What if the secret to being a successful entrepreneur had nothing to do with your business plan, resources, market size, or strategy? If your success or failure weren’t dependent on how much money you have, where you grew up, or the level of education you received? Here is the truth, the difference between success and failure is right between your ears.
In his new book Mr. Monkey and Me, business leader, Mike Smerklo, lays bare his broad range of experiences and mistakes, as well as lessons he’s learned from renowned entrepreneurs. In the book, Mike gives readers an actionable approach to mental toughness that will help any entrepreneur start, grow, and run a successful business.
Drew Applebaum: Hey listeners, my name is Drew Applebaum and I’m excited to be here today with Mike Smerklo, author of Mr. Monkey and Me. Mike, I’m excited you’re here. Welcome to the Author Hour podcast.
Mike Smerklo: Thanks for having me.
Drew Appelbaum: First, tell us a little bit about your professional background?
Mike Smerklo: I was the first person in my family ever to go to college and like a lot of folks in that situation, I came out just trying to get a job and make a little bit of money. I started off as a CPA, of all things. I was a public accountant, and I walked in and I think three days in said, blank, what have I done? I did that for a couple of years and then I went to investment banking, I really learned in both those jobs the fundamentals of business.
I hated the jobs, they kind of sucked the soul out of my body, but they’re really good foundations. Then I went to business school and moved out to Silicon Valley in the late 90s. Did a little more investment banking and then really began my entrepreneurial journey. I went to work for two great entrepreneurs, Mark Anderson and Ben Hurwitz, for a startup in the valley in the late 90s.
I did that for a couple of years and then decided to go off on my own and from there, I started what’s called a Search Fund, and raised a small amount of capital to go find businesses to buy. As luck would have it, I bought a business, ran it for 13 years, had a great run. I started my own venture capital firm five years ago, Next Coast Ventures and I run that out of Austin, Texas.
Drew Appelbaum: Nice, congratulations, and what inspired you to write this book?
Mike Smerklo: Well, Mr. Monkey and Me is really about the mental aspect of entrepreneurship and the inspiration came from, not just my own experience, which was certainly filled with a lot of ups and downs, but watching entrepreneurship and helping advise when I was an investment banker. Then watching two amazing entrepreneurs, Ben and Mark. And then doing it myself and now, having invested in over 50 companies. I found the topic of mental health and mental preparation for entrepreneurs to be sorely lacking in content.
It really shows up mostly as the 10 things that Elon Musk does before six AM, or what Mark Zuckerberg eats for breakfast, which, you know, really don’t do you anything, it’s kind of like eating Doritos when you’re hungry. It tastes good for a minute but afterward, you’re still hungry and you feel kind of disgusting. That was the content that was out there, and I really wanted to try and supplement it with Mr. Monkey and Me.
Drew Appelbaum: Now, you mentioned that there are a lot of tips for entrepreneurs in here but can other folks from other walks of life read this book as well?
Mike Smerklo: I think so. Really, what the book tries to lay out, in addition to telling some good cringe-worthy stories of the things I did wrong, it really just tries to lay out addressing the inner voice that I think is in every one of us.
That inner voice for me shows up as fear, uncertainty, and doubt. But the voice in your head that’s telling you, you’re not good enough, you’re not going to make it, or the idea that you’re considering is really a dumb one. I group that all together in a caricature which I call Mr. Monkey. Then I lay out a formula called the shape formula for how to address and overcome that voice and I think it’s certainly critical for entrepreneurship, but I would argue, could be helpful in a lot of walks of life.
Not the Usual
Drew Appelbaum: Now, to kick things off, you mentioned in your book right in the beginning, this book isn’t the usual crap. Well, you don’t use crap. Crap is the edited language. What is the usual crap and how is your book different?
Mike Smerklo: Yeah, I think the usual crap, again, I’m testing myself to use the right words but the usual stuff–will say that–is either very specific to business ideas when it comes to entrepreneurship, how to write a business plan, legal documents for raising capital, things like that. Or it’s the fluff piece, the short-form content which drives me nuts which I eluded to before. I just saw one the other day, it was funny, it was literally “Jeff Bezos‘ Six Tips for Success.”
Now, Jeff Bezos is the wealthiest man in the world, he runs Amazon, he’s been doing it for 25 years. I struggle to think of what six things that Jeff Bezos does right now that’s going to help Sam Smith or Sally Smith who is just starting off in a business, really get ready for it.
So, I think that’s the usual stuff you see and I wanted to do just the opposite–show you the real world, get you ready for the mental aspects, and most importantly, hopefully, provide a bridge to give you the courage and energy to get off the couch and start your business.
Drew Appelbaum: Let’s go all the way to the beginning and tell us a bit more about your childhood and how that formed the inner voice which you call Mr. Monkey.
Mike Smerklo: I came from very humble beginnings, as I mentioned I was the first person in my family to go to college. I was surrounded by a lot of disease, a lot of divorce, a lot of alcoholism, a lot of broken marriages. Not exactly the role models that kind of pats you on the back and says, “You can do it.” And what I drew from that was not a pity for me, but it was really just how much that influenced and challenged me whenever I tried and do something new.
I left Toledo, Ohio, where I grew up with an energy that said I wanted to do something different with my life. I saw a lot of people that were working hard and trying their best but really weren’t achieving much in life. I felt like if I could work hard, get some direction outside of that environment, I could succeed, but every time I went to pull myself up–and I see this all the time with entrepreneurs–Mr. Monkey was there telling me I couldn’t do it.
I was a white male growing up in America in the 70s. I still had it better than most, so I don’t want to take that away. But the point I’m trying to make is that that monkey, that person, that whatever it is that was telling me every step of the way, has always been trying to drag me back down to my roots. That’s what I think a lot of people can relate to and I hope I can help them overcome it as I’ve tried to.
Drew Appelbaum: Now, do you think that everyone out there has an inner voice and Mr. Monkey speaking to us?
Mike Smerklo: I think even Jeff Bezos has Mr. Monkey. I think what the difference though is, I think Mr. Monkey shows up very differently. In my mind, and I’m going to call him a he, he could be a he, a she, an it, it doesn’t really matter. But in my mind, I personified him finally, as a big hairy beast trying to kick my butt. He is omnipresent, he’s always there, and he’s sneaky and he changes.
You know, it’s fun, before I did this podcast, he was on some of my office, I was going to try and get a screenshot of him, but he ran off and you know what he said to me? He said, no one’s going to listen to this podcast, this is stupid, what are you talking about? And he scampers off.
The point is, he’s always there, he’s never going to go away. So really, I’m trying to help myself and others address it, learn from him, and I said turn him into a frenemy. He’s not going to be your best friend, he’s never going to go away, so how do you get something from him and learn from him and grow?
Drew Appelbaum: Are there other truths about Mr. Monkey?
Mike Smerklo: The things I would summarize as truths are I do believe everyone has them, as I said, and he’s never going to go away. I think the other thing is he, in my case, he’s going to find your weak spots and he’s going to pick out things from unexpected areas and he’s really sneaky. Those are the truths.
The other side of that is, you don’t have to listen to them, you can soak up some of the things that he’s going to tell, or he’s telling me and really, maybe there’s some good advice there. But the point is, the other truth is you can manage it.
Knowing that everyone has it and that it’s manageable I think is the first step forward.
Ask for Help
Drew Appelbaum: Now, everyone has these in their life and you talk about some of life’s failures in the book. Tell us about a failure that comes up right now, top of mind, and if there was one, a lesson that came attached with it.
Mike Smerklo: I told a story in the book–I was starting off as a CEO, I bought this company and I’m filled with imposter syndrome. I’m trying to figure out how I could possibly do this job, we were growing, and I needed to hire a head of sales. It’s all in the book, but the short answer is, I made a massive mistake in hiring.
There’s something to be said, that if you hire someone, and I didn’t know this at the time, but when you hire someone with a coke addiction, they turn out to be not very reliable employees. This is one of the hundreds of mistakes that you’ll learn about if you read Mr. Monkey and Me, but it was a huge hiring mistake.
The biggest learning from that was I wasn’t getting help–I was trying to do this all on my own. I see this all the time with entrepreneurs, a general belief that you have to have all the answers, that you need to push forward, and that no one really can understand exactly what you’re doing. The big lesson, and hopefully there’s a few of them in the book, is that no matter what you’re trying to do, someone out there has done it before. So, having the awareness, having the mindset to be thoughtful about where you need help, and then being aggressive at seeking it out.
It was something I got very early on in my entrepreneurial career. I turned a near-death experience–meaning my career as an entrepreneur almost ended very quickly–into something that then became a lifelong habit of seeking help, getting advice, and then trying to put that into practice.
Drew Appelbaum: Talk to us about the shape mindset. What is it and what is the goal of looking at things in this way?
Mike Smerklo: Well, the shape mindset is an aggregation of what I have seen, as I mentioned in the start, from entrepreneurs I worked with and now as a venture capitalist, working with leading entrepreneurs, that are driving amazing businesses. What I tried to do was summarize the attributes that I see of mental health.
Where do I see entrepreneurs, myself included, making mistakes and learning? What are the core attributes that can really provide a foundation for success and mental toughness?
The shape formula, I am happy to go through it, but it’s five simple letters. It’s self-awareness, help, authenticity, persistence, and expectations. Each one of these, they can be taken on their own, but I think when you build upon that, like Maslow’s hierarchy of needs if you will, it really does provide a framework for mental toughness and tenacity. I think will get you through all the ups and downs that are 100% part of being an entrepreneur.
Drew Appelbaum: Now how easy is this process to incorporate into your life?
Mike Smerklo: Well, I think like everything else, I wish I could say easy to understand, hard to put into practice, but I don’t mean to be daunting. I think that when people read it, I don’t think you are going to find, to be very direct, you’re not going to find anything and say, “Oh my gosh, I never would have thought of that before,” but I tried to put it forward in both a framework that is easy to understand.
At the end of each chapter, I give four or five of what I call Monkey Minders, which are ways to take each of these attributes, the five that I just mentioned, and really put them into practice, things that I have learned or seen others do. So, my goal of the book is to help people one, understand the importance of mental tenacity and healthiness, and two, have a framework and then provide them with very specific and actionable things that they can do to begin to develop their own mental shape.
Drew Appelbaum: You bring up someone in the book, Greg Reyes, and you mention him almost as a semi role model for you. He is quite the character in the book. Tell us about your experience and time working with him.
Mike Smerklo: Well Greg is a fascinating character. I mean this is an individual who was the alpha male of alpha males in Silicon Valley in the late 90s, he took a business public, made hundreds of millions of dollars, and then had a great tragedy. He ended up going to prison for a couple of years for some technicalities around backdating stock options. So, he is a wonderful human being that has gone through an amazing experience.
But the point of why I bring up Greg is he was really my first real example of what I thought a CEO or entrepreneur should be. I describe him as George Clooney meets NFL linebacker, a very powerful alpha male character. When I thought of my own monkey and I was fearful and nervous, I looked at somebody like Greg and said, “Boy that’s who I should be. I should model myself after him,” and for some period of time, I tried to show up like him as an entrepreneur.
I talk about in the book other role models like Ben Horowitz, who was a great entrepreneur who’s gone on to be a legendary venture capitalist in Silicon Valley. I also try to role model my behavior after Ben in certain situations.
The point of it is, is that it is great to have role models and mentors that you see out there, but in some way, someday, you have to find yourself, your own authenticity.
I talk about in the book that Greg was a great initial person for me to model myself on, but I didn’t really click in, in terms of a leader and as a successful entrepreneur, until I candidly found my own voice and some blend of all of the above.
Drew Appelbaum: You have a great story in the book and you mentioned that moment where you found out you are not Greg and you needed to find your real authentic voice. Do you remember that moment and can you talk us through it?
Mike Smerklo: The company was growing rapidly and I brought in a new head of HR. He was a really wonderful guy named Ray Martinelli, and he started to develop some very strong HR practices, and one of them was to rank every employee. We probably had about 100 employees at the time, and so we would rank them on a two by two grid, like a consultant would, and say, “How good are they at their job and what’s their potential?”
We were going through this process and it was one of those days when you have been in a conference room all day, your head is starting to wander, and I am sitting there trying to act like I am alpha male Greg. I got my feet up on the table. I probably had a chew on my mouth, embarrassingly enough, you know trying to act the whole part, as I am going through the process thinking to myself, “Boy, this is really good stuff, this is what a real entrepreneur CEO does.”
Then suddenly Ray puts up a name on the board in the category of need to move out of the organization, which means fire. I will call the person Donno because I want to protect his privacy a bit, but Donno was the lifeblood of the company. He was one of those employees that was kind of a jack of all trades master of none but one that everyone loved, one that brought forth the right energy, really was a cultural ambassador around the company, and in a lot of ways was the glue that kept us all together.
But he didn’t have the attributes that really meant that he should be continually promoted through the organization. It was at that moment where I thought about what a role model like Greg would do. Fire him immediately, get him the hell out of here. I thought about what a role model like Ben Horowitz would do, and Ben was this just incredibly balanced but a right to the point person and Ben would probably say, “Put him on a plan, see if he makes it. If he doesn’t make it, move him out.”
Then I thought about what does Mike want to do? I had gotten into entrepreneurship because I really wanted to improve my life but really I wanted to build something special. I wanted to have a company that meant something. I wanted to have a place to work that people enjoyed and that they were passionate, and they had a really strong culture. So, I turned to my team and said, “I don’t know what to do.”
You can imagine as I am role modeling myself as an alpha male when I turned to my team and said I don’t know what to do, my imaginary friend, Mr. Monkey is jumping up and down, “What did you say? You did you just say, you don’t know?” But anyway, it starts yelling and screaming, and really the short answer of this long-winded story is, it forced me to ask, “What do I want?” And it was really the first time I think in my entrepreneur journey where I said, “I want to do what’s right. I want to have this person be part of the team,” and my whole team agreed.
We found a great solution and it turned out to be a brilliant thing because this individual Donno went on to help us in multiple ways but I never would have gotten there had I not really peeled back, gotten to my authentic self and candidly, putting Mr. Monkey aside and didn’t listen to all the BS he was trying to put my head.
Drew Appelbaum: I love that story of finding your voice and with all the highs and lows in what you call the rollercoaster of entrepreneurship, would you do it again? Would you do it differently or would you be a CPA and just take the safe road?
Mike Smerklo: Absolutely not. Let’s me say it this way, I laugh because ignorance is bliss in some part of your life. I would do it again, I haven’t done it again largely because I know how hard it is. So yeah, the point in life, it was the greatest thing that ever happened to me professionally. It allowed me to elevate my life and my social-economic standing more than I could ever imagine. I like the life I have now, I would never even dreamed of it.
If I go back to my 16 or 18-year-old self, having said that, I do now know how hard it is. I really respect anybody who’s bold enough and strong enough to jump into the arena. I think the difference is in what I try to portray in the book is just to understand what you’re getting into. You are jumping into a big deep cold pool of water with lots of waves. It doesn’t mean you shouldn’t do it. I think right now, the world needs more innovation and more entrepreneurs more than ever.
It just means be thoughtful, be aware, and if you can, take some of these tools to prepare yourself as you start off on the journey.
Drew Appelbaum: Now your stories in the book are incredibly entertaining and you could see the whole cycle of forming who you are now and I think it is a really great story but inside of it, you fight against writing a memoir. What was the pushback about writing a memoir?
Mike Smerklo: Well, I call them anti-memoir because for anyone listening, you know Mike Smerklo is not exactly Jeff Bezos or Mark Zuckerberg. So, it is not a household name. My story, I joke, it’s been a good story but it certainly is not in the entrepreneurial hall of fame. I did not think, and maybe this is the monkey, I didn’t think it to be memoir-worthy and really that wasn’t the point. The point wasn’t for me to sit back and have my peers go, “Wow, look at that great story, he’s so amazing.”
That’s not the point, and I think when you read it, you’ll quickly realize that’s not the case. More it was a matter of trying to give back, trying to help other entrepreneurs or aspiring entrepreneurs take the plunge. As I said a minute ago, I believe that entrepreneurship is the most critical thing in the world right now.
Some of the problems we’re facing, I laugh and say, “Do you want the government to solve it? Do you want not-for-profits to solve it with the best intentions, or do you think entrepreneurs are going to tackle some of the biggest and most challenging issues facing humanity and our planet?”
I am going to bet on entrepreneurs. So then the question is, how do we get more entrepreneurs to raise their hand, how do we get more diversity in entrepreneurship? How do we get more people that are thinking of big ideas but just have that fear and the monkey and voice in their head telling them not to do it, how do we get them to step forward and raise their hands? That is the whole purpose of the book and why I hope people do give it a read and I hope that is what they get out of it.
Drew Appelbaum: Well, I’m glad you put Mr. Monkey aside for a bit as the book is incredibly enjoyable to read, and writing a book is no joke, so congratulations on finishing. Now, if readers could take away one thing from your book, what would you want that to be?
Mike Smerklo: In all seriousness, I think that if someone like me, without great role models, without education at the start, can find a way to get through this and get to some level of success, I think just about anybody can do it. I really do, and I don’t mean that to be humble bragging or too self-deprecating, but I believe that anyone can do it.
I just want them to have the right framework and to raise their hand and really go after it because entrepreneurship done right has the potential to change individual’s lives, communities and at the grandest scale, the world, the planet, and humanity itself.
So, the one thing that I hope they take away is if I can do it, anybody can. But also there is a tool kit, there are some resources and I believe that you can apply them. Your chances for success can go up dramatically.
Drew Appelbaum: Mike, this has been such a pleasure and I am so excited for people to check out this book. Everyone, the book is called, Mr. Monkey and Me, and you can find it on Amazon. Now besides checking out the book Mike, where can people find you?
Mike Smerklo: Well, on my website, which is mikesmerklo.com that’s the easiest one. We’ve got some great resources for entrepreneurs. There is a lot of content there, it also has a quiz that is all about the mental readiness to be an entrepreneur and it is not a pass-fail so don’t worry about that, but it is there to help you think about what attributes you may need to improve on. Then on social, I am Mike Smerklo on all of the major social channels.
Drew Appelbaum: Awesome, Mike thank you so much for coming on the podcast today.
Mike Smerklo: This was a blast. Thanks for having me.