Sidetalk's Trent Simonian on building a 100% organic New York street interview brand with zero TikTok revenue

Jun 10, 2026 · Full transcript · This transcript is auto-generated and may contain errors.

Featuring Trent Simonian

Speaker 2: Yeah. It's great time. Meet you. Congratulations. We'll talk to you soon. Have a Thanks. One.

Speaker 1: Later.

Speaker 2: Let me tell you about MongoDB. What's the only thing faster than the AI market? Your business on MongoDB. Don't just build AI. Own the data platform. That powers it. And up next, we have Trent from SideTalk. He's a creator and cofounder of SideTalk. He's in the waiting room. We'll bring him in the team. And after them, He'll turn Nick's fandom into one of the Internet's most Woah. Recognizable All in my mind. Media brands. How are you doing? Take your spirit. How is New York? How is it going?

Speaker 13: You know, it's crazy out here. I'm not gonna lie.

Speaker 2: Okay.

Speaker 13: I was about to do this interview from my apartment and then I realized, hold on. Yeah. Has anyone done a TBPN interview live from the streets of New York?

Speaker 2: You gotta go to the sidewalks. This is the founder of Side Talk.

Speaker 1: This is amazing. Amazing.

Speaker 2: Know you. Take us through your media empire. Take us through your strategy. Break it down for us.

Speaker 13: Okay. So I have a little company called Sad Talk. You might see the logo and pardon the potential loss of voice from this Knicks crowd. But, you know, we kinda pretty much run around New York City and let people do and say whatever they want into our microphone. We created the Bing Bong trend years ago. We created these Knicks videos. Unfortunately, there's little bit of chaos outside of Madison Square Garden due to us. Mhmm. But, yeah, we're pretty much let people say what they want in New York, and it's it's pretty fun and entertaining.

Speaker 2: What's the secret to a good street interview?

Speaker 13: You gotta keep it shareable and engaging. It sounds obvious, but, like, why would you wanna watch an interview of someone talking about something boring or low energy or anything like that? What would you want to send to your friends? And that's kind of the difference.

Speaker 1: So you guys people about like language model diffusion and like that. Always.

Speaker 13: Always. Always. Always.

Speaker 7: That's what we love talking about.

Speaker 2: Token prices and that. Yep. Yeah.

Speaker 1: Yeah. Gotcha. The people wanna see. We're gonna start

Speaker 13: talking about that outside the Knicks game type thing.

Speaker 2: Yeah. Where where so I I understand that a lot of the, you know, man on the street interview format these days, it it it can be very prepped. It can be there's a PR person that's pitching some successful business person for the what do you do for a living. It looks candid but in fact it's staged. Do you ever participate in that or is everything candid? Is that part of the brand?

Speaker 13: We're a 100% natural on the streets. Don't know what you're gonna expect. Okay. Yes, sir. Organic.

Speaker 2: But it's

Speaker 13: been really cool too.

Speaker 10: Yeah. Yeah. Please. Bye.

Speaker 2: Then my my follow-up is like then if you aren't prepping and understand who you're gonna be interacting with like how do you vet like where is the bar? If you see somebody walking and they have a baseball hat on and they probably don't want to be bothered, is there some sort of social contract where you shouldn't like the the is there a doom scenario where everyone in New York is getting asked what do you do for a living 15 times when they walk to go get their morning coffee?

Speaker 13: Yeah. Honestly, it's it's a bit of an epidemic going on. I actually am kinda scared that I'm gonna get pulled up on right now and ask what I do for a living or what song I'm listening to.

Speaker 3: Yeah. But Oh

Speaker 2: yeah. That's another one.

Speaker 13: The the people the people of New York, I think they distinctify side talk a little bit from that. Mhmm. They know we're not there to to ask them something like, I don't know, so so cookie cutter like that.

Speaker 2: Sure.

Speaker 13: And I don't know. Now people come to us when they see the microphone, which is great. And, yeah. We we we just go with the flow.

Speaker 2: How do you think about monetization? Short form monetization, notoriously hard, but you have some merch. Break break down, like, the business side of the business.

Speaker 13: Yeah. It's actually very interesting. You would think that you would that, you know, I would have made a dollar off in TikTok by now.

Speaker 6: I don't

Speaker 13: think I've ever gotten paid for TikTok or Instagram, literally, not a dime, which is which is fine. It's cool. I want TikTok pulled through. But now it's cool. We do a lot of branded work

Speaker 2: Okay.

Speaker 13: For companies. So we've worked with everyone from the NFL to Netflix, Nike, Google, Amazon, creating a lot of content for them. So they'll come to us with a product or an event that they wanna highlight, and they say, hey, you know, you know how to get clicks and views, and Yep. We kind of pretty much apply our formula to that and then create a really good video for them.

Speaker 2: Okay. I I have like a hot take and I want you to walk me through whether you agree or disagree. I think you should just do a mid roll ad in a three minute Instagram reel because I see the branded integrations. It's like, oh, there was this example on Subway takes where someone's take was Android's better than iPhone. It went massively viral on rAndroid. And then the second and then Google was like, oh, we'd love to work with you on another take that's the same thing but it's branded. And those sponsored takes, often don't go as viral. It's hard to get branded content to go viral. But in some of these longer three minute videos, if I'm locked in after two minutes, I would sit through a ten second mid roll of like, hey, this was brought to you by this. Thanks for sponsoring this video. And then it's just all organic content around it. Does that work? Is that already happening? Are you thinking about that? What's the deal?

Speaker 13: Definitely. We one thing we really like doing is kind of like a natural integration. Mhmm. So we just did something with Nike, which is really cool, where they hit us up for these Knicks colored shoes.

Speaker 2: Okay.

Speaker 13: You know, okay. Who better to get word out about these Knicks colored boots than side talk. So we had people wear them in the episode. We were talking about them. We had to react to them. I think that feels authentic because that's kind of something we would do anyway. Mhmm. It it did really well.

Speaker 2: That's good.

Speaker 1: Predictions for tonight.

Speaker 13: We know if you're losing me by the way.

Speaker 2: A little bit. Yeah. It's a little patchy.

Speaker 1: We are losing you, but the energy is still there. Predictions for tonight.

Speaker 13: Nixon five.

Speaker 1: Nixon five?

Speaker 10: What's the plan for

Speaker 2: covering the game? Is this any isn't

Speaker 1: it in your Isn't it kind of in your best interest for it to be all seven games? Like, you know, more more

Speaker 2: More content.

Speaker 1: Yeah. More attention. You kinda want, you know, you we we obviously want your Knicks to win, but you don't want them to win too fast. Got

Speaker 13: a win in seven, I would like seven. If we can guarantee seven, that would be great. But listen, we need to get the win more than anything.

Speaker 2: Okay. What what the process of a shoot day? How early are you getting there? Who are you bringing with you? How big is the team?

Speaker 13: Definitely. It depends on what we're doing. We do such a wide variety of stuff. We can randomly go to a hot dog eating contest in Coney Island. We can go highlight a random character in Brooklyn. We can go obviously film these Knicks games. It was pretty dependent on what's going on, but with the Knicks games, we kinda show up in, like, the third quarter as it's ending. Unfortunately, we can't bring our equipment into the stadium, so we look. You just have to stand there and watch the game on our ESPN app and hope that the Knicks win or we hear, you know, someone just scored, something like that. And then the chaos erupts. We go into the chaos. We're there for, like, hours and hours at a time. And at the end of the day, people see, you know, fifty five seconds, but we're out shooting for, like, eight hours throughout these playoff games.

Speaker 2: Got it. Wild. Well, thank you so much for coming on. We appreciate you. Good luck.

Speaker 1: Yeah. We will we'll feature some of your videos in in tomorrow's episode from tonight. Good luck out there. Have fun. Be safe.

Speaker 2: Yeah. We'll talk to

Speaker 3: you soon.

Speaker 1: I'm hoping for I'm hoping for Knicks in seven personally. Let's do it. But can't guarantee it yet. So have have fun out there. Thank you for thank you for this walk and talk.

Speaker 13: Thank you, guys. Appreciate you.

Speaker 1: Yeah. Great to hang, dude.

Speaker 2: Appreciate it. Thank you. Let me tell you about CrowdStrike. Your business is AI. Their business is securing it. CrowdStrike secures AI and stops breaches. We will be joined by the CEO of Snowflake in just a few minutes. Thank you for tuning in. We need to move on to the story.

Speaker 1: Cannon says, the cashier at Home Depot just asked if I want to round up to support the SpaceX IPO.

Speaker 2: SpaceX IPO is gonna be big Friday. We might have a surprise guest. It's gonna be fun. Also, there's this crazy meta story going on. Not meta, the company, but, like, story about a story behind Ty Morse. He's going all out trying to get an Elon interview, and it's been fascinating watching him build the craziest set in podcasting history. We're rooting for you, Ty. Good luck. Hopefully, you land it. It is the quiet period, so it might be difficult, but I think that there's a plan to extend the effort and everyone's rooting for it to happen. It's been viral on X many many times. Also, Bloomberg's reporting that the SpaceX IPO is four x oversubscribed. Do they know that already? Does do do you get that information at this point? That's really good news for the market, for this for the overall. There was an interesting article. I mean, we can go through some of this. I think this was in The Economist SpaceX talking about, where is it? Can the market swallow SpaceX, Anthropic and OpenAI? Watch out for indigestion. But they talk about the float, the free float. This was very interesting. So obviously the company might be worth a trillion dollars. How much of that trillion dollars is actually actively being traded? Like sure Fidelity might at any point in time have a price at which they're willing to buy more and a price at which they're willing to buy to sell their stake. But founders are often locked up. Founders often want to maintain control. Employees are locked up for a certain amount time. Certain investors might be locked up unless you're Bill Gurley. Don't try to lock him up. Nobody can lock him up. He's a wild man. But the float is important because if it's a trillion dollar company and the CEO passed away a generation ago and there's all financial managers in, it's only owned by hedge funds. This was the story of Take Two before Strauss Zelnick came in. Take Two, the makers of Grand Theft Auto, It was entirely held by shareholders, by financial investors. And they were unhappy with the management team and the management team didn't have any equity. And so he was able to raise his hand and say like, I'll run this thing. And they were like, absolutely. Thank you. And they let him take over the company without really putting anything up. He didn't need to do a hostile takeover like bring a bunch of capital to bear to get control of that company and become the CEO. And it's been a fantastic success for him and fantastic success for Take Two shareholders who stuck along stuck around for the Strauss Zelnick era. But the float matters. And Microsoft, it's 100% floated. The free float is 100% because the founders have moved on and divested and they're not locked up. At Apple, it's like 99%. Broadcom is also at 98%. NVIDIA at 96%. Amazon is at 91%. Only Jeff Bezos is considered sort of off the table. Alphabet at 90%. Tesla at 89. And Meta is notably, of the big tech companies, the lowest free float at something like 88%, 86%. And the reason for that is because Mark Zuckerberg has a lot of control. If he sells his stake, he loses control. So no one's expecting him to sell even if the stock goes way up or whatever. Like, he's going to maintain his position because he wants to run that company. Now, SpaceX is in an interesting, interesting place. So 13% of Meta's shares are owned by Mark Zuckerberg. SpaceX plans to release locked up shares in a series of tranches if its IPO issues $75,000,000,000 of shares valuing the firm at its hoped for $1,800,000,000,000 valuation, the initial free float because if you buy the IPO, you're not locked up. You can sell the next day if you want. Technically, this means

Speaker 1: it's not like the whether whether somebody's like buying through, you know, investing through like JPM Yeah. Morgan Stanley Goldman. Goldman, all these pieces. Like, technically, you can go and sell. Yeah. They just might restrict you from other IPOs. So you would like And and this happens like on all the different apps, you know, Robinhood, public, etcetera. If you're buying into an IPO, they they basically are asking you nicely, do not sell. Don't don't flip don't flip here. Yeah. But people can. Yeah. And so with how many retail dollars are flowing into this, I expect a lot of people that are buying buying, you know you know, basically buying the IPO

Speaker 2: Yeah.

Speaker 1: To start trading almost immediately.

Speaker 2: Exactly. But So it's importantly, it's only 4% of the free float. So only 4% of that $1,800,000,000,000 is a lot of money, but it's only 4% will be really free trading. And then of course during the IPO process you're vetting investors and you're trying to get the people that will hold forever. And Elon has done a fantastic job of that with the indices. So he's gotten the NASDAQ, the S and P and a few others to like commit. So although NASDAQ has already shortened the seasoning period before index inclusion to fifteen trading days, the Russell slashed its waiting time to five days. Most share indices wait firms in proportion to the value only of the shares released for public trading. And this is important because people look at the S and P five hundred and say, wait, S and P five hundred, a $2,000,000,000,000 company coming into that, your weight, if you're just buying the S and P five hundred is going to be more than 1%. It might be in the single digit percent. That's a lot. And we've been talking about the S and P four ninety nine for the bears. Right? In fact, the initial weight in the S and P 500 will be around point 1% because it's just that 4% free float and then it increases over time as the shares get locked up. We actually have a chart here of how the lockups work and it takes basically

Speaker 1: Yeah. There's

Speaker 2: whole year, almost two, for everything to get unlocked and it's also triggered based on share price appreciation. So if the shares trade up 30% or more, then more shares become unlocked and the road to a 100% lock up ending happens slowly. And so just a little bit of an interesting deep dive into how the SpaceX IPO will fare. Anything else to talk about on that story before Apparently, we move

Speaker 1: senator Warren Yes. Has urged the SEC to halt SpaceX's IPO citing governance risks, Elon Musk's control, and potential foreign, especially Chinese investment concerns. She also highlighted SpaceX role as a US defense contractor. Has never met a business that she liked. I think except maybe I don't know.