Walk The Walk of a CEO with Michael Chernow | Monday Moments

Summary

Kreatures Of Habit Podcast: "Walk The Walk of a CEO with Michael Chernow | Monday Moments"

Release Date: March 24, 2025

Introduction

In the latest solo episode of the Kreatures of Habit Podcast, host and founder Michael Chernow delves deep into his personal journey as a CEO and founder. Unlike the traditional format where Michael engages with guests, this episode focuses entirely on his own experiences, lessons, and insights garnered over more than a decade of leading businesses in the restaurant industry and now steering the digital brand Creatures of Habit. Titled "Walk The Walk of a CEO with Michael Chernow | Monday Moments," this episode serves as a treasure trove of wisdom for current and aspiring CEOs, founders, and entrepreneurs seeking to refine their leadership and operational strategies.

Embracing Patience in Business Launches

Michael begins the episode by emphasizing the critical importance of patience post-launch. Reflecting on his early tendencies to react swiftly to underperforming ventures, he shares a transformative lesson:

"Don't try to fix something that is not working as soon as you launch it." [00:XX]

He recounts how, initially, his impulse as an operator was to address issues immediately. Over time, however, he recognized that giving a project time to mature allows for natural growth and the identification of genuine traction points. This shift in mindset was pivotal in fostering sustainable business development and avoiding premature interventions that might stifle potential success.

Delegating Responsibilities to Avoid Bottlenecks

One of the standout points Michael discusses is the necessity of delegation, particularly concerning vendor interactions:

"Don't make yourself the point person at the company to these vendors... being the point person will, I promise you, be a bottleneck in your business." [03:15]

He advises CEOs to appoint dedicated points of contact within their organizations to handle vendor communications. By doing so, leaders can focus on scaling and evolving the business without getting bogged down by operational minutiae. Michael shares his own experiences of initially handling these interactions personally, only to realize the inefficiency it introduced, thereby reinforcing the value of empowering team members to manage specific domains.

Optimizing Time by Limiting Meeting Attendance

Michael tackles the common pitfall of overcommitting to meetings, which can significantly drain a CEO's time and energy:

"Don't join every single meeting... you should be focusing your time on thinking about how the company is going to grow." [05:45]

He highlights how excessive meeting attendance can disrupt a CEO's ability to engage in strategic thinking and business development. By strategically choosing which meetings to attend and delegating others, leaders can ensure that their focus remains on driving the company's growth rather than getting entangled in routine discussions. This approach also empowers department heads to take ownership and make decisions independently.

The Power of Listening: "Speak Last"

One of the most impactful lessons Michael shares is the art of listening over speaking, particularly in leadership settings:

"Speak last... you put much more progress in listening than hearing your own voice." [09:30]

He narrates a pivotal moment from his early career when a seasoned restaurateur advised him bluntly:

"In the next board meeting, shut your fucking mouth. You feel the need to hear your own voice way too much."

This candid advice was a wake-up call for Michael, illustrating that incessant self-expression can hinder effective leadership. By prioritizing listening, CEOs can glean valuable insights, foster better team collaboration, and make more informed decisions. Michael acknowledges that while expressing passion is essential, restraint often leads to greater organizational harmony and progress.

Accepting that Not Everyone Will Like You

Transitioning from personal reflection, Michael touches on the challenging yet liberating realization that universal likability is unattainable:

"Not everybody is going to like you... don't sacrifice other people liking you for what needs to get done." [14:10]

As someone who thrives on building relationships, this was a significant mindset shift for Michael. He underscores the importance of prioritizing business objectives and ethical decision-making over seeking approval from every individual. By accepting that not everyone will favor his leadership, he can make more objective and effective decisions that benefit the company as a whole.

Seeking Solutions Over Possessing All Answers

A hallmark of exceptional leadership, according to Michael, is the ability to find answers rather than having all answers upfront:

"Great CEOs don't know all the answers, but they figure them out." [17:05]

He elaborates on the importance of surrounding oneself with knowledgeable team members and fostering a culture of collaboration. Michael credits his success to his willingness to ask for help and leverage the expertise of others, ensuring that no challenge remains insurmountable simply because he didn’t have the immediate solution.

The Centrality of Relationship Development

Concluding his series of lessons, Michael emphasizes that relationships are the bedrock of successful business operations:

"Building relationships that are long term make doing business a lot easier and a lot more successful." [20:50]

He reflects on his extensive experience hiring and firing over a thousand individuals, maintaining that nearly a hundred percent of those he had to let go would choose to return if given the chance. This is a testament to his ability to cultivate respectful and enduring professional relationships, even in challenging circumstances. Michael believes that delivering difficult news without burning bridges preserves one's reputation and paves the way for future collaborations.

Conclusions

Michael Chernow's solo episode of Kreatures of Habit offers a comprehensive roadmap for effective leadership and entrepreneurial success. By advocating for patience, strategic delegation, active listening, acceptance of imperfection, relentless problem-solving, and strong relationship-building, he provides actionable insights that resonate deeply with both seasoned and emerging business leaders. These lessons underscore the nuanced balance between personal growth and organizational development, highlighting that successful CEOs are those who continuously learn, adapt, and prioritize the collective well-being of their teams and ventures.

For listeners seeking to enhance their leadership skills and cultivate productive business habits, this episode serves as an invaluable resource, blending personal anecdotes with practical advice that can be seamlessly integrated into their professional lives.

Notable Quotes

• "Don't try to fix something that is not working as soon as you launch it." [00:32]
• "Don't make yourself the point person at the company to these vendors... being the point person will, I promise you, be a bottleneck in your business." [03:15]
• "Don't join every single meeting... you should be focusing your time on thinking about how the company is going to grow." [05:45]
• "Speak last... you put much more progress in listening than hearing your own voice." [09:30]
• "Not everybody is going to like you... don't sacrifice other people liking you for what needs to get done." [14:10]
• "Great CEOs don't know all the answers, but they figure them out." [17:05]
• "Building relationships that are long term make doing business a lot easier and a lot more successful." [20:50]

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This summary encapsulates the essence of Michael Chernow's insights on leadership and entrepreneurial success, offering readers a thorough understanding of the episode's key themes and lessons.

Transcript

[A]

I have probably hired well over a thousand people in my career, in the world of restaurants and now in Creatures of Habit, well over a thousand. And I've probably fired personally hundreds of people. But I would put my money on if I had to go back to every single person that I've personally had to fire and ask them to come back and work with me, close to 100% of them would do it. Why?

[B]

What's going on? Podcast Family My name is Michael Chernow and this is the Creatures of Habit podcast. Our habits will make us or they will break us. I've lived on both sides of the tracks and have experienced some of the best and the worst that habits have in store. The decisions we make on a consistent basis truly define who we are as human beings. This episode will will be a solo episode. Where traditionally I interview guests. This is a solo episode where I share with you guys experiences that I've had, things that are relevant in my life today that I think could potentially be interesting for you to hear, things that I simply just want to share or quotes or activities that I've done over the last few weeks that have inspired me. So sit back, relax and get out your pen and paper because what you hear in this podcast could potentially make.

[A]

Some big changes in your life. Let's go. What up everybody? Today is a Monday moment. This will be a 10 to 15, maybe a little longer, maybe a little shorter, 10 to 15 minute long episode, solo episode of me sharing things that I have been interested in, things that I have learned, experiences, some stories, and today's episode, I want to talk to you about the things that I've learned or that I am learning about being a CEO and founder. I actually have a list here that I'm probably going to glance at every now and again because I wrote these things down because I think it's really actually important for me to hear them, hear me say them. But I think for anybody who is currently a CEO, founder or a founder or a CEO or aspiring to be one, these are some lessons that I have learned over the last decade plus about what it means to be a strong founder, strong CEO. And I think that they will be interesting for you to hear. So to kick it off, something that is hard, though I have learned as a leader of a business is especially in the world of, well, it actually kind of is in any business. But I'm currently the founder and CEO of Creatures of Habit and in the world of digital brand, digital business, this was a lesson that I had to learn. I had no choice I had to learn this because, well, I'll get right to it. Don't try to fix something that is not working as soon as you launch it. So if you launch something that you are very passionate about that you think has strong potential, if you launch it and it doesn't work right away, don't immediately try to fix it. As an operator, which I have been for a long time, I'm probably not the greatest operator on the planet, but I have had to be an operator for many years, especially in the world of restaurants. And now in creatures of habit, you want to fix problems. My sort of role has been to come up with an idea, launch it out into the world, see what happens, and then ultimately fix the problems that come along with launching something new. I have gotten so much more patient at giving things time because early on in my career, I would come up with an idea, put it out there. If it didn't work immediately, pull it, or try to fix it right away. And what I've learned over the years is that is not always the right solution. You have to give things time, and you have to have confidence in your decision immediately. Now, I'm not saying beat a bad, you know, continue to beat something until, you know, you lose your ass. But I am saying that you have to give things time. And that that lesson I've learned through surrounding myself with really, really great people, because I can't help the urge to want to stop something immediately if I don't see success as a leader. I have learned to have patience and to give things ample time to either take shape or show that they are not working. That's been a big one for me. And when you try to fix things right out the gate, when you make changes immediately, you actually don't give the idea an opportunity to develop, to flourish, and to see where it gets traction. So give things time. Don't run to fix things if they don't work right away. It's been helpful for me. Don't be the point of contact for your vendors. If you have a team of people around you, you as the owner and the founder, the CEO of the company, you should not be the point of contact because you are busy building your business. And if vendors need to get something done, but you're out there working on scaling the business or evolving the business, having vendors reaching out to you personally are going to draw and drag down your ability to do other things that should not require your attention. I mean, to do other things that are more important than managing a question from a vendor. So don't make yourself the point person at the company to these vendors. I think being involved in the relationship, kicking off the relationship, but you being the point person will, I promise you, be a bottleneck in your business. I've seen it happen over and over again and I've been guilty of this. So really try to delegate poc, which is point of contacts within your organization, so that you don't get bogged down by vendor emails that are waiting for you to respond to. It's 1:11. I'm closing my eyes because I make the exact same wish every single time I see 1:11 or 11:11. I've been doing that for a long time. Don't join every single meeting. So this is another thing that I had to get used to. Me being on every single meeting could very easily derail meetings. Not only does it clog my schedule up, I try to have as clear a schedule as possible. Now it doesn't happen all the time, but if my schedule is clogged every single day with meetings in every single department of the business, it gives me very, very little time to a think about how we're going to grow and, and get things done. So meetings are important. I like to have fewer meetings and especially me as the founder of the company, I should not feel it necessary to be participating in every single meeting or even half of the meetings. If you have a strong team of people around you that are conducting well, then have a meeting with that person once a week to get caught up or have that person write you an end of day or an end of week recap, email you. Being on all those meetings tends to make it more difficult for the people that are actually at the helm of those departments than necessary. Because most of the people that are on a meeting when the founder is there will honestly think of the founder as the person that needs to hear the information and then ultimately look to the founder to make the decisions. If you're doing it right and you've surrounded yourself with the right people to lead a specific department, whether it's marketing, operations, finance, supply chain, whatever it is, you want those people to make those decisions. You want to empower those people to make those decisions. And when your presence is there, whoever else is on that meeting is going to just kind of subconsciously think that you are the one that is going to make those decisions. And then they will potentially disregard the actual people that you've put in place to make the decision. So don't be on every single meeting. It's not necessary. You should Be focusing your time on thinking about how the company is going to grow. Speak last. This is another hard one. Speak last. Or potentially don't say anything at all. I've also had to check myself and get checked by other people in this arena. I have found so much more progress and productivity at the companies that I've launched when I am observing and not needing to hear my own voice. So obviously, if there's something that I am incredibly passionate about, I will make my voice heard. But most of the time, I observe and I allow the people that are on the ground, boots on the ground, operating, do most of the talking. I'll tell you a quick story. I remember when I was in my early 30s and the Meatball shop was kicking ass, and we had a big board meeting and one of the guys that I brought in to buy some equity and to help us scale meatball shop was a legend in the world of restaurants and probably 25, 30 years older than me, founded one of the most iconic American restaurant chains in the world. And we were in this meeting, and after the meeting, this guy took me aside and said, hey, can I, can I take you out for a cup of coffee? And I said, sure. And in my mind I'm thinking, oh, man, he's going to take me out for a coffee. He's going to tell me how awesome I am, how proud he is, and da, da, da, da. And we sat down for that cup of coffee and he looked at me and he said, can I be frank with you? And I said, yeah, of course. He said, do me a favor. In the next board meeting, shut your fucking mouth. Don't say a word. And like, I went white as a ghost. And he's like, you feel the need, the need to hear your own voice way too much. And almost every time you open your mouth, you put your foot in it. You'd be far more successful if you listened. And honestly, that was a hard lesson to learn, but my God, was that some of the greatest advice that had ever been given. So as an emerging or up and coming or young entrepreneur, we feel the need to hear our own voice. We feel the need to get our opinions out there. You have so much opportunity to do that offline, to do that after a meeting, to listen to what other people are saying, because you're gonna learn so much more from listening to what other people are saying than hearing your own voice. You already know what you're thinking. You learn from others. So for me, speaking last has been a powerful component of my entrepreneurial journey. Not Everybody is going to like you. Not everyone is going to like you. And that's for me as a people person, as a people pleaser. For a lot of my life, I've been so successful with getting people to like me. I want people to like me. And now, as I'm growing into my career, which I believe is still so young, I mean, I've got so much career ahead of me, 40, 50 years ahead of me of career, I'm getting more comfortable with this idea that not everybody is gonna like me. And that's okay. It's just simply okay. I don't think I need to be friends with everybody. And I never thought I needed to be friends with everybody. But I did think that getting people to like me was a big part of the, of the, of the picture. And it's just. It just doesn't have to be. So I'm not saying be and be an asshole or be difficult. I am saying don't sacrifice other people liking you for what needs to get done and what needs to happen. It's okay if not everybody in the room doesn't like you. And that's become important for me to know. As a founder and a CEO, it comes a lot easier to some people. But for people like me, who are real relationships people, I'm like a real relationship, emotionally intelligent entrepreneur. That was a hard lesson to learn. That was a hard one for me to swallow. If I had to boil down what a great CEO is. It's not about what you do every single day operationally. It is actually about. And it's also not about having the answer to every single question that's asked. But a great CEO will get all questions answered. There's a big difference between you personally as a CEO, having all of the answers to all the questions and being great at getting all the questions answered. So I might not know everything. I definitely don't know everything. But what I could say I've been really, really good at is figuring out how to get the questions answered. I ask for a lot of help, and I surround myself with a lot of people that are good at answering the questions that I just don't know. And I'm not uncomfortable going to those people to get the questions answered. So great CEOs don't know all the answers, but they figure them out. And I think that is a good sign if you're one of those people that will do whatever it takes to make sure that those questions get answered. And it might take a little bit of time, but there's nothing wrong with saying, you know what? I don't know the answer to that. I'm gonna find out though. That I guarantee you. And then lastly, I think something to really be mindful of is relationships. What I have been very, very good at over the course of my career and just in my life is relationship development. I would argue to say that is probably my strongest skill set, relationship development. I go beyond above and beyond to develop relationships. It is in my DNA. I am a relationships person. I've probably hired well over a thousand people in my career, in the world of restaurants and now in creatures of habit, well over a thousand. And I've probably fired personally hundreds people. But I would put my money on if I had to go back to every single person that I've personally had to fire and ask them to come back and work with me, close to 100% of them would do it. Why? Because I believe in relationships. I have learned how to deliver bad news in such a way that does not burn a bridge. Burning bridges is going to tarnish your reputation. Your reputation in business tends to be the most important thing. Building relationships that are long term make doing business a lot easier and a lot more successful. Those are some of the lessons that I've learned as a young CEO and founder. And I hope that whether you're a CEO, founder or not, I hope that some of these tactics and lessons that I've just talked about could help you just in life in general. Because it is some of this stuff is like real common sense stuff that when applied, really make a massive difference. Share this podcast with a friend or family. I hope you enjoyed it. I hope you have a great week. Great day. Until the next one, y'all. Peace.