You are building or have built real wealth inside a company whose shares now sit on your balance sheet in a size that makes you uncomfortable. Vesting schedules, RSUs, EMI, tender windows, bonus deferrals: the instruments are clear. The question is what to do with them, and when.
It is the price of having been early, or senior, or both. The shares that made the career are now the shares that make the anxiety.
You already know, intellectually, that you are too concentrated. What you need is a plan for unwinding that does not accidentally hand half of the proceeds back in tax.
Our work begins with the question most other advisers skip: what is this wealth actually for? The answer rarely reads "maximise terminal value." It reads, more often, as a set of commitments (to a second house, a set of children, a retirement date, a philanthropic instinct) which, once named, let us work backwards to an allocation that serves them.
From there the mechanics follow: tender participation, 10b5-1 windows where applicable, hedging structures for concentrated positions that cannot yet be sold, tax-aware sequencing across pensions, ISAs, VCTs and EIS where appropriate, and the quiet work of building a liquid reserve that lets you hold the rest of the stock with a steadier hand.
For executive clients the value of our Guardian:CONNECT approach is most visible at the edges, where a share-sale decision has CGT, share-scheme and pension consequences that need a single coordinated answer, not three conflicting ones.
Sort before you allocate
Your wealth (the bit in the ticker and the bit outside it), sorted into three jobs, before any investment decision is made.
One coordinated answer
Your tax accountant, your share-scheme lawyer, your financial planner, all looking at the same sequencing decision, at the same time, with a single written recommendation.
Tranches, windows, wrappers
A multi-year sequenced unwind of concentrated stock, written down as a schedule, so implementation happens at the earnings window, not in a panic.
Why most executives underestimate how much of their financial future is really tied to the fortunes of a single company, and what a reasonable path out looks like.
How we sequenced a four-year unwind of restricted stock around earnings windows and a firm exit date, without the client becoming a forced seller.
The arithmetic of the 60% marginal band, and three structural moves that materially improve net take-home for executives sitting inside it.
I came in thinking I needed someone to manage a portfolio. I left with something more useful: a four-year sequence of decisions written down, in English, that my wife, my lawyer and I could all read on the same page.
Come with a share schedule and a question. Leave with a clearer view of what the next three years ought to look like.