Overcoming The Struggles of Leadership and Embracing The Fears of Entrepreneurship, A Review of Ben Horwitz's The Hard Thing About Hard Things

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John: Welcome to another episode of the present professional today. We’re here to talk about entrepreneurship from a different lens, looking at it from a realistic perspective with the review of the book, the hard thing about hard things. And, you know, what that book really goes into is the things that maybe we don’t talk about when it comes to being a CEO or starting an entrepreneurial or startup venture and the things that really go along with that struggle. So here in this conversation, we’re going to talk about some of the ways to endure that struggle, some of the ways to look at creating your culture, some things about the ways that you can make it through and enjoy the process. So speaking of that, it takes courage first to take the lead and it takes courage to step out on your own to follow your dreams to even, you know, you’re just starting a side hustle. Maybe it’s not the dream or the passion. Yet, you know, there’s there will be highs and lows. There will be struggles. There will be frustrations. But then in the end, you know, are you learning something? You know, are you moving forward in the face of fear? And, you know, one thing in this book, the hard thing about hard things by Ben Horowitz that, you know, Tony and I both read and, you know, want to bring a lot of the highlights into this show. The one thing that really stood out for me was the courage development process. He talks a lot about the difference between fear and courage, and that courage isn’t about not having fear, it’s about moving forward in the face of fear. So every time you face a choice, whether that’s your first choice to step out on your own, the choice to go promote your product, to believe in your product, your process, your service, and move out there and step in front of new crowds, put yourself out there, the more that you do that is where you develop courage. Now, do different folks have different baselines? Sure. Different starting points. And I’m sure there’s a lifetime of conditioning that says, where is your baseline courage at whenever you step out to do your own venture? no matter where you’re at, you move forward by moving forward in the face of fear. So every time you face a choice, you know, the one that is popular and easy and wrong, is the one that doesn’t take much courage. That’s letting fear win by taking the easy route. But then, when you choose to dig in and do what might be a little lonely, but it’s a more difficult and right choice, and right choice for you, when it comes down to it as the leader, as the CEO, as the owner and operator, that’s how you build courage. And that was the first one that stood out to me. Where are you at, Tony?

Tony: Man, you know, for me, it was really looking at the theme of the entire book. To me, what I noticed is that the reoccurring theme throughout the chapters and in the stories he provided and just kind of like where he was coming from was really about survival. And that was like the number one takeaway for me is that Really, entrepreneurship is literally about surviving. So if you’ve ever been an entrepreneur in any way, then you then you feel me on that. You know where I’m coming from, because when you have to create your own income or create your own revenue, You you see the world different and so he he kind of really goes in depth about that but you know i want to just start there and say that survival is the first step i think like when people step in entrepreneurship you have this huge dream and vision and. things you want to accomplish and you see yourself at the mountaintop or at the top of the hill or whatever your visualization might be but getting there is such a process that you don’t you cannot see what you don’t know is coming so it’s potholes there’s traps there’s hard times you know there’s so many parts of it it’s almost like You know, going to war to it to a degree, like when you are a soldier and you step out into the battlefield and you feel that you’re going to win the war, but you don’t know how you’re going to win. And so I translate a lot of what he said to to that right there is just having that survival mindset. A couple of things he said that kind of relate to that to me. One was when you’re running a startup, you only experience two emotions. He said you experienced euphoria and terror. And I’m like, that’s interesting. I don’t know how 100% true that is, but I do get it. Like he talks about a lot of times where when you run in a company and you are potentially short on cash flow. And you get ready to have to fire people that you really wanted to hire and you vetted them and you selected them and you did all the things to make the right hires. But then you are CEO and you have to let them go because business isn’t going the way that you projected or Things happen in the market. I’ve experienced that. I’ve experienced having to let people go in the first company that I founded. And so, and I still run that company, but having to let people go, it was, it was difficult. And, but you have to make those choices. And then the other piece that I thought was interesting back to the survival pieces, he talked about eating dirt and he called it something else, but I’m using the word dirt for our PG 13 audience out there. But. He said, if you’re going to eat dirt, don’t nibble. And I can relate to this because I know that, like, again, back to my company, I found it when I first started, like there were times in the first year or two where my mindset was like, man, I’m just sometimes you just got to eat the dirt. You know, sometimes you just got to eat dirt and be right there. And basically what my metaphorical mind says that that means that you were just grinding and you grind in and you’re not really worried about the things that everybody else is worried about. You’re not thinking like how everybody else is thinking. You may be in survival mode. You may be in trial mode and it’s hard, but it’s temporary. And so, you know, back to the whole piece about what the books, the theme of the book to me, what I took away ultimately was that it’s hard running a company. It’s hard being a CEO. And it’s also hard if you’re not the CEO. and you’re working in a startup environment and you are an executive, it’s hard for you too. And maybe you’re not either. Maybe you’re a manager at a Fortune 500 company. It’s hard for you too. Leadership is hard everywhere. And so adopting the mindset of, I’m going to focus on survival versus everything’s going to be perfect all the time. I think it’ll help you go a long way.

John: Mm-hmm. I agree. And just to, you know, talk a little bit more about the structure of the book, what folks can get from the book is, you know, I would say that, you know, if you’re wanting to run a startup, you want to raise capital, you want to, you know, start dealing with investors, you want to start building a leadership team. Like if you want to scale an organization or you are part of a scaling organization, I feel like this book gives you. It’s almost like a handbook for all of those crappy situations that you’ll run into. It’s all of Ben’s learnings throughout starting multiple companies and growing multiple companies and being near failure, dealing with investors, hiring and firing executives. It’s really a handbook for all of those difficult situations that’ll come up along the process. But then at the same time, there’s a story element to it as well. So there’s always a story. There’s always context that he puts it into, which which I love and. you know, he talks a lot about how to, you know, take care of the things that seem really complex and he gets right down to the point. And that’s one thing I, I really loved about the book. And, you know, for another example of that was, you know, when he’s talking about culture, you know, programming your culture, you know, how do you create a culture? What is a culture? And the one thing that he said that I loved that I, uh, I, you know, I’ve seen in a lot of organizations is the straightforward comment perks are not culture. And, you know, I see a lot of organizations say, you know, that, you know, we care about our employees. Here’s a subscription to calm. While that’s a nice perk, but you just have to know that that is not part of your culture. It’s really, does culture, is it aligning with driving your business forward and your identity? I think that’s a big thing when you’re starting an organization or a venture, is understanding your identity. It’s like, what do you want this company to be? What do you want it to stand for? And, you know, what are the behaviors that support that? Right? And then so it’s, you have your identity, but then does that align with driving your business forward? Right? Like there is, there may be, you know, a company that needs to move fast, test and learn often that, you know, has a very specific audience that they’re selling products to, you know, then there’s maybe another platform that’s, or another company that’s an overall platform that sells multiple products that is a, uh, you know, really just kind of an online marketplace or something. There are just so many different business models, but then how do you set up the identity of your culture? You’re the behaviors that you want to drive the success of your business, right? And then you know what also drives the success of your business. People wanting to work there. Great, smart and trustworthy people wanting to work there so you know that’s another part of your culture and you know he talks about some some ways to do that and some ways that. to work with what people want, right? And maybe, you know, maybe the smartest person for the role doesn’t have the right intentions or behavior for that specific role. So, I mean, he really does go into the nuances of how to program your culture and really how to program your culture based on what you want to accomplish. So, You know, I think that that’s just one example, but there are so many different things as he goes through each of the chapters. So highly recommended if you are looking and you’re going through some of these struggles and some of these growing pains that, you know, as difficult things come up, there is always a chapter to reference here.

Tony: Yeah, I mean, like you said, it’s almost a handbook for building a company. He said that when you’re expanding your team, consider to hire for strengths over weaknesses, have clear expectations of who you are hiring with the realization that there is something seriously wrong with every employee in your company, including you. I thought that was interesting. Like, dang, that’s very straightforward. And then he said that involved multiple people in your brainstorming processes, but make the final decision solo. And I think that’s important because people don’t talk about that a lot these days. We live in a very inclusive environment where it’s always everybody’s opinion. It’s everybody given an input and you want everybody to have a voice and a seat at the table. Yes. However, according to Ben, he says that you should make the final decision solo. And he says that because consensus based decisions tend to sway the process away from strengths and toward weaknesses. I thought that was interesting, too, because you wonder why it would sway toward weaknesses. And he didn’t. I don’t have the notes on why he unpacked that more, but I would say that from my understanding, it may be because fear is involved. And as a CEO, And as a leader, like John said earlier about courage, it’s not about not having fear, but it’s about standing in the face of fear and doing what’s right and what’s hard and what’s necessary. And sometimes only the CEO will be willing to do that. Everybody else might just be trying to protect their job or protect the integrity of the business for whatever reason or way they view it. But that protection can sometimes be limited. And if you think about things that grow, things that expand or things that happen that are really big, almost like gave an example that there’s no blueprint to being an entrepreneur. He said there’s no blueprint to running for president. You know, there’s no blueprint for those kind of things. And with that in mind, that’s how you can shift away from strengths and going towards weakness, because a group decision may be based on a blueprint. But a CEO would be like, well, how did we get here? You know, CEO can look around the room and say the only way we got to this table where we have eight people making this decision is because we made hard choices to expand the business. And now we’re here. But everybody else might not have this same mentality. So I just thought that was very interesting that when it comes to brainstorming, he suggested that you make the final decision solo. And I know that culturally today speaking, that is probably something people wouldn’t wanna hear because that’s one of the hard things about hard things.

John: Yeah, we are moving more and more towards a consensus culture. And I would also add that coming to a consensus culture, it adds a lot of time. We’re in an environment and an economy, and especially if you’re on the tech side of business, which, I mean, let’s be real, every business is involving tech these days, and you’ve got to move fast. Inspiration is out there and it’ll find someone. If you’re not moving and you’re not willing to fail and test and learn and put yourself out there, then someone else is going to do it. I think that that’s another part of it is, yes, including everyone to gather the information that you need to make the decision that you feel is the best for your organization. And the CEO is the only one that is going to have 100% oversight over the history, all the arms and legs to the deal, the investor side of things, the cashflow side of things. You’re supposed to see this overall picture. And when you come to the table for a consensus, if you’re relying on that for the end decision, there are so many heuristics and biases that come in whenever you get in a social setting. I think, like you mentioned, Tony, moving towards the weaknesses side of things. Naturally, it’s a prospect theory, the Daniel Kahneman theory that we, I guess it’s not really theory anymore, is it? But prospect theory anyway. It’s been proven out time and time again that humans are just collectively and individually way more inclined to avoid risk than seek reward. That’s just period. It’s a sales tactic that you’re taught in any sales training that’s worthwhile to go to, is we’ll teach you some part of prospect theory, how to make your clients Fearful to take action and you know, that’s your customers, you know, if you’re working larger deals It’s more like what are they? What are they missing out on by not working with you is Way more attractive to get someone to make a buying decision than saying here’s what you can gain by working for me or by working with me or buying our product and it’s you’re missing out on this and your competitors are doing this and this. That’s just a little tangent on prospect theory, but just to highlight that I believe what you’re saying and that moving towards weaknesses and avoiding failure and avoiding risk. well, that’s not where the game’s playing. You got to take risks, you got to be willing to fail. That’s another thing and just circling back to the fear and courage, it’s got to be willing to fail, to take the risk, to create the company, create the dream, do what you want to do, create the side hustle. You got to be able to take a little risk there and to manage risk, evaluate and manage it.

Tony: and eating dirt. Yeah, right. Yeah, seriously. I mean, you think you’re going to have gourmet if it’s going to be gourmet all the time for you? You’re sadly mistaken. You know, it’s definitely. It’s supposed to be hard. I mean, that’s why it’s not a bunch of successful CEOs running around the country, because again, it takes you back to that survival mode. And, you know, he said something that I thought was interesting. Chapter eight, which was the first rule of entrepreneurship. the title of that chapter that the first rule of entrepreneurship is that there are no rules. And, um, you know, that chapter was very interesting because he gave a lot of stories about that. But what I thought was very timely for me, at least was hearing him say that the secret to being a successful CEO is that there are none other than making the best move when there are no good moves. And. You know, there’s a there’s a theory or a subject matter and research in the same kind of subject called polarity management and polarity management is how do we manage the problem? So are we you go with polarity management, you go into scenarios and you ask yourself or your team, are we looking to solve this problem or are we looking to manage this problem? He’s either way. We got a problem, but Our culture tells us to solve every problem, like don’t leave the room without marking this problem off the list, like checking it off and moving on to the next problem. But some problems exist and they aren’t going anywhere because they are problems that are immovable. You know, maybe it’s the way your company is structured. Maybe it’s the cap that you have from a budgetary standpoint. Or maybe it’s a cultural fit with an individual. Or maybe it’s an absence. Or who knows what it may be. But some problems are not solvable in the moment. So you may have to put your thinking cap on with you or your team and realize that you need to make the best move as opposed to trying to solve the problem. Because sometimes there are no good moves to make, as Ben said. I just want to throw in polarity management for folks that are struggling with a team that wants to solve every problem and make everything perfect. And just realize that sometimes it’s about moving the problem along. It’s like if you have a dummy tire on your car and there is no way to get a regular tire right now. You just riding with that donut for a little while and it just is what it is. You know, tell the team that we just we had a flat and here we are. We’re moving on and we’ll fix it later because you don’t want the process or the car to slow down so much that you no longer moving forward.

John: And and, you know, there’s one thing we haven’t really talked about yet is, you know, is the struggle personally. Right. The, you know, enduring all of these ups and downs and the roller coaster, it can take a toll on you and the entrepreneur, the CEO, the leader, and. You got to support yourself. whether that be with your personal practices, with the community to help, you know, share the, not really share the burden, but to just share yourself with. And it’s like when you’re able to share with people authentically and connected, it will automatically take some of the pressure off of your shoulders. Like something to remind you like why you are, why you are living this way in the first place. You know, why did I choose this? Like really connecting to your why and connecting to the people that will be there to support you, you know, whether your organization succeeds or fails, like having the times when I’m questioning my intentions moving forward with Humescence and my organization. A lot of the conversations I’ve had with people that I love, people that would support me no matter what decision I make or what happens have been some of the biggest moments in, you know, in the trajectory of, you know, my development as a leader and growing the organization is, you know, what I’ve been doing to support myself from a community, from the connections, from where I want to spend my energy and time, the relationships that give back to me, and then also my personal practices that I don’t want to compromise on. My meditation practice, my nutrition, my exercise, the things that support my energy to be able to stand up in the face of fear and move forward and to figure out these problems at their priority level. right because you know like you were mentioning the problems are going to be there it’s you know which one are you going to work on now which ones are worth solving and you know i think like when you’re When you’re thinking of the problem management or polarity management, it’s about seeing what’s important and what’s urgent. What do we have to take care of now? Then sometimes when everything’s important and urgent, and you’re the CEO, you’re in the struggle. When you’re losing, when you’re losing sleep, when you’re dreaming about solving, solving problems, you’re in the struggle. It’s. You know, and that’s the thing is lean on other people. Have a mentor, have someone that’s been there before you have a coach, someone that can be a reflection of your subconscious mind and help you see the thought patterns that maybe you’re keeping you stuck or that are moving you forward. There’s so many different ways that you can support yourself, but make sure that you are and be honest with yourself. Know that things are going to be difficult. Know that there’s going to be a struggle. Don’t try, don’t lean into that human tendency to bend or avoid the truth or tell yourself a different story just to feel better. Ask for help, or just make the decision and move forward. You’re going to be okay. And whatever you can do to support yourself, to let that be true for you, that I’m going to be okay, lean on it.

Tony: You know, Ben also said in the book, to echo that, is that you need two types of friends in your life, I guess when you’re a CEO. But I think in general, you probably need these two types of friends in your life. He said, one, you can call when something good happens, and they’ll be excited for you. And then one, you can call when things go horribly wrong. So to your point about community, if you don’t have that period, find that. I think we all need people that we can talk to, you know, and it doesn’t always have to be therapy. We always we always say, you know, go to therapy or, you know, even getting a coach, which I think is important, but also have friends. So it’s not always so transactional people that you can text and say, I’m dealing with this problem. I need help trying to solve it. So. I just want to double down on that and I think one thing I’ll say to. Back to kind of how I started thinking about the book with the survival mindset is that Ben says that there are peace times and war times. And so as a CEO, sometimes you’re in peace time CEO mindset and then sometimes you’re in war time CEO mindset. There were two things that I wanted to bring up with that. He said that when it comes to culture, peacetime CEO spends time defining the culture. Wartime CEO lets the war define the culture. I thought that was super interesting. Peacetime CEO works to minimize conflict. And wartime CEO heightens the contradictions. Super powerful. countercultural. I think that we want at least environments that I’ve been in, not that I’ve led, but environments that I’ve been in and worked in. I see people wanting everything to always be peace time and peaceful time when it comes to leadership and doing the hard things or running a business, a company, an organization, a nonprofit, whatever it may be. And I think that there’s only certain type of leaders that really understand that sometimes it is Wartime and you don’t have to call it wartime that you know is a taboo word for you, but you know I’m gonna use that cuz been used it in the book, but When it comes to wartime, I mean, sometimes you, you know, when you’re dealing with the polarity management, are you dealing with, with issues that you said, like you mentioned, John, there’s several issues at once and you can’t pick one over the other. Well, sometimes you just got to lock the door, right? Sometimes everybody needs to stay in the room until we figure it out. So it is like that sometimes. I think sometimes as a leader, there’s going to be times where you stay up super late. I’ll wake up super early. You know, I’d be up at three o’clock in the morning. Everybody’s sleeping. You’re up. Working on things that need to get done. That doesn’t have to be every day because maybe that’s not sustainable. But, you know, there’s an ebb and flow of life that is natural. And it’s not always peaceful time. And if you operate in peacetime, when it’s actually wartime, I think that’s how your company can sink because if you’re in a competitive market, I guarantee you that the industry leaders, they know the difference of what time it is and they know when it’s peacetime and wartime. And if you only think it’s always peacetime, then you’ll be left behind.

John: You got to do what it takes, you know, do what it takes. It just comes back to making that hard decision when the hard decision is the right decision. So, my friends, check out The Hard Thing About Hard Things. It was a book that was actually recommended to me by one of my executive clients and I was blown away by a lot of the stories and how things can you know really apply and The what I loved about it was really the the directness of it so like he tells it like it is and You know, it’s the reality of some of these situations so support yourself Step forward in the face of fear into what you want to create and ask for help. Have resources like this have people that you can reach out to a network that supports you and. Move forward. Thank you for listening to the present professional. You can check us out at the present professional podcast.com. We’d love to hear your feedback ideas for episodes and please write us and review us anywhere that you’re listening right now. We appreciate you as listeners and have a good one. My friends.