Enjoy The Cocktail, Not The Shot

Episode 29

In this episode, Scott and Robert will talk about whether you should focus on learning a broad set of skills or develop skills in a specific niche. We'll talk about the pros and cons of each approach and how they apply to life as an entrepreneur.

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this Stretch Goals Quick Hit, Scott and I are going to be talking about how it’s not about the shot, but the cocktail.

Scott: That’s right. This is the Stretch Goals podcast where each week, we’ll share insights and lessons learned based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Scott Davis.

Robert: And I’m Robert Dickerson.

So I heard this phrase mentioned on the Seeking Wisdom podcast from Drift. If you haven’t checked out that podcast, you should. It’s really good podcast around entrepreneurship and just about learning in general and growing your company. They had an interview. They were talking about whether you should focus on learning a specific skill and spend your time on that, and so that’s the shot. Or whether you should focus on a broad base of skills, the cocktail, and what’s more valuable. So they were talking about how the cocktail and this mix of skills is more valuable.

I think in entrepreneurship, that’s true because you put on so many different hats. You’re asked to do so many different things. Even throughout my career, I’ve thought a lot about this is whether I should learn a specific skill set or whether I should kind of be broad. I think my career is kind of … I’m more broad where I can work in a lot of different areas but maybe I’m not an expert in those. I think you’ve kind of done something similar. Maybe you’re a little bit deeper on iOS and focused on that. I thought this would be cool idea to talk about in this episode.

Scott: I did both and here’s how. When I was younger, I needed a broad range of topics in my arsenal. I needed to be a jack of all trades so that I could work on absolutely everything and gain my experience. At a certain point though, I saw the need to be an expert in a specific topic instead of everything just because it’s difficult to keep up with everything, especially when you have family and kids. Just because it’s something that made me more interested in what I was doing. So when it came to mobile development, I specifically decided to focus on iOS. It doesn’t mean I can’t develop Android apps. I have and I will. But what it means is that I am an expert in iOS. I know that with 100 percent certainty. That I could pass any interview, by anyone, on the topic. That was my goal. I wanted to be an expert. I wanted to know absolutely everything about iOS development for iPhone and iPad.

What’s great about this is, I have a broad range of experience meaning I can do web, I can do back end, I can do front end, design, all of it. I can do absolutely all of it but I’m an expert in one thing. I think the lesson that I learned from it, and that’s not to say that I won’t become a jack of all trades again as technology shifts and the needs of startups and businesses in the world change. For me right now, I’m passionate about one specific topic and I still do all the other things as needed.

I think it’s a good skillset to have. I say, be broad while you’re learning and getting experience. Then as time and situation presents itself, become an expert in one thing.

Robert: Yeah, I think we all have different interests and different passions so that may lead people to go down specific path and try to learn more about a topic. Whether that’s marketing, whether that’s sales, whether that’s product development, right? We all kind of have that niche where we want to learn more. I think if you can grow your skills in different areas and see opportunities … You know, as an entrepreneur, you have to tackle things in all these different areas and so you have to learn quickly, different pieces in all these areas. But even if you work in a corporate job in a corporate world, there’s value in moving around within the company to hone your skills in different areas and get out of your comfort zone. That is really important to get out of your comfort zone.

Scott: Absolutely.

Robert: A lot of people don’t like to do that. They like to have the same job, they know what the expectations are. They come in everyday and do their work. But when you shake things up, that’s when you learn. That’s when you grow as a person and grow your skills. If you want to become an entrepreneur, those are the opportunities that you have to tackle and you have to be confident that you’re going to learn something even if you don’t know anything. If you go from being the smartest person in one area to being the person with the least amount of knowledge, you’re just starting from scratch. You have to do those kind of things to grow your skills.

Scott: Yeah, I think if you look at the startup ecosystem, you’re right. You’re wearing 10, 15, 20 different hats. That’s great because, again, you’re expanding your skillset and you’re gaining knowledge and experience. But if you look at the corporate world, you don’t see a CEO who’s also the CFO and also the CIO and the CTO, you know what I mean? At a certain level, being an expert in one field becomes a need.

But in the startup space, it’s the exact opposite. As your company grows and you’re the CEO and you’re making all these decisions, eventually an investor comes in and says, “Hey, you need to bring in a CFO because you’re spending too much time on the financial side.” So then you can take one hat off. Slowly but surely, as you move up in the world, that need sort of changes and it’s dynamic. I’m not saying that you should never be a jack of all trades, I’m saying it’s extremely beneficial to be in that situation, to expand your skillset.

Now also, affords you the ability to decide where you want to be. Maybe, you decide that you really like finance while you’re being the CEO of your own company and then you end up being a CFO at Yahoo or something. That’s great, that experience. By being exposed to all those things, allows you to decide what you’re most passionate about.

Robert: I think being able to communicate with the different people, different groups, and understanding enough to be able to identify their struggles and what they’re trying to accomplish, you don’t have to be an expert. I think you hit on a good point is that, you want to hire people that complement your skillset. You bring in experts to help you in those specific areas. That’s the great thing about growing in the company is that you can hand pick those people to come in and complement what you’re doing and be better in all these different places. It’s the team mentality that really helps you in the end, grow as a business.

Scott: Sure. One thing I’ve noticed in the tech space specifically, is that salary ranges can vary by a lot but they tend to vary in favor of more money for experts in one field, versus someone who’s jack of all trades. If you see a position right now and it says back end dev, that usually means 10 or 15 different technologies that you’re using to maintain servers. But if you see iOS developer, the salary’s going to be about 40 grand higher and they’re only going to be working on one thing.

Expertise in the technology field, and I don’t know if this applies to other fields, it might, but if it’s a hot technology, there’s a large price discrepancy. If it’s not a hot technology, then there is none. Remember when Java came out, 15, 20 years ago. Java developers were billing out at two to three times the rate of a C++ developer. Again, that comes down to being an expert in a specific thing so that’s in favor of the shot instead of the cocktail in terms of salary. But again, what happens in that scenario, is as that technology becomes less important, the salaries come down and then you have to shift your expertise to somewhere else. Or you chalk it up to learning and adding that to your arsenal and your jack of all trades scenario.

Robert: Yeah, that’s what I was going to say, is that you can start off high, especially in an engineer development world. But as that technology progresses, you get new people coming out of college or new engineers, new developers that have a stronger understanding if you’re not keeping pace. Exactly like you said, you kind of cap out and so people start looking for these younger engineers that are cheaper and that have skillsets in these new technologies that they can apply.

Where I’ve seen it is where people like program managers, sales associates, and stuff. People that have an impact on the financial success of the business, those are the people that start being really valued over just the people developing the product because they’re having a financial impact on the growth of the business. Whether it’s right or wrong, those people start moving up into the higher salaries and things of that nature. So developers and people like that with a specific skillset, maybe get passed along.

That’s just something to think about. There’s ebbs and flows in all this and it kind of goes back to the, “You’re always learning, you’re always looking for opportunities.” I think it translates well into entrepreneurship as well because you’re always kind of learning where you fit within the startup space and how you can use your technology, how you can use your team to kind of grow your company.

Scott: The one thing I want to say about my time in the corporate world is that, I always felt frustrated because I was a jack of all trades at that time. I always wanted to work on everything that came down to the business. It was like, “Oh, I can do that. Let me work on that.” And they would give it to another team, another individual. I didn’t like that. I always wanted to work on everything. That’s why I was a jack of all trades.

I was constantly frustrated with that because what happens in the corporate world, generally, not always, is that they have a team that does front end development and they have a team that does back end development and they have a team that does databases. Well guess what? I want to work on all of them. Well guess what, you can’t. Not in that environment. So that becomes very frustrating and then it almost forces you to be an expert in one field because that’s all you’re working on all the time. That was frustrating for me. I remember hating that about the corporate world.

Robert: That’s funny. I was the same way. I think it’s about the ownership. The ownership piece for me was the part that kind of frustrated me the most was owning the whole product instead of just owning this little piece. When the product wasn’t successful, even though you got your piece done and it worked, the product can not be successful 'cause all the pieces coming together didn’t work. So that the ownership piece is what really frustrated me is that I wanted to be able to control the success or failure and not have somebody else controlling the budget. Telling me I couldn’t do this, I couldn’t do that. When you don’t have control of all the pieces, it doesn’t matter how well you do in your specific niche, it could still be a failure. To me, I saw that too many times that I had to try to do it for myself. Be able to control all the different pieces and own it.

Scott: Right. I want to be the entire puzzle, not just one piece.

Robert: Yeah. I like the idea that success or failure rest on my shoulders. I have no one else to blame but myself if my company fails. It’s on me to do it. But then I have the flexibility to make those decisions quickly. I don’t have to wait for somebody to approve a budget or I don’t have to wait for this person to set up a computer, or whatever it may be. I could just move forward quickly and get things done.

Scott: It’s the Michael Jordan complex. You want the ball, with the two seconds left, down by three. You want to be that guy who puts the team back on top.

Robert: One final point I want to make too is that there’s not enough time to learn everything either. So you have to kind of balance that when you’re focusing on what you want to do within your company, what skills you want to learn. You have to figure out how to distribute your time among all these different tasks, especially if you’re focused on kind of being a more general person. It’s important that you figure out where your niche is, where you want to be, what makes the most sense for your business to help you grow. Then like, Scott, you were saying, hiring people that complement those skillsets and maybe they can help you even grow faster.

I have a trainer that I’ve been using at the gym and within six months, he’s helped me go way farther than I ever could have within … For myself, right? Even over a multiyear time period. To get mentors, to hire people like that that can help you, kind of push yourself forward, I think that’s really important.

Scott: I agree.

Robert: All right, so let’s wrap it up and hope this episode was useful for you as your … You know, you’re thinking about it’s not just the shot, it’s the cocktail of entrepreneurship. So go on out and get a drink and think about it.

Scott: Turn that into a bumper sticker.

Robert: Yeah.

Scott: Thanks for listening to this episode of the Stretch Goals podcast. You can access the show notes for this episode and listen to other episodes by heading over to stretchgoals.fm.

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.