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

1102: How to be “Lucky” by Hacking Hidden Markets to Get More What You Want with Judd Kessler

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Judd Kessler discusses how to navigate the hidden markets that decide how scarce resources—like time and attention—get distributed.

You’ll Learn

  1. Why some people seem to score more coveted resources
  2. The counterintuitive advantages of settling
  3. An easy way to become the more appealing candidate

About Judd

Judd B. Kessler is the author of LUCKY BY DESIGN: The Hidden Economics You Need  to Get More of What You Want and the inaugural Howard Marks Endowed Professor of Business Economics and Public Policy at the University of Pennsylvania’s Wharton School. For his work on the hidden market of organ allocation, Kessler was named one of the “30 under 30” in Law and Policy by Forbes. He is an award-winning teacher as well as a sought-after speaker.

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Judd Kessler Transcript

Pete Mockaitis
Judd, welcome!

Judd Kessler
Thanks for having me.

Pete Mockaitis
Well, I’m so excited to talk about this stuff. This is a concept I don’t think people even know exists. Can you share with us what is a hidden market and why should professionals care about them?

Judd Kessler
Great question, my favorite question, because I’ve been thinking about hidden markets for a long time. So let me tell you what I think of as a visible market, the kind of markets we’re used to, and that’ll help us think about what a hidden market is. So visible markets allocate things by prices changing. And they’re easy to do business with, and we’re used to them. If you want something at a store, you go, you see what the price is, you decide whether to buy it. If it’s worth the price, you buy it, and if not, you don’t.

And this is how economists often think about markets. We think that prices move around to decide who gets what. But that’s not how all markets work. A lot of markets don’t have prices that decide who gets what. There’s a lot of people who want something and either the price is too low, so there’s more people who want it at that price than we have things to give. Or we don’t have a price at all. There’s lots of markets where we decide we don’t want to let kind of the richest buy access to the thing.

And in that second case, we have what I call a hidden market, where there’s something that decides who gets what, it’s just not prices. And so, you have to understand what it is that’s allocating the scarce resource.

Pete Mockaitis
Okay. That’s as fun, brain expanding. Can you give us an example of how this might apply in the professional world?

Judd Kessler
Yeah, it’s much easier with examples. I give you the theory bit first, but the examples are lots of products that you purchase have prices that are kind of too low from the standard economics, kind of sense of what prices are supposed to do.

So, if you want live event tickets or you want a restaurant reservation at a kind of popular place, in these cases, there are more people who want the thing than they have available to serve. And for a variety of reasons, the artists that are having that concert decide that they don’t want the price to just rise until only the rich can afford to go.

Pete Mockaitis
You know, I was going to ask, is that why? Because I’m thinking, if these Taylor Swift tickets or whatever sell like within seconds of them opening up, like, my immediate thought is, “Well, shouldn’t they just increase the price?” So, is the artists or others making the request to keep it at a lower rate?

Judd Kessler
Yeah, and people debate about why they do this. So, one argument is, well, think about the restaurant first. That, I think, is a little easier for us to think about. Like, the restaurant might like a line around the block or stories about how hard it is to get a table. They might think that kind of keeping prices low enough that they’re getting a lot of people who want to eat there, and that’s kind of creating its own buzz, is going to be helpful to be able to fill the restaurant for months and years.

I don’t think Taylor Swift needs to do that. Like, I don’t think she needs more buzz, but she might have different reasons to keep the price low because she has a bunch of fans, and if she were to set kind of market-clearing prices, prices where only one person wants to buy the ticket for each seat, then those prices would have to be very high and that would make it untenable for a lot of her fans to actually be able to afford tickets.

And as a billionaire, it might not be a good look to be charging $1,000 for a ticket. She’d much rather charge $99. But, of course, then it creates a frenzy for getting the tickets and a hidden market that pops up to decide who gets the tickets and who doesn’t.

Pete Mockaitis
It’s probably less fun, I’m imagining as well, as a performer if it’s like everyone in the seats is a multimillionaire. It’s like, “Okay, the vibe in here is not as enjoyable.”

Judd Kessler
No, and that is an absolute issue that, you know, kind of we think about in lots of different markets. So, it’s not just concerts, right? If you think about a baseball fan who sits in the cheap seats all season, and then the World Series comes along and prices are much higher, right, well, that fan might be the one who’s going to enjoy the seat the most and also kind of bring the most excitement to the stadium.

But if you price that fan out and you sell the ticket to somebody who’s never been to a game, but wants to say they’ve been to the World Series, that might not be a good use of that resource, and it might be less fun to kind of be in the stadium on that day. And the same thing is true in hidden market. I mean, there’s lots of hidden markets. I’ll give you a million examples, I’m sure, during the conversation.

But we also don’t, at Wharton where I teach, we don’t just raise tuition until only we can fill the class with just people willing to pay a very high price. That would not be a cohort of students that we would kind of think are the best fit for our school. We have different market rules, a hidden market that decides, “Okay, who is going to get admitted to our program this year?” And we don’t base it on price because we care about who actually is filling the seats in our classrooms, just like the artists might care about who’s filling the seats of the stadium.

Pete Mockaitis
Understood. Okay. So, there’s our concept. And your book, Lucky by Design: The Hidden Economics You Need to Get More of What You Want, you suggest that there are things that we can do to have more luck, to be the ones who are in the seats more often.

Judd Kessler
Yeah, so there’s lots of different examples in the book of these hidden markets. Basically, any time there are more people who want something than we have goods or services available to give to everybody. And so, what we need to do as market participants, as people who want those things, that scarce resources, we have to see that the hidden market is there. We have to be able to kind of see through the hidden nature of it and identify it.

Then we have to learn what the rules are. And that’s kind of a key thing, because there’s lots of different rules that determine who gets what in these markets. And the rules differ by which market you’re in. But then once we see the hidden market and understand the rules, then we can develop a strategy that actually lets us succeed.

Then we can figure out, “What is it that I have to do in this market to actually get what I want?” And that’s what I mean when I say getting lucky by design. It’s kind of you’re figuring out the hidden market, its rules, and how to play in it.

Pete Mockaitis
Okay. Well, so in the case of concert tickets, it seems, as far as I understand, maybe you got some inside scoop, Judd, a music fan, it seems the name of the game is, get on your computer, poised and ready to go, the second tickets become available.

Judd Kessler
This is what we call a first come, first serve race. So, we’re familiar with first come, first serve, but this is a race. It’s whoever clicks the fastest, gets the thing. And this is a very common type of market rule. So, it’s for the tickets for a lot of shows and sporting events. It also happens for restaurant reservations. If all the reservations for next month are released at the same point in time this month, you have to be there ready to click.

And, there, one key strategy, obviously, is, like, you have to know that this is a race and then you have to be ready to go on your highest speed internet, with your finger on your mouse.

Because a lot of times you’ll be playing in a hidden market, not realizing that the market is there, you’ll show up to make a reservation or to buy a ticket, only to find out that everything is taken. And it was taken weeks ago when the race started and you happen to not know that the race was on, you’ll miss it entirely.

Pete Mockaitis
Well, it’s funny, it sounds so simple, but you say, you have to see that there’s a hidden market there. You need to know the rules and then you need to develop a strategy to do so. That seems, in some ways, very, “But of course,” and yet I think that we overlook a lot of these things, like, “Hey, I want a lot of stuff. And it seems like I keep missing out.”

Judd Kessler

Yeah, “How did that person get that reservation? How did that person get the tickets? How were they able to do it? I showed up to Ticketmaster an hour after the tickets were released, and everything was gone.” It’s like, well, it turns out an hour is too long a period. You have to be there the minute it opens. And that might not be obvious to folks. But even if it is obvious, there’s other ways, other kind of strategies you should be thinking through when you’re running in these first come, first serve races.

Pete Mockaitis
Ooh, tell us, Judd. What do we do?

Judd Kessler
So, this is a strategy that comes up a lot in a lot of different hidden markets. And it kind of works against our instincts. And so, we have to think about when we should use it. But then we could potentially use it successfully. And I call it settling for silver. So, silver as in silver metal, as opposed to going for gold. So going for gold, being going after the thing that you want more than anything that kind of is, the most desirable option for you.

So, imagine, I tell the story in the book, I’m trying to get my wife a reservation at a very difficult to get reservation restaurant called The French Laundry in Napa Valley. They have only 60 seats. It has three Michelin stars. It’s also crazy expensive, but it was her 40th birthday. So, it was like, “All right, let’s give it a shot.”

They release all of the reservations for a given month on the first of the preceding month. So, at 10:00 a.m. you have to be there, ready to click. And in that situation, I might decide I want to go for gold. I might decide that I want to get the absolute best reservation that I can, the thing that I think my wife would want the most, maybe 7:30 p.m. on Saturday night.

The problem with that strategy is that a lot of people want to eat dinner at 7:30 p.m. on Saturday. It’s a very desirable time. And so, if I go for that, if I go for the thing that I really want, then I’m facing a lot of competition. There’s a lot of people that are trying to click at the same time as me.

It also turns out, this is very true in the live event space, also now more so in the restaurant space as well, there are also bots and, like, computerized programs competing against me to get those so that they can secure them and then sell them to me later at a higher price, if I’m unlucky.

But while I’m kind of going for gold, there are other people who are settling for silver, who are saying, “Look, I would love to eat at 7:30, but maybe that’s too aggressive a strategy. Why don’t I try for something less desirable? What if I try for a 5:00 p.m. reservation or 4:30 reservation? There’s going to be a lot fewer people racing for that. And if I go for that, I’m substantially, more likely to get it.”

And so, you, as a participant in this market, you have to think like, “All right, do I really want to go to the restaurant and I kind of care less about exactly when I go? I prefer 7:30 to 4:30, but it’s not that big a difference. Like, the key thing is getting to eat there.” If that’s the case, maybe settling for silver, even though it kind of feels tough because you’re settling, it’s right there in the name, maybe that’s a better strategy.

If you absolutely want to go at 7:30, you only want it if it’s the best, you know, the ideal thing for you, then you go for gold, but you kind of deal with the fact that you’re less likely to get what you want.

Pete Mockaitis
Yeah. You know what’s funny, this brings me back to, I’m thinking about high school, Model United Nations. And so, the most desirable countries to represent were those who had the permanent five seat veto power on the Security Council.

Judd Kessler
The power. The power in Model UN.

Pete Mockaitis
And we’re just, like, well, “Hey, if we want to be in the Security Council, everybody wants the permanent five seats, so let’s go for some nations that are on the Security Council, but don’t have one of the permanent five seats. In that way, we can get what we want with less competition. And is it such a big deal if we don’t have that veto vote? It’s fine.”

Judd Kessler
And this settle for silver strategy is one that students, you know, time of the year, you’re starting to think about applying to colleges, this is where this strategy might come into play.

So, college admission is another hidden market. And this time, there’s a participant on the other side of the market who’s deciding whether or not to admit you. So, I call these choose me markets, right? Unlike first come, first serve, where whoever clicks fastest gets it, and it’s kind of algorithmically decided who wins the race and who doesn’t.

With choose me markets, the market participant on the other side is trying to kind of suss out whether you’re going to be a good fit for them. It turns out, colleges in the US, they really like when they get high-quality candidates, but they also really like to have high yield. They want a large fraction of the folks who apply and are admitted to matriculate.

So, their concern with yield, their concern with getting people who they admit to matriculate, leads them to like applicants who apply early, and in particular early decision, where you’re basically committing to go if you are admitted. Now what’s the difficulty with early decision as an applicant? You can only apply to one school early decision, because if you get in, you’re committing to go.

And so, the colleges reward you with a higher chance of getting in if you apply early. But this is a case where you, as an applicant, have to decide, “Are you going to go for gold or are going to settle for silver?” Because if your dream school, your actual first choice is, like, really a reach and really unlikely to admit you, even if you apply early decision, then that might be a waste to go for gold. Like, you might use your application, your early application on your ideal place, but it might be that the competition is too stiff.

Go to your second or third choice school, maybe that’s a school that will admit you if you apply early, but might not admit you otherwise. Then, all of a sudden, you’re using your early application kind of effectively, it’s kind of getting you into this second or third choice. Sure, it’s not your dream school, but it might be the more realistic option for you. And that might be the strategy that you want to play in that market.

Pete Mockaitis
Well, now let’s not just talk about admissions. Let’s talk about career, job-hunting stuff. These principles sure seem to apply. We have one role opening available and hundreds of candidates applying on LinkedIn jobs, etc. So how shall we think about this hidden market strategery to boost our odds?

Judd Kessler
Yeah. So, again, this is a choose me market. There’s you as the applicant applying, maybe there’s 250 applicants applying to the same job posting. I’ve seen those numbers as estimates for how many people apply on average to a given job. And there’s a firm on the other side that’s trying to screen through those job applications.

So, I think from us as the applicant, on the applicant side, I think the traditional thing to think about is making sure that we look good as a candidate. We want to kind of make it so that the firm finds us very appealing. And one of the ways we do that is by kind of making, you know, being great and investing in skills and things like that.

What we often don’t think as much about is kind of the firm’s thoughts about us and our interest in that job relative to other options. So, in a lot of these choose me markets, just like the college wants to know that you will matriculate if you are admitted, like they kind of care about yield, firms care a lot about it for a different reason.

They want to hire folks who will stay with the firm for a while, “If I’m going to hire you, if I’m going to train you, I’m going to invest in you, I’m to plug you into my team, I want to make sure that you’re actually going to be a good investment and be with the firm for a while.” And so, one thing that we don’t think about as much, or maybe as much as we should, is, “Are we communicating to the firm that they are actually, like, are one of our top choices?”

And we would not only be happy to accept a job, right? Obviously, we’re applying, so we would think you would apply only to jobs you would take, but also that we’re likely to be there for a while and add a lot of value to the firm. And the way we used to send those signals, and maybe in some markets we still can, is through things like long, detailed cover letters, right?

So, the reason we have so many people applying to every job posting is it’s so easy to apply. You press a button and your application goes. But to signal that this is actually, like, one of your favorite job opportunities and, thus, probably a job that you would stick with if you were given the opportunity, those jobs we give extra attention to.

We write kind of long, detailed cover letters that explain why we would be a good fit for the firm, how we see our background fitting in and adding value, and we’ve researched the firm, and so it’s clear that we care. And in the old days, you would only do that for, you know, it takes a bunch of hours to write that cover letter, and you would only do it if the job was really one of the few that appealed to you.

The reason I say it’s kind of something that used to work, and might not work for all that long anymore, is that large language models are making writing that cover letter kind of vanishingly easy. And so, that way that we used to signal to firms that we were a good fit for them, that we were really excited to be there, it’s kind of, it’s not going to be something we can rely on forever.

Pete Mockaitis
Just very recently, I had a podcast guest, Madeline Mann, who’s discussing some of these ideas. And one alternative signal is, if your LinkedIn profile headline is matching the kind of role that they’re thereafter. So, if you say “food marketing” and, sure enough, it’s a food marketing role, “Well, that looks good.” Like, you are for real. You’re into this. As opposed to just any kind of marketing or any kind of food.

Judd Kessler
And that’s great because that’s the kind of signal that you can’t send to multiple different firms about different roles, right? You have to pick one and it’s a public statement that you’re making to kind of everybody that, “This is the thing that I care about.”

There’s a tradeoff there because it could be kind of limiting. Like, maybe you do have multiple interests, not just food marketing, but marketing of other products, other consumer packaged goods, for example, then you are kind of, you might want to have signals that you can send to a subset of firms.

And those might be things, like on LinkedIn, kind of engaging in a real way with folks that are already at the firm, kind of engaging with their content and making comments. It could be networking.

There’s a way there to signal that, “This is a firm that I care about. I clearly have talked to a bunch of people that work there and gotten to know the place,” in a way that can’t be replicated with AI.

Pete Mockaitis
Well, and in terms of knowing the rules, I mean, that can be so wildly different, job post to job post. Some job posts, unfortunately, aren’t even really available to outsiders. That’s just a formality. They got to check the box, the legal, the HR, the whatever, compliancy thing. So, there’s that.

Or other times, it’s like, “Well, we’re going to do this just in case someone just blows our mind with a wildly awesome resume, but most likely it’s probably going to be someone that we’ve talked to at some point earlier in the process and we’re vibing with.”

Judd Kessler
Yeah, and it’s funny, when you think about how much energy to put into a job application, say, or networking with the firm, then it’s you on the other side of that. You want to know that the firm is actually serious about hiring somebody before you invest. And that’s the analog to the firm wanting to know that you’ll stick with it if you get hired. It’s the same problem, just from the other side.

So, I think probably seeing if the job posting is being advertised widely by the firm, they don’t do that when they’re posting the job just for a legal requirement, just to like kind of say they did it. But if you’re starting to see them kind of posting, or people that work there being like, “Hey, we’re looking to fill this role. Great people, come apply,” all of a sudden, that’s a signal to you, like, “Oh, maybe they actually are looking for somebody. Maybe the person they met early in the process turned out to take another job, and now it’s up for grabs.”

But again, in that environment, you’re on the side where you have to decide how real is this job opportunity. So, I can understand why people play a numbers game applying to lots of jobs. You want a job, but a successful kind of efficient outcome, in the econ speak, efficient way of kind of that market resolving is when a firm finds somebody that’s going to be a good fit. And that means both they like the candidate and the candidate likes the job.

Pete Mockaitis
Well, let’s say we’re zooming into, okay, you’re in a job right here, right now, and you would like to have cool projects, cool opportunities, advance, receive promotions, etc., are there any hidden market principles or strategies that you’d surface for us here?

Judd Kessler
Yeah, so I love that because if you start to think about what a hidden market is, it’s when there’s a scarce resource, “We’re not going to just raise the price to decide who gets it. We’re going to have some other set of rules.” Well, that describes our time and attention very well.

We have a limited amount of it. We’re not going to have people pay us to respond to their emails or take a meeting. Maybe some consultants or corporate lawyers might do that. But for the rest of us, we are deciding how to allocate our scarce resources to the projects and the people and the activities that matter most to us. And so, thinking about the same principles of, “What is this market trying to achieve? And is it doing it? And is it doing it in a way that we kind of value?”

So, when I look at a hidden market, and particularly as a market designer, kind of deciding how to allocate my resources and in this case, my time in my email inbox or the time on my schedule or kind of which projects I focus on, I think about whether the allocation is efficient, meaning it puts my resources to the best use. I think about whether it’s equitable.

Like, if I want to treat two people kind of fairly, the same, am I actually doing that? If I have two managers, and I want to make sure that, kind of, both are happy with me, like am I doling out my resources appropriately?

And then is it easy for market participants? Are the people who are trying to get my time and attention, like am I making them go through an ordeal to get it? Do people, do my subordinates have to send me 12 follow-up emails to get me to respond? Like, that’s not an easy way to operate.

And so those same principles can help us kind of think about, “All right, are we designing this in a way, our own allocation of time and attention, in a way that actually achieves our goals?”

Pete Mockaitis
Yes, that gets me thinking. And so, do you have any fun examples or stories of any clever professionals who were doing some things?

Judd Kessler
Yeah. So, this was something that I came to when I was doing research for the book. So, it’s going to start out outside the office, but I’ll bring it in. So, the Colorado River runs through the American Southwest and delivers water to California and a lot of the states in the Southwest, into Mexico. And the way that the rights to the water in the river were allocated was using a hidden market with the market rules, “First in time, first in right.”

And what the rules were was that whoever was the first to tap the water from the river to kind of pull it out of the river for their use, it turned out to be California in 1901. They pulled it out to irrigate their farmland and they’ve been using it ever since. And the rules were, whoever tapped the river first, if there was a drought, that state got their water rights kind of guaranteed.

And the states that tapped it later, like, think Arizona, their rights were subordinate. So, if there was a drought, California would still get their water, but Arizona would not. And you think about that and you think about, this was a race that was run 120 years ago. And at that time, Phoenix, Arizona was less than 10,000 people and now it’s almost 2 million, so it doesn’t seem like, like those rules don’t make sense, “Why should we give California all the water that they want and Arizona has to cut back? Should we care about how efficient the water use is and whether the allocation is fair?”

And I was reading about this, and I was like, “Yeah, this is so silly. Why would anyone have these rules?” And then I looked at my calendar for the week, and I was like, “I’m doing this constantly. Every recurring meeting that I’ve set up is first in time, first in right. A year ago, I started this project. I set up a meeting. Once a week on Thursday, 10:00 a.m., we’re going to meet every Thursday. And now I schedule a meeting for a new project.”

I have to squeeze it between these meetings I set up months or years ago for projects that, independent of how valuable that hour of my time is, I’ve kind of set up a system that looks like the system I was making fun of when I was reading about it.

And so, that for me has got, I basically pulled off all my recurring meetings. My teaching, obviously, sacrosanct, I teach when I teach, but any kind of project, it’s like, “We’re going to decide case by case whether we should be meeting or not.”

Pete Mockaitis
Well, yeah, that is compelling, to look at those recurring meetings and see, “Is that sensible?” And it’s funny how we just accept, “Well, this is what the calendar says.” It’s like, “Well, wait. Wait a minute. Wait a minute. I actually have some authority, autonomy, in driving this thing here and saying, ‘Hey, like I recently changed my recurring podcast meeting times to facilitate school pickups.’”

It took me weeks before I was like, “Oh, yeah, it’s kind of tricky. I mean, I got podcast interviews there.” It’s like, “Oh, I could just change the slots available for people to take for their interviews.”

Judd Kessler

This is like so much, so many of the hidden markets that are out there, and that I talk about and saw when I was researching the book. Like, a lot of them are just historical accident, like, “We always did it this way, and so we continue to do it this way.” So, it’s true of, when you put a meeting on your calendar that recurs, it’s kind of set it and forget it, and you have to remind yourself, “No, it is under my control,” as you just said.

But we talked at the beginning about live event tickets and having to click faster than everybody else. It is not clear to me why we use first come, first serve races for ticketing. Like, I understand why when, before credit cards and before the internet, like it made sense to say, “All right, people have to be there physically to buy tickets from the box office or buy tickets from a record store that would sometimes sell them for concerts.”

And you want it to be efficient so you want people who care more to get the ticket. So, what are we going to do? We’re going to have a line and the people who wait the longest, like they’re clearly the most kind of motivated. Now there’s some efficiency gains there, in the sense of like you’re giving the tickets to the real diehard fans because they’re spending the night, you know, overnight, camped out in front of the Box Office.

It might not be equitable. There are some people who don’t feel safe sleeping on the street in front of Box Office or a record store. And it’s not easy. I mean, it’s an ordeal to spend the night there, but you could understand why you would do it that way. You move it to the internet and now it’s whoever can program the fastest bots gets to buy up the tickets.

And it’s like, “Why are we still doing first come, first serve?” Like, when you look at these markets and the market rules, and you think, “Oh, well, of course we do first come, first serve. That’s how we’ve always done it.” But maybe that’s not the right way to do it anymore.

Pete Mockaitis
Well, yeah, absolutely. Well, you got me thinking in terms of there is…well, that’s a fun title you have – market designers. I was like, “What exactly does that mean? Oh, that’s what this means. Thank you.” There are so many ways that can achieve the outcomes that you’re after, it’s like, “Yeah, we want the diehard fans.” And so, it could be very well, especially with all this technology, it’s like, “Okay, well, if you’re on the email list, how long you’ve been on that email list? How often?”

Because, I mean, my own email software will tell me who are my most engaged email subscribers, in terms of opens and clicks, and how long they’ve been around and they’ll even, like, put some numbers on it. So, it was, like, you could very well roll that out in terms of the super-engaged email subscribers are the ones who get the first crack at being able to buy these tickets.

Judd Kessler
And there are innovations in that direction. Like, the Ticketmaster has something called “Verified Fan.” I think it’s more about, like, trying to figure out who’s a bot and who’s a real person. But you can, and they have kind of built-in, like, “Okay, do you stream Taylor’s videos? And are there ways to kind of indicate that you are more engaged?”

But another way that I like, and I talk about in the book, is how about just flexibility in when you will see the show and where you will sit? So, if you asked me how to allocate tickets to The Eras Tour, I would say, “Well, what if we just did, like, kind of lottery section by section? And you could say, ‘I will sit in any section of any stadium within these four cities on any night.’”

That person will have a higher chance of winning than somebody who’s like, “I only want to sit in the premium seats on the Saturday performance in my hometown.” And that is a way of indicating that you are a real fan of basically being, ultimately, flexible to move around the rest of your schedule. And so, kind of a lottery structure, which gets used for kind of rush tickets and in other contexts.

That strikes me as a nice way of saying, “These are the people who really value it because they are basically entering themselves in for every possible chance to get to see this artist perform live.”

Pete Mockaitis
And it also has me thinking about the movie “War Games,” where the computer says something like an interesting game, the optimal choice is not to play. And sometimes, as you really think through these hidden markets, and you understand the rules and how they work and what you have to gain or lose by participating, you may make smarter choices, like, “Oh, it’s not worth playing this game at all. Maybe I need to try to invent my own game over here. I got to invent a different opportunity to accomplish what I’m after, rather than entering the meat grinder mosh pit over here.”

Judd Kessler
No, and people do that. They look at markets and they think about, “How difficult will it be to be a market participant? And what is the chance that I get what I want?” And when you look at that, when you see the hidden market, you understand the market rules, and you think about what strategy you’d play, you might decide, “You know what? I’d rather not.”

There’s a great ice cream parlor about 10 blocks from my apartment, and on some Sundays, they give away free sundaes at 3:00 p.m. And my kids are like, “Oh, it would be great if we get a free sundae.” And it’s like, “Yeah, but I think it’s going to be crazy when we get like, we’re either going to have to arrive super early or there’s going to be shoving matches.”

And it’s, like, even if the whole family goes and we get five free sundaes, like, it’s probably not worth it. We’ll pay full bore for the sundaes some other time, right? But we have to decide in these situations, like, “Is this a market that is really worth it for us to be in?” Or should we be trying to go to a different restaurant, go to a different live event, wait until there’s less demand for this kind of very popular show and go see it later?

Pete Mockaitis
Lovely. Well, Judd, tell me, anything else you really want to make sure to mention for professionals looking to be awesome at their job, thinking hidden markets and being more effective?

Judd Kessler
Yeah, I mean, there’s other examples in the book that are kind of about not just how we allocate time and attention, but how we allocate other resources within the firm, like financial resources or kind of budgets that you might be in charge of allocating. And it’s the same kind of logic of thinking through “What are the incentives you’re creating for people on the other side of the market?”

So, I teach in one of my classes for executives in the executive MBA program at Wharton, about American Airlines had their AAirpass, and other airlines had similar products where they basically sold unlimited first-class tickets. Like, you could buy a pass that basically gave you as many first-class ticket flights as you wanted for as long as the pass holder lived.

And it was a strategy in the late ‘80s and early ‘90s to get a bunch of cash early when the airlines needed it. But it turned out that when you set the price of an airline trip to be free, but it’s very costly for you to provide that because it’s crowding out a paying customer, then, all of a sudden, you are kind of creating this incentive for folks to fly constantly.

Many of them are still alive and they cost the airlines millions of dollars a year. And it might not be a smart move for you to offer kind of membership style services where you give a lot of benefits away for free that kind of continually costs you. And it kind of speaks more broadly.

Like, if you’re in charge of budgets, like use it or lose it budgeting where you give folks money, and you say, “If you don’t use it, we’re going to take it back. Or, worse, if you don’t use it, we’re going to take it back and give you less next year.” Like, you’re creating the same kind of incentives of people to just, you know, at the end of the year, be like, “Oh, we haven’t spent this all. Let’s go on a spending spree.”

Pete Mockaitis
“All right, 50 iPads. I guess we’ll buy them.”

Judd Kessler
“Yeah, that’s what we need.” And research shows, like when the government does this, and they evaluate the projects that get bought at the end of the fiscal year, they’re bad. They’re not good projects. They’re the groups that have these funds kind of just spending the money so they don’t have to give it back to the US Treasury.

Pete Mockaitis
And really thinking about the market participants and their incentives can really help cut through a lot of the noise. And I’m looking at on my bookshelf, I got Thomas Sowell’s “Basic Economics,” in which he says that, “We really shouldn’t evaluate policies based on their intentions because most of them are great. But we should really think about what are the incentives that are creating and, thus, the likely behaviors.”

And it’s funny, as I think about some digital marketing type stuff, and people really stress the algorithm, it’s like, “Ooh, how can I get to the top spot of Google or the recommended videos in YouTube?” And so, they think about all these things, “Well, there’s my keyword density, and there’s my thumbnail, and there’s my, compelling clickbait-y title,” whatever.

But often, it actually could get pretty simple. It’s like, “Well, what Google wants people to do is keep Googling. So, if you want to be in the top spot, ideally, you will just phenomenally address the question that people are Googling. Or, what YouTube wants people to do is keep sticking around YouTube and being served ads.”

So, ideally, if you could be so engaging and captivating that they watch your whole video and then want to watch more of your videos, then you’re doing just what YouTube wants and they’ll automatically get the memo and try and shove you in places. And so, I find that this approach of just thinking from the higher-level principles, the participants and their incentives, can cut through a lot of noise to get you after. What do we really got to focus in on here?

Judd Kessler
Yeah, and a lot of times, I mean, I think we’re trained to do this, to think that kind of we have to outsmart the system, that, “Oh, we have to kind of play a strategy that’s too clever by a half.” And it’s like, “No, sometimes you don’t want to do that. Sometimes you want to just deliver high-quality content because that’s what’s going to be the best possible outcome.”

But you’re exactly right, that thinking about the incentives of the people that you’re participating in the market with, whether it is people competing against you or people on the other side of the market who you’re interacting with, is the ball game. I talked about your time and attention, I used to want to be a good professor and I want to be responsive to my students. That’s the intention of the policy.

When students would email me, I would try to respond as quickly as possible. And I realized a lot of the questions they were asking me about were stuff that they could easily find out if they read the syllabus or kind of did the old meme of like, “Let me Google that for you,” where you, speaking about Googling, just like kind of saying, “Hey, this is something you can find out on your own. You don’t have to ask me.”

It made me realize, like, I have to stop responding to these emails because I’m creating more work for them. They have to email me and wait when, really, I should be teaching them to kind of gather the information, get the information on their own. And I’m creating a ton more work for myself because I’m responding to all these emails I don’t need to.

So, if I just kind of lay off and say, “Hey, if you have a question, look at the syllabus. If you ask it to me, you know, I’ll get back to you, but it might take a couple of days.” Like, that has dramatically shut down the number of, kind of unnecessary communication, kind of waste of everybody’s time, and particularly mine, that I’m doing, again, because of this change in the incentives that I set up for people on the other side of the market.

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

Judd Kessler
So there’s a quote by Seneca, the Roman philosopher. It’s attributed to him, these old quotes, you never know. “Luck is when preparation meets opportunity.”

The other one is one that I worked really hard to make sure was in the book. It’s in a footnote. One of the market rules that I talk about is first come, first serve waiting lists, where you put your name in, you kind of wait. So, I got in this quote from The Simpsons, where Homer comes back from the video store, and Marge, his wife, asked him if he got the movie, and he says, “Well, they put us on the waiting-to-exhale waiting list, but they said, don’t hold your breath.”

I was like, “I’m going to get that in. I’m going to, really. I’m going to do it.” Editor back and forth, but it’s in there. It’s in there, it made it in.

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

Judd Kessler
Yeah, so there’s a great one that I talk about in the Choose Me Markets chapter. It’s a dating study, and it kind of dovetails really nicely with the labor market studies. A lot of the economics that is happening is the same across those two. But it’s a South Korean dating market, and folks have to pick 10 people that they want to match with and maybe kind of meet in real life.

And the researchers vary whether they have eight or two signals, special kind of, they call them roses that they can send along with their proposals to meet with somebody on the other side of the market. And it’s a really great study that looks at kind of, “What is the effect of these signals? And are people using them correctly?”

And they, typically, do not. Everybody sends their roses to the kind of most attractive people on the other side of the market. But the optimal strategy there is to send them to people who might be surprised to learn that you are interested in them, that you are kind of, they might have thought you were out of their league, and here you are kind of saying, “No, I’m actually really interested in you.” That’s when these roses, that’s when these signals are super effective. I really liked that study.

Pete Mockaitis
All right. And a favorite book?

Judd Kessler
So, I have to say the kind of book that comes before this one, in terms of a pop economics book about market design, is Al Roth’s book, Who Gets What — and Why, which kind of sets the stage for a lot of what I talk about in my book.

Pete Mockaitis
Okay. And a favorite tool?

Judd Kessler
So, I really like the snooze feature in Google, in Gmail. I used to use Boomerang, a kind of third-party add-on, but this has really helped in me achieving some of my goals. Like, for example, not responding to student emails right away, so I can just snooze it for three days, and then respond. So, I won’t forget to respond if they do need help, but it trains me not to just kind of react to the fact that somebody sent me 12 follow-ups.

Pete Mockaitis

Okay. And a favorite habit?

Judd Kessler
So, I have gotten in the habit of making sure that I get some time for myself, maybe not every day, but a couple of times a week. So often that’s working out, but sometimes it’s just going for a walk. And in the book, I talk about how important it is to give some of your scarce resources, like your time and attention, to yourself, but I’m trying to live that better. But actually, I find it makes me more productive and more attentive and engaged when I am devoting time to other projects or people.

Pete Mockaitis

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

Judd Kessler

So, I would point them to JuddBKessler.com, B is my middle initial for Benjamin, and that’s my website. They can also go to GetLuckyByDesign.com. It takes them directly to the book page. And they can find me on LinkedIn.

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

Judd Kessler
I think they should think about the hidden markets that they control, and whether their rules that they have set up for those markets are actually achieving the things that they want them to achieve, or whether they’re kind of, they’re doing what they’ve always been doing and kind of the inertia is holding them back. And I think if they look at these markets with fresh eyes, they might be much happier with the outcomes that get generated.

Pete Mockaitis
All right. Judd, thank you.

Judd Kessler
Thanks so much for having me.

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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