Daven Michaels and the art of leaving the shop

The opening party had everything a young clothing designer might want: a Melrose address, a fashion show, people worth photographing. Then Daven Michaels opened the doors for business, and hardly anybody came. In his recollection, the first days were quiet enough to make the debt feel very loud. He had borrowed to get the place going. A good party, it turned out, was easier to arrange than a paying customer.

He tried staying open late. There was a restaurant and bar next door; perhaps a drink would improve someone’s appetite for new clothes. Eventually, a customer bought something. Then came the episode he still enjoys telling: while Michaels was out running errands, Jack Nicholson visited the showroom and bought clothes for friends attending a Prince concert. The famous customer arrived at a useful moment. Michaels, naturally, missed him.

The business was precarious, the adjustment was practical, and the breakthrough involved another person. Across the years that followed, the 123Employee founder would repeatedly rearrange those ingredients. He would also keep asking how much of himself a business was entitled to consume.

An empty shop, then an audience

Michaels began designing clothing for musicians at fifteen. He remembers an only-child household where his parents encouraged his ideas, including the foolish ones. The early customers were musicians with limited audiences. Then music television helped turn appearance into part of the performance, and the young designer found himself working in a business whose audience was expanding rapidly.

He recalls dressing acts including Prince, Madonna, Cyndi Lauper, Duran Duran, and the Thompson Twins. These are his memories of the work: backstage access, travel, and the strange acceleration of watching small rooms give way to much larger venues. For a teenager interested in making things happen, it offered a fairly persuasive alternative to sitting still.

Yet he has resisted giving himself exclusive credit for the timing. He talks about preparation and relationships, then leaves room for good fortune. Plenty of qualified, hardworking people, he observes, never get the result they hoped for. There is some relief in hearing a founder admit that the universe occasionally supplies the lighting.

“Proximity is power.”

Daven Michaels

A pager, a party, a production crew

His next substantial change was into communications. The starting equipment, as he describes it, was modest: a telephone, a desk, a chair. Within five years, he says, the company operated in sixty American cities. He sold the business in a deal involving equity, and a subsequent acquisition added to his financial room to maneuver.

This was the pager era, when a message on a small device could send somebody searching for a telephone. The technology belongs to another landscape now. The business problem is recognizable: reach people, coordinate the work, and make a service available beyond the place where its founder happens to be sitting.

With money from the exit, he returned to entertainment. He organized electronic-music events, performed as a recording artist, and moved into music production. He remembers events drawing audiences in the tens of thousands. The work put him on both sides of the performance: bringing people together and giving them something to gather around.

Television followed. He was entering a field he still had to learn, so he hired people who knew the work. They taught him as they did it. He acknowledges that his television period produced no major hits. That is a useful detail in a career otherwise easy to compress into applause. The staff could teach him production; they could not guarantee an audience.

The freedom had to be organized

The outsourcing business emerged from work he needed done himself. An initial team in the Philippines helped with his own operations; the possibility of offering that arrangement to other entrepreneurs developed from there. The attraction was practical. Smaller companies needed marketing, customer service, and administrative help, even when they could not assemble a large staff around the corner.

123Employee became the business built around that arrangement. Its enterprise offering describes voice services, online and offline marketing, customer service, and virtual assistance. Its Philippine work centers supply the physical infrastructure behind work a client can commission from elsewhere. A remote business still has people showing up somewhere.

One early employee, Carl, occupies a particular place in Michaels’s telling. He describes paying performance bonuses that helped Carl fund his education, help his sister through school, and send money to their mother. The account gives an individual face to an industry more often discussed through hourly costs. For Michaels, the relationship became part of the reason to persevere through an uneven beginning.

He has also been precise about the life he wanted his company to support. Travel mattered. So did pursuing projects without being permanently stationed at a work center. Systems and colleagues made that possible. The laptop was the portable end of a larger arrangement.

His advice about what to hand over has a revealing commercial qualification. In a later business conversation, he recommended outsourcing income-generating activities that a team can effectively perform, so the additional revenue can help pay for the help. Routine tasks can follow. A founder with a narrow budget may find that a more useful starting point than simply clearing the most irritating jobs from a to-do list.

His own remote-team guidance is less breezy than the travel pictures might suggest. He emphasizes recognizing weaknesses, finding the right personal role, and hiring well. A video about the subject was filmed on Maui. The setting is pleasant; the instructions concern preparation, management, and rewards. Even a business run near a beach needs someone to decide who is doing what on Monday.

Putting the operating manual between covers

Outsource Smart, published by McGraw-Hill, turned these operating questions into a book. Its subtitle makes the intended bargain explicit: be your own boss without letting the business take over. The book became a New York Times bestseller, giving Michaels an audience beyond the people buying staffing services or attending a talk.

Its contents are tellingly practical. There are chapters on hiring and training a virtual assistant, managing the relationship, creating leads, maintaining websites, producing articles and video, and checking quality through both good and difficult periods. The promise of more time occupies the cover. Inside are the jobs required to earn it.

Books became another business. At Michaels Press, which he founded and leads as CEO, the work includes editing, design, marketing, and helping entrepreneurs develop an author platform. The team includes book strategist Michael Drew. Michaels had learned how a book could carry a business idea into new rooms; the publisher helps other entrepreneurs attempt their own version.

His writing interests extend beyond instruction. His catalog includes The Virtual Entrepreneur, a story about a businessman confronting his own failures, while Michaels Press also lists The Mad Hatter. Fiction gives him another way to work with ambition and its consequences. His career has supplied plenty of material about what people want from success, even when the book is not an operating manual.

The next room is in San Juan

Puerto Rico gave this long interest in people a local address. Michaels made the island his home and founded San Juan Social Club. He has described wanting to bring people established on the island together with newcomers for conversation. The format gave a traveling entrepreneur something rather specific: a community to return to.

There is continuity with the music years. A gathering needs a place, a reason to attend, and enough care that people want to come back. Rooftop events, dinners, travel, and cruises offer different settings for the same social work. The subject of the conversation has changed since the dance floor; the need to bring people through the door remains.

The project now extends into publishing and recorded conversations. San Juan Social includes a magazine and podcast alongside its club and cruise offerings. Michaels’s business broadcasts feature entrepreneurs and other people working on the island. His current conversations include the practical work of making introductions, finding resources, and connecting groups that may otherwise pass one another without meeting.

San Juan Social Club reports more than 7,000 members since 2022 and more than 65 events hosted. There are now several ways to stay in touch with the community between gatherings. A member can take part in a room, on a trip, through an interview, or on a printed page.

Three thousand reasons to show up

One of the clearest examples of what the network can do sits outside the usual business-event photograph. In a toy drive with Vimenti, the club collected 3,000 gifts. Michaels oversaw the collection. Families connected with Vimenti and the Ernesto Ramos Antonini community received the toys, with the organization’s staff helping handle distribution.

Families chose from educational and entertainment gifts. Its executive director, Barbara Rivera Batista, thanked the club for helping preserve the excitement of the holidays. A collection total can sound abstract until it becomes a table of things children can pick up and take home.

There is a satisfying distance between that scene and the anxious Melrose shop. In the first, Michaels needed people to come in and buy something. Here, he had helped bring people together to give something away. Both required organization. Both depended on getting beyond a good idea and persuading other people to take part.

His career has kept changing its clothes: fashion, communications, music, staffing, books. The recurring ambition is easier to recognize. Build the arrangement. Find the people who can make it work. Leave enough room to have a life, and enough reason to invite somebody else into it.