Wrestling with Risk at 30

Most mornings and nights, when the kids are down, I open my laptop or phone to a list of ideas and things to do. It's long. It's always been long. My problem isn't generating ideas, it's choosing which ones to actually commit to and focus on.

I'm ambitious and restless. I love building. But lately, I've been contemplating my decisions more than the ideas themselves.

The Big Paths I've Been Considering

Sandbox Fellowship — A year to build a startup while getting a master's degree. On paper, it's exciting. In reality, it's a $100k burn. With a baby coming in the next year, it feels too risky for this stage of life.

Join a smaller startup — Higher equity, exposure to founders, the chance at a meaningful outcome. But it's still someone else's vision, and it could pull me away from my real goal: being a founder.

Cofounder Route — big potential fast-forward, but higher risk of partnering with the wrong person or chasing the wrong idea.

Stay at Podium — Stability, benefits, predictable paycheck. The safest option. But it carries its own danger: complacency and lower upside compared to what I believe I'm capable of.

The Paradox

I recently heard the quote from Warren Buffett: "You don't risk what you have and need for what you don't have and don't need."

Been thinking about this quote a lot now that I've got two kids, a mortgage, and the normal responsibilities of life stacked on top of ambition. The cost of downside risk has gone way up.

And what I can't ignore is that it only gets riskier from here. More kids, more obligations, less flexibility. So if not now, when?

Where I'm Leaning

Right now, the smartest move looks like staying at Podium. But not just to play it safe. The plan is to use the stability to stack savings, sharpen my distribution skills through writing, and take on a small amount of freelance work to generate cash flow. That turns “staying put” into an active strategy of building runway and optionality while avoiding too much risk.

I’ll keep experimenting like a founder on the side. And I’ll keep cofounder conversations open, but only commit if a short sprint proves real traction.

The Big Question

I don't have the perfect answer. I'm a 30-year-old dad of two, husband, son, engineer, and entrepreneur who wakes up most days with more ideas than time.

So the question I keep circling back to:

How do you balance ambition and responsibility?

If you’ve walked this path, what helped you know the right time to swing bigger?