Scaling for Freedom: The New Entrepreneurial Mindset | Mac Lackey

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There's, there's three things I end up spending a lot of time with entrepreneurs on because there's the mindset and strategic and all the stuff that feels great, and there's the practical reality of your day-to-day life as an entrepreneur. And for most every entrepreneur, there's three things on there that are the things that truly destroy us tactically. Mac, it's a pleasure to have you on the show today, man. Thanks for taking the time with us. Yeah, Ryan, it's great to be here.

I appreciate it. Yeah, long time coming, uh, but very glad we got here because I think your, your tact, the, the, the position that you take around this idea of scaling for freedom is something that, you know, I get a ton of questions about, and, and I'm not an entrepreneur coach. You know, I am an entrepreneur, currently CEO of an AI company, but, but you know, I don't do any coaching whatever, but you get these side messages, right? And they seem to be around this... There, there seems to be like a, a, a, a really messy moment, a- at least that I'm seeing, where, um, some of the traditional stuff either isn't working as well as it did, or people are worried 'cause they see AI.

At the same time, I think burnout over the last 20 years of tech kind of grind hustle culture is, is starting to get to people. It seems like the, the generation in their early 20s is maybe looking at their life a little differently than, "I wanna be locked in a, in a garage for 20 hours a day." Um, like, uh, maybe we just start there. Like, w- where did this, where did this come about for you? Like, when you started building all these businesses and growing them and exiting from them, like, how did the idea of doing that to have freedom start to come into your own life?

Yeah, it's such a good question, and I think it's, it's incredibly relevant. I mean, even the way you sort of position it, I think the, the last decade or two, um, hustle culture has just become this, like, badge of honor, and I think it's, it's sad. Entrepreneurs kind of feel like that's what they have to do. They have to accept these incredible trade-offs, whether it's personal freedom or health or time with friends and family, to go build a business so that at some point in the future, hopefully they can live the life they want, and I, I just sort of fundamentally disagree with that. And so for me, um, you know, my journey, I started my first company, this, this ages me for sure, but you know, first quarter of 1995, Netscape launched the commercial web browser.

I started an internet company almost immediately thereafter, so it was really early in Web 1, and I built and sold two companies in my 20s. Those companies were definitely defined as kind of garage startups, you know, under-resourced. I came from kind of no, no resources. So incredible, uh, success in terms of I felt very fortunate and blessed to have built and sold companies. It was, it was amazing, but I was probably a classic workaholic.

And then in that second business was sold in July of 2000. My second, uh, or my first daughter was about to be born in August of 2000, and that, that moment is where everything changed for me because I imagined this life as a father, something I was incredibly excited about, and I wanted to be there for kind of every moment. You know, I wanted to be home for dinner. I wanted to coach the soccer teams and go to the school plays. And in that moment, every one of my friends and peers and even mentors said, "Mac, you're a workaholic.

Like, how are you gonna be home at 5:00? Like, all you do is work." And I made a decision literally a week before my daughter was born. I kind of leaned down to my wife's, uh, belly and said, "I don't know how, but I'm gonna be there for everything." And I wasn't really willing to accept that I was at the end of the entrepreneur journey.

I was gonna have to be a lifestyle guy to be a present father. So incredibly long story short, I, I just made the decision. I am committed to being there for my kid, and ultimately I had two girls, but initially it was the one. And, uh, the way I always sort of position this, which I think is super relevant, is my daughter was born August 21st of 2000. I dropped her off for her freshman year at NYU August 23rd of 2019.

So literally 19 years almost to the day, I dropped her off for her freshman year of university, and I looked at her and I said, "You know, I wasn't the perfect dad. I made plenty of mistakes, but I was there for everything. Like, I carved the pumpkins. I was home almost every night for dinner at 5:00, but I also built and sold four more companies." And so over those 19 years, I sort of lived the case study that I didn't know how it was gonna work.

I didn't know if it was even possible, but I was just not gonna accept the trade-offs that everybody was telling me I had to accept. And so at this point, you know, I sort of look back over that. I feel really fortunate, but that moment in 2000 where I just decided I'm not going to follow this traditional path and accept these trade-offs because that's not gonna be my life. I didn't know if it'd work or not, but, um, that's kind of when it all changed for me and led to a very different life. How did you make it work?

So I think, um, yeah, I mean, y- with the benefit of hindsight, things are much easier to see. When it, when it sort of started, one of my favorite, you know, very brief stories I'll tell you is right after she, you know, was, was home from the hospital, um, of course, she wouldn't know if I was there or not, right? She's a baby. But I had already decided I'm gonna be home for dinner. And so in order to be home for dinner, I set an alarm at 4:45 so I could leave the office and get home in about 15, 20 minutes.

And the very first day it happened, I was up on the whiteboard in front of my company, I was running a tech business at the time, talking strategy. The alarm goes off at 4:45. I literally dropped the dry erase pen and turned around and walked out of the office, and I'm positive that people in the room thought like, "Oh, clearly Mac's gonna, like, pop back in and say, 'Ha-ha.'" But I got in my car and drove home. And the next day almost, you know, the same scenario.

I was with my leadership team in the conference room talking about something. Alarm goes off 4:45, literally walk out of the, the office. And what happened was such an unbelievable positive. Um, I was committed to leaving, so I was prepared to deal with the consequences of stuff just kinda gets dropped, things don't go well. But after just a few days, the dialogue in my office very quickly shifted to not I wonder if Mac's gonna leave at 4:45, but Mac is gonna leave at 4:45.

Who's gonna prepare the PowerPoint? Who's gonna take a call from a customer at 5:30 'cause Mac's not gonna be here? Who's gonna... You know? So all of a sudden people started adjusting schedules and planning and proactively imagining Mac's not here, so who's gonna do it?

And then within a week or two it was not who's gonna do it, who's the best person to run the meeting? Who's the best person to take the call? And so I really truly watched these employees, teammates of mine that I didn't realize I was actually holding them down because if Mac is in the office, Mac's gonna run the meeting, Mac's gonna hold the dry erase pen, Mac's gonna take the call. So I literally kind of threw everyone in the deep end with this just, you know, I had an absolute forcing function of I'm physically walking out at 4:45 no matter what. And the company adjusted, employees stepped up, people rose to the occasion.

So I literally realized that the constraints and forcing functions I was creating for my own life by optimizing what mattered to me, I was actually building a better business. Um, you know, fast-forward several companies later, my very last company which I sold back in 2018, I had... I was the largest shareholder. I, I was, you know, CEO or chairman maybe by title. I had no role in the company.

I had a desk, but people didn't know if I was in the office or not, or if I was even in the country or not. Like, everything ran with or without me the same way, people, processes, technology. So I just kinda learned to use these forcing functions to build better businesses that extracted me from the day-to-day. If we can stay in that, in that, uh, early days company when you started to set these boundaries, what were some of the, um, initial either mindset changes as the CEO or, or even tactical operational changes that, that you made, not, not necessarily as your team adjusted, but that you personally as the leader made in order to allow them to flourish more and to, and to continue to support this new culture that you had created? Yeah.

What a great question. Um, a couple things, you know, come to mind. Number one, it, it was a, it was a personal decision, but it had kind of a, a tactical implementation which is, um, number one, I'm not willing to accept the trade-offs, and so that's a personal decision. But I also have an obligation. I'm a fiduciary to shareholders and partners, and, like, I can't perform at a lower level.

So I basically had to say if I'm going to, you know, not accept the trade-offs and optimize for what matters to me, which is time with my family, my business performance has to be the same or maybe even better. So I have to be more efficient and more, you know, hyper-focused on time and efficiency. Like, I might be in the office three hours less, but I gotta get as much or more done. And so that mindset was a, was a big shift for me that I was looking in the mirror and saying, "Mac, you have to perform at or better than when you were sitting in the office three hours more, two days more," whatever the case was. Now that performance orientation became a, a great shift for the entire organization because I was able to look at anybody else and say, "I don't care when you're in the office or not.

This is a performance culture. You get your job done, you perform at or above and we'll be great. If you don't perform, I don't care how long you sit in the office." Like, it's a performance culture. So a lot of those things started with me looking in the mirror trying to hold myself accountable, and then shifted to the way we built companies, the way we thought about things.

Yeah. I, I had a very similar experience with my last company. So what my home industry is the insurance industry, uh, property casualty insurance, and I started a, a national commercial insurance agency, digital commercial insurance agency. So, uh, our value proposition was essentially you can deliver the same amount of value digitally as you could in person, 'cause... And I don't know how familiar you are with property casualty insurance, but the... at that time, so this is, uh, uh, uh, um, uh, 2020.

I started- Mm ... seven days before COVID hit. Oh, wow. Not the best time to start a business, but, uh- Yeah ... we, but we made it work. Um, at that time, there was still the belief that I had to be in the same room with- The holidays are here, and that means it's the most wonderful time of the year to save with Rakuten. Use Rakuten to stack cash back from your favorite stores on top of holiday sales.

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Terms and conditions apply ... you for you to appreciate what I was doing with you, and I wanted to bust that on its head. And, uh, I found that traditional insurance salesmen and women pr- producers, they, they could not vibe with that. They, they couldn't get through their head that they, that they didn't have to be in the room, right? And what I found was, uh, there was an immense amount of talent sitting in single moms and moms with young kids that had been tossed aside because they could not, simply could not work a traditional nine to five. They just, they're, they had responsibilities to their children, and they just, they had to take time, or their kid pukes in the middle of the day, and they gotta run out or whatever, right?

Right. Um, and so I started scooping up all this talent, and it was like a... It was really a, a, a, I got a lot of flack because we had the same exact methodology, and it was a forcing function. Like, like, it wasn't like I had this brilliant idea. It was more like, I need to be able to find people who can do the job, right?

And, and, and basically we, we said the same thing. We were like, "I literally don't care. You have X amount of work that you have to get done. Here's your numbers that you're agreeing to in your contract coming to work with us. I don't care if you get them done at 9:00 PM, 1:30 in the morning, or whenever.

You just have to hit your numbers, and that's it." And it's like it... There's, um... In explaining that to people, though... And it worked incredibly well for us.

Uh, we exited for, uh, uh, four years from the time that we started and very, very good. But, but in explaining that and sharing it on here, I've sho- shared on this show before, I... And I... This is where I'm going with this question, is like I get... A lot of people will lip service me, "Oh, that sounds cool.

It's..." And they go right back to top end heavy, be here, activity-based, uh, per- you know, performance reviews, and I, I struggle with w- why is that, why is moving to a performance culture particularly hard for, for most leaders, most founders, right? I think you go through it enough times or maybe I think tech is a little more vibes with this. But outside of tech really, a lot of businesses struggle with moving to this kinda performance-based culture. Why do you think that is?

Yeah. It, it's, it's a great point. I think it's heavily ingrained, um, in business culture, in entrepreneurial culture. I even, you know, mentor and coach entrepreneurs now that will say, you know, "My leadership style is I lead by example, and how can I lead by example if I'm not in the office working more than my employees? I want to show them the way that you work hard and you do these things."

And I, and I normally smile and say, "You know, I understand, um, but what you're showing people is a broken paradigm." It is, "Yeah, let me punch the clock and show you how many hours I can work, not how I can perform, how efficient I am." And I sort of took the other approach. One of the things that I still say all the time is, and this was very difficult for some of my early companies and my, you know, the constituencies around me, but I always used to say, you know, "I work seven days a week and I play seven days a week. Like, Tuesday and, and Sunday are no different to me."

Like, but people have this really funny, you know, mindset around nine to five, Monday to Friday, and I said, "Well, I have, you know, daughters that I want to drive to school, and so I am not gonna be in the office at 9:00 because that's when they need to be at school. And I have, you know, daughters that I want to coach their soccer team post school, and maybe that's at 4:00." And so I kind of adjusted my schedule, and people have often under- misunderstood. That didn't mean... I've, I've never said I didn't work hard, you know?

I, I feel like working hard is a core attribute of my whole philosophy, but I got to choose when, where, and how. And so a lot of mornings I would wake up really early, 4:00 in the morning, 4:30 in the morning, and I might do two hours of incredibly deep, uninterrupted work before my kids got up, and then I would literally turn off the computer, go make pancakes, drive my kids to school, and then I would go to work again. And, and sometimes I would put them to bed at night a- and I would go back to work, or I would decide to work on a Sunday because th- they had a school play on a Tuesday. So this, these are self, um, imposed constraints that people have. Like, and, and it's pervasive.

I'm not, you know, I'm not naive about it. Like, a lot of people when I say stuff like that, they're like, "Yeah, that would never wo- work in my culture." I'm like, "Well, that's because you haven't set it up so that it's based on performance," and then people are very happy that I might be working on Sunday because then they show up Monday to a very, you know, a lot of great work that otherwise would have waited till Monday night or Tuesday. And so it's, it's really a cultural decision. But what's wonderful about it for entrepreneurs is there is a direct correlation.

So, you know, I've built and sold six companies. I've spent a lot of my life talking to entrepreneurs now about the exit process, and one of the things that I discovered is there is a direct correlation between three things that matter. One is the exit, exit ability or exit value of a company, the ability for a company to scale, and for a founder or key executive's personal freedom, and people really think those things are diametrically opposed. Like, hey, if I'm not grinding in the business, the exit value is going down or it'll be harder to sell. It's actually the opposite.

Nobody wants to buy a company where the founder's in the critical path. If you're in all the meetings and making all the decisions and all the SOPs have your name on them, that is not a good business. It doesn't scale, scale very well, and it's really hard to exit. And if you do exit, you're gonna be in an earn-out for years. And so for me, when I discovered that, it was sort of like, okay, if I design a business that's really designed so I could sell it at any point, high, high exit value, high exit optionality, then I'm basically ensuring that I have a more scalable, efficient business and one where my personal freedom goes up.

Like, sign me up for that all day long. But I think entrepreneurs just for whatever reason have just believed this hustle thing that you just have to sacrifice and grind until one day You can sell it and then you finally can travel with your kids or do whatever you care about, and it's just not the facts. Yeah. You know, I'm, I'm a case study for that. Uh, the business that I was in prior to the, the last one that I started and exited from, I, I was that I'm gonna show you the way, right?

Like, I'm gonna do the things and you follow me along. I literally started, um... I had been telling, um... I had a, I had an individual on my team, she was incredibly talented, you know, gregarious, you know, she's, she's got very, very good-looking woman, just like, like she like drew you in, right? And I, and she's on my marketing team.

And I said, "I need you, or I would like you to start telling some stories yourself about the business. Like, create a kinda sub-YouTube channel." She was very good with video. That was like her specialty. And I was like, "You know, you talk about the business of all those things."

And sh- you know, and she was kinda putting it off. I could tell she was putting it off. She was like, she was nervous, right? And I, and I completely understand that. So one day I literally just created a, a YouTube channel, like sub-YouTube channel of our businesses for myself doing it.

Like, and she, and, and sh- I get this message from her, "You mother..." You know what I mean? She knew what I was doing. Yeah. And like at the time that felt like the right thing to do, but here I am, all of a sudden now I have this YouTube channel that I'm, that I'm building like on the side and I'm like, "What?

This is so stupid. Like, why would I do this? This is just another job that I just created for myself." And it was, it wasn't in... And I think that experience trained me to exactly what you're saying.

And guys, I mean, uh, uh, listen to what Mac is saying. This is, this is the maturation, I believe, of, of the truly great leaders, is when you... Rogue Risk was the name of the, the business that I, my most recent business. When I removed myself from the process and became kind of like of service instead of the service, th- like you said, all of a sudden people started solving problems I didn't even see or didn't even know about, and taking off in different directions. And it was like the whole business opened up when I got out of the way.

And I think in retrospect, a lot of that was like my ego, like, like I'm the point of the spear so I gotta be the point of the spear and things have to go through me. Yeah. And, and the minute I changed that and started empowering my people, w- we went faster, further than I could've ever imagined in a, in a, in a period of time. I mean, my initial, my initial exit strategy was eight years and we sold in four, and that's only because I got the hell out of the way. Um- Exactly ... and so, so when you, when you come across someone, someone calls you, then, "Hey, Mac, I'd love to, you know, hire you for some coaching, you know, we're whatever," and you see that, particularly that part around the ego, like, like, you know, how do you start to break that down? 'Cause I, I feel like that's a blind spot for a lot of entrepreneurs.

They feel like they're doing the right thing and they can justify it. Right. But at its core it's kind of the, their ego is the reason they are, they're remaining in that spot even though they know they should probably get out of the way. How do you start to break that down? Yeah.

So, you know, one of the things that is, is really critical, um, it's kinda like, you know, Tony Robbins I think used to always say that, you know, we don't achieve our shoulds in life, we achieve our musts. So I try to really understand if someone comes to me and says, "Mac, I need your help," it's like, you know, let's talk about what that means. I need to, you know, free up time 'cause I've neglected my family, my health is suffering, or I wanna sell my business. So we sorta start with, okay, how important is this goal? Like, are you committed to making these changes? 'Cause if someone's saying it but they're not committed to making the changes, they'll just go right back to old behavior.

So there is something important about how important it is it to you as an entrepreneur to scale your business, to have the freedom. 'Cause most entrepreneurs, not all, but most entrepreneurs start a business designing it on paper for what they want. They want the freedom, they wanna make money, they wanna scale it, they wanna enjoy it, they wanna be able to sell it one day and maybe, you know, have life-changing outcomes. But then they kinda like get in the grind and they build this cage around themselves, and they stop realizing that the business is no longer doing those things. Like, they're buried in the day-to-day, they're working more hours, they're probably, maybe their business is making more money, but because they're reinvesting their personal wealth isn't going up. Like, it's all tied up in the business.

So to me, I almost always have to take them like, let's look at how important this is. And then the thing that you have to do is you have to realize today in this moment as an entrepreneur, maybe you are the best person to answer the call, make the decision, write the code, design the logo, make, you know, all these things happen, but one, that never scales, right? You can't be the best at all those things 'cause that's not your actual unique ability or talent. So we have to say what is the thing that you do that's critical to the success of the business where you should be spending 80% of your time? Everything else we have to get off your plate, and ideally we're getting it to someone that that's what they are uniquely good at.

If you're doing finance because you're capable and you're probably better than your bookkeeper, you need to hire a controller or a CFO or a fractional resource because you're not going to move the needle as a finance resource. So to me it's kind of breaking these things down that their goals are really critical, and then finding out what do they need to uniquely focus on to move the needle. As I always say, I mean, I literally look at my to-do list myself every day and same thing, every morning of my life I look at it and go, "There's 50 things I could do. There's three of them that move the needle, and that's what I gotta do today." Not to get too tactical, but can you talk through that to-do list process?

Um, because I think this is critical for, for particularly for leadership, right? You, you, like you said, I, I, I could go through this notebook that I have here, and there's probably 1,000 checkbox tasks that actually need to get done, right? But you said, like, that sh- if I went through them chronologically, that would be the biggest, you know, that would be the most inefficient way to do it. So- Is it, do you, you know, I've heard some people just keep a running list and then every night they kind of pick their top three or like what is actually your process for making sure that when you show up in the morning you know what you want to work on and, and what's gonna move that needle the most as you described? Yeah, it's, it's, um, it, it's almost exactly again my s- my style, my system, you know, partially because of, I suppose, you know, age and what I was doing at work when I was building my companies.

I am definitely a notebook guy. You know, it's, it's at my desk back here, otherwise I would show you. It, it's literally like, you know, constantly making notes, um, circling tasks that need to be done, and that's just to make sure I cap- capture them. But the reality is very, very similar to what you said. I look at that usually at night before I kind of shut down and then in the morning and say, "Out of this list, what are the two, three, four things that are aligned to my personal goals and dreams?"

I mean, I literally, I do have laying right in front of me, I have a, you know, my daily non-negotiables that are kind of my key things, and I look at my list and say, "Are they aligned with what I care about most in my life? Time with family, having impact, you know, helping entrepreneurs." Okay, that's a key filter. Will it move the needle? Um, and then almost everything else on my list, I, I created an acronym forever ago.

People have a million acronyms. Mine was DAD because that was my focus. I want to be a great dad, which means everything on my to-do list that doesn't move the needle in a significant way needs to be delegated, automated, or deleted. So, and I delete a lot of stuff, and people really struggle with that one. I'm like, "This, this just has to be off my list."

Um, the only other thing I would say, which is really interesting, is I have, uh, two assistants, and one of my, my executive assistant, I literally have a daily stand-up with her. She's, uh, you know, I live part-time in Barcelona, so she's in Barcelona. Sometimes I'm on her time zone, sometimes I'm in the US. We have a daily stand-up, and I tell her, "You tell me what the most important thing I do today is," because she knows all... I mean, she checks my emails before I see them.

She knows what's in the to-do list. She sees all the things. Because I want her to be another level of filter to me. What she thinks is the most important thing that I do for my day probably should be on my top three because it's I owe somebody something, you know, a follow-up, or I needed to record something, or, you know, whatever it is, she has a really important sense, and that's that ego thing you talked about. I try to strip away all ego and I say like, "You're my, technically my assistant, but you can tell me what to do.

Tell me what the smartest thing for me to do today. What's the most important thing? If I have to cancel something, what's the smartest thing for me to cancel?" Like, I literally put that filter and that weight on her because she's, you know, she's good at what she does, but she has broad insight into what's on my list and what really matters to me. She'll tell me almost every day I'll agree to meet with someone, and this is tough for me.

I try to be a nice, good, friendly person, and she'll s- and I'll say, "Oh, my, you know, friend from high school wanted to have a coffee next week," and she'll literally be, um, as I'm saying it, shaking her head no. And I'm looking at her and she's like, "Remember, you don't have time to do that." Yeah. Like, you're trying to impact the world and help more people. You can definitely send a nice note to your friend, but you can't meet him for a coffee.

You know, and of course I can override that and say, "Ah, he's one of my best friends, I am gonna meet him." But having that sort of accountability and filter to like, I don't waste time on stuff that's not gonna be aligned for me and help try to do what I want to do in life. Yeah. I, I, um, dude, dude, talking about the deleted part, I, I, uh, I had this awakening again at, at, at the last company. I was g- I had like 100 and something emails in my inbox, which is crazy, right?

I hadn't, I hadn't gotten an assistant yet at that point. And like one Saturday morning I woke up and I'm like, "I'm just gonna go all the way to the bottom and like see what's there." And I'm looking at these things, and like at the time they seemed important enough to like keep as unread, and I'm going, "Well, that... Delete, delete, delete." And I got all the way down to like 15 emails and I was like, oh my God, like look how many things that were completely unimportant, that had zero impact, that I actually didn't need to follow up on or whatever, that were just sitting in my inbox creating like noise in my brain 'cause I'm looking at 100 emails and it feels overwhelming every day, when really there's only 15 in here and probably even 10 of those are simple just, you know, one-sentence follow-ups.

A- and we, we allow ourselves to, to get caught in, "Well, geez, I gotta respond to everything," and it's just simply not true. Yeah, it's, it's, it's... If I could say, I mean, the to-do list, I'm glad, I'm glad we talked about that. There's, there's three things I end up spending a lot of time with entrepreneurs on because there's the mindset and strategic and all the stuff that feels great, and then there's the practical reality of your day-to-day life as an entrepreneur. And, and for most every entrepreneur, there's three things on there that are the things that truly destroy us tactically.

One is, um, the to-do list that we kind of talked about high level. The other is our calendar and what we allow on our calendar and how we block time and manage time. And the third is the inbox. And I, yeah, I'm literally looking at, I have my two monitors up as we're recording this, and my inbox that I'm staring at says, "You've hit inbox zero 65 weeks in a row." And, and that is, that is, doesn't mean I don't...

I get a bunch of emails, but my very strict kind of, you know, guidelines on how I follow up, if I follow up, if my assistant follows up, if this is better done. I do a lot of asynchronous, you know, record a quick video because I care about people that I'm working with or in my life. So I'd rather record a nice video and, you know, send you the link to it because it's when I'm sitting on the back porch later in the day, but I send a nice note, "Ryan," you know, "Great talking to you," blah, blah, blah, you know, "Here's the three things we talked about." So I, I try to really let my inbox not dictate my day at all. And then the final one is, is the calendar, which is, it just destroys people.

And I, I do this coaching session with my group, and I'll show them even, you know, again, I know this stuff. I've lived it a lot of my life, but I'm, of course, I'm guilty of letting things drift. And I show people what my calendar looked like two years ago and just pick a random week versus what it looks like now. And now my, my pre-blocked calendar, like my mornings every single day is the same. I start at the same time.

I have pre-blocked time for, you know, flow state and mental health and, you know, things that are priorities for me. When I'm in Barcelona, I have lunch with my wife every day. You know, and those things are like non-negotiable, non-movable. And, and then I have a few blocks where I'm like, "This is when I'm gonna coach or work with clients or help friends." And that ability to kind of get in the zone versus what it used to look like, I'm running multiple companies and I'm going between sales meetings and talking about product, and I'm talking to my financial advisor.

I mean, like context switching all day, different times every day. So I don't- I'm not one of those morning routine people. Um, personally, I actually like a very clean calendar, so I pre-block a lot of time, which just basically means I have total flexibility. If I decide to just go for a walk and not do anything for half a day, like my calendar kind of accommodates that. That scheduling 15-minute increments and being at the gym by this time, like that feels anti what I'm trying to do with my life, which is live happy and free.

Yeah. And so it works for some people, but for me, I have to pre-block time so I have a lot more control of my calendar. So those three things, if you, if you get those three things right, then I think it literally transforms your life as an entrepreneur. Yeah. And I think the, the i- one of the main ideas that I take from that is I, I think a, a derivative thing that not people, that people do not give enough, uh, conversation to is this idea of noise, right?

That's constantly in your head. And when you don't know what your day is gonna be because it's different every day, and, uh, people are randomly dropping stuff into your calendar that you don't know is there, you don't know why it's there, et cetera, et cetera, all that it, it, it ... And you even said it, context switching, right? Like all these things create noise that allow- that doesn't allow you to reach, one, your peak energy state, or two, your peak, uh, clarity or focus on the topic that you're supposed to be talking about. 'Cause now you're like going, "All right. I just got off a sales call.

Now I'm talking to HR." And, uh, and you, you ... It takes you time to get in, and you're not listening, or you're thinking about the last call you had. And, you know, one of the things that I've really tried to work on in 2025, uh, and I would put this noise underneath this topic, is energy management, right? Like I find, similar to you, I n- I put, I put blocks.

I use like the focus time in the Google Calendar is my way of, of having that. Like, I will not allow someone to schedule something over the top of focus time. And, and I've gotten pushback from the team. They're like, "Well, we need to talk to you." I'm like, "Then find another time."

Or cr- like you said, create a quick Loom video, explain it to me, and I'll watch it as soon as I can, and I'll be able to give you an answer. Like, because if I don't have those blocks of time in there, I can't actually do, right? We c- we don't actually, we don't actually get the, the space to do the creative work in whatever capacity that creative work takes to, to solve the big problems, which is ultimately, you know, what we're doing most days. And that, uh, I mean, guys, i- if you're listening to this, you know, and, and go back and, and re-listen to that section, and I'll probably end up pulling that section out as well, 'cause it's ... This is the core.

I mean, if you wanna hear about like some crazy marketing strategy you had that, you know, blew your company up X amount, but you can't even get to that if you don't have those three core things settled in your brain. Like, you literally can't even ... You don't have the brain capacity to come up with the idea to implement the strategy. Um- Yeah. It's, it's the one that, that's really ...

I mean, there, again, to-do list, inbox, and calendar are all like equally challenging for most people. The one that I think is the easiest to solve for but for whatever reason a lot of people struggle is, is calendar. And I always say like, "Let's, let's talk about what, what your calendar looks like today, current state, versus what I call the dream calendar. What would your dream calendar be considering," exactly like you said, Ryan, "what's your energy?" Right?

Like, are you energetic in the afternoon? That's when you wanna be doing sales calls. Or are you creative in the mornings that you wanna like be thinking or meditating or writing? And, and let's d- let's forget all the stuff that you have. Let's just lay it out like it would be amazing, and then let's consider things like, do you wanna, you know, take Fridays off?

Do you wanna be able to travel on the weekends? Do you wanna take one week a month off? Not that you can do it yet, but that's the goal. And so we start off with like current state and future state. And then it's just a simple reverse engineering thing.

And when I'm coaching someone, that's what we'll do is we'll say, "All right. Well, in order to get from where you are to where you wanna go, let's just do two things for the next two weeks. Let's block Friday afternoon after 1:00, and just literally block it in your calendar. You and I both know that if you have an emergency, you can open it up. But let's just go ahead and pre-block it going forward.

And then let's take a whatever, some other day, and put a two-hour block for nothing but creative thinking, strategy. Can you do that?" And most people are like, "Yeah. I can do it as long as I know I can change it." I'm like, "Great.

Do that." And then you just start picking away. And then before, you know, it's another three or four weeks and it's like, "I think we can probably take Fridays off now, you know? And let's just go ahead and pre-block it. There's always emergencies.

There's always exceptions. Let's pre-block it." And then you literally watch people's lives and the way they run their business transform because they control their calendar. And it's just that simple. Like you said, all the brilliant marketing strategies and distribution plans and code that you can write, those things are, of course, critical But none of them can happen the way they should happen at scale or, and/or your life on the journey is going to suck if you don't manage those three things.

And I have way too many friends that they're m- you know, plus or minus my age, I'm 54 now, and they're, you know, my kids are, you know, one's out of college, one's about finished with college, and I'm an empty nester. And I look back and say, like, I s- enjoyed and spent so much time with my kids. I have a lot of friends that are, they just sold their business or they've, you know, s- semi-retiring and they've made so much money and they're like, "But I miss my kids growing up," or, "I'm, you know, falling apart, you know, mentally and physically because I've neglected my health for 20 years while I was grinding, and I finally sold my company for $50 million and now it doesn't matter, I can't travel anyway," you know? Yeah. So I, I really feel so strongly that, that people make these changes because that's what leads to a more scalable business, a business you can sell, but it's your option versus being forced to sell it.

Um, and so yeah, this is, this is as sexy as the other stuff is, these three things are what really make the difference in an entrepreneur's life. You know what's really funny too, and I'm, I'm sure you know this as much as I do, when you, when you sit with like other successful entrepreneurs a lot of times, this is the stuff they wanna talk about. Yeah. Like the real primetime players, like- Yeah ... they don't care about the marketing strategy or the big sale, or even, I mean, they'll talk about product a little bit once in a while. M- more and more like, you know, maybe a little bit of, um, uh, aggrandizing what they did, right?

Like, "Oh, we built this cool thing," whatever, and it's fun. But when you, like when you're sitting in a circle, they're talking about time, how do I get more time with my family? How are you managing comms? How are you making sure you have... I mean, this is the core stuff that people really dig into when you're actually having these conversations with, with high-level successful people.

Um- So true ... and I, I, I just wanna touch on and, and I'm, I'm interested in, in this for you, and then I, I wanna move on to a different topic. But, um, health management, right? I've been saying for years on this show, your health is a competitive advantage. If y- if I'm sitting across a negotiation table, whether it's virtually or, or in person, from someone who is not physically fit, I can tell doesn't manage their energy, they look hungover or whatever, right? Like you know you're gonna win that negotiation.

Like you're gonna, you're gonna outthink them, you're gonna outmaneuver them, you're gonna outpace them because they just haven't managed their energy. And they may be smart as hell, and they may have h- h- been, been successful. But you can, you can outmaneuver them becau- simply because of your health. How were you able to, I mean again, I know this kind a goes into your whole, you know, taking control of your life, but how were you able to fit energy in and, and how did you prioritize, uh, your health and stuff along this journey? I mean, six, six successful exits is i- incredible in and of itself, let alone you look like a very fit, healthy guy and, you know, how were you able to get through all that?

Well, well I appreciate the kind words. I, um, yeah, I think a, a lot of it, you know, I was, soccer was my kind of passion, you know, growing up. I played at a, at a pretty high level. And post, uh, playing I, you know, I continued to use soccer as an outlet for kind of the mental and physical, you know, part of my, my non-work life, my non-family life. And so I, I continued to play up until not terribly long ago.

I was playing four or five days a week, you know, pick-up games, indoor, outdoor, and that was great physical, you know, kind of the, the physical side of, of my health. Um, but also a massive stress reliever, you know? Like I just, I just love playing soccer. And so, um, you know, prioritizing that, I was very fortunate that I found a group that was willing to, 'cause I, I mentioned earlier, I was a very early morning person. Most people play soccer on the weekends or after work, and I found a group here in, in the US where I am now that was playing three mornings a week before people go to the office.

So we'd meet at 5:30, 6:00, 6:15 depending on when the sun came up, play soccer for an hour, then shower, then go to the office. And to me it was like my day is already so good because I've, I've had fun, I've hung out with some friends, I played soccer, I got some, you know, fitness in. So that was a big part of it. And now, I mean, I'd be the first to admit if you, if, if you knew me really well, people know that like, soccer was such a big thing. I don't, like I don't love to run.

There's not a lot of other like forms of exercises. One of the big reasons we live, you know, half the year in Barcelona is it's a lot easier for me to be intentional about those things when I'm in Barcelona. I walk everywhere, every day. I walk to get coffee, I walk to have lunch with my wife, I walk my dog, I get fresh air, I get sun. And where I grew up in, in the US in Charlotte, North Carolina, it's a great city, but I have to get in my car to drive to get a cup of coffee or drive to meet someone for dinner.

And, and so I don't, I have to be much more intentional. I try to design my life where I don't have to think about those things so much, you know? And that's why Barcelona for us is, is wonderful because just by doing the things that I naturally wanna do, I'm getting more exercise, I'm eating healthier food, et cetera. If I, if I was in, you know, some other city, I wouldn't have those same kind of benefits. And so I try to be, you know, intentional and sort of design my life around what makes that stuff easy for me.

Yeah. And that, that feels like a through line for your success and, and I think for many people is, is this intentionality, right? Like setting boundaries and being intentional about the things you want and going and getting them. Uh, so you've- You've now, uh, uh, parlayed all this success and, and, and business knowledge and, and love for soccer, and now you own your own, you own a soccer club. Yeah.

Talk to me a little bit about that decision because, uh, you know, I've never owned a professional sports team myself, although hearing from different people on po- you know, there's, that can be a hit-or-miss relationship and, and opportunity. But I, I've, you know, I'd love the, the decision to, to, to, to purchase the team and, and how, how has applying, um, your entrepreneurial skills to a, a sports franchise, how has that translated? Yeah, it's, it's, um, it's been a really, really fun, like, chapter, you know? So as I mentioned, I, I literally have been a lifelong soccer enthusiast. I used to call myself player, now I say fan 'cause I don't play anymore.

But, um, it- it's been a big part of my life. I mean, you know, growing up it's all I thought about, all I wanted to do, all my goals and dreams were soccer-related, and I was, you know, very fortunate to, you know, check off a lot of those, you know, kind of goals. And then, uh, I got into the business world. A lot of my companies were... I kept weaving back around to, you know, soccer was a through line for me.

So my first company, which was an early internet company, some of our biggest clients were soccer businesses and, and you know, 'cause that's what I wanted to work on. My second company was kind of the, the fusion of early technology with the sport of soccer. I built one of the largest kind of media platforms on the internet. So it's been a through line. My family and I, I pulled my daughters out of school when they were nine and 12 to travel the world.

That's, you know, really, again, uniquely possible because of the way I designed my companies. I was still running companies while doing it. We ultimately moved to Barcelona, um, to have a new experience, and while I was living there, it sort of became this almost, like, bucket list dream, but it was very far out in, in time, in the future of, like, it would just be so cool to buy a soccer team in Spain and maybe when I retire. That was kind of my thinking is I'll get a little place in Spain and retire, and I would love to own a little team. But, um, you know, fast-forward and, and really about five or six years ago, I just started thinking about what's going on in the global kind of game and the business.

What I feel like the American side of sports business is really being, you know, kind of cast around the world. You can see it across a lot of sports, the entertainment value and pre-game and all the things that really didn't exist in Spain. And I was like, "You know what? This isn't a retirement thing. This is a business opportunity.

I, I, I wanna do it," you know? And so kind of sped up the timeline and yeah, it's been about three and a half, four years ago that we, uh, bought a team, and it's 115-year-old team in southern Spain, so multi-generational. It's beautiful, uh, right at the Strait of Gibraltar, so if I'm sitting in my seat, I'm literally looking at the Rock of Gibraltar over the back of the stadium. Morocco's 14 kilometers away. So it's, it's just a beautiful location.

And then to kinda answer your question, you know, it's, it's... I hired a CEO. I have a whole, you know, much more qualified group of people that make day-to-day decisions and coaching staff and recruiting players. I have no role in the club other than, you know, I mean, I, I own it, but I, I, I get involved in things that I'm excited about, but I know that, you know, there are other people that are better at making decisions than me. So it's been, um, it's been a lot of fun.

I've tried to apply a lot of lessons learned and, and business lessons to it, but it's, it's a very different business. And, and 115 years of doing things, I underestimated how resistant to change people would be. I come up with something like, oh, I'm a big brand guy. I love, like, brands and logos. I'm like, "Let's update this, and let's change that."

And I mean, people are like, "Whoa, can't touch the logo. That's been here 100 years." You know? So it's been a funny experience. Uh, in some ways there've been some challenges.

I mean, I've learned already some crazy lessons that, you know, come along with sports team ownership at any level. But yeah, it's been a really, really fun chapter overall. Where does the team s- and, and, um, uh, I'm not as familiar with how... I mean, I know there's, like, different leagues and stuff. Uh, h- where does it fall, like, in relation to some of the other teams that maybe a, a, a US audience might know well, like?

Yeah. So yeah, so it's a, it's a good question. So, um, in Spain there are five tiers of professional soccer. Um, we are in the dead center, so third division, uh, technically. And in Europe in general, and Spain certainly, you know, it's the system of promotion and relegation, so at the end of every season teams are moving up and down from first division to second division to third division to up.

And so, you know, for example, over the past year or two in our division, we play against, you know, teams like Malaga and Ibiza that were formerly first division teams. Malaga was in Champions League eight years ago, but they've been relegated down to our division. And so... And we're also playing against teams that started, you know, in very low divisions, maybe even pre-professional, like amateur level, that have just over decades have become professional. So it's, it's really crazy competitive.

In terms of comparing it to the US, um, you know, some people think, "Oh, it's, you know, it's third division Spain," and like, you know, we probably would beat at least half of the MLS teams in the United States. I mean, there are a few MLS teams that are, of course, at another level, but this, this level is really competitive. Um, and it's neat to see, you know, we have a range of, you know, very young players that- Turn professional, they sign their first contract with a club like ours. We sold a player to Real Madrid two years ago. We have some players that are at the end of their career, and they played in Germany or Russia or somewhere, but now they're older and can no longer play first division, so we might be the last club they play for before they retire.

So it's, it's a neat... You know, there are a lot of stories built into any sports team, but, you know, young players that are hoping to make it that, you know, don't go to school, dropped out of high school to turn pro, won't go to college, and so this is their one shot in life. It's a lot of that human interest kind of stuff wrapped into it. Is the goal always to ascend? Are you trying to just be the best in your division?

Like, how do you manage... Are you, are you constantly managing to ascend to the next level? Or, like, I guess, how do you, how do you work all that out? Like, what's your, how are you structuring your, your strategy there? Yeah, it's, it's, um...

I mean, ultimately most clubs, certainly our club, the goal would be to promote to the next division. There are, you know, very real, significant, meaningful financial benefits to that. You know, the, we have a TV contract. It goes up by seven and a half million a year just with one promotion. I mean, it's, it's a very meaningful, you know, scenario.

But where we're different than, I don't know, other people perhaps, a lot of people look at sports team ownership, and it is kind of an ego or trophy thing. You know, like, they just wanna say, "I won the championship. I won the trophy." And they'll over-fund and lose crazy money to win a trophy. Like, that's just not our strategy.

I mean, w- we do wanna promote in the future by building very methodically. We started two years ago with the back office. Like, I, I inherited a group of players and coaches and didn't change anything. Started with how do we run finance, how do we run operations, how do we... You know, literally in the back of the house, and we've slowly moved up to last year we traded 15 players, we got a new coaching staff.

And so we're just kind of, you know, trying to make smarter decisions, run it like a business, and over time if we're so fortunate to, you know, run it well and assemble a group of players that, that, you know, fight for promotion. This season, um, we really, towards the end of the season, we were in a, kind of a winning streak and really found our rhythm, and the difference between where we ended up at the end of the season versus going into the playoffs was one, one win. And I think if we'd a had, like, two or three more games, we would've been fighting for the playoffs. And then it comes down to do you do well in the playoffs and get promoted or not? But for me, I was very happy with where we ended up.

I thought it was a great season. You know, we're not doing it again for ego, and even if we, even if we did promote, it's not like, you know, we would, uh, do anything different. It would be that same strategy again. You know, hiring good people, managing day to day. Um, so it's, I've learned a lot, but it's been a really fun experience thus far.

Yeah. Uh, one last question on the, on the soccer piece. Um, h- how is it different managing fans as customers than, say, customers as customers? 'Cause it s- seems like, you know, you, you have things like if you change the logo, most of your customers would be like, "Eh, okay. Well, you know, I like your product or I don't." But a fan might say, "I love you guys, but now I'm gonna, you know, shitpost on some Reddit board or whatever the equivalent is- ... because I don't like the logo anymore," and now you gotta deal with that.

Like, h- how is that dynamic? And you've run a media company before, so maybe it's similar in a little bit, but, like, I- I'm very interested in that. No, it's, it's such a good and funny question because that was, was and has been an eye-opener for me. Um, my CEO, who's, you know, a b- a business partner of mine now that runs the day to day, he lives in southern Spain. He, he was formerly a first division, uh, co- or CEO in La Liga in Barcelona, and, and, you know, so he's overqualified.

And, and he told me, he said, "Look, every decision you make, no matter what it is, good or bad, for any reason, some percentage, 5 to 10% of the supporters or the fans are going to hate it and going to be very vocal about it." And early on, I felt incredibly welcome. I was, uh, candidly, I was a little bit worried as an American buying this team that they were gonna be like, "Oh, you know, capitalist, doesn't know anything about soccer." And so I spent the first year going to every home game, letting people know that I cared and I wanted to be there. It wasn't just a, you know, capitalist thing, and it was like I really love it.

I would just sometimes sit up in the box with their jackets on, and, like, I'm down in the sports bar with our fans having a beer before the game , you know? So I really wanted it to be different, feel different. But the reality is, after a short period of time when people are just excited 'cause there's change and there's something new, then it segments into those people that understand what you're doing and probably get it and are supportive, and those that you can do no right. I mean, there's literally... So I get direct messages to my social media account sometimes from people about, like, which player's playing or not, and I'm like, "I, I have nothing to do with that.

Like, I have a coach." "I don't decide who plays." You know? And it's... And, and I, you know, they're passionate, which is such a good thing, and, and they're, they care so much about their team and their club.

And as a human, especially one that actually, again, try to be a good person, I wanna explain to people, like, "Hey, we've invested, you know, a million dollars over budget this year to make things better." But, but then people will literally send me messages and be like, "Just put more money in the club." And it's like, you, you don't understand actually what we're doing. We're, we've put a lot more than we probably should have in. So yeah, I, I smile just because it is true.

Like, I've just decided, like, there's gonna be some fans that it doesn't matter what we do. We could win the championship and they're gonna complain about how we won it, you know? It's likeWell, as a lifelong Bills fan, I can say I completely understand their side of the aisle even though- Yeah ... you know what I mean? You, you, I got buddies, it's, it's so funny. You know, I, I, I feel for you, and it, I was, you know, in getting ready to, to chat with you, I, I really wanted to spend some time in the soccer club 'cause I find it, I find that business model so intriguing.

I'm a lifelong baseball player and played football. I, I unfortunately got injured or I probably would've played football in, uh, college, but ended up playing baseball because, uh, of an injury. But, um, like, it, it's, it is a wild dynamic, right? No matter how good a service you have, no matter where you are, like from a standard business perspective, no one's tattooing your logo on, on their arm or their leg, right? Yeah.

But when you have a sports club, you know- Yeah ... they, they, they're gonna tattoo it. They're gonna wear the jersey, the hat. They're gonna, you know, they're gonna do all these crazy, have flags and shrines. I mean, I, I don't know if you've ever driven through Buffalo, New York, but literally their thing there is they, these guys build shrines, and I mean that in the purest sense of the term, to the Bills in their garages. And on game day, all their garages are open, and you can drive through neighborhoods, and it's like, you're like- It's so cool ... what is going on?

You know? Yeah. And the, the amount of passion, and Josh Allen can throw 39 touchdowns, and people are still talking about how, "Well, if only he was a more accurate passer." It's like he won- Yeah ... the MVP this year. What are we talking about?

So true. Uh, well, Mac, I, dude, I could talk to you for hours. I appreciate you. Uh, this has been wonderful, and, and I really appreciate the tactical stuff 'cause I do think that it, it is very easy, especially with social media and with a lot of, you know, maybe even people that are trying to do the right thing but, but aren't necessarily giving the right advice, or they're going for the wrong types of metrics in their advice. They, they don't slow down to talk about these actual tactical things that drive true leadership and, and how we actually get there.

So I, I appreciate that, man. Um, if, if someone wants to just get in your world more and just kinda be in, in, in what you're creating, what you're talking about, where can they go to, to get involved in your work? Yeah, thank you. Um, so I have a, like a personal website, um, at, you know, it's basically maclackey.com, so M-A-C, uh, Lackey, L-A-C-K-E-Y. So maclackey.com, you know, is, is my kinda core website.

On social media, it's kind of @maclackey on YouTube and across the social channels. And literally just in the past few months, I have made a commitment to try to truly put out more content for, for the reason you said, which is I feel like there are a lot of people talking about these very esoteric high-level things, and those things are important too, but I've just been trying to share, you know, very tactical changes people can make. I wanna help people. I wanna ... You know, I know that for every person that joins one of my group programs or coaches with me, there's 1,000 more I can help that they'll never need or want to join something, and that's great.

I wanna put a lot of stuff out there. So, so yeah, I, I, I think if people are interested, follow me on social media and, and send me a message. You know, my team and I, we really truly try to help, and if, if, you know, we can help someone, send them a free resource, recommend something, send them to someone else that can help them, uh, we certainly wanna do that, so. Well, I appreciate you, man. Thank you so much.

Thanks for having me. I- Let's go. Yeah. Make it look, make it look, make it look easy. Hey, stand up Thank you for listening to The Ryan Hanley Show.

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