Jerry McNamara, a leader of five companies, known for their growth and workplace excellence. McNamara aims to impact 5 million people in five years through better businesses, focusing on work-life balance. He operates "Proven Chaos" and "Best Places to Lead."

Jerry shares his challenging upbringing, leaving home at 16 due to an alcoholic mother. He learned resilience, community importance, and personal responsibility, highlighting the power of self-preservation.

McNamara emphasizes perspective, community, and intuition in leadership. His success comes from the right environment and overcoming life's challenges, advocating for hiring individuals who have triumphed over adversity.

Finally, McNamara discusses forgiveness and growth. His journey to forgive his mother transformed him, underscoring intentional living and positive impacts on future generations. He urges leaders to join communities like business roundtables for growth and overcoming challenges, demonstrating the value of forgiveness, community, and intentional leadership.

Want to learn more about Jerry's work? Check out his website at

Connect with Jerry on LinkedIn at


Key Points

• Jerry McNamara has led five companies in five different industries and runs Proven Chaos, a company that helps CEOs create compelling companies that outperform and still make it home for dinner (0:10)


• Jerry believes that perspective is important and doesn't make comparisons about challenges. He hires people who have had difficult things happen in their life and figured a way out the other side. He is grateful for the life he has and wouldn't be the same person if he grew up in a white-gloved family. (5:50)


• Jerry developed strong intuition from growing up with alcoholic parents and pays attention to everything differently. He believes that acknowledging people and saying "I see you" is a gift and important for leaders to do. (8:20)


• Craig asks about finding communities for business leaders, and Jerry recommends getting a mentor, coach, or roundtable, and emphasizes the importance of putting ego aside and seeking help from others (15:10)


• Jerry and Craig discuss the power of community and how it can provide solutions and support during challenging times, with Jerry sharing his experience running office hours and connecting people within his network. (17:13)


• Jerry experienced forgiveness at two levels: releasing themselves from the burden they were carrying and having a moment of emotional reconciliation with their mother (19:14)


• Jerry emphasizes the importance of conscious intention and letting go of anger and frustration in order to be one's best self (22:22)


• Jerry encourages having hard conversations and owning one's 50% of a relationship, and reminds listeners to say what they need to say for their own sake (23:40)


Craig Andrews    00:07
Today, I want to welcome Jerry McNamara. Jerry has led five companies in five different industries, in B to B and B to C, in both products and services. You know what? I think that covers the gamut. So his companies have been recognized as franchise 500 franchise 502 times, Inc's fastest growing two times, business journals fast 53 times. And Trend magazine's best places to work. Jerry runs Proven Chaos, a company driven to help CEOs create compelling companies that outperform and still make it home for dinner. It's that last part that's so critical. Jerry also runs the best places to lead show, and I would suspect part of the reason he does that is Jerry has set a mission to positively impact 5 million people in five years through better businesses. Jerry, welcome.
Jerry Macnamara    01:16
Frank. Thanks for having me. This is going to be a super fun conversation. I mean, your story is extraordinary. So I love having conversations that are peer to peer and just sharing experiences that we've learned along the way. So thank you for having me.
Craig Andrews    01:32
It's a delight. And I'm looking at my notes and I'm just trying to figure out where to start, but it seems like we need to go back to 16, actually, maybe let's back up one year. Tell us, what was your life like between your 15th and 16th birthday?
Jerry Macnamara    01:55
Well, jeez. Puberty is a fun, real fun time as you're starting to learn things and have acne and try and figure out the world and girls and all those fun things. But like many people in the United States, I grew up in a broken home with two parents that were sick, and I ended up leaving home at 16 after going through rehab five different times with my mom. And I didn't really see my mom from the time I was 16 until I was 31 or 32, when she was dying of liver failure. And that was a seminal experience for me. I learned a lot about community, about love and loving care and caring, and that family is where you feel comfortable. And so I say that all the time. I have the biggest family in the world because of those attributes.
Craig Andrews    02:56
Let's back up, because therE's something I want to make sure we don't gloss over. I mean, there are people in their 30s living in their parents basement who haven't found the boldness to go out and start their own life. You left at 16. Just thinking about that, that kind of scares me as a parent. Of course there's fear, sure, but there's a lot of uncertainty at 16. I mean, what was going on that so compelled you that that was the most logical choice for you to make.
Jerry Macnamara    03:36
I have shared this story before. I don't share it very often, but I was in a situation where my mom, who was wonderful when she was mom, but really difficult when she was Sandy, the alcoholic, and I was having an experience with her, a verbal altercation, and had a baseball bat in my hand, and my mom was asking me to hit her with baseball bat. And I remember swinging as hard as I could, Craig. And to this day, I am so thankful that I swung at the bed and didn't swing at my mom. And I literally laid that bat down. And I thought, I am not going to jail for the rest of my life because of this difficult situation. And that was when I just decided I needed to save myself. Because sometimes you want more for other people than they want for themselves. And so I learned an important lesson in that, and that's that I'm only 50% of any relationship now. I'm going to own my 100% of my side. But if I want more for you than you want for yourself, then I can't help you. And so you have to come forward to the table. So it was that moment where I just thought, okay, time to walk around the hole. And having gone through rehab a number of times, one of the things that they talk about is this analogy of someone walking down the sidewalk and falling in the same hole again and again and again and having the difficulty of having to pull themselves out. And eventually you get to the edge of the hole, and you've learned enough times that it's time to walk around the hole and continue on. And so that was the state that I was in at that point in time.
Craig Andrews    05:20
There's so much of that scene I'm just still trying to get my head around.
Craig Andrews    05:29
That's heavy. I just spent two days in mastermind with other business owners, and we were just talking about challenges and challenges in the economy and what have you. That's a challenge that's on a whole nother level that I don't even think about.
Jerry Macnamara    05:48
I say this all the time. My favorite word in the English language is perspective. And I really believe that the deeper and wider perspective that you can intentionally cultivate, the better the quality of your life. And so I've had a lot of fun and success, and I'm grateful for that, for being in the right place at the right time with the right people, in the right opportunity. But I've also been in the Deep Valley and been, jeez, how could the two people who should love me the most not be in positions to love themselves, let alone to love me in the way that they needed to. And so I had to grow up pretty fast. I was lucky to be in the right community. And, yeah, I don't make comparisons about challenges, because people's challenges are unique unto themselves. And so, for you, you just overcame a massive challenge. You're still 80% to 85% of the way back. I think comparison is the thief of joy. But challenges are real to people. And I say this all the time. I hire from the scratch and denial in business because business is hard. And I want people that have had difficult things to happen in their life and figured a way out the other side. And so I certainly would not wish upon my worst enemy some of the difficult things that happened to me. But I sure am glad they happened to me, because it made me the person that I am. I'm very joyful and grateful for the life that I have for my family, for my friends, for the people that I serve. And I don't know if I grew up in a white gloved family, that I would be the same person. And so, yeah, it was troubling at times, challenging at times, but I'm sure glad it happened to me.
Craig Andrews    07:54
One of the things I've noticed in children of alcoholic parents is, as a general rule, not an absolute rule, but as a general ruLe, they have intuition at a level that I just absolutely envy. And I see it sort of the flower rising out of the ashes of the despair. But do you feel that about yourself, that you have strong intuition?
Jerry Macnamara    08:20
Totally. You pay attention to everything differently. Because I never knew what situation I was walking into at any given moment. And so I was highly intuitive to say, okay, I see these things. I see the way the door has not been closed 100%. I call it spidey sense. Right. There are spidey senses that I have developed just in interacting with people, how they're showing up, how they're distracted. And if you lean into that and you're willing to have interesting conversations with people, boy, it matters, because people see that. You see them showing up both positively and in ways that they might need some help and some guidance and some hugs along the way. I remember a situation. I was working out at a gym, and there was a woman that had come to know there. I didn't know her very well, but I could just sense there was something off with her. And I went over to her, and I said, are you okay? There's a look of worry and just anxiety on your face. And she looked at me, and she said, my mother was involved in a hurricane, and we haven't heard from her. She lived in the Caribbean. Haven't heard from her in two days, and I'm very worried. She was moved to tears that I saw that in her and that I had the courage to say, I see you. And I think sometimes leaders miss the mark because we don't want to create awkward situations. But wait, is it a miss on the human condition not to acknowledge people and say, I just see something in you that's just not 100% right? I think that's a gift. But to your point, yes, I think I do see the world a little bit differently than other people.
Craig Andrews    10:27
Well, in that is a lesson you were talking earlier about, comparison. It's easy to compare in, oh, I wish I had this. I wish I had that. And I would say in any situation that you're in, some of the things that you hate the most about the situation, if you look at it right, are gold mines. Are gold mines of opportunity. And for you, in just a horrible situation, I would say you've mentioned God a couple of times. I don't believe that's the situation God wanted you to grow up in, but that's the one you grew up in, and it gave you this unique ability.
Jerry Macnamara    11:12
Yeah, I say this all the time. It didn't happen to me. It happened for me. And that's not to say that, oh, jeez, great. That should happen for everyone. But I was lucky. I was identified as an at risk kid. Someone, one of my friends, I don't know who it was, told that I was going through a difficult time. And so I saw the school counselor every week and did that in a counseling environment. And it's very easy to have moments where you say, why me? Why is this happening to me? And Ellen Schenken said to me, why not you? I go, shit, you're right. Why not me? Right? And so the grit and the resilience and all of those things got me to a place of, wow, all of these things happened for me, and none of us are exempt from the risk of hard things happening to us. I'm 49. I'm more than halfway through my life, statistically speaking. Right. But nothing's guaranteed, right? Accidents happen all the time. And so I think it's an imperative for us to show up with conscious intention and a joyful, grateful heart to go make the impact that you want to go make. You have to live your life on your terms. That is your responsibility. That's what I've learned in that difficulty, to say great. How do I serve the world? How do I make an impact? Because I think one of our responsibilities is to be a good descendant. My kids do not know my grandparents, their great grandparents, they never met them. They don't know their names. And so in about two generations, no one's going to know my name. But you know what? I'm not going to take on hedonistic tendencies to satisfy whatever my wants of the world are at the cost of being a good descendant. And so I want to make good choices and leave the world a better place for my kids, kids and their kids. And that's a good legacy that I think you should leave.
Craig Andrews    13:36
I love that. I absolutely love that. One of the things that you said. So when you were going through all this, you mentioned the importance of community.
Jerry Macnamara    13:45
Craig Andrews    13:46
And so what was your community and how did that help you in that era?
Jerry Macnamara    13:54
Hmm. Well, first of all, I think community is everything. Community is connection. Community gives life meaning. Because I think sometimes people think we do life alone, we don't do life alone. And so you just have to say, who are the people around me? Who is my tribe? And really, for me, that's values alignment and impact alignment. What's the dent that I'm going to try and go make in the world? For me, it's a better world through better business because I think that's the skill set that the world gave me. And so I'm going to try and go do that. But I don't know. Isn't life just more fun together? When you look up, when are you having the most fun? It's when you're doing challenging things, when you feel like you're doing aligned work and you're doing it with people that you love.
Jerry Macnamara    14:57
I think that's a core piece that when you lose community, I think that's when you start to lose hope, and that's when bad things happen.
Craig Andrews    15:10
So, for business leaders, what type of communities do you recommend? What do you recommend? How do you find it?
Jerry Macnamara    15:21
So, for you, you just came back from a mastermind. I was just looking this up. It's somewhere on my personal blog, and I said the biggest mistake that I made as a senior leader in business was that I had never gotten a business mentor, a business coach, or a business roundtable. And I think that's a great place to start to minimize. I'm in this alone. I have the impostor syndrome. There's other really talented, really capable people who are going through the same exact things as you, and I believe it. We're better together. And if you can just get out of this place where your ego gets in the way. The ego is the enemy. I love Ryan Holiday's book, the Ego is the Enemy. I mean, when you start thinkiNg, know, how does this impact me versus how does it impact the company or the community? I think you've lost your way a little bit. And so, yeah, find people around you. I mean, one of the things that I do is every Thursday, so later on today, from two to 03:00 I run office hours, and it's a free come as you are, come as you can. We've had, like, 300 people, 397 people come since November 2019, since I've been doing it. And it's just the opportunity to come in and say, hey, I have this hard thing going on. Do you have any ideas for me? And you get not only me, but whoever's there that day, usually there's five to 1215 people that show up. But there's lots of different communities. Whether it's your church community, whether it's your volleyball league, whether it's your business association, you have to have people around you to live a life of meaning.
Craig Andrews    17:13
Yeah. The person who leads our mastermind, one of the things he says, every mastermind, he says the answer is in the room. Whatever problem you're facing, the answer is in this room. He's not saying he has the answer.
Jerry Macnamara    17:33
That's right.
Craig Andrews    17:35
He's saying somebody in that room has the answer to whatever you're facing. And it sounds like that's what I hear you talking about in all things.
Jerry Macnamara    17:46
Because what happens is, oh, hey, I know a guy. Which is how it always started for me. And it was my wife's idea. I give my wife all the credit and all the things, because people would say, oh, I know this guy, Jerry probably can help you. And I'd get the, hey, do you have five minutes? Which it's never five minutes. So she said, why don't you just put, like, make an hour in your week and allow everyone to come during that? Have it. We now have a core group of people who show up on a regular basis. Some just swing in for a session, but I don't always have the, you know, over the last four years, Craig, the fun part about it is the communications used to come through. You know, Ryan dement is talking to Isaiah Rosic and Nathan is talking to. I mean, those are the fun things that happen where the community sustains and nourishes itself. You just happen to be the connector and the platform for it. And that is an amazing service. It is so humbling, for sure. Yeah.
Craig Andrews    18:50
So we're running out of time, but there's two things I want to make sure we cover.
Jerry Macnamara    18:56
Craig Andrews    18:57
We wrap up. One of the things that you said was you talked about the situation with your mom, but you said later in life you reconciled and you experience true forgiveness. Can you tell me what that means?
Jerry Macnamara    19:14
Yeah. So, for me, I experienced forgiveness at two levels. One was when I realized that I had to release myself from the burden that I was carrying. It was too heavy to walk, and so I had to offload that. And so I wrote my mom a letter and told her that I forgived her and forgave her. That was a moment of release for me. And then a second moment came when my mom really acknowledged her actions and the impact, and we had a really great man emotional moment. And that was like it all just fell. Know? My mom was a fallible human being just like I am. Craig, let me raise my hand. I'm not a perfect human being. I have made so many mistakes over the course of my. So, you know, it's just that moment where you say, it's okay. Neither of us have to have this burden because it's not serving us. And I say this all the time. If our thoughts, our feelings, or our actions aren't serving you, change them. You're the only person that can. And so I had that moment of the next level of what I call true forgiveness. It didn't matter. Everything that we had happened was in the rear view mirror, and we had this just beautiful life together in the front windshield. No one did more with know Willy Wonka's golden ticket to life than my mom did. It was amazing. She got to see me get married. She got to see my two kids. All incredible things, because I was open to rekindling a relationship and having forgiveness. Because, again, if all of us are judged on our worst days or our worst moments, none of us stand up. None of us. And so we all have to be on bent knee and say, I missed the mark there, Craig. I'm really sorry that that happened. That's not how I aim to show up as a human being. And then we have to be owners of our side of the relationship to say, yeah, I'm a fallible human being, too, and I'm doing the best that I can, too.
Craig Andrews    21:35
Well, thank you for sharing that. It's both tender and powerful.
Craig Andrews    21:44
I can speak for myself. There are relationships in my life that I'm trying to figure out what forgiveness looks like and how to put that to work. I'm sure I'm not alone in that. And so I hope people take inspiration from your story because you had a lot to forgive, but how powerful that forgiveness was in your life.
Jerry Macnamara    22:09
Yeah. And I think there's for me, if I can share. I did a lot of work on myself and who I wanted to be and how I wanted to show up and bringing conscious intention. I just didn't float like a leaf in the wind. It was like, no, here's the type of person that I want to be. Here's how I want to show up. I think about things in terminal states. So I'm very clear about what I want people to say at my funeral, what I want them to say to my kids and to my wife and boy. I couldn't be the person that I wanted to be if I held on to that frustration, that disappointment, that anger, all of those things that go along with broken relationships. And so, I don't know, I just ask people who are holding on to those things, how's it working out for you? Because you can't be your best. I could not be my best until I could get to a place of peace to say my mom was doing the best that she could. And in societal's norms and expectations, it wasn't great. But when my mom was healthy and great, there was no one better than my mom. I mean, no one. Everyone loved my mom. I remind people that if it's not working out for you, then change it. Have the hard conversations. I held my mom's hand so many times. Two bouts of lung cancer, heart valve replacement, multiple skin cancers. I mean, you name it, my mom. Twelve inches of bowel taken out. We used to call her the ox. So say what you need to say. If not for them, for you. So that you can own your 50%. I only own 50% of our relationship. Today. I came prepared. I was ready for it. I was going to own 100% of my 50%. Now. If you didn't want to have a great time, then we weren't going to have a great time, because I'm only 50%. So when you look up, my mom wasn't ready to own her 50% of the relationship at a certain part of our life. And then she did. And it was wonderful and it was magical. But you have to just own your 50%.
Craig Andrews    24:41
That is such great advice, Jerry. I could go in for another hour. I easily could. This has been so amazing. I think you have so much wisdom to share with people. Obviously, one of the places they can capture some of this wisdom. Is your show best places to lead? How else can people reach you?
Jerry Macnamara    25:01
I think that the two best places are to go to, our website. And if you ever want to come to office hours, Craig, I'd invite you to come to office hours. It's a fun group every Thursday, two to 03:00 Eastern time. You can see the link at the top of that page. And we're pretty active over on LinkedIn. So if you just search my name, Jerry McNamara, you'll find me on there as well.
Craig Andrews    25:25
Well, that's great, Jerry. I do hope people reach out to you. I do hope they shop office hours. Thank you for coming to leaders and legacies. And thank you especially for your commitment to impact 5 million lives in the next five years. I believe you're going to, based on our conversation today, I believe you're going to pass that.