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Case Studies

Navigating New Wealth With Confidence

Turning a Liquidity Windfall Into a Multigenerational Legacy
Background

New Wealth, New Complexity

A business owner in his mid-40s had recently gone through a major liquidity event, selling 70% of his company to private equity while maintaining a minority stake. Despite his tremendous business acumen, his family found themselves in uncharted territory — navigating the complexities of this influx of significant wealth — and didn’t want to make any costly mistakes.

The principal was referred to Legacy Knight by a family friend who had gone through a similar experience and was a client. From their first conversation with Legacy Knight, it was clear the family was seeking more than investment guidance and advisory-level oversight. They sought a steward who could help them establish a legacy.

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We were proud of what we built and what we earned. But, when the deal closed, we realized we needed more than a roadmap for what comes next — we needed a partner who knew what we didn’t know and who would provide more than a cookie-cutter strategy.”

Family Principal

Challenges & Objectives

While every engagement with Legacy Knight is bespoke, the pain points clients experience  at the outset do have similarities. The challenges faced by this family are some of the most common we encounter, as are their broad objectives.

Challenges Included
Lack of prior experience managing personal wealth at scale
Concern about making costly, early missteps
Anxiety about the post-liquidity tax season
Uncertainty about long-term strategies like wealth transfer, estate planning, and philanthropy
Objectives Included
Identifying a partner that would take charge
of an integrated team with other advisors
Continuing to grow wealth long-term
in a cost-effective and efficient manner
Securing a future with a partner that thinks both entrepreneurially and multi-generationally

Legacy Knight's Approach

We approached this family proactively and holistically, treating their situation as a one-of-one event. At the same time, we prioritized building trust — showing clear respect for our client’s founder-CEO background and experience.

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Discovery

As we do with every client, we began with discovery. Here, we worked through an exhaustive checklist of potential needs to identify immediate financial concerns, long-term desires, preferred methods of engagement, and Legacy Knight capabilities that wouldn’t play a prominent role at the outset.

Through this process, we not only unearthed their goals, but also learned more about their stressors following the accumulation of this new wealth. In addition, we found alignment on the principal’s risk profile and the lifestyle services we could offer that would enable them to live their ideal life.

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First-Year Tax Guidance

Understanding that they were entering a new world of tax complexity, the principals fully trusted Legacy Knight to take the lead. This client was proactive enough to contact Legacy Knight when the principal’s company sale was still on the horizon, allowing us to do the maximum amount of estate planning before the sale process actually began. From there, we explored and implemented strategies to mitigate, defer or reduce tax liability from the sale while also laying the foundation for long-term tax savings.

Post-sale, we coordinated directly with their CPAs and navigated all documents, identified errors, and ensured every obligation was met. This all was done with the minimum amount possible of family involvement.

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Integrated Team Coordination

This client sought a partner they could trust to act on their behalf, and Legacy Knight became their external center of gravity — leading their team of lawyers, advisors, and private equity contacts. At the outset of our engagement with the family, we established a weekly meeting cadence that allowed us to understand their needs and objectives in intimate detail while building rapport with their other advisors.

From there, we adjusted to a monthly meeting rhythm before shifting to quarterly updates. As always, our goal was to take a posture of leadership and, as efficiently as possible, unburden our clients to the greatest extent we can.

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Bespoke Investment Strategy

Armed with a clear picture of the family’s risk tolerance and goals, as well as the knowledge that they were partially drawn to Legacy Knight for our understanding of alternatives, we crafted a tailored investment portfolio to help realize their goals.
 
This resulting portfolio was modeled after top endowments and family offices, but also incorporates exclusive opportunities to which Legacy Knight has access and other asset classes that are of particular interest to this client.

A more unique goal, and one we took just as seriously, was the principal’s life-long desire to be a professional sports team owner. The process of vetting and attaining a trophy asset like this is something not uncommon at Legacy Knight, and we got to work by first drilling into his risk tolerance and goals beyond pure ownership. From there, we collaborated with investment bankers experienced in this arena before identifying the ideal team, performing diligence on the financials, meeting with existing ownership, and negotiating favorable terms.

We then worked directly with the league on the principal’s behalf as the deal moved toward closing. Throughout the process, we sought to make it as simple as possible for our client, providing status updates and representing him whenever possible while also ensuring he could step in and be present during critical times or for moments that simply interested him.

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Long-Term Planning

Looking further into the future, the principal shared several priorities with us. We first assuaged their concerns about generational wealth transfer, working alongside their legal counsel to create a clear estate plan that also included an educational component to help future generations maintain good stewardship of their wealth.

We advised on insurance decisions and philanthropic strategies to maximize their internal advantage and external impact. Critically, we developed customized reporting dashboards that not only were tailored to their specific needs and portfolio, but also completely aligned with the depth of information the former founder desired.

Outcome

A Trusted Partner Delivering Peace of Mind

With each of its services, Legacy Knight continues to deliver the clarity and confidence this family needs to live their best lives. From overcoming the initial hurdles of new wealth to planning for a future of perpetual prosperity, Legacy Knight has taken a leading role in securing their legacy.

We’ve made them comfortable moving beyond the demands and personal sacrifices of business ownership and transitioned them into the life of comfort they’ve earned. And they know they weren’t handed a templated playbook; instead, we coauthored a strategy designed to create the best possible outcomes for them.

In Their Own Words
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When you ask them questions, there is a reason for everything. They’re not playing from a standard book. There’s an intention behind everything. They’re good people to their core, which is an important thing in this business. It’s not purely about the return. It’s about who you’re dealing with on the other side.”

Family Principal
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2026 Tax Updates

2026 Estate Planning Themes

A Look at the Legacy of 2025

Grow your wealth and protect your legacy.

We are invested in enhancing and securing your family’s wealth for generations. The journey starts with understanding your unique objectives and leads to real peace of mind.