Single Family vs. Multi Family Offices: Which Structure Makes Sense and When

June 3, 2026

Choosing between a single family office, or SFO, and a multi family office, or MFO, is not simply a question of cost or investment strategy. It is a risk management decision. Single family offices provide a high degree of control and customization, which can be well suited for families with…

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5 Strategies to Reap the Benefits of a Stabilizing Real Estate Insurance Market

June 1, 2026

After a prolonged period of rising premiums and tighter underwriting, the commercial real estate insurance market is beginning to show signs of stabilization. Following several years in a hard market cycle, many organizations are seeing insurance premium reductions, increased underwriting flexibility, more favorable terms and broader policy options across a…

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Oswald Employee‑Owners Support Greater Cleveland Food Bank Through Day of Caring

May 28, 2026

At Oswald, commitment to community is more than a value. It is something we put into action. This week, Oswald employee‑owners came together for a two‑day effort to support the Greater Cleveland Food Bank, helping address food insecurity across Northeast Ohio through both donations and hands‑on service. From Oswald Tower…

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Creating Inclusive Family Planning Pathways for a Modern Workforce

May 28, 2026

The workforce is constantly evolving, and so are employees’ needs and expectations, especially when it comes to their benefits. A one-size-fits-all approach is no longer enough. Today’s employees want benefits that make a real difference in their lives.   One way to deliver true value is through family building support.  An increasing number of employers are recognizing the importance of comprehensive family planning and fertility benefits.…

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Why Overlooked Personal Risks Can Disrupt Long-Term Financial Plans

May 27, 2026

Market volatility often dominates conversations about wealth. Yet recent financial commentary suggests that everyday personal risk may pose a more immediate and lasting threat. A widely shared analysis highlighted how uninsured or underinsured events, such as liability claims or property losses, can disrupt financial plans far more quickly than market…

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Controlling Employee Benefits Costs with Captive Insurance

May 26, 2026

When employee benefits costs keep climbing, it’s hard for employers to feel in control. Rising medical costs, more high-cost claims, and the growing use of specialty drugs gene therapies all hit the bottom line, leaving many employers feeling like they are just watching the numbers go up.  But employers don’t have to sit back while the costs…

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How Successful Family Offices Think About Personal Risk Differently

May 20, 2026

When people talk about risk in family offices, the conversation often begins and ends with investments. Market volatility, asset allocation, and return assumptions tend to dominate attention. Many family offices, however, recognize a quieter reality. Some of the most significant risks families face are personal, not financial. Litigation, liability, liquidity…

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Health Insurance and Plan Choices are Key to Retention | Oswald M&A Advisory

May 19, 2026

Employee benefits have become a key part of the hiring and retention of employees in today’s hiring market. There is increased stress on compensation as demand for higher salaries and pay rates come from potential hires and the existing workforce. An employer’s willingness to put the time and effort into…

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Private Equity Risk and Insurance: Workforce, Benefits Considerations During Due Diligence

May 12, 2026

Today’s headlines are filled with talk about inflation and rising prices. Although the recent Consumer Price Index reporting has showed a slight curve in trend, businesses will continue to deal with the balancing act of absorbing cost increases while retaining employees. The cost of labor and benefits continues to rise,…

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Workforce Fatigue in Aging Services: Its Impact on Safety, Claims and Cost of Risk

May 6, 2026

In aging services, some of the most significant insurance costs are not driven by catastrophic events, they are built over time through everyday operational strain. Workforce fatigue is one of the most overlooked drivers of claims frequency, severity and ultimately, total cost of risk. It often develops gradually, yet its…

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