The Vintage Software That Lives On At Chess.com

The Vintage Software That Lives On At Chess.com

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| 225 | Fun & Trivia

Chess.com wasn't always Chess.com, as you know it today. In the days before millions of members, before Puzzle Rush or Chessable/Courses, before you could even play a game with someone halfway across the world, there was a small chess software company that needed a web address. Now, more than 30 years later, you can still enjoy that company's product right here on Chess.com. This is a story about vision, persistence, and survival. 

To begin, imagine you're living in the 1980s, even—especially—if you never actually did. There is no Chess.com, which is already not great if you want to play a game and no one else around you does. But it's even worse for training tactics. Books of puzzles—diagram after diagram, usually organized by theme, with solutions in the back—are pretty much your only option. But surely there's a better way?


Background

Ralph Nagel didn't even begin studying software until he was 27, but he was still a professional engineer before he ever considered creating his own chess program. In 1987, he began working at a chess software company called Heuristic Software, a job that would permanently turn Ralph into a lover of chess software.

In the 1980s, chess computers were still in their earliest stages. By the end of the decade, however, you could buy them for the home. This bad boy, sold at Radio Shack, was rated about 1800 Elo at maximum difficulty: 

The name "2150L" was aspirational, with an actual strength rather lower.

Ralph worked for Heuristic, which made that board and other chess electronics, for four years. "It was amazing," he says. "A fully running, established company with IMs on staff, [it] got me hooked on chess and chess software."

But Heuristic did not survive as a company, losing its contract with manufacturer Saitek in 1991. The next year, Ralph had an idea for a chess puzzle program and created a prototype, but he wasn't satisfied with it. Until one day...

The Vision

The original prototype Ralph wrote only offered one hint to the puzzle solver. That's still one more hint than you get from most books of puzzles, of course. Nonetheless, "when you look at the answer to a tactics puzzle" in a book, Ralph notes, "if you are not correct, the answer is now completely given away. The process, the experience, the struggle of discovery is no longer possible." 

The trick was finding a way to overcome this problem. Heuristic's collapse had left Ralph working construction when he had the idea for what he calls stepped hints: "We were digging a stepped foundation into a very steep and rocky hillside," he recalls. "I was running a jackhammer for days, cutting the two foot steps into the hillside." And that's when the idea hit him: What if the solver, instead of hoping to be right and checking the book, or relying on a single hint that may or may not help, could be guided along the way into a true understanding of the puzzle with hints as they went?

A hillside construction site in Saint Maarten like the one where Ralph Nagel had a realization that would launch the first content available on Chess.com. Photo: Paul Sableman/Wikimedia, CC.

After modifying his prototype, Ralph was satisfied. "Now I've got something!" he recalls thinking. But he still needed to turn his idea into a reality. It would be another year before he quit his construction job, satisfied that stepped hints could be patented.

Now I've got something!

—Ralph Nagel, after devising the stepped hints concept

Persistence

Ralph applied for a patent in August of 1993. It was finally issued in late 1997. Work continued unabated in the meantime on what would come to be called Chess Mentor. The new company, which Ralph named Aficionado, obtained the URL www.chess.com in 1994 for nothing more than the registration fee. Even with just a prototype of its product, Aficionado received a $140,000 publishing contract, with royalties, from a company called Interplay.

Ralph designed all of the functionality, screen layout, and designed every pixel of on-screen graphics. An old coworker of Ralph's joined the company and did the programming, with Ralph performing quality assurance.

But that wasn't all Ralph took on. He fulfilled all the orders himself. He would burn Chess Mentor onto a floppy disk, with a manual he would print himself, and mail it out.

Older millennials might still remember using a 3.5-inch floppy disk, but to anyone younger: yes, you could hold data on these. George Chernilevsky/Wikimedia, public domain.

Ralph was tech support and customer support, manning the phones himself and reading every one of the feedback postcards he had inserted that came back.

He was the marketing department—creating, writing, buying, and placing ads in Chess Life and Inside Chess magazines, and also pitching his product at chess tournaments, where he met another investor who contributed $75,000.

One of the ads for Chess Mentor, this one in the June 1996 issue of Chess Life (p. 17). Note the website.

Then there was the actual content, as we'd call it today. Several masters contributed, but none more than the late IM Jeremy Silman. Silman, who Ralph remembers as "off-the-charts funny," not only wrote the most content, but he also introduced another key idea: positional studies. The stepped hints could really shine as players not only could solve tactics but also understand the strategic complexities of a position, too.

A tactics problem in the Chess Mentor interface.

In many ways, Silman was the key to the whole project. "I wasn't positive that the whole system would work," Ralph recalls, "or that any masters would write for it. But Jeremy picked it right up, with no authoring system yet, and just volcanically turned out nearly error-free content. And we were off and running."

Jeremy [Silman] picked it right up... and just volcanically turned out nearly error-free content. And we were off and running.

—Ralph Nagel

Other titled players did endorse the product and/or contribute some material besides Silman, including GM Nick de Firmian, GM George Koltanowski, and IM John Donaldson

A still-unopened original copy of Chess Mentor on floppy disk.

By 1997, it was time to renegotiate the publishing contract with Interplay. Ralph outsourced the negotiations to his partners, the former coworker and the investor from the tournament, but things fell through. And then they fell out. By the time the patent was issued, Ralph was no longer part of the company.

Survival

By 2005, without Ralph, Aficionado was financially bankrupt. Chess Mentor and the www.chess.com domain name were sold off for $55,000, and one of the three cofounders of the company that purchased it was a Stanford Business grad by the name of Erik Allebest. Even following the purchase, the www.chess.com web address wouldn't begin to turn into Chess.com the company as you know it for another several months. In the meantime, the URL continued to serve as a pitch for Chess Mentor.

ChessMentor.com was just one click away from Chess.com during the transition period.

In 2006, Silman introduced Erik and Ralph to each other, and they have retained a correspondence to this day.

If you know where to look on Chess.com Lessons, you can still find Chess Mentor material right now, going on 30 years after its creation. And not just find it, but use it. Here's a screenshot from our Critical Challenges lesson, which still namechecks the company: "This module contains a sampling of challenges produced by various members of Aficionado's staff, shareholders, and endorsers including GM Walter Browne, GM Nick de Firmian, IM John Donaldson, FM Mike Arne, and NM Art Wang."

The specific study pictured can be found here and was one Ralph wrote himself.

As for Ralph himself, he admits things weren't easy after his departure from Aficionado. Still, he got his last job in part because his interviewer had bought a copy of Chess Mentor. Ralph was able to stay with that company into retirement, where he continues to enjoy chess. "Mostly my rating is in the 1300s," he says. But the game "is still so interesting and satisfying... Chess is a bloodless blood sport. Go is more elegant... but there's no blood. No drama."

Ralph not only still plays chess, he teaches it, first to his own kids and grandkids, and now in schools.

A brochure for Ralph's chess club.

As for what Chess.com became, Ralph is a fan, and he continues to play on Chess.com daily as he has since 2007. "It was gratifying to see Chess.com grow and do everything I'd ever thought of, and things I'd never imagined. A hell of a lot better than seeing Chess Mentor die." 

It was gratifying to see Chess.com grow and do everything I'd ever thought of, and things I'd never imagined. A hell of a lot better than seeing Chess Mentor die.

—Ralph Nagel

Ralph and IM Danny Rensch with a copy of Chess Mentor in December 2025!
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Nathaniel Green

Nathaniel Green is a staff writer for Chess.com who writes articles, player biographies, Titled Tuesday reports, video scripts, and more. He has been playing chess for about 30 years and resides near Washington, DC, USA.

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