https://www.listennotes.com/e/c97f510081874551b16a3f21b6c0c7ed

All right, today we are diving into one of the most controversial questions in entrepreneurship. Should you quit your job to start a business? And I'm going to tell you something that might surprise you. Sometimes the answer is heck no. And sometimes, well, sometimes those boats get burned for you whether you like it or not. And here's what I mean. I've had my boats burned for me. Sometimes by choice and sometimes by force. I've watched friends make the leap and crush it. And I've watched other friends destroy their families, chasing a dream that should have just stayed a side hustle. So by the end of this episode, you're going to know exactly when to take the leap and when to keep your day job. Plus, I'm going to play you a conversation I had with a good friend of mine, Stephen Hale, who actually did burn the boats the right way. And his story might just blow your mind. But first, I'm going to tell you about the great boat burning debate that's been messing with my head for the last 15 years. All right, let's start with the elephant in the room. There are two competing viewpoints. In my head, I'm a walking contradiction. On one hand, when there's no plan B, plan A has to work. So burn the boats. Go all in, Force yourself into a corner where success is the only option. And the second idea is it is foolish to put all your eggs into one basket. Smart people always have backup plans. Only idiots risk everything on an unproven idea. So which one of these viewpoints is right? Well, here's the thing that actually drives me crazy. I kind of believe both of these things are true at the same time. And before you think I'm some wishy washy fence sitter, let me explain my logic for you. If you've never heard of Dude Perfect, they're these guys who became YouTube millionaires by making trick shots. I'm sure you've heard of them. Basketball from a helicopter, golf balls into moving cars, that kind of stuff. They have this incredible documentary on YouTube. I highly suggest you watch it with your family. And there's this moment in the documentary that perfectly encapsulates burning the boats. Done right. So Dude Perfect started as five buddies down at Texas A and M. They started making trick shot videos, they started going viral, they started getting sponsors, but it still wasn't like a business that could support all five of their families. So three of them went on to get full time jobs after college, and two of them, the twin brothers, were working on Dude Perfect full time. And it wasn't working. They were working remotely, pulling all nighters, working on the weekends only. And the two brothers were kind of feeling burned out and they were feeling slighted because they were doing most of the work and they were about to break up. They almost quit Dude Perfect entirely. Their families thought they were crazy, et cetera, et cetera. Until one day they sat down, they had a pivotal conversation and they said, we can't just be lukewarm. We gotta be all in or all out. Do we wanna quit this? No. There's something here. Can this support our families right now? Absolutely not. But we need to have faith and belief that it will, that it can, especially if we put all of our focus into it. So the three guys that had full time jobs quit their jobs and all five went all in on Dude Perfect. And they say specifically that that was the biggest inflection point they'd ever experienced. After that point, everything just came together. Bigger and bigger sponsors, better videos, more virality, more money. It was a runaway success. And it's not a coincidence that it happened right when they went all in. They had no backup plan. It had to work. They cared about it more than they ever cared about it because of that inflection point. That's what burning the boats looks like. When it works, plan A becomes the only plan. So plan A has to succeed. I took an entrepreneurship class in college and our professor taught us about what's called the wing walkers code. Now, if you can picture a wing walker, he's walking across the wings of an airplane and he never lets go of one railing until he has hold of the other. Which also means don't burn the boats. Don't let go of the main thing until you have another thing. And I also believe in that too. It just depends. It depends on who you are, depends on the situation. How much experience do you have in the field? Are you able to go back to your job if your business doesn't work out? Some people are, some people aren't. How competitive is the market that you're in? Both of these viewpoints feel right to me. Both feel smart. It just depends on you. It depends on understanding the difference between burning the votes by choice and having them burned for you. And I've experienced both. So picture this. I'm 25 years old. I just sold my first real business called Phone Restore. I'm feeling pretty good about myself and I've told the story before, so I'm going to make it really quick. Long story short, the deal with the buyer did not go as well. As it was supposed to have gone, and it got a little ugly, got a little contentious, my income went to zero overnight, literally unexpectedly, by no fault of my own. Luckily, I was working on something else. Of course I was. I'm always working on something else. But I had to make that work. And I had such a chip on my shoulder from this deal that was quickly going south that that further added fuel to the fire. And that next business was how I made my first million dollars. It's how I built this house that I'm living in today. And had that deal not gone south, who knows where I'd be today. I don't think I would have had as much drive. And since that moment, I've had a couple other burn your boats moments, and they've worked out just as well, if not better. And conversely, whenever I have a really profitable business and I'm still tinkering with other ideas, those other ideas just don't go as well. Because as soon as I hit some roadblocks or friction or I get annoyed with customer acquisition, then I just move on to something else because I'm able to, I have that luxury. I had this company called Presto Cars once, and it was a concierge car buying service, and it was working great, but I hated it, so I quit it. It could have been a big, big business, but my main business was crushing it and making a lot of money. So I just didn't have the drive. So a lot of this also depends on you. What type of person are you? But me, when there's no other choice, I have to make it work. Here's another personal story for you. So, as a member of the Church of Jesus Christ of Latter Day Saints, I've never tasted alcohol or drugs or any of that. So when I go to networking events and someone offers me a beer or something, the temptation to drink that beer is exactly.0, 0.0%. Because as a kid, I made up my mind I am never going to touch that, and I never have and I never will. And it's easy to say no, because it's not even an option. Like, I would not go to Walmart right now and key all the cars in the parking lot. That's not a temptation. It's not even an option. It will never happen for me. Now fast forward to when I'm 31 years old. I look in the mirror and see how fat I'd gotten in my twenties. I was £260. And I knew I had a change. I had to lay off the carbs. But most people fail at diets and I was no exception. I had tried diets in my 20s. I heard about keto. I tried it and there was one secret hack that worked for me and I just treated carbs like alcohol. That's it. Just as if there were alcohol sitting on the table. There was no chance I was going to drink it if there were carbs on the table while I was on keto. It just wasn't an option. I just convinced my brain that. That it was alcohol or that it was keying all the cars in the Walmart parking lot. It wasn't an option. Once I flipped this switch in my brain, eating carbs wasn't even a temptation anymore. And I lost 60 pounds and I kept it off. That's a burn the boats moment right there. It's not like anyone took carbs from me. And it wasn't an option. I made that choice strategically. Now, don't misunderstand. I'm not saying that if you suffer from any addiction, you can just will yourself to stop. I know it's a lot more complex and more difficult than that, but for me, in this specific circumstance, it worked great. So your burn the boats moment doesn't have to be quitting your job. It can be smaller, more targeted decisions where you simply eliminate the option to go back. But here's the thing that's going to make you a little mad. When people come to me with their business ideas and ask if they should quit their six figure jobs, I almost always tell them no. And they're coming to me hoping that I say yes. They want me to be the guy that says, go for it. Chase your dreams, burn the boats. But the thought of me encouraging someone to do that scares me to death. I've never had to quit a big awesome job, so I really have a hard time advising someone else to do that. Especially when they have a family. Especially if they might turn out to be a crap business owner. I don't know. So there's a key distinction here that everyone is missing. Burning the boats is not taking a poorly calculated risk. If burning the boats is done right, it should feel like an obvious decision. And you're going to hear that in the conversation we'll get to in a minute. It should feel like the only decision. I'm used to someone else lighting the match when my boats were burnt. That's not normal. Sometimes that fire arrow comes out from behind the ridge and lands right on my stern and there's nothing I can do about it except figure out how to swim. So here's the million dollar question. How do you get all the benefits of burning the boats without the stupidity of taking massive, poorly calculated risks? So let me paint you a picture. Meet John. John makes 180 grand a year working at a corporate job. John wants to open a mini donut stand. Not just one stand. He's all in. He wants to create a franchisable model that he can scale nationwide. So John comes to me and says, chris, should I quit my job and chase this dream? And here's my answer that makes everyone mad. No, John, you shouldn't. But here's what you should do. We can be creative because constraints equal creativity. So do this, John. Burn the boats by committing to a plan. A smart plan. And here's exactly how it'll work. Day one, John sets revenue goals within a reasonable time frame. If these goals are hit, he quits his job. If they're not, he stays. The boats are burned on the commitment of the plan, not on the paycheck. Months one through three, John spends nights and weekends learning everything about the mini donut business. He's not playing around. He's treating this like his life depends on it. Because eventually he will. He wants it to. But months four and five, John finds and buys a mini donut cart on ebay. He's not going to finance 200 grand for a storefront. He's starting smart and small. Month six, John learns how to operate everything in his spare time. He's making donuts in his garage. He's perfecting recipes. He still hasn't quit his job. He's figuring out how to work the equipment, how to repair it. Month seven, John spends every single weekend at fairs, festivals and farmers markets, slanging donuts and learning the ropes. This is where the magic happens. This is where John finds out if he's cut out for this or not. Month nine, if the numbers are working, John buys a second cart and hires his first employee. Remember, he still hasn't quit his job. And if, for whatever reason, this business doesn't work out, he has learned a valuable lesson for only a few thousand dollars and not having to quit his job instead of hundreds of thousands of dollars and quitting his job. Do you see what's happening here? John is burning boats on the commitment level while keeping his financial safety nets in place. He's eliminated the option to be casual about this business. He's eliminated the option to quit when it gets hard. But he hasn't eliminated his dream or his ability to feed his family. This is how you burn boats intelligently and strategically. You remove the ability to be half hearted without removing your ability to survive. And here's the thing, most people aren't going to do this. You know why? Because it's actually harder than just quitting your job. When you quit your job, you get this rush, this dopamine hit. You get to tell everyone you're an entrepreneur now. You get to feel like you're living the dream. But when you do it the smart way, you're working 60 hours a week. It's not sexy. 40 at your day job, 20 plus on your side business. You're grinding in the evenings and on the weekends while your friends are watching Netflix and there's no glory in it. And yes, you care about what people say because everyone does. You don't have a dramatic story to tell at parties. It's just smart, methodical progress towards a goal. But here's what happens when you do it this way. By the time you actually quit your job, it doesn't feel like burning boats at all. It feels like the obvious next step because you've already proven out the concept. You've already built the foundation. The boats don't get burned. They get upgraded to a yacht. I try to read and respond to every single response to my newsletter. And here's what I've learned about most of you listening right now. You either own a business or real estate or you want to. Both categories will always need a burn the boats moment eventually. Maybe it's to open location number two. Maybe it's to quit your job and go full time. Maybe it's to make that acquisition you've been thinking of for months. And here's something I've noticed in thousands of conversations with these entrepreneurs. I can't remember ever talking to someone about a major trial they faced without them telling me something like, but man, did things get so much better afterwards. There's a pattern there. The struggle isn't the end of the story. It's the setup for the comeback. Many of you listening or watching right now are probably going through some serious suck. I don't know what that is. Maybe your business is struggling. Maybe your marriage is struggling. Maybe you're stuck in a dead end job that you hate. Maybe you're drowning in debt or dealing with family issues or health problems. But I don't know your situation. But I do know this. Your greatest days are ahead of you. And we will always learn the reason for our trials. Maybe in this life, maybe in the next. But what I've learned about burning Boats, whether by choice or by force, is if you burn the boats and run out of coconuts, you're about to find a herd of cattle in a spring. Not what you expected, but maybe even better. If you burn the boats and you get desperately homesick, you're about to be rescued. If you burn the boats and you feel hopelessly foolish, you're about to be vindicated. Now, I'm not going to give you a cliche like, what doesn't kill us makes us stronger, but I will say, and this is a CK original, what doesn't kill us reveals the strength that we've already had all along. So you can do this. Whether you burn the boats, keep a plan B, do both. The choice is yours. But now at least you know the difference. So, with that in mind, please enjoy this conversation I had with my friend Stephen Hale, who worked for an awesome publicly traded company making hundreds of thousands of dollars a year with great benefits. And he left it all behind to start his own business. Let's see how it went. So tell me, when the seed was.

First planted back in April 2023, there was no inclination. I didn't have a desire, didn't need to. We received a different employment agreement from our company at that point, which was pretty limiting, or at least it felt that way for me. So they put this non compete, non solicit in front of a new employment contract. I had my attorney look at it. I know my boss had his attorney look at it. My boss just up and quit one.

Day because of this agreement.

Sent us an email and said, hey, it's been great. And I peaced out. And we were like, that's wild. Like, he didn't call any of us. He didn't tell us. It just happened.

And that was like the first kind of warning sign, like, okay, something's shifting here.

Yeah. And we could see a little bit of a culture shift. Again, I still like the leadership over there. They're good people. But there was a shift. And so after consideration, it's like, well, if I sign this, you know my options if I want to leave or go somewhere else to become a partner or grow or, you know, have my clients or whatever, would be very difficult. And so made the choice to not sign with one of my other partners. We talked and decided that we would try to do this on our own.

And here's a question. If they never put that new agreement in front of you, okay, you just stayed under the same agreement, what are the chances you ever would have done this? Because I just find it very interesting that like you were good, you were set, but because of the fact that you had to like suddenly make your career much more limiting, it got you kind of shopping around and thinking in a different way.

Right.

I don't know if I ever would have. I know, like I made an agreement with myself that, you know, that I wanted to have ownership. I knew that's where real wealth comes from. It's from ownership. And you know, I talk myself into, oh, stock is ownership. So I'm fine, I'm good here. And yeah, the longer I stay, the more stock I'll have, the more ownership I like. You know, the direction of the company. I think it's really smartly built. So yeah, I had, I had no reason and I don't know if I would have left.

I want to pause on that because that seems just like an interesting framework for life where like the optionality was actually more limiting than not having the options.

Right.

If you can go with the next from 2023 to 2033 saying, oh, I could leave it anytime because my agreement.

Is so loose I could do whatever.

I want, like that just means you're never going to do it.

Yeah.

Whereas when they kind of force you to make that decision, you're like, gulp. Let's start thinking about this a little more seriously.

Right?

And we weren't the only ones out of that group, out of our advisory services group, I mean, over the course of a year for main groups left. So I put in my notice in August and I had a two month notice period. They made me stay my two months. So waited my two months and we started Oak Bridge on October 1, 2023, me and one other partner. It was like, website needed to be built, corporation documents need to be filed, logos need to be designed, all that fun stuff. Like it was all the things and it's really fun and really exciting. But we also knew that like starting October 1st, we did not have a paycheck. And again, we didn't get any outside investment. So it was up to our savings or getting, you know, support from family members or whatever it may be to fund the business. And really it wasn't, we didn't have any employees, so we were only funding our own business or funding ourselves. But we quickly hired contractors and things like that. And all of a sudden you start seeing kind of expenses roll through and every deal was really big for us. It was like one of our clients is taking a chance on us. I mean, in their mind they probably weren't taking a chance. They knew Us really well and they knew the work that we did. Yeah, but every single one, I mean, was like a huge victory. It was so important because it brought validation to what we were doing. So that's kind of the quick of like getting to kickoff.

Where was your mental state at for that first quarter? Were you worried? Were you confident? Were you waffling back and forth between the two?

I was preparing for the worst and hoping for the best. So we were. You know the phrase that we use in our house a lot is pray as if everything depends on God and work as if everything depends on you. And it was a lot of that.

It's a good one liner.

Doing everything we could to make sure that we were bringing revenue into the business, delivering a very high quality product to everyone. And then we started hiring people about mid year last year. I knew how many kids were under payroll, so I knew how many mortgages I had to pay and I knew how many kids mouths I had to feed and it kept me up. We were doing well. Like we were well above what we anticipated. We were hoping to do like $2 million in our first year and we ended up of revenue. We thought that'd be great. Like five employees. We ended up doing, you know, almost three times that and had a lot more employees. I think at the end of year one, we had the end of our first of 20, 24, we had 25 employees.

Wow.

First full year.

First full year. So In October of 24, we were interviewing for a chief of staff. So it was our first non revenue generating individual. During the interview I told her that, I said, yeah, we have. She was like, what is, what's the biggest worry about the business was that or what keeps you up at night. And I said this number. I was like, the number 17. She's like 17. I was like, yeah, that's how many kids and how many mouths we have to feed.

That's the children of your employees.

Yeah.

That's an interesting number to keep track of, but.

Well, it was my kids, it was my partner's kids, it was the kids of our employees. It was everybody. And she's great. And she came back and her email responds back to me. She was like, she has three kids. She's like, I really hope that we can make that number 20. I would love to work for you guys. I was like 20.

Having the opposite effect.

Yeah. No, and we hired her. She's great. She's been amazing addition to the team. Very fortunate. But yeah, it was very stressful.

Were you constantly waffling Back and forth between confidence and insecurity.

We had all the confidence in the world that we could keep this going, but it was more of just a, okay, so when are we going to get paid? When am I going to start feeling comfortable again? Right. And I'll. Yeah, I don't know if I'll ever feel comfortable.

Was it. Nor should you. What does David Goggins say? Was there ever a time you had to rely on friends or family to.

Help support you during this?

Yeah. I have a benefactor and I have a family member who helped and we owe a lot to that family member. Got us through the first few months, which was great.

You don't seem like the type of.

Person to want to ask someone for help for anything, much less money.

No, I don't. I don't like it.

I think one way you could look at this is do you hate asking for help more or less than you hate not chasing your dreams?

Yeah.

Imagine a world where you don't start this business. You keep the job. Ten years from now, you pull out a phone and you watch your life play out as if you never quit. You knew what happened, Right. What's it like to watch a video of what your life could have looked like? You're watching a video of your life today of how it actually looks versus what it became. If you never quit.

I think there would definitely be a little bit of like envy and jealousy of is so fun. Like again, with hindsight, at the time it was very stressful, but it is so fun to build and dictate. Like, this is how we want to treat our employees. This is how we want to recruit our employees. This is how we want to treat.

This is my decision.

Right. It's like, this is how we're going to pay them. Like my employees make so much money. They do so well and I'm so happy for them. Like life changing money. They're doing great. I'm really pumped for them. This is how we want to go out in the market. Right. We don't have to report to shareholders, we don't have to report to a boss. We can just go. I think with hindsight, I've always wanted to build from like when I was a kid, like throwing newspapers at like 8 years old to like mowing lawns as a teenager doing all that stuff. It was always so fun to just build something.

I feel like building is in our DNA. I don't know if it's man's DNA or humans DNA. I can't speak for women.

It's Our God complex.

It's something, but I'm completely sold on that. I feel like the people that are most unhappy, whether they own a business or they have a job, are not building. You know, you can build inside a company that you work for and have joy and fulfillment.

I think that's the key to it for me. I love building.

Like, even if, like, go. If I go mow my lawn, just seeing something change from one form to another is so gratifying. You know, like crafting the perfect email or video or whatever it is. Like, we need to be creating and industrious and building and progressing. It's progressing, Right. We need to be moving forward whether you have a job or have a business. And I feel like that's the whole.

Unlock to all of this.

It's just building.

Yeah, and they've talked about that. As far as, like, employment satisfaction is. You need purpose. You need to feel stretched. You need to feel pushed. If you feel like you're doing the same thing every month over and over and over again, your job satisfaction goes down. I mean, like, I swore after I went to EY that I would never go back and work in a corporate office, because I remember, like, Dolores and Accounts Payable who just, like, hated her job, but she had been there for 30 years and didn't want to do anything else either. Right. But she was just stuck in that loop, you know, that's not the kind of environment I want to be around. Like, I. I need to feel pushed. I need to feel like I'm growing and developing. And so, yeah, I think there's something to that. And the overall satisfaction we get out.

Of life, how much harder would it have been to quit?

Had you waited five years, you had.

The same employment contract, same flexibility. It gets harder, right?

Yeah, yeah. The money just gets better.

The longer you say, and then I'll do what I love, the more likely you are to never end up doing what you love. I wish this were my quote.

I heard it somewhere, but it's something.

Along the lines of, salary is the price you pay to not chase your dreams.

It's such a warm blanket, and it is comfortable. You never want to, like, let it go. It's so consistent. There is something so nice about on the 1st and the 15th, seeing the money roll in.

I don't know what that's like.

Well, for the rest of us, I'll speak to the audience. It's nice. It's so great. But, you know, it is the price you pay. And like I tell my son all the Time. He's like, I want to go. Do I want to work it? Like, in and out for 17 bucks an hour? I'm like, okay. Or look at this, look at these economics. Look at how this, this flows. You know, if you just spray garbage cans.

Yeah.

You could spray six garbage cans and make a week's worth of salary at, you know, in and out, and it's all yours.

What advice would you give people that are on the fence about starting something or quitting something?

I think with hindsight, I overestimated the risk where I thought it would be too risky. Right. The worst that could happen when I started this was like, I'd have to go get another job.

The irony is that other job that you are, quote, forced to get, that job could end up being awesome.

Yeah.

You know, I probably would have made more money. Right. Like through this point. But that's. So that was the risk. But at the time, it felt like it was everything, okay, let's do this. Let's throw everything into it. We talked about, we called it burning the boats. Right. Like, I never even told myself that I had another option. I didn't tell myself during that time that I could just go get another job. I was like, no, I'm all in. I'm never even gonna let that thought creep in. It's this or nothing. So you just kind of throw yourself into it and it works. Right.

Funny, because I've done things where in. In hindsight, it was a lot riskier than I thought at the time.

Tell me one of those.

What was like, how did that work?

Like, signing a five year personal guarantee lease on a $3,000 a month retail store for a concept that I knew nothing about as a 23 year old with a new son.

See, but like, like, I talked to a guy yesterday and he's really young too. And I'm like, you're like 22. You have really nothing to lose. Worst case, what? You file for bankruptcy. Okay. You can't afford a home anyways. Like, no one can.

Yeah. Homes have literally never been more unaffordable.

Right? Yeah. Like, you have nothing to lose. Like, this is your time. Like, I really am jealous of, like, those that start young. When I started, it was like, I have four kids. You know, they demand a lot and there's a lot of expenses and there's a lot of things we have to take care of, and we have a home and a mortgage and like, all this stuff. But, man, like, if you're young, it's awesome.

I think it's Important for kids, like, for you to spend time with your kids, obviously, but for them to see that you work, that you have a work ethic that.

I'd agree. I'd agree. I think it's. I mean, you can't replace. The only thing that is a very limited resource is your time. And so you really want to make sure that you spend it appropriately. And I missed. I would say I missed that early in my career where I probably prioritized work a little bit too much, but that might have been the time and season I needed to. Maybe. But now I feel like I'm allocating my time more appropriately, spending much more time, much more quality time with my kids and with my wife and, you know, the business and kind of everything else that goes along with it.

Anything you would have done differently if you could go back in time, I.

Would have done it sooner. Again, like, time is our only real resource. One of my favorite books is Good to Great. And I think one of the key underlying principles there is, you know, if you find what you love or you find what you're passionate about, and it doesn't have to be like a specific, like, oh, I only love woodworking and you have to be a woodworker. It's like. Like, my favorite thing in the world is to, like, again, just feel stretched and feel engaged. And I love solving problems, and that just brings me a ton of joy. And that's what this job does. And so once you find something that you are really passionate about and that. And for some people, it might just be making money. Like, I just really like making money. It's like, great. Once you find it, like, just pour everything you got into it. Burn the boats. Don't give yourself an exit. Know that you have one, but just don't give it to yourself and go for it. And if it fails, you learn and you move on. Right. The only time you fail is if you don't learn anything from your experience. And my kids would be disappointed in me if I didn't mention it. We work a lot in the house of just understanding what's within your control. And a lot of times I feel like. And I've built up a little bit better of a tolerance of it now, like, not worrying about the things I can't control within my business. There's so many things I can't control. You can control your attitude. How do you adapt to. Or how do you react to bad situations and. Or good situations? How do you react to good news, bad news, your effort, how much time are you putting into it? Are you giving it everything you got and then your integrity, right? Are you doing it honestly so you can go to sleep at night and everything else is outside of your control? So it's one of those where it's, you know, take care of those three things and let the chips fall.

Stephen, where can we find you for all the healthcare professionals listening that have a six figure deal for Steven?

Oh guys, I do have a Twitter but I am not active so you could find me there but it probably wouldn't be the best. You can reach out to me. I do have a, an email address for my business. It's Stephen Oakbridge. As for advisory services.com or you can find me on LinkedIn. Stephen Haim. Yeah, happy to talk.

All right. I hope I inspired or encouraged you today to do what you think you should do. We'll see you next time on the Kerner Office.