Most Businesses Fail Because Founders Can’t Sell

23 Apr 2026 · 21 min · 8 chapters

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In short

Most businesses fail because founders (often technicians) don’t know how to sell; sales can be taught through psychology, conversation skills, and negotiation framing.

Guest

Brian Well, serial entrepreneur (co-built 10 companies across five industries; peak value over $500M), dropped out of high school, author of The Psychology of Sales and Negotiation and The Dropout Multimillionaire.

Key claims

Sales failure patterns are consistent: talk too much, “act like a salesperson,” and use technical jargon. Start negotiation with “no.” Ask questions, shut up, and match the buyer’s information style (data vs emotional). Use simple presentation (not a 20-minute dissertation).

Notable examples

Insurance training led to 12 policies from 20 leads; window sales example used “delta” pricing ($300–$1,000) and “drop back and pot” to offer lower options if the buyer won’t commit. Restaurant electrician negotiation: manager offered $600 vs $1,200.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Brian's Journey to Sales Success

1:33 to 4:10

Brian shares his personal story of discovering his sales talent after leaving landscaping.

“Start with the fact you dropped out of high school, built 10 companies.”

Common Sales Mistakes

4:10 to 6:50

Discussion on frequent errors salespeople make and how to overcome them.

“Well, a lot of people suggest sales can be taught, but, you know, it's not a skill necessarily.”

The Power of 'No' in Negotiation

6:50 to 8:22

Understanding how starting with 'no' can influence negotiations.

“what is a Belgian slash and a six inch nails?”

Transforming Technicians into Salespeople

8:22 to 13:02

Strategies for helping technically skilled individuals learn to sell.

“And I have been, every single negotiation starts with no.”

Understanding Sales through Information Processing

14:01 to 16:50

Learn how to tailor your sales approach based on how individuals process information.

“who else you've looked at buying it from, and why you didn't buy it from them, you will tell me exactly how to close you.”

Effective Questioning Techniques in Sales

16:51 to 18:28

Discover how to ask questions that guide customers without making them feel interviewed.

“Do you have any idea what windows like this cost?”

Setting Expectations and Closing Deals

18:29 to 20:18

Understand the importance of setting price ranges and managing customer expectations in sales conversations.

“I'll say, well, let me ask you something.”

The Importance of Listening in Business Success

20:19 to 20:30

Learn the vital lesson that recognizing smarter people can accelerate business growth.

“is the difference between your success today or your failure tomorrow, 100%.”
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Transcript

Automatic transcript. May contain errors.

0:00John Jantsch:What is the reason most businesses fail has nothing to do with their product, their market, or even funding? And everything to do with the fact that the founder never learned how to sell. Hey, it's John Jantsch here. I've got a quick question for you. Are you a consultant, agency owner, or fractional CMO who feels like you're reinventing the wheel with every new client, or worse, giving away strategy for free? Well, you're not alone, and that's why we created the Fractional CMO Plus Certification. It's a three-day live experience where you'll license the duct tape marketing proven strategy first approach.

0:33John Jantsch:You'll learn how to turn strategy and strategy engagements into a product. Our next certification is right around the corner. Head on over to dtm.world slash certify. That's dtm.world slash certify. And book a call with a live advisor or, heck, you can just chat with our AI advisor too to see if this is a fit for you.

1:06John Jantsch:hello and welcome to another episode of the duct tape marketing podcast this is john jance my guest today is brian will he's a serial entrepreneur who dropped out of high school went on to build or co-build 10 companies across five different industries collectively worth over half a billion dollars at their peak he's the author of three books including one we're going to talk about today? No. The psychology of sales and negotiation. So, Brian, welcome to the show. Hi, John. I appreciate you having me today. It's going to be fun. Start with the fact you dropped out of high school, built 10 companies.

1:38John Jantsch:At what point did you realize that maybe this selling thing has a lot to do with my success? You know, it's funny, John. The first company I did was landscaping, and I only did it because I basically had no education and no job skills, and I thought anybody could dig a hole and mow grass, right? So that's what I did. And I did that for 10 years and that company did well until it dipped. That's one of my favorite sayings. And I ended up losing everything, almost went bankrupt, lost the house, the cars, made a couple of critical errors in business that I carried with me for the rest of my life. But what was interesting when I got out of the landscaping business is a buddy of mine, he said, hey, you should come sell insurance with me.

2:21Now, mind you, I'm thinking, you remember the movie Groundhog Day?

2:24John Jantsch:Oh, yeah. With Bill Murray? One of my favorites, yeah. And you remember Needle Nose Ned and every day he tries to get Bill and one day Bill just knocks him out in the street. That was my internal picture of an insurance salesman. I did not see myself walking around with a briefcase and a hat, you know, chasing people down on the street. And I told my friend, no, I'm not selling insurance. Never. I'm a landscaper to start with. So he bugged me and six months goes by and he kept showing me big checks. And finally I said, all right, how do I sell insurance? And he said, give me$500. I'll give you some leads.

2:57I'll take you on one appointment and then I'll turn you loose. That's the worst way to train a salesperson, I gotta tell you. So that's what we did. We went on one appointment. We went into this house. We came out. He goes, I just made$500. And I was like, oh my gosh, that's incredible. So I took these 20 leads. And a week later I showed up at the office and I had sold 12 insurance policies. and the guy that owned the agency, I walked in, I put him on the table and he goes, what's that? And I said, those are the insurance policies I sold this week. And he goes, how many leads did you get? And I said, I had 20.

3:30I said, is that not good enough? He goes, oh my God, that's like top 1 % in the country. What did you do to sell those? I remember saying, I don't know. I just sold them. I had no idea, John, I could sell. I tell my kids all the time, you probably have talents you don't know yet. One of the talents I did not know at the time was apparently I could sell. Within six weeks, I was producing 50 % of the revenue in this company, this agency. Six months later, I broke off. I started my own agency. A year and a half later, I sold it to a venture capital firm. That was my first sale. And we turned it into a company that went public.

4:05I didn't know I could sell. I just could. And I don't know why. But then I turned it into a system of selling and sales management and training and wrote the book. And, you know, that's what I do.

4:16John Jantsch:Well, a lot of people suggest sales can be taught, but, you know, it's not a skill necessarily. You kind of backed into it as like, I had that skill. I don't even know what I was doing. So how do you kind of reconcile that with the idea that you're now taking people who maybe say, I don't have that skill and you're teaching them? You know, it's interesting. most salespeople fail for exactly the same reasons every single time. Number one, they talk too much. Yeah. Number two, they act like a salesperson. If I can just get you to learn how to have a conversation with somebody and not act and sound like a salesperson.

4:58You know, a salesperson's, their voice goes up like an octave and they talk really fast and they're excited. Like, hey, John, how are you, man? I'm glad you came in today. And you're like, dude, you're a salesperson. Stop doing that, right? And then if I ask you about a product, you have to give me a 20-minute dissertation on everything there is to know about everything about this product, and I don't care because we know that psychologically people only remember 30 % of what they hear anyway. So the more you talk, the less they hear. And then the more you talk, the less they want to listen to you and now they just want to leave so if i can get you to number one have a conversation instead of sell and number two learn when to shut up your sales closing race will go through the

5:39John Jantsch:roof right out of the gate my father was a kind of an old-time salesperson he sold he was a manufacturer's rep and you know he'd go into these towns and go around the square to you know the stores that were there and i used to go with him every now and then and i remember he's like really we got this great new product. I'm going to show this person today. Walks in. He's like, hey, we got this great new product. And the guy's like, oh, that is nice. Can I get 10 cases? Got out his pad, sat it down, gave the pen and left. I was like, well, you didn't even tell him about it. He's like, I took the order.

6:14John Jantsch:And it just lasted with me forever. A lot of people talk themselves out of orders. Oh, yeah. And the third thing is they talk too technical, right? I remember I was doing a project out in Seattle a year or so ago. And I always, if it's a small sales team, I like to go out with the salespeople and listen. And I went out with their top salesperson. And he went in to see this customer and they were selling windows. And he's like, yeah, and these windows have the Belgian slash and the six inch nails. And they do this and this and the customer is nodding their head. And I stopped. I said, hey, John, can I ask you something?

6:51what is a Belgian slash and a six inch nails? That sounds like a band. And he goes, I don't know. I said, and he said something different. And I looked at the customer and I said, did you hear six inch nails? And they go, yeah, that's what we heard too. And if I hadn't stopped John and asked the question, they would have the whole time never known what he said. Right? You can get too complicated and lose your client so easily. And I tell people, look, don't use tech talk. Yeah. Talk at a fifth grade level. stop, do check-ins, you know, pause for effect, just like I did right there. And, you know, there are a few things we can teach you to make you better.

7:30We may not be able to make you the best, but we can make you better.

7:34John Jantsch:So you start your, I think this is not your first book with this, the word no. Is there a story behind, you know, why you've kind of lashed onto that? Yeah, because the most powerful word in the English language is no, without a doubt and that's on both sides of the sales process i can't tell i've got so many stories about the word no the genesis literally believe it or not comes from richard branson and he wrote a book and one of the things in his book he says is if your first offer doesn't insult them you've offered too much huh and no matter what because if you're talking to somebody who's a negotiator they're never going to offer you what you want and if you're selling something, you're never going to sell it for, you know, never going to offer for sale for what you actually want.

8:19So we already know right out of the gate, both sides are going to say no. Right. So we start with no. That's what we always start with. And I have been, every single negotiation starts with no. I'll give you a, I'll give you a funny example. I own some restaurants. I have a manager that works for me. And I was sitting in there with a general contractor one day and the manager comes up and he said, Hey, the electrician's here. and he wants to fix the outlet and the lamp and he wants$1 ,200. I said, offer him$600. And the manager looked at me and goes, what do you mean? I said, go back. He's already here.

8:55He's either going to take my$600 or he's going to go home. He goes, but it's$1 ,200. I said, listen to me, just go offer$600 and come back. He comes back, he goes, he'll do it for nine. I said, take the deal, right? And the manager was like, I don't understand what just happened. And the person at the table goes, do you do all your negotiations that way? I said, yes, I do. Whatever you tell me, it's no.

9:19John Jantsch:That's an interesting point because negotiation, the word negotiation is in the title. But I think a lot of people think selling is, I have this offer, I give it to you, you pay me, you don't pay me. That negotiation is really not even a part of the deal. It's like, do you want it or not? And what you're suggesting is it should be a part of every conversation or at least every transaction. So you've been to the mall, right, John, to a store to buy a suit or pants. Those people are technically salespeople, but they're not selling you anything. No. That's retail, right? Salespeople are true salespeople that are going out and trying to sell a product or a service, and those things are negotiable, period.

9:58John Jantsch:If you're a consultant, agency owner, or a fractional CMO who feels kind of exhausted from starting from scratch with every new client, well, this is for you. The Fractional CMO Plus Certification is a three-day live experience built to help you stop being the bottleneck and start leading with clarity. You're not only going to learn, you're going to license all of our systems, documented processes, and practical tools all grounded in the duct tape marketing strategy first approach. We're going to help you turn strategy engagements into a product you can sell over and over again. You'll also get one-on-one support and join a community of marketers who actually get what you're building.

10:39John Jantsch:Our next certification is coming up soon. You can learn more at dtm.world slash certified. dtm.world slash certified. So what do you say to that? A lot of times, I mean, a lot of my listeners are, you know, they don't have sales teams. I mean, the founder is selling out there. And a lot of times they got into the business because they were good at doing something like landscaping, for example. So how do you turn that person, especially the person who's like, I hate selling. How do you turn that person? I mean, obviously, one of the pieces of leverage you have is the fact that, well, if you don't sell, you're going to be out of business.

11:16John Jantsch:But how do you turn that person into somebody who could successfully sell? So my first book, John, is called The Dropout Multimillionaire. And I talked a lot about this in that book. And we like to say that every successful company has four personalities. And I don't care if it's Apple, computer, all the way down to the guy who just started his own business. You have an entrepreneur who's a big thinker, who's also usually a salesperson, but not always. You have the entrepreneur, you have the technician, you have the manager, and you have the salesperson, right? Most businesses are started by technicians.

11:53And they're not salespeople. And as I like to say, my books are famous for Joe the plumber, right? Joe's a plumber. He works for XYZ Plumbing for 20 years. He goes out every day. They're paying him 50 bucks an hour. One morning, Joe wakes up and says, why am I charging 150 an hour? I'm only getting 50. I'm going to start my own business and we're going to call it Joe's Plumbing. So Joe starts Joe's Plumbing. If Joe's Plumbing fails, it will not be because Joe is not a good plumber. It will be because Joe is not a good salesperson or a manager, one of the two. But Joe thinks that all there is to business is the technician part, not understanding that he doesn't understand how business works.

12:35He doesn't understand how insurance works and payroll works and sales work and, you know, managing people. None of those. He doesn't get that. And so that's why most businesses fail is because they're started by technicians. If you are a technician, understand that you don't know how to do sales. Bring somebody in who does.

12:54John Jantsch:No question. I think a lot of people jump out of work and decide to start a business and don't realize just there's a lot of moving parts. So if somebody came to you, they were a newbie in like a class or coaching or something you were doing, what would be the basic principles? Kind of map out the basic principles that you would teach or that have really worked for you over the years. You mean a new business owner? Yeah. Who wants to get better at selling? Oh, at better at selling. Yeah. So the first thing we're going to do is we're going to, and I hate to say this, but I'm going to go out with you on a couple of sales calls to find out what you're doing right and what you're doing wrong.

13:32And then we're going to develop a system for you to learn how to sell. So in my book, we lay all these things out, but it literally gets into the things we've already talked about, which is you need to bring your presentation down to a few words, not a five-minute dissertation. You need to quit selling and just ask questions. That's one of the most powerful sales tools there is. If I can find out what you want, why you want it, when you want it, who else you've looked at buying it from, and why you didn't buy it from them, you will tell me exactly how to close you. But that's a series of questions.

14:10If we want to get into high-level sales, then we'll start talking about learning who the other person is. Some people give and receive information differently, as I like to say. John, if you're an emotional person and you live on your emotions and what's going to feel good and do good, and I try to give you a bunch of data, your eyes are going to roll back in your head. If you're a data person, and I can tell that very quickly when I first start talking to you, and I start giving you all the emotional reasons why you should do something, and you keep going, no, just give me the numbers, right?

14:45How you receive information, how you give information is how you receive it. I need to pick up that small thing, and my sales tactic has to match how you receive information. And then my close ratios will go up. Matching that with Not talking too much, asking a ton of questions and letting the person close themselves. These are things we teach that I would try to teach somebody. And then it's learning when to shut up. Like, that's the huge one. Just stop talking. So the point you make about reading, you know, how somebody wants to be sold, how they process information, how they learn.

15:22John Jantsch:I mean, doesn't that take a long time to really get good at? I know one of the things that they teach all the time is just what you talked about. go in and probe, right? Ask questions, ask questions. I don't really like that when somebody comes in and I feel like I'm being interviewed because I'm like, I don't really know you that well yet. I don't trust you necessarily. I'm not going to give you, you know, all this information you're asking me for. So how do you deal with kind of, I mean, how do you teach people to do that reading, you know, how somebody needs to be, again, I'm, you know, years of experience.

15:52John Jantsch:You probably learned it because you've seen everything, but how does that newer person who is really may be feeling a little uncomfortable with this, like this new approach that they've been taught. I mean, well, these things are going to all be product specific. So let me just, let me give you one, right? I have a company that does window and door replacement. Okay. So when I walk up to the door, I'm like, Hey John, how are you doing? I understand that you're looking to replace some windows today. Is that right? Yeah. Well, which ones are you looking to replace? Well, I'm thinking the ones on the front of the house.

16:23Why do you want to replace those? I mean, why not all of them? why just these? And you're going to say, well, because I either want a bigger window or this one's fogging up or, you know, I need a double pane. So these questions aren't really interviewing you as much as why are you wanting to replace these windows? And when you say, well, this one's leaking and this one's leaking and I know what a double pane here

16:42John Jantsch:or I want a bigger window, I'm like, okay, great. So you're looking at a double pane window. You want to do this and this. Have you shopped with anybody else? And you'll say yes or no. Do you have any idea what windows like this cost? And you're going to say, well, not really. And then I do what we call, we set the Delta, right? And I'll say, well, just to let you know up in advance, Windows costs, and I know this because I did this with a window company, Windows costs between$300 and$1 ,000 a piece to replace. $300 is going to get you a base level. $1 ,000 is going to get you the Mac Daddy. What range are you going to be in?

17:16I'm going to set the range. And the reason I set the range is because I don't want you to come in and say, I thought they were a hundred bucks and I just spent a half a day with you.

17:24John Jantsch:Yeah. right right i also want to turn i don't want to pitch you a thousand dollar window when you say my budget's 200 or it's in my i never ask somebody a budget i always give them a range i let them pick in the range you want the cheapest at 300 you want me to talk about the thousand let's go in the middle okay you know people ask the budget question i'm always you know what are you looking to spend that's my favorite question i mean i'm like as little as possible i mean i'm just starting people don't ever ask somebody what their budget is and they go why i'm saying because Because they'll lie to you.

17:58I don't go into the car a lot and say, I'm really looking to spend$52 ,560. Right. Right? I'm not going to do that. I'm going to lie to you because I think you're going to manage me. Now, if that same person says, Windows costs between$300 and$800 a piece, now you know you're not getting it for$200. You're going to give me at least, you're going to start at$300,$500,$800. Where do you want to go? Because I could spend all day talking about Windows. Let's talk about what's important to you. And by the way, if we're going to get into super high-level sales, John, if they pick the 500 and we get to the end and they're not willing to commit, this is what we call the drop back and pot.

18:35I'll say, well, let me ask you something. To be very fair, I just told you all about the$500 windows. And those may be what you want. Would you have any interest in hearing about the$300 window? Because if you say yes, you could never afford the 500 in the first place.

18:53John Jantsch:so do you find that these principles that you teach it doesn't really matter the industry b2b b2c doesn't really matter huh no it is what look people are people i don't care if you are the ceo of ibm you still go home and fight with your wife and your kids are throwing up on you and you know you're just a person so you also wrote the dropout multi-millionaire what lesson from that book do you wish you'd learned 10 years earlier you know i spent my first 10 15 years in business trying to do everything myself trying to be the smartest guy in the room particularly when you get under pressure too many entrepreneurs fall back into the red personality zone where they get very autocratic and you will do it my way and blah blah and it wasn't until i met my business partner Steve, who was way more successful than me.

19:47And that even took a year before I broke down and I said, you know what? I'm going to listen to you. And when I did that, we went from zero to we sold our company for$80 million three years later. You know, at some point you have to understand that there are smarter people than you, as smart as you think you are. There are people that know more about certain things that you need to listen to. Finding somebody who's been there and done that, John, who's willing to come in and help you and tell you, and then your ability to take that advice and listen to it is the difference between your success today or your failure tomorrow, 100%.

20:27And I didn't know that when I was young.

20:29John Jantsch:I think that's a great place to end it today. Brian, I appreciate you taking a moment to stop by the Duct Tape Marketing Podcast. Is there anywhere you invite people to connect with you and find out more about your work? Yeah, brianwellmedia.com. My books, my training, everything's on there. You can find everything you want to know. Awesome. Well, again, I appreciate you stopping by and hopefully we'll run into you one of these days out there on the road. Appreciate it, John. Thanks for having me.

From the publisher

Why do so many businesses fail even when the product is strong? In this episode, Brian Will explains why founder sales skills—not funding, markets, or strategy—often determine whether a business survives. He shares practical sales conversation techniques, negotiation strategies, and simple ways entrepreneurs can close more deals by asking better questions and listening more. If you’re a business owner who avoids selling or wants a clearer sales system that actually works, this episode shows how improving your approach to sales can unlock real business growth.

00:00 Introduction

02:42 Turning Talent Into a Sales System

04:16 Sales Mistakes and the Power of No

07:34 Why Negotiation Starts With No

10:49 Core Sales Principles That Close Deals

12:54 Ask Questions and Build Trust

15:15 Talking Price Without Losing Sales

18:51 Final Advice for Sales Success


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