Big IPOs, Bigger Feelings: What to Ask Before You Chase the Headlines

You can't open a news app right now without running into another story about the IPO rush.

SpaceX went public in the largest IPO in history, debuting at a valuation north of $2 trillion. OpenAI and Anthropic have both filed for IPOs of their own, with private valuations pushing the trillion dollar mark.

I get why people are curious. These aren't obscure companies. They sit right at the center of some of the biggest shifts happening in how we work and live.

And when a story gets this much attention, it tends to raise the same questions in almost everyone.

What if this is the next Amazon? What if I miss out? What if everyone else can see something I can't?

Those are normal, human questions. I'd ask them too.

They're also exactly where investing gets messy. Excitement has a way of dressing itself up as certainty. Urgency starts to feel like analysis, even when it isn't.

Some of these companies might turn into once in a generation stories. Others might not. Nobody actually knows how this plays out, no matter how confident anyone sounds on TV.

So before I'd ever encourage a client to put money into a hot IPO, or any investment that falls outside their plan, I'd want to sit with a few questions first. Here are the ones I come back to, over and over.

1. What would change my mind?

This one does a lot of work. If your honest answer is “nothing,” that's worth noticing.

A good investment idea can flex when new information shows up. A decision made from excitement usually can't.

2. Would I still want this if nobody else were talking about it?

Headlines create attention. So does everyone around us getting excited at the same time. It's easy to feel sure about something when the whole room agrees with you.

Take the noise away for a second. Does it still make sense for what you're actually trying to build?

3. How would I feel if this dropped 50%?

Use your real numbers here, not round ones. A 50% drop sounds abstract until $20,000 turns into $10,000, or $100,000 becomes $50,000.

That question tends to reveal whether you're looking at your actual comfort with risk, or the version of yourself you wish had more of it.

4. What job is this investment doing for me?

Every dollar in your plan should have a purpose. If someone asked why you own something, could you answer in one sentence?

That's usually a good test. Speculation isn't automatically wrong. Mistaking speculation for a long-term strategy is where people get hurt.

5. What am I giving up to make room for this?

Money has to come from somewhere. Before it moves, it helps to know what it's moving away from.

Sometimes that trade makes total sense. Sometimes it quietly pulls you away from something you already decided mattered more, like a home, a career change, retirement on your terms, or simply the freedom to make a choice without checking a spreadsheet first.

That's really what this comes down to for me. I care a lot less about whether SpaceX or OpenAI turns out to be a great stock. I care a lot more about whether the decision in front of you still serves the life you're actually trying to live.

Big headlines have a way of making the next move feel obvious. A plan built around what matters to you creates a little space between the headline and the decision.

Sometimes that space is all you need to see things clearly.

If something outside your current strategy has caught your eye, I'd love to think it through with you. Not to talk you out of it. Just to look at it together, in the context of everything else that matters to you.