Brad Feld

Category: Books

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Soundarya kept me updated, and I got the unpublished manuscript for Unshacked five months later.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.


I’m a fan of David Walton and his near-term sci-fi books. In 2015, I read a few of his books, wrote a post titled Awesome Near Term Sci-Fi – David Walton, and promptly forgot about him.

Eleven days ago, I got the following email from David.

Mr. Feld:

Since you’ve enjoyed my books in the past (e.g. Superposition), I’m letting you know I have a new one out. No worries if you’re not interested; just letting you know. Hope all is well with you and yours.

When paleontologists Samira and Kit uncover dinosaur skeletons in northern Thailand, they find the remains of an ancient genetic technology that nations will kill to control. Catapulted into a web of murder and intrigue involving the Chinese Ministry of State Security, a powerful Asian crime syndicate, the CIA, and a beautiful Thai princess, Samira and Kit don’t know who they can trust. Torn apart by competing factions and stranded on opposite sides of the world, they race to discover the truth before the world goes to war. Can they bring the past to life before it kills them all?

“Walton has brought hard sci-fi roaring back to life.” –Wall Street Journal

I went and looked up the books he’d written and realized I’d missed the last two: The Genius Plague and Three Laws Lethal.

I started the The Genius Plague on Saturday morning and finished Three Laws Lethal last night. They were both spectacular.

It’s easy to relate to The Genius Plague since we just experienced a pandemic that is trying to shift from epidemic to endemic and failing (according to some) while being a non-issue (according to others). But what if the first order impact of the disease was something other than death and the second order impact could go in multiple directions, depending on … Ok, I won’t spoil it for you.

Three Laws Lethal was even more delicious. I expect many readers of this blog know Asimov’s Three Laws of Robotics. But do you know the Three Laws of Warfighting AIs? Mikes played a central role and I kept waiting for a Mike and Ike reference, but it never appeared. Maybe there will be a sequel.

David – well done. Your newest book Living Memory is on my Kindle and I’m starting it tonight after Life Dinner with Amy.


Since Matt Levine is so effectively covering anything interesting in the world of the Twitter deal (and all kinds of bizarre, random, and complicated crypto, fraud, debt, and other financial stuff), I think I’ll stick with book reviews for the time being.

Andy Dunn, who I only know indirectly, wrote an important book titled Burn Rate: Launching a Startup and Losing My Mind. While it covers the story of Andy’s company, Bonobos, it’s really about mental health and entrepreneurship.

While there might be other entrepreneur autobiographies like Burn Rate, I can’t think of any. The closest is Tracy Kidder’s awesome book titled A Truck Full of Money about Paul English, an entrepreneur I do happen to know.

Tracy’s book is a mix of Paul’s entrepreneurial story combined with his experience being bipolar. Andy’s book is his entrepreneurial story combined with his experience of being bipolar. Both are remarkably brave books. Andy’s autobiography is particularly powerful since he is extremely detailed about several of the manic experiences that he had while running Bonobos.

While I don’t know Andy, I know several of his investors. His description of how they handled the situation of discovering Andy’s mental health diagnosis made me proud to know them. Andy decided to proactively hold a board meeting to describe what had happened that resulted in him ending up in the hospital and jail. One of his board members, Joel Peterson (who I don’t know), is remarkable.

“When I got out of the hospital, I walked straight into handcuffs. The City of New York charged me with misdemeanor assault and felony assault of a senior citizen.”

“Has there been a diagnosis?” Joel Peterson asked.

“The diagnosis is bipolar disorder type I. I was originally diagnosed when I was twenty, and I’ve been in denial about it for sixteen years.” A brief silence.

“I know a few folks who have dealt with what you’re dealing with, Andy,” Joel said calmly, holding true to his role as my professional father figure, “including more than a couple of entrepreneurs. It’s entirely manageable. I have full faith in you to take care of yourself, and I have full confidence in you as our CEO.”

Andy covers the rest of the board meeting discussion, including questions from board members about whether he was getting appropriate treatment, his legal situation, and the game plan for addressing any publicity around the situation.

A while ago, I was at a dinner with a bunch of VCs and entrepreneurs, including several very famous ones. One of the entrepreneurs stated clearly that if he ever talked openly about his struggle with depression, his board would immediately fire him. Fortunately, this was not the response of Andy’s board, as they took in the situation, asked questions about it, and made rational and deliberate decisions about what to do going forward. It’s worth noting that Andy was still the CEO of Bonobos when Walmart acquired it several years later.

I’m hopeful that Andy’s book will continue to help destigmatize mental health in entrepreneurship. Thanks, Andy, for being willing to write such an intimate story about your experience.


Steve Case’s new book, The Rise of the Rest: How Entrepreneurs in Surprising Places are Building the New American Dream, is out. I read it on Sunday, and it is outstanding. If you are interested in understanding how high-tech entrepreneurship has evolved from a primarily coastal phenomenon to one that covers the entire US in the past decade, grab this book now.

Steve is a great storyteller. While he tells the entrepreneurs’ stories, he has been part of helping create them. He created Rise of Rest and did the first of many bus tours in 2014. I was part of the one in Denver, and my partner Chris Moody was part of the one in Birmingham. They were each awesome experiences.

This is the story of what happened on those bus tours, people who were connected, companies that were amplified, financings that happened, and cities that were energized around entrepreneurship.

For the past dozen years, I’ve spent plenty of energy on democratizing entrepreneurship. I’ve worked with Steve and his team on multiple initiatives, including Startup America and Up Global. Steve’s supported me on several things I’ve done, including writing the foreword to Startup Communities: Building an Entrepreneurial Ecosystem in Your City.

When I was a young entrepreneur in my 20s, Steve was a hero of mine. My AOL username was bfeld, which was where my Twitter handle (and everything else I signed up for on the web came from.) Now that I’m a middle-aged something or other at 56, Steve’s still a hero of mine. I expect this is true for many other entrepreneurs.


About a year ago, I decided to take a summer vacation from blogging. I didn’t feel like blogging when summer ended, so I extended my blogging vacation indefinitely. I figured I’d wake up one day and feel like blogging again or not. That summer vacation (from blogging) lasted a year.

Initially, I was working on a new book that I got bored of midway through the summer. I put it on the shelf with several other partially completed books. Google Docs now has a surprising number of my started but unfinished books.

Sometime in the fall, Matt Blumberg (Bolster CEO) approached me about doing a 2nd Edition of Startup Boards. Matt and I were on the board together of Return Path, his previous company, for almost 20 years. So when Mahendra Ramsinghani came out with the 1st Edition of Startup Boards in 2013, Matt gave me plenty of feedback on the book. Then, in fall 2021, he correctly suggested that the book needed a significant refresh.

While I always felt the 1st Edition was an important book, I never loved it. Mahendra and I worked hard on it, but I felt like I forced a lot of my writing at some point. Long-time readers of this blog know I had an extended depressive episode in the first half of 2013, and this book was one of the chores that I felt like I just had to get done in that period. Mahendra was kind and patient with me, but I’m sure there were moments when he wanted to scream something like, “Brad, will you just do the writing you said you’d do so we can get this book finished?”

So, we decided to do a 2nd Edition which is now finished and shipping on 6/15. I’m psyched about it. Matt contributed a lot of new content, and I had a chance to rework and refactor the entire book. I had plenty of energy for it, and, given that I’ve written a few more books and thousands of blog posts since 2013, my writing has continued to improve.

Early in the refactoring, we got feedback from several women that the 1st Edition wasn’t very accessible to them because all the sidebars and quotes were from men. So I made a Google Sheet of all the sidebars and quotes, and my brain broke for long enough that I had to go for a walk. So even though I thought I was self-aware and engaged in gender equity in tech in 2013, my actions, at least concerning this book, didn’t match my words.

Subsequently, we replaced about 50% of the sidebars and quotes with new ones from women and people of color. We also changed the pronoun dynamics to use the Singular They, which I am trying to do in all my writing (if you are interested in this topic, Khan Academy has an awesome video.)

Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors 2nd edition launch day is 6/15. If you are interested, pre-order it now.