Should you REALLY Burn your Bridges? When Failure IS an Option

The Entrepreneur Ethos

November 18, 2020

“If you have nothing to lose, burn every bridge.” On this episode of Entrepreneur Ethos, Jarie Bolander and I talk about the fine-line situation that comes with having a “Plan B.” People say “Failure is not an option” … but I failed way more than I succeeded on my road to prosperity. 

The bridge you need to burn is not the bridge to a “Plan B” ... but the bridge back to the unacceptable. To the dead-end job, the bad relationship, the “life half lived.” Burn that bridge, and keep beating at your craft until you succeed.

We also talk a lot about sports, as well as…

  • Our childhood sports coaches’ favorite lessons. Spoiler alert: my favorite coach-ism was “Get your butt out of your ass!”
  • How team sports prepare you to run a business.
  • The two game-changing lessons I took from Stoicism.
  • How you can actually be at a disadvantage if you come from a rich family.

About the Show: Jarie Bolander is the host of the The Entrepreneur Ethos.

Full Transcript

Jarie Bolander: My name is Jarie Bolander. Welcome to “The Entrepreneur Ethos” podcast. On this podcast we’re going to take a deep dive into the traits, values, beliefs and skills of all sorts of entrepreneurs to learn how to build a more ethical, inclusive, and resilient world. Let’s get started.

Hey, everyone. I wanted to jump in quickly and let you know about the release of the audio version of my book, “The Entrepreneur Ethos,” narrated by David A. Conatser. If you want to support the show, you can buy it wherever audio books are sold. Links are also in the show notes.

Now onto my guest for today: Dylan Ogline. Founder of Ogline Digital, a digital marketing company. Dylan’s route to entrepreneurship started at 14 when he started selling cellphones on eBay after reading the book “Rich Dad Poor Dad.” He scrapped his dreams of winning a college scholarship as a hockey player, and instead, dropped out of high school to educate himself on become a business owner. After many different stats and failures, after his initial success selling cellphones, he was advised by a mentor to focus on one thing. That one thing was his digital marketing company, which he has built over just a few years into a seven-figure business.

Though still young, Dylan has put in the time to try and fail. And it’s through the lessons he’s learned through both coaches and mentors, as well as his own experiences that has brought him to finally achieving success. He reinforces the teaching that you can’t ever give up, drawing on the wisdom of stoics. He also things the most important lesson to learn is to never lose touch of what it’s like to struggle. It’s getting through the difficult times that gives you the strength, tolerance, and growth to eventually succeed. He practices gratitude daily and wants to pay it forward and help others, and now also offers programs to help people start their own digital agencies. Now, let’s get better together. Dylan Ogline, welcome to the podcast.

Dylan Ogline: Thanks for having me, man, glad to be here.

Jarie Bolander: Yeah. Appreciate your time today. I think we found each other through if I’m not mistaken.

Dylan Ogline: Yeah.

Jarie Bolander: Which is the one I’ve been getting lots of great guests, which I know you’ll also be an awesome guest.

Dylan Ogline: Oh, no pressure now.

Jarie Bolander: No pressure, right? Well, what’s interesting, I heard you on “Money on My Mind” podcast, which I was actually on that one. I was episode three and I think you’re episode five, so in talking to him, a 16-year-old kid.

Dylan Ogline: Yeah, he’s an awesome kid, man.

Jarie Bolander: Just crushing it. I really enjoyed talking to him. And it’s just really cool to see this sort of evolution of podcasting, and helping people, and lots of kind of like these conversations are really important. So I really appreciate your time.

But I really want to understand a couple things from you. First off, I want to understand how you got to do your business today, which is a digital marketing business, and we’ll talk all about that. But before we get in all of that, like I always like to say is, “Well, why don’t you tell me how you got to do what you’re doing today?”

Dylan Ogline: Sure. So that’s a long story.

Jarie Bolander: We’ve got time. Take your time. Take your time.

Dylan Ogline: Yeah. Yeah. So I’ll try to condense it, I’ll guess. So I started my first business when I was 14 selling cellphones on eBay, there’s where it all got started. And this was really after I picked up a book, “Rich Dad poor Dad,” by Robert Kiyosaki, my brother had it sitting around. And I read that and it just sparked the entrepreneurial bug, I guess you could say. I also come from a family of business owners and whatnot. And so yeah, so started that business, and it was actually doing pretty good, I was probably making a couple thousand a month. Which, when you’re that age, I had all the money in the world.

Jarie Bolander: You’re on top of the world, man.

Dylan Ogline: I didn’t know how to spend the money fast enough. And that lasted for a few months, probably about a year, close to a year, and then I got shut down because my merchant account got shut down because they figured out I think it was around tax time. They were like, “Oh, like we need your date of birth,” and all this stuff, and they found out I was under the age of 18, so they shut me down.

Jarie Bolander: Wow.

Dylan Ogline: But it was just like good timing because this was 2003, 2004 give or take. This was the infancy of Google ads. Really back then like banner ads were popular, but this kind of targeted, direct response marketing was starting to become a thing. I don’t even think Facebook had launched yet. Maybe they had launched. I can tell you Facebook ads was certainly not a thing.

Jarie Bolander: No. I think maybe Facebook was still only on college campuses. I mean you’re probably right. It was infancy. I think MySpace was around, they were the big deal.

Dylan Ogline: Oh yeah, MySpace was huge back then. But MySpace ads I don’t think that ever became a thing.

Jarie Bolander: Yeah, I think they figured that out.

Dylan Ogline: They probably had banner ads, but that was it.

Jarie Bolander: They probably had banner ads, right.

Dylan Ogline: So towards the end of that business I started playing around with Google ads and just caught that bug, I guess, and started like reading all these marketing books. I probably picked up is it “21 or 22 Immutable Laws of Marketing,” which every business owner needs to read that book, and just picked it up from there. And after that, got shut down, I spent probably the next 12 years bouncing around from one thing to the next not getting anywhere, not really having any kind of success whatsoever. At my peak I had nearly a million dollars in debt. I had ten-ish business projects.

Jarie Bolander: Wow.

Dylan Ogline: I was up to my eyeballs in my debt. I didn’t know what a vacation was. I forgot what sleep looked like. And, yeah, so reached a tipping point, and after a conversation with a long term mentor, I just scrapped everything except for one single service, which was direct response digital marketing advertising management. And one single business, one single service, just scrapped everything, focused on that and that was it, and everything started to spin in the right direction after that. That’s how I got into what I’m doing.

Jarie Bolander: Wow. So focus.

Dylan Ogline: 15, 16 years in three minutes

Jarie Bolander: Well yeah, it’s like I’m the overnight success in the last 15 years, right?

Dylan Ogline: Yeah. Yeah. Yeah.

Jarie Bolander: I mean I’m all for championing the successes as well as what I like to call survivors, right? Because a lot of people don’t survive the entrepreneur journey, or not in the way they think they’re going to survive it. And so when you see all these famous entrepreneurs, you’re like you feel bad that you’re like, “Uh, how come I’m not doing a million a month, or six, seven, eight figures? I should be able to crush this. How hard could it be?” And you’re literally like just starting out, did a course, or whatever.

And so it is always good to have that perspective that this entrepreneur journey, I mean, it’s a lifestyle, right? Like I can’t see myself doing anything else, and I’m curious if you ever thought about doing something different than what you’re doing right now.

Dylan Ogline: In terms of going down other kinds of businesses, certainly. Certainly if you would have asked me five years ago would you own a digital marketing agency, absolutely not. That’s not going to be the thing. But always owning a business, that was yeah, since I was 14, that’s what I wanted to do. And then also probably two other interests or some kind of coaching, but I figured that would go more towards athletics. Because, for me, I still am a hockey player, but hockey coaches when I was younger just had a massive impact on my life, and made me a better man.

And so I always like had an interest to kind of help other people with that. But that, some kind of coaching, and then getting into public service some day. I always kind of envision that, but more as like I’m retired and now I can put 100% of my effort into that. I don’t need to worry about paying the electric bill off of being in public service of some capacity.

Jarie Bolander: Right. Right. You’re the wise old statesman.

Dylan Ogline: Oh wow.

Jarie Bolander: Back in the day. Well, I mean I’ve toyed with this idea too. I’m a little older than you so.

Dylan Ogline: How old are you?

Jarie Bolander: Almost 50.

Dylan Ogline: Really? It must be the webcam, you must have the…

Jarie Bolander: It’s the webcam, yeah.

Dylan Ogline: The webcam’s making you look better.

Jarie Bolander: Yeah, everyone’s got to get the Logi HD 1080p and you’ll look 20 years younger.

Dylan Ogline: That’s the secret.

Jarie Bolander: And they don’t even pay me to say that, right? But no, I mean I’ve toyed with that idea as well because I’ve had some experience in politics here in San Francisco, and the frustrations around that are immense, and you can imagine. I think you’re in Florida, so the politics in Florida are a little different than here in California. They’re the same problems, just manifested in a different way.

And it is funny that you bring up the coaching aspect because when I was in high school I played soccer, which is European football, and some great coaches. And my dad also coached the soccer team that I was on when we were kids. And the power of a good coach, especially athletics, and I know people are like, “Oh, it’s about the winning and losing,” and there’s like a bad connotation about that, but I always found that the coaches that I’ve had have been really instrumental in also making me a better man. I mean, just how to play fair, how to work as a team, how to handle loss, how to handle…

Dylan Ogline: Not giving up.

Jarie Bolander: Not giving up, another great one, or hey, you didn’t put the practice in, you’re going to suffer on game day. And I had this coach in high school, it was my varsity soccer team, is Coach Woodall, and we called him Woody, and everyone called him Woody. And this guy, he would run with us, like he was that intense, and he was fast, he was also the cross country coach I think. But I remember there were these like Woody-isms that I just remember. It’s just burned in my brain because it was so like monumental. And all these little Woody-isms were just these manifestations of how much he cared for us and trying to impart how to be a better man, which is lost nowadays, honestly.

I’ll probably get a lot of hate for this, but I don’t think we teach young boys how to be proper men anymore. I mean I just don’t see it.

Dylan Ogline: I agree with that.

Jarie Bolander: And I think a lot of that I think is because of this, I don’t know, there’s a lot of tension amongst all that. But his best saying was, “Get your butt out of your ass.” And we’re like, “Woody, like that’s an oxymoron.” And he would say these things all the time. Like I remember one time we had this thing called Repeat Hill. You played hockey, so you were always on the ice, but we had to go do hill runs.

Dylan Ogline: Oh we had to do that too.

Jarie Bolander: Oh, okay.

Dylan Ogline: It’s similar, yeah.

Jarie Bolander: Similar, yeah, so we had Repeat Hill because we were in the hills of Belmont, California, and we had this Repeat Hill. And he’s like, “Okay guys, whoever pukes on my shoe can quit.” And you’re like, “Okay, I guess this is going to be hard.” And just stuff like that where we bonded because we were all in the suffering together and it was fun, and those lessons are-- what are some of the lessons…

Dylan Ogline: 30, 35 years later that stuff still sticks with you.

Jarie Bolander: Oh yeah. Yeah, it’s amazing. I mean, so for you, were there any things like that when you were playing hockey or you’re still playing hockey, right?

Dylan Ogline: Yeah. Well, I mean now it’s like adult league. They call it beer league or whatever. We don’t know what we’re called. We’re all terrible.

Jarie Bolander: But fun, right? It’s all fun.

Dylan Ogline: Yeah, it’s fun, and there’s a lot of sportsmanship. I think a lot of being a man stuff comes out in sport. But I honestly don’t remember anything in particular that they said to me, it was just be don’t be a sore loser. Just small stuff like that. And not just the hockey coaches, teachers as well, even though I dropped out of high school. Like there were teachers that they just had an impact on me like, “Be a good person. Treat everybody equally.”

My parents, they did that stuff too. And then I’ve had mentors, I’ve had business mentors that taught me stuff like that, like “Always treat the customer fair.” Just all that stuff. And so that’s what drove me to. Again, I don’t remember anything, I mean I’m terrible at remembering quotes, terrible at remembering names and authors, and stuff like that. But I’m able to take away the big lesson there, so that’s the impact they had on me, and that’s why I always had that kind of desire to do some kind of coaching or teaching. The only problem is, is that especially amateur hockey coaches, unless you’re going pro you don’t make any money at all.

Jarie Bolander: No. No. It’s all for the love of the game.

Dylan Ogline: It’s all for the love of the game and just helping people. And I didn’t want to be poor. So that’s why I focused on business because I wanted to be able to turn on my heat whenever I wanted to and not be hungry. And yeah, so that’s how I got here now.

Jarie Bolander: I mean because I noticed on your website that you are starting to offer coaching or program or some education on how you created your digital marketing agency. So is that sort of like that manifestation of this teaching and coaching desire?

Dylan Ogline: Well, yes, that is the end result of it. Over the years though, like I would meet people at industry events or whatever, even when I didn’t really have any financial success, the fact that I owned my own business and I was 23, 24, I would meet people that were maybe in their 30s and they were like, “I want to start my own business. I don’t even know where to start. What do I do?” So I started mentoring people just that I had met out at industry events or whatever. And that kind of manifested itself into, “Well, everybody seems to want to start their own business.” Then I got the agency to work, so then I reached out to those people. I think the very first “version” of my program-- in quotes “version.”

Jarie Bolander: Yeah, air quotes, yeah.

Dylan Ogline: Yeah, it was just maybe five or six videos in Google Drive. Just recorded some quick videos with some quick lessons, threw them up on Google Drive. There was no website or anything. Reached out to those people that I had mentored before and was like, “Hey, couple hundred bucks, you get access to this, and then we’ll do like a weekly call,” and that was it. And just then I had another version, and now I just launched the third version of the program. So it’s weird how it just continues to reiterate itself.

Jarie Bolander: Yeah. Well, I mean I think the thing that like sports also taught me because now I do Brazilian Jiu-Jitsu as sort of my trying to recapture some of the glory days. No, no, I know how bad I am. I just do it because it’s fun. But the whole learn, do, teach kind of methodology that really like instills in you a sense of if I know something I need to teach something. At least that’s my philosophy. Because the people like the mentors I’ve had, the coaches, the teachers who took the time to like explain some of these things to me, or read a book, or someone took the time to write it down, or I take an online course or whatever, that just seems like a powerful way to kind of have this cycle of goodness. This continuing effort to make the world better. And I truly believe that entrepreneurship is the way that we’re going to do that. I can’t see a better way.

I mean you need governments, and organizations, and institutions to provide sort of the frameworks, loose frameworks, kind of the guard rails for which to operate. But boy, I mean, helping people create businesses, helping them help other people. Making communities more sustainable, more resilient, more inclusive, building up these real like pillars from the ground up just seems like a great use of time. And not only that, I think the sports stuff helps with that because, oh, we’re a team, like we can’t do it alone.

Dylan Ogline: We’re all in this together, yeah.

Jarie Bolander: We’re all in this together. And I know for a fact the times when we were really like when we were playing soccer and we were really vibing is when we were working as a team. Once we started to kind of go the bad path where we’re all being selfish or mad at each other, it just collapsed. I mean it was so stark. It was just what happened? Like it’s like you guys weren’t playing as a team, get your butt out of your ass. And you’re like, “Whoa, whoa, whoa stop.” It’s interesting that you said that you dropped out of high school, and I do know a lot of people that the formal education process is a bit cumbersome, and people have talked about how it’s basically just making factory workers, and the creative among us. Although I did get through high school and also went to college and grad school. It was hard for me because I’m just like, “This is just I don’t want to sit here and why do I have to learn this stuff?”

Dylan Ogline: Learning meaningless stuff.

Jarie Bolander: Yeah. Yeah, yeah. And like in my style, and maybe the same with you, and this is why I’m curious like learning styles differ a lot. And even with entrepreneurs, like some entrepreneurs, they’re like, “I just got to go grind it out. I got to do it.” Others can read it in a book, others hire a team. I mean how has your learning style kind of impacted how you’ve run your business and do you think that moment where you’re like, “Okay, this school stuff’s just not for me,” how did that feel? How did that all kind of pan out?

Dylan Ogline: So it’s kind of two very different reasons. Of why I quit high school was actually because of hockey. So just like everything was hitting me all at once in my life. The goal with hockey, even though I wasn’t that good, I wanted to go to college and when I was 13, 14 I’m starting to think. People are telling me like, “You need to start thinking, like where are you going to go to college for? Where do you want to go? What do you want to do? You don’t have to make up your mind now, but you need to start thinking about it.”

And it wasn’t in the cards for my parents to pay for college, so it was, “I’m going to need to get a scholarship,” right? So my goal was just play as much hockey, try to get as good as I can so that I can get some kind of scholarship, even if it’s at a D3 school, like not D1 because I’m certainly not that good. Just some kind of scholarship so you can actually go to school.

Jarie Bolander: Right.

Dylan Ogline: And I was at this one game, you could like mentor with the varsity team, because I never even got to varsity, I was never old enough.

Jarie Bolander: Right.

Dylan Ogline: And I was at this one game, and I’m watching like a prep school from Pittsburgh. I forget which school. And I’m watching them play, and they’re just so much better than me. And it just it hit me that like all of these people, like they’re so much better than me because they started way earlier. I started playing when I was maybe like ten or 11, I forget. They started playing when they were like four or five. Which it’s only five years difference, but when you’re that age, that makes a colossal difference.

Jarie Bolander: Oh, it’s like orders of magnitude each year.

Dylan Ogline: Yeah. Exactly.

Jarie Bolander: It gets crazy.

Dylan Ogline: Each year you get like ten times better.

Jarie Bolander: Yeah. It’s amazing.

Dylan Ogline: Yeah. So I realize that at the same time I was starting to think like, “Hm, I want to go into maybe business, that’s what I want to go to college for.” At the same time I picked up “Rich Dad Poor Dad,” so I’m starting to think of that. At the same time, I’m dating this girl where her dad and I got along really well, and he was like the vice president of like one of the biggest businesses in the area. So I had him influencing me, I’m reading this book, I’m like getting this realization that all these people they’re so much better than me because they started earlier. And I’m like, “If I continue down this route, maybe I can get into college, maybe I can get some kind of scholarship to pay for it. Then I’m going to be into business when I’m like 23, 24. But if I start doing that stuff now, I’ll be like ten years ahead of the game. So I know it’s not going to be easy, but I’ll be ahead of the game.”

So that’s when I started my first business and then I started taking all these business classes in school, and I’m correcting the teachers, they’re teaching like the wrong stuff. And this is off of like reading three business books, and I’m like, “You’re completely wrong. Like what you’re talking about is like five years ago they changed the laws or whatever.”

Jarie Bolander: Right.

Dylan Ogline: And, yeah, so like all this stuff hits me at one time, and it wasn’t like I was going to quit, I convinced my parents to let me do home schooling, and somehow they said yes. I paid for it, and never even opened the books, never even took a single test, and just focused on business. It was like, “I believe that if I start now, it’s not going to be easy, but ten years from now I’ll be ten years ahead of the game. Everybody else that’s getting out of college and is like, ‘Oh, I’m going to start my own business or I’m going into the business world.’ Sure, they might have a degree to show for it, but I’m going to have ten years of experience to show for it.”

Jarie Bolander: Yeah. Which arguably…

Dylan Ogline: I don’t recommend that to anybody. It was absolutely stupid. Go to school, kids. Finish high school.

Jarie Bolander: Well, I mean, like yeah, in some respects it’s not for everyone, and you got to have a back-up plan, right?

Dylan Ogline: I didn’t have a back-up plan. There was no back-up.

Jarie Bolander: All right, have a back-up plan, clearly.

Dylan Ogline: Yeah. That’s a good idea.

Jarie Bolander: I work with a bunch of professional athletes, and as you can imagine, professional athletes their whole lives have been focused on sports. And so they’re like the cream of the crop. I work with two NFL athletes right now. I used to work with a couple more. But, boy, like you go in their neighborhood where they’re from, and typically they’re the one of the only ones that made it out, like “made it out.” And they were focused, “Okay, I’m going to do sports. I’m going to do sports.” But then they start to realize it’s like, “Well, what happens when I retire or I get hurt? Like I got to do something else. Like what’s my back-up plan?”

And but it’s an interesting point because a lot of the time the focus on sports, or one single thing, or like burn the boats and just we’re going for it. One, to focus, as you saw. Like you focused on one business after all the ones that you talked about, and it started to be successful. Focus is important, but not I think to the detriment of your whole life, right? I mean I know there was Elizabeth Holmes who was the CEO of Theranos, the notorious Theranos, that is now completely defunct, and she’s being prosecuted for fraud because they made a lot of stuff up, and anyway.

Her whole thing was, “No, there’s only plan A.” And I’m like, “That’s actually a really dumb thing to say.” I mean, you may have a focus, but you’ve go to know like you’ve got to have the fall back. I mean every great tactician, every great strategist, every great warrior, every great like generals, like I got a back-up plan in case the world’s going to… Like oh my gosh, there’s cloud cover, now what? I mean you’ve got to adjust, you’ve got to adapt and overcome.

And what’s interesting is that when we were talking a little bit before is that you’re a big fan of the stoics. And this is all coming towards you didn’t have a back-up plan, but you adjusted, right? And were you, as a young person, more of a stoic or did that stoicism kind of come out of, “Oh wow, I may need to adjust some things, and I really don’t know what I’m doing.”

Dylan Ogline: Stoicism. That really just I picked up a book somewhere and just read the first paragraph, and I was like, “Wow, this like this can maybe guide me.” There are two things that I take away from stoicism. One is-- and I’m going to mispronounce it-- momento mori?

Jarie Bolander: Yeah, momento mori.

Dylan Ogline: Remember mortality. You’re going to die.

Jarie Bolander: You’re going to die. Yup.

Dylan Ogline: So recognize that, always be mindful of that. That helps me with like my meditation and showing appreciation. Just like I appreciate every moment because I recognize that I’m not guaranteed the next one. And the other main thing I take away from it is just simply not making emotional decisions. Always just recognize and accept your emotions whether it’s anger, sadness, happiness, love, lust, could be anything. Recognize those emotions, but when you’re making decisions, try to make the logical decision. And I mean there’s a lot to say with death in regards to that. Like being logical about death. But yeah, when it comes to making business decisions or whatever where you’re under pressure, always think, “Am I making the emotional decision or is this the logical decision?” That’s the two main things that I apply with stoicism to my life.

I would like to jump back though. You mentioned about burning the bridges and stuff like that. I believe you have to walk a fine line. I think if you have nothing to lose, then burn every bridge. If you were struggling to feel that fight and the motivation then I think it’s a good idea to burn all bridges and there is no other option, you can’t fail. You mentioned a general, there’s a story of a general who-- this might be fiction or not-- where they go to battle, and it’s like on an island. And when they get there they burn all the boats. And like all the soldiers are panicking like, “Oh, what if we need to retreat?” And the general’s like-- and you might know who this actually is, I don’t know where this story comes from-- but he’s like, “Well, you better win then because there is no retreating. I removed that option.”

Jarie Bolander: Yeah. Yeah. I think that might have been a Spartan.

Dylan Ogline: Yeah, a Spartan story, or something.

Jarie Bolander: Well, there’s a couple of them like that where…

Dylan Ogline: Yeah, you burned the bridge, you burned the boats. Now with like your athletes and whatnot where realizing that whatever you’re working on is going to end, I think that’s a little different. It’s definitely smart. You want to have like, “Hey, I recognize I’m not going to be an NFL athlete forever. I need to have a plan after that.” I think that is smart. But whenever you don’t really have success going yet, and you’re trying to make something work, removing failure as an option can really light a fire.

Jarie Bolander: Yeah. Yeah. I mean, I always say failure is not really an option. Well, failure is an option, but it’s never the final result. Because, for me, the failure just leads to the next opportunity. So what’s interesting about the whole burning the boats, and burning the bridges, and everything is that failure is relative to where you’re at, right? I mean life and death is different. You either survive or you die, okay? So you take life and death out of it, which we will. The rest of it is just a series of learning experiments. And you’re right, if you’re young, and you’ve got really nothing to lose, and you can place some bets, and okay, this failed, that failed. It’s not really failing, you’re building up these skill stacks, or these talent stacks.

Dylan Ogline: 100% agree.

Jarie Bolander: Because each “failure” is really just the next evolution of the learning. As a young person, this is a hard thing to swallow because you’re like, “Gosh, I just want to like get something under my belt. I got to feel like I’m making some progress.”

Dylan Ogline: I like the direction you’re going here because I have failed way, way more-- ten, 20, 30 times more than I have “succeeded.” So, yeah, I think if we’re specifically talking about business where I see you have these people who they start their first business, and maybe like a month into it like things aren’t taking off or whatever, and it’s like, “Welcome to the game.”

Jarie Bolander: 
Yeah. Yes.

Dylan Ogline: That’s how it is. It might take 30 iterations of your business or this business you’re working on might completely fail. It’s you keep going until you have that business success. You just keep beating at your craft until you succeed. So as an athlete, you might lose the game. You might have a losing season but you still go to the gym, you still go to practice, you don’t give up, you keep going. For me, that’s where the failure’s not an option. You might lose battles, but you don’t ever give up on the war.

Jarie Bolander: Right. No, no, true. And I’m glad you clarified that because there’s the bluster of “failure’s not an option, we’re just going to crush, crush, crush.” Like if you’re of the Jocko Willink mindset, which is not really his…

Dylan Ogline: Yeah, I love Jocko.

Jarie Bolander: Yeah, I mean it’s subtly that way, but he’s way more nuanced than that because he understands, “Well, you’ve got to pivot, zig and zag, and cover and move,” is what he likes to say, and you’ve got to adjust. Because, again, the world is so random or it can be so random that you can never anticipate everything that’ll happen. You just can’t. And so like the best example is COVID, right? So what really like struck me about COVID, and I remember in San Francisco we shut down March 15th, the weekend of March 14th and 15th everyone’s like, “Hey, Monday, shelter in place,” right?

So I remember, I was with my fiancé Minerva, and we’re at the store. And it’s chaos, I mean absolute chaos. Lines, there’s no toilet paper, there’s this whole like… And because I’m like, “Eh, is this really that bad? They say it’s just the flu, right?” And then I’m like, “Oh, oh my gosh. I need to adjust my thinking pretty quickly, because, like wow.” And then I started to realize it’s like within a week or within a day, a couple of days, all those businesses that relied on foot traffic, that relied on in-person-- travel, conferences, all of them-- like overnight 90%, 100% of their business is gone.

Dylan Ogline: Yup.

Jarie Bolander: And you’re like, wow, well therein lies the lesson, right? The lesson of well, if clearly you couldn’t have done anything to prevent that, but how you react to it is your thing about well, failure is not an option because I’m going to figure out a way to make this work. Is it going to be virtual conferences? Whatever I’m going to do, I got to figure this out, and I’m not going to quit, which is also like sports, we talked about the sports taught me is even when you’re losing, don’t quit. Keep putting out the perfect effort. Keep putting the effort out. Because in sports, as you know, sometimes the last minute of the game you win it. You’re like, “How did that happen?” We had more heart, right?

Dylan Ogline: Didn’t give up.

Jarie Bolander: We didn’t give up. I remember we were playing a game, it was like the last quarter, and we were down like two to nil, and like in soccer that’s like a blowout, right? I mean two to nil, no one ever scores, right? That’s why Americans don’t like it as much.

Dylan Ogline: No, we don’t.

Jarie Bolander: Yeah, right, and hockey.

Dylan Ogline: That’s why.

Jarie Bolander: Yeah, that’s why, because it’s so boring, right? But it’s the beautiful game. You got to love the beautiful game. But I remember it’s like everyone’s a little dejected, but then one guy, he’s like, “I’m not going to give up, and I’m just going to keep hustling and hustling and hustling.” And I remember, you could see the other team was sort of slacking a little bit because they’re like, “We’re up two nil,” right? All of a sudden, we score. Now it’s 2:1. Now the momentum, like when people talk about sports momentum, and they’re like, “What does that really mean?” It’s a real thing.

Dylan Ogline: Oh, it’s real. It’s real.

Jarie Bolander: Because just like in battle, the tide of battle can be turned by individuals pulling the collective together, pulling the troops together, and really like stellar performance. And this guy scored, and we’re like, “Hey, we got a shot.”

Dylan Ogline: Tie this.

Jarie Bolander: Yeah, we could tie this, right? We just kept on going, and kept on going, then boom we scored another goal. So now it’s 2:2. We’ve got five minutes left and it’s like, “Wow.” And we just felt like on top of the world and because we didn’t give up. And because when, as you know right, the clutch players, the clutch players in all sports, and even in business you see this in business too. Like those sales people that just won’t give up, the biz-dev person that’s just like dogging the deal, maybe some of your clients or your team that’s just like, “God, we ‘ve got to get this done.” It’s like this is so important. That little bit of extra effort that “I’m not going to quit until the game’s over,” that sportsmanship, that perfect effort, I’m just going to keep going until I can’t go anymore, the best thing an entrepreneur can do. I mean, sometimes you lose the game, right? Sometimes you lose the game.

Dylan Ogline: Yeah. But then you get the lesson.

Jarie Bolander: 100%.

Dylan Ogline: So you have to realize like even if you lost, even if your business closes done, even if it fails or whatever, which again me personally I can sit there and I could say, “I have failed a lot more than I have succeeded. I still tried to take a lesson away from all those things.” But for me, where the burning bridge comes from is like, again, it’s a fine line.

Jarie Bolander: 100%.

Dylan Ogline: It is a thin line. Where if you have that back-up plan, or something like that. I didn’t have parents who were going to pay my mortgage or something like that.

Jarie Bolander: Yeah. Well, there’s that.

Dylan Ogline: If I didn’t make it work, I would go hungry, like there would be no food. And a lot of people they have that, they keep that back-up plan, and they give up in the third quarter.

Jarie Bolander: Yeah.

Dylan Ogline: Because, well, we’re not going to work. And it’s like, no, you don’t give up until there’s nothing left to give.

Jarie Bolander: Yeah, until the buzzer sounds, right.

Dylan Ogline: Until the buzzer sounds. And then if you sill lose, well, then you look, evaluate what was the lesson, and you go back to the next game, you go back to battle again, you don’t give up. There’s a lot to be said about that, man.

Jarie Bolander: Yeah. No, and I agree. I mean what’s interesting about like my family’s the same way. I mean my parents weren’t going to pay my mortgage or help me out because just they didn’t have the means. I mean it’s not that we were hungry or anything, but it’s like, hey, we got our thing, you do your thing. And I think the level of discomfort and the level of what you really need to survive, a lot of people that haven’t like gone down that path of like, “Oh, I can’t eat today, how am I going to make my mortgage? Oh, I got to work a double shift.” When you do that then you’re kind of you level set what you can handle.

Dylan Ogline: Your pain threshold.

Jarie Bolander: Your pain threshold, right, and I think the stoic’s similar right there. They like always up how much you can tolerate. And then obviously, don’t let the emotions get to you. But when you have that mentality, and you have that hustle, and you have been like conditioned to be like, “Okay, we don’t give up til the game’s over.” One, it’s freeing, I think. It’s just this freedom that’s pretty amazing and hard to explain.

But also what you need to survive is not as much as some people think, right? So if you’ve never had the means, if you never were rich or whatever, like the level of what you need to survive is pretty low. I mean, to be honest, right? It’s like I can live on ramen and I’m good, right?

Dylan Ogline: Yeah. That’s absolutely fine. I’m fine with just a glass of tap water.

Jarie Bolander: Yeah. Exactly, right? And that was the other thing during this whole pandemic thing where you really see a lot of people struggling, but then also kind of pulling together and reassessing like what matters. And I’m curious as you’ve been through this journey, have you kind of assessed what really matters to you? And I know now you’re successful, and you have a successful digital marketing business, but how has that assessment been? Have you reflected on that?

Dylan Ogline: So I would say for me there’s two things. I continuously try to practice gratitude towards everything. So I look at things like this is something I teach students to a certain degree is I hear a lot of people, they say-- especially with business—“Well I don’t have like rich parents that I can borrow money off of to start my business or whatever.” And they’re like, “I come from poor means, I come from a poor family.” And I’m like you’re lucky for that. The worst thing that can possibly happen to somebody is that they become comfortable.

Jarie Bolander: Oh yeah.

Dylan Ogline: The comfort is an absolutely terrible thing.

Jarie Bolander: Oh yeah. Oh yeah.

Dylan Ogline: I consider myself so, so lucky that I came from a small relatively poor country town in Pennsylvania. I look at people who their parents are millionaires, and they’re going to get a million dollars whenever they die, or they have a trust fund. And I’m like, “I feel so bad for that person.”

Jarie Bolander: Yeah, I’m with you.

Dylan Ogline: Because they’ve never wanted, they’ve never struggled. And, yeah, so like that deep fire just isn’t there because they’ve never tested that pain threshold. They don’t know what real struggle is. I don’t even know what your original question was to be honest.

Jarie Bolander: No. No.

Dylan Ogline: I continuously feel this gratitude.

Jarie Bolander: This is good anyway. Just keep going. Keep going.

Dylan Ogline: I continuously feel this gratitude that like that shit that I went through when I was a million dollars in debt, losing sleep, like how am I going to get out of this mess? I am so thankful that I went through that.

Jarie Bolander: Yeah.

Dylan Ogline: In the moment, I think this was probably the big shift because I had that kind of stoicism background, and before it like reached its peak badness in my life. In those moments I specifically remember the low point for me was I was doing a flip house. I bought this house for like $35,000, and I ended up losing money on the deal, ended up losing like $3,000 or $4,000. But I had like maxed out all my credit cards, so I’m like trying to finish the project, but I’m like I don’t have anymore money. So like I’m trying to cut corners as much as I can, so I wouldn’t turn the AC on. This house is in Florida, it’s like July or something like that. It’s 100 degrees and the ceiling I think was popcorn, they call it popcorn ceiling or whatever.

Jarie Bolander: Yeah.

Dylan Ogline: And for some reason I was taking a spray bottle. Like to scrape it off, the best way is to like get it wet and then you scrape it off. And, dude, it’s just everywhere. That was like six years ago. That was 2015.

Jarie Bolander: Wow. Wow.

Dylan Ogline: And I remember sitting there and I’m like drenched in sweat, I’m covered in dry wall, and I’m like, “Well, I’m glad I’m in this moment right now. Like this sucks, but I’m glad because dude, this is pretty bad.” Like that pushed my pain threshold. So by pushing that pain threshold, when I go through other struggles it’s like, “Well, it wasn’t as bad as that.”

Jarie Bolander: It could always be worse.

Dylan Ogline: It could always be worse.

Jarie Bolander: It could always be worse. Yeah.

Dylan Ogline: Yeah, it’s just like lifting, or something like that. Like 100 pounds might be heavy to somebody, but if you continue to lift 100 pounds, and then you lift 150 pounds, and then you lift 200 pounds, all of a sudden 100 pounds becomes pretty light to you because you increased your pain threshold, your tolerance. And again, I have no idea what the original question was, and why I went off on that.

Jarie Bolander: Well, I mean that’s the goal.

Dylan Ogline: That’s my answer.

Jarie Bolander: Yeah. Yeah.

Dylan Ogline: Whatever the question was.

Jarie Bolander: That’s the whole the obstacle is the way of stoicism where you embrace the struggle, and being comfortable with being uncomfortable with the situation you’re in, which is something that I’ve always tried to champion. And it’s not like you got to suffer all the time, right? I mean there’s a certain part, of course we all don’t want to be masochists, but when you struggle and you push the limit of your tolerance, then you learn a little bit more about yourself, then your threshold of pain and suffering goes up a little bit.

Now there’s times where you completely collapse and you can’t handle it, and that’s when you need a team, and a tribe to support yourself, which I’m sure if you absolutely hit rick bottom I’m sure your mom and dad would be like, “Okay, come on.”

Dylan Ogline: Here’s some ramen for you.

Jarie Bolander: Here’s some ramen. Let’s take a break and figure out what the hell you really need to do with your life. I mean I always had that with my parents. I mean, the desire to not do that was really, really strong to not go back home. But I mean that’s what a tribe’s all about, that’s what people that love you all are about, that’s what that support network of a community of entrepreneurs where we’ve got each other’s back, right. Because that’s important. Because this job is a hard job, right?

Dylan Ogline: I think we’re kind of conditioned as a society where I don’t think the bigger problem is getting through the bottom. The bigger problem is once you start to go up and you start to get success. Whether that’s athletic success, or financial success, or whatever you lose sight of the bottom. You forget what the bottom looks like.

Jarie Bolander: That’s a great, great point.

Dylan Ogline: So in stoicism, what is it? Like once a month you’re supposed to wear the cheapest fare? Like basically like once a month you’re supposed to wear terrible clothes, you’re supposed to eat the cheapest food, you’re supposed to like sleep on the floor with like just no pillow. I mean everybody’s got different extremes, but in stoicism they talk about this kind of like pushing your limit and reminding yourself of I can get through the badness. A particular story that I remember with stoicism, it might be Marcus Aurelius, I don’t remember who it is. But for those of you who don’t know, he was one of the emperors, right?

Jarie Bolander: I think so. I think so.

Dylan Ogline: So no matter who it was.

Jarie Bolander: We’ll fact check that.

Dylan Ogline: Fact check me after this. I’m going to butcher the story. But the story that I took away from it was this emperor, which back then these people were gods. They could walk out onto the street, murder somebody, and nobody would question them. They were worshipped like gods. And like once a month he would sneak out of the palace or whatever they called it, and like live with the poor. For like just one night or whatever, live with the poor, eat their food, live on the street, sleep on the street to condition yourself to one: feel gratitude and how lucky you are, how lucky you have it. And just be like, “I could lose it all and I could still get through it.”

So people can go through struggle, your Mercedes might get repo-ed, or you might not be able to eat organic foods, and you might need to go to ramen noodles. Like conditioning yourself that like I can survive that is a very, very, very powerful tool. And I’ve seen a lot of people where they start to get success and they forget that. So that then whenever maybe things start to slide a little bit, they panic. Because like, “I wouldn’t be able to survive off of ramen.” But it’s like you did once, or I guarantee you, you could.”

Jarie Bolander: Yeah.

Dylan Ogline: So I think that’s probably the bigger. Most people can be conditioned to handle the struggles when they’re starting out but it’s really whenever you start to get success that you lose sight of the bottom

Jarie Bolander: Yeah. Well, Dylan, I think that’s a great place to end. I really, really appreciate your time, and it’s great to get to know you. Such an insightful discussion.

Dylan Ogline: Thanks, man. I wish I could articulate the whole stoic experience a little better, but I hope that helps you.

Jarie Bolander: Oh, yeah. I mean, you’ve got time, my friend, you’ve got time so. All right, take care. Thanks for listening to “The Entrepreneur Ethos” podcast. I hope you enjoyed this episode as much as I did creating it. My hope is that you learned something that can make you a little bit better. If you enjoyed the podcast, please do share it with friends and review it on Apple Podcasts or Spotify. You can also join my email list by visiting to get my thoughts on what I’m doing to get better as well as what I’m working on. You can also pick up my book, “The Entrepreneur Ethos” if you want to learn the traits, values, and beliefs that I think we need to build a more ethical, inclusive, and resilient entrepreneur, and frankly, world community.

Feel free to follow me on Twitter @thedailymba and let me know if you have any questions or recommendations for a guest you’d like me to talk to. Also drop me a note if you try anything we talked about on this or any other episode. I’d love to hear what’s working for you. Until next time, keep getting better.