April may be the month known for its much-needed showers, but rain or shine, one day this month, planner Steve Cassaday and the 15 members of his firm, McLean, Va.-based Cassaday & Co., will pick up the litter on a 1.5-mile stretch on Leesburg Pike, which runs through scenic Great Falls. The good deed, which Cassaday has spearheaded for several years now, is just one of several civic and charity events he helps organize each year in the greater Washington, D.C., area.

While other planners marvel as their work weeks grow, Cassaday really does seem to have it all-a sizable firm, lots of time to devote to both charities and his family and one of the biggest personalities you'll ever want to meet. Shyness is not a word in Cassaday's vocabulary. So it is not surprising he quantifies his success by readily admitting that he makes six to seven times the average annual advisor income of $100,000 and works just 30 hours a week to do it.

How does he run a firm with $330 million in assets and still manage to spend a year as the president of his local Financial Planning Association chapter? Or take his family skiing on the Park City, Utah, slopes that were used by Olympic skiers just a couple months after the Cassadays were there? "My objective is to make myself obsolete in this firm," Cassaday says, only half joking.

He works toward that goal, according to those who know him, by using a pragmatic approach to practice management. In fact, Cassaday is unabashed that he is capable of building his firm around his personal goals. The 450 clients who work with Cassaday & Co. (the typical client has about $1.5 million) generated about $2.4 million in revenues in 2001. Most are former federal government employees in their early sixties who have retired recently or are planning to shortly. Cassaday expects to grow the firm's by 10% to 15% "without breaking a sweat." He's also not shy about telling reporters that he likes really nice homes, cars and vacations.

"It's true, his personality is a little bit bigger than the average planner's," laughs Paul Jurgensen, a senior vice president and advisor with Advest in Washington, D.C., who knows Cassaday from the FPA and area tennis courts. "But his personality fit in with the FPA because he brought in leadership capabilities. He's enhancing the finances of the organization, and it shows," Jurgensen says.

Like a lot of former brokers, he adds, Cassaday broke with the traditional brokerage model and applied his ability as a successful salesman to planning. "I think his firm is on the cutting edge," Jurgensen says.

Today, he's routinely called upon by the FPA and other groups to elaborate on how he uses his "delegate, eliminate and automate" brand of practice management to gain personal and financial freedom. One of his favorite topics is his "go-negative early" philosophy. Unlike many advisors, who spend hours doing preliminary planning work to impress a prospective client whom they may never see again, Cassaday uses his psychology degree from Radford College to do what he calls a bit of ethical persuasion. "We go negative right away," Cassaday says. "We tell the client: 'We're expensive. You have to transfer everything to us, and you have to adhere to our rigid discipline of investing.' Essentially, we get people to tell us why they have to work with us. If someone isn't convinced, we've only wasted 15 minutes."

Cassaday wasn't always so supremely confident. Frankly, he's spent a few semesters at the financial services industry's school of hard knocks for salespeople. He started his career as a broker with Johnston, Lemon & Co. right after graduating from college in 1977 and became the regional brokerage firm's youngest vice president. He was recruited three years later by EF Hutton & Co. But there were a few storms brewing on the horizon. For one, several Hutton brokers in his office perpetuated a check-kiting scheme on unwitting investors.

Fearing what bad publicity could do to his own book of business, Cassaday accepted an offer to assist in the opening of a PaineWebber office in Old Town Alexandria, Va. The office closed three years later, thanks, he says, to questionable management decisions and the 1987 market turmoil. Cassaday found a new home at Prudential Securities as a senior vice president and assistant branch manager in 1988, but he was already growing disenchanted with the brokerage world and being buffeted by others' bad decisions.

Then disaster struck, and Cassaday and his wife, Mary, lost their 22-month-old daughter in a horrible accident. Cassaday says he decided then and there that he was going to spend more time at home with his family. "I wanted to make a significant amount of money without having to work 40 hours a week," he says. He discovered Royal Alliance, which remains his broker-dealer today and finally made the leap to independence in September 1993.

Despite the break, his former life followed him. A longtime client sued Cassaday over limited partnerships. "The arbitration started just after my leaving," the planner says. "It was the worst thing that happened to me. Not only did I not do anything wrong, it was completely unfounded. In the '80s, you sold partnerships. Anyone who didn't wasn't in the business." To Cassaday's relief, PaineWebber and Prudential paid to settle the case. Still, it was an eye-opening lesson when one friendly client who filed a grievance told him it was nothing personal, but the client's attorney told him he'd be "crazy" not to sue.

The reality of launching his own business quickly absorbed Cassaday's attention. Working off a card table in his living room, Cassaday employed the help of his wife and a neighbor and spent the better part of 24 hours filling out client-transfer cards. He brought 95% of his clients to his new firm.

Today, Cassaday's fee-based firm practices asset allocation, and he invests along with his clients in a carefully selected group of about 45 mutual funds. Most client portfolios are fairly homogenous, and Cassaday makes no apologies for it.

He also doesn't brag about the pounds of planning his firm provides. "I don't sense that they're believers in the necessity of the big book version of planning," says Tracey Baker, a planner with Coopers, Jones & McLeland Ltd., in Fairfax, Va. Baker, who also knows Cassaday from the local chapter of the FPA, says his firm is more apt to take the big picture view, saying to a client: "You're here and you need to get here."

Cassaday admits that he's unlikely to produce cash-flow analysis detailing how much clients should spend on toilet paper. He did thousand-page plans in the 1980s that he says are useless today. "Clients want to know that you're watching their money, you've developed a strategy for them, you give them easy-to-read reports and an occasional love note."

It's not about overpromising either, Cassaday says. "What we say is: 'Here's our best guess. The chances of these actual numbers materializing are probably zero, but we'll send you a detailed explanation every 90 days and have as many discussions as you need."

"We don't find a lot of worth in binding a 40-page document that's going to change in a year," concurs Barry Glassman, one of Cassaday & Co.'s four senior planners. These days, the firm's planners find more value in client contact, even meeting monthly with some clients if the situation warrants it. "We tell clients to call us with anything that has a dollar sign in front of it. We helped a client who's been in a car accident buy a car and other clients figure out if a 15-year or 30-year mortgage fits their needs."

The family-centered life Cassaday was so determined to create more than a decade ago has become a reality, and his extended "family" gets bigger all the time. To celebrate two of his sons getting to play hockey at the MCI Center in Washington, D.C., Cassaday brought his entire staff. He followed it up with dinner and a Washington Capitals game for everyone, says Linda Stewart, the firm's director of client services.

Last year, Cassaday's family grew to include a group of less-privileged teenagers in Washington, D.C. Under his direction, the local FPA chapter sponsored its first charity gala, raising almost $38,000 to benefit The Good Samaritan Foundation, a program that provides year-round mentoring and academic and leadership training to a select group of high schoolers.

"Steve took the reins, and at no small cost, really made the event shine," says Baker, a local FPA board member.

"He's a man of his word," says The Good Samaritan Foundation's executive director, Eugenia Mercer. "And I understand he's convinced the FPA to do it again this year."