Today on the Edge of Innovation, we’re talking about entrepreneurship and the challenges that entrepreneurs face.

Show Notes

The One Minute Manager by Kenneth Blanchard

The Myers-Briggs Personality Test

Elon Musk lives in a Virtual World

The Challenges of Entrepreneurship

Jacob: Welcome to The Edge of Innovation, hacking the future of business. My name is Jacob. I’m here with Paul, and we are talking about one of my favorite topics today. We’re talking about entrepreneurship. What are challenges that entrepreneurs face? I have been involved with entrepreneur work. Paul has been involved with entrepreneur work since I was in diapers maybe.

Paul: Probably, yeah.

Jacob: Probably. So we’re going to be talking about the challenges that face entrepreneurs today, and so just to get us started, Paul, would you just talk us about, talk to us about what entrepreneurship is? What is it about?

Paul: Well, at its fundamental, it’s starting a business and it’s all of the things that are involved with that. And you might think, “Okay. You know, what’s a business?” Well, a business, you really have to define. I mean, we’re starting a business. What is a business? And I think that the – I’m going to make up my definition for a business and say that it is a service or product which you’re offering to people that they will pay for. So you exchange value for money.

Jacob: Yeah, it’s a value proposition for financial gain.

Paul: Right. So… You know, in the postmodern, might I say, millennial mindset, there are some people that believe you should just give me money because I exist. That’s not what business is about.

Jacob: It’s not about that?

Paul: No. Not currently. It might change, You know, in Star Trek—

Jacob: I thought you were just going to give me money because you liked me.

Paul: I might. I might. But you can’t necessarily plan on eating next week because of that.

Jacob: Based off of that. Yeah.

Paul: Based off of that. You know, and in Star Trek, you know, there’s this altruistic, everything is provided and it’s an interesting paradigm shift.

But that’s not where we’re at least yet. So what do you do? And there are lots of businesses out there. All of those had to be started by somebody. The person who started that, or the collection of people that started that are called entrepreneurs. And that is something that is a deliberate choice. Many people might back into it. And I think on one of our earlier podcasts, we talked about the idea that….So many people might back into this idea of entrepreneurship because they want to bake cakes.

Jacob: Right. We were talking about that earlier.

Paul: Right. So you want to bake cakes, and you say, “Okay, so I’m going to open up a cake shop.”

Jacob: Right. Because I want to do this on my own.

Paul: I love it. Very quickly, it becomes not about baking cakes. It’s about, well, how do I get the flour? How do I pay for the flour and the sugar and the icing and all these different things? And how do I do that?

Jacob: What are the legal ramifications of the company?

Paul: Legal and how do I get a store? And how do I paint the walls, and what are the legal…

Jacob: Yeah. What are the qualifications for the employees and how do I keep everybody on task?

Paul: Well, yeah. I mean, not even… But even just the fact that I have to file taxes. You know, the fundamental business license and all these different things that are… It’s like peeling an onion, you know, that you need to… Oh, well, if you have more than 20 people, all the rules change. And so how do you do that? And there are these sick people out there that enjoy discovering that and I’m one of them. It’s a challenge that I get energy from. But it’s, you know, and there’s always a new thing.

Like we were talking about, “Well, we should do this and this and this.” Well, I, you know, based on my experience, like, well if we do that, we have to get this kind of license and we have to do this and this implication for reporting. And we might have to pay extra taxes on that. The person who had that idea didn’t have a clue about those things, and it’s like, “Oh my gosh. That’s sobering.”

And, and so there’s a lot of wantrepreneurs out there. It’s a well-worn—

Jacob: Is that a phrase unique to you?

Paul: No, not at all. But there’s a lot of people who believe they want to be an entrepreneur, a wantrepreneur. But the fact of the matter is that there’s nothing stopping you from being an entrepreneur. A lot of people say, “Well, if I had money,” or “If I had this,” or “If I had this.”

And I heard a talk recently by an executive, Bob Doll, and he was saying, you know, “We’re all given the same amount of time.” You know, so if you’re aware of the different circles out there, Bill Gates and, you know, they took something. They had the same amount of time. Bill Gates wasn’t wealthy, you know. He was upper-middle class but his parents weren’t, you know, rich. They couldn’t give him a million dollars or something. And he made something happen. He went through the hard work.

And I say, being an entrepreneur is the hardest thing you’ll ever do.

Jacob: Yeah. It is. It is… I mean, in some ways, it’s a bit of a grind, but it’s constant work. It’s constantly innovating, pressing forward…

Paul: Yeah. You wake up every Monday, and you’re unemployed. Because see, when you wake up and you have a job, whatever it might be, all you have to do is get yourself there and reasonably perform, and even if you don’t feel like it, it will happen.

With an entrepreneur, you can’t just show up.

Jacob: That’s interesting. I never quite put it in that category. But that’s definitely how I’ve felt with the entrepreneur work that I’ve done where it’s… If I don’t show up, nothing happens, and then there’s no money.

Paul: Right. Exactly. And…or goal. You know, you’re not meeting your goal. You’re not moving towards it. And one of the, the most difficult things for an entrepreneur to deal with is that transition from doing it all yourself to getting other people to do it. And that’s one of the biggest lessons you need to learn, is you need… It’s not about doing it yourself. You need to figure out how to get other people to do stuff for you. Because if you do it all yourself, you’re limited. You only have 24 hours in a day.

Jacob: Yeah. In this whole category of delegation is what you’re talking about. Actually, I have on my desk because I’m going to be reading in the next couple of weeks, The One Minute Manager.

Paul: That’s a short, good book.

Jacob: Oh, man. It’s super short. But even just the first few pages have been super helpful because this whole category of delegation, I mean, I personally never went to business school, but it doesn’t seem to be very well sufficiently covered in the entrepreneurial literature because it’s… The moment you go from month one to month two, and you’re building momentum, you have to start delegating.

Paul: Absolutely. And it’s the key, I think, stumbling block for a lot of entrepreneurs. So a huge challenge there is that you need to change the way you do things, because now it’s not about me coming up with the best idea and I’m going to paint the picture. That would be great, you know. And I create a business that paints one picture a week. But if I really want to move past that, I need to get other people painting the pictures for me.

And that’s a hard thing, you know, to do. So I think it’s also… You know, a lot of people… Well, I think a lot of people in this sort of wantrepreneur have a romantic notion of what an entrepreneur is. And that’s because, you know, like everybody wanted to be a rock star, wants to be a rock star, because they see the romantic notion of the successful rock stars.

Jacob: Yeah. Or they see, for example, like Steve Jobs was fantastic and he was a visionary, and he did these great things. It’s like, well bro, first off, you aren’t Steve Jobs, no matter who you are. You’re not Steve Jobs.

Paul: Yeah. That’s true.

Jacob: But, I mean, it was, you know, regardless of all the, you know, the ways in which you could critique Steve Jobs, he was a force of nature in terms of just the amount of work that he produced.

Paul: Well, that’s true. I don’t think it’s that helpful to look at him as a model.

Jacob: Yeah. I don’t either. I would agree.

Paul: Because he’s an outlier. He’s an anomaly. You know, you need to look at… And I think this important for smaller businesses. You know, you have a photo… You’re a photographer. And you’ve got your store, and you know, or your studio or whatever it is. And you’re largely doing that. You will inherently be limited by that fact if you’re the only photographer. And so there’s an aspect… There’s wantrepreneurs who just talk about it. But there’s the wantrepreneurs who are in business who want to be bigger than that but aren’t doing anything to make themselves bigger than that.

Because the first thing you need to do is hire another photographer and say, “Okay. This is how you do it. This is how you do it. This is how you…” And then hire another one. And hire another one. And you know, you can’t just be doing it yourself. The minute you do it all yourself, you’re doomed, because it’s not going to scale.

Jacob: So that’s some of the challenges that present for people wanting to be an entrepreneur. What are some of the questions that they should be asking? So what are some of the questions that they should be asking to move themselves towards entrepreneurial work?

Paul: Well, I think first of all, you need to assess whether you’re wired to be an entrepreneur. And do you… How do you react to stress? Do you thrive in it? Does it compromise your health? I mean, stress is bad for everybody. So it’s really, is it stressful to be going through and dealing with cash flow or dealing with the people doing the work.

Jacob: Have you ever done, like, a personality test?

Paul: I have. Yes.

Jacob: I found that really helpful just in terms of, like, a practical thing. I think people with… So if somebody is listening to this and they’re like, “Okay, how do I respond to stress? Oh, I binge on ice cream.” Well, that’s an effect of how you respond to stress, but actually, you can kind of get some keys from, like, a Myers-Briggs personality test. So I did a Myers-Briggs personality test, and when you start reading through what they call the shadows of your personality, so what you respond when things get difficult where do you go? What are the shadow that…? And it’s helpful to understand.

So, for example, my personality is I’m very relationally-based. And so when I experience the stress of entrepreneurial work, my personality goes to assuming that that’s personally intended, like, so that I inject… Because of my, the positive side of my personalities, I build relationships easily. It comes naturally. But when things get stressful, my stress level takes me to thinking, “Oh, this is personal.” And so—

Paul: Well, it probably is in your case.

Jacob: Probably.

Paul: Sorry. I’m playing to your insecurities here.

Jacob: Yeah. But I would say in terms of trying to figure out how do you respond to stress that’s an easy step forward, to try to determine…get an object analysis.

Paul: Yeah. I think you’re right. You know, I can’t tell you what you’re problems are and what’s going to stop you, what you’re stumbling blocks are going to be. And it’s interesting, I’m working with somebody who is starting a business, and I’ve given them some advice, and they are not following it, you know. So it’s not within their perception that that is the right path to go. And it’s easier to do what they’re doing. And that’s fine. And they will probably get a business that will grow to a certain point, but it will stop at that point.

Either there’s a vast difference between building a small business with like a couple of people and a big — not a big business, but, you know, a 50 to 100, 200 person company. Those are mostly done through deliberate actions of the entrepreneurs, of the founders. It doesn’t just happen. It’s deliberate systematic work that you do.

Jacob: Yeah. So what are other person questions that entrepreneurs should be asking themselves?

Paul: Well, are you focused? Can you—?

Jacob: I’m sorry. What were you saying?

Paul: Yeah. Who were we talking about? Again, you know, there’s lots of shiny things in the world. And you’re going to be interested in that, and man, it’s a lot easier to be distracted by that. You need to have a singular focus on what you’re goals are. And you need to be constantly re-evaluating that, you know. Do you doubt your ability? You know, in some ways, you need to doubt your ability, because you’ve got to go and get help. And you have to get that help to invest in you. But then there’s the other extreme of that is if you doubt it, you’ll become paralyzed. “I can’t do anything, because I can’t do that. I can’t do that.”

Jacob: I wonder as well if a question for you to personally wrestle with moving towards being an entrepreneur or being an entrepreneur — what’s your support network?

Paul: Yeah, that’s a good point.

Jacob: You know, whether it’s your wife, your husband, or your friends or family, it seems to me that people who have healthy networks thrive, even in difficult entrepreneurial situations. Whereas people who don’t, they seem to flounder in a way.

Paul: Yeah. It would be interesting. I think that’s accurate for the majority of people. But I think there are the loan wolfs. I think Steve Jobs was probably a lone wolf. And Elon Musk, I get the sense that he’s a lone wolf.

Jacob: Yeah, but he’s in a virtual world of a lone wolf.

Paul: It’s a construct in his own mind.

Jacob: Construct. Right.

Paul: Yes, that’s true.

Jacob: Sorry.

Paul: No, I agree, you know. If you don’t know what we’re talking about, look it up. It’s fascinating.

Jacob: Yeah. It’ll be in the show notes.

Paul: Alright. Okay. So, you know, and as you’re starting a business, there are so many things that you need to do. How do you know those? Well, you can buy a book. That will tell you some of them, tell you one person. But you’ve got to have mentors and people out there that you can follow and ask questions. And I’ve found that it’s a joy to share that with people, you know. “Oh this. You should do this.” Or, “You should do this.” Or, “You should do this.”

Most people want to share information.

Jacob: Yeah. And I think for truly successful entrepreneurs, some of the double joy of being an entrepreneur and seeing something build and thrive is then being able to turn and help other people.

Paul: Well, because you now get to be involved in building and thriving again.

Jacob: Exactly. Yeah. There’s the Russian… Or there’s a Russian proverb that joy shared with a friend is double joy. It’s, I think, especially entrepreneur work, that’s definitely true.

Paul: It is. But I do know that there are a lot of entrepreneurs who have had to go it alone because nobody saw their vision. And, you know, that’s really true. And that being alone is hard with that vision, and it’s a bet that you’re making. And you’re all in. Because you’re either going to be proved right or wrong.

Jacob: It’s a pass/fail—

Paul: Well it’s a pass/fail, but it’s loaded with fail because if you miss on any number of things, you could, you will fail. Whereas pass, you have to be successful on almost everything, you know, so it’s not pass/fail. It’s like, I’m either going to be… If there’s 100 questions on the test, I’ve got to get them all right. And that’s just hard.

Jacob: Yeah. That’s very difficult. So what are some of the external questions that people should be asking?

Paul: Well, I think, you know, this is more work than you can ever imagine. And if you imagine it to be a certain amount, double or triple or quadruple it. It is relentless.

Jacob: Yeah. I’ve had friends talk to me about “Oh, I want to start a company,” and I… Great idea. I’d love to see them start a company, but just making the external observation, I think when they think of work, they think of 35 to 40 hours a week.

Paul: Yeah. It’s not at all that. I, in running my businesses, you know, maybe to my fault, you know, I’ve spent 80, 90, 100 hours thinking about my business every week. You know, it’s you’re always on.
Jacob: Yeah. Especially if you are, you know, the CEO of, or the lead on an entrepreneurial work, your headspace is the business.

Paul: Yeah. Absolutely. And there’s a cost to that, that your family, to your friends, and you need to weigh that cost. Is the money I’m going to make, going to outweigh that. And you know, my kids are in their teens, I don’t want to sacrifice that and having looked back and say, “Oh, I missed their teenage years.”
Well, yeah. Now we’ve got a lot of money, but they don’t know their father. So, you need to count that cost.

Jacob: Cat Stevens wrote about this. Didn’t he?

Paul: Yes. No…

Jacob: “Cat’s in the Cradles”?

Paul: No. That’s not Cat Stevens. That’s Jim Croce.

Jacob: What?

Paul: Yeah. The cat, “The Cat in the Cradle” is—

Jacob: Cat and the silver spoon.

Paul: Yeah. That’s Jim Croce.

Jacob: Jim Croce. Are you kidding me?

Paul: Yeah. Cat Stevens is a man who has a name that says “Cat,” but oh my gosh. We will have remedial class in pop culture and music on our next podcast.

Jacob: I’m sorry. I got those wires crossed.

Paul: Boy, you did.

Jacob: Anyhow, a “Cat’s in the Cradle” moment. You don’t want to have that as an…

Paul: Well, yeah. That’s dramatically portrayed in that song, you know, that, it basically talks about what your priorities are and one of the things that’s, you know, key to me is I work to live. And that is not necessarily compatible with being an entrepreneur.

Jacob: Right. It certainly… If being an entrepreneur is narrowed enough in terms of life goals, saying, “I want to work to live, rather than live to work,” making that distinction narrows the field even further.

Paul: Yeah. Absolutely. It’s very difficult to be a part-time — you know, working 40 or 50 hours a week — entrepreneur. That’s part-time. You’ve really got to be all-in on this. And you know, come into this with your eyes wide open.

Jacob: Yeah. So, any other external observations before we start closing up?

Paul: There’s so much, you know. There’s legal, procedural, marketing, technical, competition. Just the product, the customer service, customers, love them or hate them, you know, you need them, and they’re great when they’re great, and they’re hard when they’re hard. And you’ve got to deal with that. And you’ve got to be a counselor to your employees. And you know, it’s very difficult, and you can’t just have one thing that you do, like making the cakes. You’ve got to deal with the fact that your baker that you just hired, is now sick. Who’s going to do the cakes today? Well, I know I can, but that isn’t going to scale a business, you know.

And so there’s lots of these crises that occur, and you have to be wired so that you don’t go off the deep end and be, “Oh my gosh. The world’s going to end here.” Or, that can’t be stressful, you know. So I think that’s the biggest thing, is that it’s hard. Not everybody is wired to do it.

Jacob: So it seems like maybe some people shouldn’t be entrepreneurs?

Paul: Absolutely. Yeah, absolutely. Yeah. You wake up every Monday, and you’re not employed. Nobody is going to do it.

Jacob: And that’s a helpful principle or reality, I guess, to keep in mind with being an entrepreneur. Can you, as your make up as a person, it’s not necessarily a diminishing of your value in the least, but can you handle that sort of, you know, going to bed Friday night. You will be unemployed by Monday morning.

Paul: Right. Exactly. I mean, you know, not everybody can be a linebacker in the NFL, but some guys are wired that way, and they love it. And the hits don’t bother them, at least initially. But, you know, it does take their toll, you know. But, but I would not enjoy that. I would not find that exhilarating, you know. So we’re wired differently.

Jacob: Yeah. So we’ve been hitting a little bit of the negative side of…or just the realities of being an entrepreneur. It does some to me that if somebody has the wiring and composition, I think they can either grow into or be coached into being a fully thriving entrepreneur and somebody who embraces the realities of what’s engag— what they’re engaged in. But can you give us kind of a final, like, positive note for entrepreneurs?

Paul: Well, I think that, you know, I work with a local school, college that has an entrepreneurial area. And what’s interesting is, you know, I’m not a Steve Jobs. I’m a… you know, If Steve Jobs is an A-level, I might be a C or D-level entrepreneur, you know. Maybe even an E. I don’t know.

I understand some of the things about it. I haven’t done as… I haven’t been willing to compromise in a lot of ways or sacrifice. And what I find is, you know, people have this idea for this new widget. And then I say, “Well, is there any competition? Who else is building it? “And they’re like, “I don’t know.”

You know, so this is your tiger to take by the tail. And you need to pour yourself into it. And you know, just like you hear stories of musicians or book writers, “I sent it to 10 companies, publishers, and they all rejected me. And the 11th took it.” Well, you’ve got to keep going. And you’ve got to have that faith. You know, that story of the 10 is J.K. Rowling. You know, she sent it to 10 publishers. They all said no.

Jacob: Well, even… We were talking over lunch today about Stranger Things. And I believe it’s the same type of story where they presented to several major networks, you know, did their own.

Paul: You’ve got to believe in what you believe in and go after it. And, you know, there will be setbacks. I want it to be all peaches and cream, but it’s not. And I would, I would venture to say that I don’t know if the risk-reward payoff is necessarily worth it for all entrepreneurs. I think it’s probably the exception that it’s worth it, because in our own human nature, we will do too much and spend too much time away from our families. And if you could rewind that life… So the successful entrepreneur and they go through, and they have a terrible relationship with their children and their spouse and they are very successful money-wise.

And I’ve met a lot of these guys — Wall Street guys and a lot of the people in, you know, Connecticut outside of New York. And boy, they have worldly standards. They’ve succeeded.

Now, if we rewind that and go back at that critical moment where they choose to be the entrepreneur and redirect them, I don’t think their life would be all that much worse, and maybe even better.

Jacob: Well, and you know, honestly, this is maybe a topic for another podcast, but you and I were talking about this earlier, that at the core of, I think, maybe genuinely good entrepreneurial work, is not the widget or the product that you are trying to achieve or the business you’re trying to build, but it’s the people. So and that includes the whole range of people from your family to the employees to your customers. Are you trying to better them? Are you trying to serve them, help them thrive? Or is this just basically about you and your widget that you want to get out there and get your name up there?

Paul: Yeah, I mean, you know, it is. If Steve Jobs was reduced to the iPhone, I think that would be pretty sad, you know. He was a person. He had a wife that loved him. He had kids that loved him. You know, he had relationships, and I think those are what’s really matters, you know. Yeah, the iPhone is really cool, but I wouldn’t be that, you know. It’s interesting how we sort of, you know, the Wright Brothers, they invented the plane. Well, they were people too, and I’m sure things made them laugh and smile and things like that. And it wasn’t all around the plane.

Jacob: Yeah. Well, I think that’s a great note to end on. Entrepreneurship is about starting a business, but we want businesses and entrepreneurial work that serve and help other people to thrive.

Paul: Absolutely.

Jacob: Thank you for listening to this episode of The Edge of Innovation, hacking the future of business. I hope that this was helpful for you. We’d love to hear from you if you have any questions, or if you have any comments. Please visit us at Paul where you can find the show notes for this episode and all of our previous episodes and where you can get a hold of Paul if you would like to talk to him personally.

Thanks again. Have a great week.

Also published on Medium.