In this informal live‑show, host SPEAKER A, co‑host Sam Anderson, and guest Rich Miletto of Miletto Packaging discuss a mix of community shout‑outs, Rich’s extensive background in fantasy sports, his passion for NASCAR, and how he broke into the industry through networking. The episode opens with acknowledgments to partners (Bev Assets, Alias Advising, On the Rocks Advisors) and a celebratory mention of Jay Williams’ Freebird‑branded NASCAR car. Rich explains his long‑standing involvement with fantasy sports—starting with hand‑scored line‑ups 25‑30 years ago, evolving to online platforms, and now contributing to fantasyguru.com with football and racing content. He recounts early exposure to racing (Indy 500 at age 3) and a move to Charlotte to pursue NASCAR opportunities. A pivotal moment came when he joined a 32‑team “pros‑and‑joes” fantasy league, designed custom shirts, and leveraged contacts (Jeff Manz, Howard Bender, Bob Harris) to secure coaching and work opportunities, emphasizing his love for pattern‑finding and coaching. The host also references Rich’s swimming background in Georgia. The conversation remains conversational, enthusiastic, and peppered with informal language, setting the stage for later packaging‑related discussion.
Chapters
With myself, my co-host Sam Anderson, and our guest today, Rich Miletto of Miletto Packaging. Welcome, Rich.
Thank you very much. Really appreciate you guys having me, man.
Absolutely, dude. Um, we will get into it, uh, here in a second. We'll probably pick up where we were, uh, just leaving off. Uh, but first we'll call out, uh, Sam and Alicia with Bev Assets, uh, myself and Alias Advising, Ryan Halliman and On the Rocks Advisors, who may be joining us this morning. I know he was at softball, uh, yesterday evening with, uh, his daughter. And, uh, last but not least, Jay Williams. And, uh, shout out to Jay and all the posts I've seen on LinkedIn of his Freebird branded NASCAR car. And there's our obligatory Freebird can this morning. So congrats to Jay on, uh, that partnership, which is fucking crazy. So good for you, man. That's awesome, dude. It's— Jay's a beast, dude. His team's wild. They're all fucking killers. Like, it's— that whole story is crazy. Um, yeah. Jay and his team are animals. Um, let's talk packaging. Let's talk Rich Miletto. So before we get into work, you and I were talking a little bit about your swimming background, but you also on the bio you sent us, do you still help people with fantasy picks, like fantasy sports and shit?
Yep. So, uh, in the evenings, off, off, you know, off hours, things like that. Um, I do some work for a website called fantasyguru.com. Yeah, um, if you've ever seen the show The League, that's the website they talk about using on there. Uh, the website goes back a long way. So I do some football and racing content. So when you were talking about Jay Williams and the NASCAR stuff, I'm a big NASCAR guy. At one point I moved to Charlotte to try to go work in NASCAR.
No shit.
So yeah, so that— when you said that, that, that was pretty exciting stuff from, from my perspective, right? But, uh, yeah, I, uh, do a little bit of football and racing over there. In fact, last week, if you followed my bets You're up 4 units. So, you know, we, we try to help people make some money over there on the fantasy and betting space, if you will. So I got to ask, I mean, obviously you have a sports background.
You mentioned swimming in high school and college down in Georgia. But like, how does one become a fantasy guru? Right.
So, right. You know that. There isn't really a great one. Um, how I ended up— how I ended up getting the chance. So I've been playing fantasy sports going back, call it 25, 30 years.
Sure.
Like, I've been playing so long that, you know, we joke. I remember when we used to hand score our lineups and send them to each other, or, you know, we have to call each other and say we agree, and we're scoring out of the newspaper box score, right? Um, now it's all automated on, on the internet, stuff like that, but that's how far back we go.
Sure.
I would just say that I've watched a lot of football and racing. I mean, my wife jokes about stuff that I can recall and remember. I mean, I've been a sports fanatic since I was like 5 years old, literally. Like, my first racing experience was at Indy 500 qualifying when I was 3. They handed me over the fence. Um, I remember going to the The Red Cross tent from getting a splinter in my hand from the wood stands. And they haven't had wood stands since the '80s.
I was gonna say, I've been there. They have— they don't have— I'm 36, they don't have wood stands anymore.
Yeah, no, no, no, it goes way back to the early '80s on that. Um, so, and what I actually did was I, um, got invited to a big league. I had kind of through Twitter and stuff kind of made some connections to the pros, if you will, the guys doing the radio shows and whatnot.
Sure.
And got invited to kind of a league that was a Pros and Joes. It was a big 32-team, 2 copies of every player. It was real full defense, real kind of complicated stuff. Well, in this league were some other guys I really enjoyed listening to on the radio. And so at the time we had done a football podcast and we had talked to a guy, says, you know, take your shot when you get the opportunity. So I was like, you know what, this draft is taking forever. We need shirts. So I Took a poll, designed a shirt. Everybody wanted them. Well, the big guys I got addresses from because I had to send these shirts out to. So Jeff Manz, Howard Bender, Bob Harris—these are guys that are big names in the industry. I had their addresses, so I put together basically a cover letter outlining my experience, my insight, offering you know hey could I do a little work for free? Kind of prove my worth. And I heard back from all of them, and all three gave me some sort of opportunity one shape or form. And I really appreciate Jeff Manz's approach. I love Bob and Howard. They're They're amazing humans, but Jeff really focuses on coaching more than most. And I've always been a big fan on coaching and schemes really dictate more than anything else. I like to find patterns, so I kind of gravitated to him. So that's how I ended up there.
I'm sorry, man.
You guys, I'm gonna stop for a minute. I apologize, but I don't know what— do you see it streaming on LinkedIn?
I don't, but I was gonna say I've had that issue before where it's been doing it and I just
