Business Culture & Productivity | LiveIntent, Chief Business Officer Jason Oates (Podcast 251)

You can't build a great culture by ripping into each other and allowing other people to rip into each other, because as soon as they actually realize that that's okay, then all of a sudden you got a bunch of people around, and then that just starts to really ruin the beauty of a culture and productivity starts to fail and people aren't happy. And if people aren't happy and motivated, you're not going to thrive.

All right, you're going to love this interview. I just had Jason Oates, the chief business officer for Live Intent, on the podcast today. He went into some really, really cool areas. Fascinating company. Talked about balance, talked about his relationship with the CEO, talked about how to evaluate ideas internally when a company's scaling. They got about 275 employees right now. Got into a lot of stuff around strategy and core values. Talked about bad revenue and how to have defensible revenue, and then talked about how to be a lot harder on the issues and softer on people. Some really great wisdom stuff in there as well. So you're going to love the episode. We'll see you on the inside. Interestingly enough, he is only the first company in history to ever have two guests from the same company. On about two years ago, we also had Brett Pinniger, who was the chief operating officer on, as a guest as well. Strange that we actually made this happen, but you're going to love the episode. We'll see you on the inside. So, Jason, welcome to the Second Command podcast.

Thank you. Thank you for having me. I've been looking forward to this.

Yeah, same. It was fun to actually just kind of go through some of the initial information that you sent over to us. And what I'm most intrigued about is how you and one of your close friends have kind of built this out almost from the get go and had done other things together. And what do you think it is that has allowed you to stay friends through this long journey?

I met my wife in April of 1999, met Matt two weeks later, and basically married both of them. You know, not long after that, we became close friends right away and we would, you know, we just started debating ideas and throwing up stuff and ended up working together at DayTran Media, built multiple companies within DayTran Media, you know, together. And when he left, and we did that for about six years together, then he left and started live in 10.1.0, which I won't go into what that does, but asked me to come over, didn't like the original business. We pivoted the business together. Came up with several ideas, sold the pivot through to the board, and then I came on as president. But, you know, we've been together, working closely together and close friends since April of 1999. And I think the reason that we. We get along so well is one, I think our brains operate a little bit alike. You know, we're a little bit different. And so, you know, we're pretty hyperactive. You know, I won't label us, but anyway, we're, you know, we have a lot of energy and we see the world really differently in a lot of times, the same ways. And we see this, kept on identifying the same kind of issues, and we like working on this, you know, certain things together. But there's also just a lot of sheer, you know, just respect, trust in each other. We've never burned each other. We don't talk about each other, you know, like, think, treat each other well as friends. And then we. That. That same energy goes into our business relationship. I see no difference between a business relationship and a. In a relationship with anybody. You know, it's. It's. Treat people very well and treat them like you'd like to be treated. And then when we do debate and we argue, yeah, we'll do that. But we do it respectfully, and it might get heated because we're both passionate. We're both, you know, probably two of the most impatient people, you know, at least within the company, according to some surveys, like we've taken on these personality tests, like we're exceedingly impatient. But it works, you know, because we understand each other, because everybody.

It's because everybody else is too slow. It's not because we're impatient, just because they don't move fast enough.

It's really one of our biggest strengths and one of our biggest weaknesses. Always.

They all. That's so true of all of them.

Right.

So you said something that I liked, and it was that you don't talk shit about each other. And I was speaking with a client recently, and I said that sarcasm doesn't scale, that, you know, when there's two or three in a room, you can be sarcastic with your buddies, but as soon as you start doing it around others, it doesn't scale. Is that just part of your normal DNA that you just like? You can be fun and laugh, but you're good to people?

Yeah, yeah. I'm not very good at. I just. I learned early on that I wasn't very good at it, and I never got any benefit from it. Right. You know, it just. It just doesn't it just doesn't seem to work. I feel like you lean in with love, kindness, respect, you know, have some emotional intelligence and really try to have an open heart and mindset around someone. You just learn so much more.

Yeah.

In that modality than. Than the opposite of that. And I also think it just eventually erodes. Eventually something's going to be said that can't be unsaid.

Yeah.

And that is just the beginning of an erosion of a relationship. And as you pile that on, you know, eventually, maybe when you're younger it's funny or, you know, eventually it gets really tiresome and then it usually kind of is the beginning of the end.

I don't even think it's so funny as younger. We just don't know any better yet. Right. Canadians have a very hard time with it. Canadians are famous for sarcasm. I'm Canadian. And. And it's kind of the. I forget who it was, but they said it's the lowest form of wit and just doesn't scale at all inside of a company. In starting out as friends together, you said something and you said, you know, we're not going to go into what Live Intent did before, but it wasn't really the model you liked. And then you decide to get involved in the model you did like, is that again, speak to kind of your core values or your cultural fit, or was it more the DNA of, like, your skills match the new model better or what was that?

I think that, you know, Matt and I had spent eight years or more very, very deep in the world of email. We had built the largest list management company in North America. You know, we ran esp Email compliance company. Like, we were very. Steven Affiliate network. Like, you know, all this stuff was really centered around email. And so we really do understand that channel and its impact on marketing and advertising and everything else. And so we had been thinking about this idea for like, 10 years. This is not. This didn't. Wasn't like, hey, you know. But when we said, okay, let's come up with some ideas for a pivot, there's a summer. We're like, for three months, just every weekend, we were sitting in his room driving our wives and our new babies crazy because we had to pivot, we had to come up with something. So literally every weekend spending time at LBi in his bedroom and sitting out in the water or at the beach went back to this idea. How do you become the largest email company in the world that doesn't have any email addresses, it doesn't have to send Any email. That would be really cool, right? How do you do that? Right. Because the worst parts of sending email in our perspective is actually being in email was deliverability, getting the email into the inbox, engaging consumers and then having all of that personal identifiable information in your systems that could be hacked. And it's just dangerous. It's just kind of like we really don't want that. And what we came up with, and we had been talking about this before, was we could do ad serving and email so that we never have to send anything. We can let the New York Times send it. And then when someone opens up the New York Times and turns on images, we could do real time decisioning and then place content or advertising or marketing messages in that. And if we got every publisher in like North America doing that, that could be huge. And if we're the only ad server that works in email now we're the dart of 1998. That actually is the first ad server that ever worked on the web. Because before that I started in 1996, we were hard, the world is hard coding ads on websites. There's no ad serving, there's no site ad serving. It's hard coded. So you get every impression like no targeting. Yeah, well they fixed that, you know, back then, but that had never been done in email. And so we were like, we could be the only company with the drill bit that actually gets down into the gold that we want to get. And if we're the only ones there and Apple can't do it and Google can't do it, Verizon can't do it, like that'd be a pretty strong position. Because what we Learned in the 90s is the first mover in ad serving. It's a commodity, it becomes commoditized pretty quickly. So even though competitors come across, you're probably not going to get unseated. Unless you're a jerk, unless you're being bad service and you're raking people over the coals, you're being greedy. So we decided right out of the gate, let's not be greedy, let's provide amazing service, give them no reason to replace us. And that way when competition comes, we're in a really good, strong position to kind of hold the land grab that we just grabbed.

Do you carry that kind of level of strategic thinking, and I'm using the word strategic thinking versus strategic planning carefully. Do you have that kind of thought process around strategy or strategic thinking in the day to day of the business too? Where you.

Yeah, yeah, I think I Think this is more in the nature of, I mean both have to happen. But the strategic thinking, the ideas and the things that come out of reframes and insights that maybe people, other people aren't seeing is more interesting. And it can also be really powerful. The planning is like, you know, you're playing against. The idea has to be solid, it has to be inspiring, it has to make people think and have like a delightful like oh, you know, like that's usually what we're trying to find. We're trying to find new product or something. Because if it has that wow or like factory, I think then it's got a good chance of at least getting the attention of people. But I also, I think a big part of that is where can we actually provide something where it is really hard for anybody else to actually do that? So we don't like bad revenue. Bad revenue is an idea you can implement. You can maybe make a bunch of money but then it's going to erode because a bunch of other people are going to do it. And so if the thinking isn't there and the ideas aren't there, eventually you're going to end up on a treadmill or worse than that.

Totally.

So we really like good revenue which is sustainable revenue that can continue to build and then be as like an annuity.

So in terms of you running the business as kind of the chief business officer and best friend or super close friend to CEO, how, how much time do you build into your calendar or what percentage of your time do you build into your calendar to think and to be strategic versus like in the day to day execution in meetings?

I like how you said built into your calendar. Cause that's exactly what I do. If I have an idea. People know I, but I'm, I'm definitely adhd which means I've got a lot of ideas that are coming in. And so if an idea comes in that I think is, oh, that's really interesting if I think about that idea, you know, two or three times. Well that's because it's actually there's something there because if it's not, I'm going to stop like the waste of time. I don't like to waste my time thinking about things that don't matter. But I'll write it down and I'll put it in my calendar, give myself an hour, give myself a half hour and literally just sat down and then just brain dump and really just go and hyper focus, hyper focus on that idea like anything else in then if I feel like There's a there there. I might do it again and then maybe invite someone, have a debate, call Matt, you know, be like, hey, I've been thinking about this.

I love it.

And then just kind of go off, and then we'll just go off together. And, you know, it's like, is there a there there? What do you think? You know, if there is, then he'll usually be like, all right, go after that.

I like that you actually put it in your calendar and spend the time on it. And then you said that you hyperfocus. It's interesting. So I have 17 of the 18 signs of attention deficit disorder, clinically diagnosed. My ex wife used to joke, saying if I was paying attention during testing, it would have been 18 for 18, but. And then I heard somewhere that I have HD add. I've got the high definition attention deficit disorder. I can't focus, but when I do, it's crystal clear. So I notice I can focus for like 15 to 30 minutes, really tunnel into something. And then I get distracted or bored of my mind's racing or I have to switch places in the company. I got to sit somewhere else, and I got to move around and sit in a different zone, which, I don't know, it feeds my brain in a slightly different way.

It's just like a slight dopamine hit.

Yeah.

That change of space can just be like a little bit of a, you know, I think just a feeder to satisfy the need.

It's a new distraction. I love working out of coffee shops. We live globally now. We were in 23 countries last year. And I'm still building my companies and doing everything I'm doing. And I love to be able to sit. I just wrote my sixth book that comes out next week called the Second in Command, and. And I. I did a lot of that work in coffee shops because I. I had to focus because there's so much distraction that it was amazing. And I got to keep drinking espresso, which is good. I'm sure that the whole, like, time of building the company live intent with Matt has been easy, right?

Yeah, it's been a cakewalk. There's been no issues. And.

Yeah.

12 years of bliss.

Bliss. Yeah. Wedded. Bless. Yeah. So how do you have the. Because I think you mentioned it. The healthy debate, the good debate, and how do you work through the conflict, the natural conflict and frustrations? Can you walk us through some examples?

Yeah, I think that, you know, and also as a group, it's not just, you know, it's definitely not the Matt and Jason show and I'm taking, you know, responsibility for anything other than what I do. And actually I'll give some credit to someone, I'll give credit to our current CEO, who is Brett Pinniger. He was a consultant with Matt and I on our last business daytrain, Media Net Margin, all that stuff. Storm Post was a bunch of businesses within a business. And you know, he would come in and we would work with him either once to sometimes up to four times a year and have him come in and do like full day or two day off sites where we would align. When you're building something from scratch and you're just a lot of iteration, a lot of change and a ton of debate, you know it's going to happen. So just meeting, doing planning, like big planning sessions once a year doesn't cut it. Literally having to do that every quarter. So you keep course correcting over and over and over again. But what Brett did, because he recognized I think right away what he was dealing with, these two power kegs, you know, powder kegs of people that were super impatient. He created like a good framework for us to actually debate in. And so we would crowdsource, we debate, we'd make sure that we'd make sure that the person could, could explain and express what was really happening. And then, you know, if you could actually explain it, then you got it. Like if you can, if you can argue their argument just as well as they can, to some degree, that's fine, that you actually have some idea what they're talking about. You can start to sit in their shoes a little bit. Also not interrupting each other and not biting at each other and being sarcastic and rolling our eyes at each other like, you know, that we were doing a lot of that. We don't naturally do a lot of that, but you get a bunch more people in the room in these planning sessions and there's just certain attitudinal things that don't work, you know, then all of a sudden you're arguing about the way that you're discussing stuff and you're arguing about all the other emotional stuff that's going on instead of actually talking about the real issues. So really also down, if you can strip away some of the crap that's distracting and that heightens emotions, then you can really start to dive in. You get into the real issue and then really dissect it and very much understand it and taking the time to do that. Can't we just make the decision? Well, we can't make this decision if we have non buy in. If we don't have buy in, then we could say this is what we're going to do, but then you're going to run off and do something else. So making sure you have that debate to the point where everyone says, yes, we're gonna do this, and by the way, we're gonna do this. And you know, like, you can't just leave this room and do something else. So then holding each other accountable instead of leaving the room and then someone eroding the thing that we agreed to because they don't agree with it. You do have to align. You do absolutely have to fall in line if you're gonna do something incredible.

Yeah.

And it just slows you down and costs you money if you don't.

I talked about that in my, one of my books called Meetings Suck, where I said when you have the good discussions and the really good debate, when you leave the room, there has to be consensus. You can't walk back to your teams and say, well, we made a decision, but I disagree. It's like, stay in the room and keep, keep working through it.

Right.

So the other thing that when you're kind of operating at the level you're operating at and you're working so closely with the CEO, founder and even other members of the leadership team is having, as you call it, the respectful debate or debating respectfully. Do you have the debate in front of others or do you ever pull away and try to do it privately? And what's your thought process around that? I call it kind of mom and dad arguing, but not in front of the kids.

Oh my God. Yeah. I'd say early on we were terrible.

Terrible at it. Yeah.

Oh my Lord. We were terrible at it. I was laughing and you can see me squirm. Yeah. Not just Matt and I, but, but, you know, as the executive team. Yeah. We had open, open debates and arguments around everybody on a regular basis. We was only 12 people. Like the first, like a few people, 3 and 12 and then 15 and 20. We definitely learned over time to, to, to keep our voices down and maybe put ourselves in an off site and put ourselves in a different place. Even though we love each other, we're, we are going to hear you're, we are going to go at it. Yes. It's kind of the nature of our personalities sometimes we're, I think we're a lot softer now on each other and ourselves and other people. I will say that after knowing each other for 20 years, we're both a lot more secure in who we are. We are a lot more comfortable in our own skin.

Yeah.

You know, and. And. And we've learned so much. And I gotta give credit to Brett. Brett has been like, you know, a life coach and a business coach in a lot of ways. That's really important. Those softer skills really translate to building better culture. You can't build a great culture by ripping into each other and allowing other people to rip into each other, because as soon as they actually realize that that's okay, then all of a sudden you got a bunch of, you know, people around, and then that just starts to really ruin the beauty, you know, of culture and productivity starts to fail and people aren't happy. And if people aren't happy and motivated, doesn't matter how much you pay them, you're not going to thrive.

No. Like, we need to be like, the CEO needs to be that chief energizing officer. Right. And I speak about this in the book the Second Command, that mom and dad are supposed to fight and argue and debate, but not in front of the kids, because it scares out of the kids. Right. The kids don't know that. Oh, like mommy and daddy just actually had sex after they argued, too. Like, they still love each other. Right. They were just passionately debating this thing, you know, not that you and Matt are out there, but. And by the way, now I realize why I know the name Brett Pennegar. Brett was a guest on the Second in Command podcast, episode 123. You're going to be the first company in history to have two guests on the same podcast. So this will be interesting to go out. I'm like, I know the name Brett. I know the name Brett Pinniger. So I literally pick up. I pick up my phone and. And I had to Google it, and there it is. Live intent, episode number one 23.

That's great.

Isn't that crazy? I will link to Brett's episode in this episode, too. We'll cross link the two of them.

Oh, yeah.

It'll be really interesting to get this perspective from inside the organization. So you talk to us about kind of the early stage of what the business genesis was going to be. Is that what Live Intent does now then, is. Are you in that, or is this a completely different business model today?

Yeah, the business, you know, it's evolved greatly. It's expanded a lot. You know, we started as just simply the first and only ad server that could work in email. That was enough right there. And we knew that. New York Times, Wall Street Journal, Washington Post, every major holding company and every major publisher that was sending emails or alerts or like whatever it was, transactional emails, that they had no way of actually serving ads in real time and doing what modern ad serving should do, which is make sure the right ad gets the right person at the right time. And you know, we've been saying that for, for years. It just didn't. So very simply being the first ad server that could actually work and then building an exchange on top of it so we can aggregate all of the inventory from all of the publishers together into a biddable environment, building a DSP and an SSP display side platform and supply side platform that can actually bid into the inventory so that advertisers can access the inventory and then making sure that Google and Verizon and AOL and everybody else could also bid into the inventory. So we get bid density. So on one side you're monetizing email for publishers, on the other side you're actually making it available for advertisers to come in and do advertising and marketing. Right. So those are two sides of our business. And that is still the core of Live Intent.

How did you fund Live Intent?

Matt had raised a really decent amount of money. He learned early on that is a big part of what Matt has always been really good at is raising money. So he had raised a decent amount of money for live intent 1.0. They spent about half of it and just could not find the market a revenue model that would actually work. So when he asked me to come over, I was like, dude, we're both going to go down with the same ship. I was like, that's not going to work. Like, I don't try to explain how this makes money. He's like, I can't. He's like, try. And he was. And I was like, there's no market. So anyway. But then we, we came up with the idea, came up with three ideas and they took this one because they looked at a background like you two and Mel. That makes sense. It's like chocolate and peanut butter. That just totally makes sense. You two should go do this. They were very happy to be like, yeah, this is what you're born to do.

Why does chocolate, like, I love chocolate peanut butter, but like, it really doesn't make any sense going back that far or did it because it's so good. But like an Australian would think we're weird, right? Because they hate peanut butter. They must think it like, it's like peanut butter and Vegemite. I don't know.

They secretly like peanut Butter. They don't want us to know because they don't want us to think.

And by the way, I did pay attention to everything you said about the business bottle, but chocolate and peanut butter is like squirrel.

Right, I know.

It leads into a question, though. And how many employees does Live Intent have now?

I think we're at 270 right now.

Okay. So right around there, you're at a size of an organization where, you know, there's some politics and you've got like strong leaders and good funding. You've also got a lot of people with ideas and opinions. But you talk about focus. How do you say no to people that you like and respect? But maybe the idea is not now or it is definitely a no.

Well, I think that you just brought up the right number. One way of actually saying no is timing. I would say that, that it's one of our biggest challenges was either Matt and I coming up with ideas or somebody else coming up with an idea and then discovering that it's too early or building it and then realizing you built it and no one's coming because it's too early. That is, that's, that's the most painful or one of the most painful things in our work experience. Is that. So, yeah, we're super protective now of running at something, creating a minimal viable product. If we think the timing is wrong, if we don't think we have the right resources to do it right, if we think it's bad revenue, I mean, we're going to build this thing. Yeah, we could actually make another millions of dollars. But then there's no defense of it. Someone else is going to start doing it, it's going to maybe erode and then we're going to have to make up for that revenue. So there's a lot of pieces that I think go into it, but we do spend a lot of time in planning and we do it with cross functional teams. We do it through the wisdom of the crowd because you never know, introduce these ideas. When it gets to the point we do bring it to cross functional groups and say, all right, let's talk through this and let's really prioritize. Is this really what you want? Is this really what we needed to do? And can we build it? How much does it cost? You know, how much engineering is it going to take? That's so hard to get engineering and resources. So we do, we're very, very, I think, measured. And then by the time we were done with the conversation, usually the person that had the idea one isn't married to the idea. They're just married to coming up with ideas because we need ideas to build on. And so learning to actually let go of your own ideas, but then following the data, not opinion. If you're using data and analysis to come up with a yes, you know, why a yes or no then? It's not a personal thing. I don't like your idea. Yeah, I think your opinion is off.

That's the old Google adage, right? I don't really care what your idea is or what your opinion is. What's the data say? I'm sure they say it in a nicer way than that. I never say things properly. It's strange that I've ever been able to write a book so I can barely speak English. It's weird that I would ever write in English. How did you and Matt in the early days kind of divide and conquer, who was going to handle what? And then as you scaled up and built out a leadership team, how do you continue to divide and conquer and decide who gets to do what?

Early on, my focus was around building out the sales team, building out the sales development function, you know, for the team, then building out the account management. Because early on there's no accounts. Because first off, we started with nothing, literally nothing. So trying to bring in supply and demand so that you can actually build the system to start off with, that was really hard. And so big part of my focus is actually bringing in the supply, bringing in the demand, coming up with the process by which we do that, who are we actually going to go after? And then I spend a lot of time with customers and always have. So I spend a lot of time working with customers. You know, it's usually, you know, on the edge of new things that we're doing. And it's not like I'm getting deep into the core, but when as we're building new stuff, in the beginning it was all new stuff is actually just being very close to the end customer and the prospect and then iterating and helping feed information into product. Matt spends more time and always has on product engineering, the building, the architecture, and then also just, you know, he is a wealth of ideas. Like Matt, even more than me, definitely. He never stops. He never stops iterating. This idea is always spinning off, just constantly spinning off. Even in things that we've already built or that we're building before it's even built, there's new ideas coming out of it now. That's a blessing and a curse when we can't Muck with it. We probably shouldn't be mucking with it anymore. We just make sure that Matt's focused on something else.

How do you decide when the customer feedback that we're getting. If the software could only do X, I'd be happy. Or if the software could only do Y, I would, I'd purchase. How do you know when that is true versus how to handle objections better and just get them to buy what we've got.

So one, we tend, I think most everybody in the company only sells what we have. We try not to divulge what we're building sometimes, especially early on, because we don't want people to talk about it. Yeah, I'm the worst offender, but it's also my job. For instance, if one customer has an idea and I can't find five or 10 other people that are actually, oh, dude, that's a really interesting idea. I'm not going to build it. There's no way. And early on, it's so alluring. We had a huge top two telecom company. Early on. It's like we started building Live Intent. We need this. And we had to decide early on. It's like, are we going to build that? Are we not going to build that? That's not core. And we did it a couple times because it was 70% of our revenue.

Yeah.

And then we stopped. So we said no. And this is one of our tenants saying no to get to yes. Say no to say yes. We do that all the time. We lost the client. I actually fired the client personally. Said, sorry, we can't do that.

Oh, I know.

Well, then we're not. I'm like, I'm aware you're going to walk away from us. I'm so and so. And we are. I was like, it doesn't really matter. We're not going to build that and we're not going to condone that, this kind of behavior because honestly, there's some, some real legal issues around. We're not going to do something that we think is going to potentially put us in danger right out of the gate. We're not going to do it. And so I think that's really important. You got to stick to your guns.

I used to coach a top tier cell phone provider, coach the CEO and the second command at sprint for 18 months. Was that your potential client?

I wouldn't tell you if it was.

They're both gone anyway. Like, Marcelo Claret is no longer there and Jamie Jones, who is there, seem like he's no longer there. But they sold The T Mobile. But that's what I'm talking about is these companies that seem so alluring with so many big ideas. Often it feels like these executives are just pushing paper and projects to stay busy versus having any intent of ever getting it to the finish line. How do you know if it's going to get to that finish line?

Well, I think you have to first step. You have a deep, deep purpose of building it in the first place. And the only thing worth building is something that's definitely defensive or that you can defend, but also is a big artery. It's got to be a big, big artery of opportunity. And it has to be something that can actually generate tens of millions of dollars, not something that's just going to be a little side project. So you have to be able to see something that others aren't seeing and then quickly develop it. And then make sure whatever that is is that it is defensible. And not everybody can do it. In fact, maybe few, very few, if anybody could do it. This stuff is still coming up. I'm. One thing I love about our business is that there's so many things that we can spin out of it. I don't think I'll ever be tired. I do not belong in a company that's not actually entrepreneurial and continuing to build. No, it's time for me to leave.

Yeah. Yeah. You'd be horrible. You and I would be horrible in the corporate world. Like, we would die inside of Sprint. Couple other questions. What was it like giving up the president role? You gave up the president role and moved into a chief business officer role. I'm guessing you were probably like 40 at the time. Like, or.

Yeah, I've had to do that several times. The one thing I've gotten really good is firing myself and replacing myself with somebody else. And it's actually been a something that I've done several times. Even as chief business officer, I'm actually hiring. I'm being hired and fired on a regular basis to build things. I was the chief people officer. I didn't change my title to chief people officer. You know, I've built out. The nice thing about that CBO role is that I'm the hired gun. If there's something that. That, you know, if Matt's like, you know, this has to get done. He's like, oh, hey, Jason, can you go build the people. Org? We're going to go from 75 people to 150 people. I'm like, 150 people? That's terrible. Well, that's Gonna be scary because all sorts of things go wrong at 150. If you read, you know.

Yeah.

Anyway, there's. There's a lot of, you know, the human condition of 150 relationships. Numbers.

Number.

Yeah. And so, yeah, I was like, I actually left kind of the rev Org and left talking to customers and doing sales and doing all the stuff that I'm really proficient at, actually make sure that we weren't in a train wreck a year later. Going from 50 to 150. The same feeling every time. So when I went from president to cbo, it's painful every time because I fall in love with whatever I'm doing. And that is true, you know, but I was a big part of the decisioning because at the time, we're like, okay, there's things that we need to do now as we're thinking about maybe, you know, considering either eventually going public or being acquired. That is not my expertise. It's not something that I'm very good at. But as a very decently large shareholder of the company, what's more important, My ego or solving the problem and actually making sure that I am not the reason why this company is not actually successful and then moving into different things. When I first started doing the idea of building out the culture and the whole process around people and really understanding what that was, I've never read so much in my life, and I had so many amazing people around me, you know, quickly trying to get me up to speed and understanding of what that would take from the whole organization, but it would take for me, and it was scary as hell for a long time. And then I started falling in love with it. I really, really do love change. I like that. I just like what it does, and it's painful every time, but I like the outcome. So I become addicted to it. But then when I had to go back into the rev work and I had to start building out some other stuff, I mourned. I definitely mourned. It was hard. It's okay. It can be painful. But that's usually just all ego. And I worked on killing my ego years ago, so.

Interesting. That's what I was guessing on the way on the age side as well, because I think that's where some of the wisdom comes in. Last couple of questions. What do you think you've had to do over the years to really work on your skills? Like, what skills have you developed or had to work on? Cognizantly?

Patience is probably the single largest thing, is actually kind of holding my tongue and thinking about things a little bit more deeply before I speak. My emotional intelligence has definitely climbed dramatically. I think being older definitely helps. But also I've really worked hard. I've spent so much time, you know, reading, debating, understanding people, understanding how to motivate people. I think early in my career maybe I treated everybody more the same. I treated work people differently than they treated the people I loved. And it got in my way. I think my temper, you know, early on in my career wasn't helping me. And those are the things that I actually worked super, super hard on because I realized early on that it didn't work and it wasn't got my way. And then when I really started becoming softer on people and harder on issues, but was able to keep people more, you know, still accountable, but listening, you know, having more of an open mindset and actually not acting out of an inward mindset and an ego place, that really changed everything. It changed my relations with my son, it changed, it changed my relationship with my wife, with my friends, my co workers, my executive team. That's been the single most difficult journey, but the best journey. Focus on the issue, you know. But sometimes, maybe out of my own insecurities, when I was younger, I was harder on people. It just didn't work. I wasn't getting the outcomes that I actually wanted to try and get and wasn't developing the relationships that I wanted to develop. And so it takes some work.

Imagine that. All right, let's go Back to the 22 year old Jason Oates. You're just kind of getting going in your career. What advice would you give the 22 year old you that you know to be true today, but you wish you'd known back then.

So I think one of the things a 22 year old is have the conversation around what is balance versus not balance, how important is balance? It depends on what you want to accomplish. If you want to build something that's never been built before, there's no balance early on if you're really trying to establish yourself, like working your tail off. So I don't think you just get there through hard work. I think you have to get through the smart work and you have to find ways of actually finding moments where you can be present and moments where you can actually regenerate your energy and finding healthy ways to do that and making sure you take time out of your every single day to do that. But is it really going to be full balance if you're really trying to do something incredible, something extraordinary? I'm not talking about doing this the corporate job where it's all right, this is what you do. You do this, this and this every day. That's different. That's actually pretty Easy to work 9 to 5. If you're an entrepreneur, you're building something or creating something that's never been done before. Just so I would say, you know, it's going to be a little bit lopsided, but in that time where you can be present with yourself and be kind to yourself without relying, say, on alcohol or just something else.

Yeah.

But finding that way where you can have an activity that is presencing for you, there are times where you have to cut some things out and then really fully focus. I would say to somebody, you know, work your tail off, work harder than you've ever worked in your life, but find some way of finding peace so that when you do take a break, you're literally really taking a mental break and you're refueling. Oh, here's the other one. You can work really hard, but sleep. I got that wrong. I didn't sleep enough, and that affected my mood, that affected my memory and my energy.

Yeah.

So sleep. Try to. You know, I would say that's really important.

Love that I think about the balance. Like you're like on a teeter totter in the way, like, you'll never be perfectly flat. Just allow the weaving back and forth a little bit. Right. Like balancing on a surfboard. It's not perfectly flat. You got to kind of enjoy the roles, too, so. Jason Oates, chief business officer for Live Intent, thanks so much for sharing with us on the Second Command podcast.

Thank you so much for having me. I really appreciate it.

But they almost need to teach all their employees to start living within their means, which is something that this generation has forgotten to do. But, you know, the Gen X, maybe not even so much Gen X, but certainly the baby boomers and above, they understood that, like, they had money coming in, they budgeted, they lived within their means, they cut.