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KF #5. Business Insight Archives - How to be Awesome at Your Job

865: The Universal Principles of Successful People with Dave Crenshaw

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Dave Crenshaw says: "Fail early."

Dave Crenshaw shares valuable insights on how people succeed, gleaned from his guests on The Dave Crenshaw Success Project podcast.

You’ll Learn:

  1. One thing every professional should learn
  2. The trick to multiplying your career opportunities
  3. Why to take that risk now—not later

About Dave

Dave Crenshaw develops productive leaders in Fortune 500 companies, universities, and organizations of every size. He has appeared in Time magazine, USA Today, FastCompany, and the BBC News. His courses on LinkedIn Learning have been viewed tens of millions of times. His five books have been published in eight languages, the most popular of which is The Myth of Multitasking—a time management bestseller. As an author, speaker, and online instructor, Dave has transformed the lives and careers of hundreds of thousands around the world.

Resources Mentioned

Dave Crenshaw Interview Transcript

Pete Mockaitis
Dave, welcome back to the How to be Awesome at Your Job podcast.

Dave Crenshaw
Hey, Pete, I really appreciate it. It’s very generous of you to have me come back again. What is this, the third time?

Pete Mockaitis
I think so. I think third time is the charm, so the first two that we botched, we’ll, hopefully, redeem ourselves.

Dave Crenshaw
Yeah, exactly.

Pete Mockaitis
So, Dave, I’m intrigued, you are up to a whole new project, and, in fact, your name is on it, and I hope it’s successful. It’s called The Dave Crenshaw Success Project, a podcast. And we talked about this back when you were just conceiving it, and it’s fun that it’s up and out in the world. So, I first wanted to hear a little bit of the story. You pursued this project not with the goal of advancing your empire as an expert, speaker, course creator, dude but something else. What’s the scoop here?

Dave Crenshaw
Yeah. Well, so those who aren’t familiar, I’ve written books and I’ve got courses, over 30 courses on LinkedIn Learning. I know you’ve got, gosh, a lot more than that and you’ve been very popular on that platform. And I do speaking as well, but what I wanted was something that inspired me and scratched the itch that wasn’t required by making a lot of money.

And I had a lot of different versions, and I think you and I had some conversations about different things that I could pursue but what really moved me, the thing that got me going was the idea that I want to create something for my kids. So, I have three children. My son is 17, I have a daughter who’s 13, and another daughter who is 10, my youngest, and I thought, “I want to leave a legacy to them. What could something that I can create to help them be successful but, at the same time, other people will benefit from?”

And that’s where this idea of The Success Project came from, and if I were to sum it up in a sentence, it’s that I am getting the stories of others, and you’re one of those people, we did an interview, to learn universal principles of balanced success. So, I know a lot of times in a podcast interview you bring someone on who has a book, they have a course, and you’re going to discuss that, and I think that’s great.

My goal is a little bit different. I bring someone on and I want to hear their story, and in their story, I want to figure out “What are the things that would make any person successful? And how can we apply that to ourselves? How can I apply that to my kids?”

Pete Mockaitis
Well, hey, I’m all about universal principles, so, indeed, this is a great fit here. And so, I’m intrigued then, your kids, they also play a role in the production, I understand.

Dave Crenshaw
Yeah, the first and the most fun one is my daughter Darcy, who’s 10. She reads the outro. It’s the cutest thing you’ve ever heard in your life. It’s completely unfair for me to put that at the end because you are powerless to resist it. And my son, he does the editing, which is wonderful because now I can pay him as an editor, which helps him prepare for college.

But the fun thing that I’ve also started doing, I don’t think I had started this when you and I did the interview, Pete, is we’re doing bonus episodes where we’ll sit down and have a conversation about a principle that we learned. So, for instance, one person I interviewed was Tahani Aburaneh, and she was a refugee in Jordan, and she went from that situation to being a millionaire in real estate. And she talked about how gratitude was so essential for her success, and how her mom taught her to be grateful even when they were in these really, really difficult conditions in a refugee camp.

And so, I sat down with my kids and said, “Let’s talk about gratitude. Let’s talk about how we can be more grateful and some ways we can implement it.” So, I’ve got the regular episodes that we release where we’re hearing these stories, but then I’ve decided to have a little fun with some bonus episodes with my kids. And that’s sort of why I chose the title that I did because The Success Project is open-ended enough that it gives me a lot of latitude to try a lot of different things that will help the listener be successful and help my kids be successful.

Pete Mockaitis
Alrighty. Well, so lay it on us, Dave, what are some principles that have really already popped off the page? Let’s hear, how many interviews have you done, first of all?

Dave Crenshaw
I’m around the 20-interview mark. So, gosh, what do you have, 2,000?

Pete Mockaitis
Oh, shucks, 860-ish.

Dave Crenshaw
Yeah, okay. So, I’m an infant learning to crawl at this point, but I’ve started to see some really interesting threads, and I’ll start with one that I did not expect at all but it makes sense when I say it, is the importance of studying business. It is amazing to me how many people I’ve interviewed who maybe do something that is different than business.

For example, Angie Ford is one person. She owns several music schools and daycares. She studied piano, that’s what she wanted to be, was a concert pianist but, for some reason, she was interested in business and got a minor in it. And because she did that, that enabled her to be successful as an entrepreneur. And I have seen that one thing repeated over and over, whether or not that was their primary interest, someone took the time to study the principles of business and accounting and marketing and sales.

And so, I’ve told my kids, and right now, it’s kind of funny. Right now, every single one of them wants to be a writer. I did not expect that either. And so, I tell them, “Hey, study whatever you want in college, but the one requirement that I’m going to make of you is that you have to at least minor in business.”

Pete Mockaitis
Okay. So, the business skills are handy in terms of there’s just a business side to everything. No matter what you’re doing, whether you’re a baker or doing music or daycare, there is a business side. And whether you’re the owner or somewhere lower within the hierarchy of things, having that understanding is common and handy.

Dave Crenshaw
Right. Even if you’re a middle manager in a Fortune 500 company, and you’re hired to do one specific thing, let’s say communications, understanding how the company operates, and understanding cashflow and the things that determine a stock price and all of these things, they make you more savvy and more able to understand and read the tea leaves, so to speak, about what is going to be coming in the future.

And I think that you don’t have to go to college to study it. I think that, I mean, certainly listening to this podcast, someone who’s made the commitment to do that, already that says a lot about their character and their desire to learn. I think that you could start reading books. I think that there are certainly courses on LinkedIn Learning that will help you learn these skills. I would carve out part of your schedule each week, each month, to give it some attention.

Pete Mockaitis
And I’m curious about some of your favorite resources, like learning business. Business is quite an umbrella that… is it fair to say that you’re saying a general survey understanding of management, accounting, finance, marketing, strategy? Is that what you mean by learn business?

Dave Crenshaw
Correct, yeah. Whether you took that in college, whether you’re getting it on your own, you’re saying, “Hey, I want to get a good understanding.” I know one thing that’s been really helpful for me in my career is economics. I’m turning and looking at my shelf right now. I’ve got a couple of books about economics, one called Basic Economics.

And sometimes we’re always looking for the next new title that’s going to give us some cool principle, and that’s great. I built my career on books like that but I think there’s something to be said for digging down into the fundamentals. And I recommend taking the time to drill down on some of just the fundamentals because those will influence how you perceive things that are happening in your career.

Pete Mockaitis
I dig that. Is that Basic Economics by Thomas Sowell?

Dave Crenshaw
Yes, it is.

Pete Mockaitis
I have that book. It’s a little thick. I haven’t finished it but I loved one of his points, which was to evaluate policies not based upon their intentions, because they’re all good, all policies have good intentions, but rather upon the economic incentives that they create for the different players and stakeholders.

And that made a whole lot of sense when I read that, like, “Oh, yeah, I can see how sometimes, when things don’t quite work out,” I think rent control was an example he used. It’s really helpful to put yourself in the shoes of each of the players there, like, for example, the landlords and see, “Huh, given this legislation, what might they be more or less inclined to do because they’re going to be affected by these new set of rules?” And that was a big lightbulb for me, actually.

Dave Crenshaw
Yes. And see, that’s beautiful, and that says a lot about you, the fact that you would remember that principle from reading that book. And just understanding that, if you’re in a managerial situation, now you’re going to say, “Oh, if I change something, what’s the effect on the individuals that are following me?”

And that nugget of knowledge is so basic and it’s so fundamental but it’s so useful in the same way that water is useful to our physical survival. It’s a basic, it’s a fundamental, and we want to at least spend a little time consuming those things. My career, The Myth of Multitasking, a big influence that economics had for me was the idea of microeconomics and switching costs. That’s my love of economics, and learning it is what led me to help people with time management.

And someone listening to this might have that same experience with accounting, and they enjoy that concept of first in, first out, or whatever the principles are that they’re reading, and they can make that a part of being a bricklayer. That’s a terrible example, but they can make that, those principles a part of any career that they have.

Pete Mockaitis
Yeah, and it can help you get an understanding of all sorts of mysteries. You mentioned brick laying, one of my great mysteries, Dave, is why home renovation professionals, whether the electricians or plumbers or masons or whomever, it seems like historically I’ve had a heck of a time finding someone who would actually show up and do things. And then when you do find a winner, you’re like, “Oh, my gosh, you are my plumber for life,” “You’re my electrician for life.”

But I think the principles of economics can help illustrate that. My leading theory right now is, “Hey, Pete, you are a small fry with a small job, and it takes me lots of time to get over to you and to the hardware store, etc. to get a small amount of revenue versus there are people with much bigger jobs, which take me the same amount of time and to get there and get the materials, and yet produce a whole lot more moolah for me and the team to take care of business.” That’s my current theory, at least.

But without an understanding of economics, I might just be…well, I guess I’m still frustrated because I don’t have a plumber or whatever showing up, but at least that demystifies that or inspire some ideas, like, “Huh, maybe I can work with a contractor and bundle a lot of stuff at once so I would be a more appealing customer in a world in which they could be pretty choosy when there’s not as many home renovations pros as there is a demand for their services.”

Dave Crenshaw
Yeah, that’s a great example. And to kind of put a bow on this, I think what we want to do is say, “How does this apply to me?” I think the tendency of most people, and I’ve seen this in my coaching and training, the tendency of most people is to listen to new knowledge and say, “That doesn’t apply to me. Well, I’m going to ignore that part of what I just read because that doesn’t apply to me.”

The question we want to ask ourselves is, “How does this apply to me? How can I make this principle of accounting apply in my job in HR?” And if you just take the time to drill down and think about it and pause for a second, you’ll find applications.

Pete Mockaitis
That’s cool, and I like that taking the time to actively think. And when you’re drawing a blank, I’ll tell you what, I have been playing around a lot with this, with AI and ChatGPT. I did it a year ago and thought that was kind of some cool tricks, but now with the upgraded powers, it’s pretty cool. Like, that’s the kind of a prompt that can really spark some ideas going. It’s like, “Hey, I am in this business and I just learned this concept, how is this at all applicable to me? And then give me 10 ideas.” And then it does, it’s like, “Oh, okay.”

And then that’s what I found to be most useful for. Its final product, headlines, and teasers, and copy is inadequate in my opinion, but as a little brainstormer thought partner, I’m finding all kinds of fun little uses there.

Dave Crenshaw
Yeah, I love it.

Pete Mockaitis
And then that might be another subject associated with learning stuff that’s a principle, like learn business. We mentioned basic economics and basic principles of business. Are there any other resources that you found just absolutely killer?

Dave Crenshaw
Well, one common thread that I’ve seen so far in the interviews that I’ve done, I’ve seen this also with people that I’ve coached through the years, is taking advantage of bonus opportunities. And what I mean by that is…well, I’ll give you an example. So, I interviewed Kwame Christian. You know Kwame, right? Have you had him on your show?

Pete Mockaitis
Indeed.

Dave Crenshaw
So, one of the things that he mentioned was that he took advantage of debate club as he was going to school. And he participated in that, and that participation opened up his eyes to the idea of negotiation and how to have difficult conversations. And I’ve seen that several times where someone is, they’re going to school, they’re participating in something, and there’s this ancillary opportunity that isn’t really going to show up on a resume for a job application, and they go participate in it, and that participation leads them to something new.

And it goes back to that idea of people think there’s one path to success. The path is you pick a career, you go to school and study that career, you get your grades then you go and work somewhere. But the reality is it’s the little opportunities that you might take for granted, the things that are going to help you figure out what you really want to do, and they’re going to help you grow in your career.

Pete Mockaitis
That’s cool. And I believe you highlighted that as a theme in my interview when you had me in terms of, “Oh, that stuff you were doing in college, in high school, in terms of giving that speech. You’re like, ‘Oh, speaking is awesome. And it’s interesting that other people are terrified of this, and yet I’m super jazzed about it. Hmm, there’s a lesson there.’”

Dave Crenshaw
Yes, and it also highlights the idea that go where your strengths are. And I was just reviewing the interview that I had with Kwame, he said, “Go where your curiosity is.” And it’s not so much about your passion. Your passion can be useful but I was passionate about playing music and being a rock star, not necessarily a very usable career for me.

But I was curious about entrepreneurship, I was curious about time management. I would go to the extra lectures where I went to school, and listen to entrepreneurs talk about their experience. Those things that I was curious about are the things that became most influential in my career. So, someone listening to this, you can ask yourself, “What am I most interested in that maybe isn’t a part of my career at the moment? Am I giving myself opportunities to immerse myself in those things?” and do a little bit of it even if it’s outside of the everyday work that you do.

And when you do that, you’re opening your mind, you’re opening your time, you’re opening your opportunities to probably what is going to lead to the most success in your career.

Pete Mockaitis
That’s really cool. And something that’s come up in my podcast a number of times is folks to actually look back at what you were super interested in when you were younger can have some real clues for you. Like, before you were obligated, mandated, directed, desperate for cash, any number of pressures entered your world, what was just kind of interesting to you that you were curious about, that you dug into.

And you may very well not become a professional baseball player or a rock star or a magician, kind of whatever that might’ve been, but there’s something under the surface there in terms of, “Oh, with the magic tricks, it was delighting an audience,” or with rock roll, it’s kind of learning a thing and just getting immersed, or a sense of mastery, and sort of see just kind of “What’s the thing underneath the thing if you’re not going to be a pro sports guy or a rock and roll person?”

Dave Crenshaw
Yeah, what are the principles, what did I gain from this experience? And whether or not you’re in that career, what you learned in it will help you the most. That’s something I see with my wife who is a high school swim coach. And the reality is most of the kids that she coaches won’t be swimming past high school. Most aren’t even going to get a college scholarship. So, what are the moments within that extracurricular activity that give them an opportunity to grow and learn life skills about hard work, and persistence, and working with team members?

Pete Mockaitis
That’s good. That’s good. I’d also love to hear you, Dave, tell me, did you see any conventional wisdom get skewered along the way in terms of maybe there are some tropes or standard-issue truth, wisdom, guidance, that is bellied about that your guests have actually revealed, “No, actually, it turns out that’s wrong, and here’s a better way”?

Dave Crenshaw
Yeah, that’s a really interesting question, Pete, and I’m going to tread delicately here with it.

Pete Mockaitis
Can’t wait.

Dave Crenshaw
But I think it’s important to be said that I think there is a concept out there that having a family holds you back, that your kids are going to slow you down and keep you from being successful if you choose to have kids. Or, even, “I need to wait later in my life to get married because marriage to my spouse is going to hold me back.”

And I have found that in both of those cases, the opposite is true. Let’s talk about children for just a second. Or, even if you choose to be a caretaker of someone else. What that does is it enforces limitations in your day. First, just setting aside all the wonderful benefits of being a parent, which there are, just from a structural standpoint in your career, it forces you to not work crazy hours.

And if you love your children, you’re going to want to say, “How can I spend time with them? And if I have to spend time with them, that means that I won’t be able to wake up at 6:00 o’clock in the morning and work all the way to 9:00 p.m. I’m going to have to find breaks.” And that relationship creates a boundary that forces you to figure out how to be more productive.

It’s really sloppy productivity to allow yourself to work long hours. You’re just masking a bunch of inefficiencies in your day when you allow yourself to work those hours. But if you say, “I’m not going to go past 5:00 p.m.” and I call this principle the finish line. You define what your finish line is in the day, “I’m not going to cross that.” Well, if you have to stop working by 5:00 p.m. because your kids are going to be coming home, you’re going to have to figure out, “How can I get everything done?”

And if you have to figure that out, now I got to say, “How can I do a better job at delegation? How can I do a better job of automation? How can I do a better job of focusing on what’s most valuable?” So, that’s one of the first themes that I’ve heard come up several times. And the other one is the value of a great partner.

And, however you structure that partnership with another human being, whether that’s through marriage or just through a long-term committed relationship, the idea is that person creates a ground and a balance to what you’re doing. And, of course, this is assuming you’ve made a great choice, or at least a good choice, but having that person in your life creates stability, creates confidence, and you can divide the labor between the two of you in a way that’s useful, and that will help you grow in your career.

Pete Mockaitis
That’s cool. And I’ve also heard stories that once folks become aware, “Oh, we’re pregnant. Baby is on the way,” suddenly, the motivation…

Dave Crenshaw
Oh, that’s my story.

Pete Mockaitis
Yeah, the motivation, the seriousness really gets kicked up a notch, it’s like, “Okay, no, for real, I’m going to make this thing work.”

Dave Crenshaw
Yeah. When I give my speeches about The Myth of Multitasking, that’s one of the first things that I bring up. The two words that changed everything in my life, and changed my career, were, “I’m pregnant.” And when I heard those, I thought, “My gosh, I need to start getting more focused, and there’s this life coming in this world,” and that caused me to make that transition from maybe just pursuing my passion to pursuing a passion that was profitable. And that led me to returning to my work as a business coach and preparing how to be an author. That story still colors everything I do to this day.

Pete Mockaitis
So, we’ve covered some things that are great to do. What are some things you really recommend that we not do?

Dave Crenshaw
Yes, I would say don’t be afraid to fail. A lot of people are so concerned that something isn’t going to work out, that they stop from making any kind of attempt. And I would say do not allow that to prevent you from taking risks. And, especially, don’t allow yourself to say, “In the future, at some point, I’m going to take this risk.”

The earlier you take that risk, the less costly it will be. So, if you’re listening to this right now and you’re just starting your career, and you’re not married, and you’re just coming out of college, whatever, now is the best time to take that sort of risk, so don’t hold back. And even if you say, “Well, I’m married and I’m a little bit further down my career,” now is a better time to take that risk than five years from now, or ten. Fail early.

And that will create more opportunities. And if you fail, great, but you can recover from it. And I wasn’t afraid to fail early in my career, and I did, and it took a while to recover from it, but that was also an opportunity to learn and to grow. And that is often just as, if not more educational than an official college degree.

Pete Mockaitis
That’s a really cool perspective there, to take the risk earlier gives you more opportunities to recover, or to pivot, or to take advantage of the things that you’ve learned, the relationships you’ve built, the discoveries that you’ve made, as opposed to if you wait ten years, or however long, you will just have less time to pivot, sort it out, make good things from the pieces and the ashes that have emerged from that failure. That’s really cool.

Dave Crenshaw
Yeah, I know someone who just began their journey as an entrepreneur and owning their own business, and that’s great that they’re pursuing it, but the sad thing is they’re on the downward side of middle age, and for 30 or more years, he’s always wanted to own his own business. That’s a long time to hold on to that regret. Whereas, if he pursued it earlier, either he would have succeeded or he would not have that anymore, and say, “You know what, I took a try at that, I don’t have to think about it anymore.”

It’s funny, that’s part of the narrative that my wife and I have around my attempting to be a rock star. I had a band, I wrote songs, and sang keys, and I was doing that in my mid to late 20s. Now I can look back and say, “Wow, I’m glad I’m not doing that anymore. That was crazy.” And we’ll go somewhere and I’ll see a band setting up or something, and I’m, “Oh, my gosh, I’m so glad I’m not doing that.”

But if I had never done it, where would I be right now? “Oh, I could’ve done it.” I’m like Uncle Rico in Napoleon Dynamite talking about how I could throw the football over those mountains. Give it a shot. Even if you do it part time in conjunction with the job that you’ve got, give it a try now and then you can confidently move on with your life, or something amazing will happen because of your hard work and because of the risks that you took.

Pete Mockaitis
Yeah, that’s cool, to get a real sense of what is the reality associated with this dream. And I think folks have found it really does go both ways in terms of, “Hmm, professional music or being a lawyer or whatever, is just the coolest or is, wow, not for me. Good to know early and reorient from there.”

Dave Crenshaw
Indeed, yeah. That’s it, do it now. Give it a try now and you’ve still got time to learn from it and to do something else if it doesn’t work out.

Pete Mockaitis
All right. Well, Dave, tell me, anything else you want to make sure to mention before we hear about some of your favorite things?

Dave Crenshaw
Well, one thing that I really thought about and, as you mentioned at the beginning, you’ve done 800 episodes, another principle and a pattern of success is consistency over years, and I’ve seen this in my work with entrepreneurs. They’ll get started, they’ll start a business, they’ll go for a year, maybe two, and then they start getting bored, and they start doing something else.

And sometimes, well, you’ve seen this, Pete, let’s just talk about podcasting for a second. You go online, and how many podcasts do you see listed that have one to three episodes, right? There are 8 million podcasts but how many of them really go beyond the first five or so episodes? Not most. Most are less than that. And it illustrates the idea that when we start something, we’ve got to stick at it for a while. We got to keep going at it for a while.

And I’ve seen this with my own career, for instance, my courses with LinkedIn Learning. I started out in 2011 when it was Lynda.com, and it was my first course. There’s so much value in being a part of that and having a partnership with someone, like in my case, LinkedIn Learning, and your case as well, for 12 years. When you’re in the pipeline that long, more people have an opportunity to learn about you.

And if you think about something that you’re passionate about, I’m talking to the listener now, if you think about something you’re passionate about and you want to pursue, make a commitment to do it for a good long while. And just the principle of longevity and consistently doing it will lead to paying off. I like to say that impatience is the enemy of success. And the reason why it’s the enemy of success is it causes us to pull up roots too early.

And I use pulling up roots because I’m thinking of, like, a farming metaphor. We plant the seeds, we put water on them, and then we go away for a little bit, and then maybe we come back a little bit later, and we look at it, and go, “Oh, well, it hasn’t grown anything.” A lot of people in that situation go, “Well, this was terrible. I’m not doing this anymore,” and they just rip everything up, when we’ve got to give it time, we’ve got to keep nurturing it, we’ve got to keep feeding it, and then, after a while, you’ll start to see the fruits of your labor.

So, I recognize that what you’ve accomplished, Pete, in your podcast, a lot of it is talent, a lot of it is the hard work, but a lot of it, too, is just the fact that you have just kept at it for 800 episodes.

Pete Mockaitis
Yeah, it’s true. Things do pay off with consistency over time. Not always. Sometimes it’s like, “Hey, entrepreneur, that concept just isn’t hitting the mark for people.” And so, I think it’s a matter of saying…

Dave Crenshaw
But you’ve got to give it enough time to really figure that out.

Pete Mockaitis
Exactly. And so, I think about it from a hypothesis-driven thinking in terms of, “Okay, what do we need to learn? What are testing?” And I think, “Hmm, I’m kind of bored. I want to do something else,” is not a great reason as opposed to… I think about my failed businesses, it’s like, “Hmm, not a single person ever bought this thing. It seems they don’t actually want it after all.” So, then you could just say, “Well, maybe let’s pivot, adjust the offer.” Or if there’s no good adjustments to be made, it’s like, “Okay. Well, it’s time to say goodbye and move on and collect the learnings.

Dave Crenshaw
Yeah, and I’m aware of the paradox of what we just talked about because, just before this, we were talking about failing and failing early. And now I’m saying, “Keep at it for a good long while.” So, the question is, “How can you tell the difference between the two?” If you don’t mind, Pete, I’m going to turn that on you for a second. How do you personally tell the difference between when you’ve failed and when you just need to stay consistent?

Pete Mockaitis
I think it’s really a matter of looking at the evidence and, ideally, thinking about sort of tests, experiments, hypotheses, like, “What would need to be true for this thing to be successful?” and to see if there are some indicators. Like, I think in this business world, if it’s like, “Hey, you know what, we have successfully gotten 20 clients who are just love, love, love what we’re doing here, but we haven’t quite managed to get to a breakeven positive cashflow point.”

Well, I think that says you got something. I would not walk away from that lightly or if you’re bored. I would say, “Well, let’s figure out what are the remaining challenges we have to solve, and then solve them,” versus, “We’ve tried a dozen different marketing channels and not a single person has opted to part with their money for this thing we thought was so cool. Maybe this thing isn’t really resonating.”

And then you might choose to say, “Exit entirely,” or say, “Well, maybe it needs to be tweaked to make it more appealing, or maybe there’s a different segment that would really be into it. Maybe we were trying to go broad but, at the end of the day, this is really going to appeal to roofers, and we’d go all in on roofers,” or kind of whatever the segment is. So, I guess that’s how I would think about distinguishing it, is, “What evidence and signals have we collected to indicate this thing could be a winner versus not?”

Dave Crenshaw
Yeah, I completely agree with what you said. And so, if I were to put my own spin on it, I would say break it into milestones. So, it’s so easy when we engage in an experiment to think only long term, “Five years from now, this is where I’m going to be and I’m going to cash out of my business and own a private island.”

But the real question is, “What is the experiment of this month? What’s the milestone that we’re trying to accomplish this month? Were we successful in accomplishing that? Was I able to get this many customers because I was able to get this many people to listen?” whatever it is. And then you move from that milestone to the next one that’s maybe a little bit bigger.

So, you want to create a pattern of success but also set the milestones of success at more realistic and reasonable things in the beginning, so then you just go from success to success, bigger and bigger, as you go along. Or, you have a string of months where you’re not hitting any of the milestones and you stop, and say, “Okay, maybe there’s something wrong with this experiment that I’m engaging in.”

Pete Mockaitis
That sounds good. Well, now could you share a favorite quote, something you find inspiring?

Dave Crenshaw
Yeah, my favorite one, and someone who really inspires me is Bob Ross. And I know Bob Ross has almost become a meme these days but the reality is, as an educator and his ability to reach people, he had a gift that not many people possess. So, as someone who teaches people, I look at the way he does it.

Obviously, my personality is not quite the same but his love, his passion inspires me. And so, one of my favorite quotes, and I got a big custom poster made, it’s framed on my wall, and the quote is, “Every time you devote time to practice, you haven’t lost. You’re always a winner.” And if I’m reinterpreting that phrase, I’m saying, “Everything that you do is practice. Everything that you attempt is useful. Even if you fail, if you can learn from it, then you didn’t fail at all. You’re still winning.”

And, boy, Pete, do I refer back to this mentally when I engage in those experiments that don’t work out.

Pete Mockaitis
All right. And a favorite study or experiment or bit of research?

Dave Crenshaw
I’ll answer this in an indirect way, probably not what you’re expecting. But as a coach and as an educator, I’m a big believer in the experiment of one. And what I mean by that is sometimes we’ll read a study, and it will say, “Seventy percent of people found that taking a break at work makes them more productive, it makes them more effective.” And that’s something that I teach. But what I want to, instead, say is don’t rely on the experiment of others because you might be in the 30%.

Don’t take my word for it. Try it yourself. Give yourself time to try something that you’ve heard for the first time, and experiment it. I like two-week experiments. Really give it a try for two weeks, and then, at the end of that, assess, “What did your experiment of one give you? Did it work for you? Are there any adjustments that you’d make?” Then, that way, and you keep referring back to it, now you’re becoming the scientist of your own life rather than depending on other people to tell you what you should do based on some study.

Pete Mockaitis
All right. And a favorite book?

Dave Crenshaw
Actually, I’m going to mention something that is really off the beaten path but something I’m passionate about, and it’s Hustle 2.0 has a series of books. And I would encourage anyone to look it up. Hustle 2.0 is a program that teaches people who are incarcerated, how to turn their lives around.

And so, the books, they’ve got three of them, teach people who have been through trauma, and teach people who have been through some really rough life experiences, how to overcome it, how to be stronger on the other side. And the curriculum is written by people who have been incarcerated. And the reason why this is top of mind is I just recently went to the Utah State Correctional Facility and met a lot of people who have used this book, and I’ve read it, and I’ve even talked about it with my kids.

And it’s so powerful to see how a book written by someone who has been in that situation can completely change their lives. So, yeah, it’s a hard one to get but you can find it at Hustle20.com.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Dave Crenshaw
Everyone likes to ask me, “This is a time management guy, what’s your favorite tool?” And my favorite tool is the one that everybody already has, they just don’t use it properly, and that’s your calendar. I just use that for everything. Even if I’m scheduling time to take time off, I’m scheduling everything in the calendar and I’d wager to guess that everyone listening to this could do a little bit better job of using their calendar to help them be productive.

Pete Mockaitis
Okay. And a favorite habit?

Dave Crenshaw
I’ll share one that I didn’t do for a long time. I’ve done a much better job recently of taking care of my physical health. And if we’re talking about the podcast, too, one of the things that I want to do is interview people who have balanced success. And I’ve learned through the wrong way that not being healthy ruins everything.

It doesn’t matter what you’ve accomplished in your career, in your life, if you’re feeling physically miserable. It’s not much of a success at all. So, I’ve done a much better job of the habit of exercising regularly. I try to do it at least five times a week with both cardio and some lifting. And, boy, it’s made everything a lot better for me.

Pete Mockaitis
All right. And is there a key quote you’re famous for, Dave?

Dave Crenshaw
Well, one that pops to the top of my mind is “Whenever you say yes to one thing, you’re saying no to something else.”

Pete Mockaitis
That sounds like an opportunity cost.

Dave Crenshaw
There you go, exactly. There’s that economics influencing things. And it works in a microeconomic situation, a nano economic situation. When you’re making choices in your day to say yes to something, something has to give. It’s always a tradeoff. So, say yes to the most valuable things, and say no to things that are less valuable.

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Dave Crenshaw
The easiest place is DaveCrenshaw.com. Crenshaw is C-R-E-N-S-H-A-W. And you can find my podcast there, you can subscribe to it there, all sorts of stuff. And, of course, if you’re on LinkedIn, please look me up and follow me on LinkedIn as well.

Pete Mockaitis
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Dave Crenshaw
Well, it didn’t come up during our conversation, or I had mentioned it just briefly, be grateful. That’s another principle of people who are successful. Every day, look for something that’s going well, and express gratitude for it. And what that will do is it will make you more open to the things that make you happy, and make everything you do for work more enriching and rewarding.

Pete Mockaitis
All right. Dave, this has been a treat. I wish you much fun and success with your Success Project.

Dave Crenshaw
Thank you very much, Pete. Really generous of you to have me on. Thank you.

456: Finding Enrichment Through Side Hustles with Nick Loper

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Nick Loper says: "Think of your side hustle as an experiment... you take something away from every experience."

Nick Loper discusses the many benefits to having a side hustle—and how to start yours.

You’ll Learn:

  1. How side hustles can empower you as a professional
  2. How to turn your ideas into low-risk side hustles
  3. When to turn a side hustle into your main hustle

About Nick 

Nick is an author, entrepreneur, and a lifelong student in the game of business. His latest role is as Chief Side Hustler at SideHustleNation.com.

He’s been making his living online since before it was cool. Along the way he’s picked up a thing or two about small business, marketing, and outsourcing—and is happy to share the experience with those working hard to make their side hustle dreams a reality.

As the host of the top-rated Side Hustle Show podcast, Nick explores a different business idea each week and helps listeners discover the path to income streams.

Items Mentioned in this Show:

Nick Loper Interview Transcript

Pete Mockaitis
Nick, thanks for joining us here on the How to be Awesome at Your Job podcast.

Nick Loper
Well, thank you for having me. I’m wondering if I’m qualified because I don’t know if I’ve ever been awesome at a job that I’ve ever had. But I appreciate the invite, man.

Pete Mockaitis
Well, I think you’re awesome as a podcaster and a reviewer, and so I think you’re very qualified. And, speaking of qualifying, I love the weird segue, I understand you had some success in an early job of swimming, and you went all in with the shaving and everything. Tell us all about this.

Nick Loper
That’s true. I don’t know if this was really necessary for the district and state level at the high school swimming. This is not Olympic trials or anything. But I was a decent freestyle swimmer back in the day, and what was really fun and interesting about this was being able to continually shave, maybe pun intended, time as fast as you thought you could go, “Hey, this is a dead sprint,” and then the next week being able to beat that, and the next week being able to beat that. It was really, really kind of eye-opening. And the coach was like, “You’ve been dogging it the whole season, man. What’s going on?”

Pete Mockaitis
Well, that is cool and rewarding. And I think that it’s really exciting when there is some sort of a, for me at least, there’s like a number that’s associated with performance. And you do some things and you feel different, but then there’s also a number reinforcing it, whether it’s a revenue figure, or what the scale tells you, or something, that just lights me up too.

Nick Loper
Yes, it’s a very quantifiable sport, and that was one of my dad’s points very early on when I started swimming, he’s like, “Look, you’re only really ever racing against yourself. You can’t control what the guy in the next lane over is going to do, so just try and beat your best time.”

Pete Mockaitis
Yeah, that’s a good lesson. That’s a good lesson. And, another weird segue, you share a lot of good lessons on your Side Hustle Show podcast, and that’s a topic of interest for our listeners. So, I want you to orient us from the beginning, first, can you define for us, precisely, what is meant by the term side hustle? And maybe do you know where the term came from because I see it all the time now?

Nick Loper
Well, for me, a side hustle is anything that you’re doing to earn money outside of traditional employment, outside of your day job. And, in previous generations, maybe this was called moonlighting or a second job, but to me there’s a more entrepreneurial connotation than just delivering pizzas or bartending as a second job.

There’s this upside potential where it’s like, “Okay, maybe this could be more time-leveraged or maybe this could be a business that grows beyond just time for money,” and that is really exciting and empowering to me. The side hustle term itself, I found some etymology that dated it to like the 1950s but it’s really been over the last 5 or 10 years where it’s kind of become part of the national parlance, I suppose, and that has increased in popularity.

Pete Mockaitis
That’s right. And I guess I find that interesting because I think the word hustling in some communities can refer to illegal activity but that’s not what we’re talking about here.

Nick Loper
Yeah, it’s very much, at least in my case, comes from an old baseball coach of mine who’s like, “Look, you’re going to have bad days at the plate, you’re going to have bad days in the field, but hustle never slumps.” Like it’s the one thing you can control your own effort. And so that’s kind of where the term really comes from, for me, not like hustling, like I have to scam anybody, but like, “Look, I’m going to control the effort that I can control in the time that I have.”

Pete Mockaitis
Totally. And you’ve had a wide variety of side hustlers on your show, and they’ve got some really fun stories. So, I’d love it if you could share with us maybe just a few of the more noteworthy examples of side hustles you’ve encountered from your guests.

Nick Loper
Yeah, there are so many. A lot of them kind of in the online business space, “I built a blog and I sell advertising,” right, whatever. But some of them were just like plain old brick and mortar, like you hang up the call, and you’re like, “Well, crap, I could do that.”

For example, one guy I met, he called this America’s simplest business, and he’s been in business since the early ‘80s, just picking up trash from parking lots, and he built this to like a $600,000 a year operation by the time we talked last year. And he outsourced the trash pickup by that point, but he called it getting paid to take a walk. And he says, “It’s the perfect side hustle because you got to do it early morning or late at night when the cars are in the parking lot.”

And he called up a property management company, and says, “Hey, who handles your liter pickup?” The landscapers don’t want to do it, and he had all these reasons, but it was a cool little business. So, that one comes to mind.

One of my favorite guests is Rob “The Flea Market Flipper” Stephenson out of Orlando, Florida, just a crazy take on the buy low, sell high business model, the same business model as Walmart, same business model as every retail store in the history of business. But, in his case, looking for really weird and random items that most people aren’t going to give a second look, a lot of cases big bulky items that the seller doesn’t have room to store, or they’re kind of afraid of how much it’s going to cost to ship, he’s got relationships with uShip.com was the site that he recommended for over land inexpensive cross-country shipping.

But he had some crazy stories about a prosthetic leg for 30 or 40 bucks at the flea market and turning it around for a grand the next day on eBay. Like, “How do you know what the stuff…?” and he’s like just walking around looking at what the comps have gone for on eBay, like a Husqvarna concrete polisher, just whatever random stuff he could find.

And I asked him, “Like, are you afraid of the deals drying up?” because he’s quit his job, he’s doing this full time, six-figure business, “Like, what happens if you don’t find the next concrete polisher or the next…?” what was the other one? It was like an exercise bike, like for physical therapy offices, “Like, what happens if you don’t find that deal?” And he’s like, “Look, my limit is not the deals. My limit is like the time and the inventory storage.” I think he ended up getting a warehouse to deal with some of the inventory storage or a storage unit or something.

So, that one is super fun, kind of in the product space. One in the online world that was really eye-opening to me was a drop shipping example. So, drop shipping is e-commerce but you don’t touch the inventory. You set up relationships with suppliers or distributors, and they ship the product to the customer on your behalf.

And this guy that I talked to was selling these giant commercial bounce houses. And he’d gone through a very specific product research process where he’s like, “I need the product to be over $500. I needed to get X amount of searches in Google every month. I need it to be not something that’s readily available at Walmart, even Amazon.” And so, he’s selling these like multi-thousand-dollar giant plain old bounce houses, and he said he sold over $300,000 worth of them in his first year, driving traffic primarily through AdWords and how like pay per click advertising but now investing more into SEO. And so, I was like, “That’s crazy. Like, never had to touch the inventory himself.”

Pete Mockaitis
That is wild. And I didn’t even know that there were concrete polishers and I’m wondering if my concrete is a little lackluster if I can polish it after the fact, or is it more so at an earlier stage of concrete production?

Nick Loper
Yeah, I’m not in that industry. I couldn’t tell you.

Pete Mockaitis
You made me feel mad about my concrete. It doesn’t shine the way it probably used to. This home was built many years ago. Well, so that is wild. And so, I want to get your take then, whew, so I guess, of course, of all the benefits to be gleaned from side hustling, I mean, one is, hey; money, two is, I guess, stories or exercise or fun. But I guess I’m thinking for folks who do not aspire for their side hustle to go full time, does it enrich the experience of the worker at work having a side hustle going?

Nick Loper
I think it definitely made me a better employee because, in my corporate world, in my corporate life, I was like at the bottom rung of this Fortune 50 company where if I didn’t show up, it would make zero meaningful impact to this business.

Pete Mockaitis
That doesn’t feel good.

Nick Loper
You hit your numbers, you don’t hit your numbers, like it’s not a blip on the radar, versus when I come home, nights and weekends working on my side business, which was a footwear comparison shopping website at the time that would make affiliate commissions from Zappos and Amazon and these other online shoe stores. If I spent the weekend hustling and making a ton of new ads and updating the inventory, I could see the benefits of doing that to my bottom line for the rest of that week, the rest of that month, versus at my day job, where it’s like I was going to get paid the same whether or not I worked really hard or didn’t. It was a kind of weird relationship.

Pete Mockaitis
It’s like the movie Office Space.

Nick Loper
Yeah, but being the CEO on the side kind of helped me see the bigger picture at work too and, especially, because in my job I was interfacing with car dealers as a manufacturers or reps for Ford. And so, some of these dealers had been in business for generations, some of them had their charter signed by Henry Ford. And to come in in his early 20s and tell these guys how to do their business, it was a weird kind of place to be in but I kind of speak in their language a little bit because I have this business experience on the side.

Pete Mockaitis
Yeah, that is handy. So, you got some global perspective in terms of how the business is operating maybe a bit more strategically. You’re able to inform better connections with some of the folks here that you’re reaching out to. And how about some of the others, like your guests, have they shared some either skills they’ve acquired that were serving them at their day jobs as well?

Nick Loper
So, probably the thing that draws most people to side hustling is the extra income component. And when you’re starting out, I kind of frame it as a side hustle snowball kind of a reversed Dave Ramsey type of deal where it’s like I’ve itemized out my expenses, smallest to largest, and then I try in like a line item, erase them with non-job income streams, maybe that’s dividend investing, maybe that’s a little bit of freelancing over here, like, “What can I erase?” especially if I have an annoying expense, like, “Oh, my gosh, my car insurance just bothers me that I have to pay this. I want to cross it off and make that free.” I think it’s kind of a fun way to build it up.

But, like you mentioned, building skills, working on something that’s meaningful, that’s challenging, that’s impactful, that’s creative, all of that stuff really plays into what is a benefit of doing a side hustle. On top of that, really empowering to earn your first income outside of your day job, and to say like, “Oh, I’m worth more than what it says on my business card. Like, I have value in a marketplace outside of my own paycheck.”

I know for my wife that was really empowering and kind of a big confidence boost for her. But let me flip it around. Like what drew you to starting the podcast on the side? Like what benefits have you seen, if any, for work?

Pete Mockaitis
Oh, sure thing. Well, in a way, I was sort of already self-employed doing my thing, and I thought the podcast would be cool in terms of generating leads for training services and whatnot. And so, it’s a little bit of that, but it’s really kind of going in new directions. I think that’s what’s been fun, is the surprises in terms of I do not even know what I was really getting into, but then it sort of sparks all kinds of cool things like I’m talking to fascinating people like yourself. And then I’m learning all sorts of things from those people as we’re chatting in terms of real skills as they’re sharing what they know.

And then sort of developing some expertise because I’ve been kind of clueless sort of when it comes to marketing, I think, and now I’m getting a bit more sophisticated in terms of I can more readily I think call out, it’s like, “No, that’s absolutely not worth it at all. I’m going to pass on that.”

Nick Loper
Well, you’ve clearly done something right. Like, I’m curious, what do you think attributes to the growth of the show?

Pete Mockaitis
Oh, sure thing. Well, I think that, well, I was going to ask you about idea validation as well for side hustles, but I think I started a number of businesses that didn’t really produce revenue, if you will.

Nick Loper
Sure. Sure. I think we’ve all been there.

Pete Mockaitis
I’ve had some folks say, “Oh, you shut down because you weren’t profitable.” I was like, “No, no, it’s not that the profit was zero. In fact, that was negative. It’s that revenue was zero.” And so, even partnering with brilliant people, you know, all the right credentials in terms of like fancy consultants, fancy business school degrees, just brilliant intellects, and we had an idea, and I think a couple in particular.

One was called Launch Point, and that was to prep folks, post-high school pre-college, in that little interim summer, it’s like, “Hey, let’s get you a bunch of skills you need to excel in college and not drop out.” And it was interesting that folks weren’t really biting on that a whole lot. Later, I learned that even some prominent marketers have tried that concept and not had as much luck.

Another one was low-cost online math tutoring using workers who are smart, are in the developing world, and can have a great living wage at a smaller price point. I thought, “This could be really cool.” But then it’s even like those who were low income already had sort of free tutoring services, and those who are high income wanted the very finest and they have no qualms paying 50, 60 bucks an hour for a tutor for their folks.

So, I think the difference here was, for the success of this show, was that I just refused, I just got fed up, it’s like, “I am not going to build something people don’t want even if I’m super excited about it and think they should want it, I’m just not going to do it.” So, I went a little bit, I wouldn’t say overboard, but I spent some real time in terms of I used three different quick survey tools to assess, “To what extent do people have an interest in listening to a podcast about skill-sharpening insights? And to what extent is that kind of similar to some shows but also unique?”

And when I saw that those numbers looked really compelling, I said, “Okay, folks genuinely want this. It’s not just something I think would be fun,” but I do, I think it’s fun. And so, I was raring to go. I think that made the difference. It’s like folks are fundamentally interested in this concept, and I see it even with my Overcast advertising, if you’ve ever done that, is that my taps and my clicks and my subscription rate, amongst other podcasts that are advertising on the platform, are like way higher than what they project.

So, it’s like, “Okay, this is a resonant concept anywhere you slice it.” Oh, you got me going, Nick.

Well, since we’re flipping tables back and forth, I want to get your take. When it comes to a side hustle, I think it’s very easy for folks to get super excited about something they’re into, fill in the blanks, artisanal candles or something, and then they maybe want to go big and say, “This has got to be huge.” How do you recommend mitigating risks and validating ideas before you lose all your money?

Nick Loper
Sure. Well, that’s the beauty of side hustles, almost by definition it’s got to be low risk because it’s on the side from your day job. Ninety-nine percent of people I talk to is all bootstrapped self-funded businesses, not taking in outside investment capital or anything like that. So, it’s like, “What can you get off the ground? How can you prove with the model quickly, inexpensively, and see what’s going to work?”

The biggest risk, especially for people who are still working in jobs, especially a job that they love, is like, “What if my boss finds out? Like, what is my employer going to think about this?” Like, that’s one of the bigger issues that tends to come up although with the data, I think, it’s like half of all millennials have some sort of side hustle, 44 million Americans overall have some sort of side hustle. It’s becoming more and more commonplace where it’s like, “Okay, look, your employer doesn’t own 24 hours of your time, energy, and attention.” It’s like, “Hey, look, they’re paying you for these eight hours, and after that, whether you run a marathon or run a business, like what business is it of theirs?”

But on the idea validation side, the quickest thing that I found is like to actually ask somebody to buy. And we’ve seen this in the physical product world that’s like, “Okay, I’m going to make a small bet on inventory upfront rather than like I’m going to buy a warehouse, or I’m going to buy a container shipment from China. Like, okay, how can I validate this on the cheap, on the kind of audience-building side, the blogging, podcasting, YouTube side of the world?” It’s kind of like, “What content is already out there that people are paying attention to? Can you tell if these people have been at it for a while? Does it look like they’re making money or does it look like this is just a hobby for them and kind of get a gauge based on some statistics?”

Similarweb.com might help you kind of gauge some traffic. Tubebuddy.com like for YouTube can kind of give you a gauge, although YouTube is pretty public about like, “This person has seven million views,” because they want to pump that person up too for social proof. And then, on the service side, it really is just like, “Here’s what I can do for you. Here’s the price. Would you buy it?”

A friend of mine hosts these urban hiking tours in San Francisco, and she saw walking tours, and Segway tours, and bike tours, and bus tours, and she’s like, “Well, shoot, I’ll throw my hat in the ring. How about a hiking tour?” She loved going hiking in all these different trails within the city limits, and found a handful of people who were like, “Yeah, that sounds awesome.” Those people seeded her profile on TripAdvisor and some other sites with the initial reviews, and she started to get some traffic organically after that. But she had paying customers from day one.

Pete Mockaitis
Yes, absolutely. I think the key, as you say, “Would you buy it?” It’s not like you’re speaking in a theoretical context, it’s like, “No, here and now, are you going to part with your cash for what I got?” because there can be a world of difference between survey hypotheticals and, here we are, trying to exchange.

Nick Loper
Right.

Pete Mockaitis
Well, so then, that’s great and I think that may take a bit of courage for some who maybe are reluctant to engage in some of the sales conversations. Have you encountered that and do you have any pro tips for folks who are taking those first steps into selling?

Nick Loper
It is an awkward thing or can be an awkward thing to stick your neck out in a way and ask for money and have confidence in the value that you’re going to provide but it gets easier over time. And you kind of recognize that nobody is awesome at it right out of the gate, and it gets more comfortable, like I‘ve sold some advertising on certain sites, and it’s nice to be able to say like, “Here’s the rates. Here’s the PayPal link, go. If you want this, I’ll plug it in for you right away. Otherwise, hey, no hard feelings.” So, it can be as simple as that.

Like, I used to sell house painting, and the close was always like, “What do you think?” It’s like the lamest close ever instead of like, “Okay, I’m going to leave, my trucks parked out front. I’m going to leave in 10 minutes. It’s this price.” It’s kind of a low, a casual way to have a conversation, like, “Look, we’ve been talking for an hour, I’ve walked all around your house, this is what you told me you wanted, here’s the price. What do you think?”

Pete Mockaitis
Yep, all right. There you have it. And it’s just so simple, and I like that. I’m really putting myself in that moment and think about a painter, and “What do you think?” is it also feels a lot less cheesy than, I don’t know, you might encounter any number of pieces of advice associated with, “So, when can I schedule you for your dream painting or something?”

Nick Loper
Right.

Pete Mockaitis
“That’s cheesy and that is pretty presumptuous, I didn’t say that.”

Nick Loper
Yeah, “When can I get you on my calendar? When is it good for you? Like, I got the first week of June open.”

Pete Mockaitis
“What do you think?” All right, just that simple. That’s cool. I want to talk a little bit about the time element. So, you mentioned that you’ve got a number of hours outside of the eight-ish that you’re doing work at your day job, and you’ve got some expertise when it comes to leveraging your time with virtual assistants. Can you tell us a little bit about this and how that might be an effective way to get more hustling on the side with a limited number of hours?

Nick Loper
This is one way to kind of add some leverage to your day in that you don’t have to be the one doing all the work. I think, in the early days, it probably makes sense for you to be doing it provided it’s something that you know how or can reasonably learn how to do. My first hire was like a web development team, so I was like, “If I learn how to do it myself, the site probably still wouldn’t exist.” So, there are certain cases where it’s like, “Oh, I just got to hire an outside expert.”

But there’s other cases where it’s like, “Okay, I’ve been doing this myself, I have a process in place, but it’s not rocket science. I don’t need to be doing it myself. I could bring on some help to do that.” And this is really where I’ve had the most success in hiring outside help is plugging people into a specific role or task where it’s getting hours of work off of my plate in exchange for just a little bit of upfront training, and say, “Here’s the process. Can you follow this recipe?” And you’re providing feedback and training, coaching, of course, but ultimately saying, “This is your responsibility now.”

Pete Mockaitis
And so, you’ve taken a look at a lot of services that provide this. Have you found some that you are pretty reliably high quality and you dig?

Nick Loper
I have a dedicated service for podcast editing, that’s called Podcast Fast Track. I’ve got a kind of a website maintenance service, I consider it kind of like a website insurance at this point where if something breaks or if I want to change something, they’re kind of on call 24 hours a day, and just send them a note, “Hey, can you move this thing?” Because I’ve gone down the rabbit hole of trying to tweak things myself and hitting refresh and being like, “Oh, no, I got the white screen of death in WordPress. This is bad news.” That’s called Zen WP is a service I use over there. They’ve been really good.

But it’s really kind of itemizing out where your time is going and saying, “Okay, could somebody else do this as well or better than me? Or is my time better spent elsewhere?” And it’s kind of how I’ve gone about the delegation phase, and still learning. So, I just got off a call this afternoon about like, “Do you really need to hire like the executive assistant right-hand person type of role? And here’s why. Here’s how to do it.” So, that’s probably next on my plate.

Pete Mockaitis
Oh, cool. Cool. And so then, I’m thinking, if folks are, they’re eager, they’re hungry, and they say, “You know what, side hustle sound really cool. I’ve got a number of ideas,” what do you recommend might be some of the very first steps and if you don’t have a whole lot of extra time or money but you want to get a taste? What are some of the starting tidbits you’d recommend?

Nick Loper
Starting points. If you’re in the idea searching phase, I encourage you to hit up SideHustleNation.com/ideas. That’s my constantly updated laundry list of part-time ways to make extra money that you can start today. No opt-in required over there. If you’re the person that has a handful of ideas and you’re trying to debate, “Well, which should I take action on? Which would be most worthwhile to pursue?” you can create kind of a weighted decision matrix with a handful of questions that might be pertinent, like, “How excited am I about this? What’s it going to cost to start up? What’s the profit potential long term? Is this scalable or could I eventually remove myself from the day-to-day operation?”

You can come up with 8 or 10 different questions, kind of along those lines projecting out 12 months or 24 months, and kind of assign a number score to each of those and see what the little matrix spits out. And you might find, “Well, that’s not what I really want to work on.” It’s like, “Well, go with your gut in that case.” So, if they’ve gone through that exercise a handful of different times and your gut will tell you if the numbers lie.

Pete Mockaitis
You know, I’ve done that exact thing and, boy, I remember exactly the context when I was in college and I had to figure out, “Okay, I got summer options, there’s some travel, there’s some trips.” And then I thought about, “Okay, what are my criteria? What am I going to score them at?” And then as I really just thought and just forced myself to think through them just made me realized, “I don’t think they’ll be that much fun. I don’t want to do that.” I was like, “How did this even get to be a finalist in the first place?” And so, yeah, I love that. It’s like you do the numbers but you’re by no means a slave to them. It’s just the process itself can be rather informative.

Nick Loper
And the last thing you need is a second job that you hate, so I think that’s a really important piece especially if you’re in the position of like, “Hey, it works okay, it works good, it’s paying the bills. I’m not struggling to make rent next month,” like, okay, then don’t start a side hustle doing something that compromises your enjoyment.

Pete Mockaitis
Yeah, I’m with you. And let’s say you’re a little bit farther down the track, you’re like, “Holy smokes, it looks like people are really into this side hustle. Maybe it should be my full hustle.” Are there any sort of telltale signs or indicators that it might be a nice time to jump?

Nick Loper
Telltale signs. Probably a couple. The first is their track record of revenue. So, a lot of people are out to replace their day job salary which is awesome but kind of hard to do on a part-time basis. If you think about it, like, “Man, you’ve built something that’s legitimately time-leveraged if you manage to do that.” Probably the more important metric is to cover your expenses, like, “Does this cover my monthly fixed costs?” If so, fantastic, especially given an extra 40, 50 hours a week to dedicate to it.

Like, look at the upside, right? Like, if I’ve been able to get it here part time, think about what I’d be able to do when I go full time. The second thing is like if you can’t stop thinking about it, if you only had more time, like if you’re super energized and energetic about it, and it’s like, “Okay, now is the time to make the leap.” Some friends of ours gave the example of like they’re quitting their job to pursue some business in like electronic motorcycles or something. And they’re like, “Well, what happens if it doesn’t work out?” “I’ll go get another job. That’s okay.” And so, it’s kind of the think of the downside, think of the downside risks. Usually not as life-threatening or as damaging as we probably make it out to be.

Pete Mockaitis
Yeah, I hear that. It’s like, “Worst case scenario, I’d burn through my savings and I had one, or two, or three years of fun with these motorcycles and we can resume.” So, that’s good. And maybe this is a nitty-gritty question, but I know some, when considering making a leap, health insurance in particular as a sticking point. Any pro tips on that front?

Nick Loper
A lot of my friends in the personal finance space use a health-sharing service. It usually has a Christian component to it, like you got to swear on the Bible to uphold Christian values. Liberty HealthShare is one that is probably less Bible thumping than Medi-Share which is the other popular one. But those two have significantly lower costs than going on the national healthcare exchanges. The risk is it’s not insurance, and they won’t tell you that it’s insurance, and that’s how they get around the federal mandate loopholes, but the cost savings are attractive enough to have a lot of people are putting their trust and faith in those.

Pete Mockaitis
Sure thing. And I guess so it’s not insurance but, I mean, at the end of the day, they pay your hospital bills, right?

Nick Loper
Yes, so they pay your claims. The question is just how long. I’m curious, like, how big is your risk pool? Somebody gets terminal cancer. Like, what are you going to cover? It’s a weird thing where it’s a little bit scary to me. I still have health coverage through my wife who works full time, so we look at it as a team sport. But if she was ever to leave that job, we would probably just go with one of the off-the-shelf plans and just chuck that up as a crazy expensive monthly expense.

Pete Mockaitis
Yeah, I hear you. But I guess, now I’m thinking, you got my wheels turning, just like when you said, “Hey, what’s the worst that can happen?” I guess maybe it’s like you got to buy real insurance over the long term.

Nick Loper
Yeah, which is a significant number to add to your line item budget. And for our family, the last I looked it’s probably 1200 bucks a month minimum for pretty crappy coverage.

Pete Mockaitis
Such is the American challenge.

Nick Loper
I know. Your Canadian listeners are like, “What are they talking about?”

Pete Mockaitis
“What’s that about?” We love our Canadian listeners. Thank you. Well, tell me, any other things you want to make sure to mention before we hear a few of your favorite things?

Nick Loper
The biggest thing for me is to think of your side hustle as an experiment, kind of put on your scientist hat and say, “Okay, my hypothesis is this. It’s going to work. But if it doesn’t, that’s not the end of my experiment. Like, I’m going to go pivot back to something else, taking what I learned from that, and move onto the next thing.” So, in that way, like what I’ve really found is that failure is inevitable in a lot of cases, like you’re probably not going to hit a homerun in your first bat. But, on the other hand, it’s also impossible because you take something away from every experience.

Pete Mockaitis
Thank you. Well, now, could you share a favorite quote, something you find inspiring?

Nick Loper
The one that I probably point to is Thomas Edison’s “We don’t know a millionth of 1% about anything.”

Pete Mockaitis
Yeah, I find that comforting actually. And how about a favorite book?

Nick Loper
Favorite book for me is The Go-Giver by Bob Burg.

Pete Mockaitis
Oh, yeah, we had him on the show.

Nick Loper
Oh, nice. Yeah, so you know all about it. It’s about providing value first, being helpful first, and that really kind of solidified a mindset shift for me. I was like, “You know, I got into the business for the noble purpose of like, ‘How do I make extra money?’” And I was like, “Well, money follows value. Like, how can you be of service to others?” And so that was an important read for me.

Pete Mockaitis
And how about a favorite tool, something you use to be awesome at your job?

Nick Loper
How about TextExpander. Actually, I got some of these. TextExpander is awesome for like these keyboard shortcuts and snippets, and LastPass is something that I probably couldn’t live without.

Pete Mockaitis
And a favorite habit?

Nick Loper
Go-to habit is the practice of naming your top three priorities for tomorrow the night before so when you wake up you know exactly what to work on and in what order so you don’t have this 45-minute ramp-up period of like, “Well, what should I do today? Let’s see what’s going on on Facebook.” It’s like, “No, yesterday Nick said this was what’s important. Let’s go.”

Pete Mockaitis
All right. And is there a particular nugget you share that seems to resonate with folks, they quote it back to you a lot?

Nick Loper
The Side Hustle Show soundbite I probably refer to most is from Ryan Finley way back in episode 72 when he said, “The best opportunities aren’t visible until you’re already in motion.” And when he said that, and this was probably 2014, I was like, “Yeah, that sounds kind of hippy.” But, over the years, I’ve really recognized that to be so, so true. Once you get started, it’s so much easier to stay started. And the conversations that you have and the ideas that come up as you’re working, as you’re doing it, like never would’ve come to you had you just still been sitting on the sidelines.

So, the best opportunities aren’t visible until you’re already in motion. So, that’s my biggest challenge, like getting people off the sidelines and into the game, because once you do it, it’s like you can see the matrix, all the lights go on.

Pete Mockaitis
And if folks want to learn more or get in touch with you, where would you point them?

Nick Loper
SideHustleNation.com is the home base. I mentioned SideHustleNation.com/ideas as a good place to start, and just nick@sidehustlenation.com as email.

Pete Mockaitis
And do you have a final challenge or call to action for folks seeking to be awesome at their jobs?

Nick Loper
Yeah, maybe you could consider this as the challenge, is to think of the skills and interests and areas of expertise that you already have, and see how that might apply to a side hustle. So, for example, on my resume in the past, I was a ski instructor. So, I could say, “Well, what if I did private ski lessons?” I was working as a cashier at a restaurant, I was handling money, like, maybe I could do bookkeeping for certain businesses. Not every job or not everything on your resume is going to naturally translate to a freelance service, but I think you can get the creative juices flowing with, “Okay, what inventory of my existing skills has demand in the market?” And that’s probably a good place to start for looking at a potential side hustle.

Pete Mockaitis
Well, Nick, thank you. This has been a treat. I wish you tons of luck as you’re side hustling and equipping others to do the same. So, keep it up.

Nick Loper
Thanks for having me.

160: Sizing Up Big Picture Strategic Challenges…FAST with Paul Szyarto

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Paul Syzarto says: "If you know there's a problem, state the facts and stick with it."

Paul Szyarto talks about his templates for overhauling businesses, the root of common business problems, and how to identify improvement opportunities.

You’ll Learn:

  1. How to assess root problems quickly
  2. Why identifying current facts is more accurate than relying on history
  3. The underlying source of tremendous confidence

About Paul

Paul Szyarto is a renowned business transformation expert. He is currently the CEO of Campana & Schott Inc., controlling all operations throughout the United States. He holds numerous degrees and certifications, including an MBA from Oxford. He is also a Lecturer at Rutgers University Continuing Education and The Wharton School, a member of the Advisory Board for Argus-Soft and DELCON Construction, and a practicing martial artist. He also teaches Krav Maga and tactical training as “The Combat CEO” at his VMMA franchise locations.

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