Business Coach Steve Sipress Delivers Guaranteed Results for ANY Business 

Marketing professionals need both an innovative spirit and plenty of persistence. Considering his nearly life-long embodiment of both characteristics, it’s no accident that Steve Sipress, Founder and President of Successful Selling Systems, has become one of the marketing industry’s most sought-after experts.

An Early Entrepreneur

Growing up in New York, Sipress learned firsthand the benefits of being one’s own boss. His father, a highly-awarded salesperson, worked from home and modeled for his kids the self-motivation and freedom such a position offered. Even more importantly, Sipress recalls his dad’s integrity and dedication to putting his clients’ interests first—leading him to become a top performing salesman and eventually an entrepreneur. He still made plenty of time for his kids, though, taking long weekends and enjoying fabulous vacations with his family. “Do you think I dreamed of life as a 9-to-5 employee? Not a chance,” Sipress smiles.

His mother, too, was an example to Sipress through her work. An English-as-a-second-language teacher to high school kids new to America, often here without their parents, his mom not only taught her students a new language, but inspired them to go after their dreams. “Wherever we went in town—whether to dinner, the movies—we would run into her former students, who now owned those businesses,” Sipress says. “They always thanked her for everything she did for them. That make a lasting impression on me, and I vowed to someday get similar responses from people I helped.”

Fortunate to have two strong role models at home, Sipress took their lessons to heart. As a kid, he was always on the lookout for opportunities to help people, as well as ways to turn any task into a competitive, business-like challenge. Even in grade school, he enjoyed being his own boss and reaping rewards based on the effort and passion he put into a job. From collecting bottles to turn in for deposit money to selling greeting cards and seeds door-to-door in his neighborhood, he was ready to tackle it. And when he landed a paper route only to discover that half of his customers had immediately cancelled due to the previous kid’s terrible performance, Sipress made it his mission to rebuild and expand the route by providing excellent, consistent service.

In high school, he was a food vendor at Madison Square Garden on nights and weekends, and worked two full-time jobs during the summer. But Sipress was also an honor student, pulling down grades good enough to get into Boston’s Brandeis University and then Boston College Law School. Naturally, he kept piling on jobs there, too. During undergraduate studies, he became the play-by-play announcer for three sports teams, hosted a call-in sports talks show, and rose to Sports Director and General Manager of the university’s radio station. Those positions led to a job as the youngest-ever producer of The Sports Huddle, New England’s top-rated call-in sports show—a job he held through his first year of law school. 

During law school, Sipress thought about incorporating his passion for sports by becoming a sports agent. But when he started working as a clerk and temporary legal secretary all over Boston, he discovered that he didn’t want to be a lawyer of any kind. Which is good, because he ended up flunking the bar exam—by only a single point. For someone who had worked and studied hard his whole life, it was a tough pill to swallow. 

In retrospect, however, he believes that failing the bar exam was the best thing that ever happened to him. “It was at that moment that I decided never to do anything ever again without giving 100 percent,” he explains. “Working full-time while in school, hanging out with friends while my classmates were in the library, and skipping classes because I thought I could just catch up before final exams had finally caught up with me. It taught me a huge lesson.”

Lesson learned, but he still needed a plan. Then a friend told Sipress about for-profit fantasy sports services. Sipress had organized and run fantasy leagues in law school as a way to stay in touch with his sports fan friends and family. But he had never heard of anyone else running such a game, and never considered doing it as a business. Excited about turning his hobby into a career, he kept his promise to himself of 100 percent effort. Thanks to effective marketing techniques and good old fashioned hustle, he was soon running a multi-million-dollar business—the largest in the fledgling industry. 

Making Marketing Work

Sipress made a lot of mistakes in that business, including turning down a multi-million dollar offer from an investor, and it went bust shortly after the Major League Baseball lockout of 1990. Once again, Sipress considers that business failure to be one of the best things that ever happened to him, because he has often been able to spot hidden major problems in his clients’ seemingly successful businesses, and turn them around before they become deadly. 

Having lost everything he had, Sipress answered an ad for management training in a door-to-door sales company. Though he had plenty of formal schooling, he considers those nine years of interviewing, hiring and training by example hundreds of salespeople to be the bulk of his education. In fact, it formed an essential foundation for the launch of Successful Selling Systems, his thriving consulting business. He’s been helping over a thousand small business owners and entrepreneurs in every conceivable type of business to implement effective sales and marketing strategies and systems. “My systems work so well that I am the only marketing consultant I know who has a money-back guarantee,” he says. “All my clients get at least a three-to-one return on their investment with me, or else they get their money back—and that hasn’t happened yet, because they usually get a lot more than just a three-to-one return.”

That kind of guarantee is possible when you’ve been running your own businesses and assisting others with sales and marketing strategies for over 30 years. His repertoire is vast, but Sipress specializes in direct response marketing. He believes that there’s power in simplicity, so he created The WOW! Strategy™, which makes it simple for every small business owner and entrepreneur to understand and start using marketing methods that deliver incredible results. 

He’s discovered that it’s essential to make his proven strategies easy to implement. The truth is that many small business owners are so focused on providing excellent products or services that marketing often takes a back seat. “Entrepreneurs make sure to get the very best people so they can put their best foot forward in the ‘doing’ part of their business, but they don’t put anywhere near as much time and investment into the behind-the-scenes areas of their business,” he says. “That’s especially true of marketing, which is the key to generating revenue and profit.”

When they do try marketing—with little to no return—small business owners almost always blame the medium (“No one reads the newspaper anymore” or “Google Adwords doesn’t work for my business”). Don’t give up, Sipress advises. Rather, the solution to disappointing results is to bring in a marketing expert who knows how to make that medium work, as well as many other marketing approaches that will pay off big time.

It’s impossible for a hands-on business owner to keep up with the ever-changing world of marketing, Sipress points out. That’s why it’s crucial to have a dedicated expert on speed dial. “The Internet has completely changed the world of small business marketing. And since the Internet is constantly changing, that causes stress and uncertainty for small business owners who don’t have a team of marketers working with and for them,” he says. “My clients not only get me—they also get my team of sales, marketing, and advertising superstars.”

But a whole new world of marketing possibilities doesn’t mean the tried-and-true approaches are obsolete. Sipress says the biggest misconception people have is that “old school” marketing methods like direct mail and radio advertising no longer work. “In many cases, they are working better than ever today, especially for those of us using the right strategies, such as in conjunction with Internet marketing,” he explains.

Still, innovation is in Sipress’ blood, so he never stops working towards new solutions for his clients. He recently launched his Automatic Contractor Profits system, specifically designed to help roofers, HVAC pros, remodelers, and other home service providers. Only one business within a given industry is allowed to use the system inside each geographical area, because it guarantees results for everyone who uses it. Up next, he’s creating similar systems for other types of small business owners.

The life-changing strategies Sipress introduces to clients—and the resulting growth within their businesses—is the most satisfying part of his career. It’s especially gratifying to make true believers of business owners who’ve been reluctant to maximize the power of marketing. “Marketing is where the money is,” he stresses. “And to get the very best returns, you need to take action by implementing extremely effective sales and marketing systems.”