Shannon returns! How to Know if You Will Win at Entrepreneurship and Love It Too? (+ a Few Biz Ideas). Part 2 of 2. Ep #064
24 Dec 2025 · 28 min
Shannon and Chris discuss how to know if you'll succeed at entrepreneurship. Start with small experiments on Etsy, reselling, or Airbnb guides to build confidence through wins. Do the manual work yourself first to learn operations, then position services as premium to avoid competing on price alone.
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And I'm thinking of myself, where I got my confidence, and that was knocking 50,000 doors in Eastern Europe for two years and getting rejected almost every time. So I'm trying to think of back to us, trying to be tactical and specific. What do we tell a 25 or a 55 year old or anyone in between that says, I want to do this, I want to do what you're doing, I want to do entrepreneurship, but I don't really. I don't really like problem solving yet, but I want it.
I want to like problem solving.
And I don't know if I'm confident yet, but I want to be confident. What do you do with that?
Welcome to the Kerner office.
This is the second part of the.
Shannon episode that we started a week ago today. Today we speak in a little more generalities about entrepreneurship, how to make your first dollar, what audiences online are the most valuable, how to have resilience as an entrepreneur. Some practical advice for people just getting started in making money outside of a 9 to 5. We used an analogy about a slingshot.
Think you'll like.
We talked about compounding.
So last week we talked a lot.
About a lot of specific business ideas. And this week we're talking in more generalities about entrepreneurship and how to get started and how to persist when things get tough. But we did talk about some tactical stuff as well. Facebook groups, Etsy opportunities, Airbnb opportunities.
If you're going to like it, enjoy, please like and subscribe.
Share with your friends and we'll see you next time.
I'm glad you brought up the accessibility part because I'm really leaning into that as well. Like it's, you can go upstream or you can go downstream, right? Like you can talk about billionaires or you can talk about side hustles. And I like talking about things that are more accessible. It's not as sexy, not as cool. What are you working on right now?
I often comment is people are in love with the end state of entrepreneurship. That's awesome. And that attracts me too, of course. But I feel compelled to share the work and the little stuff. And like we were talking about earlier, it's great. Yeah, you want to make a million dollars, but let's start with a thousand and let's get a system. Because if you make a mistake at the million dollar level, well, it has a much greater impact on your life. Right. It can be very negative because can you afford wipeout risk maybe in your 20s, but could you do it with your family in your 30s or 40s? I don't think so. You get to make those mistakes on that, on the way up. And then you take a little more risk and a little more risk. And so you. It's that mistakes or tuition, and you're building your education and your curriculum along the way. So I'm with you. And I'm doing it right now. We were talking about content creation. I've wanted to productize my knowledge forever and just didn't know how to do it. And so now I'm doing it. Some stuff doesn't work. Some stuff works. But I celebrate the small wins, the a hundred bucks, the thousand bucks. That's that to me, that gives me energy and I can feel it. And it makes me want to get up earlier, want to stay up later, want to be in front of my computer more. That gives me energy.
Yeah.
What's really interesting is I've been on YouTube and so now I have like data to back up the quote, the value of an audience when you talk about different things. Because YouTube will show like I interview people that are ultra high net worth and then I interview people that are making a few thousand bucks selling garage shelves on the weekend. Right?
Yeah.
Everything in between.
Yep.
Thank you. And one thing that I've noticed, because YouTube will break down your CPM, your cost per mil or cost per the value of the audience on a per video basis. And when I interviewed a guy named Matt who started an alpine slide, cost him $8 million, he's got a bunch of like eight figure hits. And he's very interesting, very engaging. And the CPM on those videos is like, I'll say RPM because CPM is before YouTube takes their 50 or 45% cut revenue per mil is what I actually take home. And so Mr. Beast's RPM, it's like two to three dollars. A lot of business channels are like six to $8. And when I talk to these ultra.
High net worth guys, for whatever reason, the RPM on those is like $8.
Which is above average. It's good when I talk to the.
Guys doing a side hustle, something more accessible. The RPM is over $20.
Is that right?
Which is unheard of for YouTube.
And it's like, why is that reversed?
And I was thinking about it and it's like the people watching this are.
Probably more likely to take action.
Yes, right.
Of course.
They're to the point in their life where like they're already likely successful. They're ready to go to Home Depot and buy a chop saw. They have money. Like maybe they're making six Figures in their job, but they don't like their job. And they're to the point where they're ready to take. Whereas if you look at the RPM of a motivation channel that just has Elon Musk quotes, it's like $4. Because it's just dreamers. They're not doers. What do you think about that?
I agree with you. And I think that most people, we all strive for something better. We want something better for ourselves, maybe for our kids. We. Whether it's something we want, it's a physical thing or education. So whatever it is, there's cost associated with that. Your time, money. And I think that those folks that can watch that. And as you talk about these actions are what makes it work. And like, I'll give you example.
It's tactical specific.
It's not just great strategy of like, I talk about auctions all the time, but I don't say like, hey, you should go buy this couch. These couch returns from Costco. That sounds like a nightmare to me. But I want you to get in the game and start studying liquidations and returns, because you can start on a small level and ease your way in. You can do it out of your garage and easy way out. But when I was running like three or four companies and making good money and everything else, and then Etsy came along, right? And I was like, what is this Etsy, man? And I was like, I got some time in the evenings. I had already started something, a couple of companies, like, I gotta figure this out. So I'm studying. I'm just up on Etsy. I'm just looking around what's selling. That seems like a lot. And I found that these guys and women were making these kind of steampunk light fixtures out of this black metal pipe. And they look really cool. And I was like, man, I got a spot. I was like, you know what? And they're like $750. They're selling these really nice big wall things on there. I was like, I could totally do that. Come on. I'm not there. So I went and bought all the pipe. I was shocked that the pipe to build this big thing was like 250 bucks. Got the wire, got these fancy LED bulbs, and I learned it. I was like, okay, man. And I got. I spent probably a week and the evenings building the first one. And I put it up my house, and it's still up in my kitchen, tucked up between the open beams in our kitchen. And then I talked to my wife. I was like, I'm going to make these up. And she's like, well, how long does it take? Are you going to do it? I was like, well, yeah, maybe I don't want to do it, but I could. I learned how to do it. I could. And you could have made a few hundred dollars per light and managed it and this kind of thing. But I think it's that curiosity as well. And the biggest gift for me to be being an entrepreneur is confidence. Like I've started telling people that want to be coached. I was like, really? I sell confidence that you have once you can make a little bit of money on your own. For some of these businesses and ideas we're talking about today, it changes your whole life and your whole framework. You talk to people, you're more confident. If you have a regular 9 to 5 or W2, it's going to help you there because all of a sudden you're more confident and maybe it allows you to speak up and offer different ideas because you learn something in your jaw. Your side hustle. So I think the world is just full of people that want more. And your videos coming back full circle, it just tracks those and my posts on auctions and three and a half million people that want to learn about Costco auctions. Okay, well, I know that system, but it's a system. It's not just, oh, you should go buy this and do that. So I think that's why.
Where do you think your confidence came from?
Well, when I got out of college and even when I was in college we talked about this last time I was on your show about flipping trucks while I was in school and looking for the unfair advantage of getting the magazine that came out early. You built, man, you have to solve problems like crazy when you're doing that stuff. And like, oh, this didn't work or that didn't work. And so when you're younger, I fell in love with problem solving and because in the outcome would come and you would sell that truck, make a thousand bucks. That was our whole system. Can we make a thousand bucks a vehicle? And that built my confidence a lot. And I learned a lot from my. I mean, did this before. My mom taught me that reality is flexible. It that was just a part of my upbringing the whole time is you get to create your own life, your own reality, all that stuff. So that helped me build a lot of confidence. And as I started to find a little bit of success, I didn't make a. I don't. I would say every business side hustle I've ever done I don't make a lot of money. In the beginning, we were just congratulating each other for making a hundred, you know, a hundred dollars, $150. So that is how I built my confidence over time when I realized that I didn't have to have someone else tell me what to do. And no matter what happened, the worst mistakes I have ever made, I could always start over. Because I learned the system of making money, I understood it, and I'm a product guy. So I learned the study, research, find the delta between the buy and the sell. I learned the relationship part of it. So that built my confidence because I'm.
Over here thinking, like, it's almost a chicken and egg. Like you have to try and problem solve and fail to get some confidence. But how do you do all that without any confidence? And I'm thinking of myself, where I got my confidence, and that was knocking 50,000 doors in Eastern Europe for two years and getting rejected almost every time. So I'm trying to think of back to us, trying to be tactical and specific. What do we tell a 25 or, or a 55 year old or anyone in between that says, like, I want to do this, I want to do what you're doing, I want to do entrepreneurship, but I don't really, I don't really like problem solving yet, but I want it.
I want to like problem solving.
And I don't know if I'm confident yet, but I want to be confident. What do you do with that?
Yeah, like, I get DMs like that where it's like, where do I start? And especially when I don't have any money, how do I get started? Well, I think you have to study, you have to research. The way I would start is I would have my laptop on my lap. I just wouldn't watch Netflix or Tick Tock or whatever. I'd just be sitting there. It's like, okay, well how are these people making money? Go on X or YouTube or whatever and, and just okay, like in my case, you're buying and selling stuff and I'm giving all these links to these auction sites. And, and then how much can you access? Can you put, if you don't have any money, can you put a few hundred dollars on your credit card? I don't, I don't recommend that. But that's what I did. I mean, I got 40 credit cards that had $10,000 each, and that was my first line of credit, $400,000, because I believed in myself and I was young and I was like, well, what's the worst that can happen? And so if you study and research, it's boring. It's not sexy. It's. And this is. Most people quit because, like, in my case, I look at an auction, say, I can't make any money. I looked at 10 auctions, and I couldn't make any money on any of those. Well, maybe you should change what your. Change your framework and just buy something that you can get your money back so you could, like, exercise, muscle, learn. There's a price to pay. With my handbag business that I started, I knew nothing about this stuff at all. Zero. And so it took me almost a year to really develop it. But the way I started was buying from other handbag resellers. Not a lot. They were sent. I bought cheap bags. 50 bucks here, whatever, a hundred bucks, just so I could get the experience. How did they respond to me? What emails did I get? What does the box look like? What's the packaging? Is there a thank you card inside the box? All those things. And then I created notes. I wrote a book because I was, okay, I'm gonna do this. I know how to do this. I'm gonna do this. They do this terrible. This is an opportunity. And while I was learning that, I was just researching on LinkedIn. Who works for Louis Vuitton? Can I reach out? Yeah, it didn't go anywhere. But who's the big handbag sellers? Oh, that store. Can I reach out to Macy's? Can I reach out to Bloomingdale's? Yes. I reached out to a guy and said, what do you do with your returns or overstock? And he turned me on to the Macy's liquidation website. And that's where I started. And they were mostly garbage. But, I mean, I was. I don't know if I mentioned.
But you're further along. You're further down the road.
Yes. You're swimming upstream. Think of that as fish. You're swimming constantly upstream, and you don't know where you'll wind up. Right. Most people.
But you're making progress.
Yes, you're making progress. You're getting that little thing as you're learning and you're building this foundation. And I think the. You have to congratulate yourself on the small wins, the little achievements. Oh, look, I got my resale permit. Awesome. That's huge. You don't know. 99 of people won't even do that. Right. And I got a business license and, oh, I cleared out a corner of my garage and put some racks, you know, like that rat Guy that you posted about, you built some racks and, and so you can stack stuff in there, check, write it down. I don't like to do lists. I love to did lists that I can write down what I did. It makes me feel like I've achieved more. Right. So I see what I got done today. I got this, I get this. That's what I would do to get started is it's a mental game, right? It's definitely a mental game.
Each one of those steps, like they pick up a book and they're 20% more likely to get there. All right? Now they go get a credit card and they're 40% more likely. Then they go buy some shelving to clear out the garage to buy something, they're 130% more likely to get there. Then they get their reseller certificate and it's like their successes just compound in an exponential way. Not in an incremental way.
No, it's exponential. That's right.
And you might even say like the first step is 120% more likely. And then after that it's like 30% and 40% and 30%. Like, I think you just answered my question. And this is a question I've had for a while, which is like, how do you get started? And I'm thinking to a lesson that I learned at church, which is like, how do you have faith? Well, you have to start with a desire to have faith.
That's right.
If you don't have a desire, then you'll never get it, right? Once you have a desire, pretty good chance you'll make it. And so yeah, anyone that DMs us saying, how do I get started? I don't have any money. Okay, there's something there.
Here you go. Okay.
Yeah, but I think the research. Yeah, yeah, it's definitely.
And I think you have to, you can't just want it. You have to decide, you just have to decide that this is my own, this is going to happen. And for one reason or another. When I, when my kids were little and I was like, oh, I don't want them to go to a government school, I just, we just decided they're going to private school. And I was like, man, I don't have that extra thousand bucks a month. So we had to start a business to generate the thousand bucks a month. And we did it.
And.
But we worked every night from 10 to midnight for over a year before I could bring, before we made 500 bucks a month. We weren't at the thousand yet. Took like A little over a year. And then Once we made 500 bucks, I hired somebody to do the work and I paid them the 500 bucks because it was only about an hour maybe so a day. And then as the site grew, started kicking off money took more time. We paid that person a little bit more. It was probably two years before I could take a thousand bucks a month, right. But eight years later it was generating $30,000 a month. And that's how you start. You start. I got my wife involved because I got her buy in because she said, hey, we're doing this together. And we decided to do this. It wasn't we want be really nice if we could send our kid to private school. No, we decided it was the way and we did it. We went in the hole for the first couple years and then we crawled out. So it's, it is exponential. It's. I. The analogy I really like is all this stuff is like a slingshot. And as you start, it's just this rubber thing hanging there. Everything you do, you're pulling back and you're pulling back and pulling back. And at some point in your life and for, we've had a great life but for me it always made, you know, good money. But that slingshot that I pulled tight for, like, I didn't really get to release it and really blow my life up until I was in my 40s because everything came together of all these people I knew and all these resources I had and I had a building and I had this and I had a forklift and I had all these employees. And so that little start is that you have to decide to do it.
It's so interesting because there are other guys on Twitter or in the business world that hear stories like that. Like I pulled it back for 20 years and I didn't let go until I was in my 40s. And some people take that information influencers and say, business is fricking hard, man. It's a lot harder than you think. Like just if it's, if you think it's too hard for you, keep your job man. Just keep your job. Like that's probably for you. They take this really negative approach to it because people aren't willing to put in the work. People just don't have the self control. People aren't grinders. They don't. And it's like eh, I. That same story. And it's like you can do it.
You can't do it, man.
It will always take longer than you think.
Yes it will.
Everything always. But like, you can do it because it gets easier as you go.
It does get easier. That's a great. That's very important to point out. Yeah. As you stack these skills up, as your talent stack increases, it just helps you with everything else. So, yeah, that's crucial. That's crucial.
Some of the people that they DM us. How do I start and then go do research? And I feel like that's like the first litmus test. It costs $0. And if they're doing the research and they're like, procrastinating that. And you and I just said we're both procrastinators, right?
Yep. For sure.
If they're procrastinating the research and they're treating it like a homework assignment, and then they research a little bit and they don't really like it, to me, that's a signal that they like the idea of entrepreneurship, but they're not going to actually like it. Right. Still important that they did the research. They can check the box. But, like, on the other hand, if you start doing the research and you're energized and you're not procrastinating it, and you're staying up late and you're digging and you're going down these rabbit holes, this is going to be for you. Like, you got to persist because you will like it. It is fun.
It's fun. And I think that in the beginning, you have to give a lot of energy. I'm sure I mentioned this last time, but I'm going to say it again because it's so important to me. You're just grinding when you're tired and you don't want it. It's like going to the gym. You're burnout, whatever. You got a headache. You have this trap, but you're giving lots of energy. But as you start to find stuff and things start to come together, these things give energy back to you. And that's where you get to that point where you want to stay up later, you want to get up early, you want to do these things. And that's what I look for. I look for. I tried to start a software business, and it was a disaster. And 1112 months into it, I was like, this is exhausting, dude. It gives me nothing. And then my guy that I hired to help, he bailed out on the project. And I was thinking, I'm just. I'm not into this. But I had all this content, and I was like, okay, now I can repurpose this and do something else with it. And When I'm publishing that Poshmark lock book, because I'd learned this system and pushing it. So look for the energy. Look for when it starts giving you energy back. That's a sign that things are working.
I like that.
Yeah.
So what ideas are giving you energy today? Is there anything you're particularly excited about or something that you're not even going to capitalize on, but you think that someone else should?
Yeah, I think, like, I still love the Etsy stuff. I think that's still an undervalued market. Everybody can easily make something and you don't have to make it until they buy it. That's what I love. You just have to make some samples or whatever and you can put it up there. No risk, doesn't cost you much. And I think that's if you're creative in any way or you have something to offer. I think that's amazing. Another thing I really like, because I've been doing some research on this, is the Airbnb local guides. If you live in San Francisco or you live in Dallas or whoever, and people are coming to Dallas Fort Worth from another country, why don't you go take them around, take them all to show them the best spots, the restaurants, whatever. And people are making very good money at. It's a side hustle. It's like driving for Uber. But it's that same thing. It gets you thinking on another level. And you can offer all kinds of stuff. And actually, I noticed the Airbnb guide selling, like, content, like guides, like, okay, we come in and then I have this, and you can have different levels. I'll come take you around for the day and it's 500 bucks. Or I'll give you these guides to the DFW area. And these are all the. The things that I grew up with or this kind of thing. I think that's fascinating to me. Easy, right?
Interesting.
Not easy, but accessible. Right?
You have to.
Yeah, you have to create that stuff. One thing that drives me crazy constantly with our vacation rentals is property management and cleaning services. Highly undervalued opportunity, because everybody hates their cleaning services. Everybody I talk to just go to into up in Facebook and start searching for, like, I'm in Tahoe area. But if you search other touristy areas, you'll see everybody. I need a new cleaner. They didn't do this, they didn't do that, they didn't do this kind of stuff. I think it's a big opportunity, and there's tons of guys up on X selling, like, their courses and stuff on how to start virtual cleaning businesses. I would start talking to those guys because. But I would focus, I think the opportunities in vacation rentals, I think the, the shine is off of that business right now. In general. Yeah, but I, we use them in a different way. We only buy vacation rentals for places we want to go stay. And so I use this, I call it slippery math. So you get a bunch of depreciation. Yeah. You cover the costs of all your properties that you're buying, but you get to go there three, four or five times a year. And it's amazing, that kind of stuff. So for free?
Yeah.
Yeah, that's right.
That's right.
What would you say if someone wanted to start like a cleaning company specifically for Airbnbs? And as you said, it is hard. I've had an Airbnb too. And is it possible that someone starts that and it's so hard, like they have all those headaches that you're talking about and it turns them off from entrepreneurship entirely? Or does that just like harden them and make the next one even easier?
It could go both ways, but back to the way the framework, the outlook. If you're listening to this and we're talking about these specifics, you're going to hear these underlying terms and the systems we're talking about. And a big part of it is optimism and looking at things a certain way, you could pick apart. Go look at the comments on Chris's posts and on mine. There's always people in there telling you why it won't work. Well, I don't want to hang out with those people. I want to hang out with people that are like, I'm, I want to try this. How do I learn more? Yeah, that's interesting and fun and that makes life great. Right? And I'm definitely one of those. Our best days are ahead of us people. So can you teach optimism? I don't know, but I hope we're teaching that a little bit. And so yes, it's going to be difficult. Yes, you're going to have headaches and problems and people are tough to deal with. But if you can figure out what is the difference in my solution that may others are not offering. Maybe you just offer a super concierge high end service and you're the most expensive in that area. But you bring flowers and a bottle of wine for the next guest and all these kind, really distinguishing yourself in a way that you're not selling a commodity service like cleaning, which is probably a commodity. So that's the way I would look at it, and yes, you're going to fail, but you just have to keep zigging and zagging to get through it.
Yeah. Anytime I'm doing market research, like let's say I'm in a Facebook group for Airbnb owners. There's a lot of those.
Yeah.
I find that the magic is not in the post. The magic is always in the comments. And you can find third party tools that will export the comments to a spreadsheet. And then you can upload the spreadsheet to ChatGPT and just say, what are all the commonalities? Or like, make me a word cloud from this spreadsheet. Thousands of comments, and it's like, late, late, late. It's like, wow. They just want people to be on time. And if no one's complaining about expensive, then it's like, okay, everyone's cheap. No one wants to pay more.
If you could solve that problem, maybe.
I can be more expensive.
Yeah, that's. It is. You are. You want to be like, hey, yeah, we're the premier service. We are our prices. Is this. Are this for a reason? I mean, we have a big place up there that it's basically 500 bucks every time we turn it around. Right. And so they miss stuff all the time. And it's like, it's just, it's such a simple. I don't run that business. My wife does. So I take. I'm her employee there. So I try to make recommendations, but it works out. She does that. And after. If you've worked with your spouse, having a separation of duties is crucial. I can be a micromanager. That's not a good thing for your wife. So I walk around and go, this is so simple that to organize this and to. They don't even have a checklist, like every room. And little things that are so easy. Like, you know what? Every TV needs to be turned on to be sure it's working every time you clean the house. Because it's all streaming services now. It's not just the way it used to be. And did somebody take the remote? Did the remote need batteries? We're selling a premium. We rent this place out for $1,000 to $1,500 a night. We're trying to sell a premier experience. Right. And you have to look at all that stuff because then you get a call from the guests that says the 75 inch TV doesn't turn on and we can't watch the football game. That's a big problem. That's a Big problem. And they miss that stuff. Drives me crazy.
I think the best way to start a more difficult type of business is to do everything yourself in the beginning. And I wouldn't recommend that for a lot of businesses. But, like, you know what? This house is going to take me seven hours to clean, and I'm going to do it 100% myself for a month straight, and I'm going to know everything about that house. So that way I can ensure that the quality is as good, if not better, than what I was doing. Because a lot of people, they buy these courses and these programs and they buy into the sex appeal of not doing anything. Managing properties from across the globe. And I've owned a cleaning business. It was freaking hard.
It's really hard. Yeah.
But I did it that way. I never cleaned one house.
Yeah. Yeah. And I could tell you my. We just. We bought a place recently up along a river here. It's like five acres, has a couple houses on it. And my wife cleaned the house for the first few times. It's about two hours away from us. Okay, I'm going to go up. Because she needed to understand everything that was going on to build the guide to give to the cleaner and the person that's, hey, you need to do this. And this is the way you do the sheets, because that's how you make a bed in a hotel. This is what we want to do, all that kind of stuff. I do everything manual in the beginning, and then I start looking for ways to automate because I don't know it. I don't know it enough to, like, I'm building some courses and stuff on kajabi. And yeah, I have some help, but I said I need to build one. I need to understand how to solve these issues and what's the pain points and what works and what doesn't. I'm a big fan of that. Yeah, I think it's important.
The reason there's Facebook groups full of people complaining about their cleaning business and no one's complaining that they don't have a chrome extension that tracks when their emails are opened is because it's really easy to build the ladder right from the comfort of your room anywhere in the world. And it's really hard to go clean a house by yourself with your own two hands. Which means there will always, always be opportunity in businesses that require some sort of a manual labor because it fights human nature. Yeah.
Okay. That's it for the Shannon episodes. I'll probably have him on at least once a month or so. Let us know in the comments if I should. And I think you'll agree that we should. So have a good week.
