Building a Life and Business Without Losing Yourself with Chris Kille

What happens when success pushes you to the edge, and your body tells you the truth your mind has been avoiding?

In this powerful and deeply human episode, host Dionne Malush sits down with Chris Kille, a Boston-based entrepreneur, author, and operations expert who learned the hard way that achievement means nothing if you lose yourself in the process.

Chris shares the moment that changed everything, a sudden, terrifying health scare doctors believed was a stroke, and how it forced him to confront burnout, addiction, unsustainable habits, and the lie that entrepreneurs must carry every burden alone.

This conversation is honest, grounding, and full of the kind of wisdom that only comes from falling apart and choosing to rise stronger. If you’ve ever felt overwhelmed, exhausted, or alone on your entrepreneurial path, this episode will remind you that you’re not the only one and that rebuilding is always possible.

A raw and inspiring look at resilience, reinvention, and the courage to finally choose yourself.

Connect with Chris here:

Website: https://www.chriskille.com/

LinkedIn: https://www.linkedin.com/in/chriskille/

Facebook: https://www.facebook.com/chris.kille.9/

Chapters

• 0:00 Meet Chris Killey And Mission
• 2:30 Soft Side And Dog Stories
• 4:30 First Exit Lessons And Mentors
• 8:40 Burnout, ER Scare, And Sobriety
• 15:30 Building EO Staff And Exiting Payments
• 18:30 Why Founders Resist Hiring Help
• 23:00 Embracing 80 Percent Done By Others
• 26:30 Life Upgrades From Quitting Alcohol
• 31:30 Health First: Time Blocking And Team
• 35:00 Mentorship, Community, And Standards
• 39:30 Content Pillars, Hooks, And Authenticity

Transcript

SPEAKER_00: 0:02

Today's guest is Chris Killey, a Boston-based entrepreneur, author, and operations expert who is on a mission to help business owners scale without KMS, which I'd love to know about. He's the founder of EMS Staff, a premium remote staffing company that connects fast-growing businesses with elite virtual assistants. Chris has built and sold four companies, written for Forbes and Entrepreneur.com over a hundred times and is the author of The Rise of Virtual Assistants. His story isn't just about business growth, it's about resilience. After a cardiac event caused by burnout, Chris discovered the power of remote staffing, and now he helps entrepreneurs build businesses that run with freedom and not stress. Hi, Chris. I'm so excited to see you. It's been too long. I can't even believe it's probably been two years since we've been in the same room. How are you doing?

SPEAKER_01: 0:48

I'm doing really well. I'm doing really well. I'm very I'm looking forward to doing this. This is uh this is very exciting to me.

SPEAKER_00: 0:53

Oh, cool. And I me too. And I always uh like to start with the first question is what what is one thing you want people to know about you that doesn't show up in your bio?

SPEAKER_01: 1:01

What you know, one thing that I think I want people to know about me is, you know, I'm I'm a big softy whenever it comes to to feelings and animals and and things like that. I know a lot of people uh they wouldn't guess that about me, but it's uh my my dogs kind of run my life for me. Everything, everything's revolved around my dogs.

SPEAKER_00: 1:20

I have two dogs too. What kind of dogs did you have?

SPEAKER_01: 1:22

So I have a well, they're both poodle mixes. One is eight pounds, his name's Harry. We call him Handsome Harry because he loves to uh he loves to stare at himself in the mirror. So handsome Harry. And then uh and then I have a uh poodle Australian Shepherd mix. His name's Baxter, and he's about 30 pounds.

SPEAKER_00: 1:39

Nice. I have two little wiener dogs. One's name is Hulk for the Incredible Hulk because he was little when we real little when I got him. And the other one's name is Mercy because when my husband was going through his transplant, we went to Mercy Hospital, so we named her Murphy. And the nurses were so blown away by that. We took her in onto your desk, we just got her and snuck her in the back door of the hospital. It's kind of fun. But yeah, so I love dogs. I don't have kids, so for me, dogs are it. So I do love that. I love that you are soft like that, but I kind of knew that about you, I think. Just from getting to know you at our our Apex events, which I miss so much. That was a lot of fun. We have a great time.

SPEAKER_01: 2:13

For sure.

SPEAKER_00: 2:14

You built and sold four companies. Looking back, what's the defining moment that shaped you the most as an entrepreneur?

SPEAKER_01: 2:21

I think that I would definitely say from selling my first one to selling my second. When I first exited my uh my first payments company, I've done it several times. But the first time I really I didn't know, I didn't have a mentor, I didn't have anybody that was kind of teaching me, and I really got taken advantage of. I don't think it was too malicious, but it was more of like I was negotiating with somebody who knew that they were negotiating against somebody who did not know what they were doing. I had no idea. And, you know, so being able to learn from that and establish skill sets and and and just be able to bounce back from that because I do think, you know, I left, you know, several hundred thousand dollars, if not a million dollars, on the table at that point. Being able to just kind of accept that as a learning experience, I definitely think that that's that was a turning point, a defining point in my, you know, because I realized that I have to, you know, if you're gonna succeed, you have to continue to learn, right? You can't do it by yourself. You have to get mentors, you have to find coaching, you have to read, right? So it's um, you know, definitely that's something that I that I believe was a real turning point, kind of eye-opening to realize when you leave that much money on the table because you just weren't prepared for something.

SPEAKER_00: 3:28

I can remember when we were once, I think in Dallas and we were sitting in the lobby of a hotel and we were talking about that, and you were telling me about your loss. And I was sitting there and I was like, oh my goodness, if that happened to me, I don't know if I could pick up the pieces. That was a lot, but you did. And so I keep watching you pick up the pieces. And for me, that's what entrepreneurship is all about. It's those of us that fall, which we do, right? We all have failure, and then we pick up the pieces and we keep moving on. And why I did this podcast because I was going through some grief from my dad passing away, and I wanted to do something to show that you know, we all go through things, and it's just how we pick up the resilience that we pick up with, and you're doing it. And I love that about you. So thank you for sharing that. But I know one thing happened, and I wasn't much aware of this until I read your bio about a major health scare that you had that changed your path. Can you take us inside that moment and what it taught you?

SPEAKER_01: 4:20

Yeah, so I was um fortunately it it happened. I hate that it happened, but I'm glad it happened in this way. I have always had high blood pressure, always. And we have history of heart disease in the family, and you know, I mean, you know how it goes, right? It's so I was supposed to get a I was I was in a pre-op meeting because I was supposed to get a um a deviated septum surgery. And turns out I went to another doctor, and he's like, You don't need it anyway. That's a whole nother story. But um, I was so I went to a pre-op and I got there a little bit early, and um, you know, I walked in and I sat at the lobby you know, I sat inside of the lobby and I sat down and I, you know, I have my I had my water like I always have with and I started getting dizzy and you know my face started getting hot and so I started like oh just I'll just drink some water or whatever, and it just didn't go away. And then so I got up and I was like, I'm gonna pace a little bit, maybe it wouldn't go away. So I went and I knocked on the the window and the woman came and I was like, hey, just out of curiosity, I was like, does anybody have a blood pressure cuff back there or something? I have high blood pressure anyway, so I just want to make sure that we're still and she was like, you know what? Just go have a seat. We're on lunch right now. We'll, you know, we'll we'll be with you whenever we can. Um which is fine. Right. So I went and I sat back down. I figured I could wait. Well, it just continued to get worse. And then my face started kind of like tingling and it was bright red. And so I went back up and unknocked again. And um, and she was, I was like, I really don't mean to be a bother, but you know, can is it okay? So she uh she she and another nurse came out and they they did my uh my left arm and they did that right, they let it off and then they kind of looked at each other and they're like, let's just try it again. And they did it again, and then they're like, Well, let's let's try the other arm. And so they did it on the other one, and then they're like, Are you feeling okay? And I was like, No, I oh, I told you, no, I'm not feeling good right now. Why? Why's that? Now he's scaring me, right? And um, and so then they were like, Well, let's bring you back to the doctor. So we went back and they hooked me up to one of the uh actual, like not just the blood pressure coffee, it was the machine, right, that does it. And they did it twice, and then they were like, Hey, we we think you you might be like they started asking me all these questions. They're like, We don't want to bother, but we need to call an ambulance like right now. And so, you know, they wouldn't really tell me anything because they didn't want to upset me. But long story short, we happened to be in a in a hospital complex anyway. It was one of the places that was in DFW, and so it was just a everything was, you know, the the primary was in the place where you get your surgery, was in the everything just happened to be in the same complex. And so the ambulance came and they were asking me all kinds of questions. They just wanted me, they just kept wanting me to keep talking and they were asking me like, what's your favorite song? What's your what's your birthday? And I found out later why they were doing this. But so they were like, hey, we're gonna take you over across the, you know, across the street to there just happened to be a cardiac unit over there. And so we we get we go to the cardiac, uh, they they put me in the gurney, and it's very embarrassing for me. I I don't like having anybody like making a fuss about me. I'd rather like I I would have rather just you know teeled over if I had to rather than make a scene. And so they uh so went over there and they had me on the gurney, and the guy, uh, one of the EMTs went up to the front door. The waiting room was packed. There was like a hundred people in the waiting room. And he went up and knocked on the window and talked to the person, you know, quietly. And then they just kind of waved me back. And I was like, shit, right? This is not, you know, I'm bypassing a hundred people here. They were asking me, like, what, you know, again, what are the favorite like what's what song can I sing to them? Not to sing, but you know, they just wanted to keep me talking. They put me but right back into a CT miss uh to CAT scan. And um, I found out later they thought I had a stroke, is what it was. My yeah, my blood pressure was about 220 over 190. And so they were like, hey, you know, they they thought it was a stroke, and fortunately it wasn't. It actually just turned out to be a really bad anxiety attack, but um oh my god, it was yeah, it was a wake-up call.

SPEAKER_00: 7:57

Listen, I'd had the exact same numbers happen to me. This same thing, it was anxiety, and then that was when I was 40, which was 17 years ago. The same work 220 over 190. That was my number.

SPEAKER_01: 8:09

Yeah, it was my skin was tingling. It was, I mean, it was it was scary. So that was kind of when I, you know, I was living really hard. I was going through a divorce um at the time. It was just not a very a lot of stress from work, and it just wasn't a very healthy, you know. I was I was drinking a lot, I was yeah, doing other doing other things. And uh, you know, the doctor came in and talked to me and he was like, you know, hey, listen, man, you you have you gotta get your shit together. He's like, you've got you know, health and you know, you've got these things in your family, this history, and and your blood pressure is already high anyway. And you know, he kind of explained the whole process and he was kind of like, you gotta start drinking, man. And I was like, Yeah, okay, yeah, sure, sure, sure. And then he's like, No, no, no, like you're you're gonna die if we don't, you know, not today, not tomorrow, but you know, you're cutting many, many years off your life unless you and so yeah, that was a big wake-up call for me. And that was kind of when everything went, everything went clean. I haven't I haven't had a drink since.

SPEAKER_00: 9:01

How old long ago is that?

SPEAKER_01: 9:02

It's almost two years ago.

SPEAKER_00: 9:04

Yeah. Wow. So it didn't change me the way it changed you, but it scared me enough to to know because my dad had had a heart attack at 47. So I was 40 when that happened. So as I cruised through my life in the age 47, every time I had a pain, I was like, oh my gosh, he's had a heart attack, you know. And so, but you know, I I made it through it, but it really it did change me in a in different ways. You know, I was definitely more reactive to my the pains that I had in my body and how I felt. But anxiety was so bad, and I didn't know that anxiety could cause every pain, every symptom of a heart attack, right? But you can't know, like you can't just assume it's that because it it doesn't feel like that. So yeah, yeah. So yeah, it's made some changes, which is huge. And then so since I last saw you, you have this new company. Is that correct? Is new company?

SPEAKER_01: 9:51

So I've had EO staff for four years now, technically. I was running both company companies simultaneously. So the last time when I saw you, EO was just kind of like a side hustle, just like a fun project. Excuse me, just like a fun project for me. I've since exited my my other the company that I was full-time at whenever I met whenever I met you. That's I got out of that company uh January 13th of this year. And so I've been full time with EO. That was a payment processing company, yeah, payment pilot.

SPEAKER_00: 10:20

Okay. So let me ask you this. So you're in that space of more kind of like drowning in all this stuff, right? You're you had businesses going, you had, you know, having lots of fun because that's what we did, right? We had a lot of fun when we were for using up fun. How do you believe entrepreneurs resist bringing on help? Because that's what you're doing with the VA staffing company, right? When they're drowning in the day-to-day, why do they resist it so much?

SPEAKER_01: 10:45

So I think it's for two reasons. Um, from what I've seen. One, if you're gonna hire good help and you're gonna look to hire somebody that's gonna sit beside you or somebody here in the States, things are expensive now. And there are not a lot of A players out there. So most people, and myself, I was exactly like this. I knew I needed help. This was for 10 years. And but I had a lifestyle that I wanted to keep up with, right? I wasn't willing to like Chris ate first during that time, right? And anything left over was okay, we'll see if we can find somebody. And what ends up happening is I I wasn't willing to do that, and most people aren't. So the little money that I did have and then I tried to hire people with, I was I was attracting C players or D or worse, because A players know their worth. Also, you know, they're they're not cheap, right? However, you'll usually get four to six times the output of an A player than you will of a B. So if you're ever looking, you know, you get across an A player and they're more expensive than everybody else in the market, hire them because you're gonna turn your, you know, you're gonna get a higher ROI much faster. But most people they try that route. They try to go cheap, right? Small business owner, you know, like, oh, I got to save every penny I can. I'm gonna, you know, attract somebody that's that will work for them. Let me see if can I get you to work for this? Well, you know, at the end of the day, somebody who knows their own work isn't gonna come in and work for less. Or they hire somebody, or this could be an and, and or they'll hire somebody who'll come in and they'll try to onboard them. And what ends up happening is they they don't realize that when you hire somebody, a lot of times you have to take a step or two back to be able to delegate and to be able to install this person into your business. So a lot of times they'll get frustrated and they'll just say, you know what, it's fine. I'll just do it myself. You're fired, or or we're not gonna, you know, we're not gonna do this anymore. I can do it just as good as myself, or if not better than you, and I don't want to have to manage your tries. But what they don't realize is that, you know, it's only a temporary setback initially. You have to onboard somebody the right way, and then you never have to deal with it again because you can put together playbooks and standard operating procedures and and have an entire process around it, but there is a little bit of work up front. And that was at least where I went wrong over and over and over again. Just kind of, you know what? No, no, don't worry about it. I'll just do it myself. And um, and that's where you that could steer you wrong.

SPEAKER_00: 12:54

See, it's freeing though when you finally let it happen. So even for myself, you know, I didn't understand it until one day I realized that Rockefeller had the right idea when he said, I'd rather have one percent of a hundred people than a hundred percent of my own efforts. Yeah, exactly. That's so huge when you think about that, because now as an owner of a brokerage has 215 people in it, you know, I can't possibly work as hard as all 250 of them do. You know?

SPEAKER_01: 13:19

Of course not. Yeah. And then the you know, the other thing too is it's like people are, oh you know, and sometimes it's not going to be good as as as well as you could do it, right? Can't can't be done, you know. Dion, you're the you know, I'm sure you're the best at what it is you do. And somebody who you bring in, right, they maybe they can only do 80%. But you know what? 80% done by somebody else is a hundred percent awesome. That's what one of my mentors says, and it's like, look, you we're always chasing perfection. Yeah, that's Dim Martell. So, you know, yeah. I wish I could say 80% done by somebody else is a hundred percent awesome.

SPEAKER_00: 13:52

I love them writing that one down. So, what has been one of the hardest lessons you've learned as an entrepreneur? Because outside of you know, the health scare, because that's something, you know, you never know what's what's happening there. You can't predict it all the time. But what's something that's really been on your mind about that lesson that you learned?

SPEAKER_01: 14:10

I mean, I think for me, having that catalyst, I knew that I needed to stop drinking, right? It was I had you could go back through my Facebook, my DMs, and from 15 years previous, whenever like before I was married, whenever I was dating, I was you telling people like, hey, I'd I would rather not meet for drinks. I had a problem. I mean, that's you know, I didn't want to admit it, but but I did. I had a drinking problem. And it wasn't like I would sit around and think about drinking all the time, but it was when I started, I couldn't stop. It was, you know, you get the thing, and what it was never one drink, never. It was, you know, one drink turns into four o'clock in the morning, turn, you know what I mean? And there's a lot of people out there with me. Like that, you know, I'm an A, I'm an I'm an A personality. I'm a hard driver. And I know a lot of people just like me that work hard, play hard. And for me, with alcohol, play really, really hard. But learning and knowing that about myself and having the right, having having the right motivations to be able to actually implement that and stick with it. I haven't had a hangover in two years, right? I have, I don't, I used to miss at least one day of work, at least every single week because I was hungover. And so, you know, I don't, I don't deal with that anymore. I'm not, you know, my my credit card companies, they hate me because I'm not going out to that's I'm not, you know, two, three hundred dollar dinners or and I just don't do them anymore. I'm saving a lot of money that way. I've lost a lot of weight. You know, it's just, it's been, it's been incredible to just live, you know, working out again all the time. And so when I started taking care of myself, that was when everything changed. You know, my income's up. I'm much happier. I'm, you know, I'm not taking anxiety medications anymore. I stopped, you know, I stopped taking, you know, I stopped taking Adderall. I don't, I don't have the need for it anymore. It was, you know, it's just everything changed. And that was the biggest lesson that I think I took away from all of that. And it's just, it's been incredible.

SPEAKER_00: 15:59

Plus, you have this beautiful new relationship. What's actually not new, but it's newer, right? You look so it's I love it.

SPEAKER_01: 16:05

I am because you know, and she played a big factor in that too. So, you know, this is kind of something I don't talk about often, but Ashley, who's my fiancee, she doesn't drink, her family doesn't drink. I mean, they'll they'll have a drink occasionally, but alcohol is not doesn't play a factor. It's strange because we'll have people over for like 4th of July and things like that, and no one brings beer. Usually, you know, there's people drinking beer the whole time, they bring they bring soda and you know, wild side. And it's crazy because it's just like never around. So that's that's awesome for me. But, you know, she had been in some relationships before with some with some people and you know that that drank heavily. And, you know, I mean, I can't speak to them, but I can tell you that she had standards in place that, you know, if you so I and I knew that, you know, she I had had a couple um, you know, moments where I was like, you know what? I think that I'm gonna lose this one if if I, you know, again, because I'm sure I've lost other relationships from my drinking before, but you know, she was a big factor. I I didn't want, I didn't want to lose her. And I knew that if I continued on the path that I was going to, it was not, it was bound to happen. Absolutely. And so, um, you know, so that was just another set of motivation and and consequences for me because I respond really well to consequences. So, you know, being in this relationship is the best relationship I've ever had, right? It's you know, we don't argue, we don't fight, it's like we have disagreements, but we talk about like adults and uh you know, hurry games.

SPEAKER_00: 17:29

Drinking every right, you don't have drinking yet, yeah, because then you get we went to we went to Longhorn Steakhouse, yeah.

SPEAKER_01: 17:35

Okay, so I used to be like this big steakhouse snob.

SPEAKER_00: 17:38

I remember what was within Texas, right? Every what?

SPEAKER_01: 17:41

Man, I'm not if we're not going to if it's not 400 bucks, I don't want to go. It's one of those. We went to Longhorn Steakhouse last week, right? Or last weekend. I've never been to Longhorn before. I mean, that's the first time. It was pretty good. It was$38. When do we left?

SPEAKER_00: 17:57

That's ridiculous. And it was good, yeah.

SPEAKER_01: 17:59

It was 38 bucks. And I was like, okay, right. So, and that was appetizer, entree. We split a rack of ribs, you know, appetizer, entree, bloom and onion, rack of ribs, and a dessert. And$38. And so I was like, oh my gosh. So, you know, that's one of the things about being up in Maine, you know, there's not a there's not a lot of fancy stuff up there, and I'm and I'm cool with that. And uh, but yeah, so my my wallet thanks me, and my credit card companies hate me now.

SPEAKER_00: 18:26

But you know, this would have been Yeah, those days in Texas were expensive, that's for sure. When went to Apex, it was so you remember that? Were you there that one night where that the guy that the salt bay guy were you at that?

SPEAKER_01: 18:37

Yeah, I was one of the ones who organized that one.

SPEAKER_00: 18:39

Yeah, do you remember how much that was? I don't even know because I didn't get to see the book.

SPEAKER_01: 18:42

Yeah, it was about sixty thousand dollars to eat. Yeah, it was that was I think what there was more than 20 people there, right? And there was one person, yes. I think it was and what ended up happening was the guy who ended up kind of taking control of that. I'm still friends with him, I'm not gonna say his name, but the guy who took control of that ordering, because they were like not everybody's ordering, like one person needs to order. So the guy was sitting across me, he took control, he was order, order, order, order, order. Well, then when the fucking bill came around, he dipped, he was gone. And and so I'm sitting there going, Oh my god, because I'm the second one here. And and the bill, if I wouldn't, I don't know if it was 60, it was more than 40. So it was in between 40 and 60, right? Can't remember. I was I didn't have the money. I don't know how much you I don't have no way.

SPEAKER_00: 19:26

I wouldn't have been able to pay it that way.

SPEAKER_01: 19:27

No way. And you know, everybody's drinking, there's all these, you know, entrepreneurs there and stuff. And so, but fortunately, one of one of the people that was in the group at the time, she came in and she picked up the entire bill and she's got it like that, apparently. So it was uh thank you very much.

SPEAKER_00: 19:42

Oh, the huge attack write-off, right?

SPEAKER_01: 19:44

That's what that's what it was. Yeah, that's what it was for. But it was uh woof, yeah. No, that was I've never been a part of anything like that before, but that was a lot of fun. We had a great night.

SPEAKER_00: 19:53

So much. It was so great, it was a unique experience. I'll never forget it. But yeah, when I heard about the key paid the whole bill, I was like, oh my goodness, yeah, that's not something I could do. Even like, yeah. So, anyways, so how do you balance all this? Like you're writing, you're leading companies, you know, you're protecting your health, which is the biggest thing now, and your relationship. How do you keep that balance?

SPEAKER_01: 20:13

Yeah, so my health comes first, I time block, right? So my you know, I prioritize sleep and I prioritize the gym, and it's a non-negotiable for me. So I have time on my calendar that is just, you know, typically I go to the gym from 9:30 uh to 11:30 or 9 to 11. It's you know, basically I took two hours, and that counts my commute and my shower and stuff like that. So two hours total. We usually work out for a little over an hour. We're just under health comes first. Um, obviously, I've got an incredible team around me. And so, you know, my my executive assistant, Faye, she and I, we just we communicate so well and she's so intuitive and she's very up, she has an operations background. So, you know, for her to be able to um to be able to come through and it's just it's we get along and I'm able to delegate so much through her. And then she actually, you know, she's like my chief of staff. So I'll brain dump on her, and then she goes and and makes sure that the appropriate people are are you know delegated to, and then she keeps uh she keeps everybody in order. And that's one of the things that we teach here. So it's you know, when a new client comes on for us, we we train their executive assistant how to do that.

SPEAKER_00: 21:22

That makes sense.

SPEAKER_01: 21:23

That's what it's that's what they're there for. You know, it's it's they're there to assist you, not to be, you know, you shouldn't have to wonder what they're up to, right? Um, you shouldn't have to wonder what'd you do today? Would you do the, you know, it's so there's there's a lot of things. And so yeah, for me, time blocking and I prioritize my health, I prioritize my sleep. And then I just have a great network of people that want to win together.

SPEAKER_00: 21:43

So tell me about mentorship and how important has that been in your journey. Like we talked, you talked about that a little bit at the before, but tell me more about that and maybe who's been the your favorite mentor along the way or somebody that's really helped change to you to be the person you are today or help.

SPEAKER_01: 21:58

Yeah, I mean, so for me, I go through seasons and um and that's the easiest way to kind of describe you know my life as a whole. And it's almost funny because kind of like decade by decade. So, you know, I have been an entrepreneur. I started my first business whenever I was a kid. And whenever I really went into business full time for myself, I think I was 21 or 22, and it's because I couldn't hold a job, right? So I just, you know, we're being honest here. I would get a job, I would get fired. Get a job, I get fired, get a job, I get fired. So I was like, oh shit, if I'm gonna have to, I'm gonna have to figure this out, so I'm probably gonna have to work from this talk. And um, it worked out, right, fortunately. But initially I didn't, I didn't want help from anybody. I was like, you know what, I'm just gonna figure this out myself. I'm you know, very stubborn and and strong-willed. I was like, I will figure it out. And I did for the most part, you know, for a little part. But then um, you know, about uh 2020, 2021, I started, you know, started like, you know, it's maybe it's time I learned. Maybe I could start. I'd never spent a dollar on self-improvement. Never, never once. I thought it was stupid. And, you know, then then I joined a group where I met you at and you know, started meeting people who had been there before, right? Where uh I'm like, hey, I'm about to do this. Where I'm, you know, talking to one of my one of my buddies, Adam, about something. I'm thinking he's like, oh, you know, maybe instead of doing that, I don't know if you've if you potentially looked at it this way or something. And it the reason being is because I've been there, I've done this before. And and I've experienced that. And so what I learned was when you start hanging around with networks, because look, being an entrepreneur is lonely, right? A lot of times you're the you're the big fish in the small pond, a lot of times. Most times your friend, your family, and your friends have absolutely no idea what it is that you're going through. They don't know how the stress and the the just the the the shit that's happening in your brain, right, every single day and how much stress it is and how it's you it's it's hard. And so when I found groups of it sounds so cliche, but like-minded people, right, that were there hanging on, being able to sh for and it's like it's not so lonely anymore. And then all of a sudden now, you know, you you you're you're meeting people that that are willing to show you the roadblocks and where the landmines are. And you know, part of it for me too is you your bullshit meter come starts to get into play. I really didn't have one then I was forced, I was forced to grow one because you know, not everybody out there has your best interests in mind, right? But you know, when you uh when you start associating with with groups of people who are doing things at a higher level, especially when they're doing it higher than you, man, it is so cool to learn and to be able to build and foster those relationships from people. And some of my best friends came out of those groups.

SPEAKER_00: 24:31

That's really cool. I mean, I've definitely met some amazing people during that time. And, you know, I'm still looking for it again. I feel like I'm searching everywhere for that same kind of group, you know. It was so good. We just it was a really great bunch of people. So I do miss that. And I've been, you know, coached or mentored pretty much my entire real estate career. And prior to that, as a graphic designer, I didn't do that. You know, I just did it all on my own and figured it all out and so fuddled my ass and then got back up and did it again. But, you know, I see today the importance of it. And it is really true about who you hang around with, it makes the biggest difference. So if you're out there hanging around with people that are drinking every day still and partying, you're you're gonna sooner or later, you might just crack, you know, and it's it's just the way it works. So, you know, I I appreciate that about you, that how much you've grown from that. And if you had a look at freedom as you see it today versus your burnout experience in prior two, I know you told me a little bit about your cool little town you live in in near Boston. What does freedom look like for Chris today?

SPEAKER_01: 25:30

For me, I still think that a lot of people might say, oh, freedom just be able to do whatever I want, whenever I want. And, you know, to a point, I think a lot of people, if you get into that with mentality, then I think your purpose kind of goes away, or at least it's it's not defined. Freedom for me is being able to live life on my terms without fear of having something taken from me, whether it you know, my house or my cars, or you know, be able to be financially secure enough to do what I want when I want, but still being able to utilize my time in the way that I see fit, moving towards, you know, my, you know, the the the goal that I am trying to accomplish at the time, moving, making sure that I'm working within my principles and you know, trying to make sure that that you know, I'm living life on my terms as cliche as that sounds, but but it really is I don't want to have to be dependent on somebody else. I never want anybody to be able to have leverage over me or be able to force me into a situation where I have to do something at risk of, you know, if I don't, I'm I'm risk losing, you know, anything really for that matter.

SPEAKER_00: 26:35

Yeah, that makes a lot of sense. And freedom is different for everyone. Maybe we don't all have the same idea of what that could be. But one thing I've been noticing lately is your social media, it's looking really good. Like there's some really great reels that you're doing. And I sit there and I'm like, wow, that is so good, you know. So how you've been published over a hundred times, that's a lot. What is your process for creating content that keeps resonating and positioning positioning you as the authority because it's really working, Chris? From what I see.

SPEAKER_01: 27:05

Thank you. I appreciate that. For me, from a content perspective, it's about organization and it's about hooks. So um, and that's still something I believe I struggle with. Um and I I have a coach, you know, for that that's literally helping me with how to write a hook, how to write a better hook. And um, so for me, I had my content pillars, right? And then so it's basically here are your here are your principles, right? Here's what we're talking about. So, and that could be top of funnel, middle funnel, bottom funnel. So top of funnel is something that's not business related at all. It's just my personality. For example, I have a video on um on a roast beef sandwich at this restaurant that I like in Charlotte, North Carolina that has if you if you aggregate all the views, like from you know, it's it's published in a lot of different areas and shared quite a bit. If you if you aggregate the views, it's over two million views. It's about a roast beef sandwich that I like, a French dip sandwich at this restaurant called 131 Maine in Charlotte, North Carolina. Might as well just plug it, whatever. But I didn't get a gift certificate or anything from it. It's just I was telling a story on camera about a sandwich that I liked. And so that got so much engagement and you'd people fighting. Like they people you think people fight over politics, talk about food, you know, it's like crazy. And you say, Hey, you know what? It's their opinion, right? It's and I'm just like, dude, it's I I like the sandwich. I don't know what to say, right? So um, you know, so you have your top of funnel content like that, which is just to show your personality to to your people, and then middle funnel content, just general business stuff, and then bottom of funnel, and that's like that's gonna be stuff where I talk about VAs and I teach and I want to say, hey, here's how you do this. And as expected, your bottom funnel content usually doesn't do that hot because you know it's people aren't, you know, they're not most people don't want to learn about a virtual assistant, and that's cool, right? But it has to be there for the people who who do. So I focus most of my content around top of funnel things, things that I like to talk about, funny stories, you know, stuff that's happened to me, you know, in the past. And you know, just like I don't just having fun in front of the camera. And uh um, that was really difficult for me at first to figure out. I thought that everything had to be Mr. Teacher, you know, talking head, Alex Ormozy guru type shit, right? And don't get I'm not taking anything away from him. But for me personally, I haven't earned any, right? Like I I don't I haven't sold a hundred million dollars worth worth of stuff, or I don't have, you know, 10 books that are, you know. I mean, I'm an Amazon bestseller. That's cool, right? You can't take that three categories, right? Can't take that away from me, but far, far removed from you know, from Wall Street Journal, New York Times, right? And so, you know, yeah. So for me, I start with content buckets, right? And which are gonna be the core principles, the things that I talk about over and over and over again. And then I, you know, decide if it's gonna be top of funnel, middle funnel, bottom funnel. And then I try to come up with a hook like what's something that I can say that will get you to watch past three seconds. So, like I like I was just on a call with my coach like an hour and a half ago, and he was going through some of my hooks that that I He's like, hey, we're gonna we're gonna switch these around, we're gonna have these reshot because we think it could be better. It could be as simple as like, you know, entrepreneurs waste their time on this, right? Something well, that's the way I say it because I'm very direct. But he's like, What if you said, you know, 95% of CEOs have better, you know, have have better time management skills just because they do this one thing of like, oh, okay, so that's that's the same thing that I was gonna say. It's just in a much, much more, you know, attractive so just little things like that, you know, get them past three seconds, and then you know, there's uh really it's fun, it's just like it's just a game.

SPEAKER_00: 30:33

That's a lot of things you're doing too. And I think if anybody listening should watch, I think they should watch how you're doing it because it's it it's interesting. And like I would before we even go on, I just listened to a couple more and I was like, man, he's funny. He has a lot of good stuff. So thank you for sharing all that. It's fun to learn about it because with AI taking over like it is, which I love AI and don't I mean I use it a hundred times a day, but there's still something about being real. Probably why they called it reels, right? Yeah, yeah. So yeah, and I love AI, and you know, I'm learning some hard lessons about it though, where I think that it works, but it doesn't. And you know, even websites and with you know, with YouTube, YouTube doesn't want AI videos on there. And so when I think I'm so many videos and all this stuff, and I threw an AI one on there, it gets zero light.

SPEAKER_01: 31:18

Yep. Yep. You know, but AI is still really good from a from an organizational standpoint, right? If it's if you want to get, like, for instance, your content buckets, right? You want to put them together, man, that can help you do that. But you know, then you could you've got to be the one that takes that takes the wheel after that and really really brings that human element to it.

SPEAKER_00: 31:37

For sure. So I I wanted to compliment you on that. So it's really thank you. Cool. So if you could give one system or leverage principle to every entrepreneur listening, what would it be? What's something you could lead them with?

SPEAKER_01: 31:49

So one of the things that that we teach are, you know, we have what's called our 360 roadmap. And that could be for a normal employee, it could be for a virtual assistant, it could be anybody in the company, but it's basically when you hire somebody, the path over the first 90 days, what it should look like, right? Here's your clear deliverables. Here is the, you know, by the end of month one, you should have this, these three things, or whatever. And it and it every role is different. But to an entrepreneur, if you're just starting out, or if you maybe have employees, maybe you don't, maybe you have an assistant, maybe you don't. The number one thing, and people attack me for this all the time that you should take off your plate as email manager. Okay, let me let me take a step back from this. Most people, I get three to four hundred emails a day, right? As I'm sure you do too, right? And probably everybody who's listening, out of those, probably 50 or 60 are business related. Most are spam, right? 50 or 60 are business related. Out of that, maybe four or five actually require my attention. And so just having somebody that can organize your inbox who knows when this thing comes, when this type of email or from this person or with the subject, it goes here. Basically, playing triage, right? That way, when you log into your email, most people have their in. I don't know, you may be one of the people too. Your Gmail might be up right now. It's always in the background. Oh, and so you'll you'll go, you'll see it, and you'll probably check it a hundred times a day, and you don't even realize that you're doing. And I turn that over. That's one of the first things I do. I check my email one time per day. Once, actually, I checked it twice a day because I had to log in and pull the link for this, but right before the call. But I check it once per day in the morning. And my assistant, Faye, she keeps everything completely organized for me. So when I log in, I see the emails, the only things that require my attention. Okay. And everything else has either been delegated to somebody else. If it's a simple question that she knows the answer to, she'll respond to it. Hey, Dion, this is Chris, you know, or this is Faye, Chris's assistant. I saw you emailed about this. You know, here's the answer to it. I talk with Chris, whatever, here's the thing. And just that way I can log in and I'm in and out of my email, usually at about 15 minutes now, where I go through and it's done and I don't have to think about it anymore. The other thing, and here's just a tip too. Even if you have an assistant, you can if you because you don't have an assistant, you can fake like you have one and pull this trick. When somebody emails you, you should always respond to that person within a couple of minutes. And you can put an autoresponder on there, but you want to you want to finagle it so it doesn't look like an autoresponder because you can go in and you can mess with the settings. But to where it says, you know, again, hey Dion, this is this is Faye, Chris's assistant. I want to let you know we've received your email and I have flagged it for when Chris's next scheduled email time is. That way we'll get back to you soon. Because most people like if you if you send me an email, sometimes, and I'm the same way, if I send somebody an email and I don't hear back from by the end of the day, sometimes it pisses me off. You too, but yeah, you too. I do agree. Like, come on, dude, am I not important? But yeah, if I get a response right away from somebody, hey, you know what? John, we hear you. I know you sent this message over and it's been flagged. Chris is going to get to it as soon as he can, but it's been received, it's been organized, and it's waiting for him. And so just setting something like that up, one, it buys you more time. Two, it um it it makes it to where your customer's like, wow, okay, cool. And you say you have an assistant, you you you feel more important than you, you know, more you put yourself up on a pedestal, you know, it's impressive. Yeah, absolutely. There's assistance on it.

SPEAKER_00: 35:09

Yeah, I'm gonna tell you exactly when my when I pull up my phone here. I think I work no, I think I have like a hundred and thirty thousand unread emails in my email.

SPEAKER_01: 35:17

Just so you gotta archive those. Woof.

SPEAKER_00: 35:20

A lot that I haven't even read. Yeah, because I try to just read the ones that are important. I try to have them going up in folders, but I never even thought we were that first thing they to do because I have so many emails.

SPEAKER_01: 35:30

But you have an EA, right? You've got an executive assistant. No, I get out of here.

SPEAKER_00: 35:35

No, but I have we have some, you know, I have some people working on some the some of the design stuff for me and you know the creative side, but no, not once, not ever. I have staff that doesn't they barely do any of the stuff for me.

SPEAKER_01: 35:47

So you need somebody to just watch your back and your back only.

SPEAKER_00: 35:50

Yeah, see, well, some we're preaching to the choir right here. Yeah. So thank you for that advice because that email management is a big thing. And I know it does take a lot of time out of my day just trying to sift through it. There's so many, you miss stuff no matter how good you are when you're getting hundreds now a day. So thank you for that.

SPEAKER_01: 36:06

And you know what? So, real quick, if you want, for whoever's listening, I have a playbook on this and I'll give it away for free. If is it okay if I plug it real quick?

SPEAKER_00: 36:13

We'll have to, yes. I was just about to ask you that. Good yeah.

SPEAKER_01: 36:16

I was gonna say if you if somebody wants to follow me on Instagram and my my name's right there, I am Chris Killey. Just send me a DM and you know, and just say, uh, you know, tell me that you're looking for the uh the email management, the playbook, and uh I'll send it right over to you. No, no, no, uh, no charge or questions asked.

SPEAKER_00: 36:32

Thank you so much. So let me let me ask you another question. So, how do they find your book?

SPEAKER_01: 36:36

Find the book on Amazon. You can Google my name, or you can search by my name, Chris Killey, K-I-L-L-E. And uh it's called The Rides of Virtual Assistance. I think it's like$4.99. We kept it cheap. So it's I'm not not looking to make any money off of it, just want to get the word out there.

SPEAKER_00: 36:49

So before we go, we I would love talking to you. I could talk to you all day long. Tell me something about you personally. What's your favorite thing to do outside of work?

SPEAKER_01: 36:56

Right now, yeah, outside of work. Right now, my favorite thing to do is just hang out at my lake house on the dock. Yeah, honestly. And um, I just made a video about it the other day. I I sit there, I don't do anything when I'm out there. I mean, and it's just it's so relaxed. No, not at none at all. But I go through phases. So right now I'm in that relaxed, right? Well, sometimes I'll, you know, you know, maybe in a couple months I'll be really into golf again. Or, you know, I just bought, I just bought a little sports car. And so maybe I'll start driving that, right? It's like I bought it, I wanted it, and I just wanted I wanted a red convertible. So I ended up buying an older red Porsche convertible, and that thing is so much fun to drive. So maybe that'll be into it. But yeah, I mean, just like from a personal standpoint, I love doing things that that are relaxing to me, that can kind of take some of the edge off of, you know, of running a business as you know it's tough. And you know, I feel like um, I feel like I earned it, right? And so that's you know, I love that being at up at my place because it's it's there's just nothing like it. It's just quiet and peaceful and no sirens, no helicopters, no planes, no chem, no chemtrails or anything except it's just clean and nice.

SPEAKER_00: 38:02

Yeah, I love that you have that time. You know, for me, like I I'm starting to feel with a real big sense of overwhelm right now where everything's coming at me and I have so much creativity and I keep wanting to do all these things. I want to start a new business, I want to do this, I want to and my mind just doesn't stop. And so to have that space, you know, I don't know, I think you probably know my husband had a liver transplant this year. So we spent the last five and a half months dealing with that, and we're still there. We're still he's still in a lot of breathing, you know. So, on top of all of this was that, and that was definitely the hardest thing I've ever been through in my life. And my dad dying was, I mean, number one, that was it. Then this, because it was it's been so long, we've been going through it, and sometimes I can tell him to think there was this idea to breathe. Like I need a break, you know. But hopefully I get it soon, and you know, he gets better because if when he gets better, that's gonna help me feel better about taking breaks.

SPEAKER_01: 38:50

Yeah, I've been watching you guys, I've been watching that uh that process on social media too. That's incredible.

SPEAKER_00: 38:55

It is because of diabetes. You know, he didn't drink, he didn't smoke, he didn't do drugs. It was diabetes that kicked his ass. So I did not know that. Sugar the drug. The biggest that's my biggest social media post ever about sugar being the drug.

SPEAKER_01: 39:07

I love sugar. Terrible for it. That's my advice now. I can't, I can't. I'm so oh yeah, but I'm glad that he's on that. I'm glad he's on the right path.

SPEAKER_00: 39:16

Uh me too. Thank you for being on here with me. It's been a pleasure. I hope someday again we'll run, we'll cross paths. I hope we'll see each other. Is Apex still doing things? I don't know, but I hope to see you someday soon.

SPEAKER_01: 39:26

We definitely will. We'll continue to hang out.

SPEAKER_00: 39:27

That sounds like a plan.