Creativity in Constraints & Mastering Product Market Fit with Jarie Bolander
Join host Gboyega Adebayo in an enlightening conversation with Jarie Bolander, entrepreneur, author, and host of The Entrepreneur Ethos Podcast. Explore the transformative power of creativity and resilience in the entrepreneurial landscape. Delve into creativity, guardrails, understanding your story, and how constraints can catalyze innovation. Gain insights into ethical and inclusive entrepreneurship from candid anecdotes and expert advice. Tune in for invaluable wisdom to enhance your impact as an entrepreneur.
Are you an entrepreneur, start-up, or business owner with a great founders story? Follow this link to get featured.
FULL VIDEO TRANSCRIPT:
INTERVIEW WITH JARIE BOLANDER
Gboyega Adebayo: All right. Today I get to sit down with Jari Bolander. He's a serial entrepreneur, an author, and honestly, just talking to him for over the last couple of weeks, a really cool guy.
Jarie Bolander: Appreciate that, man.
Gboyega Adebayo: No problem. So welcome. Um, I want to dive right in. And before we start talking entrepreneurship and your experience, I start every conversation with what did you want to be growing up?
Jarie Bolander: What did I want to be? Wow. Um, there were many things, actually. thing I wanted to be was a fighter pilot. and actually pursued being a pilot. was 18, I actually got my private pilot's license when And then, uh, was like, yeah, I'm gonna go in the military, do all this cool stuff.
Jarie Bolander: And then, I met a girl and changed all that as so many stories, girl. Oh man, a girl, right? Um, but aside from that, it was, you know, engineering. Um, my dad was an engineer, so We were always building stuff, tearing stuff apart. I mean, he was electrical engineer. So yeah, I mean, just love to tinker and do stuff. So I'm like, oh, I guess engineers do that. . So I'll go to school and you know, got a degree in electrical engineering and spent the first part of my career designing stuff around semiconductor Very different than what I do now, , which we'll talk more about. But uh, yeah, that's what I wanted to do.
Gboyega Adebayo: Got it. So, so for the people, what do you do now? And help me paint the picture of how you went from semi conductor chips and being kind of an engineer into This weird, ridiculous lifestyle that we all choose of being entrepreneurs.
Jarie Bolander: Yeah, yeah, yeah. So, uh, when I got outta college, I went to a startup, you know, Silicon Valley in Everyone was in the semiconductor mean, chips were a big thing, you know, they were starting to build the I don't know if it really started in 95, but I mean, everyone was building chips.
Jarie Bolander: all these computers, people computers. So kind of the dawn of the personal 2000
Gboyega Adebayo: Yeah.
Jarie Bolander: So, I, I mean, the short answer is I'm unmanageable . I really am just not, I don't like authority.
Jarie Bolander: I'm pretty curmudgeony about that. And I just wanted a independent I got sucked into the Silicon Valley dream, you know? Like, hey, get some stock options and be rich one
Gboyega Adebayo: Yeah.
Jarie Bolander: It turns out that's not the case. Um, the job's a little bit more complex than that, don't huge exit.
Jarie Bolander: the fallacy that, you know, at least on what I try to tell young I try to tell my, podcast is something, just gotta love You know? You can make it to good living and maybe you get lucky and get an exit or become wildly Chances are that's not gonna happen. So yeah, I mean, spent the better part of my career doing startups biotech and, know, sensors and And then met another girl, , uh, got married and, um, when, uh, she got sick with leukemia. I, had to start running her business.
Jarie Bolander: that was a PR marketing and strategic communications for an engineer is like the dark side, right? I mean like come to the dark side to drink minimum for marketing, right? so I started to do that it turns out I was really good at it. And one of the reasons I was really good at it is 'cause one.
Jarie Bolander: If I write, okay, like I, I, just fun and I can bang it out. And two, I could explain complex things tech marketing and startups are notoriously horrible at trying to explain what they do. just naturally like, oh wow, you understand this stuff? I said, yeah, this stuff's not that hard.
Jarie Bolander: ah, what do you mean we have this SAS product and this beautiful, I go, Come on. I, I've, I've built d n a sequencing is nothing compared to the fact. So let's just level set. Like it's not, you know, you have another great tool, another great MarTech stack tool or whatever, blah, blah, blah.
Jarie Bolander: Fine. Okay. Not that hard. So yeah, I went to the dark side pretty, you know, back then. And, first started running her, her name was Jane, my Seven years she died six years leukemia, sucks.
Gboyega Adebayo: Yeah. Sorry about
Jarie Bolander: Yeah, talk more about that a little later.
Jarie Bolander: But, um,
Gboyega Adebayo: Yeah.
Jarie Bolander: ran her company for the better part of five years until the economy kind of went sideways as we're in right And I had to go get a day job, now is, B two B Sales and marketing strategist. Yay. Sounds like a cool name, right? I'm the head of market a company called Decision Council here in in Berkeley, California, and we help B two B Company, you know, companies in the B two B space with complex products and Grow and thrive and strategy, position, you know, all the buzzword bingo stuff, right? As you all since you were a consultant, you know exactly how fun that is.
Gboyega Adebayo: Exactly. It's, it's the, it's the fun, but, um, necessary things you got to figure out.
Jarie Bolander: Yeah. I mean, and as you know, right? It's, it's like a puzzle. It's, some of this stuff is really fascinating. Like, I, I, I won't lie, I give marketing know, I bash them all the time. 'cause it's like the inexact science, right? It's this, you know, every marketer I've ever met is just like paranoid schizophrenic.
Jarie Bolander: Just fearful that they're gonna be found out as a fraud because they don't even know, understand why it works. Right? But, but this is the, this is the joy and the fun of it, right? Because the strategies we come up with, you know, shape how a company grows and you can poo marketing and PR and you can say, oh, we need performance this and performance that.
Jarie Bolander: And I'm numbers driven and data-driven, and blah, blah, blah. I mean, I'm an engineer. I'm like more data-driven than most people. Um, and then you just kind of settle down to the fact that it's really a question of having a solid strategy and trying experiments to figure out what, what's gonna work for you.
Jarie Bolander: Because I think we know the space, the solution space on what can be possible, it's so complicated and performance marketing is not the answer. Brand building's not the answer. It's like this, this tapestry. You have to like weave this tapestry 'cause you honestly don't know what's gonna work.
Gboyega Adebayo: Right. It's, it's what I have found, excuse me, what, what I have found in my experience trying to grow my business businesses has been, you're a good marketer. If you can come up with a structured framework for experimenting, because the entire game is experimentation. Now, obviously there are, you know, this is how you.
Gboyega Adebayo: um, track and do analytics. This is how you track performance. These are the benchmarks, but in terms of what you actually do is an experimentation. And so if you can come up with a very structured way of experimenting. And like learning quickly, you become a better marketer and. Coming from my background, which is, listen, I was a politics major that found his way in technology and finance.
Gboyega Adebayo: So why am I here? I don't know, but in this world of finance. In technology, experimentation really wasn't part of the game. It was all kind of logic, practical, you know, okay. How do you balance, you know, competing priorities? But, but the marketing, I see the creativity in the art appeal to it. Um, but I also see why someone like an engineer could be very, very successful at it because, or a scientist, because they have a very solid framework for experimentation.
Jarie Bolander: I mean, I think you nailed it, scientific method related to some sort And I think, I wish, I mean, I, I went to grad school, got an M B A, you know, was step one.
Jarie Bolander: In the turn to the dark side . like, oh, really? You know, you really gonna go do that? I said, well, it's interesting, you know? I'm come on we should just build stuff and people should buy it. And I said, yeah, it's not gonna happen. Um, you know, right. I mean, engineers, right?
Jarie Bolander: classic fight between engineering and marketing. It's classic, right? So, yeah, I think more marketers should, I think, embrace the scientific method. I, I, I just . I just think you're right when it turns to having, like having a framework to rapidly iterate, figure out the way it's gonna go.
Jarie Bolander: And I also think I would add to that within the confines of guardrails on what you're doing, which I think is what I say is like B two B storytelling me the guardrails in which to operate those experiments. Because a lot of times, and you've probably seen this too, Some of these things that marketers why are you doing that?
Jarie Bolander: Well, I read a paper about this B two C brand that did it, and I'm like, you're B two B man. Your B two B defense, or your B two B financial services. Like how creative, I mean, you could be creative, but like the stay within the guardrails, man. Like that's the creativity. Is it? Then the, you know, creativity is all about constraints under time, right?
Jarie Bolander: You know, like under a deadline. That is what I've found has been the most useful for me is like septic guardrails and play within the space. And I, I always like, you know, sports analogies, we were talking about Ted lasso before we hit record, which I have not seen yet. And I know I'm probably the only one on the planet I should see it.
Jarie Bolander: convinced me, I'm just gonna do it. You know? 'cause I have a, I have a visceral reaction to the un creativity of all these plus channels. Right? Don't get me started on that. Um, but you know, like from a, from a sports analogy, it's like . These are the rules of the game, you have to play within the rules.
Jarie Bolander: Now, you know, games are played, high performance games are played at the edge of the always looking for the edge of the rule set, but they're not played outside the rules, right? Because so you, so depending on what you're doing, you need to understand that. And I think that's why the two most powerful things a marketer can, can do is one.
Jarie Bolander: To your point, understand the guard rails, have a framework in which to experiment quickly. two, really understand your story. Like what, what am I telling, what am I trying to get across? 'cause, 'cause you see this all the time, it's Are you a this company or that company
Jarie Bolander: It's like, what are you like fundamental. You need to know that.
Gboyega Adebayo: Yeah. And I think that, and we're transparently, we're living this right now with the insular. We're, you know we're having these conversations of, okay. Is the problem that.
Gboyega Adebayo: we're seeing with the business a go to market problem or a product problem, right? Because I think there is a easy trap to fall into where you try to solve everything with a new feature or a new function.
Gboyega Adebayo: And sometimes it's just stepping back and saying, are we just telling the wrong story? Are we not resonating with the audience that we expected to? Um. I always joke and say, I'm not a creative person. I'm super creative within the box though.
Jarie Bolander: Mm-hmm.
Gboyega Adebayo: If you tell me where I can play and the assumptions that I have to use, I can come up with some madness.
Gboyega Adebayo: It's where you say it's the art of the possible. That's where I struggle.
Jarie Bolander: Well, I think that's where everyone struggles and I mean, that's actually a really astute point that most people don't understand about creativity.
Gboyega Adebayo: Hmm.
Jarie Bolander: creativity is about constraints. It it's, it's a hundred percent true. It has to be because you just can't be like, yo man, like, let's just free to be you and me.
Jarie Bolander: You know, Madden like you've ne never, nothing ever gets done, right? So for me, creativity is constraints on a deadline. I love the show, and this is gonna sound silly, it's, uh, project Runway. I think it
Gboyega Adebayo: I mean, I, I know, I
Jarie Bolander: You've heard of it, right? You know where these people are making clothes, right?
Jarie Bolander: And it's on a deadline, and it's these different styles. And I'm just fascinated beyond fascinated because there's some good, solid work done on a deadline. Like there's no,
Jarie Bolander: like, it has to get done. You're like, okay, do it. That's an artist, that's a creative.
Jarie Bolander: The constraints matter a lot,
Gboyega Adebayo: Right.
Jarie Bolander: I think if you've got good constraints and good guardrails and that, that means you've defined the problem, you're going after understand the story you're telling, making some decisions because again, a lot of times marketing, in fact, I was talking to someone the other day.
Jarie Bolander: It was on, it was on LinkedIn. And someone's like, yeah, storytelling doesn't matter. And I'm like, yo, whole stop. Like, I don't believe that. He's like, well it's, it's the rumination on all this creativity, not me taking action. And I said, well, I agree with that. The fact is constraints make you make decisions and decision making's Marketers are schizophrenic. They're like so worried about making the wrong decision because everyone's like, what do you do? I mean, we're in, we're in the middle of a recession now, right? What's the first thing people do? They cut marketing. well, we can't measure it, you know? Uh, we gotta constrain, you know, you know, like financial wonks folks that all they do is like, you know, figure out the numbers, you know, good on them.
Jarie Bolander: But like, there's no, like soon. Your finance job will be done by a robot .
Gboyega Adebayo: Yeah.
Jarie Bolander: rules, it's rules-based. Right. So, but the thing that people don't grasp is the, again, I think you, you nailed it. Like the framework, the experiments. How fast can I do a cycle of learning? We used to say cycles of learning when I the fab, that's chips.
Jarie Bolander: How many cycles of learning is this gonna take to solve? That takes commitment and, and like, This is the plan, and if it's wrong, I'm wrong. Move on. But you're right quick. Iterations within a framework is just super
Gboyega Adebayo: Yeah.
Gboyega Adebayo: Cycle to say that one more time cycles
Jarie Bolander: Cycles of learning. Cycles
Gboyega Adebayo: Cycles of learning. I'm going to have to pull that one into my vernacular because I was having a conversation yesterday with someone around Not to make this about me, because we'll, we'll get back to you, I promise. But we were talking about a business problem and I kind of told him, I said, I'm very good at incorporating things.
Gboyega Adebayo: I'm good at connecting the dots and being like. You gave me five different random things and I can tell all of these things in a cohesive story that makes all the sense. I'm very, very good at that. Where I sometimes struggle and want to get better at is, okay, now this is the picture. Here's the roadmap to make that picture a reality and then just stick to that plan and execute on that specific plan.
Gboyega Adebayo: Because I tend to I would say this at work. I'm a good leader. I'm a horrible project manager.
Gboyega Adebayo: And so, so, you know, having that. Kind of term of cycles of learning. How many cycles of learning will this take? I think it's going to be really helpful to me just thinking about, Hey, they're going to be a couple at bats. We have to take just because you, you know, strike out the first time. Does it mean you need to look for a new thing to like incorporate and pulls the fold learning and failing as part of the project plan?
Gboyega Adebayo: More or less.
Jarie Bolander: Yeah. I mean, cycles of learning was the precursor to sprints, agile development. this, I mean, I was doing that before Agile And so, but, but the, it's similar. So the thing I really like about Agile and Sprints, and they, in some, in some, Companies for marketing, which I think is really valid.
Gboyega Adebayo: Hmm.
Jarie Bolander: I really like it. There's parts of it I don't like because it's all about like shipping in three some products you can't do that. Like if you're building a piece of hardware, eh, hard to do that, you know, complex things. But the general philosophy is really sound. And the reason why cycles of learning always stuck with me when we were in, when I was doing semiconductors.
Jarie Bolander: And we were doing a new technology node, the next generation, we would have to think, okay, how hard is this gonna be? And since the cycle time through a fab, if we did an experiment, we're talking in a minimum five to six weeks an experiment like you just had.
Jarie Bolander: And they were costing, you know, they cost a lot of money. This was no like recompile away from perfection. This was . I'm gonna spend real money in real time waiting for this process to go, and then I've got to test it. So I really had to know the discipline was, you know, we're about to spend 250 grand on this experiment, you better make sure you get something out of it.
Jarie Bolander: Whereas,
Jarie Bolander: you know, software and marketing things, you're not spending that much money. You know, you're spending it, you know you have opportunity costs, but you're not spending hundreds of thousands of dollars. So the mindset shifts. The, the power of thinking of things, and especially innovation and solving a problem as how many cycles of learning, how many sprints is that?
Jarie Bolander: Then you can kind of quantify along the way, like, oh, well, hey, this new technology node is an example, got like five or six different process nodes that all have to work and we've never done them Well, that's pretty innovative. You can apply the same thing to any, Say, okay, so how do we prove one of these?
Jarie Bolander: What, what's the, what's the experiments we need to do in order to say, you know, one of the things was, what would be called, uh, contacts between metal layers? how the, the, the pitch between contacts and a metal layer heart, it's a hard problem, right? How are we gonna solve that problem? And then we would run experiments to do that.
Jarie Bolander: And so if you, if you say, here's the goal we're gonna get to, and you break it down into these cycles of learning. For these sprints, then you know, the one progress happens. And two, it's the discipline of knowing what the result should be being like, oh, huh, that didn't work.
Gboyega Adebayo: Yeah.
Jarie Bolander: next . You know,
Gboyega Adebayo: Right. Right. Right. no, that's helpful to kind of paint that picture and thinking about it as the evolution of agile or the evolution to agile makes a lot of sense because I was having similar conversations as a consultant about agile finance or agile funding. Which is essentially, Hey, you're a really big company.
Gboyega Adebayo: You should fund everything like VCs fund startups. Don't give them the whole check up front,
Jarie Bolander: Tranche it. Yeah.
Gboyega Adebayo: trot it. Like, Hey, you try this. Okay. That stops. That didn't work. Let's stop. Let's not keep going with this 200 million project. Let's. Pivot and figure out and reallocate those funds. So it makes a lot of sense.
Gboyega Adebayo: One of the things, excuse me. One of the things I do want to explore with you is your experience, not only as an entrepreneur, but as a lead generation expert and finding product market fit, because I think a lot of the things that we've been talking about is, okay, build your thing fast. And try to find out if it works well, finding out if it works as product market fit.
Gboyega Adebayo: So I'd like to what's your framework for early stage, you know, finding product market fit in the early stages of companies because it can be very costly
Jarie Bolander: Yeah.
Jarie Bolander: Oh yeah. No, no.
Gboyega Adebayo: if you, if you, if you, if you do it in an efficient
Jarie Bolander: Yeah. No, it, and it's hard to do. I mean, that's where companies go to die, right? great idea. And then, uh, no one wants to buy it. Like, you know, I, I always say now that products are democratized and that it's all about the better story. I mean, best story wins. And what I mean by that is product, market fit, marketing, That all, that's all that matters To a first product get all bent Jari saying, I get it, but there's 10,000 MarTech tools. 10,000. How many AI tools are there gonna be like 500 now? They're probably exponentially growing. Do we really need all those silly tools?
Jarie Bolander: No, of course not. What do we, what we need is, of course, those problems to be solved, obviously, and. They're all competing to see who's gonna win. Right? that's fine, but you know, I get inundated with all these does this work, does that work, And so I actually came up with this framework.
Jarie Bolander: it came from, I first read about it from Superhuman, email tool? think it, I think the CEO's name is He did just a fantastic writeup product market fit that he, built. He got that from somebody else. So obviously this is, all great artist steel, right?
Jarie Bolander: So I stole it from He probably stole, he stole it from someone else. And you know, Um, and we've actually implemented this, I, when I was working at my old firm, one of our clients, Sutro, Iot a water testing robot that floats in your pool. We implemented this there and it was extremely effective.
Jarie Bolander: They still do it to this day, two years later. It drives all of their product development, their customer support, their, any, you know, customer satisfaction, you know how they're doing. It's in all of their, uh, OKRs. It's, it's just a powerful, powerful and it's basically a product market fits survey.
Jarie Bolander: That combines net present, I mean, sorry, net promoter score with some fundamental questions Um, now you have to have a little bit of traction in order for this to effectively work.
Gboyega Adebayo: Yeah. Hm.
Jarie Bolander: hard to do this with, you don't have many customers, even if, I mean, even if you have free customers and it doesn't take many, know, I think if Had, you know, anywhere from 25 to 50 customers, probably get some good signal out of this, but the more the better, right? I think to date, Sutro product market fit survey is probably running about 2000 respondents gosh, I don't know how many, have a lot, way more, uh, customers
Gboyega Adebayo: Yeah.
Jarie Bolander: um, Basic premise, which again, I got from Raoul, who the question that's the one of the most important in the whole if this thing didn't exist, how disappointed would Now, this seems counterintuitive 'cause everyone's like, oh, how great are you?
Jarie Bolander: You Um, but you want to turn towards the negative because there's this thing called loss version. Like people don't wanna lose things. Right. That, you know. If I gave you $10, you'd be like, oh, great. If I stole $10 from you, you're gonna be a lot more upset. Right. You know, this loss of virgin I would say five to 10 x stronger emotion, primarily.
Jarie Bolander: 'cause we're wired that way. Right? We're wired to prevent loss, prevent us getting killed, . Right. You know, and generally, you know, positivity and success. The dopamine hits, then it goes away. Right? So
Gboyega Adebayo: Right.
Jarie Bolander: framing it as the loss. Is a very powerful thing. And so the answer to that question's only three answers, very disappointed, somewhat disappointed, or not Those are the And what's really powerful about that single question for product market fit is that it gives you a pretty good indication on how useful your product is and how sticky. know, within reason. Okay. You know, people debate, well, you know, I hear all these PE people say, oh, you know when you have product market fit?
Jarie Bolander: 'cause you just know. And I'm like, yeah, okay. Yeah, if you're growing 10% a week, of course, but come on man. Like I need some practical measure, not your like gut feel, which is you need your gut feel. But come on, like not all of us are a Y Combinator company. Right. You know, come on. You know what I mean?
Jarie Bolander: You know. And so market fit survey, that first question. What's interesting is there's some mathematics behind term, it's this idea called the Optimum Stopping ever heard of this, but it's actually something from computer science and the idea is there, like if you are looking for a solution or you're looking for a house or whatever, right?
Jarie Bolander: Um, there's a point where . It's the, it's the optimum place to stop looking and then literally taking the next best offer that's above the, what you've seen in the past. So what does that Well, if you use the dating analogy and you say, okay, I'm gonna live to be 85. I hope we all hope, right? Or longer.
Jarie Bolander: And I want to take, I'm gonna use the optimum stopping principle, right? To pick a mate. Then and get married, then I should not get married before I'm 27.
Gboyega Adebayo: Hm. '
Jarie Bolander: cause that's roughly 30, 30, 30 Right. Or set And that's a little bit strange. And you're like, well why is that?
Jarie Bolander: Well it's been proven given, you know, all things considered the highest probability of success. Is to look for about of the time and then take the next bet. Take the offer. That's better than what you saw in the past, right? You just like, and you're, you're good, right? And you got a higher probability Two shoot.
Jarie Bolander: So not so much too longer. Doesn't matter. It washes out, right? So if you take the optimum stopping principle and you apply it to product market fit, You can, you can reverse the math and you can say, Hey, if, if 36% of the people I've responded would be very disappointed that this does not exist,
Gboyega Adebayo: Yeah.
Jarie Bolander: that's a high signal that, okay, product mark, I'm, I'm starting to get product market fit.
Jarie Bolander: Now I need to figure out what, I need to find those people that co and then I need to just expand that. And so then the next question you ask is, You know, given this product, who are the type of people that would use it? seems like, why don't you just ask 'em who they are? Well, no, no, we, you want these all freeform.
Jarie Bolander: Because what people do is they'll not only respond about them, but they'll think, oh, you know these other people. And you're like, okay. Got it. And then the
Gboyega Adebayo: Yeah.
Jarie Bolander: do you like about the product? The next one is, what do you dislike about the product? final one is, How can we improve it? There's another one, and then there's the N P s question, right?
Jarie Bolander: A score one to 10, blah, blah, blah. Now those are the core questions, and I think if you take quantitative approach, really study those, that information, will know the roadmap to get to product market fit. Now, it may take you longer than the money you have . That's the caveat, but, I've, but . Not only is it backed up by data and my experience and the experience of these other people, it seems like a solid framework and let's just experiment with marketing.
Jarie Bolander: And it could be features and functions. It hey, what people love. We need to do more marketing messaging on that. What people hate, we need to fix or we need or we need to do a pro. I mean, six or seven questions from people that have used your product or bought your product are just gold that no one taps into.