Ep. 251 – LiveIntent CBO, Jason Oates

Today’s guest is Jason Oates, speaker, storyteller, coach, founding executive and Chief Business Officer for LiveIntent.

Jason is a brand ambassador focused on pipeline fulfillment for LiveIntent – when he’s not singing 80’s pop hits with the company band Rif.

LiveIntent is a people-based marketing platform reaching over 250 million people monthly as they consume email newsletters sent to over 2,500 publishers and brands. As CBO, Jason is responsible for building new functions within the company to drive sustainable growth, mentor and develop people and contribute to the culture. He is also a thought leader and speaker in the AdTech and Martech community and often speaks at conferences and events such as Cannes, eTail, RampUp, DMA, and Brand Innovators.

Jason started his career in 1996 as the first “Interactive” media planner/buyer at DMB&B. He spent the next 15 years building and leading digital marketing functions for JMCP, Avenue A, IMS, and Datran Media, working on brands like P&G, GM, eHarmony, and Verizon.


In This Conversation, We Discuss:

  • The journey to build LiveIntent from a group of friends who have remained friends through the years.
  • Why Jason believes his emotional intelligence has risen dramatically during his time with the company.
  • The strategies Jason and his CEO Matt Keiser use to navigate the inevitable conflicts and disagreements that arise.
  • The importance of building a supportive company culture to help your people thrive.
  • Why Jason stepped away from his role as President to become Chief Business Officer.



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You are going to love this interview. I had Jason Oates, the Chief Business Officer for LiveIntent on the podcast. He went into some cool areas, fascinating company, and talked about balance, his relationship with the CEO, and how to evaluate ideas internally when a company’s scaling. They’ve got about 275 employees. He got into a lot of stuff around strategy and core values.

He talked about bad revenue, how to have defensible revenue, and how to be a lot harder on the issues and softer on people. There is some great wisdom stuff in there as well. You’re going to love the episode. Interestingly enough, it is only the first company in history to ever have two guests from the same company on. A few years ago, we also had Brett Pinegar, who was the Chief Operating Officer as a guest as well. It is strange that we made this happen. You’re going to love the episode. We’ll see you on the inside. 

Jason, welcome to the show.

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

It was fun to go through some of the initial information that you sent over to us. I’ll ask about what LiveIntent does in a bit, but what I’m most intrigued about is how you and one of your close friends have built this out almost from the get-go and had done other things together. What do you think it is that has allowed you to stay friends through this long journey as well?

I met my wife in April 1999. I met Matt two weeks later and married both of them. Not long after that, we became close friends right away. We started debating ideas and throwing up stuff. We ended up working together at Datran Media. We built multiple companies within Datran Media together. We did that for about six years together, then he left and started LiveIntent 1.0, which I won’t go into what that does.

He asked me to come over. It didn’t like the original business. We pivoted the business together, came up with several ideas, sold the pivot through the board, and then I came on as President. We’ve been working closely together and close friends since April 1999. The reason that we get along so well is our brains operate a little bit alike. We’re a little bit different and we’re pretty hyperactive. I won’t label us.

We have a lot of energy and we see the world differently and a lot of times the same ways. We kept on identifying the same issues. We like working on certain things together. There’s also a lot of sheer respect and trust in each other. We’ve never burned each other. We don’t talk crap about each other. We treat each other well as friends. That same energy goes into our business relationship. I see no difference between a business relationship and a relationship with anybody. Treat people very well and treat them like you’d like to be treated.

When we debate and argue, we’ll do that, but we do it respectfully. It might get heated because we’re both passionate. We are two of the most impatient people at least within the company, according to some surveys that we’ve taken on these personality tests. We’re exceedingly impatient, but it works because we understand each other.

It’s because everybody else is too slow. It’s not because we’re impatient. They don’t move fast enough. 

It’s one of our biggest strengths and weaknesses always.

It’s true of all of them. You said something that I liked. You don’t talk crap about each other. I was speaking with a client and I said that sarcasm doesn’t scale. When there are 2 or 3 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 part of your normal DNA that you can be fun and laugh, but you’re good to people?

I’m not very good at that. I learned early on that I wasn’t very good at it and I never got any benefit from it. It doesn’t seem to work. I feel like you lean in with love, kindness, and respect. You have some emotional intelligence and try to have an open heart and mindset around someone. You learn much more in that modality than the opposite of that. It eventually erodes. Something’s going to be said that can’t be unsaid. That is the beginning of an erosion of a relationship. When you’re younger, it’s funny or but it gets tiresome and then it usually is the beginning of the end.

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

Matt and I spent eight years or more very deep in the world of email. We had built the largest list management company in North America. We ran an ESP compliance company. We were very steeve in the affiliate network. All this stuff was centered around email. We did understand that channel and its impact on marketing, advertising, and everything else. We had been thinking about this idea for many years. This wasn’t like, “Hey,” but when we said, “Let’s come up with some ideas for a pivot,” there was a summer where for three months, sitting in his room, driving our wives and our new babies crazy. We had to been to pivot. We had to come up with something.

Every weekend, I’m spending time with him in his bedroom instead of out in the water at the beach. We went back to this idea, “How did 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 cool. How do you do that?” The worst parts of sending emails, in our perspective, were deliverability, getting the email into the inbox, engaging consumers, and then having all of that personally identifiable information in your systems. That could be hacked. it’s dangerous. We don’t want that. We had been talking about this before. What we came up with was we could do ad serving and emails so that we never have to send anything.

We can let the New York Times send it then when someone opens up the New York Times and turns on images, we could do real-time decisions and then place content, advertising, or marketing messages in that. If we’ve got every publisher in North America doing that, it could be huge. If we’re the only ad server that works in email, now we’re the Dart of 1998 which is the first ad server that ever worked on the web. Before that, I started in 1996. The world was hard coding ads on websites. There’s no ad serving. There’s no site ad serving. It’s hard-coded. You get every impression.

They fixed that back then, but that had never been done in email. We were like, “We could be the only company with the drill bit that gets down into the gold of what we want to get. If we’re the only ones there and Apple, Google, and Verizon can’t do it, that’d be a pretty strong position,” because what we learned in the ‘90s is the first mover in ad serving is a commodity. It becomes commoditized pretty quickly.

Even though the competitors come across, you’re probably not going to get unseated unless you’re a jerk or you’re being bad service. You’re raking people over the coals. You’re being greedy. We decided right out of the gate, “Let’s not be greedy. Let’s provide amazing service. Give them no reason to replace us. That way, when competition comes, we’re in a good, strong position to hold the land grab that we grabbed.”

Do you carry that level of strategic thinking? I’m using the word strategic thinking versus strategic planning carefully. Do you have that thought process around strategy or strategic thinking in the day-to-day of the business?

It’s more of the nature. Both have to happen, but the strategic thinking, the ideas and things that come out of reframing, and insights that maybe other people aren’t seeing are more interesting but they can also be powerful. The idea has to be solid. It has to be inspiring and make people think and have a delightful like, “Oh.” That’s usually where we’re trying to find a new product or something because if it has that wow or holy crap factor, then it’s got a good chance of at least getting the attention of people.

A big part of that is where can we provide something where it is hard for anybody else to do. 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. 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. We like good revenue, which is sustainable revenue that can continue to build and that be as like an annuity.

In terms of you running the business as the Chief Business Officer and best friend or super close friend to the CEO, what percentage of your time do you build into your calendar to think and to be strategic versus in the day-to-day execution in meetings?

I like how you said built into your calendar because that’s exactly what I do. I’m ADHD, which means I’ve got a lot of ideas that are coming in. If an idea comes in and I think, “That’s interesting.” If I think about that idea 2 or 3 times, that’s because there’s something there. If it’s not, I’m going to stop. I don’t like to waste my time thinking about things that don’t matter.

I’ll write it down. I’ll put it on my calendar, give myself one hour, sit down, brain dump, go, and hyperfocus on that idea like anything else. If I feel like there’s a dare there, I might do it again and then maybe invite someone to have a debate. I call Matt and be like, “I’ve been thinking about this,” then we’ll go off together. It’s like, “What do you think?” He’ll usually go after that.

I like that you put it in your calendar, spend time on it, and then hyper-focus. It’s interesting. 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’ve been 18 for 18. I heard somewhere that I have HDADD, I’ve got the High Definition Attention Deficit Disorder. 

I can’t focus, but when I do, it’s crystal clear. I can focus for 15 to 30 minutes, tunnel into something, and then I get distracted or bored, and my mind’s racing, or I have to switch places in the company. I got to sit somewhere else. I got to move around and sit in a different zone, which feeds my brain in a slightly different way.

It’s a slight dopamine hit. That change of space can be a little bit of a feeder to satisfy the need to change the subject.

I love working at 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 I love to be able to sit. I wrote my sixth book called The Second In Command. I did a lot of that work in coffee shops because I had to focus because there were so many distractions. It was amazing and I got to keep drinking espresso, which is good. I’m sure that the whole time of building the company LiveIntent with Matt has been easy.

It’s been a cakewalk. There have been no issues. Many years of bliss.

You mentioned the healthy and good debate. How do you work through natural conflict and frustrations? Can you walk us through some examples?

As a group, it’s not the Matt and Jesse show. I’m going to take responsibility for anything other than what I do. I’ll give some credit to someone. I’ll give good credit to our COO who is Brett Pinegar. He was a consultant with Matt and me on our last business Datran Media, Net Margin, and all that stuff. It was a bunch of businesses within a business. He would come in. We would work with him either once to sometimes up to four times a year and have him come in and do full-day or two-day offsites where we would align.

When you’re building something from scratch, there’s a lot of iteration, change, and debate. It’s going to happen. The meeting, doing planning, and big planning sessions once a year don’t cut it. You have to do that every quarter, you can keep course correcting over and over again. Brett recognized right away what he was dealing with these two power gigs, people that were super impatient. He created a good framework for us to debate in.

We would crowdsource, debate, and make sure that a person could explain and express what was happening. If you could explain it, then you got it. If you can argue their argument as well as they can to some degree, that’s inspiring that you have some idea of what they’re talking about. You can start to sit in their shoes a little bit. Also, not interrupting, biting, being sarcastic, or rolling our eyes at each other. Not 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 are certain attitudinal things that don’t work.

All of a sudden, you’re arguing about the way that you’re discussing stuff and all the other emotional stuff that’s going on instead of talking about the real issues. Also getting down, if you strip away some of the crap that’s distracting and that heightens emotions, then you can start to dive in and get into the real issue, dissect it, and very much understand it. It’s taking the time to do that.

A lot of people are very impatient around, “Can’t we just make the decision?” We can’t make this decision if we have a buy-in. If we don’t have buy-in, then we can say, “This is what we’re going to do,” but then you’re going to run off and do something else. Making sure you have that debate to the point where everyone says, “Yes, that’s it. We’re going to do this.”

You can’t leave this room and do something else. Holding each other accountable instead of leaving the room and then someone eroding the thing that they agreed to because they don’t agree with it. You do have to fall in line if you’re going to do something incredible. It slows you down. It costs you money if you don’t.

SIC 251 | LiveIntent

LiveIntent: You do have to fall in line if you do something incredible, and it just slows you down and costs you money if you don’t.


I talked about that in one of my books called Meetings Suck where I said, “When you have the good discussions and the good debate, when you leave the room, there has to be consensus. You can’t walk back to your teams and say, ‘We made a decision, but I disagree.’ Stay in the room and keep working through it.” The other thing when you’re operating at the level you’re operating at and you’re working closely with the CEO or Founder and even other members of the leadership team is having 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? What’s your thought process around that? I call it Mom and Dad arguing, but not in front of the kids.

We were terrible at it. I was laughing and you can see me squirm. Not just Matt and I, but as the executive team, we had open debates and arguments around everybody on a regular basis. The first was only a few people, 3, and then 12, 15, and 20. We learned over time to keep our voices down and maybe put ourselves in an offsite and in a different place.

Even though we love each other, we are going to go at it. It’s the nature of our personalities sometimes. We’re a lot softer now on each other, ourselves, and other people. After knowing each other for many years, we’re both a lot more secure in who we are. We’re a lot more comfortable in our own skin. We’ve learned so much. I give credit to Brett. He has been a life and business coach in a lot of ways. That’s important.

Those softer skills translate to building a better culture. You can’t build a great culture by ripping into each other and allowing other people to rip into each other. As soon as they realize that’s okay, then all of a sudden, you got a bunch of people around. That starts to ruin the beauty of a culture. Productivity starts to fail and people aren’t happy. If people aren’t happy and motivated, it doesn’t matter how much you pay them. They’re not going to thrive.

The CEO needs to be that Chief Energizing Officer. I speak about this in the book The Second Command. Mom and Dad are supposed to fight and argue and debate, but not in front of the kids because it scares the shit out of the kids. The kids don’t know that Mommy and Daddy had sex after they argued. They still love each other. They were just passionately debating this thing. Not that you and Matt are. I realize why I know the name Brett Pinegar. He was a guest in Episode 123. You’re going to be the first company in history to have two guests on the same show.

What date was that?

It was a few years ago. You talked to us about the early stage of what the business genesis was going to be. Is that what LiveIntent does now then? Are you in that or is this a completely different business model?

The business evolved greatly. It’s expanded a lot. We started as simply the first and only ad server that could work an email. That was enough right there. We knew that the New York Times, Wall Street Journal, Washington Post, every major holding company, and every major publisher that was sending emails, alerts, transactional emails, or whatever it was had no way of 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. We’ve been saying that for years. It didn’t exist.

SIC 251 | LiveIntent

LiveIntent: Make sure the right ad gets the right person at the right time.


Simply being the first ad server that could 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 or Display Side Platform and SSP or Supply-Side Platform that can bid into the inventory so that advertisers can access the inventory and then making sure that Google, Verizon, AOL, and everybody else can also bid into the inventory so we get bid density. On one side, you’re monetizing email for publishers. On the other side, you’re making it available for advertisers to come in and do advertising and marketing. Those are two sides of our business and that is still the core of LiveIntent.

How did you fund LiveIntent?

Matt had raised a decent amount of money. He learned early on. That is a big part of what Matt has always been good at, raising money and managing investors. He had raised a decent amount of money for LiveIntent 1.0. They spent about half of it and could not find the market fit and a revenue model that would work. When he asked me to come over, I was like, “We’re both going to go down with the same ship. That’s not going to work. Try to explain how this makes money.”

He is like, “I can’t.” I was like, “Try.” He was like, “There’s no market.” We came up with three ideas, and they took this one. They looked at the background like, “You two and email? That makes sense.” It’s like chocolate and peanut butter. This totally makes sense. You two should go do this. They were very happy to be like, “This is what you were born to do.”

I love chocolate and peanut butter, but it doesn’t make any sense going back that far, or did it? It’s good. An Australian would think we’re weird because they hate peanut butter. It’s peanut butter and Vegemite.

They secretly like peanut butter. They don’t want us to know.

I did pay attention to everything you said about the business model, but chocolate and peanut butter are like a squirrel.

I know, but those are those mixes where all of a sudden, things work.

It leads to a question. How many employees does LiveIntent have?

We are 270.

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

You brought up it right. The number one way of saying no is timing. One of our biggest challenges was either Matt and I 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. One of the most painful things in our work experience is that.

We’re super protective now of running at something, creating a 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, we’re going to build this thing. We could make another millions of dollars, but then there’s no defense of it. If someone else is going to start doing it, it’s going to maybe erode, then we’re going to have to make up for that revenue.

There are a lot of pieces that go into it. 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. When you introduce these ideas and it gets to the point we do bring it to cross-functional groups and say, “Let’s talk through this. Let’s prioritize. Is this what you want? Is this what we need to do? Can we build it? How much does it cost? How much engineering is it going to take?” It’s hard to get engineering and resources.

We are very measured. By the time we were done with the conversation, usually, the person that had the idea isn’t married to the idea. They’re coming up with ideas because we need ideas to build on. Learning to let go of your own ideas, but then following the data, not opinion. If you’re using data and analysis to come up with why, a yes or no, then it’s not a personal thing, “I don’t like your idea. I think your opinion is off.”

That’s the old Google adage, “I don’t care what your idea is or what your opinion is. What does 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 been able to write a book because I can barely speak English. It’s weird that I would ever write in English. How did you and Matt in the early days 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 on building out the sales team and sales development function for the team, then building out the account management team because early on there are no accounts. First off, we started with nothing. We do nothing. Trying to bring in supply and demand so that you can build the system to start off with was hard. A big part of my focus was bringing in the supply, bringing in the demand, and coming up with the process by which we do that and who are we going to go after.

I spend a lot of time with customers and always have. I spend a lot of time working with customers. It’s usually on the edge of new things that we’re doing. It’s not like I’m getting deep into the core. As we’re building new stuff in the beginning, it’s being very close to the end customer and prospect, and then iterating and helping feed information about the product.

Matt spends more time and always has on product engineering and building the architecture. He has a wealth of ideas. Even more than me, he never stops iterating. His ideas are constantly spinning off, even if things that we’ve already built or that we’re building. Before it’s even built, there are new ideas coming out of it now. That’s a blessing and a curse. We probably shouldn’t be mucking with it anymore. We make sure that Matt’s focused on something else.

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

Almost 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. I’m the worst defender, but it’s also my job. For instance, if 1 customer has an idea and I can’t find 5 or 10 other people that are, “That’s an interesting idea,” I’m not going to build it. There’s no way. Early on, it’s alluring. We had a huge top-two telecom company early on. When we started building LiveIntent, “We need this.”

We had to decide early on, “Are we going to build that or not? That’s not core.” We did it a couple of times because it was 70% of our revenue, then we stopped and said no. This is one of our tenants, saying no to get to yes. We do that all the time. We lost the client. I fired the client personally, “Sorry. We can’t do that.” “I know. We’re not going to do business with you anymore.” “I’m aware.”

“You’re going to walk away from us? I’m so-and-so.” I was like, “It doesn’t matter. We’re not going to build that. We’re not going to condone this behavior because honestly, there are some real legal issues around it. We’re not going to do something that we think could potentially put us in danger right out of the gate.” That’s important. You got to stick to your guns.

SIC 251 | LiveIntent

LiveIntent: We will not do something we think could put us in danger right out of the gate. We will not do it. You need to stick to your guns.


I used to coach a top-tier cell phone provider. I coached the CEO and the Second in Command at Sprint for eighteen months. Was that your potential client?

No, and I wouldn’t tell you if it was.

They’re both gone anyway. Marcelo Claure and Jaime Jones are no longer there. They sold to T-Mobile. What I’m talking about are these companies that seem alluring with many big ideas. Often, it feels like these executives are 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?

First off, you have to have a deep purpose in building it in the first place. The only thing worth building is something that’s defensive or that you can defend, but also is a big artery of opportunity. It has to be something that can generate tens of millions of dollars. That’s something that’s going to be a little side project. You have to be able to see something that others aren’t seeing and then quickly develop it and then make sure it is defensible and not everybody could do it. This stuff is still coming up. One thing I love about our business is that there are many things that we can spin out of it that I don’t think I’ll ever be tired of. I do not belong in a company that’s not entrepreneurial and continuing to build. It’s time for me to leave.

You and I’d be horrible in the corporate world. We would die inside Sprint. A couple of other questions. What was it like giving up the President role and moving into a Chief Business Officer role? You were probably 40 at the time.

I’ve had to do that several times. The one thing I’ve gotten good at is firing myself and replacing myself with somebody else. It’s been something that I’ve done several times. Even as a Chief Business Officer, 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, the Chief People Officer. The nice thing about that CBO role is that I’m a hired gun. If Matt’s like, “This has to get done. Jason, can you go build the people org? We’re going to go from 75 people to 150 people.” I’m like, “That’s terrible. That’s going to be scary because all sorts of things go wrong at 150.”

There’s a lot about the human condition and when you have 150 relationship numbers. I left talking to customers, doing sales, and doing all the stuff that I’m proficient at to make sure that we weren’t in a train wreck one year later going from 50 to 150. It’s the same feeling every time. I went from President to CBO. It’s painful every time because I fall in love with whatever I’m doing. That is true, but I was a big part of the decision because, at the time, we’re like, “There are things that we need to do now as we’re thinking about maybe considering eventually going public or being acquired.”

That is not my expertise. That is not something that I’m very good at. As a very decently large shareholder of the company, what’s more important, my ego or solving the problem and making sure that I am not the reason why this company’s not successful? Moving into different things. When I first started doing the idea of building out the culture and the whole process around people and understanding what that was, I’d never read much in my life. I had many amazing people around me quickly trying to get me up to speed and understanding what that would take. From the whole organization, what it would take for me?

It was scary for a long time then I started falling in love with it. I do love change. I like what it does. It’s painful every time, but I like the outcome so I’ve become addicted to it. When I had to go back into the reward and I had to start building out some other stuff, I mourned. It was hard. I realized it can be painful, but that’s usually all ego. I worked on killing my ego years ago.

That’s why I was guessing on the way, on the age side as well, because 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 work on your skills? What skills have you developed or had to work on cognizably?

Patience is probably the single largest thing that is holding my tongue and thinking about things a little bit more deeply before I speak. My emotional intelligence has climbed dramatically. Being older has helped, but also, I’ve worked hard. I’ve spent so much time reading, debating, understanding people, and how to motivate people. Early in my career, maybe I treated everybody more the same. I treated work people differently than they treated the people I loved. It got in my way. My temper early on in my career wasn’t helping me. Those are the things that I worked super hard on because I realized early on that it didn’t work and it got my way.

SIC 251 | LiveIntent

LiveIntent: Hold your tongue and think more deeply before speaking.


When I started becoming softer on people and harder on issues but was able to keep people more still accountable, listening, and having more of an open mindset. Â and not acting out of an inward mindset and an ego place changed everything. It changed my relationship with my son, wife, friends, coworkers, and executive team. That’s been the single most difficult journey, but the best journey by far.

Did you say harder on people and softer on issues?

Softer on people. That was a big piece of it, focusing on the issue but sometimes, maybe out of my own insecurities, when I was younger, I was harder on people and it didn’t work. I wasn’t getting the outcomes that I wanted to try and get. I wasn’t developing the relationships that I wanted to develop. It took some work.

Let’s go back to the 22-year-old Jason Oates. You’re getting out in your career. What advice would you give the 22-year-old you that you know to be true now, but you wish you’d known back then?

To have the conversation around what is balance versus not balance. How important is the 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. As my son who’s at Brooklyn Tech taking a Double AP course in Physics as a junior in high school, he has no balance. Balance is a wonderful thing to have. I try to balance out doing things and giving breaks, but it is lopsided.

If you’re trying to establish yourself, work your tail off. I don’t think you get there through hard work. You have to get through smart work, and you have to find ways of finding moments where you can be present and moments where you can 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 it going to be full balance if you’re trying to do something incredible, something extraordinary. I’m not talking about doing a corporate job where, “This is what you do. You do this every day.” That’s different. That’s pretty easy to work from 9:00 to 5:00.

You’re an entrepreneur. You’re building something or creating something that’s never been done before. It’s going to be lopsided, but in that time where you can be present with yourself and be kind to yourself without relying, let’s say, on alcohol or something else, but finding that way where you can have an activity that is presenting for you. For instance, I was playing on a semi-pro pool player. I was singing in bands. I quit both those things when I started LiveIntent and I had a baby.

There are times when you have to cut some things out and then fully focus. I would say to somebody, “Work your tail off. Work harder than you’ve ever worked in your life. Find some way of finding peace so that when you do take a break, you’re taking a mental break and you’re refueling.” Here’s the other one, “You can work hard, but sleep.” I got that wrong. I didn’t sleep enough. That affected my mood, memory, and energy. That’s important.

I think about the balance like you are on a teeter-totter in a way. You’ll never be perfectly flat. Allow the weaving back and forth a little bit. Balancing on the surfboard, it’s not perfectly flat. You got to enjoy the roles too. Jason Oates, thank you so much for sharing with us on the show.

Thank you so much for having me. I appreciate it. Have a great day.


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