The Stakeholder Conversation Most Founders Never Have

Most founders hand out options, file the paperwork with Carta, and move on. The mechanical part gets done. The meaningful part gets skipped.

That’s a missed opportunity. Not just for the team. For the business.

There’s a difference between someone who works for a company and someone who builds one. The mindset is different. The relationship with Monday morning is different. When people genuinely understand what equity means and what it could mean, something shifts. They stop thinking like employees and start thinking like stakeholders. That shift is not small.

But here’s what I’ve seen get in the way. Most people have an unhealthy or underdeveloped relationship with money itself. So when you hand them options, they don’t know what to do with that information emotionally or philosophically. They either dismiss it (“it’s probably worth nothing”) or they fixate on a number that doesn’t exist yet. Neither response is useful.

Before equity can change someone’s relationship with their work, it has to connect to something real for them. And that requires a conversation about money that most workplaces never have.

Money is a tool. That’s not a new idea, but it bears repeating because most of us were never taught to actually think about it that way. We were taught to earn it, spend it, save it, and stress about it. We were not taught what it’s actually for.

I think about money as serving three primary purposes. The first is security: the stability to weather uncertainty, provide for your family, and not make fear-based decisions. The second is experiences: the memories you create, the places you go, the shared moments that shape who you and the people you love become. The third is doing good: stewardship, contribution, using resources to make things better beyond yourself.

That’s it. Three things. When you orient money around those three purposes, it becomes a tool with a job instead of a scoreboard with no finish line.

Now layer in something I first encountered through Sahil Bloom’s work on the Five Types of Wealth, and which has become a useful lens in my own coaching: financial wealth is just one dimension of a much richer picture.

There’s time wealth, autonomy over how you spend your hours. Physical wealth, the health and energy to actually enjoy what you build and live long enough to see it. Mental wealth, clarity and peace and the absence of chronic stress, which is often the first casualty of building something. And social wealth, the relationships and community and belonging that compound quietly in the background while we’re busy chasing the other stuff.

Financial wealth matters. It creates optionality. It removes obstacles that stand between you and the life you actually want. But you can win financially and lose in every other dimension. That’s not success. That’s a very expensive version of empty.

Here’s where equity becomes interesting. When you understand what financial optionality actually unlocks, equity stops being an abstract number in a cap table and starts being something else entirely. It becomes a potential catalyst for all five dimensions.

More financial cushion creates more time flexibility. More time creates space for health. Less financial stress contributes to mental clarity. Security strengthens relationships. Each one feeds the others.

That’s not a pitch for equity. That’s just how it works.

And the deeper truth is this: the value of any equity stake is not set by the market. It’s set by what the team builds together. Every time someone strengthens the operating discipline, sharpens the focus, improves a system, or shows up with more intentionality because they feel like a real stakeholder in the outcome, the business becomes more valuable. And when the business becomes more valuable, so does everyone’s stake in it.

I think about the founders I work with who are navigating the messy middle, somewhere between startup and durable scale, building something that genuinely could become significant. Most of them have equity conversations that are purely mechanical. They treat it as a retention tool or a compensation workaround.

What if instead, it was the beginning of a different kind of relationship with your team? One where people understand not just what they were hired to do, but what they’ve been invited to own.

That’s a different kind of organization. One where the Monday morning feeling is different. One where people are thinking like stakeholders because they actually are.

The question worth sitting with isn’t what your equity program is worth today.

It’s what you decide to make it worth together.