Founder Mistakes: Know the Problem You Are Solving with Carol Malakasis
31 Jan 2026 · 6 min
Carol Malakasis on why founders fail: they build without selling and can't explain what problem they solve. She recommends a ten-word tagline, testing messaging on LinkedIn, and learning sales yourself before you hire someone else to do it.
Chapters
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How much time do you have?
We have roughly 37 minutes.
Okay, I think we're good. So, you know, I think it starts even before going to market or deciding we need to go to market. So there's this idea which you just mentioned a few seconds ago, that, you know, if I build it, they will come. No one's going to come. Nobody knows how. How can people know? And you know, I've seen this so many times where I speak to founders and I'm like, okay, great, what have you done so far? What's your sales strategy? Or what are you looking to accomplish? And they don't have an answer. And to me, as a salesperson, because I've been selling for 11 plus years now, it baffles me because these are some of the smartest people. They've gone to an Ivy League school, You know, they're engineers, they built this product, they understand the different possible applications, but sales is almost like an afterthought. And when you tell them, no, you need to sell it, you need to start talking to people, it's almost like a light bulb goes off. So, number one, it's the mistake that I see often is that there's this notion of people will come to me, so we need to go through that hump of, no, no one's going to come. And now that we're both on the same page, that no one's going to come. Let's talk about how you need to start thinking about your process. Number two, and this also used to surprise me a lot. And again, I'm surprised because I'm a salesperson. So some things come easy to me. Right? Or you don't need to explain them to me because I've learned them over the years. When you ask them, what problem are you solving? They can't really give you an eloquent, short and sweet answer. And then I have to go dig through the different layers and understand and listen. I'm happy to do that. That's my job. But I'm thinking, if I'm here with the best of intentions to really listen to you and understand and I'm not able to do it, how do you expect this stranger, you're going to email or target on LinkedIn to understand? So, number one is the messaging. And a method that I found that's simple and works well is to kind of get them thinking, what problem am I solving? Who am I solving that problem for? Who are the different players in the space already doing what I'm doing right now, and how am I different or better? And that's when they're like, okay, got it. Right? Because you need to be able to explain what you do to anyone, no matter their level of industry knowledge or expertise.
And how do you help them get to that point of being succinct? Right? Because I hear from founders all the time. It's like, what do you do? Well, we are the new, up and coming, innovative, disruptive, transformational tool that will let. And it's this, like, how do you help them get a little bit more succinct with their messaging iteration?
We'll run it over and over and over. And you know, every LinkedIn profile has or should have a tagline, right? Well, next to your name, you say, I help SDRs be better. Or mine is, you know, I help sales founder build and scale their first sales Playbook. So you need in one sentence, in ten words or less to tell me what you do. So we'll run it over and over and over till it gets to that place.
I like that. And then, so I guess what do you do if they're not sure what problem they solve? I'm still shocked by how many founders. They build something because they think people will want it, but it doesn't actually solve a problem. So actually, I'll rephrase this question. When you're looking at companies to get involved with and, you know, to invest in and work with, I guess what do you look for in terms of the product or the problem that they're solving to say, ooh, this is good.
You know what it is? And I feel like there's two questions in there. So let me take a slight left turn, if that's okay.
Absolutely.
When I look at who I'm going to work with, I don't so much look at the product. I look at the founder. Are they coachable, like a sales rep? If I'm going to hire a sales rep, and they're not coachable, they're not open to feedback, they don't trust the process, and they're like, oh, I'm excited. I'm going to run with this process. Doesn't matter what I do, doesn't matter how many times I say what I'm going to say. Doesn't matter if I hold their hand, doesn't matter how many scripts I write, they're not going to do well. And I think the positioning and the messaging and the willingness to follow, that goes a lot, goes a longer way than the actual product itself. I mean, I'm sure you've seen this in your career where you have the cure for cancer and no one knows about it and it doesn't matter. Or you could have a very mediocre product. But if the person is so passionate and their positioning is so strong and they have the excitement and the process and they want to go talk to everyone about it, people will buy it. So I think that it's not so much the product that we look for, it's the person and how ready they are to commit, to learn how to sell, how much they trust the process and how much of a burning need this is for them to actually go do it.
I love that as a call out to, like, do they need to. Are they dabbling? Are they dabbling? They just, like, have this idea of being a founder. So, okay, so let's go another layer deeper here. So, okay, I've come, I'm working with you now. I've identified the problem. I've got it succinct. I'm open to coaching, but I'm a product guy, Carol. Like, I'm not a salesperson. I can't talk to strangers. So how do you work with them to embrace that a little bit? Because I do think a lot of early founders, and you actually probably see this even more than I do of like, they build it and they're like, well, I'll just hire someone to sell it. And they never get involved. So, like, how do you help someone who isn't a salesperson actually feel comfortable with selling?
You know, I think there are stereotypes around salespeople that a lot of founders have, and I think that there's stereotypes around engineers that we as salespeople have. We see them as nerds that don't know how to talk to people. And then I need to teach them in how to get good at it and embrace it. So I think it's about understanding if I get good at founder sales, what will this do for me? And it's not about just being a brand evangelist. It's about having a process and really learning how do I get someone that's a prospect and turn them into a paying customer. And if I master this process, then when I'm ready to hire my first AE or my SDR to help me with top of funnel, I can plug them into that process and they're going to use it and everyone's going to be happy. And I don't need to figure that out. Or, you know, I've seen it a lot where a founder will say, well, you know, I don't want to deal with this. I just want to build and I'm going to hire a VP of sales. Well, first of all, a VP of sales is going to cost you a lot of money. And secondly, VPs of sales tend to be quantitative oriented. They don't want to necessarily roll up their sleeves and build process. And if the founder has no prior knowledge of obstacles in the process, how you need to run it, how you want to be thinking about it, they can communicate with that vp. So there's often a clash. And I think that when they realize the importance that this is going to, how important this is going to be and how much it will help them. Not burn through cash by hiring the wrong people. Not burn through cash because they're burning through great leads because they don't know how to close them. Not burn through cash because they're onboarding customers that are not a great fit and they churn it just opens their minds to all the possibilities and all the which ways where they can communicate with their customers. And I think that once they start to realize that, they really love it and they get good with the idea that this can be superpower for me and I want to get good at it.
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