
The Account Experience Podcast · 2025-12-24 · 30 min
Key moments - from our scoring
Substance score
49 / 100
Five dimensions, 20 points each
Lou Shipley brings decades of operating experience to a conversation about what separates successful founders from those who stall. His book 'Unlikely Entrepreneurs' challenges the Silicon Valley mythology by profiling 13 real founders, many starting businesses in their 40s and 50s - research shows 44 is the optimal age for entrepreneurial success. Shipley emphasizes that effective leadership isn't about dashboards; it's about direct customer engagement. When he became CEO of Black Duck Software, he implemented CustomerGage to route every low NPS score directly to his inbox, then personally called dissatisfied customers like Amazon to understand product gaps. This approach - listening rather than pitching, letting customer feedback drive product pivots - led to Black Duck's shift toward open-source security, eventually selling to Synopsys for a premium. For CX leaders, Shipley's core insight applies directly: recording and analyzing sales calls, sharing unfiltered customer sentiment across engineering teams, and building accountability around what customers actually say creates organizational alignment. He also discusses how his sales education courses at Harvard (with Mark Roberge, HubSpot's first CRO) combat the persistent stigma around selling by teaching it as listening and problem-solving, not coercion.
Research cited in 'Unlikely Entrepreneurs' shows 44 is the best age to start a company because founders at that stage have experience, networks, accumulated capital, and have seen failures - not because of age itself, but because of maturity and resources.
He set up CustomerGage to route all low NPS scores to his desk, personally called dissatisfied customers like JP Morgan, and learned that banks were manually curating open-source security vulnerabilities - insight that led him to pivot from license compliance to security products, driving growth and eventual acquisition by Synopsys.
Most build a product first, get venture capital, then try to sell it; Shipley advocates the opposite - validate that your idea sells first, then build the product, then secure financing.
Recording calls reveals what competitors are saying, what customers actually value, and what messaging works - sharing this unfiltered with engineering teams (not just sales) prevents defensive reactions and drives alignment around real customer needs.
CEOs who listen to 30-50 minute sales calls learn everything needed about a company: whether customers like the product, sales team quality, pricing competitiveness, and who the real competitors are - all faster than reviewing reports.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a handful of genuinely operational insights buried in the episode - NPS routing to CEO, tying engineering bonuses to score improvement, and the JP Morgan pivot story - but they are heavily diluted by book-promotion chat, personal relationship anecdotes, and a mid-episode sponsor read. The ratio of actionable ideas to filler is low for a 30-minute runtime.
if any score came in from zero to six, it got routed to my desk as CEO
I tied the bonus to whether they the net promoter score went up
A few genuinely counter-narrative ideas appear - the research-backed '44 is the optimal founding age' claim and the 'sell before you build' sequencing invert common startup orthodoxy - but the bulk of the episode recycles widely-circulated advice: listen to customers, sales is misunderstood, founders need resilience. Nothing is truly first-principles.
the best age to start a company is 44
I said, why don't we do it the other way around? Why don't you see if your idea sells, then build the product
Lou Shipley is a genuine multi-time operating CEO with verifiable scale experience (0 to $500M at Avid, Black Duck sold to Synopsys) and a real academic role at HBS, making him a credible practitioner rather than a pure thought-leader. However, the episode is structured around book promotion rather than extracting deep operational knowledge, which constrains how much of that caliber actually surfaces.
We took it from 0 to 500 million, went public
every day that JP Morgan software developers were curating a, a handwritten list of security, open source security vulnerabilities that went up to Jamie Dimon's desk
The episode lands above average on specificity thanks to named companies, real dollar figures, and concrete data points - the JP Morgan story in particular is vivid and instructive. But several sections of the book discussion stay at a surface storytelling level (brewery founder loves beer, pizza seller in Naples) without extracting the underlying mechanism or metric.
we got a zero net promoter score from Amazon, which one of our was one of our top five customers
There's 950 students at HBS in a given class, and about 450 of them I'll take
The host is the guest's long-term mentee and simultaneously runs the episode's sole sponsor (CustomerGage), producing an inherent conflict of interest that eliminates any meaningful challenge. Questions are largely set-up prompts, the host repeatedly inserts his own stories and self-promotion, and not a single claim is probed or pushed back on throughout the episode.
I also became. I'd wanted to be an entrepreneur before. Didn't know quite how to do it, but it was really in my 40s that it came together
Yeah, I really agree.
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of The Account Experience Podcast, Adam Dorrell sits down with Lou Shipley - former three-time software CEO, Senior Lecturer at Harvard Business School, board member at CustomerGauge, and author of the new book Unlikely Entrepreneurs, already a top-three Amazon bestseller ahead of launch. Adam and Lou reflect on more than twenty years of working together, using that shared history to explore what really separates successful B2B companies from the rest. Lou shares key lessons from his book, including why entrepreneurship doesn’t follow a single path - and why experience, judgment, and empathy often matter more than youthful bravado. A central theme of the conversation is customer and account experience as a leadership signal. Drawing on Lou’s time at Black Duck, they discuss how listening to customers cuts through operational noise, reveals hidden risk, and exposes growth opportunities long before they appear in dashboards or forecasts.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Lou, what's the one thing you've learned from writing the book?
Speaker B: Well, if you want to have a bestseller, you got to be a bestseller.
Speaker A: Hi, I'm M Adam Durrell and I'm the host of the Account Experience podcast. If you're new here, welcome. And if you're a regular listener, you'll know that Account Experience lives at that junction of relationship road and action avenue. And it's that point where B2B customer insight turns into real commercial impact. For each episode, I like to meet up thinkers and leaders, uh, who can challenge how we build trust, loyalty and long term B2B relationships. Today's Conversation is a little bit different because we're focusing on the founder's perspective and, uh, what really separates companies that grow from those that stall. What can leaders learn from the moments that don't go to plan? My guest today is someone that I've known personally for more than 20 years. I've worked for him early in my career and he's been a mentor to me ever since. Lou Shipley is our guest today and he's a three time software CEO. He's a senior lecturer in entrepreneurial management at Harvard Business School where he's pioneered the sales education as a completely new thing there. And he's previously lectured at MIT Sloan to a really great, uh, academic background. And he served on the boards of companies like Wasabi Technology, Fair market and also CustomerGage. And lose released this new book, it's called Unlikely Entrepreneurs, which is out in February. And I'm already delighted to hear that it's in the top three at Amazon already. So we'll hear about that. That's a remarkable achievement. And what makes Lou, I think, especially relevant for this podcast is his belief that customer experience cuts through the noise. I mean, he stepped into leadership roles, he just didn't look at dashboards or forecasts. He wanted to understand what customers were really telling him. So we'll get into that. So today we'll talk about the lessons behind unlikely entrepreneurs and why customer experience is such a powerful leadership signal in B2B and what it's like build and lead companies later in life. Well, it's a pack show already. Lou, welcome to the Account Experience podcast. Thanks for being here.
Speaker B: Thanks, Adam. Great to be here. It's been an honor to be working with you for. I think it's. I've been on the board for what, 13 years?
Speaker A: Yeah, I think so. And before that. So we've. No, well, we won't give away how old we are, although maybe we'll get into that because there's an interesting chat in your book about that, isn't it?
Speaker B: Yeah, yeah. There's a chapter on, uh, entrepreneurship as a second act.
Speaker A: So, you know, let's start with the book. I mean, you spent years teaching, operating and mentoring founders. So have you had some personal learnings? First of all, writing the book and then maybe starting to promote it? I'm really fascinated to find out what the journey's been like.
Speaker B: Yeah, it's been really fun, Adam. I was approached by former, uh, colleague from MIT Sloan, Trish Favreau, uh, a couple of years ago who said, um, I think there's an idea for a book of unlikely entrepreneurs. I mean, the idea here being, you know, we talk about, when we talk about entrepreneurs, it's often the college dropout or Silicon Valley billionaires. That's not what this book is about. This book is about the person around the corner who's starting a business, who's starting of business. And they're unlikely stories, their wins and losses and how they build great companies. So it's been really fun. We interview 13, profiled 13 different entrepreneurs. We have about another 15 experts who weigh in on what they did well and what they could have improved. And so the idea is, if you're thinking about being an entrepreneur, maybe it is for you. And, uh, this is a good book to read. And it's fun, it's storytelling, it's stories about really interesting and unlikely people.
Speaker A: Now, if I think about the journey that you've been on, I mean, I've been lucky enough to sit in some of your Harvard classes about entrepreneurship, and yet you, I think you pointed out to me that it's not been a recommended academic track for many years, and yet this has now become a very popular course at Harvard that you're teaching. Why do you think that entrepreneurship has not had that academic study track before?
Speaker B: Yeah, it's very interesting. And by the way, you also came in and did a class with us. So. So there's two pieces. There's the entrepreneurial piece and, uh, so many people coming out of both MIT and Harvard now want to be founders. They want to be like you. They want to start a business, they want to be their own boss. It used to be like, when I went to Harvard Business school in the 90s, it was like sort of Fortune 500 CEO school. It wasn't to start a business. Now, about almost a third of the students start businesses. They don't necessarily just go to consulting or banking or private equity. And so as that Entrepreneurship interest has grown. It has had another interest in sales. Because why is that? There's still this myth out there that if you build a great product, the world will beat a path to your door. Not the case. You have to have the best product. You have to have the best sales team. So we've taught. We have four courses at Harvard now on sales. One is founder selling. The next one is from, you know, you get your first million, how do you get to a billion? And then if you're running really large sales organizations, how do you do that? So. So it's been very interesting to see how the market has responded to both entrepreneurship and sales.
Speaker A: I love the way that when I've seen it, it's not just a theory that you're teaching. I mean, your students really get involved. How did you manage to construct a, uh, you know, a course where that happened for these?
Speaker B: I took a course. I was teaching at mit. I brought it over to Harvard. I did some of the classes myself. I also teamed up with a fellow named Mark Roberge, who is. He was the first salesperson, the first CRO at HubSpot. Saw that through the public CRO. Terrific guy. And he and I, what we added to the sales team was the sales class was coaching. Each student gets a coach, and they can practice sales and get feedback on how their sales calls are going from a professional sales coach. So we have about 70 coaches that provide feedback to the students. That's why the class is so popular. There's 950 students at HBS in a given class, and about 450 of them I'll take. You know, they'll opt into this class, and it's because I think they get a lot of feedback. They learn and overcome their disdain and fear of selling. Like, you know, it's hard. It's. Some people really don't like sales. And so you have to overcome your. Your disdain of the function or your misunderstanding of it and get good at it.
Speaker A: Yeah, I think you're right. I mean, sales can. If you ask a dozen people, they'd probably say sales is a bit of a dirty word. Yeah, it's what makes our world tick, isn't it?
Speaker B: Well, Adam, name another function in business that has a sign that says don't do it.
Speaker A: You see?
Speaker B: Soliciting sign. You've never seen, like, no marketing or no finance or no strategy. It's only. And then, uh, not only that, but it's a euphemism. It isn't even sales. It's soliciting. So people have to get over this, you know, uncomfortable feeling about selling. And what we teach is selling is not about pitching or coercion or convincing. It's about listening and understanding whether your product solves somebody's problem. And if they do, then there might be a match.
Speaker A: I'm going to pick up that listening part that you've just done, and m. I'm going to make that bridge to what most of the listeners, uh, to this podcast think about, because most of them are thinking about customer experience. They're not directly selling to the customers. And yet your book's got a lot of valuable lessons for this group. So what can the audience take away from. Did this audience of CX leaders take away from the lessons from your book?
Speaker B: Well, let me. Maybe I'll just tell Adam the story about when I was a CEO of Black Duck. I got there, the company had only done, like, annual customer surveys. And I was like, you guys got to bring in a real product that can do this daily. So we brought in Customer Gauge. Terrific product. And I, I had it set up so that if any score came in from zero to six, it got routed to my desk as CEO, I would get it like I'd get a. Any other email. And I remember one day, specifically early in my time at Black Duck, uh, we got a zero net promoter score from Amazon, which one of our was one of our top five customers. So I picked up the phone and called the guy who gave us a zero and I said, um, I'm the CEO of Blackdog. I see. Really don't like our product. Can I help you? Why don't you like it? And the guy was really taken aback that the CEO of a company would call and want to know, what don't you like? And boy, you can't get better unless you know what customers don't like about your product. You guys helped us to learn that you not only have to survey your users of your product, but also, you know, the decision makers. And all through the organization, you get a sense, uh, there how what's this company's reputation really inside. And the different NPS scores that you showed us for different people within each, each company was fascinating. So we had to design how we were going to cover those accounts based on the information Customer Gauge gave us.
Speaker A: Yeah, I think that's. I love that moment that you brought up. That also taught me a lot, actually, because you were one of the few CEOs that we were able to interact with straight away. And we're talking years ago now, you know, from when, when this happened and uh, there was something I took away about cutting through the noise in the organization that you've got all of these people covering their asses. You know, it's like, oh no, we know the customer. You know what's going on there and you like, you go straight to it. Can you expand a little bit more on that about how in the organization you've been able to cut through? Because I guess that's at the heart of entrepreneurial. Is it?
Speaker B: Well, it's at the heart of uh, everything. So it really. And uh, the first chapter in Unlikely Entrepreneurs is called the problem with the Problem. And it gets back to this whole notion of how big a problem is your problem that you want to solve for your company. Clearly, customer gauge customers had a real problem. You solved the real need. Customers were in pain because they didn't have your product. Now a lot of entrepreneurs don't do the necessary work to understand the pain of their product problem. But in the case of Black Duck, you know, we really needed to rework the product to get the customers to be happy with it and to get our Net Promoter score up in order for us to grow. So I felt like I could learn everything I needed to know about a company. I still feel this way today, Adam. Um, I can learn anything I need, everything I need to know about a company. By making a sales call, you find out does the customer like your product, what's your salesperson like, what's your pricing, your competition? Everything comes out of like a 30 or 40 or 50 minute meeting. And I felt that that's what your product gave me. The uh, ability to then go to the engineering team and say, our customers don't like using our product. We have to fix this or we're going to fail. And by the way, I got a lot of pushback from the Black Duck engineer. They did not like me telling them this. They're like, no, no, it's fine. No it's not. And we're not going to grow unless you fix it. So I remember I tied the bonus to whether they the net promoter score went up. So your product gave us all this great data on what people actually thought. So if you're not close to your customer, you're going to fail. You're not going to be able to grow the customer and develop. What I think is most important is these enduring long term relationships. You have them at customer engage with your big customers. They love you guys, they learn from you. And I think that's what it's all about in the B2B world is developing that trusting, long term, enduring relationship.
Speaker A: Yeah, I really agree. By the way, I'm picking up on what you're saying about when you went to see the engineers. It wasn't you speaking. You had the voice of the customer in your hand. It's not me, it is what the customers are saying. Guys, read it and weep.
Speaker B: That's exactly right. And one of the controversial things I did was I put the customer gauge information all around the company. And by the way, engineers don't like to be told that their net promoter score for the product they work on is minus 13. They didn't like that. But you can't fall off the basement floor, right? You need to know where you are. And it's like you can't get better unless you're fixing what's wrong.
Speaker A: But you had a huge success story in the business. And, um, I think in part it's because you were listening to customers and fixing things and getting the product right.
Speaker B: Well, I'll give you an example there, because Black Duck at the time was and still is the leader in open source license compliance. You know, is this the open source that your company's using? Is that safe and secure? But what we found, I, I had worked my previous company, turbonomic, we had sold to JP Morgan and we won the, uh. JP Morgan has an award each year called the hall of Innovation Award to the best startup that the company that J.P. morgan uses. In that year we wanted it via Turbo. The next year I went Black Duck and I went to see JP Morgan and I learned just by listening, I wasn't pitching or anything, just by listening that this is in 2015, that every day that JP Morgan software developers were curating a, a handwritten list of security, open source security vulnerabilities that went up to Jamie Dimon's desk. So what you're doing well, we have 10,000 applications. We're like, well, we should be doing open source security. So we pivoted the company and a lot of people didn't want to do it. And I'm like, if this is happening at JP Morgan, weakest bank in the world. There's a market here and that's what we do. We build some security products and eventually we're sold to Synopsys because of our security product. Really the growth there. But again, how did it happen? You go and listen to your customers. You don't pitch them, you listen to them.
Speaker A: Yeah. Can I share one story with you that we got from them the last year? Because it's in the similar vein about listening to customers, we have started to record all of our sales calls. And we've not been doing this before, but this has been a game changer because first of all, we listen to it back and it's quite painful for people to go, oh, that happened. We listened to it in a group sometimes eating a pizza or I'm cycling home and I'm listening to this thing, and you go, oh, we shouldn't have said that. But of course, you get this great signal that comes out of it. And with AI, we learn something really good. Ian, our CMO was able to put the call through some, uh, AI software, and we were able to pick out what people said about our biggest, uh, competitor. So we got a real battle card from 150 comments from about our, uh, competitors. That's really helped us.
Speaker B: So, yeah, how powerful is that? I mean, think about it. If you, if you just do what so many companies do is you build a product, you give it to your sales team, you, you figure out how to sell it as opposed to doing it with them. Um, I used to sit on the sales floor as a CEO and take the calls, listen to the calls. I used to listen to the sales calls, you know, on my commute in and out of the office. And I'd learn, you know, does someone get the message down? Or, uh, what competitor is giving us trouble? What's our pricing? You can learn so much just by listening. And to not take advantage of that is so, is so dangerous because you're not going to know where the market is by doing what you're doing. By the way, I applaud you for doing that. You know, Adam Clay did that at Black Duck. You know, we didn't even have gong or the kind of tools we have today. We did it all ourselves. We recorded the calls, but it made a huge difference in a culture of building accountability. And here's our message. Here's how we're all going to talk about it.
Speaker A: Yeah, I agree. In fact, big shout out to Adam Clay, who's driven the sales process and customer gauge. And now sales is not a dirty word in our company. We really look forward to it. It's really driving it. And we had also a shout to one other person I would like to mention. Ross Morgan, you may also know. Oh, yeah, uh, he was with our kickoff last year, the most popular session we had on our kicks with Ross. So it was like a real turnaround in our business about thinking about commercialism. It's really a nice thing,
Speaker C: this podcast is sponsored by CustomerGage, and they're the experienced leader in the CPG market. And let me tell you why. They're contacting more people in the independent trade and modern trade than any other customer experience company out there. And you'll know the brands that they work with. We're talking Coca Cola, AB, InBev, uh, Heineken. Just e takeaway. They're literally pulsing millions of contacts around the world in more than 60 countries multiple times a year, delivering those insights to thousands and thousands of frontline employees in those companies. But, you know, it's not just the CPG business Customer Gauge is famous for. They're ranked number one for B2B customer experience by Gartner. However, if you're in the CPG business and you have not contacted Customer Gauge to understand what is going on in your business, you're seriously missing out, because we know there are other people out there just doing it once a year. Well, Customer Gauge gives you customer insights 52 weeks a year, right to the front line in real time. It's going to absolutely transform your business like nothing else. But, uh, don't take our word for it. Listen to the podcast and they'll tell you exactly why.
Speaker A: If I can. I just want to pivot back to the book because, uh, by the way, I'm really, really looking forward to read it. But one of the things that I was able to get some advance information on was something you wrote about, which is about becoming an entrepreneur, uh, later in life. And I'm fascinated by this because I think the, you know, everything we see from films like the Social Network to, you know, people become an entrepreneur when they're in their dorm room at Harvard or in their 20s. And yet you're saying that the data doesn't necessarily point to that. Love to know more.
Speaker B: Yeah, well, so Trish Favreau and I, she works at mit and she, she worked with the. The researchers that did. Did exhaustive research on what's the best age for being an entrepreneur, meaning what's your highest likelihood of success? Because so many companies do fail. And the best age to start a company is 44. And in our book, we profile three entrepreneurs who did it in their 40s and 50s. Dave Piccarello, who start. Who had a really successful career as a consultant, but he loves beer and he wanted to start a brewery. He started Twin Barnes Brewery in, um, Meredith, New Hampshire. And we tell his story. It's just a fun story because he and his partner Bruce just, they love beer. And now they have a thriving Business. And he did that. Charlie Tillinghast, who's a classmate of mine from Harvard Business School, was the president of NBC News Interactive. Like, it's a pretty big corporate job. He did that for many years. They launched a media channel called Breaking News. You might have. You might have seen it. And when Charlie left the company, MSNBC dropped that product because he just didn't think there was a market for it. So he went and created another version of that product called Factual. He's the CEO of this company, facto thriving business. So it's a great example of when you're older, you have, you know, you have experience, you've seen failures, you have a network, you might have a little cash if your kids are through school. It's actually, uh, almost a better time, in some cases, a better time to become an entrepreneur. As. And I think the pressure on students to do it in their 20s is sort of unnatural. You shouldn't feel badly that you don't start a company if you don't have a real problem to solve. And I. That's one of the reasons Mike should go back to my fourth class at Harvard was I saw so many students starting companies because they wanted to be founders. And then they built a product and they got venture capital. Then they tried to figure out how to sell it. And I said, why don't we do it the other way around? Why don't you see if your idea sells, then build the product, then get financing and build a playbook of how you would sell, sell this. So that class has helped the students really understand. Maybe my idea is good and I'm going to go run the company. Or maybe I need to find another idea or join a company. And it's nothing wrong with that either. You shouldn't feel pressured to do it just because it's so popular now.
Speaker A: It's really interesting. Can I reflect on my own journey for a moment? Because I also became. I'd wanted to be an entrepreneur before. Didn't know quite how to do it, but it was really in my 40s that it came together. And I think it was all of my early learnings in sales and marketing that really paid off. I came into this with a good set of skills that I don't think I've had before.
Speaker B: Well, and you saw a problem, and you're like, I think there's a business around this problem. And you and I worked together back in the early 2000s, and we were so good at marketing, uh, and positioning. And then I guess I can't remember the Origin story of how you found this problem. But I know you called me and talked about it so I think there's a business here.
Speaker A: Yeah, well I think it was a Sony and I was like nobody's acting on this feedback and there's something there and I had this, I had this part but there's something else and this is interesting. Let's get deep for a second because you know you've been, you've been mentoring me for a long time. I think I went through quite a long period of having a lack of confidence. You know they call it imposter syndrome. We weren't getting the results we wanted to a customer gauge and you know you and the board were also kind of critical about some of the things that I did. I went through a tough patch with that personally and it took again me a while to really lean into it to go actually no, I am strong here I am doing this. So there is the entrepreneurialism on entrepreneurship I suppose it's not for the faint hearted, is it?
Speaker B: Uh, no it's not. It's a journey and we talk about this as we profile our different entrepreneurs. The first one in the book, the first startup as you know that I joined was Avid Technology and built when there was a pioneer, the inventor of digital nonlinear editing. Bill's story is one of overcoming real hardship, really really tough personal hardship and creating you know, non linear editing and all the Hollywood films are edited on the avid. Amazing business. We took it from 0 to 500 million, went public. It was an incredible ride but he overcame a lot of hardship and I think that's part of what is actually I don't want to give away the last line of the book but there's a, there's entrepreneur another one who's more our age guy named Merle Thuramali. I met him, he was a founder of Net6 that got acquired by Citrix right before reflect at the company I was running got acquired by Citrix. We got to be good friends. He founded two more companies after that and now he's finally retired and one of the. Adam, you'll love this. One of the things he told us as Trish and I interviewed him is he said, you know what's really important to me is the supermarket test. I'm like Merly, what's that? He goes well the supermarket test is you walk along in the supermarket and someone who used to work for you sees you. One of two things is going to happen. Either they're going to hide behind the Cheerios and not let Us. See you going. Hey, M. Merle. Great to see you. I worked for you at Blah Ah blah blah. And he said, everybody comes up and wants to talk to me. I, you know, I start, you know, I worked at one of your companies or all three of your companies where I started my own company. And it's like, entrepreneur is a gift. Entrepreneurship. It's a gift that keeps on giving. And why do we do it? Like, why do you keep doing it? It's hard, struggled through this, but you still persevere because the satisfaction of doing it well is so powerful. And the customers that you at CustomerGage have closed and then grown. These brands are incredible. These are the number one brands in the whole world.
Speaker A: Thanks for saying that. But I think it's the same with Camilla, my co founder and myself is that we can't imagine doing anything else. Just wake up in the morning, it's just another problem to solve. And it's that puzzle, uh, that, that solving a puzzle, getting to a goal. I think that's what drives us is you can't stop it. Uh, it's hard to get off.
Speaker B: It's interesting you say that because I remember my first job out of college. I was working at Paine Weber. It was a big financial services firm. It's called UBS now. And I remember walking down. I was living in New York City. I was walking down the street and it was a beautiful June day. I really would have rather been playing golf or hiking or something. And I was walking along. I'm like, you know, if I didn't show up at this company, no one would know. Like 43,000 people. Like, if Lou didn't show up, like, who cares? Kangaroo's earnings were fine whether Lou showed up or not. And I was like, I got to do something else. I got to go to a company where if I don't show up, we might miss our numbers or we might go out of business. And I really, like, I'm not dissing working in a big company. There's. For a lot of people, that's the right thing to do. I'm not judging it, which for me it wasn't. And whether my m startups got to go public and were really big, I would leave them after they were too big because I just wasn't happy there. I wanted to go back to that startup, back to that idea, back to that. I don't know who you are. Why is this thing worthwhile? It takes a lot to build something from nothing. Like, you've done a customer gauge. So that's why I did six and now I spend all my time with startups. I like people like you or David Friend, founder of Wasabi. Kevin Prichette, founder of Fair Market. They created something from nothing and that's incredibly satisfying when it works.
Speaker A: Yeah. And I think it's a certain pride in what we do because it helps the economy go around. I mean we're growing wealth and that sort of stuff. But I mean if you reflect on where you've been because you've been this incredible several careers and we were talking just now about how you've done this and then you pivoted to almost becoming a full time lecturer and then now you're an author. How do you think about these phases in your career and thinking about where's the entrepreneurial side in these two other areas.
Speaker B: So, you know, I was really fortunate. I got my break at mit. My friend Howard Anderson, he's in the book and um, you know, asked me to come in and do some lecturing and then he asked me to run a course and I did that for a number of years. I taught with Kirk Arnold and Dennis Hop. It was Jim Schutzer, had a great time at mit. I still love mit, but I, I found I had to do that while I was a full time CEO, which was hard. And I remember before, each time I'd go to class I'd call my wife and say, I can't do this. I don't have enough time, I shouldn't be doing this. I'm trying to run this company. And then on the ride home I'd say, man, that was great. I wanted it for the students. I'm so psyched to get back. So I was fortunate that I got into it sort of young and then when I sold black duck, I decided, you know, why don't we do it? So I'm full time now at hbs and it's great because my daughter's there. So, um, I'm able to go to school with my doctor is, but you know, I didn't really ever think it was going to be a full time job. And with the book, what I'm liking is it kind of like you, I like doing new things. So I'm a B2B infrastructure software guy my whole career. This is a B2C business. Yeah, yeah, I'm doing it. It's a blast. We're number two on the Amazon charts right now for business entrepreneurship. And we haven't even shipped the book yet. Looking forward to it. No one's even reviewed Any of you,
Speaker A: hey, listen, let's, let's sort of close this down a bit because there's so many great stories that we could pull out of it. But I mean, if there's one ide hear from unlikely entrepreneurs, uh, you know, your hope stays with people after they finish the book. What would it be?
Speaker B: Yeah, well, look, uh, there's 13 or 17, sorry, entrepreneurs. We profile and there's so many great stories, but let me pull out a couple that are really telling. One is a guy named Scott Ginsberg, who's the founder of Titan Casket. This is a $10 million online casket business in the US when you say
Speaker A: casket, that's what put. You put dead people in, right?
Speaker B: Yeah, exactly. So, like, who would have ever thought you can sell these online? But he, he knew pain people went through and they were burying a loved one and how funeral homes work and all that sort of stuff. He's like, I wonder if this would work. So this sense of curiosity, do you think I could. I remember he asked his wife, do you think I could sell one online? She's like, why don't you try it? And he did. And then he brought in some people from Amazon to help and ship big items. And it's growing like crazy. So the curiosity, I wonder if, like that's, that's the first and the most important thing. I think entrepreneurs have kind of like, dear idea. I wonder if there's a business out of net Promoter score. Like the stuff you were seeing Sony and Bill Warner at Abbott. He had the visceral pain of trying to make changes to film and video editing. And he's like, why don't I digitize this and cut and paste full motion video like that's done with a word processor. When you're doing text editing. Ah, uh, boom. A whole industry is born. Like, that's what's so interesting is how curiosity drives this. And I think we cover, uh, American entrepreneurs. We have, uh, English entrepreneurs. Uh, Matthew Riley, the, uh, founder of Daisy Group, started as a typewriter repairman and now he's a billionaire. I mean, these are just great stories. Enrico Porzio is the biggest pizza seller in Naples, uh, Italy. So we have not just American stories, we have this globally. And entrepreneurship, I think, is one of those things everybody agrees on. Like, you know, whether you're right or left on the political space. Everyone agrees entrepreneurship is great because it helps drive business, create jobs and create satisfying jobs.
Speaker A: Yeah, I think that's a really nice concept to take away. Now people want to get the book or they want to find out more and follow Lou Shipley. How can they do that?
Speaker B: Yeah, you could buy it on Amazon or wherever you, you shop for books, you can go to my website, Lou Shipley.com and there's a little slash for a book. You can pre order it today if, uh, you pre order it today. By the end of December, we're giving out these really cool hats. If you want. If you want an unlikely entrepreneur hat.
Speaker A: I do want one. Yeah.
Speaker B: I'm just for hosting on the podcast,
Speaker A: but, um, I've already ordered a few books. My goodness me.
Speaker B: But we're having fun with it. And I was saying to my wife, when Trish called me originally my co author called me and I said, I don't want to do it unless we're going to have a bestseller. It's just not worth it because it's a lot of work to write a book. It's a ton of work. It's. It's hard. So here's my, uh, I can distill it down to this. It takes to have a bestseller. It takes a bestseller. I think there's this concept out there. If you write a great book, you know, like, like I said before, about products and software, the world would be to pass through door. Not at all. If you have a great book, you still have to sell that book. You have to tell people why it's good because you're competing for people's attention and there's a lot of other stuff out there right now.
Speaker A: Yeah, I think so. Also, I've really noticed you're posting some great stuff on LinkedIn. So that would be my tip if anyone's out there. If you follow Lou Shipley on LinkedIn, you're going to get some great content out there. It's always really good. Lou, I've loved speaking with you today. It's really great to do and best of luck with the book and a fantastic 2026.
Speaker B: Great. Thank you very much. Thanks for having me.
Speaker C: It.
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