Cary Jack, founder of The Happy Hustle and author of the book by the same name, makes a case most founders never consider: measure success by freedom, not revenue. In his early 20s, Cary and his brother had seven-figure funding deals on the table for a New York tech startup, and Cary was working 100-plus-hour weeks on four or five hours of sleep. They ripped up the paperwork instead. That decision led him to Bangkok, where he rebuilt his life around the 10 alignments of his Soul Mapping System. In this conversation, Cary puts host Eric Berman through the assessment live, explains why digital overload quietly drains entrepreneurs, walks through the ROADMAP framework he uses to sell online, and names the "more disease" he sees in high performers. The result is a practical look at how ambitious business owners can keep growing their income and impact without sacrificing family, health, faith, and fun along the way.
In this episode, you'll discover:
- Why Cary Jack treats freedom as his primary KPI and uses Tony Robbins's definition to judge every opportunity that crosses his desk
- How the 10-area Soul Mapping System scores your life from one to five, and why Eric Berman's honest 29 out of 50 is a useful starting point
- The digital detox rules Cary uses, including screen-free first and last 30 minutes, two hours of airplane mode, and one hour of social media
- How the ROADMAP sales framework moves from rapport to pull, using ethical scarcity and urgency instead of pushy closing tactics
- Why the "more disease" infects high performers and how practicing contentment and gratitude helps entrepreneurs keep what they earn
Episode Summary
Cary Jack opens with a line that sets the tone for the whole conversation: plenty of people compete on their bank accounts, but he competes on freedom, meaning how much creative time and financial freedom he can hold onto in any given week. For Cary, that is the scoreboard that matters. Host Eric Berman calls it out right away as a KPI most entrepreneurs never track, because they are busy watching sales and business metrics instead.
Cary's path to that view started with burnout. In his early 20s, he and his brother built an algorithm that quantified feedback, shopped it to companies including Microsoft and IBM, and lined up seven-figure funding deals around a five-year exit plan. Cary says he was working more than 100 hours a week on four or five hours of sleep, with no fulfillment. Sitting in front of the investor paperwork in their Queens apartment, the brothers decided they could not take the money. Cary explains that the business was chasing money rather than their values, and that his brother wanted work tied to sustainability. Cary moved to Bangkok, where he started writing The Happy Hustle and launched his podcast.
The heart of the episode is the question Cary asks every entrepreneur: are you chasing your own definition of success or someone else's? He frames it with a travel analogy. You can get from LA to New York by jet or by bicycle, and every vehicle carries trade-offs. Going fast is great, Cary says, but 100-hour weeks can cost you family, fitness, faith, and fun. He points to the value of pausing long enough to ask whether you are on the right path, and he has made freedom and peace the filter for every decision.
From there, Cary turns the interview around and puts Eric through the Soul Mapping System live. Its 10 alignments cover selfless service, optimized health, unplugging digitally, loving relationships, mindful spirituality, abundance financially, personal development, passionate hobbies, impactful work, and nature connection. Each is scored from one to five based on the last 30 days. Eric scores himself candidly, including a one on selfless service and a one on digital habits, and lands at 29. Cary's benchmark is 40 or above for someone who is happy hustling. Rather than treating a low score as a failure, Cary recommends choosing the two lowest areas and building a simple daily habit for each, tracked with a checklist magnet his team sends members.
Along the way, Cary shares a practical remedy for several areas. For service, he recommends scheduling generosity on autopilot, such as monthly Kiva microloans to entrepreneurs in developing countries or a local Rotary chapter. For health, he emphasizes environment, sleep, and what you choose not to eat. For finances, he lays out the ROADMAP sales framework. For growth, he follows a 30-30-30 routine of reading, listening, and watching content tied to his current goal, which right now is AI.
The final stretch moves to community and contentment. Cary explains why the Happy Hustle Club serves a specific niche of outdoor-loving male entrepreneurs, caps membership with a one-in, one-out model, and enforces a strict standard for integrity. Eric relates it to keeping Speakeasy chapters small enough for real relationships. Cary closes with the "more disease," the constant craving for more money, status, followers, and toys, and argues that contentment and gratitude are the cure. Both agree that as AI floods business with technology, real human connection and staying in your zone of genius are what will set entrepreneurs apart.
Big Ideas Discussed
Make Freedom the KPI That Guides Every Business Decision
Cary Jack's core argument is that entrepreneurs should track freedom as seriously as they track revenue. He describes competing on how much creative time and financial freedom he can possess each week, and he borrows Tony Robbins's definition of freedom: doing what you want, with who you want, as much as you want, whenever you want. Once he adopted that definition, Cary says every decision became a simple test of whether it brings him more freedom and peace or less.
The reason this matters is that most founders default to someone else's scoreboard. Cary chased ego, status, and money in New York until he realized he was pursuing a version of success that was not his own. His jet-versus-bicycle analogy captures the trade-off. Speed is valuable, but if the vehicle you chose costs you family, fitness, faith, and fun, it may cost more than you are willing to pay. For a business owner, defining your own freedom score turns an abstract value into a filter you can actually apply to deals, hires, and growth plans.
Score Your Whole Life Before You Try to Fix It
The Soul Mapping System gives entrepreneurs a fast, honest snapshot of 10 areas of life, each rated from one to five based only on the last 30 days. Cary insists that the scoring stay real: past volunteer work does not count toward selfless service, and mentoring someone who will probably work for you is not selfless. Eric Berman's live result of 29, below Cary's happy hustling benchmark of 40, shows how quickly the exercise exposes gaps that a busy founder might never name out loud.
What makes the system practical is what happens after the score. Cary recommends picking the two lowest areas and attaching one small daily action to each, then checking it off. He describes a refrigerator magnet his team sends members as a simple habit tracker, and he suggests focusing on one alignment per month to cover all 10 within a year. Cary shares the story of a burnt-out seven-figure business owner who told him the program changed his life within 30 days, which Cary credits to bringing intentionality to each area.
Treat Digital Overload as a Hidden Business Risk
Of all 10 alignments, Cary singles out unplugging digitally as the one most systems overlook, arguing that tech usage largely dictates happiness. Eric admits he scored himself a one. Cary's remedy is deliberately simple: no screens in the first 30 minutes after waking or the last 30 minutes before bed, airplane mode for at least two hours a day, and a one-hour limit on social media using the phone's built-in restrictions.
Cary practices what he describes. He says he usually keeps no social media apps on his phone, logs in from his desktop for about an hour, and lets his team run his accounts. His advice for entrepreneurs is to be more of a producer than a consumer on social media. He also builds the rule into his community: at Happy Hustle masterminds, anyone with a phone near the table owes 50 push-ups on the spot. For founders, the lesson is that attention is a resource, and protecting it is part of running a business well.
Sell With the ROADMAP Framework Instead of Pushing
Cary says sales has been his favorite skill since childhood, and he shares the ROADMAP framework he uses to sell online. It starts with rapport, then identifies the obstacle holding the prospect back and the aspiration they are reaching for, so you can show how your product fills that gap. Demonstration means showcasing client success, testimonials, and social proof. Match means making sure the prospect is the right client, which Cary says protects you from selling to people you will regret serving.
The last two steps are about closing with integrity. Ask means directly asking whether anything else is holding the prospect back, while preparing responses to the three most common objections: time, money, and spouse. Pull replaces pushing with ethical scarcity and urgency, such as a capped number of spots or a bonus for deciding on the call. Without those elements, Cary says, you will keep hearing that someone needs to sleep on it.
Cure the More Disease With Contentment
Cary coined the term "more disease" for a pattern he sees in high performers: a constant craving for more money, status, fame, followers, toys, and cars. His view is that more is not the remedy. Instead, he points to the power of contentment, which he describes as getting crystal clear on what you truly desire and practicing gratitude so you can both get it and keep it. He acknowledges the idea sounds a little woo-woo, but says he wants to give more people permission for less.
Cary grounds the idea in what he has observed working with entrepreneurs. He says he has seen under the hood of thousands of businesses and keeps meeting people who have everything but lack peace, joy, and fulfillment. Eric admits he has been guilty of chasing more simply because he could. Cary adds that grace matters, too: everyone is on their own path, and the useful question is what you do next.
Questions We Answer in This Episode
What is Cary Jack's Soul Mapping System and how does it work?
Cary Jack's Soul Mapping System is a self-assessment that scores 10 areas of life from one to five based on the last 30 days. The areas are selfless service, optimized health, unplugging digitally, loving relationships, mindful spirituality, abundance financially, personal development, passionate hobbies, impactful work, and nature connection. Cary says a total of 40 or above means you are happy hustling, while 39 or below means you have work to do. He recommends starting with your two lowest scores and building one daily habit for each.
Why does Cary Jack measure success by freedom instead of revenue?
Cary Jack measures success by freedom because chasing money and status burned him out in his early 20s. He says he competes on how much creative time and financial freedom he can possess each week, using Tony Robbins's definition of freedom as doing what you want, with who you want, as much as you want, whenever you want. Cary now filters every decision by whether it brings him more freedom and peace or less.
Why did Cary Jack walk away from seven-figure funding deals?
Cary Jack walked away because the startup he built with his brother was misaligned with their values. After 18 months of 100-plus-hour weeks, they had seven-figure funding deals and partnership offers ready, but Cary says he was chasing money rather than something he was passionate about, and his brother wanted to work on sustainability. They ripped up the paperwork, and Cary moved to Bangkok, where he began writing The Happy Hustle.
How can entrepreneurs do a digital detox without quitting technology?
Cary Jack recommends a simple daily routine rather than quitting technology entirely. Avoid screens for the first 30 minutes after waking and the last 30 minutes before bed, turn on airplane mode for at least two hours a day, and limit social media to one hour using your phone's restriction settings. Cary says he keeps social media off his phone, logs in from his desktop, and has his team run his accounts so he can produce more than he consumes.
What is the ROADMAP sales framework Cary Jack uses?
ROADMAP is Cary Jack's seven-step framework for increasing sales conversions. R is rapport, O is the obstacle holding the prospect back, A is their aspiration, D is demonstration through client success and social proof, M is matching to make sure the client is a good fit, A is asking what else is holding them back, and P is pulling them in with ethical scarcity and urgency. Cary also advises preparing rebuttals for the three most common objections: time, money, and spouse.
What does Cary Jack mean by the more disease?
The more disease is Cary Jack's term for the constant craving many high performers have for more money, status, fame, followers, toys, and cars. Cary argues that more is not the cure. He recommends practicing contentment, which he describes as getting crystal clear on what you truly want and cultivating gratitude so you can both achieve it and keep it. He says he has seen many successful entrepreneurs who have everything but still lack peace and fulfillment.
How does Cary Jack recommend giving back as a busy entrepreneur?
Cary Jack recommends scheduling selfless service so it happens automatically. He donates monthly to several organizations, including Kiva, which provides microloans to entrepreneurs in developing countries and lets him relend the money once it is repaid. He also suggests joining a local community program and mentions his membership in the Rotary Club. For the Soul Mapping score, Cary says the giving must not be business related, so mentoring a likely future employee does not count.
Full Episode Transcript
Read the Full Episode Transcript
Freedom as the Ultimate Entrepreneurial KPI
Announcer: Welcome to Inside the Speakeasy podcast, the private room where today's sharpest founders, innovators, and renegade thinkers come to trade the ideas [unclear] industries. This show is brought to you by HighLevel, the AI-driven business operating system trusted by over 2 million businesses to help automate, scale, and create real leverage. HighLevel isn't just a tool. It's the engine behind some of the most agile and high-performing teams on the planet. If you're ready to streamline everything, amplify your reach, and actually build a business that works for you, you're in the right place. Visit www.GoHighLevel.com/Speakeasy-Mastermind-Promo to get an exclusive 30-day trial for being a listener of the Inside the Speakeasy podcast. Enjoy the show.
Cary Jack: There's a lot of people who compete on their bank accounts, and I compete on freedom and how much creative time and financial freedom I can possess in any given week. And that's where I like to win.
Eric Berman: So like many entrepreneurs, you're probably burnt out and you're struggling and you're asking yourself, there's got to be a better way. Well, I have some good news for you. There is a better way. It's the Happy Hustle way. And I'm so stoked to bring on Cary Jack. He's got a top 1% podcast, USA bestselling book, and he's got an incredible system called the Soul Mapping System. And on this podcast, he's going to walk me through the Soul Mapping System, 10 different areas where I need to be ranking myself to get better. I want you to follow along the Soul Mapping System. We're all going to do an assessment together and we're going to learn some amazing things about how to get our happy hustle on. Welcome, Cary Jack.
Cary Jack: Thank you, brother. Honor to be here. Appreciate you, man.
Eric Berman: Yeah, no, I mean, you and I have had some great convos and a lot in common. In fact, you just actually had me fall off my chair a second ago saying like, your goal is to get the 20-hour week. Tell me what you just said there. That was like, whoa.
Cary Jack: Oh no. I was like, there's a lot of people who compete on like their bank accounts and I compete on freedom and how creative, how much creative time and financial freedom I can possess in any given week. And that's where I like to win.
Eric Berman: I love that. Okay. So that's a good KPI for yourself. Are you getting it each week?
Cary Jack: Yeah.
Eric Berman: I don't think most of us think in those terms. We're thinking in like the scoreboard of our sales and our business metrics, but not about... I love that. [unclear] So you were burnt out. Let's just take a step back. I want the audience to understand your career background, how you got here today. I mean, you're running with lots of entrepreneurs. You're in front of a ton of people and you're seeing the burnout. It's real. Great, great solves for that.
Burnout and Walking Away From Seven-Figure Funding Deals
Cary Jack: Yeah. I mean, well, first and foremost, I burnt out myself. So I was basically a victim to the grind culture and I was chasing ego and status and power and money and all the things that society deems important, quote unquote. I had this tech startup in New York City, grinding like a damn dog. Never had a real job. Always been an entrepreneur, kind of eat-what-I-kill kind of vibe. Just very much not going to take a corporate gig ever and never will.
Eric Berman: Oh, scary.
Cary Jack: Yeah. I had this algorithm that I built with my brother that quantified feedback, and it had a lot of legs. And so we had shopped it around with Microsoft and IBM and a bunch of seven-figure funding deals for this grandiose five-year exit trajectory back in New York City in my early 20s. And you know what happened was I was just grinding like a damn dog and working 100-plus-hour weeks, getting four or five hours of sleep a night, just on this hamster wheel and [unclear] but no fulfillment. You know, like just freaking smoked. And I ended up sitting in front of a stack of papers from a ton of investor capital and all these clauses and all these deals, and all this was looking me in my face, but I couldn't take the money. I couldn't take the deals. We said no to all the partnership deals. My brother and I, with tears in our eyes, were just ripping up this paperwork at our dump of an apartment in Queens, New York. We were sharing a king-sized bed and he snores like a train. But, you know, we were just the fake-it-till-you-make-it kind of thing. But we had all of it in the palm of our hands after working so hard 18 months straight. But dude, I just couldn't fucking do it. I was like, I can't take this money. I can't take this opportunity. These are investors ready to put money in [unclear] with tons of it.
Eric Berman: Yeah.
Cary Jack: Yeah. And all these, like, we had just so much. The idea still has merit today, but it really just wasn't something I was super passionate about. It was more chasing, like I said, money. And that wasn't [unclear]. So I ended up folding up, ripping up the paperwork, moving to Bangkok, Thailand, actually figuring out over there a better way to work and live in alignment. I say I put the happy in my hustle. For about a year I was over there and I started writing The Happy Hustle, the book, and created the podcast, and just kind of this whole movement blossomed. And yeah, as they say, the rest is history. Fast forward, we have our mastermind community. I know you do too. We were just riffing on that: our club, our annual program. And now we have this [unclear] happiness program, which is SaaS that we're building out. And yeah, a lot of cool stuff happened, but it all started with that decision to say no.
Eric Berman: I'm going to go back there in a second. I don't want to get into some of the cool things you're doing yet, because I'm going to have a hard time thinking, okay, you work your ass off, finally get to this point that you've been saying, well, we got to get, we're working hard to get to this point. You get to this point and you say, we don't want it. So like, how does that even happen? Shouldn't it be the opposite? Like, how did you flip it? And how did your brother feel about that?
Cary Jack: Well, my brother, he was aligned as well, because he's a very big environmentalist and he wanted something to do with saving the planet. And this business was not that. And so it just was misaligned for our values. You know, fast forward, he now is like a Harvard-certified sustainability strategist who speaks at the United Nations. He's like the Elon Musk of the sustainability world. Mark my words, he will change the planet and its trajectory. He's brokering nine-, ten-figure deals every week with Fortune 100s to help them go green. So he's living his purpose and I feel like I am mine. So it was one of those things where God just was like, this is what that path looks like, and here's potentially another alternative route. So I think it was more of a divine thing that kind of steered us away.
Redefining Success and Choosing the Right Vehicle
Eric Berman: So you guys are sitting there and you're grinding, you get these offers. And you guys have these probably very, very emotional, difficult conversations of like, okay, we just grinded for 18 months, got to this point. And you look at each other saying, do we actually even want this? Now that we got here, do we want it? I assume that at that point, you're thinking, okay, if we take this, it's almost like if you open this, you're going to have to then go do more grinding. Is that kind of a conversation?
Cary Jack: Yeah, precisely, man. And that's the thing, just to your point. I don't think enough entrepreneurs pause. The power of a pause really can be monumental. You have to realize too, what version of success are you chasing? And is it your definition or someone else's? Like, I was chasing someone else's version, not mine, right? So now, like I said, freedom is at the forefront of every decision that I make. Does this bring me more freedom or less, right? Freedom and peace. That's truly... I just love peace. Peace, you know, is prosperity, in my opinion. And so when I now redefine my version, that wasn't it. And now, this is it.
Eric Berman: You said something interesting though, and I love that. You're looking at freedom, and that's a big KPI that I think is a huge takeaway, if nothing else already. It's just for people to think about the freedom scoreboard, if you will, the freedom score. How do you define that for yourself?
Cary Jack: I think Tony Robbins, you know Tony, he has the best definition, I think, which is doing what you want, with who you want, as much as you want, whenever you want. Basically, that is true freedom. And so that's what I adopted.
Eric Berman: Love it. Love it. So you're now able to choose projects. And I think there's another lesson in there. I look back at that entrepreneurial mindset: you're running 100 miles per minute on that path. And the ego, like you said, gets in the way and says, well, I'm just going to win because I'm on this path. And I know I can score and I know I can do it. I can do it. And you're like, holy shit, I've been on the wrong path the whole time. What am I doing here? Do I really want this? And you had the fortitude to stop.
Cary Jack: Yeah. I mean, I always kind of equate it to, and it's a silly analogy, but it's like going on a trip, right? You want to get from LA to New York, and you've probably heard this, but you could choose what vehicle. You take a jet, you're going to be there in a fraction of the time. You take a bicycle, you're going to be there, and it's going to take a lot longer. You could take any form of transportation in between, right? But each vehicle comes with pros and cons, right? I just ask all of my friends and my fellow entrepreneurs out there, what vehicle are you actually in? And is it the one that's serving you the best? Because going fast is great, but it might cost you more than you're willing to pay. Because that's where the 100-hour weeks, that's going fast, that's grinding. But what does it cost you? Pretty much everything: family, fitness, faith, fun, all the F's, right? So is that the right vehicle for you? It all depends on your goals. And so that's where it's coming back to what does success actually mean for you.
From Montana Ranches to Living Around the World
Eric Berman: Love it. Love it. Okay. And I want to jump into some of the cool things you're doing, but I got one more question on the past. I thought it was interesting. So Cary lives out in Bozeman, beautiful mountains, and we were just talking about the four seasons. And then you were heading over to New York for a while. Dude, how's that transition? Like, are you like, I got to get back home? Like, that's the opposite.
Cary Jack: Oh, it was like, what the heck am I doing here, every day. I look at the rats on the subway and the people, a lot of them act like rats. And I'm like, what the fuck am I doing here? [unclear] Growing up on a ranch in Montana half the year, in the mountains of Montana, where I would hunt and hike and cowboy. And then my mom lived in Sarasota, Florida, so I was at the beach, surf, skate, and sports, right? I felt balanced in terms of these geographic locations. Plenty of drama between my parents and an interesting upbringing. Nonetheless, everyone has their story and their shit. Mine's no different. But I will say, traveling all over the world, like I lived in Bangkok, I lived in Barcelona for a year, I lived in Rio in Brazil for a year, roughly, in South America, traveling all around there. Lived in LA, New York, Chicago, Miami, all the places pretty much. Montana is the shit. Hands down my favorite place ever, even still, growing up here. It's not like I'm just some podunk redneck, which sometimes people mistake me for. But the truth is I choose to be here because it is the best. And I don't want everyone to up and move here. After Yellowstone, that show, now everyone is migrating. But the winters are cold and there's lots of grizzly bears. That's where I'll leave it. So don't come. You gotta interview.
Eric Berman: You can come.
Cary Jack: Yeah, no, we gotta interview first before they can get into Bozeman now.
Eric Berman: There's a gatekeeper. I like it. The secret's out. Yeah, nuts. So New York was definitely a negative on the list. What was your favorite international spot that you were hanging out in for a while? Was it Bangkok?
Cary Jack: [unclear] Spain was cool. I really liked Argentina and Buenos Aires. Bali is an interesting spot if you're into that kind of beach vibe. It's like Australia's Cozumel. All the Australians and New Zealanders run amok there. So it's a little bit not my favorite, a touristy kind of spot. But Thailand's awesome. Land of smiles, they call it. It really puts a lot of respect in you when you travel. I just highly recommend everyone travel, because you learn so much about yourself, culture, people, language. It's just the best form of education, in my opinion.
The Happy Hustle Movement: Harmonizing Ambition and Well-Being
Eric Berman: Okay, that's a good segue. So I'm going to take us back to Thailand. You started this whole movement, the Happy Hustle, and you're doing amazing things in there. And you're teaching some great stuff. You got members, you got different memberships, you got different programs. Talk to me a little bit about the Happy Hustle movement, what you're teaching. And I want everybody here listening to get some of the key takeaways that you're teaching to your community.
Cary Jack: Yeah. So our whole premise is, how do you systematically harmonize ambition and well-being? Right. So ambition, meaning crushing it, yes, as an entrepreneur, increasing your income and your impact, because we only serve entrepreneurs. Technically, our content lands with pretty much anybody, but that's who we serve at our highest level. And well-being is like, how do you also be an awesome husband, amazing father, and [connected to] God, and a community servant, and a holistically happy human, right? That's what real success means to me, in my opinion: having personal and professional life harmony, right? Crushing it in each area. And I know a ton of people, you and I are both friends with, unemployable, and we know a bunch of wealthy people who have lots of money but lack in fulfillment, lack in joy. They're struggling with mental health. I mean, it's a real factor. And so after sitting in the room [unclear], I wanted to almost change the paradigm. Like, what does true success and freedom look like? What can it look like? And what's the system to get you there? So that's where I kind of sat down and just scratched my own itch of, what are the key areas of life I really want to focus on? And that's where the 10 alignments of being a happy hustler came to be. And that's our whole Soul Mapping System. Happy to elaborate if you'd like.
Eric Berman: Yeah, no, I'd love to. I want to get some takeaways. I love the name, by the way, Soul Mapping System.
Cary Jack: Yeah, yeah. All our stuff is slang and not PC. I say a ton of dick jokes and cuss words, so I'm sorry in advance if that offends. You can handle it. It's all right. I only serve guys in our mastermind, so it's all just like high-performing, nature-loving, badass dudes who, you know, a lot of them were ex-athletes or military. So they get the banter. Right. Yeah. So the Soul Mapping System. Eric, if you're feeling froggy, I'm going to put you on the spot and I'll just put you through the assessment live. It'll take two minutes. If you're feeling brave, I'll put you on the spot and then everyone else can play along with us. I know he didn't expect this. I'm going to reverse interview.
Eric Berman: I can cheat. I got editors, but hopefully we won't use those. We'll just go with it.
Live Soul Mapping: Selfless Service, Health, and Digital Detox
Cary Jack: Okay. So I'm going to ask you a series of 10 questions, essentially, and you're going to write down a score for each of these 10 different areas of life. Okay. So if you're listening, I highly recommend being an active participant, not a passive listener. You'll get way more juice out of this squeeze if you actually play along. And again, keep it real. Give yourself an honest score. So the Soul Mapping System, as we say, it's your soul's map to the blissfully balanced promised land, right? And I know balance gets a bad rap, but I truly believe balance equals happiness. That is something I'll go to the grave with and put on my tombstone. And if I didn't get cremated... I'd rather just end up in the mountains. Soul Mapping starts with S, selfless service. Give yourself a score in the last 30 days. I don't want you to say, oh, I [volunteered] in high school, that was great. I'm happy for you. But last 30 days, we want a real look at it like this: gifts given, insight, finances, and time. Did you actually give to causes and people that you believe in? And no, it cannot be anything business related. So, oh, I'm mentoring this kid who probably is going to work for me. That's not selfless. You know what I mean? We're talking real selfless service. So, self-score, one to five, okay?
Eric Berman: It's like giving to charities and all that kind of stuff.
Cary Jack: Yeah, basically stuff like that, and your time as well. Do you want to share your score at the end or do you want to reveal it as we go?
Eric Berman: You tell me what's better.
Cary Jack: I'll go. Let us know where you're at.
Eric Berman: One. Okay. All right. I was honest. The last 30 days, I've been pretty buried in the event and all the other things.
Cary Jack: Yeah, I get it. So far, you're crushing it, just to be clear. One is like an F, you're failing, and then subsequently two, three, four, you know.
Eric Berman: I wasn't much. I'm embarrassed to admit it, but it's the honest answer right now. I have not been good with service lately.
Cary Jack: Dude. And I appreciate the bravery. And that's the thing. In order to grow, you need to know. Like, what you measure, you can manage. All those adages are cliche for a reason, right? So now we'll move on to optimized health, right? Optimized health. Do you have the body, the mind, the emotional energy that you desire? Like, are you feeling optimized, or maybe you've been shoving crap down the pie hole and not moving that ass, you know? So where are you at?
Eric Berman: Three.
Cary Jack: One to five. Five is an A, crushing it. One is an F, like you're failing. Where are you at in optimized health?
Eric Berman: Yeah, three.
Cary Jack: Okay. Three. U, you unplugged digitally. This is one that a lot of systems overlook. And especially now in the modern-day world, you got to measure where you're at in your tech usage, because it largely dictates your happiness.
Eric Berman: One.
Cary Jack: One. Okay. All right. Yeah. I always ask, do you have a system or barrier set up, like detox time, or are you just...
Eric Berman: I'm seeing those articles out about these digital detox restaurants now.
Cary Jack: That's so cool. I didn't even know that.
Eric Berman: It's going to become a movement. Yeah. They're saying you got to check your cell phone at the door, and they're getting great [unclear].
Cary Jack: Yeah, I mean, that's a small bit of what you're talking about. If it's just, yeah, like, go with your loved one. I mean, come on already. Well, so at our masterminds, if they bring their phone, or anyone has their phone near the table, they have 50 push-ups right there on the spot they got to do.
Eric Berman: Love it.
Cary Jack: Yeah, we have a penalty.
Eric Berman: Love it.
Cary Jack: Like, yeah. So again, easy stuff. In the book I have remedies for each of these. This is something where it's not like, oh, now you just got a shitty score, sorry. For example, digital detoxing: just the first 30 and the last 30. First 30 minutes in the morning, last 30 minutes before bed, just no screens. Just let that be sacred time with God, your family, a book, whatever. And then airplane mode, putting that on for a minimum two hours a day, and then limiting social media to one hour. You can put a setting on your phone where it just turns off your access to social media. I actually went as far... I don't even have social media. Actually, now I will just be 100% transparent: I'm buying something off of Facebook Marketplace, so I had to download it on my phone, a nice big grill guard for my truck. But the point is I usually don't even have social media on my phone. I just log on to my desktop for an hour. My team runs all my socials.
Eric Berman: Those are some great tips. Thank you for that.
Cary Jack: Yeah. One hour a day. Just be more of a producer than a consumer on social, and you'll be so much [happier] and make a lot more money.
Eric Berman: Let's keep that rhythm going if you don't mind, because I think these are great takeaways, and we'll come back to the S and the O. What's your quick tip on the S and then the O?
Cary Jack: So for selfless service I always just say schedule. So I like a company called Kiva, K-I-V-A, which is an organization that gives essentially microloans to environmental entrepreneurs in third-world countries. And so I've been donating every month. I give a ton of money just on autopilot to a bunch of different organizations, but that's one I really like because it empowers entrepreneurship in these third-world countries. And then they give the money back and then I just give it to other people. So every month I'm giving microloans.
Eric Berman: I've heard of that program. I'm starting to hear about that. Cool.
Cary Jack: Yeah. And then get into a program in your local community. Like, I'm part of the Rotary Club. That's a massive organization, one of the biggest in the world. They're doing a lot of good in local communities. There's like 50,000 different chapters or something. For the O, I talk about ENERGY, which is environment, nutrition, exercise, rest, [unclear], youth. So the six key pillars of any real health. The biggest thing that oftentimes gets overlooked is your environment, right? It's like you're sitting there, soaking up toxic blue light, breathing in recycled air, getting beamed by electromagnetic fields, constantly on your devices. You wonder why you feel like donkey dick. It's because you're freaking not meant to live like this. You got to get outside, you know? But the point is, you got to just be conscious of your environment. Obviously exercise, nutrition, all that stuff. And it's more important what you don't do and what you don't eat than what you do. Like, if you don't stay up till one o'clock and you get good sleep, you're going to feel better. If you don't eat that extra Ho Ho or Twinkie, or even one to start with. Again, little simple stuff. So those are a couple of tips for those.
Loving Relationships, Spirituality, and the ROADMAP Sales System
Cary Jack: And now we're on U, unplugged digitally, and we got your score there. So now we're moving on to loving relationships. So everyone should have three scores. Now write down a score for loving relationships. And this is your inner circle, like your spouse, your best friends, family members.
Eric Berman: I'm giving myself a five on that one. I get a five.
Cary Jack: Yeah, your kids. Yeah, so it's like, how much love do you actually have in your life right now? How much plentiful pleasure? How much peace, call it? Just give yourself a score. And then obviously, you could have the opposite: angst, despair, lots of adversity. So just be honest in love and relationships. That's an awesome score for you. So now we're moving on to mindful spirituality. And I don't care about one religion or another. I'm not religious. I'm spiritual, personally. You know, my dad was Catholic. My mom was Jewish. I'd go to a Christian church; I loved the music. But I then did a ton of Tai Chi and Kung Fu growing up and learned from a Taoist priest this whole martial arts way of life. So now I'm big in the Eastern. I've always been. So it's just like, I believe you have to have faith in a higher power, something bigger than yourself. You know what I mean? That's my take. And so I would just ask, how connected do you feel to God, or to the divine, or whatever you want to call it, source? Just give yourself a score, one to five, in this one.
Eric Berman: I'd say probably a two.
Cary Jack: Two. Okay. This is just a couple of, as we call them, Happy Hustle hacks. We talk about SITS. I do acronyms inside of all of our acronyms, which is, again, super meta. And this was before ChatGPT would spit out a ton of these. I spent freaking weeks in a cabin in the middle of nowhere creating these damn acronyms. And sometimes I laugh because I'm like, gosh, it would have been so much easier. But SITS: sit your ass down and just chill in the still. That's my reminder to breathe, meditate, and just pray. I pray around every meal. It's a trigger for me just to give thanks and gratitude, and I pray every night with my family. So again, prayer doesn't have to be religious. It can be just a connection, a time to listen and pause and ponder.
Eric Berman: Love it.
Cary Jack: Okay. Now moving on to abundance financially. Lots of people think this is the most important alignment, but actually they're all equally important. So give yourself a score, one to five. Five is like, you know, you're crushing it. You got a whole system to save, spend, and invest wisely. One is you're living paycheck to paycheck, failing right now, really struggling. So where are you at?
Eric Berman: Three.
Cary Jack: Three. And here's the thing. High performers are always hard on themselves. So it's all relative for each person, but it is important to just give yourself an honest take on your numbers and where you want to be. Like, you might have massive goals, and that's what it is right now, your true state. It's just important to know in order to then pivot accordingly. So for this one, I talk about the ROADMAP system for increasing your sales conversions. I love sales. Sales has been my favorite skill to hone ever since I was a boy. I was called Coercion Cary, for better or worse. But ROADMAP, I'll hit you real quick, but this is how I've sold millions of dollars online, typically in my underwear. And it's very simply ROADMAP. R, rapport. So you got to build rapport first and foremost, kind of like a talk track for your next sales conversation. O, obstacle. So you got to know where they're at and what's the obstacle holding them back. A is the aspiration. Where do they want to go? What's the goal? And can your product or service fill that chasm? Then D is demonstration. You actually have to showcase future success and talk about client success and testimonials and leverage social proof. A lot of people miss that. M is match. You got to match and make sure it's the right client. How many people do you know that have sold the wrong people and then just hate their lives and are miserable fulfilling their services?
Eric Berman: Chase the money.
Cary Jack: Yeah. You and I have both done that, I'm sure. And it sucks when you've sold the wrong people. So match: make sure it's a good fit. A is ask. You got to ask the damn question: hey, is there anything else holding you back from taking action on this opportunity today? And they'll tell you, right? And be prepared ahead of time with your key three objection busters. What are the three things you hear most commonly? Time, money, spouse, right? You need to know what your rebuttal is going to be to those things, right? And then the final is P, pull. I don't like to push. I never push, but I pull, right? I pull them into the opportunity with ethical scarcity and urgency, right? So you have to have that in your offer, or else you're going to get the, you know what, I need to sleep on it. And that is what you hear if you don't have good scarcity and urgency. Scarcity would be, hey, you know, we only have 15 spots and 13 are sold, so this is your chance now to take action. We're not going to hold spots, so you're going to miss out. And then urgency would be, oh, you know what, you could get a $1,000 bonus if you do take action on the call today, or some type of extra thing, a discount, whatnot. But that's the ROADMAP system to increase abundance financially, if you need a little pro tip.
Eric Berman: Love it. That was a bonus tip. I love that.
Personal Development, Passionate Hobbies, Impactful Work, and Nature
Cary Jack: All right. Now we're going into the P, right?
Eric Berman: Everything you hear on this show comes back to one idea: proximity. I wrote the book on it, literally. Proximity Pays, my bestselling book, available now at proximitypays.com.
Cary Jack: Yeah, the P. So the first P is personal development. I'm sure a lot of your listeners and viewers are high on this one. But again, you're either growing and evolving or you're shrinking and dissolving. That is the choice, right? So in personal development, just give yourself a score, one to five.
Eric Berman: Yeah, four.
Cary Jack: Love it. Yeah, my little Happy Hustle hack here is the 30-30-30 system for guaranteed growth: 30 minutes of reading in the morning, 30 minutes of listening in the afternoon, 30 minutes of watching in the evening. It hits the brain centers differently, but it's all inspirational, educational content. That's why I like to hit it on those three different mediums. And when I do this, I just make it related to my goal. It's not like random knowledge. It's like, what is my goal right now? Like, I'm learning a ton about AI and all the different use cases, so my 30-30-30 is largely dedicated to that. So that's the little pro tip there. Next is passionate hobbies, which I find a ton of people lacking. We're always giving to our freaking families and our friends and our colleagues and our team and our clients and everyone but ourselves. And we feel freaking guilty having fun and doing shit that we enjoy. So where are you at in passionate hobbies?
Eric Berman: Fuck. I mean, I said that's going down. That's going backwards.
Cary Jack: Okay. Make sure you're writing these down, because we're going to total at the end.
Eric Berman: Okay. All right. So two.
Cary Jack: So my whole thing here is, we have these four factors of fun. When you're picking a hobby, you want to make sure, one, that it involves people that you want to be around, right? Two, that it's potentially a life-beneficial skill. Three is that you're going to have fun. And four is that you're actually going to grow, right? Doing things that check all those boxes, like learning salsa dancing. You're doing it with somebody you care about, hopefully, right? You're going to be around people who are lively and fun. You're going to grow. Dancing's actually really good for longevity too. It connects the right and left lobes of the brain. So anyway, there's a lot of stuff like that where we put our guys through it to make sure they pick the right hobby, not just something. But spending time guilt-free is the key: do fun shit. I love fly fishing. I love horseback riding, playing soccer, going and doing my martial arts and kickboxing and whatnot out here now, and Krav Maga. And then I'll go dancing with my wife when I can. Now I've got a baby, so it's been a little different schedule. I've got a two-month-old daughter, so all that's been put on the back burner largely, but now I just take them with me. Okay. Bringing it home with impactful work and then nature connection. So impactful work, give yourself a score here. And that is, again, do you feel [unclear], right? And then purpose, which is that inward calling on your heartstrings, right? And then purpose, which is that outward serving mission, like actually helping people you want to help, [unclear]. Little Hello Kitty cats that are just putting more plastic in the planet. No offense if that's your business, but fuck, it's not for me. Is it impactful, actual work? Ask yourself that and give yourself a score of one to five. Where are you at?
Eric Berman: We're going five on this one.
Cary Jack: Let's go, big daddy. Come on. Yeah. All right. So now we've got the last one, which is nature connection. And this one is, how often do you actually get outside in nature, unplugged, just really soaking up this beautiful planet, Mother Earth, right? And then I loop in being a conscious consumer and actually practicing sustainable things as a part of your ethos. Not buying plastic water bottles from freaking Walmart, and not just being excessive with our supply chains. We don't need that plastic wrapping on our books. You don't need to ship them in plastic. They'll be okay in a box. Right. So it's making choices like that, that just focus on the triple bottom line: people, planet, and profits. It's not my term. This is a big term in sustainability. But if you can hit all three, then you're really connected and using business for good.
Scoring the Assessment and the Happy Hustle Club
Cary Jack: [unclear] Add it up. Everybody add it up. And this is, again, a score that is just going to be telling, to say where you're at right now in terms of happy hustling your dream reality and where you potentially have some room to grow. So where'd you land? 40 and above is you're happy hustling. 39 and below means you've got some work to do. So what's your score?
Eric Berman: I got work to do, my friend. I thought you were going to go like 30 to 40. I'm like, oh, geez, I didn't even make that range. I'm 29.
Cary Jack: Okay. Hey, man, look, now it's in order to grow. So what I say typically is, just pick your lowest two that you want to work on, and then you just create a habit. With our stuff, we actually have a Blissful Balancer. You should have gotten one in the mail. Did you get mail from me yet or no?
Eric Berman: I think so.
Cary Jack: I'll send it to you. Okay. I'll need to confirm your shipping address with my team. So we have these magnets that go on your refrigerator, and you just write out an action step for each of these different alignments. And then every day, you just check it off if you did what you said you're going to do. Like, hey, I'm just going to give 15 minutes to somebody who needs it without any type of law of reciprocity top of mind, right? That could be for selfless service, right? Nature connection: I'm going to go outside for 20 minutes and just sunbathe and ground to the earth. Just sit there. You just check it off. I mean, it's an action. It's a habit tracker. It's super simple. If you focused on one a month, you'd hit all 10 within a year, and you can be really happy hustling. We get guys turned around in literally 30 days. I just had a guy who signed up for our program, completely burnt out, running a nice seven-figure business, but stressed to the gills. And in 30 days, he's like, this changed my entire life. [unclear] worth the investment, my whole relationship with everyone that I come in contact with. His words, not mine, but he's like, this was the best decision I've ever made. And it's simply because you're just putting intentionality into your actions in these areas. You know, it's a system that supports every component of entrepreneurship, and life at that. But especially for entrepreneurs, it works.
Eric Berman: Love it. So speaking of that segue, this is amazing. So thanks for this. Very eye-opening. I love it. You've got an acronym and solutions for everything. Tell listeners a little bit about the Happy Hustle stack, if you like. Like, how do they get into your tribe? What are the different programs you offer?
Cary Jack: Yeah, thank you, man. Well, a little caveat: if guys or girls want to go deeper, at thehappyhustle.com we have the book for free on the website. We have the assessment if they want to take it, the online version. It's all there. If you want the hard copy of the book, you got to pay for it, but you can download the ebook for free. And that just goes deeper. So just to tie a bow on that, if anyone does want more resources, it's all there. The club, our Happy Hustle Club, is exclusively for high-performing male, badass, nature-loving, outdoor entrepreneurs who want to mix business with pleasure and go on epic adventures. [unclear] community.
Eric Berman: And I just want to clarify something. He loves men and women equally, so I don't want anybody listening to [take it the wrong way]. There's also a learning there, because we've talked about this in the office: it's about finding your niche. And the lesson there is the niche that he happens to be working with is that niche. Doesn't mean he doesn't like the other niches at all. That's just where he's working, and he's having more [traction] because he's focusing on that niche.
Cary Jack: 100%, yes. I am not sexist, I promise. I love the women in my life. I have a daughter, a wife, sister, mother; very much an advocate. I have a lot of women friends who are entrepreneurs that I pull back the curtain for, show them what we're doing, and send all the women that apply their way. But it's just for our stuff. Personally, I know men need a sacred place where they can really take the armor off and connect on a raw, primal level. And on the campfire, talking about the real shit, everyone signs NDAs to come on our stuff. It's like the Vegas rule out in the wilderness, you know? So it really is one of those things where we just created a space to keep it 100% honest. So that's why we made that choice. But yes, it is important to really nail your avatar. And I believe, talking marketing, I'd rather be the magnet than the megaphone, right? So I'm constantly magnetizing my perfect people with our copy, with our ads, with our social proof, with our testimonials, with our content, rather than attempting to, hey, buy my shit, look at me. Like, I can help everyone. I'm like, uh-uh, we can't help everyone. It's not for everyone. And we tell you, we have a strict no-douchebag policy. If I get a whiff of douche, you're fucking out. We just don't tolerate it. It's in our bylaws. Even if you paid, you get no refund. We kick you out of the club. You've got to embody the ethos: reciprocal respect, [unclear], and inspirational integrity. Like, one of the guys tried to fool around on his wife at one of our masterminds. We're like, well, that's not integrity. You're out, man. Not the right event for you. Not the right club. Not the right thing. If you want to go do that, that's fine, that's your choice, but [unclear] is not who we are. We keep our standard as high as possible in that capacity. So I think that's really been the secret sauce for us: just vetting extensively. We have the four quarters paradigm ethos, which is, would you rather have four quarters or 100 pennies? I'd rather have four ride-or-dies who I know, if I need them, they pick up my call, rather than being in a [group] with hundreds and thousands of people where no one knows each other and it's surface contact. We cap our club. It's a one-in, one-out model. And anyway, I say all that to say, yes, the club has three different tiers. We have a $100K program and a $30K program, at the time of this recording. And then our one-off masterminds are $9,500. So it is a little bit higher-tier price point, but it always comes with a happiness guarantee: personal or professional ROI, or your money back. And we've never had to give money back. So [unclear]. Yeah, it's working. We're getting, like I told you, 11.2 ROAS on Meta ads right now. And now we've got a new problem: keeping up with demand.
Eric Berman: So, yeah, I mean, it's similar. The last thing you said, even within Speakeasy, that's why I don't make my city chapters [huge]. I'm not trying to get, you know, hey, let's be EO. I love EO, but like in Vistage, let's get hundreds of people in the city. I'm like, well, you can't really build relationships with that many. So let's cap it at a certain number so we can get to know each other and have that pick-up-the-phone, call-people-locally kind of thing. So yeah, I agree with that philosophy. It's dead on there. Well, very cool. I got tons of ideas and tips, and I can't wait to get the magnet and do some things. What did I not ask you today that maybe we didn't cover?
Curing the More Disease With the Power of Contentment
Cary Jack: One thing that I like to share, specifically with high performers who are probably listening to this show, is this concept that I coined, the more disease. And I really think it's infected a lot of people, specifically high performers, now more than ever. We're constantly craving. It's like a freaking disease. More money, more status, more fame, more power, more people, more likes, more follows, more toys, more cars, all of it. All more, right? And in my opinion, more is not the remedy. Exercising the power of contentment is the cure to this infection. And the power of contentment means getting crystal clarity on truly what it is that you desire, and then practicing an attitude of gratitude in order to not only get it, but keep it, right? So constantly waking up in that grateful state and just vibrating at that frequency, realizing that you attract your reality, right? And everything in it. And I know it's a little woo-woo, but I want to give more people permission for less. You know what I mean? It's a little counterintuitive, but man, I tell you, I've seen under the hood of thousands of businesses. All my circle is entrepreneurs. We know a ton of the same people. And I see people with all the things lacking so much of the peace and joy and fulfillment. And so that just isn't success to me. And so I just want to share that concept of the more disease and how [unclear].
Eric Berman: I'm glad you did. I think that's so profound. And I think for people who listen, Cary's got the opportunity, I mean, you hear about some of the entrepreneurs he's dealing with. He's got this special set of lenses. He's probably talking to all these people and seeing this commonality of unhappiness, and where people are, and it's just like they're chasing the more disease. And I mean, I'm guilty of that. I look back and say, me too. This is the ego pushing. And we are high performers, so we think we can achieve more and let's just get that. And you're doing shit over here like, why am I even doing this? Well, because I can, and I think I can win. And you're just like, what the hell are you doing? Just get back, stay focused, be happy with the stuff you're doing, and go deeper there. I mean, one of the biggest regrets I have is that, something I really regret, being on a certain path [that wasn't] the right path for me. And you had the courage and the knowledge to hit that eject button at the right time. Otherwise, you'd still be hanging with the rats in New York, potentially chasing something, like, what the hell am I doing here?
Cary Jack: At some point you've got to give yourself grace. We all are on our own path and our own journey. It's just, now, what are we going to do moving forward into the future? For me, especially as a young father, it's like, man, being a father gives you that level of peak human bliss, hearing Dada. So why do we give so much of our energy away to followers online that we've never met, or so much attention to haters who aren't even perfect for our product anyway? It's like, fuck them. Just focus on the people you love and being present as much as possible. And I just want to say this, man: I don't claim to be the guru of shit. I really don't. I am legit just a reporter. Here's some things that are working for me. Take what works, leave what doesn't. That's my stance. I don't want to be [an] online guru BS. I think there's a ton of foo-roos, fake gurus, out there. I just want to be authentically me. And so why not just take some of the homies with me and get paid to do it? Like, I'd go camping anyway. Don't tell these guys.
Community, Zone of Genius, and the Craving for Human Connection
Eric Berman: Isn't it weird? Because you and I are aligned on building community. It's just like, what seems so fun and natural to us, the average entrepreneur doesn't [see]. Just getting organized people together has such value for people. But you're like, I've been doing this my whole life. I'm always the guy that brings people together. Like, yeah, high school parties. [unclear] You look back in life and you're like, you're the wrangler of all your buddies. And you're like, holy shit, how good is this? I'm getting paid. And this goes back to the thing we talked about. You're doing what you love to do, that you're naturally good at, and you enjoy it. But sometimes you don't think that this is actually a special skill, because you're so good at it and you figured it out.
Cary Jack: Yeah. Well, and that's just to your point, man: staying in your unique zone of genius. I think that's one of the most important skills as an entrepreneur nowadays, because we can get so sidetracked with all the other tasks. Now, with AI and the inundation of technology, we even more need to lean into our God-given human gifts, right? Because that's what's going to separate you as a business owner nowadays: how real can you be? You know, I think, and we talked about this, the more in-person events that you can do, the better, when it comes to... well, let's say not more, let me say quality. Just having those connections. People are craving connection. I don't want to say do a ton of shitty events, but the point is, having that as a part of your business model. Connecting is what people are craving. This loneliness epidemic is running rampant.
Eric Berman: The value of the communities we're all building. Well, you and I could go on for hours, Cary. I always appreciate getting a chance to hang out with you and talk. We talk to so many similar people, and I love what you're building. I love the difference you're making for all of us that need it. So I appreciate you, and I look forward to seeing you soon when I come out to Bozeman later this year.
Cary Jack: Yeah, man. Yeah, I'm stoked to see you and hang and kick it with you. And yeah, any way I can serve you or your community, always happy to support. I really want to help other people put the happy in their hustle, specifically my people, which are entrepreneurs.
Eric Berman: I love it. So yeah, I love it. All right. Well, thank you so much. Talk to you soon.
Cary Jack: All right. Peace and love, everybody.
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About The Guest
Cary Jack
Cary Jack is the founder of The Happy Hustle, a company whose mission is to educate, inspire, and entertain entrepreneurs while reminding them to enjoy the journey, not just the destination. He is the author of the book The Happy Hustle, which he began writing while living in Bangkok after walking away from a New York tech startup he built with his brother, and he hosts his own podcast. Cary created the Soul Mapping System, a 10-alignment framework for harmonizing ambition and well-being, and leads the Happy Hustle Club, a capped community and mastermind for high-performing, outdoor-loving male entrepreneurs that mixes business with adventure. He is also building a happiness software program. Raised between a Montana ranch and Sarasota, Florida, Cary now lives in Bozeman, Montana, with his wife and young daughter, and makes time for fly fishing, horseback riding, and martial arts.
