272: Think BIG with Mark Josephson

Mark Josephson, Executive Coach, three-time CEO with three exits, Founder, Advisor, and Investor, is driven by a mission to empower leaders and think big to achieve clarity, purpose, and lasting impact in their organizations and lives.

We learn about Mark’s journey from leading three companies to successful exits to coaching leaders and teams to unlock their potential. He explains the Wouldn’t It Be Great If framework, a four-step approach to setting ambitious goals: pushing away from the desk, asking bold questions, identifying what needs to be true to achieve them, and brainstorming without constraints. Mark also introduces the Balcony vs. Dance Floor framework, which helps CEOs balance strategic vision with operational focus. He shares lessons from his entrepreneurial journey and insights from his podcast Critical Moments.

Think BIG with Mark Josephson

Good day, dear listeners. Steve Preda here with the Management Blueprint Podcast. And my guest today is Mark Josephson, Executive Coach, three-time CEO with three exits, Founder, Advisor, and Investor. Mark, welcome to the show.

Thank you, Steve. I’m so excited to be here. Thanks for having me.

Oh, it’s exciting to have you. You have built two companies up to exit. Oh sorry, three companies. That’s very impressive. And you’re advising other companies. And now you’re going to advise our listeners, which is very cool. So, let’s start with my favorite question, which is, what is your personal “Why” and what are you doing to manifest it in your practice?

Great question. I believe that we have a choice that we make every single day that we wake up to put goodness in the world or to take goodness out of the world. And I wake up every day, most days anyway, with the intention of helping the people I meet, the people I come across have better days than they did yesterday. It is that simple. I want to make a positive impact on the people around me. I will say that I have three goals as it relates to those “Why” more personally and I borrowed this from somebody else so I didn’t invent this but it resonated. Number one, I want to stay married to my wife. And I’m specific because that’s the most important relationship that I have in the world. We will be celebrating our 26th wedding anniversary next week. And we met in college and have been together for over 30 years. So it is the number one most important thing that I need to do every day is make sure my wife is happy. Number two is I want to be thin and fit and why I say that is because I want to live a long time. I want to be healthy. Another really important relationship in my life is with me and my health and well-being. So I want to take that seriously and the third goal, Steve, is that I want my sons and I’m blessed with three sons, 22, 20 and 17. I want them to call me when they need help. That’s it. I’m going to be really happy and healthy and will die a happy man if those things are true.

It sounds like that’s a great formula. Relationships, purpose, and more relationships. It helps.  I mean, they say that these are the three most important things that are required for happiness, so, definitely, you seem to be on the right track. No surprises there. Well, before we talk about the framework, I’m curious about these three businesses that you ran and exited.

Sure.

Tell me a little bit about that. Is this, is all this private equity, what companies did you find them? How did you come about it?

Sure, so to start at 10,000 feet, I’ve spent 30 years in technology startups with being born and raised in dot-com one in the 1990s. And I was blessed to be at a high growth company that went public and sold. And I ended up having 12 different jobs in five years there, like truly a rocket ship kind of ride. That was a company called about.com. And I got my MBA in the world there. That was incredibly foundational for me. I have been the CEO three times. The first two times I was hired in, and the third time I was a founder. The first company was a company called Outside.in. In 2008, it was a Union Square Ventures company that was trying to organize the web’s information by location. We believe that the explosion of independent and self-publishing created a lot of news and information that would be a whole lot more valuable to people if they could place it in some context. It was 2008. The iPhone was just coming out. The intention was to build a consumer application. We ended up pivoting and building a B2B Sass platform for media companies to aggregate, curate and publish news and information at a lat long, at a very specific location. We sold that business to AOL in 2011. AOL at the time was making a big investment in local, and they had many problems, two specific problems in their business. The editorial costs were too high, and the ad products and monetization were too low. So the intent was to use the aggregation software platform that we built to improve the cost structure and efficacy of the team at AOL Local. I spent two and a half wonderful years there, loved almost every minute of it until I was called back to my calling, which is to be a leader at a high growth, smaller company. And the second company was link shortening company, Bitly. And you may know the bit.ly, the really small links.

Yeah, we use them.

So, Bitly is one of the most widely used and least understood businesses that I’ve come across. But even in 2013, when I joined the company, the global usage was in the billions, not in the hundreds of thousands, I mean, truly the billions. If the usage was here, monetization was here. So, over the first three years in that company, the usage kept growing, but we got monetization to the level that we were profitable and growing. And then we sold to private equity at that point, three years into Spectrum Equity, San Francisco and New York. I then spent three years inside of private equity, scaling the business a couple of times over that. The third time as the CEO, I made the classic case of hubris. I could start something after being hired in CEO. And I started a company with some venture funds called Cast Iron. And Cast Iron is Etsy for homemade food. And we sold that business to a private company in October of 2024. And it’s being expanded and growing. Yeah. So, pretty diverse set of things.

That’s good. That’s good experience. And now you’re here and you’re giving back. So please give something back to us in the form of a framework. What you talked about in our pre-interview is that, it’s really important for CEOs to be able to tap into the thinking of their team and to allow them and empower them to brainstorm well. So tell me about your framework, how to achieve that?

Sure. Let me start by saying this framework started as a conversation between my wife and me about our personal lives and our strategies that we’re trying to, how we wanted to live our lives. Our kids are getting older. The first one is about to finish high school. And I had, this was the time I was starting to think about leaving Bitly, like, all of that stuff was going on. I remember ‘cause I had a cocktail, she had a glass of wine, and we pushed back and we’re thinking, I said, wouldn’t it be great if I never had to ride New Jersey Transit ever again? And wouldn’t it be great if I could be at every single one of our son’s lacrosse games his senior year of high school? Because I’d missed 90% of them before. And there’s a bunch of other things. But what that turned into was a plan to make those things happen. We weren’t looking at the next week saying, how do I make that game on Wednesday at 3? Because that’s actually really hard to do. I’ve got a meeting, I’m going to be in the city, I’ve got employees, I’ve got all this stuff. But it’s actually almost easier to say, how do I go to every game versus go to any one individual game? And the reality of the world and the wall that’s in front of you at that time makes it really difficult to make those decisions and those leaps. So that’s translated into a framework that I use with my clients today, and it’s Wouldn’t It Be Great If. And Wouldn’t It Be Great If is just that, it is freeing yourself. I urge my clients to literally push back from the keyboard, sometimes put their feet up. If it’s late in the day, let’s have a drink. But let’s think about why you started this business or you’re in the job. What are your personal motivations? Is it to win or is it to just get by? What are your hopes and dreams that you want to accomplish in this business? And oftentimes I’m encouraging them or unlocking for them the true ambition that they have, which is to be really big and really successful and build the best software company in the world. That’s why you start these things. And they can be really big and meaningful. And a great example, and then I’ll talk about how we use it, is a lot of my clients just went through annual planning. An annual planning is a really complex way of exercise and negotiation with the leadership team, with your investors, with your own hopes and dreams. And I had a client came back and said, just had the team, we approved the plan. We’re going to grow it 46% next year. And I said, okay, is that really what you want to do? It’s like, oh, well, you know, our run rates, the marketing says they need more budget, sales is telling me about a product and all that stuff. And I said, but Billy, not his real name, wouldn’t it be great if you doubled next year? And it’s not outside the realm of possibility, in the growth stage of the company. And he said, well, I don’t even know how to think about that. I said, so let’s push back. Wouldn’t it be great if you doubled next year? That’s the first question. The second question is, what needs to be true for that to happen? Well, we’d need to hire 10 more salespeople and have them ramped by the end of Q1. Oh, we need to reduce churn by 15%. We would need to add a new product and move up market. But then you just keep working backwards to what would need to be true and you stack rank them and you start to attack them. And that is, Wouldn’t It Be Great If in a nutshell, is jumping far into the future, to the future you want, and then working backwards around what needs to be true in order for that to happen.

I love it. That’s great. It’s great future pacing, I think some people call this. Wonderful. So that’s your framework. Do you have a name for it?

Wouldn’t It Be Great If.

Okay. That’s the Wouldn’t It Be Great If framework.

Yes.

Love it. So let’s switch gears here and let’s talk about your podcast. So you have a podcast, Critical Moment. Tell me why you started this and what is your mission with it?

Thank you for asking. So I’m so passionate about the entrepreneurial journey and the leadership journey. The leadership journey that so many of my peers and my clients and my associates are in the middle of, and I’m sure so many of our listeners. And what I found when I looked at the landscape of podcasts, and the world doesn’t need another podcast from somebody like me, but what I do think it needs is a different kind of story. And the bell curve of startups and entrepreneurs, there’s a lot written about this over here, there’s a lot written and talked about over here, but there’s not a lot about the fat, meaty part in the middle, which is real people building real careers, real companies and real lives in tech. And so what I want to do and mean to do with critical moments is not get on the phone, a call with somebody and ask them, tell me your journey, tell me the tropey kind of, it’s not how I built this. It is one specific moment that can be really big, such as one of my guests talked about having the company just about sold, thought it was sold. A nine-figure deal, and to the point where the eight offices of the company all had t-shirts and cupcakes and champagne for the new company, for the acquirer. The top 50 people in the company had already been told what their new comp plans were by the buyer, and the next 50 people knew they were getting laid off in the transaction. That’s how real this was until the phone rang. And it was the head of Corp Dev saying, I never thought I’d have to make this call. That’s the critical moment. What were you doing? What did you do? And what did you learn from that, like real specific things that happen? I had a really powerful episode with a leader, she’s gone on to be incredibly successful. But it was the first time she was up for a C-level job in a promotion and she didn’t get it and she asked why and the CEO said, because people don’t like you. Could you imagine that moment being told that as a grown up professional who’s killing it by the way, and every single metric that the company measured itself on. And so there are critical moments in everyone’s career. Those are just two powerful examples. There’s lots of other ones as well. But I want to normalize the roller coaster of the journey and show that there are moments every day in our careers and our moments that we can learn from and make them more real.

Yeah, I mean, these tipping point moments, they really reset careers. And I have found that often when these critical moments happen, then we already are facing a flattening learning curve. And even though this is a shock, it pushes us to expose ourselves to another learning curve, and then it can become a really beneficial shift.

Yeah, and I don’t usually think about it this way, but when you’re building muscle, like the practice of lifting weights actually creates micro tears in your muscles that then have to form back over, like, and it’s kind of painful. If you’re doing it right. And that stuff happens every day. And the things that I’m most interested in in those conversations, which I think is really relevant to leaders, is how do you respond in the moment? And like, how do you react? What were you thinking when you got that feedback? Like, do you remember what room you were in? Who was the first person you called? Because you can see great leaders tune their instincts the right way and can do that. And I think you can prepare for that a little bit. If I’m ever in a situation, it’s okay to say, let me take a minute to think about that, for example. I also think there’s really important learnings that we could share. So for example, one of the biggest takeaways from that episode of the acquisition, which didn’t go through, was there were two things. One is that he had never met the CEO of the acquirer. Tried 15 times and they said, it’s just not necessary. It’s just, you don’t need, trust me, it’s a big buyer. Like it wasn’t like out of the ordinary that you wouldn’t ever get to meet the acquirer CEO. But what happened was in the final meeting, which was supposed to be a rubber stamp, because everybody but the CEO had approved it at this point, the deal’s champion was out sick. And so the champion’s, number two, had to defend the deal to the CEO who said, what? And so number one, he’s like, I’m never going to not meet the CEO of an acquirer ever again. And number two, I’m going to build champions up and down the organization and across the organization so that they can stay. Anyone can stand up and defend this opportunity. Wow, that’s so helpful to hear for anybody who is maybe a first time CEO in a conversation with a potential acquirer.

And don’t pick a champion who is prone to sickness.

Yes, that’s right.

Strong enough.

Healthy. You want a healthy champion for sure.

Awesome. So what is the most important question in your opinion a CEO should ask themselves on a regular basis?

I think it’s really important to elevate. So another framework that I use is Balcony vs. Dance Floor. And that’s the difference between working in the business and on the business. And I think it’s really important that CEOs spend time in the balcony. And I think it’s really important that CEOs actually get away from their laptop and go for a walk or go for a run or whatever it is that one does to invest in themselves because it is a fact and research proves this, that when you stop thinking about the problem in front of you and think about something else, your brain is still working on it. And it will come through. We all know this experience that happens to us, but you can manufacture that time. And I think the most important question that a CEO needs to ask themselves, ask herself on a regular basis is, what am I trying to do here and am I doing that? Really, what am I trying to do with this company and with this opportunity? There’s a lot of objective strategies and tactics, but I started this company because I wanted to achieve X, or I took an investment in this company and I told them that I was gonna get to Y. The difference between being on the dance floor and getting jostled and moved around versus the balcony saying, am I really doing what I set out to do here? The best CEOs I’ve met are methodical about their focus on the top of the mountain. It’s the ones who start to take paths and wind and get distracted that becomes really problematic.

Do you recall a moment when you asked yourself this question and you decided to shift what you were doing?

Better than that or worse than that I’m not sure. In the moment it felt worse. I remember being asked by an investor, actually I wasn’t asked, I was told, Mark, I have no idea what you’re trying to do with this company. What are you trying to do? I mean, that was a critical moment for me because I was like, what do you mean? We have board decks, we have strategy conversations, we have like all this stuff. But what the question really was is like, I don’t understand, you’re doing a lot, but why, to what effect? Are we moving up market? Are we cannibalizing somebody else’s business? Is it a competitive thing? Are you trying to get to 100 million so you can do A, B and C? Like, let’s have like the real conversation about what you’re trying to do. I know you’re operating. I know you’re growing. But what are you really trying to do? It’s a hard question. I remember it.

Even when you have a vision, this can be a relevant question to ask.

Yeah, I think so. And I think it’s a very basic one. And you asked the question about personal “Why” at the beginning, and it’s the same question. It’s what are you trying to do here? Because when you’re a leader and you can clearly define that, it’s actually a superpower. Because one, people want to help you. They will know how to help you. That turns into plans that you can roll to your team and goals you can roll to your team that ladder up to that objective. And every employee I’ve ever met broadly wants to be successful. And as the leader and the CEO, you define what success looks like in your organization, and they can’t read your mind. You have to be clear about it.

Yeah, I love it. That’s very powerful. And I think people are hungry for purpose in life. And most people don’t have a self-awareness or they don’t have the context or they don’t have the perspective to be able to come up with a worthy purpose. And if they can tap into a company, if they work for a company that has something that is exciting and attractive and they can latch onto it, it can really energize them to bring their life and soul to the company.

There’s an incredible piece that I read, and I’m going to tell the story wrong, but hopefully communicate what I want to communicate, is it’s around starting with “Why.” And it tells the story of the difference between Apple and, I’m going to say, Hewlett-Packard, HP. Both make consumer electronics. And 15, 20 years ago, they were probably making very similar products. But one feels very different than the other, and why? And when Steve Jobs would get up and talk about why you want to have the music in your pocket, why you want this all in one device versus a we are going to create a printer for you that’s going to do this many dots per inch and this many pages per minute. It’s like the feature, feature, feature versus the world is changing.

How do you put a dent in the universe? I love the Steve Jobs quote to Joe Scully when he enticed him over to Pepsi and he asked the question that, do you want to sell sugar water to kids or come with me and change the world?

That’s right. Yeah, and I don’t think it’s wrong to say that you can find a “Why” in most businesses in just about any business. It doesn’t have to be change the world. I always err on trying to find the change in the world or change our part of the world in the businesses that I’m in. But the truth is, is that businesses change and landscapes change and competitive marketplaces change. And in my very first job, I worked at a marketing firm, and I remember as we were developing strategic narratives for companies and positioning, you start with the four quadrants and you want to be upper right, but if the world is defining upper right as something that you’re not. I remember erasing the Axies names and writing in new ones so that we were upper right in redefining that and leading the world to that new tomorrow.

Yeah, love it. All right, well, Mark, thank you for coming and sharing your wisdom with our listeners. So if people would like to learn more or connect with you or get you, hire you perhaps, where should they go?

They can find me in three places. The first is on LinkedIn. I’m more active than I want to be, but I actually do love LinkedIn and the connections that I have there. You can find me on LinkedIn. My website is markjosephson.net. And if you want to hire me for coaching, if you want a one-off conversation or two, you can find me on intro.com, and you can book a meeting with me there.

Awesome. So, Mark Josephson, three-time CEO with three exits, Founder, Advisor, Investor, and Coach. Thanks for coming. And those of you who enjoyed this conversation, make sure you follow us on YouTube, you subscribe on Apple Podcasts, give us a review and so on, and keep coming back because every week we have a wonderful entrepreneur or CEO coming to share with us their wisdom. Thanks for coming, Mark, and thanks for listening.

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