The $500K Question

I was in a car with two founders recently — one still deep in the build, the other just on the other side of an exit. The kind of conversation that happens when successful people have a bit of time and space to think out loud.

The one with the exit was talking about an opportunity that had come across his desk. A well-known private company — the kind that’s notoriously difficult to get into — was raising a new round of capital. He’d been approached. The buy-in was $500,000.

The founder still building leaned in immediately. He knew the company. He was intrigued.

Then he paused.

Half a million dollars. Into a single private company. Tied up until an IPO that could be years away — if it happened at all. Even for a successful founder, that’s a significant concentration of liquid capital sitting in one place with no exit in sight.

He was interested. But he couldn’t quite get himself to the table.

I sat there listening and thought — this is the conversation most founders never get to have.

Private market investments have historically been the domain of institutional investors and the ultra-wealthy. Pension funds, endowments, family offices. The kind of organizations that can write a $500K cheque into a single company and still have a diversified portfolio underneath it.

For everyone else, the options have been limited. Either you’re at the table with enough capital to take the concentration risk — or you’re not at the table at all.

What most founders don’t know is that there’s a third option.

Through the Watermark Private Portfolio program we have access to some of the world’s leading private equity managers — Fiera Comox, Hamilton Lane, Partners Group, among others. These aren’t generic funds. They’re institutional-grade private portfolios that we build specifically for each client, diversified across companies, sectors, and strategies.

And here’s the part that surprises most people: the structure provides significantly better liquidity than you’d typically find in private market investments — the kind of flexibility that most institutional structures simply don’t offer retail investors. You’re getting private market exposure — the kind that pension funds have used for decades to drive returns and reduce volatility — without locking your capital away indefinitely.

The founder in that car didn’t need to choose between the opportunity and his liquidity. He needed a structure that let him access private markets the way institutions do — diversified, professionally managed, and without betting half a million dollars on a single outcome.

That structure exists. Most founders just don’t know to ask for it.

Private market access isn’t just for the $50M+ crowd anymore. If you’ve never had this conversation with your advisor, it might be worth having.