CHAPTER FIVE

A Letter to Mom

Dear Mom,

I finally got the chance to write you . . . after all these years. It’s just that I’ve been so very busy building my empire, my life and my future. Since I came out to visit you in California a lot has happened. I hope to come out there again to spend more time with you. I didn’t ever remember having one of those mother-son talks, like you see on TV and stuff.

Besides, I’m an adult now!

Meanwhile, I just wanted to take the time (at the beginning of my letter and on my 28th birthday) to say ‘I love you’ and that I’m doing everything I can with all that you have given to me. You always bounced back, Mom. With so many hard times that you faced. Financially, you struggled as an entrepreneur’s wife; forced to be resourceful. You were the homemaker, making our clothes and taking on the most stressful jobs to help keep the bills paid when Dad didn’t carry us. And you were strong, coping with Dad’s infidelities. You are so strong, Mother, and you have survived regardless of the odds.

One thing that I have indeed inherited from you and Dad is the initiative to work hard. Working hard for me is a natural: doing and being the best I can. I’m pursuing my talents relentlessly and by far, I’m feeling like the most resourceful black man on earth. All because of you. I don’t have one job, but so many responsibilities. Now, I haven’t been making my own clothes, like you once did, but I have been good at penny-pinching (being conservative) and cooking. When Stacy says she’s in the mood for pancakes, I know that means one thing or the other. She wants to be taken to IHOP (my lazy alternative) or I’ve got to get my black ass (oops!) out of bed and start making the batter. What a life! But just the same, thanks again, Mom.

I’m enclosing my latest videocassette of the TV show. It has an exclusive interview with Nancy Wilson that I know you’ll appreciate. Yes, Mom! Your son is reaching for the big time! Enjoy the tape and I’ll write to you again soon.

Oh! Stacy says hi!

Kiss, kiss,

Hug, hug.

Your son,

Douglass

Writing to his mother was a stretch for Douglass, since he’d been so far removed from the concept of family for years. His father was the nearest immediate member of the Gilmores that he related with on a day-to-day basis. And yet, despite how close they were with business affairs, the two were farther apart than they would have liked to admit. Convenience. That was the only “why” that kept them in close contact. But in the meantime, looking alike and (sort of) living together didn’t substantiate a bond. Being father and son was more or less coincidental.

Home Sweet Home

The Gilmore family, in the past 2 generations (at least), had never grown into a position of great wealth. Douglass couldn’t ever recall any relatives having more than a working man’s luxuries. At best, the really consistent aunts and uncles maintained their own homes, cars and middle class lifestyles, if merely due to hard, diligent work. But for sure, nobody moved to that level of affluence to deserve a 10,000-square foot, 24-room home with a 4-car garage. Not until Douglass learned about real estate.

In Douglass’s teen years, the family began to break out in different directions. Different destinies. His mother eventually sought a divorce. She left for sunny California to live with her parents who had retired there from New York decades before. Douglass’s two sisters simultaneously followed their mother to eventually marry into their own separate family start-ups. But, all told, the divorce between Mr. and Mrs. Gilmore left the family in shambles. With everyone left to sow their own oats in their very own mismatched worlds with no backbone, and no sound leadership or role models to turn to or rely upon.

Against those odds, Douglass still managed to spend many hours learning sales techniques and the many strategies of buying real estate with “no money down.” From seminars to the mail-order cassette courses, Douglass absorbed himself in the basics of finding distress properties, identifying the “don’t wanters” of these parcels, and he drew up his own offers for them. Before and during the issues which led to the breakup of his parents, Douglass was searching for a home. Inspired by pain that was pervasive and self-perpetuating in their Mt. Vernon home, he thought that closing on a new deal, a new home, in a new area might encourage a new family attitude. So for Douglass, although the Gilmores always had a roof over their heads, finding a home was necessary. And it wasn’t merely to keep the family together either because Mr. Gilmore was so busy with his own lifestyle that he had been neglecting the rent payments for 3 or 4 months.

Douglass searched for days, concentrating on the neighboring towns of Pelham and New Rochelle. He spent the most time in New Rochelle, where his parents had arranged for him to attend junior high school and part of high school. One day he stumbled upon a huge property that showed all of the signs he’d been looking for: Tall-as-hell grass. Dingy windows. Need for a paint job. This was the “don’t wanter” that he was trained to look for!

At first the home seemed unattainable because of its size. A four-story Colonial with a breathtaking panoramic view of the town’s main artery, North Avenue. This was a four-lane road that connected one end of New Rochelle with the other; the only road to do so. Just across the street was the town landmark, the Thomas Paine statue. It stood 25 feet tall and represented the history of the Huguenots, the army which battled under the leadership of then-General George Washington. To the immediate right of the house were two mile-long lakes, divided by a small bridge and walkway. Finally, just behind the lakes was New Rochelle High School, known best for its state championship-winning football team. It was also known as the #1 school in the country for its impeccable curriculum and grade-point average. Douglass also attended New Ro (the pet name for the high school) and kept no more than a A or no less than a C average in his classes. Yet he was an above average girl watcher. It was well after his school years, and his stint in the Marine Corps when he found this vacant corner property on North Avenue.

Part duty and part nuts and bolts know-how, Douglass sought out the homeowner. Digging into the town tax assessment records he discovered that the owner was a Japanese doctor who practiced acupuncture. He could not obtain a license to practice his profession in the United States as he hoped. He actually gambled on the process, but found himself caught between a rock and a hard place. Forced to continue his practice in London, the home which he’d purchased sat unoccupied for over 2 years. Thus, the New Rochelle home was useless to him and became the best-kept opportunity for an entrepreneur looking for a home.

Douglass contacted the doctor, and taking advantage of the circumstances, offered him $1,000 a month in a lease-option deal. The doctor appreciated Douglass’s aggressive approach. He wasn’t offended by the below-market offering. Instead, he was happy to have a committed buyer. Bottom line: this deal would be a family in the home, one that would hopefully take care of it, and the investment would continue to appreciate in value. This residential neighborhood was an attractive one, to say the least. Immaculately kept. It was quiet during the day and night, with the exception of garden workers, gas-powered mowers and leaf blowers in the early mornings. Every home had a large front yard. If the front yard was small, it was because of an oval driveway or a massive backyard. Most every home in the area had these amenities and all of the benefits of affluence.

950 North Avenue was no different from the rest. There was a great lawn in front, accentuated by a 230-foot oval driveway that curved around from one road to the other. The backyard was long and wide enough to fit another small home on. The house was an all-white Colonial with a crimson-red clay tile roof. There were even two addresses since the home sat on a corner property. 950 North Avenue faced the main road, while 11 Braemar Avenue enjoyed the scenery of the lakes.

The icing on the cake (a boost to Douglass’s ego) was to live just across the way from his old school where high school acquaintances used to tease him about his homemade orange tie, his high-water jeans and the overall miscoordination of clothing. The youngster had no sense of detail and nobody to show him style. But if those hecklers could only see Douglass now! He was living in a damned mansion! And it only added to his ten-ton collection of “last laughs” for everyone who was curious enough to ask themselves, “How the hell did he do that?”

Unfortunately, the doctor’s acceptance of Douglass’s offer did not come in time to salvage the family unity or to support whatever could be salvaged. So while his mom and sisters traveled westward, Douglass was left to live side by side with his father in this big home, with the most lavish living conditions, and his only responsibility was the fun and excitement of managing the ever-popular family nightclub, Gilmore’s Fool’s Paradise.

The Beginning of an Empire

New Rochelle, New York, was and is considered suburbia. And yet this community, with its Good Morning America ways, has fast become a melting pot where residents from every other country have sprouted up faster than vines. Many Spanish, Haitian, Oriental and Caribbean immigrants found New Rochelle to be an even mix of city-like resources in the most suburban surroundings. Grass. Trees. Lakes and streams; all of these elements lending their energy to the clean air that contradicts the realities of the big city only 25 minutes south. That once-upon-a-time all-white town, with its all-white infrastructure, has been forced to rub elbows with and adjust to the realities of culture and all of the spices that come with it. These realities have even forced New Rochelle into an economic surrender, where over half of its commercial businesses, including banks and restaurants, have bailed out. Four big nightclubs closed permanently. So while the majority of the city’s large businesses fled or shut down, the new opportunities opened up for niche businesses which could adapt to the shift in this town’s new cultural realities.

All things considered, with his new home, his know-how and business savvy, Douglass embarked on a new plan. This would go further than his selling shoes door to door when he was 7, or his mining for Cabbage Patch Kids when toy store shelves went dry. This venture (he planned) would be a multimedia empire which focused on an experience that the world could not escape. Black entertainment. A fan and a student of black entertainment, Douglass enjoyed recording the events through the decades. The icons stood out like massive billboards: MOTOWN; BLACK ENTERTAINMENT TELEVISION; NO LIMIT; DEF JAM & ROC-A-FELLA RECORDS. Douglass observed the growth of these institutions, much like millions of others. But unlike many who simply observed, he vowed to be a part of it. The growth and popularity was becoming so obvious. Black artists were now being seen more on video. More and more, week after week, black artists would strike pay dirt until it was no longer unusual. Now, instead of rock and pop artists, urban music became a fixture on the world’s top pop charts. Finally, America was realizing the creativity, richness and longevity of black music, regardless of the skin color behind the sounds. This was music and entertainment that was just plain addictive. The beats, the bass, and the grooves were enticing. The days of K.C. & the Sunshine Band and Hall & Oats (groups that relied on soul) were replaced by a sea of newcomers. Not just The Whispers, Temps, Tops or Miracles. But new editions like Luther Vandross, Whitney Houston and Stephanie Mills. In their shadows came Boys II Men, Babyface, Toni Braxton and the many productions of Jimmy Jam and Terry Lewis. These groups among others moved into the top ranks of popular music. They were the new A-list, to the point that rock music began to question its own mainstream appeal. And bigger than that, this all had a profound effect on impressionable young men like Douglass.

He soaked it all up, absorbed it all. He knew that the world (overall) was accepting the truth. Black talent and black culture, as expressed through black entertainment. He watched how MTV even changed its format from a rock video channel, in order to keep up with black videos, black artists, rap artists and the many events which embraced the genre. Douglass recognized all of this and he vowed to play a strong part in it. In his manifesto—unsaid and undocumented—he pledged to create that vacuum which would inevitably seduce and attract the black community en masse, inviting one and all to his empire. SuperStar Communications. Brainstorming for a substantial company name wasn’t a tough task. The name would have to have some “umph”. It would also have to indicate technology, future and endurance. The name would have to flow. It would have to look good in bright lights. Yet it would have to be pleasant enough to be accepted as a household word. And finally, the name would have to stand on its own and overcome any shadow of a doubt by its mere mention. So Douglass chose “SuperStar.” He picked the word for its many meanings and for its self-prescribing decree of the very best. The “communications” tag on the company name was a natural, indicating there was information to be shared.

To claim and register this title as his very own universal address was a great feeling for Douglass. He felt as if he’d created a new, unprecedented home for the black entertainment experience. A simple $35 filing fee and some forms were the only necessary criteria for operating such a business in Westchester County. No specific licenses or permits were necessary, just a visit to the county clerk’s office and some deliberate ideas to create a cash flow.

Douglass tried to begin a singles organization, thinking that a weekly gathering of lonely, horny people would create that cash flow he wanted. But when that seemed more wayward than not, he did a little research and thought up a plan whereby amateur performers from the tri-state area would come together under one roof—one event. He formatted the event as a variety show so that any age and any talent might attend. Next, he set up an inexpensive registration fee of $10, affordable to most anyone. After an onslaught of street advertisement, there was a big reception and audition, after which over 500 performers were scheduled for an ongoing theme of shows with 25 or 30 acts per night. Furthermore, each entertainer was required to sell 10 tickets for each of their appearances. That would create revenue and bring a consistent audience of hundreds.

So it was settled. This would be a big event. And New Rochelle would be the home of his idea. Douglass went about addressing the event with a title; one with some credibility, because surely anyone could throw together a talent show. To lend some sort of traditional edge (without the need for any such approval or permission) and to additionally create the climate of a “community atmosphere” (as opposed to a business venture), Douglass named the event The Westchester Talent Competition.

Business and Pleasure

Talk of the big audition spread throughout the county and the state. The ads in the local newspapers, in pennysavers, on posters and by word of mouth, created the blitz of attention. The event was coordinated from his home office, and ultimately became the most talked-about talent showcase in the county’s history of entertainment. All along, he’d tell himself: “It’s going just as planned. Now, make it better.” He also placed ads on the local cable television community bulletin board. And as the $10 fees began to pour in, Douglass put the money back into television commercials that were placed on MTV, CNN and various other highly visible cable channels. But to his surprise, the print ads, television and word of mouth attracted nothing close to the amount of responses that the hand-made tree signs provoked. These were his most successful tools; those 400 modestly sized slices of sheet metal with an 800 number and the words “TALENT WANTED.”

So many signs were put up in so many high-traffic areas that the message became a nuisance. People began to call just out of curiosity, and even then, some signed up and got involved. Phone calls came day and night, and along with them came the flow of innocence and naiveté, ignorance and fever. A script was created, telling the average caller everything that an amateur performer with the fever to perform would want to hear. The script made no unfounded promises, but it was attractive and suggested that most anyone should ready their $10 application fee for a try at fame. Another technique which Douglass executed was to put the caller on hold momentarily. Douglass’s girlfriend Stacy would conveniently handle calls from the male respondents, while he accepted female callers. The idea worked well. They were both passionate about the event, and they both developed savvy as they became comfortable with the routine. Stacy always kept the guys’ hearts pounding. She excited them so much they called back frequently, asking for her by name. In the meantime both Douglass and Stacy were focused, asking all callers for their full name, address and phone number. The duo talked to callers for long enough to ensure that application fee would be in hand within a matter of days.

Although she was not experienced in any management capacity, Stacy handled the tasks of organizing and arranging like a pro. She maintained a certain wisdom, but was nonetheless subordinated by Douglass’s high expectations. Somehow, their relationship was overcome by need. Stacy needed a dominant figure in her life. Douglass was boosted by Stacy’s charisma, her submissiveness—how she put on that “little girl” act—and he was allured by her dancer’s features; the results of her formal training as a youngster. She had the look of a fitness instructor, with well defined calves, good posture, and that hip-hop-video ass. Stacy’s other assets were the tight B-cup breasts, the alluring, full lips and doe eyes.

Douglass sensed an air of adventure about Stacy when they first met. She was a tagalong of a mutual friend who was just stopping by the Gilmore home. Perhaps she was more like a delivery, since that mutual friend had been planning this all along. But once she made it to the house, Stacy mentioned something about knowing Douglass’s family.

“I went to school with your sisters, plus I was in your mother’s Girl Scouts group,” she told Douglass. Such words quickly earned Douglass’s confidence. And he easily soaked it up so that it didn’t take two days for the two to get intimate. Yes, there were those obligatory gestures of courting, like the flowers and phone calls. The two also did lunch at a classy Japanese restaurant. But eventually Stacy returned to Douglass’s house without playing “hard to get.”

“This place is crazy! It’s all yours?”

Douglass shrugged, not trying too hard to be humble.

“It’s so spacious,” she went on to say. “So much . . . atmosphere. And it matches you and your free spirit.”

“If that means it looks like a bachelor’s pad, then, yeah . . . I agree with you.”

“Nah. This isn’t a bachelor pad. Far from it. And besides, I never met a guy as organized as you.”

“Organized, but single,” said Douglass with that smirk.

Stacy stayed over that night. It was a long night of personal, but not intimate, conversation. The two even fell asleep fully clothed on Douglass’s humongous waterbed. In the early hours of the next morning, with the daylight barely showing through the bedroom window, Douglass woke up to find Stacy in heat. She was hovering close to him with an exploring gaze. From that moment, cruddy breath and all, the two connected with plug-and-play perfection. They began kissing and touching. The stimulation was both original and exciting, progressively taking them into a wild and frenzied session of feverish grabbing and groping. If there was skin exposed, it was covered or palmed or squeezed. They stretched their bodies and limbs to the limitless levels of their desires. They swelled with passion, and had no regard for birth control or prevention.

Stacy finally pulled Douglass’s naked body into hers. The thrusts invoked her cries, followed by a heavy stream of tears and sighs. She didn’t want to admit that she needed him, but he convinced her again and again that she did. In the heat of the moment, Stacy expressed that she did need him and backed it up with an emotional testimony.

“It seems like I knew you for so much longer. I know that sounds like a line or somethin’, like out of a movie, but it’s true,” she said tearfully. The confession hit a peak, and Stacy abandoned every discipline, giving into a flow of affection. She pulled herself even closer to Douglass, until they could be no closer—as if she altogether wanted to be inside of him. The heat between them was part of that soft yet aggressive friction between her Camay skin and his, two shades darker. There was an instant when Douglass continuously entered her, as if in some race for a power-finish. She bounced with him until they were both breathlessly waiting for an answer . . . for a finale . . . or for some July 4^th explosion. There was a definite end, and then neither of them wanted to move, if only to linger there in that ecstasy.

After a time, their bodies shifted and they rolled over so that she was on top. She circled her arms around Douglass’s neck, then in a soft-spoken tone, Stacy explained, “I’m not sad, just . . . just in disbelief.”

“Huh?” Her sincerity slowed him and a lone tear fell from her eye onto his cheek.

“Douglass, that was my first one.”

“First what?” he asked, bewildered and frustrated. Stacy looked directly into his eyes, expecting him to understand. Then she exhaled.

“My first orgasm,” she said with her eyelids contracting, finishing her sentence. Silly.

“Ooo-kay,” said Douglass before his own eyes asked, Now what?

Expecting the moment to be more eventful, but settling for whatever, Stacy began to kiss Douglass’s bare chest. She delicately lowered her head to his waist, observing his limp penis, still shimmering from all the sex. Then, with a certain determination about her, Stacey embracing him with one hand, she pushed her straight black hair to the side, but stopped to look up into Douglass’s eyes.

“Have you ever had any diseases?” She was bashful, but still had that sense of hope in her voice. As though his answer was irrelevant, Stacy unconsciously massaged him with her palm fully gripping his erection. Douglass looked at her inquisitively thinking that This must be some doctor shit.

“I mean like sexual infections or whatever?” Stacy affirmed her position with a more determined tone.

“N-no. Hell, no.” Douglass was simple and truthful and sincere. His face expressed that yuck! as if he’d envisioned the images of puss and infection.

“You sure?” She looked at him. Her eyes smiling and not really requiring an answer.

“Sure, I’m sure.” he answered definitely. But Stacy had already begun to lower her head. She purposefully took him into her mouth, devouring him with her cheeks tight and tongue consumed with his erection. She bobbed her head up and down on him, doing her best to maneuver on the water-filled mattress.

Meanwhile, Douglass was trying hard to maintain his sanity, all but rupturing with gasps and quivers. Stacy took things a step further, overwhelming his greatest expectations. She licked and kissed her way around and below his testicles. She adjusted his legs and knees until they were comfortably cocked. Then she kissed and slurped at what had (until now) been forbidden and taboo. Having never experienced the feeling before, Douglass was hit hard with feelings of exhilaration. He shuddered. He was speechless. Part of him was a little frightened. Yet Stacy became engrossed as if she was trying to impress or gain his approval. He couldn’t open his eyes because he was squeezing them too tight. He was tense. Squeezing his face like a weightlifter.

Stacy eventually revisited his erection with her swollen lips and she massaged him with both hands until he was completely spent within her jaws. Douglass just laid there in a state of comatose, stunned at how this woman just swallowed all of him just as easy as if he was her favorite milkshake. There were no questions left in his mind. Stacy was convenient. She was a freak who could curl his toes, and now (so to speak), this nymphomaniac belonged to him!

For two years the talent showcase went from small idea to a big bang. It grew rapidly into a cornerstone of New York’s entertainment world, introducing all things amateur. People traveled from as far as Florida and Canada to be a part of the weekly showcase. The videotapes from each weekly performance created footage and content which was neatly edited together into a 60-minute TV show. The show was named “The SuperStar USA TV Show,” starting out as a cheesy video production with poor lighting and sound. The continuity was horrible and choppy—as if a naive 2^nd grade student put it together. Even the response to the cablecast was discouraging. However, the core audience—families, friends and those performers—had no other choice. Gradually, even if viewers had to cope with the growing pains of an aspiring TV producer, the show eventually developed into an entertaining, hour-long presentation.

To accommodate the needs of performers, as well as to carry out the operations of this ever growing enterprise, Douglass had gathered a small but reliable staff of supporters. Darryl was the public access studio manager who originally showed Douglass basic studio use. Greg and Lou served as publicist and public relations directors, respectively. Huey was the stage manager for the various stage shows, and Rick hosted each live event. With this support, Douglass was inspired to grow and better his labor of love. Otherwise, the project might not have progressed past a few months. But it did survive. The t.v. show aired at 9PM every Saturday night—prime time airtime—on a channel that was wedged between CBS on one side and NBC on the other. This made it inevitable for any channel surfer to “stumble” into the world of SuperStar.

In time, the production of the show began to improve, and its regional audience also increased since Douglass began to syndicate the show; making copies and then distributing them to other stations throughout the tri-state area. Many hundreds of thousands of people were now tuning into SuperStar USA, forcing Douglass to get his shit together. He was on the front line, where he had no choice but to improve—improve or perish.

The benefits from the pressure was that Douglass not only grew as a talented producer, he also sharpened his skills at editing, camera angles and hosting. As the host of The Super-Star USA TV Show, Douglass performed hundreds of interviews with aspiring artists and debut artists, until he was very good at questions and interacting with just about anyone. Soon, major names began to fill the entire one-hour show.

The toughest interview, his first major (quote, unquote) celebrity interview was Phyllis Hyman. She originally declined his request for an exclusive. But perhaps the exposure to over 2 million viewers changed her mind, and she agreed—at least, over the phone. However, when Douglass and his 2 man camera crew showed up at the Blue Note Jazz Club for the interview, Phyllis still hadn’t completely agreed. Finally, Douglass confronted Ms. Hyman’s road manager, and addressed him with that same relentless desire—the drive of a man who had confronted rejection time and time again—and in the end the interview went down as scheduled. The dressing room, an intimate setting with classy couches and mirrors and flowers, Douglass handled his questions nervously, but somehow maintained an on-air professionalism. Halfway into the interview, he became more confident. He realized that it was actually the diva herself who was having the difficulty. He slowly took account of her off-stage realities and the problems that she encountered. Yes, this was his toughest interview. But only up until Douglass found that she was human too.

That first celebrity interview virtually broke down every conceivable barrier that Douglass had, or that he thought he had. In agreeing to come on the show, Phyllis was actually endorsing the show’s existence with a clever interview and stellar stage performance. Subsequently, Douglass’s struggle to earn SuperStar’s star-power, acceptance and notoriety virtually vanished. That particular episode of the show led to further interest. And suddenly, the show became appealing for big names. Nancy Wilson, Chaka Khan, Stanley Turrentine, Rachelle Ferrell, Pam (Foxy Brown) Grier, Ice Cube, Nia Long, KRS-One, Brandy, Shabba Ranks, Queen Latifah, Glenn Jones, and Keith Washington. The stars flowed into New York and SuperStar was the magnet, as there were no other New York–based shows that claimed such a diverse audience and track record of varying interviews. The popularity of the show expanded with bigger, live audiences, regional popularity and resources that promised a successful future in the music and entertainment industries. Douglass’s dream was becoming reality fast, without end.