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.
Here’s a glimpse of what you’ll learn:
- [2:27] Why Chuck McDonald left a successful wealth management career to pursue entrepreneurship
- [06:28] Chuck’s mission to make financial literacy and business education more accessible
- [10:28] Defining exit planning as the alignment of business, financial, and personal goals
- [16:02] Common psychological roadblocks owners face when trying to let go of their business
- [21:50] What business owners should focus on at 10, five, and three years before an exit
- [26:59] The different exit paths owners can take
- [34:13] Why having a financial advisor early is crucial to bridge the “wealth gap” before exiting
In this episode…
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.
Resources Mentioned in this episode
- Hannah Smolinski: LinkedIn | Email
- Clara CFO Group: Website | YouTube
- Financial Clarity podcast: Website | YouTube
- Chuck McDonald on LinkedIn
- Cresscila
- “How Fractional Leadership Helps Business Owners Scale Without Breaking the Bank With Ben Wolf” on the Financial Clarity podcast
- “How To Align Your Bookkeeper and Tax Accountant for Financial Success With Nancy McClelland” on the Financial Clarity podcast
- “Business Development Insights With Mark Wainwright” on the Financial Clarity podcast
- The Psychology of Money: Timeless lessons on wealth, greed, and happiness by Morgan Housel
- Exit Planning Institute (EPI)
Quotable Moments
- “I had the opportunity to sell my practice back to my partners — a very attractive option.”
- “You don’t want to retire from something; you want to retire to something.”
- “Exit planning done right looks a lot like that. There were no surprises.”
- “You’re mitigating risk; you’re dealing with maybe key person insurance or an unfunded buy-sell agreement.”
- “It’s always better to make a choice when you can versus when you have to.”
Action Steps
- Start exit planning 3–5 years in advance: Early preparation gives owners time to reduce risk, build value, and explore all options.
- Align personal, financial, and business goals: Ensuring these areas work in tandem creates a smoother, more successful transition out of the business.
- Conduct a business assessment regularly: Identifying operational risks and weaknesses early improves valuation and avoids surprises during due diligence.
- Delegate and document key responsibilities: Building a business that runs without you increases its attractiveness and value to potential buyers.
- Explore multiple exit paths: Understanding options like employee transfers, private equity, or strategic sales empowers owners to choose what fits best.
Sponsor for this episode…
Clara CFO is dedicated to providing financial clarity and profit-maximizing solutions to small businesses. The team at Clara CFO are seasoned accounting professionals with a heart for small business. We help growth-minded entrepreneurs thrive through Fractional CFO services and financial education.
Whether you’re grappling with hiring decisions, profit margin concerns, or ambitious growth plans, Clara CFO provides insights, recommendations, and a clear financial roadmap to achieve your goals.
To learn more about Clara CFO Group and how we can help your business, visit ClaraCFO.com.
