When you're building a pet services empire across three states with 37 independent contractors, every minute spent on payroll is a minute you're not growing your business. For Carolina Carver, founder of Tails N' Trails, her old payment system wasn't just inefficient—it was threatening to cap her growth entirely.
Carolina started Tails N' Trails in 2017 because she saw a gap in the market. After years of paying high prices for her dogs' care—and being disappointed by traditional daycare facilities—she built something different: an outdoor-adventure-focused pet service that matches dogs with consistent, vetted caretakers for off-leash hikes, personalized walks, and in-home boarding.
"I really hated working in a corporate position, and I was paying so much money a day to have my dogs exercised," Carolina explains. "I just felt like there was this need for an outdoor doggy type daycare where you can take them on hikes."
The business model worked. Tails N' Trails grew from a solo operation to 37 contractors across Southeast Wisconsin, Central Massachusetts, and all of Rhode Island. Carolina recently completed an eight-month process to become a certified franchise—meaning she's now poised for national expansion.
But rapid growth brought a challenge that nearly derailed everything: her financial infrastructure was actively working against her.
Before Found, Carolina was using Venmo to pay her contractors. It worked fine when she was small—but as the team grew, the cracks became chasms.
"I would reach points in the week where I would max out in the amount of money I could send. And so then I would have different walkers paid on different days of the week. So every single day, I had to do a different payroll... Oh, my God, it was so bad. It was such a pain in the ass."
The problems compounded:
Weekly sending limits forced her to split payroll across multiple days
No centralized contractor database—searching for walkers among millions of Venmo users and hoping she paid the right one
Zero customer service when troubleshooting issues arose
No 1099-NEC generation for tax season
Personal and business payments mixed together—impossible to separate costs
"If I wanted to pay contractors, I would have to individually go to each person, I would have to look at my bank account," Carolina recalls. "It would just be like ten little steps in between sending the payment."
For a business that now runs payroll twice monthly for 37 people, those extra steps were eating hours of Carolina's time—time she desperately needed for everything else on her plate.
Carolina considered traditional payroll providers like Gusto, but the cost structure made them prohibitively expensive for a contractor-heavy business. "I pay 37 contractors, give or take. I did the math, and if I were using Gusto, I'd be spending around $2,600 a year just on contractor fees." For a service-based business where every dollar counts, that expense would eat directly into her margins—making growth even harder.
Carolina discovered Found while searching for a better way to manage contractor payments. What immediately stood out was the all-in-one approach: a dedicated place for all her contractors, instant payments with no sending limits, and automatic 1099 generation for tax time.
Today, Found isn't just another tool in Carolina's stack—it's the payment backbone of her entire operation.
Her workflow is elegantly simple: Pet Pocketbook (her scheduling software) calculates what each contractor earned for the pay period. Then Carolina opens Found, types in each walker's name, enters the amount, and hits send. Repeat 37 times.
"What used to take hours now takes me 45 minutes. I've kind of mastered it, so it's very quick. I can even do it from my phone."
Compare that to her Venmo days: "It would probably take me like three times the amount of time." That's over two hours saved every single pay period—four or more hours saved per month, just on the payment process itself.
The math is clear: Carolina went from spending 2+ hours on payroll (spread painfully across multiple days due to Venmo limits) to 45 minutes total, completed in one sitting. That's a reduction of at least two-thirds in time spent on contractor payments.
But the time savings extend beyond just the payment process. Because Found centralizes all her contractors in one place—separate from her personal Venmo contacts—Carolina can find and pay anyone instantly. "With Found, I use it just for my contractors. So it's very easy for me to find that person," she explains. "Whereas if you type a name into Venmo, it's like millions and millions of people."
Perhaps more valuable than the hours saved is the mental burden lifted. No more juggling multiple payroll days. No more worrying about hitting sending limits. No more searching through a sea of Venmo contacts.
And when tax season arrives, Found automatically generates 1099-NECs for each contractor she’s paid more than $600 in a calendar year—something Venmo simply couldn't do. Carolina sends these directly to her accountant, eliminating the manual, error-prone process.
"Sometimes walkers will ask me for a pay stub," Carolina notes. "While Found isn't making an exact pay stub, I can go in and click on their history of payments for the year, and then it will create a PDF that shows a list of all the payments that I sent them with the dates." This functionality helps her contractors secure apartments, car loans, and other services that require proof of income.
One stark contrast from her Venmo days: actual support when she needs it. "I can get a reply pretty instantaneously, or at least within a few hours," Carolina says. "With Venmo, you might have to wait... there wasn't a whole lot of customer service."
With Tails N' Trails now a certified franchise, Carolina is thinking about scale in a way she couldn't before. Every new franchise location will need a reliable, efficient way to pay contractors—and Found is already written into her franchisee manual.
"I have already included in my franchisee manual that Found is how they pay their contractors," Carolina explains. While she wants to give franchisees some flexibility, her logic is straightforward: "I don't know why they would choose to do something else when it's already like a clear way of running it."
New contractors are onboarded to Found from day one. Carolina has a Walker Guidebook that walks new hires through setting up their Found account, ensuring seamless payments from their very first paycheck. Standardization means any franchise owner can replicate the same efficient payment process anywhere in the country.
The time Carolina saves on payroll gets reinvested into what actually grows her business:
Handling client inquiries for Wisconsin and Massachusetts locations
Managing expansion projects like the franchise certification process
Implementing new systems such as her recent AI phone system
Personal flexibility—spending Wednesdays with her 2-year-old daughter, riding her recently rescued horse, Merry Mae
"My flexibility—honestly, that's probably like the number one thing," Carolina reflects on what she loves about running her business. "You can't do those types of things necessarily if you work for a business or something like that."
Found helps protect that flexibility by keeping the administrative burden low, even as the business scales.
With Found as her payment infrastructure, Carolina is focused on aggressive expansion:
Selling her first franchise locations with Found already baked into the operations manual
Continuing to grow contractor teams in existing markets
Expanding to new regions as franchise demand grows
"Follow our journey on Instagram as we open more Tails N' Trails locations," Carolina invites—confidence that comes from knowing her backend operations can scale with her ambitions.
Tails N' Trails' story shows what becomes possible when your payment infrastructure works with you instead of against you. Found is more than a business bank account—it's the all-in-one financial platform that lets entrepreneurs like Carolina focus on their mission while the platform handles the complexity of managing contractor payments, 1099s, and growth.
For a business built on the premise that pets deserve better care—and that entrepreneurs deserve the flexibility to build the life they want—having the right financial partner isn't just convenient. It's what makes everything else possible.
Carolina Carver founded Tails N' Trails in 2017 to provide personalized, outdoor-focused pet care that prioritizes consistency and relationships over traditional daycare models. The company has grown to 37 contractors across Rhode Island, Massachusetts, and Wisconsin, and recently became a certified franchise. Learn more at tailsntrailspets.com.
Disclaimer: The information on this website is not intended to provide, and should not be relied on, for tax or legal advice.
¹Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. The funds in your account are FDIC-insured up to $250,000 per depositor for each account ownership category. FDIC insurance only covers the failure of an FDIC-insured depository institution.
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Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. The funds in your account are FDIC-insured up to $250,000 per depositor for each account ownership category. FDIC insurance only covers the failure of an FDIC-insured depository institution.
¹Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, Member FDIC. The funds in your account are FDIC-insured up to $250,000 per depositor for each account ownership category. FDIC insurance only covers the failure of an FDIC-insured depository institution.
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