporters speak ‘tech’, but they’re probably curious about it. Imagine you’re writing all your emails to your great uncle Bob who is an artist. If he wouldn’t understand what you’re talking about when you mention MAUs, then spell it out.
  • Shout-out to a person/product that’s helped you out. If there’s a product that’s saved you lots of time, or a team member who’s been a hero, make sure to give them a hat tip. I’m a huge fan of Click to Tweet, for example.
  • Validation: any outside press, milestones, or accomplishments that can help show your reader that they should care about you and want to be part of your success.
  • Why we’re doing this: the ‘we’ here can refer to your team, or to you and all your readers. Why should they care? Why should they continue to invest any time in you? What are you adding to their life?
  • Something amusing: make yourself personable. Some call it unprofessional, but I like to include a GIF. For example, this illustration of Hitlist’s preferred sorting algorithm.

KEEP IT SHORT: 500 words or less.

This is the formula I’ve developed over a year’s worth of updates (you can see the archive if you like at blog.hitlistapp.com), but I’d love to hear tips and what’s worked for you if you in the comments.

TO RECAP, the core elements of an engaging update:

  1. Last month’s focus and how you did
  2. This month’s focus and an ‘ask’
  3. Something educational or exclusive for your reader
  4. Shout out to a person/product that’s helped you out
  5. Outside validation that you’re worth anyone’s time
  6. Why we’re doing this
  7. Something amusing

If you find this useful, consider sharing it using the conveniently placed buttons around the site.

And as always: check out Hitlist on iOS or Android, please one click tweet about Hitlist, Like us on Facebook, and follow us on Angellist!

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Weekend project: Vamoose

One of my favorite things to do over the weekends is to take a sidestep from full time development of Hitlist, my startup, and poke at other ideas that we’d love to eventually address within the travel space. In 48 hours I get to meet new people, learn about the latest technologies, and build and hopefully validate a feature that we might eventually incorporate into Hitlist.

This weekend I teamed up with Matt Duran, a student at University of Maryland Baltimore County; Dan Zhang, who is doing grad work at UT Austin; Drew Desautels, a Boston-based transport industry consultant; and Brian Shaler, a vagabond programmer (and teammate from the Playover project at the Mashable hackathon) to build VAMOOSE, a flight/hotel/car search plugin, for the Amadeus HACK@1050 in Waltham, MA.

The idea behind Vamoose is pretty straightforward: we wanted to create something that would make it easy to check how realistic it might be to travel to places that you’re reading about/investigating online. So we built a simple chrome extension that allows you to check air, hotel, and car rental costs without leaving the page you’re on.

Screen Shot 2014-11-09 at 11.41.12 AM

By far the coolest thing about this is the NLP work that Brian Shaler put together. It parses the available information on the page you’re viewing – text, metadata, etc – and tries to guess which location is being discussed, then fetches the prices automatically, so it’s one click to get a snapshot of your overall trip cost. Compare this to the process of opening a new tab, going to Kayak.com, typing in your origin, destination, picking a random date that might not be optimal, and waiting for the flight search results… then doing the same on booking.com and carrentals.com.

How this works:

  • the app used Readability to parse the relevant article text out of the page,
  • then used Node Natural to extract the root words in the piece (ie to identify ‘Chile’ from ‘Chilean’ and ‘Santiago’ from ‘Santiago’s’),
  • then looked for matches in the geonames.org City Names 1000 data set, an open source database of all cities with a population of >1000 people.
  • When there are duplicates (as in the case with Portland Maine / Oregon, Birmingham Alabama / UK, etc), we default to the city with higher population, which is not the most sophisticated way to handle this but hey, it’s a hackathon. With more time we might have searched for other context on the page, or tried to use browsing history to inform the prediction.
  • Once we have a city name, we use the Google places API to get lat/lon coordinates, which we then plug into the Amadeus ‘nearest airport’ API to figure out the destination airport. We use the individual’s IP address to predict the origin airport, and then plug both into Amadeus’s ‘inspiration’ API, which returns low fares for random dates (drawn from a cache of recent searches called from the Amadeus API). If for some reason the inspiration API doesn’t return anything, we fall back to the Low Fare API, which requires a specific date – we arbitrarily picked a week long trip two weeks from the current date. Again, if we’d had more time, we would have tried to make it easier to adjust the dates and built a settings page where you could pre-select dates that you were interested in traveling.
  • We also plug the destination city into the Amadeus hotel search API and the car rentals API to get an approximation of the costs for both.

If for some reason Vamoose isn’t able to detect the location you’re considering, you can alway manually enter the location you’re looking at. We use Google Places Query Autocomplete to get the city name, then the same process as above to return your results.

Screen Shot 2014-11-09 at 11.23.26 AM

Dan Zhang also built a very cool plugin for Facebook that automatically scans the page for place names and inserts a small symbol, Screen Shot 2014-11-09 at 12.01.36 AM, right next to them so you can find the nearest airport. So when you’re looking at pictures of your friend’s cute kids that you’d like to visit – or the wild beach party in Mexico you want to join – you can find out where you’d need to fly without having to leave the page. It takes the place name and plugs it into the Google Places API and then the Amadeus nearest airport API, as above. We wanted to link this up to the the other search function so that it would also show flight, hotel, and car rental prices with one click, but we ran out of time.


And because it wouldn’t be a hackathon if we didn’t have a little fun, we attempted to address the ‘sustainability’ challenge by introducing a new way to measure carbon emissions: Camel Count. Put simply, no one knows what a ton of CO2 really is. You can’t envision it. Camels, on the other hand, apparently emit 42 kg of CO2 per day, according to this article which posits that Australia should get carbon credits for killing feral camels (#notanonionarticle). You can understand, sort of, what someone is saying when they say that a trip from New York to Paris will do the same damage to the environment as nine camels will do in a day.

The code for the hack can be found on github here: https://github.com/dzhang50/rlt

If you’d like to install the hack, you can:

  • download a ZIP file from github (at the bottom of the column on the right) and unzip the file
  • go to the hamburger menu at the right end of the search bar in Google Chrome > Settings > Extensions > Load unpacked extension
  • Select the ‘ext’ folder from the unzipped github file
  • You should notice a blue circular Chrome logo at the top right of your search bar and the Vamoose logo next to locations on Facebook

It was a huge pleasure to play with the Amadeus APIs and meet such awesome people. And the judges seemed to like us too: we were awarded the ‘Entrepreneurial Prize’ as the overall winner.

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Hitchhiker’s Guide to Travel Startups

You’re thinking of starting a travel startup. Congratulations! You’re joining the most competitive, saturated market in the startup universe, or as Y Combinator partner Garry Tan terms it, “the most common bad startup idea.” According to PhoCusWright, 750 travel startups have collectively raised $4.8bn in the last eight years (’05-’13, so that doesn’t even count AirBnb and Uber’s massive raises this year). But hundreds more have failed to raise funding and/or gain traction.

Don’t let that discourage you. There’s a reason we all keep trying to disrupt this multi trillion dollar industry: planning, booking, and making the most of travel could be improved in so many ways. The tools to try and create something new have never been so accessible. Gigantic funding and and a strong existing brand can actually stifle innovation.

T-Rex tries to chart exponential growth
T-Rex tries to chart exponential growth

Here’s a list of resources I’ve found valuable in the course of building my own travel startup, Hitlist, which might help you get further faster. I’ve tried to make this as comprehensive as possible, but it’s naturally informed by my own experience. Therefore the information below is most relevant to US-based startups working on technological innovation (as opposed to building a brand/lifestyle business). I’d LOVE feedback/edits – leave them in the comments or you can contact me on twitter @gillianim.


  • PhoCusWright is the default industry body for research and analysis. Subscriptions and buying individual reports are out of most startups’ budget ranges, but there are useful tidbits online. See if you can make friends at more established companies that can share reports with you until you’re grown up enough to pay for your own.
  • Tnooz has long been the rag of choice for intra-industry gossip, analysis, and breaking news. With a distinguished list of contributors and an active community (as seen through the comments on most articles), it’s worth a daily read.
  • Skift plays in the same space as Tnooz, but is a few years younger (and has some ex-Tnooz writers on staff). They generally don’t feature outside writers but do have sponsored content. The newsletter is excellent and they’re entering the conference game with their own ‘Future of Travel Forum‘ in October.
  • ThinkwithGoogleeMarketerMarketWatch, and HUGE have also put out some interesting travel industry research.


  • David Ambrose of Steadfast VC has put together a fantastic list of angel investors and VC funds that have invested in travel companies in the last few years.
  • Skift crowned Erik Blachford, Sam Shank, Hugh Crean, Brad Gerstner, and Rich Barton ‘The Five Angel Investors who rule the world of travel.
  • In the VC space, General Catalyst and Thayer Ventures are well known for their focus on travel. Sequoia deserves special mention for, characteristically, getting into almost every major success in recent years (ITA, Kayak, AirBnb). Accel and Insight have also made a number of notable investments in the space.

Side note: as far as I can tell, the only woman represented on any of these lists – and the only woman I know of who has led any part of that $4.8bn invested in travel – is Sonali De Ryckr at Accel in London. Granted there are fewer women in venture capital in general, but they also seem to be disproportionately uninterested in travel investments.

CONFERENCES/EVENTS: this is not meant to be comprehensive – these are the conferences that fellow travel founders have found most value for money. H/t to David Litwak of Mozio, Alex Bainbridge of TourCMS, and Paige Brown of Dashbell for their insights.

  • PhoCusWright (various US locations, November, from $3499). The research company remains the indisputable king of the travel conference game. Its annual conference, held somewhere in the US, has historically attracted the who’s who of the travel ecosystem. The price tag is steep and so it’s important to go only if you have a clear agenda on what you’re hoping to get as your ROI from the three day event. There’s a smaller European edition in Dublin in May.
  • ITB (Berlin, March, 60 euro). Bring your walking shoes if you plan to go to this massive trade show. It’s very similar to World Travel Market, in London in November, but for some reason seems to attract more notable industry people. Expect lots of exhibition halls with every facet of the industry (from baggage handling systems to Disney tours) represented. A great opportunity to learn and network at any of the hundreds of coffee/cocktail hours. Hot tip: the LGBT pavilion has the happiest happy hours.
  • The inaugural Skift Global Forum (October, New York, ~$1200, with a much appreciated discount to $440 for startups) was a sell out smashing success: one commenter called it the ‘TED of Travel’. More intimate than the other conferences, and packed with good people to know.
  • Web In Travel (Singapore, late October, from $2000) the premier travel conference in Asia.
  • GBTA (various locations, July). The Global Business Travel Alliance holds a number of satellite conferences around the world but the annual Convention in July is the most effective for networking and BD.
  • Airline Information (various locations, main conference in December in New Orleans this year, from $599) geared towards airline ancillary revenue, cobranded credit cards and loyalty
  • HITEC (various US locations, June, from $645) geared towards the hotel and hospitality technology industry
  • WTM (London, November). Slightly smaller version of ITB (see above).
  • Many of the major companies (Amadeus, Concur, Datalex, Sabre, etc) throw their own conferences which can be high value.


  • Hackathons can be an amazing way to connect with other people intent on building the next big thing in travel. Tnooz sponsors a few throughout the year, and Mashable and Emirates Airlines have also done travel-related events in the past
  • PhoCusWright’s Travel Innovation Summit offers an opportunity to present to the who’s who at the conference in November – but at a cost of $15k ($6k if you get a scholarship)
  • BTN Innovate has an ‘innovator’s lab‘ where ten startups get to present
  • the Airline Information conferences have a ‘Lion’s Den’ which sounds like Shark Tank with less obnoxious judges
  • Web In Travel has a startup competition – would love more details from anyone who’s done it in the past


  • Travel Massive (various locations) is the most established meetup of travel industry folks. It’s a little different in every city (they’re active in more than a dozen, listed here) but tends to be heavier on bloggers/travel agents than on people involved in the technical side of the industry.
  • Travel 2.0 (New York, Boston) puts on educational and networking events specifically for aspiring or current travel founders.
  • Young Travel Professionals and Millennials in Travel are both networking groups that throw events in a number of different cities (mostly NYC & LA).

INCUBATORS/ACCELERATORS: if this is your first startup, you may want to consider one of these 3 to 6 month programs that typically provide seed funding, office space, mentorship, and an opportunity to present your company to investors at a ‘demo day’ in exchange for a nominal amount of equity (5-10%). The right accelerator can push your startup to achieve in 3 months what might take others 3 years.

  • Y Combinator (Silicon Valley, 3 months, 2x/year) has a rich legacy in travel startups. AirBnb is the obvious standout success, but Hipmunk, Flightfox, Airhelp, FlightCar, etc have also worn orange.
  • Startup Chile (Santiago, Chile, 6 months, 2x/year) loves to fund travel startups, but typically doesn’t provide much value add. Unless you count a subsidized six months in Chile as a value add. On the upside, they don’t take any equity in the company.
  • TechStars (various locations, 3 months, one starts nearly every month) has a decent legacy in travel. FlexTrip (Boulder), DealAngel (Boulder), Wander (NYC), have all been acquired. Dashbell (Boston) and others have raised subsequent rounds.
  • RunUp Labs (Bloomington, Indiana, 3 months, 1x/year) the ‘first dedicated travel startup accelerator’ just had its first demo day on August 1st. Unclear where they’ll be going from here.
  • Traveltech Lab (London, no set term) offers free office space and opens January 2015. We’re excited to hear more about it – applications are open now.

BOOKING APIs: if you want to allow users to view live pricing on your site/in your app, you’ll want to either build or connect to an API that can provide live pricing and availability information. These can turn into revenue streams for your app in two ways: either you will act as a travel agency yourself, earning a commission off every ticket booked through your app, or you will send your traffic to a booking partner in exchange for a lower referral commission. Becoming a travel agency is much more involved: you will need to provide merchant services (customer service, insurance, etc). Depending on how well funded you are or how agile you want to be, it might make sense to refer to partners at least until you prove your business model.


  • Skyscanner has a robust, well documented API that is offered for free to select partners. You can try emailing them but networking your way to an introduction will be more useful.
  • Orbitz / Cheaptickets (same parent company) offer an affiliate API, but I’m not sure what kind of commission they provide.
  • Expedia, Priceline, Travelocity, and Kayak have all offered flight APIs in the past, but most won’t anymore unless you have a very strong ‘in’
  • Sabre, Travelport, Amadeus, and ITA all offer paid APIs, but you will need to provide end booking services or link to another partner if you want to make a commission.


Tours and Activities

  • Viator has a white label program, widgets, and direct API for selling their tour & activity inventory on your site
  • TourCMS also offers an API for tours and activities, but you will have to make commercial agreements and set specific commissions with your booking partners
  • Excursiopedia has an XML API, “smart” widgets and simple deeplinks for content websites to distribute their inventory of >30k tours & activities with a simple flat commission of 6%
  • Festicket has an API for – you guessed it! – festival tickets


  • Rome2Rio has a number of very useful APIs for everything from geolocating to the nearest airport to navigating from, well, Rome to Rio.
  • CarTrawler.com for car rentals
  • Mozio offers an API for airport transfers
  • Airports/airlines: the official Airline Coding Directory is sold by IATA for $519, but OurAirports and OpenFlights offer free alternatives
  • Wcities offers a reasonably priced API for basic city information
  • Sabre has a number of APIs and caches of old data for analysis

MAJOR COMPANIES TO KNOW: by market cap (source: Skift)

This Quora post of the largest travel startup exits goes into more detail on the movements of big companies in this space.

  • Priceline ($65bn)
  • Las Vegas Sands ($60bn)
  • Disney ($47.1bn)
  • Galaxy Entertainment ($36bn)
  • Delta ($33bn)
  • American Airlines Group ($29.4bn)
  • Carnival Corp ($28.3bn)
  • Hilton Worldwide ($25.1bn)
  • Wynn Resorts ($21.3bn)
  • Southwest Airlines ($20.5bn)
  • Marriott ($19.3bn)
  • Amadeus ($19.1bn)
  • United Continental ($18bn)
  • Host Hotels & Resorts ($17.4bn)
  • Starwood Hotels ($15.2bn)

NOTABLE TRAVEL STARTUPS: Diego Saez-Gil of WeHostels has compiled a great Quora post with the major exits in the travel space in the last decade or so. Some of the biggest travel startups (defined loosely as those that haven’t yet reached an ‘exit’ – either by IPO or acquisition) are listed below – I’ve tried to highlight all the ones that have raised over $10m, and also some notable up-and-comers. Douglas Quinby at PhoCusWright also issues a ‘State of Travel Startups’ report every year which is packed with interesting insights.

VOCABULARY: if you’re not already in this industry, it’s important to know the distinction between the basic tiers of the travel booking/distribution system, as follows:

  • OTA = online travel agency (Expedia, Priceline, Orbitz, Travelocity) – online retailer of travel products
  • Metasearch engine (Kayak, Skyscanner) – aggregator of OTA content, drives warm leads to OTAs and direct to airline websites in exchange for a referral fee. The important distinction from an OTA is that you do not make your end booking on a metasearch engine. Metasearch engines make lower margins than OTAs but usually make up for it in volume.
  • GDS = Global Distribution System (Sabre, Amadeus, Travelport, ITA) – centralized repositories of fare and availability data for flights, hotel rooms, car rentals, etc. GDSs sell this information to OTAs and, increasingly, metasearch engines (Amadeus in particular has made strides in developing search as a service).

IF YOU THINK THIS IS USEFUL please share it with your friends. And remember, as this GIF illustrates, if you can roll with the punches and move fast, you may be able to make the competition fall on its face.

The power of startups

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Weekend Project: Playover

This past weekend, I teamed up with the amazing Tadhg Pearson, Brian Shaler (also known as doge_js), and Kyle Kahveci to put together a hack for Mashable’s Travel Hackathon sponsored by Emirates Airline and hack/Reduce.With only seven hours, there wasn’t much time for polish, but we pulled together Playover, an app that helps you intentionally search for trips with 6+ hour layovers. Why, you ask? Because layovers suck, but they don’t have to. Oftentimes you’re flying through great cities like Paris, Munich, London, Istanbul, or New York. Rather than moping in the airport, or planning a separate vacation to Paris, why not just schedule a long layover to at least get a taste of the city?

We didn’t have time to knit the back end and front end together as we’d wished, but the core of the app is live if anyone wants to play around with it at playover.herokuapp.com.
Tadhg mastered the back end, Brian was responsible for the front end, Kyle did design, and I attempted to bring together the necessary APIs and ensured that no TV crews got in the way of the gentlemen doing their work.
We took second place but are all winners because, you know, we learned a ton. And supposedly Mashable is sending us sweatshirts.

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Finding and Hiring Talent at an Early Stage Startup

I was recently asked what I consider the hardest part of founding a startup. The answer, of course, is that it’s all hard: finding the right idea, prioritizing, executing, and evaluating when or if to change course.

But if I had to choose the hardest piece of all, it’s finding the right people to work with. It’s tempting to shelter your baby startup from all outside influences. As long as you and your cofounder(s) are the only ones working on it, you’re in control. Ceding some of that control to new hires can be terrifying, especially if you don’t know them well. But if you really want your baby to grow up and be a self-sustaining or, ideally, world-changing business, you need to allow others to help shape its development.

So the following are some tips which I hope might be helpful as you embark on your search for employees 1, 2, 3 and… well, that’s as far as I’ve gotten, so when I know more I’ll try and report on that.

Finding People Worth Hiring

AngelList is probably the best job board to find startup-minded talent, but there’s a lot of noise to sift through. I use AngelList the same way many people use Tinder: I ‘like’ anyone that looks vaguely interesting, and if they ‘like’ me back I delve into their profile and see if they’re actually worth pursuing.

– Use your trusted networks. People often overlook things like their facebook timeline, their college’s job board, their floor hockey league email circular, etc. It’s like they’re ashamed they’re hiring. There is nothing wrong with being in a position to hire talent. Shout it from the rooftops. Put it in your email signature line. You never know when your mom’s friend from church has a son who happens to be sick of his job at Zynga and wants to move back east. And connections, even loose ones, help ensure that you don’t get stuck with a psychopath (more on that later).

– Be visible in the community. Present your startup at meetups and conferences, or try and get press. If you can’t get on a panel somewhere, organize your own event. If you can’t get press, publish a blog post or an infographic others might pick up. Answer questions on Quora. Be active on social networks, especially Twitter. If you were a talented startup-person, would you rather work for a respected, contributing member of the tech community or an MBA who has never built a business before?

– Poach! The people you really want to hire probably aren’t on the market: they’re already doing good work at a successful company. But their souls might yearn to be at an early stage start up. Help them achieve inner peace. Look for startups that have really taken off in the last 2-3 years, and identify the people that have been there from the early days. They obviously had and probably still have interest in working at a smaller company. Also, just as importantly, they’ve vested into most if not all of their equity (assuming standard 4-year vesting), so have less reason to stay in their current job. Woo them. You have something in your arsenal that is, to the right person, more attractive than money: the opportunity to build something new and innovative, or at least have fun trying. 

The Interview Process

– Letting the interviewee talk, rather than badgering him or her with questions, can surface the most interesting responses. Without being too awkward about it, try and leave enough time after an interviewee gives an initial answer so that he or she can add more. Example of a conversation I had once:

Me: what do you consider a good work-life balance?
Him: I think if you’re really concentrating, you can pack a really good day’s work into about four hours. And if you’re producing good work you’re going to be concentrating so hard that it’s difficult to perform well for more than four hours. So I really try and optimize my time, and of course I’m on call for more than four hours a day, but that’s probably what’s sustainable to consistently put out really good code.
(at this point I’m thinking that he’s probably right and this is pretty reasonable, but I wait just in case he wants to say more)
He continues: also at the end of the day I’m really quite lazy. I like my free time. I basically want to work the minimum amount possible. Fortunately as a coder I can usually get things done pretty quickly and no one really knows how long they should take so I can kind of set my own hours.
Me: …….

Needless to say, I’m not sure why this guy thought that was going to make me want to hire him. But I’m glad I waited and got the full picture.

– for a startup it’s important to ask the question: ‘If the company hit hard times, what would you do?’ If they say ‘I have student debt and/or a family to support and couldn’t take a reduced salary’, or something along those lines, they shouldn’t be disqualified. Nevertheless, it’s important information to know, and better to have that kind of conversation up front rather than when you’re against the ropes. Startups are so sexy these days, and lots of people interview for jobs at startups without really appreciating what that means: low pay, low job security, little to no benefits, all for the sake of an upside that is 90% not going to pan out.

– always hire people smarter than you, as long as they respect you and aren’t earning such a high salary that they’ve got no skin in the game.

Closing the Deal

– So, psychopaths. They exist, and they can ruin your company. Do your due diligence. Try and find some connection in the network of the person you’re hiring. I don’t actually like asking candidates to volunteer a reference, as I’ve always found that to be a pain when I was interviewing for jobs. I usually inform a potential hire that I’m going to try and reach out to people in my network who might have worked with him or her (it’s important to mention this so he doesn’t feel violated if he hears you’ve been snooping, but he should also understand that this is completely reasonable thing to do). I search LinkedIn for the previous company, see if I have any first or second-degree connections there, and reach out. Blind hires probably have a greater likelihood of working out than your average blind date, but that’s not saying much.

– when hiring I’ve always started people on a 60 to 90 day contract at a fair price (usually above what ends up being their salary, to compensate them for the fact that they’re not yet getting equity or in a long-term position), then negotiated ongoing salary/equity a month or two into their contract. Locking in a salary or equity number before youve worked with the person for at least a few weeks is like raising a seed round at a valuation rather than a convertible note: okay if necessary but preferable to postpone the valuation till you have more data.

– have hires (if you follow the above they’re contractors to start) sign a standard contract and agreement off Docracy if you’re too early stage to afford a lawyer. If you have less than $100k in the bank you are too early stage to afford a lawyer. I like Gunderson Dettmer’s standard consulting agreement.

– Read Founder’s Dilemmas by Noam Wasserman. So much wisdom.

In Conclusion

If we can learn one thing from Facebook’s acquisition of WhatsApp, it might be this: that no matter how smart or dedicated you are, you probably need at least 54 other people to build a $19bn company in four years. Don’t let yourself become an overprotective, smothering parent to your baby startup. It takes a village to raise one of these things right. 

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The Complete Guide to NY Tech – ABRIDGED!

A few months ago, Steve Schlafman of RRE Ventures put together an exhaustive overview of the NYC tech landscape. It’s great, but at over 100 slides, it’s a lot to wade through, especially if most of the names are new to you.

So here’s a hopefully more digestible version, loosely modeled after Rob Go’s excellent ‘Hitchhiker’s Guide to the Boston Tech Community‘.

New York has always been a center of innovation. But when it comes to the kind of internet-enabled, venture capital-fueled innovation we call ‘tech’, the Big Apple was long considered a bit of a backwater, the kind of place a good programmer would only move if his/her significant other was trying to be an actor. Less than ten years ago, people were more likely to consider Boston or Chicago America’s second tech city.

How things have changed. New York is now the world’s fastest-growing tech hub. We can’t compete with Silicon Valley for sheer scale yet. But Foursquare, AppNexus, Tumblr, Meetup, Makerbot, Shutterstock and Buzzfeed have shown the world that NY tech is more than just fashion and finance (though Gilt, Warby Parker, and Kickstarter are also great). If you don’t believe me, read Venrock partner Nick Beim’s fantastic, data-packed analysis of ‘The Rise and Future of NY Tech’.

If you’re new to town or new to tech, here are some places to kickstart your journey into the NYC innovation community.

Mailing lists/events listings

– NYC Startup Digest
Gary’s Guide: probably the most comprehensive, but it can be hard to figure out what’s really worth going to. On the upside, often has free goodies/discount codes
This week in NYC Innovation: well curated by VC Charlie O’Donnell
Bonnie Halper’s ‘SOSList’
Kate Kendall’s ‘The Fetch’

Coworking spaces (many also have good mailing lists)

WeWork (multiple locations): slick, professionally run, and affordable
AlleyNYC (37th and 7th): high traffic, good roster of events
Fueled Collective (SoHo): founders of the successful app development shop rented out a floor of Foursquare’s space and tricked it out like the set of a GQ shoot. Magnet for clever people who all seem too cool to really be in tech
Projective Space (SoHo): minimalist decor, solid events, mostly dudes
Wix Lounge (Chelsea): free! So often crowded. But free
New Work City (Chinatown)
Secret Clubhouse (Williamsburg): the hipster coworking space
– a more comprehensive list courtesy of Mark Birch here
– and the Complete Guide to Coworking from AlleyWatch


NY Tech Meetup: with close to a thousand attendees, it’s a madhouse and you’re not likely to run into a Big Dog (successful/famous founder or investor) in the audience like you used to in the old days. However, the presentations are usually high quality and it’s worth checking out at least once
Ultralight Startups, Entrepreneurs’ Roundtable: monthly event with 4 or 5 startups pitching a panel of VCs and getting feedback. Instructive.
PandoMonthly, Startup Grind: fireside chat-style talks with notable startup founders
House of Genius: amazing invite-only event (you can apply) where anonymous panelists give feedback to two growing companies
Amusemi: ‘dining club for entrepreneurs, designers, and friends’
NYC.js: smaller than the NYC Javascript meetup, but higher quality events. They aggressively screen for recruiters, so come only if you’re genuinely interested in learning about the tech
– generally, just comb through the mailing lists and search Meetup.com for things related to your specific domain (edtech, health, maps, design)
– as a general rule, things being hosted by General Assembly and at AppNexus tend to be quite good

If you’re starting a company

– Startup Weekend ($125), Lean Startup Machine: 54 hours to build a business. Pitch your idea, if it’s selected form a team, and present how far you’ve gotten two days later. Mentors—investors, experienced founders, etc — coach teams on best practices and award a winner
– Test Tube ($5): usability testing speed dating-style: spend five minutes with someone trying out your app and then do the same with theirs. Repeat ~6 times. Great way to get a real sense of your products’ appeal. You can go with just an idea and it’s a great way to get feedback from strangers, which is much more valuable than feedback from friends
Strategy Hack ($650): one day workshop to hone your marketing strategy
NYC Economic Development Corporation (NYCEDC): lots of government resources dedicated to helping small businesses grow, notably Take the HELM ($250k grants)
– accelerators: TechStars, AngelPad, DreamIt, and Entrepreneurs’ Roundtable: in exchange for 6-10% of your company, receive $20-40k investment, work out of a shared office space, and gain access to a community of mentors who help you accelerate your startup’s development. Competitive admission. More comprehensive overview from AlleyWatch.
– or try and pitch at Ultralight or Entrepreneurs’ Roundtable (free, see above)

If you might like to work at a startup

General Assembly‘s job boards (on the wall at 902 Broadway, 4th Floor… how retro)
The Muse
– Christina Cacioppo’s job board
Made in NY job map
– Jobs at Union Square Ventures-backed startups: http://www.usv.com/jobs

Educational resources – the last few years have seen an explosion in Tech Education. Some might argue that successful entrepreneurs learn by doing, not paying $12k for a coding course. But the paid schools below have built up impressive alumni networks and also help with job placement, which may justify the price depending on your own networking prowess.

General Assembly: everything from $20 evening classes to twelve week $11.5k web development immersives
Flatiron School: twelve weeks, $12k, and arguably the best coding education you can get outside of a good university. Competitive admission.
Startup Institute: $5250 for an 8 week course with a ‘core curriculum’ and optional specialization in different startup-centric tracks (web development, UX design, etc)
Codeacademy: it’s free. Online. Started by NYers. Bloomberg apparently uses it, bless his heart
Dash: a sexier but less developed competitor to Codeacademy, also free online. Made by the General Assembly folks


TechCrunch Disrupt (early May): the tech blog’s second conference gets an appearance from most of the current Hot People in Tech. Can be useful to try and rub shoulders, but don’t pay full price for a ticket
Maker Faire (late September): take Medieval Times and replace the jousting with robot jousting. Really!
NY Tech Day (late April): quite obviously not the World’s Largest Tech Event, as they bill themselves. Still a decent overview of who’s making what
– Capital On Stage (November): one day conference where venture capitalists ‘pitch’ to entrepreneurs
– Google search ‘NYC Hackathon’ (what is a hackathon?) as these are constantly changing
*these events are often pricey, but there are always hacks to get in for free or a reduced rate – participate in the Disrupt hackathon, for example, and you get two free tickets to the $1995-a-ticket conference

Scenesters – not the ‘best’ entrepreneurs and investors, but the people that go most out of their way to be accessible and welcoming to new startup-minded people + the ones that consistently generate good social media content. Sorted by descending sum of Twitter followers, more or less.

Arianna Huffington: no explanation needed
– Gary Vaynerchuk: prolific angel investor, just launched a seed fund
Mayor Emeritus Mike Bloomberg: presided over NY’s transition to tech powerhouse, continues to be a champion of the community
Jenna Wortham: NY Times tech reporter
Anil Dash: NY tech old guard. Serial founder, prolific tweeter. blog
– Fred Wilson: Godfather of Union Square Ventures. blog
Baratunde Thurston: seems to be a staple at tech events though it’s unclear why exactly
Chris Dixon: VC@ Andreesen Horowitz. blog
Joel Spolsky: founder of Stack Overflow, but best known for Joel on Software, his coder culture-defining blog since 2000. Blogging for 14 years!!
Alexis Ohanian: Reddit founder, Y Combinator’s east coast ambassador, angel investor, book writer
Kate Kendall: Melbourne transplant, media maven, founder of The Fetch
Esther Dyson: prolific angel investor
Rachel Sklar: founder of the Li.st, an email list for females in tech, ‘Change the Ratio‘ champion
Jonah Peretti: founder & CEO Buzzfeed
Jason Saltzman: founder & CEO, AlleyNYC
Bre Pettis: CEO Makerbot. blog
David Tisch: scion of the family with their name on half the buildings in NY. Formerly found of TechStars NY, now investor at Box Group
– Charlie O’Donnell: formerly of First Round Capital and Union Square Ventures, now leading his own $10m fund, Brooklyn Bridge Ventures, which has had early successes in Tinybop and Canary. Often arranges lunches & dinners for the NY entrepreneurial community
Cindy Gallop: advertising exec turned founder of friendly porn site mlnp.tv. Force of nature
Trevor Owens: runs Lean Startup Machin
Andy Weissman: Union Square Ventures. blog
Howard Morgan: First Round Capital. Most active 60+ year old tweeter in tech?
Ben Lerer: Lerer Ventures, Thrillist founder
Christina Cacioppo: formerly USV, now building something?
– Phin Barnes: First Round Capital. blog
Courtney Boyd Meyers: The Next Web, Wired, Daily Beast writer
– Kathryn Minshew: founder of the Muse, WSJ contributor, poster woman for Women in Tech
Alyson Shontell: Business Insider
Erin Griffith: formerly PandoDaily, now Fortune
Joanne Wilson: ‘The Gotham Gal’ angel investor, blog
Kelly Hoey: founder Women Innovate Mobile accelerator
Steve Schlafman: formerly Lerer Ventures, now RRE
Shai Goldman: Managing Director at SVB, formerly heading up the NY branch of 500 Startups, Dave McClure’s global empire
– Matt Brimer: one of the founders of General Assembly, prolific party-hoster
Rameet Chawla: co-founder of Fueled, insanely well dressed
Ryan Matzner: co-founder of Fueled, insanely well dressed. Yes, both of them.
– Frank Denbow: curator of NY Startup Digest and founder of NY Startup Weekend, staple at hackathons. Knows everyone
Murat Aktihanoglu: founder Entrepreneurs’ Roundtable Accelerator
Chris Velazco: formerly @TechCrunch, now associate editor at Endgadget
Mark Birch: serial founder, blogger, man about town. blog
Niamh Hughes: former community director @General Assembly, now at Shutterstock; Sandbox network ambassador for NY
Tom Limongello: columnist @PandoDaily, abortive creator of fail whale pillows
David Teten – ff Venture Capital, HBS Alumni Angels, frequent judge at startup competitions
– Christina Wallace – director of NY Startup Institute, super connector

Getting investment

– SVB’s Shai Goldman has helpfully compiled a spreadsheet of funds raised in the last two years, which are by definition the most likely to be actively making investments today
15 NY-based Angel Groups for Your Startup to Consider from AlleyWatch

Big NY Startups

– Meetup
– Foursquare
– Thrillist
– Etsy
– AppNexus
– Fab
– Tumblr
– Stack Exchange
– Shapeways
– Return Path
– Kickstarter
– Buzzfeed
– RapGenius
– Warby Parker
– Gilt
– Artsy
– Squarespace
– Vice Media
– Sailthru
– Refinery29

Concluding Notes

– General Assembly runs a great free 1-hour ‘orientation’ class every few weeks that gives a good overview of things and people to know
– Is this comprehensive? Hell no. That’s the point. Still, please let me know of any glaring omissions or falsities in the comments, mail g at hitlistapp.com or via the social network of your choice.

Sources: Steve Schalfman’s ‘Guide to NYC tech’; SVB, CB Insights, and Orrick’s ‘Venture Capital Almanac’;  Brittany Laughlin @USV; anecdotes; hard won personal experience

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Afghanistan Part I: Scariana

A bit delayed, I’ve decided to publish bits of my recent trip to Afghanistan. 

August 6th, 2013

Flight Istanbul-Kabul
Goodbye friends, hello war zone. It’s my first time intentionally flying into a place like this, but I don’t feel unsafe. Experience has taught me again and again that the majority of people are well-intentioned. That, or the majority don’t care enough about strangers to try and do them harm.

Plus I’ve had a number of friends working an living in this area for years. I’m going to be connected to someone who knows the lay of the land from touchdown to wheels up on my way out… I think. 

The Air Ariana flight has so far been uneventful. Only a few of my Istanbul-based journalist friends are poor enough to have to take Afghanistan’s national carrier, affectionately known as ‘Scariana’, over the more convenient Turkish Air or Emirates flights. But the plane is generic, in as good condition as many flights I’ve taken in the US. 

As far as I can tell, I’m one of only two Westerners on the plane. The other is a woman just shy of middle age wearing cargo pants and a long-sleeve T shirt. I wasn’t sure what was appropriate and so am dressed in linen trousers and a blue and white linen kaftan that hits just above my knees. I have a scarf for when I land, but for now there doesn’t seem to be any reason to wear it. Many of the women on the plane don’t have their heads covered, though they are conservatively dressed. There are only two female passengers wearing head-to-toe black abayas.

The passengers are probably 90% men. The flight attendants are mostly men in dapper pilot’s uniforms, but there are also three women flight attendants: one wearing an abaya, and two wearing slacks, collared shirts, vests, and an elegant scarf/hat combo that half covers their heads but certainly couldn’t be considered mosque appropriate. 

The two men in my row, Najeeb and Mohammed, are Afghani, from a northern province near Mazar-i-Sharif. They’re studying civil engineering at Yildiz Technical University in Istanbul. Najeeb hopes to continue his studies with a master’s somewhere in Europe, but has no question that he’ll return to Afghanistan when he can – ‘it’s too beautiful to stay away.’ Their studies are in Turkish, but their English is decent – they said they have some French and German friends and so it’s easiest to communicate in English with them. They pointed out the Hazar Deniz (sea), which marks the border between Turkey and Iran, and we all remarked how gorgeously turquoise it was.

Much of the land we’re flying over is raw mountains. Occasionally, a road snakes around the side of one, or a green smear marks a river between the ranges. Very little of it is inhabited. About halfway into the flight, clouds have blocked sight of the ground except for occasional points where the mountains break over them, like islands in a bleached sea. These mountains must be gigantic.

Afghanistan sits at the nexus of so many civilizations, and it’s easy to notice this on the plane. Some of my fellow passengers are undoubtedly Turks. In a tribute to their relative Westernization, they’re the only ones on the plane with any fat. The rest are harder to identify. Both Najeeb and Mohammed are from the Hazari ethnic group, who are known (depending on who you talk to) for being relatively peaceful compared to the majority Pashto. (The Taliban are mostly Pashto). But they don’t look similar at all. Najeeb has the smooth, high cheekbones and fine features of an Iranian. Mohammed is stockier, with tough-looking skin and a dark complexion – he looks Mexican more than anything else. One woman has the pale skin and heart-shaped type of face I associate most closely with Georgia. Others look Mongolian or Chinese, with jet black hair and and dark eyes that narrow towards the tips.

Many years ago, perhaps even before September 11th, I came across a story about Afghanistan in National Geographic that featured a picture of a young girl with light eyes and hair. She had a slightly testy look, like a child who’s just been told she can’t have a McFlurry. I thought it was so strange that this western-looking girl actually lived in a country somewhere in the middle of Asia. 

I tore out the picture and put it on my wall, where she watched over my struggles with high school chemistry homework. My decade-plus fascination with this country began. And it’s time to return our seatbacks and tray tables to their upright and locked position.

later that evening
Arrival went smoothly. The woman who had been wearing cargo pants changed at some point mid-flight into a shalwar khameez. My headscarf is on. A bus ferries people from the terminal building to the parking lot, through a number of concrete barriers and switchbacks. Anyone trying to attack this airport would have a lot of battles to wage with blocks of concrete. 

Apparently I was supposed to get an ‘arrival card’ from some office at the airport. My friend instructs me that if customs gives me trouble on the way out I should just tell them that they had run out of cards for the day on the day I arrived. Oh, how I love senseless bureaucracy. 

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On Starting Startups

(originally published on Medium)

5 Days to Decide if You’re Ready to Found
A step by step process to evaluate your idea and, more importantly, whether you really want to be an entrepreneur

You have an idea that could grow into a world-changing, money-belching company. So you’re thinking of founding your first startup.

The trouble is that there’s no obvious path to becoming an entrepreneur. In the US we have exams to tell you you’re qualified to dispense prescriptions, trade securities, or educate our schoolchildren. But how do you know you have the skills to start a successful company?

You probably don’t. No one is born knowing how to build a winning startup. But that shouldn’t hold you back from trying. Skills can be learned! If you’re seriously considering taking the leap, here’s a checklist, designed to be carried out in as little as a week, that will help you make an informed decision on whether or not you’re ready to found.

1. Read Founder’s Dilemmas by Noam Wasserman.
Time to complete: ~8 hours

What are the costs and potential benefits of founding your own company? What resources (human, financial, and other) should you be assembling? Founder’s Dilemmas has answers to most of the questions you don’t even know you should be asking. A lot of popular startup books (like the classic ‘Do More Faster’) focus on case studies, which are interesting. But I really appreciated Wasserman’s systematic longitudinal studies of 1000+ startups, and the facts he drew from them. For example: the average founder has worked for 14 years before starting his or her first company, but the standard deviation is 9.8 years. So there really is no ‘right’ age to become an entrepreneur.

2. Read Venture Deals by Brad Feld and Jason Mendelson.
Time to complete: ~4 hours

Chances are you’ll need to raise money at some point. Do you know what options, convertible debt, and carry are? Are you sure? If yes, go buy yourself a popsicle, and then read this book anyway (the rest of you do just the last part).

Convincing someone to give you money is an art, not a science. But for deciding how much equity to give up, what terms to be flexible on, and what kind of person you want to take money from — it doesn’t hurt to learn from the experience of those who have gone before. Plus it will probably help save you a lot of money in lawyer’s fees.

3. Attend a Startup Weekend/Lean Startup Machine weekend workshop.
Time to complete: 48 hours

These happen all over the world — Startup Weekend and LSM are the most well known, but many clones exist. They tend to follow the same pattern: on Friday night, everyone (typically 50-100 people) shows up and pitches ideas. Attendees vote and the top 10 ideas are selected for further development. Even if your idea isn’t chosen, you’re expected to join a group and work on turning one of the 10 concepts into a ‘business’ for the next 48 hours. Mentors—investors, experienced founders, etc — coach teams on best practices. On Sunday afternoon, each team demos, and the mentors choose a winner.

If you find in the course of the weekend that you’re frustrated by the challenges of building a team, fighting for your idea, figuring out how to make something work with less time or other resources than you’d wish, or releasing something that isn’t perfect… that might be an indication that you won’t enjoy doing this for a living.

(Some of these are free, some aren’t; the paid ones may have better mentors and thus, potentially, more useful connections.)

4. Connect with the ‘community’.
Time to complete: minimum 2 meetups, 4 hours total

Most cities will have some form of startup networking scene. These are generally easy to find via meetup.com, an online organization that allows people to create special interest groups and publicize their events.

Show up to anything that looks interesting, eat some pizza, and tell people about what you’re thinking of building. Eventually, as your idea and product refines, you’ll want to target key players rather than the admittedly hit or miss crowd you’ll find at an average meetup. But at the beginning you should just get feedback from as many people as possible.

Meetups are also a great way to meet potential teammates. You’re not going to build a billion dollar startup on your own, and even if your idea and abilities are Zuckerbergian you’re not going to have people beating down your door to work with you at the very beginning.

There are almost always some interesting people at every startup-focused event. If you can find them, hey! You might be good at this.

If there aren’t any meetups in your town, you can engage with the startup community online through forums like Quora, Hacker News, and Stack Overflow, to name just a few.

5. Find role models and ask to meet with them.
8 hours to set up and have 4 meetings

Chances are you have some entrepreneurs in your network of family, friends, and former colleagues or classmates who will be happy to listen to your idea and provide some initial feedback.

If you’re interested in a specific industry, don’t be afraid to seek out the leaders in your field. I’ve cold emailed CEOs of some of the biggest companies in my industry and every single one has replied (though not all agreed to meet the first time). Entrepreneurs tend to be generous with their time and advice. We’ve been where you are now, and we’re happy to do some shepherding just as we were once shepherded. That being said, you’ll do yourself and them a favor by learning a bit about the startup landscape before you reach out. Read Founder’s Dilemmas first and then make the most of your meeting by coming in with specific questions.

You don’t need to follow this list. I’m in no way an authority on what it takes to build a successful company (we’ve still got a long way to go at TripCommon). But if you’re thinking of investing a substantial portion of your life in a startup, a bit of due diligence can’t hurt.

Ultimately, no one’s going to be able to tell you when you’re ready to found your company. You need to be passionate. You should be able to convince at least a few other people that your idea is worth building. But beyond that, it’s anyone’s guess whether you have what it takes to succeed. The only way to find out is to try. Good luck!

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Istanbul here and now

My friend Alev is keeping a fantastic blog chronicling the day-to-day developments of the protests in Turkey. If you have time for only one entry, this email she wrote at the beginning still rings very true.

Dear everyone,

I hate these kinds of emails but what’s happening in Turkey is important. I have seen the situation being misconstrued in the international media (and ignored completely by most Turkish media). I got worried calls from my parents long before my Turkish friends did, because on Friday many Turks outside Istanbul knew nothing about the protests. Now they have spread to 67 cities, thanks to social media. I don’t have a clue what is going to happen, I can only guess, but I am here so I can see what’s going on now.

Basically, this is what happens every night since I have been here (from Saturday until today): protestors gather and march, gathering pace towards nightfall, chanting for the resignation of the government. Police blast them with tear gas (more on that later) and water cannons, often at very close range. Sometimes the gas is dropped by helicopter over large areas, like last night. The protestors get angrier and more determined. Around 5AM the die-hard stragglers go home, leaving barricades blocking the road so police vans can’t follow. The protestors clean up in the morning: debris, discarded masks, paving stones, etc. Around 8PM it all starts again.

The President (Gul) tries to calm things down. The Prime Minister (Erdogan) insists that we are all extremists, alcoholics, foreigners (fair point) and anti-democratic. He is now in Morocco, which has actually calmed the situation a tiny bit.

The whys and wherefores can wait. Right now, these are the important facts:

If the police left, there would be no drama whatsoever.

Despite the scaremongering images of smashed shop fronts etc, the proportion of hooligans among protestors is actually very small. There are inevitably angry kids from the ghetto who come to these protests to throw rocks around, and they don’t care why they are there. The last few nights, I have seen protestors calming them down and getting them to put down the rocks, put out the fires, stop swearing at the police. However, the hooligan element has scared the conservative demographic – Erdogan has made much of the dangerous nature of these protests.

There is an amazing feeling of solidarity on the streets. People hand out masks, water, lotions for the tear gas, lemons to strangers. When there is a sense of panic, and people start running, a general cry of “Yavas, yavas” (slowly, slowly) calms everyone down. Football supporters wear the colours of rival teams (unheard of) and link arms, cheering each other on. I have seen two things in the past two days I have never seen in my two years in Turkey: friendly football fans and people picking up rubbish. These are both happening during a quasi-revolution – impressive.

A word on tear gas: I don’t think anyone has explained yet how debilitating it is, and how demoralising. I am so impressed that protestors have been persisting with not only sustained but increased energy, because the effects stay with you the next day in the form of a severe hangover-like grogginess and headache. Also, most protestors are on about 3/4 hours sleep.

At the time, tear gas is like a wall of pain. People have asked me what is smells like. It is not smell, it is pain. A warning note of bitterness is immediately followed by burning of any exposed skin, throat, nose and stinging tears. You cannot see and you panic. You run, you just want to get away. It is extremely effective, and so much of it has been used recently that even my friends with industrial-style gas masks cannot proceed sometimes. There is no air, just gas, so the filters in the mask are useless.

After running and returning, running and returning, hearing helicopters circling overhead and canisters being fired somewhere unseen in front, you begin to feel defeated. You feel like this could go on forever, and you wonder why you are still here.The fact that people continue their chants and their efforts to push forward is unbelievably impressive, and I am frankly humbled by the determination and spirit I have seen. I do not have the stomach for front line stuff, and I am in awe of those who do.

Please tell everyone what is going on.

The most important message is that Turkey has woken up to what it wants, or rather doesn’t want, and that is a wonderful thing. The next few days will be crucial, it’s up to the government now, but I can only echo what I saw graffiti-ed on a wall this morning: “Nothing will ever be as it was before.”



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Working Women in Arabia

Grad student asks: were you comfortable as a woman working in the Middle East?

Yes, I was. In the Levant (Lebanon, Syria, Turkey, and Jordan) I didn’t dress or act differently than I would have anywhere, and I’m not conservative by most measuring sticks. I’ll discuss below some slight changes I made while working in the more open Gulf countries (Kuwait, Bahrain, Qatar, the UAE, and Oman). If you’re going beyond those boundaries, I refer you to the advice of the Unaccompanied Lady

In the Gulf (except Saudi Arabia) normal businesswear is fine, including skirts; on the evenings and weekends I covered my shoulders and legs to my knees. But aside from that, very little separated my experience in the Middle East from any other business interaction. Occasionally more conservative men would put their hand on their heart and bow rather than shake my hand, as they didn’t wish to touch a woman not related to them. 

The women I interviewed usually wore headscarfs if not a full abaya, but I didn’t feel any pressure or judgment because I was dressed differently. 

However strange it may seem to my fellow Americans, people in the more conservative parts of the Middle East really seem to believe that many of the customs we find objectionable are ways of protecting, respecting, and/or empowering women. They don’t think women are stupid or incapable. They just consider being a woman and leader of a household as more important than career paths outside the home, for the most part. 

I did meet women at all rungs of the corporate ladder, from receptionists to government ministers. There are few, if any, professions that are limited by gender. (I didn’t meet any female taxi drivers, though I’m not sure if that’s legislated.) In fact, women are generally considered more competent and reliable employees, and are more likely to have gotten a higher education degree than their male counterparts.

But how does this shape your experience as a western woman in the ME? Fundamentally, you’re a foreigner, and they don’t measure you by the same standards they do their ‘own’ women. None of my interviewees seemed nonplussed to meet an unaccompanied, college-educated professional woman. A few times the men I met even said they hoped their daughters would grow up to be educated and independent like me (a huge surprise!). Yes, there were a few guys who wanted to ‘continue the discussion over dinner’, but all you have to say is no. And it’s not like that doesn’t happen in the Western world as well. 

I’m not going to say there was zero harassment on the street. There were occasional cat calls, whistles, or more often simply staring, but again no more than most other cities. (I also lived in China, where people would occasionally come up and stroke my hair because they’d never seen anything like it. So maybe I’m desensitized to these kinds of things). 

In a different field, or if you were planning to live and work there full-time and climb the career ladder, the differences between how men and women are treated might become clearer, but as an analyst who seldom spent more than two weeks in any one location I never felt compromised in my ability to do any work.

So if you have the opportunity: go! The Middle East is gorgeous. It’s the cradle of civilization. The food is incredible. Most of the people you meet will be as generous as they are proud of their heritage.

Most importantly, your visit, work, or time spent living in the Middle East will transform the way you look at the news. You’ll return to your home with stories of a land rich in history, hospitality, and hummus. Tell these stories. The western world needs to hear more of them. 

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How to charter a boat in Croatia

Chartering a yacht in Croatia: it’s something for the Prince Edwards, Elizabeth Taylors, and Jim Clarks of the world, not us mere mortals, right?

Actually, it’s not that hard. And if you were planning on spending 100 euro/day or more on your European holiday, cruising will almost certainly be cheaper. You don’t need to have any sailing experience. You will see more gorgeous things, natural and man-made, than you would in almost any other setting. You won’t need to unpack and repack bags. It’s even eco-friendly.

The stretch of coast from Istria in northern Croatia to Dubrovnik, close to the border with Montenegro, has been a popular cruising destination for millennia. There are three UNESCO world heritage sites, well preserved Venetian cities, and remnants of Greek, Roman, Byzantine, Ottoman, and Austro-Hungarian occupation. Add in a thriving culinary tradition, some of the best nightclubs in Europe, crystal-clear water, and four months of almost uninterrupted sunshine from mid-May to mid-September, and you can see why people don’t tend to visit just once. Go before it becomes overrun…

GETTING THERE: Dubrovnik, Split, and Zadar are the most popular places to pick up your boat. All have airports with frequent connections to most European hubs. See more details below.

THE COST: 500-2000 euro/person ($660-2600 in the summer of 2012), depending on the level of comfort you want on your yacht, plus airfare.

Here’s a breakdown.

  • Boat rental: varies widely depending on boat size/quality/age and the number in your party. Plan on 1800-7000 euro, to be split by you and your fellow boatmates.
    • Standard yachts sleep 4-12 people. You will pay a flat fee for the boat, so it’s generally cheaper if you have a full boat and so have more people splitting the price.
      In most cruising yachts, the dining table (‘saloon’) will fold down to form a bunk for two people. Therefore, yachts are generally advertised to sleep 2n+2 people, where n = the number of cabins. If noone in your party wants to sleep in the saloon, you should subtract 2 from the number of people the boat technically sleeps.
    • Any chartering company will send you the basic details of the boats they’re offering. You can google the model of the boat to find all the specs, detailed pictures of the inside and outside, and floor plans that show how many bedrooms and bathrooms each boat will have.
    • If you plan to have 8 or more on the same boat, for the love of God make sure you have more than one bathroom. Toilets have a tendency to get clogged.
    • Keep in mind you will have to account for sleeping space for your staff, if you choose to book any. It is fairly standard to have the staff sleep in the saloon.
      Staff (optional)
  • Skipper ~ 150 euro/day ($200). Unless you’re a very experienced sailor, you’ll want to make this investment. He/she will take care of all navigation and boat handling, though you are of course welcome to help. Occasionally you’ll also get lucky and have a skipper who covers the duties of the host/hostess (see below)
    • Most reputable companies in Croatia now require formal qualifications for people looking to rent a boat, so if you plan to go without skipper you should make sure you have a license (RYA preferred).
  • Host(ess) (who keeps the boat clean and prepares meals) ~100 euro ($130)/day. Often the skipper + hostess are a couple.
  • Food:
    • self catering is easy, with a choice between traditional markets or supermarkets. If you have a hostess, you will give her money to do the shopping whenever we put into port.
    • Dining on shore can cost whatever you want it to. Quaint restaurants with delicious fresh food are cheap (10-20 euro/$13-26) and ubiquitous. Many places you stop will also have higher-end options.
  • Transport to Croatia
    • Dubrovnik and Split both have airports with seasonal connections to most European hubs. Expect to pay around $1000-$1500 with some advance planning. Obviously set a Hitlist alert! You may be able to get something for much less if you fly to the cheapest hub in Europe from your home airport then catch a discount flight to Croatia.
    • If you’re coming from Europe, plan to spend around 250 euro to get to/from Dubrovnik if you fly a full service airline. You can get much cheaper if you are willing to fly budget airlines (easyjet, Ryanair, etc).
    • You could also take a ferry from Italy – there are daily services from Ancona and Pescara. Check rome2rio.com for the latest.
  • Transport within Croatia
    • A taxi from the airport to the marina should cost 80 euro or so, and cheaper transportation can probably be arranged in advance.
  • Port fees
    • berthing fee at marina – 20-100 euro ($26-133)/day, depending on the place; 50% more for catamarans
    • anchoring in a natural bay – free
  • Fuel ~100-200 euro ($130-260)/week, depending on oil prices and how much you sail
  • Cleaning – most rental agencies will charge a one-time cleaning fee of 100-150 euro ($130-200) at the end of the week.


The best option, of course, is a personal recommendation. However, keep in mind companies change from year to year, so unless you go with an established brand you may not be getting the same service your friends got in previous years.
The most well-known companies in Croatia are the Moorings (which is also strong worldwide) and Sunsail. Both are a little more expensive than what you’ll find with local connections, but are not unreasonable and are the easiest for first-time charterers.
Always negotiate the price of your charter. You should be able to secure discounts of at least 10% off the stated price, and if you book before March you can generally get up to 25% off.
Planning in advance is a good idea. Croatia has become such a prime destination that boats really do sell out and it’s unlikely you’ll find a good last-minute deal in season.
You can usually negotiate another 5-10% off the price if you pay in cash (via bank transfer) rather than a credit card.
Most companies tend to ask for a deposit of around 25% of the total cost when you make the reservation, and the balance a month before your trip.
Certain incidentals (such as the cleaning fee and the skipper’s salary, if you book one) are paid in cash.


Bookings begin on Saturday, but you usually can’t leave port until 5pm, as the chartering company will need to clean the boat after the previous group leaves. It’s usually free to stay in the home marina on your first night in case you have people arriving late.
You will have to be back in the marina either by 5pm Friday night or 9am Saturday morning – make sure you check this if you plan to have a full itinerary.
In some situations, limited marina space will compel you to raft up with complete strangers. This may mean you have strangers walking across your boat at any hour of the night or morning. Use this as an opportunity to make new friends and share the off-market Croatian booze that you mistakenly bought.
Croatian gin is terrible.
Croatian beer is delicious, in a lager kind of way.
Badel Croatian Cognac is this blogger’s favorite drink.Share this:

Exploring Turkey

This is a quick overview of the main cities to see outside of Istanbul. It’s a follow up to the earlier posts on Planning a Visit to Turkey and Orienting Yourself in Istanbul. Like both of those, it was written in conjunction with Kate Bloomer.

Flights: Internal flights in Turkey are very reasonable. If you book in advance you’re looking at roundtrip for under 100 TL (US $65), but even last minute you’ll be able to get good deals. Bulucak.com is an aggregator for internal Turkish flights, though it doesn’t always work. We’ve flown Anadolu Jet, Pegasus Airways, AtlasJet, Sun Express and Onur Air and they’ve all been legit (and much more comfortable than Easyjet/Ryanair).

Train: The train network in Turkey is slow and far from comprehensive, but that doesn’t tend to matter to people who are considering taking the train. There are apparently some lovely overnight options to Kayseri (near Capadoccia), Konya, or Ankara, though the former two do fill up so be sure to book a day or two in advance. There are also some slower, atmospheric (read: rather dingy) services to Van and Kars in the east.

Bus: most buses are extremely comfortable coach buses with a personal TV and attendants who will bring you tea and nibbles. Metro and Ulusoy often have Wifi as well. Since buses are mostly used by locals, it’s a great way to get a sense of the country outside the tourist enclaves.

Car: Highways are generally very good and international signage makes it easy to navigate. Car rental is quite cheap but gasoline is EXTREMELY expensive – count on paying more for gasoline than the car rental.
  • Cappadocia: This was the first place I visited after Istanbul and the first I’d recommend. The area has plenty to do for the active – from walking through the beautiful Ihlara Valley, visiting underground cities and rock cut churches, and wandering through the fairy chimneys. The Goreme Open Air Museum (15 TL, 8 TL additonal for the Dark Church) contains more than 30 rock-carved churches and chapels with amazing frescoes dating from the 9-11th century. I highly suggest staying in Goreme, and if possible at the Kelebek (www.kelebekhotel.com) , where the owner Ali has a beautiful boutique hotel that’s actually built inside a fairy chimney (as well as a nice buffet breakfast included in the reasonable price). The view from a hot air balloon is supposed to be incredible, but comes at a (probably reasonable) price of around 120 euro. Fly or take the train to Kayseri or Nevsehir, where a hotel bus will pick you up.
  • Ephesus: Flights are available to Izmir, and from there you can take a bus or often hotels will provide a shuttle service to Selcuk (approx. 55 km), the closest town to these stunning Hellenistic ruins. Ephesus is a marvelous sight and well worth visiting – you can walk through in about 2 hours, it costs 20 TL to get in. In Selcuk you can also visit the House of the Virgin Mary (Meryem Ana Evi), 10 km south on the hills. As you might guess, this supposedly the house where the Virgin Mary spend her last days in Ephesus. The Vatican declared this place an official Catholic pilgrimage site. The Museum of Ephesus, which contains objects found in the excavation, is well worth a visit. The most famous of the camel wrestling matches also takes place in Selcuk in January. 
  • Olympos/Lycian trail: stretching along the Mediterranean coast west of Antalya (1 hr flights from Istanbul usually 70 lira or less) is a gorgeous string of ancient Greek and Roman towns, many with magnificent ruins. The ruins at Olympos are located in a national park (that includes a lovely stretch of beach), and it’s very popular to stay in bungalows or treehouses (literally, forts in trees – only recommended in the summer!) when you visit. Myra, about an hour west, features tombs cut into cliff faces, a well-preserved theater, and the church where St Nicholas was bishop (most people don’t realize Santa Claus was Turkish!). We haven’t been to Kekova, an island off the coast where you can swim among the ruins of a sunken city, but it’s supposed to be lovely.
  • On the other side of Antalya are the also-stunning ruins of Aspendos, Perge, and Sitra. They’re great out of season but can get a little overrun in the summer (apparently – we’ve only been in January). It’s easy to visit all three sites in the course of a weekend if you stay in the old city of Antalya and rent a car (which we did for 50 TL a day in January 2012). 
  • Cyprus is completely underrated in our book. Breathtaking Crusader castles, monasteries, Greek and Roman fortified towns, beaches and wild greenery – did we also mention delicious wine and seafood? See more details in the previous entry on Cyprus. Flights from Istanbul are absurdly cheap and frequent. 
  • The Aegean beach towns on Bodrum and Cesme peninsulas range from bucolic heaven to ritz and glitz to package holiday hell. In both places, having a car is probably sensible, as it costs about 50 TL/day whereas a taxi ride pretty much anywhere will likely cost you twice that (Bodrum peninsula is well served by minibuses, but they all connect through Bodrum town, which can be tedious). Only stay in Bodrum town if you are nostalgic for the days of sweaty frat parties or that trashy stag/hen do you might have once attended. Turkbuku, on the other side of the pensinsula, has some fun clubs, including the see and be seen Macikizi (rooms go for 400-800 euro a night here, but amazingly there’s no cover if you’re just coming to party at the bar). Cesme is more Turkish – better deals, more flavor, but ever so slightly more difficult if you aren’t tagging along with someone who knows their way around. The cobble-streeted, landlocked Alacati is definitely the jewel in Cesme’s crown, full of boutiques and excellent restaurants – a bit touristy, but gets points for being mostly undiscovered by foreigners. Plenty of nice beach clubs – or just undeveloped stretches of beach – are a quick cab or drive from Alacati.
  • Pamukkale: accessible from Izmir, this is the site of an ancient spa and hot springs used since the second century BC, and though you’re not llowed to swim in them anymore you’ll still be amazed by the naturally formed white calcium pools. The adjacent Roman city and Amphitheatre of Hieropolis are stunning. Day tours from Izmir are offered for around 45 Lira (as of January 2010) including English-speaking guide, entrance fee to Hierapolis and the travertines (this alone costs 20 Lira if you’re going independently) and buffet lunch.
  • Konya: How many cities are known for dancing but offer no nightlife? The important Muslim mystic, poet, and founder of the whirling dervishes, Rumi, settled here, and his lavishly decorated tomb (the Mevlana Museum/Mausoleum) is one of the more important pilgrimage sights in the Islamic world. Other attractions include the 13th c Iplikçi Mosque, where the final sultans of the Selcuks (the Turkic tribe which invaded Turkey in the 10th century and was eventually succeeded by the Ottomans) came to rest, and Ince Minare Museum, a 13th century madrassah. You can fly directly to Konya airport from Istanbul or take on a three hour bus from Cappadocia.
  • Kars/Ani: The city at the heart of Orhan Pamuk’s Pulitzer-Prize winning novel wins no beauty prizes, but gets some points for its castle and a handful of architecturally interesting buildings. 45km east, however, is (to our minds) the most evocative and beautiful place in Turkey: the ruins of the ancient Armenian capital of Ani. Perched on the edge of a gorge at the border of Armenia and Turkey, the ruins (many of which are 1000+ years old) deserve at least a full day of exploring. Bring a picnic of the deservedly famous Kars cheese, honey, and some vegetables that you can pick up at any street market in town – there is very little tourist infrastructure. *Kars, and especially Ani, can be inaccessible due to snow in winter and very hot and dusty in summer, so best to visit in spring/fall*. Hostels in Kars run tours, but we’re happy we rented a car and had the flexibility to travel onwards to Doğubeyazıt, a city at the foot of Mt Ararat (where Noah’s Ark supposedly came to rest after the flood), where the splendid İsakpaşa Palace marks the junction of Turkey, Iran, and Armenia. Four hours further south (and served by its own airport) is the important regional capital of Van. Peppered with Armenian and Georgian churches, historic temples and mosques, the city was hit by a massive earthquake in October 2011 so I’m not sure how feasible it would be to visit in the near term.

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Istanbul Tips, Part V: Get Legal in Turkey

Here’s a quick summary on how to get a residence permit in Istanbul. It’s a follow up to the earlier posts on Planning a Visit to Turkey and Orienting Yourself in Istanbul. Because I assume that after you visit you’ll want to live here as well, naturally.
When I first got to Istanbul, it was common practice for foreigners to show up, decide they wanted to live in Istanbul, and never get a residence permit. They’d live in the country on a 90-day tourist visa, get paid under the table, and take a ‘visa run’ out of the country every three months to renew their tourist visa.
For better or worse, the Turkish government has started to crack down on its illegal immigrants. The good news is that it’s very easy to stay in the country legally. You can either get a long-term Tourist Visa or a residence permit. The only differences I can tell between the two are that 1. you must prove that you have $500/month you intend to stay for the former and only $300/month for the latter, and 2. the Tourist visa is only valid for up to nine months while the residence permit can be for up to three years and renewed indefinitely. The following are instructions for how to get your very own long-term residence permit, or uzun sureli ikamet tezkeresi, based on an email that Amanda Pearson sent me when I was first investigating the process a few years ago. I’ve updated it to reflect some recent friends’ experiences as well.
Unless your work is sponsoring a visa for you, the ‘uzun sureli’ permit is the most hassle-free to get. It assumes you are hanging out here not working or being a student, and have money in the bank to cover living expenses for the period of the permit. You’ll apply for the residence permit after you’ve entered Turkey on a standard 90-day tourist visa.
Here is the website where you can get information and forms and make your appointment to apply for the residence permit: https://e-randevu.iem.gov.tr/yabancilar/dil_sec.aspx. You will need:
  • 1 color printout of the Declaration for Residence Permit form (İkamet Beyanname Form  (completed using typewriter or word-processor).
  • 4 passport photographs. (5 if this is your first application).
  • Original passport and photocopies of pages in passport showing your photograph and last entry stamp IN COLOR they will absolutely not accept it otherwise. You will not have to leave your passport there while the permit is processing (which takes about a week or less, my renewal took 24 hours), but you need to show it when you drop off your paperwork and again when you pick up your permit. 
  • Bank Statement showing savings of $300 per month you intend to stay (so $3600 for one year), or notarised Real Estate Deed. The proof of savings needs to be in the form of a notarised document from your bank – ie a printout, stamped by the bank and mailed to you (if a foreign account). If you have a Turkish bank account, you can pick up a stamped copy in person anytime during business hours, just ask. One friend said she just exchanged $3600 into Turkish lira and showed the receipt of this transaction to the authorities and that worked ok. I think she got lucky and it’s worth getting the official documents rather than risk having to go through the entire process twice, but for what it’s worth…
On the website you can see the link to the “e-randevu”, to set the time when you go in and drop your stuff off with an officer at the yabanci mudurlugu in Aksaray if this is your first application*. It feels really hectic and you can wait a long time, but the most important thing is to get up to the waiting room and get in line for a number. Take the number, which instructs you to see an officer and/or specifies the particular desk that you go to. The process has been different each time I’ve gone. 
The officer will look through your application and then send you downstairs to pay (the table showing prices is in the bottom right corner of the web page – currently for American citizens it costs $25 for the first month and $5 for every additional month you intend to stay, plus 149 TL for the residence permit book if this is your first application). You get a receipt and bring it back up, and then they staple everything together and you are basically good to go. They give you a slip of paper telling you when you can come back and pick it up.
On your form, if you’re getting an uzun sureli permit you’ll have to fill out the reason for your stay. Just write “Serbest” (= free/unemployed).
Sometimes the appointments get backed up and you have to wait up to 1-2 months to get in, but as long as you show that you APPLIED for the appointment before your most recent visa ran out, you are ok. This is shown on your official e-randevu slip which you must provide when you get to the station on the day of (when you make the appointment, be in a position to print out the receipt). Also, note that they require you to print out the application form in color (they definitely will not take it in black and white). Make sure that you are in a position to do that when you download it and fill it out.
Sometimes the appointments get backed up and you have to wait up to 1-2 months to get in, but as long as you show that you APPLIED for the appointment before your most recent visa ran out, you are ok. This is shown on your official e-randevu slip which you must provide when you get to the station on the day of (when you make the appointment, be in a position to print out the receipt). Also, note that they require you to print out the application form in color (they definitely will not take it in black and white). Make sure that you are in a position to do that when you download it and fill it out.
It can be sort of intimidating to go through the process, but as long as your docs are in order and you don’t have anything urgent to do that day, you should be fine. The peace of mind you get by having the permit makes it totally worth it in my book.
If you need to travel after your tourist visa has expired but before your residence permit appointment, you should technically be allowed to do so. Make sure you bring a printed copy  of your residence permit appointment details showing that you made the appointment before your visa expired. If you don’t have this document you may have to pay a substantial fine and may have trouble getting back into Turkey.
*If you are renewing your residence permit, the procedure is much easier because you can go to the much smaller and more efficient Yabanci Mudurlugu in your district – just choose this when you’re making your appointment online. The Beyoglu office is on Tarlabasi boulevard about halfway down and has a very charming and friendly guy on the second floor who speaks excellent English who will walk you through the process. Unlike the Aksaray office, you have to make your payment in a different building, the tax office in Sishane; even so the entire process took about two hours when dropping off and then less than ten minutes when I came back two days later to pick up the documents. I was also able to make an appointment for the next day when I set it up online. 

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Sometimes March in Turkey is gorgeous. This year, it was a wet, snowy mess. In other words, we had a perfect excuse to fly an hour south and explore the mythical semi-country of Northern Cyprus.

Why Northern Cyprus?This pint-sized island rewards even a 1.5 day trip, though you’d be happier staying much longer. Crusader castles, monasteries, Roman and Greek fortified port towns, wild greenery, excellent wine, hospitable locals. It’s got to be the most gorgeous, safe, and compelling conflict zone you can visit.

More people should know about what’s going on in Cyprus and you can’t help but learn a little by going there. (The Guardian also thinks spending money there is a good idea.) The island is divided between a self-declared republic – recognized as an independent state by Turkey and Turkey alone – in the north and the EU member state of Cyprus in the south. The capital, Nicosia/Lefkosa, lies on the border, and walking over it (you’ll need your passport, but no other docs) provides perspective on the differences governance has on economic development. If you’d like to read up on the place, I recommend the Wikipedia summary and then the excellent work of International Crisis Group.  

Getting there: Flights from Istanbul to Ercan Lefkosa airport in the north are absurdly cheap and frequent. Turkish AirlinesPegasusAtlasJet, and Onur Air fly direct from Istanbul and a few other cities in Turkey. If you’re flying from Europe, you’ll land in EU Cyprus at Larnaca, Paphos, or Nicosia. Easyjet offers very affordable flights from London.

Getting around: Dolmus (shared taxis) go between all the major cities in the north, but you’ll want a car to be able to explore. The island is tiny: the road from Ercan airport to Girne/Kyrenia, the gorgeous coastal town where you’ll probably want to base yourself, takes about half an hour to wind over the spine of mountains that runs through the center of the country (view at right). If you rent a car in the north, you can only drive it through the Turkish Republic, but technically cars rented in the south can be taken all over the island. We couldn’t find anyone to rent one to us in the south for less than three days, but you might have better luck if you book in advance. We ended up sticking with the northern part of the island and paid 100TL (about 40 euro) for a two day rental.

What to see: The Crusader castle of St Hilarion ices the tallest mountain in the country. A contested site from the days of Richard the Lionheart’s invasion (1191) to the Turkish army’s (1974), it’s now a museum. It takes about 15 minutes to get there from the airport and at least a few hours to do it justice. Bring hiking shoes.

Other than the novelty of walking in and out of the EU, the capital Nicosia/Lefkosa doesn’t offer much to the tourist, unless you like gambling. The few historical sites are missable if you don’t have much time.

Bellapais monastery (pictured at the top and below) is mostly in ruins, but pilgrims sometimes hold impromptu services.

Still primarily known by its Greek name, Kyrenia,  the Venetian port of Girne makes a convenient base for exploration. There’s not much to see aside from the impressive fortifications, but the seafood restaurants, bars, and accommodation offerings are hard to beat. We stayed in a random hostel for 5 euro/night in March 2012. 

Farmagusta: we didn’t get a chance to visit, but apparently it offers much the same fare as Girne/Kyrenia. 

Nature: the entire northern coast seems to be one gorgeous sandy beach. Find a westward-facing spit of land and tell me it’s not one of the better sunsets you’ve seen.

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