Category Archives: Alternative Investments

Alternative Investments, Chicago Area Investment Advisor, Family Office, Fiduciary Advisor, Hedge Fund Strategies, Hedge Funds, Private Equity, Private Wealth, Selecting a Family Office Investment Advisor, Selecting a Private Wealth Investment Advisor, Selecting an Investment Advisor, Selling a Business, Wealth Management

Selling Your Small Business: A Roadmap to a Successful Exit

Posted on by Bill Seyfarth
12
Sep

 

Selling the business you’ve poured your heart and soul into is a monumental decision. It’s a moment that can redefine your financial future, secure your legacy, and open doors to new adventures. Yet, it’s also a complex journey, fraught with potential pitfalls if not navigated carefully.

Whether you’re dreaming of retirement, eyeing a new entrepreneurial challenge, or adapting to changing life circumstances, preparing your business for sale demands strategic thought, meticulous planning, and flawless execution. This guide is designed to walk you through the essential considerations every small business owner should weigh before putting their cherished venture on the market.

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Alternative Investments, Fiduciary Advisor, Private Equity, Private Wealth, Selecting a Family Office Investment Advisor, Selecting a Private Wealth Investment Advisor, Selecting an Investment Advisor, Wealth Management

How RIAs and Bank Trust Departments Are Elevating Their Investment Game Through Outsourced CIO Solutions

Posted on by Matthew Rice
05
Sep

 

In today’s fast-changing financial services landscape, Registered Investment Advisor (RIA) firms and Bank Trust Departments face a critical challenge: delivering sophisticated investment strategies and outstanding client service—often with fewer resources than large national competitors. To remain competitive and cultivate sustainable growth, many forward-thinking firms are partnering with an outsourced Chief Investment Officer (OCIO). This solution provides institutional-quality investment management at a fraction of the cost—typically $180,000 to $230,000 annually, according to Cornerstone Research—compared to hiring an equally skilled in-house CIO and support team. For these agile firms, the shift isn’t just about keeping pace; it’s about strategically positioning themselves to outperform and compete well above their weight class.

 

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Alternative Investments, Family Office, Fiduciary Advisor, Private Equity, Selecting a Family Office Investment Advisor, Selecting an Investment Advisor, Wealth Management

Family Offices: Ditch the Talent Hunt and Hire an Expert Contractor

Posted on by Matthew Rice
25
Aug

 

For ultra-high-net-worth families, your private wealth management firm—the family office—is at the heart of your financial strategy. As direct investing and complex portfolio oversight become the norm, the demand for top-tier investment talent has never been greater. Yet, many family offices are finding that the hunt for a world-class, in-house investment analyst is a struggle.

It’s not just about competing with Wall Street salaries. The challenges are often structural, cultural, and economic. But what if the solution isn’t to compete for talent you can’t get, but to hire the experts you need?

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Alternative Investments, Covered Call Strategies, Selecting a Private Wealth Investment Advisor, Selecting an Investment Advisor, Tax-Loss Harvesting, Wealth Management

Breaking Free from Concentrated Stock Positions: Advanced Tax Strategies That Transform Your Portfolio

Posted on by Sean McEvilly
24
Aug

For many successful executives, entrepreneurs, and long-term investors, a concentrated stock position is a testament to their hard work and success. It’s also a paradox: a source of tremendous wealth that can feel impossible to diversify without facing a devastating tax bill.

If you’ve built substantial equity through stock options, inherited a large position, or simply held a winning investment for years, the question remains: How do you break free and reduce your risk without triggering massive tax consequences?

Traditional tax-loss harvesting often falls short when dealing with positions that have substantial embedded gains. When your cost basis is near zero and your wealth is tied up in a single stock, the conventional wisdom of “just sell and diversify” is financially devastating.

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Alternative Investments, Family Office, Investment Strategy, Private Equity, Private Wealth, Selecting a Family Office Investment Advisor, Selecting a Private Wealth Investment Advisor, Selecting an Investment Advisor, Wealth Management

Preserving and Amplifying Dynastic Wealth: The Strategic Imperative of Private Equity for Ultra-High-Net-Worth Investors and Family Offices

Posted on by Bill Seyfarth
23
Aug

 

For ultra-high-net-worth (UHNW) investors and family offices, the mandate extends beyond mere capital growth; it encompasses the sophisticated preservation and intergenerational amplification of dynastic wealth. In an investment landscape characterized by unprecedented market dynamics, persistent inflationary pressures, and a demand for superior, uncorrelated returns, the strategic allocation of capital today will define legacies for decades to come. Increasingly, private equity (PE) has transitioned from an alternative allocation to an indispensable core strategy for discerning investors seeking to navigate these complexities and secure their financial future. Here’s why private equity warrants a preeminent position within your diversified portfolio.

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Alternative Investments, Chicago Area Investment Advisor, Chicago Area Private Wealth, Family Office, Fiduciary Advisor, Hedge Fund Strategies, Hedge Funds, Hinsdale Investment Advisor, Private Equity, Private Wealth, Real Assets Investing, Selecting a Family Office Investment Advisor, Selecting an Investment Advisor, Selling a Business, Wealth Management, Western Chicago Suburbs Investment Advisor

From Business Owner to Investor: Charting Your Course After a Business Sale

Posted on by Bill Seyfarth
22
Aug

 

Selling your business is a monumental achievement, marking the culmination of years of hard work and dedication. But as one chapter closes, another exciting, albeit complex, one begins: transitioning from the steady income of an active business to living off the total return of an investment portfolio. This shift blends excitement, uncertainty, and a new set of financial considerations.

Here’s what every entrepreneur should consider to ensure a smooth and successful journey from business owner to thriving investor.

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Active Management, Active Versus Passive Management, Alternative Investments, Hedge Funds, Index Funds, Liquid Alternatives, Liquid Alts, Passive Management, Private Equity, Real Assets Investing, Selecting an Investment Advisor, Tax-Loss Harvesting

Active vs. Passive: Tailoring Investment Strategies to Asset Classes

Posted on by Matthew Rice
16
Aug

 

When it comes to investing, the age-old debate of active management versus passive management isn’t just about personal preference; it’s deeply tied to the unique characteristics of different asset classes and how efficient their markets are. Understanding where each approach shines can be a game-changer for optimizing returns, managing risk, and keeping costs down.

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Alternative Investments, Endowments, Family Office, Foundations, Private Equity, Private Wealth, Selecting an Investment Advisor

Unlocking the Private Market: A Deep Dive into Private Equity and Venture Capital

Posted on by Matthew Rice
13
Aug

 

Private equity (PE) has long been a domain for institutional investors and the ultra-high-net worth promising access to exclusive opportunities and the potential for outsized returns. But what exactly is private equity, and how does it differ from traditional public market investments? More importantly, is it the right fit for your investment strategy?

In this post, we’ll explore the main reasons to consider—and to be cautious about—investing in private equity, delve into its various styles and strategies, including the dynamic world of venture capital, and help you understand if this alternative asset class aligns with your financial goals.

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Alternative Investments, Covered Call Strategies, Family Office, Financial Planning, Private Wealth, Selecting a Private Wealth Investment Advisor, Selecting an Investment Advisor, Selling a Business, Tax-Loss Harvesting, Wealth Management

A Strategic Guide to Hedging Your Concentrated Stock Position

Posted on by Sean McEvilly
30
Jul

 

For investors holding a significant portion of their wealth in a single stock, the feeling is a mix of excitement and unease. On one hand, a concentrated position can deliver life-changing returns. On the other, it exposes you to idiosyncratic risk—the unique, unpredictable dangers of a single company that can devastate your portfolio regardless of how the broader market is doing.

This guide explores strategic approaches to managing this risk, allowing you to protect your wealth while keeping your potential for upside gains.

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Alternative Investments, Endowments, Endowments and Foundations, Fiduciary Advisor, Foundations, Nonprofits, Selecting an Endowment or Foundation Investment Advisor, Selecting an Investment Advisor

The Big Beautiful Bill: Why This New Tax Law Is Reshaping Endowment and Foundation Investing

Posted on by Matthew Rice
29
Jul

 

The financial world for endowments and foundations just got a wake-up call. The “One Big Beautiful Bill Act,” or OBBB, signed into law on July 4, 2025, isn’t just another piece of legislation—it’s a fundamental change to the economics of large-scale charitable investing. Starting in 2026, a new excise tax regime will profoundly impact how major institutions manage their portfolios, a change that will have an immediate and compounding effect.

Important clarification: The OBBB Act specifically targets private foundations and university endowments. Donor-advised funds (DAFs), community foundations, and operating charities are NOT affected by these new excise tax rules. These charitable vehicles continue to operate under the previous tax framework and remain exempt from the progressive rate structure described below.

For any private foundation or university endowment with assets over $50 million, this isn’t a minor adjustment; it’s a call to action. The drag on returns will snowball, impacting future grants and mission-driven spending. Here’s a deep dive into what changed, why it matters, and the advanced strategies you can use to respond.

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