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Pools, Fun, Profits, and a New Wave of Opportunity with Derek Callow

Skimmer
Updated:  
March 27, 2025

What do Google, YouTube, Tinder, and Swimply have in common? 

Well, for one, they’re all brands Derek Callow has worked for. But there’s an even stronger thread woven through each of these brands—the one that drew Derek to each of them. They’re all brands that connect people. 

When Derek met Swimply founder Bunim Laskin in 2019, he was struck by Bunim’s passion for connection. So when the opportunity arose to join the company as COO in 2023 , Derek took it. He hasn’t looked back since, taking over as CEO in October 2023. 

When Derek stopped by the Between Two Stops podcast to chat with host Niki Acosta, he shared his thoughts on Swimply as a connector—of communities, guests, homeowners, and pool pros alike. 

At Swimply, fun and safety go hand-in-hand

Swimply began as a tool to help homeowners rent out their underutilized private pools by the hour. Today, the platform is much more than that. Their offering has expanded to hot tubs and cold plunges, saunas, sports courts, and more. Mainly, the Swimply mission is to connect people around the idea of getting outside and having fun.

For Swimply hosts, offering a fun environment also means offering a safe one. “The hosts that lean into Swimply really pay attention to detail,” says Derek, and they’re looking for ways to consistently offer a top-notch experience to all their guests.

The more Swimply hosts learn about quality service, however, the more they tend to realize that it’s not something they can provide on their own at scale. As the load on each pool increases, the situation gets more complex. “Sometimes people will shock their pool in a way that changes the color, and then they need to ask for help,” says Derek.  

How Skimmer helps Swimply hosts offer a safe experience

At Skimmer, the number of pool pros working with short-term rental pools has gone way up. For these clients, higher loads on the weekends mean getting the pool ready on Thursday and doing a follow-up visit on a Monday or Tuesday to make sure it’s rebalanced. 

Skimmer makes this all a lot easier, both for pool owners and pool pros. Skimmer’s service history feature helps protect against liability by allowing pool pros to upload photographs and create a referenceable service history. 

And though higher-volume pools need more attention, Derek notes that this is just the cost of doing business. “The revenue generated by pool owners can offset the cost of pool care,” he says. 

He’s also noticed that the conversation within the host community is less about finding cheaper pool care and more about finding better pool care. “Ultimately our hosts are in the hospitality business,” he says, and working with an expert pool pro allows them to deliver the best experience to their guests. 

Swimply’s reach continues to expand

Today, Swimply operates out of all 50 states in the US, as well as Canada and Australia. And it’s not just a big city phenomenon. Hosts in unique places have burgeoning businesses, simply because there aren’t a lot of pools around. “It just takes a handful of swimming pools and families,” Derek says, and the question of, “What will we do on the weekend?” 

Swimply plans to continue to expand, both geographically and product-wise (they recently introduced swim passes, allowing hosts to set up a monthly price for regular visitors). No matter what, they’ll continue to focus on creating new opportunities for connection.

Learn more about Swimply here, and don't forget to catch our full conversation with Derek below.

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