Why Founders Who Avoid Sales Always Fail with Lou Shipley

hey everyone welcome back to make it happen mondays where we talk about sales business entrepreneurship personal growth mental health and everything in between with guests who i truly respect and i think make a positive impact on the world around us now today's conversation is with lou shipley he is a senior lecturer at harvard business school at mit sloan where he teaches four sales courses to over 500 mba students a year he's been a ceo multiple times most notably black duck software where he sold to synopsis for 565 million dollars before that he was employer number five at webline zero to 15 million cisco bought it for 325 million he opened avid technology subsidiary in japan and ran their asia pacific business he's an investor through stage two capital sits on the boards including wasabi and he's got a new book out called unlikely entrepreneurs co-authored by trish favreau topics we got into this was a really cool one because i'm all about sales education ideally you know sales education in the universities right because it's just such an under educated profession it's always the default profession it's always frustrating me so whenever i get to talk to an educator who's doing it in college i love it but we started with how he paid his way through college selling door to door uh 12 hours a day getting kicked out of towns refusing to actually i think he almost got arrested for not having a solicitor's license and he called that his character building days which i think is great um also we talked about why our culture has such a disdain for sales and how you know he actually runs the sham wow exercise for his harvard business schools and tell talks about the perception and then the reality of it and he loves to see when they click and realize what sales actually is and we both are directly aligned on that he's actually gonna call um also in his book he's got a chapter called delegate sales at your own peril which means so many founders think oh i got this great product and i gotta delegate it so you know let me just hire a sales rep and that is one of the worst things founders can do and then we got into this the sas desk brow right now what's happening with ai and how sas has got to survive because he's advising a lot of these companies and i also had some fun with the guy kawasaki experiment that i ran with him or that i ran and then told him about and talked about how i knew i was in trouble as soon as guy didn't have a good answer for me when i asked you know what's the point of our conversation if i can have it with your gpt so this was a really good one because i think the future of sales is in undergrad and grad and you know the days of starting sales after school you know because you got your degree in whatever crappy degree you wanted and then getting into sales at ground zero with no experience i think those days are over so the more we can educate early the more sales professionals have a chance so hope you enjoyed the conversation as much as i did let's make it happen hey real quick if you heard me last year you know i stopped taking manual notes on all my sales calls yes i'm still using otter.ai but now i'm using their desktop app which means there's no bot jumping into my sales calls and honestly it's become way more than just a note taker with the desktop app otter captures all my sales calls and turns them into searchable insights that sink straight into my crm and then i can ask otter chat any question about any meeting or conversation i've ever recorded the best part chat is now connected with all the tools i use so if something's buried in tools like notion google drive gmail salesforce whatever i can still find it all without leaving otter but here's what i actually love about it the knowledge doesn't disappear when the call ends it lives in otter i can spot patterns across my pipeline remember exactly what was said and walk into my next call way more prepared the time it saves me is absolutely ridiculous and that's before you even get into what it does for teams i'm partnering with otter to give you an exclusive offer go to otter.ai forward slash jbsales to learn more and start selling smarter today lou shipley welcome to make it happen monday podcast my friend how you doing today doing well john thanks for having me i've been looking forward to this conversation because uh the academic side of the house from an education on sales has always eluded me and it's always been curious to me that this is the number one profession in the world but yet none of us are actually formally taught how to do it so i am extremely interested in getting to your what you're teaching over at harvard um especially on the nba side of the house but before we get there because you got a good book coming out and i think it's a timely uh conversation to have in a lot of ways but i always love the origin story my friends you got some cool stuff you were selling encyclopedias you went to trinity so back let's back up a little bit and figure out where what were the foundational components that made lulu like you're you know from your parents to your upbringing and those type of things where'd you catch that bug of sales and entrepreneurship and all the fun stuff so yeah yeah i can't find on linkedin yeah okay so so i actually got waitlisted at trinity and needed financial aid and uh as a result i needed to figure out a way to make some money and there was a company called the southwestern book company that offered maybe you remembered it 100 commission sales job so i uh the went to training uh started selling books door to door i had a little trouble with the law because i wouldn't buy a solicitor's license so i got kicked out of one town i made enough to stay in school and more than more important than the money was uh learning about how to handle rejection and failure and um that was a really great sort of basic story and then i uh basic sort of learning and then i um ended up going to um harvard business school would partly be in the second year i took a class called entrepreneurial finances which was how to how to finance an idea how to create a startup how to create something for nothing and this just john this just grabbed me this was like this was passion for me so uh since i was was not afraid to cold call i cold called the founder of avid technology who took my call and said you know you seem uniquely unqualified for a career in technology nice you went to trinity and studied history and then harvard like nah so i said well just let's just meet and i just started as a consultant and then avid didn't have somebody selling their system down south so i started selling and then they came to me and said hey would you take the rest of the world because someone has u.s and europe so i was off and running moved to japan opened asia learned and that was sort of like early ceo training because when you're in the field as a sales person as you know you're like a field marshal you're running all the functions and i was i did that in japan for three years and from there i just did a bunch of other startups and then became a ceo on my fourth one i love it so you said it actually part of your book you said the founders must become chief salesperson so was that was that kind of what dawned on you at avid was you know yes you were president yes you were i mean first of all you went to avid which did didn't avid do like uh edit video editing and you were video editing yeah like complete pioneer you know completely changed the industry it had been on film and videotape and this was a digital version of it so cutting and pasting full motion video you went to japan where sony was oh yeah yeah yeah yeah that's the best that's i was so excited everyone's like why are you going to japan well that's who owned the market and we needed to dominate in their home market and they didn't even know what digital video was you know what they had done was sort of replicated the original vcr and miniaturized it and commercialized that um it was the first vcr ampex you know american invention was the size of a volkswagen but the japanese really figured out how to miniaturize it so we lost that whole industry but then when the digital video industry came along and everyone said you know you can't fight japan so i'm like yeah you can and we're going to do it in their home market and they didn't have a digital video editor for like 10 years i was fascinated at how how easy it was to win in their home market but it was great it was great i learned a ton about selling in other cultures i was gonna say like what was some because japan is such a different culture uh i love japan i thought i i the first couple of times i visited it's i think it's one of the most fascinating cultures i've ever been to in my entire life um every i mean it's just it's it's chaos but it works like there's so many people like i couldn't believe that when i was there you know that where you know where all the um that the intersection is where like the 10 like things yeah yeah yeah my uncle when we're standing there he's like okay when the when the light turns red just walk straight and i was just like of course he's like no don't slow down don't stop just follow me and i'm like all right and then the light turned and a billion people come like mishing together and nobody bumps into each other nothing happens and it all just flows i was like what the just happened here like this is this is unbelievable so what was i mean you're in another country in a different culture that you're not i mean you're you got a family too right you were you brought your young my wife my wife moved over sight unseen and she's been uh she's been with me from the carter administration we started dating in the 70s but uh so we were high school sweethearts but she moved over and then our son clark was born in tokyo which was uh which is great but you're right it is such a different different culture and i loved it um from a sales point of view it's so different than selling here or in kind of a western society where one person can kind of make a decision right i remember selling nhk which is you know their national broadcaster the first abbot and it took the sales cycle took about 18 months it required 17 hankos which is the stamp we have a signature they have a hanko stamp 17 different people had to stamp the contract so it's really a group and consensus decision making uh process that i had to learn i had to learn how to forecast that because the americans are impatient yeah but but once you got into that market that was the biggest one in asia forest it was explosive we grew it like crazy it was so much fun and i hired some great people that are still really close friends great sales people in japan what was kind of what if you were to pull one big takeaway from that experience that you know that for instance is in the book or is relevant today uh that would be you know something for founders and people to think about what would be the one takeaway from the japan experience with that with avid um well it's it's to try and learn how uh how how the buyer wants to buy in their culture so it's it's actually quite similar to what we teach in our class that mark and i teach at hbs is thinking of it from the buyer's perspective as opposed to what so many sales organizations do you know i've got this product here the features here's the powerpoint deck here you go like no that's not how people want to buy no and that's and actually it's funny because you know i wrote a post a while back or actually an article i forget where it got picked up but uh i called it the founder's dilemma which is usually technical founders and what they do is they they i always say sales is the transfer of enthusiasm right like if you believe in which like because people buy on emotion they back it up with fact and if you so so the number one characteristic i think you need to be successful in sales is a genuine belief in what you do that what you do makes a real difference for the right person because that's the transfer of enthusiasm and what happens is with an engineer they create a product right or they do they build something and it's good right so and because they're passionate about it they go talk to friends families and fools like that's their first circle right and because they're talking to friends families and fools they usually get pretty good feedback oh that's a good idea and maybe one or two of them might give them a few bucks to buy it right whatever and then they're like oh this is easy everybody wants this i i vividly remember my first cto who was my friend from junior high school he was a technical person he's founded the company it services we went on a sales call when he when i was like fourth person on board we came out of it and he literally looked at me and he's like i don't know why everybody does i don't know why sales is so hard this is what he said i don't know why sales is so hard everybody needs this and i'm like you just saw the easiest part of the entire process here do you understand what it took to get that meeting and do you understand what it's going to take to close that meeting so the problem is they have this like inflated like oh this is easy so then they just outsource it to a vp of sales somebody else that person doesn't come in with a passion they don't come in with the knowledge they don't and they fail inevitably and then the engineer's like see i told you sales is crap and then they try to go marketing right and then they build it up and they're like oh crap i gotta do so so it's almost like sales is a second class citizen in these organizations and what i tell sales reps looking for jobs is look at leadership if leadership is engineering be very careful because and no offense to engineers they're smarter than you know they're build these beautiful things but if the mentality is the product is awesome you're not going to succeed in my humble opinion here am i am i do you see the same thing with found wow right it's it's it's exactly what john this is exactly what i'm talking about in the book the first chapter is called the problem with the problem and so many people now especially startups are so kind of cool now and the people are under pressure to actually start companies and and um if you don't understand viscerally the pain that your problem solves your cup your product solves you're you're in trouble so if you don't know how to do it instead of doing you said friends families fools you know i i have i created a course for this specifically at hbs around if you want to start a company you have to make cold calls record them we're going to listen to them in class and see if customers have pain if they have a propensity to buy if there's a complexity to see i was just talking to john mcmahon you must know john and he was he and i were geeking out on them that's exactly what what he talks about when you're looking at companies so and then delegating sales you do so there's a chapter in the book called delegate sales at your peril because then you don't create the sales culture that you want and understand how each company is unique and needs to have specific comp plans and and sales processes based on what your buyer wants and you can't cut and paste from other companies what do you so one of the things that a lot of founders do even just say they buy into that okay i gotta go sell right and and they do in a lot of ways like i i gotta go out there i gotta either raise funding right which is selling or or i gotta sell my products so one of the things is a lot of um intellectual capital stays in their brain right of how they do the things that they do the what do you suggest they how did how do they document i guess to to be able to even if they don't understand the process of sales they're doing it and there is a process to it and like the certain objections that they face how long certain things take what you know how do you suggest you you build and ride the bike at the same time um yeah and and collecting what insights and information so you can create some type of a framework for somebody else to be plugged in it yeah no that's great question so first i think the first step is to overcome your disdain of sales our culture has a disdain of sales there's no other function in business has a sign like a no soliciting sign which is a euphemism for sales yep but you've never seen no marketing or no finance or no strategy no those are fine but sales no we don't want sales and yet it's the most important thing everybody has a top line right everybody and so um i think it's first overcoming that disdain and misunderstanding of it and then once they realize oh this is what it is now i've got to practice it and get better and one of the things mark uh and i have done at hbs is you know we have 500 students in the sales class and we have 80 sales coaches so so we just record the calls and the coaches listen to them give them feedback so to your point they they start to realize oh this is what sales is it's not at all what i understood from you know media culture or anything like that this is something totally different this is really important and it's so fun to watch the transition especially talk about technical founders i've had both at mit and and harvard where students are afraid of it and then they start to to fall in love with it then they don't then they won't stop doing it they found out wow this is great i love this i had a woman uh shana opperman wonderful wonderful person ex-google started a company was so afraid of sales and she got good at it then she wouldn't stop it like shane now you got a delegate you're done then she sold her company like she's amazing yeah but that's exactly what it is it's just transition where people realize this is what sales is wow i didn't realize and can you believe how few schools have it's sales program it is unbelievable to me that it is the default profession always has well i will take that back yeah have you ever talked to um todd caponi by any chance i have not no so you gotta look him up he's a sales he's he's a he's a keynote speaker you know does sales training on he's got two books on negotiation they're fantastic by the way if you're looking for guest speakers i highly recommend him um but he's also got this pet project where he's the sales historian and he brings up store like from 1908 night and he brings up headlines that like everybody's freaking out ai is going to change everything he's like oh yeah well look at this headline back in 1912 when the printing press came out everybody was like holy shit this is going to and and what's interesting he and i forget what the timeline was but there was a time when sales was actually taught in high school and it was it was a respected profession and then it got away and then you know the 80s basically ruined it with cap you know the whole capitalism and wall street and all that crap um and then it turned into what it is but it it fundamentally is i tell this when you say that aha moment when i try to tell engineers i'm like it's if you think sales is about convincing anybody of anything you're doing it wrong sales about helping people solve problems or achieve goals period that's it yeah that's it yeah and and if you're and if your problem isn't big enough then why are we talking you know what i mean like like that's not that's why i like the perception is the perception do you find that the perception is is more based on people's experience with sales or is it the perception of the movies and the glengarry glen rosses and the wolf of wall streets that creates that perception uh really good point because we start our class with uh we play an infomercial of the shamwell guy because that's that's what i think people and then and then i asked you what how would you feel about buying something from this person and and you know the students come up with well this person is so convincing and so compelling and it's you know he's a presenter he could sell anything so that's what they think they think sales is so they they have to misunderstand they have to you know unlearn what the common culture is that they think it's presenting as you say convincing um and and it's and that it's not that it's asking questions and learning if what you have is a is a value but i have to go back to your sales history question this is so fun so i don't know if you know in in uh in 1865 what the number one product that was sold door to door in america i have no idea first of all uh ulysses grant's memoirs which was edited by mark twain was all sold door to door okay it was the number one best-selling book but the second best-selling product was was um lightning rods because everybody needed a lightning rod so it was they were sold door door to door so just for fun i decided to come up i wrote a little case at hbs called lightning rod dot ai right and i have the students sell me sell me a lightning rod and it but it goes back to the same but what is your problem well i'm worried about my house getting hit by light okay i may have something for you but instead of like memorizing the features and pitching you have to ask a few questions yeah so i love that that's why i'm curious for a sidebar here what what is your actual favorite sales movie right because everybody talks about the ones that i say when people say glengarry glen ross will for wall street boiler room i tell them those are my least favorite sales i love those movies they're funny movies they're hysterical but in my opinion that's everything that's wrong about sales in those movies so i i have a few favorites but i'm curious what if you would have identified some favorite sales movies like learning lessons like the true essence you know do you have one that stands out let me let me think about that because i i usually go to glengarry glen ross partly because i use it to sort of dispel what sales you know that this is what people think it is yeah so so the opposite right yeah right yeah so i wouldn't be my favorite but it's still a great teaching method i'll give you my two because i always give my my students these assignments i'm like here's your homework assignment you got to watch my two favorite sales movies my my second favorite you got to watch this one first because it's a little it's a little tough to get through um but it's awesome is um um pursuit of happiness okay so pursuit of happiness right when he's selling those bone density scanners against x right right and and like like talk about hard work like i thought i worked hard that guy's holding you know saving seven seconds of phone calls so so by not hanging up the phone so he can get to the place you know for his kid right you know but the problem with that movie is 95 of it's just brutal and then at the end you're like oh thank god right so that's why i always say you have to watch my favorite sales movie of all time afterwards because i'll loosen it up tommy boy right tommy boy is the greatest sales movie of all time and the reason is i talked to every rep and you actually alluded to it about there's a moment in every sales reps life where they kind of wake up and and they did it and it's just a little bit easier than it was the day before right they don't know what happened it just and i call catching your sales groove and it's when you stop pitching your solutions and you start having conversations about your solutions you start caring more about what the client needs as opposed to you know your commission check and oddly enough that's when your commission check goes through the roof and there's this beautiful scene in tommy boy where he catches his sales group right helen you look like a helen let me tell you why i suck as a salesman right and he goes through this whole thing oh i'm like jojo the circus boy the pretty new pet and then she's like wow you're sick you're twisted he's oh tommy like you tell me what we and and and in that moment he caught the essence of sales because he because before that he was trying to be his dad right you stick your head up a butcher's ass but no that you can't do that right like and then all of a sudden he saves the town so like it's this beautiful moment of confidence of relating helen you look like a helen right it's just this and i'm like you gotta watch that because it is it is what real sales is about right yeah so this is so interesting i i this is just really great so let me just a couple things so when i sold books door to door i did it for two summers and i made enough to to stay in school and um but i used to have i'd go 12 hours so you start at 7 59 a.m finish at 7 59 p.m sometimes i'd go 12 hours and not make a single sale like all you know so it's all rejection so i called those character building days yeah i'd say but then but then when you did make the sale though and it's still the same with these founders i work with like when they make a sale that feeling is so powerful it's like scoring the winning goal of the hockey whatever so i think there's that feeling of um you have to overcome the failure and i want to just give a quote of one of my favorite um uh writers neil simon remember neil simon did the odd couples so he said that um failure gets me up earlier the next morning than success and i and i just i love that because that's the essence of what you're talking about failure and and then but when you overcome it and learn how to do it well it's so it's so gratifying and then i found because i sold a couple companies to bigger companies and they make me a general manager but i didn't own sales i'm like i can't start a day without looking at my numbers like i i can't not have sales i love this book because i every day i look at where my right trying to figure out the relationship between marketing and sales i mean i have to have a number once once you love it you can't let go of it and and i think i agree it's but it's catching that because it's it's hard to get through that right it's the and what i'm you know and i'm gonna sound like an old man here you know but what the biggest thing that i'm worried about right now is is grit is absolutely because all the stuff that you and i did early in our careers you know just knocking on like i did knocking on doors i literally would get thrown out of office buildings you know that type of thing um you know writing down handwritten stuff right and that's actually going back to glenn gary glenn ross that i hadn't watched it in a while and uh and i saw it again it starts they're making cold calls in a booth at a chinese restaurant across the street from their office at nine o'clock at night i'm like oh my lord like that's what so but that grit right all that all that hard work all that stuff that you and i went through allowed us to be where we are right now as far as having this conversation we don't need a script you know we walk into conversations and and have the context my fear right now is two things one is the grit is is i don't know where it comes from uh anymore and and and the other thing that i actually would love your perspective on is the fundamentals i think the sas industry got away from them i might have a keynote called age of the agile sales org and i put i position 2010 to 2022 as the golden age of sales we were able to get away with just ridiculous stuff like i love predictable revenue model i've made a lot of money on that but i think it ruined sales the segmentation of roles and so the question is is how do we get what where do the fundamentals come from anymore more importantly what are the fundamentals in this world of ai what do you consider the fundamentals of sales so that the context to use this ai is there yeah well so let's go back to the uh your history talk got me because i was actually a history major but the um you know when the telephone came out all those door-to-door sales people well they were disrupted and so the ones that did well figured out how to start selling over the phone like now that's now that's gone just because it's a new new wave new wave of technology but every generation goes through these changes and to your point we were talking about earlier you need to now learn the new tools to use these ai tools to help you sell and and you better get good at them fast or at least not be afraid of them because if you are that's that's the real the real problem so you just have to lean in and get after it but how do you so the challenge though is it makes it so easy right now like again i call bs on claude all the time because i'm like nope uh whatever you wrote right there or whatever you would and now my 30 years experience tells me that's bs like that's a that's a that sounds like a good answer but it's not true or it's not accurate my fear is we've gone from this search engine to an answer engine and for the people who are curious that because that answer can't be right it's pulling from reddit it's you know what i mean like whatever so so but and for people who are curious like oh tell me more about that source check this give me a different perspective on this give me you know it's a superpower but for unfortunately for the vast majority of people out there who are just lazy they're going to take that answer and copy paste it and send and they don't they're not going to why that email should be written that way they're not going to why they should have the conversation with or or what aspects of the business strategy are relevant to have a conversation about and i'm just worried like how do you how do you use ai to learn while executing as opposed to just executing because i think that's what so many people are just jumping to write me a perfect email for this company write me a proposal for this company and it does it and it looks beautiful it's better than they could probably ever do but for some reason there's something wrong about it and they don't understand the learning and that way i don't understand the value of the human in that equation well it's an interesting question because you know we've seen um prognostications about how salespeople will be eliminated over and over again the last last big wave was plg yep you know like at last year it was like oh we don't have any sales people you know well look at the mark how much they're spending on marketing and they're just again it's the euphemism guess what dropbox tableau box uh click all of the plg who pray slack all of them who said i we don't need to guess who's trained every single one of those companies i've trained every single one of those companies sales teams to sell yeah yeah no exactly just to your point so so that was again it goes back to this disdain and misunderstanding of sales because people think it's the sham wow guy or whatever and instead so plg comes along we don't need sales people i i think everybody whether you're an individual or a company or a government like you have a top line and it's hard to make those numbers it's hard to grow fast so you you need you need to to use the tools to help you build it i mean and and claude i mean just we were just talking about it it's so good and getting so much better but i'm with you like i started writing my app for my book and it got a bunch of stuff wrong i just corrected it it's fine but you just can't trust this uh without questioning it so and i think i think that's partly why i'm actually going to give my uh commencement address at trinity this year nice and talking about sort of the value of a liberal arts education is that you you're it's judgment questions curiosity those are the things that are going to get us through this can you teach that i think you have to experience it um yeah i do think you can teach it but i i think you have to i think you have to experience it it's a little bit like what we're talking about developing the sales curriculum at harvard it started with 40 students this year same size class 10 years later it's 550 so people realize that i think people have to come to it themselves to realize you know that's why i never wanted to teach like required curriculum like the stuff that you have to take i just want to teach what they're interested in because then the engagement it's much more fun as you know you do you do this for a living you want people to be engaged yeah i i tell people all the time i live between the world of give a shit factor and unconscious competence i can't get you to give a shit i can't and i'm done trying by the way but as soon as you do i will give you literally everything that i got and what's that but this is the proof point for me that this is why i'm worried for the vast majority because i mean thousands of sales professionals thousands at the end of every presentation they have my email they have my instagram account and they have my phone number and i tell them all the time if you have any questions at all email me i will give you i will jump on a call with you if you dm me on instagram ask me a question i will respond and the amount of people that actually take me up on that offer is is a fraction of a fraction of a fraction of percent really yes interesting and i and i and i'm like you know look like you have to you know and and the ones that do i can tell i'm like you're gonna you know you're thinking about this the right way like because their questions are are thoughtful they're not just generic ones right but it's but that's the what i'm i think i've come to the thing with with curiosity i think you are i think you were either naturally born curious or not okay there's naturally genuine curiosity across the board but i do think that we can get people curious in things by getting them interested in things because if you are interested in something then you can get curious so it's breaking that barrier like to your point of like sales like oh the perception of sales let me show you a little bit about what this is let me get you interested in what it actually is and then it's like oh oh this is what it is now let me learn more now i'm curious about how to improve this right but it's breaking that barrier of getting them getting them interested so they can become curious that's a really good that's a really good point i think i was i was blessed i didn't realize it at the time but my dad was a college professor and so i grew up around lots of ideas i mean i i learned about sociology and economics and philosophy and religion and everything the way a college professor would teach it and i didn't realize that was such a benefit to me but i think i think if you're exposed to it kind of like you're saying you do you can you can become curious if you don't have it i think you're right you have to you have to approach it in a different way that's why i think curiosity is the superpower moving forward here like if you are curious and you're a creator man like there's there's no limits at this point but if you're just looking for the answer if you're looking for the shortcut it'll give you the fastest shortcut you've ever seen but it'll take away the all thought process to get there and and that's the critical thinking piece you know are you seeing it at the mba level you know because i i have my issues with uh you know four-year colleges that charge you know a few million dollars whatever kids in debt to get a fifty thousand dollar a job i i don't think undergrad is an actual education unless you are laser focused on what you want i think it's a social education i think it's really good for kids to get out of the house and and be in a in a structure but mbas to your point are the ones who choose i i want to go like i want to learn this so that's why i love that's an education to me but are you seeing how are you seeing that coming out of school into an mba obviously i think you're at the cream of the crop when it comes to curiosity but do you see curiosity do you see work ethic do you see those things um uh critical thinking are they an issue that you have to find a way to tap into or are they coming to this because of this class because of where they are with those innate abilities well it's a really interesting question so i i gave a sort of founding gift for the entrepreneurship center at trinity because i know if i had been exposed to this notion that i talked about before like how do you finance an idea how to how do you create something out of nothing what is a startup because prior to prior to being in business school i just worked at big companies i remember once i was working at this company called pain weber i was one of 43 000 employees and it was a day kind of like today where you'd really rather be on the golf course and i'm like if i don't show up no one's going to care like it just doesn't so this notion of how do you how do you create something out of nothing it's just that passion unlocked in me up to your point of curiosity i think if you get exposed to it at a younger if i've been exposed to it in college that's why i started the entrepreneurship center there um is or started i'm getting the first gift there's a woman named louis liz elting who gave a gift for the actual building but if you get exposed to it at an earlier age i think that unlocks more opportunity for you so i i just think it it's one by the time you get to business school you're paying a lot and you better make it worth your gonna be curious you're gonna be curious yeah it's actually funny you say that that's why i wrote that book uh with my daughter it's called i want to be in sales when i grow up because i think getting kids exposed to sales early in their lives and understanding what it really is yeah could open up a lot of doors because this is the greatest i i would say this is the greatest profession in the world when done right it's the worst when done wrong yeah there's no in between in a lot of ways well and john think about it this way because i've sort of made the transition from sales rep to sales manager to vp sales to ceo now board member you're selling at all points i'm on a board and right now i'm doing all the selling we're trying to sell company actually as a board member so you never get away from it in fact it becomes even more important the more sooner you get so you have to learn this and that's back to your comment about engineers that they have to really try and learn how a salesperson's brain actually works to understand how to work with them because we're just wired a little bit differently than someone who's a a natural engineer same same way for me i'd have to like really study to understand how to how to solve the technical problem and ultimately i was better as a ceo once i learned both sides of the brain like i learned product and how hard it was to build that but the best companies are the ones with the best products and the best sales teams not this notion that if i build a great product themselves yeah that's one you have to have the combination of the two it's just and one i wouldn't say is necessarily better than the other in the sense that they have to be lockstep right to to have to have growth to have all that fun stuff and that's why i think the appreciation for it um is is critical and almost why i wish i'm actually trying to switch this this you know predictable revenue model into and i'd love your perspective on this actually um my philosophy is like pick all the gtm roles right you got sales marketing and uh and rev ops yeah you know the three buckets um very few colleges teach sales marketing i got my degree in marketing as soon as i got out of the real world i was like what the hell is what did none of this is relevant right and rev ops most colleges don't even know what rev ops is and so so people choose these careers in the first couple of years they're just fumbling around like idiots being like i don't know what i'm doing here right so what i want to do is i want to go back to my day like when i was at xerox right when i got into xerox i got my formal sales educator it was an eight-week sales training program then there was an apprenticeship then there was this like i didn't get in territory for like six months so but when i got out i knew the business i knew how to sell i knew the clients i knew operations i knew finance i knew all of it so i was a business professional a lot of sales rep and and i think if we put like the first year of any kid's gtm i don't care what you want your first role is a gtm generalist where you are kind of a support structure for the full-time sales rep who's out there you know kind of full cycle sales but you spend a day with marketing day with finance a day with this a day with this so you get exposed to all that stuff second year you kind of pick a lane so now you're making cold calls into a pod you know maybe quarterly bonus structures and whatever else and then third year okay you're in your role i think that would a improve retention improve your sales in general because they would have perspective across the entire board of the spectrum of client service and all these other things so they could be better service to fit the client and i think financially it'll actually work out as well so what are your thoughts on like dumping sales reps because i don't think it can be the the zero start anymore because it used to be ah shit my degree sucks uh you know what i'm good with people i don't have any experience in sales let me start a job and people yeah sure i don't think you can jump into sales at zero right now and be successful with what's going on with ai so how to outside of school which this is where i i love the fact that sales wasn't an educated profession because now if the colleges pick it up they're going to give these kids a chance in this real world but that transition is a hard one so how do you address that business acumen side of the house from a sales standpoint um in school in in work and those type of things so that we can give these kids a chance because they're not coming into sales at ground zero at this point is is uh you better be a special kind of person to survive that yeah so the last company i ran was black duck software and when i got there there was um there there was no uh summer internship program for college kids and nobody you basically you had to have a job for five years to get it yeah you so we wouldn't train but so we i started going out to different schools i went to turn it with you know and so told the senior team wherever you went to school go and recruit and we built we built this amazing engine um we and it and it was all the foundational element was sales enablement what you're talking about so you had to go through our class you had to learn how to make a call by our system and then you you graduated from um from the the basically you got your wings um in out of flight school we called it flight school we had a theme for it and then then you did just what you said you go on to a pod and and you know to learn outbound learn how to do inbound but some of the students people that came through were like i'm actually more interested in sales enablement so we moved them over to that it was really a great training program to get people to understand what you know what this what it takes to win and then we gave a clear career progression once you master these steps every six months you move up so we basically built essentially like the red sox have a farm system and they promote the guy from patucket that's what we had so i didn't have to go out and recruit free agents and pay you know top dollar for everybody because we were developing our own talent so i guess to your point there's this balance of you have to be at a company large enough that has that it doesn't have to be as big as xerox and not maybe so small that you're going into a two-person startup and trying to do it all by yourself because that is that is really tough with an instructor actually the advice i give to kids coming well i don't know where it's going to go now but the advice i tend to give kids coming out of college is like if you don't really know go get a job with a logo right because they'll train you they have a process and when you go interview after that you don't have to explain what the company does right right if you're at some no-name startup you got to spend half the interview telling what the company did and who they went to but it's like i've worked at xerox it's like oh shit you worked at zero great next right so oh and by the way like i didn't even know xerox is um you know when i was going through it i didn't know how good it was or at least the perception of it was i mean when i got out into the world after that people like you went to xerox you went to the ceiling and it was like this and i was like oh yeah yeah yeah it was great you know what i mean meanwhile i kind of stepped my way through it right um anyways so let's let's talk now about so we talked about kind of the challenge these kids are facing right let's let's talk about let's shift gears a little bit on your um stage two capital and investments and and you know working with companies i specifically want to hone in on the sas industry right now um because you've seen the you know you were both part of the boom right uh rode that wave um i am i am genuinely concerned for the sas industry right now and i've been and this is a selfish question because i've made my whole career off of the sas industry specifically mid-market sas not not you you know salesforce is going to be salesforce they got the infrastructure they got the client base and everything else but these mid-market ones you know the ones like and i say mid-market even though they were valued at 2.4 billion like the sales lofts the outreaches kind of these these middle layer companies that are sas and now seeing this ai stuff come out of nowhere and being able to flip up do things that they could never you know what i mean like so regardless of whether the ai thing is better than it's throwing so much confusion into the marketplace and idiots like me who are non-technical and all of a sudden build an app i'm like wait a minute why do i have to pay you for what i just built even though my ignorance is on you know the compliance and all that stuff is not there so what are you advising sas companies to do right now to to evolve without getting destroyed now it's really really interesting question let me just um i'll mention a a new person i just met zach uh smith just joined the board of wasabi with us and uh i've been on the board for a long time company has grown really really well and he he had an argument with his cto of his company who's like well i don't really think you know i need need to to get into ai and sort of doubted it and and so he went deep and realized and actually went to some buddies at anthropic and and learned what was really going on and so what i started to see is sort of that repeating and it isn't necessarily happening in the engineering group it i've seen it happen in one company i'm on the board of the marketing group is leading the way another finance is leading the way and once everybody's oh you're doing that with fewer people with these tools and you're just digging in oh i better do this so it's the real key is how quickly the development team gets on board and realize starts to get familiar and then get ahead because you're not going to need to hire you can just have your you know your ai build ai my son my son's working at a really cool company called all hands which is the software that builds software he's the first sales guy in this company and it's like the speed of that movement is unbelievable so so this is so yes and right so the you get the sas companies who need to evolve right and their their ai's throwing a monkey wrench in all this but you just mentioned something that is the i think the underlying fear that i have is that wait a minute i can do so much more with so much less so therefore great i can reduce headcount i don't need to hire right guess what that's yet another license that a sas that that some other sas company can't sell to that company because they're losing headcount because ai is making them so much more efficient so it's almost like this cyclical like death spiral that i feel like sas is in it's like oh great oh yes we have to evolve we have to adopt ai so therefore look at how much faster and better we can evolve our product oh we don't need those that group of engineers so we don't need those um marketing people because we can do this stuff look at how efficient we are but that means you there's 30 percent less people in your organization that some other sas company can sell their sas tools yeah so so where you i think where you're going to see the biggest hit to start is the ones that have levered up right in the the whole pe thing private credit and taking on you know billions of dollars just like holy shit vista if i was if i was on the board of vista i'd be having a heart attack right now well i mean that that's happened throughout the whole industry and that's where i think the first is you know because as your as your revenues start to come down and you start stop growing when you have that debt so there's going to be a you know a rational rationalization there i think that's the first piece the other thing i've seen uh in the very small companies is just as you said like what you can do with claud or any of these other tools is the the sort of the startup tech stack now you don't need a lot of products that are out there i have a whole course on you know what you need at 1 million 10 million 100 million that's completely changed because you can just do so much of it yourself so i do think though that the the notion that like a workday or a sales force was trading in terminal value to me that almost gets me thinking all right it's a it's a time to buy because they're not going to go away yeah but i think i do think the ones that are down below the the screen that are smaller and don't react quickly are at peril that's and that's what i keep saying like i i still think salesforce is a good buy like i don't i don't i think penny office is going to figure something you know what i mean and and and again you know we live in a capitalistic marketplace right now so you know what what jack dorsey did and hacked a thousand people or whatever you know and said hey yeah it was ai i mean the market was like yay you know um good for you so i think if they have the right strategy um you know they the bigger ones can get through it it's it's the mid-market ones that i'm most i think the small ones i think the sky's the limit you like to your point like you don't need a a fountain you don't need to hire 50 sales reps and 50 engineers and all these different things like you can build basically two three people can build a billion dollar company well at this point and there's come just right in our backyard like i don't know you saw this company blitzy this is a former student and a sales coach that they're going gangbusters i mean you're seeing i mean what's interesting about this john is you're seeing where we had explosive growth startups back in the 90s and 2000s these new ai ones are even faster and it's really cool to see so you know i'm trying to just spend my time with those ones now yeah same awesome well let's let's um just finish up with kind of some of your some of your key takeaways from the book so that we can give people a little teaser here to go get it yeah you know for founders for students for for people out there like what are what are kind of your favorite highlights of the book right now and takeaways that that the audience could kind of sink their teeth into so i co-authored it with trish favreau who i used to work with at mit she and i collaborated on a few things and we thought the best way to do it was to profile with 17 different entrepreneurs and tell other people's stories to kind of give people the inspiration to think well if that person can do it if someone can figure out how to sell caskets online that was maybe my idea most of them are tech sass most like i was looking at caskets uh like beer was a sustainable sausage brand sausages yeah that's i didn't want it to just be like ai software silicon valley billionaires i wanted to think of it as like there's a woman who sells tires uh in lawrence mass who's just a kick-ass lady lover and i met her just because i popped a tire and i saw her story and she everyone said is this your husband's business like no this is my tire store so a woman winning in a man's business i just think those are fun fun stories and then the other piece of it was i had the same questions from my students about starting companies and getting their first customers design partners so i'm like i gotta write a book and so that the students asked for for time and i'm like just read chapter one and then we're gonna have a really fruitful discussion well i'm not gonna have this discussion i mean i was like it was like being an automaton having the same conversation over and over again so i think the book was kind of fun way to get students engaged cool as well and uh it's fun and we have about i think we have 20 experts who weigh in on what what these entrepreneurs did well what they could have improved that's that was fun too to get some other experts involved yeah i think you know the the best sales as you can i'm like i said i'm very encouraged that we're starting to see more colleges adopt sales as curriculum yeah for instance you do you talk to dr howard dover down at ut dallas oh i know they have a good program yeah i've heard of the program if you uh dr howard dover if you want he leads the charge uh from a undergrad standpoint related to sales uh what the program he's got down there is fantastic and even the one down over here in um bentley uh bryant so bryant has a good one yeah i know those i know those guys yeah i've hired a lot uh stephanie's a good friend and i stephanie's terrific yeah i went down there for the one of their sales uh conference you know competitions and i was one of the you know judges on some role play exercise and i'm not joking i'm watching these kids do these role plays i'm like oh my god you're better than 80 percent of the kids i train for crying out loud i'm like this right right now based on your your demeanor if nothing else so it is encouraging to see that it's it's starting to really become something that is an educated profession not the default profession yeah because there's so much to be educated on from a psychology standpoint and a you know sociology standpoint and everything well it's just that you know one of the things that's very interesting in teaching is harvard's taught use the case method for for 100 years and with gpt or any kind you can you know you can gpt a case so like how do you conduct so one of the things we do a lot of role plays where you have to think on your feet you can't ask ai in the middle of a role play in front of all your classmates there's pressure yeah and that's what it says you have to think quickly and ask questions and then tailor your pitch or it's just very interesting how you can use a lot of what we've done in sales to make a class very engaging yeah yeah i mean i'm doing the same thing with my curriculum i'm trying to figure out how to you know plugs ai into it while still well like going back to it getting back to the foundations and the fundamentals but augmenting with ai so that we can but but i still feel like we need the why we need the foundation we need the fundamentals so you can understand why that output is what it is why you should ask that question why you should present it a certain way versus a different way and and that's the key right now is like not just this not just the ai but yeah this too so let me let me just give you one example this is kind of fun a couple about 18 months ago harvard asked the faculty would you like to have a digital twin made an avatar and i was like sure and um so they got sort of popular and they started using it in classes and people think they seem so it's really weird people meet me and they're like i think i've met you i'm like no i think you've met my avatar it's a lot better looking yeah a lot smarter you might have this kind of weird indian accent but uh i'm gonna so i'm gonna send you this you're gonna love this and then we can finish up um so you know guy kawasaki right yeah yeah so i had him on the podcast a while back and this is what there's about two years ago and this is when i knew i was in trouble as a not as somebody who transferred knowledge making money transferring knowledge this is when i knew i was in trouble and you'll love this experiment i'll send you the details of it because it was fantastic um so somehow i got him on right whatever and with everybody like i want to make sure i do my prep work so i'm not asking the dumb questions everybody else asks right and so i the day right the day before google had uh posted a video of him at google where he was talking about ai and he had said in the video he said if um i created his kawasaki gpt and he's like i put all my every book all 17 books every podcast everything i've ever done i put it on this jp and he said in the interview he goes if you ask kawasaki gpt a question you will get a better answer than if you ask me so i said game on so the night before i interviewed him i interviewed his gpt oh this is great the day of i didn't tell him i interviewed him asked the exact same questions in the exact same order and at the end i go hey guy i gotta let you know i know you're a huge ai fan here he goes yeah i go i gotta let you know man i've already had this conversation with you and he goes what i go yeah you're you're gpt and he and he laughed he goes well because he just come off of surfing 65 years old started surfing he's like well then why am i not still surfing i go actually guy that's the question i wanted to ask you is it if i can get better because i was like i gotta be honest with you you're you were right your answers last night were better interesting and i said if i can get better answers from your gpt what the is the point of this conversation and he said well like you deferred a legacy and i go no no no no no that's for you for somebody like me who's trying to learn something from you what is the point of this conversation and when guy kawasaki didn't have a good answer for me on that i knew i was in trouble fascinating yeah yeah it's it's that's so interesting and i have found with my avatar that because i thought at first i was gonna because i get so busy with students that want office hours i was like can you just use my avatar but they don't like it they like the in-person stuff a lot better it's good for certain things obviously like role plays and those type of things but when it does come to a conversation like this like humans are going to want humans right i i just think that there's going to be that need um but but man when it comes to like one-way learning like me sitting through a lecture versus engaging with an avatar that knows exactly how i learn and and you know what i mean like i'd rather yeah yeah and then have the beer with the the the professor so that we can go talk about some you know interesting things but learning yeah no it's fascinating really good interesting world we're living in my friend so yeah no really good most interesting podcast i've done uh that's that's great it's good so thanks for having me on and you know um hopefully yeah well actually i should finish with one thing because this is yeah tell people where they can find out more information on amazon unlikely entrepreneurs if you don't like it it's a perfectly good door stop if you actually need a door stop i had one of those made up too love it love it now quick question outside do you do anything that um like uh that non-students can come to so like events or evening like those type of things that people could kind of get to some exposure to some of the stuff that you're working on um i'm i'm working on an online class right now that's going to be open to to everybody yeah so that should be uh in the fall i'll have that out very cool all right well for those everybody listening again it's lou and it on on linkedin just to make sure is it is it under lewis or lou yeah under lou shipley yeah l-o-u all right l-o-u shipley go look him up on linkedin check out what he's doing definitely get that book because i think it is a timely thing for all of us to get some perspective here and figure out how to get through this weird world that we're all living in lou so thank you all thank you for coming thank you so much for your time very interesting conversation yeah i really appreciate it all right everybody hope you enjoy the conversation as much as i didn't like i always say at the end of all these podcasts go out there and make somebody smile today because no matter how bad your day is going or how bad you think it went if you make somebody smile you know you had a good day and the world needs a lot more of that right now so thank you all very much and i will see you on the other side hey thanks again for listening to the show and for all your support throughout the years this is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or g2 if you've already gone through my training or sign up for my newsletter any of those will help ensure i can continue to bring you free content and great conversations like the ones you just heard without having to annoy you with sponsors again let's make it happen in 2026 together