Chuck McDonald is the Founder of Cresscila, a company dedicated to assisting small business owners in creating value through education, optimization, and strategic vision. After a distinguished 20-year career in wealth management, during which he held key roles in marketing, sales, client optimization, compliance, and staffing, Chuck established Cresscila in 2024 to pursue a new chapter inspired by the successes and lessons from his clients. As a Certified Financial Planner and Certified Exit Planning Advisor, he leverages his extensive experience to empower entrepreneurs to transform blind spots into opportunities, ultimately enhancing profitability and lifestyle. Chuck's mission is to equip business owners with the knowledge and tools necessary to achieve success beyond their expectations.

Letting go of a business is never just a transaction, it’s a transition. Yet too many owners only start thinking about an exit when it’s already on the horizon, missing crucial steps that could make or break their financial future. What’s the biggest blind spot owners have when preparing to exit?

According to Chuck McDonald, a seasoned exit planning advisor and former wealth manager, most owners don’t realize that exiting a business is as much a personal journey as it is a financial one. He highlights the importance of aligning business operations, personal goals, and financial readiness years in advance. Without that alignment, owners risk regret, missed value, or even a failed sale. Chuck explains that many founders are deeply intertwined with their businesses, making it hard to delegate or detach when the time comes. By starting early, removing risk, and building a self-sufficient team, owners not only increase valuation but also create the freedom to transition on their own terms.

In this episode of the Financial Clarity podcast, Hannah Smolinski sits down with Chuck McDonald, Founder of Cresscila, to discuss what most business owners miss when planning their exit. Chuck breaks down the true meaning of exit planning, the emotional roadblocks owners face, and how to prepare your business to be buyer-ready. He also shares how to protect your personal legacy while maximizing value.

Kristine Nguyen is the Founder and Principal Accountant of Pretty Books, an accounting boutique in Seattle that provides bookkeeping, tax, and back-office management services to small businesses. With extensive experience setting up and managing accounting systems across various industries — including retail, information technology, food and hospitality, and nonprofits — she enjoys working with small businesses and exploring different tools and technology to create efficiency and transparency in business operations.

Choosing the right bookkeeper for your business isn’t as simple as hiring someone to balance the books. Depending on your needs, you may require a meticulous, process-driven professional, an analytical thinker who can spot financial trends, or someone who blends both skill sets. How do you determine what kind of bookkeeper will best support your business’s growth?

According to Kristine Nguyen, an accounting expert with years of experience helping small businesses manage their finances, the key is understanding what you truly need from a bookkeeper. She highlights that some bookkeepers excel at structured, repetitive tasks like processing invoices and reconciling accounts, while others focus on financial reporting and deeper analysis. The mismatch between business owners’ expectations and a bookkeeper’s actual role often leads to frustration. Kristine explains that identifying whether your business requires operational bookkeeping or strategic financial oversight can prevent costly hiring mistakes and set you up for long-term success.

In this episode of the Financial Clarity podcast, Hannah Smolinski speaks with Kristine Nguyen, Founder and Principal Accountant of Pretty Books, to discuss how business owners can find the right bookkeeping support. Kristine breaks down the differences between bookkeepers, controllers, and CFOs, shares key questions to ask when hiring, and explains why bookkeeping has become more technology-driven. She also provides insights on setting expectations to build a productive accountant-client relationship.

Sanjit Singh is the Fractional Chief Revenue Officer at Boltt, a company empowering B2B companies to accelerate revenue growth and establish scalable sales models. With over 12 years of experience leading teams in Fortune 500 companies, he transitioned into entrepreneurship, co-founding multiple tech startups, including LeadCrunch, which he grew to a $24 million run rate before exiting at Series B. Over the past five years, Sanjit has focused on providing fractional growth leadership, helping companies overcome revenue plateaus and achieve new levels of success.

Scaling a business is exciting, but what happens when growth slows, sales stall, and marketing efforts don’t translate into revenue? Many companies struggle to pinpoint the root cause of their stagnation, leading to wasted resources and frustration. At what point does bringing in outside expertise make the difference?

According to Sanjit Singh, a seasoned revenue strategist, companies often hit a ceiling because they lack the right sales and marketing structure. He highlights that many founders rely on ad-hoc revenue strategies that may have worked early on but aren’t scalable. Without a clear growth engine, businesses waste time on ineffective tactics or experience friction between sales and marketing. Sanjit explains that a Fractional Chief Revenue Officer provides the leadership and strategy needed to align teams, optimize revenue processes, and unlock new growth opportunities.

In this episode of the Financial Clarity podcast, host Hannah Smolinski speaks with Sanjit Singh, Fractional Chief Revenue Officer at Boltt, to discuss when businesses should consider hiring a CRO. They explore how to recognize the warning signs of stalled growth, the importance of choosing the right revenue model, and the impact of aligning sales and marketing. Sanjit also shares key mistakes companies make in business development and how to fix them.

Ben Wolf is the Founder and CEO of Wolf's Edge Integrators, a leading fractional COO firm specializing in helping businesses scale efficiently. He began his entrepreneurial journey by building operations at a healthcare startup, transforming it into the largest organization of its kind in New York State within three years. Recognized as a pioneer in fractional executive leadership, Ben authored the bestselling book Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach and hosts the Win Win Podcast.

Many business owners struggle to step away from daily operations, making it difficult to focus on long-term growth. Fractional leadership offers executive-level support without the high cost of full-time hires. But how does a fractional integrator actually help a business scale?

According to operations expert Ben Wolf, a fractional integrator ensures smooth execution across all functions, allowing the owner to focus on strategy instead of daily operations. Instead of hiring a full-time executive for $250,000 or more, businesses can bring in an experienced leader part-time to drive execution, align teams, and remove operational bottlenecks. Ben explains that many companies remain stuck in trial-and-error mode for years, testing different strategies without real traction; whereas a fractional integrator brings proven systems that accelerate growth. This approach helps businesses scale efficiently without the financial burden of a full-time hire.

In this episode of Financial Clarity, Hannah Smolinski and Ben Wolf, Founder and CEO of Wolf's Edge Integrators, explore the benefits of fractional leadership, the challenges of hiring experienced executives, and how business owners can create a self-sustaining company. Ben shares actionable advice on building a strong leadership team, reducing operational bottlenecks, and using a 12-month rolling budget to improve financial decision-making.

Nancy McClelland is the Owner of The Dancing Accountant, a firm specializing in bookkeeping, tax preparation, accounting, and advisory services for small businesses. With over 30 years of experience, she helps businesses streamline financial processes, improve compliance, and adopt best practices. Nancy also educates bookkeepers through her Ask a CPA membership community and writes an award-winning blog at TheDancingAccountant.com. She has been recognized as a Top Client Services ProAdvisor and one of Ignition’s Top 50 Women in Accounting.

Managing your business finances can feel overwhelming — especially when your bookkeeper and tax accountant seem to operate in completely separate worlds. Without clear communication between them, mistakes happen, deadlines get missed, and tax season turns into a stressful scramble. So how can you ensure these key financial professionals are working together to support your business success?

According to Nancy McClelland, a nationally recognized CPA and financial educator, alignment starts with clear roles, regular communication, and a shared commitment to accuracy. She highlights that many business owners assume hiring both professionals means everything is handled, but in reality, lack of coordination leads to costly errors and duplicated work. By fostering a team mindset, setting clear expectations, and ensuring that financial records are tax-ready year-round, small businesses can avoid last-minute panic and make better financial decisions. Nancy also emphasizes that technology can bridge communication gaps, making it easier for bookkeepers and tax accountants to collaborate effectively.

In this episode of the Financial Clarity podcast, host Hannah Smolinski sits down with Nancy McClelland, Owner of The Dancing Accountant, to discuss how business owners can align their bookkeeper and tax accountant for financial success. They break down the importance of defining responsibilities, creating an accountability chart, and scheduling regular check-ins. Nancy also gives practical advice on leveraging technology to streamline bookkeeping and tax preparation.

Lynn Rivest is the Founder of Lynn Rivest Consulting, a firm specializing in helping small service-based business founders define profitable positioning to attract high-value clients. With over 23 years of experience in digital marketing and strategy, Lynn has worked extensively with founders to refine their messaging, improve client acquisition, and streamline their business models for maximum revenue. Her approach combines simplicity and focus, enabling businesses to gain clarity and stand out in competitive markets.

Positioning your business in a crowded marketplace can feel overwhelming. How do you ensure your message stands out and reaches the right audience?

According to Lynn Rivest, a digital strategist and business advisor, positioning is about defining your business’s unique value and ensuring it resonates with the right audience. She highlights that without clear positioning, businesses often struggle to explain their value, leading to missed opportunities and ineffective marketing. Positioning acts as a guide for all business decisions, from product offerings to marketing strategies, and helps you focus on what matters most to your ideal clients. Lynn emphasizes that strong positioning not only amplifies your message but also saves time, resources, and money by attracting the right clients and simplifying other aspects of business, like referrals and messaging. 

In this episode of the Financial Clarity podcast, host Hannah Smolinski sits down with Lynn Rivest, Founder of Lynn Rivest Consulting, to discuss strategic positioning and differentiation for small businesses. They explore why positioning is essential for standing out, how it amplifies business decisions, and why differentiation is critical for success. Lynn also shares insights on identifying and serving your ideal clients while implementing positioning strategies effectively.

Mark Wainwright is the Principal Consultant and Founder of Wainwright Insight, a firm specializing in fractional sales management and consulting for professional services firms. With over seven years of experience, Mark focuses on helping businesses refine their sales pipelines, build future sales leaders, and create client-centric sales processes. He is also the co-host of the Breaking BizDev podcast, where he explores the intersection of sales, marketing, and business development for professional services.

What’s the secret to turning technical professionals into confident sales leaders? For many service-based businesses, the line between delivering exceptional work and securing new clients can feel blurry — if not overwhelming. How can businesses build a sales process that is both strategic and empathetic while maintaining the integrity of their craft?

According to Mark Wainwright, a fractional sales management consultant and expert in professional services sales, the key lies in structured and client-centric sales processes. He highlights that great sales aren’t about being pushy but about curiosity and inquiry. By teaching technical professionals to approach sales as an organized and logical process, they can develop confidence and achieve better outcomes. Mark’s framework — Create, Choreograph, and Contract — guides businesses in proactively identifying opportunities, orchestrating seamless sales conversations, and establishing solid agreements, ensuring long-term success.

In this episode of Financial Clarity, host Hannah Smolinski sits down with Mark Wainwright, Principal Consultant and Founder of Wainwright Insight, to discuss building a sustainable and healthy sales pipeline. They explore Mark’s insights on empowering technical professionals, the importance of realistic pipeline management, and how to overcome common misconceptions about sales. Mark also shares actionable strategies for staying solo while scaling impact effectively.

Jackie Meyer is the Founder and President of TaxPlanIQ, a software platform that equips tax advisors with tools to streamline tax planning and maximize client savings. A CPA with extensive experience, Jackie previously owned an award-winning CPA firm and developed the ROI Method of Value Pricing to align services with client value. She is also an educator and speaker focused on improving financial literacy and efficiency for professionals and small businesses.

Are you paying more taxes than you should? Many business owners assume their CPA or tax preparer has every deduction and strategy covered, but the truth is tax planning often goes beyond the basics. What strategies can keep more money in your pocket while staying compliant with the law?

According to Jackie Meyer, a pioneering tax strategist and educator, true tax planning is about going beyond simple projections to uncover actionable strategies that minimize liabilities. She highlights the importance of asking the right questions when engaging a CPA, such as whether they offer advanced tax strategies or attend ongoing education. By focusing on proactive, ROI-driven planning, individuals and businesses can save tens of thousands of dollars annually.

In this episode of the Financial Clarity podcast, host Hannah Smolinski hosts Jackie Meyer, Founder and President of TaxPlanIQ, to discuss actionable tax planning strategies that save money and increase value. They cover the critical differences between tax preparation and planning, how to identify when tax planning is worth the investment, and practical tips for finding the right tax professional. Jackie also shares insights into value pricing and how it transforms client relationships and CPA practices.

Laura Shiel is the COO at Clara CFO Group, a firm that specializes in offering strategic financial guidance and support to small businesses. With a diverse background in accounting and finance, Laura’s experience spans various sectors, including public accounting, financial services, and corporate finance in a Fortune 500 company. She holds two esteemed credentials in the finance world: she is a Certified Public Accountant (CPA) and a Chartered Financial Analyst (CFA). As a fractional CFO, Laura is dedicated to helping small business owners achieve their personal and professional aspirations.

Navigating the complexities of growing a business while ensuring financial and operational alignment can be a daunting task. How can small businesses effectively merge financial expertise with strategic leadership to achieve their vision?

According to Laura Shiel, a seasoned financial strategist, integrating a CFO into EOS implementation provides critical financial insight and operational clarity. She highlights how fractional CFOs, by participating in Level 10 meetings and quarterly strategy sessions, ensure that financial implications are considered at every decision point. This alignment fosters efficient problem-solving and sharper decision-making. Laura emphasizes that CFOs bring valuable outside perspectives from working with diverse clients, allowing them to introduce best practices and innovative solutions that elevate the EOS process.

In this episode of the Financial Clarity podcast, Hannah Smolinski speaks with Laura Shiel, COO at Clara CFO Group, to discuss how outsourced CFOs play a transformative role in EOS. They cover how CFOs contribute to long-term visioning, enhance decision-making in leadership teams, and create future financial plans to meet growth targets. Laura also shares her insights on when to bring a CFO into the EOS process and how finance and operations are deeply intertwined in achieving business success.

Laura Shiel is the COO at Clara CFO Group, a firm that specializes in offering strategic financial guidance and support to small businesses. With a diverse background in accounting and finance, Laura’s experience spans various sectors, including public accounting, financial services, and corporate finance in a Fortune 500 company. She holds two esteemed credentials in the finance world: she is a Certified Public Accountant (CPA) and a Chartered Financial Analyst (CFA). As a fractional CFO, Laura is dedicated to helping small business owners achieve their personal and professional aspirations.

Scaling a small business can be exciting but overwhelming without the right systems in place. How can business owners bring structure and accountability to support growth without getting bogged down by chaos?

According to Laura Shiel, a seasoned CPA and COO, implementing the Entrepreneurial Operating System (EOS) provides clarity and organization, helping teams set clear roles and realistic goals. She emphasizes that EOS allows companies to transition from reacting to everyday issues to proactively driving strategic growth. This structured approach, she notes, empowers everyone on the team to align around the vision, paving the way for sustainable success.

In this episode of the Financial Clarity podcast, Hannah Smolinski speaks with Laura Shiel, COO at Clara CFO Group, about their journey of implementing EOS at the company. They share insights on defining roles and responsibilities, setting 90-day “rocks,” and running effective weekly meetings to keep everyone on track. Laura also offers advice on the benefits and challenges of self-implementing EOS, with practical tips for small teams looking to adopt this transformative system.