Sales as the System and Why Founders Must Own the Problem with Lou Shipley

Summary

Podcast Summary: Revenue Builders with Lou Shipley
Episode Title: Sales as the System and Why Founders Must Own the Problem
Release Date: April 16, 2026
Host(s): John Kaplan (Co-Founder, Force Management) and John McMahon (Five-time CRO)
Guest: Lou Shipley (Three-time CEO, Harvard Business School Professor, Author of “Unlikely Entrepreneurs”)

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Episode Overview

In this dynamic and candid conversation, sales veterans John Kaplan and John McMahon sit down with Lou Shipley to dig deep into the realities of building great companies through effective sales systems, founder-led selling, and a relentless focus on understanding the real problems worth solving. With stories from the trenches, frameworks from Shipley’s new book “Unlikely Entrepreneurs,” and strategic wisdom from decades in the field, the trio explores myths about sales, why emotional connection to the problem is critical, and how founders and sales leaders can foster resilient, adaptable cultures that drive outsized success.

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Key Discussion Points and Insights

1. Lou Shipley’s Sales Origin Story

• [02:02]—[04:16]

• Lou Shipley started his career selling books door-to-door on 100% commission to pay for college.
  • “I was too cheap to buy a solicitor’s license... so I had a little trouble with the law, but I learned how to sell, handle rejection. Those skills came in very handy.” (Lou Shipley, 02:23)
• Handling rejection and learning the fundamentals of sales were transformative, setting a foundation for later entrepreneurial ventures.
• The analogy between commission-based selling and startups: “It’s the same thing—if I get it right, there’s going to be a lot of money at the end.” (Shipley, 03:14)

2. Sales as a Misunderstood, Essential Skill

• [05:43]—[07:53]

• Sales is often maligned and misunderstood in broader culture.
  • “There’s no other function in business that has a sign, like sales does: ‘No Soliciting’... but the reality is, you’ll be using it in every facet of your career.” (Shipley, 07:53)
• The perception of sales as less prestigious is one of the barriers talented people must overcome.
• Sales skills are equally important for board members, founders, and leaders—not just front-line sellers.

3. The ‘Seller Deficit Disorder’ and Buyer Expectations

• [08:25]—[10:22]

• Thousands of years of data confirm two main reasons buyers resist sellers:
  1. Sellers don’t understand their business.
  2. Sellers don’t listen.
• Overcoming this “seller deficit disorder” is critical; sellers have about 30 seconds to start building trust.

4. ‘The Problem with the Problem’: Root Cause Selling

• [10:24]—[16:11]

• Great products and companies are born from founders who “feel the pain viscerally.”
  • “If you understand the pain viscerally, then you have a better way to start and know what to build.” (Shipley, 11:24)
• Founders must validate that the problem is real and significant beyond personal experience. Shipley requires students to make 100 cold calls to non-friends/family to validate need.
  • “A hundred? Like, yeah, a hundred. Don’t call your mom, don’t call your friends, call a hundred.” (Shipley, 12:24)

5. Emotional Connection and Customer Discovery

• [16:11]—[20:27]

• Success aligns with emotional connection to the problem—when what the company sells truly matters.
• Intellectual curiosity and customer immersion are key for sellers to understand the true impact of their product.
  • “I’d go sit with engineers... ask discovery questions... and then they’d show me the downstream implications.” (Kaplan, 15:13)
• Being curious enough to shadow customers or even visit unlikely venues (e.g., karaoke bars in Japan) to uncover use cases can land huge deals.

6. The Founder Must Be the Chief Seller, Especially Early On

• [20:27]—[27:33]

• In early-stage startups, founders (especially technical founders) often want to delegate sales too soon.
  • “I work with so many technical founders that delegated the sales function before they understood it themselves. That’s a big mistake.” (Shipley, 25:55)
• Successful founders translate their problem empathy into teachable, scalable models for sales teams—not just searching for ‘unicorn’ salespeople who can magically sell anything.
• Sales leadership requires learning to abstract and build teams as the organization grows; founders who can’t transition to CEO behavior may start to “flail.”

7. Frameworks from ‘Unlikely Entrepreneurs’

• [23:05]—[32:21]

• The book features stories of non-traditional founders (e.g., the online casket seller, the badass tire store owner) and practical takeaways.
• Focused on wins, losses, and “murder board” methods for exposing weakness by stress-testing your ideas internally before the market does.
  • “If you were a startup and got $50 million from a VC, how would you kill our company?” (Shipley, 32:49)

8. Coachability, Self-Awareness, and Adaptability as Competitive Advantages

• [37:46]—[40:31]

• Coachability in leadership is critical; avoid companies led by uncoachable founders, regardless of technology strength.
  • “If you see a CEO that doesn’t seem at all interested in being coachable, I’d run away as fast as you can.” (Shipley, 37:46)
• Adaptability is as important as coachability, particularly as markets, products, and customers continually change.
• Key questions to ask a potential employer or founder:
  • Why does a customer have to buy now, from you?
  • What’s your real defensible secret sauce?
  • How has the organization adapted or pivoted in the past?

9. Ideal Customer Profile (ICP), Propensity to Buy, and Sales Complexity

• [44:25]—[48:08]

• Successful startups focus on a narrow set of use cases and customers, maximizing fit and ROI.
  • “Let’s narrow that thing down to three or four use cases... I’m not out there hunting into case number nine, outlier.” (McMahon, 46:34)
• Startups should cut their target market by (1) those who can buy, (2) high propensity to buy, and (3) low sales complexity.
• Resist “total addressable market” traps; tight focus enables repeatability and rapid growth.
  • “You’re bred to believe you need a huge TAM, but fewer ICPs is better.” (Shipley, 47:21)

10. Sales Culture and the Superior Sales System

• [51:08]—[54:40]

• The best companies have “great products and a great sales organization and a meaningful sales culture.”
  • “If I switched products with my competition, could I still outsell them?” (McMahon, 52:03)
• Sales needs to be the “tip of the arrow”—central and valued. Organizations where sales is peripheral do not scale.
  • “If sales is not tip of the arrow... I can’t help them. They don’t work.” (Kaplan, 52:42)

11. The Future of Sales: AI and Timeless Fundamentals

• [55:19]—[58:26]

• The entrepreneurial spirit and focus on solving real customer problems remain foundational, even as technology (like AI) changes the landscape.
  • “I see a lot of improvement in helping with ICP, using AI modeling... but I view this whole tech stack change as just another wave.” (Shipley, 55:19)
• AI can automate some sales drudgery and speed up ICP modeling, but “more things change, the more they stay the same”—success hinges on emotional connection to real problems.

12. Sustaining Entrepreneurial Spirit for Longevity

• [58:26]—[60:30]

• The most enduring companies continue to “disrupt the status quo” and infuse entrepreneurial thinking, whether at year 2 or year 180.
  • “There’s 33 million companies in the country, only a thousand are over 100 years old.” (Shipley, 59:54)

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Notable Quotes & Memorable Moments

• “If you understand the pain viscerally, then you have a better way to start and know what to build.” (Shipley, 11:24)
• “There’s no other function in business that has a sign like sales does: ‘No Soliciting’…” (Shipley, 07:53)
• “If you see a CEO that doesn’t seem at all interested in being coachable, I’d run away as fast as you can.” (Shipley, 37:46)
• “If I switched products with my competition, could I still outsell them?” (McMahon, 52:03)
• “John Morgridge, founder of Cisco... at 92, describes himself as a sales guy. That tells you everything.” (Shipley, 53:45)

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Timestamps for Important Segments

• Lou’s Origin Story & Door-to-Door Lessons: [02:02]–[04:16]
• Why Sales Is Misunderstood & Critical: [05:43]–[07:53]
• Seller Deficit Disorder & Buyer Expectations: [08:25]–[10:22]
• ‘Problem with the Problem’ & Validating Pain: [10:24]–[16:11]
• Customer Discovery Stories (Karaoke in Japan): [18:54]–[20:27]
• Founder Must Drive Early Sales: [20:27]–[27:33]
• The ‘Murder Board’ Framework: [32:21]–[35:31]
• Coachability & Adaptability: [37:46]–[40:31]
• Ideal Customer Profile, Propensity, Sales Complexity: [44:25]–[48:08]
• Sales Culture & Sales as the System: [51:08]–[54:40]
• The Role of AI & Timeless Sales Truths: [55:19]–[58:26]
• Longevity and Entrepreneurial Spirit: [58:26]–[60:30]

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Key Takeaways for Listeners

• Sales is the system that drives repeatable, sustainable company growth—more important than product alone.
• Founders must intimately own and lead the sales process in the early stage, translating visceral problem empathy into scalable playbooks.
• Focus and disciplined ICP targeting yield faster growth than chasing broad markets or endless use cases.
• Strong, adaptable sales cultures and self-aware, coachable leadership are essential for scaling.
• Emotional connection to the problem solved is the secret sauce—no matter how technology changes, this never goes out of style.

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Resource Mentioned:
Book: “Unlikely Entrepreneurs: Wins, Losses and Crucial Lessons on Building Great Companies” by Lou Shipley & Trish Favreau

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[End of Summary]

Transcript

[A]

Welcome to the Revenue Builders Podcast, a weekly show featuring B2B sales leaders and executives. Hosted by five time CRO John McMahon and Force Management co founder John Kaplan, the show takes guests in the barrel behind the scenes with the people who've been there, done that, and seen the results. Revenue Builders covers best practices for scaling and growing your business while sharing the pitfalls to avoid. Enjoy today's episode.

[B]

Welcome back to Revenue Builders, the podcast for people who don't just want to hit a number, they want to build a legacy. I'm John Kaplan and today my co host John McMahon and I are joined by a man who has lived every single stage of the sales journey. I'm talking about Lou Shipley. Now, on paper, Lou is a heavy hitter. A three time CEO, a Harvard Business School professor, and the author of the new book Unlikely Entrepreneurs. But before he was teaching MBAs at Harvard, he was a 19 year old kid knocking on doors in Illinois for 12 hours a day, selling books on 100% commission. This is my kind of guy. In this episode, we're peeling back the curtain on what it really takes to scale. We dive into Lou's unlikely frameworks, including the problem with the problem, the murder board and the sales gene myth. If you've ever felt like an outsider, or if you're a leader trying to turn a sleepy lifestyle culture into a high performance machine, this conversation is your roadmap. Stick around. You're about to find out why the founder of Cisco still calls himself just a sales guy. And why your best character building days are often the ones where, where you don't make a single sale. Let's get into it with Lou Shipley.

[C]

So Lou, your origin story is really a cool one. The way I could summarize it is you're going to college, you gotta pay your way through school. You start selling books door to door, you're on a path to go to Wall street. And sales becomes a big part of your life. Do you mind picking up the story?

[D]

There's. Yeah, sure. So I, right, I needed to, between freshman and sophomore year, needed to make up the difference in financial aid. I went to this company called the Southwestern Book Company and they had, they would train you for a week in Nashville and then you're given a territory. I was given DeKalb, Illinois. And the rule of this company was every town has a park, every park has a bench. So they're like, you had to figure out where you're going to. So we slept in the park the first night. Then we finally found a place. But I was too cheap, I was selling a lot, but I was too cheap to buy a solicitor's license. So I had a little trouble with the law because I got kicked out of town for not having a solicitor's license. But I, but I learned how to sell, handle rejection and those skills, you know, came in very handy. Plus 100% commission is actually a really good, good deal. Like if you can, if you can do the work you make, make a lot of money. So I had no trouble paying for school after that.

[E]

And isn't the handling of the rejection, isn't that the, the toughest part to get over when you first start selling?

[D]

Yeah, John, I think so. I think people think it's going to be hard to think of you're an SDR today, like, oh, this is going to be too hard. But once you get into it and make it a habit, it's not that hard at all. The harder thing about the book selling actually I had some good stories was I got egged by the kids in the neighborhood because there's this book guy on a bike driving around. Rejection comes in all forms. But no, I think overcoming that also learning who to call on how to structure a deal, all that, you know, basically in a little, little transaction. But I, I can't get over how, how much I enjoyed the notion of moving from a salary job, not salary, just an hourly payment to this 100 commission plan. It was like why didn't I do this earlier? I should, I should have done this earlier. And I think it's directly related to like going into startups and you know, working for equity. It's the same thing. Like if I get it right, there's going to be a lot of, a lot of money on the end, at

[C]

the end of it, you know, just before we move on, I, I'm just thinking about like the three of us have similar stories on the beginning, our first beginning taste of sales and I know you, you've written event. We're going to talk about the book. I'm just going to plug it here real quick. Lou's got a, a book that came out in February, I believe of 2026. It's called unlikely Entrepreneurs Wins, Losses and Crucial Lessons on Building Great Companies. So we're going to be talking about a lot about the backdrop in that, in those experiences kind of door to door. I remember I was carrying, back in the day I was carrying 80 pound typewriters for Xerox. Everybody else had like a cart. I was a former football player and I couldn't wait for the cart because there was so much politics, there was wasn't enough carts. So I carried my 80 pound typewriter down the up and down the streets of Toledo and people are slamming doors in my face and, and I actually remember that incredibly fondly. Like I remember you just saw the real raw reality of people. I heard people talking behind my back. I and I kept showing up. Is there things that the three of us like other things, like traits from that when we're thinking about what makes great sellers, maybe today when we're, we're kind of far away from those experiences, are there traits that you might just, are there any traits that you see that, that could give people an inkling that they might be pretty good at sales?

[D]

Yeah, I mean I think people don't realize how good they could be at it until they give it a try. And we were talking a little earlier until they overcome their disdain of sales and our culture sort of mispositions, misalign, you know, malign sales, you know, incorrectly because it's actually so critical. Like I think about it, I know you guys are CEOs and investors and board members. As a board member, you're still selling like if it comes down to one sales call for the company's acquisition, it's often like the board person that has to make the phone call, make the sale. So learning this skill is so critical, I think, and overcoming your disdain of it and it's, I think it just takes some experience and learning what really good sales is as opposed to what people think it is in our culture.

[C]

Johnny One of our favorites, Adam Aarons was selling knives in your, I mean this is an incredible story. Was selling knives to Judy and she called you and I mean share that story.

[E]

Came home one night, Friday night.

[D]

Yeah.

[E]

Did a week and I walk in the door and Adam Aarons, who became the CR worked for me a couple times and rose through the ranks from first inside salesperson all the way to be, you know, CRO at Okta and a couple other companies. He was selling Cutco knives at the, at the kitchen table. And I thought well, this is going to be interesting. So I grabbed the beer out of refrigerator and sat down with them and started throwing them some at first easy objections and then did more difficult objections. And the kid handled them like flawlessly. And I thought okay, this is interesting. So I said okay, I'm going to buy the knives. But hold on one second. I ran upstairs, went into my, you know, my bag and grabbed one of my business cards and handed it to Him. And I said, when you graduate college, if you want to make more money than any of your friends, you call me. I made him the first inside sales guy at ptc.

[D]

Oh, that's fantastic.

[C]

Amazing. Yeah, amazing. And now he's an operating partner at a Israeli cybersecurity venture firm, which is just really cool after his. After his exits. Really cool.

[D]

There's one thing on this topic of why it's maligned and misunderstood. I mean, there's. There's no other function in business that has a. A sign like sales does no soliciting sign. Please don't do this function where you see no marketing or no finance or no strategy. Those things are cool. Like, only don't do this. And don't even call it sales, call it soliciting, call it a euphemism for the word. But the reality is you have to overcome that and realize how important it is. And like, you're going to be using it in every facet of your career.

[C]

So when we started force management 20 some years ago, I actually studied this. Like, I felt like sales was the greatest profession on the planet and was the hardest. Like, for me, if it was so easy, you know, why do they pay people so much? And my trouble was I was having trouble connecting, like, what makes a great seller. Because when you want to move from individual contributor to like leader, if you're unconsciously competent about what makes you good, if you don't know what makes yourself good. So anyway, so I started studying a little bit and it goes back thousands of years. Lou. There's two main. There's two main things that. And we created something called the seller deficit disorder. There's two main things that a buyer of goods and services thinks about. A seller of goods and services, and we've all experienced it. Two main things, they've been surveying them for the last 50 years and. But I believe it's Egypt old. Thousands of years old. Number one, when they ask, when they survey buyers, the first thing they come back and say, do you don't understand my business? Number one is the number one reason why you have no solicitation signs. You don't understand my business. Number two, you don't listen. So those two things are thousands of years old that make up the big challenge. And we've all experienced it. You go in to buy a car, you go in to buy, and they're just not listening to you. They're not trying to understand. They're not going from an outside in versus an inside out. They're like, hey, this is on sale now you want to buy this, this is a great time to buy or what have you that I believe and over. I call that the seller deficit disorder. And you get about 30 seconds when you first interact with people, when you're In a buyer versus a, you know, a seller role, you get about 30 seconds to begin to overcome that. If not, it's over.

[D]

That's great.

[C]

So now I know like in your book you I want to talk about the pivot first so but I want to dip in here because it's related to you talk about understanding the problem so viscerally like you've turned this into the next generation of like how do you come up with great products, great companies. And you begin with this topic of the problem with the problem. The problem with the problem. Can you kind of tell us what you're. Because it's so, so relevant for sales.

[D]

John, we've been in startups that have grown really remarkably. My first one was Avid Technology. And by the way, this is a fun story because since I had been selling books door to door, when I decided I wanted to get into a startup, I cold called Bill Warner, the founder of Avid and he said, he said look at my resume like you seem like uniquely unqualified to have a successful career in tech.

[E]

Well, thanks a lot.

[D]

So I ended up getting along. He hired me as a consultant. But what Bill Warner, the founder of Avid experienced when he was trying to make changes to a video using the analog technology, film or videotape and he thought why isn't this digital? Why don't you digitize this and then cut and paste full motion video the same way we could all cut and paste words in a word processor. And it was so obvious to him. But the pain he felt through not being able to do what he wanted to do was when I say that that's a problem worth starting a company on. I've seen so many students through my years of teaching now really want to be entrepreneurs for all the right reasons. But they come up with an idea that's really not worthy of starting a company. And so you know, if you understand the pain viscerally then it's, you know, you, you have a better way to start and know what to build. Back to what you were saying John, at the top, you don't understand my business. No, I understand. This is why I'm fixing it with this solution. But if you don't have that, how do you get third party validation? You got to get back to what we were talking about, you know, Getting uncomfortable and cold calling. You got to call 100 people when I tell this to the students. Like, oh, a hundred. Like, yeah, like a hundred. Don't call your mom, don't call your friends, call 100. And I have a class, I had this class yesterday where the students are required to bring in their recorded cold calls and we all listen to them together. And of the class of like 30 students, I only had like three or four actually do it in the week. Like a lot of them just don't do it. It's hard. And so getting over, overcoming that fear because if you don't do that, you're gonna, you can really waste a lot of time in your career on a company that really has no right to exist.

[E]

And so you have to get comfort. I love that saying. You have to get comfortable being uncomfortable.

[D]

Yeah, yep, exactly.

[E]

And in that process, you know, you learn not only about other people, but you learn a lot about yourself.

[D]

Absolutely.

[E]

You're forced to look into the mirror after every sales call, whether it goes good or bad.

[C]

You.

[E]

I've always found, like, because, Lou, I've had those days in the beginning of some startups where I make 100 phone calls in a day and I don't get any meetings, didn't get any demos. You come in the next day and you're thinking, man, if I have another day like this, this may not be the right profession for me. And then you make three or four calls and all of a sudden you get three or four meetings and you're like, wow, yeah, maybe this actually work, you know, but you learn because it's. Because you're reflecting and you're learning a lot about those conversations you had. And more than just the people, you're learning a lot about yourself.

[D]

Well, it's interesting you say that, John, because when I was selling bookstore to door, I had a couple of guys from other schools I was doing it with when I was out in Illinois and we, I had a couple days where I worked 12 hours and didn't make a sale.

[E]

Right.

[D]

And we'd call, we called those character building days. That work will pay off the next day. Just like you're saying 100 calls and then four. Damn. Like, you just don't know the relationship. You just have to keep working at it to get, to get to the success.

[C]

And we're onto something here that I think is so critical for if you're a leader, if you're a seller, if you're going to join a company, this topic of the problem with the problem and we'll talk about how to investigate that. But for me, when I. The most successful times I've had in my life is when I am emotionally connected to solving the problem. What I do matters. Like if I'm selling those books and I believe that what I do matters or if I just think I'm selling books. And I was lucky. Like, I worked for some two great companies. I worked for Xerox, which helped me understand problems, but it was a highly competitive marketplace. And then I went to PTC and they really focused on the problem. Like wait, you don't understand, John. Like this little bidirectional associativity that they have. Let me teach you. Because I wasn't an engineer, I didn't understand design through manufacturing. Let me teach you the pain that's actually associated with that. And then what they did was they made me go sit with engineers that, that in companies. And I would say stuff like, because I was intellectually curious, because Xerox taught me how to ask discovery questions. I'm like, I don't get what the big deal. It looks like Microsoft Global find and replace. And they're like, that's exactly what it is. I'm like, well, why is that a big deal? And then they start to show me all the scrap. They start to show me the product launches that are delayed. They start to show me the downstream implications. So can you help us get in the mindset of how do you help a company find the problem with the problem? And I know your chapter is a little bit different than that. It's first like understanding the problem, but the emotional connection to it is I think once you get that man, you can get people to wake up at O Dark 30 and slay dragons if they believe what they do matters.

[D]

Yeah, yeah, yeah. No, it's really interesting. So in that chapter I talked about Bill Warner. The other. The first time I became CEO was a company called Reflectance Software. And I had done a few startups. John and I worked together for a brief period. We'd sold this company Webline and I wanted to be a CEO. So I went and spent some time at a VC and I was just screening deals and I found this founder and he's a really sort of hard scrabble, tough guy from New York, really good developer. He had worked on the trading floor and he supported internally developed applications for First Boston. And when the applications that the developers didn't work, they developed didn't work, he was on the trading floor. There's like real time, like big money on each trade, he'd have phones or staplers thrown at him. Like, he's going, this thing just doesn't like. And they were screaming at him. So he's like, there's a real problem here. So he developed a software that could basically understand the user's experience with the application before the user did. Like, what are the. What are the early signs that you're going to have a performance problem? But that was, again, like. And I went down, before I joined that company as CEO, I had a software, I had a laptop set up with the product, and I went out and demoed it to, you know, like a Half a dozen CIOs of Wall street to see if the dogs eat the dog food. You know, it was his problem. But then you've got to figure out, is it just one isolated problem or does this start to fit across other use cases? And I found out of those six calls, I got three pilots. And I'm like, all right, I'll join the company. But I think that's. That's you. You have to. As you're joining a company or whatever, you have to realize you're going to be on the front line. You're the chief salesperson. As a CEO, you have to be able to do it, because you can't just delegate this. You got to know it. And then you got to. Just as you were saying, the cost of that problem that PTC solved was, like, visceral. And of course, you wouldn't know it as not an engineer, but you got, as you said, you got to be intellectually curious to figure out why. Why are there. What's the cost of this, this problem?

[C]

And when customers get emotionally connected to solving the problem, the sale is so much easier. So if I could give anybody any advice, we're on a topic. So great. What is the biggest problem you're solving and why does it matter? And when you can get so, so many people like, wow, I'm going there because John McMahon is the CEO there. Not nothing against Johnny. If you did that the five times he was CRO, you would have made a crap ton of money. That's not my point. But, you know, when you're making decisions, there's so many, so many McMahons and Shipley's out there. When you're making decisions about where you're going to go, if you're not emotionally connected to what that thing does and how it does it, how it does it differently and why it exists, this, then how in the world are you going to sell it?

[D]

Yeah, yeah, yeah. No, I think the term you used about intellectual curiosity is like the key thing because oftentimes I found with all six of my startups, customers did things with the products I had no idea they were going to do. Like when you really sat down and interviewed, like, holy cow, they're using this for. I got to tell you this one, this one story. This is early days of Avid. I, I started selling in Japan because first I was a consultant and they said, hey, can you sell down south? We didn't have a rep and I started selling. Then I boss came to me, this is great. He goes, well, we have someone running North America, we have someone running Europe. Can you run the rest of the world? That was my title, Rest of world. Okay. So the biggest market was Japan. So we went over there, we started selling in Japan, doing well, and they got this one big order, like three avids, which is like 300 grand for a karaoke company. And they asked for a couple of features and they offered to buy 10 more, which would have been the biggest, biggest order in the company's history. I'm like, well, what do they, what do they want to do with that? And so I couldn't figure it out. So finally I went with my sales rep who kind of like John's story about the knife salesman. Our top rep in Japan had been a car salesman, great guy, Yoshio Takahashi, terrific guy. I worked with him again in a heartbeat. Anyway, I said, takashan, you got to take me to a karaoke bar. And I went with a legal pad and a pen and we, we drank beer and watched karaoke. And I finally figured out what features this customer wanted to put into the Avid. We put them in and we got the biggest order in the company. So just whatever it takes. It just takes digging in and trying to understand what your customer is trying to solve.

[E]

Yeah, but, and to that point, Lou, because you touched on it just a little bit earlier, is, you know, when the CEO of a founder, you know, founder led type company, you have to actually be. And I find the same thing with CRO. The CRO thinks that they're only a salesperson when they join a raw startup. But at the end of the day, they're. They're mostly product management. They're trying to dig in, like you said, into what are the use cases that this product can go into, what are the pains in those use cases, and how does our product fit or not fit into those different use cases. And then as the company becomes bigger and you win, you know, 2030 customers and you start to move a little bit more out of product management and more into being a, being a real CRO or CEO.

[D]

Yeah, no, that's exact exactly right. I mean the, my experience, my third time as CEO is with at Black Duck, which had been well known for open source license compliance. But when I first got there, my first, first couple of weeks, I said I got to go out and talk to customers. And we got a call from JP Morgan and this is the time just 10 years ago, Jamie, JP Jamie Dimon was asking his, his staff to curate a hand, hand curated list of open source security vulnerabilities in all their 10,000 applications. It was going up daily. And so I started just asking the question, like, why are you using this? Because they weren't looking for license compliance, it was about security. So to your point, John, like, I was like, that's way bigger than license compliance. So we completely repositioned the company around open source security, which is a much bigger market, faster growth, sea level issue. But it all came from meeting with a customer and understanding what they're trying to do. And I was like, I went back and told the people we're going to change. And you know, a lot of people didn't want to change, but that's where we had to go because that's where the market was going. So I think to your point, you have to sort of see where markets are going and be willing to make changes on that.

[C]

So. So Lou, let's dive into the book a little bit. Yeah, I'll give it, give the name again, Go out and get this. It's a fantastic read. There's some interesting things and I want to spar with you a little bit on a couple of them because when tech founders get involved, the sales thing seems to be a bigger divide. But the book is called Unlikely Entrepreneurs Wins, Losses and Crucial Lessons on Building Great Companies by Lou Shipley. I'm assuming we can get it everywhere. We can get at Amazon, we can get it everywhere.

[D]

Barnes and Noble. Yeah, actually I co authored it with a woman named Trish Favreau from mit, who I used to work with. So she, she helped me with it and we did it together.

[C]

So why did you write the book? And then let's dig into some of these principles because you got some pretty cool frameworks.

[D]

Yeah, so actually it was originally her idea. I was teaching, actually I was teaching the sales class at MIT before I was at Harvard and I worked with her on a few articles and she called me one day and said, I think there's an idea for an unlikely entrepreneur, a book on this because my dad could have, I thought my dad should have been an entrepreneur. He was smart enough, he had great ideas, but he just didn't have. You just have the confidence to give it a try. And so do you know people like that? Like, yeah, I've spent my entire career with entrepreneurs, some more unlikely than others. One of the guys we talk about, which I love talking, the most unlikeliest entrepreneurs is Scott Ginsburg who sells caskets online. Titan Casket, which is like, who would have thunk you could sell a casket online? He sells like a $15 million high growth business now. It's just terrific. So I wanted to tell these stories for a couple of reasons. One is they're unlikely, but they're, they're not about like what you hear, you know, billionaires doing AI. It's not that there's anything wrong with that. It's just more it might be someone who lives around the corner from you that's running a business. And like there's a woman who runs a tire store who's just, just so badass. I love this lady, Massachusetts, she's just great. But there's some great people. I wanted to tell the stories and maybe inspire other people to say I can do this, you know, and then also weave in lessons of wins. We talk about wins, but also losses. I'm involved with a lot of companies that failed and I've, I've got the, you know, I, I've invested in companies that went to zero, like big write offs. And it's like, what do we do wrong here? To John, John Man's point, like, what, what are you learning? Like, what did you do wrong? How do you look in the mirror and say, what did I do wrong on this company? Because everything seemed right and then it's a massive write off. So I wanted to sort of think what, what did people do well and what could they do better? And then maybe inspire people to, to start some, some new businesses.

[C]

And in your book you talk about these three stages of founder led sales. And here's where I started to go. I got to talk to Lou about this. I want to spar a little bit because you have a heavy, heavy point of view that the, that the founder needs to be an integral part of sales. And I'm wondering. And a lot of the, the, and I love how you set it up. The unlikely founders, like anybody can be a founder. You, you do the, the difference between a, you know, a Silicon Valley 22 year old something versus a 44 year old something. I want to talk a little bit about this. If I interject technical, like software sales does, do the principles still hold up for you? First talk about the sales of like, you know, excuse me, the principles of sales and why founders have to be completely the first sellers and that kind of stuff. Tell me that first and then is there differences with technical founders?

[D]

John was, John McMahon had said before how hard sales is. And I think there's this notion that, still a notion today that if you build the best product, you know, the world will be the path to your door, the product will sell 100%. And so that's a total bullshit. Like, in fact, we have John, John McNeil coming into our class to teach this, We've a Tesla class at HBS about how he taught Elon Musk what a sales funnel was, you know, after Musk had predicted Wall street what his profit was going to be like. So there's still this notion if I build this great product. And technical founders, I love them, but they often think sales is just for dummies. Like what do we need these people for? That's just sales. The reality is where I got this point, point of view is I work with so many technical founders that delegated the sales function before they understood it themselves. Understand, all right, typical sale, it's going to take five steps, seven steps, 10 steps. They just say, I'm going to hire this great guy and let him figure it out. Well, I think that's a big mistake because you don't understand how to train that person. And then they bring in a lot of things from their other companies that may or may not be relevant to what your, your specific product is. So I've seen that. The other thing just to go back on this mindset piece is I think for an engineer to like really dig in to understand how a salesperson's mind works is just as important as what you were saying about the intellectual curiosity for a salesperson to understand how technology works, how an engineer's mind works. So you need both of them to have the great company. But oftentimes I think there's one that overshadows the other.

[E]

Yeah. What I think happens a lot of times, Lou, that I've seen is when it's a tech founder, they spend so much time building the product and they believe that everyone is going to buy their baby. And I tell them, yes, at some point everyone's going to buy your baby. But right now you have a certain amount of money and you don't want to. You want to use that money judiciously. So what we need to do is build the ICP and try to figure out which customers at this point and the capabilities of your product are going to deliver the most amount of value to those customers. And a lot of times they just don't listen. So they're going to like everybody from JP Morgan Chase down to some small startup firm and they're trying to sell a product in all those different avenues. They get burned, they burn the money and then they have a really hard time getting another round of funding. And it's all because they didn't focus. They think everybody's going to buy my baby. And, and a lot of times, to your point, they don't really like sales reps. Yeah. Don't want to pay them. They hate the fact that sales reps make more money than some of the developers and it drives crazy.

[D]

Right.

[E]

You know, they have to change that mindset.

[D]

Yeah. I mean, no one wants to be told their baby is ugly, but sometimes it's the truth, Right?

[E]

Well, the baby doesn't have to be ugly, but the baby's just not a great fit for, let's say JP Morgan Chase. When you come out of the gate. It could be a much better fit for some other organization.

[C]

The baby's still in the womb. Most of the time what I find is the baby's still in the womb. And here's why. With technical founders and Lou, you talk about in the book, I love it when you talk about, hey, having experience like the 22 year old that comes right out of college, develops the thing and you know, and doesn't have experience of working in an environment. Like the best technical founders that I've seen are the ones that were working to solve the problem. And the he couldn't get the he or she could not get the attention of the company that they were supporting, like Kodak, Xerox, all these big historical companies, Geisberg, Johnny, back at PTC days, all these incredible billionaire founders that turned into incredible products. They were sitting in an environment, visceral understanding of the problem. But here's the next generation of it. Just because you have a visceral understanding of the problem, you typically, if you have that kind of mind, you typically, that's a rare breed where you have the ability to articulate that problem in a way that gets somebody else to get emotionally connected and excited about fixing it. And here's where the technical founders go wrong. They're like, why the hell can a seller from IBM or from Oracle or whatever. Why the. With all that fricking training, why the hell can't these people come in and sell stuff? And then what they start to do, Louis, they're like, okay, I need people with only this type of background. And they're trying to find these rare birds that are so technically oriented and with the hope that they can be sellers. And it fails miserably. But the most successful founders are the ones that, like, I have to figure out how to get what's in my head into the hearts and minds of others around me so it can scale. And that's, you know, I think that's why you guys have been so successful. Johnny. And we started a company doing it 20 years ago. It's getting that information in, that visceral understanding of the problem into a scalable model. And the technical founder comes to the realization that says, or any founder, I can't scale this on my own. I need experts. Have somebody coming in and bringing an old playbook to your problem is dangerous.

[D]

It's very dangerous.

[C]

And you talk about it in the book.

[D]

Yeah, I mean, in the book, I talk about the flailing founder. And I've seen this so many times where you're really good when it's the early days, you're in the middle of everything. But as you realize, as you get old, as the company matures, your job is to abstract yourself and be a great team builder of all the different things, functions. So I don't. I don't know if you guys are. Are hockey guys, but the guy I talk about this leadership chapter is a guy named Mark Fusco, who is the Hobie Baker winner in 83, is a friend of mine, and he talks about hockey is the perfect training ground for being a CEO, because you have to know where the puck is at all times and know what you're going to do with it when you get it. It's like being a CRO or being a CEO. You have to understand where things are going and. And you can tell when a founder is starting to flail because they. They try to use the things that worked in the past as opposed to realizing they got to get out of the middle of everything and then become a CEO and hire a team.

[E]

Yeah. Hey, I want to switch gears a little bit. In the book, you talk about the Murder board.

[D]

Yeah, yeah, yeah.

[E]

Where you basically, you know, have these ideas and you think, you know, I got. I can. I can generate a new company and I can. Then I can, you know, I can get some money. But you Put it, you put your idea in front of a murder board to basically shut your, shut your product or your idea down and actually learn from, from it. Can you talk a little bit about that?

[D]

Yeah, no, I, I, I have a couple friends that have been in the army and spent time in Afghanistan and Iraq and talked about how they plan their missions and, and then, you know, come up with a plan and then you just, you just sort of break it down by, this is going to go wrong, this is going to go wrong. Which is exactly the same thing that happens when you're doing a product launch or launching a new company. So I think trying to institutionalize that, whether it's in a product group setting or I used to do it as a CEO, we have an off site once a year and say, all right, if you were a startup and you got 50 million bucks from a Silicon Valley CEO or VC, how would you kill our company? Like, what would you do? And then just really dig in. And what you're trying to do is expose your weaknesses so that because no one wants to recognize you have or say, your baby's ugly. But every company has their weaknesses, and it's only by being really honest with it about it that you can get that you, you get better. The analogy I use, I'll go back to Black Duck was I thought it had a culture of optics, which was this notion of, you know, everything's, make everything sound better than it actually is. But how do you get better if you're making it sound better than it actually is? So if I were looking in a circus mirror, you guys are looking at me right now. If I look in a circus mirror, I could say I'm six five and blonde and ripped, but you're looking at me.

[E]

Love those circus mirrors.

[D]

So don't look in the circus mirror. Look in the mirror and figure out what you got to do better. And that's sort of the whole idea behind the murder board of you. We're going to be wrong in some respect. And then how do we, how do we think about fixing it?

[E]

Yeah, but don't you think that's even a good idea for somebody who just thinks they're getting ready to get in front of a bunch of VCs?

[D]

Absolutely. Absolutely. Yeah. I always found when I was fundraising, like my seventh or eighth, eighth pitch was my best one. Because you screwed up in your early ones. I did this all the wrong way because I went to my, my first time raising money. I went to my number one VC candidate and did it for the first time and it was a total disaster. So I just learned, yeah, you've got to, you got to go through and practice to get better and realize what's working and what isn't. And the tough questions, how are you going to handle them? What's a good way to handle them? What's a bad way to handle them? It's also interesting, John, you're an independent board member. Like I find that that role as an independent board member was what was so helpful to me as a CEO. Someone to say, you know, Lou, you're kind of screwing up here. No one's telling you this, but you really are screwing this up. And I ended up getting fired as a CEO without really reading that and understanding I wasn't doing as well as I thought I was. And so that's a, you know, that's, that's a, you know, continuous learning thing. I think of like what, what do you learn from your failures? So that's why if you use a murder board, you realize you're going to fail. How do we get out ahead of it and build this culture of continuous improvement?

[E]

Yeah, this point have people shoot you down right now where it doesn't cost you anything to get shot down.

[D]

Yeah.

[C]

Let's talk about this point because my experience, my brother and I were playing golf the other day and we're walking down the golf course and we're talking about people that had these surefire talked about this one guy that went to Ohio State to play golf. His, his roommate was John Cook. He was from a high school and he used to, you know, play golf on his knees and play against the top guys in the state in Michigan and play golf on his knees with two clubs and beat everybody and he never made it. And I talked about a friend that I had that, you know, went to Stanford and had, you know, wanted to go to Stanford and went to Stanford and realized that there were a lot of people like him. And he actually had a really, really difficult time. He wasn't used to not being the smartest person. And so I want to hit on this self awareness and I want to hit on this for the listeners that we have right now that are like these AI companies and whatever it is, whatever the leading edge technology is when you're going to pick a company, the authenticity of a leader. I don't care if they're, there's no excuses. The excuse department's closed if you're not self aware. So when you ask about problems and challenges, there's a way to do that. It's like, hey, what do you love most about your product? What causes you pause? Is the greatest way to ask a technical founder about what's going on. But if they don't talk about any of the pauses and everything's great, they're not self aware and they're something bad's around the corner. It's just the ones that I find. And Johnny, you gave me this feedback when we started the company years ago. You're like, you can lead a horse to water, but if they don't like participate in their own rescue, like if they don't believe they have a problem around, go to market, you're going to have a tough time convincing them they have a problem around go to market. Luke, can you and Johnny, can you very specifically talk to sellers that are listening to this and going, I'm loving this podcast. What can I do with this? When I start to look at companies and start to interview and what things would I start to see in the companies that would be advantages and what would be red flags?

[D]

This is so interesting. I write about this in a chapter because one of the things I found being a good independent board member is the closest thing to being a CEO when you really feel like your work is helping build the enterprise value of the company. And the hardest thing is to interview for coachability. So I stopped interviewing for coachability. So the only way I'm going to find out if someone's coachable is I got to work with them for a year to see if they're actually coachable. And I found I wasn't as coachable in my early years as a CEO as I got to be later on when I realized we all have to be coachable. So if you're looking at a company and you can see a CEO that doesn't seem like they're at all interested in being coachable, I'd run away as fast as you can. I don't care how good the technology is, you're going to fail. And you have to have a culture of this continuous improvement comes from being coachful to realize, you know, maybe I was wrong on that thing there, maybe I was wrong here. And you are wrong all the time. And so we One of the guys I interviewed is a guy named Will Keller who's a friend of mine who runs a coaching business. And he has a coachability index, a quiz that he uses as he decides who to to work with and coach. And I think it's just really important to think about that because we all have been on teams or been around mentors or realized there's such value in coaching and if you don't think someone else can make you better or you can't get better, then that's, that's a real, that's a real danger sign.

[C]

Yeah, Johnny, you've talked about that a bunch before and you extend that into. Because I understand the relationship of an independent board member. Let's go down to the role of like a top seller that's looking to make a move and might not have that kind of visibility or viewpoint into that person in board meetings and that kind of stuff. But it's this, Johnny, it's this extension between coachability and I think, what do you do? You call it adaptability? You call it, what do you call it?

[E]

Adaptability. Yeah, coachability. A lot of people are coachable and you can coach them three or four times and then you find out that they don't change. So they don't take that hard look in the mirror and then adapt to the changing environment around them. You know, it starts startups, the product's always changing, the market's changing, your customers are getting Sparta, the competition's changing, your messaging needs to change. And if you're not changing and adapting all the time, you're going to get left behind. You're going to be a dinosaur in a fast growing startup. But, but going back originally, you know, if I'm looking at a company, I mean, it's as simple as asking the three whys, you know, why does the customer have to buy? Why do they have to buy? No, why do they have to buy from you? And the big one, why do they have to do it now? Why can't they do a workaround?

[D]

Right?

[E]

And if they can't answer those three questions, and I usually disguise those three questions, but if they can't answer those three questions, I'm checking my watch and I'm out the door. I don't even really care about whether or not the CEO is that coachable or anything. But then you want to know, okay, so if that's the case, so tell me what your real secret sauce is in there. You know the, you know why they have to buy from you. Now tell me why that's defensible. How are you going to defend that? You know, are you going to. And if they say it's not defensible, somebody could do the same thing tomorrow.

[D]

Wow.

[E]

Okay, so now it becomes, now it definitely becomes more about the CEO and how do they approach the sales process and how do what type of company they're trying to build. And it always also worries me when somebody says, yeah, and what I'm going to do is I'm going to sell this company. Well, I don't want to be part of a company where they think from the start they're going to sell it. Yeah, that means you're taking shortcuts. You're not really doing things the right way. That, that just, that just smells to me.

[C]

This is so relevant for our listeners right now that are like sellers, sales leaders that are looking at companies. They're looking maybe to move maybe into a new space. For me, I just like to give this advice in the startup companies, if you're not getting access to the CEO, I wouldn't join a company, a startup company without getting access to the interview in a startup company, full stop. And I would think that if I was a CEO and a seller was asking to speak with me, that would mean something to me, if it was beneath me and that would tell me everything I needed to know. Now, when I'm there along this, I want to give some very concrete advice is I would ask about they're thinking and you can't. Are you coachable, are you adaptable or whatever. It's hard because it's just like sales. You get the art of the question. Tell me, give me some examples where you feel like you've been right on it from a market perspective and you get validation and you're thinking that you're doing exactly what the customer needs you to do. And then could you please give me some examples of where you found that you had to pivot or where you were missing the mark and what did you do about it? Walk me through how the organization adapted and pivoted. And I think, man, first of all, if I had a seller asking me that question, I would be, I would love the curiosity of that question. And secondly, I'd really have to stop and think about my answer because at Force Management, I can give you a bunch of examples of where we thought we were killing it and we thought we didn't need to pivot. We. Or then when we need to pivot, the gyrations that we had to go through to match our processes to customers. So give me your thoughts on that, Lou.

[D]

Yeah, I mean, it's what's relevant to both. What you both said there. If you're thinking as a salesperson analyzing a company, there's another good book, not mine or anybody else, that it's called Competing against Luck, which talks about a theory called the jobs to be done Theory and it's basically every job that needs to be done has substitutes it. And so a lot of, a lot of early stage companies think that the only way to solve a problem is the way they're thinking and doing it. This unique and differentiated. But, but the reality is whatever job is to be done could be being done in a way that's very low tech or that sort of thing. So I recommend thinking about that as like what really, you know, not just the use case that's important but like what's the job, the product's doing, how's it done and if they didn't choose you, how would they get by without it? Because you may not, they may not have the top problem. It may be if it's problem number four or five, I'll just use the old way and spend my money on something that's solving a more higher urgency thing. Something that if I don't fix this, I'm going to get fired.

[C]

Johnny, is that related to your propensity to buy that you always talk about in the sales process or the icp?

[E]

Well, yeah, so most I go through like a three step process in building the icp. I build an ICP customers that I think can buy, then I cut it by who has the highest propensity to buy. And there's different factors based upon your product that can, you know, tell you whether or not some companies or people or Personas have a certain propensity to buy. And then especially in startups, I like to then cut it by sales complexity. So if I'm a small company and I'm just getting started and yes, originally JP Morgan Chase and Morgan Stanley showed up on the top of my icp. But then when I said high propensity to buy, maybe two of them stayed in there. But then when I get to sales complexity, whether it's in serve or you know, insurance or the government, those guys are getting cut off the list because I, I don't have enough time right now to spend 120 days negotiating a contract. And I'm not so sure that I actually want the business because then I got a tiger by the tail.

[D]

Really good.

[E]

Those three ways really helps you to narrow down the focus on, on where you're going to spend your time, where you're going to spend your resources as a startup in sales, in marketing and in development and point all your arrows in one spot.

[C]

That seems like something that could show up on the murder board.

[E]

Lou?

[C]

Yeah, and I know, I saw you're going to make a comment real Quick. And I'll just the. Some of these technical founders that are in the J.P. morgan, that's where they started in the IT organizations maybe. And they couldn't get J.P. morgan Chase to fix the problem. They saw it as a huge problem, but they couldn't fix it while they were there. Then they start a company and they go after the JP Morgan chases. I mean, sometimes it works and a lot of times there's still no propensity to buy to solve that problem.

[D]

Yeah. No, I just like the way John laid out the icp, propensity to buy and sales complexity, all three together. Because they are very different and distinct. And definitely if you, if you get each of those, then your likelihood of success is much higher.

[E]

Yeah, man. When I first went to Blade Logic, I sat down with the executive team and I said, hey, let's talk about the different use cases and make a long story short, they listed 13 use cases on the whiteboard. And I said, well then I need to quit. And they said, what are you talking about? And I said, I can't build a salesforce that's world class. And selling to 13 use cases. I looked at the development guy and said, I'm sure you can't build a product that's world class in 13 use cases. The same in marketing. So let's narrow that thing down to three or four. And now if somebody wants to come and that's where we'll point all our arrows. Now if someone wants to come in and buy, use case number nine. Okay. But I'm not out there hunting into use case number nine, outlier. Qualify them really quickly. And if it's going to be a long sales journey, forget about it. I'll go, I'll stick with my top three or four.

[D]

So but John, this is so interesting because it's in some ways for an entrepreneur or early stage salesforce, it's counterintuitive. You're. You're sort of bred to believe I need a huge TAM. I need a, I need a. 10 use cases better than one. But what you're saying is so interesting. I actually just did a case on this last week with a guy who, who joined a company, a CEO, a company at 20 years old and got to 8 million. 20 years. 8 million. That kind of sucks, right? So he joined and it was 30 million in three years. How did he do it? And it was exactly what you're saying on a different scale, but focused down on fewer ICPs. They went from like 30 to 4 and then grew faster. And it's like, all right, now you're really getting to this point of, is this really a problem? I'm willing to pay for you're propensity to buy.

[E]

Hey, it's the old Jesse James, you know, why do you rob banks? Because that's where the money is. That's where I'm going now. I could rob hospitals, I could rob railroads. I could do all that type of stuff, but there's just not as much of a higher return on my investment. And that's the thing that a lot of entrepreneurs leave out is I only have a certain amount of money, and it's all about the productivity of my salesforce and the value that my customers are going to receive. Because if they receive a really high quantifiable value, I'll be able to extract more value from them. They'll stay with me longer, and I can continue to upsell them.

[C]

Yeah, I think this conversation for the seller sitting in the car, on the track, walking the dog or whatever, this is so powerful for me. Just thinking about our audience is that if you're interested in a company and they're explaining the company with the, like, rainbows of opportunities and how the product can just do everything, and they're not focused on use cases, and they're not focused. Johnny. I think about, like, I was kind of unimpressed when I first interviewed with ptc. I'm coming from Xerox. I've got so many products to sell, and I go to PTC and they're like, this is the problem that we solve. Like, this is the use case, and this is how we solve it. And we solve it so well that we're, you know, we're going from zero to a billion in less than 10 years in perpetual software licenses, a faster growth rate than Microsoft. Like, I almost couldn't comprehend it at first. It was like, it was so simple. But the beauty for me was it was so regimented and so processed that the repeatability, the scale was phenomenal.

[E]

What we did is we then knew it so well. We dragged the customer through that pain. It's almost pain to crawl through a bunch of, like, a floor full of glass. And, yeah, all their pain. Like, come on, Mr. Customer, let me remind you about how you do all these types of things. And by the time we dragged them through all that glass, they were like,

[C]

yeah, okay, but Johnny's been a little facetious. Lube. Like, what they did, what we did so well was, okay, we know the problems there and we know that we're. We have a Visceral understanding of the problem. They had to teach me that I was coming from hardware, I never sold software before. So they had a mechanism to teach me and get me emotionally connected to the pain of the buyer. And it's just, it's coming out again. And this, like, it really kind of all begins. And that's a big theme of your book. Book, you know, it all begins with the problem. And Johnny, you know, extends it to the propensity to want to fix that problem. You talk about, Lou, the number of alternatives, the types of jobs that are going to fix that problem. It really starts with that, that understanding of the problem.

[D]

Yeah.

[E]

You also talk about in 2026, the differentiator you say is. Is a superior sales system more than. More than a product moat. Can you talk a little bit about that?

[D]

Yeah. I mean, I still think there is. In the same way as we began this conversation, there is this disdain for sales, misunderstanding of sales and what really good sales is. Like, you guys just described it perfectly from ptc. I still think there's this, this notion that, you know, a great product company can be a great company without a great sales team. And I just think that's wrong. I think the best companies have great products and a great sales organization and a, and a, A meaningful sales culture. This is another thing we talked about in the book is like, what kind of sales culture do you want to have? And companies have cultures, whether they're written on the wall in a, you know, mission statement or not, but they have. But I think having what kind of sales culture you have is really critical too, for, for how you want to be, how you want to run the place, you know, performance based.

[E]

And the way to think about that, Lou, the way I've always thought about is if I switch the products with my competition, could I still outsell them?

[D]

Interesting. That's a great way to. And I think yes, I think culture.

[E]

And if the answer is no, then you got a problem with your salesforce.

[D]

Right.

[C]

That comes from bear Brian, originally in Alabama.

[E]

Let's say you know your product and you know that the competition has an inferior product. But if I switched products, can my sales team still outsell them? And there's plenty of examples in this world and in history where the inferior product won simply because the sales team

[D]

was so much better. Yeah.

[C]

So this is a red flag for me right here. If you go in and Lou, I want you to expand upon what you really mean by sales culture. But if sales is not the tip of the arrow, it's not the tip of the arrow. And everybody is aligned behind the tip of the arrow. Those cultures, for me, they don't scale, they don't work. You could have the greatest product in the world and sales is a second class citizen. Okay, maybe they're not doing this, maybe they're not doing that. Like the company owns that. It's not like those sellers suck. The company owns that. And I see it so much when I walk into companies doing what I'm doing for the last 20 years, when sales isn't even the most important thing in the company. Like it's not even in the top five. Like, I can't help them. I can't help them. They're like, you know, cause I can't make their product better. I can help their sales organization. Talk a little bit more about what you mean by culture.

[D]

Well, I just got to tell you this one story because a couple weeks ago I was up in New Hampshire and I went to church and neighbor is John Morgridge, the founder of Cisco. Right? Like Cisco, obviously, great company. And he didn't know who I was and didn't know some people. And he was introducing himself and someone said, john, what do you do? And he's like 92 now. So he's like, I'm a sales guy. That's the founder of Cisco. Describes himself as a sales guy. To me, that tells you everything. Like if the founder of a company that's that famous said that that's what his job was, to build routers and sell routers. Like, that's. I just thought that was so cool. This guy's given away more money than you can imagine. And he still just describes himself as a sales guy, which is. I think he's really proud of that. And anybody on this call, you should just be really proud that you're in this profession because it's such a great profession. And to think about somebody like that that just says, yeah, I'm a sales guy. I didn't say I founded Cisco. No, I'm a sales guy.

[C]

Can we talk a little bit about. Great story. Can we talk a little bit about what you're seeing? You've done sales with Robert's, you're doing that at Harvard, you've done it at mit. You're like, you're a student of the game and you're helping us all be students of the game. What are you seeing right now? Speak to our audience to up your game in the sales world. What are you seeing are some of the biggest things and how are you approaching that? And then also, if you wouldn't mind, give us a little flavor on what you think AI is going to do to our profession.

[D]

Yeah, yeah. So when I've been teaching, a lot of what's happened is the people coming out of these schools today are just a lot more entrepreneurial and they understand. Like back in the day when I went to Harvard Business School, it was like you went to be public company CEO. Now so many people want to start companies. They've seen what this is something. Our country is so good. We live in the most dynamic economy in the world. So the most complex economy. You got to be good in this economy. Right. But you're lucky to be here in the most competitive economy in the world because the opportunities are so great. I mean, imagine if you live in some other country that didn't have everything we have. And so I think mastering sales is the key thing because like John did or John McMahon did and I did, multiple different industries that we had to just learn and figure out, all with kind of a sales bent to it as it relates to AI. I still am seeing. This is why I kind of wrote that chapter about the problem of the problem. I'm still seeing people with like technology in search of a solution. And yes, I know the basic AI tools are really great. I do see some companies that are automating the stuff that salespeople naturally don't like to do. And I like those kinds of companies. And I see a lot of improvement in terms of helping with icp, using AI modeling to. To help with this and automate a lot of this stuff that we used to have to do manually. But I kind of view this whole tech. Tech stacks change as the stuff we went through in our entire career. Like when I graduated college, the IBM PC was out. There's no Internet, there's no Microsoft. No, there was Microsoft. There's no Google, there's no Amazon, there's no Facebook. Think about the changes. And the changes that are going to be going forward are even bigger. So you have to be on your game. You have to be. I think John's word adaptable is actually better than coachable to. Because, you know, we're in this dynamic economy. You just have to. You have to dig in and learn and get uncomfortable again and again and again as you, as you continue to relearn your trade.

[C]

I like that the advice I'm giving people is the more things change, the more they stay the same. And what I mean by that, as you come down to like your. I think one of the Favorite chapters in your book for me is the. The around the problem and the problem. I think that the, the more you attach yourself to the actual pain. Now, what I think is interesting about AI is the way that the problem gets solved, how fast it gets solved, how, how many steps are, you know, the productivity and efficiency behind it, I think are really, really powerful. So now more than ever, I think the way that you're solving the problem, so if you're on the problem and the way that you're solving the problem and the complexity, the speed, the connectivity of the data, that is an interesting time to be alive. I think it's the greatest time to be alive in the history of our world. But for me, it begins with the problem. With the problem. If that's not there, it doesn't matter.

[D]

So it's interesting you say, because my co author and I went back and forth. We spent about three months debating what we were going to call the book because we could have. We almost called it the Problem of the Problem because to me, it's like the whole thing. But we wanted it to be marketed to entrepreneurs. I just got to tell you this one story. You're going to, you're going to love this. So I, you know, put together like, this is a startup. Like, it's the first time I wrote a book. You know, I put together my target market. I thought it'd be VCS, founders, PE shops. My first big order was from one 8Y old company, HP Hood, you know, the milk maker. Okay, what the hell is. What are these guys doing? So I talked to the CEO and he's like, oh, no, we would never survive 180 years if we weren't entrepreneurial. They Hood now is the number two producer of milk in the country, but they sell it as an OEM at a Walmart. So they're not, you know, they change their business model. Their top three products are lactate, Almond breeze and oat milk. So, you know, there's. There's 33 million companies in our country. There's a thousand that are over 100 years old. So everybody needs to take these entrepreneurial lessons to heart, because to survive in this country, it's brutal. We're so good at creating new companies because companies are continuously disrupting the status quo. So actually we almost called it that, John, but we ended up calling it unlikely entrepreneurs. We thought that would be a little catchier.

[E]

That's a great story. And the fact that you said that there's 33,000 companies in America and only 1,000 are over 100 years old.

[D]

33. 33 million. If you take so 33 million all the way up to, you know, IBM or Bank of. And only a thousand of them could make it over 180. 100 years. And these guys made it 180 and they're the ones buying the book. I just thought that was so cool, you know what I mean? Because it's like, it just goes to show you how hard it is to survive. You know, we're talking mostly today about startups, but it's still hard to make it from year 70 to 80. Like, look at Cisco now. Like, John, you and I were there when it was like the most valuable company in the world. Now it's like, you know, it's good company, but it's not like a world beater anymore.

[C]

Such a great tie in to the, to the book. Lou Shipley's book. Unlikely Entrepreneurs, Wins, Losses and Crucial Lessons on building great companies. No matter where you are, if you're a startup, if you're. I love. The point is that if you don't have the entrepreneurial spirit, you're going to be at risk no matter where you are, whether you're starting up or whether you're inside a company trying to make a pivot, you got to learn that entrepreneurial spirit. And there were so many great lessons in there. Great job on the book. Go get the book. Lou. Thanks for coming on. Amazing, you guys.

[D]

This is great. It's nice to see you again or to meet you, John. But John, man, it's nice to see you. Where do you live now? Are you. Where, where are you?

[E]

Which John?

[D]

John McMahon? Yeah. Are you Master?

[E]

I'm living in Florida and in Rhode Island.

[D]

Okay. Okay. How about John Cattle? Because I'd love to get together, have a beer with you guys.

[C]

I'm in. I'm in. I'm in Charlotte, North Carolina, and Marco island, just about 30 minutes south of Johnny in Florida.

[D]

Nice.

[E]

Okay, you're aware though, I'm.

[D]

I'm based here in Massachusetts and then I spent a lot of time up in New Hampshire.

[C]

You're going the wrong way, brother. Come down here.

[D]

Hold on.

[E]

Wearing mess Andover.

[C]

Next time you come down to Florida, give us a heads up, all right? If you got a good. If you're a good golfer, John doesn't. He becomes Joe Pesci if you beat him. So just be prepared for that. He's all nice on a podcast.

[D]

But I was, I've been working on my game. You know, I'm a. Basically a hacker. I'm a 14. But I was, I was going through

[C]

this stuff about, oh, hacker Johnny. You got that?

[D]

I heard that culture of continuous improvement. I'm like, I'm always talked about this culture with continuous improvement. I'm working so hard on my golf game. Why do I suck? How come I can't get down to a 10?

[C]

Well, you come down and play with us. Johnny will tell you why you suck. I'll tell you that much. It's what he does to me on a round all time.

[E]

All right.

[C]

Great to be with you, Lou. Thank you so much.

[E]

Thank you so much, John C. Thanks. And thanks to everyone for listening to another episode of the Revenue Builders podcast.

[D]

It's awesome. Thanks, guys.

[A]

Thanks for listening to today Today's episode. If you enjoy the content, please subscribe, rate and review the show to help us reach more people. This show is brought to you by Force Management, where we help companies improve sales performance, executing the growth strategy at the point of sale. Check out forcemanagement.com for more information.