Category: Books
I love to read.
As a kid, my idea of a good time was being in the hammock in the backyard of my house in Dallas, Texas, reading a book. My parents supported this, letting me read anything I wanted from their bookshelves (I read The Drifters at much too young an age). I loved buying books, and today, I have an infinite number of unread books on my Kindle. I vary my reading diet and log it all in Goodreads (ignore the stars).
One of my “book heroes” is Ryan Holiday. We met at a dinner at SXSW in 2007 or 2008, and I’ve been a fanboy ever since. I’ve read all his books, happily get his monthly reading newsletter (which motivates me to buy a book or two he recommends each month), and am inspired by his Painted Porch Bookshop.
His op-ed in the New York Times on April 19, 2025, titled The Naval Academy Canceled My Lecture on Wisdom stopped me in my tracks. Nothing much is surprising me daily anymore (per my long-time philosophy about my business life, that now applies to a much broader range of things, that I wrote about in Something New Is Fucked Up In My World Every Day.)
The first book I remember reading about censorship was Fahrenheit 451. I remember being repulsed by the idea that a government would ban (and burn) books. I was young (probably less than ten) and followed it quickly with 1984. Yeah, I read a lot of dystopian sci-fi as a kid.
Thoughtcrimes, Newspeak, and Doublespeak were grotesque ideas to me. I hated the idea of the Memory Hole. I grew up feeling like it was important to read everything, even if I didn’t like it or disagreed with it.
I still try to do that in today’s world, but I limit it to reading. I don’t apply the same concept to watching videos or TV. I don’t learn verbally and have trouble synthesizing information when visually stimulated. While my retention from listening is fine, I don’t effectively incorporate ideas unless I read or write something about them. I’ve tried to address this by taking notes when listening to a video or a lecture, but that doesn’t work for me, so I’d rather just read the transcript.
Ryan described a story about James Stockdale, which he would have discussed in his canceled Naval Academy talk on Wisdom. The story aligns exceptionally well with the meta-level of his talk’s cancellation and includes a great ending.
“Compromises pile up when you’re in a pressure situation in the hands of a skilled extortionist,” Mr. Stockdale reminded us. I felt I could not, in good conscience, lecture these future leaders and warriors on the virtue of courage and doing the right thing, as I did in 2023 and 2024, and fold when asked not to mention such an egregious and fundamentally anti-wisdom course of action.
Book: Scaleup Arabia: Journeys & Lessons from Top Founders & Leaders Driving Growth in MENA & Beyond
In addition to writing books, I love supporting books written by friends.
Amir Hagazi has published his newest book, Scaleup Arabia: Journeys & Lessons from Top Founders & Leaders Driving Growth in MENA & Beyond. The image above shows some of the founders highlighted in the book, and the image below shows some of the companies discussed in the book.
While I don’t do book blurbs anymore, I have written forewords for Amir in the past on two of his prior books, Ecosystem Arabia: The Making of a New Economy and Venture Adventure: Startup Fundraising Advice from Top Global Investors, both of which I recommend.
If you are interested in scaleups (I love that word as a complement to startups) and are interested in companies in MENA, this is the book for you!
Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom
Dan Caruso’s new book Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom is available for pre-order, to be released on February 4, 2025.
Order your copy today on Amazon or Barnes & Noble. You can also subscribe to Dan’s Bandwidth newsletter to receive updates on the book release and launch events.
Dan asked me to write the foreword, which I happily did. See an excerpt explaining why I loved reading this book.
Bandwidth Foreword Excerpt
In April 2024, Dan asked me to look at his manuscript. I read the introduction and, within a week, the rest of the book. Reading it reminded me of places where my path crossed his, such as Exodus acquiring Service Metrics (a Mobius investment), which returned our entire first fund. Of course, several years later, after the result of a horrifying merger with Global Crossing, the combined Exodus-Global Crossing went bankrupt. Or, the day Howard Diamond, CEO of Corporate Software (another Mobius investment), walked into my office and said, “Level 3 is acquiring us for $125 million,” to which I said, “Why the fuck would a telecom infrastructure company buy a software reseller?” And then there were stories Dan didn’t even know, like the time I sat in Level 3’s office in Broomfield, Colorado (five minutes from my office in Superior, Colorado), in 2001, praying Level 3 would buy Interliant (a failing public company I was co-chair of) for no other reason than Level 3 had bought other failing public companies. And, no, Level 3 didn’t buy Interliant, and yes, Interliant did fail.
Before reading Bandwidth, I saw the Internet Revolution through the lens of software and Internet companies. I knew some of the stories of Qwest, Enron, Global Crossing, Level 3, and others—but didn’t appreciate the details and magnitude of the Bandwidth Boom and Bust. The adventurous stories of business legends such as Phil Anschutz, Craig McCaw, Jim Crowe, and even Carl Icahn were exciting to read. The exploits of bad actors such as Joe Nacchio, Gary Winnick, and Bernie Ebbers were even more exhilarating. Epic battles of hostile takeovers, botched business plans, phoenixes rising from ashes, and entrepreneurs who persevered reminded me why I get so much fulfillment from helping start-ups become large successes and enduring companies. And why I am willing to fight for any company in which I’m involved.
As I read, I also learned a lot more about Dan. I now know why so many people have strong feelings about Dan—some think he walks on water, while others wish a big wave would knock him over. In this book, he openly shares the challenges he had to overcome and the pivots he had to make. At each step, he is delightfully self-deprecating and aware of what worked and what didn’t. I, for one, enjoy watching him continually do extraordinary things. Put me in the “Dan walks on water” camp.
Are you interested in AI? Do you enjoy science fiction? Do you have an opinion about how AI will impact the human species? Are you enthusiastic about it or worried about it? Or do you think you know the answer?
Dave Jilk (my first business partner and one of my closest friends) recently published EPOCH: A Poetic Psy-Phi Saga.
When Dave described the idea for the book he was working on during a long hike four years ago up and around Green Mountain in Boulder, I was fascinated with what he had decided to take on. AI wasn’t front of mind in the same way as today, but Dave had been doing research in that arena for around a decade. When we talked about AI, our discussions usually revolved around aspects of AGI. I was mainly in listening and questioning mode since Dave’s knowledge and thoughts quickly went beyond my understanding of – well – all of it.
Dave could have taken his deep understanding of AI, technology in general, philosophy, and psychology in multiple directions with an extensive writing project. But yet another book explaining AI or philosophizing (or rhapsodizing) about it would be … boring. And while I’m enjoying reading lots of AI-inspired sci-fi, AI is now a routine trope that is being woven into more complex sci-fi.
So, Dave decided to write a poem—a very long poem—an epic poem about AITHER, the first fully human-level artificial general intelligence. It is a memoir by AITHER, entirely from AITHER’s point of view. As the first human-level AGI, AITHER muses extensively about identity and purpose, future selves, the importance of beauty, the nature and ethics of technological progress, cultural influence and hegemony, humanity’s tragic flaws, and existential risk.
There is also a soundtrack because every book needs a soundtrack. If you like album-length soundtracks, Dave subsetted a soundtrack for the wireheading scene.
But EPOCH is not simply an epic poem about the first human-level intelligence AGI. It is filled with allusions to books, poems, songs, academic papers, paintings, and films. In Dave’s words:
“These are not merely passing linguistic echoes; in most cases they connect with the point made or the topic addressed. As a whole they are also an important thematic element of the book, and are called “osculations.”
EPOCH: A Poetic Psy-Phi Saga took Dave four years to create. I read the first half about two years ago and the completed draft about nine months ago. I remember vividly telling Amy, “Reading this book is a lot of work, but it is totally worth it.”
If you want more of the backstory, look at the EPOCH website.
But know that I strongly recommend you buy a copy of EPOCH: A Poetic Psy-Phi Saga right now if you are interested in AI, sci-fi, philosophy, psychology, technological progress, humanity’s tragic flaws, or a fantastic work-product from four years of effort.
Book: Unshackled: A Practical Guide For Highly-Skilled Immigrants To Thrive In The United States
I recently wrote the Foreword for Unshackled, a new book co-authored by Soundarya Basubramani, a writer from India, and Sameer Khedekar, a veteran immigration lawyer. Unshackled breaks down how legal immigration works in America in a way that is friendly, accessible, and human. It’s filled with raw stories of high-skilled immigrants who walked unconventional paths and actionable guidance to navigate those paths.
Last August, Rajesh Setty sent me an email request from Soundarya when the book was just an idea. Soundarya shared her vision for the book and why she wanted to write it. Unsurprisingly, the motivation stemmed from personal frustrations with the immigration system in the U.S.
Legal immigration, especially for high-skilled immigrants, has been important to me for over a decade. I was deeply involved with the Startup Visa movement back in 2010. When that ultimately failed, I began supporting several grassroots movements like the GEiR program, invested in companies founded by immigrants, am an investor and board member of Boundless, an early LP in Unshackled Ventures (unrelated to this book), and even became the executive producer of a movie called For Here Or To Go. Unshackled seemed another step in the right direction.
I met with Soundarya and Sameer on a video call in late August. Their pitch had promise, and I encouraged them t set up a crowdfunding campaign. They did this, and I was one of 612 people who supported the campaign, which raised $48,340. Soon after the campaign ended, Soundarya received a $50,000 grant from Emergent Ventures for the project.
Soundarya kept me updated, and I got the unpublished manuscript for Unshacked five months later. I read it over one weekend, and I loved it. The book didn’t feel like a legal guide. Soundarya and Sameer managed to break down how legal immigration worked in simple and engaging language while capturing the raw emotions in the firsthand stories of immigrants. Having seen the book come to life from a mere idea just nine months ago, I agreed to write the foreword.
Less than a year from its inception, Soundarya and Sameer are hosting a grand event to launch their book on July 22nd, 2023, in Sunnyvale, CA. While I cannot attend the event, I hope you can make it and support a worthy project. Doug Rand, who currently serves as an advisor to the Director of USCIS, is set to be there for a fireside chat on the past and future of immigration policy.
Soundarya and Sameer – congratulations on publishing this important book. And, Rajesh, thanks for connecting us.
John McPhee’s Levels of the Game was published when I was three. I’ve read many books about tennis, but it’s still my favorite, with String Theory: David Foster Wallace on Tennis coming in a close second. Both books share extraordinary writers and a topic I can relate to, given my short but profane junior tennis career.
I’ve become annoyed by the writing that ChatGPT produces. At first, I was fascinated. As I saw more of it, I began seeing patterns. After reading Stephen Wolfram’s article What Is ChatGPT Doing … and Why Does It Work? my observation shifted to impatience. Most of my ChatGPT efforts now are making it hallucinate.
I finished Draft No. 4: On the Writing Process a few minutes ago. I enjoy reading books about a craft by a master of a craft, especially when it’s a craft that I practice, even if I’m not that good at it. Tennis is one example. Writing is another.
After reading Draft No. 4, I envy writers with excellent editors. For the books I’ve written, I’ve enjoyed my relationship with my editor, but he mostly plays the role of project manager. My experience, compared to Jerry Colonna’s relationship with his editor, is completely different.
I had continuous insight into this difference while reading Draft No. 4. McPhee is a spectacular writer. He has also been blessed with over 50 years of great editors, including The New Yorker’s Robert Gottlieb. While writing can be extremely solitary, the relationship between writer and editor can be a beautiful dance. If you want to understand that in-depth, grab a copy of Avid Reader: A Life by Robert Gottlieb.
ChatGPT badly needs an editor. Apparently, it agrees.
As an AI language model, I don’t have personal preferences or needs like humans do. However, it’s always beneficial to have human editors or reviewers involved when using AI-generated content, including the responses from ChatGPT. Editors can help ensure the accuracy, clarity, and appropriateness of the generated text for specific contexts or purposes.
Human editors can review and refine the AI-generated content to improve its quality, correct any errors or inconsistencies, and adapt it to the desired style or tone. They can also help mitigate biases that may inadvertently emerge in the generated text. By combining the capabilities of AI with the expertise of human editors, the overall quality and usefulness of the generated content can be enhanced.
Therefore, involving human editors can be a valuable step in refining and improving the output of AI language models like ChatGPT.
When I asked ChatGPT, “Can you turn the above text into an essay in the style of John McPhee’s writing?” I got the following.
When it comes to discussing the involvement of human editors in the utilization of AI-generated content, one cannot help but ponder the profound influence of their collaboration. As an AI language model, I lack the personal inclinations and requirements of human beings. However, the inclusion of skilled editors in the process undoubtedly enhances the overall quality and effectiveness of the generated text. In the realm of AI, where the capabilities of language models like ChatGPT have flourished, the expertise of human editors is essential to refine and polish the output, elevating it to new heights.
Editors possess a unique ability to discern and rectify any inaccuracies, inconsistencies, or inadequacies that may manifest within AI-generated content. Their discerning eyes scrutinize every word, sentence, and paragraph, ensuring a level of precision and clarity that may elude the algorithmic mind. By judiciously reviewing and refining the text, editors bestow upon it a coherent and lucid nature, making it more comprehensible and impactful for specific contexts and objectives.
In the delicate task of mitigating biases, human editors exhibit their paramount importance. While AI language models aim to emulate human language patterns and produce coherent responses, they can inadvertently perpetuate biases ingrained in the data they are trained on. Editors, with their conscientiousness and attentiveness, serve as gatekeepers, identifying and rectifying any biases that may inadvertently emerge. Their involvement acts as a crucial checkpoint, ensuring the AI-generated content does not unwittingly reinforce discriminatory views or perspectives.
Apparently, ChatGPT decided to use fancier words. While I don’t know McPhee, I expect he’d cringe and Green 10 before giving it to his editor.
The four things I enjoy the most in life outside my work are reading, writing, running, and being with Amy. When I encounter a writer like McPhee writing about writing, I enjoy my brief time in a parallel, recursive universe.
Chris Heivly released Build the Fort: The Startup Community Builder’s Field Guide. I encourage you to get Chris’s book if you are a startup community builder or are interested in startup communities.
When Ian Hathaway and I started working on The Startup Community Way: Evolving an Entrepreneurial Ecosystem, we initially talked to Chris about writing a few chapters. Chris became an extensive thought partner with Ian, and we eventually decided to write two books. The Startup Community Way would be conceptual but filled with examples to make our points, and then a second book would be a practitioner guide.
Writing a book is difficult; eventually, Ian and I decided one book would be enough for us. Chris was enthusiastic about writing the practitioner guide, so Ian and I strongly encouraged him to proceed.
I met Chris a dozen years ago when he wanted to learn from my experience in Boulder as he began to help build the startup community in Raleigh-Durham, NC. He visited me in Boulder in late 2016 as he was thinking about helping the 15+ cities within a 4-hour drive from his home in Durham, NC, build startup communities. David Cohen and I had discussed something similar for Techstars. In our conversation with Chris, we proposed that he join Techstars to work on this together.
Chris led an effort at Techstars that evolved into the Techstars Ecosystem Development process. He immersed himself in this and has spent much time bridging theory and practice.
Chris – thank you for writing the second book I didn’t have the energy for.
Some day there will be a genre called “startup fiction.” I mean, if science fiction, which is a sub-genre of fiction, can have libertarian science fiction and recursive science fiction, surely startup fiction belongs in a sub-genre of a sub-genre of a sub-genre.
Please Report Your Bug Here by Josh Reidel is an excellent example of startup fiction. I began reading it at the end of the day Saturday after finishing The Age of A.I. and Our Human Future. I enjoyed Reidel much more than Kissinger, Schmidt, and Huttenlocher (even though I greatly respect them.)
Reidel was the first employee at Instagram. While the first thirty pages started like yet another explore the bay area startup thing book, it quickly twisted into something more enjoyable. When I picked it up yesterday afternoon after a long run and a nap, I didn’t put it down until it was time to go to sleep, which meant I was finished with the book.
I hope there are a lot more books like this. It balances startup stuff with the cynicism of the experience while placing it in a fictional world. It unexpectedly merges with believable near-term science fiction, which has a delicious parallel universe theme. And, if you believe in the infinite parallel universe theory (or just the multiverse) and haven’t yet renamed your company multiverse (yes, there is one), you can quickly get lost in a sequoia tree. In Oakland.
I assume that Reidel meant to riddle the book with tech industry easter eggs. If this was unintentional, it’s even more fun since that would be my brain doing its thing on Planet Brad.
I hope there are a lot more books like this. I’ve been thinking about writing a fictionalized version of my SPAC experience, and Please Report Your Bug Here inspired me to take that idea more seriously.
I read two books by Ted Conover over the weekend.
Amy gave me the first one as a present. A few years ago, we bought a bunch of land about an hour’s drive away from Aspen. I’ve been spending a lot more time in the middle of nowhere Colorado, especially now that I have a trailer on the land and Starlink. My hikes and trail runs (without Starlink, but with a Garmin inReach for safety), which are still in the day hike category, take me deeper into the middle of nowhere.
Amy’s been highly supportive of this new hobby of mine. She’s not interested in the hiking or trailer, but she likes to visit the middle of nowhere for limited periods, as long as she gets to drive back to Aspen.
Conover’s Cheap Land Colorado was outstanding. He writes about his experience in the San Luis Valley, where he lived part-time for extended periods (commuting back to New York to see his wife and teach at NYU.) Conover didn’t just observe – he became part of the community. He eventually bought some land and made it habitable for him. The texture of his writing is beautiful. The characters are fascinating. The history was all new to me about a part of Colorado I know little about and have only been to once when I visited the Great Sand Dunes.
Looking through his biography, I noticed another book by him titled Whiteout: Lost In Aspen. He’d written it 30 years earlier. After Amy and I bought a place there in 2017 and started living there part-time, I read a few books about the history of Aspen. But I hadn’t read much recently other than The Slums of Aspen: Immigrants vs. the Environment in America’s Eden, which I discovered when reading the extremely disheartening Billionaire Wilderness: The Ultra-Wealthy and the Remaking of the American West.
Even though it was written 30 years earlier, Conover’s style was similar. Whiteout: Lost In Aspen (as does Cheap Land Colorado) takes an ethnographic research approach, similar to what I learned from a graduate school class I took with John Van Maanen in 1988. In the parallel universe / path not taken life, I’d be an ethnographer. Maybe there is still time.
Aspen of 1991 has a lot of similarities, and issues, to Aspen of 2022. As I’ve gotten to know people who have lived there full-time for more than a decade, I hear many of the same complaints that appear in Whiteout. The names of the restaurants are different, but the feel of the town and surrounding area is the same. The notion that Aspen was about to lose all of its beauty and special magic was a big part of the narrative in 1991 and is still around today.
Amy and I have lived in Colorado for over 27 years. This is home now. Conover writes beautifully about it.