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The Bigger Stage w/ Matt Stone is a conversation series about leadership, relationships, and the stories that expand influence.
Matt Stone sits down with CEOs, founders, leaders, and creatives to explore the human moments behind growth—how trust is built, how visibility changes responsibility, and how storytelling becomes a leadership skill as stakes rise.
This show is for entrepreneurs and leaders stepping into bigger roles, bigger audiences, and bigger impact—who want to lead with clarity, credibility, and connection, not performance.
BBR Show Pre-Launch Conversation - Michael Allosso
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Matt Stone: [00:00:00] Welcome to the Building Business Relationship Show. I'm Matt Stone, and before we officially launch, we're exploring what matters most when it comes to relationships in business. These early episodes are about testing ideas, learning from guests who have different ideas about different things, and I, we've got a great one today and hearing what you think belongs in the conversation.
Matt Stone: So please listen in, watch. Share your thoughts and help us shape what this show becomes and helping us shape what the show becomes today is Michael Allosso, who's really a master communication expert. He talks a lot about self-awareness. He does talks all over the country. I met him through a mutual colleague and friend in actually in another country. So we were connected outside of the U.S. who said, Matt, you need to connect with this Michael Allosso guy. And sure enough, we had a call and I was like, man, this guy has been doing this a long time, knows his stuff. And does it with an entertainer's flare.
Matt Stone: And that's because your background includes a lot of [00:01:00] theater in New York City and elsewhere, and so you bring that theatrical knowledge and background to the work of self-awareness and communication and helping people be better at the interpersonal stuff, but also sharing their own stories.
Matt Stone: Tell me how I did Michael.
Michael Allosso: Well, there's no need to feel alone. Just listen to me and Matt Stone. Yeah. You, uh, you, that was pretty good. Did you put that through artificial intelligence to say what you just said?
Matt Stone: I didn't think for myself at all. It was. I didn't even, who are you again? Uh,
Michael Allosso: It was very accurate. It was good. It is weird that someone from the UK introduced us, uh, the Jersey Boy and the Boston Boy, whatever it is, you know, who knows? Life's precarious that way.
Matt Stone: So Michael, ultimately, it all boils down to the driver of most of what's important in life, right? Relationships. And so I like to start these off by asking you to reflect on [00:02:00] a relationship that had a significant impact on your business and your life of course.
Michael Allosso: Every day I have a relationship that impacts my business, Matt. There's no day that goes by that doesn't. And if one goes by that doesn't, shame on me. And so of course the easy, the softball that you threw me is you start with Mom and Dad, that Mom and Dad create an environment where I can develop business acumen because of our relationship.
Michael Allosso: I was one of those people who had a mom and dad that stayed with me my whole growing up time and stayed with each other, which I guess is for the US is a big deal and weird and unique, and neither of them graduated from the 10th grade. They both dropped out of high school to work because their families were poor.
Michael Allosso: And they had to support their family. So think about the relationship that once I was born, the relationship that they had with a child, and I'm a [00:03:00] middle child, so think about that. The weirdo, middle of three boys, and all those stats and stories you hear are true. We're bizarre, were unusual. We march to our own drummer, we dance to a different tune, and whatever we've got on the outside, inside is mush.
Michael Allosso: Just feelings and sensitivity. And so my parents with very little formal education kind of figured that all out. And so my dad was a fireman and uh, my two brothers would go with him on his side jobs. So every fireman back in those days would have side jobs, 'cause you couldn't make enough as a firefighter
Michael Allosso: to support your family and because you had days and nights off, 'cause you were working 48 hour shifts, then you'd have a couple of days off, he would paint houses. So both brothers, both my brothers would go out on him and his with him, and customers would say, oh [00:04:00] Joe, how nice you have two sons? Isn't that lovely?
Michael Allosso: And he'd say, well actually I have three sons, but the other son is the son you'll never see. So I became the son you'll never see. And so I don't know as a kid whether I felt like my dad didn't love me, or I knew my dad knew I was special. And maybe it was both. Who knows? Who knows? Are you a schrink, Matthew Stone?
Michael Allosso: Can you help me with this? So, because that relationship with my dad, 'cause I was much closer with my mom. Um, 'cause my brothers, you know, my dad was a jock. He was built like a brick house, like he was so strong and muscly and so were my brothers. They were three sport superstars, and I was watching _I love Lucy_.
Michael Allosso: So when you ask about relationships, yeah. My mom, whom like I was so close with and spent so [00:05:00] much time with my dad, who is kind of this worship figure and Lucille Ball. Those are the three first important relationships and for Gen Z, if you don't know who Lucille Ball is, shame on you. Just go look it up right now.
Michael Allosso: And so those are my first three big relationships that impacted myself as a business person because if you ask me to separate personal from business, shame on you, then I don't know you as well as I do because we both know how silly that would be, is that one informs the other. That what we both work on, Matthew, is how we create one human being that glides beautifully between act one and act two.
Michael Allosso: So act one our business life and act two our personal life. And if those become two entirely different people, where is the authenticity in the moment? Who are you? Who are you really? So [00:06:00] in theater we call that immersion in the role. So yeah, we play different roles. You know, I'm dad, I'm husband, I'm podcast host.
Michael Allosso: I'm podcast guest. I'm keynote speaker, I'm director, I'm actor. There are different roles, but in each of those roles, I immerse myself in the role, which means I bring authentic Michael Allosso to all of them. And if he's not present in one of those roles, then. Mm. It's not gonna be real. 'cause people always say, wow.
Michael Allosso: Then what happens when an actor plays, um, a murderer? Right? What the actor, the excellent actor does is finds the humanity in the murderer, what piece of himself or herself is in the murderer. So that murderer can be a real person. And yeah,. the actor isn't a murderer. They do have to immerse themself in the role.
Michael Allosso: And they spend as much time finding why the characters like them as they do, is why the character is different from them. And [00:07:00] imagine that as a metaphor for how we all related to one another. You know, that we're finding what's the same about us, rather than always looking at what's different from us. So I'm sure I took that answer in a wrong direction, Matthew, but that's the only authentic answer I have.
Matt Stone: Well then it can't be the wrong, the
Michael Allosso: Right.
Matt Stone: answer, right. You're hitting on all the themes too. Um, you know, the lack of distinction between a business relationship and a non-business relationship. Is it a human you're dealing with? Then, you know, it's a human relationship.
Matt Stone: It's just a different context. You're reminding me of how important it is to use the, understanding from improv and from acting and things like that to better understand how we play our roles in our work and our life.
Michael Allosso: Yeah. Because you know the number one rule of improv is yes, and
Matt Stone: yeah.
Michael Allosso: so you understand "yes, and" right, Matt? So if we're doing improv and you say, Michael, there's a spider on your shoulder. I can't say, oh no, there isn't. [00:08:00] Then the improv dies. I have to say, oh yeah, it's my friend Charlie. You wanna meet him?
Michael Allosso: Or I have to say, ah, ah, I have to accept what you give me. And then I add my own thing. That's what relationships are. Yes, and is that if we start from a no place, then we're in trouble. You know? Like, like your first question is still like haunting my soul. Who, what are those relationships that impacted me as a business person?
Michael Allosso: And I wasn't lying to you. And I say it happens every single day. I was on this flight from, this was last week, the week before, from Phoenix to Medford, Oregon. Like, do you know Medford, Oregon?
Matt Stone: I do.
Michael Allosso: Home of marijuana? Yes. They, they.
Matt Stone: And other things.
Michael Allosso: It's great people there and they know that I'm gonna, they know I'm gonna stereotype them all as weed smoking hippies because it, the, the whatever it is they explained [00:09:00] to me, the environment is so fertile that they grow a lot of weed.
Michael Allosso: Um, and so I was on this flight and uh, I got upgraded to first class and I swear to you, 50% of the time when I fly first class, a story like this happens. Um, and so we're all getting on, and there were a few people ahead of me and one of them was a woman who sat in her seat.
Michael Allosso: It was one of those planes that had two seats on one side, one on the other, and we're all getting on. And the woman in front of me was super attractive. Um, a petite blonde, well dressed international kind of person. She had sort of, kind of like a Melania Trump dialect, so I couldn't place exactly what country it was, but it was cool and hot and she was on the phone with somebody and she was dropping F bombs every other sentence.
Michael Allosso: Like she was like, and very like, her face looked like she had just smelled the [00:10:00] right fart on the way in and couldn't get rid of it. So she's on the phone and I'm behind her, and do-dee-do-dee-do, and so we're walking down and the one of the people got on before us sat, this woman, by the way, was gonna be sitting next to me.
Michael Allosso: I didn't know that at this moment, but the woman across the aisle from us, um, was sitting there and she had put her suitcase above our seat because this side had a little teeny weeny weenie uh, overhang and this side had one where you could put your 500 pound suitcase that so many people bring on and don't check.
Michael Allosso: I check my bag to be courteous to other people. So this poor woman who had sat down evidently put her bag up there. And so the woman in front of me is walking and she looks and looks at the woman and said, is that your bag? And she said, yeah. She said, well, you have to move it. And [00:11:00] she said, why?
Michael Allosso: Because that is my space. You have put your suitcase in my space and, and the woman said, no, I got on before you. Uh, it's my space. No, it is above my head. Move it. She said I'm not moving it. Oh really? You think your f-ing not moving it? Flight attendant. So she calls for the flight attendant. Now, Matt, you know, like all these people are boarding and it's kind of like a Pez machine that's defective, like we've all backed up.
Michael Allosso: So the flight attendant elbows her way down, says, what is the problem? And the woman says, that woman has put her suitcase in my spot. Tell her to move it. And the flight attendant paused for a moment and said, but there's a spot right here, um, at the space, seat before yours. I can't put it there. That's not convenient for me.
Michael Allosso: What if I need my papers during the [00:12:00] flight and the flight attendant said, I'd be happy to get your papers for you now and help you. Oh, I see. So you are f-ing right. You and the flight attendant are F-ing right. Well we'll see about it. What is your name? She says to the flight attendant. Flight attendant says, I'll give you my name later.
Michael Allosso: I have to seat a whole airplane. Could you please sit down? So the woman's, I'm totally shortening the story. Like every detail of it is delicious, Matt. But you know, this is
Matt Stone: it's.
Michael Allosso: short show. So she sits down next to me. I'm texting Peggy, my wife, during this, like, what's going on? Just so I don't like make eye contact with anybody.
Michael Allosso: Peggy writes back, stay out of it. Because she knows that I'm gonna probably wanna reprimand this woman. So we get in our seats and I'm kind of doing this. Finally, everyone's seated. The flight attendant [00:13:00] comes back and she says to the woman, you wanted my name, my name is Yolanda. So what? I don't know that name.
Michael Allosso: What? Yolanda. Um, wait, uh, move your, your, your lapel is in the way. Move it. Don't move. Stay still. I need to write it down. And so poor Yolanda stood there while the woman wrote it down. So what I did was, I'm trying to decide here. I I just can't be still. I, I have to do something. So as the flight took off, I found easy for me to find reasons to go to the bathroom.
Michael Allosso: So I went to the bathroom because I wanted to tell Yolanda that she had done a brilliant job. That I admired her poise, her calm, her centeredness, with how this could have been all incendiary. It could have been horrible. And she made it even. And Yolanda turned to me like kind of a little bit [00:14:00] teary and she said, Mr.
Michael Allosso: Michael, thank you so much. I'm like, that means the world to me said, but I have to tell you, I'm a police officer and I've seen this before. This isn't a new story. It doesn't bother me. What you did for me really matters. What she did? I'm used to it. Don't you worry about me. What can I get you? And that, that alone would've been a wonderful story.
Michael Allosso: So that Yolanda was the person who made the most impact on me that day in my life. The most important business relationship I had that day, Matt. But that's not good enough. If I'm Michael Allosso and I'm you in your best day, and I wanna make a difference in the world. So you know what I did next? I befriended the woman next to me.
Michael Allosso: She dropped her earbuds and was on the ground looking for them, yelling at people around, can you find it? [00:15:00] It fell near you. Look. And so, I got down on my knees and we did it together and, and I said, you're kind of having a bad day, it looks like. Oh my! And then she laughed. She actually smiled, and I know this sounds weird, but we kind of bonded on the way and we, we walked off together and so,
Michael Allosso: what I had to think about is that, yeah, Yolanda made a huge impression on me and, and formed my business ethos that day, but so did the woman next to me. Um, that they were both important characters in helping me decide who I am as a business person and what my mission is on this earth. What I'm trying to do if I say, my company's called You On Your Best Day, and I make a difference in people's lives, I can't just say that in words.
Michael Allosso: I have to live it. And so both of those relationships had a certain magic. And what it always comes down to for [00:16:00] actors, Matt, is what is your objective? What is your desired result? So if my desired result was to repudiate the woman next to me, then I would've told her her behavior was despicable. And who do you think you are Ms. Rich lady reporting this poor person just trying to, and, and Matt, what would that have accomplished? She probably would've yelled at me and yelled at three more people, and definitely the next flight attendants, she would've butchered them. My objective was to make her better so that maybe the next flight attendant, she might think a little before she tries to humiliate them to that degree.
Michael Allosso: And so business relationships happen before our very eyes every day. Every day we have obstacles and our job is to turn those obstacles into opportunities to create who we are as business people. And so that, that's the most recent one, only because I had knee surgery last week and I haven't been able to [00:17:00] leave the house or else I'd have others, all my relationships this week, are with Peggy, my wife, who is the most important character in my story,
Michael Allosso: and Teddy, my dog, who is the other most important character in my story. And I had knee surgery and the next day he got neutered. So I have been nursing him instead of myself. And of course all my friends joke and say, ha ha ha. Did the surgeons get confused?
Michael Allosso: Does Teddy have a good knee now? And you got neutered? Ha ha ha ha. Yeah. But those relationships happen via text and email.
Matt Stone: Yes, that's where you say, well, this relationship we can end right now. No. Um, so, uh, no. But I think what I'm also realizing now why I've been so drawn to people who have a theater background in their approach to whatever it is that they do, is that you see every interaction as an opportunity. that, that the way you're describing the flight attendant, I have a [00:18:00] friend, whom I met on a plane flying over the Pacific Ocean. Um, and I admired the way he was a purser at the time. He's stepped down from being a purser, but he was an international purser, so he is like the boss of all the flight attendants on the plane. And there was a problem with a passenger and a seat that wasn't working and it was like premium economy. And anyway, there was all this stuff and I watched the way that he navigated it and without giving the details of my story, it was masterful, just masterful. And I, I just said, dude, this is what I do for my business. And I said, I have to say I wish I could take you like this Yolanda woman, you know, bottle what you've got and I'm like, dish it out
Michael Allosso: Right on. Right on.
Matt Stone: You know what? We, we ended up becoming friends over that. We stayed in contact. I had him on a podcast years ago.
Michael Allosso: Awesome.
Matt Stone: Um, but even if we hadn't, I still would've considered whatever length of time that we [00:19:00] were on that flight, that was a relationship. It's a relationship. It doesn't have to be something that endures beyond that moment. It can be a person at a register. It can be the woman sitting next to you on the plane and you're like, I'm gonna choose to pull, instead of push right now. I'm gonna learn about her. And I found that to be a much more growth oriented, energy choice to make, um, and to frame it as a relationship has been really important
Michael Allosso: I, I love that Matt. You articulated that so well. Um, people often wanna introduce me is that I teach presence, and charisma. And question always is, can you teach charisma and presence? How do you? And I think people misunderstand what charisma and presence is. Yeah, certainly there's an element about being interesting, but it's so much more about being interested.
Michael Allosso: That's what real charisma and presence is. Being genuinely interested in another human [00:20:00] being. And so why I was drawn to you, for example is 'cause I felt like when we met, you weren't just giving me a monologue about yourself to try to impress me. I felt like you were genuinely interested in me, and that's why I'm here on the podcast.
Michael Allosso: I, I don't do podcasts for people who are interesting. I do podcasts for people who are interested. Uh, I remember one of the first podcasts I did, it was over, and then the podcaster said to me, i, I respect you so much. Do you have any criticism for me? And I said, do you really wanna hear it or are you just being perfunctory in that question?
Michael Allosso: He said, no, I really wanna do, I do wanna hear it. And I said, are you aware that you spoke for 80% of the podcast? And I spoke for 20%? Well, yes. 'cause I was so interested in telling people... Do you wanna hear my feedback or not? I said that probably [00:21:00] isn't such a good idea. I felt like the podcast was more about you than it was about me.
Michael Allosso: I was kind of wondering why you invited me, uh, was I an accessory for you? And to the guy's credit, Matt, we became friends after that. And he hired me to work for his company and he did my retreat up here in Maine and was stunning by the way. And generous and like this was really a true learner, someone who really appreciated feedback and so when, when he asked me the question, he meant it.
Michael Allosso: Most people who asked me that question don't mean it. They really don't want to hear it. He really did, and he used it. That's a relationship that changed me.
Matt Stone: And it only happened because you were honest with him too. He asked, but you had to be honest with him. You couldn't just say, oh no, it was great.
Michael Allosso: Exactly. Well that, that there's no love in [00:22:00] that to, yeah.
Matt Stone: And it's vulnerable for you. I mean
Michael Allosso: Yes,
Matt Stone: It takes an investment, a co-investment of him actually asking and meaning it, and you being willing to give it to him, like really give it to him, and then willing to hang with him as you do the back and forth. It's beautiful when it works like that.
Michael Allosso: It is, and I live for that. That's what I look for in a business relationship. Because I wanna be made better. Uh, I'm so generous that I wanna make everybody better. And, and yes, and I wanna be better. I wanna be better too. And he made me better. He made me better. And to me, these are the great business relationships where we continue to grow, where magic happens.
Michael Allosso: And I use the word love and I don't use that accidentally. I can't do what I do without love. If I didn't love him, I certainly would've done what you suggested. No, you did a great job. Thank you so much for having me. Bye-bye. Lot easier. Lot easier. [00:23:00] Not why I'm on this earth.
Hi, Friends. I just wanted to jump in here really quickly because if you're enjoying my conversation with Michael Allosso, and he's got so much to share, so much rich knowledge and expertise, and he's just an incredible human being. But if you're feeling a little bit stuck in your leadership role, in your job, in your life, if you're feeling like you're, you're leading off the cuff and kind of hoping, um, that you're doing a good job or you're just feeling kind of stuck or, or dried up and don't have access to your vitality, uh, to your creativity, or you just wanna have more fun in life.
Michael does a fantastic retreat and this year it's May 28th to May 30th, 2026. It's called Awaken Your Potential. It's a two and a half day immersion retreat in the Northeast, and I just wanted to make sure that you knew about it. This is not a paid ad. This is because I like Michael and respect him and want you to know about it.
Go to michaelallosso.com and [00:24:00] you'll find the retreat information there. I'm also going to put the direct link along with the main web URL in the show notes. Okay? So check out the retreat and I know you won't regret it. Alright, back to the program. Thanks for listening.
Matt Stone: We need to wrap up now, but I, I'm endlessly curious about all these topics, so i'm gonna have to invite you on the show when we launch, if that's okay. Uh, we're gonna do some panel discussions and laugh a lot. I I can't wait for your voice in that if you're willing to do it. But help us shape, because you have such a creative mind and you've had so many experiences, what is it that we should feature on this show? What are some topics that we should talk about that maybe the topics talked about, but the angle isn't? What would be cutting edge to talk about that you're not seeing elsewhere?
Michael Allosso: The best book I've read in this week of recuperation is David Brooks, _How to _[00:25:00] _Know a Person,_ and you know how egotistical we can be, Matt. One of the things is, I can't lie, I'm reading I'm, and I'm actually listening because I can't take my eyes off Teddy because I'm so afraid he is gonna lick his wound.
Michael Allosso: And so I'm there holding Teddy, like playing toys with him without making him jump and listening to David Brooks. And I'm saying, oh my gosh. Like he's me, but 10 times more articulate and more eloquent and uh, and shaping it in such a wonderful format to make it so digestible. And so I think what you should have on the program are people who help us to understand other people really well. And not just understand,
Michael Allosso: but give us tactical tools, real [00:26:00] time things, activities, actions we can do to impact other people. Theoretical people bore me. Philosophical people bore me. People who talk and don't model what they're talking about bore me. So I think meeting you the way I met you and knowing how, um. external, you can be that there need to be external people who make a difference outside, who like you are rich with emotion, love, compassion, passion on the inside. Too general or does that make sense?
Matt Stone: It makes perfect sense and I, it's so, yeah, and I, but I like how you put it because the way you put it is gonna be, um. It's gonna make it even more useful. And I'm, I'm taking serious notes on these answers. I mean, I really think, I [00:27:00] alone cannot make this show everything that it needs to be. It by very definition, it has to be highly collaborative and, have a healthy feedback loop and get people's input.
Matt Stone: I wanna talk about the stuff that we're not talking about. And talk about it in ways that we're not talking about it. And start bringing things into the business conversation that people are like, wait, that's a business conversation? Yeah. It's a business conversation. And start normalizing, pulling from that palette into that closed business universe and kind of breaking the paradigm a little bit.
Michael Allosso: A hundred percent
Matt Stone: That's my goal. So...
Michael Allosso: Go at it.
Matt Stone: Maybe I'll wear a chicken, chicken suit next time.
Michael Allosso: Ah, you know, on my resume is chicken suit. I was a print model for many years, as you can tell, from my attractive physique. And I was cast in so many diverse roles, including a chicken
Matt Stone: A chicken.
Michael Allosso: For a bank, I was a chicken, that's my modeling career. [00:28:00] Chickens. Um, yeah, I was a software pirate.
Michael Allosso: Very, very attractive.
Matt Stone: A software pirate...
Michael Allosso: I was a software pirate on the cover of New England Business Magazine.
Matt Stone: Oh my god.
Michael Allosso: Software Pirate.
Matt Stone: I love it.
Michael Allosso: Aren't you proud of m e now?
Matt Stone: Yeah, this is the beauty of people is that when you get to know people, you find out, oh, their path wasn't linear either. They've got all this crazy stuff that they're bringing to the table, and you know, half the time you're helping someone do something that, and you're drawing for, yeah, there's the theory and there's this other, but at the end of the day, you're helping them do something that you figured out when you were 10 and you stubbed your toe
Michael Allosso: Right on.
Matt Stone: or you, you know, you were in the playground and Billy the bully taught you something and you never forgot it, and now you're helping a CEO with the same thing that
Michael Allosso: So true,
Matt Stone: figured out in the playground.
Matt Stone: Right?
Michael Allosso: Right. A hundred percent.
Matt Stone: yeah.
Michael Allosso: Well said. You're good, brother.
Matt Stone: Well Thank you for your time and most of all your heart, uh, your heartful and, and playful [00:29:00] sharing of a really a Costco sample. There's a lot more where that came from. So we are going to invite Michael Allosso back on when we launch for sure. And let me just close out by saying thank you for listening to the Building Business Relationship Show.
Matt Stone: This pre-launch phase, as I said, is all about discovery. So if something sparked your interest, share it with us 'cause we, we really do want to hear it from you. You can send me an email directly, matt@mattstone.co. matt@mattstone.co. You can send a direct message to me and say, Hey. This is what I think, or this is what you should do, you should put on the show. I may or may not like it, but it will be valuable no matter what. So do share those thoughts, ideas, guest suggestions, help us shape the conversations that come. And of course, make sure you subscribe, especially on YouTube. Look for the show on YouTube, same name, uh, and you'll be the first to know when it launches.
Matt Stone: And in the meantime when new content drops. Thanks again for watching. We'll see you next time.
[00:30:00]