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Wilmington Tennis is a Toronto-based startup that just wants to get people in the greater Toronto area on the court. The company's timing couldn't be better. With the rise of Canadians stars Milos Raonic and Eugenie Bouchard, everyone wanting to play tennis.

Wilmington Tennis is a startup that just wants to get people in the greater Toronto area on the court.

The company's timing couldn't be better. With the rise of Canadians stars Milos Raonic and Eugenie Bouchard, everyone wanting to play tennis.

But there's a not-so-small catch: this private company owns no courts of its own. Wilmington teaches people at their condos and homes, runs after-school programs in school gyms and partners with non-profits such as Tennis Canada and Jumpstart to give lessons to at-risk youngsters.

While things are moving along nicely for founder and program director Carolynna Gabriel – herself a competitive tennis player in her youth and a recent grad of the Ivey Business School at Western University – and her three-year-old company, the business needs more options for growth.

"Much as I love being a dispatch system, it's not scalable," says Ms. Gabriel. The company currently has two full-time staff and two part-timers. The number of instructors grows to15 in the warmer months.

Since launch, Ms. Gabriel has had her eye on the 101 courts at 39 Toronto District School Board schools that sit almost entirely unused. Some of them are so rundown they actually get locked in the summer.

So for the last two-and-a-half years, she's been trying to forge a partnership with the TDSB to share courts. The project might happen, but only after a lot of waiting, much confusion and lots of frustration for this business grad used to dealing with private companies and non-profits.

"The process has been so slow, we could have been teaching tennis for a third school year by now," says Ms. Gabriel.

Her approach would see her company offering free lessons to students during gym-class time – 50 hours per school per year – at 10 sites to start across the city. Wilmington would fix up the courts and maintain them. (About half of the courts would require $6,000 each for a resurfacing, the rest may need up to a $50,000 rebuild, per court.)

In return, the company would get access to the courts during off-hours to teach lessons to the public, for a fee of about $50 an hour, the going rate in the city.

"It's a fantastic opportunity to give us a home base, and set up mini clubs," says Ms. Gabriel of a potential relationship with the TDSB. Such a program would also allow the company to satisfy its ethical goals of giving back by getting more people playing the game. "Tennis has always been stereotyped as an elitist sport. That's what we are trying to change. You don't need to be rich to play tennis, you just need access."

But getting the ball rolling with the TDSB has been anything but easy. It took Ms. Gabriel nearly six months to figure out who to talk to at the board. "You go through five layers of administration and no one wants to talk to you or help you. If someone could have drawn a map for me, it would have been invaluable."

"This seems normal to me," says Anthony Taylor, principal of SME Strategy, a management consulting firm in Vancouver. He says of Wilmington Tennis' timeline and experience with public servants is fairly typical. "It's not [TDSB's] job to change things, it's their job to run things as they are. They're not inclined to change."

Even if a public organization likes an idea, there are layers of approval staff must go through. "We can't shorten the process," says Carla Kisko, associate director of finance and operations for the TDSB of working with public companies, not Wilmington specifically. "That's the way this works and it's part of our rules. And it's the right thing to do because we're dealing with public money." She says getting an idea anywhere with the board takes a minimum of six to eight months, as it moves through various committees and gets different levels of approval.

To get noticed in a highly structured organization, Mr. Taylor suggests finding people to champion your project. "You have to knock on a bunch of doors, talk to as many people as you can, wherever you go. You never know who is going to be the one to help you move it forward."

That means networking beyond the organization too. Attending events and galas where politicians, influencers, celebrities and businesspeople will be, and talking up your project is key. "Get in people's faces, that's what you have to do," says Mr. Taylor.

Be sure you have a strong pitch and that pitch is not just about your short-term goals, but a larger vision. "If that vision is big enough, you could get some big players on board." Eventually, you'll talk to someone who gets passionate about your project too, and has the right connections to trigger action.

For Ms. Gabriel, after more than a year of talking to TDSB officials and getting positive feedback, but little movement, she finally got an audience with school trustees. They loved her deposition and just a few months later the board issued a request for expressions of interest (REOI) – a precursor to a request for proposals (RFP) that finds out who in the market might bid on board-wide project related to tennis, and what they offer.

These kinds of RSPs are typical when it comes to public projects, according to Ms. Kisko. "We are a public organization and we have to open things up to competition."

For Ms. Gabriel, seeing that more than 30 other organizations have downloaded the REOI documents means her competitive edge is long gone. She doesn't have access to anything more than the company names – but most are paving companies. "I'm confident we have a strong position."

But furthering her anxiety is the fact that the deadline for the REOI was bumped three times throughout the fall of 2014. No one's been clear on when the decision will be made. "I'm worried the entire 2015 season will be lost," she says.

Mr. Taylor says the public procurement system is such that even innovators can lose out, so it's important not to keep your eggs in one basket. If you win with a public contract, you can win big. If you lose, you want to make sure that you also have other, smaller projects in progress.

Importantly, avoid looking at your time and energy investment in a public project as a potential waste. You need that first big client to prove you can deliver. In Ms. Gabriel's case, landing one school board will give her the clout to replicate her model in other cities. "You need to keep pushing a big idea along, it'll be worth it in the long run," says Mr. Taylor.

Already other jurisdictions are calling Wilmington to ask about tennis lessons. For Ms. Gabriel, the long slog through a public process may be over soon.

The rules may be different here than they are in private business (and on the tennis court), but there are rules you can understand over time.

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