Most Businesses Fail Because Founders Can’t Sell written by John Jantsch read more at Duct Tape Marketing
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Episode Overview
In this episode of the Duct Tape Marketing Podcast, host John Jantsch sits down with serial entrepreneur Brian Will to unpack the real reasons most businesses fail and why it has little to do with product, market, or funding. Drawing from his experience building 10 companies worth over half a billion dollars, Brian explains how sales, not technical skill, is the true driver of business success.
The conversation explores practical sales psychology, common mistakes founders make, and actionable strategies to improve closing rates. Brian also shares his unconventional journey from high school dropout to successful entrepreneur and breaks down why mastering communication, negotiation, and human behavior is essential for any business owner.
Guest Bio
Brian Will is a serial entrepreneur who has built or co-built 10 companies across five industries, collectively valued at over $500 million at their peak. A high school dropout turned business leader, Brian specializes in sales systems, negotiation strategies, and business growth. He is the author of multiple books, including The Dropout Multi-Millionaire and The Psychology of Sales and Negotiations, where he shares proven frameworks for scaling businesses and improving sales performance.
Key Takeaways
1. Most Businesses Fail Because Founders Can’t Sell
- Failure is rarely about product or market. It is about lack of sales ability.
- Many founders are technicians who lack skills in selling and management.
2. The Biggest Sales Mistakes
- Talking too much
- Sounding like a stereotypical salesperson
- Overloading prospects with technical details
3. Sales Is a Conversation, Not a Pitch
- Asking the right questions is more powerful than presenting features.
- Customers will tell you how to close them if you listen carefully.
4. Simplicity Wins
- Communicate at a basic, clear level, around a fifth grade level.
- The more complex your explanation, the less your customer retains.
5. “No” Is the Most Powerful Word in Sales
- Every negotiation starts with “no.”
- Setting expectations and anchoring price ranges improves outcomes.
6. Never Ask for a Budget
- Customers will often mislead you.
- Instead, provide a price range and let them choose within it.
7. Match Your Sales Style to the Buyer
- Emotional buyers respond to feelings.
- Analytical buyers want data.
- Adjust your approach quickly based on cues.
8. Founders Must Build Around Their Weaknesses
- If you are not a salesperson, hire or partner with one.
- Success requires entrepreneur, technician, manager, and salesperson roles.
9. Listening Is a Competitive Advantage
- Knowing when to stop talking dramatically improves close rates.
10. Growth Comes From Letting Go of Control
- Brian’s biggest lesson is that success accelerated when he stopped trying to do everything himself and trusted more experienced partners.
Great Moments
00:02 – Why Businesses Really Fail
Brian explains that failure is usually due to lack of sales skills, not product or funding.
00:54 – Discovering a Natural Talent for Sales
Brian shares how he accidentally discovered his ability to sell insurance.
03:52 – The Three Core Sales Mistakes
Talking too much, sounding like a salesperson, and being overly technical.
05:35 – Talking Yourself Out of the Sale
A story illustrating how over explaining can lose deals.
07:04 – The Power of “No” in Negotiation
Why every negotiation starts with rejection.
09:57 – Why Technicians Fail as Business Owners
The Joe the plumber example highlights missing business skills.
12:29 – Ask Questions, Don’t Pitch
How questions reveal exactly how to close a deal.
14:47 – Practical Sales Example (Windows)
A real world walkthrough of effective sales questioning and pricing.
16:40 – Why You Should Never Ask for a Budget
Customers will mislead. Set ranges instead.
18:13 – The Lesson Brian Wishes He Learned Earlier
Success came when he stopped trying to do everything himself.
Memorable Quotes
“Most salespeople fail for exactly the same reasons. They talk too much and act like a salesperson.”
“If I can get you to have a conversation instead of selling, your closing rates will go through the roof.”
“Every single negotiation starts with no.”
“If your business fails, it won’t be because you’re bad at your craft. It will be because you can’t sell or manage.”
“The more you talk, the less they hear.”
John Jantsch (00:02.122)
What are the reasons 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 Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. My guest today is Brian Will. He's a serial entrepreneur 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.
Brian (00:40.654)
John, I appreciate you having me today. It's gonna be fun.
John Jantsch (00:43.348)
So, 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?
Brian (00:54.648)
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 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 of critical errors in business that I carried with me for the rest of my life.
John Jantsch (01:05.683)
Yeah, right.
Brian (01:23.81)
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 with Bill Murray? And you remember Ned, 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. And I did not see myself walking around with a briefcase and a hat, know, chasing people down on the street.
John Jantsch (01:34.856)
yeah. One of my, one of my favorites. Yeah. Yeah.
John Jantsch (01:46.048)
Yeah.
Brian (01:51.022)
And I told my friend, no, I'm not selling insurance. Never. I'm a landscaper to start with. So he bugged me and 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.
John Jantsch (02:13.642)
you
Brian (02:15.061)
So that's what we We went on one appointment. We went into this house. We came out. He goes, I just made $500. And I was like, 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? 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, 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. And one of the talents I did not know at the time was apparently I could sell. And within six weeks, I was producing 50 % of the revenue in this agency.
John Jantsch (02:58.421)
Mm.
Brian (03:08.587)
Six months later, I broke off. 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.
John Jantsch (03:30.474)
Well, a lot of people suggest sales can be taught, but it's not a skill necessarily. But you kind of backed into it as like, 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.
Brian (03:44.813)
I
Brian (03:52.654)
You know, it's interesting. Most salespeople fail for exactly the same reasons every single time. Number one, they talk too much. 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.
John Jantsch (04:02.442)
Yeah.
Brian (04:15.854)
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 asked 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 safe's closing rates will go through the roof right out of the gate.
John Jantsch (04:55.776)
My father was kind of an old time salesperson. was a manufacturer's rep and he'd go into these towns and go around the square to the stores that were there. I used to go with him every now and then. I remember he was like, really, we got this great new product. I'm going to show this person today. He walks in and he's like, hey, we got this great new product. The guy's like, that is nice. Can I get 10 cases? Got out his pad, sat it down, came to pen.
and left. was like, well, you didn't even tell me about it. He was like, I took the order. And it just lasted with me forever. A lot of people talk themselves out of orders.
Brian (05:35.663)
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 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 customers nod their head. And I stopped, 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 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?
John Jantsch (06:12.946)
You
John Jantsch (06:27.21)
Yeah, yeah, yeah.
Brian (06:28.622)
So you can get too complicated and lose your client so easily. And I tell people, don't use tech talk. Talk at a fifth grade level. Stop due check-ins, 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.
John Jantsch (06:54.314)
So you start your, I think this is not your first book with this, the word no. Is there a story behind why you've kind of latched onto that?
Brian (07:04.874)
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. can't tell. I've got so many stories about the word no. And the Genesis literally, believe it 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.
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 it 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.
John Jantsch (07:36.629)
Mm-hmm.
John Jantsch (07:54.186)
Thanks.
Brian (07:59.791)
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. He's either going to take my 600. He's going to go home. He goes, but it's 1200. said, listen to me, just go offer 600 and come back. He comes back. 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.
John Jantsch (08:40.96)
Well, that's an interesting point because the word negotiation is in the title, but I think a lot of people think selling is, have this offer, I give it to you, you pay me or 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? So, and what you're suggesting is it should be a part of every conversation or at least every transaction.
Brian (08:56.419)
Yes.
Brian (09:04.536)
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.
John Jantsch (09:13.524)
No, no.
John Jantsch (09:24.234)
So what do you say to that? A lot of times, mean, a lot of my listeners are, you know, they don't have sales teams. 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? 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. But how do you turn that person into
Brian (09:43.672)
Yes.
John Jantsch (09:54.519)
you know, somebody who could successfully sell.
Brian (09:57.423)
So my first book, John, is called The Dropout Multi-Millionaire. 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...
John Jantsch (10:01.311)
Mm-hmm.
Brian (10:26.572)
are started by technicians and 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 gonna start my own business and we're gonna 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 that. 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.
John Jantsch (11:28.938)
Yeah. No, no, no question. I think a lot of people jump out of, 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?
Brian (11:39.33)
Yes.
Brian (11:55.342)
You mean a new business owner?
John Jantsch (11:56.754)
Yeah, who wants to get better at selling? Yeah, yeah, yeah, yeah.
Brian (12:00.374)
better at selling. Okay. 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. 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's sick. 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.
John Jantsch (12:27.114)
Hmm.
Brian (12:29.934)
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's going to feel good and do good. And I try to give you a bunch of data. You're going to 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.
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.
John Jantsch (13:58.314)
So the point you make about reading, you know, how somebody wants to be sold, how they process information, how they learn. 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, 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. how do you...
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, and 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?
Brian (14:47.982)
Well, these things are gonna 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. But which ones are you looking to replace? Well, I'm thinking the ones on the front of the house. Why do you wanna replace those? I mean, why not all of them? Why just these? And you're gonna say, well, because...
John Jantsch (14:52.382)
Yeah. Right.
Brian (15:16.526)
I either want a bigger window or this one's fogging up or I need a double pane window. So these questions aren't really interviewing you as much as why are you wanting to replace these windows. And when you say, this one's leaking and this one's leaking and I don'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 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.
John Jantsch (15:19.786)
It's all the sun all day. Yeah.
John Jantsch (15:30.453)
Mm-hmm.
Brian (15:46.061)
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 a thousand dollars 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.
John Jantsch (16:08.874)
Mm-hmm.
John Jantsch (16:14.922)
Yeah. All right.
Brian (16:16.27)
Right. I also want to try to I don't want to pitch you a thousand dollar window when you say my budget's 200 or if it's in my I never asked somebody a budget. I always give them a range. 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. OK.
John Jantsch (16:23.882)
Mm-hmm. Yeah.
John Jantsch (16:31.508)
Yeah, you know, people ask the budget question. I'm always, you know, what are you looking to spend? That's my favorite question. And I'm like, as little as possible. mean, I'm just trying. It is.
Brian (16:40.174)
Yeah, that's a terrible people don't ever ever ever ask somebody what their budget is and they go why I'm saying because they'll lie to you. They want I don't go into the car lot and say I'm really looking to spend $52,560. Right? I'm gonna lie to you because I think you're to take advantage of me. Now, if that same person says Windows costs between 300 and $800 a piece.
John Jantsch (16:54.898)
Right?
Brian (17:05.646)
Now you know you're not getting it for 200 bucks. You're gonna give me at least, you want me to start at 300, 500, 800, where do you wanna go? Because I could spend all day talking about Windows, but let's talk about what's important to you. And by the way, if we're gonna 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 punt. 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 could never afford the 500 in the first place.
John Jantsch (17:42.504)
Ha
So do you find that these principles that you teach doesn't really matter? The industry, B2B, B2C, doesn't really matter?
Brian (17:52.855)
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.
John Jantsch (18:03.914)
So you also wrote the Dropout Multi-Millionaire. What lesson from that book do you wish you'd learned 10 years earlier?
Brian (18:13.55)
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.
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, 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%. And I didn't know that when I was young.
John Jantsch (19:28.126)
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?
Brian (19:37.484)
Yeah, BrianWillMedia.com. BrianWillMedia.com. My books, my training, everything's on there. You can find everything you want to know.
John Jantsch (19:43.816)
Awesome. Well, again, I appreciate you stopping by and hopefully we'll run into you one of these days out there on the road.
Brian (19:48.943)
Appreciate it, John. Thanks for having me.
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Episode Overview
Certified Facilitator. Her work focuses on helping leaders build self-awareness, navigate complexity, and create cultures rooted in trust and accountability.
Episode Overview