Yes he did, you've cottoned onto what Columbus was doing for a sizable chunk of the 1480s. Before going to Spain, Columbus' first choice of patron was John II of Portugal. The Portuguese king listened to Columbus' proposal, loved it, but was smart enough to gather scholars to study the proposal in detail. These men, being better at math than Columbus (who based his entire plan on his own miscalculated circumference of the Earth, d’Ailly’s misjudged width of the Atlantic Ocean, and Toscanelli's wildly exaggerated size of Asia), quite rightly pointed out that he had vastly underestimated the length of the voyage and that he and any men with him would die. Despite this, Columbus somehow rated a second interview with John, but ended up being thoroughly upstaged by an explorer name of Dias who showed up with the hot news that it was in fact possible to sail around Africa.

So Columbus went to Spain (I broke these up by country for brevity, but to be specific, he returned to Portugal for his second interview with John after this first visit to Spain) and presented his proposal to Queen Isabella. Like John, Isabella also gathered a council of learned people she could lean on to dissect the proposal, and like John's advisors, Isabella's advisors were also better at math, history, and geography than Columbus, and besides, the Spanish crown was a little tied up with a little war with Granada. However, Isabella and Ferdinand didn't have another explorer suddenly show up out of nowhere to make Columbus obsolete, and they apparently still thought his idea had some merit, because the crown paid him an allowance for two years, hoping he would stick around and not go shopping for other patrons.

Which did not stop Columbus from trying his luck with a third monarch. He was being paid good money (roughly the same pay that a sailor would make, on top of free room and board) to not leave the country, so he sent his brother Bartholomew to England to inquire if Henry VII was interested, but to little success. One source I've read claims he was kidnapped by pirates before reaching Henry's court, but most others agree he was turned down by Henry and made his way to France, where he was turned down by Charles VIII, and finally arrived in Spain in 1494 to find out his brother had sailed back and forth across the Atlantic already.

Columbus's luck finally turned around in 1492. He was prepared to give up on Portugal, Spain, England, and set to travel to France. But the war ended in Spain's favor, and the pressure was on to not let Portugal own the entire Asian sea trade. So Isabella and Ferdinand took a chance on the lucky idiot.