I Created Financial Freedom Faster Than I Learned How to Be Free | Tyler Hennessee
Key Takeaways
- Developing early childhood independence to avoid being a burden can lead to a lifelong struggle with asking for help and carrying invisible pressure.
- Pursuing financial success and explosive business growth does not automatically grant freedom from the constant demands of work.
- High personal expectations can cause even monumental professional achievements to feel ordinary, pushing ambitious leaders straight into the next goal without celebrating.
- Experiencing profound personal losses, such as the loss of a best friend and a father's debilitating stroke, can shift a leader's perspective to fear regret far more than failure.
- Transitioning away from a long-term identity—such as decades in ministry—triggers a profound identity crisis that forces entrepreneurs to discover who they are beyond their title.
What if you finally create the freedom you've been chasing—only to discover you still don't know how to stop working long enough to experience it?
After nearly 20 years in ministry, Tyler Hennessee stepped into entrepreneurship and built a business that has grown more than 800% since January. But behind the explosive growth is a familiar struggle: hundreds of people with access to him, a mind that rarely shuts off, friendships receiving less of him, and the uncomfortable realization that while he teaches others how to buy back their time, he's increasingly giving away his own.
In this conversation, Tyler opens up about the childhood independence that taught him not to burden others, the lifelong pressure to perform and prove his worth, the losses that changed his relationship with time, and the identity crisis that followed leaving ministry.
Ultimately, we wrestle with a question every ambitious person eventually has to answer: Are you stewarding your time as intentionally as you're stewarding your success?
In this episode, you'll learn:
- How learning "no one is coming to save you" as a child helped Tyler become extraordinarily resourceful—but also made asking for help feel like burdening someone else.
- Why being loved and encouraged by his father still didn't eliminate Tyler's need to perform, achieve, and continually prove his worth.
- Why Tyler believes pursuing money as the goal eventually destroys peace—and how he's trying to pursue extraordinary success without making it his identity.
- How losing his best friend, watching his father suffer a debilitating stroke, and losing his closest business mentor changed Tyler's willingness to postpone the life he felt called to live.
- What happened when Tyler left a 20-year identity in ministry behind and suddenly couldn't answer the question, "Who am I now?"
- Why explosive business growth has created more financial freedom—but hasn't yet given Tyler freedom from the constant demands of the business.
- The uncomfortable contradiction Tyler is confronting today: he knows presence, relationships, and time matter most, yet still has to consciously remind himself to stop, slow down, and experience them.
Key Time Stamps:
- 05:02: The childhood belief that made asking for help feel like being a burden
- 14:26: Why every accomplishment still left me asking, "Did you see what I did?"
- 16:16: When high expectations make even your biggest wins feel ordinary
- 24:38: I couldn't admit I was struggling because Hennessee men don't show weakness
- 29:12: The moment I finally broke after years of refusing to cry
- 36:31: Why chasing more money and finding peace may be incompatible
- 41:37: The pressure I carry that nobody else is putting on me
- 43:30: My business grew 812%—and my reaction was, "Cool, what's next?"
- 45:31: Losing my best friend changed the way I love the people still here
- 49:20: The day my childhood hero collapsed in my arms
- 54:21: Losing the people I loved made me more afraid of regret than failure
- 56:49: I left the identity I'd carried for 20 years—and had no idea who I was anymore
- 1:08:00: The uncomfortable truth about how often I actually feel "off"
- 1:22:34: I have the success I wanted—and I'm still learning how to enjoy it
- 1:26:49: Am I stewarding my time as intentionally as I teach people to steward their money?
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Frequently Asked Questions
Who is Tyler Hennessee?
Tyler Hennessee is an entrepreneur and former minister who grew his business by over 800% after transitioning out of 20 years in ministry, while navigating the internal costs of high achievement.
What led Tyler Hennessee to become so independent at an early age?
Growing up homeschooled with a mother facing physical ailments and a hardworking entrepreneurial father, Tyler learned to problem-solve early to avoid being a burden.
How does Tyler Hennessee's childhood impact his ability to ask for help today?
His early decision not to burden his parents taught him to fend for himself, making it difficult for him to ask for help or admit when he is struggling as an adult.
What is the core conflict Tyler Hennessee faces with his business success?
Despite creating financial freedom and experiencing explosive business growth, Tyler struggles to slow down, stop working, and be truly present for the relationships that matter most.
0:01 Paul Salter: Tyler, there are many levels, layers, complexities to the journey that has led the two of us sitting across from one another today. And before we dive into all of that, I actually want to go backwards to where it all began. And something in our preparation that you shared with me really stood out. You said that there were struggles in early childhood that forced you to become independent pretty early on. What was happening? Tyler Hennessee: Man, we're jumping right in. I love it. So I mean, I I will say I I I am blessed to have two parents that stayed together and you know poured into us. But I was homeschooled till fourth grade. So it's me and my sister back in Kate well, we were in Fort Worth, Dallas area for a while, and then in Houston, Katy, Texas area for a while. But as a homeschool kid, one at that age, maybe back in the eighties, I'm gonna age myself real quick, but you know, late eighties. Paul Salter: Mm-hmm.
1:03 Tyler Hennessee: it was you d we did things on our own. We didn't have like a co-op or people we went and met with and stuff like that. And and I my my mom had a lot of physical ailments. So because of that, she was our homeschool teacher. My dad was a full and entrepreneur businessman, and he was out of the house all day. And she a lot of times, you know, was unable to to be present. So because of that, my sister and I learned to a problem solve. You know, you don't realize it when you're going through it, but looking back on it, I learned to problem solve. I learned to be self-sufficient. I learned to play by myself and be imaginative and creative and stuff like that. You know, that was only until about fourth grade, but that set a precedent that I didn't realize was going to affect me the rest of my life.
1:45 Paul Salter: How old were you when you first remember feeling like you needed to figure things out on your own? Tyler Hennessee: I would say probably around like eight years old. around that stage and and and in a great way. I look I mean, we all have probably different opinions on upbringing and and how to, you know, raise our kids and stuff like that. But I I definitely was not raised by parents that are just like handed us everything. They didn't spoon feed us and you know, we went through bankruptcy when I was a a a younger kid, didn't know that, but because we lacked a lot monetarily, they still took care of us. Obviously, we had food and shelter, which I'm very grateful for. but I I remember just having to kind of fend for myself, figure things out a lot of times. And you know, my dad was always there for support and and asked for guidance and stuff, but it was he's very old school too. My dad had me late in life. He was thirty-nine when he had me, when they had me. So like, you know, pretty older dad, old school. He's born in the nineteen forty-five. So very, you know, choose the hard road, hard things are gonna make you better. trial by tribulation, you know, trial and chisel and all that type of stuff. So yeah, it's remember just being like, you know, that's where that not to jump on that too early, but that's that phrase hard makes you better that we talk about inside my company. Cause anytime my kids say something's hard or we have a bunch of whiners across America who tend to like, you know, always point the finger and blame somebody else. I was not raised that way. I was raised to figure it out. So Paul Salter: So when you were young, figuring things out, left to fend for yourself, as you said, what did independence mean for that young boy back then?
3:17 Tyler Hennessee: Man, you're really bringing me back, Paul. I'm trying to think. I I think just realizing that no one wasn't gonna necessarily come and save you. And I I mean I I gained a lot of I mean, we all have insecurities, right? But I think I became pretty confident in what I was doing because if you actually did it yourself, you're like, I I'm confident learning to even, you know, make make food and as a as a young kid and figuring things out with relationships and I I I've always just been lean towards just being very blunt, very direct, very honest with people, not beating around the bush, not trying to make people dislike me. If if you don't, that's all right type deal. but I think I think there was more psychological effect than I've ever even taken the time to I've not sat sat there and dove real deep to figure out, you know, I I I've spent time on personality tests and all that type of stuff. And you and you start realizing, that might be a part of my childhood. But I I do think the independent side derive from that and then it matched with my personality of just I'm a go-getter by nature, I'm a competitor by nature, I'm a hustler by nature. And so a lot of that stuff I think, you know, did derive from that that time period.
4:27 Paul Salter: So I what comes to mind for me as I listen is, you know, this independence was clearly so valuable as I talk about nonstop. You know, we always develop these set of intangibles and characteristics that serve us really well. They're born out of a need to get our needs met. We've already mentioned, you know, you were left defend yourself. Typically, along the way, at some point in life, they start to kind of flirt with crossing over between superpower to kryptonite. But for you, I want to know was independence more about I don't wanna burden my mom, I don't wanna ask for help, or was it more about survival or even freedom for that young boy? Tyler Hennessee: Yeah. I I would actually say the former. So like and I wanna be really clear, not i i I I'm I'm gonna be transparent with you about everything, but I I didn't feel like necess at the time for sure, like I was left to fend for myself. You don't you don't know any different, right? When you're a child, you're like whatever your home is like, you think everyone home is home is like. You don't have no idea, you have no context. So my my parents were were My dad, you know, was home every night and my mom was there every day. it's just I think I didn't want to be a burden, if I'm being completely honest. I felt like she has she had a bunch of surgeries and migraines and you know, you don't want to add on to what they're dealing with. And so yeah, I mean that that definitely, man, that's like even singing out loud right now, it's sad. It's kind of sad to think about. But me, my sister to this day, man, my sister's three years older than me. She is one of my, you know, top three best friends in the entire world. We we and that's that's rare for a lot of siblings. We love each other, we have each other's back, we have completely different lives, but we've like respect one another and just really grew tight. We had no idea how much we bonded. and and a lot of it came from that. You know, we spent a lot of time together.
6:05 Paul Salter: Yeah. Yeah. Yeah. Well go one step further for me then. So you you acknowledge, which I kind of heard listening between the lines too, like you didn't want to be a burden. That's totally understandable. What would you say that chapter of your life taught you about asking for help? Tyler Hennessee: Yeah, so I suck at that. I'm I'm hopefully getting a little bit better. I don't like to feel like I'm I don't want to be needy and I don't want man, like there's definitely some tons of psychology behind that and probably all sorts of what I've had, you know, I guess I don't know if therapy or whatever you wanna say is needed on that end. But yeah, I don't like to be a burden to anybody. I like to be I like to bring value in any relationship that I'm in. Like As as you and I get to know each other more, I'd want you to be like, man, you know what? That that guy didn't just come do a podcast, but like he actually brought value. Like I that's the way my mind thinks instantly. But I also think when you add value to someone else's life, they tend to return it too. You know, there there is this kind of reciprocal emotion that can happen. but yeah, there's that has stayed with me for sure. I I don't want to I I do struggle asking for help in general. there's no doubt about it.
7:16 Paul Salter: Yeah, I admire and appreciate the vulnerability and the honesty there. So if we kind of move our journey along, you know, you're learning to be independent from a young age. You're also watching your dad run a business. You already alluded, he's running this entrepreneurial lifestyle. What did being a business owner look like through your eyes as a young kid? Tyler Hennessee: Yeah, so he had to change a couple of times, but I mean the the context of this is pretty wild. So my dad's sister's husband, so my uncle, but I if you go one phrase over, I'm like, wait, I gotta do the math. But it's it's my uncle. So my my uncle is Bob Perry, Perry Holmes. If you live anywhere in the South, people know Perry Holmes. He's literally one of the top national builders in the entire country. but my dad and him had started a business together at one point from their uncle in the building company. And they kind of split ways. I don't I don't from my understanding what there was no animosity, but Perry took on Perry Homes and my dad took on a Hennessy Homes. And in the I think early eighties, my dad was number one builder in Houston, which was a major deal. And then, you know, I there's some interest crisis and all that stuff. And then we went into bankruptcy, I believe, in eighty five, eighty six. I was very young. I didn't have any like I said, I've no idea. But My dad going through that, where a lot of people I think quit and you know, it's it it's it's hard to ever get back. He went and worked for someone else, a dear friend in the landscaping business and did sales and all that type of stuff, built it back up and then started Hennessy Building Company in the late eighties, and that started to to perform again. And so you you fast forward years and years and years, you he ended up having a very successful business. Wasn't wasn't near not near Perry, but enough to provide for our family, right? And you know, but my my observation was just my dad worked hard. I remember like in being a homeschooler, he would bring me in his truck. Back in the day you could ride in the front seat. I or maybe you couldn't, but we did I ride in the front seat and remember like j going up to job sites and I just thought it was so cool because he was a home builder, you know, watching The concrete get poured, watching the the framing go up, watching the roof go, and and how he would communicate with his subcontractors. I I at that time had no context, but man, he was extremely relational. My dad is one of the most anybody who meets my dad loves my dad. Like super, super relational, kind, the most generous man I've ever met. I remember he would like don't know what what they're doing, but Hannah Hennet's one twenty dollars, Hennett's one a hundred dollars, and he's already paying.
9:49 Tyler Hennessee: He's like, hey, you did a good job with this part. And and they would gravitate towards him. So I loved watching, because he called himself the builder. I'm like, you're actually just in charge of the people who who build, you know, figuring out what building actually is. Like you need to know how it works. But yeah, I think it was cool to watch him have his hand in a lot of different things. And so I I loved it. And I would go, I would ask you to work with him as much as possible. I just love being on job sites. Paul Salter: Yeah. Paul Salter: Are qualities that you saw in your dad back then as a young boy that you brought forward to how you operate in your business today? Tyler Hennessee: A hundred percent. Like so much of who I am today, I credit to him for sure. I mean it it makes me a little sad right now sitting out like my dad had a stroke three years ago and basically a deal dehabilitating one. He's still alive, but he's in a wheelchair for life and it just it sucked the life out of him. So he was definitely my idol, role model, someone I was very, very close with. And man, he like truly he would my dad to a fault gave probably too much. So he gave what we didn't have. So he was just a a giver. He was, you know, radically changed when he was like 33 years old and, you know, lived for the world and all this type of stuff. And then, you know, we were we are people who like you know follow Jesus. We're people and and I don't I don't push my faith on people. But when I to see his story and who he was Air Force, military man, played Division one football, you know, ladies man, all this type of stuff. Kind of was the guy. And then got so humbled at, you know, 32 years old radically. his character, man. Like I remember leaving a grocery store and they gave him back. I'm not kidding, it was less than a dollar. Like they messed up on the change. And he had me go back inside and bring it to him. And stuff like that impacted me a lot as a child. Cause I was like, man, like why it's si 60 cents. What are we doing? And he's like, Well, we gotta do what's right. And so those things, his generosity, his humility, never like From w again, in his time, like he was all central All American. Like I said, he he was the gu first guy to get a full full ride out of his out of his school meridian. Like he had tons to brag on in an earthly sense, but he had been humbled so much that he he walked that way. And so I I definitely wanted to be that way.
12:05 Paul Salter: So you have this front row seat to an incredibly hardworking man with the utmost humility, this, you know, giving heart. And he's also really good at what he does. Was there ever an expectation, whether spoken or unspoken, that you were gonna eventually follow your dad into that business? Tyler Hennessee: Yes. I don't know I don't know if he ever like said, you need to take over, but it was definitely unspoken in fifty different ways. Like I always it got to a point and I'm like, I wanna I wanna be and that was as y as a young kid, there was a pride level to me. I love seeing Name Hennessey on the signs. and I and and I loved our last name. I still love our last name. I think it's a cool last name. And so you know, I would see Hennessey Hums or Hennessey Building Company or Hennessey Real Estate, City West Realty, and I thought that was just so cool driving around town, seeing my dad's name. And again, he presented it so humbly, but I was like, That's cool. Like I wanna I wanna be that guy. And so that was that was there for sure. Yeah.
13:04 Paul Salter: Did you feel like you were the one choosing that path, or did it simply feel like who you were supposed to become? Hmm. Tyler Hennessee: The second, the latter s I think is who I was supposed to become, I think. And he didn't I d I really don't feel like he pressured me because when I didn't choose that path, I mean, he didn't push at all. He really didn't. but it looked so cool to you you think until you're actually in charge of something, this looks all fun and you're getting to tell people what to do. And golly, like running my own business today, it's it's it could be further from the truth. it just means all the pressures, all the stress, all the hidden, all the invisible things that no one knows is on you. And now you're responsible for other families and So yeah, it's changed a lot, but n it it was not pressured, but I definitely thought, you know, there's maybe come a time when I'm gonna get a take over this business.
13:50 Paul Salter: How much did making your dad proud influence what you thought you needed to do, what you thought you needed to accomplish? Tyler Hennessee: Yeah, I think that that's still probably something to this day. I mean, I think I don't know if that's in us all innately, but I wanted to please both my parents, but I definitely wanna make my dad proud. Like I tried in sports. And he would all he always told me he's proud of me. He always told me he told me that he I only remembered his dad telling me he loved him one time. And he told me he loved me every day. To this day, if I call my dad, he's gonna tell you I love you, bud. so I think I definitely wanted I know I wanted to to please him in basketball, or, you know, Paul Salter: Hmm. Tyler Hennessee: Trying out for football and realizing I was too small to be what do you I was skinnier and not as, you know, as strong and those types of things. so I wanted to please them in that and then get getting into get my real estate license at Texas at the it was the hardest state in the country to get your real estate license in. And most people I think it said 25% pass. I'm not a good test taker and I literally like aced the test and I was like, Look, dad, you know, I I'm about to be, you know, be in your be with you. And so I think what I need to realize, he was always proud of me. This I didn't need to do those things to earn it. But man, it's it's definitely still in me. There's almost like this performative, I want to prove my worth. But man, it's like my wife will tell you like any of my accomplishments. and I've I've had some really pretty huge things happen in the last few years. I don't celebrate very well. It's like as soon as it happens, I'm like.
14:50 Paul Salter: Yeah. Paul Salter: Mm-hmm. Tyler Hennessee: That was supposed to happen, on to the next. Because I'm just it's it's just a constant performance. It's like just trying to do the best of what I got. Paul Salter: Was there ever a point or a moment where maybe a decision you made or an action you took in order to you in your mind make your dad proud was actually incongruent or inauthentic to who you were?
15:38 Tyler Hennessee: That's a great question, Paul. Like something that I tried to achieve just to please him, you're saying that wasn't really true? Paul Salter: Yeah. And knowingly or unknowingly at the time, of course. Tyler Hennessee: Yeah. Man. I really don't know. I don't want to mix something up for you, but I I would say a a lot of especially childhood into like tw early twenties, I think everything I did, I want to be dad, you see what I just did? Like do you see that, Dad? and and the phrase, my wife hates this, but they'd always be like, Well, of course they my my their response was always, Of course you did, or you know, I wouldn't expect anything less. And as kind as that is Paul Salter: No. Tyler Hennessee: It always is like like, not I I mean, I I I really, really hope this doesn't sound arrogant 'cause I I mean it the exact opposite. But like when high expectations are on you, it's almost like no matter what you do, no one's ever impressed or ever really pleased. And so there's always been this like Dude, is any is anything impressive? And and and and but the the bottom line is that I that identity, that confidence needs to come from within. And for me it comes with my in my faith, you know, to be like, I'm secure here. I don't need to do these things to to to prove it to anybody else. But that that's that's been a constant battle throughout my life, for sure.
16:53 Paul Salter: So reconcile this with me, because on one hand, your dad is a one of very few father in that generation saying I love you, saying I'm proud of you, yet here you are constantly driven, pursuing more and more, more in order to make him proud. What do you feel that, you know, late teenager young man in his early 20s needed or wanted to hear after an accomplishment from his dad? Tyler Hennessee: Yeah, man, I mean, you you're good at these questions, brother. I I don't know for sure what I was seeking other than just maybe validation, just to know that like maybe some i I at at the core of that, I'm sure there's insecurity, there's lack of being seen, lack of being known. d despite again their love for me was was great, but the absence was still there. And so I think just constantly have you have you seen what I've done, have you seen the work I'm putting in? so I think just constantly trying to seek that approval, which is, you know, the older you get, it it's like even when you get the approval, it's like it's on to the next thing. It doesn't really it doesn't fulfill. And so I think it was just constantly chasing that. I I don't know what I wanted other than 'cause again, he I'm so proud of you. I love you. but it was always the the way I'm wired today onto the next thing. I gotta get better, gotta get better, gotta get better. it's just never finding that true contentment in what you you've gotta find in a different way, I think.
18:26 Paul Salter: So eventually you go off to college thinking business is probably where you're headed, but something happens in college that completely changes the trajectory of your life. And in describing this chapter of life while preparing for our conversation, used a pretty strong word to describe it. You said you were broken. What broke? Tyler Hennessee: Okay. Tyler Hennessee: Yep. Okay, so I'll have to rewind just a touch to give you let you know who I was, but there was I mean, I I I I can't put this on anybody else, but who I I was in in high school, th it's this weird mix of I do believe I've always been myself and authentic, but also constantly trying to impress and constantly trying to perform, right? So however you want to marry those two things together, I don't think I was being fake, but it's just like I wanna prove that I'm the the best basketball player. Or that I can get the girls or you know, whatever it is, just like the this pride element of even when my dad know beck, yeah, w I can take whatever girl I wanted to the dance. Just the that that arrogant facade, that part. and I was I've I I wasn't the best, I'm not saying at everything, but I I was been fairly successful in whatever I put my time and energy into, which I think most people should be, but I don't do anything halfway. If I'm doing it, I'm giving it everything. I I don't have a second I don't I have I have one gear and it's it my dad always called it my second gear in basketball. He's like you just start in the second gear. So with that, I I did all stuff in high school. I had a girl a long-term girlfriend going into college and we actually stayed together for a while and I get into college and now it's trying to find who because I was at a a a private school. I stayed there for basketball. We were actually better than all the public schools in our area. And so every year I'd like go to look at a public school. I'm like, we keep on beating the public school. I have a better opportunity here. And I again I wasn't I'm I'm six foot tall and and a hundred, probably a hundred and
20:25 Tyler Hennessee: 50 pounds at the time, graduate. I was real, real thin. so I I don't have like any college offers other than North Lake and Irving, Texas was a junior college. I go try out, I make the I get offered a spot on the team, but it's to be on the bench. And I've never been on the bench. And so pride and things are swelling up and I'm like, and and the guy I'm competing with is six three, same position as me. I would have put him in front of me. We could do all the same things, right? So I'm battling, I I'm not the guy anymore. So I ended up going to Texas State and San Marcus, which is actually where we live now. A lot this full circle moment we're back where went to college. But man, went there, did intramural sports, and I was trying to find my new identity. So there was definitely this like, who am I now? Like at my private school, I was important, obviously known. It's small. You can consider yourself cool, whatever. I mean, it's just whatever whatever it was. And now I'm at this college of thirty-five thousand students. No one knows who I am. What am I gonna do? And then me and that girlfriend, we break up and she was younger than me and and then so now there's like that's gone, my friends are gone. It's just an identity crisis. So I started to to seek new things and try to figure out who I was and I I was raising a family that my like I said, my dad was radically changed at at thirty three and so we were raised in a Christian household. There's so much junk throughout America on Christianity, by the way, not to get in a tangent on that, but like I think Christ Christians Do a horrible example of showing what it means to be actually even a good person or someone who loves on people and selfless and all that. But my my dad exemplified that, my mom did, and so I was raised that way, but it wasn't necessarily where I found my identity at the time. It was in myself. And so, you know, getting to college and people start pouring into my life and There's a guy named Grayson Belvin when I was you know, again, I'm I'm at this point getting in the first lonely season of my life. I'm nineteen years old. I think it was the second semester. I'm like, man, I don't really have all my friends. Who am I?
22:27 Tyler Hennessee: I go take my first guitar class. I never played an instrument in my life. I've done some hip hop and stuff like that through high school. I was grow grew up in Houston. If you know those days of the 90s, that was that was what it was about. take a guitar class and I start like writing because I'm I'm an imaginative, creative person by nature, and I I like to write anyway. So I start writing. Grayson grabs hold of me. This guy worked at a a college ministry at Texas State called Crosstalk, still going on to today, which is really cool. And he just took hold of me, man, and like Paul Salter: Mm. Tyler Hennessee: I don't know if this word will resonate with everybody in the audience, but the word discipleship is basically like entrusting to other people, reliable people who will be qualified to teach others. So it's like I'm you find one or two or three guys that you pour your life into that you entrust that they're reliable enough to go teach this to other people. And so he chose me and a few guys. It's just like, hey, I just want to, I just want to love on you, get to know you. And I'm like, what's the catch? You know?
23:24 Paul Salter: Mm-hmm. Tyler Hennessee: And man, he's the first guy. I remember the first place he took me was to a bar here in San Marcus. And he's a he's a pastor, and I'm like, we're going to a bar, you know, what's going on? And he orders a beer and I'm like, what is happening? You know, and he was just the most real, authentic, cool guy I've ever met in my life, and just shared his life with me and poured into me. So I can pause there for a moment I can get into the details of what happened after that, but that's kind of where where things started transitioning for me. Paul Salter: Yeah. Paul Salter: Let me reflect and rewind for. So what I'm hearing is, you know, you're coming into college from a previous experience of big fish in a small pond to now small fish in a freaking massive pond, which is interesting because earlier you already said there's a little boy within you who wants to be seen, who wants to be acknowledged, which is infinitely more challenging when you're going into a school of 35,000 people with only few people you know. You mentioned You're learning the hard way, you're not the guy, you're trying to find your identity, and you glossed over this lonely season. Take me into the lonely season. If I'm looking at your life from the outside, what am I seeing? And then what's happening that I'm not seeing?
24:26 Tyler Hennessee: No. Tyler Hennessee: So I remember being in a dorm room. Man, I can't even this is sad. I can't remember the guy's name. I apologize that he ended up seeing this, but I was with him for six months. That shows you how probably much I was struggling. And I I would never admit that I was struggling, right? So I'm it because I gotta be tough. I can't can't admit that this is hard. I want people to think that everything's together. And it wasn't, you know. I felt man, I just remember like the first moments of my life going to bed and being like, I don't like this. I don't like it here. I don't feel known. I don't know anybody. I'm not important anymore. so it was man, it was just like probably a lot of dying to self, a lot of pride getting ripped away. and the only thing what most people in my college town at that time would fulfill that with was just going out to the bars and getting drunk or hook up hook up culture, all that type of stuff, which I'm not even trying to preach to that demographic, but like that never fulfills long term for anybody. And and so By the grace of God, I didn't go down that route, but I definitely was just like I stopped like for people who have my same background, I was you know, I was used to going to church every Sunday. I stopped going to church completely. I was like, screw this, like this is all fake. I don't like the people who like lift their hands up at church and then end up being just as bad during the throughout the week, or they're not who they say they are, are all the people screwing people over, or people are claiming to to know Jesus and it does seem fake. And I'm like, I don't want to do the fake. I one thing I know about me, I'm real. I'm raw. I'm authentic. I'm not doing this. And so I I I isolated myself, man. I didn't really I don't even know my roommate well. Like I said, I couldn't remember his name. But yeah, just very sea lonely season where I just felt like empty, truly.
26:21 Paul Salter: Why couldn't you admit it was hard? Tyler Hennessee: that would be that would be explaining that I is weakness and Hennessy men are hard and Hennessy men don't cry and all this type of crap, you know. which I l I love my my family and I love the generation we come from. But that was like that old school mantra of you don't really show emotion and you you you win. Paul Salter: So was there a pivotal moment that you feel I think you said it, I might paraphrase, but you said it really well. Like, you know, your identity's being stripped away from you, your ego, your pride are all being, you know, kind of just ripped apart as you're navigating this isolated lonely period of time. What was the actual breaking point, the point where looking back, either you did or you at least wanted to have some form of massive emotional outpouring?
27:13 Tyler Hennessee: Yeah. So I I I could I could talk to you about this for any or anybody for hours. There there's so much miscommunication or misrepresentation of like I just said earlier, Christianity or our faith in Jesus and all these different religions. And people find out like I was a pastor and that but I'll tell them I'm not religious. Like, wait what? I'm like, I'm not religious. Religion is a bunch of rules. Religion is like I gotta do these things. What I told you earlier, but I gotta do these things to earn something. I was like, a relationship is I already love you and I want to, I want to please you and those types of things. So I had that that background and I but I'm I've run from it. And I'm like, I don't like this. Like I I everyone I know in that world seems to be fake and it doesn't it's not what I want anymore. That guy, Grayson, was the first kind of real Christian that I met that seemed like he was actually pouring into me. He was actually spending time with me. He ended up inviting me to like a a weekend away. It was like a conference where you literally get out in the hill country in Wimberley, Texas. And he's like, Yeah, maybe we just go there. We we spend time together, we pray together, we We have teaching to to talk about like some of stuff even asked me right now, like where's your identity? where's your hope? Where's your peace come from? And I was like, bruh, I'm not going. I'm I'm out. Like I I don't wanna do the game. He was like, you beg me, beg me to come. Him and his actually his cousin, Tabitha, they kind of got together and they paid my way for free. And they're and they and I remember being picked up the morning, I'm like, You're coming. So I go to this event, man, and it's like it's only like 30, 40 people. People like playing guitar and singing. And remember at this time I've already started playing guitar and I'm learning guitar and I'm enjoying it. That guitar was my outlet, by the way. That lonely season, I played guitar for hours every day and and didn't realize how much like it was, man, so cool how it was a precursor to later in life. But I I became pretty, pretty competent at it. So they invite me and I remember sitting there rather singing or teaching, my arms folded, sitting down, everyone else is kind of engaged. I'm like,
29:12 Tyler Hennessee: I'm not doing this. I'm not doing this. And that last night, man, I just really felt like I got that's when I got broken. Like I remember a guy coming and praying over me and talking to me and just saying, dude, he's like, You're you're harboring. I didn't tell him this. I know, bro, we're getting getting out, we're getting out there, Paul. So he he said, Man, you're harboring anger towards your mom. and God's wanting to do this and stuff, this stuff in your life. And I'm like, who told you that? Like, where'd that come from? Paul Salter: Yeah. Tyler Hennessee: And so I remember like literally falling to my knees physically and just bawling my eyes out. Like I didn't cry and I don't rem I don't think I cried. Like I don't remember crying literally in probably eight to ten years before that. I don't remember. Even in my car alone, like I I would not let myself cry. And I was on my knees just sobbing and I was like, don't know what I'm doing, don't know where I'm going, don't know who I am. And this whole like, I don't want to do this fake relationship thing with Jesus. I want this to be real. And that was the moment that I feel like I got kind of radically changed into it's not about me. It it it's it's about a much greater purpose. It's about serving and loving others. It's not about how great I am. It's about like kind of like truly dying to self and letting go of self and finding fulfillment in such a greater purpose.
30:23 Paul Salter: I hear your relationship with faith, religion fundamentally changed in that moment. And of course, maybe that was the first seed that was planted and now it's been nourished since. But if you stay in that moment, you know, you get home from that weekend experience, what began to fundamentally fundamentally change in the way you showed up and behaved on a daily basis? Tyler Hennessee: Yeah, so man, this is this is like one of those like I I talked to so I work with a bunch of business guys now and I and this is this is the not a flex. I work with guys who make, you know, two or three million a year, and I work with guys who literally make over a hundred million a year on a regular basis. And I'm I'm in that kind of circle of people now for for whatever reason. And the most common thing I hear to this day is man, I'm making all this money, I don't have peace, I don't have hope, I don't have contentment. I don't my marriage is broken. I don't know how to raise my kid. Like that, it's common. And so I would say for me, after that moment, for the first time in years, I I started to have like true peace, true contentment, true purpose. And I started to be like, you know what? And and I started getting friendships after that because I think I started becoming healthier. And it was like, man, like, and don't get me wrong, that like temptation and that fleshly desire to be seen and heard, like that's still here to this day. I just learned through years and years and years of squashing it to go, that's old self. That's not who I am anymore. And so I think it was just realizing that like there is so much more, like there's so much more fulfillment to truly, to serving and loving others than then to to elevating self. And and that that was kind of that that epiphany and conviction that I had.
32:02 Paul Salter: You come out of college with clearly a very different understanding of who you are, what you want in life. Then you meet Amy. You get married, and only three months later, the two of you are leaving all you know behind, friends, family, familiarity. You're moving across the country. I want you to take me into your marriage those first couple years, when you're at that point in your journey getting heavily involved in ministry. Tyler Hennessee: Yeah. Paul Salter: What did life look like for the two of you those first couple of years? Tyler Hennessee: Yeah, hard. We just leave it there. No, so ended up getting my business degree in marketing minor a a and a bachelor's degree at Texas State and was like, I still, even though my life had changed, I wasn't gonna go into business, still wasn't gonna go work for my dad because I I was like, That's what I'm supposed to do, that's what I need to do, that's what I was bred to do, and got called from a church in Austin to come do a one year internship as a worship leader. Did that for a year and then got called to the largest Baptist church in the country in second Houston, fifty-five thousand people at the time. And I was like, this is kind of a big deal. Like I'm gonna go do that for a little bit. That turned into three years. On the third year of that, I meet Amy. I get connected with Amy. Like her dad, this is so so crazy. Her dad was a a music minister as well, a a few miles down the road. And she was three and a half years younger than real and we realized we'd gone to the same dances, the same like events, multiple times, never met each other before. But someone who knew both of us was like, You guys need to get connected. So I can save that for another podcast. But we got connected and just instantly hit it off. we got into that relationship and fast forwarded eighteen months in full, we're married. And I'm so I guess I was at the church for two years at the when I met her and then about the three year mark after that. And so we are literally married, I and just built my first home ever on my dad for for myself. I I just finished it. My me and my college roommates, a few lived there, I'm like, man, I'm doing it. Got this nice custom home. Me and my wife are gonna move into here. And I get a call from Shreveport, Louisiana. If anybody's even heard of that place. I hadn't heard of it. I'd never even heard of it. And the guy was like, What larger than life man Tom Harrison, who I love to this day. He's like, Hey, I'd love for you to come out and consider working here at our church. And I was like, nah, not interested. Great church, great home, great family. Just got married. one thing I know not to do, you don't move and you don't change jobs when you first get married. You're not gonna do it. And he just he's like, Well just i i consider like a a a free trip on us to come see the place of you and your wife. And I'm like, Whatever. So we fly to Shreveport, dude. It was like
34:36 Tyler Hennessee: One of the most jank airports you've ever seen in your life. Just like one anyway, or we we land and we're from Houston. We're like, where is this place? So, anyways, we get there. Long story short, we end up working at that that place, but we leave her her family, my family, all the friends we've ever known, the business stuff that I've ever known. Now I'm like, I guess for sure I'm not taking over my dad's business. It's not even a part time offer anymore. We're going all in and we know not a soul. And we moved to Streepport, Louisiana. Paul Salter: What was the driving force for you personally that led from you doing what seems to be a complete one eighty? Tyler Hennessee: Mm-hmm. Tyler Hennessee: Yeah, so it was that kind of that following that that piece, following that that new not just doing what myself wanted to do, realizing I'm like, Okay, taking over my dad's business is still about Tyler. Taking over my dad's business is about making a lot of money. Taking over my dad's business is all the things that I've I'm trying to leave behind. Do not get me wrong, there was crazy tension there. Like in everything Emmy was like, I mean, I I I felt from a young age like that I could make a lot of money. But I I don't know how that comes across, but I just I'm like I I feel like I had the personality for I'm a hustler, I'm a hard worker, I love talking to people, like relational, all that stuff. And but I think my motives would have been just to get rich. And that doesn't really the long term do anything for anybody other than you end up getting probably more lonely and stuck. So because of that Yeah. Yeah.
35:59 Paul Salter: Well, Paul's there. Reconcile this for me. I'm curious. What I hear, and you can tell me I'm wrong, you'll never hurt my feelings, is there's a part of you who you said, you've got the intangibles, the drive to make a lot of money and through serving others, yet you made this decision because you felt peace was the driving force to, you know, go this 180 away from the lifestyle of hustling and grinding. My question from that is can chasing more money, more success, and peace. Tyler Hennessee: Yeah. No, I'll run. Bring it on. Bring it on. Paul Salter: coexist? Tyler Hennessee: I think if your if your goal is just more money and more success, they cannot coexist. If it's a byproduct of your hard work and effort, then they can coexist. If you can underst if you understand what I'm saying on the difference that if if the goal is simply I want to make more money so I can say I make more money or keep you up with the Joneses and people who try to pull the the the contest of who who's done more and their and success is only based off of value, dude that's the most re I think it's the most rid ridiculous adult monopoly game I've ever heard my entire life. There's always someone who's done doing better. Like Get off your high horse. Stop thinking you're so important. The guy who's making 300,000 is probably extremely happy he's making 300,000. That's better than 95% of the country. But there's a guy making 40 million right now, right next to you. Like and and and so forth and so forth. So I I believe that if your hope is it our security or confidence comes from money, it will ruin you.
37:32 Paul Salter: So you make this decision, you move across the country no, not quite across the country, but to middle of nowhere. We'll call Street Fort Louisiana that. what did Amy specifically learn about you during those first few years in Louisiana that has probably helped her better understand who and where you are today? Tyler Hennessee: Yeah, I just find out more. Tyler Hennessee: So one thing we both we align on a lot, but what we both align on, we're not we're not, we don't follow the crowd in almost anything. So we're always going to use wisdom, common sense, good judgment on making our own decisions, just because the crowd saying this is the best option, or the government, or whoever it is, we're we're going to research and figure out what's best. And so, and and Amy loves change. Amy's a kind of a go getter outgoing. like let's just let up for adventure. And so for her, at first, you know, we had man, we're she's she was 22 and I was 26. We're little little kids. and she's never really left her home before. And she's like, let's go. This is this is great adventure. But she'll tell you her story for the first three years we were there, she basically experienced that kind of lonely, not depressed I've never really seen her depressed, but that lonely dark season like I had in college. Because we get there And I start to make friends with everyone at my church. And I'm known at the church and and it's it's like it's more natural for me. And she's kind of stuck at home and and and figuring things out and and getting lonely. I I would say what she learned about me though is that what she already knew, but gotta see an action. I'm really, really big on action. Don't tell me you believe in something unless you're gonna show me. Like I w I wanna prove it by what you do. Don't tell me you care about your health unless you're gonna work out and eat better. Don't like don't tell me you wanna get stronger unless you're gonna go put in the work or or even with business. Don't tell me your goal is to make five hundred thousand or a million if you're not gonna put in the work to make it happen. So I I I think she just learned that if I start something, I'm gonna finish it. even if it's building a a chair in the back, you know, in the in the kitchen. I don't I don't stop till it's done. And so just like we we were gonna do things the hard way and we're gonna grow through it. So we and we and we went through some marital stuff of just like when you're with each other only and me trying to help her make friends and figure that stuff out in the first few years of marriage was very tough.
39:55 Paul Salter: She married a man in ministry. And over the couple years, couple years, couple decades later, she eventually watched you evolve into a rapidly growing entrepreneur. What is that transformation required from her? Tyler Hennessee: But she said she would never do by the way. Tyler Hennessee: So she's had to be very supportive through all the all my crazy and all my ideas and all the things that and she is, man. Like this is like I said, I wanna be clear, we we've definitely had our struggles and still have struggles. I mean, we're human, but she is the most supportive woman I've ever met. She is the most encouraging woman I've ever met. My for I don't know why, but my my wife thinks I hung the moon and she she builds me up, she encourages me daily. She supports what I do. She's like, I'm ride or die, Tyler. Like if this all blows up, I'm with you. I go live when you in a tent in the backyard. Like she is that woman. Having that, which one, it does two things. She didn't realize this doesn't mean for it to happen. It puts a ton of pressure on me. Like, I don't wanna, I don't want 'cause she's not gonna leave me. We don't even bring up the word divorce. But I I don't wanna let her down. Same as our like I don't wanna I don't wanna let my kids down. I I want to make sure I'm taking care of them. At the same token, I know that she actually means that she's with me. Like she's not with me for any type of monetary gain. We're I gotta see 16 years with her in ministry of us not making very much money. So I she's already proven she was never with me to make money. She's with me because she loves me, loves my heart, loves what we're doing, our purpose. So it just it gives me, man, like a total freedom, kind of unabandoned, like let's let's freaking go.
41:32 Paul Salter: What's feel like to carry that pressure, not to let your wife, your children down? Tyler Hennessee: Yeah, it man, I I think most of it probably comes internally, you know, the pro maybe from this conversation is traced back to childhood. But I just I I I kinda live with a an internal pressure on myself that I I don't even know how to get rid of. Like I'm just constantly I don't I don't want it to be my fault that something goes wrong. I don't want it to be I don't want to be like Tyler this happened because you didn't put in the the time. This happened because you failed. This happened to me. Like I want to be like, well, I if if something goes wrong to be like, I I gave that everything I had and it just didn't work. And so there's just I kind of keep this internal pressure on myself.
42:15 Paul Salter: What happens or what's the experience like when that internal pressure starts to rise? Tyler Hennessee: Stress, anxiety, restlessness, those types of things a lot of CEOs probably deal with and just man like putting putting expectations on myself that nobody else was putting on me. So yeah, I I think it I I that's definitely a fallibility that I that I carry with me that I don't I don't want to carry with me. Paul Salter: How do you take the edge off? Tyler Hennessee: for me, so I spend time every morning just in complete stillness and quiet. Every morning when I first wake up, no phone, no nothing. I just I normally look out at my backyard, I pray, I read scripture. and those th those moments are amazing. A lot of times going back to the piano or guitar and singing, that that brings me some peace. whenever my phone is not with me brings me more peace. 'Cause when my phone's with me, I can guarantee you right now, when I picked that up after this podcast, I'm gonna have a hundred messages to respond to. So it's just it n it never ends. You you can't ever finish a checklist. And so it's just it's it's never ending.
43:27 Paul Salter: Who's the one that continues to add to the to do list? Tyler Hennessee: This is going into a therapy session, Paul. What are you doing? It's it's me. It's like I am the the achievement mindset of again, we were we we this in this year, we've literally we've grown 812% exactly since January. If you told me that in January, I'd be like, that's freaking incredible. And I literally was like, cool, on to the next month. And And I so I have a hard time just ca I I I I that's something I I I'm aware of and I'm trying to get to a place that I'm like, hey Tyler, like in enjoy and appreciate and sit in some of the the goodness and don't just always go thing. But I'm I I look at my life as a a vessel. I'm wanting to maximize, I'm wanting to pour it all out. Like I wanna I want to get every ounce that I can out of it.
44:24 Paul Salter: Yeah, there's an interesting dichotomy. I I hear and I echo that. You want to maximize your potential, your gifts, and give them to the world. Yet you actually become more ineffective if you don't manage your ability to pause the to-do lists, you know, rest, recover, play, slow down. And what's I'm gonna use the word timely, and I'm gonna use that word very neutrally, is that the last couple of years of ministry and then into the transition into full blown entrepreneurship. You experienced several encounters with mortality in a relatively short period of time. Your best friend committing suicide, your dad's debilitating stroke, and then one of your mentors, your dear, dear friends passing. And I really want to begin to understand, you know, what did these repeated encounters with mortality teach you about time and how did your relationship with time change? So I'll start with your friend. Thirteen years ago, you lost your best friend to suicide. How did losing someone that close change you?
45:26 Tyler Hennessee: Mm-hmm. Tyler Hennessee: Yeah, I don't think I I don't think anybody can explain it unless you experience it. And that's not it's just it's one of those things that and I I don't watch that on anybody. But I grew up with this guy since sixth grade, loved him he was he was deeper than a brother because I didn't have brothers, you know, and we just we spent every waking second together. He went to Texas State with me. After that first year, he he was one year younger. So we roomed together for three years at Texas State. And then we actually roomed together when we graduated in Houston in an apartment. So we were we were very, very close. And I'm still, you know, his family I love to death. And so we we knew he worked for my dad for ten years. So he worked for the Hennessy Company for ten years. So he was doing what I what I w there's a little jealousy there on my part. He was doing what kind of what I wanted to do. man, like when I got that phone call, I remember I was actually leaving church on a Sunday and I had a voicemail from his stepdad. And man, I I pulled over. That was the second time I remember like I I was uncontrollably just like screaming, yelling, crying. like I i i I couldn't I can't articulate the feeling I had. It it was deeper than nausea and deeper than a gut punch. It was just like, what's happening? Because the finality, death is so crazy. You start you start like let your brain go down the death train, man. It it it's it's it's final. I'm like, I'm not gonna be able to see him again. I'm gonna be able to man, I had dreams for years, not months, years, where he would be alive in my dreams. And still to this day, every once in a while creep back in. And it's so real. So man, it changed me a lot just because I'm I'm still, even though I'm in ministry, I still have this kind of hard mentality and you know, didn't tell people we love them enough. And and me and him did towards the last year, which I'm very grateful for. But other guys that I care about just learning to tell other dudes like I love you, bro. I got your back, like I'm here for you. If you need something, if you're struggling in your marriage, if you're struggling psychologically.
47:20 Paul Salter: Yeah. Tyler Hennessee: it it changed that for sure. And so my softer side, the r the real core of who I am, the tenderness, started to come back out for sure. Paul Salter: Yeah. Hmm. Paul Salter: That's beautiful silver lining. And I I'm really happy you had that experience. What did grief look like for you back then? Tyler Hennessee: Yeah, I lot my again went up went to secluded 'cause that's my natural thing whenever something like that happens. And remember like just I'm married, you know, my my wife knew him very, very well. So we're all hurting. But I went in my master room and shut the door and and just kinda prayed and cried and processed and was angry. You know, man, and I I got asked to officiate his funeral. So like I never done that in my life. First funeral I do, I'm up there telling people about my best friend, it was just like it was a outer body experience. Like one of the most surreal things I've ever experienced in my life. and man, like and when I say the the the church was packed. Like you like standing along the walls, people were in the lobby. It was it was a really cool celebr like celebration of his life. But yeah, it it it impacted me to this day. I still my kids know him. They they you know, they weren't even born yet, but they know him from stories and there's a picture of a little rose from his from his funeral and stuff. But it it impacts you in every way and it makes you Paul Salter: Hmm.
48:37 Tyler Hennessee: appreciate time more. It makes you more I'm very deep in the relationships I'm in. And so people don't wanna be deep and I don't it's like I I can play the fake shallow game with you and we're but I'm like, you're not now you're now you're not in my circle. And the only way you get my circle is if you're gonna be vulnerable, transparent, real. I don't I don't have time to do the the the the game. Paul Salter: We fast forward 2022, your dad suffers a debilitating stroke. What changed for you when someone who had repeatedly represented strength and entrepreneurship throughout your entire childhood suddenly became so vulnerable?
49:20 Tyler Hennessee: Yeah, I was man, I don't know. I don't wanna s put on I don't wanna put levels to these things. I I I can't put levels on the comparison. So I was watching Dallas Cowboys again. My mom called me said, I think something's wrong with your dad. And I drive over to their house. We lived in the same city at the time. And I got through. He was outside on the rocking chair. And I don't know if he'd even had the full-on stroke yet, but he was just sweating and didn't look like himself. And again, we're still very, very close at this time. I still, anytime I have problem in ministry or just I'm already starting and I am already exploring the business ideas again. That's coming back. Where I'm like, Dad. I really think I'm about to be moved out of the walls of the church to do ministry in a different way and help people with finances and investing in business. I feel like my view of money has changed in a very healthy way. And I want to teach this to the masses. And he was supportive of all that stuff. But I show up, man, sweating, just kind of not not all good. And I man, he he this is crazy. He stood up and we do like the kind of walked him inside. He's moving slowly. He literally he weighed 200 pounds at a time. collapses in my arms. Like collapses. And so I I have my dad's weight on me and I drag him about ten feet. I I don't even know how 'cause I I weigh a hundred and seventy five pounds. And so I'm dragging him and I literally get him on the on the a chair and he's kinda laying across of it. And it was just like I don't know what's happening. I call to people from the neighborhood. I have a bunch of connections in that city. Call the ER doctors like bring him right on, bring him in and And the rest is kind of history after that. Just like he just went, he spiraled downhill. He was working out five days a week, seventy seven years old at the time, the most healthy you would have thought he was sixty-five. Extremely healthy, extremely vibrant, all the stuff. And it just like plummeted, man. So it was it was still this day it sucks. It's like he's still here on this earth, but in a lot of ways he died that day. You know, it's just things have never been the same. And so, yeah, there's a gut punch.
51:13 Tyler Hennessee: Say the least. Paul Salter: What's that like for you in those quiet moments having what seems to be a similar yet dramatically different father who's present now? Tyler Hennessee: Just roles have reversed and that's okay. But like now I'm in charge of their will and the trust and which they don't have no they've lost everything through the the the stroke too. So managing those things and trying to manage two elderly people who's he's still he's the kindest man you'll ever meet. It's just when I allow my brain to go there, it's just heavy. It's not fun. It's like it's just like, dude. In a lot of ways you you almost wish that he could have could have passed away for his own sake. It's just hard to watch him be in this new state. I know that's extreme to say, but man, it's hard to watch someone you love just not be able to do what they want to do and and with grandchildren, all that stuff. It's heavy. It's it's the it's the parts of life that none of us can really understand. And it's like that's why my hope and my faith is what it truly what carries me through that type of stuff.
52:15 Paul Salter: Yeah, I appreciate you talking about that. And you mentioned it. It's like this is happening on the verge of fully stepping into entrepreneurship. You suffer another dear loss about a year later. And if we collectively put them together, did those three specific experiences make you less willing to postpone this life that you originally felt called to live down the path of entrepreneurship? Tyler Hennessee: They very much had an effect on it. So when Uncle Mike passed away about a year later, he was my my mentor, business guy. The guy looked up to, I would say more than anybody on earth, because he ran a very successful CPA firm and did some real estate stuff. And we were starting to work on things together. He was the guy. That I called at this point, now that my dad's had a stroke, the only person I called for wisdom, advice, taxes, that type of stuff. And he was just man, I I wish you could meet him. The coolest, coolest guy I've ever met in my life. And just just an awesome dude. Everybody loved him. the loudest person in the room, and and very wise and fun. I golfed with him, holidays with him, all that type of stuff. So and when he got his cancer, you know, just that that we knew that there was potential he could be passing away. But I was at his house, you know, four or five days before he he passed and he asked me to be the executive executor on their will, which was an honor, but also very tough. Cause it's like, man, I'm about to help to help manage their stuff and love their family. And yeah, dude, it it it wrecked me. And that that one's the most painful right now because it's it's still the most recent and he's gone. And so that part's like when I have struggles in business, you know, my best friend to this day, I call about everything, but
53:49 Paul Salter: Mm. Tyler Hennessee: I missed that kind of older figure that was able to help me and stuff. And and but him passing, I think made me be like, dude, Tyler, what's the worst that's gonna happen? You're gonna go try this entrepreneurial life? Your worst case scenario is going back to a W two. Like my worst case scenario is my present scenario. Like, wh why why can't I take a leap of faith and try this? So Paul Salter: Mm-hmm. Paul Salter: Hmm. So do those losses make you more willing to risk failure? Is that what I'm hearing? Or less willing to risk regret? Tyler Hennessee: Less willing to to risk regret. And and Mike Mike told me, the one who passed away, he's like, You you will be doing this within the next two years. He's a mark my words. When I was like, Man, I don't know if I can do it. He goes, I'm telling you. He called me Skywalker. but he's like, Skywalker. It's happening. He's like, I I know you too well. I've already heard it. He's like, once you get over this mental mental hurdle, he goes, I you know, it's it's gonna I'm trying to not use the phrase he used. It's probably inappropriate. He's it's gonna be all out. And so he Yeah, he gave me the confidence for it. So Paul Salter: It's all fair game here. What were you actually afraid might happen in making that leap from W two into the adventures of entrepreneurship?
55:04 Tyler Hennessee: think I think it was less about the W two man. I mean th don't get me wrong, there's like a a a really broken false security. That comes from W-2 that I think is ridiculous. I kind of preach against. I'm not saying W-2 is bad, but that security is ridiculous. It was more about persona and identity again, because now my identity had been in this new world for for gosh, after if you add up all the churches 20 years. So I am now identified as this person, as this role, as helping in marriages, helping disciple men, helping lead in music, teaching. that's who I am now to people, like the persona I think. And I'm not saying it was it was never fake. It was extremely genuine. But I had never lost my passion or love for business and hustling and building things and creating. So I was worried about what everyone was gonna say, what they're gonna think. Am I not who I say that I am? Am I actually a chaser of money? Am I actually a chaser of these things that I I I'm not? But Paul Salter: Hmm.
56:02 Tyler Hennessee: Is my life gonna look that way? And how and trying to prove myself to everybody again. So that that was very painful. Still it's kinda hard. but yeah, that was a part of it for sure. Paul Salter: When you say it's still kinda hard, do I hear that there's maybe grief around losing what we'll call that version of yourself? Tyler Hennessee: Yep, absolutely. And I met I mean, friendships that I don't I think if I picked up the phone, I think they'd still answer and we're still friends. But like the that time and that proximity has changed things dramatically. So it's just I hate that I carry that, but I I do carry that. It's just like, man, like I thought we were really close and really deep. And it's like when when I chose chose a different occupation and definitely when I moved, you know, it it was almost like a cut it off.
56:49 Paul Salter: Hmm. What was left? Like who were you when you weren't the pastor anymore? Tyler Hennessee: I didn't know. Dude, that was so like you pile up my dad's stroke, Uncle Mike passing away, and me leave my job on the matter of about a two year period. I had no idea who I was. My friends who maybe watch this, man, I got I'm a big time golfer. Dude, I was so messed up mentally. Anybody who golfs, I got the shanks, I got the yips, I was I couldn't even play golf. Like I went from a pretty decent guy, like I couldn't physically even get to a round feeling normal. Paul Salter: Mm. Tyler Hennessee: And so it's like I was just like spinning. and Paul Salter: Take us there. Give give us a like a paint a picture of that experience. You're spinning or out of control contrasted to the version of you that used to to lead, disciple, mentor, and have so much control. Like what was that like?
57:39 Tyler Hennessee: Well, again, I think a lot of times I would keep it internal because I don't want to burden people. So I had a hard time telling people that I'm struggling. And it's not it's not that I like if you ask me, I'll be like, I suck at this. I'm bad at this. I don't even know have a clue what this is. I'm ignorant on that. I I I am anybody who knows me, knows me will tell you that I'm transparent. I'm a I I I'm I'm like the same person on this podcast as I'll be anywhere else. But I I do struggle burdening people and I don't want them to be like, my gosh, like why what are you whining about? No one said that to me, but I don't I don't wanna be that person. And so I think I was like, Tyler, you gotta figure this out. You gotta figure this out. And I just remember being like, I can't go to my dad. Who is my number one confidant? I can't go to my uncle, who was then my number one confidant, and I have no one that I can actually share this with. And while I try to share it with pastors or ministers, not they're great, but they have no context, no understanding for the business world that I'm talking about. So then I start seeing other business guys that they don't even understand my faith or understand that like, I'm actually real about this. Like, this is this, I'm not leaving my faith. I am, I'm transitioning to a new season. I just it it it's It was hard. I don't know what else to say other than that. I just felt ki kinda lonely again.
58:53 Paul Salter: Yeah, I hear loneliness, I hear perhaps misunderstood. Tyler Hennessee: Yep. Yeah, I felt misunderstood my entire life. So that's never changed. Paul Salter: Tell me more. Tyler Hennessee: just y y y y y you can't control the narrative. That's the bottom line. You know, you grow up and you start learning. I I could do I could do everything wrong or everything right and the narrative's still gonna be what the narrative's gonna be. You still have people that will twist your words, twist your your motives, those types of things. so it it I I have come I I've come way more to grips with it and realize I can only control what I can control. And the people pleasing side of me is is by the day getting removed better more and more. Like, man, like I I can't. Like it it's so draining trying to make sure to let people know my motives are as good as I I can make them, you know. So it's it's just growing up, man. Learning like this is this is who I am. I'm doing like people who are closest to me and around me that see me on if my wife was saying you're not who you said you were or you're saying this on a podcast and you're acting different, dude, we would be having a total would this would be a therapy session. But she sh I I know she'll say this. She'll say, I'm the exact same person. Like and and I I try to walk in the light as much as I can and and keep things, you know, with integrity.
1:00:11 Paul Salter: How'd you continue to carry? Like again, you described, you know, you're loss. You have no idea who you are when you left the pastor identity behind. You're you're struggling in what probably is your one safe space outlet, the golf course, even. So clearly something is it's not even shook in your swing, it's shook to your core. Did you just continue to repress, repress, and let time heal? Or did you ever reach a point where there was a Tyler Hennessee: Yeah. Exactly. Paul Salter: Clear concerted effort to start releasing that pressure valve. Tyler Hennessee: It it was mentally tormenting. Again, you have to realize type A personality, competitive, never pleased, like always seeking even in golf if I'm doing golf, I want to be the very best I can be. I'm not a scratch golfer, but I got down to a decent handicap at one point. It was very low single digit, and then it just starts blowing up. I I've never I don't think I've ever told anybody this publicly, so I don't mind. I mean it it golf wasn't the problem, right? At all. It was a byproduct. It is it's not it's not even one percent of the problem. But I'm so pissed that I can't enjoy my outlet. That I I hired a golf psychologist from Oregon, dude. And I had like 16 calls with him. And he he was like, he's yeah, this is 100% mental. Like none of this is a skill set, none of this is physical. And so I but I I was like, I have to fix this, but that wasn't what I needed to fix. I needed to fix internally just what I was struggling with and and grieving better, letting go of admitting that things were were not gonna be the same. Excuse me. So it was more of that. But yeah, time and then a group of friends that I would it wasn't an official therapy session, but I think it was therapy. I think healthy therapy happens inside of healthy relationships anyways. Like if you're actually confessing sin or talking about struggles and being transparent with people that trust you and love you, you can you can experience that therapy together. And so I had a group of men that I dealt with for about two years and we really helped each other just do a lot of stuff, all of us.
1:02:07 Paul Salter: Take me to that first moment because you've told me this whole time, you just bottle everything up, you don't want to be a bird, but here you're telling me you reached a point where you felt comfortable enough to really open up. So that first moment you found the courage, the strength, maybe even the faith to be vulnerable. What was that like? Tyler Hennessee: Yeah, I mean, it's this weird like I guess this like use this word earlier, like this weird dichotomy where I feel like I'm trying everything in me to be real with anybody I talk to and truly authentic and not putting on this facade at the same time, I don't want to burden people. So however however you marry those two ideas, that's that's me. It's like I wanna be real with you, I wanna be vulnerable, but I don't want you to be like Ty Tyler's calling, he's gonna be a a burden to me. So that I I live with that kind of this group of guys was just there, all pastorally trained and licenses. One of them was a licensed therap therapist and and just dear brothers and friends of mine. And so I think we just started meeting for breakfast and we were just talking about like our own marriages and then our own struggles. And it was just more of like just being raw with one another and knowing it wasn't going anywhere else. made it made it a lot easier and just realizing you're in good company with the struggles that we have, that that was that was healing for me. but even th those guys who I love to death, like s since I moved and left ministry, it's like again, like I I think if I called any one of them we're we're good. But just like those relationships kinda died. And it's th that that stuff is is still hard to to swallow. So what what am I the problem here? What or is it just because is that or is it just pockets and seasons of life? And I think that's more what it is. It's like that was a great season. This is a great season. This is a hard season and we just kind of go hop to the next season type deal.
1:04:04 Paul Salter: Well, now we're in this season of rapid, explosive growth. In fact, the last couple of years you've been on this hockey stick like trajectory you mentioned earlier, eight hundred and twelve percent growth just from January. You also mentioned to me in our preparation for this call, people don't see the lost sleep. When family time gets interrupted, the hundred messages that are waiting for you the moment we finish this podcast, everybody texts you, everybody wants two minutes, everybody has all of this access to you. If I were to follow you around for a week right now, what would I see on the outside that looks exciting? Tyler Hennessee: Well, I I don't know if this would be exciting to you, but I I am probably one of the least routine people you'll meet for better or for worse. So these guys online that are all like 'cause most entrepreneurs are like you gotta do things the same way every day. And they get up at five AM and cold plunge and all and I'm not making fun of it. Go do it. If that works for you, it doesn't work for me. Because of my not clinically, but my ADD personality. I can think about 14 things at the same time. And then when I'm finally ready to tackle something, it's gonna get destroyed. I'm going all in. and I'm creative, like I told you. So each day I try to make it look a little bit different. I don't want to have the same seven meetings in a row on Monday and then Tuesday. I try to even move my I I I work out three to five days per week. I move that. Sometimes it's at 8 a.m. Sometimes it's at 5 p.m. And so that that's me. I also have I I my assistant knows I don't want to have, like I said, five. Strategy calls in a row. I want to have a strategy call, then go be on a podcast, then go to do some creative planning, then go to do some vision casting, then meet with our CRM team, then meet with my branding guy. The eclecticness just me meets my that B side of my personality, that creator, that musician, that whatever you want to call it, that artistic side of my brain needs eclecticness in my in my schedule.
1:06:03 Paul Salter: So then what would I not see? Because we've got all this outside success. We've got the variation from day to day, hour to hour. It seems very strong relationships in your business. What's happening underneath that that I would miss? Tyler Hennessee: Yeah. Tyler Hennessee: probably the need to I I I need to and I've I've I have implemented these rules in my family. As as as much as I go, I do have time with my kids, you know, daily and and my wife as well. So we are very, very, very close family. My kids are homeschooled and we've we've kind of structured it that way for right now so that I can spend as much time with them as possible. My relationships with them, because of my childhood, even though again, a lot of it was good. I try to be extremely present. So even in between these meetings, I know after this podcast, I'll have a thirty minute window. I'm gonna go play with my my my little boy and little girl, spend a little time with them. Just be present, face to face. So in the middle of busyness, that's always happening. I feel like outside of golf, and even now that's getting interrupted, I have very little time for myself to truly decompress. So as outgoing as people probably think I am, and people think like outgoing personality, a personality, I only restore when I retreat. So I've gotta be secluded. I've gotta be by myself, I gotta decompress. That's always been there too. So more introvert extrovert than just extrovert. And so I think you'd probably miss some of the like I'm not shown on the outside, but the the weight that I'm carrying on the finances, the homes, the upbringing, the being a good husband, being a good father, being a good manager, being good to my executive assistant, making sure I'm helping my consultants grow their families. Like I'm I'm I'm constantly thinking about and this isn't like look how selfless Tyler is 'cause I think about me, but I am thinking about everybody else and am I doing a great job with them.
1:07:57 Paul Salter: Do ever feel like you're truly off? Tyler Hennessee: I'm sorry. Paul Salter: You ever feel like you're truly off? Tyler Hennessee: Rarely. And it's just in this I I've only been full time business since really I January of twenty five. So I mean I w you're looking at a year and a half. I mean this I was doing part time stuff from twenty twenty till now. Dabbling, real estate, that type stuff. But I've been all in since January of twenty five. Unless we go on a vacation where I turn my phone off, that's the only time I feel off. Because I'm sure you'll resonate with this, but even if I take off, I know that all I'm doing is piling up my list for when I come back. And so even on the golf course, which this is dumb, but like I'm like, I I want to answer a few emails or a few text messages, so I don't have a ton to do when I get get back that night or that day. So I think that's part of it. And but and maybe learning to go, not everyone needs to be responded to. and some people can wait till 48 hours or next week. So again, I do have these disciplines and these rules in our family to try to protect that. So the time is there. It's more of getting the mind to align with the time that's actually available.
1:09:05 Paul Salter: So I hear the time is there, the presence is still coming on board to catch up. Tyler Hennessee: Yep, that's it. Paul Salter: When everyone has access access to your team, your clients, who gets what's left over? Tyler Hennessee: Well, I I hope my family would not feel like they're getting left over. but probably the friendships I need to be working more more on and and then just cut some internal time for myself to to dream again. Like that the the business derived From creativity, the business derived from me dreaming and vision casting and those types of things. And so and we and we're like me, I had a conversation this morning with a business consultant. So I'm I'm actively working on bringing people in to help, even if it means removing parts of my equity or whatever it might be, to make because like I I can't remove the 20 years of experience I have in ministry and the context I have. I I I actually think it's what differentiates me from every business person. I feel like it's what some people might see as, my gosh, you don't have the the 30 years I have. I'm like, dude, I have 20 years of relationship skills that you can't imagine. And dealing with conflict and dealing with heartache and dealing like that does shape you in a different way. And so I I really look at it as a as a pro. I I I have those skills and so now just trying to make sure I don't lose these truths and these disciplines that I have and make sure they're incorporated inside of this business world that I'm trying to trying to juggle on a daily basis.
1:10:33 Paul Salter: Moments the last two years where feelings of loneliness have crept back in. Tyler Hennessee: Yeah, for sure. And it's like, I I I I you know, I told you my sister's one of my best friends. I tell my wife and other friends, it's like I d I I I really don't hurt for people. Like I have too many people in my life. I talk to too many people. I have man, I kid you not probably twenty different pockets of people that I can go. That's a friend group I can go hang out with, that's the golf group, that's the fantasy football group, that's the business group, that's the real estate, that's the HELO like I have these pockets, but since this world we live in now, so much of it is digitized and online and all that, it it is I'm still trying to figure out how to find that that that deep rich community again. And and don't get me wrong, we moved twice in the last 12 months. So like we moved from Louisiana to a rental home, built a home. So we were just getting our feet grounded here in, you know, Wimberley, Texas area again.
1:11:30 Paul Salter: It's interesting. Like if we go back to how we opened this conversation, something you told me in the beginning is you learned very young how to be independent, how to figure things out. And now you're describing entrepreneurship as lonely. At times you mention, you know, a little difficulty finding the right person, the right partner, trusted people to onboard to your team. And sometimes you're left in this adventure feeling like you have to figure things out for yourself. Do you think that entrepreneurship has rewarded this survival skill that you've developed long before you even own the business? Tyler Hennessee: One thousand percent. Yes. Cause I'm I am I I can play the part that I need to play, you know, but I'm very resourceful. I'm a connector. I'm always working on you know, I hope this is craftiness and angles and how do how do I work this into my business and and make us both win where we're everybody's happy. But like I'm constantly hustling it to figure out the best way to make it thrive and and help those in my in my circle, you know.
1:12:25 Paul Salter: Yeah. Paul Salter: Has that independence, that skill ever made things harder than it needs to be? Tyler Hennessee: for sure. For sure. I mean there there's there's the definitely both sides of that coin. So the independence is like I can ha and I don't I don't like say this out loud or I I think even have the conscious thought. But at the end of the day I'm like, I can do this by myself. Like I'm not saying I don't want, because I definitely want and desire people around me and with me and and it and not to be Tyler down. I want it to be us working together for this common goal. But at the end of the day, I'm I'm so resilient that I'm like, I'm not quitting. So like if you quit on me, it's gonna hurt, it's gonna suck, but I'm not quitting whatever I'm doing until it's time to be it's until it's finished or I'm called to something else.
1:13:20 Paul Salter: It's interesting because you said earlier, you know, what probably doesn't get as much time that that maybe could or is deserving is friendships. Yet you then you meant to say, you know, you've got twenty pockets of friends. If you were to choose, you could go engage in. You believe relationships are one of your greatest currencies. I mean, you've got multiple doctorates in relationship building, if you will, from all of your years in ministry. What happened? Where help me understand the disconnect? Relationships are important, my friendships are important. I'm putting very little time into my friendships. Tyler Hennessee: Yeah, I mean, if you could help me figure that out today, that'd be a great successful podcast. I mean, y y always I always want to put the blame back on myself for looking internally, you I don't want to blame everybody else, but probably just struggling to try to be known of who you actually are. you deal with and one thing I've seen in business that I really like for the most part, and you know, we can't put a blanket statement over anything, but in the ministry world, I feel like there was a lot more. hidden jealousy or people don't wanna see you succeed more than them or if you have if you have more in anything or you're better. It's like they might say the right words but their actions seem like I don't want I I I I'm actually waiting and hoping you fail. And I'm not saying that business people don't have that a little bit too, but what I've experienced in the business world with my friends in the business world, because a lot of my friends, most of my friends are way more successful than me. if we're doing it on monetary gain or size of business. Mine's still very new. And they're all want to see me win. And when a big deal happens, they're cheering me on and they're like, and so like I I'm gonna butcher this phrase, but like it said, you're you're never gonna have people above you like pulling against you. It's always people below you. and however you want to
1:14:57 Paul Salter: Yeah. Paul Salter: Yeah. Tyler Hennessee: Paint that picture. And it's just like, and I don't, but I don't view myself as above anybody, like I told you earlier, based off of my monetary gain or success. And so I just I wish more people cheered for and pulled for. It's been that's fine. I I really have gotten over this for 90%. But you know, choosing business, I was like, why are my friends not supporting this? Like, why are they not publicly supporting this? Paul Salter: Hm. Tyler Hennessee: all the stuff that happens with social media is just re ridiculous. And so that was hard. But now all my business friends are extremely supportive. Now the business has started to grow. Now a lot of those friends are coming back in. I'm like, were you ever really a friend to begin with? Like, why are you coming in now? I told you this five years ago, six years ago, but now you now you're interested. And so that's for each one of them to deal with on their own. I'm I wanna I wanna be respectful and loving to each one of them when whenever we meet, if they become clients or I help them. But yeah, the friendship side is just we've moved twice.
1:15:42 Paul Salter: Mm. Tyler Hennessee: I'm still trying to get my grounding here where we're at, and then trying to figure out where to pour our time into. Because we have limited time. And so I don't want to try I don't I can't be friends with 20 people at a high level. I think I'd be hi friends with maybe two to three people at a high level, truly at a high level. And then you have another pocket outside of that, and then you're more acquaintance circles. But yeah, that's just trying to figure it all out. Paul Salter: Yeah. Yeah. One of the themes throughout our entire conversation has been this word hard. In fact, your literal personal, I don't know if we call it brand or mantra is, you know, hard makes you better. And I asked this question, not intending to be facetious, do you today believe hard always makes you better?
1:16:29 Tyler Hennessee: Yeah. Tyler Hennessee: No. I believe if you respond to it the right way, yes. Like I I believe when hard things happen in your life, the trials, the heartache, the the losses that we've talked about on this call, the friendships who weren't really friends, the people who throw stones at you, the people who leave you, the people, whatever it might be, or sickness, financial issues, all these things, you have a choice. Are you going to say, woe is me? I'm the only one going through that stuff. You have no idea what I'm going through. It it it it this is always my case. This always happens to me. I think that type of mantra, that type of mentality, that type of verbiage, I'm like, well, of course it does. That's that's what you believe. And you keep on vocalizing it too. And you you're gonna always stay in that stuck position. Or You say it's I'm not saying we can't say that this sucks or this is a difficult. I think you can. But what are you gonna do about it? And so if you choose to say, This difficult thing happened, how am I gonna grow from my dad's stroke? How am I gonna grow from Uncle Mike being passed away? How am I gonna grow from my my best friend, you know, dying years ago? How am I gonna grow from leaving my job? How am I gonna grow from people questioning my integrity? I can continue to do the right things and push through it. And I believe time and time again, it just refines you, shapes you, chisels you, brings the people who you're are actually trying to attract to you. It's it's it's a magnetic.
1:18:07 Paul Salter: How do you distinguish between a hard season that's developing you and one that's unnecessarily costing you? Tyler Hennessee: We can you flush out the s the ladder a little bit? What do you mean unnecessarily costing you? Paul Salter: You know, what I hear, and this is full of me kind of connecting some of the dots and filling in the gaps, like you're and I'm gonna oversimplify as well for sake of simplicity, like you're wired to seek hard because hard, what we could say, hardship or adversity is a catalyst for growth. Like from the outside looking in, we all know that to be true. It's a reason that everybody listening, you myself, have had the success we've had. What I have noticed in 17 years of coaching with that type of mentality. Knowingly or unknowingly, we can become prone to seeking out hard for the sake of seeking out hard, for staying longer than we should, for holding on to something longer than we should. So I'm curious, you alluded to it earlier. There are hard seasons of life, there are good seasons of life. Like with the wisdom you've accumulated all these years, how do you discern the difference between productive and unproductive?
1:18:54 Tyler Hennessee: Gotcha. Tyler Hennessee: That's a okay, that's a fantastic question. I think that's a very wise question. So, things that are outside of my control, which is basically everything about other than how I respond. Like I can't control, right? just because we've used these examples already. The the people who passed away or my dad stroked, those things were completely out of my control. So I can stay in that season and just continue to like I don't talk about it a lot. If you bring it up, I'll I'm happy to have the conversation, but I'm not like, well, I'm struggling with business because my mentor died. I'm struggling because I don't have anybody to talk to anymore. Like that's you choosing to stay in that season as opposed to responding from that season and going, all right, I need to make some changes. I'm gonna keep going. So my choice is to wallow in it or to start start growing from it. And so I think it's just a daily conscious effort. To to not say, I'm not gonna seek a hardship to seek a hardship. Life is already hard enough. Life is hard enough as it is. I don't need any extra help to make this harder. But just the the simplest, best analogy, you'll you know this, but like running or working out. It's like you are not gonna get faster if you don't do sprints. You're not gonna get faster if you don't do long, long distance. You're not gonna get bigger biceps or chests, you don't do bench press or curls or push-ups. It's not gonna happen. So it is only gonna happen through the endurance of of that pain or that struggle. And so I just think it it's it's your attitude during that stuff. And so for me, it's just it's it's the response. It's how do I respond to this adversity? not just trying to stay there. Like I don't think I stayed in my dad's but those things we talked about. I think I moved pretty quickly, pretty rapidly. Probably I needed to grieve a little longer.
1:20:42 Paul Salter: Mm. Paul Salter: Hmm. Tyler Hennessee: But my my MO is like, let's go. Like this is done. I can't I can't change this. It's time to respond. Paul Salter: I almost hear an element and I swear I think it's like a cliche or a motto from somewhere, but it's like it's choose your heart and choose how you'll respond. Tyler Hennessee: Yeah. yeah. Choose the choose the hard way. Like that's I don't claim to be the it's just and I understand like all the the the jokes that can come with the phrases. It doesn't matter to me. It's just choose the hard way, choose the narrow way, hard things make you better. And so it's just it's more of a for my family of like, hey, it's not if it's when it's gonna happen and how are we gonna respond? So we don't wanna live in the hard season. We don't wanna seek the hard season, but it's going to happen. And if we build up enough temperament, build up enough resilience, build up enough miles, then we we really face those things just a lot, a lot smoother, a lot cleaner. It's you don't have to repeat the same mistakes over and over and over again.
1:21:52 Paul Salter: Well said. Two decades of pouring into people, building relationships, changing, and I imagine literally saving lives into a two going on year three journey of from the outside looking in, team is growing, f income is growing, impact is growing, relationships is growing, kids are homeschooled, you get a lot of time with them, thriving, growing marriage. On the outside, all of these boxes are checked. It looks wonderful. You've been vulnerable enough to allude to some of the behind the scenes. My question is, with all of the success I just described on the outside, do you feel that you've learned to fully enjoy it?
1:22:34 Tyler Hennessee: No. I told you I'll be honest with you. no. I think I'm very much still learning how to like I have to kind of consciously tell myself, mean my little girl, she's ten years old. earlier today she came across my lap and I'm sitting there holding my my ten year old in my lap. And I was like, Lord, I don't want this to ever end. Like the the the season is so close to being done. And I'm like, hey baby, will you still crawl up my lap when you're 18? She goes, Yes, daddy. You know, and I'm like, there's probably no way, but I'm praying she does. so it's like I I I but I'm in that moment. I literally have to make Tyler. Like my my I know my phone's not with me at this moment. Good, you're right. But I have to make B B be in this moment. And so I'll do it when I go and walk with my wife. I will tell I mean it's crazy, call it what it is. Some people probably just naturally do that. I'll be on a walk with my wife. I'm like, Tyler, be in this moment. Like slow down. And that that that is some like through talking to counselors and stuff like that, realizing like when I when I play golf. Like when I was struggling to stop and to kind of look around and look at the sky, smell, like to be like, dude, there's some really good things going on. Like this, this game is not it. And so in the same way, I have had to teach myself to do those habits so that I don't stay in that kind of lull or that I gotta work, gotta grind, gotta grind. Like that's this is so unhealthy.
1:23:57 Paul Salter: When it comes to your entrepreneurial chapter of life, building your team, you know, 800% income this year, greater impact, bigger relationships, what hasn't success give you, given you that you thought it would? Tyler Hennessee: So I I I teach a lot on time. our bus business is even about helping people buy their time back. And so as I'm sitting there trying to help people buy their time back, I'm giving up more and more of my own time. And so I the the irony is not you know, I I I see the irony full fully. And Again, like there are those pockets of time that I had that I didn't even have my W Two. And at any point, I could be like, hey, the rest the day is off. I can I mean when you're in charge, you're in charge. But what good does that do? And so I I'm still trying to figure out how to balance that fully. I man, between you and me, I don't want to just I don't want to retire. I don't want to be off. I think that just leads to more loneliness, depression, those types of things. I think we're meant to work. I think we're meant to have an impact. So that balance, I've never been great at it. And I'm more aware of it. at this at this stage of my life, I'm just trying to learn how to incorporate it to go, dude, you got to completely set it aside, completely be present with your family or with your friends, whatever it is. So for me, that requires specific disciplines of turn your phone off, leave it in another room, those types of things.
1:25:17 Paul Salter: So what I hear, and I'm glad you called yourself on that because I heard that as well, is though it seems to me you've created financial freedom faster than you've learned how to create freedom from your business. Tyler Hennessee: Yes, sir. Paul Salter: Who owns your time right now? Tyler Hennessee: my staff, my like my team. I don't even call my staff my team. my community, I have since January we've added 181 people to the community. There's over 500 total. And a lot of those people have direct access to me. great people, but they they don't have the because like, dude, here's the bottom line. Again, the 20 years of ministry have helped me a lot realize I I know I'm not important. I'm not some big timer. There's always someone who has a hundred thousand-person community, and it's all relative, but those community members don't realize. Even having a hundred 100 is a ton of people who have direct access to you. So if you have 500 plus all your business partnerships, plus your family and people, like you said, hey bro, can I get two minutes? I'm like, no, like I no, you can't. Or I just don't respond to some of those and be like, you never respond anymore. It's like, dude, like I need to schedule it out in this season of life. I do believe the season will end as well. And I'm trying to kind of incorporate it where I have. You know, some right hand men that can or women that can handle those jobs and a fulfillment team where I'm out of those seats so that those things start getting handled by other people that I can be like I I do want to jump on a phone call with you and say what's up, but that's normally yeah, I gotta get back to that.
1:26:49 Paul Salter: I'm gonna ask this question very intentionally with my word choice in a way that I hope will leave you with a seed of curiosity planted well beyond this conversation. If time is one of the resources God has entrusted you to steward, are you stewarding yours as intentionally as you teach people to steward their money? Tyler Hennessee: I mean, Paul, that that that was the best question of the day, because you just hit me between the eyes. and I don't wanna I'm not gonna plead ignorance on it. Like I feel like I'm I feel like I'm very aware. Just a lot of experience, a lot of time on that, but It there is something in my personality or whatever that that combats the truth of what I know is needed, if that makes any sense. So like I know that this is vital and I would preach it from the rooftops to anybody, but man, man, it's like as hypocritical as that is, I'm not intentionally going screw this, screw this truth. I'm just going, I naturally lean here. So it's like I know this truth is here, but I naturally lean here and it it it and I wrestle with it. So it goes against my flesh and and what I what I yeah, what I what I want to do, I guess. So yeah, I need to work on it for sure.
1:28:13 Paul Salter: I appreciate you sharing that. You are not alone by any means. It's the knowing and the being. It's I know to do this, but I'm embodying that. And candidly, and I think you said it well, it's it's noble intention. You know, you're doing all of this for the right reasons. It's how do I allow all of it to coexist? And that's life's gate greatest puzzle or game, if you will. Tyler Hennessee: Yeah, no doubt. It's tough. I mean, it's like I said, it's easier s to say something than to do something. And so yeah. Paul Salter: Well go building off of that, what has specifically the in this chapter of life, what has success cost you?
1:28:56 Tyler Hennessee: I mean, i it depends on how you define success. If we define success the way business owners define success, it's probably cost me some friendships, it's cost me some loneliness, it's cost me some Tyler Hennessee: I mean, those are the first things that pop in my mind. I don't I don't feel I really overall I I feel content. I feel hopeful. I feel excited about this next season. I feel excited about the season I'm in. I I am just I'm never here. I never stay like all right this is great let's stay here. I just I'm like, how do we grow this? How do we build this? How do we make this better? I said, leave like if you got a sponge, like till that last little drop comes out is how I look at my life. So I think it's probably cost you people more and more and more of like what I've always felt. People like, what do you like, why why, Tyler? Like, why aren't you content here? And I'm like, I am content.
1:29:56 Paul Salter: Mm. Tyler Hennessee: With who I am as a person, but I'm trying to maximize what I've been given. I'm trying to steward what I've been given. Paul Salter: Contrast for us your definition of success, your first year in ministry, compared to your definition of success today. Tyler Hennessee: I think s success would be what I just said. I like the word stewardship is a cheesy word, probably in the maybe it's in the church or maybe in the I don't know. But I I I am when I use words as a lyricist and someone who's done that, I I the words matter to me a lot. Stewardship is truly like maximizing whatever abilities you have. It's not just monetary. Like you said, you you said it perfectly with time. And so I I think constantly. I there's my ADD. Paul.
1:30:46 Paul Salter: I wanna understand how has your definition of success evolved over the last twenty-two years? Tyler Hennessee: there you go. Thank you. I don't I don't I need to kind of probably flush that out with you. I think in ministry it was am I pouring into people? am I being present with them? Am I being real with them? Not being holier than now, be like, hey, I'm a normal dude. Like one of my favorite things to be like, mean I I I would have never guessed you're a pastor. And I kinda took that as a compliment 'cause I'm like, hey man, I love people and I want a steward well and I want to pour in your life, but like I'm a normal guy with normal struggles. So success there was just making sure I was doing those types of things, still leading my family well, leading my wife well as best as I could. In business, man, I I I know it sounds funny. I don't think it's actually changed a whole lot. It's like it's just my the tool has changed. I'm sorry. In ministry, I didn't have nothing I don't want to present myself as having a lot of money. That's not it. And but admission I didn't have any extra money. And so I didn't have that to steward. In business I do have extra money, so now we steward in a different way of giving more monetarily and sharing with others. It's all about w with what you've been given, how are you maximizing it? And so I believe it or not, I actually don't think it's changed a whole lot. It's just a different it's just a different vehicle, different job title.
1:32:03 Paul Salter: I respect that approach. I really like how you framed that and stuck to what I'll just call your core values and just brought them to a different arena to continue to serve others. Tyler Hennessee: Yeah, absolutely. I appreciate that. Paul Salter: Yeah. I appreciate you. I appreciate this conversation, your honesty, your candor, your vulnerability every step of the way. Thank you for joining me. Tyler Hennessee: Man, absolutely, Paul. You you asked some of the best questions I've ever heard. You're very, very good at what you do and definitely brought a lot out of me. So I appreciate you having me today very much. STOP RECORDING (AUDIO & VIDEO) HERE. Paul Salter: Absolutely. And we'll stop it there just so my editor knows. But dude, seriously, that was a blast. I really appreciate it. Tyler Hennessee: Yeah, you as well, man. I had a lot of fun with you. You you you're asking questions, bringing me back, making me think. It was r it was really good. You did very good, man. Paul Salter: But thank you for that. Yeah, that's the goal. So I'm glad it landed.
1:32:45 Tyler Hennessee: Yeah, is so is this your f is this one of your full time gigs? Is this a a side gig for you or what how does work? Paul Salter: So my yes and no. So my primary means of providing and serving is one-on-one coaching. I'm a mindset and performance coach, a credentialed hypnotherapist. So I work with this audience, the founders, the CEOs, high-level execs. I've podcasted since 2018. I've got one longstanding one, which funny enough used to be called the Scratch Golfers Mindset. So when you had that golf psychology thing, I'm like, yo, dude, you're a million people do that. I I have golf clients all over the world. Tyler Hennessee: Right. Tyler Hennessee: Yeah. So what what I went through is not abnormal, you're saying? Paul Salter: No, no, no. But you and you said it so well. I had to sh I had to like bite my tongue to shut up. But I always tell my golfers or any athlete I work with, like you bring your whole self to the course. You don't just struggle with anxiety on the course, you're struggling somewhere else. We gotta get to the root of it. And it seems like that's what your guy was telling you.
1:33:36 Tyler Hennessee: Yeah. Yeah, a hundred percent. And I but I c I mean, and it's still like I am not the same from two years ago. Like I'm I'm still working my way back in, but I realize it was so performative, like thinking you care what people think on the golf course. Like these dudes don't care. You're playing with a bunch of amateurs. Like no one cares. Yeah. Paul Salter: Mm-hmm. Yeah. Yeah. Absolutely. So then yeah, this I've got a podcast that's like coming up on episode two hundred. And then this is my new project, my baby that I'm most excited about candidly. And it will debut this Sunday, the twentieth. And you're gonna be my either sixth or seventh kind of in the chamber. So I'm staying ahead and yeah, man, really enjoying it. Tyler Hennessee: Heck yeah. Yeah, me too. I I love that you're doing that. So make sure you collaborate with us on YouTube so we can help get it out there for you too. And if you have if you're willing to share whatever files you have, my team will will you know, tag you and using our our payment. Yeah. So we'll we'll help.
1:34:24 Paul Salter: perfect. Yeah, I'll give you access to a good you can just send into your team, but a Google Drive folder of already cut up caption clips. Yeah. All M19, dude. Yeah. that's so funny you'd even know that. That's funny. Tyler Hennessee: Awesome. Well, how did you Jake by the way, Jake Rossweiler? are you nineteen? I just didn't realize that. I didn't even know that. That's hilarious. We could have talked about that for forever. Okay, so you're a golfer. Okay. So now it's so I I got this isn't you might be way better. I got down to a two point nine in twenty twenty ish, which was my best I'd ever met. Well Bro, when I say I went to like a twelve in a year, it was like it was Paul Salter: I am, yep. huh. yeah. Paul Salter: I am nowhere near there. That's awesome. Tyler Hennessee: It it was like and me shooting at eighty four or eighty five or ninety five, whatever, it looked like a hundred and twenty. It was just like it was hor horrible. So I'm still working my way back and I just I I I do some finicky things. I'm like, is what it is. I've gotten over it. So Paul Salter: Yeah, that's rough.
1:35:17 Paul Salter: I feel that w do you have another trip already booked? Tyler Hennessee: no, I went on a few this year. I'm I'm gonna are you going to Austin by any chance? Okay. I'm gonna go to Laura Lum with that one day to meet up with them and then I'll probably do some next year. But for right now I think I'm I'm set. Paul Salter: No. But you Paul Salter: Okay, there the one in February is down in is like just north of Tampa, Florida, where I'm at. So if you make that one, let me know. 'Cause like a couple of guys I'm trying to invite to come early. I'll take you guys out to my club or stay late, whatever works. Tyler Hennessee: Heck yeah. I'm meeting with do you Myron Golden by chance? Paul Salter: I know of him, he's a member at my club. I've never actually met him in person yet. Tyler Hennessee: Okay, so I was on the phone with him yesterday. He he's a client of mine. so he joined my community a few months ago. And so he's flying me out to to to see his I don't know, production studio. And we're gonna do a video together, maybe a podcast as well. But that's if y'all at the same club, I'll hit you up. We can maybe all play golf together. I don't know yet. That's that's the problem Myron. It's probably gonna be the week of and I'll have to text you and see if we can make it work or not. Paul Salter: Okay. Okay.
1:36:03 Paul Salter: Okay. Paul Salter: Yeah. Yeah. When are you coming down? Okay. Paul Salter: Yeah, let me know. Like I said, I he either like there's two sister clubs 10 minutes away. I don't know which one he's officially a member at, but I've seen him at both. Yeah. Tyler Hennessee: Yeah. Well that's cool. Well awesome. Well I I didn't realize you were nineteen. Well that's that's good to know. that's so funny I did not connect the dots on that, but Paul Salter: Probably for the better it gave us a blank slate. Tyler Hennessee: Yeah, that's that's true. Well thank you for yeah having me today. Had a lot of fun with you. Paul Salter: Yeah, dude. Thank you. I always like to ask, based on this conversation, you know, kind of what I'm looking for, the candor, the vulnerability. If anybody comes to mind in your circle, your network who you think would be willing to have this type of depth in a conversation, I would always greatly appreciate an introduction.
1:36:55 Tyler Hennessee: I got an ideal person for you. I when you first started talking, I didn't have anybody, didn't have anybody, and then a name popped in my head. he's been through a lot. This dude's been prison and now a successful guy. We're in business together. He's in M19. Do you know Jake? that's not what I'm gonna tell you. Paul Salter: I think I who are you gonna tell me, Jake? okay. Jake I'm talking with Jake tomorrow. That's funny. Uhhuh, yeah. Okay. Huh. Tyler Hennessee: Really? There you go. Yeah, I know Fruget. You're talking Jake Fruget? Yeah, I know Jake very well. We'll leave that to the side. Micah Pilke. Paul Salter: Okay, I don't know my cup. Tyler Hennessee: Mike Kapilke is a developer here in Austin. He has made a lot of money recently and just a great dude, vulnerable. he'd be a good person to have a conversation with. Paul Salter: Okay. Awesome. And you said he's in nineteen? yeah.
1:37:37 Tyler Hennessee: Yeah, he's been quiet in nineteen, but he just joined recently. Micah Pilkius P I L. Yeah. Paul Salter: Okay. Yep. I found him right away. Yeah, cool. Yeah, dude, if if it feels right like for a text intro, you don't need you can give him your brief experience. I can close the deal if you will. that's awesome, dude. Well thank you for that. Tyler Hennessee: Yeah. Yeah, absolutely, Paul. Appreciate you having I'll I'll I'll set you up in a group text and you can take it from there. Paul Salter: Perfect. And hold tight one second. I'm actually just going to stop the
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