The Firefighter Who Walked Away From Early Retirement And Chose Entrepreneurship with Jesse Flocken – EP 292

Interview with Jesse Flocken

The Firefighter Who Walked Away From Early Retirement And Chose Entrepreneurship with Jesse Flocken

“I can’t do this for one more day.”

Jesse Flocken had what most people would consider a dream life: a stable career, a guaranteed pension, a great family, and retirement within reach before his 40th birthday. But after years of working 24-hour shifts and missing valuable time with his family, Jesse and his wife Courtney began reflecting on a question they often helped others answer: “What do we want to be known for at the end of our lives?”​

That clarity forced Jesse to confront a difficult truth. After writing his resignation letter just to see how it felt, he realized he couldn’t go back to firefighting for even one more shift.​

Today, Jesse is an entrepreneur, growth strategist, and founder of Clearly Relevant, a marketing and business growth company that helps brands scale through better systems, attract better leads, and close more business. But what makes Jesse’s story so compelling isn’t just the business he built after leaving the fire department. It’s the mindset shift that completely changed how he defines success, fulfillment, and freedom.​

In this conversation, we discuss how clarity can help you realize that opportunities are actually distractions, why so many high achievers struggle to slow down long enough to define what they truly want, and how building a business around your values can create deeper fulfillment both personally and professionally.

In this episode, you’ll learn:

Why Jesse walked away from a guaranteed pension just four years before retirement to pursue entrepreneurship and a more intentional life.

How writing his resignation letter before making the decision gave him the clarity to know he was making the right choice.

✅ How defining what you want to be known for at the end of your life can help you reverse engineer a more meaningful life and business.

Featured on This Episode: Jesse Flocken

✅ What he does: Jesse Flocken is the founder of Clearly Relevant, a marketing and growth agency that helps businesses scale through systems, branding, SEO, paid advertising, and strategic growth initiatives. A former firefighter, Jesse now helps entrepreneurs create businesses that align with their values, relationships, and long-term vision for life.

💬 Words of wisdom: “Once we figured out where we’re headed, all these things that I thought were opportunities were actually just distractions because they were in the complete opposite direction of everywhere that we wanted to go.” – Jesse Flocken

🔎 Where to find Jesse Flocken: Website | LinkedIn | Facebook | Instagram

Key Takeaways with Jesse Flocken

  • Why Relationships Matter More Than Business Titles
  • The Decision To Leave His Firefighter Career Four Years Early
  • The Workshop That Changed Jesse’s Life Direction
  • Writing A Resignation Letter Before It’s Time
  • Why High Achievers Struggle to Slow Down
  • Building a Life Around Purpose and Relationships
  • The Difference Between Success and A Life In Alignment
  • Lessons From Bob Goff and Radical Generosity
  • How Marriage Shapes Business Leadership
  • Why Most Businesses Have a Systems Problem
  • The Power of Shared Experiences in Relationships
  • How To Learn More & Connect with Jesse

Why So Many Successful Entrepreneurs Feel Empty

Inspiring Quotes

  • “When you’re generous, you’re never poor.” – Jesse Flocken
  • “I don’t want to ask anybody to do something that I haven’t done.” – Jesse Flocken
  • “Once we figured out where we’re headed, all these things that I thought were opportunities were actually just distractions because they were in the complete opposite direction of everywhere that we wanted to go.” – Jesse Flocken
  • “The people that I know that are the happiest and the most successful are the ones that built something that brought others with them and didn’t sacrifice family and friends along the way.” – Jesse Flocken
  • “If you can’t enjoy your life now, you’re going to be miserable later.” – Jesse Flocken

Resources

Want My Team’s Help?

  • Tax Strategy Masterclass
     Learn the 28 most effective tax strategies the wealthy use to save thousands.
    lifestyleinvestor.com/tax

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Read the Full Transcript with Jesse Flocken

Justin Donald: What's up, Jesse?  Good to have you on the show.

Jesse Flocken: Hello. Yeah, I'm excited. Thanks for having me, and excited to see you again.

Justin Donald: Well, this is fun because it's really neat when I have friends that become lifestyle investors and join our Mastermind. So, it's like we had a friendship first. We're able to continue building and fostering that. And then I love seeing the ecosystems kind of mix with people that I've known beforehand. And then all the people that I'm in pretty close relationship with these days because the members is kind of where I spend most of my time. And you just fit in so well. You and Courtney are just a blast. People love hanging out with you. You stand out because you look so darn young, like Fountain of Youth young.

Jesse Flocken: Thank you.

Justin Donald: And so, it's like people are always like, "Man, how's he built all this? He looks so young.” It's amazing. So, love having you here. Welcome to the show.

Jesse Flocken: Thank you. I think something that's unique about even us talking when we first originated over some pickleball, but I think it was, after a while, it had taken us some time to either hanging out or becoming friends to where we're like, "Okay, now we can talk about what we do.” And so, I thought that was unique about both of us because most people in most circles will just jump right into like, "Oh, so what do you do?” and like, "What's this give-take look like?” And both of us, we're almost adamantly not saying anything and just getting to know life. And so, I thought that was pretty unique.

Justin Donald: I love it. Well, I just love slow playing the business thing because you'd get to know people. You get to know the most important parts of people, the parts that are more important than what do you do. What do you do for a living? Like, I want to know who you are at your core and how you treat your family and other people, and like that matters to me. And by the way, shout out to the late John Ruhlin, one of our closest friends. Collectively, you and I, like Courtney and you and Jennifer and I, a testament to him, he brought us closer even from the grave, like, what a great soul. And I'm so glad that we've gotten to know you guys better, and he really brought us together. So, pretty awesome.

Jesse Flocken: Yeah, and I think just a testament to that too of just showing that like when you're generous, you're never poor, in the way of just radical generosity, not just financially or monetarily, but also just relationally. And even that, again, that way that we met through that was just relationally generous. We were just introducing everybody to everybody and really enjoying that time. And that, for sure, is John Ruhlin was the ultimate connector.

Justin Donald: He was. He was. And he lives on. I still have one of these things on my desk that reminds me of him, and I've got one in my bag. So, yeah, a soul lost too early, but he's doing great work even from beyond. So, we know he is smiling down at us from heaven, and so happy that I got the many years that I did with him, and we're actually flying out to St. Louis to spend some time with his family with all his lovely ladies, here in about a month. So, looking forward to that. Exactly a month, actually.

Jesse Flocken: Alright. One more testament to how we met. I do think it was kind of funny that when the Ruhlins were deciding where to live in the country, there was these Austin folks and these Gilbert, Arizona folks, and we were kind of back and forth. And once we met each other, we're like, "Okay, like, you're pretty cool. I get it, I get it.” And then they just didn't move to either of us.

Justin Donald: That's right. We are battling trying to get them. “Let's convert them to our city.” And then you see the poll, you're like, "All right. Well, I get it now.” Because it's not about, I mean, when you're moving, it's all about like, who are the people there, right? And we're going to get into relationships because this is something that you're super strong with, but I just want to give you props because this podcast is something for the longest time you didn't do. I remember when we first started talking, and I'm like, "You've got a great message, and your business is booming, and you're doing cool things for people, doing cool things for big businesses too. But you could blow it up so much more by telling your story, even just personal branding beyond your business.”

And so, it's cool to see you stepping into your power. I mean, you sent me a text, and you're like, “Hey, I'm about to do my first keynote, and you've been on a few podcasts now, and so I'm proud and excited and happy to see you taking this path, and for our audience, just excited that you're going to share your message with us.

Jesse Flocken: Yeah. Thank you. And I think that one of the things that I'll talk about later is that I don't want to ask anybody to do something that I haven't done. And so, we'll talk about my journey from leaving. I sort of had an opportunity at some passive income through the pension system and other things, and I left that to pursue this, and we'll talk about that. But truly it's, I had said no to everything. I mean, something unique about Courtney and I is we haven't had social media for over 10 years.

Justin Donald: I love that. So cool.

Jesse Flocken: And we've actually ran into people in like the coffee shop in our neighborhood that moved away and moved back. And like, they didn't even know, like, "You have two kids?” We're like, "Oh yeah, sorry. He wasn't born by the time we got rid of social media.” And so, with that, though, I didn't even know that it was out of my comfort zone. It just wasn't in my purview. And so, thanks to you, I do appreciate you encouraging me to step out there because I do think that more people have benefited from the value of the experience, from other entrepreneurs to people looking for a career change, to where some people didn't even know that I do marketing or growth or any of those things. They just knew that they're like, "Yo, you're the what's next guy,” just because it was just encouraging them to do what we had done.

Justin Donald: So, I want to talk about what's next, but before we get into that, we got to talk about your career because you used to be a firefighter.

Jesse Flocken: Yes.

Justin Donald: So, you had a pension, like everything was lined up. You only had a handful more years to just kind of what do people say, to ship it in? You're almost there, but you walked away from that. You walked away. You could have hit the easy button. You didn't. You had this burning desire to do something else. And I want to talk a little bit because there are some lessons that I think you learned, I think everyone learns from choosing a different career path, and there's risk doing something else. There's fear of the unknown. There's fear even of the known, but there's definitely fear of the unknown. And so, I even remember talking to my brother-in-law, Ed, about this, like he's about to retire. And so, he spent his entire corporate life with one company, and he's even like, "Oh my gosh.” And for him, it's like wrapping up any day here.

And so, it's like, what's next? And even though he's going to be wildly successful and whatever the heck he wants to do, because that's just how he's wired, there are still nerves. There are still nerves. So, talk us through what led to the decision, and I know there are people that are listening to this or watching this that are in this situation right now. They're not loving what they do. They're not waking up so eager to go to work or do professionally what they're doing. And they are in desperate need of a change but maybe don't have the confidence to make the move.

Jesse Flocken: Yeah. Well, I would say a couple of things. One is I am relentlessly optimistic. However, that really, people usually correlate those things as like, "Oh, you're optimistic and excited. And so, that was part of it.” And I want to just, before I even start, like that is nothing to do with it. And it actually started well beyond anything with me. And I'll say that we got to this point where I was kind of burning the candle at both ends. I was a firefighter for 15 years, and I was only four years away from a pension for the rest of my life. I could have retired at 39 and had passive income essentially forever. And the thing that really hit me was a couple of things. One, just taking way back, I'll share that, or sorry, leave that for another time, about how I started my business.

But essentially, like I accidentally started my business, almost from the fire station in some ways. And my very first client was a Fortune 100 client, and it was just accidental. I was like, “Hey, you guys work with you guys, and I'll just help.” And they're like, "Well, no, no, we need you to be more as a part of this.” And so, I kind of was like the dog that caught the bus in the way. And so, that was slowly going in the background. So, I don't want to make it sound like it was just fully overnight. However, it was this decision of where I just felt like I'll just kind of paint a day in the life of what it looked like. I was a firefighter, and my schedule was where I'd work, say Monday, Wednesday, Friday, 24 hours.

And when I would go to the station, I'd go at six in the morning, shift change started at like seven or so, and then I'd work 24 hours. The next Tuesday I'd get off of work, and it was like 7:30 to 7:45, depending on the calls for that day. I'd get home, I'd have 15 minutes with the kids to go to school, and that's like shower, change, get all who knows what off of me, change as fast as I can. Get them to school by 8, and then I would go to the office, and then I'd work until five, and my kids were young at the time. So, then like they had early bedtimes at that point. So, I'd see them from like 5 to 7:30 maybe. And then I'd be gone for another 36 hours because I'd leave before they were awake.

Justin Donald: That's tough.

Jesse Flocken: And so, it just got to this point where, on paper, it looks awesome. I mean, most firefighters have some sort of second job, I would say. But it looks awesome on paper because it's, oh, you work 10 days a month, and you have the rest off. However, when it doesn't fall right and you have a young family, I realize like, "Man, to really make my pension worth it, I wouldn't have to stay five more years. I'd probably have to stay, like an additional five after that.” And then my 7-year-old at the time would be 17. And then I might as well work as long as I want like, what am I doing this for? And so, it became this fast-forward a little bit. We still were at a… I'm going to kind of split the story in half here really quick.

So, Courtney, my wife, had been really successful in Fortune 100 sales, then went to medical device sales, and was really successful there, ended up becoming a salesperson of the year at the time. Now, it be in a legal gray area, but she was required by her company for her entire 100% quota while she was on maternity leave. So, she was only in her territory for 75% of the year, still beat everybody else by a landslide, and then won salesperson of the year. And during that time, and the reason why I bring that up and split the story there is because she had just recently, our nanny was kind of going through a big life change and was quitting. And Courtney just really felt like, "Okay, like this is the time. I need to stay home with the kids,” at literally the pinnacle of her career.

And she was doing awesome, and it was great to see that paycheck coming in. And with that, her mom years and years ago, she was, I don't normally tell this part of the story, but so impactful to know like your impact you can have on kids later on, you might never know it. And her mom was working in a salon in small town Ohio years and years ago, and Courtney's soccer games were on Saturdays. And this lady was like, "Oh no, like, Sandy, you got to come in, you got to work Saturdays like it's non-negotiable, this and that.” She's like, "Well, my daughter's games are on Saturdays, so like, I'm out of here.” And she quit, and she went to the salon down the street, and like five people went with her. We're like, "All right, see, we're out of there.”

Well, that story came up when Courtney was looking at some life change and then that helped her go from one Fortune 100 company to another one. And so, at this point, it was not uncharted territory for us because we're like, "Oh, there's a big life change. Something's not gelling,” and we were just burning the candle at both ends. So, now back to where I was with the fire department, we had done this workshop for serial entrepreneurs that we do for just charting out, like what the next season of life looks like beyond some sort of success, and trying to map that out. And I was like, “Courtney, we have to figure out where we want to go and what we're headed, and why.” And it's not about the amount of income if you don't know who's on the journey with you or where you're headed and all those things.

So, we just kind of started mapping out our life through this workshop framework that we do with clients and ship the kids off to grandma and grandpa's house. We'd just redone our backyard and kind of a nice like resort-style pool and greenery, and we're like, "This is the perfect place.” And we did this workshop, and it starts out basically like, what do you want to be known for at the end of your life? And then we kind of reverse engineer that in some different categories and family and friends and health, spiritual. And we got to this part where we're like, "All right, what are the top things that have to happen this year in order for all these other things to be true?” Because at this point, we had a ton of opportunities in front of us, what I thought were opportunities.

And then all of a sudden, as we're doing this, I realized like, "Man, like all these things, like once we figured out where we're headed, all these things that I thought were opportunities were actually just distractions because they were in the complete opposite direction of everywhere that we wanted to go.”

Justin Donald: It's a great distinction. Opportunities actually being distractions once you gain clarity. That's powerful.

Jesse Flocken: And so, with that, it was really this defining moment of we hadn't really talked about it, and this is where Courtney and I's version of the story like differs a little bit. We'll never know what really happened, I guess, but when we wrote this down, I just remember, we hadn't talked about it because the workshop you do like together, but separate, so you like share afterwards, so it doesn't affect how you're writing things. And it's not meant to be meant as a couple. And we just did it as a couple, and it was pretty cool. And when we turned it around, I remember my number one thing and her number one thing were both quit the fire department, and we really hadn't talked about it that much.

And so, I was originally like, "All right, we're going to go down like maybe I'll quit in six months and kind of figure this out and what that looks like.” And she's like, “Jesse, I'm not going to send it. I'm not going to do anything. Just write your resignation letter right now, like, write it.” And so, a friend of mine, Bob, always talks about, he is like, "Oh, just write your resignation letter and give it to your wife and say, 'Hey, three bad days in a row, you just send that thing in. You don't have to tell me. I'll know. I'll find out.’” And so, she's like, “I'm not going to send it for you. I'll put it in the safe.” And so, I wrote this letter of resignation.

Justin Donald: What a powerful exercise, by the way. You write it before. It's like, “I'm not quite sure, but let me just write it.”

Jesse Flocken: Totally.

Justin Donald: There's clarity in the process.

Jesse Flocken: Absolutely. And if I wouldn't have quit and I still would've done that, I would've went back a totally different person, like truly. And so, through this, as I'm writing the resignation letter, I'm like, “Courtney, I can't go back even for one day.” Like, it was so drastic that I was like, "Now that I know where we want to go, just one more day pursuing something that's in the opposite direction is not just a step backwards. It's an about-face step in the totally wrong direction. And so, it sounds harsh, but I'll preface it, but I didn't say goodbye. I didn't like go back. I never worked a single shift again. It kind of looked like I was dead because my room was exactly as I left it. My locker was exactly as I left it. All my stuff was exactly as I left it.

And I wasn't planning on not coming back. And I literally just up and quit, and I left, and I started burning down some time and some other things because I had accrued a lot of years of sick and vacation time that I wanted that runway. And on the flip side, I'm a very highly relational person, but my crew had just split up from promotions and other things. So, the people who I was with for 14 years were, that was like the first time we weren't also going to be together. So, if they were there…

Justin Donald: Made it easier.

Jesse Flocken: Yeah, I probably would've went. And so, went back for like a tour of farewell tour or whatever. But with that, it was a really defining moment of like, "Okay, like I got to do this.” And matter of fact, if these other things in our lives are going to be true, then we've got to run at this full speed like I can't even waste one more day. So, that was kind of the start of that.

Justin Donald: I love that. So, it's interesting to me, though, because you were able to do it. It was almost like you were empowered. So, you took the time to reflect. You took the time to dream and figure out what could it look like if you did something different or what would light you up. You took the time to communicate this with your wife. So, there's a lot of intentionality around that. And you're known in the circles of influence that you have with talking about the question, like, you have a question, that's what's next? What's next for you? Asking other people, what's next?

So, why do you think so many high achievers struggled to pause long enough to gain this type of clarity, or pause long enough to, or even like, I would say there's this lack of intentionality out there where people are just running on autopilot and running on default. Life is on default. It's not by design, it's not intentional. So, like, why do high achievers have such a hard time slowing down to get the clarity they need for what's next?

Jesse Flocken: Yeah. Well, I'm going to combine like five books into one idea here, but we think of like Dan Sullivan talking about it's who, not how, and we talk about like how we're just meant to build like we're creators. Like, we're meant to build, and if you stop building or stop working, even if it's a work optional or retirement or whatever that is, like people who stop working are just like, "Oh, they just pass away.” Like my father-in-law, we joke that we're like, "All right, one day he is going to be in someone's yard like digging a ditch and landscaping, doing what he loves because he won't stop because when his friends stop, they went away.”

And so, with that, I think it comes back to this innate purpose, that again, like combines like lots of books out there, but it's this innate purpose to build, have purpose in general, what are you working towards? And I know on this podcast, you've had some guests in the past who've talked about like they've achieved it all. And they were like the most depressed they've ever been in their life. And it came out of left field. They were like, "Oh, people said this,” and like, it just hit me like, shocked.

Justin Donald: I should be happy. I'm not. Yeah.

Jesse Flocken: And this is where, when we talk about the Lifestyle Investor, one of the things that I most resonated with when my version of your story is that you talk about how I was, you say like, "My passive income was covering my lifestyle long before I was ever a millionaire.”

Justin Donald: That’s right.

Jesse Flocken: And for me, my active versus passive lifestyle was what I wanted it to be years from now and my goals exceeded right now. And so, part of it was I wanted to achieve the lifestyle piece, again, without the lavishness or other things that people think of. There’s lifestyle creep and income, and that’s not what I’m saying, but I really, doing this workshop, something, the clarity and the purpose that came was people want to build, they want to be known for something. So, I had to figure out what do I want to be known for at the end of my life. That was a different exercise in that.

But then the last thing was, how does this fit into how I’m going to love my family, how I’m going to be a better husband, how I’m going to love my wife, how I’m going to be a better friend? I had a lot of friends also, who had reached the top, had massive exits, other things, and they came to me and kind of like, I wouldn’t say shambles, but came to me in like a pretty serious identity crisis, like we were talking about a little bit, to where they’re like, I don’t know what’s next. I’ve always just built something.

And now, I actually contractually can’t build something for a while. And so, when they were left in a room with themselves, they’re like, all that’s left is me. And so, I say all of this because for me, the defining moment was, who is on this journey with us? That was a question we had to ask. It wasn’t just Courtney and I. It was our kids, it was our friends, it was our street. It was all of the things our extended family, what’s that look like for our faith? Are we going to go serve and help others? Are we going to go do these? Are we going to bring our kids on these trips? Are we going to, like, one things, like we want better marriages around us? So. we’re like, all right, we’re going to start bringing people to Disneyland with a friend of ours who has workshops there and we’re going to bring people to Maui for these marriage retreats and other things.

And so, once we had that guiding North Star, if you will, it became really clear how we needed to fund it and what we needed because, and forgive me for missing the original question here, but coming back to it, I think that something that’s really important for all these entrepreneurs that are looking to make a leap, I think it’s so head down. Like right now, there’s someone listening that’s like, I am so head down, I can’t even see what’s next because they’re trying to build. And that’s what I wanted to start with is getting head down, trying to build something.

And what I find is there’s actually some members in the community that when I schedule a call with them, they go look and see if they have a vacation booked because they know that the last time, they were so heads down on investing and caught up in the excitement of all of it. They’re like, oh, yeah, I forgot. Like, we need to go hell vacation and splurge a little bit and take care of those other pieces.

Justin Donald: That’s right, that’s right. Well, like hearing the way you lay it out. I know you have a lot of frameworks around it. I think you and I run into a lot of people and probably, a lot of people listening to this call run into a lot of people that on the outside, they look very successful, but on the inside, they’re not. And this is a little different than the identity crisis. I mean, I think when someone has an exit or someone transitions into a new position or does something, like, there’s a true death to the ego, what you kind of are known for or what you think you’re known for or what others assign meaning or value to based on what you’ve done and then who you are in that moment. Like, that exists and that’s a real thing.

And entrepreneurs, primarily entrepreneurs, other professions too, like you’re going to go through that. And that’s a big transitional type of thing. But I think that there are a lot of people that have a hard time actually living the life that they want, and so they build this facade of success versus building an aligned life with the right values, the right people, showing up the right way for their family. And I’m curious like how you see, like, how can you tell the difference between that?

Jesse Flocken: Yeah. I mean, I actually started to go down there and I distracted myself. But I talked about how there’s some entrepreneurs that have come to me in a hard position, and then there’s other entrepreneurs that I know that they have built their life around bringing others with them. And so, some of the most successful folks that I know, they’re the ones that they didn’t get to the mountain alone. They didn’t celebrate alone. They didn’t take the paycheck alone. And it’s not saying there’s anything wrong with that either, but the people that I know that are the happiest and the most successful combined are the ones that built something that brought others with them and didn’t sacrifice family and friends along the way.

And so, I think about this entrepreneurial journey and all of these, even the people who are going from active to passive and things like that, the number one distinction is if you can’t enjoy your life now, you’re going to be miserable later. And most people get, again, heads down on the build and thinking that the build is going to achieve a lot of the goals that they’re looking for. But when you’re standing in line, I mean, we go to Disneyland quite often.

Justin Donald: And by the way, you can give Bob Goff a shoutout. I mean, he is like one of the most amazing human beings I’ve ever met. I’ve heard him speak a number of times. I’ve gotten a chance to hang out with him, and so, like through my own eyes, I’ve witnessed the kind and wonderful human he is. So, feel free to share kind of the impact that he’s had on you and the power even of mentorship because he’s been a huge mentor for you and Courtney.

Jesse Flocken: Yeah. A lot of people, for those of you who don’t know who Bob Goff is, he’s an author. First book was Love Does and Everybody Always. And then he wrote some more business-minded books about one’s called Undistracted. It’s holding up my laptop right now actually. And another one’s called Dream Big. And through that, one of our goals, like I was talking about, of bettering friends around us, marriages around us, those things, he does this thing called The School of Whimsy and brings people to Disneyland. So, we bring like 60 to 80 adults to Disneyland with a few other folks in his world. And it’s just so fun. We do a couple day workshops. We’ve brought people, we’ve invited you guys. But we do that.

And part of that is truly just aligning things. Again, like monetary value doesn’t help us. It doesn’t change anything, but the people that we bring along with us, it truly is a way that we can see like, hey, if this is one thing that you want to be known for, you want to be radically, like, one of the things is I want to be radically available to those around me, good times and bad and that comes with some caveats. And then I had to write down like, all right, well, what sacrifices might I have to make to do that? And one of the sacrifices like, all right, that means when it’s not convenient, I’m still going to be available.

Also, not just that, speaking of Bob Goff quotes, he talks about know who your six is. And most people think of like military terms, like, watch your six, look behind you. And what he means is like, who’s your six of, like the people who are going to carry your casket when you’re not here anymore? He’s like, treat those people differently. Answer the phone when they call. Walk out of a meeting, walk out of other things.

And ever since then, it’s been something, even when Courtney calls or my kids call from school or something else, I’ll make sure that I answer it. And Courtney and I have a rule, I’m sure a lot of people have this rule of like, all right, if you call twice, I know it’s an emergency. And sometimes you’ll call twice and be like, oh, I just forgot. And I’m like, but I would rather answer it anyways, you know?

So, it’s those moments of those things, and Bob’s been a huge influence of that. And actually, as we’re talking about this, not to make the whole thing about Bob, but it is really special when you said something about what you’re known for. Bob has another quote where he says something along the lines of like, strip away the top couple things of what you’re known for, and what’s left is who you are. And so, get really comfortable with that version of you. And that’s probably back to pulling on the string and bringing this a little bit full circle of when you encouraged me to do podcasts and speaking and other things like that and kind of share this message of my own journey, the thing that I kept pulling on was that, like most people in my life don’t even know what I do.

And as a marketing person, that’s like the epic marketing fail in that way. But as a person, people know I’m generous. People know that I care about people. I’m a connector. And so, as other things of where I’m just radically trying to be in people’s corner to pursue something because marketing and marketing systems will help you grow your business. But if you don’t know what you’re doing it for or why, then it doesn’t matter.

Justin Donald: That’s right. Now, talking about relationships, you’ve touched on this a lot. And I think that you’ve got a unique perspective here. And similar for me, I believe that my marriage and a lot of my closest relationships have really shaped the way that I view the world, have shaped the way that I prioritize what I do and who I’m doing things with. But I’m curious for you, like, how has your marriage and your personal relationship shaped the way that you lead and build businesses?

Jesse Flocken: Yeah. No, that’s a great question. And so, just the time of us recording this, we had the Lifestyle Investor Mastermind, big live event.

Justin Donald: Oh, that was awesome.

Jesse Flocken: Yeah, it was awesome.

Justin Donald: From active income to passive income, and even from an estate standpoint, sometimes when you actually want passive income to be active income and to offset it, it was so fun.

Jesse Flocken: Yeah, it was awesome. It was a lot of fun. I mean, if you’re not a part of it, you should for sure look into it. But while Courtney and I were there, a couple of people asked me like, oh, man, which one was better and this and that, and which event from the September to the May event? And I was like, this one for one reason because Courtney’s with me and…

Justin Donald: That’s great.

Jesse Flocken: I mean it from so many different layers. It’s not just because of who she is and our relationship. It also is that the way that I feel empowered to have conversations, even when she would go upstairs to chat with the kids or something else and work out some other things, I still felt more empowered knowing she was around, just as that. And Michael, who I think might be on here soon, actually, he was talking to me and he’s like, man, it just seems like you guys have so much fun. And I was like, thank you for saying that, because there is no doubt.

Justin Donald: King and queen of fun. I mean, that’s you guys.

Jesse Flocken: That we have fun. So, with that, back to how does that impact building businesses. And what I would say is from the very get-go, when we have business partnerships or anything else, I say we’re making an agreement, we’re making some sort of partnership with Courtney and I first. The marketing comes second or other things. We have a lot of leverage there for this engine. But like, what you’re getting with us first is really important because our relational capital, our relational equity, but also what we stand for, we can’t go into this business knowing that we’re going to be tied down and you’re going to be tied down like we are doing this to multiply. Like fun is contagious, but also like strategic growth is even more contagious because then, people see like, okay, we’re just building this system and this business.

One of my friends said that, his name’s Devin, and Devin talks about how he’s like, I don’t care if it’s shoveling poop or shoveling gold. If you show me the numbers that the other one is worth more than the other one, he is like, I will show you how to run a business. If you know how to run a real profitable business, it doesn’t matter the industry. He said, most of my industries, I know nothing about the product. I know how to run a business.

Justin Donald: That’s right. And think about a turnaround specialist, they’re industry agnostic. They can jump into any industry and turn a company around. It’s amazing. I’ve worked with some of these people. It is so incredible. But it is such a system and protocol that it doesn’t matter what you do.

Jesse Flocken: Yeah. Well, and we always talk about like, I was on a sales call today actually, and we always talk about how, like, most people that I talk to, I talk to 20 or 30 people a week and they don’t have a leads problem. They have a systems problem. And the same way, back to this question about marriage and how does that affect what we’re building, it affects that, if we’re not hiring people to better our life outside of this, then like that’s going to negatively impact our family, our marriage, all of those things.

And then, if the team isn’t, like, I would never, ever hire somebody, that my wife wasn’t like, oh, my gosh, I love this person. Or how are they going to help the team? How are they going to help the environment or the culture? Like, if there was someone that I was like, oh, probably rubs me the wrong way, which hasn’t happened to date, because also, I probably interview in a way that, like it has to fit the team environment, our culture, coworkers, I really try to have everybody as actively involved as possible and still do the role.

But it’s really important to build around, it’s almost lifestyle businesses. And again, I say that loosely because some people build lifestyle businesses as solopreneurs and have a high income to produce that lifestyle, versus what we’re talking about is we want a scalable, profitable, exitable business to suit our lifestyle, because that’ll allow us to give back to the company, to our friends, to all those people. So, it does have a big impact.

Justin Donald: That’s awesome. And I do love that you involve Courtney in the decision making because I do the same with Jennifer because I think that often, women are more intuitive than we are. There are certain people that just have intuition and discernment and it just oozes out of their body. And luckily, for us, we have that in our wives, and so it makes us more well-rounded and more complete. So, I mean, Jennifer sees things that I don’t see all the time, and I have just learned I have to trust that discernment because she can pick up on things that I am truly oblivious to. So, I love that you guys do that.

And it’s always fun having spouses together, and part of the reason I love for our mastermind events, like I want both spouses there, I want both people to learn so that the conversations can be enriching and deep and you can actually have transformative life type of conversations and changes and I think these stimulate it, like the event is intellectually stimulating, so it stimulates great conversation that continues on beyond the fact. And it’s hard to regurgitate everything to someone that’s been home after you’ve gone through a three-day event. So, I love that you guys are doing it together.

Jesse Flocken: And our kids aren’t young anymore. I mean, they’re young-ish, but not like babies in diapers and all that stuff. But I do remember telling someone, like, hey, you got, like, the reason why we do the Disneyland trips or the Maui trips, like the Disneyland trip’s not a couple’s thing. But we make it, we invite people and encourage them to bring a spouse because I’m like, you don’t want to be having the time of your life and have these epiphanies. And then, especially if your kids are young, you’d be like, oh, man, well, that’s great. I’m glad you had fun, but you know, hey, honey, I was getting puked on and thrown up on and up three times last night. Like, go have fun. Like, that doesn’t feel good for anybody. Oh, great. So, I do think that it just catapults things to a next level to have shared experiences, but also meaningful conversations. One quick thing I’ll say is that back to the intuition and discernment, things like that, we actually have a rule in our house that if it’s a no for one of us, it’s a no for both of us.

Justin Donald: That’s great.

Jesse Flocken: And I can’t tell you how powerful that’s been in our marriage, in business, in entrepreneurship, in school and sports, and all of the things combined because, number one, like, you and I know, you can be 100% right and 100% dead wrong in how you go about it. And I don’t ever want me to be right and hurt to feel wrong or vice versa because then it just sets up a point where, like, if one person loses, you’re both losing. Like, there’s only one marriage here.

Justin Donald: That’s right. This is good.

Jesse Flocken: So, I think it’s just a good rule of thumb for anybody listening as they’re going into entrepreneurship. I’ll actually share this very short story. I had a client come to us and was looking for next radical purpose in their life. Like, okay, Jesse, I want to do the workshop. I’m going to build this business. We have a lot of incubator businesses that come for startups and home services or lawyers or things like that and really excited. Like, man, here’s the cash flow I can do. Here’s what it’s going to look like, all this stuff. I was like, awesome. I was like, what’d your wife say about it? And she’s like, oh, no, she’s totally not on board. I was like, how do you think you’re going to grow this when half of you is not on board? Because you’re going to get into meetings and other things, like, you’re not even going to be able to think straight if that’s the case.

And so, alignment is really important to me and any clients that we come on. And then also, I tell people who are single in pursuing stuff. I’ll tell them, hey, don’t think about this now, but still, who is on this journey with you? It’s not, just because you don’t have a girlfriend or a boyfriend or a spouse or whatever, doesn’t mean there’s not other people. You have friends on this journey with you. You have family members on this journey with you. And where is the space for them? How hard can you grind until someone else is in the fold? So, I do think that all of this comes back to just alignment and making sure that the thing that you want to be known for somewhat aligns with the direction you’re headed, and it has to be separate from your work because that’s going to fuel the growth in your entrepreneurship.

Justin Donald: I couldn’t agree more. This has been awesome, talking with you. Where can our audience find out more about you, Jesse, and your company?

Jesse Flocken: Yeah. So, can go to ClearlyRelevant.com, and if it’s something where, again, if you’re looking to radically grow your business, then that’s something that we can help you with from branding ads, SEO, website, and then also the funnels. The systems is what helps people grow, so ClearlyRelevant.com.

And then from the purpose standpoint, a lot of entrepreneurs want to do this workshop, anywhere from a 90-minute to a two-day workshop. Had Benny Fisher, a mutual friend of ours, he flew out here and did a workshop and it was awesome to get to see him not too long ago and do that in person.

Justin Donald: Love it. Shoutout to Benny.

Jesse Flocken: Yeah. And because he had an exit, a lot of your folks talk about exits and just looking at that, like what’s next and that excitement. And so, if you’re (a) either looking to go and make the entrepreneurial leap or (b) you have a business that you want to grow, then just book a free call. And I tell people this all the time until my team tells me not to say it anymore, but you don’t have to be a client for us to help you. And so, give me a call. I can connect you with the right people. I’m happy to do a free discovery audit, things like that. If folks want to reach out and have a discovery call, I can even do a free one pager for just mapping out this next season of life or the next season of their business.

Justin Donald: Love it. Well, thank you. That’s super generous. And shoutout to Benny. I know Benny listens to the podcast, so congrats on the exit. I knew it was coming up. I didn’t know that it was complete, so congratulations, buddy. And I like ending every episode with a question for our audience. So, if you’re watching this or if you’re listening to this, what is one step you can take today to move towards financial freedom and really just move towards living a life that you truly desire on your terms? Not by default like most people, but by design.

I challenge you to pick something that Jesse talked about today and implement it immediately and move into being on purpose and on point and intentional. So, thanks so much, Jesse. This has been great, and we’ll catch everyone next week.

Jesse Flocken: Yeah, thank you.

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Justin Donald is a leading financial strategist who helps you find your way through the complexities of financial planning. A pioneer in structuring deals and disciplined investment systems, he now consults and advises entrepreneurs and executives on lifestyle investing.

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