"It’s not a bookkeeper — it’s like a colleague, a partner, really, truthfully. I can reach out to her anytime, have a conversation anytime. It’s all inclusive. I feel like I have this financial partner to work with me whenever I have questions."
— Betsy Ross, Certified Sommelier and Business Owner
The Challenge
Betsy Ross had spent decades mastering the wine world as a certified sommelier, building deep expertise in running wine programs and managing hospitality operations. When she opened Wine House on Main in December 2021 in Kennebunk, Maine, she assumed that experience would translate seamlessly into business ownership.
What looked like a charming small wine shop was actually two distinct businesses under one roof — a retail shop and a wine bar — each with separate tax requirements and reporting needs. A growing wine club added yet another layer of complexity requiring independent tracking. The financial architecture was far more demanding than Betsy had anticipated.
“In 2024, I didn’t even do taxes or look at my books once the whole year. I was doing it all myself by not doing it.”
The avoidance spiraled into crisis. Penalties for late taxes, improper filings, and missed deadlines began piling up. The mental weight invaded every corner of Betsy’s life — straining her relationships and making it impossible to be fully present with her young daughter.
“It was helplessness. I was like, I am not succeeding. I don’t know what to do. I am panicking.”
The Solution
The turning point came after Betsy invested in business fundamentals through Tony Robbins’ Business Mastery course, where she was introduced to Donald Miller. Following Miller on social media, she kept hearing about BELAY — though her immediate reaction was resistance. At roughly $500 a month, the cost felt out of reach for a business owner who couldn’t yet pay herself.
Then she did the math. Tallying up everything she’d spent on penalties, late fees, and filing errors, the calculation shifted entirely.
“I kind of looked at all of that and was like, wow, I’ve spent more money on that. I’d rather spend the money on someone who can help me not pay penalties, stay on top of things, and then all the other benefits that come with feeling confident because I now know where my business stands.”
In May, while undertaking a major renovation of Wine House on Main, Betsy secured a new bank loan and budgeted for proper financial support for the first time. BELAY matched her with bookkeeper Claire, who got immediately to work untangling a full year of neglected books. Claire implemented weekly reporting, built separate tracking for the retail shop, wine bar, and wine club, established systems to monitor waste and discounts, and ensured all taxes were filed on time — ending the cycle of penalties entirely.
“Something that was important for me was finding somebody who can talk to me easily. She knows how to talk to me to help me understand. She’s patient, she’s so kind.”
"I am not helpless anymore. I’m still financially growing, but it’s not helpless. Now there’s a path and a vision of how to work and build and grow. Where before I was just spinning, spinning, spinning."
— Betsy Ross, Certified Sommelier and Business OwnerThe Impact
The transformation was immediate and far-reaching. For the first time, Betsy had clear visibility into every segment of her business. The wine club — which she had been running generously without any real insight into its margins — became a vivid example of what financial clarity makes possible.
“I can see how much wine I’m giving away and need to change my tune. I can see how much waste is happening. Before I didn’t care about any of that because I just needed to stay afloat. Now we’re digging deep into these fine details and making adjustments that are better for the business.”
The partnership with Claire also redefined what a bookkeeping relationship could be. Rather than a transactional service that left Betsy with unanswered questions, Claire became a true financial collaborator.
“It’s not a bookkeeper — it’s like a colleague, a partner, really, truthfully. I can reach out to her anytime, have a conversation anytime. It’s all inclusive. I feel like I have this financial partner to work with me whenever I have questions.”
But the most profound change was personal. The financial stress that had consumed Betsy — straining her relationships and robbing her of presence as a mother — began to lift. What she gained wasn’t sudden profitability, but something she valued even more: a clear path forward.
“I am not helpless anymore. I’m still financially growing, but it’s not helpless. Now there’s a path and a vision of how to work and build and grow. Where before I was just spinning, spinning, spinning.”