Cloudflare TV

Silicon Valley Squares

Presented by Dan Hollinger
Originally aired on 

A send up of Hollywood Squares where Cloudflare experts fill the celebrity squares and answer high and low-level Cloudflare questions to help two guest stars (customers, AEs or new hires) get a a tic-tac-toe, or possibly the Silicon Valley equivalent - a TCP handshake (SYN, SYN-ACK, ACK)

Game Shows

Transcript (Beta)

Hello, hello. Welcome everyone to yet another episode of Silicon Valley Squares. Thank you for joining us here at birthday week.

Hopefully we are the nice palate cleanser to all of the deep intellectual discussions going on about the future of the Internet.

I'm your host, Dan Hollinger. And on this episode, we will be reviewing 90s hip hop.

So I want everyone to stop. Let's collaborate a little bit. Let's listen.

And we'll see if we can come up with a brand new invention. Okay. Now, if you're new to the show, I have two contestants here, Lee and mill.

Each of them will be trying to get a tic tac toe by asking our lovely Cloudflare celebrities trivia questions, 90s hip hop trivia questions.

And they'll be trying to get three across three down or three diagonal.

So with that, I'll kick things off and Lee, would you mind giving a quick introduction of yourself?

Yes, I am Lee Carlson.

I am an executive assistant here at Cloudflare. I support our CFO. This is my third or fourth time on Silicon Valley Squares.

It's my favorite game. And I also help with the segments for the Cloudflare TV segments that we have each week, or I help every other week, but I help on a regular basis.

So I'm happy to be part of the team.

Glad to have you on the show. And, and mill, how about yourself? Would you mind giving a quick introduction?

Hi, everyone. My name is mill. You've probably seen my name thrown around.

I do the beer meeting music and stuff. So yeah, I'm part of the IT teams about to be my two year this month.

And yeah, it's my first time doing this.

So this is exciting. Can't wait to get this done. All right, well, welcome to the squares.

And it sounds like you already got an advantage if you're used to doing music as part of your day job.

Maybe, maybe. All right. And how are all my squares doing?

You guys ready to go? Sure, why not? Ready. So I'll bring the board back up and Lee, the choice is yours.

Where would you like to kick things off?

I am going to start with the center square, Ryan Knight. All right, Ryan, where are you calling in from?

San Jose, California. San Jose. Well, welcome to the squares.

Would you mind giving a quick introduction to all of your Cloudflare TV fans?

Yes, I am Ryan. And I head up the team that handles community and social stuff at Cloudflare.

And that's all the Twitters and stuff. And this is my idea to do hip hop.

I'm very excited. Is that the technical term that the Twitters? The Twitters.

Okay. Twitters. All right. Well, your question to kick off this show is what group put out the hit rap dance track Tootsie Roll in 1994?

So I think that was either it was at Hershey, or was it Eminem's?

So I want to say the Quad City DJs, but I think they did Come on, Ride That Train, but also produce songs for a lot of different Miami based one hit wonders.

And this one is actually the Masters of the Booty Shake, 95 South.

All right, Lee, do you agree or disagree with that?

That very nice idea of the Booty Shake, history lesson.

That was suspiciously too much information. I would agree with that.

So I say I disagree with the answer. You disagree with the answer? All right.

The right answer was 69 Boys. So the center square goes to you. Bring that up.

If anyone wants to do the Jeopardy music or sound effects. Boom. All right, Mill, the board is yours.

Where would you like to go next? I will start with Lytton.

All right, Lytton. Would you mind giving a quick shout out to all of your fans on Cloudflare TV?

Sure. What's going on, everyone? Lytton. I'm currently based here in the New York suburbs, but I'm going to be joining the team down in Austin once the world opens up again.

Been here for about two months now. Love it. Love the team.

Love what we're doing. And it's a good time. Awesome. Well, welcome to the squares.

Your question. Name at least one other rapper, Tupac Dizt, on the track, Hit Em Up.

Oh, man. I would have to say, I mean, there were a lot if I remember, but he definitely went after the Notorious B.I.G.

All right. Notorious B.I .G.

Do you agree or disagree? I agree. Agree? I agree, too. I actually know the answer to that one.

You should have picked me then. All right. Oh, there's the Notorious B.I.G.

It was a few of the bigger names were the Notorious B.I.G. Lil' Kim, Puff Daddy, and Mo Deep were all Dizt on that track.

Thank you, Lynn. You're welcome.

All right. So, Mill gets on the board. And let me fix that X. I've got it going, you know, known for my perfectionism.

Lee, where would you like to go next?

I'm going to go with Kit. All right, Kit, welcome to the squares.

Would you mind giving a quick introduction?

Sure. Hi, guys. My name is Kit, and I work out of the San Francisco office.

I'm an EA, and I support the head of sales ops and the head of America sales.

And I'm super excited to be here. I'm usually working behind the scenes for Cloudflare TV, so I'm excited to be here.

Awesome. Glad to have you. Your question, Keep Their Heads Rigging by Dr.

Dre was featured on the soundtrack of which 1995 movie?

Now, Lee, I know you don't think I look over 18, but I grew up in the 90s, and this happens to be my favorite comedy of all times.

So, believe me when I say it's Friday.

I want you to repeat the question. The question was Keep Their Heads Ringing by Dr.

Dre was featured on the soundtrack of which 1995 movie? And Kit said Friday. I'm gonna have to agree with Kit on that.

All right, it was Friday. All right, so Lee gets the square.

And we got a potential win on the board.

Mill, where would you like to play next? Yeah, I need a block.

So, Suzanne, please. All right, Suzanne for the block. I know you already have your Silicon Square is regular almost to this point, but would you mind giving a quick introduction?

Love to. My name is Suzanne Aldrich, and I lead a team of field solutions engineers on the West Coast.

And I'm calling in today from Marin County, California.

Oh, Marin. Hopefully, it's not too hot up there. It is baking.

And it's also, it's not necessarily known as like a center of hip hop knowledge.

So, take all my answers with a really big grain of salt. All right.

Suzanne, your question. This was actually written in from someone on our support team.

Name two songs by the artist Sisqo. Okay, Sisqo. I'm not entirely sure. Normally, when I'm thinking Sisqo, I'm thinking VoIP and AnyConnect.

So, let me think.

We still get those tech jokes in there. Yeah, maybe like a like a Rump Shaker or Back That Ass Up.

All right. I'm not going to repeat those. But do you agree or disagree?

I have to disagree. All right. That is correct. Those were, I was looking for things like Enter the Dragon, the Thong Song, Wild Wild West for some of his, you know, quote unquote hits.

So, no Switches or Routers? No, that's a different Sisqo.

Okay. All right. So, here is the state of the board. You successfully got that block.

Leigh, where would you like to play next? Let's go with Rebecca Klayman.

All right. Rebecca, welcome to the board. Where are you calling in from?

Thanks. Yeah. So, I'm usually based in San Francisco. But I came all the way out to New York to rep the East Coast, East Coast hip-hop.

And so, I'm calling in from New York and I lead the brand team at Cloudflare.

Awesome. So, we can get some East Coast, West Coast, you know, beef going here on the squares.


I know what some of those words mean. All right. Rebecca, your question. Bone Thugs and Harmony started in this Ohio city.

So, I love that this question is for me because I'm visiting my parents and my dad is from Ohio.

And I don't know if you'll find another, like, hip-hop group that gives, like, a shout out to the Cleveland Browns.

So, Bone Thugs is from Cleveland. All right. Rebecca says Cleveland.

Do you agree or disagree? That sounds like a very reasonable answer to me.

So, I'm going to agree. All right. It was Cleveland. All right. So, X gets the square.

And here's the state of the board. All right.

Mel, where would you like to go next? I'll go with Stregi.

Ryan. All right. Ryan Stregi, welcome to the squares. What do you mind giving a quick intro?

Yeah. I'm the only person wearing his gold chain, apparently, for the whole thing.

So, you know I'm serious about it. Hey, this is kind of like a chain, you know?

That's a tie. But I'll give it to you. I'm in the Austin office.

But, you know, I'm from North Dakota. So, I know a lot about, you know, rep.

All right. All right. So, you should be good for this question, then. What was Mob Deep's original group name?

I'm going to go with just Mob.

They got Deep later on. Yeah. All right. Just Mob. Do you agree or disagree?

I have to disagree with that one. All right. Do you know their original group name?

It's on the tip of my tongue, but I totally forgot.

All right. It is the Poetical Prophets. I had Prophet, but I didn't have Poetical.

All righty. So, Mill gets the square. And the block. So, now, where would you like to go next, Leigh?

We have a competitive game won. Let's do Ashley. All right.

Ashley, welcome to the squares. Would you mind giving a quick intro? Yeah. I'm Ashley calling in from Burlingame, California.

I run our corporate events team and also running the Cloudflare TV team.

So, I'm excited to be on here. Yeah. That's it.

Awesome. Glad to have you. Your question, true or false? On the song Big Papa, Notorious B.I.G.

washes down his T -bone steak and cheese eggs with Welch's grape juice.


I have a visual of this in my head, but I think it was... Got the song going? Yep.

It's like in the back of my head right now. I'm playing it. But I think it was maybe ocean spray grape juice.

So, I'm going to disagree. All right. Ocean spray. So, she thinks it's false.

Do you agree with or disagree? I would agree with Ashley's answer.

All right. It actually was true. It was just Welch's grape juice. Darn.

Should we all sing it together? I do encourage singing on this show. I do not impede that.

You guys... T-bone steak, cheese, eggs, and Welch's grape. That is how it went.

All right. So, Mill gets the square and the win opportunity. Mill, where would you like to go next?

My teammate, Eddie Palmer. All right, Eddie. The pressure's on.

You guys still have to work together after this. Yeah. I love the guy.

I love the guy. All right. Would you mind giving a quick introduction? Eddie. IT team.

Currently the hermit at the SF office every Monday and Friday. That's about it.

Mill's my boy. How's the office doing these days? It's bone quiet. It's really quiet, but it's cool.

I mean, you know, it's fun. At least you have all the snacks to yourself, right?

No. No snacks. No snacks? No. As soon as they put the snacks out on the table and the beer, it was gone within like 20 minutes.

I think word got out and went down to grab a six pack.

All gone. But that's all good. Nicole spoils me.

That's all right. All right, Eddie. Your question. Which of the following rappers guested on the Beastie Boys Ill Communication album?

Was it Nas, Snoop Dogg, Chuck D, or Q-Tip?

I don't know this one.

I can never. I lose all kinds of rep. It was from center square here.

Yeah, it was Q-Tip. All right, saying Q-Tip. Do you agree or disagree?

I don't know because I thought it was Chuck D. But since my boy Eddie, you know, he's my guy.

But hold on. Can you trust Eddie all the time?

I trust Eddie. I gotta trust Eddie. He's my guy. I thought so too, but then he let me down.

All right, so Mill, you agree? I will agree with Eddie. Okay, it was Q-Tip.

So Mill, you take the square and game one. I mean, who's always trying to put Tribe Called Quest on the beer meeting music?

All right, well, that brings us to our center point.

And game one was brought to you by Birthday Week. It's our birthday.

And if anyone wants to sing, feel free to help yourselves. Hopefully you guys, everyone's been enjoying all of the amazing Fireside chats and new products we've been launching.

Happy 10th birthday, Klaffler. I was expecting cake.

I was also expecting cake. There is no cake. The cake is a lie. I can sneak in a few more nerd references.

We'll be okay. All right, and with that, we'll move on to game two.

Mill, first choice is yours. Where would you like to play? I will go with my guy Z, because he did not go last round.

Thank you. I appreciate you.

All right, Zadoon, would you mind giving a quick introduction? Sure. I'm Zadoon.

I'm a systems engineer on the cache team. My job is to make sure everything is stored on our, and that's it.

I just like to basically keep things to myself.

I see that. And I must applaud the suit. That is, you know, very well done.

Thank you. I don't know whether you're trying to one-up me here. This is my show, you know.

Well, yeah, the first time I went there, I wasn't wearing a suit.

And you were wearing a suit, and I felt out of place. So I said, you know what?

I'll show him who can wear it better. All right. It's got a nice three -piece.

I like it. Thank you. All right, your question. What does WuTang's C-R-E-A -M stand for?

I see. I want to say cache rules everything around me.

Now, I know what you're going to say.

He works on the cache team, and he just said cache rules everything around me.

He's trying to self-promote. It's perfect. I get it. Trust me on this one. That's the answer.

All right, Mel, do you agree or disagree? You know, I'm just going to agree with what I'm doing, because I'm just going to agree.

Oh, really? I don't even agree with myself, but let's go with that. Okay, don't worry about it.

We're still good. Depending on how he's pronouncing cache, which I assume he meant like monetary cash.

Monetary cash. Yeah, although we do have shirts.

I've seen shirts around Cloudflare that say cache rules everything around me, and that is correct.

That is what that stands for. So Mel gets the square.

All right, let me bring up the board, and Lee, where would you like to play next?

Um, let's go with, when did Jason Kincaid come on the board?

Is he actually on? Oh, oh, I got a typo.

All right, well.

I think that would be me. Yeah, that would be. All right, let's do Lytton, Lytton, Lytton Thomas.

Lytton Thomas. All right, your question is, this late 80s group was made up of Dr.

Dre, Ice Cube, Eazy-E, DJ Yella, and MC Wren. I'll use the, um, the acronym as opposed to the full name.

I don't want to have more HR violations.

I'll just call them NWA. All right, NWA, do you agree or disagree?

I agree. All right, it was NWA. All right, so X gets the square, and Mel, you're up next.

Where would you like to play? I'll have to go with Ryan.

All right, how you doing?

Have you known all of the answers to all these questions? Uh, yeah, yeah.

Okay. You could have shared them with, like, all the other squares if you'd want it.

All right, your question.

Who sings the hook on Jay-Z's Can't Knock the Hustle? So I want to say Drake, because I think that's a good one.

He's the first rapper who can sing, but he would have been nine years old then, and he wasn't actually a thing.

So there are a lot of 90s R&B divas, and not Mariah, not Whitney, not Tony Braxton.

This was Mary J. All right, Mary J. Blige, do you agree or disagree? I'm gonna have to go with the 90s guy real quick with Ryan.

So I'm gonna agree. All right, it was Mary J.

Blige. So Mill gets the square. Ryan. That was a lucky guess, Mill.

I don't know, he had so much confidence, though, in that answer. Mill is killing it in this game so far.

Not sure why. All right, Lee, board is yours. Ashley, I have to go for the block.

All right, Ashley, your question in game two. Okay, hopefully I can help you.

He's going to give me the right answer. All right, so I'm gonna set you up for a song.

You can speak the lyrics, so you're good. But can you complete this infamous Nuke Dog lyric, laid back, with my mind on my blank?


Okay, I think most of us know the answer to this one. I will say, I hired Snoop Dogg, my previous company, to do an event, and he canceled on me four hours before, so I didn't listen to Snoop Dogg for a while.

I was pretty upset by that. So, with my mind on my money and my money on my mind.

All right, that is correct. So, Lee gets the square.

Way to go, Ashley. Square for that appearance, and if so, how much weed was included on that writer?

That's why he was four hours late. No, he never showed up.

He canceled. All right, Mill, board is yours. Where would you like to play next?

I'm gonna go with Kit. All right, Kit, your question. Which record label featured artists such as Dr.

Dre, Tupac, and Snoop Dogg? Well, it would be Tupac, and everyone knows that from the 90s, the best West Coast rappers were on Suge Knight's record label, a.k.a.

Death Row Records. All right, Death Row Records. Do you agree or disagree?

I agree completely. All right, it was Death Row Records. So, Mill gets the square.

I want to go with my card and say I don't know anything that was mentioned here.

That's okay.

That's how I feel on all the technical shows. I'm getting a taste of my own medicine as well.

I grew up with 90s country music, so most of this is like just a foreign language to me.

All right, Lee, the board is yours. Where would you like to play next?

I would like to go with the girl that said, back that ass up. All right, Suzanne.

Your question for game two.

Ali Shaheed Muhammad is part of which rap group? Okay, I'm gonna have to use like a little deductive reasoning here.

Rap group. Could this be the given name of the artist, also known as Old Dirty Bastard from Wu-Tang Clan?

I don't know what's going on here. Is that your final answer? Yes, it is. All right.

Agree or disagree? I disagree. All right, Ali Shaheed Muhammad was part of Tribe Quest Love.

Suzanne just wants to say as many offensive words as possible. I mean, I can't bleep anything on this show.

I'm just like putting that out there. What's the rating for this?

Definitely not PG-13, right? I don't know, we used to be a late night show.

I mean, we still are, depending on what time zone you're tuning in.

My cheeks are so red. All right, Mill, board is yours. Where would you like to play next?

Whoa, dang. I gotta go with my guy, Eddie.

All right, Eddie, your game two question. What was the name of the Fresh Prince's DJ?

Jazzy Jeff.

All right, DJ Jazzy Jeff. Do you agree or disagree? I agree. All right, it was DJ Jazzy Jeff.

So let me get the X on the board or the O on the board.

And Lee, the board is yours. Where would you like to go next to start wrapping up game two?

We are gonna go with Miss Rebecca.

All right, Rebecca, how are you doing today? I'm doing all right. I'm sorry, I lost my background.

I feel like I'm breaking the fourth wall here. I know, the production values are ruined.

It's where we're doing. I know, I'm so sorry. All right, your question.

Illmatic was the first studio album released in 1994 by this artist.

Illmatic, I feel like you mentioned something similar earlier. So I'm going to say Beastie Boys.

Beastie Boys. Do you agree or disagree? I really have no idea, but I'm going to agree because it just sounds like a good answer.

All right, it was not the Beastie Boys.

It was Nas. I get a sense ill was just a very popular slang term in that decade.

Ryan, can you check me on that one? Especially in the East Coast rap that I thought Rebecca was the master of.

Good word. As a fellow New Yorker, I'm mortified you said that.

Yeah, you know, these squares are just so ill.

All right, Mill, rhymes with ill. I'm working on my raps. You can wrap up game two.

Where would you like to play? Oh, I got my guy, Ryan Stregi. All right, Ryan, for the double win.

Yeah, you got down and across. He has two points. Now I got to ask the really hard question.

Yeah, no pressure. All right, Ryan, to end up the show.

What does OPP stand for? I know this one. Did the rating just change? It is old people problems.


You know, those East Coast, West Coast rappers, you know, really, really care about the old people problems.

I'm going to have to disagree.

All right, it stands for other people's property.

So with that, Mill takes game two with, I think, first ever double win.

And way to go, Mill. We are, there's the state of game two.

And unfortunately, game two was not free. Game two was brought to you by Cloudflare Secure Access Surface Edge.

Get a little sassy, especially on this show.

If you'd like to learn more, check out slash teams dash sassy.

Turtle X. How do I get my own ads up here? Oh, you just got to pay me. In either iPads, Bitcoin, cash.

All right, and with that, we're at the end of the show.

I want to thank my contestants, Mill and Lee. I want to thank all my squares. Did you guys have fun?

Yeah. I learned a lot. All right, well, thank you all for dialing in.

Hopefully, you enjoyed whether you caught the live stream or recording. Good afternoon, evening, or good night.

And enjoy the rest of birthday week. Thanks, Dan.

Thanks. Bye.