General Catalyst, Four Books, Ten Years and Lots of Billions

I first met Hemant Taneja in November of 2013. We were set up by a PR person who thought I’d find Hemant interesting, and we planned to meet at 5 pm at the bar at Café Luxembourg on the Upper West Side of Manhattan.

I’m not sure what we ordered. A beer? Cocktail? We sat on barstools and I, wearing my journalist hat as tech columnist for Newsweek, likely started with small talk (Why are you in New York?) and then asked Hemant about himself and his work.

I had not before heard of Hemant. I was not familiar with his firm, General Catalyst. I knew tons of VCs and had relationships with the top firms, but General Catalyst, or GC, at the time was a lesser player. Hemant was best known for having made a major early bet on Stripe, which, in 2013, I couldn’t understand. Stripe was tiny, and it seemed to me and a whole lot of others in tech that Stripe was just another me-too payments platform, which the world wouldn’t need. (Of course, Stripe turned out to be one of the more brilliant early-stage investments. It’s now worth north of $100 billion.)

As we talked, Hemant told me about a concept that he called “unscaling.” Basically, it’s the idea that AI, the cloud, mobile devices, internet of things and other recent technologies will increasingly allow companies to do the opposite of mass-production, mass-marketing, mass-media and all the other twentieth-century “economies of scale” stuff that was designed to sell the most of the same thing to the most people.

Instead, unscaled companies will increasingly offer highly-individualized products and services that seem to be built specifically for one person. Much of that is happening today, accelerated by AI.

I’ve always been a sucker for big ideas that seem to explain something about how the world is changing, and I remember coming away from that meeting with the unscaling theory circling my brain. I started slipping the idea into Newsweek columns. I talked about unscaling some more with Hemant. The next time I was in the Bay Area, I visited him at GC’s small office there.

Sometime in 2015, after I’d written a few times about unscaling, Hemant and I met again in New York and he suggested that we should do a book together about it. I had just finished co-authoring Play Bigger, which would come out in June 2016, and was ready for a new project. We put together a proposal and sold the book idea to the publisher Public Affairs. Oddly enough, the editor who bought it was John Mahaney, who bought and edited my first book, Megamedia Shakeout, 22 years earlier.

So, Hemant and I wrote Unscaled: How AI and a New Generation of Upstarts Are Creating the Economy of the Future. It came out in 2018, apparently a good four years too early. At the time, the topic of how AI was going to upend industries across the spectrum wasn’t yet on most people’s radar. Now it’s all anyone in business talks about.

One of the chapters in Unscaled focused on healthcare. By the time the book hit the market, Hemant and General Catalyst were investing big in healthcare technologies, with a belief that AI could reinvent the sector. We decided healthcare needed a whole book of its own. Hemant brought Steve Klasko into that project. Klasko was CEO of Jefferson Health in Philadelphia, and was partnering with General Catalyst. The three of us wrote and published UnHealthcare: A Manifesto for Health Assurance.

One goal of that book was to establish a new category of healthcare that was all about using technology to keep people well and out of hospitals and doctor’s offices, and we called that category “health assurance.”

UnHealthcare came out in 2020. Almost immediately, Hemant and I started on yet another book, this time about how “responsible innovation” and how to build companies that would help (and not hurt) society. Intended Consequences was published in 2022. In tandem, Hemant set up the non-profit Responsible Innovation Labs, which helps founders build responsible-innovation companies.

Throughout all of this, Hemant was remaking General Catalyst, and he and the firm were hitting home runs with both companies it invested in and, more unusual for VCs, companies it helped start. Stripe and Samsara were big investment wins. So was Snapchat and Airbnb. Hemant co-founded Livongo, which eventually got bought for $18 billion.

In the early 2000s, GC was a regional firm based in Boston and had $257 million in assets under management (AUM). By late 2024, its AUM was $33.2 billion and GC operated nine offices globally, including in Silicon Valley, New York, London, Berlin and Mumbai. In 2025, when Time magazine ranked America’s top VC firms, General Catalyst landed at No. 2, just behind Accel and one ahead of Andreessen Horowitz.

After Intended Consequences I thought we were done writing books. But on another visit to New York, over another cocktail (this time at the Crosby Hotel Bar, in November 2022), Hemant said we should do one more – a book that would capture the core principles that guide him and his firm. I remember thinking: That seems like something a lot of people would want to read, given GC’s outsized success and Hemant’s growing fame.

At the heart of those principles would be General Catalyst’s belief that companies that benefit society and solve hard problems like climate change and the U.S. healthcare mess offer the best returns over the long haul. I loved it and signed on.

The book took about 15 months to complete. BenBella Books published it on Sept. 23. It’s titled The Transformation Principles: How to Create Enduring Change. The book details nine of these principles:

— The business must have a soul.

— Navigating ambiguity is more valuable than predicting the future.

— Creating the future beats improving the past.

— Those who play their own game win.

— Serendipity must become intentional.

— For great change, radical collaboration beats disruption.

— Context constantly changes, but human nature stays the same.

— The choice between positive impact and returns is false.

— The best results come from leading with curiosity and generosity.

Available wherever books are sold.

 •  0 comments  •  flag
Share on Twitter
Published on September 28, 2025 12:08
No comments have been added yet.