My daughter, who teaches tennis for me during the summer but runs her own car-detailing business during the winter, said something interesting to me recently: “I make more working for myself.”
I smiled because I understood the sentiment. As she matures, she will come to appreciate all the costs associated with self-employment: insurance, taxes, equipment, marketing, transportation and the absence of a guaranteed paycheck. But knowing her—and knowing myself—I suspect she will willingly accept those costs in exchange for the opportunity to build something of her own.
She is an entrepreneur through and through.
At 14, she designed a logo, built a website, printed business cards and began marketing her car and truck detailing business. Today, when she is not teaching tennis or playing tournaments to maintain her UTR, she can detail as many as three cars in a day at $150 per car. She is now recruiting staff so that her business can service several cars simultaneously.
That sounds remarkably similar to what a successful Director of Racquets does: recruit professionals, build a team, create programs, manage schedules, generate revenue and assume responsibility for the customer experience.
It also raises an important question:
Are private clubs unintentionally excluding some of the racquets industry’s most entrepreneurial talent by insisting that every leadership position fit within a conventional W-2 employment model?
When the Position Changes, the Candidate Pool Changes
A prominent seasonal Director of Racquets position recently became available at Jupiter Island Club in Hobe Sound, Florida.
The outgoing director had originally hired me as an independent contractor several moons ago, and I worked at the club for five winter seasons. Before arriving, I had already served as a director at a smaller club in Jupiter. I carried workers’ compensation coverage, had obtained the appropriate exemption for myself in Florida and operated as an established independent business.
I even brought my own equipment and used my own software for bookings and payments. I worked hard and thoroughly enjoyed five wonderful seasons serving the club’s members.
I have always carried corporate liability insurance. As my company and its responsibilities have grown, I have increased that coverage to $8 million. I employ professionals, maintain business systems, invest in equipment and accept the financial risks that accompany operating a company.
The outgoing director had also operated independently. With his departure, however, the club decided that the seasonal position would return to W-2 employment.
That was the club’s decision, and I understand the reasons behind it. W-2 employment can provide consistency, institutional control, administrative clarity and important protections for both the club and the employee.
But the decision also changed the candidate pool.
Several strong prospects reportedly withdrew or lost interest once they understood how the position would be structured. I was not selected, but had an offer been made with W-2 employment as a nonnegotiable condition, I would have politely declined.
It simply would not have made sense within the structure of my existing business.
I already generate revenue through a substantial summer position and year-round consulting and management assignments. I maintain my own retirement plan, insurance coverage, business infrastructure and professional staff. A traditional seasonal benefits package would not necessarily compensate for the restrictions, opportunity costs and loss of independence associated with stepping back into an employee relationship.
I doubt I am alone.
In another recent search for a leading Director of Tennis position, the preferred candidate reportedly declined the offer after the club would not consider an independent arrangement. He had spent several years building his own business and did not want to return to W-2 employment.
The club had every right to maintain its preferred structure. The candidate had every right to decline it.
But the result illustrates a reality that clubs and search committees should recognize: the way a position is structured can materially alter the caliber and character of the people willing to consider it.
Classification Is Not Simply a Choice
There is an important legal distinction here.
A club cannot treat someone as an independent contractor merely because both parties prefer a 1099 arrangement. The title in an agreement does not determine the worker’s status. Federal and state authorities examine the actual relationship, including how much control the club exercises, who makes the financial investment, who supplies the equipment, whether the individual can realize a profit or loss, how permanent the relationship is and whether the person is genuinely operating an independent business.
A director who works fixed hours, follows the club’s detailed instructions, uses club equipment, supervises club employees and depends primarily upon that club for income may properly belong on the club’s payroll.
Calling that person an independent contractor does not necessarily make it so.
But that is not the only model available.
Instead of attempting to reclassify what is fundamentally an employee position, a club can consider genuinely outsourcing all or part of its racquets operation to a properly established management company. That company can employ its own professionals, carry appropriate insurance, invest in operating systems, manage payroll and accept responsibility for producing agreed-upon results.
That is a business-to-business relationship—not merely an employee receiving a different tax form.
Are Clubs Hiring Employees—or Seeking Business Leaders?
For years, the club industry has spoken about running a racquets department as “a business within the business.”
If clubs truly believe that, they should be willing to consider leaders who have actually built and operated businesses.
Entrepreneurs understand payroll because they have had to meet it. They understand revenue because their own survival depends upon generating it. They understand recruiting, retention, insurance, marketing, customer service and risk because those responsibilities cannot be passed upward to another department.
That does not mean an outsourced model is appropriate for every club or every position. Some clubs want—and need—a traditional employee who is fully integrated into the management structure. Others may determine that their level of operational control makes W-2 employment both the proper legal classification and the better business decision.
But clubs should make that determination deliberately, not automatically.
The initial question should not be, “Has this position always been W-2?”
It should be, “What operating model will best serve our members, protect the club and attract the strongest possible leadership?”
Expanding the Search
The racquets and golf industries may be overlooking an entire category of talent: experienced operators who no longer regard themselves primarily as employees.
These professionals have created companies, developed brands, hired staff, purchased insurance, assumed financial risk and built revenue streams across several properties or markets. Many will not abandon those businesses for a seasonal job, regardless of the club’s reputation.
A search limited to candidates willing to accept conventional employment will naturally exclude them.
That does not necessarily make the search unsuccessful. It does, however, make the talent pool smaller.
Before launching their next executive search, clubs should evaluate more than compensation, benefits and reporting lines. They should consider whether traditional employment, genuine departmental outsourcing or a carefully structured management agreement best fits their objectives.
The answer will not be the same for every club.
But if clubs are willing to question the default model, they may discover a larger and more entrepreneurial group of leaders—professionals prepared not merely to administer an amenity, but to build and operate a successful racquets business.
Ed Shanaphy is President of SBW Associates, Inc, the holding company of BeyondTheBaselines.com. After gaining his M.A. from the London School of Economics, he served as CEO of one of Europe’s largest entertainment and music conglomerates, Haysbridge (UK) Ltd, before returning to his native USA and establishing one of the nation’s leading management consultancies in the private members club arena. He looks forward to the day he can work for his daughter.
