The size of an investor's check tells you the least about them

Picture two term sheets sitting side by side, offering identical amounts of money for identical equity. The first comes from an investor who spends half the call asking sharp questions about your industry, mentions two people worth introducing you to before you even ask, and lingers afterward to talk about something unrelated to the deal entirely. The second comes from an investor who barely engages beyond confirming the number, pushes for a larger option pool just to be safe, and starts angling for more board control before due diligence has even started. On paper, these two offers look the same. Alejandro Cremades argues they are not remotely the same deal.

His reasoning starts from a fact founders often underweight: once an investor is on your cap table, they are there for the long run. Divorcing a spouse, he notes bluntly, is often easier than divorcing an investor. That permanence is why he insists founders look past the check itself and evaluate three things: what expertise the investor actually brings, who they can connect you to, and how financially solid they are themselves, since an investor stretched thin elsewhere brings that stress straight into your relationship with them.

The reverse also matters. Cremades is equally direct about the red flags that should make a founder walk away regardless of the number attached: outright greed, values that don't match yours, or worse, plain unscrupulousness. He points to Mark Cuban's investment in Motionloft as a cautionary real-world example, where the founder was later pursued by the FBI over allegations of secretly angling to cash in while raising money from others. Cuban is a sophisticated, experienced investor, and even he ended up entangled with a partner whose values didn't hold up. The lesson Cremades draws isn't that due diligence guarantees safety, it's that vetting has to run in both directions, and that bad partnerships can damage everyone attached to them, investors included.

He closes the thought with a line from Cuban himself, one Cremades clearly takes to heart: it is much better to have one percent of a billion dollars than a hundred percent of nothing. Greed, in other words, isn't just an ethical problem, it's frequently a strategic one, because chasing the biggest possible slice tends to shrink the pie everyone is fighting over.

Before ranking any investor by the size of their check, score them separately on the expertise, connections, and financial health they bring, since those three things will matter long after the wire transfer clears. Read every clause for signs of a future control grab, an unusually large option pool request, or pressure for board control ahead of schedule, and treat either as worth a direct conversation. Ask plainly when this investor last funded something and how their other investments are performing, because a stretched or struggling investor brings that pressure into your relationship whether they mean to or not. And pay attention to whether they're genuinely curious about your business or only about the return, since that difference tends to show up again, at the worst possible moment, later on.