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#420 Steve Jobs In Exile

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#420 Steve Jobs In Exile

This transcript explores the critical 12-year period when Steve Jobs was exiled from Apple, as chronicled in Jeffrey Cain’s book *Steve Jobs in Exile*. After being ousted in 1985, Jobs struggled with direction, briefly considering a quiet life in Paris before founding NeXT. His early leadership was flawed: he overspent on a $100,000 logo, built a costly manufacturing plant, and wasted resources on revenge ads against Apple. His volatile management style—praising employees one moment and tearing them down the next—created a toxic culture. Despite these mistakes, Jobs showed signs of growth, hiring talented renegades like designer Hartmut Esslinger and logo creator Paul Rand. A critical lifeline came when Ross Perot invested $20 million after seeing a PBS documentary about NeXT. The period forced Jobs to evolve from a brash, vengeful entrepreneur into a more disciplined and visionary leader. This transformation was essential for his later return to Apple, where he would re-found the company and achieve one of the most remarkable turnarounds in business history. The story underscores that failure and exile can be catalysts for personal growth, even for the greatest innovators.

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For a long time, people have been asking me, can you make a podcast on failure? There's a brand new book called Steve Jobs in exile, the untold story of next and the remaking of an American visionary, and it was written by Jeffrey Cain. And that is what this episode is going to be about, because the book is exclusively about a chronicles that 12 year period of exile between when Steve Jobs gets kicked out of Apple and then he returns to Apple. It is probably the defining point of Steve Jobs life because you will see one of the most brilliant entrepreneurs, maybe the greatest entrepreneur to ever live, just make mistake after mistake after mistake. And the longer he's in exile, the more the pressure builds because he's burning through his entire fortune. And yet because we know what happens after he returns to Apple, this is somehow one of the most inspiring stories because of Steve's refusal to quit and then his ability to transform, to build himself into the kind of leader and entrepreneur that deserves to run Apple. And before I jump into this book, I want to read you a paragraph from another book because I want you to keep in mind these few sentences from this other book. This book is called "The Return to the Little Kingdom." That book was primarily about the first few years of the history of Apple, but there's an updated version where the author Michael Moritz writes this, "Many are familiar with the re-emergence of Apple. They may not be as familiar with the fact that it has few, if any, parallels." When did a founder ever return to the company from which he had been rudely rejected to engineer a turnaround as complete and spectacular as Apple's? While turnarounds are difficult in any circumstances, they are doubly difficult in a technology company. It is not too much of a stretch to say that Steve founded Apple not once, but twice. And the second time he was alone. The book that you and I are gonna talk about right now, Steve Jobs and X-Isle tells in great detail the personal transformation that Steve Jobs had to go through to be able to re-found Apple. I'm gonna get right into the book. This has every waking moment of his adult life had been spent building Apple. Long days, longer nights. Now he had no real friends, no other life to turn to. Steve decided to disappear for a while, to step away from his old life and to think. Suddenly he was gone and nobody knew where the hell he was. And they didn't know if he would come back. So Steve Jobs is going to officially get kicked out of Apple in September 1985 before that he's stripped away of all his power. So he spends the summer in Paris, trying to figure out what the hell he's gonna do next. And he talks about this in an interview. He says, "You probably had somebody punch you in the stomach and it knocks the wind out of you. If you relax, you'll start to breathe again." That's how I felt all summer long. And so during the summer he goes to Paris with his girlfriend at the time, this woman named Tina. And so at the time he's wondering, he's like, "Okay, well I have this fortune, maybe I'll just live a quiet life in Paris." And so his girlfriend wrote him a letter about this time that they were together when he was at a major turning point in his life. And this is what she wrote. We were on a bridge in Paris in the summer of 1985. It was overcast. We leaned against a smooth stone rail and stared at the green water rolling on below. Your world had cleaved and then it paused, waiting to rearrange itself around whatever you chose next. I wanted to run away from what we had come before. I tried to convince you to begin a new life with me in Paris to shed our former selves and let something else course through us. I wanted us to crawl through that black chasm of your broken world and emerge anonymous and new in simple lives where I could cook you simple dinners and we could be together every day, like children playing a sweet game with no purpose, save the game itself and the next sentence. Perfectly describes Steve Jobs, but Steve couldn't stay away from work for long. He still wanted to build and create. And so Steve gets kicked out of Apple. He decides, hey, I'm going to build a computer for the university market. I'm going to target academics. And so he winds up poaching his co-founders. I think there's like four or five co-founders of next. Directly from Apple, this causes Apple to sue Steve Jobs. And that lawsuit is about the only thing that the company has. It says their new company had no name, no business plan, no product, only a vague vision of building computers for universities. And there's a bunch of things going against them. It says at this point, Steve wasn't yet regarded as an undisputed genius in the industry. Instead, people saw him as a terrible infant. He could sell anything, but his reputation was poison. When Steve tried to poach other great Apple engineers, they refused to follow him. And so one of Steve's first moves was actually surprising. And why is it actually being a good idea later on? He didn't know this at the time, but this is actually going to introduce him to Ross Perot. Ross Perot is going to be one of his major backers and one of the largest investors in next. So Steve decides, he says that strong teams need a visionary story to believe in. So he actually hires this filmmaker named John Nathan. And Steve asked John to come and film next his first team retreat. What John films there eventually winds up as this documentary and PBS that's called entrepreneurs. And so we'll get to Ross Perot a little later on, but in this documentary, Steve is telling his team, we have 18 months to build an entire new computer along with this operating system from scratch. And even back then, he was repeating this mantra that he would say over and over again throughout his career, that great artist ship. And he's telling them how he thinks about recruiting. Now this is going to be fascinating because there's a lot of things that he says that he believes in. And during this period, this period next, how his actions and his words rarely match. And so there's ideas that Steve professes to believe. And at this time in his career, where we are, when he's 30 years old, trying to start next, he believes that we can't do it. So he's watching George Lucas, because he's going to buy Pixar from George Lucas because George Lucas is going through this divorce. And he's watching how George Lucas builds his company. He's like, oh, I want to do the opposite of that. So this is what he says. George was cast out from a 35 million divorce settlement and was threatening to fire the division's entire team if no buyer emerged. His approach to creative work seemed to be to assemble the world's best team, complete the movie, and then quote, blow them out, which means dissolve the group and then start fresh next time. Steve found this approach revolting. At next, he was determined to build the opposite, a permanent ensemble of brilliant people who would stay for the next impossible project and the next one after that. And Steve wanted rocking from team members, which he describes as full body absorption of the company's DNA. That's what he says at the beginning. He turns over every single one of his co-founders and almost every single executive. But they make the point later in the book that when he gets to Apple, he finally builds a team and most of those people are with him for over a decade for the rest of his life. And so he talks about the way the Steve thought about hiring. Steve demanded a certain temperament. Steve respected talented people who could fight. You had to be willing to push back against Steve. Your ideas would only survive if you could evangelize them and convince all the smart people around that this was the best option. The culture was so intensely combative that when next veterans moved on to other companies, their new colleagues would tell them to dial it back. They had been conditioned for a kind of intellectual warfare that didn't exist elsewhere. That is something that Steve keeps with him, even when he returns to Apple. In fact, Ed Cappemoll told this great story where Steve was talking about he had fired two people from Apple's board. And the reason Steve gave Ed surprised Ed and Steve said, it's because they didn't ever disagree with me. And so at the very beginning of next, Steve gets captured by this idea that he wants to make a computer in the shape of a cube. It says Steve became obsessed with the idea that a computer's form could deliver emotional satisfaction alongside raw functionality. Steve hired a European design firm and tasked it with designing a perfect cube. They called us to said you've got to get on the next plane to Europe and see what we've come up with. We have something far better that's going to change the shape of computing forever. And this story just may be laugh. Steve flies to Europe, sits through this design presentation. The designers are like, hey, every computer in the future is going to look exactly like this one. They pull off the curtain and it's in the shape of a human head. It is laugh of the idea of the computer singer and desk of the shape of human head. And then Steve's response is, I think, predictable. He fired the designers. And then he calls up a designer who'd previously worked with him at Apple. This is the founder of this firm called Frog Design. His name is Hartmut. And what Steve liked about him was that he was a renegade. In fact, this guy's mantra was form follows emotion. He thought that computers should feel human, intuitive, and even sensual. That's right up Steve's alley. Because if you remember when he went back to Apple, he said that he wanted to make products that you could lust after. So Steve finds his designer. The next thing he does is he wants a logo for next. So he goes and tires his guy named Paul Rand and Paul's another renegade. Another entrepreneur that's hell bent on doing things his own way. Paul was one of the most respective figures in American design. He firmly believed as did Steve that a logo should convey something essential about a company's value. He had created iconic logos for IBM, UPS, Westinghouse, and ABC. Paul did not suffer fools gladly. When Ford Motor Company invited Paul to redesign its logo, he walked into a conference room with 50 executives and immediately asked, who makes the decisions here? Then he presented only to that person while the other 49 people sat watching. When Steve spoke to Paul for the first time, he asked if Paul could present him with a few options for next logo. No, Paul said, I will solve your problem and you will pay me. Paul's price, $100,000, whether or not next ended up using the logo. It was a monumental sum, but Steve agreed. And so the reason I'm bringing this up is because it's one of the most important themes in the history of next. Steve had too much money, he had too much personal money, and he got way too much money for his investors. And so he stopped watching his costs. He repeats that's over and over again later on, where he essentially admits, we did the exact opposite of what we did when we started Apple. And again, we have an example where what he's saying in his actions don't match up. He's speaking to the staff, hey, we need to be disciplined about cost control, but he has this champagne taste. They say he had champagne taste that he'd gotten used to. And so as a result of this, the company's burn rate is just climbing. And this would be the story, year after year after year it only gets worse. And so I said, Steve, wanted every facet of Nexus image to be perfect. He wanted a New York ad agency, a top-tier public relations firm, a full marketing staff, a receptionist with a prestigious college degree who could remember the names, faces, and positions of every visitor who walked in the door. When I got to the end of that paragraph, I just wrote down the note that I left myself as a question. Did Apple have any of this before they had a product or any customers? The answer, of course, is no. The $100,000 logo fee spawned an inside joke on Nexus staff a new unit of financial measurement called the Millie logo. One Millie logo was at $100, a high-end computer monitor might run 20 Millie logos, a designer sofa, 70 or 80. Steve overheard the joke and he didn't laugh. Before we jump back into the story, I want to tell you about the presenting sponsor of this podcast, Ramp. One of the main themes in the history of entrepreneurship is constantly attacking and questioning your costs. This is something as you're here in this episode that Steve Jobs did when he started Apple and something he failed to do when he started next. Ramp helps many of the most innovative businesses in the world do exactly that. The median company running on ramp, cuts to expenses by 5%, a religious dedication to controlling costs also helps increase revenue because you can pursue opportunities you couldn't otherwise. We see that in the ramp data to the median company running on ramp also grows the revenue by 16%. So when you're running your business on ramp and your competitors are not, you have a massive competitive advantage that compounds over time. Ramp is the only platform designed to make your finance team faster and happier. Many of the top founders and CEOs I know run their business on ramp, I run my business on ramp and you should to make history's greatest entrepreneurs proud by going to ramp.com today to learn how they can help your business save time, save money and grow revenue. That is ramp.com. And so he's getting pitched by ad agencies and says Steve's feedback was hard to predict or to plan for and could be searing. Par way through an ad agency pitch meeting Steve cut off the already nervous executives with a request. He wanted a phone book brought him once it arrived. He leave through a few pages then looking up he said this makes for more interesting reading than the shit I'm hearing from you guys. He was material. Nexus team members often refer to this as a hero shithead roller coaster. He could lavish praise on your work one moment then turn around and tear your part in front of the room the next. You never knew where you stood. And it's interesting to note there's this other great book. I've read three times. I've done like one or two podcasts on it's called Creative Selection is written by the guy named Ken Cocienda and it's about the golden age of Apple when Steve goes back the second time and he actually interesting part about this is Steve fixes this when he goes back to Apple because in that book Ken Cocienda said that Steve was always easy to understand when giving product feedback. And so this hero shithead roller coaster is happening next and it happens one time in front of Paul ran the guy this is I'm the logo Paul's like 30 years older than Steve doesn't suffer fools so he calls him out on it and he actually gives him great advice says Paul saw the danger in Steve's volatility after listening to Steve ran about graphic design the logo designer cut him off between now and when you have a product you are the product my friend and so you better be nice to people. And so this book does a great job of going into detail why these little things matter it sets the tone for the entire company especially to start up somehow a hundred thousand dollars have become the company's standard spending unit as if Steve's logo had set the baseline for what constituted normal expenses Steve ironically criticized the team for buying new equipment instead of scrounging for deals we have stopped nickel and diming for stuff and this all adds up he said I don't see that start up hustle. And so one of the recurring themes of the book is the fact that when he started next a lot of his motivation was to get revenge on apple in fact when he was an older and wiser man he said the older I get the more convinced that motives makes so much difference and he talked about the difference of why you're doing what you're doing why you're building the company you're building why you're building the product you're building and you see he probably had the wrong motivations at the very beginning because he's literally running wall street journal ads taking shots at apple keep in mind he has no product he has no revenue he doesn't know what he's doing yet and yet he's wasting time and energy and resources doing shit like this this is what the ad said the personal computer industry is now being handed over from the builders to the caretakers that is from the individuals who created and grew a multi-billion dollar American industry through those who will maintain the industry as it is and work to achieve marginal future growth I can guarantee you there is life after apple and again this kind of spending reflects his priorities it says so much of Steve's motivation at next was about sticking it to apple at apple it was about building the best product it was about building insanely great products and about a year into this Steve sits down for an interview and there's just a few things that he said in this interview that I thought was interesting because he gives you an insight to how he thought about himself definitely not as a businessman says whenever you do one thing intensely over a period of time you have to give up other lives you could be living you have to have a real single-minded kind of tunnel vision if you want to get anything significant accomplished especially if the desire is not to be a businessman but to be a creative person and then he's asked well you're the CEO of next isn't at the very definition of a businessman and Steve responds myself identity does not revolve around being a businessman do I recognize that this is what I do I think of myself more as a person who builds neat things and that is very common with people trying to build neat or great things they want to retain control over the process as much as possible and sometimes that instinct can lead to disastrous decisions which in this case is them building their own manufacturing facility in Fremont California Steve thought that building a next operated manufacturing facility that was 30 minutes away would give him tighter control over the manufacturing process he also had a ridiculous idea this is one of the craziest ideas I've ever heard he envisioned that this facility would enable an elaborate buying experience just like Ferrari customers fly to Italy to pick out their cars straight off the assembly line so would next customers if you're going to buy a great sports car what's the best way to do it he would say you fly to Europe go to the factory and buy it there people are not going to buy their computers this way that is crazy and again at the same time he's saying this next is cash reserves are rapidly dwindling the bank account balance was dropping every day and it says revenue was nowhere on the horizon and right as his cash balance is dwindling he gets a lucky break on November 5th 1986 Ross Perot happened to tune into PBS and on came this documentary called entrepreneurs the next morning Ross leaves Steve a voicemail and says if you ever need an investor call me Steve didn't want to look desperate so he waited a week and they picked up the phone and they quickly hammer out a deal Ross is going to put 20 million dollars into next for a 16% stake in the company he becomes the company's largest outside shareholder but as one prerequisite of the deal is that Steve has to have more skin in the game so he asked Steve to put in another 5 million of his own money so incomes 25 million dollars more to the company and a secret deal where the book says that Stephen Ross has struck a second secret deal it would never appear in any press release or regulatory filing they didn't even write the terms down to sell the next computer Ross was willing to mobilize his high level government networks and his sales force from the company he was planning to start this is a company called Perot systems it would build on his past success selling technology to the military intelligence agencies and the federal government remember this part for later the word mccurial is used over and over again to describe this version of Steve jobs wait till you see some of the bizarre decisions he makes where he were torpedo deal after deal after deal when his company has no money and is producing just a handful of computers and so this version of Steve has no trust in his team he's micromanaging every single thing he's essentially trapped in a prism of his own perfectionism and this is going to cause his company to his bleed tens of millions of dollars for says in early 1987 Steve's pursuit of perfection was devouring the timeline every revision push deadlines further back and every prolonged debate over this or that component drove costs higher yet no one could make decisions without Steve and Steve couldn't stop perfecting while Steve demanded revolutionary technology every delay allowed competitors to catch up rendering the technology less novel Steve was caught in his own trap he believed that his vision was perfect and it didn't need changing yet he couldn't stop tinkering with it and again this is where his words are not matching up with his actions because he's preaching to his team this is what he's telling them at the time the most important thing you're competing with is not another company but it is your own ability to execute he seems to be blissfully unaware that they are unable to execute at the moment so this debate is raging on and we'll see this other recurring theme that Steve caused the problem then shifts the blame of that problem to somebody else and then fires that person so he's just churning through people says even as debate rage on nexus VP of manufacturing Linda Wilkin had to begin building the company's factory with no firm decision on the circuit board a choice that would dictate the factories plan Linda did the rational thing and prepared for both possibilities when nexus factory schedule inevitably slipped rather than blaming his own indecision Steve took out his frustration on Linda and he fired her and the entire company gets stuck in this loop for months and years each time the chip designers got close to a final layout Steve would change his mind add this he say now move that his perfectionism about the chip's appearance created months of delays and no one around him is telling the truth when Steve asked how long it would take to finish the ever changing design the engineers knew the honest answer about a year working seven days a week but they also knew that that timeline would never fly so they lied one more month they'd say each time Steve asked and so Steve comes up with with this thing called the deep shit list. It's a of existential threats that he said if we don't solve these threats, we're going out of business. And so he would light into the two engineers that are called Big Dave and Little Dave in front of the entire company and say if you guys don't figure this out, we're going out of business. And this is the crazy thing that happens next. So a week or two later, Big Dave and Little Dave, they have an announcement. Guess what? We're ready to ship the master chip design to Japan. We solved everything. Steve goes on the hero's shit head roller coaster. So this is oh my god, you guys are geniuses. We're going to give you $25,000 bonuses each at the time that's equivalent to half a year's salary. So he hands them the check. The two Dave's are like, this is great. They leave. They go back to their office. They pack up their belongings. They walk out the door and they never come back 90 days later, the final chip arrives in the manufacturer. The team snaps it into the computer to try to test it. Nothing. It doesn't work. As a result of this, the release schedule, again, they don't have a product to have no revenue. The release schedule for the computer has to be pushed back a full year. And this just continues. This time went on the deep shit list started to look less like an existential priority list and more like Steve's personal wish list. He kept piling on features, adding costs and making last minute demands. So at the very beginning and next, Steve has a like advisory council of all these people that work in academia. They're advising him on the kind of technology they need, but they also talk about, hey, it's really, really, really important that your computer cannot be more than $3,000 per computer. You have to stick to that. And so it's Steve does something bizarre at the next meeting with this council. He keeps the details of the cube hidden and instead distributes this beautifully printed 18 page brochure about the next logo. Let me read you this note when I first read this about what's going on here. We still don't have a prototype to show you the finished product won't come anywhere close to the price you've stated you're willing to pay. But hey, here's 18 pages on how our logo was designed. This is why I refer to this time period. This is like Bizarro Steve jobs. It is a version of Steve jobs is just making the opposite decision that an intelligent entrepreneur would make and he's doing at the time where his company, we're in the 80s. His company is burning to a million dollars a month. And yet just like with the story of Raspur randomly seeing this documentary and saying, I'm put 20 million to this company, Steve winds up next to the CEO of IBM at a dinner and IBM wants to license operating systems for their computers. And this is the deal that Steve sold to the CEO of IBM. It says IBM agreed to 30 million dollars on signing the contract and another 30 million dollars on shipping and then royalties on every copy they ship a total investment of 60 million, which is three times how much Raspur put in and a windfall that brought them years of runway. Now it's fast 40 or the more he raises the more he spends. And so we're back in a bad position. Nexus financial outlook was also looking seriously great. The company had 25 million in the bank, but needed 27 and a half millions to survive the year to make it worse. They needed to sell 16,000 machines by year end. They'd never do that by the way. And at this time, the team could barely get a single computer to boot up properly. Keep in mind as I read this next sentence to you, they haven't shipped a single thing yet. He decided that Steve Jobs decided that common spaces would be outfitted with $2,000 chairs and $10,000 sofas. Every desk would bear the highest quality phone Steve could find priced at $450 each. Remember, we're in 1988. And so he has at least one person trying to tell him the truth. It's one of his co-founders, Gennie Daniel Luin. So he writes this memo to Steve. He goes, "We are over a year late. The competition has progressed more than we expected. Our product is at twice as expensive as we imagined. The computer is still not working. You must reset expectations." Steve woke up to this reality after spending a week with the computer on his desk. The computer takes several minutes. My guess is five plus minutes to boot. My computer crashes every hour or two. With the current state of our software, the industry will laugh us into bankruptcy. We are running out of time. And again, I think these two paragraphs are super important to understand that if Steve never changed, there's no way he would have had the success he had when he went back to Apple for months. When Daniel tried to raise these exact concerns, Steve had dismissed him, saying that you're not spending enough time with the product. Now Steve was seeing the problem for himself. The sales team had a name for this Steve phenomenon. They called it Go North. The joke went like this. Steve hires a salesman and tells him Go North. He goes to Sacramento. "Keep going," Steve says. He goes to Oregon. "Go North," Steve says. He's in Washington now. "Finally the guy's calling from the Arctic Circle. What the hell are you doing up there?" Steve explodes. And Steve has another problem. His biggest investor is losing patience. When Ross Perot goes to these board meetings, he penetrates Steve's reality distortion field. This is what he says. You shouldn't introduce a product before you can ship it. He said, "What is it going to take to get the sales? How are you going to build the rest of the company?" These are very simple, straightforward answers that more than one person will come from the outside and ask. And they don't have answers to. Ross's newfound skepticism worried the team. He was their main benefactor. The company's largest investor and a source of outside credibility. And so they finally have a computer that they're ready to start manufacturing. Remember, the price is supposed to be $3,000. They're supposed to be selling to universities. The price comes in anywhere from $10,500. Or if you want a larger hard drive, it's $12,500 to put that in context. That's more at the time. It was more than the average year of tuition at a private university. And so it says, "In November, the first cubes finally shipped by the end of the year, next had shipped a measly 205 computers. Even with rock bottom production targets, the factory couldn't keep up. Steve would get phone calls like this. You know the 12 machines we promised you today? Well, there's only eight because four of them didn't pass the paint test. So it talks about his perfectionism. Also, he didn't take into account that all his design changes added complexity, which made running his factory nearly impossible. And in this case, Steve had insisted that the cube have this magnesium casing. And the problem with that is the magnesium casing was prone to microscopic air bubbles, which would be revealed because Steve also insisted that every cube had to be painted matte black. And this is a problem that his engineers had foresaw before production. And they warned Steve about it during development and Steve brushed aside those concerns. And so now you fast forward many months to even years later. And it's impossible for him to scale. Remember, he said he was going to be doing, you need to do 16,000 in a year. They can't even do 12 in a day. And then the ones that are shipped out a ton of them are being returned because they have defective parts. And then their return and next doesn't have a system for tracking why the machines failed and why they were returned. And so a summary of where we are in the history of next, it says the company was set to run out of money in a matter of three months. They had flawed, expensive hardware running unfinished software. And yet Steve is doing stuff like this at this point. One day Steve appeared in Berts office in a panic. We're selling everything we can make. He said, Bert laughed. Next was making eight computers a day. Before we get back into this episode in the last two minutes of this episode or some of my favorite parts of the entire episode, I need to tell you about two tools they should be using for your business. The first one is axon by app love and Steve Jobs said this great quote where he says a small team of A players can run circles around a giant team of C and B players, given that you're well advised to go after the cream of the cream, you need to build a team that pursues the A players. And that is what app love and has done. App love and has built a $150 billion public company with just a few hundred people because their ad platform converts ads into revenue for your business. Their advertising platform axon connects you with over a billion potential new customers. Axon allows you to capture undivided attention. Axon ads are full screen videos that are watched for an average of 35 seconds. That is retention that blows other ad platforms out of the water and you can launch in minutes. You set the goal axon achieves it. There's no complex setup, no expertise needed and axon scales quickly. Other businesses have seen immediate results scaled to hundreds of thousands of dollars of spend per day and increase their revenue by millions. So you want to get started quickly before all of your competitors are on axon and you can do that by going to axon.ai forward slash founders. And then I want to tell you about Vanta. Vanta Vanta Vanta helps your company prove your secure. So more customers will use your product or service. Vanta is an AI powered security expert who scales with you. The more your business grows, the more complex your security needs get. And that complexity can turn into chaos. Vanta, tames that chaos for you. Vanta automates compliance, continuously monitors your controls and gives you a single source of truth for compliance and risk. So whether you're a fast growing startup or an enterprise company, Vanta fits easily into your existing workflows. Ramp actually uses Vanta, which is a huge positive indicator for me because Ramp is so stringent on buying software instead of building it themselves. Vanta helps you build a company that your customers can trust. Many companies will not sign contracts unless you're certified and this is causing you to lose out on the sales, which is why the average Vanta customer reports a 526% return on investment after becoming a Vanta customer. Automate your compliance, security and trust with Vanta go to vanta.com/founders and you'll get a thousand dollars off that is vanta.com/founders. And then we see Steve's deal making ability. So early on, he decided, hey, we're not going to use a floppy disk. Instead, we're going to use an optical drive. The optical drives barely work by the way, but they buy them from Canon. And so he convinces Canon to put a hundred million dollars into next and return for their 100 million dollars, they get 16.67% stake in the company. And then we get to one of the most serious underlying problems that he has is the fact that no one around him is telling him truth. No one around him is telling him the truth. At the time, the company doesn't even have a COO. He's getting a lot of pressure because now Canon also has a board seat that you need to find a COO. He doesn't even have an HR manager. So he hires this guy Phil to become HR manager. to then hopefully also help them find a COO. And so Phil meets with all the executive team for about an hour without Steve. And so over an hour, all the company's leaders open up about next culture issues and their frustrations with Steve. Then unannounced, Steve walks in. He purchased himself on a chair at the end of the table and says nothing at first. Then he breaks in. While everybody at this table feels very free to tell me everything that's on their mind, Steve said. The room filled with silence. Phil turned to Bud, who was sitting next to Steve. Bud, what's on your mind? Bud's eyes dropped, he said nothing. Phil moved to the next person. Gary, what about you? Gary looked down at the table. One by one by one. They all froze. Seconds ago, they had been griping about Steve. The moment he entered the room, everyone clammed up. When Phil conveyed the team's harsh feedback to Steve, he was very much taken aback. And so again, we have Daniel Lewin being the one fighting back at the time. Their operating system, next step, is not finished. And so they had previously agreed, hey, we're not going to ship more than 2,000 units until this operating system is finished. And Steve decides, no, we have to sell 25,000 computers or we're going out of business. And so Daniel's like, I'm not placing that order. And so Steve said that if you're not ordering the inventory as the marketing chief, whose department is running sales, then you're not going to be making those decisions anymore. And then the marketing department now belongs to Steve. This decision to fire the head of marketing leaks to the press. Daniel, who is still-- this is the funniest part. Daniel still remained next to his primary spokesman. So the man who had just been stripped of his marketing role now had the unpleasant task of explaining to reporters while he's actually a promotion. After Daniel finished spinning his own demotion to the press, Steve stripped him of that press job too. And Daniel is looking back on it. He said, there were no adults in the room except for me. We're now four to five years into the history of next. The company's in deep, deep trouble. And yet, they keep messing up the basics. When Steve ran an ad in the Wall Street Journal offering anyone who wanted a life-size brochure shaped like the cube, it turned into a self-defeating blunder. With 5,500 requests waiting, the team realized the brochure didn't fit into any standard envelope. Millions in advertising spending and no god damn envelopes. After rush ordering custom envelopes, the team then discovered at the post office that special envelope sizes required special postage. By 1990, they felt the only choice was to scrap the cube and start over with a more advanced machine. They looked at the alternatives. Lose $54 million over the coming year, retreat, and retrench, or sell the company. The time has come to look at our business proposition. Every operating assumption we had has been proved wrong. The product wasn't ready. The budget has collapsed. And the strategy keeps shifting. We are set up for continued failure. Now, keep that in mind because what Steve does next, you're just not going to believe. A month later, Steve pulls yet another rabbit out of his hat announcing a new higher margin IBM deal. They are now going to give him another $30 million. But this deal doesn't ever happen. Why? So Steve and one of the salesmen are traveling to Dallas to make a presentation about the IBM deal. At the airport, Mark says, hey, we have a problem. The venue's huge. There's projection screens on both sides of the room. They needed two sets of slides. They only have one set. It is not clear to me why they couldn't just duplicate this. But Mark suggests, hey, why don't we just skip the slides entirely and we could just launch straight into the demo when we get there. Remember, they're out the airport. And this is Steve's response. So Mark, what you're telling me is I don't have the tools I need to get my job done today. You know, I'm just really busy and I'm not going to go. Steve turned around and walked out of the airport. So Mark flies to Dallas and has to make a presentation to 800 IBM engineers alone. The fact that Steve didn't show up, it says the IBM executives read the no show as a lack of commitment to the relationship. The deal was effectively dead with IBM. Steve had overestimated his power and he knew it years later. He invited and Pixar co founder Ed catmell that he had learned a lesson from the collapse of the IBM deal. Never overplay your hand. He's doing that at a time he knows that his company's going to burn 54 million dollars a share. This is crazy. He does it again. Remember that story told you earlier, Ross Perot is like, hey, we're going to sell. I mean, except this company, we're going to sell next to the government. So it says after months of negotiations, the deal that could unlock hundreds of millions of dollars in government contracts was finally ready to close. Pat Horner, who is the CEO of Perot systems, flies to next, sits in the conference room with the contract spread across the table. Daniel Lewin goes up to Steve, hey, we're going to sign the deal. You coming in Steve looked up and said, no, I don't want to sign the deal. I don't want to do business with the government. Daniel walked back to the conference room and had to tell them that Steve wasn't coming and that there would be no deal. Within minutes of pat leaving and getting back on the plane, Ross Perot calls. He is told Steve is unavailable. Daniel gets on the phone with Ross Perot instead. Daniel, this is Ross. You know, on any given day, I can call and speak to the head of the FBI or the head of the military of Panama or the White House. And they put me right through. I'm in business with you. Why can't I talk to Steve? Ross was done with the magic show. He had studied the company's fundamental and he was completely concerned with what he saw. He ripped through the numbers. Next had burned $39 million while planning to lose just $3 million. Without $56 million from IBM and Ross, the startup would have been dead a long time ago. Steve employed 69 manufacturing staff or company, barely shipping a product. And devoid of all reasons, Steve forecassed sales of 11,000 computers this year. And this is where Ross Perot finally realizes his initial mistake. You know what my mistake was? I gave Steve too much dang money. When you have too much money, you just don't have that hunger. And you start spending money on floating staircases and $10,000 shares. Which Steve did both of. And there's a great sentence about this few pages later. He was choosing purity over survival. Let's go back to this idea that they are many, many years into the company and they still can't even handle the basics. So in the summer of 1991, Steve invites Andy Grove to the next off-side retreat. Andy, who's the co-founder of Intel, had been a mentor to Steve. And it says Andy entered a meeting room with next senior leadership team gathered before him. He skipped pleasantries and posed a seemingly easy question. What business are you in? Hearing no response, he began pulling each person in the room one at a time. Andy asked profoundly simple questions, but revealing ones. After six years in business, next own leadership couldn't agree on what business they were actually in. And not only that, they're lying to themselves. Remember, everybody around Steve's not telling the truth. Now they're lying to themselves. They have this accounting trick. And they said they were using this accounting trick because they wanted to hide the poultry sales figures from Steve. The team reported sales figures by determining the number of units given to distributors. Not sales to final customers. Distributors didn't have to pay right away. They got the machines on credit. Next then immediately counted these as sales, even though no money had changed hands and no actual customers had purchased anything. This practice was called channel stuffing. And it made next look successful on paper while machines piled up unsold in warehouses. When distributors failed to sell the machines, they couldn't pay next either. Suddenly, Nexus reported sales tumbled, and the company was owed over $10 million from distributors holding all those machines. Next was yet again on the precipice of bankruptcy. It had burned through the $100 million cash injection from Canon two years earlier. Now that Steve had alienated Ross Pro and IBM, the most straightforward paths to raising more money were shuttered. That left Canon as the last major investor standing. So they tell Canon if you don't extend another loan, next might collapse. And your entire $100 million investment might go up and smoke. Canon agreed to give them another $40 million. At the exact same time, Steve kept cycling through manufacturing leaders. He would find one VP of manufacturing hire them. They'd be the VP for six months or nine months or 10 months. Then Steve would get frustrated and he'd get rid of them. Steve always seemed to blame them for his decision to build a machine for a market that didn't exist. As Nexus leaders study the problem, a consensus began to emerge. They should abandon high cost hardware in favor of selling high margin software. But Steve wasn't on board with this plan yet. That's obviously where they have to go. He clung to hardware like a lifeline. A software pivot would mean abandoning the beautiful objects that Steve loved to make. And the crazy thing is through all this chaos and dysfunction, they actually developed a great operating system. It just takes Steve a while to understand what he has. So Steve eventually acknowledged what everyone had been trying to tell him. Corporate America discovered that they could use next step to build their in-house mission critical custom apps. Five to ten times faster than any other operating system. These companies came to us and said, you don't realize what you have. You have potentially the biggest breakthrough in the computer industry that we've seen in the last decade. Next was teaching Steve something he never learned at Apple. How to transform failure into fuel. Now here's another example of good idea, bad execution. Steve wasn't going to give up. He's trying to recruit, we're going to call him PVC. That's what they call them. They refer to him in the company. He's going to be Nexus chief operating officer. So Steve wasn't going to give up. He learned that the best people were worth the wait. When you meet somebody that good, you know you're going to be settling for second best if you compromise. I've always found it best not to compromise and just keep chipping away. So Steve finally gets his man. And like a year or two later, this guy PVC tries to sell next behind Steve's back. And so something that's obvious to everybody around Steve that we have to stop selling hardware and just transform into a software company is still something that Steve will not accept. Finally, the financial situation of next to get so bad that he has no other choice. And I think this next session gives you insight into Steve understood how bad this was. because he's trying to recruit yet another CFO. and he refuses to let the incoming CFO see next to his books. And he says, he told him that he wouldn't reveal his accounting books because he wanted to hire risk takers. Steve insisted that everything was fine and this guy named Marcel believed him. Then Marcel gets hired, dives into the books, discovers a devastating truth, that next was effectively bankrupt, that Steve had been living in a financial fantasy, and then he quits. And it gets so bad that by December 1992, Steve has to pick up the phone and call Canon yet again. And by this time they'd already poured $140 million into the company. And Steve says, if you don't deposit another check for $20 million by Monday, I'm going to shut the doors. In exchange for the $20 million, Canon would purchase next his hardware division. Next we'd get the cash, which would give it enough runway to survive, and then hold on to its software operation. This is so important because this final failure of Steve having to relinquish what he loved the most, which is building hardware. This is when we, again, we're, we're four years away from when Apple is going to buy next. This is when Steve starts to change and to transform. And so it says those who work closest to Steve notice something changing. The pattern that had defined him for years was finally breaking apart. The wild emotional swings that colleagues had learned to brace for up, down, up, down. The crashes seemed to hurt more and the highs couldn't lift him as high. Each betrayal left him rawer than the last. Daniel Lewin pointed to a passage in Ernest Hemingway's novel, The Sun Also Rises, that captured what everyone was witnessing. How did you go bankrupt? One character asks another. Two ways. Gradually, then suddenly. Steve's transformation was following the same excruciating arc. And so the news of this failure is all over the media. And here's an example of what was being written about Steve Jobs at this time. Sometimes it's hard to tell whether Steve Jobs is a snake oral salesman or a bonafide visionary. A promoter who got lucky are the epitome of the intrepid entrepreneur. Jobs' dream of building another great computer manufacturer like Apple is dead, dead, dead. Steve had been trying to recreate past glories at Apple when the rest of the world had moved on. He took that lesson to heart. When the world changes, you have to change with it. And once they lean into what they're best at, this is the first time they actually have any kind of success. And the problem was Steve would board out of his mind. And so it says, even if boring could pay the bills, it couldn't hold Steve's interest. As the company pivoted to enterprise software, Steve's attention wandered. He began stepping away from next. He let us manage the company. It was a major shift for an infamous micro manager. That year the company achieved its first profit of a million dollars on revenues of almost 50 million. After nine years of losses, next was finally stepping into the black. And the previous year Steve actually recruited Larry Ellison to join Nexus Board and he gave them some really good advice which they follow. And Larry Ellison said 70% of the IT projects fail in the world. Larry advised the next team to start a professional services group to ensure that the success rate is 100% on your projects. Next did exactly that establishing an internal group to consult on company projects. It was a valuable addition. It gave us insights into what our competitors were doing. The group also came up with ideas for new products. Next survived the year 1994 by building practical solutions to maintain problems. So to do this invention of new products that actually get Steve excited again. So inside next they developed a thing called web objects. In 1995 this idea was a revelation so at the time each and every web page was hand coded resulting in an identical experience for every visitor that made building the online future impossible every time an online store had a price change you'd have to touch 10,000 web pages to rebuild. That's untenable and that is what web objects would fix. He gathered a company together in auditorium. We have this new technology called web objects he announced. The internet is going to be the most important technology transformation of the next 15 or 20 years we're going to burn the boats the future of this company is web objects. Steve followed Larry Ellison's playbook where you're absolutely moving into the consultant selling mode Steve announced following the footsteps of Oracle would be the best example instead of simply selling web objects software licenses. Next would deploy teams of consultants to work on site with clients for months at a time implementing and customizing web objects for each company specific needs this approach would generate much higher revenue per customer and deeper client relationships. Steve had struck a chord everybody was lining up we had meetings every 15 minutes with big customers and one of the first people to see this potential is actually Michael Dell and so it says Michael wanted to build a website that would allow customers configure their PCs online. They could choose processors memory features etc then check out with a credit card a complete vision for ecommerce before ecommerce existed when he asked IBM to build a website the company quoted Michael a two year timeline. Then he tried next they said we get that ready for you in one week within a year del's web objects powered online sales exploded growing to three million dollars a day and quickly becoming the core of the company's distribution strategy dell represented the next generation of tech manufacturers. The web was a clean slate that would place the aging behemoths and nimble challengers back at the same starting line together so the person that worked with Steve jobs for the longest consecutive time was Ed cat mold the co founder picks are I think it was for. 24 short years I actually just met Ed cat mold I spent a few hours with them actually got to go to his house you probably already know this but I have another podcast besides founders that podcast is just my name so if you just search David center if you're not already falling that podcast you should. Because my conversation with Ed cat mold beyond a few weeks and he told some incredible stories and the conversation we had about working with Steve jobs and there's incredible stories about Ed working with Steve jobs in this book so I want to read the section to you. Throughout their partnership Ed had developed a unique approach to working with Steve that avoided the explosive confrontations others experienced I never had one of these loud yelling arguments with Steve ever the secret is understanding how Steve's mind work Steve did not want to be guided in his thinking he wanted to know what the facts are on which to base something Ed once had a disagreement Steve that stretched across three months he was just wrong Ed said the fact that he had a powerful personality and he could think and talk faster than I could didn't make him right. Rather than escalate Ed would present his case and then wait eventually Steve would say oh you're right and that was the end of the discussion the transformation was real and lasting the this is such an important part this is I love this section this is again one of the most important parts of the book the whole point of you and I sit and and talking about this today the people who this is what Ed this is Ed camel talking the people who were with Steve by the end of 95 pretty much stayed with him for the rest of the day. By November 1995 Steve had become the kind of leader people wanted to follow long term and he was humbled now listen to the new Steve jobs. There's no way the Steve that got kicked out of Apple would say what this Steve jobs is going to say right here which is directly related to the point that Ed camel was making above so this is what Steve said if you don't treat talented workers right they can go get another job in 10 minutes. So a strange thing happens which is the sort of the hierarchy of power inverts and the CEO is actually at the bottom so I sort of feel like I work for most of these people because they're the ones that are doing all the brilliant work. Now the timing of this is so important because as Steve is transforming as next is now on the black at the exact same time Gil Emilio is the CEO of Apple and they are bleeding money they can no longer create their own operating system and the Gil realizes we have to go out and buy another operating system. And there's two great sentences here that I think really summarizes the problem that Apple's having this time so it says Apple had no hits of its own to speak of it produced a mess of middleing products with bewildering names like cyber dog Apple script hypercard fire wire open dock power PC. The old Apple had made two things the Apple to and the Macintosh and they had made them well and here's this remarkable twist of fate that changes history there is a product manager and next this guy named Garrett rice he's reading in the newspaper that Apple was prepared to spend tens of millions of dollars on this other operating system called B which they thought was just a pale imitation of Nexus technology and so Garrett rice asked the question why don't we just frickin call Apple that's what he says. If Apple is looking at B why not just buy the real thing. Garrett believe that next stood on a dragons horde of technology that everyone seemed to be overlooking so Garrett calls this woman Ellen who's the CTO of Apple to time and pitches her on her answering machine. He did not focus on Steve he's said talked about Nexus technology and he argue that if Apple wanted to be thorough it should at least look at next Ellen who again is the his the CTO of Apple said I hadn't even thought about that imagine how different history could be if Garrett rice didn't ask the question why don't we just frickin call Apple and so one Steve here's about this he does the smart thing he calls guild directly and gives him a simple message BOS was the wrong choice for Apple. Gill then in turn invites Steve to come make his case in person and regardless of the time and place in Steve's jobs life history one place you don't want to be at is in a presentation dual with him because Steve invited to pitch and the founder of BOS is invited to pitch and look at the contrast in what they did so Steve walked into girls conference room and he pitched Apple's leadership on an entirely new strategy built around next as he began to detail. next steps innovative features, Gil noticed something different about Steve. He wasn't the same person as the self-absorbed entrepreneur Gil had once known. In his place, Stuart a very pragmatic, specific, and precise executive. When the time came for a technical demo, he turned the floor over to Avi instead of doing it himself. This is Avi Tafanian, most likely mispronouncing his name, but he was the head of software engineering next. So it says at the time when most personal computers struggled to play a single video file smoothly, Avi showed that next step could handle them and more. We had productivity apps, we had games, we had quick time movies, four of them on the screen, 3D models all going at the same time. The Apple team knew they were witnessing the future. And when Apple engineers would question or bring up concerns, it says Steve did not dismiss their concerns as he might have in the past. He acknowledged them, suggesting that they were the kind of solvable engineering problems that accompany all technological advances. Steve was very smooth. After a little more than an hour, the next team left the room. They had made a strong impression. The founder of B walks in and he pursued a different approach. He hadn't brought anyone else from his team. He wasn't carrying a laptop. In fact, he had prepared no presentation whatsoever. Because the two teams had been kept separate, he had no idea what Steve had just done. His pitch was your technical people have met with my technical people. So you know the strengths of our solution. Steve had demonstrated his product superiority through working code. The founder of B offered only entitled assumptions. Three days later, Steve invited Gille to his home and they started the negotiation to purchase next. Steve opened offering the company at $12 a share, which would have made the total acquisition price $500 million. $12 isn't possible. Gille told him, "Well, what's the number you're looking at, Steve asked? I think I have a shot at convincing the board to take $10. I don't think I can get a penny more than that." The negotiation turned out to be speedy. Steve didn't care about squeezing every penny from the deal. The negotiation was different from any Gille had experienced. The traditional scene, a corporate boardroom in the typical players, corporate lawyers were replaced with two men haggling in a kitchen. Later, they called it the fastest acquisition of scene in the world. The whole pricing discussion took five minutes. Even as he worked to seal the deal, Gille's allies gave him stark warnings about what Steve's return might mean for his own leadership. I remember sitting in a meeting and saying to Gille, "If you buy next, Steve will end up running the company." But Gille didn't understand how much firepower Steve had. Either that or he felt he could harness it. And you can't. Steve doesn't know how to do anything, but lead. An apple alumnus who had known Steve since the early 80s put it more colorfully. So this guy calls Ellen, who is the CTO of Apple, and says, "Ellen, Steve is going to fuck Gille so hard his eardrums will pop." Gille felt he could hold his own against Steve. Next executive stock Gille failed to grasp what Steve's 12 years in the wilderness had given him. Steve came away not only with better skills for building technology, but better strategies for getting exactly what he wanted. This is the crux of the book I'm going to read it again. At 43 years old, Steve had returned to the former home that had thrown him out. Apple was his again. And this time he was ready.

Podcast Summary

Key Points:

  1. Steve Jobs’s 12-year exile from Apple (1985–1997) was marked by repeated mistakes, including overspending, poor strategic decisions, and a focus on revenge against Apple.
  2. During this period, Jobs founded NeXT, but his lack of cost discipline—such as paying $100,000 for a logo and building a lavish manufacturing facility—drained his fortune.
  3. Jobs’s leadership style at NeXT was volatile, creating a “hero/shithead” roller coaster for employees, though he later learned to control this when he returned to Apple.
  4. A key turning point came when Ross Perot invested $20 million in NeXT after seeing a PBS documentary, providing crucial funding.
  5. Jobs’s exile forced a personal transformation, enabling him to become the visionary leader who would later re-found Apple and engineer its spectacular turnaround.

Summary:

This transcript explores the critical 12-year period when Steve Jobs was exiled from Apple, as chronicled in Jeffrey Cain’s book *Steve Jobs in Exile*. After being ousted in 1985, Jobs struggled with direction, briefly considering a quiet life in Paris before founding NeXT. His early leadership was flawed: he overspent on a $100,000 logo, built a costly manufacturing plant, and wasted resources on revenge ads against Apple.

His volatile management style—praising employees one moment and tearing them down the next—created a toxic culture. Despite these mistakes, Jobs showed signs of growth, hiring talented renegades like designer Hartmut Esslinger and logo creator Paul Rand. A critical lifeline came when Ross Perot invested $20 million after seeing a PBS documentary about NeXT.

The period forced Jobs to evolve from a brash, vengeful entrepreneur into a more disciplined and visionary leader. This transformation was essential for his later return to Apple, where he would re-found the company and achieve one of the most remarkable turnarounds in business history. The story underscores that failure and exile can be catalysts for personal growth, even for the greatest innovators.

FAQs

The book chronicles the 12-year period between Steve Jobs being kicked out of Apple and his return, highlighting his mistakes and personal transformation.

He aimed to build a computer for the university market, but was also motivated by a desire to get revenge on Apple.

He wanted a permanent ensemble of brilliant people who could engage in intellectual warfare, pushing back against his ideas to ensure the best options survived.

It referred to Steve Jobs' unpredictable behavior, where he could lavish praise one moment and harshly criticize the next, creating an unstable atmosphere.

He hired designer Paul Rand, who demanded a flat fee of $100,000 regardless of whether the logo was used, and Jobs agreed due to Rand's reputation.

Ross Perot saw a PBS documentary about NeXT and called Steve Jobs, eventually investing $20 million for a 16% stake after Jobs added $5 million of his own money.

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