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23 Jun The 8 Financial Challenges That Keep Business Owners Up at Night — And How You Can Improve the Numbers

Posted at 18:16h in Blog by

Running a business is a bold act of vision. It starts with an idea — maybe sparked by passion, necessity, or the refusal to settle for “good enough.” You take that idea, risk your time, energy, and resources, and begin to build something from nothing. You put your name on the line. You create jobs. You serve your customers. You pour yourself into the day-to-day grind, often with more grit than sleep, fueled by belief in what your business can become.

Because eventually, every dream meets the reality of operations. Payroll is due. Rent is due. Customers delay payments. Vendors raise prices. You may be working harder than ever — yet somehow wondering why your profits aren’t growing, or why the bank account looks thinner than expected.

Continue reading or partner with Siegel Solutions to take the first step toward financial clarity and growth.

The real test of any business isn’t just in the idea or the execution — it’s in the numbers.

  • Are you making money?
  • Are you keeping it?
  • Are you spending it in the right places?
  • And most importantly: do you actually know what your numbers are telling you?

 

These aren’t just financial questions — they’re leadership questions. Because numbers don’t just reflect your business performance — they shape your decisions, your confidence, your growth strategy, and even your peace of mind.

And when the financial side isn’t under control, everything else starts to wobble. Growth stalls. Stress builds. Uncertainty creeps in. You might even start questioning whether you’re truly succeeding — or just surviving.

The truth is, even experienced, successful entrepreneurs face these challenges. Because money problems don’t always come from lack of effort or ambition. More often, they come from a lack of clarity, structure, or support in the financial side of the business.

And that’s exactly what we’re here to explore — the financial pain points that keep business owners up at night, why they matter, and most importantly, how to turn them into strengths. 

Cash Flow Crunch

A cash flow crunch happens when your business doesn’t have enough cash available to cover expenses — even if sales and revenue look good on paper. This often results from late customer payments, unexpected costs, or poor alignment between when money comes in and when it goes out.

Cash flow is essential to daily operations. Without it, you can’t pay employees, rent, or suppliers — even if you’re technically profitable. A shortfall can lead to missed payroll, strained vendor relationships, or increased debt, and it pulls your focus away from growing the business.

How the numbers can be improved:

  • Forecast cash flow regularly to anticipate upcoming gaps
  • Tighten up invoicing and payment terms to get paid faster
  • Schedule vendor payments more strategically
  • Build a reserve fund to cushion seasonal or unexpected dips

 

At Siegel Solutions, we create rolling cash flow forecasts, help optimize your receivables, and provide real-time insights so you stay ahead of shortfalls, not surprised by them. With better visibility and planning, you can make smarter decisions and run your business with confidence.

 

Mounting Expenses & Shrinking Margins

Shrinking margins happen when your costs increase faster than your prices or efficiency. You may be making more sales, but rising expenses — like payroll, materials, or overhead — slowly eat into your profit without obvious warning signs.

Even with steady or growing revenue, declining margins mean your business is keeping less of every dollar earned. Over time, this leads to financial strain, especially if you’re putting in more effort without seeing a meaningful return. Profit erosion also limits your ability to reinvest, hire, or weather unexpected challenges.

How the numbers can be improved:

  • Review your gross and net margins regularly to spot early declines
  • Audit vendor contracts and supply costs to find savings opportunities
  • Adjust pricing based on value and market conditions
  • Refine or discontinue low-margin products or services

 

At Siegel Solutions, we help you analyze where your profits are going, identify cost leaks, and track margin trends over time. By using data-driven insights and strategic support, we help you protect — and rebuild — your profitability before it impacts growth.

 

Inconsistent Revenue / Seasonality

Inconsistent revenue happens when your income fluctuates month-to-month due to seasonality, irregular sales cycles, or reliance on a small group of clients. Even if your annual numbers look solid, cash coming in unevenly creates instability.

When revenue is unpredictable, it becomes difficult to plan, invest, or grow with confidence. You may overextend during strong periods and scramble during slow ones, creating stress and short-term decision-making that slows long-term progress.

How the numbers can be improved:

  • Use forecasting tools to anticipate revenue dips based on seasonal patterns or sales trends
  • Diversify income sources to reduce dependency on specific clients or times of year
  • Develop recurring or subscription-based revenue models for more consistency
  • Create reserve plans during peak months to support leaner ones

 

We help businesses understand revenue patterns and build reliable financial forecasts. At Siegel Solutions, we show you how to prepare for slow months, strengthen your income streams, and operate with more financial predictability all year long.

 

Slow Growth or Flat Sales

Flat or slow sales growth means your business has hit a plateau — you’re maintaining, but not moving forward. This can result from outdated offerings, limited marketing reach, or operational bottlenecks that restrict capacity.

Stagnation is risky. Even if things feel stable, flat sales over time erode momentum, prevent reinvestment, and leave your business vulnerable to competitors who are still growing and evolving.

How the numbers can be improved:

  • Track revenue trends by product, service, or segment to pinpoint slowdowns
  • Review capacity and processes to find growth blockers
  • Invest in high-ROI strategies such as marketing or automation
  • Align budgets with realistic, data-backed growth goals

 

At Siegel Solutions, we help uncover what’s holding your sales back and identify clear, measurable paths to growth. Whether it’s improving your pricing model or optimizing your resources, we turn stagnant numbers into forward momentum.

 

Low Profitability Despite High Sales

This occurs when your business brings in strong revenue but still struggles to generate meaningful profit. It often means you’re selling a lot — but your margins, pricing, or cost structure aren’t optimized.

Revenue alone doesn’t sustain a business. If your profit margins are too thin, growth becomes expensive and exhausting. You might be increasing sales but still not seeing the results in your bank account, which leads to burnout and cash strain.

How the numbers can be improved:

  • Measure profitability by client, product, or service to see what’s working — and what’s not
  • Identify and reduce operational inefficiencies that increase delivery costs
  • Reevaluate your pricing strategy to reflect value and true costs
  • Refocus on high-margin offerings and consider eliminating low-margin work

 

We help you break down your revenue to understand exactly where profit is being made — and where it’s being lost. At Siegel Solutions, we guide pricing decisions, cost analysis, and strategy adjustments to help you keep more of what you earn.

 

Lack of Financial Visibility

Many business owners either don’t receive timely financial reports or don’t fully understand the ones they get. When numbers are unclear or overlooked, financial decisions are made on instinct instead of insight.

Without visibility into your numbers, it’s easy to overspend, miss opportunities, or overlook problems until they’re serious. You may feel like you’re always guessing, which limits your ability to lead effectively and confidently.

 

How the numbers can be improved:

  • Generate timely monthly reports that are clear, accurate, and actionable
  • Use dashboards or key metrics (KPIs) to track performance in real time
  • Review your financials regularly to stay informed and spot trends early
  • Partner with professionals who can interpret and explain the data

 

At Siegel Solutions, we deliver clear, customized financial reports and dashboards — and we take the time to walk you through them. With better visibility comes smarter planning and stronger control over your business.

 

Falling Behind on Technology

If your financial systems rely on outdated software, manual entry, or disconnected tools, your business is likely spending more time than necessary on routine tasks — and missing out on useful insights.

Technology is essential for speed, accuracy, and growth. Falling behind not only wastes resources, but can also make you less competitive. Manual processes create more room for error and reduce your ability to adapt quickly.

How the numbers can be improved:

  • Adopt cloud-based accounting systems for better access and automation
  • Integrate tools like payroll, invoicing, and expense tracking to reduce duplication
  • Use automation to handle routine tasks and free up your time
  • Leverage real-time data to make faster, better decisions

 

We help you implement modern financial tools that fit your business and budget. At Siegel Solutions, we streamline your systems, introduce smart automation, and ensure your business runs more efficiently — and with less stress.

 

Trying to Do It All Alone

What it is:

Many business owners act as their own CFO, bookkeeper, and strategist. While this may work in the early days, it quickly becomes unsustainable as your business grows.

Wearing too many hats increases the risk of burnout, slows decision-making, and leads to financial blind spots. Without expert support, you’re more likely to miss key insights or delay critical changes.

How the numbers can be improved:

  • Outsource your accounting and finance tasks to experienced professionals
  • Work with a trusted advisor who provides perspective and accountability
  • Set up regular financial reviews so you’re never flying blind
  • Focus your time on strategy and leadership, not just bookkeeping

 

At Siegel Solutions, we act as your outsourced accounting team — from day-to-day accounting to high-level strategy. We take the weight off your shoulders so you can focus on leading, growing, and succeeding.

 

Running a business isn’t just about having a great product, delivering excellent service, or building a team. It’s about making decisions every single day that impact the future — decisions about hiring, pricing, spending, investing, and growing. And every one of those decisions relies on one thing: the numbers.

The truth is that most business owners don’t struggle because they lack effort, intelligence, or ambition. They struggle because they lack visibility. Without clear financial data, without the right tools, and without trusted advisors, they’re forced to rely on instinct — not insight.

Over time, that lack of clarity leads to something far more damaging than just a bad month. It creates stress. It creates hesitation. It creates stagnation.

 

When you have control over your cash flow, confidence in your profitability, and clarity in your financial reporting, everything changes:

  • You stop guessing and start planning.
  • You stop reacting and start leading.
  • You stop surviving and start scaling up.

The difference between a business that thrives and one that constantly struggles often comes down to one thing: financial infrastructure and support. That’s where a trusted Client Accounting Services (CAS) firm can make all the difference.

 

At Siegel Solutions, we’re more than bookkeepers. We’re strategic financial partners. Our mission is to provide world-class service and cutting-edge financial solutions to help you:

  • Understand your numbers
  • Make better decisions
  • Unlock profitability
  • Create sustainable growth
  • And sleep better at night

 

Whether you’re just getting started, navigating a critical growth phase, or preparing for long-term expansion, our team is here to give you the tools, guidance, and confidence you need to lead your business forward — with clarity, control, and peace of mind.

 

✅ Let’s move your business from uncertain to unstoppable.

Partner with Siegel Solutions today and take the first step toward financial clarity and growth.

 

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Antonio Tony Martinez
Senior Partner Development Manager

Tony brings over 15 years of QuickBooks knowledge with him and has been recognized as a top performer year over year. Tony will play a critical role in helping our team grow your QB business by managing the relationship between Siegel Solutions and the QuickBooks Solution Provider Program. Tony is focused on optimizing results for strategic partners of all shapes and sizes.

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Noah

Noah Raney
Senior Account Payroll Manager

Noah is our dedicated Intuit Senior Account Payroll Manager who can help you find the right payroll solution for you and your business. He is well versed in all of the QuickBooks platforms being desktop/online/standalone and payroll has been his world since joining Intuit 13 years ago. Whether you are looking for ways to save on time, reduce inflated payroll costs or just get set up with the best discounts, he is here to help. Your success and satisfaction are of utmost importance!

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Sean

Sean McCaffery
Global Channel Sales Partnerships and Alliances Leader

Sean McCaffery has more than 15 years of experience leading channel sales and cloud solutions in the US and Internationally. Sean has held leadership positions with Avaya in Europe growing the channel business with resellers and distributors in key countries driving double-digit growth. He then joined Rackspace Technology and was instrumental in developing sales growth strategies in cloud adoption for customers and partners. Most recently, he ran channels at Dizzion responsible for dynamically growing and expanding the partner ecosystem through SaaS-based VDI solutions before joining Intuit. Currently, he runs the QuickBooks Solution Provider Program supporting the strong business that solution providers and ISV partners have established as well as finding new opportunities to drive emerging mid-market growth together!

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Gabor

Gabor Terebesi
Payments Account Manager

Gabor Terebesi is an Account Manager with the Payments Team of Intuit for over 15 years. He works in the partner division for Intuit payments to ensure Intuit partners along with any clients of theirs are in the most suitable and financially cost-effective solution accepting payments through eCommerce, QuickBooks, mobile payments, or any other options necessary for their business.

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Aimee Garneau
Accounting Manager

Aimee joined Siegel in 2022 as the Accounting Manager overseeing the accounting and bookkeeping team. Aimee brings 18 years of experience with increased responsibility with privately and publicly held companies. Her experience lies with SaaS-based companies as well as in healthcare, consulting, education and nonprofits. Prior to joining Siegel, she held accounting leadership positions with Waban Projects, Elastic Path, Moltin, and Ned Davis Research. Aimee loves partnering with business owners to establish financial reporting and results that promote growth and expansion. When Aimee is not working, she loves spending time with her family and friends and exploring all New England has to offer. She is also an avid Red Sox fan and enjoys going to Fenway Park when she can.

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Jeffrey Siegel
CPA, CEO

Jeff has spent the last twenty years working providing solutions to emerging growth businesses. After graduating from Northeastern University, he spent five years working with two multinational CPA firms in an auditor capacity building a foundation for understanding how business work. He later went on to work in various controller and CFO roles before starting Siegel & Associates (previously Siegel Financial Group) in 2000. In those roles, he sold a company to ADP, raised funds for a major expansion of a large regional IVF clinic, and helped set up accounting and financial structures for dozens of companies. Since starting Siegel & Associates, Jeff has worked with hundreds of clients providing accounting system solutions. Those solutions include setting up QuickBooks in a single-user environment putting in QuickBooks Enterprise in a 30-user environment and integrating various add-ons including inventory, CRM, and e-commerce. He is a Certified Public Accountant, a QuickBooks Pro Advisor, a QuickBooks Advanced Pro Advisor, and an Intuit Solution Provider certified in Enterprise Solutions, Point of Sale & QuickBase. Jeff is also a Microsoft Certified Systems Engineer

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Lori Swartz
Client Support Manager

After graduating from Boston University, Lori spent eight years working in various managerial positions for two national companies. In those positions, Lori developed the skills necessary to manage multiple projects, clients, and resources. She later went on to work for a management company that handled over 25 real estate properties with multiple tenants. Lori joined Siegel Solutions in 2003 as a client services manager where she utilized her skills developed to manage multiple clients and multiple staff. She recently moved into the client support manager role where she is responsible for meeting with and onboarding new clients, managing and maintaining our technology stack along with QuickBooks setups, conversions, training, and consulting.

In her free time, Lori enjoys spending time with her family. She loves to travel, music, and theater.

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Janet Jodoin
Bookkeeping Associate

Janet joined Siegel Solutions in May of 2022 as an Associate Bookkeeper. In her younger years, while raising her family, she completed her degree in Business and she spent 20 years in the trades as a custom designer. Janet also has 16 years in corporate management. Her strong team support, training, and development led her to support and manage Human Resources. Janet's desire to change careers has led her to return back to bookkeeping at Siegel Solutions. In Janet's free time she enjoys spending time with her growing family. Her personal favorite is creative landscaping in her yard. She also enjoys working alongside her partner in construction and remodeling.

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Tricia Gullage
Associate

Tricia Joined Siegel Solutions in 2022 as a bookkeeper and works with our clients to keep their day-to-day bookkeeping in order. Tricia has 12 years of bookkeeping experience working for a large construction company for 10 of those years handling all their accounting and Payroll. She met Jeff our CEO while working there and decided she wanted to join our team.

When not working Tricia enjoys spending time with her family and friends. She recently moved up to the lakes region in NH and loves going to concerts, enjoying her time boating and snowmobiling.

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Ed Jaworski
Professional Services Manager

With over 21 years of corporate experience at PeopleSoft Consulting, Sun Life Financial, and KPMG, Ed brings a big business approach to small business solutions. Prior to joining Siegel Solutions in 2022, Ed helped small businesses get the most out of QuickBooks for 21 years as a co-founder of SMB Partners and the founder of Solutions for Office Software.

Ed is an Advanced Certified QuickBooks® ProAdvisor, a Certified QuickBooks® Point of Sale ProAdvisor, a Certified QuickBooks Enterprise Solutions ProAdvisor, and a Certified SOS Inventory Consultant. Ed holds an MS in Computer Information Systems from Bentley University and a BS in Business Administration from Northeastern University.

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Debby Mono
Firm Administrator

Prior to joining Siegel Solutions in March 2023, Debby had been working in administrative and executive assistant roles for many years in various fields. Her extensive background in these positions has provided her with a range of skills and knowledge that are valuable in her new role as a Virtual Administrative Assistant. She graduated from Suffolk University with a Bachelor's Degree.

Outside of work, Debby can be found at football fields or dojos cheering for her sons. She also enjoys hikes with her dog, Sawyer, reading, sports, and live music. She and her husband also love to entertain family and friends.

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Letitia Cote
Senior Associate

Letitia has an accounting degree and has been working in the Accounting/Bookkeeping industry for over 25 years. Tish is also an Acumatica Business Consultant. Outside of work, Tish has 4 grown children and 5 grandchildren, she loves to ski, hike, bike, and be outdoors. Tish has worked with Jeff for over 10 years.

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Andrea Alencar
Associate

Andrea graduated from Bridgewater State with a Bachelor's degree in Accounting. Andrea joined Siegel Solutions in 2022. Andrea has gained accounting experience working in various industries including a CPA firm, legal, hospitality, and telecommunications. Before coming to Siegel Solutions Andrea previously worked as a bookkeeper and staff accountant.

Andrea has 4 kids which keep her busy. Outside of work, Andrea enjoys spending time with her kids, being outside, cooking, and going to softball/baseball games.

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Mike Derrico
IT

I started my career in 1983 when I designed and built a device to share a computer program, written by the president of a local bank and his son, running on an Apple Lisa computer. The device allowed the large and expensive Lisa's computer to be shared with bank employees. With this program, and with my device, we started a company to market this unique solution to banks. At this point, computer networks were just starting to be used in businesses. I transitioned my efforts to providing support for migrating banking terminal/mainframe functions to the emerging Personal Computer networking platform. For the next decade, I worked with, and beta tested, numerous technologies to integrate the banking functions from dumb terminals into the now smart desktop computers. After working with a few small consulting firms, I started my own company focusing on providing I.T. support to SMBs. More recently I am now doing the exact opposite by helping customers migrate their PC applications and data from their local computers to The Cloud. A few years ago, I joined Siegel Solutions to add my years of I.T. experience to their firm.

In my spare time, I like to travel, fly my drone and, most importantly, spend time with my family. I also still enjoy tinkering with technology.

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Pat Jaworski
Associate

After spending most of her corporate career in the insurance industry, Pat joined a QuickBooks consulting firm providing bookkeeping services to several small companies. Late in 2022, that firm merged with Siegel Solutions, Inc., bringing Pat and her clients to the group. She provides services to clients in a variety of industries: fitness, construction, beauty, equine care, and medical billing, to name a few. She enjoys supporting her clients by keeping their financial records in good shape and allowing them to focus on growing their respective businesses.

Pat resides in the 495/MetroWest area with her husband Ed, daughter Abby and Duffy, their lovable, energetic golden retriever.

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John Brakey Campos

Senior Account
Payroll Manager

John has been with Intuit for over 18 years, serving in a variety of roles across the organization. For the past 8+ years, he has focused on payroll and workforce management solutions, helping clients streamline operations and make informed decisions. John is passionate about working directly with customers to understand their unique needs and recommend the best solutions to support their teams.

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DeeAnna Keyes

Sales and Marketing Associate

DeeAnna Keyes, has been our Sales and Marketing Associate since December 2023. She brings a wealth of experience, having worked at Intuit with a focus on Quickbooks Online and Quickbooks Desktop. With a robust sales history and a license as a real estate agent in Virginia, DeeAnna is a versatile professional. Outside of work, she cherishes family moments, indulges in camping with friends, and finds joy in entertaining at home with her husband and four children.

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Janice Kats

Associate

Janice Kats graduated from Carl Sandburg College with an Associate Degree in Accounting in 1992 and has been working in the accounting field ever since in various jobs doing AR, AP, payroll, office management, and bookkeeping before joining Siegel Solutions in late 2023.

In 2022, she made the decision to branch out on her own and started her own bookkeeping business, working from home.

She is a mom to 3 grown children and a grandmother to 5 grandchildren and enjoys spending time with her husband and two dogs and following her grandchildren in all of their sports.

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Alyssa Bradford
Firm Manager

Alyssa Bradford joined Siegel Solutions as Firm Manager in March 2025, bringing with her a strong background in operations management and a hands-on, "boots on the ground" leadership style. Known for her excellent communication skills and practical approach to problem-solving, Alyssa plays a key role in driving efficiency and fostering team collaboration at the firm.

She is a graduate of the University of Hartford and lives in Franklin with her husband and son, where they enjoy making the most of nice weather together as a family. In her downtime, Alyssa enjoys HGTV and Food Network shows.

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Cynthia Moncayo-Mena
Associate

Cynthia joined Siegel Solutions in March 2025 as an Associate. She has a Bachelor's in Accounting from New Jersey City University and over 10 years of experience in accounting.
She is married with two children and enjoys reading and exploring new places to visit!

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