#327 Dean Croshere’s Assertive Approach to Startup Success: Facing Fears and Forging Ahead

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Mehmet: Hello and welcome back to a new episode of the CTO show with Mehmet. Today I'm very pleased joining me, Dean. Dean, thank you very much for being with me here on the show today. The way I love to do it is I prefer my guests to introduce themselves because I have a theory the best one who can introduce [00:01:00] himself or herself is the person.

Mehmet: So the floor is yours. Tell us a little bit more about you, your journey and what you are up to currently. 

Dean: Thank you so much Mehmet. I am super excited to, uh, talk to you today. Um, I have a, a background in business, but, uh, over the years I have come to learn that, um, assertiveness is where I really like to spend my time thinking and talking to people.

Dean: Um, I think that, um, emotional awareness, um, and leading from desire is absolutely critical to getting, um, What I want and I very much enjoy talking about it. And, um, I have this kind of crazy career path. Um, I, uh, my, my path started when I was, uh, you know, 23 years old, just out of college, I was living on my ex girlfriend's couch and I had, uh, I had clicked on a Facebook ad for a job that would get [00:02:00] me, um, A, uh, you know, they were, they were going to place recent college graduates, uh, entry level jobs.

Dean: And I got a job at the factory down the road, um, through that link. And, um, I had been working at that factory for about a year when, uh, my boss called me into his office and said, Hey, Hey, Dean, how'd you like to, uh, get a job? Uh, in Thailand running this factory that we're starting over there. Um, and I said, no, I'm going into the peace corps.

Dean: And, um, that was a Friday. Uh, Monday I came back and, uh, about that job. Um, and it was still available. And a month and a half later I had sold everything I owned. Um, I had. Turned 24 in the meantime, and just 24, I was in Thailand and I had the keys to a factory. Um, and, um, it was pretty intense, uh, experience, you know, I had sort of had this overwhelming experience of trying to [00:03:00] learn how to run a factory, how to run a factory in Thailand, learn a little bit of Thai.

Dean: Um, and I, I had this moment when I first set foot in Thailand and realized that I did not know how to properly say hello. Um, in, in Thai. Men and women talk differently and I hadn't quite figured that out yet. Um, and so, you know, the beginning of a very steep learning curve and, um, also in Thailand, I sort of, uh, had this opportunity to observe the world around me from a, quite an outsider's perspective.

Dean: Um, I was in an industrial state with a lot of other, um, a lot of other, mostly, uh, European and American businesses. And got to meet with a lot of. Founders and, uh, people who are, you know, twice my age at the time and tried to figure out what it is that makes a successful leader. Um, and then, you know, I left [00:04:00] Thailand and went and got my MBA and studied that more and did some consulting.

Dean: And I have found that the, uh, the people who are the most successful, the people who are the best at asking questions. And what makes me the most successful is not only when I ask questions of others, but when I ask effective questions of myself. And that's really been a major part of this journey and a lot of what I, uh, enjoy talking about.

Mehmet: That's absolutely fantastic journey, Dean, I would say. Um, Like you, you mentioned, you know, in your introduction a little bit about the emotions and, you know, the, the, the thing that around it, when, when we decide to start a business or to go take a new role now from purely startup perspective or a new business perspective.

Mehmet: I know this from my own experience as well. So it's a big step. People usually they feel [00:05:00] very scared, very afraid. Um, and some people they just give up. So I know that, you know, you, you identified this as a major, uh, barrier for, for startups and your business, but can you a little bit elaborate on, I know you talk also when, because I, when I was preparing for the episode about five core feeds, you believe that they are the most You know, the terminal and how actually as entrepreneurs, we can navigate these challenges.

Dean: Yes. Thank you. Um, yeah, so there's five core fears is a, is a major part of, um, running a business. Um, and they, they really sort of, um, show up. Show up a lot. And I think that's part of understanding, um,

Dean: what it is that we need to happen. I mean, when I, when I talk about the five core [00:06:00] fears, um, usually it's, it's talking about a product company and. Um, we, we see this over and over again. Um, GOC, my company is a, um, an IOT engineering consulting company, or at least it has been, and, um, we work with a lot of startup companies and we sort of see the same, um, mistakes over and over again.

Dean: Um, and then the first one we see is that the product doesn't do enough, right? It's just like. Desire to add features. So as to be good enough. Um, and personally, I think that's a reflection of a co founders. Or a founder's fear that I am not enough, right? Like I need to make this product so great that everybody's going to love it, which might be a reflection of my desire to be seen as sufficient.[00:07:00] 

Dean: Um, but the, the general points as, as a, um, as I'm thinking about A product is to be able to say no to feature requests, right? Like I will have a desire in myself, um, to add features, to have my product be good enough. Um, and certainly people working for me and even customers sometimes will say like, wouldn't it be cool if it did this thing?

Dean: And it's like, yeah, yeah, I could add that feature. But at the end of the day, usually customers need a real big problem solved, and it's best to solve that problem as simply as possible and avoid overcomplicating a product, especially early on with features. Um, we've certainly all used tech products that, uh, You know, it's just like this used to be great, but then every year we've added features to it, and I've kind of lost track of what all these features are and what they do.

Dean: And really, I just need it to work. Another product, [00:08:00] another fear that comes up very often with early stage products is a fear that the product doesn't look good. Um, you know, we're all spoiled by our iPhones and whatever else. He's like very beautiful, incredibly well engineered products. Um, but making a product look good is expensive.

Dean: And if it's a B2B product, like, A project box is probably fine. It just needs to actually solve a problem. Um, and it almost certainly doesn't need to come in a well designed box. I think Apple also spoiled us with very beautiful boxes. But like, I'm gonna throw that away right away. And I'm not Apple and I don't have Apple's money.

Dean: I'm a startup. I mean, just make a product that solves a problem. Um, the third one that I like to talk about is, um, testing. Um, testing is really scary for a startup, right? Like I want to get my product in the market as soon as possible. I [00:09:00] want to get revenue as soon as possible. And also like, what if it fails?

Dean: What if, you know, testing reveals that the product. Isn't going to work. Um, like that's a scary moment to like, I want to slow down. I want to spend money to test and potentially fail before I even get the product on the market. Like, I've got a limited runway. Like, let me just put on the market and deal with failures later.

Dean: Um, and we've definitely seen this in the past. And almost always spending a little bit of time and money testing is worth the cost. Um, the pressure to ship is high, but, um, when a global fleet of devices gets bricked by a bad update, there's no undo button and that's millions of dollars that could have been saved by spending a little bit more time building infrastructure and building a, um, [00:10:00] Oh, a good testing plan that actually, that actually works.

Dean: Um, and that that sort of infrastructure thing is is a big deal that startups often skip. Um, the fourth one is is a fear of asking for help. Um, that's frankly, kind of a masculine problem. Um, like there's the old thing about men not wanting to stop and ask for directions. I guess these days it's kind of outdated now that we all have GPS.

Dean: But, uh, help. Is useful. Um, there are people out there that are really, really good at solving almost any problem that you're facing. And. Unless the problem that you're trying to solve is a core feature of your product. It's almost always better to ask somebody else to solve it. Um, it's like, if you're trying to build a house and you decide that the way you're [00:11:00] going to start building this house is get an ax and go out in the woods to cut down some trees, like it's not.

Dean: The fastest way to build a house. We should say like, I want a house that has three rooms and two bathrooms and then go buy it, go hire a, uh, you know, a specialist to design and build the house for you because they're good at it. Um, and they can do what you want easier and better than you can hire experts, which, you know, as somebody who runs a consulting company, feel self motivated, but also like we see this problem and we're often brought in to fix the problems that were.

Dean: Would have been cheaper if they hired us years sooner. Um, and that's sort of related to the last one, the fear of admitting mistakes. Um, we quite frequently see clients who would be better off just saying like, we made some mistakes in the past and we want to throw away a [00:12:00] significant amount of work we've done and start over because continually fixing the bugs is more expensive than just starting over and doing it right.

Dean: Um, oftentimes when we're in this world, there's a, um, a not ceo, like a, a, a C level manager who has a huge amount of ego tied into the success of the product and they're unwilling to tell the ceo that like this stuff we've spent all of this time energy building needs to be tossed and rebuilt. Um, there's ego challenges there and there is.

Dean: quite possibly like my job on the line. Like if I went and admitted that I messed up or at least I was doing the best I could and made mistakes, then I, uh, then I'm something bad could happen to me and I don't want [00:13:00] to admit that as a mid level manager and so I'm going to keep Doubling down on my past mistakes.

Dean: Um, and there's quite possibly also, uh, emotional issues from the CEO here who might be avoiding conflict. Maybe he kind of knows that something's going on here and, uh, wants to just pretend that things are okay and just believe they're, um, call it a CTO or, or chief engineering officer, um, VP engineering, maybe, um, wants to just believe them when they say that, like, they can make this work, um, the costs.

Dean: Of that conflict could be high. And so, um, I think it's, it's very common to avoid that conflict, but conflict is so, so very important for a successful organization. 

Mehmet: Dealing all the five, you know, core fees you just mentioned to me looks like, because I, I took some notes. Majority of the [00:14:00] time, I'm not sure if, you know, you would agree with me or, or not, um, Communication is is is part of maybe crossing these challenges and and converting them to something useful because You know, if I take for example the first one if i'm if I don't go ask the customers Okay, is this what you want?

Mehmet: I would not know right and for example asking for help. It's very obvious and of course again admitting the mistake so it looks like You know, communication here is, you know, beneath all these fears because people sometime, maybe also, I'm not sure if I can say this, but they get scared that, oh, maybe I will say something and people will misunderstand me.

Mehmet: So they have this kind of. Imposter syndrome. Like, oh, people will not get what I'm trying to say. People will will will will misunderstand me. Is this is this something which you agree with me on? 

Dean: Yeah. [00:15:00] Um, so that's, you know, I mentioned assertiveness a little bit in the, uh, in the opening here. And I think that's where this is showing up here.

Dean: Um, there's in order to be assertive, um, there's a quote from, um, uh, an author by the name of, uh, David Rico. Um, he wrote how to be an adult, um, which is not a business book, but I take as sort of a business manual, um, because, you know, he says the secret to assertiveness is to strongly ask for what you want and be okay when the answer is no, and.

Dean: So, you know, there's, there's this fear that if I get rejected, that is a rejection of me personally. And so people aren't going to ask for help because they're scared of what that's going to mean for me personally. Right? Like I want help. I want somebody who's good at this. And I'm scared that if I [00:16:00] ask for that, I'm going to be admitting that I'm not good enough.

Dean: Um, and potentially somebody might say, no, like you're bad at this, like, you know, laugh at you or something like there there's, um, it's important to be able to understand that what I want is to find the best possible person to resolve this. Um, and I know that I want that. And so I'm going to start asking around to try to find that.

Dean: Or maybe I'm going to try to figure out, like, what is the best possible set of features. And like, I want to know what you need and quite likely customers are going to say like, Oh yeah, like I would love it to. You know, rub my back while it's waters, my lawn or whatever, right? Like I would love it to do all these things, but trying to, um, really hear a customer when they talk about their problems and understand which ones are the ones that like, they are actually driving their decision making, um, and, and [00:17:00] believing them.

Dean: When they say, no, I don't want the feature that you want me to want, right? Like perhaps I'm trying to invent a back massaging water, a lawn watering device. And like, I'm looking for somebody to give me that feedback. And I could probably find somebody to say like, yeah, that'd be great. Um, but the no. And my emotional reaction to a no, like noticing in my body how it feels when somebody says that, like, they don't want the thing I want them to want is going to be very key in understanding whether I am manipulating the people around me or just hearing them when they tell me what they want.

Mehmet: Absolutely. You know, I can't agree more with you on this one. And one thing you mentioned also maybe in the introduction. you know, a concept that I know I felt, you know, how much passion you are about it. This is leading from desire. So, um, how, if you [00:18:00] can explain like how this is like, uh, like more conventional than the standard leadership methods or approaches that we know.

Mehmet: And if you can just, you know, give me an example that can highlight that. 

Dean: Yeah, absolutely. Um, so when I talk about leading from desire, I talk about, um, knowing what I want. Um, I, uh, the only way to get what I want is to ask for it. Um, unless I get lucky and somebody just stumbles into it and I can't ask for what I want if I don't know what it is.

Dean: And it turns out to often be a harder question than it appears. Um, I like to use the old Toyota five wise. Thing is an example. Um, you know, uh, Toyota talked about, um, uh, using five wives as a way to understand the [00:19:00] underlying causes of a problem like that with the, the Boeing, uh, issues recently, right?

Dean: Like there's a hole in the plane. Why? Well, the door plug blew out. Well, why? Well, because the bolts weren't tightened. Well, why? Well, because nobody thought the bolts needed to be tightened. Like why? Okay. Now we're getting to like, Theoretically, there's some sort of systemic issues at Boeing where they don't aren't prioritizing safety.

Dean: And, you know, it's taking quite a few wise to get to, to the real issue. And I think that's also important with, with. Um, you know, it's easy enough to say, like, I want to make the sale. Why? Because it would bring in a bunch of money and like, well, why do I want a bunch of money? You know, because I want to buy a new house.

Dean: Like, okay, it's great to want a new house, but like, why? Like, okay, well, I want the validation of the house. Maybe I want the safety of the house. Um, I want to be seen like that. There's, there's some, um, questions [00:20:00] that I feel like if I understand why I want these things, it's easier to make the higher level decisions, um, and to have fallback choices when the, uh, first choice.

Dean: I make doesn't work. And I like to talk about my company. Cause I've talked about, I've talked about the consulting geocene does, but, and I also mentioned briefly that like, that's what we have been doing, but we're actually making a pretty big pivot right now. Um, juicy and has been a consulting company, but we are pivoting into being a product company.

Dean: Um, we're switching to being a, uh, a carbon credits validator in the cookstove market. And the reason we are doing that is because. We had a bunch of internal conversations about what we actually wanted to be doing. Um, the consulting was going fine. Like we were making a pretty solid income and we had some great clients and we're doing some, some [00:21:00] great work and we were proud of it.

Dean: But at the end of the day we were also spending a fair amount of time complaining about making other people's products that like we're getting to a point in our lives where we wanted to be doing a thing that And be able to say like, Hey, I made this, I made decisions to make this product for myself.

Dean: And we also then sat around and said like, we want to be involved in climate change. And our CEO, uh, got his PhD working in this. Uh, in, in the cook stove market, and there's a big opportunity right now, um, to, to work in validation in this space. And so we knew it was time and we were ready and able to take advantage of this opportunity, um, because we had been having a lot of questions about what it is that we, the leaders of this company wanted to be doing with our lives.

Dean: [00:22:00] And with our time and with our energy. And so we had the, um, the confidence in each other that we would be willing to make this, uh, this transition and it wasn't unanimous. We actually, as a part of the transition, we had a co founder leave and we had, um, we had another employee, another, um, early employee leave and that.

Dean: That sucks. Um, but also it doesn't right because they, they didn't want to go in the same direction we did and they're doing different things now. And the things they're doing are exciting to, um, it's just, um, we were afraid of what would happen when we broke up the team and we decided that our desire was more important than our fear.

Dean: And so we went for it. It's exciting and scary. 

Mehmet: Yeah The five why's you know, i'm I'm a big fan as well because it helps in multiple disciplines, by the way, not in [00:23:00] the business context only Um, i've read a book once It was a person development book. I can't remember now the title, but again, they mentioned they are the five why's to find your purpose actually.

Mehmet: Uh, so, so, and of course in, in the business perspective, uh, it's very good, especially in the early days for founders and co founders to ask these questions because, Hey, we have a nice idea for a product or a service. Okay. Why you want to do it? And then when you do this iteration. And I think this is back to the communication, the assertive communication that you were mentioning, Dean.

Mehmet: It's very much related because once you Ask these good questions these good wise I would say to yourself then you can ask it to others So it makes like a holistic, you know, a a one I would say You know idea that that make things much much easier to to understand comprehend and communicate it to others.

Mehmet: So Uh, [00:24:00] I like also the five hours just you know, I wanted to say this now In the introduction as well You You know, talking about emotions and all this. So you mentioned something about attachment theory in business. Um, so why it's important and how understanding, you know, this attachment thing can help, you know, us in business context, for example, um, having, you know, Bad partnerships or maybe, you know, get attached to a feature in a product perspective.

Mehmet: So if you can shed some lights on, on the attachment theory in business. 

Dean: Yes, of course. Thank you for asking about that. Um, attachment theory is a, a pretty significant, uh, theory in, in human relationships. Um, it, it perhaps if, uh, uh, any of your listeners have done any, um, relationship [00:25:00] counseling, um, they may have heard something about it.

Dean: Um, it's the, the basic idea is that, um, as, as young kids, we, um, learned that, um, safety came, um, from either, um, trying to, um, control or, or avoid, um. I'm being close with our parents. Like you can, you can watch very young children and how they relate to their parents and say like, oh, okay, they are either anxiously attached or avoidant attached, uh, generally speaking.

Dean: Um, and that those patterns show up in adults as well. Um, and. Usually this is talked about in the terms of romantic relationships, but it's also generally quite observable in other sorts of relationships. And usually we [00:26:00] find that people who are generally anxious attached will find themselves in relations relationships with people who are avoidant attached, that there's something about the, um, the different strengths that people find attractive and also you know, infuriating.

Dean: Um, and so it's useful to understand these dynamics, um, to understand how people are relating to one another in a business, especially co founders. That's a strong, very important relationship with, uh, that often has attachment, uh, strung along with it. But, um, people will usually relate to many people in their lives.

Dean: in similar ways. Um, not always. Um, it's entirely possible for somebody to be anxiously attached with one person and avoid and attached with another simultaneously. Um, but the way this often shows up is, um, you'll see one partner who is anxiously attached, who [00:27:00] is Um, more likely to, uh, create a conflict with somebody who is avoidant attached and also, um, more likely to try to repair the relationship after sort of, uh, a break.

Dean: So the anxious attached partner will come in and say, hey, I think, uh, we, you know, you're not, you know, Pulling your weight. I need you to do X, Y, and Z and avoid an attached partner. We'll say like, no, no, it's fine. Like maybe we shouldn't be doing that. Or maybe, you know, that, that isn't important or you're crazy that we need to do that or whatever.

Dean: And then the anxious attached partner will get frustrated and sort of disappear and then come back and be like, you know, I'm sorry that like I put that on you. You're right. Like maybe it's not important or maybe I can handle it or maybe we'll hire someone else to do it. Um, and often that. Will cycle, um, where there will be a pattern of the anxious attached [00:28:00] partner creating a fight with the avoidant attached partner.

Dean: And then, um, sort of a back and forth happening as the tension grows and then bringing some sort of a break between them. And then, um, the avoidant, um, the, the avoidant attached partner sort of, Um, has some distance from the anxious attached person, the anxious attached person storms off and then the, um, eventually the anxious attached person comes back and, and, and repairs the relationship and, and then they cycle again.

Dean: Um, have some romantic relationships, have some professional relationships. It's worth understanding. It's very hard to break out of. But it is definitely possible. And the way to break out of it is through the assertiveness and self awareness stuff, or just changing the dynamic. But, um, it's hard. 

Mehmet: [00:29:00] Yeah. Now if I want to combine what we talked about today, Dean, like, you know, whether it's about, you know, the, the We talked about the fields and how they can overcome them.

Mehmet: We talked about, you know, the communication. We talked about the attachment theory and we talked about desire. Of course, at the core of every startup is a value that the co founders, they sit together and they put, and it defines, you know, of course the trajectory of that startup plus the culture of this startup.

Mehmet: So if, if I want to take all this and I want to Put it in a way that I can build a value that can last for longer time and I'm saying longer time And I asked this to co founders. I asked this to coaches on this show I asked too many people and I like to get you know, these insights because everyone Has their own view about it.

Mehmet: My question always is the following. [00:30:00] Why the culture divert at some state? There's a breaking point. After that, you start to see things getting messy. So first, will this help to maintain this culture that the co founders put together at the very beginning and how they can maintain this using these Um, you know, theories and, you know, the, the leadership style, how they can maintain as long as possible, the same culture, the same, you know, intimacy, if you want to call it when they started all together, because at some point we know it, it breaks.

Dean: Yeah, I mean, I guess there's, um, I, I guess my reaction is like, do we need to keep it together for a long time? Um, that feels like trying to control an outcome, which feels, uh, sort of [00:31:00] manipulative, right? Like we're going to try to reach a goal, What we wanted years ago is what we still want. And maybe, maybe you do, right?

Dean: If the co founders are able to come together and say like, What do I want now? Like, what I want now is the same thing I wanted then. And like, we can agree on that. Um, and maybe they're going to come together and say like, Actually, you know, I don't, Still want that. Or maybe, you know, in retrospect, I'm learning that, like, I think I said, I wanted that, but I want something different.

Dean: And I think the, uh, the best approach to creating a successful company is to have the flexibility. And to, uh, to be aware of, of my desires in, in fairly real time so that, you know, I, I can adjust that, like maybe one of the partners needs to leave, or maybe one of the, uh, or maybe the company needs to pivot or the values need to change.

Dean: [00:32:00] Um, but what I want now as the person I am now with my current life state or the current state of the company or the current state of the market or the economy or whatever the factors are that are affecting this are different. Um, I guess I would want, I would recommend designing a company around Um, being agile and flexible as opposed to trying to create a value system that will last forever, or at least for a very long time.

Mehmet: That's a, you know, I like to hear different opinions, different approaches. I'm learning. It's a learning curve for me also as well. And thank you for sharing that Dean. Um, you know, as we come close to the end, um, if I want to, because you know, You've done it all and you've seen it all. So if you want to give a couple of, um, you know, advice for fellow entrepreneurs who are just starting out or they are on the verge of [00:33:00] starting out, especially the ones who might be currently sitting and, you know, facing maybe a pivot or about to take a major decision point.

Mehmet: So what is like final advice you can give us? 

Dean: Yeah, I mean that's I would go back to those five ways. I really asked myself. What is it that I want and try to make decisions for my desire as opposed to What I think I should be doing I would really keep in mind Um, the, uh, the set of expectations that have been placed on me by others.

Dean: And instead, um, think about what is important to me as a person, because the only way I'm ever going to be happy and get what I want is if I do what. I know I I want that's important to me in my core. 

Mehmet: That's great advice. Uh, dean [00:34:00] finally um This is a question. I ask also to all my guests anything like I didn't touch base you want to to mention it and Also like where people can get in touch with you and know more about your current company.

Dean: Yeah, I definitely uh Recommend checking out geocene. com. Um, our companies, uh, we're moving hard into this, uh, carbon credit validation space, uh, absolutely love talking about carbon credits, definitely love talking about cook stoves and also love talking about, uh, the impact of, uh, emotions, assertiveness, uh, and, uh, attachment theory as it relates to business.

Dean: Um, if you're interested in any of that, reach out to me, you can hit our contact form that goes to me. Um, So I'd love to love to hear from you. 

Mehmet: Sure. I will make sure that I will put the link in the in the show notes Dean, thank you very much, uh for being with me today. I know it was late for you also, [00:35:00] uh in in On the west coast in the u.

Mehmet: s So thank you very much for making it and this is for the audience If you just discovered this podcast by like thank you for passing by if you did like this episode please subscribe to our podcast wherever we're on all podcasting platforms and You Tell your friends and colleagues about it. And if you are one of the loyal followers who keep coming and keep sending me their messages, thank you very much for doing so please keep them coming and thank you very much for tuning in.

Mehmet: We will meet again very soon. Thank you. Bye bye.