I bought a PSA 9 Shining Magikarp 1st (Neo) and a PSA 6 Rev. Holo Electrode (Legendary Collections) together as my first PSA Card purchase. I think Electrode arrived in the mail first, so I guess technically its my first psa card haha. To this day i still have both in my collection:D
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A PSA 10 Gold Star Charizard back in 2017. I paid $1000 for it and I said to myself, you’re crazy paying this amount on a card 
So, 
You old me 
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I believe it was a PSA 9 Jolteon holo from Jungle.
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PSA8 Charizard Base set for 140. I was an idiot and sold it 6 months earlier this year for 160. So went yolo and bought a 1st ed 8.5 Zard.
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Metapod baby (PSA 10 1st ed, recently)
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PSA 9 1st Ed Fossil Dragonite in April of this year @ $300 - sold it a few months later at $550 when I learned more about my collecting style and found it didn’t fit in my collection anymore.
Back then I had a goal of collecting favorite sets/species in PSA 9 (1st Ed, if available). After buying a few 9s, I found myself still keeping an eye on 10s and wanting to “upgrade”. I scaled back my collection goals and focused instead on 10s of certain species (Dragonite + Arcanine) and other specific cards that I had a nostalgic attachment to.
PSA 10 Japanese Entei and Suicune from Neo 3! Love those cards
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First PSA card was one of my submissions from maybe 3 or so years ago, my personal Gold Star Umbreon, got back into the hobby around then.
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I’m surprised we haven’t seen any comments yet with people stating: “I’ll let you know when I get my first.” or something alone those lines. I bought my first PSA-graded card little over 1.5 year after I came back collecting again. This thread goes to show how popular graded Pokémon cards are. Even if you are a binder collector, a lot of people still own at least one graded card. 
Greetz,
Quuador
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Last June I bought unlimited base PSA 9 Charizard, Blastoise and Venusaur for $300. At the time I was so nervous about spending so much on 3 pieces of colorful card in some plastic and came close to selling them to try and get most of my money back. My girlfriend was livid when she found out but luckily I did keep them. Now they’re worth around $2000 and I get to be insufferably smug, pretending I’m some hotshot investor/collectibles genius. I have since bought around 600 graded cards and have no money or life.
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To this day I have never owned nor even handled a graded card. Not a real big hobby where I live and those who are into Pokemon just play. I don’t keep many cards if any at all so I don’t hold onto any card long enough to consider grading them.
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Munch Pikachu Promo PSA 10! Back then I thought it was crazy to be paying 100 dollars for a cardboard in some plastic, but loved the art. Ended up getting the complete set in PSA 10. Nothing quite like it!
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My very first purchase back in the hobby was almost the exact same thing. It was a complete set of 16 PSA 9 1st ed Base holos from @garyis2000 for $990 back in 2009.
My second purchase in the hobby was a PSA 10 1st ed Base Charizard for $700, also in 2009.
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I have not purchased a graded card yet but I did submit some cards to CGC and will be getting them back soon so those will be my first. Seeing all of these graded cards and hearing the stories about how they’ve been obtained and the coast has been great!
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My first PSA graded card/s (two because they were in the same submission). Sent these through Ludkins back in 2013!
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It’s nice and reassuring to see that basically all mentioned cards appreciated in value by 100-xk% since they were purchased.
Congrats to all of us, I guess
Shiny Rayquaza from Hidden Fates, bought it 2 months ago
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First graded card was a base set first ed charizard psa 7. I bought it in 2014 I think for 450 dollars. I sold it last spring for 2300. Wish I waited just another 2 months for a couple thousand extra!
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Charizard EX Black Star promo PSA10. Still one of my favorite artworks. Great question, I had to go all the way to my first few eBay purchases to find out.