StartUp Chess

Having finally had the opportunity to sink my teeth into Garry Kasparov’s very entertaining book: “How Life Imitates Chess”, I cannot help but be in a zugzwang state of mind. Isn’t it fascinating, how the different pieces in chess, so readily resemble the different stakeholders in a startup?

I feel another Startup Symphony coming along.

The King

Who else but the Investor. Whether it’s the power-tie, suspender super I-bankers of Wall Street or the slovenly business cazh clad VCs from the valley, these regal check writers are the ones that keep the entrepreneur in the game. I love the analogy, since most investors so accurately mimic the movements of the King piece in chess. They might be able to move in all directions, but the most many will do is hop over to a single square. They open doors, but it’s up to the entrepreneur to charge through. Switching from offense to defense, too many checks and you just may find yourself in a down round or worse — in Checkmate Chapter 11.

The Queen (Vizier in Arabic)

Founder (and yes, we need more female founders). The Queen is the most powerful piece in chess. She has the ability to move anywhere in the board (but she can’t just simply jump the way a Knight can, perhaps due to all the weight on her shoulders).

Early queen attacks are considered rare in high level chess, but there are some openings with early queen development that are used by high level players. For example, the Scandinavian Defense, which often features queen moves by Black on the second and third moves is considered sound, and has been played at the World Championship level. Some less common examples have also been observed in high level games such as the Kentucky or Danvers Opening), which is widely characterized as a beginner’s opening (one of my favorites to test the mettle of an opponent), especially when it is part of the development of the embarrassing Scholar’s Mate.

This is indeed antithesis to the startup world, as the Founder must be actively involved in all opening moves. Only when entrepreneurs have mastered their middle game is it advisable for them to take a back seat and watch the other pieces play.

On rare occasion, experienced chess masters may choose to sacrifice the queen as part of a risky Fool’s Mate strategy. This is often used by many seasoned investors as well, who tend to throw founders under the bus in favor of more senior management.

The Rooks

Developers, mostly because of their brute blunt force and habit of charging up and down the field of play.

In medieval shatranj, the rook symbolized a chariot as the Persian word rukh means chariot, and the corresponding pieces in the original Indian version chaturanga have ratha (meaning “chariot”), in modern times it’s mostly known as an elephant to Hindi speaking players (not to confused with the Arabic chess elephant), while east Asian chess games such as xiangqi and shogi have names also meaning chariot for the same piece.

Ancient Persian war chariots, like modern day web developers, were heavily armored, carrying a driver (designer) and at least one ranged-weapon bearer, such as an archer (Full Stack of Arches). The sides of the chariot were built to resemble fortified stone work, giving the impression of small, mobile buildings, causing terror on the battlefield. No wonder many developers are always on the go.

In the West, the rook is almost universally represented as a crenellated turret. One possible explanation is that when the game was imported to Italy, the Persian rukh became the Italian word rocca (“fortress” or salad), and from there spread in the rest of Europe. Another possible explanation is that rooks represent medieval siege towers — the piece is called torre (“tower”), in Italian.

Another possibility is that, as chess moved to Europe long after chariot warfare had been abandoned, a different symbol was needed to represent the rook’s concept of feudal power (the chariot being a method of warfare only used by the elite, very similar to medieval knights), and as such the Europeans adopted a castle to represent a lord and his feudal power, further supported by the (albeit later) name for the rook, the “marquess”, named after a nobleperson. Finally, the chariot was sometimes represented as a silhouette, a square with two points above representing the horse’s heads, which may have been seen to resemble a building with arrowports to the medieval imagination. An exception is seen in the British Museum’s collection of the medieval Lewis chess pieces in which the rooks appear as stern warders or wild-eyed Berserker warriors.

More important, to quote Howard Stauton, “the Rook, or Castle, is next in power to the Queen,” which is no wonder that many entrepreneurs love to do some startup “castling” by safely switching around their investor kings and developers.

For a full appreciation of the power of the Rook in the endgame, check out the Philidor position (more on him later).

The Bishops (Alfil or Elephant in Arabic)

Marketing. Definitely. No other reason than the fact that Bishops can only move sideways and that elephants, like great marketeers, never forget. You ‘feel’ me right?

Just like in the world of marketing, there are both good bishops and bad bishops. In the middlegame, a player with only one bishop should generally place friendly pawns on squares of the color that the bishop cannot move to. Reminds me of a certain marketing manager strategicallyplacing CTA Banner Ads in a competitor’s social media feed(s). This allows the player to control squares of both colors, allowing the bishop to move freely among the pawns, and helps fix enemy pawns on squares on which they can be attacked by the bishop. Such a bishop is often referred to as a “good” bishop.

Conversely, a bishop which is impeded by friendly pawns is often referred to as a “bad bishop” (or sometimes, disparagingly, a “tall pawn”). The black light-squared bishop in the French Defense is a notorious example of this concept. However, a “bad” bishop need not always be a weakness, especially if it is outside its own pawn chains. In addition, having a “bad” bishop may be advantageous in an opposite-colored bishops endgame. Even if the bad bishop is passively placed, it may serve a useful defensive function; as the well-known quip from Romanian Grand Master Mihai Șubă is that “Bad bishops protect good pawns.”

In a famous position from the game Krasenkow versus Zvjaginsev, a thicket of black pawns hems in Zvjaginsev’s black bishop on c8, so Zvjaginsev is effectively playing with one piece fewer than Krasenkow’s White. Although the black pawns also obstructed the white bishop on e2, it did have many more attacking possibilities, and thus is a classic good bishop vis-à-vis Black’s bad bishop. Zvjaginsev’s resigned after another ten moves.

Finally, a bishop may be fianchettoed (from the Italian fianchetto meaning ‘flank’), for example after moving the g2 pawn to g3 and the bishop on f1 to g2. This can form a strong defense for the aforementioned castled king on g1 and the bishop can often exert strong pressure on the long diagonal (h1–a8). A fianchettoed bishop should generally not be given up lightly, since the resulting holes in the pawn formation may prove to be serious weaknesses, particularly if the king has been castled earlier on that side of the board.

Knights (Husan or Horse in Arabic)

Business Development. They hop around from meeting to meeting, client to client or vendor to vendor. They enjoy free reign. They have no master.

Knights, just like their business doppelgängers, more is a weird bendy way. Grandmasters and founders alike need to be aware of all the angles before putting these important resources into play.

In chess, just as in the startup world, there is a huge debate into whether or not a knight is more valuable than a bishop (by the way a rook is easily considered more valuable than either a bishop or a knight, so yay for developers!). In general knight and bishops are approximately equal in strength, but depending on the game (startups) situation either one may have a distinct advantage.

Less experienced players tend to underrate the bishop compared to the knight because the knight can reach all squares and is more adept at forking (a new reason why most business development executives have expense accounts for those corporate lunches and dinners).

Bishops usually gain in relative strength towards the endgame as more pieces are captured and more open lines become available on which they can operate. A bishop can easily influence (just like marketing managers and their influencers) both wings simultaneously, whereas a knight is less capable of doing so. In an open endgame, a pair of bishops is decidedly superior to either a bishop and a knight, or two knights. A player possessing a pair of bishops has a strategic weapon in the form of a long-term threat to trade down to an advantageous endgame.

Two bishops vs. king can force checkmate, whereas two knights cannot. A bishop and knight can force mate, but with far greater difficulty than two bishops. Another reason why marketing and business development tend to not get along too well.

In certain positions a bishop can by itself lose a move (see triangulation and tempo), but a knight can never do so. The bishop is capable of skewering or pinning a piece, while the knight can do neither. A bishop can in some situations hinder a knight from moving. In these situations, the bishop is said to be “dominating” the knight. How many business development executives have been complaining of waiting for marketing’s new campaign?

On the other hand, in the opening and middlegame a bishop may be hemmed in by pawns of both players, and thus be inferior to a knight which can easily jump over them. A knight check cannot be blocked but a bishop check can. Furthermore, on a crowded board a knight has many tactical opportunities to fork two enemy pieces. A bishop can fork, but opportunities are rarer than an Oak and Smoke tri-tip.

Enemy pawns are very effective at harassing knights because a pawn attacking a knight is not itself attacked by the knight. For this reason, a knight is most effective when placed in a weakness in the opponent’s pawn structure, i.e. a square which cannot be attacked by enemy pawns.

Whereas two bishops cover each other’s weaknesses, two knights tend not to cooperate with each other as efficiently, just like those Type A BD FTEs. As such, in chess at least, a pair of bishops is usually considered better than a pair of knights.

Interestingly enough, legendary World Champion José Raúl Capablanca considered a queen and a knight as a usually better combination than a queen and a bishop. I would personally bet the other way in business, and take a founder and a smart (digital) marketeer over a Founder plus BD resource anyway, well, except if the founder was a technical co-founder.

Finally, compared to a bishop, a knight is often not as good during the endgame. As the knight’s potential range of movement is more limited, this often makes it less suitable in endgames with pawns on both sides of the board. However, this limitation is less important in endgames with pawns on only one side of the board. Furthermore, knights have the obvious advantage of being able to control squares of either color, unlike a lone bishop. Nonetheless, a disadvantage of the knight (compared to the other pieces) is that by itself it cannot lose a move to put the opponent in zugzwang (see triangulation as well), while a bishop can. In this position, if the knight is on a white square and it is White’s turn to move, White cannot win. Similarly, if the knight was on a black square and it was Black’s turn to move, White cannot win. In the other two cases, White would win. If instead of the knight, White had a bishop on either color of square, White would win with either side to move. Marketing beating business development, again and again.

Pawns

Employees. Not in the sense that pawns can be sacrificed, but in the sense that they are the vanguard (front line) of any company.

Grandmasters and founders alike know that both pawns and employees in their nature, must only move forward or simply perish (watch out especially when new employees take their first, highly motivated, double square step, you don’t want them getting slain en passant by your opponent’s pieces).

To paraphrase the musical chess master from France François-André Danican Philidor’s famous quote “Pawns are the soul of chess” — “Employees are the soul of a company.”

Remember, when pawns reach the end of the board (the ESOP promise land), they can be promoted into Queens! As Grandmaster Anatoly Karpov, the world champion before Kasparov, once famously said:

“the only difference between a prodigy and a patzer is how far into the future a player could see.”