Having started in comedy with his group Dutch West, Sam Reich was later hired as director of original content at CollegeHumor, an Internet comedy company. Responsible for boosting the content team, Reich produced shows for TV and online that include Adam Ruins Everything; Rhett and Link’s Buddy System and Badman starring Pete Holmes.

In 2018, CollegeHumor launched a subscription-based streaming platform called Dropout. According to Reich, who was CollegeHumor’s chief creative officer at the time, this was in response to the “difficulty in receiving advertising dollars on traditional media platforms for mature content”.

Then, the bottom dropped out. In 2020, CollegeHumor’s parent company InterActiveCorp (IAC) withdrew funding, which laid off all but seven employees. Still able to see the potential, Reich bought CollegeHumor. With the newly-minted title of CEO, Reich placed more focus on unscripted productions like Um, Actually, Dimension 20 and Game Changer; rebranded CollegeHumor to Dropout; and rode out the pandemic and SAG-AFTRA strike. At the tail-end of 2023, Reich announced that Dropout subscriptions had grown to a point where it was profitable enough to go into profit-sharing with its employees.

On the wave of a new season of shows, we talk to Sam Reich about Dropout, puzzles and the joys and trials of Game Changer.

SAM REICH: I can't believe it's 1:30 in the morning over there. I can't guarantee you're not dreaming up this interview.

ESQUIRE SINGAPORE: [laughs] Oh no, not again. Do you guys work from home?

SR: We do for the most part. We have a studio space and there are a couple of people who come in for post-production. For the most part, we just come in for shoots and the full-time staff works from home.

ESQ: Let's get this interview started. Sam... where are you from?

SR: [laughs] The fact that this joke has travelled internationally is really annoying.

ESQ: But are you surprised that Dropout is known outside of the United States?

SR: Are you kidding? I’m super surprised. And flattered. We went to the Edinburgh Fringe [last year] for the first time and had an amazing time. I was shocked by how many Scots knew about Dropout. It’s really cool to see our work getting out there.

ESQ: What’s the ratio of American subscribers versus the rest of the world?

SR: It’s predominantly US. I want to say... something like 60 per cent US. And then, there’s the second tier, which would be English-speaking countries. So, a fair portion of Europe, Australia, Canada... we’re popular in Germany for some reason. That ranks high on the list. Germany and India. I think that English is spoken in enough places now, for better or worse, that we have more international fans than I could ever imagine.

ESQ: You’ve mentioned before that you were hesitant to be in front of the camera. But you dropped out of school to be an actor.

SR: Yeah, originally I got into this business to be an actor... a dramatic actor. I took an acting class where the teacher said that I should act based on the first impression I gave when I walked into a room. For instance, Sam is short so he should do comedy. And that was the beginning of my comedy career.

I found a lot of warmth in comedy but not a whole lot of work in show business. It’s just really hard to make a living at this. The farther I stepped away from acting, the more money I made. I became a director, then a producer and then an executive... by the time, I became an executive, I worried that casting myself in things would be an abuse of power. I wanted to put myself in a position where I was supporting the careers of other people, who wanted to do what I wanted to do originally. It wasn’t until Game Changer came along. This was a show that no one really wanted to make. I kinda pitched it and got a lukewarm response. No one could wrap their heads around the idea and no one wanted to host it. I said, all right, I’ll take this particular bullet and now I am a gameshow host-CEO, which is a hyphenate I don’t think I share with a lot of people.

ESQ: The title will look great on your LinkedIn profile.

SR: [laughs] Exactly. It’d be a good business card where it says CEO on one side and gameshow host on the other.

ESQ: We discovered Dropout by chance with a Breaking News episode on YouTube—"True Facts About Grant Anthony O’Brien"—where embarrassing facts about Grant (a Dropout writer and performer) were revealed. And that led me down a rabbit hole of other Dropout content and I decided to buy a [Dropout] subscription.

SR: I love hearing about people's different entry points into Dropout. Game Changer and Dimension 20 are usually the popular ones.

ESQ: You’re also a presence on your social media. It’s a little endearing... that someone of your bearing is doing TikTok and [Instagram] Reels.

SR: [laughs] Yeah, I get made fun of for this a lot. Just before signing on to this call, I posted another sketch that I made in my spare time on Instagram. I didn’t have time to do TikTok but I’ll go back and upload to it afterwards. I think I’m one of the few people who loves what’s happening to comedy, thanks to platforms like this. I love how democratic they are. By the way, the House just passed [a bill] to ban TikTok in the US this morning; I’m very sceptical that that will happen.

Anyway, my interpretation of what happened is that TikTok was the first platform that you leaned into this idea of discoverability. So, what you were presented with, first and foremost on the platform, was people you didn’t know. Then given its rise in popularity, Instagram followed suit and created Reels; YouTube followed suit and created YouTube Shorts... TikTok created an opportunity to get seen. That hasn’t existed in our space for a long time. It’s really hard to find an audience doing this, it’s really hard. So, I love it and I want to participate in it. Even though... [laughs] the other day, one of my cast members/writers asked me, so what are you getting out of this financially? The answer is, less than nothing. I’m wasting money doing this. Money and time.

ESQ: You’re one of the rare exceptions as an independent streaming subscription platform to crawl out of a hole and find success. Do you have any advice for people trying to do what you do? Or were your circumstances akin to a perfect storm that will never happen again?

SR: If somebody wants to become a CEO/gameshow host of a niche subscription platform, I probably can offer a lot of advice. I think how we’ve ended up here is pretty niche and unique, and lucky, in terms of breaking into the business in general. This, at least, holds true in the United States. I don’t know whether it’s the same over [in Singapore] but it is still very hard and very privileged [that I get to] do this for a living.

I think that our industry has—that is the same in so many other industries—a kind of hollowing out of the middle class that’s occurred, where it’s just harder for folks to float to the top. It’s a system that right now, especially with all the consolidation we’re seeing, is rewarding people who are already at the top way more than it’s providing an avenue for younger and aspirational folks. On the other hand, the Internet has afforded young and hungry entrepreneurial creators better opportunities than ever before. So, if I was just starting, I’d focus on how I get attention online.

ESQ: How different are you from your Game Changer host persona? Is that the real you on camera?

SR: I mean, it is. You know, I think that there’s a very nuanced distinction between Sam on stage and Sam in real life. I do think when I’m in presenter mode, and then I break because one of my players does something funny and I laugh, that’s sort of a quick jump from one Sam to the other. But I was raised on Monty Python and there’s something about comedy in a suit that’s always resonated with me. I love stuff that’s formal and a little surreal. There are a few episodes of Game Changer that require me to be a little bit more of a “straight man”. For those episodes, I do try to unnerve my players with my common confidence, my stoic-ness. In this last episode of Game Changer, I say, Sam says “Don’t flinch” and a body falls from the ceiling... I have to play that straight or the joke doesn’t land. But inside I’m giddy all the time. [laughs]

ESQ: One of your more famous catchphrases is "I've been here the whole time". It's something that you utter at the start of every Game Changer episode. Is there more to the statement?

SR: You know, there's a very pragmatic reason I say that. The original reason is because as the other players take the stage, I'm announcing the show as well and you wouldn't normally know that the announcer and the host were the same person. So, when the camera cuts to me, I'd say, "I've been here the whole time" as a sort of welcome.

But it has taken on a kind of a different quality as the show's gone on. I've introduced the idea of my great-grandfather magician counterpart, Samuel Dalton [from the "Escape the Green Room" episode], who exists somewhere deep in the lore of Game Changer. There's a Loki, god of mischief, quality to the phrase, "I've been here the whole time". I'm always watching. So I embrace it, even though it's not what I meant.

ESQ: But as the seasons go on—and I wish longevity for the show—is it getting harder to come up with themes for the show? Because one of the factors for Game Changer is, you know, the element of surprise.

SR: You’ve just encapsulated the stress of the show. Every season we back ourselves further and further into a corner where it’s harder to be original. And for a show called Game Changer, that’s the pressure. How do we keep reinventing the wheel? And every season we have to step a little further outside the box to find ideas that feel like they’re going to surprise, not only the cast but, also the audience of the show. And, by the way, remain true to, what I feel is, the show’s character.

ESQ: And what is that?

SR: For instance, I’m not super inclined to leave the set altogether. There’s more and more reason to do so [as demonstrated in] our two-part season finale, where we leave the studio for a completely different location. But it’s almost like when someone gives you a cardboard box and you have to put something wildly different in that cardboard box every episode but the box doesn’t change its shape so how do you do that? Every season we say, how are we going to top the next season? And every season we say, that’s next season’s problem.

ESQ: I can't wait to see the new season and what you have in the years to come. And also how you're going to get yourself out of the corner you painted yourself into.

SR: [laughs] You and me both. I think this next episode of Game Changer—the one that airs in two weeks—is a good one. And the one that airs two weeks from now is also one of my favourites we've ever done.

ESQ: It sounds like every episode that's coming out is the best one you've ever done.

SR: [laughs] The one coming out that I'm excited about is called "Bingo". You'll know when you see it.

ESQ: I’d assume the writing room for Game Changer is small.

SR: It’s small. Really small. It’s myself; my creative writing partner and head of development, Paul Robalino; it’s a writer whom I love and trust a lot, Ryan Creamer; it’s our head of production, Kyle Rohrbach, and my production designer, Chloe Badner. Recently, we brought in my director and editor, Sam Geer, early into that process.

Except for Ryan, the people who work on Game Changer lead departments on the show. That conversation is more of a production. It’s one part creative and another part logistical. I want those meetings to be practical. What’s the point of having a room full of creative folks if the moment I present my ideas to production we can’t do them?

What I did this past season is that I have 10 folks that I go out to for pitches. Then I take those pitches to the group. With them, we mull the pitches over; beat them up; cut ideas in half; sew two ideas together... that’s how we write a season. As the seasons wear on, I lean less and less on comedians and more and more on game designers. Now, the folks pitching the ideas are those with backgrounds in escape rooms and interactive experiences. I find their backgrounds are better suited to where the show is going.

ESQ: You're also a magician.

SR: Sure. But an aspiring one.

ESQ: Was magic something you took up during the pandemic or when you were young?

SR: It's funny, I was just reviewing some home VHS footage from when I was two and three years old and it was my first ever magic show. I've been into magic for almost my whole life. My school assignment was to create a coat of arms for myself. We had to come up with a sort of a [motto]; mine was "Imagination. Illusion. Humour. Art." I was seven at the time, just to give you a sense of how long this kind of stuff has been in my DNA.

During the pandemic, I found a magician offering lessons—Jason Ladanye on TikTok—and I started two years of training and some sleight of hand with him. It was really fun and really humbling because you learn fast that the stuff is not at all easy. It takes years and years to get good at. Jason is one of the best there is.

ESQ: What's your forte? Cards? Coins?

SR: Cards. I love the elegance of a simple Bicycle deck and this notion of portable magic, you know? Magic that you can take with you. Magic that you can do with someone else's deck of cards. Mentalism is interesting to me. I find it very intimidating and big stage magic like David Copperfield's kind of magic, I've no interest in at all.

ESQ: There's this weird crossroad with magic and humour that magicians often get made fun of by comedians. Do you get to perform for your peers?

SR: I do and people ask, for sure. I also think because they run in the same circle of performers, you'd be surprised about how little I get made fun of for magic as a hobby. It's like all of us here on the east side of Los Angeles are nerds and geeks. You have to be a particular kind of person to love and learn that kind of stuff.

I think it was Teller from Penn and Teller, who said, "Sometimes, magic is just someone spending more time on something than anyone else might reasonably expect." And that's how I feel towards Game Changer, where we put so much effort into creating the fun and surprises of it.

Do you know the Dimension 20 e-art puzzle in "Escape the Green Room"? Took me hours to figure that out. But the whole time, I was just thinking, oh, they'll love this. It's like a little gift for your friends.

ESQ: By the way, I loved that episode because I thought it was going to be a normal escape room. But then you added lore to it. There’s a storyline. I was like, Oh my God, he went that extra mile.

SR: Yeah. It’s pretty high. My creative partner on that episode was Tommy Honton an escape room designer and I learnt a lot from him. Tommy has a terrific escape room here in Los Angeles called Stash House and he told me that the most exciting escape rooms are the ones with background. So, that’s where the seed started.

And then he said, the biggest advantage we have going into this episode, is that it only needs to happen once. As opposed to a traditional escape room, which you can reset over and over again. At that point, it became, Oh, we can put breakables in the room. A breakable clock, a breakable guitar and then it all started to fall into place.

ESQ: It just shows the kind of mind to conjure up themes for Game Changer. It's almost akin to a supervillain's mindset where they set up elaborate death traps and schemes.

SR: If you go back and watch season one of the show, we were still figuring out its identity. [We only figured it out] until season four. If you were to describe the show as a cocktail, it's one part improv comedy; one part British panel show; one part prank; one part magic trick and one part avant-garde art project.

Part of this for me is education. As I'm out in the real world, I'm doing escape rooms or playing social deduction games or seeing theatre. I'm taking notes, Oh that's a really interesting fact. I bet that could be incorporated into the show at some point.

ESQ: What are you watching and reading? Do you even have time for that?

SR: I do. I read a lot of fiction. My favourite book last year was Sea of Tranquility. It's this perfect little time travel book. I watch a lot of mystery. I've been watching The Tourist on Netflix. It's awesome. Amazing performances, an engrossing mystery. The show manages to spin three plates at the same time. It's really good.

I'm also watching shows at the Magic Castle. I'm playing games... I've started playing Blood on the Clock Tower. Again, awesome. I've been seeing a lot of theatre shows again like last year's Fringe. Now that was instructive because people were putting up shows that I'd never considered. It blew my mind. I went to a show called Temping, where only one person can be in the room at a time. You sit in a cubicle and there's a computer in front of you. The "show" centred around the e-mails and the phone calls that you were getting as you temped for this actuary office. Totally outside-the-box stuff... that gets me so excited.

ESQ: Would you like to bring Game Changer to the Fringe?

SR: I would love to if I can convince my business partners that there's any good business reason to do that. And—spoiler alert—there isn't. It would be pure joy if I could. We're toying around with more live stuff in general.

ESQ: Do you watch Taskmaster?

SR: Of course, I do. Alex Horne (creator of Taskmaster) is actually a new buddy of mine. It's funny, I was afraid to watch Taskmaster because it was during the pandemic season of Game Changer and folks started telling me that I should watch it as the shows have so much in common. I didn't want to watch it because I was afraid to derive too much inspiration from it. I didn't want people to feel like I was ripping it off.

But I watched a few episodes, got totally hooked and now I've watched every single one of them.

ESQ: Can we talk about the pandemic? I know, it’s a period that many would want to forget-

SR: It’s still happening.

ESQ: I’d always thought that the pandemic started in 2020 and I realised that it’s called COVID-19... so it started a year earlier. We saw the smoke but we didn’t think the fire would reach us. Your Game Changer season set during the pandemic was amazing. The ingenuity that came out from doing episodes with everybody remotely working from their homes. Did you just want to pause the series during the pandemic or did you feel like doing something...?

SR: We needed to do something. We had a season of Game Changer and a season of Dimension 20 in the can but the clock was ticking and [these episodes] were going to run out and we needed to produce content. We’ve signed a deal with IAC to take over [Dropout] two days before lockdown in Los Angeles and we needed to satisfy these subscribers. In a way, coming up with that season was [brought to a bear] but, in another way, I’m a firm believer that restrictions help assist with creativity.

It’s easier to write poetry that rhymes than poetry that doesn’t. So, the restriction helps. We did episodes that we would have never done in the studio. Not nearly as many people have watched the remote seasons, I get it. Even when I go back to watch the stuff that was filmed over Zoom. It’s... triggering. Thank god, we’re not doing this any more but I am proud of it. There are a few of those episodes that are some of my favourites.

ESQ: You managed to get people like Tony Hawk and Giancarlo Esposito to guest on that season.

SR: That was a really rare situation insofar as no one had anything to do during the pandemic [laughs]. We have some higher-profile guests on next season's Make Some Noise, which is a short-form improv show that I'm excited about. Our experience has been that once people get a flavour of working with us, they will be excited to work with us again. Case in point, the drag queens from [Dimension 20's "Dungeons and Drag Queens" episodes] have been back a bunch. Paul F Tompkins recently started to play with us and he's been back a bunch. It's really fun to have the family expand in that way.

ESQ: You’ve cultivated a nurturing workspace. Your staff and performers look like they genuinely like one another. More family than workmates. In Singapore, it’s rare to see that sort of camaraderie in the workplace, let alone a CEO of a company putting his employees’ welfare before profits.

SR: I can’t take sole credit for this. This new version of the company meant that we could, sort of, start over. And we think long and hard about the kind of people that we want to work with at every level. Especially in a corporate environment, where there are many invisible powers, where [at Dropout,] it’s just us and that’s humbling. And I think that’s something people respond to; they are watching people who make that stuff.

There isn’t some sort of mysterious force behind us or the people who own the company that aren’t us... we are it. When you boil it down that way, we’re just human beings trying to make something and trying to get other people excited to make something with us. To do that, we need to show them—not only kindness and respect—but also reverence for their talent. And talent is really what powers the platform. The reason why Dropout is successful—and you can point to a lot of things like “the organic marketing strategy is clever” or “we’re making good decisions about finances” or “the P&L is well balanced... but the real reason why Dropout is successful is that someone comes out on stage and does something amazing. And for that to happen, you better respect it and have reverence for it.

I think it could be—and maybe it’s a little cynical of me—that in our industry, there are a lot of folks who get into content creation, they aren’t creatives. When you have too many people who get into our business from non-creative positions, meaning they were promoted through [fields that] aren’t like writing, directing, acting, etcetera. They don’t have quite enough respect for what it actually takes to make the product. I think that’s maybe the biggest difference in terms of our company’s DNA or how it’s set up: all of us at a high level are creative folks and we care deeply about other creative folks.

ESQ: We wanna keep to the theme of our discussion and incorporate a puzzle within this interview. Maybe readers who have come this far can figure out how to finish the rest of this url (http://esquiresg.com/_ _ _-_ _ _ _-_ _ _ _-_ _ _-_ _ _ _ _-_ _ _ _ ) and win a prize.

SR: Wow, very cool. You’ve permission to rewrite my responses [to fit the puzzle].

ESQ: Is there any point in Game Changer that you’d want to be a contestant instead of being a host?

SR: You know, truthfully, no. I know fans are so eager to see it happen. I’m nervous for whoever has to host instead of me. But I’m the show’s quality controller. If you take me out of that part of the creative process, it just wouldn’t be very hard for that episode to live up to the others. Forgive me if that statement is a little bit self-aggrandising but I feel so badly for the person who has to take on the stress of trying to come up with a Game Changer episode instead of me. It’s hard at this point. It is hard to come up with this stuff so I wouldn’t necessarily wish it on them.

ESQ: Hypothetically, if you could have someone to fill in as host, who'd it be?

SR: Folks have talked about who'd take on that mantle. Most specifically Brennan [Lee Mulligan]. A lot of people on Reddit want me to play in an episode and have my wife, Elaine, host it. But never say never. Maybe one day.

ESQ: I feel that the closest thing to you being a participant and getting pranked is on Breaking News.

SR: Breaking News has become where Grant [O’Brien] and the cast get their revenge on me. The next season of Breaking News, there are no less than three episodes targeting me. It is [starts laughing] wild. What they will do, I left to their own devices.

ESQ: One last question, how has your wife, Elaine [Carroll] contributed to the Sam Reich of today?

SR: This is an amazing question that I’m so glad I got the opportunity to answer. So, thank you. Being in a loving secure relationship for as long as I have has allowed me to focus on work and creative output in a way that’s extremely privileged. Elaine is unbelievably supportive and our relationship is so profoundly uncomplicated compared to what I often see in the world.

Because we live in a [time] of dating apps and the huge amount of choices they bring, I can’t recommend enough for falling in love and marrying young. [laughs] I think it allowed us to start building a life early, which contributed hugely to what I’ve managed to do now in my 30s—I’ll be 40 this year—yeah... it’s one of the best decisions I’ve ever made.

Game Changer, other originals and more are streaming at Dropout