Survivor Ghost Island has arrived! Every week, Parade’s Mike Bloom will bring you interviews with the castaway most recently voted off of the island.

Risk and reward are the key components of every decision throughout the past 35 seasons of Survivor. In a season that embraces an attempt to undo the bad decisions of those contestants gone, but not forgotten, it would make sense for the castaways this season to truly grasp that risk/reward bull by the horns and take it for the ride of their lives. Enter Jacob Derwin. The Long Island native and former Survivor blogger spent his six days in the game making dicey calls, whether it was talking up his tribe in order to get sent to Ghost Island, risking his vote for a chance at an advantage, or making a bluff of finding a hidden immunity idol. But much to his and former player Wes Nale’s chagrin, he did not get a biscuit by risking it, as his status as a social outcast of Malolo sent him out of the game with both his heart and feet in pain.

When Jacob’s feet hit the sands of Fiji (a feeling he would become all too familiar with after his shoes got accidentally carried away in the tide), he looked around at the people he would be playing against for hopefully the next 39 days and had a sense of deja vu. It was a social scene that reminded him of growing up, where he would be the first to admit he wasn’t very popular and stuck out like a sore thumb. He noticed that he and Donathan Hurley did not have the most imposing physiques, and anticipating getting targeted. As a result, he struck out to find an idol. His literal distancing himself from the rest of his tribe made him an easy target, and that’s even without them knowing that he poured the camp’s rice through his Bigfoot sock to find his own elusive prize in an idol clue. When Malolo lost the first Immunity Challenge, Jacob’s hair still had an air of defiance, telling everyone that he felt their tribe was one of the best of all time. But this turned out to all be a ruse, as he had now become a target even on the other tribe to get sent to Ghost Island and not attend that night’s Tribal Council.

The Survivor gods may have been in play with that decision as well, as the most prominent superfan on the cast was the first to get exposed to Ghost Island, a mausoleum of catastrophic choices, accented by a shelter adorned with torch snuffers from the previous seasons. But the gods were looking to play games with him as well, specifically a game of chance. He was instructed to choose one of two bamboo canisters. Choose wisely, and he earns an advantage; choose poorly, and he loses his vote at the next (and for him, first) Tribal Council he attends. Jacob went for broke and ended up picking the correct shoot, only for him to yell something close to “Shoot” when he found out he now had a Legacy Advantage to give to someone on the other tribe, which he gave to marine animal trainer (and noted puzzle dodger) Morgan Ricke. He realized he could benefit from what James Lim would go on to call an “information imbalance,” and fabricated an idol along with a story of being gifted one on Ghost Island. He walked back to Malolo with his new crafts project, but teacher Brendan Shapiro was quick to give it a poor grade. Malolo lost the next Immunity Challenge, and Jacob hoped his reputation with Naviti would get him out of Tribal Council once more. But they instead chose Donathan Hurley, who despite losing, had his moment of triumph when his tribe and host Jeff Probst convinced him to make a key dive to continue the challenge. Facing the vote for the first time, he sought a connection with Stephanie Johnson, and in a tale as old as time, he told his “Beauty and the Beast” alliance partner about what truly happened on Ghost Island. This reveal proved to Stephanie how much Jacob trusted in her, and she genuinely debated keeping him in over someone like Michael Yerger who may not be on her side. But when the votes came in, the self-described “neurotic, paranoid indoor kid” was sent back into his natural habitat after nearly a week of Survivor filled with highs and lows.

Now out of the game, Jacob talks with me about whether Survivor made him revert to his old self, why he chose to give Morgan, the Legacy Advantage, and what he hoped to show his friends and family from his time on the show.

You said in your final words that you felt embarrassed and leaving “hurt on a very deep level.” Where did those feelings come from exactly?

Just the fact that I went out so early, that’s all it was. I had a pretty good feeling going into Tribal that I wasn’t going to make it out. My plan was a little farfetched and had a lot of moving parts. There was no certainty on whether it was going to come together. So it was just knowing that I only got to see six days of the game. You spend a lot of time getting ready for this thing. You spend a lot of time, a lot of years thinking about it. To only get a couple of days is not a great feeling. Still not a great feeling, and it’s a hard one to shake.

You talked before the season about how you had to figure out social dynamics as you progressed in life, not starting out as the most popular kid. Did going to Fiji bring out the middle school version of Jacob?

(Laughs.) I said it a lot of times on the show, [but] I really do stick out like a sore thumb. Don’t get me wrong; you’ve got to remember once again that you miss a lot in six days in two hours. I did build friendships; I did make friends and build relationships. I think, to this day, a lot of them endure. But it wasn’t everyone. Unfortunately, I had trouble connecting to a lot of people who are stylish and hip. I may have been comic relief for them at times, [but] just because you think someone is funny doesn’t mean you want to work with them, spend time with them, and get to know them. I think, maybe sans Laurel or Stephanie, nobody asked me anything about my life. Nobody wanted to bond with me. Every conversation I had about strategy out there was initiated by me because nobody wanted to talk with me about it. For about three days, I would go around, and I’d be like, “So, who are you thinking about? Who’s on your radar?” And people would go, “I don’t know yet.” That happened for maybe four out of the six days, so it was infuriating. You can blame it on me because I’m different from the rest of the group. I have a lot of different interests, sensibilities, sense of humor, and a look about me. You also have to look at the rest of the people and consider maybe how they were acting too. Obviously, they voted me out, so it doesn’t really matter what I think about them. (Laughs</em.) But it’s complicated.

Let’s talk about those relationships. You just mentioned you connected a lot with Stephanie and Laurel, and we saw a bit of that on the show.

Just a little bit of the Stephanie. (Laughs.)

Just a tad, a little Beauty and the Beast going on there! But all three of you do have a diehard love of the show in common. Was that something you were upfront about during your time on the show?

I knew pretty early that everybody knew I was a superfan. I kind of stand out. In Game Changers, when Sandra was coming into the game, she pretty much knew how she was perceived. A two-time winner, the whole “queen” thing. So she played it up, and for a while, it worked. I had a similar thought where everyone knows I’m a superfan the moment they see me, so I might as well play it up. I’m dropping stats around camp. People are asking, “Who is that player?” and I’d say, “Oh yeah. That’s Kourtney Moon from One World. She got evacuated!” Just dropping random knowledge and hoping someone would be like, “Here’s my guy.” I had to believe that with a theme like this, other people on my tribe would know the game as well as I did. I was hoping I could reach out to them and endear to them through the nerdy Survivor stuff. And it worked a little bit; I made some friends out of it. But other people weren’t willing to be open because they had other attributes. I’m not out there for my abs; some people have those though. I had to kind of figure out how I can connect, and that was the one way that made sense for a few people. It’s funny with Stephanie. We connected early; we were being friendly and joked around a lot, probably [on] Day 1 or 2. It’s kind of funny that on the show’s it’s like “Jacob meets a girl, girl talks to Jacob, Jacob spills beans.” But it was more complicated than that. The people I found myself connecting with were definitely the other big fans.

But to that point, your superfandom almost becomes a double-edged sword when you come back with the fake idol, and Brendan calls you out on not having a note to go with it!

It was a good read. I give Brendan all the credit in the world for that. I thought of it ahead of time, realizing that I don’t have the parchment. I can’t make that up; I can put things on a string and say it’s an idol, but I can’t my own [note] in the dirt. So I had to deal with it and hope my bluff was strong enough and my story was strong enough that they might buy Ghost Island is a spooky place where things just happen to disappear sometimes. Unfortunately, it only got about halfway there. It was enough for some intrigue and make people consider changing their plans, but it wasn’t quite enough.

Speaking of bluffing, I want to talk about that moment in the first episode post-Immunity Challenge. You brag about your tribe to get Naviti to send you to Ghost Island, but when you do that, you pull a Syndrome from The Incredibles, and you monologued!

(Laughs.) “You caught me monologuing!”

Yeah! Why did you choose to vocalize that after the fact? Did it have anything to do with this idea in the second episode where you hope Naviti will just keep sending you to Ghost Island?

You completely got it. The moment they said, “We’re going to send Jacob,” my thought was, “Oh, that worked! Maybe if I make them hate me, they’ll send me again next time.” (Laughs.) That was the whole idea: Send Jacob out of spite over and over and over again. And that would have been fine with me. At that point, it’s sad to say on Day 3, [but] I was just trying to figure out how to make it to the next Tribal. I wasn’t thinking about at that point nurturing every individual relationship. I wasn’t thinking about being the Mr. Likable Guy I wanted to be in the pregame. At that point, I’m thinking, “How do I make these people make me suffer in some way?” And I thought if I made them not like me, they would keep sending me! Thus the Syndrome-esque monologue.

So going to Ghost Island, you receive this Legacy Advantage, and you chose to give it to Morgan. What was it about her that stood out to you?

I was torn between two people: Desiree and Morgan. I liked Desiree’s style; I thought we would get along and have a lot of things in common. I got good vibes from Desiree. But I got to see Morgan a little bit in the first challenge, where she’s bashful about the puzzle. She gave off a super likable, smiley friendly, and seriously athletic, vibe. So I thought, “This person seems super steady, super strong, and super friendly.” I didn’t know if I would mesh as well with Desiree and with Morgan, just based on first impressions. That was kind of the idea. I tried to pick the person who I thought would be the most steady and subtle with it. Someone like Domenick…no. I’m not going to give it to Domenick, not going to give it to Chris, not going to give it to someone who’s been invisible like Chelsea. I want to make sure to give it to someone who’s middle of the road, not super visible but not super-invisible, and strong enough to hang in there for a while. So she just made the most sense.

Ghost Island has this inherent benefit and cost. On the one hand, you get the chance to go for an advantage, and you’re safe from being eliminated at that Tribal Council. On the other hand, you’re away from your tribe, and you come back with suspicion as to what you may have found there. Overall, do you think your trip to Ghost Island helped or hurt you?

I think it gave me an opportunity to save my ass. And I think I got close! There were probably other ways I could have handled the situation; I’ve been thinking about it for many, many months now. I’m sure there was a different approach that might have worked. Look, I don’t doubt I would have been voted out first had I not gone. So in that way, it was helpful. Of course, when you’re the only person to know about this mysterious thing, everybody’s going to be wondering about you. It makes the target on your back even bigger. But the targets were already there. So maybe it hindered me a little bit, but it was 100% worth the risk.

Speaking towards possibly doing things differently, do you think Michael was the correct person to target?

Stephanie and I were not the only people talking about an early swap; I’ll tell you that. That conversation had been had with a few other people. I think the pitch is a solid one still. “Hey, a swap’s going to come. We don’t know who’s going to be on our tribe. Why not take out one of the stronger guys while we have a chance?” Everyone can tell Brendan and Michael are leading the fray right now, so why not? Why not shake things up? Why not take a little bit of control while you can? Why not take out a threat before he gets away from you? (Sighs.) It’s hard to convince a bunch of people in the early stage of the game to take out the guy who helped them win their first reward, who’s clearly a physical beast and making puppy eyes at all the girls. It’s hard to say, “Let’s get out the guy who everyone loves.” But it was the best idea I had. I didn’t want to target someone else like me, like a Laurel. I didn’t even want to target James, even though he was the other obvious target. These are people I wanted to keep around because they were the only people who would probably work with me. Brendan and Michael weren’t going to work with me. I tried to work with Libby for like a minute on the first day and realized there was nothing going on there. It was just about picking someone who I could potentially rally other people against if they could see my perspective. But of course, that assumes that anybody cared about my perspective. (Laughs.)

You said in your Day After video that you hoped your Survivor experience would show your friends and family how far you’re willing to go to benefit them. Can you elaborate on that?

I had trouble articulating that, even back then. I’ve had a weird social life. (Laughs.) Some people may say I have no social ability, or that I’m “special.” I said it a thousand times in the pregame stuff, but I’ve not always been the most popular guy. I’ve not always got along with a lot of people. I’ve had trouble making friends for a very long time. I’m at this point of my life now where I’ve lost a lot of people, and a lot of people have said, “Okay, we don’t need to deal with Jacob anymore.” But there have been a lot of people who have stuck around, who have been supportive and made my life so much better by being in it. I owe everything to them, or I’d just be a lonely mess. I wanted to win this thing not just so I could move out of my parents’ house, but also so I could use the money to find some way to get all my artistic friends together to make something. I want to benefit the people who I love and show me that same love. I’m undeserving. At the watch party I was at, I had a few friends there, and them just sticking around and being there for me. For someone who wasn’t really getting a lot of that when he was growing up, to have it now, I treasure it so deeply. I thought this would be a cool opportunity to benefit them a little bit too. I hope they see how far I’m willing to go. I’m willing to go and embarrass myself on national television. (Laughs.)

Lastly, please tell me production gave you a new pair of shoes after you walked out of Tribal Council.

(Laughs.) I got a pair of shoes from production, those damn Vans! I had shoes waiting for me back at Ponderosa. (Laughs.) I still have those shoes now. That’s the benefit of only lasting a few days; your shoes are not too wrecked yet. You can wash them out and still use them.

And it’s a nice relic to your time on Survivor. It’s almost its own Ghost Island artifact!

I have a lot of weird stuff, man. (Laughs.)