On Boards, Culture And The Keys To A Successful Career In Business With Dennis Chookaszian And Becoming A Top-Rated Podcaster With Jeremy Slate

Three main factors contribute to a successful career: competence, attitude, and networking. It is the interplay of these three key components that, when done right, will get you to places in any business. Sharing his wisdom on this with Dr. Diane Hamilton is Dennis Chookaszian, the retired Chairman and CEO of CNA Insurance Companies. Dennis shares some important concepts from his personal philosophies on corporate and personal governance, the “Pick Two” concept, and the “Marble Theory.” He also talks about introducing gender, racial, and thought diversity into public boards, the role of culture in company success, and the power of perception in the workplace.

Podcasting started as a hobby for Jeremy Slate. Now, his Create Your Own Life Podcast, which studies the highest performers in the world, has received many awards, including a top rank in iTunes for the business category. He should have seen it coming when his podcast attracted 10,000 listeners in its first 30 days. How exactly did he make it happen? Listen in as he shares some of his secrets to podcasting success with Dr. Diane Hamilton. If you’re an aspiring podcaster, you might want to listen to this for some valuable tips about niching, building media credibility, podcast planning and production, and podcast promotion.

TTL 759 | Successful Career


I’m glad you joined us because we have Dennis Chookaszian and Jeremy Slate here. Dennis is the retired Chairman and CEO of CNA Insurance Companies and Jeremy is the CEO and Cofounder of Command Your Brand Media. We are going to talk about boards, podcasts, having a meaningful life and having a great career.

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On Boards, Culture And The Keys To A Successful Career In Business With Dennis Chookaszian

I am here with Dennis Chookaszian who is a retired Chairman and Chief Executive Officer of CNA Insurance Companies. During his career, he served as the director on the boards of thirteen publicly traded corporations and 50 private corporations. If I read your bio, we’d be here all day. I want to get into welcoming you to the show, Dennis. You’ve done many interesting things from being a trustee at Northwestern University to a member of the National Board of Boy Scouts of America. You had an impressive background and I can’t wait to chat. Welcome to the show.

Thanks, Diane. It’s a pleasure to meet you.

We chatted a little before the show about all the different things that you are working on. There are many different ways that we can go. I know you teach as I do. It’s interesting to look at some of the work that you’re working on to develop a successful life. You and I both have our own systems. Mine was what inhibits curiosity and determining those factors. You have something you’ve worked on and I want to get into that. Before we do, I would like to get a little more of a background on you. I gave highlights of where you ended up and what some of the boards and things that you’ve done, but can you give us a little background story on what led to that success?

That factors into the two courses that I teach at the University of Chicago. The course is called Corporate Governance, but then part of the course is called Personal Governance where I talk about ways to build a successful life. A quick background on myself, I was a chemical engineer at Northwestern, an MBA at the University of Chicago, Master’s in Economics in the London School of Economics. I’m a CPA. I’ve got a very technical background in both computer systems and finance. My career was built on that. I was in consulting for eight years before I joined CNA. I was in CNA for 27 years. I was a Chief Financial Officer for fifteen years, and then president and chairman, CEO.

After I retired and I started doing what I’m doing now, which is serving on boards and doing a lot of private business things, I’m still very active. A couple of quick things, we all have our own personal philosophies, but the one that drives me and the one that you suggested is something which I teach my class that I call Pick Two. There are three things in everyone’s life. You have your work life, family life and personal life. Your personal life is defined as those things that are of interest to you that are not being done with your family. When I say pick two, the answer is there not enough hours in the day to do all three successfully, so you have to pick two. In my case, I have a lot of strong outside interests that I had when I was younger. I knew I could not have a successful both family-life and work-life if I did them.

I fundamentally gave them up and those are things which I don’t do. The only things I do now and it’s been true since I started working are either things that I’m working on or I’m doing with my family. The one way to make that a little easier is to try to convince your family to do things or personal ideas for you that you like, then you can blend the two but it’s a family activity. In my case, one of them was skiing and another one is golf. With my children, I taught them all to ski and play golf when they were younger. Now we do a lot of skiing and play golf together. That’s a little bit of a blend, but that’s a way of trying to get a little bit of the balance in your life.

The other element of it is how to be successful in life. In being successful in life, I have a little model. There are three keys to success and these three keys to success on the business side of what you do are first, you need a technical competency. Second, you need a specific attitude that I’ll describe and finally, third, you need networking. If you’re going to be successful in a business career, one thing you have to realize and particularly now that there are many intelligent people out there, many people around you that have the training and education that you have. You have to find a way to stand out. Everyone needs some technical competency before they do anything else. The competency could be something like skill in computer programming, financial analysis or a softer skill like ability to deal with people. It could be a negotiating skill.

You have to have something that causes you to stand out to cause you to be identified. It’s not a lot different than in sports. If you played basketball or any sport that you play, there’s going to be something about your athletic performance where people are going to notice that and it’s going to cause them to remember you. You can dunk the basketball or you’ve got an amazing tennis forehand or whatever. You’ve got something that causes you to stand out above the crowd. If you don’t have that, you look like everybody else and you never get noticed. It doesn’t matter what it is, but you have to find some technical competence.

Does it have to be positive? Can you have Charles Barkley’s golf swing?

[bctt tweet=”If you’re going to be successful in a business career, you have to find a way to stand out.” username=””]

You can, but that is not going to be good because you’re not going to think positively about someone. It’s got to be something that stands out on the positive side that people say, “That shows accomplishment.” That gives them the willingness to move you along rather than someone else. The second element of it is the attitude. We all know that you deal with people every day. There are some people, in the morning, you get up, you’re going to go to deal with somebody and sometimes you dread going and meeting with certain people. Other people, you look forward to meeting with. You want to be the person who has that positive attitude that everyone looks forward to meeting with and is always the person that is doing things for others.

How do you do that? We have a thing I call the Marble Theory. It’s that you go to a new job and the first day on the job, they tell you, “Here’s your job. Here’s where you’re going to sit.” They tell you all the things about it and then they give you figuratively a bag of marbles. You say, “What’s this?” That bag of marbles is your score system. You start with a certain number of marbles in the bag. From that time on, you are adding marbles or you are deleting marbles from the bag. When you run out of marbles, you’re fired. It doesn’t matter how smart you are.

How do you end up with marbles being added or deleted from the bag? The way you add marbles to the bag is you’re nice to the administrative people. You always show up early. If there’s a conference call, you’re always on the call 3 or 4 minutes before everyone else and nobody’s waiting for you. You’re always volunteering to do something. If someone comes into your office, you offer them a cup of coffee. There are all these things that you do that are the niceties or the civilities, the way of dealing with people and the way you’d like to be dealt with. Those things add marbles to your bag. What deletes marble from your bag are the opposites. When you do things that are the opposite of that.

The person who is going to be successful is the person with a lot of marbles in the bag. If you get to a point where there’s going to be a choice between two people and they’re equally competent, the one with more marbles is going to win. That’s a very important factor. If you do those first two things, technical competency and attitude, the third thing is the critical factor. That’s networking, because you can’t put your light under a bushel. What you have to do in any circumstance, you have to be always thinking about how you promote yourself from a networking point of view, and not in an offensive way. What you want to do is you want to find how do you take advantage of every opportunity that you have to get your word out there, get your name out there.

I’ve been on 13 public company boards, 70 private company boards, and 20 not-for-profits. I’ve been on 100 boards. The reason for that is I’m constantly letting people know I’d like to do that. They’ve seen what I’ve done in other places. If my attitude is the positive one and they like me, then I get selected to be on those boards. I’m always networking and that’s a critical factor. The key to success is those three things. Find your technical competency, have an attitude that makes you a person that everybody wants to be with, and finally network. If you do those things, you will have a successful career.

Those are all great tips. As you’re talking about being on boards, I’ve had a lot of people on the show talk about women on boards and how do you become a board of directors. I serve on a lot of board of advisors and committees. I’ve talked to a lot of people about this, and I know they’re trying to get more women on boards. In California, they had their law and all the things that they’ve put into effect. A lot of times, I agree the networking is critical, but how do we get women or others on boards if they haven’t been CEOs in the past or in C-Suite necessarily where you’re trying to get more diverse boards? I’m curious what you think about that.

The issue of diversity on boards is not just women, it’s also racial diversity. Why do you want diversity? What you want is a diversity of thought. You want people who come from a different background. If everybody comes from the same background, you don’t need a board, you need one person and that person has the background. I will tell you from all of my experience having served on 100 boards, factually, I can point to case after case where not every time, but women bring a different perspective than men that’s exceedingly valuable in a board situation. Someone who grows up with a different racial identity than the norm in this country is also going to bring a perspective that’s exceedingly valuable in this decision making.

It’s going to be different in different elements of it, but there’s no question that that brings a lot of value. It’s a critical factor. That’s something I identified when I was at the very early part of my career as something that needed to happen. When I went to work for CNA, the company that I eventually became the CEO, I went in as the Chief Financial Officer in 1975. At that time, we had 100 officers in the company and there was only one woman. This is the insurance industry which was white males. That’s the way it was structured. We had one woman and at that time, we had no African-Americans. There were very few Hispanics and people of Asian descent in the company. It wasn’t there. It was a white male organization at the top.

When you went down the organization, the organization was more than half female because females did the work in the company. They had good jobs but they weren’t in the senior management rank. I made it a goal to try to change that. By the time I left CNA, 25 years later, 50% of our officers were women. I was the CEO. I had three major people reporting to me that ran the businesses. Two of them were women and one was a man. Our African-American account moved up to 8%, which was still lower where I wanted it to be in the officer group. It was an improvement, but it wasn’t as strong as I wanted to be. We did make our goal of 50% women in the officer group.

It was something you can do something about. Depending on whose numbers you want to believe, but the number of women on public boards has hovered between 15% and 20% for the last twenty years, in spite of people saying they wanted to increase women on boards. There’s a reason for that. There is also a solution to it. Having served on many board selection committees, here’s how it works and particularly now. Let’s take public companies. Private companies are a different story. In a public company setting after Sarbanes-Oxley, it’s no longer true that the way you get on the board is you play golf with the CEO. If you go back to 1990, I called the boards of directors the old white boys club because they were all old white males.

TTL 759 | Successful Career
Successful Career: If you get to a point where there’s going to be a choice between two people and they’re equally competent, the one with more marbles is going to win.


How did you get on the board? You played golf with the CEO. That’s how you did it because the CEO wanted somebody on the board that was going to support them. You wouldn’t put somebody who’s going to be your antagonist on the board. When Sarbanes-Oxley occurred back in 2002, by law you were required to have consideration of the board membership done through a nominating governance committee and the CEO’s influence was substantially diminished. It didn’t happen on one day. It happened as it evolved. As it evolved, the CEO’s influence no longer selects the board members. More than likely in a board situation now, you’ll say to yourself, “We’re going to bring someone in. What are the characteristics?” First, you list the characteristics you want for a board member. What’s on top of most boards list? A former CEO.

What else is on the list? It might be a financial skill, technical skill, industry, regulatory, marketing, internet. There are other skills. You list them. Also, on the list is diversity. When you look at that, you’re going to give that list to the recruiting firms. Usually, the way you get candidates is there are four major firms that do most of the board search and then there are others that supported as well. Those four are the dominant ones. They know them well. If you give them a list of candidates, they’re going to come back to a list of qualifications. They’ll come back to you with ten candidates. What are you going to get? You’re going to get 8 white men, 1 African-American, and 1 woman.

When you select from them, they’ll all be equally qualified in some more than others. What’s the probability that you’re going to select the woman or the African-American person? They’re 1 in 10. Maybe, they get selected a little more than that. Maybe they’re selected 15% of the time. When you do that, what happens? You never change the composition. It stays where it is. The reason for that, some people say, “There are not enough qualified women or African-Americans.” That’s complete nonsense. I have been on board after board. I have no problem finding qualified women and minorities, not just African-Americans, but also Hispanic and Asian.

However, the problem is there are way more white men. The supply of white men is large compared to the supply of minorities and women for that position because women hadn’t risen yet through the ranks of the vice president level and so forth to fit that qualification level. When they search, they do find more white men than women or minorities. You get the wrong balance. What I say to my boards when I’m on the board and they develop the criteria, “Take diversity off the list. It’s not an objective.” They’ll say, “Diversity is very important. We want that on the list.” I said, “No, it’s not because if it was important to you, you would take everything else off the list and have only diversity.” They said, “What do you mean?”

I said, “When we go to the recruiting firms, tell them to do not give us a candidate unless they’re diverse. I want to get a list of ten diverse candidates, women and minorities. If you give me a white man, he’s not going to be selected for the board. Don’t give me a list with a white man. If you don’t do that, you will never change the composition. It’ll stay 15%.” You have to decide what’s your objective because if you ask for a broad list and say best athlete, you’re never going to get a change in the composition of the board. It won’t happen. That’s why it stayed where it is. On the boards that I’ve done this, I say this very forcefully, I’ve gotten a number of my boards to be able to do that and take action and we’ve made a change in the composition percentage on those boards by doing that. The way we did it is by saying we’re going to only bring on a diverse candidate.

How about diversity of knowledge? I hear a lot of focus on CFOs and maybe technology people, but what about cultural experts? What about people who are HR experts? We know everybody’s hired for their knowledge and fired for their behavior. We aren’t focusing on behaviors. That’s where everybody’s losing money with the Gallup poll showing $500 billion a year loss in engagement and all that. Are board members talking about those issues? Do you need cultural experts on the board?

I’ve had this discussion many times. You have to break your question down into two parts. Is culture important? Does that make a difference in the success of the company? My answer to that is absolutely, yes. It’s critical. You must attempt to develop the right culture and it starts the tone at the top. It starts with the board and the CEO. The question is, do you need experts at the board level? I’d argue that the answer to that is no because the board can only do one thing, which is to set the tone at the top and set the structure. It’s the management team that has to implement the culture, and you need your experts a level down. You don’t need them at the board level.

A board level knowing a lot about HR or whatever is of no value. What is he going to do at the board level? He never hires anybody. He never has any impact on it. What my dictum is, which is how you run a board, the role of the board is very simple. It should be noses in, fingers out. The fingers out part is the reason why you don’t want some culture expert on the board because they’re not going to do anything that knowledge. They can’t. They go to a board meeting 5 or 6 times a year. They’re there for 3 or 4 hours. What are they going to do?

What you want on the board is people who will have these noses in, know what’s going on, set the tone for the company as a whole, and understand that you’re going to set the right culture, the right ethical challenges. You don’t need to be an expert to do that. That’s something that any CEO, CFO and anyone who’s had a marketing knows. You don’t need that skill at the top level. That’s already embedded in everybody that you bring onto the board, hopefully. Where you need that skill of how you build culture and programs is in the company reporting to the CEO. That’s where that role needs to exist.

[bctt tweet=”Perceptions may be subjective, but they are powerful. If you strive to do something, you have to consider what the world thinks of it.” username=””]

You teach some of the things we’re talking about in your courses. I was looking at your background and some of what you teach. We talked a little bit before the show that you also focus on wealth and life status. Is that something that’s in your courses? I’m curious if you’re speaking to groups outside of universities as a speaker often. What is your main focus?

I teach the two courses at the University of Chicago. I have up until December 2020. I teach at two universities in China. I’m in China 2 or 3 times a year teaching at a Chinese University. I’m teaching CEOs of Chinese companies how to apply modern management techniques. I also do a lot of public speaking. I probably do 20 or 30 speeches a year on various topics or seminars that I teach. I do quite a bit of that. I have one element in my course at the University of Chicago. It’s a 10-week and 3 hours a week, and 2 hours and 45 minutes of each course is Corporate Governance. It’s how you run companies, Sarbanes-Oxley, legal standards, marketing, all of those issues. The last fifteen minutes of each class is called Personal Governance. It’s how to lead your life. One of them is the Marble Theory that I discussed, then Pick Two, and one of them is relationships with your significant other. I have a number of things like that. I teach them in that element of the course.

You’ve talked about the Marble Theory. I was wondering if you thought that any of the marbles were subjective or are those all?

Absolutely, and it’s going to be different in different places. One example would be appearance. I’ll give you one that’s very subjective. In the US for example, if you look at who is the senior leaders of companies and the senior presidents, as a general statement, senior leaders do not have facial hair. If you look at the presidents of the United States, in 1800, every president had big facial hair. By the time you got to 1900, facial hair went out of style for the presidents. There hasn’t been a president with a mustache or beard in the last 75 or 100 years. The reason for that is it’s not in style. It doesn’t appear presidential. As a consequence, it’s not there. In the CEO’s of companies, generally speaking, facial hair has not been one of the elements.

If you strive to do something, you want to try to consider what the world thinks of that. I don’t care at all about facial hair one way or the other. It’s the same thing for women. If you look at women in their dress, because a woman has an ability to dress more modestly and more businesslike, or more like she’s going to a party. If you look at the women who are in the senior leadership roles, you never see them dressed in clothing that makes it look like they’re going to a party, flamboyantly or in an immodest fashion. Women who are in leadership roles understand that you need to dress for the part. Is that a subjective thing? You bet. The people in those positions are like that. If you want to be one of those, why do you want to try to be something different? It’s because you’re going to stand out in the wrong way.

You bring up an interesting point because my next book is coming out soon as about perception in the workplace and how every culture looks at things in different ways. A lot of this is some of the stuff you talk about. As a woman speaker, it’s challenging to get up on stage and not have somebody analyze what we wear so much more than the men. Even if the things like to the knee and the right length, you’re still going, “Is it too tight? Is it the wrong color? Is it the shoes?” Nobody is doing that to men. Do you think that that’s something that’s ever going to change?

I have a very strong opinion on this. The answer is it’s genetic. This is in your genes. This is male versus female. That’s not going to change. When a person walks into the room, if a man sees a woman walk in and a man walks in, most men can’t tell you what the man even had on, but the man will notice the way the woman is dressed and her appearance. They will notice her because they’re genetic. It’s built into their DNA.

What about women noticing other women?

Women will do the same thing. When women walk into a room, they notice other women, they notice what they have on. When I go out with my wife, she can tell you whether a woman wore that same dress five years ago. Women examine other women carefully and less so for men. That’s the way it is. That’s not going to change.

Don’t you think that we need to get over that the women are hard on each other sometimes? It puts an extra bit of pressure on women speakers that maybe I’d like to see changed to some extent, but you’re saying it’s probably won’t.

TTL 759 | Successful Career
Successful Career: You want diversity because you need diversity of thought. If everybody comes from the same background, you don’t need a board, you need one person.


I’d like to see change also. I’d also like to make sure that it never rains on a day when I’m on a golf course. It isn’t going to change. When you look at someone if you’re a woman, you understand that it’s part of being a woman. People are going to notice your appearance. If you’re a man, they’re not going to notice it so much. That’s the way it is. Since that’s the way it is for women, the answer is to use that to your advantage. Dress in a powerful way because for a woman, for example, if it’s in a corporate setting like a public company, a woman should be wearing either a pantsuit or an appropriate length dress, not tight, not revealing. When she comes in, she will be perceived in a more powerful way. If she comes in provocative clothing, that’s the only thing that registers on people.

It’s an interesting difference that I’ve seen changing a little bit in different generations that they don’t focus on that. Even when I go to companies like Apple where everybody’s younger, the guys are wearing beards on their faces now.

You make an important point there. In some companies, a beard is a sign of importance of status or it’s good to have like at Apple. In the tech industry, having a beard is fine. Not only fine, it’s positively thought of as attractive. I also teach in the University of India. In India, I would say that almost all of the leaders have at least a mustache and some have a full beard.

It is a different look that we’re seeing. I came from a time when it was super formal Mad Men days. It’s interesting to go to offices and people are wearing Lululemon to work. I don’t miss the business casual, which again was easier for men than women because they could wear what they used to wear, those Docker pants. We ended up still having to wear dresses, which were as equally as uncomfortable because they didn’t have a female equivalent. It’s interesting to look at how the world has changed.

Looking at your background, you’ve been in the industries and things that are similar to things I’ve been in. I was in banking and sales related areas since the ‘80s. It has a lot of changes that we’ve seen throughout those years. I thought it would be interesting to focus on the things that we did because you’ve had an amazing career, and you do many wonderful things. I appreciate you being on the show. A lot of people would probably like to know how to follow you in case they want you to come to speak or they want to take your course. Can you share how people could find you?

You can find me on LinkedIn and it’s my name Dennis Chookaszian. I do public speaking. I do a number of things over the years. I do a lot of writing and I distributed to controlled distribution lists, but I don’t have a blog that I’m publishing.

You’ve got so much background, anybody that’s looking for board member information, looking at what you’ve come up with is amazing. You’ve worked with many great groups like the Boy Scouts of America and all the things that you are members of, Director of Nortwestern Memorial Foundation, and President of the Foundation for Health Enhancement. This is impressive stuff. I appreciate you being on the show, Dennis, this was so much fun.

Thanks, Diane. I appreciate it. I enjoyed talking with you and your audience.

Becoming A Top-Rated Podcaster With Jeremy Slate

I am here with Jeremy Slate who is the Founder of the Create Your Own Life Podcast, which studies the highest performers in the world. He studied Literature at Oxford University. He has received many awards as Number One Ranking in iTunes for the business category for his podcast. He was one of the Top 26 Podcasts For Entrepreneurs To Listen To in 2017 and 2018 by CIO Magazine and Inc. All of them are following his work. I’m excited because a lot of people are interested in creating their own podcasts. It’s nice to have you here, Jeremy.

[bctt tweet=”There is no such thing as magic internet money.” username=””]

Thank you for having me, Dr. Diane. I’m stoked to hang out with you.

Please call me Dianne.

My mother-in-law’s a chiropractor and I feel people that have earned to get that title deserve it. I always like to try and give people credit where it’s due.

It’s respectful and a lot of people always ask me that, but I’m like, “I’ll answer to anything, but Diane’s fine.” You have a successful podcast and your website is appealing for people who want to know how to do this, to watch and listen to some of your old podcast. There are amazing people on your show. I’ve had a lot of billionaires and fascinating people on my show as well. A lot of people ask me so many questions, “How do you do a podcast? How do you get those kinds of people? How do you become highly rated?” There’s a lot of things I want to talk to you about, but I want to get to the point where this is what you’ve done in your life. What led up to this? Can you give me your backstory?

It’s like a Beatles song. It’s a long and winding road. I have my undergrad degree and a double major in Catholic Theology and Torah. I studied at New College, Oxford in Literature and then I came back and did my Master’s in Early Roman Empire and Propaganda. It’s not an applicable skill in the world of getting a job. I loved ancient history. I was very interested in how the Roman emperor convinced people he was God. I went down a very interesting path studying that. When I came back, it was 2011 and that was a weird job market. Especially that I had a Master’s degree, I was overqualified for a lot of things, but under-qualified to be a college professor, which is what I wanted to do.

I ended up getting a job painting houses during the day because I’ve worked as a house painter as a teenager, and then managing a gym at night. I was working about 16 to 17 hours a day busting my butt hoping I could find a job at some point in time. I happened to run into a priest friend of my family. I live in New Jersey and at a private school, you don’t need a teaching certificate to order to do that. They got me an interview and I ended up teaching at a private school. It was rough since I didn’t have any classroom management skills. It was like, “Here are 40 kids, here’s you. Good luck. I hope you survive.”

I wasn’t a very happy person early into that journey. In 2012, my mom ended up having a bad stroke and it made me look at a lot of different things in my life and what I was doing and made me decide like, “Do I want to keep doing this?” I had made a decision that I was going to find something different, but I wasn’t looking. It took about a year until my wife was presented with a network marketing opportunity, which I didn’t know what that was. I saw this presentation and I’m like, “I’m going to be a millionaire next week. This is going to be incredible.” It didn’t work like that, but I then went from there to selling life insurance.

I sold products on Amazon and left my product for $1 promo code on my listing. I lost all of them in about 20 minutes to one address in Maryland to someone was much smarter than me. I ended up giving up my entrepreneurial dreams from there. I taught myself how to build websites from YouTube videos and reading some blog posts. I worked at a friend’s marketing firm. While I was doing that, I started a podcast as a hobby because I’d been a listener since 2006 and I enjoyed podcasts. I started a podcast, it took off, we had 10,000 listeners in our first 30 days and that led us to everything we’re doing now.

That’s quite a bit of listener. How did you do that in 30 days?

A lot of boots on the ground work. I approached it not knowing much about online marketing. I had built a small email list. I had about 700 people on it and I had reached out to some of those people and I knew the main metric was getting people to subscribe and review the show. Subscribes are much higher weighted than reviews, but reviews are good for social proof and they have a little bit of effect in ranking in Apple Podcasts. I mailed to that list. I texted everyone on my phone, I called everyone on my phone. I was grabbing friends’ phones when we are out with friends or out at a bar or whatever it may be. I reached out to people on LinkedIn and that was before I knew what automation was. I wrote a couple of thousand messages by hand, which is a little crazy. I got about 60 something reviews in my first week of doing it. We had a good first week listening. That was when iTunes New and Noteworthy was still open. It froze for about two years after that, but I hit New and Noteworthy. We got promoted for about eight weeks and that helped us with that first month of a great launch.

TTL 759 | Successful Career
Successful Career: Subscribes are much higher weighted than reviews, but reviews are good for social proof and they have a little bit of effect in ranking.


It’s interesting how to start off a podcast if you have certain things. I was fortunate to be interviewing billionaire like Ken Fisher and people that I worked with as a professor, and had connections to some interesting people to have on my show. A lot of people, when they’re starting their podcasts, they don’t have those kinds of connections. Maybe they don’t have the mailing list that you mentioned you already had or have your connections. They want to get this monetized right off the bat. It’s a lot harder than you think to monetize a podcast. Do you want to address what the challenges are with that?

I think people have this false idea about it as well. They see what Joe Rogan’s done. They see me Entrepreneur on Fire. They see a lot of these big shows. I feel like it’s anything internet-based. People think there’s this thing called magical internet money and it doesn’t exist. What people need to look at a podcast for is the incredible networking tool it can be. You and I are sitting here chatting and the reason we connected is about a podcast. It’s an incredible networking tool. At the same time, it’s a credible branding and positioning tool as well, which has been pretty awesome that I’ve been able to raise my own awareness and my space. I didn’t start with a business, but I built a business out of that because people started asking me, “Can you help me with this?” I recommend to people like, “If you’re going to start a podcast, it should promote something else you’re doing.” It shouldn’t be looked at as a monetization vehicle right off the bat. It should be promoting something else you’re doing, creating opportunities and also, new business for you.

I had John Lee Dumas on the show and others like him. He’s from Entrepreneur on Fire that you mentioned. It’s fun to see what people have done in this space to get noticed. It is a challenge to recognize what you’re doing. For me, I want to interview people who I find interesting. I see a lot of people who have a focus on how this can be their next big paycheck for something or other. If you’re looking to be at the level of John Lee Dumas, it takes years sometimes to get the following and to do the PR and everything. You talk a lot about basics of PR. I want to know what kind of PR you think is helpful for people who have a podcast.

It also depends on where you’re at as well because you have to understand that in order to help yourself, you need to build a media portfolio first. One of the things I always teach people is you need to have a media page on your site and you need to start working with a lot of local media. I say, “Find whatever your small pond is.” For me, it was a small newspaper. It went to every house in the county I live in. I grew up in a small town. Nothing happens there. If I wrote a press release and sent it in, it got printed.

That’s one of the best ways to do it. Start finding out what your small pond is. It may be a small newspaper. I also live in a lake community that has a magazine that goes around. You need to find out what that small pond is and start building some media credibility there. Start building that media page on your site. The interesting thing about a lot of those is since everything’s digital now, there’s a paper version of those, but a lot of them have online versions too, which also hit Google News.

That’s going to be a great way to build a lot of that first press credibility. You can start reaching out to some smaller podcasts, some other types of media and things like that. From there, you can climb the stairs. You start with shows that maybe have less than 20 episodes and less than 20 reviews. As you’re climbing up, you get to maybe shows that have 100 episodes and 50 reviews. It’s there as you continue to build that credibility as you’re going up. Honestly, the thing you always want to do is start with press releases to small local press because it’s going to help you to build some credibility so you’re much more acceptable when you reach out for media features.

When you say press releases, are you talking about newswire type of releases where you’re spending hundreds of dollars or are you talking about pitches to a local media company?

If people don’t know how to write a press release, I would recommend Google and HubSpot press release. They have a good article about it. What you do is you write a press release and you go to these small local newspaper’s dailies, weeklies, or newsletters. You go to their site. Usually, you’re going to have to scroll down to the bottom because it’s not going to be up on the top and you’re going to look for either newsroom, news tips, editor or something like that. You’re going to write that press release to that editor or that newsroom or whoever it may be.

If your pond is small enough, they’re probably going to print it right off the bat if your news story is also newsworthy as well. That means, is there something interesting about what you’re doing? When I hit 50,000 downloads, it’s not a big deal in the world of podcasting but in the world of media, they don’t quite understand that. It sounds interesting. That was newsworthy. That was one of my first podcast-related news articles. That’s a great way to go because a lot of these small locals are going to print stuff without even editing it and even using the title you create as a press release.

[bctt tweet=”A podcast should promote something else you’re doing. It shouldn’t be looked at as a monetization vehicle right off the bat.” username=””]

You’re using podcasts many ways to do other things. A lot of people do that with their podcasts. You talk about building a million-dollar network through podcasting. What kinds of things are you building off of the podcast?

First and foremost, it’s the connections that you’re making off of the podcast. When I started my show, I made a list of 100 people I most admired. I reached out to a lot of those people. The cool thing about that is there maybe business opportunities in terms of they may have a joint venture they’re working on. There may be something in the future you can do together, or now I’m 800 episodes in and I’ve been putting it off for years and I’m finally writing a book.

I’m going to write about a lot about the people that I’ve interviewed and spoken to on the show, and also ask their help in launching it and getting it out there and helping it get to a bestseller status. You want to see how a lot of these people that you’re talking to can not only enhance your own credibility. Meaning, the more people that you speak to that are credible, the more credible you look. At the same time, how can you do business opportunities with them and how can you use it for something long-term? It doesn’t have to be writing a book, but you also want to have some future vision on it with where is this going and what might we do together?

You bring up a lot of things. Dr. Gilda Carle and I talk about media docs videos that we created. We talk about how you get people to follow the show. Not only that but how you get people on the show who you’d like to talk to, who are interesting, and the interactions you have. There’s a lot that goes on behind podcasting that people don’t recognize that takes a lot of time. A lot of people think they’re just going to put a microphone in front of them and it’s going to be easy, and it’s going to show up in the air somewhere. Do you want to speak a little bit about the challenge of what it takes to do it? I don’t know how much of it you do yourself or that you hire other people to do, but there’s a lot of different aspects to it that people don’t even consider.

In the beginning, I did it all myself. Eventually, you figure out what works and you start having some revenue and stuff like that and you can start outsourcing. In my humble opinion, I don’t think you should be putting money towards things that aren’t yet yielding money. I did a lot of the efforts myself in the beginning and that includes the original design work for the show. You need some decent graphics so that you can get that first barrier of entry if people want to even check out your show. You have to do show editing. I had to learn how to use Adobe Audition and Adobe Premiere.

I had to learn about good microphones. I started out with a cheaper one, which is an Audio-Technica, which is under $100. Now, I have a Shure SM7B, which is a studio-quality microphone, but I didn’t start there. I’ve gotten up to higher quality stuff. You have to do a lot of stuff, even scheduling guests. One of the things that I do that a lot of people don’t even consider and I’m sure you do, is I have a running spreadsheet of a content calendar. What are the things that I’m going to have coming out the three days next week and the week after that so I can put in the future episodes there?

I think a lot of podcasters are thinking about, “I need two episodes for next week.” They’re not thinking in the future. You have to put that there if you’re running it as a professional. There are a lot of different things you have to consider in terms of doing that. Editing is not quick and easy a lot of times, unless you’re going straight from conversation to tape, which if there are outtakes, it’s going to be something you got to handle. There’s definitely a lot of work and episodes can take hours to put together if you’re not systemizing and figuring out how to outsource them, once you can find a revenue source.

I like to use templated shells. I use GarageBand a lot if I’m not using Camtasia or some other form to edit things. I don’t cut out a lot of stuff. I had one guy got stopped by the police while we were chatting. I cut that out. If a dog barks or if you’re on mute for a second or whatever it is, it’s not that big a deal to me. I like a real show, but some people want it absolutely perfect. Do you think that makes a big difference?

It’s to a point. I had a guest on one set, it was a great interview. He said “like you know” 86 times and it made it hard to listen to. You have to look at when does things that we may cut hurt the listenability of it and when is that important. Also, at the same time, I interviewed a former baseball player. When I asked the question, I got tongue-tied and it came out weird, and he started laughing. That’s not something I wanted to have in the final cut. You have to look at when does it fit and when does it not fit. Sometimes, it’s fine for the conversation flow and it’s not a big deal. It’s learning what works where and what needs to go.

When I do my shows, when you’re talking about that, it reminds me of what makes me tongue-tied and what I like to do and what I don’t want to do. The hardest part for me is after the show, I do the editing of putting it together into one show. Say two people are on the same show, I combine them at the beginning. I might do an intro later and say who’s going to be on the show that day. That is when there’s nobody on the other end and I have to talk off the top of my head to myself like that. That’s the hardest part for me. Is that hard for you or what’s the hardest?

TTL 759 | Successful Career
Successful Career: Find out what your small pond is and start building some media credibility there.


It was weird at first, but I feel like at some point you get used to it. One of the things that I do as well is I do the same thing you do. I record an intro after and I talk about what we discussed and everything. I do take some notes on what I’m going to talk about. I do have a pretty consistent way that I talk about it. We’ve had the same sponsor for a long time, which has been Audible. I talk about the book I’m recommending. I talk who the guest is and 3 to 5 things you’re going to learn from them. I feel like eventually, you get past that uncomfortableness of it and understand that it does help the show flow. I feel like the listeners get dumped into a conversation and they don’t have those little things. It may not grab their interest as much. They don’t know what to stick around for. You’ve got to understand the bigger purpose and why you’re putting that in there.

How did you get Audible as your sponsor? A lot of people ask me how you get sponsors.

There are a couple of different ways we’ve done it. They’ve done some paid spots with me off and on over the years, which has been great. I’ve found that we’ve made more money by using their affiliate program for podcasters because you get paid per free membership you get away for Audible, which is great. You make $15 for free membership to give away. We give away a lot of memberships. I’m always telling people what book I’m currently reading. The people at Audible are going to let them go grab one if they’re willing to go over and check it out. We’ve done some paid spots for them with a typical CPM, but I’ve found that giving away the book I’m currently reading on audio version has been a much better and more lucrative way to do it.

I do my own affiliate programs from my curiosity research and all the things that I do. I think that affiliate programs are effective. A lot of people have affiliate pages and different things on their sites. When you’re doing a podcast, when you share that, “This is how you can get this,” that’s a great way to do it. You looked a lot about how to grow your business and that’s why you’ve done so well. I noticed you talk a little bit about the future and media and how to become your own media company. I want to touch on that a little bit because a lot of people want to know how to have their own media company.

It’s like you see a lot of the content being created now. It is more story-driven. It’s more about like the companies have a voice. Even Trader Joe’s has a podcast now. It’s giving you an opportunity to have a conversation with people and not be a nameless faceless company anymore. The media you’re creating is now a relationship-building tool and because of the way media is being consumed. Especially there’s a lot more video being consumed now, which has been driven me to even start to do a little bit more. It is definitely a harder media to deliver on. Companies need to be able to create a lot of that stuff in order to start connecting with people in order to start making more of a relationship because brands are finding it harder to compete because they don’t build relationships with people anymore.

They’re big nameless, faceless companies. Since we’ve been driven more towards personal brands, people feeling like they can connect with people online, companies have to create great media, whether it’s a podcast, a YouTube show or a small clip and posts they create for social media. If you want to survive and grow, you have to be creating those pieces now. You have to realize, what does your audience want? Is it meal tips? Is it more education around your products and services? Is it something that’s going to help them in their personal life so when they think of you, they think of those wins they’ve had in their personal life and that’s why they want to do business with you? You need to be thinking about and considering a lot of these things and going more long-term with them. A lot of companies look at it and they’re like, “If month 1 and 2 didn’t make us any money, we are going to cut the program.” You need to realize that that’s the direction where media is going and in order to make it work, it’s more of a long tail thing.

There’s a lot of promotion that’s involved in making sure that podcasts are successful. When this show comes out, everybody’s going to see it on Facebook. They’re going to see it on LinkedIn and all the different sites. How do you promote your podcasts with the different social media sites?

The first thing is understanding what the native content is for each platform. That means the content that does well on that platform. Facebook likes a lot of videos and photos. Instagram loves photos. I haven’t seen my videos do as well anymore. LinkedIn for a long-time loves video. Now, they’re like long-form written content again, which was popular a couple of years ago. For me, I’m writing long-form written content that tells a story. You have to realize that that first three lines on LinkedIn is your place you’re going to hook somebody and get them to read the rest of the post before that “See More” button. I tend to tell a story about the episode or about something I learned in my life and realized that I only have 1,300 characters to do it.

You are skipping lines in between because you want to make it mobile-friendly because most people are reading on their phone. For me, our biggest and most active network, though it’s not the network I have the biggest following on, is LinkedIn. We get a lot of engagement over there. We get a lot of views over there. A lot of likes and comments, and a lot of that drives back to the show. We’re focusing on telling stories in long-form written content, but making sure we keep it to 1,300 characters because that’s where they cut you off. Make sure you have the right hashtag as well because the thing I’ve been finding, and I’m sure you’ve seen this too is now with the way hashtags are going, LinkedIn tells different brands and individuals that are in different areas. It’s like, “This post has a hashtag on it. You should go comment on it.” Because of that, we’re getting conversations with brands that may not have been aware of our content before as well. For me, the biggest opportunity out there right now is LinkedIn.

What are your most popular hashtags for what you talk about on your show?

#Greatness and #Extraordinary are the good ones. A simple podcast interview, honestly, because a lot of people think of it, but there’s a lot of traffic to it. It is a good one as well. I also have one for the show which is #JustCreateYourOwnLife because the thing you want to think of is if people search the hashtag, they can then find all your content. That’s also important to do as well because it was like making an aggregator for yourself.

You can do that on Twitter and the other sites as well. That’s important. I use #DrDianeRadio for different reasons. Sometimes I all use #CuriosityCode. It’s a curiosity-based thing. it’s great to have one that you own that does showcase you. I’m curious, you’ve interviewed many interesting people. Is there any particular interview that stands out or a few people you’ve interviewed that you go, “That was incredible?”

I interviewed Jonathan Goldsmith who you may know is the most interesting man in the world. He did all those commercials and all those memes about him. People have looked at him and they said, “Jonathan, you were successful so late in life,” because he started out as a cowboy actor and then he left Hollywood, and then came back into these commercials. He goes, “I made a whole bunch of money in network marketing. I became a multimillionaire over there and people don’t know about that.” It made me look at that and it’s like people have different definitions of success. Just because we see a certain thing, it doesn’t mean there’s no success there. That’s a big deal as well. I got to interview former CIA Director and Four Star General David Petraeus. That was cool to talk to somebody at that level and learn, how did he find mentorship? How did he operate day-to-day? How to deal with other people? It’s very interesting to see how people at that level operate like.

I learned something from every show. I’m doing three hours of interviews that air a week, which is quite a bit after many years of doing this. It’s a lot of people. You learn something from every interview. It’s great that there are people out there who have done it and who want to share the value of what they’ve gotten from it. I was looking forward to having you on because I know you’ve done so well with yours. A lot of people want to follow you and learn more from you. I was wondering if you had a link to share or something, you’d like for people to know.

If they are interested in learning about the podcast, that’s over at JeremyRyanSlate.com. If they were interested in our conversation about media and they want to figure out how they can start getting on the right podcast, and maybe they’ve even failed at that. I don’t want them to make all the mistakes that I had and take that as long as I did to figure it out. I put together an awesome piece for them called The Seven Reasons You’re Not Getting Featured on Your Favorite Podcast. They can grab that over at CommandYourBrand.com/sevenreasons.

This was fun. I enjoyed our conversation. Thank you for being on the show, Jeremy.

Thank you for having me, Diane. This was awesome.

I’d like to thank both Dennis and Jeremy for being my guest. We get many great guests on the show. If you’ve missed any past episodes, you can catch them at DrDianeHamilton.com. You can find out more about Cracking the Curiosity Code and The Curiosity Code Index, as well as the Perception Power Index. In terms of speaking and writing and everything that I do is on the site. I hope you take some time to check it out. I hope you enjoyed the episode and I hope you join us for the next episode.

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About Dennis Chookaszian

TTL 759 | Successful CareerDennis H Chookaszian is an American businessman and former Chairman and CEO of CNA Insurance. He also served as a director on the board of thirteen publicly traded corporations, and currently serves on the board of the Chicago Mercantile Exchange. He is currently a professor of strategic management at the University of Chicago Booth School of Business.

An Eagle Scout, Chookaszian serves on the BSA National Executive Board, the organization’s governing board.[4] In 2007 he was awarded the Boy Scouts of America’s Silver Buffalo Award for his work with the organization.


About Jeremy Slate

TTL 759 | Successful CareerJeremy Slate is the founder of the Create Your Own Life Podcast, which studies the highest performers in the world. He studied literature at Oxford University, and is a former champion powerlifter turned new media entrepreneur. He specializes in using podcasting and new media to create trust and oping leader status. In iTunes, he was ranked #1 in the business category and ranked #78 in the Top 100.

Jeremy was named one of the top 26 podcast for entrepreneurs to listen to in 2017 + 18 by CIO Magazine, top podcast to listen to by INC Magazine in 2019 and Millennial Influencer to follow in 2018 by Buzzfeed. The Create Your Own Life Podcast has been downloaded over 2.5 million times. He’s also a contributing editor of New Theory Magazine and Grit Daily.

After his success in podcasting, Jeremy and his wife, Brielle, founded Command Your Brand Media to help leaders use the power of podcasts to change the world.

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