We first offered customers the chance to trade stocks using a touchtone phone (and later, a personal computer) under the name Accutrade. We needed our advertisements to explain how the service worked but also to give customers a warning: when a stockbroker gave them “advice,” it was just the firm’s company line. Asking a broker for advice was like asking a ventriloquist’s dummy. So, for this ad from 1994, we decided to use Buffalo Bob and Howdy Doody, the dummy that starred in the famous 1950s children’s television show, to introduce them to a smarter choice, Accutrade. This spot angered a lot of the traditional brokers, but it was all true.

An Ameritrade subsidiary, Aufhauser & Company, offered the very first online trades.  You can see in this spot, which I did not help create, what the style of advertising was like before we decided to take a new approach.  Aimed at the most frequent traders, it’s a hard sell and nothing more.

In 1997, we rebranded the entire company as Ameritrade and lowered our price per trade to eight dollars.  At such a low price, I knew we could only make a profit if we had a huge increase in the number of customers.  That meant going beyond the sophisticated investors who had been our first customers and appealing to people who might feel stock trading by computer would be too hard.  Our new “8 Bucks” campaign featured ordinary people – a businessperson on her way to work, a firefighter, a guy who loves basketball – who felt excited about the low price and at ease with trading by computer.

By 1999, we were reaching a far broader and more diverse range of customers, but we still had to explain the difference between online trading and what had come before.  This ad used a lot of appealing emotional elements – a loving father and daughter, beautiful cars, a boat, even a cameo by a bunny rabbit – to make sure that our potential customers sat still to hear how our service worked and why it was better than trading with a traditional broker.

After more than twenty years of trading stocks for our customers, we got noticed by the national media.  In this profile from 1999, CNBC treated us like an overnight sensation and made some little digs at us for being from Omaha and having an office building in a shopping mall.  But we won their respect because the little startup from Omaha was now the sixth-largest online broker – and growing fast.

When we got started with touchtone and online trading in the 1980s, we were offering an alternative to the mainstream, “normal” trading.  But by 1999, we were the mainstream.  When online brokers, overwhelmed by the demand for their services, suffered outages, the media and the government demanded that we restore and maintain this now-essential part of the economy that we had created.  In this interview with Marketwatch from 1999, it’s clear how times had changed.

In 2000, we had an advertising breakthrough, even compared to our past successes.  Traditionally, ads for brokerage firms had been serious and boring like ads for banks.  I wanted something funny, to show that our service wasn’t just less expensive and faster, it was part of the good life.  We found it when OgilvyOne Worldwide hired Michael Maronna, a twenty-two-year-old, former bike messenger and film student, to play the part of Stuart, an irreverent office assistant who teaches his boss to trade online.  Stuart became a national sensation, and Maronna even made a cameo appearance at President Clinton’s annual White House Correspondents’ dinner.

Ameritrade was at the cutting edge of online trading technology even as it offered the lowest price.  But soon our competitors had the same general technology that we did.  Now we had to compete by showing people that they could reach their investing goals better with us.  This ad from 2001 shows that the Ameritrade customer could succeed where it counted.  She handles a nightmare boss and trades stock from her desk, all without losing her cool.

When markets are up, it’s easy to get people excited about trading.  But when there’s a bear market, it’s more difficult.  In this ad from 2002, we shifted our focus away from ease and price.  Instead, we emphasized how well-informed our customers became when they used our online analytical tools, and how quickly they could respond to shifts in the market thanks to our trading technology.  The Bear in this spot wins the game of pool, but the Ameritrade customer still comes away feeling prepared.

Just because we were winning over customers who were new to online trading, we had no intention of losing the sophisticated traders who wanted the most sophisticated analytical tools.  This ad from 2004 promised day traders that they could have as much success and fun as our less-experienced traders if they signed up for our deluxe offering, called Apex.  Winning and holding our customers was a never-ending effort, and it built the company into the largest online broker, measured by the number of trades, in the world.