How Koloa Kai Vacation Rentals Supports Sustainable Growth with Topkey

Jed Stevens and his wife Lisa Stevens Wegner have owned and operated Koloa Kai Vacation Rentals on Kauai since 2015, and they’re committed to growing their business in a unique way: slowly and sustainably.

“We’re never going to overstress our staff or compromise the service to our guests or owners for the sake of getting larger,” says Jed. “I get to take my son to school every morning and pick him up most days. I want my employees to have as much work as they want — but not too much, so they can enjoy their life.”

Those employees include three front-office staff, two maintenance pros, a business development rep, and a team of housekeeping and maintenance contractors. Jed and his wife split their time between Kauai and Newport Beach, CA, so having a strong local team is essential to their company’s success. After starting with a single property in 2015, Koloa Kai has grown to just under 50 by early 2024 — all while maintaining positive experiences for its owners, guests, and employees. 

Jed credits his sustainable success to a focus on efficiency. “We continually get better and more efficient at what we’re doing, and that increase in efficiency is what allows us to bring on new properties — because now, we can handle it.”

Before Topkey: constant reimbursements and operational redundancies 

To help facilitate this slow-growth approach, Jed and his team have adopted technology solutions like LiveRez Ignite, Breezeway, KeyData, Beyond Pricing, and Lynx to manage their portfolio. As an operations-minded business owner, Jed also heavily relies on Smartsheets and Quickbooks to manage his custom-built AP system. 

But for a few years, Jed and his team were dealing with a big roadblock to efficiency: financial operations. “As expense management goes, it was really messy,” he says. 

Jed had a personal credit card in his name for major purchases, but he wasn’t always on the ground. So when a property’s microwave broke, and a maintenance tech went out to fix it, they would often end up at Home Depot to buy a replacement — on their personal cards. Employees knew Jed would reimburse them right away. He set up a Smartsheet form so they could submit a request and send Jed the receipt. But the whole system didn’t sit right with him. 

“You’re asking them to lay out their money for the business, which isn’t fair,” says Jed. “They’re not equity stakeholders. For them to put in their personal capital at any point is kind of inappropriate.”

So Jed would send reimbursements via Venmo or Paypal the same day. But that only shifted the burden from his employees to his operational accounting.

“The last thing I want to do is ask employees to carry a balance for me, but paying them back the same day put a cash crunch on me,” he says. “I’m not pulling from client trust accounts to put money back on their card — I’m pulling from operational accounts. So if that happened early in the month, I would be carrying that balance for the owner for weeks.” 

Additionally, this expense management approach was far from foolproof, and took up a lot of Jed’s time and energy. “It was all carried around in my head,” he says. “I had to make sure that when I grabbed a receipt, I filed it in my file system, and then I remembered to put it on an owner statement. I’m sure there were things that I reimbursed my employees for that I didn’t get reimbursed by the owners properly for. I’m sure there were tons of leaks in my system.” 

This approach didn’t fit into Jed’s philosophy of enabling growth through efficiency. He needed to streamline his financial operations so he could level up his business. 

Introducing Topkey

Shortly after appearing on a customer panel with Breezeway in 2021, Jed received a LinkedIn request from our founder Jon. He wanted to see if Jed was interested in becoming a pilot customer for Topkey — a new financial operations platform designed specifically for the vacation rental industry. Jed saw the vision, and Koloa Kai became one of Topkey’s earliest customers. 

And once Jed could issue Topkey business credit cards to his employees, “It was a sea change,” he said. “The people in the field could make the purchases they need to make the properties function. Topkey made expenses frictionless.”

Today, six of Jed’s employees, plus Jed himself, use Topkey cards to make purchases on behalf of the company and its homeowners. With Topkey’s expense management system, reconciliation takes much less of Jed’s time and effort. 

“Everything comes into Topkey where I have the ability to categorize and track expenses,” Jed says. “Our number of transactions went up substantially, but I knew the categorization would be taken care of.”

Topkey benefits: protecting cash flow, saving time, and improving employee experience

With Topkey, Jed’s once-messy expense management system is streamlined and simple — leading to improved cash flow, valuable time savings, and a better employee experience. 

Protecting cash flow to support growth

As Koloa Kai added properties to its portfolio, Jed encountered a challenge familiar to the short-term rental industry: “Growth is expensive.” 

When new properties were onboarded, Jed would often frontload the expenses necessary to make a home guest-ready. But since he was reimbursing employees directly for many of those purchases, Koloa Kai’s cashflow was threatened. 

The employee credit cards provided by Topkey alleviated that burden. Now, Jed doesn’t have to dip into operational accounts to cover those costs and receives owner reimbursements through the client trust process in time to pay the cards in full. 

Saving valuable hours during crunch time

Before Topkey, Jed touched every transaction two or three times in order to close the books: when he reimbursed employees, when he categorized expenses within his own AP system, and when he categorized expenses again in Quickbooks, his operational bookkeeping software. Topkey eliminates these redundancies. 

“The ability to sync transactions from Topkey to Quickbooks is huge,” says Jed. “With Topkey, I categorize the expense by property and which of the accounts in Quickbooks it belongs to. Then I hit ‘Sync’, and it goes to Quickbooks, and I don’t have to touch it again. It’s a huge relief.”

For Jed, this translates to at least eight hours of time saved every month — but those hours are worth their weight in gold. 

“That time would come as a crunch during the month-end processing, not an incremental 30 minutes here and there,” he says. “I spend a lot of time and energy making sure that I’m not being crunched by multiple things at that time, because it’s when operational or other accounting stuff comes up. Those eight hours, for me, are worth about four times that number at the end of the month.”

Improving the employee and owner experience

Jed’s early system of reimbursing employees was “tough on employees, tough on accounting, and tough on operations,” he said. All that changed with Topkey.

“Topkey is removing obstacles for the people on the ground to get their job done,” says Jed. “It completely solves the problem of ‘How do I pay for this?’ ‘Am I supposed to pay for it?’ They have a card, and they know it’ll work.”

And if there’s ever an issue around spending limits — such as a maintenance crew buying multiple appliances in a given month — it’s easy to resolve. “I can get on the dashboard, bump up their limit, and they can immediately try again and make the purchase,” Jed says. 

Why Topkey: Koloa Kai values intentional design and continued innovation

Like many property managers, Jed didn’t fully grasp the complexities of short-term rental financial management until he was already running his business. 

“It’s a dichotomy of having both an accrual accounting system and a cash accounting system, and it breaks people’s brains,” he says. “By definition, a client trust account is run on an accrual basis — you’re not recognizing that income when you get a booking and take that chunk of the money. You must wait to recognize that income until the stay is complete, when you know the money has been earned. But your operations run on a cash account basis. When you get money in, that’s when you recognize it. You can’t just have Quickbooks run your client trust accounting system unless it’s run on an accrual basis.”

And he believes that complexity requires a purpose-built solution — a tool that bridges the gap between these two different accounting processes. 

“What’s really awesome about Topkey is the intentionality built into it that can help you route the charges that need to go back to the client trust accounting system in a way that makes sense,” Jed says. “But you can also send that same information to your operational accounts. Topkey is built in the middle to help both of those processes work properly. That’s the secret sauce that can be hard to understand until you really experience it.” 

Additionally, Jed appreciates working with a company that listens to feedback and continually invests in improvements to make the product easier — and more powerful. 

“When I choose a partner to work with, one of the main things I look at is not just what is their current offering — but where are they going? What are they going to be developing?” Jed says. “I’d say right now, Topkey has already developed a best-in-class solution. But I’m confident they’re going to continue to develop and add features. A bunch of suggestions I’ve made along the way have been listened to and some have been implemented. The company’s on a great track and I’m happy to continue to be working with them.”

At the end of the day, Jed is structuring his own business around driving efficiency to empower sustainable growth that creates a better life for his family, his employees, and his owners. Topkey makes that possible by streamlining and securing Koloa Kai’s financial operations — and Jed believes other managers like himself can benefit in the same way.

“The companies that make the headlines are the big ones that are moving fast and growing huge,” Jed says. “But I think the real story is that most of the property managers in the space manage between 20 and 60 properties. If we help empower these people to do it really well, we can improve lives on three sides of the transaction: the owners who are going to get better service and better money, guests who are going to get a more consistent and higher-quality stay, and business owners who are able to make a better living and have a better life. By working with these systems that make efficiency possible, we can achieve all of that.”

Financial operations can create headaches for property managers of all sizes — and we’re here to help. 

Schedule a demo to see how Topkey can streamline your STR finances. 

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‍*Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC.

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