[00:00:00] Dylan Bain: Welcome to Intuitive Finance. Today, we’re going to be speaking with true luminary of the tech world Mr. Mark Sylvester. His pioneering three-decade career saw him play an instrumental role in developing Maya, the 3D software that reshaped the entertainment industry and earned him accolades such as the Sci-Tech Awards and even an Academy Award for his efforts on the animation software.

[00:00:19] But that was just the beginning for Mark’s career. Mark was ahead of his time even in 2003, forging the very first social network for the TED Conference. He’s a celebrated innovator. Mark’s “see what you think” philosophy has driven entrepreneurs and creatives worldwide to think differently about their businesses. As the mastermind behind the TEDx Santa Barbara Salon series Making Waves, he brings global thought leaders together to discuss everything from tech to social justice.

[00:00:46] Beyond this, Mark isn’t just an industry legend. He’s a seasoned podcaster in his own right and the force behind the transformative audio education format, PodClass. A fervent believer in the power of stories, he’s also the executive producer for the StorytellingSchool.com, using applied storytelling to craft compelling narratives for brands. From software development to storytelling, Mark’s journey epitomizes innovation and his impact in the industry is immeasurable.

[00:01:14] I am so excited to have Mark on the podcast. So let’s dive into today’s conversation.

[00:01:23] Intro: We’re saying goodbye to the rigid numbers and strict budgets, and putting relationships back at the heart of personal finance. This is more than a podcast. It’s an invitation to reimagine your money story and journey with us through a landscape of intuitive strategies and abundance. Join a community that nurtures transformative financial mindsets.

[00:01:45] Welcome to Intuitive Finance. I’m your host, Dylan Bain.

[00:01:56] Dylan Bain: Mr. Mark Sylvester, thank you so much for coming on the podcast. I am delighted to have you here.

[00:02:02] Mark Sylvester: I’m glad to be here, Dylan.

[00:02:03] Dylan Bain: Fantastic. And I just kind of want to tee this up. I know a little bit about your backstory, and I’m really excited to get into it. Can you give us the 30,000-foot view of Mark Sylvester?

[00:02:15] Mark Sylvester: My mom said when I was eight that if I didn’t stop talking, my brother would never learn how to talk. So I’ve always been involved in communications of some kind or another. That’s a thread that’s gone through all the decades of my life.

[00:02:35] Dylan Bain: Excellent. So when you talk about communication and you’re looking at like — how do you integrate in communication? Talk to me a little bit about like, where does that start for you? When you talk about — I know that you’ve done entrepreneurship, where does the communication piece start?

[00:02:50] Mark Sylvester: Rather than going back biographically to decades — like my 20s was cooking, my 30s and 40s was doing software, developing computer animation software for motion films and visual effects video games. And then my 50s and 60s was creating software for the TED conference called Intro Networks, was large community-based software. And then that’s taken me up in the last 10 years is around Storytelling School, TEDx Santa Barbara, being a showrunner on podcast and helping people find their voice and build community through that.

[00:03:28] Through all of that, the ability to communicate an idea quickly and crisply and with intention is important whether I’m in the kitchen giving orders to my brigade, or I’m communicating to the market about why computer animation is important, or I’m talking to companies about why they want to have a more robust dialogue with their employees, or I’m interviewing someone for TEDx Santa Barbara — all of it comes from what’s the idea of this communication?

[00:04:06] Why is it important? What are the stakes? And what do I want the person to do? What’s the call to action? It might just be listen up or might be go do something. It might be whatever it is, but there’s some — well I’ve learned some very essential components. It doesn’t matter who you’re talking to or how many people you’re talking to.

[00:04:27] Dylan Bain: What are those essential components? And I love how you mentioned when you were — as a chef you’ve got your entire — it’s the yes, chef thing. I think we all associate. In working on as chef, you obviously you have a vision in your head, you have to communicate that. But I imagine that like those elements are going to be present with the software too, and all the different things you — what are, if we’re going to put a fine point on it, what are these elements?

[00:04:51] Mark Sylvester: Don’t waste people’s time. You don’t need to say a lot of stuff. You can say things very quickly and succinctly. So don’t waste people’s time. Just tell them what you need to tell them. But have intention, like know why I’m opening my mouth right now. And a lot of people don’t.

[00:05:09] What’s the intention? What do I want out of this communication? What do I want them to get? What do I have later learned? What do I want them to feel? So there’s some nuance to that communication, I think, where I had to go back now in my twenties and my thirties. I might be paying more attention to the emotional state that I’m creating in someone who’s receiving a communication. So if I’m the boss, I want them to feel safe and secure and confident that they can do this thing I’ve asked them to do. Where when it’s yes, chef world, it’s just like, hey, just do what I tell you to do, right? And that’s not a healthy communication environment. You get the job done and you have to do it quickly. But you don’t really care about people’s feelings. I think I would go back and have a different sense were I to do that today.

[00:06:03] But the number one thing is, what’s your intention? And understand and communicate the stakes of what you’re trying to get done. Like, stakes are so important. If it’s low stakes, it’s low stakes. That’s fine. There’s no judgment into that. But if it’s a high stakes thing, this is really important: communicate that. So someone knows, oh, I need to pay attention right now. This is really important.

[00:06:32] And how you do that? Through your tone of voice, through eye contact, through making sure the person’s listening to me. And I play this game where I want to see if I can get their heads nodding because I want them mirroring me. Okay good, you’re listening to me. Great. In Japan, they have a great mechanism to let you know that they have physically heard your words. And they go, hai, hai. That doesn’t mean I understand, I agree. It doesn’t mean — all it means is my ears are working and I heard you. I learned that because I thought I — I misinterpreted that. Like, a lot of times we’re just giving nonverbal cues back to the person who’s speaking that yes, I’m paying attention, yes, I’m listening. That does not mean they’re cogitating at all.

[00:07:23] So you want to be able to, like, my intent is to communicate a high stakes thing I need you to do. And I’m going to ask some questions to make sure that you got it, you understand what the stakes are, and you understand what you need to do. And that can be five sentences. Doesn’t have to be a speech. I could — I think we speak too much. We can get our message out in a shorter period of time.

[00:07:49] Dylan Bain: I love that. When I was doing my MBA in graduate school, I had a writing coach. We always had to do these quick summaries of everything we read. And we read this like, 20-page article and you wanted one paragraph. And he used to say that we — you wanted to have the concise, so that every bite was nutritious. Because you never want to be in a situation where you think you’re dazzling them with brilliance, but really you’re baffling them with bullshit. And I took that away from graduate school of like, how do I pinpoint exactly these things?

[00:08:18] I want to go back to one thing you said because I think you did a great job in saying, let’s talk about these stakes. Like what’s at stake here? And I think about like when I was a teacher — when I was teaching mathematics, my students, I’d be like, yeah this is going to be on the test. And that was like, communicating the stakes. And for some of them, that was life or death, and some of them that just meant they didn’t care. But I want to tie that in the communication of the stakes to what you said about the emotions of what are you invoking in this person. And how are you making sure when you’re talking to them that you’re not — hey this is really important to me, but you’re not overwhelming them with the idea that you just put a boulder on their shoulders?

[00:08:57] Mark Sylvester: Great way to think about that. If you’re really present — that’s the other thing I wish I would have known when I was 20 about being present. If you’re really present and paying attention, this message is not about me, it’s about you. When I give a talk, the talk isn’t for me, the talk’s for you.

[00:09:17] Oh, I’m giving a keynote. Yeah. Yeah? For them. So that’s the higher order bit, the black belt level way of thinking about it is that this communication is for them. So I need to be tuned in, what do they need? They need to know, yeah, this is a little above your pay grade, buddy. You’re going to really have to stretch. This is tough. But you know what? I got you. I got you. So you get going. I think you can do this. Or I wouldn’t have asked you. However, if you get stuck, just come on back. I got you. Don’t worry about it.

[00:09:52] So now, how does that make you feel? I got you. You’re safe. Let’s like, oh, okay. Like, and now what do you want to do is, well, I’m gonna, I’m a climber, man. I want to get that done. You know, I’m going to, cause I would like to be seen. By you, my boss, as someone who can take a challenge and rise to the occasion, because you might ask me to do something hard again, and that’s going to be good as I move up in the organization.

[00:10:21] So I think if you pay attention to the person you’re talking to, like my wife, Kymberlee, she has a superpower. She has many, but one that I really appreciate is her ability to read a room. So we do a lot of workshops and whether it’s an improv workshop or it’s a communication workshop, a storytelling workshop, a branding workshop, whatever it is. And she has a plan that she’s studied the room. She knows what we’re, we need to do. She knows what they need to hear, but she’ll call audibles. We have cues to one another. She’ll call audibles throughout that. And I’ll say, hold it. We just missed three pages of stuff because she knew she’s reading the energy in the room of how people are. And now no one knew that, but that’s the high level bit that you want to be able to do is like, if you’re leading a team meeting, you know?

[00:11:22] Now, thankfully, when I was leading teams and doing all that, we did not have phones in the room, right? We didn’t have distractions, so I think that’s probably a really big challenge. I would have a basket and everybody throw their phone in the basket these days. And if it’s not that important, then maybe you don’t need the meeting. Like if it’s okay that people could be doing other stuff. That’s fine. Go do the other stuff. We’ll let you know what happened, right?

[00:11:55] Which gets into a little meeting theory that I’ve used all my life, which was, there’s only four kinds of meetings.

[00:12:03] There’s an information meeting. We are going to sit and listen to someone give us information. Those are over. Send an email. Those are over. We don’t need that.

[00:12:15] Number two is a brainstorming meeting. Hey, we don’t really know how to solve this problem. So we’ve invited you because we feel you have a little domain expertise. You could help us solve this, we’re not, all we’re looking at is brainstorming. So now I know coming into the meeting, oh this is gonna be fun, I’m just gonna — I wonder what the problem is, and I’m kind of teed up, I’m excited about it.

[00:12:39] Third kind of meeting is a decision meeting. We are going to send you an email ahead of time so you have all the information. We all collectively need to make a decision, so we’re going to leave this meeting having made this decision or these decisions. Okay, we all set? Good, good, great. That’s what we’re doing.

[00:12:59] Again, that’s — the communication ahead of the meeting is the intent, what I want to have happen. What are the stakes of this? Hey, this is a big product decision. We’re laying out the roadmap. We’ve all had all of our little meetings. Now we’re coming together as the senior team and we’re going to map out the next three, six, nine months. Okay, stakes are high. This is your role. We know what you do. There’s the call to action. All the pieces, same pieces are in there, right?

[00:13:26] The fourth kind of meeting is a no agenda meeting. Lunch, dinner. Hey, we’re just getting together because it’s good for us to get together when we’re not working. Part of good leadership is building camaraderie with the team where you’re not working and you’re not being judged either by others, like did I do the right thing? Did I say the right thing to my whatever? No, let’s do whatever it is that’s fun. Go play volleyball. Go have coffee. Go have — I used to do no agenda breakfasts once a week, and with seven o’clock in the morning, we’d go and talk about whatever you want.

[00:14:06] I don’t care. Ask me anything you want. Okay. You know, now it’s an AMA. It’s a thing, but that’s the kind of thing where people get to know, like, and trust you because there’s no agenda. So those four things, but the idea of communication is embedded in that.

[00:14:23] Dylan Bain: So for anyone who’s listening who works in the corporate world, your statement that the information meeting is over, send an email, just nourishes my soul because of how many things that meetings have been in where I’m like, this could have been an email, this could have been a YouTube video, this could have been anything but me having to be physically present. Which I think relates right back to your — when I asked you about elements of communication, first thing you said was don’t waste people’s time, right?

[00:14:48] Nothing will kill morale on a team is if the leader is constantly trying to tell them stuff and put them in meetings. Because on a lot of levels, it feels like they’re trying to do that because they want to feel self-important, which then goes back to the stakes of like well, I’m here to make you look good, I’m not here to actually achieve anything.

[00:15:06] Mark Sylvester: Right, right. I calculated at one point — I calculated what the per minute cost was of every kind of meeting we had. And if you were late, you paid me because you wasted all those people’s time. This meeting is costing me $67 a minute. You were five minutes late, you can get me 300 bucks. Put it in the kitty for treats. What? Yeah. Well, come on. You know what time the meeting was? We’re here. You weren’t. That cost money. We couldn’t work. You know how many times that happens? How many times people had to pay? Word gets around real fast.

[00:15:47] Dylan Bain: I think that’s brilliant at a lot of levels, to be able to put that monetary value on it, of what the time is stakes. Yeah. Well, and it’s also its own form of communication. Our time is valuable. Your time is valuable. So you shouldn’t allow people to waste it. So when you’re talking about these communications, and obviously this is a huge part of that. You talked about being a chef and you talked about being an entrepreneur. What would you say is the role? And you talked about improv. I’ve done improv because I enjoy doing theater and I enjoy acting and singing and things like that.

[00:16:22] But I would love your thoughts on the utility of improv. And I asked this question because I believe that there’s a lot of people when you say, hey, improv can improve your sales. It can improve your presence at work. It can improve your confidence. I think a lot of people think like, oh, you want me to go play games? They think it’s frivolous. And I know that you have some thoughts on that, and I would love to have that discussion.

[00:16:44] Mark Sylvester: We just did a workshop two days ago. We were hired to come in to a CEO — a mastermind of CEOs. We were in a manufacturing facility, like the hardcore old school. It was here, it was an hour north of us here in Santa Barbara. I was like, what are we doing at this place? And we were in their conference room, which they dubbed the crow’s nest because one wall was glass and you could look out on the manufacturing floor and they make drill bits for horizontal drilling, trenching. And there was like, all these people and all these big machines. It was very industrial.

[00:17:27] And we’re there teaching a class called Permission to Play. And we were doing — it’s applied improv, it’s how does improv help in communication, in confidence, in all of the things that leaders need. And improvisation is listening. So, like, what’s interesting is all these things are very adjacent to one another, okay? All the things I do. We didn’t talk about martial arts. We haven’t talked about cooking. We haven’t talked — but they’re all, I think they’re about being present, about listening, about getting out of your head.

[00:18:07] And I would say that the thing that I try to communicate — because Kymberlee and I add completely different points of view. Not different, but different ways of thinking — they’re not collisions — when we’re coaching these people. And for me, it’s improvisation at its finest is when you understand the rules of the game, right? There are some rules, okay? These are the rules. Great, cool. And that you are so present and you trust yourself so well.

[00:18:41] Like, I know one of the rules is everything you say is true. That’s one of the rules. So that means an improv, everything I say is true. There’s a Martian, there’s a this, there’s a that. Yup, there is. So they’re going to say, yep I — yes, there is. Oh my gosh. And he’s so well-dressed. So I’m kind of, I’m going to “yes, and” that.

[00:19:04] Well, how great is it in the office or in a meeting where someone says, Bob that’s a great idea. And we could probably start a whole campaign in the Midwest around that. Oh, now Bob feels heard. Everybody sees how I didn’t go, come on, Bob. That’s silly. We can only do that in the Midwest. And I see, so I can “yes, and” him. There’s a thing called “yes, but.” Yeah, but it’s going to be really expensive. Yeah, so I theoretically yes do, but I put a but in there. “Yes, but” right? Or I do “no, but.” No, come on, you idiot. How many times in business are we in a meeting where someone, some maybe younger person got lots of ideas. They haven’t been beat down yet by the corporate hierarchy. And they have this great idea. And then someone goes, oh, yeah, that’ll never work. We can’t do that. Just no, just not going to happen.

[00:20:12] How do you “yes, and” in a “no, but” culture? That was a question we got, which I thought was great, right? And we had a really good exercise that we did immediately afterwards for that. And it was two of us.

[00:20:27] You and I now, let’s do this right now. You and I, we know each other. We work for ACME Corp and we’re in charge of planning the party for this weekend, big party. Big party, huge party. You and I are in charge. And you’re going to give me an idea like, hey, we need to, or we’re gonna. Whatever your idea is, doesn’t matter. And I’m going to say “no, but,” and I’m going to add to that and you’re going to “no, but,” and add to that. So we’ll do three or four sentences back and forth.

[00:20:58] Okay. We’re starting to party.

[00:20:59] Dylan Bain: All right. I really think that we need a DJ to set the mood.

[00:21:02] Mark Sylvester: No, that’s going to be really expensive getting speakers and stuff. We ought to just — I’ve got a Bluetooth, like we’ll just bring that and put on like, Spotify or something. “No, but.” No, so you’re denying my idea.

[00:21:18] Dylan Bain: Okay. No, but I think we need to have a human touch that can really read the room and set the tone to get the most out of this.

[00:21:27] Mark Sylvester: No, but it would be someone we don’t know, and I just, that would upset people. Okay, so. That’s “no, but.” We’re just no-butting each other. So now we’re going to do the same thing, different aspect of the party planning. Okay, we were talking about the music. Except now this time it’s going to be “yes, but.” So you can start.

[00:21:47] Dylan Bain: So I think that we should really have centerpieces to set the table and show people that this is serious.

[00:21:53] Mark Sylvester: Yes, but let’s get them at Michael’s because I only have like a $75 budget.

[00:22:00] Dylan Bain: Yes, but we want to have this be an announcement. Put a pin on it.

[00:22:05] Mark Sylvester: Yes, but I don’t want to appear frivolous.

[00:22:08] Dylan Bain: Yes, but we want them to take it seriously.

[00:22:11] Mark Sylvester: Okay, so that was “yes, but.” Now we’re going to yes and so same thing, another aspect of the party.

[00:22:18] Dylan Bain: I really think that we need to get this catered.

[00:22:20] Mark Sylvester: Oh yes, and I know that Susan in accounting loves those little hot dog things that are wrapped in pastry. We’ll make sure we get some of those for her.

[00:22:30] Dylan Bain: Yes, and we can make sure that we have vegetarian options so that everyone feels included.

[00:22:35] Mark Sylvester: Yes, and the kids in accounting, the kids we just got from college, they’re vegans, which is fantastic. So we’ll make sure that we even have vegan options.

[00:22:46] Dylan Bain: Yes, and charcuterie boards are huge right now, so I think we should include some of that in it.

[00:22:52] Mark Sylvester: Yes I love those, and we could probably even get a whole selection of like, pickles and olives and zinc.

[00:23:01] So, in which one of those interactions did you feel better?

[00:23:07] Dylan Bain: It’s incredible to me. I know the game here. And in that last one, I’m like excited to have a party. I’m immediately bought into it. Like I kind of tingle, almost.

[00:23:17] Mark Sylvester: Exactly. So when you find someone, someone who’s listening to this, is living in a culture where there’s some people that do “no, but”, maybe bring in an improver to come in and run a workshop. But play this game with — we did that in less than five minutes and it helps them see, oh, okay. I got it. Okay. And it might take a little while, but actually that interaction challenged me to think more about applied improv, right? How do we really apply it? So it’s listening. It’s not thinking ahead. Because there was no way I could add in something because I have to respond to what you’re saying. Now we’re talking about the music. Now we’re talking about the centerpieces. Now we’re talking about the food. I wanted to talk about like, the PowerPoints or the — where are we going to video? We’re like, what are we — like, because I had a story in my head. How many times do we go into a conversation with all the stuff we want to say? Like oh, I can’t end up, I’m going to do the plot as opposed to like, listening.

[00:24:30] I’m here for you. I’m not here for me, I’m here for you. How can I help you? And then I’m going to respond and trust that if I’m a caring, evolved individual, and I’m not an asshole, and I don’t need to be a smart aleck jerk, but I’m — and you’re a human and I care about how you feel — sincerely care, then I’m going to be listening and reacting. And all I want to do is hear you, react emotionally to what you said. How did what you say make me feel? ‘Cause if you can get a sense of my emotions, like if I’m like, oh my God, I’m like, yeah, let’s — whatever that emotion is. My state is going to impact your state. And at the end of the day, if we really believe that we want to live in a relational world rather than a transactional world, then we’re going to pay attention to things like listening, eye contact, emotions, how does someone feel — because the relationship is the most important thing to us. Not the transaction, not the thing.

[00:25:51] The centerpiece was not important. What was important was the feeling you were trying to get across to the people and communicate to me that you thought better centerpieces were going to convey a better sense of status in the party. And that’s what you were trying to communicate. I was like, no. So I was killing your emotions around that.

[00:26:14] Dylan Bain: The idea of relational versus transactional, like what a beautiful way to pinpoint that. Because I’m just thinking of like different jobs that I’ve had, relationships — some romantic partners where you get into this place where it becomes transactional and then you start feeling used — it’s the difference between — being at a job where you want to stay, even though you could go someplace else and get paid better because you want to stay because you know you’re valued because you can see that the real, the real life thing impacts what you’re doing.

[00:26:44] But I also think just that in listening to you talk about what a leadership piece this is. That I’m here for you. I’m here to serve you. I’m here to actualize you. That’s my role as a leader. And I’m going to listen and I’m going to look at you as a whole person and bring that forward.

[00:27:01] I think that gets lost in leadership, as particularly you hear entrepreneurs where they’re like, yes, we’re going to — it’s like a military operation to them, right? They’re like, we’re going to go in here. We’re going to grind. We’re going to grind ourselves to nothing. And like, some people are like, yes Brian, we did nothing. And other people are like, I want nothing to do with that. I’d love your thoughts on that leadership piece — as somebody who’s led kitchens, who’s led software companies, who’s led workshops — what is that essence in that leadership that comes into from your improv?

[00:27:30] Mark Sylvester: Looking at it through the lens of, improv is a team sport. It’s like I say to my wife Kymberlee a lot. Something will come up and we will have accomplished something. And I say, our relationship is a team sport. It is. Improv is a team sport.

[00:27:50] My job is to, number one, take care of myself. Know who — if I walk out into a gold stage and my scene partners come out from the other side, I have to take care of myself. Who am I? How am I walking? Do I have a little hunch? Am I? I’m this guy. So maybe that’s — all I’ve got is that. And, but I know I’m the guy who’s kind of wiggly and squirmy. And if I’m the guy who’s wiggly and squirmy, what’s my point of view? Maybe I can’t make decisions. Maybe I’m just — I don’t know what to do, maybe my voice is like that, I — that starts to happen. So I’ve taken care of myself first.

[00:28:33] Now, the next thing is my partner’s coming out and hopefully they’ve taken care of themselves. So now we come out now, what’s the first thing we’re going to do? We’re going to look each other in the eye. We’re going to look each other and try to get a sense. And this all happens in nanoseconds. And I’ll get a sense of, who is that person? How can I react to, so someone might read, they see that and they go, oh God, she didn’t take out the trash again. Did you, Bobby? That might be that initiation. And now we’re going back and forth and we don’t have to win.

[00:29:06] What we’re trying to do is build a relationship. We know each other, but we’re trying to help the audience understand the situation, like what’s happened. The audience has just tuned the channel to these two people that are on stage, and they’re in the middle of something, and what’s going on there?

[00:29:25] So one of the things that’s interesting about improv Is you don’t want to win. Winning’s not fun to watch.

[00:29:33] Dylan Bain: Okay tell me, like, I’m super excited about this because in leadership, I think about this all the time. Connect not wanting to win to leading a team to success.

[00:29:47] Mark Sylvester: So I don’t need to win. We need to win.

[00:29:52] Dylan Bain: So the leader is really bought into the team. This is not about the leader’s ego. This is not about the leader’s accomplishment. This is about, like you said, I’ve got your back.

[00:30:02] Mark Sylvester: If you don’t have followers, how can you be a leader? Yeah. I mean, have you ever heard of gamification? Do you know what that is? So gamification has five rules. One, you have to opt in. I have to want to be there. Oh, I have to want to play the game, so I have to want to come work at this place. Number two, there have to be clear rules. I need you to be here on time, I need you to do this, I need you — there’s some clear rules. Any game has rules. Number three is there’s a scoreboard. There’s a way to measure how we’ve done in whatever it is. Whatever it is. Number four is an important one. There has to be an obvious leader. The notion that it’s the collective, I get that. And yes, there’s a collective, and there’s a leader.

[00:30:56] And the fifth rule is it has to be fun. People are going to just, it’s fun to play. So that’s — you can gamify literally anything, and I’ve done it a hundred times. You can gamify anything and you make it fun. You just, okay well, we’re all here. Great. Here’s the rules. This is what we’re doing. And here’s how we’re going to measure what we did, you know? It could be by applause, could be by how did you get the lesson? Did you — all of that stuff? And she’s the leader, and let’s have fun. Yeah. Very simple.

[00:31:30] And I think that, I think you have to have enough ego strength to get through the down cycle on anything. There’s always a down cycle. That’s just the law of physics. Natural law, you’re going to be happy, you’re going to be sad. You’re going to have lots of energy to push through, to get to the trade show, to do all this stuff, and then afterwards, you’re going to be here. There’s always going to be that. So knowing that you’re going to have that, how do you modulate everybody’s energy and have everybody — just kind you can’t rah all the time.

[00:32:11] Nope, this is the time where we’re just going to sit and chill. Everybody cool? Yeah, we’re just chilling right now. We’re good. We did it. There’s a lot of lessons we can get from the military on that, right? Or sports. That’s why we love working with ex-military, ex-first responders, people who’ve been in sports, whether they’re solo sports or team sports. And we love that because they understand the discipline, they understand the ebb and flow of, okay, we all gotta work really hard and then we can lean back.

[00:32:47] Dylan Bain: Well, in those down periods — again, kind of going back to what you were talking about, the four different types of meetings. It sounds like the best time for an unstructured meeting, right? Where you can say, we’re going to chill. Like, let’s just break bread. Like, things are hard right now. Let’s just look at each other as humans.

[00:33:01] Mark Sylvester: Yeah, exactly. Exactly. And

[00:33:05] I think that entrepreneurs, there’s this mistaken notion, in my opinion, that you have to be on all the time. You know, you have to be on all the time. No, you don’t. No, you don’t. You don’t have to be right all the time. You don’t have to, you don’t have to be, it’s just like — you’re human. They have a really good idea, I need all y’all’s help to get — turn this idea into a product, and then that product turn into a business, and that business turn into generational wealth.

[00:33:45] That’s the — for my whole career in software, especially in animation software was that we get lots of ideas from customers, from internal, from engineering, from marketing, from my partners. We all had ideas. So I had this philosophy that developed through those years, where it’s like, I’m pretty convinced that 1% of those ideas are good. Let’s keep having them, right? It’s a numbers game. Let’s have, keep bring them. And then we’re going to have ways to sift through to come up with that, that move, that’s through, that’s the one.

[00:34:27] And that’s a lot of work to get to the one. Okay well, now we need to make that a product or service. Something we can exchange for value, we can sell. It’s another curve. Those are all the things you need to do to make it a product. Whatever it is. It’s a video, it’s a widget. It’s an app, it’s — I don’t care. Whatever it is, if you’re going to sell it, you’ve got to develop it and you’ve got to turn it from an idea into a product or a service. Again, I think there’s probably a 99% fall off of people who can actually turn the idea into a product. I might be being harsh, but it’s an 80/20 for sure.

[00:35:15] Okay, cool. So now I’ve got this product or service and we’re excited about it. And this is the early stages of I’m building my company. Like we’ve got a — we have a prototype. That’s part of the product process. It’s not a product yet, but it’s a prototype. But now I’m going to bring some more people on and we’re going to get it productized. Well, the next thing is that, okay, let’s make a business out of that. That’s yet another order of magnitude of energy and effort and expense.

[00:35:44] And again, I think you have another 80/20 fall off of people can actually turn it into a business. Okay, great. Great. How many people say I’m going to do a podcast and don’t make it out of past five episodes or make it past 20 episodes? That’s a product. There’s a value exchange for that thing, but they don’t turn into something sustainable or whatever. The restaurant is open for 18 months or 6 months when it closes, because they haven’t figured out how to make it sustainable or how to have that business last.

[00:36:22] The next one is the one that, that I’m really interested in is how do I generate generational wealth? What are the things I’m doing to that business so that thing can last for 10, 20, 30, 40 years? How are we thinking? And this is a very Japanese thing that was — that I was exposed to at Wavefront early on when they said, we worked with Sony and we worked with one of the grandsons and he couldn’t understand culturally how we were so quarter driven. Everything was quarter driven. And he was brought up to think generationally, 10 years, 20 years that just this culturally, he had a hard time understanding our, hey, let’s go. We got to go. We got to go. We got to, he’s all, Mark-san, calm down. You have time. No, I don’t. I gotta — long term, right? And that was 40 years ago.

[00:37:28] So that deeply impacted my that you still have to deliver quarterly results. We had public companies. So I get all that. But I think leaders need to be the ones who can say, what’s the long game here? Where are we going? Where’s, what are we building that’s going to outlast — I mean, seriously, are we building something that can outlast us?

[00:37:54] Dylan Bain: That is an amazing breakdown of those different steps. One thing that stood out to me a lot, where you were talking about — 1%, and I think that 1% numbers probably actually get like, 99% of all the ideas that come tumbling out of a brainstorming meeting are going to be not viable. And the thought that goes through my head is like, what — even if it was 80/20, that means four out of every five, what a falloff rate and failure. And having to be like, to get to that idea, and then you have to do it all over again to go from idea to product, and then product to business, and how much failure you have to do to get there.

[00:38:31] And I think that’s where most people don’t want to do this. If they lose track of it, or they say, well, I can’t fail — and I personally think this is the fault of our education system, because you can take the test one time and then you’re done, right? I would love your thoughts on that failure piece and how do you navigate?

[00:38:46] I mean, you’re somebody who’s done this in multiple venues — whether it’s cooking, whether it’s improv, whether it’s TEDx, whether it’s working with Wavefront and your software company — what is the relationship with failure and how do you communicate that to your team while the team might be failing?

[00:39:04] Mark Sylvester: I redefine failure. And this comes from my martial arts. It’s just an opportunity to train. It’s an opportunity to train. Remember, we have scorecards. We didn’t measure up, whatever that meant. Okay, got it. And then enter another thing that comes from the military, which is an after action review, which I don’t think is given the level of importance it should have, and I won’t say should. When you see how important it is, you will adopt it into your life. Three things: what went well, what needs work, what went wrong. What went well, what went wrong, what needs work, okay?

[00:39:50] After everything you do, what went well? Are we — we had the product spec right. We had the right people on the team. We had the — what went wrong? The demo failed. Look at that. With the Bing demo where they got the, or it was the Google Bard demo where they asked it a question and it gave the wrong — okay. How much work had been done? How much we think about that? How many hundreds of people and one thing…

[00:40:23] So what went wrong? What needs work? Well, maybe we do more testing of whatever it is. Kymberlee and I are religious about that. We call it the dub — the three W’s. Religious about it. Anytime we do something in public, any workshop, when we were driving back from the applied improv permission to play workshop. What went well? What needed work? What went wrong was — this is how Kymberlee got introduced: I’d like to introduce Kymberlee Weil. She’s a NCAA Woman of the Year.

[00:41:06] Dylan Bain: Just talking off his phone the whole time.

[00:41:08] Mark Sylvester: Oh my God! So, what we learned from that is, let’s give a four sentence intro — somebody can have a bio that can be in the printed materials, but let’s give a four sentence intro to the person that’s something that they can just remember, and if they have to read it off the piece of paper that we give them.

[00:41:32] So I think back to failure. Yes, you could call it failure and no one wants to fail. The whole thing — move fast, break things — I mean, I get all that. I disagree with it. We are going to fail. A batter who is at the top of their game with a .387 batting average is a rock star, which means they failed how many times? Right? But do we sell it? No, no. It’s like, what do we learn from that? It’s an opportunity to train. And if you don’t intentionally have a reflection to look back, and as the leader, don’t let everybody be victims. Oh, well — if Bob would have done this — or blaming or any of that kind of negative stuff, that doesn’t help you at all. Well, maybe we need to improve our HR screening so we get different kinds of people. What, whatever it is, it’s a way of looking at it to say, we want to get better at this. And we didn’t do as good as we wanted to. Our scoreboard, we didn’t measure up to what we wanted.

[00:42:43] What could we do? It’s an opportunity to train. What do we need to do? Do we need to work out more? Do we need to do better specs? Do we need to have better review of our numbers? Do we need to have better comms with our customers? Do we need — not go to these kinds of trade shows, whatever it is. Have that intentional thing without any judgment around it.

[00:43:03] Well, you made that idiot decision. That’s not helping anybody. It’s the, team wants to succeed for whatever reason. The team has set a score, whatever that is. I’ve been trying to improve my W2. I’m trying to improve my quarterly results, my shareholders. I want to be happier. I want to be healthier. I want — whatever it is — again, I’m agnostic about what you’re — we’re scoring, have you put together a thing so you can score and you can win. Yeah, that looks good. I like that. Go get them.

[00:43:38] Dylan Bain: Right. And I love how you said — not having a judgment call on it, of like yeah, I face planted here. Okay. Let’s just, I’m clinical. I’m not critical. I’m going to just be very focused on it. Because I think that people will get into these shame loops. They’re so focused on them. They missed the mark, and somehow missing the mark meant something bad about them, but going back to your example of how do you build generational wealth, there’s going to be a lot of failure in that.

[00:44:07] And even when you brought up Google and I have a computer science background, so I know how they train AI, right? That AI had to — I mean, it’s amazing piece of technology, but it failed literally billions of times. And that’s how those models are actually designed to learn, is to learn from their failures, which has created things like ChatGPT, Google Bard, and all the other ones.

[00:44:30] So like, I kind of feel like that’s a huge takeaway to be looking at it and saying, I need to not judge myself. I need to be present for myself. I need to lead myself. I need to listen to myself. What am I saying? Everything that you were talking about, I think can be reflected right back on to us.

[00:44:47] Mark Sylvester: If you only ever remember three words from this conversation, the person who’s listening. If you look at every situation, good, bad, ugly, everyone, it’s an opportunity to train.

[00:45:04] We got that from Master Rick, 9th Dan Hapkido Grandmaster. And he’s a philosophy prof at UC Davis and a 9th Dan martial artist. And whenever we’re up north, and if we can get over to Davis, we go in and train with him. And you train and he philosophizes, you train and he philosophizes and he’s brilliant to be around.

[00:45:34] But you could say, gosh, it’s a beautiful day to go. That’s an opportunity to train. I’m like great — what? He goes, well, you could probably turn your gratitude up a little bit. Oh yeah. Yeah, you’re right. In his world, everything is an opportunity to train because we are working, we’re trying — in martial arts, there’s many mantras, but one of them is seek perfection of form. Like we didn’t spend any time — we talk about improv, but I’m a 2nd Dan black belt myself, and the time spent on the mat and time spent in life, it’s another one of those very little bit of time on the mat and it impacts everything in your life.

[00:46:23] We have a mutual friend, Robert Wunderlich there in Denver who’s on the mat all the time — living a martial life is about being present and being there. I am in charge of your safety when we’re sparring. I am very in charge of your safety. I, as a black belt, I’m even more so. I mean, I know how to get my punch right there and not hurt you.

[00:46:52] I think what’s been if — in reflecting back all of the things that I learned how to run a kitchen, how to run a software company, how to — the 257 things to become a black belt, the various rules and hundreds of hours we’ve done in improv training, the communication stuff we’ve done. What’s fascinating to me — and layer on top of that 10 years of meditating every day — all of those things lead to being present, in the moment, reacting. And having a plan, but also reacting to the things around you.

[00:47:38] And you had asked in the very beginning, if I could go back to my 25 year old self, I would have told my 25 year old self to start meditating because it’s not what you think it is. I had a mistaken notion of what meditation was. I was going to be a Baptist minister when I was 18. That’s what I wanted to be.

[00:47:59] Dylan Bain: I was going to be a Catholic priest at 18. So we’re in good company.

[00:48:02] Mark Sylvester: There you go. I was baptized Catholic, but then I was in the Jesus freak movement. And so I was going to do that. And I found that that wasn’t the path I was supposed to be on, but I had thought meditation was something that was Buddhist and okay, no I’m a Baptist. Well, I’m not a Buddhist, so I can’t do those things.

[00:48:23] And it wasn’t until I was 55 that we did a whole life challenge through CrossFit gym that Traver was running. Traver ran CrossFit, Central Coast CrossFit here in Santa Barbara, and they did a deal, which was a multi-week whole life challenge that was wellness, fitness, and nutrition. And in the wellness side, we had to download this app called Headspace, which was brand new at the time, and we had to do it for 10 days.

[00:48:54] And I just loved what I learned in those 10 days. How to modulate, how to be present, how to breathe, how to just be here now. I never really learned that. So as a 25 year old, I would say don’t wait till you’re 25. In middle school, start meditating. Right? Taking a little time to just to sit and be quiet and learn that you can control your monkey brain. You can control, overwhelm — all of those things are, I won’t say easily managed. All those things are manageable.

[00:49:34] Dylan Bain: I think that’s a great place to leave this conversation, Mark. This has been an amazing conversation, discussion. For people who are listening, where can we go to find more Mark Sylvester?

[00:49:44] Mark Sylvester: I am not kidding on the Internet. MarkSylvester.com. S Y L V E S T E R. Pretty easy. And it’s all there. I was very lucky to be very early in the internet and very early in websites and even being a tech person early on in the early eighties to be ahead of all that.

[00:50:06] I remember going — leave you with this. Went to a trade show, and one of our competitors from Toronto was in ’99. He’s in trade — it had to be before that. Didn’t matter. But, you know, you go to the trade shows and everybody gets a booth shirt there, but he’s going to be out of where the booth thing, whatever it is, and there they were so excited because they had a website. So on the back of their shirt was this long ass website embroidered onto every single shirt. They went, wow, good for you. You’ve got a website. Wow, that’s bringing value to your customers. Now you’ve got a website — he was just, he was so excited to show this to me because we were friends outside of our competitive nature. And he just went, Oh, I could have “yes, and”-ed that, but I know, but it didn’t.

[00:50:59] Thanks for having me on Dylan.

[00:51:01] Dylan Bain: Thank you so much.

[00:51:03] Outro: Thanks for listening. The conversation doesn’t end here. Please share the show with friends, and make sure you keep up with all the latest updates on Instagram and Threads at @TheDylanBain and dive deeper into the world of finance with me at DylanBain.com where you’ll find insights, resources, and strategies to reimagine your money story.