Jarie Bolander: Mastering The Art of Marketing Through Storytelling #221

In this SaaS District episode, host Akeel Jabber interviews Jarie Bolander, founder of StoryDriven, about the pivotal role of storytelling in B2B marketing. Bolander shares his personal journey—from a petroleum engineer to a PR/marketing consultant after taking over his late wife’s firm—and how that experience taught him that a compelling story is the single most important metric for startup success. The conversation explores why many B2B founders neglect narrative, the impact of story on pitch decks and investor perception, and how storytelling can differentiate a product in a crowded market. Bolander outlines the foundational frameworks he uses—Aristotle’s rhetorical triangle (pathos, logos, ethos) and the hero’s journey/three‑act structure—and introduces his “big idea” concept that combines problem definition, emotional appeal, and credibility. He provides concrete steps for marketers and founders: shift from a product‑mindset to a solution‑mindset, clearly define the problem for the target “hero,” craft a concise big idea, and align the team around it. The episode also contrasts B2C and B2B storytelling, emphasizing that B2B marketers must make the buyer the hero of their organization. Bolander discusses challenges around self‑promotion, recommends resources such as his StoryDriven scorecard, and cites books like The War of Art, Category Pirates, and Loonshots. The interview wraps up with rapid‑fire personal questions, revealing his practice of Brazilian jiu‑jitsu and his advice to learn how to sell.
Chapters
Hello, hello everyone. This is your host, Akeel Jabbar, and welcome back to another episode of SaaS District. In today's episode, we'll be talking about mastering the art of marketing through storytelling. Today we have our guest, Jari Bolander, joining us. Jari is the founder of StoryDriven, A company that utilizes storytelling techniques to accelerate brand awareness and generate leads for B2B businesses. He has a track record of working with startups where he has successfully raised over $10 million in funding and played a key role in a $750 million exit. So welcome, Jari. Super excited to have you on the show today.
Yeah, Akhil, thanks for being here. You're— I know you're on vacation and you're doing this anyway. You're so dedicated to the cause. It's a Just an honor to be here. I really appreciate it.
Oh, no, thank you. Thank you. So I'd love to talk about your background. I'm also an engineer myself. I used to be a petroleum engineer, and then you transitioned to the world of marketing. I did this as well back in 2015, I believe 2014. But yeah, I'd love to hear your story.
Tell me. Yeah. So both of us went to the dark side, right?
Yes, exactly. Exactly.
You know, you're an engineer and, you know, rational, reasonable. There's physics, You can't break the laws of physics, right? Then you get to marketing, it's like, welcome, 2-drink minimum, come on in, right? We don't know what we're doing most of the time, right?
Yeah.
So, I mean, I got into doing sales and marketing storytelling consulting actually through my late wife, Jane, who owned her own PR and marketing firm.
Okay.
She died 6 years ago from leukemia. Which was obviously not a great thing. But when, you know, when she got sick, I had to take over her business. And so I rapidly transitioned from founder of a digital health company to PR and marketing maven. And I had no clue what the hell I was doing other than the fact that I write okay. You know, I wrote a couple of books and really learned from her and then learned from just my experiences that really the best story wins hands down, full stop. I mean, you can build anything, to be honest. And I just found, you know, constantly over and over again that getting the word out about what you do, getting the story straight, understanding how to align internally was pretty much the one metric for success that not a lot of B2B companies either understood or paid much attention to. So after that sort of epiphany, I just started again, went to the dark side, did a bunch of startups and helped a bunch of startups with their messaging and positioning and Now I'm at Decision Council where we do B2B sales and marketing consulting and found that the secret sauce is that narrative, just so critical. And it's hard to do, hard to get right. But once you get it right, it's like magic.
It's interesting you say that because I speak to as well CEO founders from startups at early stages, pre-market fit. All the way to publicly traded CEOs, and I see their pitches. I see they pitch me all the time, and the difference is you know the product isn't that much better. Like I look at the product, I look at the team, and I look at their backgrounds, and I'm like, you guys are not that much better. We have a really, really nicely, beautifully crafted presentation. It's just it's on flow, it's on tempo, communicates effectively. And so I just noticed that, and I was like, well, what's what's going on here? But I I would love to hear more about the importance of what you've seen in storytelling and you know B to B marketing. And how does that impact the overall business from, you know, brand awareness, lead generation, all the metrics that we're tracking here?
Oh yeah, for sure. And then I think you nailed it right on the head. I mean, I wrote a book called Story Driven Decks a while back, and the guy that wrote the foreword was this guy, Steph Nasser, over at OpenVC. I'm not sure if you're familiar with OpenVC, but it's a platform that founders can try to pitch VCs, right? So if you've been in the startup game long enough, literally, if you're seed, pre-seed, friends and family round, whatever, like your startup, it's all about raising money. Like, that's just the way it is. And Steph, he himself has looked at like 3,000 pitches. I've looked at hundreds and hundreds of pitches, and he did this great thing. He did this open VC. They called it the roast. So they would literally roast people's pitches. And so I watched all the videos, took everything that they were talking about, and then all the experience I had. And I wrote this book, right? And you nailed it when it was The difference between getting the next meeting, which is the only thing that your first pitch deck needs to do, is like, just get me interested enough so I can take a meeting, was how well it was put together. Was it well designed? Did it tell a cohesive story? Did it hold together?
Yeah.
It needed the team and the traction, but if you looked at all those decks, 80, 90, I would say 90% of them failed to tell a good story. And it just makes you as an investor, because I've done investment as well, when you see a good deck, you know that they were thoughtful and they thought about what they were trying to do. And it's your first marketing collateral that matters. And if it's not done right, you're just going to throw it in the trash. I mean, I don't know, how many decks have you seen in your career, right?
Yeah, probably 1,000, I would say.
Yeah. And you keyed on to the most important thing.
Yeah.
And everyone may complain, oh, it's about the price, should be about the team. No, it's the presentation, it's the story, it's getting past the noise. I looked at 1,000. I don't have time To understand what you do. I only have time to figure out my criteria of, did you spend the time to do it? Does it tell a cohesive story? Am I interested? That's all I have.
Yeah, exactly. I mean, the only time I could say where I'd probably skip the filtering of that level is if it's like a close friend who I know is an entrepreneur and he's reaching out to me with some kind of napkin email, right? Then I'll have the conversation. But otherwise, yes, if I don't know you and if I'm trying to If you would like to have a meeting, then yes, all that matters, right? That's how you can differentiate it. That's the only way.
For sure.
For sure. Why do you think is it that most people, even myself, I think I can say for the longest time, even now I still struggle with it. Why do B2B marketers, founders hesitate to include this as part of their vision of their strategy and showcasing their solution versus focusing on the product and just getting the product perfected or raising the capital or whatever it is?
I think the main reason is they're afraid to summarize what they do in a clear, concise, and compelling way. I think once they, you know, they got your attention, they want to shoot their shot, right? So I always tell people the one question that your deck, your pitch, your elevator pitch has to invoke in the person's mind that you're telling or pitching is, You want them to say, tell me more. Like, tell me more. That's all you want them to do. You don't have to inundate them with data and bullshit bingo, right? Like buzzword bingo. You just don't. And I think the confidence in saying, giving them enough to say, tell me more, is what's lacking. And I also think people don't really understand the power of The person— like, we're all people who resonate with stories.
We—
it's baked in our DNA. I mean, you and I are talking on Zoom because our ancestors told the best stories, just full stop, hands down. Like, there's no doubt, right?
Mm-hmm.
And I think people that don't tell stories for a living or don't— haven't crafted a story, they get nervous because It's hard to do right. And they just revert back to, oh, I'll just tell them a bunch of features, right? And once you get past the fact that product is democratized, and to your point, you've seen how many of the same product, it's like, this stuff's not hard to do, right? And you and I are both engineers, so we know in our gut, like, yeah, I could build that.
Yeah, exactly.
It's the story around it.
How—
why am I gonna believe you? Why are you the team? You know, and people have a real hard time because it's more subjective. You know, it's a little more squishy. And I also think people don't have the confidence. I really think the confidence is lacking.
They don't feel they don't have a compelling enough story to tell.
There's that, or they think that that doesn't matter as much, especially in B2B. You know, if you're in the B2C or direct-to-consumer, oh yeah, of course, it's all people buy an emotion and validate on logic. Well, B2B is the same way. It's not— we're all human.
Yeah, that's true. You know, there's also the other side. You know, it's interesting you say that they were compelled to— where we don't feel compelled to ask. We also hear Other side where I've mentioned that to folks who are like, hey, I'd like to hear more, you know, I extend that out and maybe they don't hear it as well. So there's the other side too of like being able to identify it when you do ask for it to follow up on that as well.
So it's— Yeah, for sure.
What would— so, you know, if you're— if I'm looking to compel, you know, so you have this, you decide that this is important to you, you want to build storytelling into your B2B strategy. Where are you pulling from? What are you pulling together in order to create and compel a great story here? What's the best framework you wanna approach this with?
Yeah, so the best framework that is basically the basis for every other framework in marketing, especially any kind of influence peddling, any kind of communication that tends to, you know, marketing's job is to influence people to take action. Bottom line, right, is Aristotle. Aristotle's rhetorical triangle. He's the godfather, great-great-great-great-great-great-grandfather of persuasion. He had his rhetorical triangle, which is 3 parts. The first is what's called the pathos or the emotion appeal. First and foremost, you always got to appeal to the emotions. That's full stop. If there's no emotional appeal, no one cares. Story is about change and emotion and invoking action. Like the status quo gets interrupted because I invoke an emotion. Second part is called the logos or the logical progression to go from I have a problem to this is the solution. So every, you know, every company has to, oh, I have a problem. Company, what is the logical progression to get me to the solution? And then the last one is called the ethos or the credibility. Why should I trust you?
Hmm.
You know, why should I trust you to be able to solve my problem? Very simple. And it's basically also the 3-act structure of any play. There's also something called the hero's journey, which is Joseph Campbell. If you've seen Star Wars, Die Hard, any movie is based on that hero's journey. So basic framework and that's the basic framework starting point I use for story-driven. You know, I didn't invent any of this stuff. Like this stuff's been around for thousands of years. It's just applying it to B2B marketing has not been done very effectively. There's great people that do it, you know, guys over at like Wynter, wynter.com, you know, Peplaya does a good job, you know, Metadata does. I mean, they do an okay job, but there's no one sat down and said, well, How can I apply this to B2B marketing or in general, how can I apply it to marketing, but specifically B2B marketing? And I think those are the basis, those frameworks. And then of course, you know, you build on top of that, of what I, what I've done. And I think it's fundamentally, it's in all of us. I mean, if I always say, if you've ever gotten a date, you've ever gotten married, you've ever convinced someone that you've told a good story.
Yeah. Yeah. I mean, it's interesting, right? So you, you know, you're in this world of the B2B world and, you know, LinkedIn, et cetera. Or in the dating world, essentially, you have these stories. People are sharing their stories online, and then you're thinking, how can I come in with a story to share that's equal or outshine them? Right. In some ways, because that's— you have to push. Otherwise, why would you share a story if no one's going to listen to it if it's not as exciting as what the others are? How do you go about that, and why is that so important?
Yeah, well, I think there's a lot of noise in the world, right? I mean, if you're in If you're in marketing, if you're in like SaaS marketing tools, there's 10,000 of those things. Do we really need another SaaS marketing tool? No, we don't actually.
Exactly.
But what we do need is we need solutions to solve the problems that marketing people have. So it's really in the way you craft your solution to a problem that a potential prospect has, right? So that is what's gonna resonate. It's, I need to solve a problem. You can help me solve the problem. It's no surprise that people are focused more on solving problems, right? That, like, that's what I care about, right?
Yep.
And so I think more importantly, what you wanna do when it comes to that Is it's not about like telling the most awesome story you can. Like, don't get me wrong, like you can strive—
If you're an email marketing tool, like how exciting can you make the story?
Exactly. You can't. But there's always, so I always say you gotta have your big idea, right? This is another part of my kind of framework. So the big idea is what, why do I care? What pain do I solve and what, why am I unique? And your big idea has to have those 3 components because that's the opening hook, that's the beginning hook, that's the emotional appeal. So even if that's quote unquote boring or not as exciting as something else, it's unique to you. You make it your own because someone's gonna resonate with that. You just have to find the people that are gonna resonate with that. And so it never has to be perfect, but it has to be your authentic self. It has to be like, we can deliver on this. And every company has something unique. And if you don't, why are you even around? There's gotta be a compelling reason to buy, right? So yeah, I'd say that.
Makes sense. What can we learn from the— so B2B is this Yeah, you have these products, email marketing tool. B2C, you have a lot more exciting products that you can, you know, sounds like it just seems as the stories are way more easier to put together and craft that maybe we can learn from and try to apply with those tactics or strategies.
Oh yeah, for sure. I mean, I think the reason why the B2C side has resonated so much with the storytelling is because it's usually a single person that's buying something, right? Like, you know, you go to Canva, which is also B2B, but also, hey, B2C, right? It's just, you can start right away and start creating, right? You've got all these brands that where there's only one single decision maker and that single decision maker happens to be the consumer who happens to be able to, who is really not justified it on logic, but the emotion that it pulls into. So there's this great brand called Easy Plant. I don't know if you've ever heard of Easy Plant, but I wanted to buy some plants for my apartment and I could go down to the nursery, buy a plant, a pot, everything. But the problem I have is I don't know how much to water them. It's like a real pain. Easy Plant, literally solves this problem. They're like, it's self-watering, it's in its own plant, we'll ship it to you, easy peasy, no fuss, no muss, right? And their marketing is, this is a big problem for someone that wants a plant. I'm going to kill it. I don't want to kill the plant, right?
Right.
And the way they just tell the story is just, it's solving this problem I have in a way that's pretty unique and novel. And yes, someone else could do it. Sure, of course. But I resonate because, gosh, this is a real problem I have. And when it's a single person, single consumer, it's very easy to talk directly to them.
Right.
Whereas with B2B marketers, you know, you've got your personas, you get your buying committee, but that still doesn't mean you can't talk to them personally. And I think that is the one thing that B2C gets. They make the personal appeal, they make it, they make the problem personal, you know, and that's, that I think is what we lack in B2B.
Well, it actually makes sense. I mean, B2C, this is a product that's gonna solve your personal problem in this way, you know, you're solving the problem, but at work, So maybe we don't value it as much because it's not paid from our own pockets, you know, the business. I don't know. I wonder if that's kind of the psychology behind it, why B2B is less personal, because it doesn't feel like it is solving my problem and like the resource and for the business.
But I don't know if it's actually mine. Right. And you have a big stake in it when it's your personal money as opposed to your company money. But I do think if you look at like a buying committee in B2B, There's all sorts of levels in an organization. There's gonna be the tactical person that's gonna actually implement the tool. There's the manager that's gonna be overseeing that and using it. Then there's the C-level that's gonna approve it and look at the strategy. What's the ROI? Blah, blah, blah, blah, blah, right?
Exactly.
Each one of those has a story they're telling themselves about why they need, you know, Wynter, why they need Salesforce, right? They just, there's a narrative and honestly, As the example of Salesforce, there's way better tools than Salesforce that are way cheaper. Yeah, but people will just buy Salesforce because you never got fired for buying Salesforce, just like you never got fired for buying IBM. But it's, it's, it's the story they tell each other. It's not as good, clearly, but the story people tell it.
It's the safest option. Yeah, right.
Yeah. And so the motivation is not necessarily the best solution.
It's Yeah.
What's the solution that's not gonna get me fired?
Exactly. How can I make this person's job? There you go. There's the answer. How can I make their job more easier, get them a raise, and get this person noticed? Yeah.
I mean, think about it. And the way I think about it is you're in the hero-making business. This is what we say at Decision Council all the time. It's like we're in the hero-making business and you're like, what does that mean? It's like, it's not about us. It's about the hero, like our client, the hero being a hero to their organization. And that's the thing that's different about B2B as opposed to B2C. B2C, the consumer and the hero are the same. B2B, it's usually you're selling a tool to make someone else the hero of the organization. Like you get Salesforce, the reason why you buy Salesforce is so that your CMO or your sales, you know, you're making the VP of sales more productive, better, faster, cheaper, whatever. You're making them the hero of their organization. It's not you. You're the mentor. You're the one that's helping. You have the knowledge. And I think when you sort of shift from, I am not the hero, I am the mentor helping the hero save the victim from the villain, like in every great, you know, every great movie has that.
Robin, Batman and Robin. Yeah, whatever.
Or even, you know, even Star Wars. Look at Obi-Wan Kenobi, right? It's like Luke's the hero, but Obi-Wan's the mentor. Yoda is the mentor. They're the ones with all the knowledge. They're the ones that are the most, have the most power.
That's called the magician archetype, I believe, right?
Yeah, in some cases. Yeah.
What would you say, or maybe so, you know, kind of to wrap this up, if I'm a B2B SaaS marketer today or founder, what are some actionable steps you can share with them to enhance their storytelling abilities today and start effectively communicating their brands out?
Yeah, I think the first thing is you have to find the solution. Like you have to have a solution mindset, not a product mindset. So I'm solving a problem. What problem am I solving? Who do I need to talk to in order to get my solution to solve their problem? And that is a more emotional, that is evoking an emotional appeal, an emotional response to Oh, this is a problem I have. And then you need to be credible that you can solve the problem. So I say, I would say, what problem are you solving? Like, to really clearly define the problem that you're solving for your hero, which is gonna be, you know, VP of marketing, you know, director of demand gen, whoever it is, right?
Yeah. Yeah.
That's one. Like, really get clear on that. And then I think the second thing is really create something called the big idea. That is a little bit beyond just the tagline, but it's like a very clear, concise, and compelling statement that is meant to align internally. Like, this is what we do. And this sounds shocking, but there is not a lot of B2B companies I've worked with that actually do that.
What they say and what they do, you mean?
Or just the big idea, you know, like, it's not that big, you know, like just a single statement. It's like your elevator pitch, but like, because most of them deal with, these are the products we sell, not the solution, like, not, this is not the problems we solve.
Yeah.
And mostly they don't say why, like, why does this matter, you know? So I'd say those 2 things are the most important.
Seems so simple. You make it seem so easy, right? We just kind of—
Well, the simple stuff most is the hardest, right? Like somebody the other day was saying to me, explaining what you do or teaching someone what you do is way harder than writing down what you do. And it's true because the simple takes— when you take complex ideas and make them simple, That is infinitely harder than just spewing a bunch of complicated buzzword bingo. It just is.
I completely agree. Cool. This has been awesome. Ready to kind of shift gears and go to the second part of the interview, the rapid-fire questions?
Yeah, let's do it. Yeah, yeah, let's do it.
All right. What's one activity outside of work that gets you into flow state, Joey?
Brazilian jiu-jitsu. Oh yeah, I'm a blue belt in Brazilian jiu-jitsu. So I do that in order to really, you know, get in the flow state and really make my problems less small.
Yeah, that's awesome. What's one piece of advice you wish you had known? And if you can go back, you would tell your Say 20 or 25-year-old self.
I would say learn how to sell.
Learn how to sell.
Really?
Yeah.
That's my biggest flat spot is self-promotion and selling. That's the reason I'm on your show.
Yeah.
Yeah.
Fair enough. Yeah.
You know what I mean? Like, it's especially as engineers, right? I'm sure you've had the same. It's like, it's just so hard to self-promote. It's so hard to sell. And I really think that skill, that's one of the skills I'm working on. So I really appreciate you having me on the show and talking about this because it's helping me build that muscle.
No, I totally understand. What got me good at selling was when I was like 16, I did door-to-door sales for a year and I got really, really good at it. I realized the same thing you're describing. I got really good at it by selling other people's products. But yeah, but when it comes to selling yourself, I'm really good at product marketing and sales for others. But then it's like, whoa, selling myself and my story, this is a totally different game. So I get it. Kudos and respect for you for being here.
For sure.
Yeah. What are some of the biggest challenges you're currently facing in order to continue to grow your, you know, brand StoryDriven? Is there anything, you know, you're looking forward to, to continue to grow going forward?
Yeah, I mean, I think it's the promotion and getting over the yucky feeling of self-promotion. Yeah, you know, it's, it's a hard thing to do. That's why it's such a skill that needs to be fostered. I mean, the reason I do my own show, The Entrepreneur Ethos, is I practice talking to people. Like, it's hard for me as an introvert to do.
Yeah.
So it's, you know, like anything, it takes practice. But it's like the one thing that's like, how do I get the word out? How do I be thoughtful? How do I not be that guy? You know, it's like Orly, Selly, Selly. Yeah. And it's just, yeah, it's just a skill. You just gotta be okay with it.
Yeah. Just keep practicing the work of the muscle, right? Yeah. Is there any maybe favorite resources, you know, books or mentors or people you follow in the space that have been, you know, most instrumental to your success over helping you these last few years?
Yeah. Yeah. I mean, The War of Art by Steven Pressfield's a great book. that I highly recommend everyone do. I've just got into this one thing called Category Pirates. I'm not sure if you're familiar with them, but really opened my eyes to, you know, how to create a category of one and how to do all that stuff, which is great. And then there's a great book called Loonshots, which is just about how to come up with crazy ideas, you know, which is awesome. So yeah.
Loonshots?
Is that what it's called?
Yeah, Loonshots. Oh, cool.
Yeah, it's a great, great book. Not moonshot. Loonshot.
I know. Yeah.
Someone said you misspelled that. I said, no, it's loon, as in really crazy, really nutty.
Oh, it's probably a book. Yeah. How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries.
Yeah, it's a great book. Fantastic book.
Awesome. Check that out. Jory, what does success mean to you today? Whether personally, business, financial, life-wise, there's no right answer.
I think it's freedom. Freedom to do what I want to do. I think that's what I'm really trying to figure out. I love the idea of free to be you and me and do what I want to do. Also, of course, make a living and not have to starve. And I think that's more of the creative artist in me. So I am really— to me, success is the freedom to do what I want to do, build an independent life that completes me, and not have to worry about You know, money, my next paycheck kind of thing. That to me is the ultimate.
I agree completely. Love it, Jerry. So where can founders, marketers, anyone listening in get in touch with you, learn more about you and or your company if they wanna, and also learn about your scorecard as well?
Yeah, so getstorydriven.com is the story-driven, you know, B2B marketing stuff. There's also something called a scorecard. It's called Scorecard Marketing if anyone's interested. You can go to scorecard.getstorydriven.com and that will allow you to take a free quiz that'll give you an assessment of, hey, this is where I'm at in my storytelling journey, along with some ways to actually improve it. So one of the things I'm really trying to do and foster is not only getting the word out about the power of storytelling, but, hey, this is how you can do better. This is how you can make things better. And again, it's Not that I'm some genius at it, it's just that I just so happen to study story a lot and I realized, oh, epiphany moment. Oh man, you know what? You can apply this to B2B marketing and you get great results. And it's just, you know, it's something that I've always been curious on and love to help people. So I hope everyone can, you know, check out getstorydriven.com or go to the scorecard at scorecard.getstorydriven.com and See what it's all about. Yeah.
Awesome. Yeah, guys, make sure to check it out. I mean, as we talked about, like, this is stuff that is transformational to your business. Doesn't matter how good your product is, how good your financials are. If you don't have a good story, you will not raise capital. I mean, it'll make it a lot harder to raise capital. So I hope you guys make sure to check them out. getstorydriven.com. And thanks again, Troy. I really appreciate you joining today.
Oh yeah, anytime. Anytime. I really appreciate what you're doing and Thanks for having me.
Thank you.
Thank you.
Cheers. Thank you all for watching this episode and joining SaaS District today. Don't forget to like, subscribe, and hit the bell for future episodes where we interview top leaders in the SaaS industry. If you're a SaaS company looking to grow and unlock the true value of your business, get in touch with us at Horizon Capital and myself or one of our consultants We'll provide a free assessment to help you get there and hit your goals. If you have any feedback or suggestions for this podcast, please comment down below and help us improve our content for you all. Thanks again, and see you on the next one.
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