Deep Dive with Jonathan Shapiro

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This is a podcast episode titled, Deep Dive with Jonathan Shapiro. The summary for this episode is: <p>In today’s deep dive episode, Matt interviews CEO coach and multi-time CEO Jonathan Shapiro. They chat about his career, from bringing comics onto the internet at United Media to becoming a CEO, and then making the move into executive coaching.&nbsp;</p><p>Tune in to hear Jonathan share the lessons he learned about management and good leadership that changed his career. </p>
Jonathan's early career at United Media
03:41 MIN
Transitioning to DoubleClick
05:03 MIN
Privacy and data in 90s and 2000s
05:01 MIN
Becoming CEO of Lillian Vernon
05:09 MIN
Making moves to MediaWiz and PetCare
07:53 MIN
Building the PetCareRx business
07:10 MIN
The importance of coaching and mentorship for CEOs
03:37 MIN

INTRODUCTION: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster. And I'm here today with my friend, Jonathan Shapiro. Jonathan is a CEO coach. He is a former three- time CEO. He has an MBA. He also has a really interesting master's degree in something called applied positive psychology. And Jonathan, among other things, was on my board of directors at Return Path for at least two or three years, kind of in the early days of the business. So Jonathan, it is great to have you here.

Jonathan Shapiro: Thanks, Matt. Great to be here.

Matt Blumberg: So, let's talk a little bit about your career and some of the things you've done along the way. We'll start quickly. Maybe we'll even skip over the first thing you did, which was management consulting at McKinsey.

Jonathan Shapiro: Paid my dues.

Matt Blumberg: I was a management consultant. It feels like you're paying your dues, you're learning a lot.

Jonathan Shapiro: Yep.

Matt Blumberg: But your first internet job, internet 1. 0, which a lot of our guests for these Friday in- deep with interviews were around at the dawn of the internet. Your first one was a little different than a lot of other people. So you worked at United Media. If I remember correctly, your job was to bring Dilbert to the internet.

Jonathan Shapiro: Yes. It was a little broader. It was bring all the comics, the United Media as a distributor of comics and columns represented to the internet. And so, we launched the Dilbert Zone, and snoopy. com, and the Comix Zone in 1995. And in 1996, we had a top 50, according to Yahoo Internet Life, which only us OGs, internet OGs, remember what that is or was. But according to Yahoo Internet Life, the Dilbert Zone was a top 50 news, information and entertainment site back in 1996.

Matt Blumberg: I believe that. I think Dilbert and Moviefone were on that list together.

Jonathan Shapiro: There you go.

Matt Blumberg: So you had no internet experience in 1995, no one did. You were hired, I think you were a BD or a corp dev job at United Media. What was it like trying to figure out the internet? And then how did you get from there to DoubleClick, which is where I met you?

Jonathan Shapiro: Yeah. So it was great figuring it out. It was so exciting. Actually, when I had gone to business school, orientation at business school, you get asked the question, " Okay, what are you going to do?" And back in 1990, coming out of McKinsey and The Media Practice, I saw what I thought was the future, which was the intersection of media and technology. And I thought that was high definition cable. I thought the cable visions of the world were going to own this space, and it was going to ride on their pipes, and all that was going to happen. And being an indentured servant to McKinsey after my business school, I went back to the firm. And as that world was emerging, the media world and the technology world, it became more clear that the internet was the thing. So I get to United Media, and we've got all these assets. And I don't know if you know this, but Kevin Ryan was the CFO at the time.

Matt Blumberg: Right. No, because I remember that because that's how you ended up inaudible.

Jonathan Shapiro: Exactly. So Doug Stern, Kevin Ryan, myself, Benji Burtett, who was an executive there, we're all sitting around going, " Okay, how do we leverage this IP?" And the answer was, " Let's get it on the internet." And I raised my hand and said, " Oh, I want to do that." And they gave me the opportunity. So we built out the Dilbert Zone, the Comix Zone, et cetera.

Matt Blumberg: So you find yourself running a top 50 web property at some point early in your life and early in your career. And United Media, I actually don't even know what... I assume the company is still around. I assume it still does what it does.

Jonathan Shapiro: It does, but in a very different context. It was a division of Scripps- Howard.

Matt Blumberg: Okay. The Scripps inaudible newspaper?

Jonathan Shapiro: Yep. Scripps now really the cable giant. This was funny. HDTV was starting at the same time, this internet effort was starting. And we were so successful at United Media with the internet, they were sending their executives to basically talk to me and the team, " How do you guys do this?" So it was kind of fun.

Matt Blumberg: Right. It's good to be one step ahead of the rest of the class, right?

Jonathan Shapiro: Yeah. Exactly.

Matt Blumberg: All right. So you're in early internet content media. There's this startup in New York called DoubleClick. DoubleClick is trying to figure out what internet advertising's going to look like. So I assume Kevin got there first. The CFO recruited you to join him. How many employees were there when you joined?

Jonathan Shapiro: There were 107 when I joined. But the trajectory was as follows, and it's actually formative to this positive, positive psychology stuff later in my career. So Kevin leaves to join DoubleClick. He's employee number, I think five. And we have a conversation. He says, " You should really consider coming." And I'm like, " Yeah, I'm not so sure." Things were going well at United Media, but we stayed in touch. That was in early'96. By late 1996, we had our hit show. Things were going really well. And in full disclosure, Doug Stern, the CEO, calls me into his office at the end of'96 in December. And he says to me early, " Hey, Jonathan, are you going to be around at the end of the day?" I'm like, " Yeah." " Come see me." And I'm thinking, I'm getting a promotion. And so, I walk into his office and he sits me down and he says, and I've never forgotten it, " Jonathan, you have no constituency." I was like, " Wait, that doesn't sound like a promotion. What does that mean?" I didn't use those words, but I was a little flummox, I'm like, " Excuse me." And he repeated himself and I was still not... It wasn't sinking in. And finally he just says, " Jonathan, no one wants to work with you. You got to go." Now, that was a wake- up call.

Matt Blumberg: Wow. I actually never heard this story before.

Jonathan Shapiro: Yeah. So that was very troubling. Literally I was the leader of the team that was crushing the internet in 1996. Again, Scripps- Howard was sending their internet executives to me and to our team to say, " How do we do this?" But I had a lot of bad leadership practices, I hadn't learned how to be a leader, I hadn't learned what management was like. I was feeling-

Matt Blumberg: Management consulting teaches you a lot of things. It does not teach you that.

Jonathan Shapiro: It does not. And I was suffering from that lack of education. And so, I actually left United Media. McKinsey wanted me back. So I went back to McKinsey and was an internet specialist. This was funny. I'd kind of built a reputation in New York. In fact, Fred Wilson had become a friend because he did the Yo! Yo! Dime deal, which was predicated on the Dilbert property that I helped write due diligence. Anyway, long story. I get to McKinsey, I'm doing internet work. But it's clear that the firm at that point wasn't ready to do the kind of internet stuff at the scale that the internet required. And so, eight months in, I'm having breakfast with Kevin, and he says, " You really should come to DoubleClick." And I thought, okay, I'll go to DoubleClick. Funny little sidebar. I had promised McKinsey two years. Ennius Bergsma, great guy, McKinsey director, who hired me back, said, " Jonathan, the only thing I'm worried about is you're going to leave before the two years is up." And I looked him in the eye and said, " Ennius, I will not do that to you. I am here for two years." Eight months later, I had to walk into his office and say, " I'm really sorry to do this, but I'm going to have to break that promise." And what I did to assuage, basically my guilt was, I worked for McKinsey formally for the next three months, but I wasn't on their payroll. I was on DoubleClick's payroll, and I was moonlighting. During the day, I was at DoubleClick at night. I was finishing up the Bertelsmann online project for McKinsey. So I was doing two jobs, but it worked out.

Matt Blumberg: Yeah. And so, DoubleClick was, I don't know if it's fair to say, invented internet advertising, but certainly was one of a couple of companies that were real pioneers in the network concept internet inaudible.

Jonathan Shapiro: 100%.

Matt Blumberg: You were there a bunch of years. And when I met you, which was kind of middle of your time at DoubleClick, I think, or maybe toward maybe even the back half of it, you had just engineered the acquisition of Abacus.

Jonathan Shapiro: Correct.

Matt Blumberg: Which was an old school catalog data, direct mail, direct marketing company. And I think right after I met you, either you ended up on the front page of the Wall Street Journal or DoubleClick ended up on the front page of the Wall Street Journal, and you were in the article somewhere as destroying people's privacy. So I know you had a couple different roles to DoubleClick, but let's focus on that moment for a minute. So I think today the world of privacy and data is so different than it was back then. And I mean, I always tell people, assume you have no privacy and do the best you can to manage it. That's maybe a little bit of a jaded view. But there's stuff that becomes commonplace over time that people just get used to, that would've been considered ridiculously intrusive 20 years ago, or 23, or 24 years ago

Jonathan Shapiro: And was.

Matt Blumberg: And was at the time. That's right. Because the worst thing that was going to happen to you before that was someone was going to call you at dinner as a telemarketer and irritate you. Or you'd get a catalog in the mail, you didn't quite understand how that catalog got inaudible

Jonathan Shapiro: Yield and streamline.

Matt Blumberg: Right. But what was it like being in the eye of that storm? You said you came out of McKinsey, you didn't have leadership and management training, you certainly didn't have crisis management training.

Jonathan Shapiro: No. Wow. That experience was also very formative. Kevin knew my story from United Media because he'd been there. So I made it a point to learn how to be a good leader and correct the mistakes I was making. Once I got to DoubleClick, I was having some success doing that. When the Abacus thing hit. So I led the effort to buy it. And the thesis behind it was, if you know direct marketing, the best predictor of what you're going to buy in the future is what you have bought in the past. The only better predictor of what you might buy is what you were searching for. And the Google guys had figured that out. So we bought Abacus at DoubleClick because it was-

Matt Blumberg: Google guys hadn't figured it out in 1998 because there were no Google guys.

Jonathan Shapiro: No. By'90, yeah, they were figuring it out in the early 2000s.

Matt Blumberg: Overture had figured it out, or-

Jonathan Shapiro: Yeah, Yahoo. And when we bought Abacus, the thesis was simple. If we could take the data, Abacus was a database of all the transactions from the thousand largest catalogs in the United States. So literally they had, Jonathan bought this T- shirt, this pair of sneakers, and this camping seat from LL being on this date. We figured if we could aggregate the data and we believed that all these catalogs were going online. We believed that all that data would be available in an online context for targeting advertising. We would have the technology of Dart would be supercharged, and it would be a knockout blow for any of our competition. We were very excited about this.

Matt Blumberg: You were probably right.

Jonathan Shapiro: Yeah. I think it was one of the reasons Google bought DoubleClick. It was for the data, because at the time they bought it in 2003, DoubleClick was serving the majority ads on the internet. And if I serve an ad to you at a financial page, or if I serve an ad to you on a catalog site, they tell you different things. So the thesis I thought, and we thought was right, but we immediately ran into the privacy buzz storm. And so, no did not have crisis management tools, but we learned pretty quickly. And I got to say, one of the leadership lessons I learned here was from Kevin O'Connor, one of the founders of DoubleClick, superb guy. I think everyone who was part of DoubleClick with O'Connor around would tell you that they admired him greatly. So one of the things that happened and was just a great leadership lesson was, as we were suffering the slings and arrows in an executive meeting, I said, " I guess I've seen this movie. I know how it goes. Someone's got to die on the sword. I guess you guys have to can me." And O'Connor said in that meeting, " You did not make that decision alone. We made it as an executive team. And no one's fallen on their sword. We're fighting this through." And I was like, " Okay, I will follow you through any brick wall you ask me to run through." And so, leadership lesson, get your teams back, be there for them. That was impressive.

Matt Blumberg: That's huge. Let me ask you to reflect on the business decision there for a second. So in the rearview mirror, knowing that it was inevitable that data was going to be the internet, and the internet was going to be data, and privacy was going to change, or people's perceptions were going to change over time, was that the right thing to do at the right time? Was it too early? Should you have done more?

Jonathan Shapiro: Hard to say. I don't know if the timing was perfect. So I'm not sure if we got it at the right time. If we'd waited, we might not have been able to get the asset. But I think we could have done a couple of things much better. One was we could have acknowledged what was likely going to be a problem and prepared better. And two, I think we could have gone deeper, not only just providing, just riding along all these catalog sites, but being there for them with an analytics tool and maybe a Shopify kind of equivalent, so that we were deeply embedded in their platform, which would've given us a more natural way to access and leverage the data on their behalf, which is what the Abacus Co- op was about.

Matt Blumberg: All right. So you leave DoubleClick and you then started a run of being CEO at three different companies in three different spaces. Lillian Vernon, sort of old school cataloger, moved online, MediaWhiz and PetCareRx. So these were the years that you and I were in a CEO forum together. So these are probably the years I'm very familiar with about your career. But I'd love to think with you about those three things. So you take over your first company as CEO. You're still honing your leadership skills as it were. You have the founder, presumably still present somewhere in the company...

Jonathan Shapiro: Very present

Matt Blumberg: ...Face of the brand, name on the door. And the company was owned by Strauss Zelnik at Zelnik Media at that point, wasn't it?

Jonathan Shapiro: Zelnik Media and the Ripplewood Holdings guys were the capital behind it. But Strauss and the Zelnik Media team led the way.

Matt Blumberg: Right. So Strauss, legendary media CEO, Lillian Vernon, queen of Tchotchkes and catalogs. And enter Jonathan, fresh, first time CEO. What was that experience like and what was the biggest thing you got out of it?

Jonathan Shapiro: So it was another great education. Part of both the DoubleClick and the Lillian Vernon educational part was my awareness that there was a lot for me to learn. So I was very open and eager to figure out how to be a great leader, like watching O'Connor, watching Strauss, who was a fantastic leader. And so, at Lillian, one of the things that Strauss taught me and working for him taught me was, I was the accountable party. We were going to run this business based on clear metrics and expectations. And I was going to be held accountable to what those were. And the worst thing to do was to surprise Strauss. You just didn't want to do it. And I remember-

Matt Blumberg: You never want to surprise your board, your shareholders.

Jonathan Shapiro: Exactly.

Matt Blumberg: Particularly don't want to surprise him.

Jonathan Shapiro: But he was great. One of the things that was a great model was he wanted to be disagreed with. He didn't object to you having strong opinions, hopefully loosely held. But he taught me it was okay to argue with the boss if the focus was what's the best path forward. So the great example there was he wanted me to do radio advertising or he wanted us to do radio advertising. And I thought that was the most terrible idea ever, because I didn't see how it was going to really work for the Lillian Vernon catalog. We had a debate. He said, " I want you to test it." We tested it. And what we discovered was, it was only effective in really high Lillian Vernon density markets. It wasn't a great tool. And he was able to say, " You were right, Jonathan. We shouldn't roll this out." Strauss is right a lot. So for him to be able to acknowledge that, hey, my young CEO first time got this right, was very powerful. I actually over time, we expanded and the platform. Rick Bennett became the CEO of Direct Holdings, which held Lillian Vernon and the time life property. I ran Lillian Vernon for him. And Rick was another great leader. He taught me to be requiring, how to be requiring and supportive in the same way. So the model of, " Get me my sales," that's not being requiring right. In his model, which Rick taught me was being requiring was establishing, " This is what excellence looks like, team. Let's go get it. Let's require excellence of ourselves and let's measure ourselves against it." And then your job as the leader, once you've defined it, is to make sure that the people around you have what they need to achieve it. If they're not achieving it, you have to figure out if it's a will, a hill, or a skill problem. And then if it's a hill, you've got to clear it. If it's a skill, you've got to try and coach to it. If it's a will, you've got to inspire. And if you can't do those, then you've got to make a change. And that was a very powerful leadership lesson.

Matt Blumberg: Yeah. For sure.

Jonathan Shapiro: The most important thing that happened to me there was when we sold Lillian Vernon. So we took it from a catalog company. We got its online sales up from 5 million to 80 million. We sold the business. And the team at Lillian Vernon, I was going to be moving on. That was kind of known. And Michelle Groskovich, my head of merchandising, comes into my office in the two- week transition period and she says, " You got to come to the conference room. The new CEO is running amuck. We need your help." So I get up out of my chair and I run down, and it was my team, the Lillian Vernon team, and they threw me a party.

Matt Blumberg: And so, I hope you called whatever his name was from United Media and said, " I got a constituency now."

Jonathan Shapiro: Yeah. I didn't. But that's what had happened. And I was so grateful that I'd had the opportunity to learn how to be a good leader, and then I'd developed those skills. And that was the proof point. I'd done well at DoubleClick. That was the point where I felt like, okay, I'm not quite O'Connor or Zelnik yet. But this team will follow me in that I've earned that. And that was really powerful and meaningful.

Matt Blumberg: So if you think about the next two companies that you ran, MediaWiz and PetCare, and you talk about them together separately, how did you hone the craft while learning different businesses? And MediaWiz I guess you're familiar enough with it from inaudible

Jonathan Shapiro: Yeah.

Matt Blumberg: PetCareRx, that's completely different from anything you had done in your career.

Jonathan Shapiro: Yeah. PetCare was related because it was an online retailer. And through the Abacus and then MediaWhiz basically selling to those guys, marketing services, I developed some of the understanding. But MediaWhiz was a real leadership challenge in the sense that it was... The Lake Capital team had put together four companies. And there weren't four CEOs, there were four founding teams. All of them had at least two. One had three founding partners that were still in the organization. And so, it was an interesting time. My model for leadership at that point had become, can I inspire followership? Lillian Vernon had sort of... What I'd learned is I want to be able to inspire this team to follow the vision that I've created with them and the strategy, the path towards that vision. Can I inspire these founders in the same way? And got there in April of 2007. I was promised by the Lake Capital guys, " You have 90 days to figure out a strategy. But the markets are kind of hot, we may want to move quickly here." 30 days in, Kevin Rowe, who was the operating partner, great guy. Kevin calls me, he's like, " Jonathan, we're having a lot of inbound interest. We're going to go to market in May. We need this strategy now." So we put together a strategy. We went to market and we were crushing it. And by the way, the founding teams were doing that. I was still learning the business, getting up to speed. But a large portion of our revenue was driven by subprime lending. I don't know if anyone remembers what happened in late 2007, early 2008. But the capital markets for subprime lending, mortgages, and the rest of it, it went away. And so, literally, we had term sheets at very attractive prices to sell the business. We had to pull them. We had to stop the deal because when our subprime lending clients stopped marketing, and literally they just stopped.

Matt Blumberg: They just stopped because they all blew up.

Jonathan Shapiro: Exactly. We couldn't explain that and retain the value. So we pulled it. And they were saying, " We'll be back in early 2008," and obviously, that didn't happen. So this, which was a rocket ship of growth. Literally from the time we put out our first sim to the first sale meeting, buyer meeting, we had to raise. We raised our forecasts because we were just on fire.

Matt Blumberg: And that happens all the time with companies who are talking to private equity buyers.

Jonathan Shapiro: Exactly. Exactly. " You know that 130 we said we were going to do? No, we're going to probably do 135- 140." And so, we went from rocket ship to real crisis. And that was when some of the lessons I'd learned had to come into play and I had to learn some new ones. So how do you stay positive when literally the four founding teams were excited because they were going to get a second bite at the apple and it was going to be big. And that all goes away. So how do you stay positive? How do you keep the team energized and those kinds of things? And so, it started with, I had to create some hope for the future. And I am borrowing from what I eventually learned from my master's degree. But hope theory is, you've got to have a goal, you've got to have a pathway to the goal, and the people involved have to have agency. So the goal is the vision. Here's where we want to go. If you're the CEO, you are accountable for your organization for this. They got to know where you're going. What's the vision? They got to know how they're going to get there. What's the strategy? You don't necessarily have to create it on your own, but you have to make sure everyone understands the strategy. And then it only works if everyone in the organization really sees what's their part. How does even the billing clerk from your linked ads product, how does she understand her role in this whole thing? And you got to drive that down. And so, we started there, and we started painting a picture for the future of how MediaWhiz could become this great organization. And we did that sort of'07 rocket ship crashing to earth in'08. We were able to build back the business. At its peak, it was about$ 130 million. We got it back to$ 120 million by 2010. But it was never going to be as profitable because the subprime marketplace is very profitable. And we didn't have that available to us anymore. So frankly, the price tag that the Lake Capital guys wanted wasn't likely. I brought them a deal. It wasn't going to be what they wanted.

Matt Blumberg: inaudible.

Jonathan Shapiro: Yeah. I didn't know how to create what they wanted. So when the Goldman guys came around and wanted me to run, they were looking for a CEO for PetCareRx, I moved on. I was like, " Okay, let's give that a shot."

Matt Blumberg: All right. So PetCareRx for a couple of years, e- commerce, totally different application of it. What was your biggest learning from that few years?

Jonathan Shapiro: Yeah. Well, some business related, some positive psychology related. Because way back at Lillian Vernon in 2004, I had said to my wife, " One day, I'm going to go be Dr. Happy." And she said, " What do you know about being happy and who's going to listen to you?" And I was like, " Those are two interesting and potentially hostile questions." But I started as part of my leadership learning, really digging into the field of positive psychology. Started by the book The Paradox of Choice, where at Lillian Vernon, I needed help figuring out how much choice around a product that we'd had a hit product, the mini tote should we do? We had three of them, red, white, and black, leather handle. And my chief merchant wanted to do five fabrics and 20 colors. And that felt like too much. Anyway, read that book, found the field of positive psychology, saw its application to leadership and said, okay, I'm going to study this. Was on my own until 2012, reading everything I could get my hands on from Seligman, Frederickson, Ariely, Tal Ben- Shahar. If you read anything in positive psychology, these are the guys and gals. And so, I was reading all this material, I got to PetCareRx, and I was like, okay, let me see if I can fix PetCareRx, who'd been around for a long time, but had never made any money. It was an online retailer. It was focused on pet medication, mostly it was flea, and tick, and heartworm medications. But you could get a prescription filled through PetCareRx. And so, how can I apply what I've learned into this context as well? And so, one of the things was in addition to having a vision, mission and strategy, that mission part... Hope theory is, what's the vision? What's the strategy? And how do you create agency? The mission part, this is the Simon Sinek stuff, is critically important. It's like, why does everyone come to work every day? And here's how we made that operative at PetCareRx. It wasn't that exciting to come to work every day to sell flea and tick medication. But what was exciting was the joy that people got from their pets and the love that they exchanged with their pets. So what we came up with was PetCareRx was in business to add a little love to the world. That was our mission. And it resonated. My call center, people would call and they answered the phone, " Hi, this is Frank. How can I add a little love to your day today?" And people were like, " That's great." By the way, the way that was operative was we figured we were there to help people have healthy pets. We did that about four or five million times every year. Every healthy pet, another wag of the tail, another meow, that was a little love. That's how we added love to the world.

Matt Blumberg: It's such a great way of thinking about how to add purpose to a business where maybe on the surface it doesn't look like there's any. And I'm a big believer that every business can draw a straight line to a higher purpose. Sometimes it may take you a little while to discover it or articulate it.

Jonathan Shapiro: Yep.

Matt Blumberg: It's super important.

Jonathan Shapiro: Super important. And if you believe in this model of leadership, which is how can you inspire followership, how can you inspire the team to follow you where you think collectively is the best place to go? Having a great purpose is critical.

Matt Blumberg: So talk about the decision to get the master's, the second master's, and to stop being a CEO, and become a coach.

Jonathan Shapiro: Okay. So I'd done all this reading in positive psychology. And frankly, despite having some academic success, I'd never enjoyed school. But I was loving the self- study of this field. And the University of Pennsylvania offered a master's in applied positive psychology on the weekends. I was like, " Okay, sign me up." So in September of 2012, I joined that program while I was running PetCareRx. And my wife will tell you that for a year, all she saw was the back of my head because I would leave at 7: 30, I'd be at PetCareRx from 8: 00 to 7:00, home at 7: 30, eat dinner. My young kids, they've had dinner, they're off. And then I'd go back to work doing schoolwork. But that was the catalyst that answered my wife's questions. What do I know about being happy? And who's going to listen to me?

Matt Blumberg: Who's going to listen to you?

Jonathan Shapiro: And what I discovered was over this, both having to learn how to be a good leader and then really experiencing the most joy from the realization that if I was helping my team succeed, that was my source of joy. That's what brought me happiness. That was the light within me. That's what I wanted to do. And in December of 2013, I'd had a disagreement with the PetCareRx board. They wanted me to go one direction, which I told them... They wanted me to compete with Amazon on price. And I was like, " How? I do not know how to do that." I had an idea that I said, all I needed was another$ 15 million and we could really make this work. And they're like, " Oh, we're not so sure, Jonathan." So we parted ways. And it was then that I said, okay, now's the time to go be Dr. Happy. And my real incarnation of that was, how do I help other leaders be their best leaders? And that's 2014 January I became an executive coach.

Matt Blumberg: So you have these couple of threads coming together here in your life. You have your development as a leader and going from, " Sorry, Jonathan, you got no constituency to cultivating followership." You have this thread and this academic, but also very practical learning about what drives happiness and fulfillment. They come together in the form of you as a coach. How do you approach your work when you're coaching a CEO? And here's why I asked the question. At Bolster, we help CEOs find coaches and we help them find mentors. And we define the two a little bit differently. We define a coach as someone who is going to help you be the best version of you. And we define a CEO mentor as someone who has been there, done that as a CEO, and can help you figure out how to do your job, help you navigate the craft of being a CEO. There are coaches who have been CEOs before, and a lot of coaches who have not been CEOs before. So you're one of the ones that has. If you buy into our framework, when you work with a client, do you approach them as a coach? As a mentor? As both situationally or as either situationally? Do you ask them what they're looking for? How do you think about that?

Jonathan Shapiro: So I actually approach it in combination. And I think actually my website still says I'm a mentor coach, surprisingly. So here's how that works. My methodology is I ask them to bring the issues and problems that they're facing, the most difficult things that they have to solve. And then we discuss some of the frameworks that I've experienced and used. And if I'm doing a good coaching job, I'm asking them the questions that allow them to discover the best answers for themselves. Occasionally, and I draw this distinction, I will tell them, " Okay, now I'm going to consult," which is being a mentor. And I clear this before we start our coaching relationship, " What that means is, I have seen this movie. I believe I have a really good answer for you. So I am strongly suggesting that you do X." But that's a very different position than what do you think the best answer is? What options have we talked about? What are you considering? And I ask my CEO clients a lot, " How are you inspiring followership? What is it that you're doing that is going to have your new tenants wanting to run through a brick wall like I would do for Kevin O'Connor? What is having them want to do that for you?" So I do think there's a distinction. I do a little of both. But when I am mentoring or consulting, I declare it.

Matt Blumberg: You declare it.

Jonathan Shapiro: And they expect it.

Matt Blumberg: To be declared. Right. That is a very, very good practice. Jonathan, this has been a lot of fun talking to you. I love your journey. I love the fact that you have found happiness in the studying, and now in the giving forth of happiness to others. Thank you for being here.

Jonathan Shapiro: Pleasure. Can I give you one compliment? So look, Grit, Angela Duckworth wrote the book, it is the combination of passion and perseverance. And sitting on your board, being a friend, being in your CEO peer group, having lived with you for the last 20 plus years, you epitomize grit. And I know it took 20 years to get Return Path from the idea to a successful exit, but that's a great example. Watching you, literally at the precipice, a number of times where it could have gone very badly, have the ability to focus forward, " What are the solutions, what's available to us?" And lead your team, inspire your team, through that, really inspirational. Taught me a lot.

Matt Blumberg: Wow. Well, thank you. That means a lot coming from anybody who I've spent a lot of time with over the years, but particularly from you. So thank you for that.

Jonathan Shapiro: Pleasure.

Matt Blumberg: And thanks for inaudible.

Jonathan Shapiro: All right, sir, talk to you.


In today’s deep dive episode, Matt interviews CEO coach and multi-time CEO Jonathan Shapiro. They chat about his career, from bringing comics onto the internet at United Media to becoming a CEO, and then making the move into executive coaching. 

Tune in to hear Jonathan share the lessons he learned about management and good leadership that changed his career.