Most Businesses Fail Because Founders Can't Sell

Summary

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The Duct Tape Marketing Podcast

Episode: Most Businesses Fail Because Founders Can't Sell
Host: John Jantsch
Guest: Brian Will, Serial Entrepreneur and Author
Date: April 23, 2026

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Episode Overview

This episode dives into why the lack of sales ability—rather than product issues, market mismatch, or capital constraints—is the real reason most businesses fail, especially when founders or technicians-turned-entrepreneurs are unable (or unwilling) to sell. John Jantsch sits down with Brian Will, a high school dropout-turned-serial entrepreneur who’s built and sold multiple multimillion-dollar businesses, to discuss the psychology of sales and negotiation, common pitfalls, and actionable frameworks for founders and small business owners to rethink their approach to selling.

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Key Discussion Points & Insights

1. Brian Will's Backstory: From Landscaper to Sales Ace

• Initial Reluctance to Sell: Brian started out in landscaping out of necessity, with no idea he had sales talent.
• Insurance Breakthrough: Friends pushed him into insurance sales. Despite lack of training, Brian sold 12 out of 20 leads in his first week:

  “I had no idea, John, I could sell. I tell my kids all the time, you probably have talents you don’t know yet.” (Brian Will, 03:32)

• Created a System: Built his own insurance agency, sold it to a VC firm, and realized he could codify and teach sales.

2. Why Most Salespeople—and Businesses—Fail

• Fatal Flaws:
  • Talking too much
  • Acting like a stereotypical salesperson
  • Overly technical explanations

  “Most salespeople fail for exactly the same reasons every single time. Number one, they talk too much. Number two, they act like a salesperson.” (Brian Will, 04:38)

• Key Advice:
  • Focus on conversations, not pitches
  • Learn to "shut up" and listen
  • Keep things simple, avoid technical jargon
• Real-World Example: Brian describes a window sales call derailed by technical terms ("Belgian slash and six inch nails") that the customer didn’t understand.

  “That sounds like a band.” (Brian Will, 06:40)

3. The Power of "No" in Sales and Negotiations

• Why “No” Matters: Every negotiation fundamentally starts with “no”—whether you’re buying or selling

  “The most powerful word in the English language is no. Without a doubt. And that’s on both sides of the sales process.” (Brian Will, 07:45)

• Negotiation Tactic Example:
  • Story of negotiating electrician work in his restaurant business—start with a lower offer to anchor negotiations.

  “If your first offer doesn’t insult them, you’ve offered too much.” (Brian Will quoting Richard Branson, 08:10)

• Application: Don’t just present an offer—expect negotiations.

4. Technicians Make Poor Business Owners—Unless They Learn to Sell

• Business Failure Pattern: Most founders are technicians (great at their craft) but poor at sales and management.
  • Example: “Joe the Plumber” leaves employment to found his own business but fails—not from plumbing, but from lack of sales/management.

  “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.” (Brian Will, 12:13)

• Key Lesson:
  • Know what you don’t know—bring in sales help or get trained.

5. Sales System Basics for New Business Owners

• Brian’s Teaching Framework:
  • Observe sales calls to diagnose issues
  • Presentation should be concise, not a “five-minute dissertation”
  • Stop pitching, start asking powerful questions:
    • What do you want?
    • Why?
    • When?
    • Who else have you considered?
    • Why not them?

    “If I can find out what you want… you will tell me exactly how to close you. But that’s a series of questions.” (Brian Will, 13:43)

• Match Communication Style:
  • Assess if the other person prefers data or emotion, then adapt sales pitch accordingly.

6. Reading the Customer Without Being Overly Scripted

• Practical Example:
  • When selling windows, ask specific but casual questions (“Which ones are you looking to replace?”), probe gently, and never directly ask for their budget.
  • Provide realistic ranges up front ($300–$1,000/example) to set expectations and avoid wasted time.

  “Don’t ever ask somebody what their budget is... because they'll lie to you.” (Brian Will, 17:52)

• If They Hesitate at Price:
  • Use a “drop back” offer—present a less expensive option if commitment stalls.

7. Universal Applicability of Sales Principles

• Doesn’t Matter if B2B or B2C:
  • “People are people. I don’t care if you are the CEO of IBM… you’re just a person.” (Brian Will, 18:59)

8. Hard-Earned Wisdom from The Dropout Multimillionaire

• Biggest Regret: Not seeking smarter/more experienced partners or advisors earlier.

  “As smart as you think you are, there are people that know more about certain things that you need to listen to… The difference between your success today or your failure tomorrow.” (Brian Will, 19:22–20:29)

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Notable Quotes & Memorable Moments

• “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.” (Brian Will, 04:05)
• “Stop using tech talk, talk at a fifth grade level. Stop, do check ins, you know, pause for effect…” (Brian Will, 07:10)
• “Negotiation should be part of every transaction.” (Implied, 09:19–09:40)
• “How you receive information is how you give information… My sales tactic has to match how you receive information and then my close ratios will go up.” (Brian Will, 14:10)

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Timestamps for Key Segments

• [01:44] – Brian’s journey: From landscaping to insurance sales success
• [04:16] – Why typical sales training fails and the real art of conversation
• [07:44] – The importance of “no” in negotiations and how to use it
• [11:22] – Why technician-origin founders struggle (Joe the Plumber analogy)
• [13:22] – Brian’s framework for coaching sales newbies
• [16:02] – How to ask questions without sounding like an interrogator
• [17:41] – Using price ranges and the “drop back” technique in closing
• [18:59] – Why sales principles work no matter the industry
• [19:22] – Brian’s biggest lesson: Don’t try to do it all alone—seek experienced help

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Conclusion

Brian Will underscores that the single biggest reason for business failure is a founder’s aversion to, or lack of skill in, selling. Success hinges on shifting from doing ("the technician mindset") to selling and leading—by listening more, tailoring communications, and negotiating every deal. Brian emphasizes that sales skills can be learned and even modest improvements can transform a business’s survival odds. His advice: Don’t try to go it alone, and always be willing to adapt, learn, and seek guidance from those who’ve already succeeded.

Connect with Brian Will: brianwillmedia.com

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Transcript

[A]

What if 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 Jon Jantz 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. 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 Certify. That's DTM World Certify. And book a call with a live advisor. Or heck, you can just chat with our a high advisor too. Just see if this is a fit for you. Hello and welcome to another episode of the Duct Tape Marketing podcast. This is Jon Jan. 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 Negotiations. So Brian, welcome to the show.

[B]

John, I appreciate you having me today. It's going to be fun.

[A]

Start with the fact you dropped out of high school, built 10 companies. At what point did you realize that maybe this selling thing has a lot to do with my success?

[B]

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 in mo grass, right? So that's what I did. And I did that for 10 years. And that company did well until it didn't. That's my. One of my favorite things. And ended up losing everything. Almost went bankrupt. Lost the house, the cars. Made a couple 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. Now, mind you, I'm thinking you remember the movie Groundhog Day?

[A]

Oh yeah.

[B]

One of my old favorites, 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. Yeah. 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. I'll take you on one appointment, and then I'll turn you loose. That's the worst way to train a salesperson, I got to tell you. So that's it. 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. 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? 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. I 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. It was my first sale, and we turned it into a company that went public. I 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.

[A]

Well. 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 is like, I had that skill. I don't even know what I was doing. So. 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 te now?

[B]

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, you 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 roof right out of the gate.

[A]

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? He's got, 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, oh, that is nice. You know, 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 was like, I took the order, right? And it just lasted with me forever. A lot of people talk themselves out of orders.

[B]

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 this, these windows have the Belgian slash and the six inch nails. And they do this and this. And the customer is nod in their head. And I stopped, I said, hey, John, can I ask you something? What is a Belgian slash and a six inch nails? That sounds like a band. And he goes, I know. I said, and he Said something different. And I looked at the customer, 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.

[A]

Right.

[B]

So you can get too complicated and lose your client so easily. I tell people, look, don't use tech talk, 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. We may not be able to make you the best, but we can make you better.

[A]

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 latched onto that?

[B]

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. So 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 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 electricians here. And he wants to fix the outlet in the lamp, and he wants twelve hundred dollars. I said, offer him six hundred. And the manager looked at me and goes, what do you mean? I said, go back. He's already here. He's either going to take my 600, he's going to go home. He goes, but it's 1200. 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.

[A]

That's an interesting point because 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 or you don't pay me that it's that negotiation is really not even a part of the deal. It's like, do you want it or not? So, and what you're suggesting is it should be a part of every conversation or at least every, every transaction.

[B]

So you've been to the mall, right, John, to a store to buy a suit or pants or. Those people are technically salespeople, but they're not selling you anything 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.

[A]

If you're a consultant, agency owner or 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 could 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. Our next certification is coming up soon. You can learn more at DTM World Certified. DTM World 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. Right. So how do you turn that person? Especially the person is like, I hate selling. How do you turn that person? I mean, obviously one of the leverage, pieces of leverage you have is the fact that, well, if you don't sell, you're gonna be out of business. But how do you turn that person into, you know, somebody who can successfully sell?

[B]

So my first book, John, is called the Dropout Multimillionaire. And I talk 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. Mm. And they're not salespeople. And as I like to say, I. 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 and 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. He 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. Yeah.

[A]

No, 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. 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. That you would teach or that. That have really worked for you over the years.

[B]

You mean a new business owner.

[A]

Yeah. Who wants to get better at selling.

[B]

Oh, better at selling.

[A]

Yeah.

[B]

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 sales calls to find out what you're doing right and what you're doing wrong, and then we're going to develop a system for you to learn how to sell. So there 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 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. If we want to get into, you know, high level sales, then we'll start talking about learning who the other person is. You know, some people give and receive information differently. As I like to say, John, if you're an emotional person and you like, you live on your emotions and what, what's going to feel good and do good, and I try to give you a bunch of data, you're gonna, your eyes are gonna 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? How 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.

[A]

So the point you make about reading, you know, how somebody wants to be sold, how they process information, how they learn that, 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. You probably learned it because you've seen everything. But how does that newer person who is really maybe feeling a little uncomfortable with this, like this new approach that they've been taught.

[B]

Well, these things are going to all be product specific. So let me just Let me give you one. Right, right. I have a company that, 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. Why 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 sitting all day. Yeah. So these questions aren't really interviewing you as much as why are you wanting to replace these? And when you say, well, this one's leaking and this one's leaking and I didn't want a double pane here or I want a bigger window, I'm like, okay, great. So you're looking at a double pane window. You want to be dismissed? 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 cost between 300 and $1,000 a piece. To replace 300 is going to get you a base level. A thousand is going to get you the Mac. Daddy. What range are you going to be in? I'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. Yeah, right, right. I also wanted. 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.

[A]

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.

[B]

Don't ever ask somebody what their budget is. And they go, why? It's like, because they'll lie to you. I don't go into the car lot and say, I'm really looking to spend $52,560, right? Right. I'm not gonna do that. I'm gonna lie to you because I think you're gonna take advantage of me. Now, if that same person says windows cost between 300 and $800 a piece, now you know you're not getting it for 200 bucks you're going to give me at least you only can 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 in pot. I'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 can never afford the 500 in the first place.

[A]

Do you find that these principles that you teach doesn't really matter? The industry?

[B]

B2B, B2C.

[A]

It doesn't really matter, huh?

[B]

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.

[A]

So you also wrote the Dropout Multi millionaire. What lesson from that book do you wish you'd learned 10 years earlier?

[B]

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, blah. And it wasn't until I met my business partner Steve, who was way more successful than me. And 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. A hundred percent. And I didn't know that when I was young.

[A]

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, connect with you and find out

[B]

more about your work? Yeah. BrianWill media.com my books, my training, everything's on there. You can find everything you want to know.

[A]

Awesome. Well, again, I appreciate you stopping by and hopefully we'll run into you one of these days out there on the road.

[B]

Appreciate it, John. Thanks for having me.