To get out of DIY-ing the books: Pilot saves Caroline from studying accounting. She gets to spend her time out with clients.
See which expenses to cut: Caroline can open Pilot’s dashboard to run quick calculations and see if she can afford a business trip, and what tradeoffs to make.
Tax prep as part of the package: Vogue Voyage’s books also prep her for Pilot to do the taxes.
"Pilot means I’m able to focus on networking, work on trips, do marketing, travel, and all the things that go into building a business."
On that sabbatical between jobs, Caroline and her partner signed up for an itinerary from a travel agency which quickly fell apart. The activities felt mismatched with their personalities and the open-top jeep tour got rained on. They had to cancel most of those plans.
There in the Azores, watching the downpour, she thought, “You know what? Maybe this is what I want to do.” She’d traveled extensively, was creative, was organized, and seemed to understand intuitively the kind of memories people tended to seek on trips. Plus, she’d be more thoughtful. “Ultimately, I want to be that person for any of my clients where they can dream and I can make it happen,” she says.
Creating a website and finding clients for Vogue Voyage was easy, as she’s naturally outgoing. But the back office wasn’t. That’s why she found Pilot. With Pilot handling the bookkeeping and taxes, she’s free to jet set on more business development trips, and be sure they earn a return
Working in tech had taught Caroline to be a systems thinker and left her adept at managing her own time. “If you’re dedicated to your craft and disciplined, it’s easy, in a way. You’re doing exactly what you want to do with your time!” says Caroline. “But you do have to be disciplined.”
She was also clever about advancing the business on her own schedule. She’d initially assumed she’d need to be certified in travel planning, so she bought a textbook. Six days into reading it, she landed her first client. So she set the book aside and did more networking.
“I'm naturally very relational, so I found meeting with clients and networking easy,” she says. “Spending time in entrepreneur circles and the networking communities has been really fun and very fruitful. Especially because, when you do what you love, that shines through.”
But coming back from the high of meeting people to log into QuickBooks and figure out whether an expense should be a “cost of goods sold - contractors” was always dreary. “The hard stuff is all the backend stuff,” says Caroline. “Which a lot of entrepreneurs say. You get into it to do what you love. And then there comes bookkeeping. That’s why I hired Pilot.”
You get into it to do what you love, and then there comes bookkeeping. That’s why I hired Pilot.
In any new venture, you’re learning all day, every day, and that’s mentally taxing. Try to move beyond creating your product to figuring out your own finances, you can easily get overwhelmed. It’s like two separate roles: Visionary and operator. It’s hard to do both.
“You’re wearing a million hats and everything’s moving and eventually you learn you just have to play to your strengths,” says Caroline. She outsourced the tracking credit card expenses, tax prep, and managing the ledger to Pilot. Pilot gives her a clean portal to log into, which syncs all her banks and credit cards. She can pull charts to look at cash flow, and her Pilot bookkeeper asks her questions and manages things.
Caroline uses Pilot to:
Pilot helps me decide what not to spend on, so I know where to invest.
Pilot’s support has allowed Caroline to focus on finding more clients, and inventing new offerings. She recently signed up her first membership client, who hires her on a sort of recurring subscription. It’s better for both parties because the more Caroline helps them plan experiences, the more she learns about what they do and don’t like, and can give even better recommendations. It’s also consistent, recurring revenue, which is vital to any services business.
“Being organized in the back office allows you to actually just execute what you're good at and do the things that got you into this business,” says Caroline. “Having that backbone of a structure that just works on its own. So you're not overthinking things and distracting yourself. Not having to work on the backend stuff is such a relief.”
Being organized in the back office allows you to actually just execute what you're good at and do the things that got you into this business.
They say it takes 100 hours to make a new friend and it’s similar with an agency—you’re always making new time investments in people and partners. Every hour Pilot saves Caroline, she gets to reinvest in listening to what people want. “It’s not just about what you’re offering, but really truly listening to those you’re working with,” she says. “It's knowing who to take verbatim and who to read between the lines with, and putting in that extra thoughtfulness to make it the easiest it can be for them.”
She’s been able to carefully manage her income and keep expenses low, which means she can afford to travel for fun and research at least once a quarter. She’s growing her network in Nashville, Atlanta, and Dallas, and putting extra time into Istanbul, Athens, Champagne, and Provence.
“My friends joke that I’m just traveling for fun and that it’s all leisure, but anyone who’s started a business knows there’s loads that goes into it,” she laughs. “I’m definitely not on a catamaran all day—I’m renting a car and driving to every single beach in Crete and filling Notion up with photos so when a client asks for a suggestion, I can make a match that makes their dreams come true.”
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Vogue Voyage provides discreet, white-glove travel coordination exclusively for ultra-high-net-worth families and executives.
On that sabbatical between jobs, Caroline and her partner signed up for an itinerary from a travel agency which quickly fell apart. The activities felt mismatched with their personalities and the open-top jeep tour got rained on. They had to cancel most of those plans.
There in the Azores, watching the downpour, she thought, “You know what? Maybe this is what I want to do.” She’d traveled extensively, was creative, was organized, and seemed to understand intuitively the kind of memories people tended to seek on trips. Plus, she’d be more thoughtful. “Ultimately, I want to be that person for any of my clients where they can dream and I can make it happen,” she says.
Creating a website and finding clients for Vogue Voyage was easy, as she’s naturally outgoing. But the back office wasn’t. That’s why she found Pilot. With Pilot handling the bookkeeping and taxes, she’s free to jet set on more business development trips, and be sure they earn a return
Working in tech had taught Caroline to be a systems thinker and left her adept at managing her own time. “If you’re dedicated to your craft and disciplined, it’s easy, in a way. You’re doing exactly what you want to do with your time!” says Caroline. “But you do have to be disciplined.”
She was also clever about advancing the business on her own schedule. She’d initially assumed she’d need to be certified in travel planning, so she bought a textbook. Six days into reading it, she landed her first client. So she set the book aside and did more networking.
“I'm naturally very relational, so I found meeting with clients and networking easy,” she says. “Spending time in entrepreneur circles and the networking communities has been really fun and very fruitful. Especially because, when you do what you love, that shines through.”
But coming back from the high of meeting people to log into QuickBooks and figure out whether an expense should be a “cost of goods sold - contractors” was always dreary. “The hard stuff is all the backend stuff,” says Caroline. “Which a lot of entrepreneurs say. You get into it to do what you love. And then there comes bookkeeping. That’s why I hired Pilot.”
You get into it to do what you love, and then there comes bookkeeping. That’s why I hired Pilot.
In any new venture, you’re learning all day, every day, and that’s mentally taxing. Try to move beyond creating your product to figuring out your own finances, you can easily get overwhelmed. It’s like two separate roles: Visionary and operator. It’s hard to do both.
“You’re wearing a million hats and everything’s moving and eventually you learn you just have to play to your strengths,” says Caroline. She outsourced the tracking credit card expenses, tax prep, and managing the ledger to Pilot. Pilot gives her a clean portal to log into, which syncs all her banks and credit cards. She can pull charts to look at cash flow, and her Pilot bookkeeper asks her questions and manages things.
Caroline uses Pilot to:
Pilot helps me decide what not to spend on, so I know where to invest.
Pilot’s support has allowed Caroline to focus on finding more clients, and inventing new offerings. She recently signed up her first membership client, who hires her on a sort of recurring subscription. It’s better for both parties because the more Caroline helps them plan experiences, the more she learns about what they do and don’t like, and can give even better recommendations. It’s also consistent, recurring revenue, which is vital to any services business.
“Being organized in the back office allows you to actually just execute what you're good at and do the things that got you into this business,” says Caroline. “Having that backbone of a structure that just works on its own. So you're not overthinking things and distracting yourself. Not having to work on the backend stuff is such a relief.”
Being organized in the back office allows you to actually just execute what you're good at and do the things that got you into this business.
They say it takes 100 hours to make a new friend and it’s similar with an agency—you’re always making new time investments in people and partners. Every hour Pilot saves Caroline, she gets to reinvest in listening to what people want. “It’s not just about what you’re offering, but really truly listening to those you’re working with,” she says. “It's knowing who to take verbatim and who to read between the lines with, and putting in that extra thoughtfulness to make it the easiest it can be for them.”
She’s been able to carefully manage her income and keep expenses low, which means she can afford to travel for fun and research at least once a quarter. She’s growing her network in Nashville, Atlanta, and Dallas, and putting extra time into Istanbul, Athens, Champagne, and Provence.
“My friends joke that I’m just traveling for fun and that it’s all leisure, but anyone who’s started a business knows there’s loads that goes into it,” she laughs. “I’m definitely not on a catamaran all day—I’m renting a car and driving to every single beach in Crete and filling Notion up with photos so when a client asks for a suggestion, I can make a match that makes their dreams come true.”
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