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Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies.
Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall.
In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator.
Lou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer.
If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most.
Discussed in this episode
- Why understanding customer pain matters more than having a great idea
- Why early selling should optimize for learning, not revenue
- Why founders can’t outsource sales too early
- How distribution becomes a competitive advantage at scale
- What makes “unlikely entrepreneurs” outperform expectations
- Why small, high-quality teams beat large organizations
- Why churn is a symptom, not the root problem
- How product-market fit quietly changes as companies grow
- Why founders must evolve from heroic sellers to system builders
- How culture becomes a real go-to-market asset
Episode highlights
00:00 – What actually makes a company great
https://youtu.be/SsHVHvQly8A?t=0
00:26 – Why early selling is about learning, not revenue
https://youtu.be/SsHVHvQly8A?t=26
01:47 – Why founders misunderstand customer pain
https://youtu.be/SsHVHvQly8A?t=107
02:06 – “If you build it, they will come” is a lie
https://youtu.be/SsHVHvQly8A?t=126
02:33 – Distribution as the real moat
https://youtu.be/SsHVHvQly8A?t=153
02:58 – What makes an “unlikely entrepreneur” succeed
https://youtu.be/SsHVHvQly8A?t=178
06:15 – Why age and experience increase founder success
https://youtu.be/SsHVHvQly8A?t=375
07:01 – Curiosity, coachability, and risk elimination
https://youtu.be/SsHVHvQly8A?t=421
09:29 – Why founders can’t outsource sales too early
https://youtu.be/SsHVHvQly8A?t=569
15:26 – Pattern recognition vs short-term ARR
https://youtu.be/SsHVHvQly8A?t=926
21:10 – Founder-led sales vs scalable systems
https://youtu.be/SsHVHvQly8A?t=1270
29:12 – Leadership, culture, and delegation
https://youtu.be/SsHVHvQly8A?t=1752
33:18 – Founder evolution from $1M to $100M
https://youtu.be/SsHVHvQly8A?t=1998
38:24 – When product-market fit starts to break
https://youtu.be/SsHVHvQly8A?t=2304
39:15 – Why churn is a lagging indicator
https://youtu.be/SsHVHvQly8A?t=2355
39:54 – Why small teams outperform large ones
https://youtu.be/SsHVHvQly8A?t=2394
44:22 – Lessons from *Unlikely Entrepreneurs*
https://youtu.be/SsHVHvQly8A?t=2662
45:23 – Final advice for founders
https://youtu.be/SsHVHvQly8A?t=2723
Key takeaways
1. Understanding customer pain matters more than having a great idea.
Founders who understand pain viscerally know what to build and why it matters. The idea that “if you build it, they will come” is still one of the most dangerous myths for startups.
2. Early selling is about learning, not revenue.
The goal of your first customers is not ARR. It’s pattern recognition. Usage, engagement, and real feedback matter far more than short-term revenue.
3. Founders can’t outsource sales too early.
If you don’t experience selling firsthand, you don’t understand your buyer’s journey. Hiring sales too early often means importing the wrong playbook.
4. Distribution becomes the moat as companies scale.
At a certain size, the best companies are distribution machines.
5. Small, high-quality teams win.
You don’t need hundreds of people to build something great. A few exceptional ones outperform large teams every time.
6. Churn is a symptom, not the disease.
Product-market fit shifts over time. Usage is the leading indicator. Revenue is the lagging one.
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GTM 177 Episode Transcript
00:00:00 – 00:00:03
Sophie Buonassisi: What do you believe actually makes a company great?
00:00:03 – 00:00:12
Lou Shipley: Founders that truly understand the pain their customers are in, almost viscerally so they know what to build. And then as a founder, learn how to sell.
00:00:12 – 00:00:26
Sophie Buonassisi: Lou Shipley is a three time CEO professor at Harvard Business School, a board director and investor and advisor, and also the coauthor of Unlikely Entrepreneurs. Early selling is really about pattern recognition, not revenue. Would you agree with that?
00:00:26 – 00:00:51
Lou Shipley: Early on, you really want to optimize around learning as opposed to revenue on those first customers because you’re, by definition, getting early adopters. It’s getting usage and understanding that you really are solving the pain point, and that the products being used and the customers really like it. What you just need is a really strong small team. You don’t need a lot of numbers, and it’s so tempting when you have a company that’s growing to like, hey, I got 100 people, I got 500 people I got, how good are they?
00:00:51 – 00:01:01
Lou Shipley: I’ve been on a lot of winning teams that just have a few. You don’t need that many people to do something great.
00:01:01 – 00:01:07
Lou Shipley: The.
00:01:07 – 00:01:10
Sophie Buonassisi: Blue. Welcome to the GTM now podcast.
00:01:10 – 00:01:12
Lou Shipley: Thanks, Sophie. Great to be here.
00:01:12 – 00:01:19
Sophie Buonassisi: You bet. Great to have you here. And a huge congratulations on the book launch to unlikely entrepreneurs is is now available.
00:01:19 – 00:01:23
Lou Shipley: Yeah. Thank you. Thanks. Yeah, it’s been been a long road, but a very fun one.
00:01:23 – 00:01:47
Sophie Buonassisi: Well, that is exactly what we’re going to dig into today. Some of the stories behind some of the most interesting, unlikely entrepreneurs that you’ve seen because you’ve been a three time CEO. You’ve led companies through acquisitions, and you now teach founders at Harvard. So curious if we zoom out sitting here today, what do you believe, if you could summarize in one line, actually makes a company great.
00:01:47 – 00:02:06
Lou Shipley: Well, and it’s hard to do it in one line. I think founders that truly understand the pain their customers are in and and can understand that pain almost viscerally so they know what to build is kind of the first thing. And that’s that’s really the first thing we teach at Harvard is understanding customer pain. So you know what to build.
00:02:06 – 00:02:29
Lou Shipley: There’s still there’s still this idea out there that I’ve got this great idea. And if I build a great version of it, the world will be a path to my door. It’s just not the case. So you just you really have to understand the customer’s pain. And then as a founder, learn how to sell. And I think a lot of people still kind of are struggling with that a little bit because sales are so maligned and misunderstood.
00:02:29 – 00:02:33
Lou Shipley: But the best founders learn how to do it and and are very successful.
00:02:33 – 00:02:52
Sophie Buonassisi: I love it. Great great advice. And we see it all the time from the venture side. And we have a saying it’s slide two of our deck, always has been from the very beginning. From fund one is first time founders focus on product, second time founders focus on distribution. And it’s an understanding that it really is your go to market now, especially with tech moats declining, that determines your success.
00:02:52 – 00:02:58
Lou Shipley: It’s a very interesting point. That distribution becomes almost your competitive advantage the larger you get.
00:02:58 – 00:03:07
Sophie Buonassisi: Your book is called Unlikely Entrepreneurs. Yeah. What makes someone an unlikely entrepreneur and and why do those founders often outperform?
00:03:07 – 00:03:23
Lou Shipley: Yeah. No. Very interesting question. There’s a couple different ways to define it. My my coauthor, Trish Favreau from MIT, who I used to teach there, and I got to know her there. She was going to call me with this idea and said, do you know any entrepreneurs and unlikely entrepreneurs? I said, yeah, I actually know quite a few.
00:03:23 – 00:03:43
Lou Shipley: So you can be unlikely for a number of reasons. You could be unlikely. For example, one of the founders and CEOs that we profile was a guy named Scott Ginsburg who started an online casket business. It’s the largest in the world selling caskets online. Who would have ever thought that would be possible? That’s doing $10 million and it’s profitable.
00:03:43 – 00:04:06
Lou Shipley: That’s an unlikely business. Some of the other entrepreneurs are sort of unlikely people we profile. And it’s not just for a for profit entrepreneurship. It’s nonprofits as well, with profiles on and Marvin Pierre, who came from a pretty rough background, growing up in New York and then through football, got his way up into college and then got a job at Goldman Sachs.
00:04:06 – 00:04:25
Lou Shipley: And then he realized what he needed to do was social entrepreneurship. He founded a high school in in Houston to help kids stay out of prisons. And so but the lessons that you have with these unlikely business models are very similar, whether it’s for profit or nonprofit. You have to understand the pain. You have to understand how to finance it. You have to understand how to lead the company.
00:04:25 – 00:04:43
Sophie Buonassisi: Yeah, super interesting examples, which you have one of our our LPs. We’ve got a community about 350 go to market operator LPs, and she’s got an e-commerce owned business where she actually sources earn interest in from. Yeah, yeah, different places. And it’s quite an interesting market in itself like for example.
00:04:43 – 00:04:59
Lou Shipley: So so we kind of focus Sophie on not we this is not a book necessarily about sort of Silicon Valley AI billionaires. Not that there’s anything wrong with them. And we all want to be part of one that’s just really sets an investor. This is more like the person around the corner that is an entrepreneur has a story.
00:04:59 – 00:05:00
Lou Shipley: We wanted to tell those stories.
00:05:00 – 00:05:55
Sophie Buonassisi: A quick pause for a company were a huge fan of yours. If you run go to market, you already know the problem. Your data lives everywhere spreadsheets, CRM, sales, calls, ad platforms. Yet you’re still guessing what to do next. Hockey stack is the AI platform for modern go to market teams, unifies all your sales and marketing data into a single system of action. Built in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale it works. That’s why teams like RingCentral, outreach, Active Campaign, and fortune 100 companies rely on hockey stack to eliminate wasted spend, take better decisions and make space to think. Learn more at Hockey stack.com. That’s h okay e y esta si.com. So let’s let’s stay focused on the human then because they’re unlikely but but they are they are in plain sight oftentimes like you said, who are these unlikely entrepreneurs that you’ve focused on for your book? How are you meeting them? How are you finding them?
00:05:58 – 00:06:11
Lou Shipley: Yeah. So we’ve we profiled 13 different, entrepreneurs in the book. Scott Ginsburg was on Marvin Pier, Katie Couric, or you may know, famous broadcaster when she left broadcast television started Katie Couric media.
00:06:11 – 00:06:15
Sophie Buonassisi: And what are the attributes that you’ve seen make people a great entrepreneur?
00:06:15 – 00:06:36
Lou Shipley: Well, one of the most interesting things in chapter seven of the book, which is called Endings and Beginnings, is we profile three entrepreneurs who started in their, late 40s and early 50s. So it’s, you know, sort of as a second chapter, the research out of MIT Sloan shows that the best likelihood of success for an entrepreneur is age at age 44.
00:06:36 – 00:06:54
Lou Shipley: And why is that? Well, you’ve you’ve you’ve got some skills, you’ve got a network. You probably have a little cash saved up. You’ve seen some mistakes made. So it’s not just the Harvard dropout that starts a company and becomes famous. It really is about people that are doing it, you know, throughout their life after after, a first career.
00:06:54 – 00:07:01
Sophie Buonassisi: Incredible. Curious what you seen, what what types of characteristics you’ve seen to really drive success.
00:07:01 – 00:07:30
Lou Shipley: Yeah. No, there’s a couple of common themes we’ve seen with successful entrepreneurs. One is, is curiosity. Curiosity, just like I wonder if we can do this and why why would it work? And they basically spend time trying to eliminate the risk. A lot of people think are entrepreneurs are risk takers. I even found myself that I felt like the process of joining a startup was always about eliminating risks by, you know, research and understanding customers pain before you jumped in and, joined the company.
00:07:30 – 00:07:55
Lou Shipley: So I think curiosity is one of them, dogged determination and just not saying not giving up like there’s there’s a lot of the, a lot of the people we profile just had really tough, tough, you know, experiences and just work through it. And the other the third thing that I found is that the the entrepreneurs that are open to coaching and mentorship do the best because you can never do this on your own.
00:07:55 – 00:08:07
Lou Shipley: You need you need a mentor. I was very fortunate in my career to have a number of great mentors that helped me through the tough times and told me the truth, even if I wasn’t really recognizing it.
00:08:07 – 00:08:16
Sophie Buonassisi: I love that it sounds like, curiosity. That is by far the number one thing that we hear to perseverance. And then more of a growth mindset.
00:08:16 – 00:08:29
Lou Shipley: Growth mindset. Yeah, I think the coaching thing is really interesting is I joined a number of boards after I saw Black Talk. I promised myself I wouldn’t be too busy. I wanted to own my calendar and then I found myself too busy. I was on all these boards and I, I said, I’m not going to join any more boards.
00:08:29 – 00:08:56
Lou Shipley: I’ll join advisory boards because I like the only we really can’t interview for coach ability. We have a couple of experts. One of them is Will Keller, who runs a coaching business. Talk about how to probe for coach ability in an interview. It’s really, really hard because who’s going to say they’re not coachable, but you get on the board with them or you start working like, this person is not comfortable and there’s you can’t teach it.
00:08:56 – 00:09:07
Lou Shipley: You have to you have to want to be coachable. I wasn’t very coachable my first 6 or 7 years as a CEO. And then I learned that it was important and I was a much better CEO when I became more coachable.
00:09:07 – 00:09:28
Sophie Buonassisi: I think team sports can be a good indication, but it’s it’s so hard. Back channeling is a little bit of the crotch in this case. And one of the things that you you teach specifically is sales. Like you mentioned a couple different topics around sales, and you’ve been quite vocal and a huge proponent that founders cannot outsource sales and selling too early. Curious why?
00:09:29 – 00:09:55
Lou Shipley: Yeah. Well, I think kind of goes back to this notion that still is. I think, pervasive in the market that if you if you build the best product, the product will sell itself. And one of the classes we teach, we we bring in the former president of Tesla, John McNeil, we talked about trying to describe a sales funnel to Elon Musk after Musk had already promised, you know, like, yeah, he didn’t really even know what a sales funnel was and how you have to have to have to teach that.
00:09:55 – 00:10:21
Lou Shipley: So the, the the problem is if you don’t experience it selling yourself and understand the uniqueness of of your product and how many stages a customer goes through on their buying journey to buy your product. If you don’t really understand that when you hire somebody, you run the risk of them just trying to figure it out. And then what they’ll often do is bring in the sales comp plan from the previous company.
00:10:21 – 00:10:42
Lou Shipley: The sales reps from the previous company. By the way, I made that mistake in my other startups because you had experience with them, you were successful. You think, oh, that’ll work here. But but each company’s so different in the context for the buyer, the buyer’s journey so different that you have to figure it out yourself. As a founder, I’d like to say the best ones are usually 15 to 20 of the first customers.
00:10:42 – 00:10:51
Lou Shipley: They close themselves and then they put on a sales person that. But then they have a playbook about here’s how our product works, here’s how our buyers buy.
00:10:51 – 00:11:04
Sophie Buonassisi: Yeah, definitely. It’s a funny time. Playbooks used to be the asset and you’d hire somebody for their playbook. And now it’s quite literally the opposite where you cannot bring your playbook and you have to adapt it. There’s so much nuance in context.
00:11:04 – 00:11:23
Lou Shipley: Yeah, I made this mistake a number of times in my career. I had been very successful in my first startup selling in Japan. I moved to Japan. I opened the office there. So for my second startup, I just assumed the Japanese market would be just as good for this company, which was totally different than the first company. And I made that very mistake.
00:11:23 – 00:11:44
Lou Shipley: I started hiring people, but there was no product market. There’s no need for the product in Japan for the second company. So I think it’s it’s that’s partly why, you know, you need to have a real understanding of each company is very different in terms of how their buyers buy or consider, you know, a product that you might have.
00:11:44 – 00:12:03
Sophie Buonassisi: Yeah, definitely. And what kind of things have you seen? You mentioned the Japanese market. But you know, you’ve you’ve led sales and been the CEO. Multiple companies, avid web line reflect in. I’m curious what kind of through lines you’ve seen from those experiences.
00:12:03 – 00:12:25
Lou Shipley: Okay. I guess there’s a couple things that I sort of believe really fiercely. One is that the, the, the the company with the best team and assuming you have a product that you know is of interest to customers, the company, the best team always wins. And so the chapter in our, our book is called on leadership is called the sled goes as fast as the lead dog.
00:12:25 – 00:12:48
Lou Shipley: And again, it’s about leading as a CEO and the need to set the culture, set the pace of the company. And and you’re responsible for building the best team. In the case of Blackrock, we had to basically rebuild the entire senior management team, save one person. And that was that was totally necessary for the company to be a growth company.
00:12:48 – 00:13:03
Lou Shipley: So some of those decisions are very hard. I find as an independent board member now, often CEOs will say, I think I got a great person here in sales or marketing or whatever, and I’ll go to a board and we’ll say, you know, I think you need to get a better one in that role. And they’re often like, no, this person is good.
00:13:03 – 00:13:28
Lou Shipley: I’m like, well, you’re running the company. I have just a board member. And but in a number of cases, they’ve come back to me six months later saying, you know, you’re right, we’re going to make a change. And that’s so it’s just about getting the best team. And it’s it’s incumbent on you as a CEO to get the best team, to hire the best team, because if you don’t do it, your high performing people will get angry with you that you brought in somebody that isn’t good and they try and overcompensate for them, which isn’t isn’t a good thing.
00:13:28 – 00:13:55
Sophie Buonassisi: And there’s a lot of founders and operators in the audience that are constantly trying to hire the best people. Of course, like you said, but also be able to manage up towards the CEO, the president and the board. And you served as president CEO at Black Tech Software. Namik and, now sit on the board for, for multiple companies and curious, why are you coming in and seeing them as perhaps not the right fit? What are the indicators that they’re not the right fit and that someone could be leveled?
00:13:59 – 00:14:18
Lou Shipley: Things move so quickly, and what works in one company or one scenario often doesn’t work in another. So you’re you’re you’re you’re hiring people, your managers or even the recruiters you use will kind of just pattern match and go fine. So Sophie was really good over here. You should really talk to her. And Sophie was really good over there.
00:14:18 – 00:30:48
Lou Shipley: But it’s it’s harder to to, to be really good in multiple companies. I know a lot of people that were really good in one company, but it may it just because a company was good. So I think you have to to be specific about this. Like I would say in the sales side, chief revenue officer or a VP, sales has to be really modern. It has to understand how all the software tools work, how to use AI, how to hire coach, what sales methodology you’re going to use. And it’s it’s I still see a lot of companies with kind of the Oracle out of the 90s sales methodology, which is old, and it doesn’t work for fast growth companies. It might work for slow growth, but it doesn’t work if you’re trying to really move fast, which is what you know, most VC companies want in speed.
00:15:02 – 00:15:24
Sophie Buonassisi: It’s interesting you say pattern recognition because when Carl Norton, he’s a crop owner, which is a portfolio company with GTM funding, actually, when he came on the podcast, he was speaking to a big point that that you’re talking to, which is the biggest mistake founders can make, is hiring sales and avoiding learning to sell themselves. But he said that early selling is really about pattern recognition and not winning. You. Would you agree with that?
00:15:26 – 00:16:06
Lou Shipley: Oh, I completely agree with you. I think you early on and we cover this in our, one on one class, the basis of selling, because most of these people that take this class are founders and trying to get their first customers, you really want to optimize around learning as opposed to revenue on those first customers, because you’re, by definition, getting early adopters. They’re not all going to stay with you. They may just want to work with you because they think you can solve a problem for them, but they’re not really the ideal customer profile that comes later after you have, you know, product market fit in that can be defined in a thousand ways. But I completely agree with, what he was saying because it’s it’s, it’s not about how much revenue you get from your first customers. It’s getting usage and understanding that you really are solving the pain point, and that the products being used and the customers really like it. And it’s very easy, even when you grow quickly to lose that because product market fit can change in another a couple of years, like your first set of customers. And your first users may be really well suited for you.
00:16:30 – 00:16:42
Lou Shipley: But as you’re trying to expand, you might not have the. Those first set of customers may not be the right ones to take you to the next level. So it’s you have to constantly iterate and be ready for, you know, the problems that might come your way.
00:16:42 – 00:16:58
Sophie Buonassisi: And if it is about pattern recognition, it sounds like a very systemized process. And you teach go to market as a repeatable system rather than, you know, a set of tactics through your courses. What is it core components founders should really design intentionally?
00:16:58 – 00:17:18
Lou Shipley: Great question. I think I think the first one is to literally I think we’re still in this in this phase is to overcome your disdain or, you know, not understanding what sales is. And a lot of people think sales have had a bad sales experience in a consumer capacity. Maybe it’s a car dealer or something, and you sort of think, I don’t want to do that.
00:17:18 – 00:17:38
Lou Shipley: I don’t want to be in sales. But my my experience is the best salespeople are not the sort of the back slapping, slapping, you know, outgoing, gregarious types. They’re a little quieter there, inquisitive. They ask a lot of questions, and they’re trying to figure out if the product they have suits what you need. And and if it doesn’t, that’s fine.
00:17:38 – 00:17:58
Lou Shipley: They’re going to keep moving on to find the right person. So I found having come up through sales, the best salespeople are really good at qualifying. Customer need understanding their product well enough to see that it really could solve a real problem for for the customer. So I think I think you’re still like overcoming the disdain of sales.
00:17:58 – 00:18:16
Lou Shipley: Like one of the things I start with in my class, Sophie, is I put up a no soliciting sign, which is like, that’s the only function in business where someone says, please don’t do this, please don’t sell me. Never see no marketing or no finance or no strategy. It’s always just no sale. And so I think people have to overcome that.
00:18:16 – 00:18:35
Lou Shipley: And I by the way, I, I’ve been really fortunate to teach some great students that started being really fearful of it. And these are people from great companies, obviously, you know, qualified people coming into these schools with MIT and Harvard, and then they overcome their fear and then they love it. They actually they don’t really want to do anything else but sell.
00:18:35 – 00:18:44
Lou Shipley: They like it so much. So I think it’s partly this evolution of overcoming your fear and then learning what good is and then, leading by example.
00:18:44 – 00:18:53
Sophie Buonassisi: I have a strong belief that it’s never the what, it’s the how. And so sales can look different in so many different circumstances. But how you actually conduct the sales everything.
00:18:53 – 00:19:12
Lou Shipley: Well, not only that, I think that’s exactly right. And and I guess you guys are early stage investors. I do a lot of early stage, but once you get to a certain point, maybe it’s a a few million in sales or whatever, you can learn everything you need to know about a company by just going out sales call, you know, you can find out the customer like what’s the competition’s your pricing and your customer support.
00:19:12 – 00:19:30
Lou Shipley: Good. Is your sales rep any good? Like just do that. One thing and you learn everything you need to know. There’s no other place where you can learn so much so quickly. And each time I was CEO, the companies that I would first start selling and then I would man the customer support lines to see what the problems were.
00:19:30 – 00:19:31
Sophie Buonassisi: How long would you do each for?
00:19:32 – 00:20:02
Lou Shipley: Well, I would actually, as a sales leader and in a in a company, I would actually sit with the sales team almost all the time. And I like to just be out with the energy. But but I also wanted to spend time on the on the phone lines where hearing what customers didn’t like, and I would do that for, you know, at least a couple, a couple hours every month and then get from where the customers were saying to me, well, I would understand, as opposed to it being filtered through product manager or head of customer success, I wanted to know really what the customers felt.
00:20:02 – 00:20:12
Lou Shipley: And so being close to the customer, not only on the good relationships where things are going well, but in the bad ones where they could go really badly and churn. You need to be you need to be on top of that.
00:20:12 – 00:20:27
Sophie Buonassisi: And that’s such a personal way of doing it, of being the president and CEO and actually sitting with the sales team day in and day out and absorbing. So kind of learning by osmosis, how do teams do that in a scalable way? Or maybe not. Not every week. And sit with the sales team every day?
00:20:27 – 00:20:48
Lou Shipley: Yeah. No, that’s a really it’s a really good question. I think. I think what you find as a CEO is, there’s always something in the company that needs work. Like it could be that your, your sales is taking off and doing very well, but your, your rev ops isn’t or your marketing needs work or you still have problems with product or customer success or finance, there’s always something.
00:20:48 – 00:21:09
Lou Shipley: So I think a good CEO is spends time in the entire company. I just liked being with the salespeople because I could feel the energy of the goals we were trying to trying to make, and when and when we lost. Like, if you don’t win all the time, you sometimes losing it’s hard and sort of leading by example, even when you lose, I think is an important and important thing.
00:21:10 – 00:21:30
Lou Shipley: One of the things I found at Blackrock was I asked everyone in the senior management team to be an exec sponsor for strategic accounts, and this put people outside of their comfort zone, like our head of HR, who was terrific, by the way. She just didn’t really like having to call customer. She wanted to run HR. It’s like, well, no, you if you’re going to have a function here, you need to know what our core value prop is.
00:21:31 – 00:21:46
Lou Shipley: And and it it’s so I think it’s really important. And the customers get it. If you’ve got a senior person talking to you they know you know at a senior staff level, they’re probably talking about, you know, you as a as a company. So I think it was really good for customers.
00:21:46 – 00:21:53
Sophie Buonassisi: That’s a really interesting approach. So no matter what function even if not on the go to market side, every senior executive is assigned, you.
00:21:53 – 00:22:16
Lou Shipley: Know CFO or chief marketing officer CTO. That was sort of very natural because off times a product people would be talking to the big customers. But the other thing I did, you know, when I first got to Blackrock, we had not surveyed customers on a daily basis or weekly or monthly. We did like annual survey. So we brought in a surveying tool, Net Promoter Score, for a company called Customer Gauge, which I’m still involved with.
00:22:16 – 00:22:33
Lou Shipley: And what happened was I would get if anything was 0 to 6, which is a negative score in NPS. I would just get it routed to my desk. So if a customer sort of was really unhappy, I remember Amazon gave us a zero once they were big customer and I called the person said, hey, I’m the CEO. Blackrock.
00:22:33 – 00:22:38
Lou Shipley: Why did you give a give us a zero? And he’s like, oh, I wasn’t expecting you to call me back.
00:22:38 – 00:22:40
Sophie Buonassisi: Yeah.
00:22:40 – 00:22:55
Lou Shipley: But you have to, you know that sends a message to the customers. We’re listening to you and you know how you feel like if you buy a product and then the customer support, experiences is lousy. You sort of feel like, oh, I know there was a competitor next time.
00:22:55 – 00:23:20
Sophie Buonassisi: Yeah, yeah, exactly. 100%. A little bit of a bait and switch you can feel like in that regard. And now you mentioned rev ups and marketing earlier. And I know you’ve written extensively about forecast accuracy. Yeah. And the single version of truth as it pertains to sales in the entire go to market motion from the rev ups, ones like why do these forecasts typically break down between sales finance, the board whoever else.
00:23:20 – 00:23:23
Sophie Buonassisi: And and how do you fix that. How have you fixed it in the past.
00:23:23 – 00:23:51
Lou Shipley: Well, I mean, I’ll tell you something. I, I have a I’m, I’m still focusing on on new mistakes. Right. I’m trying not to repeat the old ones. I’ll tell you the mistakes I made that led to the observation about how to do it. The first and the biggest one for me was was having marketing align with sales and not sort of fluffy kind of marketing goals where they could evaluate themselves, meaning like brand or marketing activities that we did if it didn’t drive sales.
00:23:51 – 00:24:16
Lou Shipley: This is an A, you know, obviously B2B infrastructure sort of enterprise software setting. But if it didn’t, if the activities they were doing didn’t drive sales, then they shouldn’t do them. And and I think there’s still this temptation to bring in a marketing person that’s going to build brand, and not that brand isn’t important. It is. But in the early stages, you only survive based on whether customers buy your product, because your venture capital funding will run out if you’re not acquiring customers fast enough.
00:24:16 – 00:24:34
Lou Shipley: So I found out I had to get the right people that were the sales and marketing leaders could really collaborate and work as a team, which I did it at Black Dog, and then I put them on the same comp plan, like they got paid when we made our sales numbers. So you didn’t have this? Well, I want to be paid for doing this marketing thing because I don’t control sales.
00:24:34 – 00:24:57
Lou Shipley: It’s not about controlling, it’s about your activities. Need to drive it. So I found that that was the way to eliminate, you know, the refereeing you do as a CEO between the different groups. Now on the rev up side, in that single version of truth, really having great sales or rev ups is so important so that you know really where you are so you can build as a CEO, build, confidence.
00:24:57 – 00:25:13
Lou Shipley: And then, you know, your reputation will grow with your board that you can really forecast. And if you say you’re going to miss and you miss, well, at least you knew that. But you know, what happens in early stage companies is CEOs don’t know how to forecast. They tell the board they’re going to make the numbers and then they miss.
00:25:13 – 00:25:27
Lou Shipley: And then soon enough you might be out of a job. So you really have to know, you know, how you’re doing and seeing if you can get ahead of some of the some of the predictable measurements of how you’re doing in the future.
00:25:27 – 00:25:55
Sophie Buonassisi: And this is probably one of the hardest times to do that. Also, just with, a lot of kind of experimental revenue being put towards a generic solutions. And I, I Jean DeWitt, she’s the CEO of resell, for example, she came on and talked about how they’re in such an interesting challenge from a forecasting perspective, because a certain percentage of their revenue is experimental, and they know that probably won’t carry forward, but they can’t predict they’re not in the prediction business how much that is.
00:25:55 – 00:26:25
Lou Shipley: It’s such an interesting point. And like I was talking to one of the boards I’m on, starting the head of customer success yesterday around lunch and talking about what are the what are the leading indicators and all these things for, you know, forecasting and for customer success, customer satisfaction. And one of the things we found was that you need to be able to, forecast the strengths of your champion and whether they can, you know, help you get renewed and get growth in your business.
00:26:25 – 00:26:55
Lou Shipley: Because to your point, there’s so many solutions out there that say, I enable this and that. It’s so hard for the big customers to figure out which products do I use for which things, because there’s there’s just this huge mushroom cloud of all these different companies. So trying to understand your the strengths of your buyer and of your champion, because if in this case, the company went on to champion has left they’ve churned accounts and that’s that’s really painful once you’ve closed really good accounts to term.
00:26:55 – 00:27:07
Sophie Buonassisi: Yeah, exactly. And you’re on the recipient as a board member and receiving that forecast and seeing it play out in real time. So that’s great advice for anyone on the input side of actually putting together that forecast for the board.
00:27:07 – 00:27:30
Lou Shipley: Yeah. And I think that there is something to having kind of been from all different perspectives and all angles, having been, you know, salesperson at a start up, a CRO, a CEO now a board member, you kind of understand and and see from different angles. You know, the CEO wants to be positive, but if things aren’t good, you you’re better off being honest with the board about where things really are.
00:27:30 – 00:27:45
Lou Shipley: And likewise, as a board member, your job is related to help them and not necessarily judge them. It’s just like, that’s why all I want to hear about in a board meeting as a board member is bad stuff. I don’t want to hear all that good stuff. Just tell me what’s wrong and maybe I can help you.
00:27:45 – 00:27:51
Lou Shipley: Because that’s, you know, I don’t want to. I don’t want to get PowerPoint into depth about how great everything is.
00:27:51 – 00:28:07
Sophie Buonassisi: Yeah. Yeah, that’s a very good point. That’s a funny balance. People have to strike around being able to showcase the value that they’re bringing, but also get their their problem solved or their other big kind of tips you’d have from mistakes, if you will. You’ve seen people make presenting to boards.
00:28:07 – 00:28:26
Lou Shipley: Well, it’s a really interesting question because you know what? Whatever function you come up through to become CEO, whether it’s product or finance or sales, you know, you’re familiar with that function. Like you could look at the finance group and understand exactly where you are, but what you don’t have training for as a first time CEOs. What how do I manage this board?
00:28:26 – 00:28:45
Lou Shipley: What is this thing? I mean, it’s you know, and you can get it really wrong and and you know, you have venture investors that have owned big chunks of the company. You have independent members. They’re kind of different. They have different roles that they’re supposed to play. So there’s no training ground other than on the job training. I’d like to create a course at Harvard Business School for this.
00:28:45 – 00:28:58
Lou Shipley: I’m just sort of too busy right now about like, how do you manage a board? Like what should you be thinking about as you’re getting ready to become a CEO? Because it’s it’s really hard and you’re like, I don’t know what’s going on here. And you’re you’re kind of the odd person out.
00:28:58 – 00:29:12
Sophie Buonassisi: Yeah, definitely. And you talked about the experience of going from the first time CEO. You’ve been a multi-time CEO. What were the biggest takeaways that you took from the first time experience over to the second and subsequent experiences?
00:29:12 – 00:29:35
Lou Shipley: Yeah. Thank you for asking that. I think coach ability, I really wasn’t very coachable the first time I thought I had all the answers and, brought in a lot of things from previous companies that some of them work, but a lot of them didn’t, I think, coach ability, owning bad hires like you as a CEO, if you bring in somebody that isn’t working out, you have to fix it.
00:29:35 – 00:29:53
Lou Shipley: Because if you don’t, your high performing team members are going to try and compensate for you, and they’re going to just they may not tell you directly, but they’re getting mad at you. So, you know, basically you have to own the hires and on the team and promote the right, right, right people and not promote people that, you know, haven’t earned it.
00:29:53 – 00:30:13
Lou Shipley: So trying to keep politics out. And then I guess the final thing, what I really learned the most at Blackrock was the importance of culture. And I think we had mentioned before in our prep about I created a role called the VP of Culture at Blackhawk, which was that senior team, meetings. It would be on house sales, house product, house finance, house marketing, house culture, house culture in Boston.
00:30:13 – 00:30:30
Lou Shipley: How is it in San Jose? How is it in London? Housing in Tokyo? And when you really commit to it, the people in the company really realize you’re focusing on it and you care about how they feel when they get up and go to work each day. And I felt like that was actually the the strongest thing we created at Blackrock was our culture.
00:30:30 – 00:30:48
Lou Shipley: We had great products, we had a great go to market system, but our culture was like no one should compete with that because people want to work there. They wanted to bring their friends there. They stayed a long time. They committed to the mission, and work through really hard times. And it wasn’t really about compensation and benefits or equity.
00:30:48 – 00:30:51
Lou Shipley: It was about being part of a great culture.
00:30:51 – 00:30:55
Sophie Buonassisi: What were some of the top ways that you found to be effective in fostering a positive culture?
00:30:56 – 00:31:06
Lou Shipley: Yeah, no. You have to be careful not to sort of put the, you know, the what do you call it, corporate objectives on the, on the wall or, you know, we, you know, all the sort of.
00:31:06 – 00:31:08
Sophie Buonassisi: Yeah, the foosball table is,
00:31:08 – 00:31:33
Lou Shipley: Yeah. It’s it’s so interesting because it’s not just that I think there’s a certain amount of energy that matters and fun and competition and team orientation, but I think, I think it was, every, every department in the company, engineering, finance, customer success, not just sales, had to realize that you were really serious about culture and about how you felt, at the company.
00:31:33 – 00:31:53
Lou Shipley: And we started before I got there. There really wasn’t a performance based culture. So we started with performance based, you know, what does that mean? What’s what’s incumbent upon you as employee? What are we going to do as a management team? And then as we started to perform, I thought the, the biggest, lever and the biggest way to really grow the culture and keep it going was to create kind of like a learning culture.
00:31:53 – 00:32:18
Lou Shipley: So people said like, yeah, I’ve got good compensation, I got a good boss, I got good equity, I’m learning. And I think people want to learn all the time. And so we would do all kinds of learning libraries and bring in speakers, and they weren’t necessarily to do with our product, but it was about are you learning? Are you getting better because because employees realize if they’re getting better than they’re more marketable when they move off to the market and move on from your company?
00:32:18 – 00:32:29
Sophie Buonassisi: Absolutely. That’s incredible. A VP of culture. Maybe we’ll see more of that coming up too, is people realize culture is actually a go to market asset, as opposed to just more of a nice to have.
00:32:29 – 00:32:53
Lou Shipley: Well, and every company has a culture, right? It may not be, you know, may not be talked about, but it happens. And and we actually there’s actually a case written at Babson about black talk about the change of culture from the founder, Doug Levin, who was an amazing founder to me, and about how the culture changed and from a founder’s culture to a CEO’s culture and how usually people think you can’t do that.
00:32:53 – 00:33:02
Lou Shipley: It’s always the founder. But in my case, it really did. It did change. And but we had to I thought that’s what was one of the biggest differentiators for the company.
00:33:02 – 00:33:18
Sophie Buonassisi: And what have you seen across multiple organizations around that transition of founder culture? You know, founder led sales overall, the founder taking that front seat to suddenly giving the reins to somebody else to run what has proven to be most effective or challenging.
00:33:18 – 00:33:39
Lou Shipley: It’s so interesting because I’ve been through this a number of times. I’ve seen it in companies I’ve worked at, I’ve seen it in companies where I came in as a CEO. I’ve seen it as a board member making that transition. And it’s hard. It’s hard because if you have the idea for a company and you get to a certain size, I mean, you took it from idea to business and that’s that’s really hard to do.
00:33:39 – 00:34:05
Lou Shipley: It’s just that recognizing the skills to take it from 50 million to 100 or 200 are often very different skill sets. Not always. Some founders make the make the transition, but a lot of them struggle with not having everything go through them and being learning how to be really good. Delegator is again, that’s the point of like chapter four is about leadership and putting your team together and then building the team that does the work, and you aren’t in the middle of everything.
00:34:05 – 00:34:24
Lou Shipley: And I think that’s just hard for some founders when they it was their idea. They got the first customers, they got the first financing, first wins. It’s like, why am I not in the middle? And your job, I’ll tell you, does a really good job with this. On the board of a company called teamwork. Zach Marie is a terrific founder who’s really scaled into a great CEO.
00:34:24 – 00:34:43
Lou Shipley: That’s rare. It’s very rare to be a great founder and a great CEO. I’ve seen great founders and good CEOs, but it’s very rare to have someone who can really learn on the job about how how their job has changed right underneath them, and if they’re going to continue to do the things that work when you’re like $1 million company, when you’re $100 million company, you’re going to fail.
00:34:43 – 00:35:05
Sophie Buonassisi: Absolutely. And now we’re talking about a little bit later stage is, as founders are, and passing off or evolving into that CEO role. What about earlier stage. Because you have to work with a lot of early stage companies to be it through investing or other means. It’s a founder only had to get, you know, three, for example, go to market things right in the first couple years.
00:35:05 – 00:35:08
Sophie Buonassisi: What would give them the most leverage from your perspective?
00:35:08 – 00:35:43
Lou Shipley: Okay. Yeah. What would what’s the most important thing? It’s it’s understanding customer pain. Understanding. Qualification of of deals so that you understand what, what, companies should be in your sales forecast, the ones that you’re going to be talking to your board about and being really strict about what gets in there, because it’s really easy if your sales team isn’t trained to put somebody in the forecast because you had a good conversation, but it isn’t necessarily moving through the stages to a, to a closed deal.
00:35:43 – 00:35:54
Lou Shipley: Adam Clayton, who was the CRO of Black Duck, used to have a term called for forecast furniture. This was stuff that you put in the forecasts. That was a piece of furniture. Didn’t move.
00:35:54 – 00:35:57
Sophie Buonassisi: Right. It’s easy to try to say yes.
00:35:57 – 00:36:24
Lou Shipley: Understanding pain, understanding, like the stages and why why thing, why companies aren’t progressing through the stage. And then and then it’s back to the coach ability and coaching and getting enough people to understand what it takes to build a system or not. So it’s not just every sale is sort of a heroic diving catch by somebody who can just happen to sell something that’s really hard to sell.
00:36:24 – 00:36:35
Lou Shipley: And that’s oftentimes, you know, first, customers are really hard to get in and startups, but you have to move beyond that diving catch mentality to see more of like, not an artist, but sort of a member of a marching band.
00:36:35 – 00:36:49
Sophie Buonassisi: Excellent. Excellent advice. And now when you are evaluating early stage founders and companies, what are the things that you pay most attention to or that stand out for you?
00:36:50 – 00:37:13
Lou Shipley: Pain and understanding the product, the pain the customer must be in to to have this be a really a killer product coach ability that’s back to you. Because if you’re not coachable and you are so determined and it takes it’s so hard to be a founder and you have to be an attorney, you have to overcome such great odds that you stubbornness is actually works for you in certain stages.
00:37:13 – 00:37:32
Lou Shipley: But then if you’re not coachable, then you’re sort of missing what everyone else is seeing as a business transitions. And that’s that’s where it’s got to be beyond you to really recognize that there’s there’s a system out there that needs to be created. And it may not be you. I mean, I honestly like the smaller companies. I did it a lot of companies that got to be really big.
00:37:32 – 00:37:50
Lou Shipley: And then it wasn’t that happiness where I went. Did other startups or my companies got acquired by big companies, and I stayed for a while, but not that long because that’s just not where I, I belong. And so not making a value judgment. Some people like smaller companies, some people like bigger companies that take, you know, incredible skills to do both.
00:37:51 – 00:38:02
Lou Shipley: It is, I think, part of what the education for a person is, is like where am I happiest? What size company? What, what scale of company do I really enjoy? So it doesn’t feel like work?
00:38:02 – 00:38:24
Sophie Buonassisi: Yeah. Finding that spot personally. And you’ve taken companies through so many different areas of the market and different points in time, and you’ve kind of written recession playbooks or founders in a way, like when growth slows and it’s not great, it’s hard to get good at. It starts go down. What should founders do first?
00:38:24 – 00:38:48
Lou Shipley: Yeah. No, that’s funny you say that because one of my classes, the second class I teach at the business school, Harvard Business School, is is talking about this. You’ve got the initial product market fit, you’ve got the growth, and then you have churn. Why? What’s happening. And oftentimes what happens is your product market fit changes as you try to sell more of your product to to your current customers or to a broader set of customers.
00:38:48 – 00:39:15
Lou Shipley: You realize that the user’s your ideal customer profile may have just changed for the way you’re selling your product, and you’re blind to it and the the the symptom is churn. But then it’s like, well, why did I churn? Well, you know, you got the customer originally, but they didn’t stay with you. So understanding usage early on in the customer journey, who’s using it and how heavily are they using it as opposed to using revenue as a metric for product market that super interesting.
00:39:15 – 00:39:21
Sophie Buonassisi: Yeah, it sounds like churn is more the lagging indicator. And it’s, diagnosis of all the different inputs that lead to that point.
00:39:21 – 00:39:38
Lou Shipley: That’s kind of what I’ve found in the many years I’ve been in. This is always trying to think through it and think differently about what could be the leading indicator of something that’s going wrong. And and that’s why I love this business is it’s so changing all the time. And what worked in a previous generation just doesn’t really work today.
00:39:38 – 00:39:47
Lou Shipley: And that’s partly why the sort of creative destruction of the software technology business leads to so much growth. Is it just it changes everything.
00:39:47 – 00:39:54
Sophie Buonassisi: And Lou, I’ve got a couple last questions for you. Sure. Are you ready? Yep. Awesome. Are there any life mottos that you kind of live by?
00:39:54 – 00:40:18
Lou Shipley: Yeah. I mean, I’ll, I’ll pick I’ll pick one that, may not be. I don’t know if you’ve ever heard this person quoted. He was actually the only, commoner to ever ascend the English throne. Oliver Cromwell. He’s not usually quoted, but he said a few good people are better than numbers. I’m actually a big believer that what you just need is a really strong small team.
00:40:18 – 00:40:34
Lou Shipley: You don’t need a lot of numbers, and it’s so tempting when you have a company that’s growing to like, hey, I got 100 people, I got 500 people I like, but how good are they? I’ve been on a lot of winning teams that just have a few. And then, you know, you have to have role players as well, but you don’t need that many people to do something great.
00:40:34 – 00:40:52
Lou Shipley: So I like that. The other one that he uses is he stops getting better, stops being good. And I think that’s really true because like if you’re not getting better every day, whatever you’re doing, I don’t think you’re gonna be any good at the end. Like, you know, like you can’t ever rest and think, oh, I’m, I’ve done well.
00:40:52 – 00:40:57
Lou Shipley: So it’s that’s it. You have to keep reinventing yourself and keep learning new things.
00:40:57 – 00:41:23
Sophie Buonassisi: Those are incredible, incredible words in quotes. And the first one, really, I mean, it’s interesting. It makes me think of the former CRO of Pro course named Dennis Landers. But he talked a lot about prices law and when he scaled price for interesting. Yeah, over eight and a half years, he had this holy shit moment where he was like about, you know, the square root of a certain amount of people at this company are the ones driving growth.
00:41:23 – 00:41:33
Sophie Buonassisi: I of 100 people, for example, 15 people are are disproportionately epic. And that’s actually what’s driving the growth. So it sounds like that same kind of notion around that first point.
00:41:33 – 00:41:51
Lou Shipley: Yeah. Well you see it all the time with small groups can do great, great things. And and it’s one of the reasons why it’s so important. I used to say to my first in my first startup, I said to the board, we had to be ten for ten, 11 for 11, 12 or 12. As you hire each person, they have to be the best for you.
00:41:51 – 00:42:10
Lou Shipley: It’s hard, like when you can be a big company like Google or Amazon. It’s really hard because you can’t have all superstars. But in this sort of earlier stage piece, I think it’s really important to to have a really high bar and then do 3 or 4 jobs yourself if you haven’t found the right person and that’s you, by the way, doing 3 or 4 jobs yourself.
00:42:10 – 00:42:16
Lou Shipley: You learn a lot about those functions. Anyway. This is a no one can do this to you when you when you do put them in.
00:42:16 – 00:42:39
Sophie Buonassisi: Yeah, exactly. Good boy, good boy. You have a book out yourself which is super exciting. Unlikely entrepreneurs talks about the wins or losses, but the really crucial lessons on building great companies, which we’ve talked about a little bit today, other than your own book and you’ve been busy writing, are there any other books that have really been impactful throughout your career?
00:42:39 – 00:43:02
Lou Shipley: Yeah, actually, I just posted yesterday on, LinkedIn, 19 books that my coauthor and I recommend for entrepreneurs. I’ll mention a couple of them. One is, Jeff Kang has a new book out, called The Experimentation Machine. It’s about AI and startups today. That one’s really interesting. Marco Bear’s sales acceleration formula is really good for understanding.
00:43:02 – 00:43:23
Lou Shipley: Like, the systems and putting systems in place for for selling. I read a book recently that I found was really interesting. It’s called Captain’s Class. And if you’re we were talking about sports before, it talks about if you wanted to do a data driven approach of what to find the best sports teams of all time, and you might think it’s talent, you might think it’s coaching, you might take it’s payroll.
00:43:23 – 00:43:51
Lou Shipley: What he decide what he found as a top 1% of the top 10% was it was a strength of the captain. The people that are the glue of the team, not necessarily the superstars. The strength of the captain is what determines great winning teams. And what’s really cool about this is I got really excited as I read this book was he talked about when teams start to form really well and, and and understand each other and don’t need like even verbal communication, they can just communicate because they know each other so well.
00:43:51 – 00:44:09
Lou Shipley: They develop what he calls a shared cognition. I think this is really cool because great companies have that there. They work as a team, they know each other, they win together, they lose together as a team. And I just think that’s a really interesting concept, and that’s really what you’re trying to do as a founder is build a team that can win.
00:44:09 – 00:44:15
Lou Shipley: You’re not going to win all the time. You’re going to have losses. But how do you keep working on that to build something greater than yourself?
00:44:15 – 00:44:22
Sophie Buonassisi: Incredible. And can you leave us with a couple of last notes on the book itself, which is available now and will be in the show notes?
00:44:22 – 00:44:47
Lou Shipley: Yeah. So we profile, 13 different, unlikely entrepreneurs. They’re really fun people, really entertaining stories. We have 17 experts that weigh in on what they did well and what they could do could have done differently. And so it’s really about storytelling. It’s not sort of a sage on the stage book. It’s more like these are interesting, compelling stories that interest my coauthors are really good storytellers.
00:44:47 – 00:45:10
Lou Shipley: So she sort of brings these stories to life. And then the seven chapters of the lessons are start with, as I mentioned before, the problem or the problem with the problem, understanding the going of your problem. And is it worthy of building a company sales? We’ve talked about that today. Financing, how you finance your company, leadership, marketing and pivoting because oftentimes your product, you know, your company fails and you have to pivot.
00:45:10 – 00:45:23
Lou Shipley: You have to change. And we profiled people that pivoted really well. And the final one is, you know, endings and beginnings. You know, entrepreneurship is a second act. So we sort of combine these great stories with seven, seven key lessons.
00:45:23 – 00:45:37
Sophie Buonassisi: Incredible. Well, I highly recommend anyone check it out. Is available now. Lou, thank you so much for the time sharing all your insights across every aspect, you know, beyond the book and even just to your experience leading multiple companies. So thank you.
00:45:37 – 00:45:38
Lou Shipley: Enjoyed speaking with you.
00:45:38 – 00:45:39
Sophie Buonassisi: Absolutely. Thank you.
