Who We Serve

Lionshead works with a range of clients — individuals, families, business owners, and professionals at different stages of their financial lives. What most of them have in common is a financial situation that has grown complex enough that they want one advisor who understands the full picture, not a collection of disconnected relationships.

We are a fee-only, SEC-registered independent RIA. We do not earn commissions, and we act as fiduciaries for every client — meaning we are legally obligated to act in your interest, not ours.

Below are examples of the clients and situations we work with most often.

CLIENT STORY

Two Careers, One Financial Life

Both partners at large corporate law firms in Manhattan, in their mid-40s with two children. When they came to Lionshead, they each had their own retirement accounts, their own investment accounts, and no real picture of what they were building together. Two high incomes, two firms' worth of benefits decisions, and an estate plan that hadn't been updated in years.

We started by getting everything on one page — reviewing both firms' 401(k) options, consolidating the investment strategy across their accounts, and setting up 529 plans for the kids with a contribution approach that fit their cash flow. We walked through their life insurance coverage and made the case for updating it. On the estate side, we worked with their attorney to put a proper structure in place — living wills, healthcare proxies, and a trust framework that made sense for where they were in life.



The day-to-day hasn't changed much for them. That's the point.

CLIENT STORY

Family Business Looks to the Next Generation

The operating head of a fourth-generation family business in Connecticut. By the time he came to us, it was a successful operation with real estate holdings, junior family members starting to take on roles, and a set of planning questions that had been deferred for too long.



The immediate issue was real estate — the business was expanding, and there were open questions about financing, entity structure, and liability. We worked through the holding company structure alongside his attorney and landed on an arrangement that made sense from both a tax and risk management standpoint.

The longer conversation was about transition. With the next generation coming in, we built a buy/sell framework that would allow ownership to transfer in a structured way — one that didn't create a tax event that could threaten the business itself. Estate planning ran in parallel, focused on moving value to his children and grandchildren without unnecessary exposure.

We manage the family's retirement assets and continue to serve as the coordinator across their legal, accounting, and financial teams.

CLIENT STORY

A New Chapter

She came to us in her early 70s after losing her husband, with assets that had been managed jointly for decades. The portfolio was in reasonable shape. What she needed was someone to look at the full picture — income, spending, estate structure — and help her understand where she stood on her own.

We built a cash flow plan for her retirement years that gave her a clear sense of what she could spend, what she should hold back, and what she could give away. We worked with her attorney to establish a living trust that reflected her wishes and would simplify things for her children down the road.



There was also a property she'd always wanted to restore. We helped her think through the financing and the eventual sale as part of her overall financial picture. When she was ready to begin making gifts to her children and grandchildren, we structured those to be thoughtful about timing and tax efficiency.

She's been a client for several years. The work has evolved, but the basic arrangement — one advisor who knows the full picture — has stayed the same.

CLIENT STORY

Laying the Groundwork

Early in his career, in his late 20s, earning well and trying to make good decisions before his financial life got more complicated. Not a complex situation by our usual standards, but one where getting the basics right matters a great deal.

We worked through the foundational questions — Roth versus traditional, how much to put into the 401(k) and which investment options to use, how to get full value out of his firm's benefits package. He had a home purchase on the horizon, so we set up a savings strategy separate from his long-term investments, structured around that timeline.



He's still a client. The questions have gotten more interesting as his income has grown and equity has started to vest.

CLIENT STORY

Into Retirement, Together

A healthcare executive moving into early retirement in his early 60s, and his wife, an educator finishing out her career. They'd saved carefully over the years and weren't anxious about retirement — they just wanted to make sure the plan they'd built informally would actually hold up.

We reviewed the full picture: portfolio allocation, Social Security timing, income needs in retirement, and how the shift from two incomes to none would affect their cash flow. The investment allocation needed to reflect a different stage of life. We worked with their attorney to put a trust structure in place.



When they decided to buy a new home and renovate it — something they'd been planning for a long time — we helped them think through the financing and what it meant for their liquidity overall. With a grandchild recently born, the conversation has started to extend to the next generation as well.

CLIENT STORY

Contemplating Legacy

A retired physician in his 80s with more than enough for his own lifetime. What he wanted was a thoughtful plan for the people and institutions he cared about — not investment returns, but a structure that would allow his estate to transfer the way he intended.



The complexity was real. His assets spanned brokerage accounts, real estate, a family limited partnership, and several irrevocable trusts. Lionshead took on the coordination role — working alongside his estate attorney to ensure alignment across all of it, managing the portfolio with preservation and eventual transfer in mind.

The gifting work was meaningful. We mapped out the annual exclusion and lifetime exemption picture, identified the most efficient assets to move, and built a multi-year plan that transferred wealth to his children and grandchildren in a way that reduced estate tax exposure without overcomplicating things for the recipients.

He had a clear sense of what he wanted. Our job was to build the structure around it.

Client scenarios presented are illustrative composites based on common planning situations. They do not represent specific clients or guarantee specific outcomes.

Stop Guessing and Get a Plan That Makes Sense

If you’re ready for clarity, support, and a partnership built to last, Lionshead Wealth Management is here to guide you—step by step. Let’s talk about what you need and make your next financial decision feel straightforward and achievable.