How Outlive Homes scaled to 73 properties without hiring a finance team

Outlive Homes was founded by Harley Courts after he spent more than a decade building Nooklyn, the tech-powered Brooklyn rental brokerage business that completed tens of thousands of transactions and represented hundreds of millions of dollars in real estate volume.

After moving from New York City to Oahu’s North Shore, Courts wanted to build a new kind of boutique brokerage: one combining home sales, leasing, and property management, powered by modern technology and a mission that’s close to home: with every closing, the company removes 10 pounds of ocean pollution.

That became Outlive Homes, now operating in Hawaii and New York.

Outlive’s entire operation — across two markets, three business lines, and 73 managed properties — runs through a lean leadership team of only four people, with no dedicated back-office finance team.

Courts credits Mercury for helping make that possible. He knew from previous experience that scaling his businesses also introduced hefty financial administration: property expenses, owner distributions, agent commissions, taxes, security deposits, reimbursements, and incoming payments. Courts often had to add more headcount just to keep the financial operations running.

With Mercury, Outlive is doing things differently. Instead of scaling back-office headcount to support growing financial operations, Courts and his team now rely on a combination of Mercury products and features to keep their finances highly organized, transparent, and built directly into their account structure. Outlive uses:

• Sub-accounts that segregate funds automatically by property and purpose
• Auto-transfer rules that set tax reserves aside without anyone tracking them by hand
• Fast, flexible payments so owners and agents get paid however works for them
• An automated Xero integration that keeps the books current without repetitive manual entry

For Courts, the value of Mercury goes beyond just saving administrative time. Being able to set up the banking structure to reflect the way the team runs the business gives them a much clearer picture of what is actually happening financially.

It’s a setup he now encourages other owners and founders to adopt.

“The exciting part for me is that anybody starting a business right now has the ability to accept money, track money, and segregate funds in ways that gives them total visibility of their business and make decisions like a mature company, all while saving time,” Courts says.

Financial sophistication takes a specific shape at Outlive: sub-accounts split by market, property, and purpose. Hawaii and New York each have their own set of accounts. Individual properties get their own checking accounts, named for the address. And money is separated by purpose (e.g. whether it's a vacation rental, long-term rental or sale), so Outlive can keep funds organized rather than pooling everything into a single balance.

For example, a long-term rental account handles rent coming in and expenses like a handyman visit going out. A vacation or mid-term rental account works largely the same way, except the money comes from Airbnb payouts or direct bookings instead of a single tenant.

Some property accounts also carry a dedicated debit card, letting Courts and his team track spend down to the property level without adding another bookkeeping process.

“By segregating, it really gives you more control and power in your own business, because you’re truly seeing the numbers in real time, not just quarterly or annually, the way most businesses have to unless they have a full accounting team,” Courts says.

That property-level visibility is especially important to Courts because Outlive is managing someone else’s asset and income. If an owner wants to understand what came in, what was spent, or what happened at a particular property, the team can get to that information quickly rather than reconstructing it later from a large operating account.

Tax obligations get the same treatment. Rather than track reserves manually, Courts uses Mercury’s auto-transfer rules to turn dedicated accounts into automatic tax reserves, with a set percentage of incoming payments routed straight into a property’s tax account.

When tax rates change, Courts can update the percentage at the account level instead of reworking a spreadsheet or manually calculating and transferring reserves across dozens of individual payments — work that would likely need a dedicated bookkeeper just to keep up.

For a property that might receive 25 separate payments in a month, that automation adds up quickly.

Outlive’s clients span the spectrum from tech-forward Airbnb hosts to long-time landlords who still maintain a pen-and-ink checkbook ledger. Whenever Outlive collects funds on an owner’s behalf — from a signed lease, a home sale, or a vacation booking — some want a wire or ACH, and others want a paper check.

“Despite how digital and streamlined Mercury is, the fact that we can also just cut a check when we need to is unbelievable,” Zach Barden, Vice President and Principle Broker at Outlive notes. Mercury’s checkbooks let the team issue physical checks without leaving its Mercury-based bookkeeping, so nothing falls outside the reconciled system just because an owner prefers paper.

For their more tech-forward clients, Outlive uses Mercury Invoicing for direct monthly bookings. The team sends a payable invoice — with credit card payment enabled through a Stripe integration — directly from Mercury’s mobile app.

That same on-the-go access extends to how Outlive pays its own agents, giving the team the freedom to send commissions whenever and wherever they need to.

“Being able to jump on our mobile phone and pay an agent out for a deal in the middle of a meeting is really what keeps our agents happy and keeps us going as a company,” Courts says. “With a traditional bank, this process would not be possible.”

Money moves through Outlive from many directions — Airbnb payouts, Stripe invoices coming in, and checks and wires going out to owners and agents. But because Courts routes all of it through Mercury, it doesn’t matter which way it’s flowing because everything lands in one system he can see and trust.

The same applies to Outlive’s broader tech stack. As they’ve scaled, the team has brought in new software to handle different parts of the business. However, with Mercury’s integrations, Courts never has to worry about losing sight of their finances as Mercury provides a financial source of truth underneath the rest of its technology stack.

Integrations also power bookkeeping at Outlive. Transactions get categorized in Mercury first, and the Xero integration keeps the books current from there, with less manual work and no separate banking system to reconcile against.

For Courts, this results in having “the cleanest possible set of books imaginable.”

Since building its finance operations on Mercury, Outlive Homes has been able to:

• Run a lean, four-person team across two markets and three business lines without hiring a dedicated bookkeeper or finance team
• Keep 73 managed properties’ finances separated by using property-level sub-accounts, plus additional accounts split by market and business line
• Save on bookkeeping by automating tax segregation instead of hiring someone to manage it manually
• Give owners greater financial visibility by organizing income and expenses at the property level
• Pay agents and owners on their terms by sending same-day payments from a phone or mailing a physical check when that’s what an owner wants — all without leaving Mercury