Brian Lamb co-founded Trust & Will, then ran into a version of the problem he had spent years trying to solve: estate planning that was expensive and difficult to navigate.
After taking an exit and looking at his remaining equity, he started digging into qualified small business stock, or QSBS. That work eventually became Promissory, the company he founded to help with QSBS trust planning.
I wanted to get into the mechanics with him. Our audience includes business owners, investors, and people with meaningful equity in the companies where they work. An exclusion can look compelling on paper. The useful conversation is about the decisions that determine whether it applies to your shares and your eventual transaction.
We also got into something that connects to my background in tech sales: an employee can do well at a company, earn substantial equity, and still face a serious cash problem when it's time to leave.
Here are the parts worth your time.
Your vesting schedule isn't your stock ownership history
You spend four years at a company. Your options vest. The company becomes more valuable. It's easy to think those four years have also been building toward every tax benefit attached to the equity.
Brian's point is that vesting options and acquiring shares are different events.
For an employee holding unexercised options, time at the company isn't the same as time holding the stock. His explanation of QSBS keeps coming back to that distinction: the company may qualify, but your own ownership timeline still matters.
The conversation also covers restricted stock and 83(b) elections. Those details need to match the actual equity arrangement. Hearing that a company is QSBS-eligible doesn't tell you that every employee has started the same clock or completed the same paperwork.
That is the question I'd want answered while there is still time to do something about it: what do I actually own, when did I acquire it, and which holding period applies?
An equity dashboard can show a substantial number. It doesn't settle those questions for you.
Leaving with equity can still require cash
I brought up the employee who spends years earning options, then leaves the company after the shares have become worth considerably more.
The options may be vested. The purchase still needs to happen.
That can mean coming up with cash to exercise, plus a possible tax obligation. The tax result varies with the option type and the facts, but the liquidity problem is easy to understand: the employee has a valuable opportunity on paper and a bill that needs actual money.
Brian discusses early exercise as something employees can ask about and founders can consider making available. Availability, affordability, and the consequences all matter. It still involves putting cash into the shares.
This matters especially for the person leaving a corporate role to start a business. I raised that scenario because the goal is often to preserve as much cash as possible for the next venture. An exercise cost and a tax payment can compete directly with that plan.
The useful time to understand those obligations is while you still have choices. Waiting until the departure paperwork arrives can turn a planning decision into an immediate funding problem.
The business can get a good price while you get a different outcome
Brian walked through acquisitions that involve a combination of cash and stock, along with questions about how the acquired business sits inside the buyer's structure.
Those terms matter to the shareholder. The headline number doesn't explain how the consideration reaches you, what remains tied up in stock, or what conditions sit around an earn-out.
This is why Brian encourages founders to have their own counsel on the transaction. Someone needs to examine the founder's individual position alongside the company's deal.
That doesn't require assuming the company and the founder are in conflict. It requires recognizing that they are answering different questions. One question is what the buyer will pay for the business. Another is what that agreement actually means for a particular person holding shares.
For the QSBS discussion, transaction structure is part of the analysis too. We talk about why an asset purchase and a stock purchase can't simply be treated as interchangeable.
I think that is a useful way to approach any exit conversation: get past the valuation announcement and follow the proceeds all the way to the owner.
A signed offer is a poor starting point for trust planning
When I asked where Promissory enters the process, Brian described working with founders at different stages. His preferred timing for setting up trusts is roughly 18 months before an anticipated exit.
That is his planning guideline, not a statutory waiting period or a promise of approval.
The underlying concern is that a last-minute transfer, once a transaction is already taking shape, faces a different set of questions from a structure established for genuine family and estate-planning purposes well beforehand.
Brian contrasts that with repeat founders who start thinking about the structure while the business and share value are still early. They have been through an exit before and understand which decisions become harder to revisit later.
An eventual deal can also fall through. He acknowledges that, and the need to weigh the facts with outside counsel.
That uncertainty is part of planning. You won't know the exact sale date years ahead of time. But you can understand what you own, who you intend to benefit, and what a transfer would mean before a buyer's timetable starts driving the conversation.
The trust strategy changes whose assets they are
I asked Brian a straightforward question: if I create a trust for my son, do I commonly serve as the trustee?
His answer described the structure Promissory uses: an independent trustee, separate investment oversight, and a completed gift to a non-grantor trust.
The important distinction is that giving shares away changes ownership and control. This isn't just a new label on the same personal account.
The conversation about trust stacking can attract attention because of the potential tax benefit. But the family decision belongs in the same conversation. Who is the beneficiary? Who makes decisions? What access and authority does the person making the gift retain under the actual documents?
Brian's answer is specific to the approach he describes. The permitted roles and tax treatment depend on the structure; putting the word irrevocable on a trust doesn't settle everything.
I'd want the ownership decision to make sense on its own terms. A projected tax saving doesn't answer whether you are comfortable transferring the shares for someone else's benefit and having the assets managed accordingly.
Give the full episode a listen. Brian makes the conversation useful for anyone whose next major financial event may depend on company equity, because he connects the potential tax benefit to the purchase, timing, transaction, and control decisions underneath it.
- Sam Silverman
Silverman Capital
