I first read Zen and the Art of Motorcycle Maintenance in college. I’ve read it at least a half dozen times since. I’ve listened to it on Audible twice. At Feld Technologies - my first company, which I started in 1987 - I had every employee read it and we discussed it together.

Ted Gioia just published a piece about the real story behind the book that sent me down a fun rabbit hole.

I knew the broad strokes of Robert Pirsig’s life. He was a Korean War veteran who studied philosophy at Banaras Hindu University in India, worked as a technical writer at Honeywell, and experienced a severe mental breakdown that led to psychiatric hospitalization and electroshock therapy - administered without his consent, a procedure that’s now illegal. He wrote the entire book between 2 AM and 6 AM in a small apartment above a Minneapolis shoe store while holding down his day job.

Then 121 publishers rejected it.

The editor who finally said yes - J.D. Landis - did so because “the book forced him to decide what he was in publishing for.” He gave Pirsig a $3,000 advance and warned him not to expect much. The book went on to sell five million copies. George Steiner compared Pirsig to Dostoevsky. Robert Redford tried to buy the film rights. The Smithsonian acquired the motorcycle.

One editor, after 121 rejections, said yes because the book forced him to confront what he actually cared about. That’s Pirsig’s thesis made real. Quality isn’t something you can define first and recognize second. You recognize it, and then, maybe, you can start to articulate why. Landis felt it before he could explain it. Every investor I know has had that experience. Every founder building something genuinely good has had the inverse - the thing they made was real, but the institutions couldn’t see it yet.

The concept at the center of the book is Quality - capitalized, because Pirsig treated it as something fundamental. Quality isn’t a subjective judgment or a metric you track on a dashboard. It’s something you recognize before you can define it - something that connects science, art, and spirituality in a way that most Western philosophy refuses to allow. Pirsig eventually connected it to the Greek areti - excellence, or virtue - but the power of the book is that he arrives at this through the act of motorcycle maintenance, not through academic argument.

I called it “a brilliant essay on quality” and I stand by that description seventeen years later. It was the first philosophy book I actually felt like I grokked (no, I am not going to let a company own that word, nor am I going to let a company own the word meta.)

Every entrepreneur I’ve worked with over the past 30 years has faced what Pirsig calls gumption traps. He defines them precisely:

“Anxiety, the next gumption trap, is sort of the opposite of ego. You’re so sure you’ll do everything wrong you’re afraid to do anything at all.”

I’ve used that quote in Techstars CEO roundtables when founders are drowning in conflicting advice during week four of the program and have lost the ability to make any decision at all.

The antidote is also in the book. During a mountain road passage, Pirsig describes the narrator’s anxiety about hairpin turns at altitude - imagining a stone dropping thousands of feet. Then they ride the road.

“It’s so hard when contemplated in advance, and so easy when you do it.”

I was listening to this on an audiobook during a pre-dawn training run in 2010, heading up Highway 36 toward Lyons in pitch blackness with 40 mph wind gusts, and I physically felt the smile break out on my face. The life lesson of that line is so powerful.

I’ve written before about wanting to see someone write the equivalent of Zen and the Art of Motorcycle Maintenance for entrepreneurship - a philosophical treatise that will stand the test of time rather than another how-to book with a framework and a subtitle. Jerry Colonna and I have talked about the need for this over the years. It doesn’t exist, or at least I haven’t found it yet.

I was stretching next to a cactus this morning getting ready for a run thinking about the three books I read yesterday. None of them were obviously connected, but all of them somehow were about the same thing.

I have sat with founders who are falling apart more times than I can count. Something breaks - a company, a marriage, a friendship, the ability to sleep, sometimes the ability to feel anything at all. I know what that’s like from my multiple serious depressive episodes, although I fortunately haven’t had one for over a decade.

James Oliver Jr. has been alongside founders in this territory for years. His book Burn Bright, Not Out - co-authored with Django De Gree - is what I wish had existed a long time ago. James didn’t write a self-help book. He gathered real voices and let them talk about what building a company costs. The Kabila Founder Mental Health Fund that James runs - free therapy for founders who can’t afford it - is something I would have pointed people toward during the hardest stretches I’ve witnessed.

I love to run. As I get older and slower I’m learning to love hiking more. When I saw Hiking Zen: Train Your Mind in Nature by Brother Phap Xa and Brother Phap Luu - two Buddhist monks ordained by Thich Nhat Hanh - in Greeley Sachs’ Composition Shop bookstore, I knew I had to read it. I have a soft spot for monks.

The book isn’t about covering miles or conquering peaks. It’s about what happens when you pay attention on a trail. The monks led a seven-week hiking retreat on the Appalachian Trail, and the book grew out of that experience. Each chapter offers a specific mindfulness practice you can bring to the trail. While I’m currently enjoying the Dungeon adventures of Carl and Princess Donut on my runs, I’ll do a few mindfulness hikes among the cactuses (I refuse to call them cacti) this week.

Paul Millerd sent me a copy of The Pathless Path: Imagining a New Story For Work and Life . I don’t think I know Paul, but the phrase “default path” - the one that runs from graduation to career to retirement without ever asking why - hit me immediately.

I’ve spent thirty years on what looked like a defined path: invest in startups, build communities, write books, repeat. But the path I’m on now doesn’t have a name. I’m focused on non-attachment (not detachment, which is different) to everything, including success, progress, and a path itself. Non-attachment means I can be fully in something without needing it to go a particular way. The default path requires attachment to every milestone. Paul’s book reinforced the framing for what I’ve been doing.

After a delightful digital sabbath with books, I’m back to playing with Lumen .

My partner Seth Levine has an important new book out today titled Capital Evolution: The New American Economy .

I saw it last night at the Boulder Bookstore in the New Hardback Non-Fiction section (bottom left in the photo below) and am going to the launch event at Composition Shop in Longmont. Join us, say hello, and buy some books!

I love the tagline from the flyleaf: “The future of capitalism isn’t left or right – it’s forward.“

In our over-politicized world, Seth and his co-author, Elizabeth MacBride, do an outstanding job of defining capitalism clearly and explaining how it evolved into today’s approach. They deconstruct the contemporary arguments “for and against,” examine challenges with many existing practices, and paint a new and compelling path forward.

Seth and Elizabeth have been working on this book for over two years. I read an early draft around a year ago and gave them a lot of feedback, so it’s been a joy to see it take shape.

Unlike my largely anecdotal books, which draw on my experiences, often with sidebars from others sharing theirs, Seth and Elizabeth did deep research for this book. I fondly remember showing up at Seth’s party barn at his house one day to see the large dining table covered with hardcover books on economic theory, the history of business (and capitalism and economics), and a bunch of other stuff he was reading as part of his extensive research.

As with Seth’s other book, The New Builders , it is both extremely substantive and eminently readable. I encourage you to buy and read a copy of Capital Evolution: The New American Economy .

Give First is now available to pre-order in Audiobook format (it will be officially released on 12/2/26).

I’m the reader, so if you are an audiobook person, you’ll have to listen to me for a few hours. It was fun doing the recording (I’ve done the audio recording for two other books – Venture Deals (Jason and I alternated chapters) and Startup Life .

Give First Audiobook on Amazon
Give First Audiobook on Audible
Give First Audiobook on Apple
Other links via RBmedia

I’ve been a long-time Cory Doctorow fan. His new book Enshitification is delicious. Yup – I understand that a shit emoji doesn’t inspire deliciousness.

Now that I’m back in hibernation (and figuring out what it actually means), I’m reading and writing a lot. I’ll probably blog some (a little, a lot, who knows) while in hibernation because I work out ideas by writing and putting them out in public (even if I don’t pay much attention to the feedback or engage) is a different type of writing for me than just “writing privately” (which is mostly a thing called journaling and valuable to me, but different …)

Cory invented a new word: enshitification. Here’s what Wikipedia says as of today:

Enshittification, also known as crapification and platform decay, is a pattern in which two-sided online products and services decline in quality over time. Initially, vendors create high-quality offerings to attract users, then they degrade those offerings to better serve business customers (such as advertisers), and finally degrade their services to users and business customers to maximize short-term profits for shareholders.

Nailed it. His examples are superb. I don’t use Facebook products anymore (I guess I’m supposed to call it Meta) because of how awful they are and how awful the company is (oops – yes – I have WhatsApp on my phone because several people in my world insist on using it, but it mostly just sits dormant for me.) I am so exhausted by Amazon and its endless quest for more margin from everyone, including all the companies that it depends on to be useful. Google is “entertaining” to me as they systematically destroy so many companies that enabled them to be amazing in the quest to become an AI company. TwitterX bwahaahahaha. And I don’t even want to bother with the enshittification of so many other things in the tech world that Cory doesn’t touch on but that fit within his thesis.

Cory deconstructs, in fascinating detail, what has happened with each of these companies.

While I don’t agree with all of Cory’s politics (e.g., I was not a fan of Lina Khan and the Biden-era FTC), I love that he’s willing to take strong positions and then back them up. But, the regulatory dynamics and regulations as part of his solution for Enshitification is only a modest part of the book. And, even though I don’t agree with all of it, his arguments have a lot of validity and useful things to understand, especially around the concept of regulatory capture and how it contributes to enshitification.

If you like sci-fi, read Cory’s stuff. If you are in the tech industry and want to be forced actually to think, read Cory’s stuff. If you are far left or far right, don’t bother, since you won’t be motivated actually to learn anything. But if you aren’t part of the “far left/right” and you are willing to read, think, and consider your position on things, read Cory’s stuff.

I approached Echoes of October with trepidation. A graphic novel about violence and grief isn’t easy terrain. But it succeeds in a haunting, urgent way. The creators have chosen to explore the year leading into the October 7, 2023 massacre through the lives of four children who each lose a parent. The children are from different locales (Gaza City, Toronto, Tel Aviv, and Daliyat al‑Karmel) which enables a textured, multi‑vantage narrative. 

What impressed me most is the restraint and care in which the story is told. The voices are calibrated: they carry sorrow, confusion, hope, anger, but rarely descend into melodrama. Because the characters are composite (e.g., everything that happens in the book is true, the characters are not), the authors manage to create space for truths without claiming to own them. 

I love graphic novels (scifi and history) and regularly have them in my reading diet. The panels breathe. There are silences, negative space, quiet facial expressions, and moments of violent disruption. The juxtaposition of children’s everyday worlds (school, family, and play) with the encroaching shadows of conflict makes the tragedy more palpable and intense.

This is not an easy read, nor should it be. Echoes of October is demanding: it expects the reader to engage, be uncomfortable, and reckon with stories that hold no clean resolution. But in doing so, it honors the complexity of memory, the weight of loss, and the imperative of bearing witness.

I recommend it to anyone willing to engage deeply with how conflict impacts children and the possibility (however fragile) of empathy.

Reid Hoffman’s new book Superagency: What Could Possibly Go Right with Our AI Future is spectacular and a must-read for every non-technologist about how to think about this “AI thing.” If you want the short version, the recent AI & I podcast with Reid is an excellent way to get a feel for it.

Reid describes his approach as “smart risk taking” rather than blind optimism. “Everyone, generally speaking, focuses way too much on what could go wrong, and insufficiently on what could go right,” he told TechCrunch recently. This resonates with me. I’m tired of the endless AI apocalypse takes.

The book’s central idea is “superagency” – basically when technology gives us new superpowers and millions of people get those superpowers at the same time. Reid uses the car analogy. Cars were once so scary they required a person walking in front waving an orange flag. Now we can’t imagine life without them.

What I love about the book is how practical it is. Reid and his co-author Greg Beato didn’t use AI to write it, but they used AI to vet it – checking facts, doing research, getting different perspectives. That’s exactly how I think about AI tools. They’re not going to replace my thinking, but they can definitely amplify it.

The timing feels perfect given what’s happening here in Colorado with our AI regulation mess. While Reid is writing optimistically about AI’s potential, Colorado has been having a complete meltdown trying to regulate it. Our state legislature passed SB 24-205 in May 2024, making us the first state to broadly restrict private companies using AI. Governor Polis signed it “with reservations” and within a month Polis, our attorney general Phil Weiser, and the bill sponsor Robert Rodriguez issued an open letter that “Starting today, in the lead up to the 2025 legislative session and well before the February 2026 deadline for implementation of the law, at the governor and legislative leadership’s direction, state and legislative leaders will engage in a process to revise the new law, and minimize unintended consequences associated with its implementation,”

This is exactly the kind of regulatory approach Reid warns against. In his recent podcast, he explained his philosophy: “I tend to be more regulatory cautious than anti-regulation.” The key difference? Start with measurement rather than prohibition. “When you start having the impulse that maybe there should be regulation, you should start with, well, how do we measure the questions that we’re worried about as harms?”

Colorado did the opposite and went straight to broad restrictions without first understanding what we were actually trying to prevent or how to measure it. The timeline since then has been a comedy of errors – multiple failed attempts to amend the law during the regular session, and most recently, an August special session that ended with lawmakers just pushing the start date from February 2026 to June 2026. That’s it. After over a year of fighting, we got a four-month delay.

Reid believes in “iterative deployment” – getting AI tools into people’s hands and then responding to actual feedback and real problems, not hypothetical ones. Instead, Colorado jumped straight to prescriptive rules based on fears rather than evidence. Reid’s approach would have been: Deploy AI systems, measure actual discrimination outcomes, then iterate on solutions. Our approach was: Assume the worst, regulate preemptively, and figure out implementation later.

The Colorado situation perfectly illustrates Reid’s point about fear-based thinking around AI. Superagency offers a much better framework – one that acknowledges challenges while focusing on AI’s potential to increase individual agency and create better outcomes for society.

Read the book. We need more thoughtful optimism and less regulatory panic. Especially here in Colorado, where we’re supposed to be leaders in technology, not cautionary tales about how fear can paralyze good policy-making.

I love books. I love reading. I love reading books.

Ensorcelled by Eliot Peper is genius. It’s a unique format that can be read in one setting. The writing is beautiful. The story, like the image on the cover, pulls you in with steadily increasing intensity. And then, a delicious twist. Amy and I have been supporting Eliot’s writing since his first book, and he’s become a dear friend. I started my weekend with this, and it inspired me to read a few more things by friends.

The Night Slayer by George Jankovic was next. I fondly remember a vacation to Hawaii with the McIntyres when their son Quinn was a pre-teen. This particular vacation was dedicated to me and Quinn reading several Percy Jackson books while lying on adjacent beach chairs overlooking the ocean. George’s book teleported me back to that week. I funded George’s first company, RF Globalnet, when he lived in Boulder in the mid-1990s. We had a failure together with a company called eVulkan, but then I was fortunate to be invited to fund NutriSystems when he and his partner, Mike Hagan, took it over as it was on the brink of bankruptcy. If you had told me in 1997 that almost 30 years later, George would write an epic YA coming-of-age fantasy series that moves faster than the Percy Jackson books, I would have laughed out loud. I can’t wait for The Princes of the Abyss to show up on my Kindle.

I’ve been remiss in addressing the infinite pile of PDFs on my Kindle from friends that are drafts of their books, so I tackled the first three chapters of the upcoming book City on the Edge by Jonathan Weber . It’s fantastic and is going to be a powerful and definitive story of San Francisco from 1990 to the present day. I’ve known Jonathan since he was editor-in-chief of The Industry Standard and was an investor in his online venture New West. Jonathan’s writing reflects a journalist’s cynicism and inquisitiveness, unwilling to accept the endless surface-level storytelling, self-promotion, and general deceit and deflection of many people. As a reward for giving him feedback, he sent me the rest of the book to read.

I’m halfway through When River Loves Deborah by Yong Kim. We are tiny investors via FG Angels in Yong’s company, Wonolo , and I hadn’t realized he’d written this book. I’m halfway through and am looking forward to lying on my couch on Thursday to finish it up.

I’m ensorcelled when I read books by friends (see what I did there…)

As I gear up for the official launch of Give First: The Power of Mentorship this week, I spent the weekend reading, playing with my 7GL, running, celebrating my 32nd wedding anniversary with Amy, and hanging out with some friends who were in town.

Ben Wiener’s book Fever Pitch: A Novel About Selling Your Vision, Raising Venture Capital, and Launching Your Startup was delightful! Ben is a partner at Jumpspeed , based in Jerusalem, Israel. We are email friends, and he has been key in helping develop and lead the Jerusalem startup community. I don’t know his portfolio well, but I do know he was an investor in BreezoMeter, an app I obsessively used during a fire season in Boulder one summer.

I’ve read some fiction that attempts to blend classic crime drama with startups, technology, relationships, and venture capital. Eliot Peper is my favorite in that category, and William Hertling (who needs to add https to his website so Google doesn’t barf on it) is a close second. Even though this is Ben’s first book, I’m adding him to that list.

If you like a fast novel that you can read in a few hours while still learning something (Ben’s H.E.A.R.T. framework: five essential elements of a pitch that mirrors how venture capitalists evaluate deals), I highly recommend Fever Pitch: A Novel About Selling Your Vision, Raising Venture Capital, and Launching Your Startup .

Nice job, Ben – good inspiration for me if I get around to writing fiction some day!

I haven’t read much in the last 30 days as I’ve been consumed with writing, speaking, and events around the launch of Give First: The Power of Mentorship . The Kindle version is now available , and the paperback version will be released on Tuesday, June 24, so I’m in the home stretch of pre-launch. It hit #1 in Startups yesterday, so if you are inclined to buy, now is the time to keep the momentum going!

Amy and I are in Aspen, so I’m having a lot less social in the evenings. That means – reading on the couch after dinner.

I finished two books last night. The first was Barry Eisler’s new novel The System: A Novel of the Deep State . I love Barry’s writing and read every book he writes. He has total mastery of the contemporary thriller with extraordinarily vibrant characters and a zillion endnotes that tie to things that are actually happening in the real world. The protagonist, Valeria Velez, is fantastic, and I hope she shows up in a few more books. And, John Rain needs to show up in the Valeria Velez series. If you like mental floss, Brad-the-book-salesman says make today a two-fer and buy The System: A Novel of the Deep State and Give First: The Power of Mentorship .

I try to only read mental floss every third book, so last night I got to work on consuming Little Black Classics Box Set (Penguin Little Black Classics) . It’s my summer reading project, which is a curated library of eighty pocket-sized books that encapsulate the breadth and diversity of literary history. This collection spans continents and centuries.

For example, here are a few summarized by my favorite AI: the searing social commentary of Jonathan Swift’s A Modest Proposal; the timeless Greek tragedy of Sophocles’ Antigone; haunting tales of the macabre in Edgar Allan Poe’s The Tell-Tale Heart; the revolutionary political theory of Karl Marx and Friedrich Engels’ The Communist Manifesto; profound reflections on life from ancient Japan in Kenkō’s A Cup of Sake Beneath the Cherry Trees; the witty and satirical juvenilia of Jane Austen’s The Beautifull Cassandra; psychological depth in Fyodor Dostoevsky’s short story The Meek One; the lyrical beauty of John Keats’ narrative poem The Eve of St Agnes; early feminist arguments in Mary Wollstonecraft’s A Vindication of the Rights of Woman; and the sharp, observational fiction of Anton Chekhov’s Gooseberries.

I read the first one in the series last night: Mrs Rosie and the Priest by Giovanni Boccaccio . I’ve never read anything by Boccaccio and didn’t know that 14th-century Italians were so filthy and degenerate (well, yes, I did, nothing ever changes, we are humans after all.) The commentary on gender, female agency, and society is sharp. I liked all the female protagonists, but Bartolomea was my favorite. The dialogue, even translated into English, is fun and spicy.

As I continue to see how good (or bad) different AIs are, I asked Gemini, “What lesson am I supposed to learn from the book.” After it gave me three tedious and overwrote paragraphs, I asked, “Give this to me in one paragraph. Use Brad Feld’s style of writing from feld.com”

“I love when a piece of writing from the 1300s delivers a mental model that feels like it was written for a startup founder in 2025. Boccaccio’s story about Mrs. Rosie is a masterclass in hacking a legacy system. You have a protagonist facing a fatal outcome from a set of rules—a legal and religious OS—that is fundamentally asymmetric and designed to benefit the people in power. Instead of accepting the premise of the game, she calls bullshit on the entire system with an argument so logical and witty that it forces the system to self-correct. She doesn’t fight the power structure with force; she uses intellectual arbitrage to expose its hypocrisy and bankruptcy. It’s a powerful reminder that challenging the core assumptions of a broken system is often infinitely more effective than trying to win within its stupid, arbitrary constraints.“

Eh – not so good. And the description is only about one of four stories.

I had a weird, unsatisfying, and not particularly restful weekend because of Colorado politics and post-exertional malaise . So, in between work, a short run, a long nap, a bunch of online Swedish death cleaning , and lying on the couch responding to endless text messages, I read Carrie Soto Is Back and The Big Gamble (Kevin Kerney Novels Series Book 7) . And when I say “read”, imagine me on the coach, with my Kindle in one hand and my iPhone propped up on my leg so I could read what came in and respond when necessary.

The Big Gamble was good. I’m enjoying cruising through the Kevin Kerney novels after consuming the entire C.J. Box Joe Pickett series  (all 25). But Carrie Soto Is Back was spectacular.

I was a serious tennis player from age 10 to 14. While football dominated Texas sports, well, forever, tennis was up there in the mid 1970s alongside soccer (anyone remember Kyle Rote Jr and the Dallas Tornados?) I stopped playing tennis when I discovered computers and girls (in that order) and started running instead. For my 30th birthday, Amy took me to Bollettieri Tennis Academy (RIP Nick Bollettieri ), which rekindled a casual interest in tennis for me and a serious interest in tennis for Amy.

Today, Amy is a tennis superfan. Our default TV channel is the Tennis Channel (turn on the TV and it goes to the Tennis Channel). She always talks about Rafa and compares all the new up-and-comers to him.

While I’m also a tennis fan, I’ve grown to enjoy watching the women’s games more than the men’s. Coco Gauff is my current fave, but I almost always root for the underdog. And while I rarely cheer for Sabalenka , she is an amazing player.

Carrie Sota was the best (fictional) female tennis player in the 1980s, winning the most Grand Slams of any player (20). She hurt her knee in 1987 and retired in 1989. The book starts in 1994 with Carrie watching the new top female tennis player, Nicki Chan win the US Open and tie Carrie’s record.

In 1995, Carrie decides to come out of retirement and compete in all the majors. If you are a tennis fan and this sounds familiar, it is a recurring theme in  real-life tennis that rarely ends well .

The drama is phenomenal, and the character development of Carrie, Chan, Carrie’s father, her love interest, and a few other minor characters is outstanding. The story moves quickly, and the tennis match sections keep up the drama and pace. Our protagonist has multiple moments of increasing difficulty that aren’t histronic or hard to believe, many of which deal with her changing reality of life as she gets a little older.

When I watched (and then read) Daisy Jones & the Six several years ago, I thought Taylor Jenkins Reid was a gifted storyteller. I don’t know why it took me so long to discover and read Carrie Soto Is Back , but The Seven Husbands of Evelyn Hugo and Malibu Rising are now on my Kindle.

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.

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!

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.

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.

• Cheap Land Colorado: Off-Gridders at America’s Edge (2022)
• Whiteout: Lost In Aspen (1991)

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.