https://youtu.be/dxdFmUiiQds
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%.
