Just add water

David and Stephanie Ciccarelli spent the past two decades building the world’s leading online voice marketplace. Now, they want to rent you a vacation property. Say hello to Lake.com 

Photo: Stephanie and David Ciccarelli

TWO YEARS AGO this month, during a lockdown respite Omicron was poised to end weeks later, friends Lori Sweeney and Stephanie Neskas went out to listen to a mutual friend sing with her rock ‘n roll garage band. During a break in the music — influenced perhaps by the mixture of freedom and alcohol — Lori showed Stephanie a Grand Bend cottage listing on her phone and said, “We should buy this.”

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The women huddled with their respective husbands, Gregg and Brodie, passing around the phone to view pictures, yelling at times over the musical din to which others were dancing, and decided to do it — that night.

“In the third week of January, we drove through a snowstorm to see our new property,” Stephanie recalls. “It was the end of Covid, or so we thought, and we needed a passion project. It definitely was an impulse buy, but it worked out perfectly.”

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The couples had never purchased a rental ­property and had a lot to learn. “The biggest ­challenge was operational, figuring out how to turn it over from week to week, living in London. It took a while to find a cleaner up there, but once we did that, things started running smoothly.”

They listed the property, christened Woodpark Cottage, on various sites and have been fully booked almost from the beginning. Like thousands of other rental owners, from Grand Bend to Muskoka, the Okanagan to Cape Breton, they had to learn the ins and outs of marketing their cottage.

There are plenty of listing options, including market behemoths Airbnb and VRBO, but a London couple with a track record of tech success is about to enter the scene with their own bespoke site: Lake.com. By focusing on lake-adjacent properties and creating a community of like-minded owners and renters, David and Stephanie Ciccarelli plan to build a platform synonymous with lake vacations and experiences.

If that sounds like a daunting task, given the existing competition, well, it might be. However, the couple spent most of the last two decades founding and running Voices.com, growing it into the world’s leading online marketplace for voice talent. David recently stepped aside as CEO but remains, “a significant shareholder,” and continues to sit on the board.

When he says, “I don’t have any plans to sell my stake in the company,” he sounds a bit like a politician being asked to reveal his candidacy early. “I’m focused on maximizing the company’s value, even if that means being patient for several more years.”

Regardless of if or when Voices changes hands, the Ciccarellis are fully engaged in Lake.com. It went live in September in something akin to a soft restaurant opening. In the coming weeks, it will hit full stride, targeting 2024’s cottage season.

Like the rock ‘n roll friends, the Ciccarellis bought a cottage during lockdown. Theirs is in Muskoka and served not only as a family retreat but also as inspiration for their next business project, something they were only vaguely searching for when Covid arrived. (They also got a puppy Golden Retriever named Honey who did not influence their business choices.)

“During that strange time, we needed hope,” recalls Stephanie Ciccarelli. “David and I both thought a lot about our childhood memories at family cottages and near lakes. We were sitting in our Muskoka chairs, and he asked, ‘What do you think of Lake.com?’ That’s how we started thinking about doing this.”

As it turns out, they weren’t the first to think of the domain name Lake.com. Famously, they spent $30,000 two decades ago to acquire the Voices.com domain name. Acquiring Lake.com was a much more expensive proposition. “It definitely was more than Voices — sizeably more,” she says, without disclosing the sum. “A small fortune,” is how David describes it. “But we’re building a brand and want a strong name that says what we do in a single word everyone can spell,” he adds.

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The least surprising aspect of the new site is how many design cues come from the Voices site. “Some ideas just work online,” David says. The new firm has hired a former Microsoft UI/UX designer, “the best I’ve ever worked with,” he adds.

Relying on their Voices experience, it’s a safe bet the couple will have the company up and running at more or less full speed early in 2024, as planned. It is headquartered in rented Toronto office space, a nod to the plans for growth, although the Ciccarellis will continue living in London. “I believe I can build a bigger company than before in one-tenth the time with one-hundredth the cost,” David says. “We can be leaner because of the tools and technology available today.”

No amount of technology and experience can placate a movement in many vacation communities to control the number and nature of property rentals. In short, locals don’t want renters descending on their slice of heaven, partying late into the night, parking illegally, dumping garbage and generally behaving like Americans on a bus tour of Europe. Although, those Americans drop a fair bit of cash, and local businesses don’t want renters squeezed out entirely.

“I don’t think our neighbours are thrilled we rent our cottage,” Stephanie Neskas says, candidly. “But we talk to them a lot and are very careful with who rents from us.” The primary vibe at Woodpark Cottage is adult sibling reunions and multi-­generation vacations. Think of the scenario in many VRBO ads.

“We’ve learned a lot about who to rent to,” she says. “When we started, we weren’t even charging a damage deposit. We figured out a few things as we went.” Another lesson: A key to attracting desirable renters is to let everyone know your cottage has no bunk beds.

They have registered their property as required and demonstrated they have legal parking to match the capacity of their cottage. They’ve also noticed they get more mature, generally less problematic renters from VRBO listings, compared to Airbnb. The former takes a larger percentage for its troubles and offers insurance if repairs or clean-up is required after a rental. A local Grand Bend cottage rental site has been fruitful, as has a listing on Cottages in Canada.

Lake.com will charge a total of 13 per cent (10 points from listers and three from renters) which listers likely will roll into the rental price. That’s more than some competitors, but David says others charge up to 15 per cent, and the key really is which side of the equation pays what. In these early days, Lake is also considering offering a flat $500 annual listing fee rather than ­transaction fees.

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He also knows local regulations will present challenges. “We’re taking a lake-by-lake approach, building relationships with local mayors, tourism boards, boat renters and others in the tourism industry. We faced similar challenges with Voices.com, navigating union rules and concerns about copyright. If you engage stakeholders early and often, issues tend to fade away when it’s understood you have the customers’ best interests at heart.”

No one goes looking for roadblocks, but you get the sense solving those issues early in a company’s development is what David enjoys most. “I took Voices as far as I could. My sweet spot is growing from zero revenue to $25 million.”

That process for Lake.com starts in earnest next month. The roadblocks will be numerous, but the couple is armed with experience and funding to solve problems and still have some time to sit in their own Muskoka chairs, next to their lake, and enjoy the experiences they plan to offer customers across Canada and beyond. Christopher Clark