Jean-Louis Gassée at Be, Inc., the company he founded after leaving Apple, in the 1990s.

How Apple’s former head of product is sharing decades of business wisdom on Medium

An interview with Jean-Louis Gassée, creator of Monday Note on Medium and author of ‘Grateful Geek’


Jean-Louis Gassée is the former head of product development at Apple — he shaped the Mac’s early history in the ’80s, releasing products like the Macintosh II and Apple’s first laptop. For the last seven years, he’s been publishing regular reflections on business and tech through his Medium publication Monday Note. Over 20,000 readers follow along as Gassée distills decades of wisdom into timely perspectives on everything from Silicon Valley Bank to the Apple Vision Pro.

Gassée’s stories contain the kind of insight you can only get after a 50-plus-year career as a leader in tech. I’ve been curious about his experience at Apple (and after Apple) for years, so we met over Zoom to discuss the company’s storied past and future, his experience on Medium, and his new memoir Grateful Geek. Here’s a transcript of our conversation, which I’ve edited for clarity and concision.

Harris Sockel: Your publication Monday Note has been going strong for over 16 years now (!). You have such a knack for getting to the heart of tech news. Why did you start Monday Note?

Jean-Louis Gassée: I began Monday Note at The Guardian, actually, over a decade ago! My cofounder, Frederic Filloux, had enjoyed a long career in European journalism, and he and I wanted to start our own series of musings on business and tech. The Guardian was kind enough to host us at first; we built a loyal readership there, but eventually one of their lead editors left and they lost interest. We needed a new platform.

Medium deserves tremendous respect for building an open platform that’s not polluted by anger and disinformation.

Frederic suggested Medium, so we gave it a shot. It turned out to be one of the easiest publishing tools we’d ever used. As a writer, there are very few dials I need to twist to get something done. Medium provides the perfect set of tools to quickly and simply write an essay, polish it up, and publish. We’ve been using the platform consistently since 2016. (Frederic moved on to other opportunities a few years ago, so I run The Monday Note myself now.)

Beyond the tools, Medium deserves tremendous respect for building an open platform that’s not polluted by anger and disinformation. I find myself blessed and grateful for that environment. Staying hate-free and anger-free is admirable in this industry!

HS: Did anything change about your approach to writing after moving from The Guardian to Medium?

JLG: I was much more aware of my political surroundings at The Guardian. It’s a liberal publication, so I had to be aware of that. I wouldn’t call it self-censorship, exactly, but I did have to pay attention to what I said.

On Medium, I feel freer. I also have more control over how my essays look. I like to keep things simple. Medium affords me a nice balance between flexibility and simplicity.

HS: I’d love to hear more about your experience as an executive at Apple. How did you end up there? What did you learn?

JLG: Sure! It was the early 1980s and I was working as CEO of Exxon’s French affiliate. I met a Wall Street analyst friend for lunch; he told me Apple was starting a subsidiary in France and needed someone to lead it. At the time, I’d been working at Exxon for seven years and was looking for a new opportunity. Apple seemed like a perfect fit — I signed my employment agreement the day of Apple’s IPO: December 12th, 1980.

Back then, things worked almost magically well at Apple. We were rebels against the computing establishment. IBM was the evil giant, and French consumers responded fantastically to our renegade branding. By the time I left my post as the head of Apple France in ’85, we were the largest Apple business outside of the U.S. That’s how I built my reputation.

Eventually, I became more outspoken on the executive team. I criticized the way we were marketing the Mac in the U.S. I thought (and still think) Apple’s attempts to win over corporate American customers were foolish. We had the LaserWriter, we had Adobe software, we had the Mac’s beautiful user interface. Lots of individuals would enjoy that! We didn’t need to sell out to corporations. Doing so would dilute our brand, I felt. I was fiercely opposed to it.

Soon after I spoke out about our marketing strategy, I was asked to start a software division in the U.S. because (and this is a tale as old as time within Apple) the Mac didn’t have enough native application software.

A few years later, in 1985, Steve Jobs tried to oust then-CEO John Sculley. I sided with Sculley, who appointed me to run product engineering in Cupertino. The Mac wasn’t doing very well (it wasn’t as compatible or customizable as its competitors, which was a major drawback in the early days). Eventually, we managed to get the Mac out of the ditch, business-wise. Finally, I parted ways with Apple in 1990. Sculley and I disagreed over the future of the company, and we decided it was best for me to leave.

It was an emotional but ultimately amicable parting. I have no beef. I still view John Sculley as my benefactor. He gave me a huge opportunity to run the product side of Apple, so I’m deeply grateful to him. For five years he was quite tolerant of my occasional vehement disagreements.

HS: Why did you side with John Sculley over Steve Jobs?

JLG: Honestly, despite all the gratitude I (and all of us) have for Steve’s contributions to the world, at the time he really didn’t know much. He knew Apple. That’s what he knew. He knew little about the wider world.

But Steve’s passion for Apple was incredible. I remember conversations in Paris — Steve visited Apple France often — where we’d talk about the world, life, and his experience being fired from Apple in 1985. He fell from his horse, dusted himself off, and created Pixar. If all you do in your life is create Pixar, you’re a titan of industry! But Steve didn’t stop at Pixar. He tried to make computers again and unfortunately called his company “NeXT,” which was a fairly obvious snub to Apple. NeXT was a technical success but a commercial failure. They had an operating system but no machine to run it. He had no “horse” to ride on, so to speak.

He found that horse when he moved back to Apple and brought NeXT along with him. He also brought Scott Forstall, among others, and they managed to rejuvenate the creaky Mac OS, turning it into a modern Unix base at the very bottom and the operating system we enjoy today.

I think Steve was burned and burnished by his experience at Apple. Being let go made him and the rest of us successful.

HS: Back to your experience on Medium — who are your readers? What’s your relationship to them? Any noteworthy responses you’ve received?

JLG: My readers are a diverse mix of folks! They’re as fascinated by the future of tech (and Apple) as I am. Many are critical, which makes sense because I sometimes post controversial opinions like this one on Intel’s culture. I welcome critical readers — I really do, I’m not being diplomatic. I write Monday Note to figure out what I think. It’s one thing to have brilliant ideas in the shower, but it’s another thing to put them on (digital) paper.

I’m 79 and change, and over time I’ve learned not to engage in a heated exchange online. I always let the heat come down before responding (regardless of whether I think my critics are right or wrong). As a result, I’ve built a kind of mutual understanding with my readers.

I have to mention one reader in particular (they’ll remain nameless, but they know who they are!). This reader has an eagle eye for typos, but also for quirks of translation when I write in English as a non-native speaker. I’m indebted to them. I love the English language; I sometimes mistreat it, but I love it. I credit that reader, and their corrections, in the printed version of my book, Grateful Geek.

HS: Is there a specific Medium story of yours that you’re proud of, or that had more of an impact than you expected? One that comes to mind for me (and that I still go back to) is your essay on Jeff Bezos’s approach to writing. Over 150,000 people have read, shared, and responded to that essay. Why do you think it resonated so widely?

JLG: I have a ton of respect for Bezos. I’ve known some of his close collaborators in my career — one of whom shared a few insider anecdotes about how he runs Amazon. I read his yearly letter to shareholders, and I now have friends deeper inside the organization who all confirm that each of Bezos’ meetings starts with a silent reading of a six-page essay. He also forbids PowerPoint; in his view, PowerPoint sterilizes thinking. Based on the responses to that essay, readers seemed to agree.

I also got quite a response from a series of essays I published about human resources. When I landed in Cupertino in ’85, I discovered that the engineers (whom I was in charge of managing) called HR “the Gestapo,” “the KGB,” and “the thought police.” Based on my experience with HR at Apple, I wrote a trilogy of essays about hiring, firing, and performance reviews — and those generated lots of conversation within my network outside of Medium.

HS: Tell me about your new book. Why did you decide to self-publish instead of seeking a publisher?

JLG: Years ago, I became friends with investor Steven Sinofsky, who self-published a masterful memoir, Hardcore Software, about what he learned as Bill Gates’ technical assistant at Microsoft in the early days. He eventually became president of Windows and was later fired by the ever obliging Steve Ballmer.

Sinofsky showed me the manuscript before he released it and explained his decision to self-publish. In addition to the freedom you gain by self-publishing, you’re able to avoid the reductive framing many publishers (especially publishers’ marketing departments) will use to sell a book.

Grateful Geek is essentially a memoir about my life and career: how I came to work at Apple and what I learned there. If I were selling it to a major publisher, I imagine they’d want me to say something about how Apple lost its soul when Steve Jobs left. They’d want the dirt about my departure, about being let go by Sculley, and about the drama over siding with Sculley instead of Steve Jobs right before Jobs was fired. But I don’t believe Apple lost its soul. And I don’t actually have very much dirt! I’m pretty positive about Apple, Jobs, and Sculley. I have no dirt or gossip to share about anyone.

So, I self-published it. I shared it with the folks at Apple and got a very positive reaction.

HS: Imagine you’re advising someone who wants to start writing on Medium — or just on the internet at large. What advice would you give them?

JLG: I would have to resort to a fairly banal, “Just do it so you can get feedback.” Don’t spend too much time thinking, because that can lead to paralysis. Find a good editor, someone to read your drafts. I have a great editor, Doug Fulton, who was the editor of the Be newsletter. (Be, Inc. was my next venture, after Apple.) We had a weekly newsletter at both Be and Apple France. So I’ve been writing more or less weekly forever.

What I like about Medium is that the most difficult part is the writing part.

Roll with the punches. What I like about Medium is that the most difficult part of Medium is the writing part. The rest is easy. I can focus on the hard part, which is to figure out what I think I think and put it in words. Lastly: Don’t question yourself, let the readers question you.