Betsy Ross is a certified sommelier who turned a decade-old dream into reality during one of the most challenging times imaginable.
After years working in the restaurant and hospitality industry in San Francisco, New York, and Boston, the COVID-19 pandemic created an unexpected opportunity: she could move closer to family in Maine and finally open the business she'd been envisioning for over ten years.
In June 2020, Betsy made the leap from New York City to the small town of Kennebunk, Maine, to open Winehouse Maine — a unique concept combining a wine retail shop and wine bar under one roof. The idea was simple but powerful: capture those moments when customers fall in love with a glass of wine and ask, "Where can I buy this?"
But the timing was anything but simple. Two weeks before her move, Betsy discovered she was pregnant. She would become a new mom and a new business owner simultaneously during a global pandemic.
"Not crazy," she laughs now. "We opened in December 2021, and we're still here, still going for it."
The Wake-Up Call
Betsy had decades of experience running wine programs and managing operations. She assumed that expertise would translate seamlessly into business ownership.
"I thought, great, I'm just going to open up this great wine shop and wine bar and do all the things I love — all the things I'm really good at — and it's going to be a great success," Betsy recalls. "I realized quickly that being a business owner and learning business is a whole different animal."
What seemed like a straightforward small business was actually quite complex. Winehouse Maine operates as two businesses under one roof — a retail shop and a wine bar — each with different tax requirements and reporting needs. Within retail, there was also a wine club that needed separate tracking.
The financial complexity quickly became overwhelming.
"In 2024, I didn't even do taxes or look at my books once the whole year," Betsy admits. "I was doing it all myself by not doing it."
The stress compounded daily. "Every morning, every day going, ‘I have no idea what my financials look like.’ Should I take a look? No, I can't do it, I'm too scared."
The penalties for late taxes, improper filing, and late fees began to pile up. The financial weight affected every aspect of Betsy's life — her relationships, her ability to be present with her daughter, every interaction tinged with stress.
"It was helplessness. I was like, I am not succeeding. I don't know what to do. I am panicking."
Finding the Path Forward
About a year and a half ago, Betsy invested in learning business fundamentals through Tony Robbins' Business Mastery course, where she was introduced to Donald Miller. Following Donald Miller on social media, Betsy kept hearing about BELAY.
Her immediate reaction was resistance. "The whole time prior, it was like I can't afford it, I can't afford it. How could I ever afford $500 a month? I can't even pay myself."
Then Betsy did the math. She looked at all the money she'd spent on penalties, late fees, and filing errors.
"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, Betsy undertook a major renovation at Winehouse Maine. She went back to the bank for another loan, determined to turn things around. This time, she budgeted for proper financial support.
"This is an investment that is worth it. I've already invested that much in penalties, I'd rather invest in moving in a better direction."
Claire's Transformative Impact
BELAY matched Betsy with Claire as her bookkeeper, and the transformation began immediately.
"Something that was important for me was finding somebody who can talk to me easily," Betsy explains. "She knows how to talk to me to help me understand. She's patient, she's so kind."
More Than Just a Bookkeeper
Betsy had previously hired a bookkeeper who simply categorized transactions. Any questions required extra time and money. At the end of the year, Betsy had to recategorize much of the work herself.
Working with Claire through BELAY is completely different.
"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."
When Betsy identified the need to track discounts and waste more carefully, she reached out to Claire. "She's like, yes, let's do X, Y, Z. We're fine- tuning asin a way that this business is evolving."
What Claire Did for Betsy:
- Got the business completely caught up on all bookkeeping from the past year
- Implemented weekly reporting so Betsy knows exactly where she stands
- Separated wine club revenue and expenses to track this growing segment independently
- Set up proper tracking for the retail shop versus the wine bar
- Established systems to monitor waste, comps, and discounts
- Ensured all taxes are filed on time with no penalties
- Created monthly reviews to analyze performance across all business segments
"We connect with weekly reports. I know exactly where I am. It's just now a different shift. It's confidence now."
Claire also developed streamlined systems that removed the constant mental burden. "There have been multiple times throughout my day where I'm like, I don't have to think about that anymore. This is amazing. I know it's getting taken care of."
From Grey Areas to Clear Decisions
Before working with Claire, Betsy operated in what she calls the "gray" areas of business — borrowing wine from retail inventory for the bar, giving away glasses without tracking it, mixing wine club expenses with retail, and never understanding her true margins.
Now, with clear visibility into every aspect of her business, Betsy can make strategic decisions she never could before.
The wine club is a perfect example. "I'm like, I don't think I've made any money on this because I wanted to be generous, but I never knew."
Now she can see exactly how much she's spending, exactly how much revenue it generates, and where margins are being eroded.
"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."
Peace of Mind at Home and Work
The impact extended far beyond spreadsheets and tax filings.
"I was so stressed out everywhere in my life and panicked. It was affecting my relationship, my being a mom."
The constant weight made it impossible to be fully present. "Now I can really sit with my daughter, read books, and not think about looking at my bank account the next morning."
The shift wasn't about suddenly becoming wildly profitable — it was about moving from helplessness to having a 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."
The ROI That Matters
When asked about return on investment, Betsy is clear about both the tangible and intangible benefits.
"Certainly financially, I believe that it will pay for itself over time because now I have a clearer picture. But having that massive weight off my back, having that stress removed is worth it in itself."
She's already avoided the penalties that used to drain her resources, and she's gaining ground with strategic decisions she couldn't have made before.
Advice for Business Owners
For business owners who feel they can't afford outsourced bookkeeping support, Betsy's message is direct.
"Think about the other investments that you're making in your business. What are your important investments? Find out what those important investments are and just budget that right in."
She points to her own experience as proof. "I paid that much and more in penalties. Had I invested in that right away, certainly I would have avoided the penalties, but I would have been on a stronger growth path years ago."
Her final words:
"This has been a total game changer for me, truly. Having the support is great, but knowing I have the support has just been wonderful."