Generalist updates
Aug 31, 2023

Introducing our newest writer

Welcoming a fresh voice to The Generalist and what that means for readers.

Artwork by 
Eleanor Taylor
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My ultimate mission with The Generalist is to build the most thoughtful publication in tech—a home for deep, original analysis, conversations, and shared discovery. Last year, we started searching for a new writer to help grow our coverage, improve our thinking, increase The Generalist’s value to readers, and ultimately, bring us closer to that goal.

Since the beginning of this publication, I’ve enjoyed sharing “behind the scenes” details with you all, charting the ups and downs of building a modern media business. With that in mind, I’m excited to share an important update. The Generalist has found its newest writer: Ben Butler. I couldn’t be happier to have him join.

While I’ll let him tell you more about why he’s jumping aboard (below), I do want to take a moment to share what it was about Ben that made Ali and me confident he is the right addition to the team. And why I think it’s good news for readers like you.

First of all, Ben knows startups. He spent five years at one of my favorite companies to study, Stripe. As long-time readers will know, I admire the payments company as much (if not more) for its culture of serious thinking and thoughtful writing as for its technological product. During his time at Stripe and, later, Evervault, Ben developed an appreciation for the rigors and rhythms of company building that far exceeds my prior operational work. He knows what it means to see a business grow 10x – and then do it again (and again). Bringing this experience to bear will not only push The Generalist to level up its internal operations but will also bring a fresh dimension to our written analysis. While I can approximate what it is like to work at a true rocketship company, Ben can speak from vivid experience.

Second, Ben is someone with a strong sense of taste. From literature to music to seed stage B2B SaaS companies, he has a distinct point of view and feel for what is intriguing, interesting, and worth digging into. He is, by nature, not a simple observer of the world but an analyzer – someone who forms opinions and is gifted at articulating them. As his colleague and a reader, I look forward to Ben pushing our thinking forward and into new directions.

Third, Ben is a creative. Outwardly, he may look like a good and proper business person with the degree and credentials to show for it. He is, however, a writer at heart. Prior to joining The Generalist, he exercised that creativity through pursuits like stand-up comedy and screenwriting. But in getting to know Ben, I quickly realized he had an urgent, unfulfilled desire to turn his passion into his profession. Ben’s drive to make writing his vocation is matched by his talent. He has a natural gift for crafting elegant sentences and nuanced arguments. In the years to come, I am optimistic that many of The Generalist’s best sentences will have been penned by Ben.

Finally, and perhaps most importantly, Ben is someone I feel lucky to call a colleague and a friend, possessing integrity, curiosity, and deep thoughtfulness. I hope you will join me in giving him a hearty welcome.

And now, a few words from Ben.

A note from Ben

New friends,

I’m joining The Generalist as their first writer. I’ve always enjoyed writing, and I’m fascinated by tech. I’m incredibly excited to combine both of those worlds.

I joined Stripe Dublin when we were a four-person team in a one-room office. Stripe globally was around 200 people, and growth was taking off. Seeing extreme product-market fit like that was an incredibly accelerated learning experience, viscerally illustrating the speed, scale, and impact great startups can achieve. I worked in operations, sprinkled with a focus on culture and company building: first to help grow the team in Dublin, and then being asked to move to Seattle to do the same there. Highlights include launching our first paid support plan and working with companies like Squarespace through the Stripe Partner Program.

Stripe also happened to be a great place for writing. While this would later culminate with the launch of its own publishing arm, Stripe always had writing at its core. Even in operations, I wrote a lot – and the standard was meticulous (emails with footnotes!). As patio11 has noted: “Stripe is a celebration of the written word which happens to be incorporated in the state of Delaware.”

As someone who has loved writing from an early age, that cultural trait was particularly valuable to me. Growing up, I’d written plays for my youth theater group and won a couple of short story competitions. I wasn’t doing much prose in my twenties, but I debated in college and semi-seriously pursued stand-up a couple of years after. I briefly merged this comedic moonlighting with my day job by hosting a late-night-style show at Stripe’s annual gathering. That was a highlight of my time there and – looking back – a big clue to my interest in that intersection.

After moving back to Ireland during the pandemic and taking some time off, I got a Twitter message from Shane Curran, founder of encryption startup Evervault: “Would I be up for a chat?” Three weeks later, I joined as employee number five, initially as Head of Talent and, later, Head of Operations. I had a great two years there, but I had this niggling feeling that I needed to do something else. I took a screenwriting class and was shortlisted for Screen Ireland’s flagship writing scheme. Even when pursuing my passion, I couldn’t leave my day job totally behind, though (the screenplay was called “Big Tech”).

When I look back on my operator career, I enjoyed the constant variety and problem-solving that it provided, but something was missing. I think the Japanese term “ikigai” sums it up best. Ikigai is the intersection of what you love, what you are good at, what the world needs, and what you can be paid for. The reality is that most people don’t have a job that hits those four things. Many people don’t even get two. I’d had some great experiences, but my heart was always elsewhere. I’d consistently dabbled in something creative, but I loved tech and didn’t think I could make a living writing. I certainly didn’t know I could combine both of those worlds.

And then I met Mario.

I’ve been a fan of The Generalist since the Stripe piece. Not only was it the best analysis of a company I knew intimately, but it was also a nerdy dream of Latin quotes and classics references. The prose was excellent, but so was every little detail: strong branding, custom illustrations, and a cogent point of view. When I saw that they were hiring their first writer, it seemed the perfect role for me.

After a couple of calls and an assignment, I flew to New York to meet the team. And what a team! Mario is an incredible writer, and I’m learning a lot from him. Ali is a world-class operator and makes me realize how unsuitable I was for operations. More importantly, they’re both wonderful humans that I feel privileged to work with. And it’s crazy to think how early we are and where it can go. The Economist was founded in 1843. The New Yorker was born in 1925. The Generalist started three years ago.

Even though I’ve always had a writer’s soul, I’ve had an operator career. Adjusting to a maker’s schedule from a manager’s will be a challenge, but it’s one that I’m relishing. Simply put, I now get to live like Roald Dahl in his writing shed, but also stay plugged into an industry I love. Where else would I get that but The Generalist?

See you on Sunday,


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