421. AMMA — Scaling Your Firm Starts With the Decisions You’re Afraid to Make
27m 19s
In this podcast episode, Michael Mogul, founder of Crisp, discusses key lessons for entrepreneurs, drawing from Warren Buffett’s final shareholder letter. He argues that chasing certainty limits growth; instead, leaders must embrace pain and uncertainty over extended periods. Mogul stresses that learning from failures is more valuable than celebrating wins, as past mistakes build wisdom for future success. For new growth investments, he advises hiring experts with proven experience (batteries included) and setting clear milestones at 30, 60, and 90 days, noting that results depend on the complexity and gap between current and target states. He warns against procrastination disguised as preparation, advocating a “ready, fire, aim” approach: commit to a deadline and work backward, scaling while solving problems in real time. Mogul also highlights that leadership effectiveness is measured by tolerance for uncertainty, and long-term thinking (5-10 years) enables sustainable growth. Overall, the episode encourages entrepreneurs to forgive past mistakes, focus on learning, and take action despite incomplete readiness.
I think it's an entrepreneur chasing certainty as a fool there, it's like the horizon. You're never going to have it and if you are only chasing certainty then your upsides going to be very low and you're probably going to be very slow to grow and evolve in the marketplace. I'm Michael Mogul, founder and CEO of Crisp, the nation's number one law from growth company. I've built my business through practice, not theory. I've started which is $500 to my name and has grown to over 8 figures in revenue over the last few years. Earning a spot on the ink 500 lists of the fastest growing private companies in America. Our approach has been to take everything we've learned about generating massive growth within our own organization and help the country's most ambitious and committed law firm owners do the same for theirs. In each episode of this podcast I sit down with innovative market leaders from the legal industry and beyond to learn from those who thrive in the face of adversity, challenge the status quo and define what it means to be a true game changer. This is Jessica, head of coaching strategy at Chris and today we're flipping the script for another special edition episode to get Michael's take on, the timeline for seeing tangible results from new growth investments, recognizing the difference between preparation and procrastination and how to know when patients with a team member become detrimental. If somebody is not also accountable for their own success and their own growth and their own development then there's only so much you can do for someone and I've gone down this path before and if I do have regrets it's looking back over the years and wanting something for somebody more than they wanted to fit themselves. That's coming up on the Game Changing Attorney podcast. Alright, here we are, another AMMA. And I am excited as we draw close to the end of 2025 and then we move into 2026, a lot of reflection taking place, probably some celebration as well. Those you listening, some of you have sure had a really great year, some of you had an okay year and some of you may have had an absolutely miserable, horrible year and if you're either of those former or those latter two, I have something for you. Actually, if this can benefit everybody, we'll put it in the show notes. Warm Buffet last month came out with his final shareholder letter. And he always puts one out before their annual shareholder meetings and this was his final one because warm Buffet's like 90 plus years old, right? And it is like eight page letter that he wrote out and just kind of his thoughts and lessons learned and it's incredibly fascinating to read it. And I'll read an excerpt from it because if we do the entire eight pages, this will be the entire podcast, but I will say here's the a few final thoughts in this from page 70. He says, one perhaps self serving observation. I'm happy to say I feel better about the second half of my life than the first. My advice, don't beat yourself up over past mistakes, learn at least a little from them and move on. It's never too late to improve. And this is warm Buffet kind of reflecting that like the second half of his life was even better than the first. And we're big believers of like future greater than past that you're in your best days can always be ahead of you and that everything that you have learned and like any lesson, right? Any experience that you've had positive negative and so on is really the building block for everything that is to come in the future. And if you're reflecting on this year and maybe it didn't go your way or just wish you had gone a little bit differently, just recognizing that the most important thing isn't necessarily that you make progress or not, it's, did you learn or not? Like did you learn lessons? Did you get data back? Did you gain wisdom that you could apply in the future? Because that's, that's all value really is, right? Like money, you could always make more of it. And the thing that I always think is just in terms of, because sometimes people ask these hypothetical questions and we go to like dinner parties, which is never, but sometimes it becomes like this, this conversation of like, well, if you had to start over from nothing, could you do it again? And it's like, you zero out all the bank accounts and you don't have any relationships or anything like it. Could you do it again? And my answer is this, yes, resounding yes, it probably half the time. I don't say that in a statistical way. I say, because the only thing that I would want to stay with me is all the lessons and experiences and the know how knowledge and like the wisdom that I've gained because that's really all the value. Well, it was like everything that came before the wins, the losses, et cetera, that's all the learning that happens that now you can go forward. And now I say, yeah, it's going to take me half, it's long probably, you're not shorter, because now I know all the pitfalls to avoid. And I know how, you know, all the things, different types of mistakes that I made and how to do things the right way and everything from my hiring operations, leadership, et cetera, that we've learned and we're still learning, right? But that knowledge is invaluable. So I look at it from the standpoint that, you know, sometimes you win and sometimes you learn. And there's going to be, you know, seasons or years where it's going to be a year of just winning. And like I said, a year of learning and maybe it was just a learning year for you. Yeah. Because this year, it's absolutely necessary. Not every year is up until the right, like, stuff, there's going to be years where it's like, man, that was a tough year. But I also look at your time horizon. Sometimes it's going to be looking at the standpoint of like, look, you know, when we laid out last few years, you know, when I started Chris, I used to look at things on like a week to week basis, sometimes like a day to day basis. Then I like my horizons expanded. I started thinking in terms of months and then quarters. And then it was like, let's win the year. It's like, let's win each quarter, let's win each month and let, you know, let's win the year. And now I look at things. Yes, those are still important. We still track those milestones. But I look ahead and I think five years out. Sometimes I think 10 years out. And we think is this decision going to make sense five years from today? And a lot of things that we were working on this year are not things that are realized this year or even realized next year. They take multiple years until they come to reality and then come to, until they pay off. But that type of long term thinking is where all the growth really happens. It's like the more pain and uncertainty that you're able to live with for a long period of time, that is really the, I think that if you could have like one metric to test whether somebody's an effective leader is how long can they live with pain and uncertainty? Some can go an hour. Some can go a day and others can go years. The other analogy I would give is that, you know, they talked about this in the seals where in like Navy SEAL, like the, if you had the run a long time, let's say you had the run like 10 miles or 20 miles or something, you knew where the finish line was. So you could think ahead, all right, I've got nine more miles or eight more miles or three more miles or two more miles, whatever, right? But imagine they just tell you to start running and they don't tell you how long you're going to run or when you're going to stop. You might be five miles in and for all you know, you're like, man, are you going to run 50 miles or you're going to run six miles, right? And is you keep running until you get the mile 20? You may only have one mile left, but you don't know. Yeah. Maybe you got 20 more. And that type of uncertainty is what creates like reach psychological havoc in somebody in their mind just because they don't know where the destination is, where the finish line is. But that is that uncertainty is what being an entrepreneur is, is that you don't know what next month is going to be or what next quarter is going to be or what next year is going to be. You can plan for it and you can put together the best plan and you can be prepared and I try to create all sorts of different scenarios. But ultimately, you have no idea what lies ahead for you. It can be very good. Yeah. Right? It could be filled with challenges and sometimes those things are inclusive. Like sometimes the best years are the ones where you navigate the most challenges. And I always look back and I think we don't really learn a whole lot from our wins. Right. You know, the things that we really learn from is when we do the post mortems of like back and saying here's where we were in wrong and here's where we were unsuccessful and here's where we can do better next time. That's where all the growth and learning comes from. So sometimes people ask you, hey, do you have any regrets of thinking back of like, okay, like that was a bad idea or you made bad hiring decision here or like this is a campaign that wasn't successful. You lost a lot of money here, whatever. And I think back and I'm like, I don't think we'd have the wins if it were not for those experiences with the learning that came as a result of it. So if I take those things away, then you remove all the ups as well. So if you just take away the downs, yeah. So I think that's why it's so important. And it's just knowing that like, like next year is going to hold new challenges and new obstacles to overcome and things to navigate. You're going to have to grow and level up from. And I guess then the echo word buffet is just just to not be so hard on your past self. Maybe you had to make decisions with the information you had at the time. And perhaps it wasn't the right decision, but you had the right intent and you've made the best decision with what info you had. And ultimately now your wiser, hopefully you've learned and now you can have a better outcome in the future. But it's time to move on and forgive yourself a little bit because it sounds, you know, I think a lot of people listen to this podcast or we're just trying to do their best. Yeah. Absolutely. So with that, let's get to the aim of main. Wow. That's a podcast, right? Yeah. See you guys next year. Now let's do it. So AMMAs, like before you get to the question, Jessica, just want to let people know, it can submit questions, it can text us 404-531-7691. You guys can submit questions about anything like leadership, culture, vision, etc. Everything except for politics, apparently, you know, whatever. With that being said, if you get any sort of value from the podcast, we would love and appreciate if you were to share the podcast with another leader who might find it valuable and or leave us a review on Apple podcasts or Spotify. Just helps us reach more people, helps us get more guests on the show and helps us keep the show free. So with that, Jessica, let's get to this week's questions. Now we get to start. So question number one, hey, Michael, I have the family law practice in Florida and I've really committed to growing the firm. I went to double our revenue in the next year. I hired a marketing coordinator two months ago and I'm already frustrated that we're not seeing a significant uptick in leads. I invested in a new CRM software and approved more marketing budget for her, but I'm not seeing any tangible improvement. I'm investing in growth. I'm allowed.
Howling her in the team to make changes, but everything seems to take forever to actually work. How long should you realistically wait before you know if something is working? I am trying to be patient, but it feels like I may just be wasting money and resources. So let me give more of a tactical answer to this because it can vary. I think at the start of that, they were saying what they want to double the revenue. Yeah. We don't know where doubling from. We're doubling from 500,000 to a million or for 20 million to 40 million. Right. Very different. Because the accomplishing, you know, the former year's possible, the latter is going to be a little bit trickier. How long is too long? How long do you know it can vary? It depends on what you're trying to achieve. It really depends on what the delta is between where you are and where you're trying to go. The larger the delta and the greater the complexity, probably the longer it takes. And I would look at it the more so from the standpoint of like, it doesn't mean you shouldn't have any expectation. Right. It doesn't mean you just let somebody go do whatever the LA want and then like, come back after three months and then you see the progress you've made and you might not align with your version of progress. Right. Ideally, when you're meeting with somebody, you're interviewing someone, you're making very clear of here's where we are. Here's where we're trying to go. And ideally, the people that you are interviewing or attracting to your business, those are people that have experts in, are there experts in what you're trying to do? Like if it's a marketing quarter, it could be a marketing expert that is, that knows how to do the thing that you were hiring them to do. Not reason, including. Like why would you hire somebody who doesn't know how to do the thing that you need to get done? Like, isn't that crazy? And it happens all the time. All the time. Like, check this out. You want to increase our intakes. So let me interview somebody who has, like, ideally, who has done that before and has done it at another offer. Oh no, they've never done it before. They've never answered the phone. They've never. Okay, so now we're going to test them with doing the thing that they've never done before and they're doing it for us. Sounds great. It's like if you had a restaurant and you were going to hire like a chef, only they've never worked in a restaurant before and they've never actually cooked food before, but you want them to cook food in your restaurant. Good luck, my friend. Let's assume you did that first part. They do come in with the batters including the expertise. Then what you really want to do is you like, you share with them, here's where we are, here's where we're trying to go. And then you want to hear their perspective on how do we do it? How long is this going to take and you proposed to me, like you're telling them the metrics of what should my expectations be at 30 days, at 60 days, and 90 days, right? Like let's quantify this specifically. You tell me because I want to double the, you know, let's say double the revenue of the firm and they might tell you, hey, that's reasonable or it's not reasonable. And I don't like to hear that's not reasonable. However, I also want people to lie to me. So I want them instead to say, hey, what you're asking for, it's not that it can't be done. Anything could be done. I mean, they can catch rockets, they're flying to the air and catching back down on like, you know, drone, like droneships. What I want to hear is this is what it would take. Yes. Right? So I want to double intakes. Okay. That then requires us to be able to generate this many inbound leads and our cost of acquisition is this and this is the amount that it would cost us to do it. And this is based on our current conversion rates. And here's how it breaks down and we're required this investment or there's another path to get you whatever. Right. And then you can determine is that juice worth the squeeze, yes or no, right? Anything is possible, but doesn't define the laws of physics. It is possible. So in that type of scenario, like if this person is proposed their targets and you have agreed to those targets, well, then it's meeting with them. And are they hitting those milestones or not? That's cute. It's setting clear expectations. But if, you know, this to me seems more like a matter of like communication of you have something in your mind that you want and you feel like they're failing to live up to it. Only they don't know exactly what it is you're looking for for how they can, you know, I promise you, the person you just hired two months ago probably doesn't want to lose their job. The person you hired two months ago probably wants to be very successful in your firm. At the same time, like, you know, they need to know what it is you're trying to achieve. And also do they have the resources support to be able to actually get it done. Like let's assume their intent is there. They're like a very driven person. They have the capability, like they know how to do it. And all say is that if you hire people that are batteries and coded that have done the thing you're trying to do before, they'll tell you how to do it. You're not going to have them like, okay, go and figure out how to do this thing you've never done before. And if you're in that type of situation, which sometimes in the early stages of business, you can't afford the ones that come batters included. You can't afford the ones that have already scaled, you know, a law firm that like yours and have doubled it, right? So you're hiring somebody that is still potential and is still learning when you can't have the same expectations for them because they're figuring it out as they go. And that means that what you think should be done in like a year may take quite a bit longer than that because you have to give them time to be able to learn and perform experiments and get feedback. All you're doing when you hire somebody batteries included, all that means is that they've already performed those experiments on somebody else's dime. So they don't have to then spend your time and money to do the same tests that they've already done and figured out. But if you have not, if you don't have that type of person, then they have to learn some way. Yeah. As we often say to like build it versus buy it and where are you in the stages of the business early on, we have to build it. We have to build and do that. And like you said, it's on your dime or are we buying it batteries included? All right. Question number two. Michael, I've been spending the past year really building out our systems, processes and infrastructure and anticipation of future growth. I run a PI firm in Wyoming and my team keeps asking when we're going to start aggressively pursuing new clients, but I still feel like we're not ready yet. I want to make sure everything is perfect with worry scale so we don't compromise quality. How do you know when you're truly ready to scale? Good. This person has no quick start. I think they should be asking you this question, not me because I don't even know how to answer this because I'm like a ready fire aim. Right? I'm that human being. Yes. And I'm like scale it and we're going to build their plan on the way down. You figured out. Even with the first summit, pick a date, start selling tickets. We'll figure it out by the time we get there. 100%. It's no different than, it's interesting. Like right now, you know, training for triathlon or any sort of like physical event or anything, any sporting event. I find that there's three, two types of people. There's the type of people that say, I'm not ready yet, but I will sign up for the race when I'm ready. Right? You'll never be ready. And they'll never be ready. Right? And then there's the type of people that are also not ready, but they sign up for the race and now they start working backwards from that date to get ready. Yes. Right? They say, Hey, I got X number of months and here's what I need to do because I've already signed up. They like posted up and say on this date, I'm doing this. They spend the money and like, that's it. Right? They make it public. But what are your thoughts on this? Because this seems more of a question just for you in terms of like you understanding this human because they're like, how do I know when I'm ready? And it's like, is there a moment or like some time, you're like, okay, 10 seconds ago, we work ready. And as of this event, now we are ready to scale because obviously there is a big difference in the sense that like some firms are not ready to do double, right? Like they may not have the capacity they need to be able to service the work and you know, those sort of things. But is there like a moment when you're like, okay, you have enough information to now move forward with the decision? With this person, there's never enough information and nothing will ever be perfect. And I think the forcing, you have to have a forcing function. Otherwise it's like, oh, let me keep getting more information. Let me keep redoing the process. Again, I appreciate obviously infrastructure systems, all of those things, but it will never be perfect. It's like all ideal conditions are met. It's not it. We very much are like, we're going to build the plane while we're flying it. And maybe what this person needs is someone to push them, like you push me or they just need to make a public commitment and work backwards from that date. So it's basically like, it's not going to ever be perfect. But you sometimes, what is it done is better than perfect. Yes. Jeff Bezos, I used to say this when he was talking about like the early years of Amazon and like what really helped them, what he believes really helped them like grow exponentially and scale that he felt was the competitive advantage over other organizations. And he said something along the lines of like, we were very good at making decisions based on an incomplete information. Yeah. So meaning that sometimes they didn't have 100% of the information, but they only had 80%. And as a whole, they were able to make decisions based on 80% and some decisions were right, some decisions were wrong. Your rate of decision making in your organization often times dictates the growth of the organization and the pace of the organization. Because sometimes you could be wrong five, six times over and then be right before somebody else has even made a decision at all. I was literally going to say that. I would just say that if you have 80% of the information here, rather than like, I mean, didn't try and figure out how do we get the other 20% because I think the chasing certainty, is what we were talking about earlier. It's actually kind of funny that comes back to this question. I think it's an entrepreneur chasing certainty as like a fool's errand, right? It's like the horizon. You're never going to have it. And if you are only chasing certainty, then your upside is going to be very low and you're probably going to be very slow to grow and evolve in the marketplace. Like you're going to be the last one. You just, let me see if the social media thing like plays out, right? So you then sit on the sidelines for 10 years where all your competitors are gaining ground and adapting and evolving and leveraging technology. Same thing with AI. You know, you're going to see the same thing. You're like, let's see if it really works for a law firm, right? Every other law firm and all your competitors are like implementing and integrating it into their practice and are becoming more efficient and more effective and more profitable. And then by the time you're like, okay, right? Now everybody's using it and you're the last one to adapt. And now all the competitive advantage of it is gone, right? And now you're the one that's left behind. So that's the problem of chasing certainty. Like you're chasing certainty in an uncertain world. That's the point. That's why it's almost one of these things is like, makes you question why some people become entrepreneurs. I'm just going to say, maybe this isn't for you. Is it like at one point was there like a guarantee of an outcome? Yeah, that's never. The whole point is that every day is uncertain and it's just not everybody can live in that. And most people don't want to live in that. They're like, man, I just want to come in. want to do my job.
job I want to get paid and I want to go home. And then there's like these freaks, these entrepreneurs, these psychopaths that come in and say, I want to take all this risk or my odds of like losing or greater than my odds of winning. And every day I'm going to navigate the unknown and we're going to try to figure it out and deal with uncertainty. And that's just and you learn to like, it's like, you know, what is a bane says from Batman he's like, make darkness your ally, right? It's like, that's what it is. It's like, you got to make uncertainty your ally. Or maybe that's not for you. So think of it either way. So question number three today, Michael, I have an employee who's been underperforming for months and I've been telling myself to be patient. He's not toxic or anything like that. He's just not great. He does okay work, but it takes so much time to get him to do things correctly. And I'm just hoping that he'll eventually pick it up. How long should I keep giving him the benefit of the doubt or do I need to make a hard call? I think you already know just looking for my blessing. Okay. I mean, you just you have a good question here when you think about it in the sense of if whatever, let's say you have your vision for your law firm and however far out you are from that, whether it's a year or two years, five years or more, you think five years from today, do you really see this person at your firm? And if the answer is no, then what are you doing with them now? Right? Because it's just going to slow you down. And like if you know your like five years from today, this person's not going to exist here. Then why do they exist today? Right? And then come up with all the reasons you're like, you know, I understand that all this other stuff. Because like we were having this conversation when I went with this person, I guarantee you, they already know this is what they're supposed to make. Yeah. Like they already know this person is not meeting expectations. But here's the problem. Because I would say I think you already know what to do. And if they were sitting right in front of us, I promise you, they would say, but you don't understand. Oh yeah. As soon as you tell them that the decision that they've already made in their mind to then act on that decision, they will say, but you don't understand this person has been with me for this time. And they have this potential and they do some good things. It's almost like you want someone to talk you out of the decision you know you're supposed to make because you don't want to have to have an uncomfortable conversation. And that's all it is. I remember years ago we were sitting around. We do our leadership off sites and we were going through like every individual in the organization. And there's one person. I remember with someone described them as, well, they're not terrible. They're not terrible. And then I remember somebody else said, well, is that the barometer of the standard of our organization that like we have people that we would describe as not terrible. Right. That exists in the organization. Right. You got some that are exceptional and you got some that are not terrible. Right. And you hear that and you're like, okay, so what do we do here? Right. I mean, look, if you've given this person coaching and you've given them resources and support and so on, we have a rule at least at crisp and you can decide what your rules are your organization. Right. Run your business how you want to run it. My rule is is that we don't coach effort. We can coach skills. We can help somebody like like navigate, you know, all sorts of like challenge adversity like if they need additional support, but we're not going to coach effort. We're not going to say, Hey, can you work hard? That should be an intrinsic motivation when somebody comes in with somebody that works here. And if somebody doesn't want to work, right. That's I can't help you. You can't teach hungry like that's that's the rule here. So when we find ourselves having an effort conversation as leaders, we have to check ourselves and say, look, we can help coach up somebody and we can help coach skill, but we're not going to coach will know. And if somebody is not also accountable for their own success and their own growth and their own development, then there's only so much you can do for someone. And I've gone down this path before and if I do have regrets, it's looking back over the years and wanting something for somebody more than they wanted for themselves, right. And you believe in a study because you're a leader, right. And you want somebody to succeed. And it's like you look at yourself and you think you think that everybody's like you, you think that everybody is this mutant freak that has, you know, can navigate the adversity that you'd navigate and they want it as bad as you do. And most people don't know they're not like you. I used to think that everybody like I was like if I can do it, they can do it. And I had all these tough moments and all this adversity and all this stuff. And I'm like, we just have to help navigate that. And it was a tough wake up call for me. It took me a few years to actually learn that not everybody is like you. They don't have the same ambition. They don't have the same desires. They don't have the same goals. They don't want to be the best. They don't want like to, you know, be in the top like 1% of whatever it is like in their career or like or whatever skill that they're developing. Some people that's just not where their priorities are. And that's okay. Enough is good enough for them. Yes. It doesn't make them bad people. It really doesn't. Right. Because that was another tough thing for me to understand. They're not inside the judgment. I was like, what do you mean? How is this person now want to be the best version of themselves? Why would any human being on this earth not want to be the best version of themselves? And the reality of it is is that look, man, the heart wants what the heart wants. And maybe they will walk that at some point in the future. Like because people can change on their own accord. They may decide five years from now that you know what? I want to lock in. And now it's important. Like I knew somebody that was basically, you know, you've got to like a scrub all through like high school, college, really never applied themselves just not at all. Right. Then gets married, wife and kids. And this guy locks in. He locks in totally changes entire life just transforms and just becomes it absolute demon. Right. Just like, you know, good way because sometimes our focus shifts and our priority shifts. So that can happen too. But we're not waiting for that to happen for the people in our organizations. You want to give somebody the opportunity to, and the, you know, and the coaching and the support to succeed. But we don't want to be coaching effort. So it sounds like you already know what you need to do. Now you should go out there and do it. But then I would actually sometimes what it's helped me is not thinking about, okay, man, this is going to be so hard to do. It's thinking, can I get to where I'm going? If I don't do this, right? Like meaning that. And also you want to be really selfish. If you don't do this, think about everybody else in your organization whose livelihood depends on the vision being achieved. Think about all the people who have like their needs. They got student loans. They got families. They want to start. They want homes. They want to buy. They want, they have like career goals of their own. They want to see the organization grow to be able to enable that vision, their own vision to become a reality. And as long as you tolerate mediocrity, it's going to make that journey much more difficult. So you are doing them into service. That's right. All right. Thank you for that. Okay. Until next time. You've been listening to the Game Changing Attorney podcast with Michael Mogul. If you found this episode valuable, here are three free ways that we can help you grow your law firm. Number one, download the first chapter of Michael's book, absolutely free at GameChangingAterney.com. Number two, you can shoot Michael a text at 404-531-7691 and ask him any question you'd like. You might just hear the answer on the next episode. And finally, number three, if you can leave this podcast a five star review, it will help us gain access to more influential thought leaders and bring their lessons learned here to you. For more information on this episode, see the show notes in your podcast app or visit leaglepodcast.com.
Podcast Summary
Key Points:
Entrepreneurs who chase certainty limit their growth; true growth requires embracing pain and uncertainty over long periods.
Michael Mogul emphasizes that learning from failures is more valuable than celebrating wins; past mistakes build wisdom for future success.
For new investments, set clear expectations with experts (batteries included) and track milestones at 30, 60, and 90 days; results vary based on complexity and delta from current state.
Preparation can become procrastination; instead of waiting to be ready, commit to a deadline and work backward, scaling while solving problems in real time.
Leadership effectiveness is measured by how long one can tolerate uncertainty; long-term thinking (5-10 years) enables sustainable growth.
Summary:
In this podcast episode, Michael Mogul, founder of Crisp, discusses key lessons for entrepreneurs, drawing from Warren Buffett’s final shareholder letter. He argues that chasing certainty limits growth; instead, leaders must embrace pain and uncertainty over extended periods. Mogul stresses that learning from failures is more valuable than celebrating wins, as past mistakes build wisdom for future success.
For new growth investments, he advises hiring experts with proven experience (batteries included) and setting clear milestones at 30, 60, and 90 days, noting that results depend on the complexity and gap between current and target states. He warns against procrastination disguised as preparation, advocating a “ready, fire, aim” approach: commit to a deadline and work backward, scaling while solving problems in real time. Mogul also highlights that leadership effectiveness is measured by tolerance for uncertainty, and long-term thinking (5-10 years) enables sustainable growth.
Overall, the episode encourages entrepreneurs to forgive past mistakes, focus on learning, and take action despite incomplete readiness.
FAQs
It varies based on the delta between your current state and your goal. Set clear milestones at 30, 60, and 90 days with your team, and track progress against agreed targets.
Preparation involves setting a deadline and working backwards, like signing up for a race and then training. Procrastination is waiting until you feel 'ready,' which may never happen.
You're rarely fully ready. Instead of waiting for perfection, commit to a launch date and figure out the details along the way. Growth comes from taking action, not perfecting systems in advance.
First, ensure they have clear expectations and milestones. If they lack experience, recognize they need time to learn. If they're an expert, hold them accountable to the targets you both agreed on.
Hire people who have already done what you need—'batteries included.' They've learned on someone else's dime. If you can't afford that, set realistic expectations for someone still learning.
Yes, but don't beat yourself up. Learn from mistakes, forgive your past self, and move forward. Wisdom from failures often leads to future wins.
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