The Four Stages of the Entrepreneurial Journey – Mike Malatesta

Listen On Your Favorite App

Does Your Business have You Stressed, Tired or Overwhelmed?

Let me help!

Let's Talk

Show Notes:

If you’re going through tough times, you should always keep going. And that’s especially true if you’re an entrepreneur. According to our guest, there is a valuable lesson and a chance to grow in every single experience.

Mike is an entrepreneur who loves helping other entrepreneurs create the futures they want and deserve. He has started, grown, and sold two 8-figure companies. These companies collectively generated more than $500M in revenue and sold for more than $180M. Mike’s also the host of the “How’d It Happen Podcast”, a top-rated podcast for entrepreneurs about their success stories. He recently published a book called “Owner Shift – How Getting Selfish Got Me Unstuck,” where he shared his entrepreneurial story and the lessons he learned along the way.

As a long-time entrepreneur, Mike has faced and conquered many challenges in his journey. But, ultimately, what helped him do that was looking at every single experience as an opportunity to grow.

In this episode of the Think Business With Tyler podcast, we chat about the importance of learning from every experience, what are the four stages of the entrepreneurial journey, why partnerships are often tricky to manage, and how to take ownership of your life.

If you’re a thriving entrepreneur, you’re going to want to hear what Mike has to say. So tune in to hear some vital lessons of entrepreneurship.


💡 Name: Mike Malatesta

💡 What he does: Mike is an entrepreneur who has helped start, grow and sell two 8-figure waste management companies. He’s also a book author and a podcast host.

💡 Noteworthy: Mike’s new book, “Owner Shift – How Getting Selfish Got Me Unstuck” examines his entrepreneurial journey and teaches other entrepreneurs how to get unstuck. His podcast is called “How’d It Happen Podcast”, and it’s a top-rated podcast for entrepreneurs with over #200 episodes

💡 Key Quote: “Show up on time. Do what you say. Finish what you start. Say please and thank you. You do those four things, you will build a culture, you will build a team, you will build trust, you will build success.”

💡 Where to find Mike: LinkedIn


Key Insights

Every experience in life is an opportunity to learn. Being an entrepreneur sure sounds ideal, but it’s full of bumps on the road, just like everything else in life. An entrepreneur since the age of 26, Mike has had his fair share of obstacles. However, looking back on some of the most challenging moments in his career, Mike believes that every experience in life can be a valuable lesson. “Everything in life is an experience that you have an opportunity to learn from or you have an opportunity to just be angry about and I was angry about it when I was going through it because I thought I wasn’t willing to accept 100% responsibility, but by the end, I got what I deserved. And I used what I learned through the process to make me a better person and better leader, better business person. […] What I learned from the experience, I think, made us all better and we survived and thrived as a result of that, partially as a result of that learning experience.”

There are four stages of the entrepreneurial journey: the dream stage, the grind stage, the break stage, and the breakthrough stage. In his newest book “Owner Shift”, Mike explores entrepreneurship. He teaches other entrepreneurs to get unstuck and create the futures they want through his own raw entrepreneurial story. The book’s subtitle gives us a sneak peek of what to expect in the book: How getting selfish got me unstuck. In addition, Mike breaks down entrepreneurship into four stages that he explains in detail in this episode. ”And I’ve come to believe that all entrepreneurs have a responsibility to themselves to go as big as they can go. And when I say big as they can go, I don’t mean just financially big because money is one part of it. It’s not all parts but going big from a capability standpoint, maximizing the capability that you have, that your team has, and that your business has, I feel like that is the job of the entrepreneur or the leader.”

Although potentially very powerful, partnerships are often tricky to manage. Mike believes that partnerships can either be phenomenal or horrible. There are so many factors that determine the success of a partnership, but usually, the best way about it is to make someone in charge of the partnership. Here’s what Mike has to say: “Most of the time in my experience, you get to a point in your 50/50 partnership where someone thinks that they’re 60 and you’re 40 and they are mad about that and the other person thinks they’re 60 and you’re 40 and they’re mad about that and then you start really competing with one another for things that aren’t helpful for either of you or for the business. So I just think it’s really tricky. My personal opinion is someone has to be in charge of a partnership.”

My future is my property. Finally, Mike opens up about some of the hardest moments in his career, one of them being the death of his trusted business partner. This devastating experience almost led him to give up on his dreams, but then he heard five words that changed the course of his life and career: My future is my property. “I had forgotten that my future was my property. I thought my future was going to be the byproduct of all the other things that are going to happen to me that I can’t control. And he said no, you can own your future. Because it’s your property. You just have to know what it is. And then you have to be willing to pay for it. And those two things, the acceptance of this perfectly designed system, and my future’s my property just helped me a ton to get my head straight and start doing the job that I was supposed to be doing.”

Top Quotes

“If what you’re going to do or what you’re going to consider is something that you would not be proud to have on a billboard, that your mother would read when she went past the billboard, don’t do it. And I certainly did not, or would not have wanted my mother to read about what I was doing. But when he said it, I didn’t get it. I thought, ‘Oh, he’s talking to somebody else.’ So I would say to people, there’s a lot of challenges in business and there’s a lot of ways to take shortcuts. There are a lot of ways to excuse behavior that you wouldn’t do in your personal life.”

“If you designed a system, and I believe this wholeheartedly if you designed a system to get you where you are, which by the way is exactly what you did, then you are capable to design a system that gets you where you want to be. So let’s just accept that as being a possibility. And once you’ve accepted that as being a possibility, breaking through becomes a lot less daunting. In fact, that becomes energizing because you want to get it out or any way. So that’s what I’m trying to do. Go big, and breakthrough.”

“Every time we don’t win, we get better to win the next time. […] So if we lose, it’s not because it’s not personal. I was taking it personally. It’s not personal. It’s just we didn’t check all the boxes. So we go back and we learn how do we check all the boxes and that goes for whether it’s a deal, whether it’s a person you want on your team that you can’t get, whether it’s whatever.”

“I shifted to I have the responsibility for, that was my what my thinking was, instead of I’m responsible for it. So for example, when we lose something, it’s not personal to me, right? It’s not I lost this and that makes me a bad person, but I have responsibility for the loss. We lost it. So what do we do? And that’s the shift in thinking from responsible to responsibility helped me a ton.”

“I needed to work with someone who could help me and I found a company called scribe media that has a process that they help authors go through to write a book and I took their course and join that process. […] It was easy to do because I followed their system and anybody that knows me when it comes to business or anything else, I wasn’t for a long time but I am very adamant about systems and processes in a business and they provided me the systems and process I needed to write the book.”


Personal Website

How’d It Happen Podcast

Owner Shift: How Getting Selfish Got Me Unstuck

Latest Podcast Episodes: