This article was originally published in issue 5 of The Magazine, published December 6, 2012 by Marco Arment; edited by Glenn Fleishman.

Loren Brichter’s Letterpress is a beautifully designed iOS game that mixes Scrabble with the ancient Japanese strategy game Go. It’s the best casual game I’ve played in years, and it’s wasted more of my time than I’ll admit.

The trouble is, as the executive editor of this publication can attest, figuring out an ideal strategy isn’t obvious. A lot of otherwise brilliant players seem to struggle at Letterpress. [Editor’s note: I have no idea what you’re talking about.-gf]

This may come from players being stuck in a Scrabble mentality. In Scrabble, the game requires opponents start in the middle and work to the edges. Oddball letters like Z and Q have the highest values, and thus are desirable to preserve and place carefully.

In Letterpress, the worth of a letter isn’t determined by how difficult it is to use, but its position. Scrabble players start in the middle, but the savvy Letterpress player starts in the corners. The objective of Scrabble is to construct words, while the point of Letterpress is to prevent your opponent from doing so.

The basics

Two players see the same five-by-five grid of letters. The game proceeds in turns in which legitimate words must be played (according to the built-in dictionary), or a player must pass. Each word you create may be used only once, may not be a prefix of a previously played word (but can end in the same letters), and must be at least two letters long.

The board's starting position.

Tapping letters on the board puts them in a row below the player avatars and scores, and above the board. Drag letters to rearrange them, or tap to return them to their position on the board. You can test words even when it’s not your turn.

Playing a word stakes a claim on the letter tiles that comprise it. Letterpress shows that tiles are claimed by changing the color, in the default color scheme, to blue (for the local player) or red (for the remote opponent).

A tile’s background is a light shade of the color unless it is surrounded on all sides on the board by tiles claimed by the same player. In that case, a dark shade is used. In any given turn, if a player claims light-colored letters from an opponent, this removes the aegis of any side-adjacent protected letters.

Demonstrating a defending letter with W.

Diagonal letters don’t count for defense, only the sides. And if a defended tile and its surrounding tiles are used by your opponent, that tile remains yours, even though it is no longer accorded special status unless you protect it again.

A player can always use tiles he or she already claimed, but gains no advantage from doing so. Tiles’ ownership shifts back and forth constantly as the game is played. Play continues until all letters have been claimed, or until both players pass their turns in the same round. Whoever has the most claimed letters at the end of the game wins.

Opening moves

The first move in Letterpress confers a huge advantage. A well-played opening can devastate your opponent. If you’re opening the game, always defend a corner letter and make the longest word you can.

Corners are important because they’re the easiest tiles to defend and keep: only two sides need to be locked down, as opposed to three or four for all other tiles. Once a player owns a corner, it is very difficult to lose it. Opening with a defended corner provides a base from which you can expand into more defended letters, thus taking control of the board.

An opening gambit takes a corner.

Often, you won’t have much choice in which corner to take, but, if you can, defend the one with the highest-value letter — either a letter that occurs but once on the board or a vowel. Even if you can’t take a whole corner, try to take as much of one as you can. You might be able to claim it in the next round.

Beyond corner conquests, occupy as much of the board as you can in the first rounds. Each time, play as long a word as you can muster — at least 6 letters. Your opponent will surely steal many of those letters back the next turn, but don’t make it easy.

Before playing your first word, study the board carefully. See what letters lie in the corners and where the vowels and most-used consonants are. Think about some of the words that might be played in the match. Visualize the possibilities by testing out words, even for future rounds, before acting on the current turn.

Also think carefully about not just the words you can play, but how your opponent could turn them against you. Choose poorly, and even the best of openers will be for naught. For example, an opponent of mine opened with AWARES, defending a corner E. Unfortunately, he didn’t anticipate I could play UNAWARES on my turn, depriving him of all but his now-undefended corner E.

Awareness of the board, and all possible permutations of a word, is critical in Letterpress. If I play POOLED, my opponent can’t play POOL, because that’s a prefix of POOLED; but if there’s an S on the board, he can play POOLS. That’s okay, because I can strike back with LOOPS. If he plays LOOPED, I can counter with SPOOLED, and so on.

While all of that is going on, the point advantage is flipping back and forth between my opponent and myself. I call this back and forth “tick-tock.” As I’ll demonstrate later, understanding the tick-tock rhythm is essential to winning at Letterpress.

If you play following an opponent’s really great opening, you’re at a disadvantage, but not an insurmountable one. Like Microsoft in the ’90s, you want to “embrace and extend.” “Embrace” the opponent’s letters by using as many as possible, and “extend” by using unclaimed letters, preferably taking another corner as you do so.

However, the current first-mover advantage might be short lived. Developer Loren Brichter told me that he’s considering adding a “pie rule,” which would allow the second player to veto the opening move. If that happens, this section will still apply, but you’ll probably want to make less aggressive openers.

Mid game

Once the game is underway, Letterpress becomes an all-out war. Like any good general, you want to keep your troops in a tight formation. Spread your letters out willy-nilly around the board and the enemy will easily pick them off. Keep them close together to make them easier to defend.

Ideally, you want to “march” across the board, claiming and defending letters line by line, building a wall as you go. If you’re able to start from a corner, you can build either horizontally or vertically — maybe both. And if your opponent gives you the opportunity to take more corners, by all means do so; just don’t spread yourself thin.

As you make your way across the board, you want to defend as many vowels as you can. According to Brichter, there are at least three vowels (excluding Y) on every board, but never more than seven. Other than ZZZ (yes, it’s legal, according to Brichter), vowel-less words are few and far between. Block them off and your opponent is cut off at the knees.

Of course, the path of glory is never an easy one. The score in a well-matched game will be a constant tick-tock between you and your opponent. For that reason, you almost never want to play a word that would leave you even or at a point disadvantage to your opponent, because he or she can then steal your letters and put you in a hole that will be hard to climb out of.

In order of priority, you want to use your opponent’s letters, unclaimed letters, and your own letters (as you get no points for reusing your own). Also, don’t fall into the trap of just stealing letters, or you’re spinning your wheels. Try to make every word a mix of stolen and fresh letters, so you can hamper your opponent as you expand. Embrace, extend, and extinguish.

Speaking of unclaimed letters, they act as something of a clock for the game. As each one is captured, the end draws closer. If you have a significant advantage, use them as fast as you can, but if you’re behind, avoid them to give yourself time to catch up. Tick, tock.


With only a few unclaimed letters left, the end is nigh. More often than not, the decisions you make here will decide your fate.

The “tick-tock” concept becomes crucial at this point, because, in a close game, the player who ends the game usually wins. When only a handful of letters remain, ask yourself before every play, “If I do this, can my opponent finish the game?” If the answer is yes, don’t do it.

Marching across the board, the general's soldiers take tiles.

One letter I’ve often found left for last is Q. It’s a tough letter to use, because it’s seen as dependent on the letter U. But in Letterpress, U is not guaranteed to be on the board. However, if the letter Q is present, there will always be an I, according to Brichter. If you want to be a Letterpress master, learn words that use Q and I, but not U, such as QI(S) and FAQIR(S).

The best thing about Letterpress is that it lets you win in style. Some players, like Marco Arment, like to use the shortest possible word to win. I like to be clever, such as playing a high-school classmate’s own nickname against him. If you’re really good, you can “smurf” your opponent by taking every letter on the board, turning it blue.

Trying to smurf your opponent.

And if no matter what you do, you still can’t win, just remember: Profanities are legal.

Thanks to Loren Brichter for his help with this article.

Special thanks to Glenn Fleishman for his editing of this article, and for Marco Arment for allowing me to republish it on my site.

2012: A Year to Remember

I've had a fantastic year. For starters, December 21st has come and gone, and most of us are still here. The world keeps spinning, like it or not.

My year was fairly uneventful until late August, when I started this site. If you're new to the site, you'll probably be surprised to learn that I began it as a personal success blog. Soon, my passion for technology got the better of me, and the focus of this site changed drastically. But in the process, I found a bit of success myself, so in a sense, I've accomplished exactly what I set out to do.

Less than a month into this site's history, my speculative post on the future of the Mac was linked to by Jim Dalrymple on The Loop. That was my first big break, and thousands of his readers came to my site. I was blown away. I've had dozens of sites over the years, but I've been lucky to be read by a dozen people, much less thousands. I even got a few mentions on Techmeme, which for me was a mark of legitimacy.

Bolstered by my newfound confidence, I tackled what I perceived to be false advertising by my hosting provider, Squarespace. Squarespace CEO and founder Anthony Casalena reached out to me, promising improvements, and I wrote a followup regarding our conversation. While some of those came to pass, others have not, and Squarespace 6 has gotten even buggier over time. Another followup is due soon.

Soon after my Squarespace posts, I received my iPhone 5, and quickly found that it used an excessive amount of data. Little did I know at the time, my initial post The iPhone 5 is a Data Pig would be huge. After narrowing down the cause to iCloud, I made a video demonstrating the problem. To this day, it's still the most popular post on the site.

During the course of my iPhone investigation, I crossed paths with veteran tech reporter (and Jeopardy champion) Glenn Fleishman. Glenn was also investigating iOS 6 data usage, and in the process mentioned me on TidBITS and on the Macworld podcast.

Three days after that podcast, I married the love of my life, Hannah. After spending most of my adult life swearing not to marry, I finally caved in. I guess it's true what they say: When you know, you know.

Things were fairly quiet from then until November, which was a huge month. Adam Engst of TidBITS invited me to write for him, I had an article published in The Magazine, and was put in charge of an ambitious project at my job.

The past month, minus this holiday break, has been the hardest I've worked in my life. I drive 50 miles to work, work anywhere from 8-10 hours, drive 50 miles home, then work until I go to bed. It's a stretch sometimes, but I'm not letting up anytime soon. I'm getting the chance to live my dream, and I'm swinging for the fences.

Of course, I didn't do any of this neat stuff on my own. I had a lot of help, so I have a lot of people to thank.


Michael Ellsberg and Seth Godin

I read two books this year that had a dramatic effect on my life: The Education of Millionaires by Michael Ellsberg and Linchpin by Seth Godin. Education gave me a plan to pursue my dreams, while Linchpin gave me the confidence.

Jim Dalrymple

Like I mentioned above, Jim gave me my first big break in the tech scene. Who knows if I would have kept writing if not for that link on The Loop? Thanks for linking to me Jim, you gave me the confidence I needed to stay on course.

Glenn Fleishman

In addition to doing a fantastic job editing my piece for The Magazine, Glenn has become my greatest promoter and a trusted advisor. For a guy as busy as Glenn to take time to help a schlub like me really speaks to how great and generous of a guy he is. Thanks Glenn, you're the best.

Adam Engst

Adam gave me my first professional writing opportunity I have had in years when he invited me to write for TidBITS. TidBITS is one of the most respected Apple publications in existence, and having been around since 1990, one of the oldest. It's a lot of pressure writing for such an esteemed publication, but it's also been an incredible learning experience. Adam and his wife Tonya are two of the nicest people I've ever spoken with. Thanks for giving me the opportunity to write for your site, Adam.

Marco Arment

Marco started The Magazine in October, and it has quickly became one of the most venerated publications in the Apple world. Glenn and Marco often try to downplay The Magazine's importance, but any new publication that pays is pretty revolutionary for aspiring writers these days. Thanks Marco for showing that publishing can still be a profitable business.

Hannah Centers

My wife Hannah has been a constant inspiration for me. She is the smartest, hardest-working woman I know. She teaches in a poor, rural town, where she has become something of a local celebrity for all she's done for the kids. She's the inspiration behind all that I do here. I couldn't ask for a better wife or friend.

Shellie Michael

Shellie was my first journalism professor, and was a great mentor to me. She encouraged me early on, and even helped me land my first writing job (which I totally blew). Thanks Shellie, you're a wonderful teacher, and I doubt I'd be doing this now if not for you.

Leo Laporte and Dan Benjamin

I wouldn't know half the stuff I do if I hadn't spent years listening to TWiT and 5by5. Thanks to Leo and Dan for creating their respective podcast networks.


Last, but certainly not least, I want to thank God for all my good fortune over the past year and a half. I know that sounds strange and trite, but I was an ardent atheist until a series of events lead me to Hannah. Since then, prayer has led to me to great things. I try to avoid religion and politics on this site, but if you need help, prayer is free and can't hurt.


In my brief time as a semi-professional tech writer, I've found out how harsh tech audiences can be, and that's made me come to terms with the fact that I've been a pretty lousy audience at times myself. While usually for well-intentioned reasons, I've often stepped out of line under the guise of holding people accountable. I've changed a lot since meeting Hannah, and I'd like to think I'm more level-headed and mature these days. I'd like to take the opportunity to make amends and start 2013 with a clean slate.

John Gruber and Paul Thurrott

I group these guys together because I've given them both a hard time for being "fanboys" over the years. Which is unfair, because they've never denied their affinity for their respective platforms. More to the point, they've made good livings from their passions, which is something to be admired.

I was especially harsh to Gruber when he suddenly left 5by5 earlier this year, as were many of his other fans. I guess I was hoping that if pressured enough, he'd "see the light," and recant. But the truth is, the new The Talk Show is much better than the old one. I don't know what was going on between John and Dan, and it's not really my business, but Gruber often came off as moody and reluctant on the old show. On the new show, he's lively and engaged, and the show gets better with each episode. I hope John and Dan can patch things up one day.

Much to his credit, Thurrott has never shied away from an argument, no matter how trollish I'm being. And he always does it with sort of a smile and a wink, which I find admirable. Truth be told, I think Microsoft would be in far better hands if they put him in charge.

Ed Bott

In May of 2011, I accused Bott of being in Microsoft's pocket after a series of articles on Mac malware that made heavy use of anonymous sources. While I'm not a fan of proclaiming anonymous sources as the gospel, that ad hominem attack was uncalled for.

I'll never shy away from pointing out inaccurate facts, inconsistencies, and poor journalism, but I will be more careful in what I say about people. One of the things I'm getting used to as a semi-professional writer is that my voice carries weight. When I was just a random commenter, I could shoot off about anything and it wasn't a big deal, but now reputations and livelihoods are potentially at stake. That's a responsibility I want to handle with the utmost care.

What's Next in 2013

I plan to keep writing and keep learning, simple as that. I don't know if I'll ever get to do this full-time, but it's definitely something to work for. I'd like to eventually get deeper into podcasting, either as a host or a guest, but I have a lot to learn about audio, and I'm in need of a serious equipment upgrade.

Regardless of what unfolds, I think 2013 will be a big year.

I hope he's right!

I hope he's right!