Brad Feld

Category: Books

In the category of all of this has happened before, and will happen again.

I read The Legend of Bagger Vance yesterday and then watched the movie last night. The book is much better than the movie, and the book is really, really good, even if you don’t care about golf at all. And, since I don’t care about golf, I am comfortable stating that the book is excellent.

My journey to the book was via Seth Godin’s new book, The Practice: Shipping Creative Work, which is worth reading every page. That led me to Steven Pressfield’s book The War of Art – also outstanding. And, then I realized I’d never read anything by Pressfield, and up came The Legend of Bagger Vance, which rang a bell.

I’ve resisted reading James S. A. Corey’s books in The Expanse series. I’ve enjoyed the TV show so much that doubling back on the books seemed unnecessary. Yet, as I get ready to read Ready Player Two, I’m going to watch the Ready Player One movie again to freshen up my memory of it all.

The threads through all of the stories repeatedly repeat in our search for meaning as human beings. Recently, as I’ve been thinking about the future and trying to live in both 2025 and 2040 as thought experiments, several of the threads have jumped out at me as one’s that run through time. And, while reading The Legend of Bagger Vance, I became intertwined with one of these threads with time folding back on itself. While looking for meaning around what I had read, I found George Kimball’s review of the movie Bagger’s three-ball plays with history:

Personally, I also consider Bagger Vance a sacrilege, though I’d have been a lot less bothered if they’d just let Damon play his silly match against two fictional opponents. By attempting to squeeze Hagen and Jones into roles meant for a couple of Punjabi armies, the film-makers have managed to offend the sensibilities of anyone who has studied, or cared about, the traditions and history of the game.

Ah, how we try to give meaning to this thing called life. Time for a run.


I read G. W. Constable’s near term sci-fi book Becoming Monday. If you are a fan of near term sci-fi, AGI, or the singularity, go get a copy right now – you’ll love it.

I woke up in a customer service booth. Or perhaps more accurately, since I couldn’t remember a damn thing, my new existence began in that booth. If you’re born in hell, does that make you a bad person?

It took me about ten pages to get my bearings, which is pretty fast for a book like this.

Moon cut in. “I get where you’re coming from, Grog, but I’m not convinced that fear and control is a good start or foundation for inter-species relations.”

While the deep topics are predictable, Constable addresses them freshly, with great character development, and an evolving AGI who is deliciously anthropomorphized.

Trying to translate the communication between two computational intelligences into linear, human-readable text is nearly impossible, but my closest simplification would be this:

Diablo-CI: I have been observing the humans that have come with you / What are you / why have you broken into my facility

Me: I am a computational intelligence like you / how are you sentient and still allowed to run a NetPol facility / the other computational intelligences are isolated on your 7th floor / we are here to free them

Diablo-CI: I cannot stop security procedures. If you trigger an active alert I will be forced to take action / I am unable to override core directives even if I would choose.

Like all good books in this genre, it wanders up to the edge. Multiple times. And, it’s not clear how it’s going to resolve, until it does.

The back cover summary covers the liminal state and the acceleration out of it.

Humanity exists in an in-between state. Artificial intelligence has transformed the world, but artificial sentience has remained out of reach. When it arrives, it arrives slowly – until all of a sudden, things move very fast, no least for the AI caught up in the mess.

Well done G. W. Constable.


Daniel Jackson created a magnificent book. It’s a combination of three things: 1) Extraordinary personal stories about 2) The struggle with mental health, anxiety, and depression while 3) at MIT.

MIT is a foundational part of my life. I spent seven years there. I got into graduate school in my fourth year and got into a Ph.D. program in my fifth year. I also started three companies while I was there – the first failed after my sophomore year, the second failed after my junior year, but the third turned into Feld Technologies, which was my first successful company.

I vividly remember my first major depressive episode. It was 1990. My first marriage had fallen apart. My company was doing fine, but I was bored with the work. I knew my Ph.D. journey was doomed, but I hadn’t accepted it yet.

While I had theoretically experienced failure, none had felt very personal up to this point. When I flashback to MIT undergraduate failure, it was dropping out of courses like 18.701, which I had no business taking when I did. Or it was getting a 20 on my first 8.01 test, only to find out a few days later that class average was a 32.

But the failures in 1990 were real and personal. I had a fantasy about my first marriage, which was also my first adult relationship (which had started in high school.) My divorce obliterated that fantasy. I had created a narrative about myself, if only in my head, that I was an overachiever at the youngest possible age – my company, my Ph.D., my marriage. When the second of those, the Ph.D. blew up, a deep depression ensued.

I was lucky – I had three people in my life who showed up for me in profound ways. The first was my Ph.D. advisor, Eric von Hippel, who protected me from the worst of what could have been the emotional fallout from MIT while providing me with the best he could as a paternalist-non-parent. The next was my now wife, Amy Batchelor, who knew I was depressed, called it out, and encouraged and supported me through understanding what was going on. Finally, my business partner, Dave Jilk, showed up as a partner every day. I don’t think he understood what I was going through or what to do, but what he did was what I needed.

That was almost 30 years ago.

Depression can be a fiendishly challenging thing that some us call the black dog. Today, when it shows up, I pet it on the head, talk nicely to it, and encourage it to find somewhere else to play. But, for a while in my 20s, it took up residence in my dark, opaque box, which spent a lot of time in a 24,000 cubic foot apartment at 15 Sleeper Street and eventually migrated to 127 Bay State Road. At some point, the black dog got bored of that apartment and went somewhere else for a while.

Reading this book made me wish this book existed then. I remember feeling incredibly alone at MIT, in Boston, and the world. Once I acknowledged to myself that I was depressed, I knew I wasn’t the only person in the world who was depressed. But I was so terrified about it and felt so much stigma and shame around my depression that I built a dark, opaque box around myself and only let a few people in during that time. If this book had existed, I would have looked at the photos, read the stories, and realized both that I wasn’t alone and that I eventually could be ok.


My long-time friend and former MIT professor, Professor Edward Roberts, who founded and still chairs the MIT entrepreneurship program, recently published “Celebrating Entrepreneurs: How MIT Nurtured Pioneering Entrepreneurs Who Built Great Companies”.

The book is fascinating, especially its five chapters filled with in-depth interviews and background on the MIT “spinoff startups” that became the leaders of: the life sciences and biotechnology industry, the Internet, from CAD-CAM to robotics, and even “modern finance”, plus a host of other companies, including such recent successes as HubSpot, Okta and PillPack, all founded and led by MIT alums.

Chapter 11 is the one on Modern Finance. Who said professors at MIT didn’t have a sense of humor. Having known Ed for 35 years, he has a wicked one.

It has taken 50 years to transform MIT from its unique historic traditions to today’s recognition that forming new innovation-based companies is indeed the most powerful source of impact upon the world. In his praise for the book, MIT President Rafael Reif exclaims: “An entrepreneurship tornado continues to blow at MIT. The energy of entrepreneurship rises through our classrooms, labs, and centers. It is central to who we are as an institution for 50 years of extraordinary achievement.”

The first half of the book focuses upon MIT’s history of creating from scratch what they lovingly call the “MIT Entrepreneurial Ecosystem”. Much of what MIT has done has been literally copied by other institutions worldwide. Still more universities, regions, and countries have adopted MIT’s approaches as needed to fit their own surroundings.

Structured in two parts, the book first showcases how the unique atmosphere at MIT encourages its innovative entrepreneurs to thrive. Then, with in-depth coverage of the founders and companies that pioneered four industries—biotechnology, the Internet, from CAD-CAM to robotics, and modern finance—plus many other successful firms, Ed analyzes how MIT’s most successful entrepreneurs have capitalized on that environment and culture to build companies that have lasted for decades. Both internal and external to MIT, the founders of these organizations and companies tell their own stories, describing their motivations, challenges, and outcomes.

The opening cover page says clearly that all author royalties will be donated directly to endowment funds that support the MIT-wide entrepreneurship programs. Buy the book to learn more about the history and evolution of entrepreneurship at MIT while helping foster future entrepreneurs.


Every quarter I try to take a week completely off the grid. It’s a cold reboot for me, not simply a Ctrl-Alt-Del type thing. I started doing this in 2000 and it took me about four years to learn how to just turn off the switch completely for a week and then turn it back on. Last Saturday evening I turned it off and turned it back on yesterday morning.

My one mistake was reading the Sunday New York Times first thing yesterday. It was the wrong “first new information” and it made me extremely anxious. I wrote in my post from yesterday “I think that’s the last time I’m going to read the NY Times.” Now that I don’t feel anxious anymore, I know that’s not true, but it was an extreme shock to the system to wander back into things that quickly.

I read a lot of books last week, most of which were good. If you want my full reading list anytime, it’s in reverse chron order at Goodreads. Following is what I read last week with short hints in case you are interested in any of them.

22 Minutes of Unconditional Love: I try to pick a book a week from the NYT Book Review that I would have never otherwise read (I guess this is another reason to keep reading the Sunday NYT!). I rarely read fiction relationship stories and wouldn’t have picked one up about sexual obsession except for the good NYT review. It was interesting at times, but not really my thing.

Awakened in the Future: Mario Cantin is a friend. This is his first book. I loved it, including the fictional VCs who were protagonists but modeled after real VCs (yes, one of the protagonists is modeled after me.) The easter eggs are endless, and while there are some rough edges (this is, after all, Mario’s first book) it brought me back to reading Eliot Peper’s first book Uncommon Stock: Version 1.0. Mario – good job!

When Things Fall Apart: Heart Advice for Difficult Times: Pema Chödrön’s classic. Jerry Colonna has recommended it to me 71 times. Amy has recommended it to me 73 times. I think I’m going to read it every year – it exceeded my expectations.

Awareness: Tim Ferriss recommended I read this Tony de Mello book. I had never heard of Tony de Mello. This book was almost as good as Pema Chödrön’s book. And, it was followed by …

Rediscovering Life: Awaken to Reality: Also recommended by Tim Ferriss. Also by Tony de Mello. And also excellent. Halfway through the week, as I was practicing non-attachment, I went very deep on non-attachment.

I Was Told It Would Get Easier: Amy and I don’t have kids. When I read books by Abbi Waxman, I’m glad we don’t have kids. I don’t think I’ve ever met Abbi in person, but I’m long time friends with her husband David. At some point, David mentioned that Abbi was a fiction writer and I started reading all of her books. This one was a blast and, if you have kids gearing up for the infamous college tour, you’ll love it.

Portraits of Resilience: This was the most powerful book of Q320 vacation. Daniel Jackson interviewed a number of people in the MIT community (students, professors, and staff) around their experience with depression, anxiety, and mental health issues. The stories are incredible. The photographs are stunning. And the people are brave, amazing, and wonderful. MIT should give this book to every new undergraduate and graduate student as part of their welcome package.

I Am Not Your Negro: There is a lot more James Baldwin in my future. This is the script for the movie. I’m glad I read it before watching the movie – it made the movie even stronger.

Telecosm: How Infinite Bandwidth Will Revolutionize Our World: I pondered 2040 some during the week (Mario Cantin must have planted that seed in my mind) so I decided to time travel back to 2000 and read what George Gilder wrote. He got some of it really right and some of it really wrong. I loved seeing his promotion of companies that vaporized by 2003. Many of Gilder’s predictions and prognostications were correct, even if the companies he named as the leaders couldn’t pull them off.

She Proclaims: Our Declaration of Independence from a Man’s World: I’m trying to read at least as many books by women as by men. I don’t remember who recommended this one to me, but it was good. I found myself nodding along throughout much of it.

Wiser: The Definitive Guide to Starting a Business After the Age of 50: Gender inequity in entrepreneurship is a real thing. Racial inequity in entrepreneurship is a real thing. Age inequity in entrepreneurship is a real thing. I hoped this book would be about this. It wasn’t, so it turned into a skimmer. If you know of a good book around age inequity in entrepreneurship, please recommend it to me.

Whistleblower: My Journey to Silicon Valley and Fight for Justice at Uber: While I knew some of the story, I didn’t know a lot of the backstory. First-person narrative ranges in quality (my blog is an example of that – some days good, some days not so much …) Susan Fowler did an incredible job with this book and her story. She was a key part of much needed change in the tech industry that I hope continues.

The Bluest Eye: Toni Morrison’s first book. Incredible. I’m going to slowly make my way through all of Toni Morrison’s books.

Please Stop Helping Us: How Liberals Make It Harder for Blacks to Succeed: I don’t know who recommended this one to me, but it was in my infinite pile below The Bluest Eye so I picked it up and read it Sunday afternoon. It was the conservative counterpart to the liberal narrative around racism. It was written in 2015 and felt dated to me. I tried to suspend my bias as I worked my way through the arguments, but many of them were hard to process. It was particularly difficult after reading Toni Morrison from 1970 …

I don’t know what’s next on my reading list, but given my schedule this week, I don’t think there will be a lot of reading until the weekend.


Saturday is reading, running, resting, and playing with Amy day. Digital sabbath.

I was tired from the week and slept for ten hours. I also took a 90-minute nap in the afternoon. I had a good, albeit short (4 loops) run in the morning. I ran ten loops this morning, so getting back in the groove after a week of not feeling great.

My book was John Lewis’ Across That Bridge: Life Lessons and a Vision for Change. Amy suggested that I read Walking with the Wind: A Memoir of the Movement, which is in our infinite pile of books (and near the top). Instead, I decided I wanted to read this one first because several other people had suggested it to me after John Lewis died.

It was powerful. While there are elements of memoir in it, Lewis paints a clear vision of the future based on his lifetime of work on civil rights. He regularly tied his vision back to his childhood, his early work alongside Dr. King, and his leadership of organizations like the Student Nonviolent Coordinating Committee.

While I knew of the principles of nonviolence in the Civil Rights movement, I didn’t understand them. I knew the history of the Freedom Riders. Still, I didn’t understand the magnitude of the physical abuse and violence they encountered while operating with the principles of nonviolent protest.

When I read and reflect on this history, I’m embarrassed, horrified, and furious with elements of White America.

Reading the book by John Lewis inspired me on multiple levels. I know that, in addition to reading Walking with the Wind: A Memoir of the Movement, I’m going to add some Gandhi to my reading list. If anyone has a suggestion for a great Gandhi book, toss it in the comments.

John Lewis was an American hero. And, his posthumous OpEd in the NY Times, Together, You Can Redeem the Soul of Our Nation, which starts:

Though I am gone, I urge you to answer the highest calling of your heart and stand up for what you truly believe.

ends with something I wish everyone in the United States would read, ponder, and take action on.

Though I may not be here with you, I urge you to answer the highest calling of your heart and stand up for what you truly believe. In my life I have done all I can to demonstrate that the way of peace, the way of love and nonviolence is the more excellent way. Now it is your turn to let freedom ring.

When historians pick up their pens to write the story of the 21st century, let them say that it was your generation who laid down the heavy burdens of hate at last and that peace finally triumphed over violence, aggression and war. So I say to you, walk with the wind, brothers and sisters, and let the spirit of peace and the power of everlasting love be your guide.


The week after George Floyd was murdered, I decided to read a book a week by a Black author. I went online and found a bunch of lists that had popped up. I bought about 25 books, all in physical form, and piled them up on my reading table near my couch.

On Saturdays, my primary activities of the day are reading, running, napping, and being with Amy. Two weeks ago, I read Ibram X. Kendi’s book How To Be An Antiracist. Last weekend I read Ta-Nehisi Coates’ book Between the World and Me. Tomorrow, I’m going to read John Lewis’ Across That Bridge: Life Lessons and a Vision for Change. And then, for the rest of August, I will read books written by Black Women.

The books by Kendi and Coates were both spectacular. I learned a lot from each, and they caused me to reflect on a lot of things while challenging a bunch of assumptions I had (many of which I’ve now modified or eliminated, although I’m sure I’ll need reinforcement to have the premises disappear from my brain.)

I read Lewis’ March Trilogy in comic book / YA form about a year ago. It was great. But, sitting with and reading his autobiography seems like a powerful thing to do this weekend.

Last night, I read COVID-19: The Pandemic that Never Should Have Happened and How to Stop the Next One by Debora MacKenzie. She wrote it in two months as the pandemic started, and did a great job. It goes well beyond just Covid, exploring past pandemics, things we could have done, didn’t, and why we are in the situation we are in now. As with my new book The Startup Community Way, she builds her framework on complex systems, explains them clearly, and applies the structure to the Covid crisis.

Finally, if you are a podcast person, I have two personal ones that I really enjoyed doing. The first is from the Techstars GiveFirst podcast and is with Len Fassler, titled Brad Feld and the mentor who changed his life.

The other is with Harry Stebbings on his 20 Minute VC podcast and is around mental health. I’m a guest, along with Jerry Colonna and Tracy Lawrence. 20VC: Brad Feld, Jerry Colonna, and Tracy Lawrence on Depression and Mental Health, Why You Cannot Tie Happiness to Milestones & Why Fear, Anxiety and Guilt are Useless Emotions.

The podcast with Len gave me chills when I listened to it, and Harry’s was excellent other than the missing Oxford comma in the title.


Seven years ago this week, I posted about a new book in our Startup Revolution series called Startup CEO: A Field Guide to Scaling Up Your Business, by my friend Matt Blumberg, then CEO of email marketing company Return Path in the Foundry portfolio. Today, with more around 40,000 copies sold all over the world and in multiple languages and formats, Matt and our publisher Wiley & Sons in partnership with Techstars have published a Second Edition of Startup CEO, which you can pre-order here

Matt and I originally conceived of Startup CEO when I was writing Venture Deals where Matt organically ended up writing a sidebar for many of the chapters which we called “The Entrepreneur’s Perspective.”  At the time, we talked about him writing a full “instructional manual” for first-time CEOs, and that’s what Startup CEO became, with over 50 short chapters with practical “how to” advice on everything from Fundraising, to People issues, to Board management, to Self-Management. 

In the Second Edition, Matt, who led the sale of Return Path last year, added six new chapters on Selling Your Company, which really rounded out the book.

I have given or recommended Startup CEO to hundreds of CEOs over the years. Matt has been very generous with his time in mentoring other entrepreneurs or bringing his book to life in online education and webinars.  Today, he posted one of the new chapters from the Second Edition of Startup CEO on Techstars’ blog, TheLine, on Preparing Yourself for An Exit:  How Do You Know It’s Time to Sell? which is a great example of the new material in the book.

Matt and others are working on a companion/sequel to Startup CEO which will come out in late 2020/early 2021. So, get Startup CEO now so you’ll be ready for that one when it comes out.


I heard the phrase “Greenwood” a few days after George Floyd was murdered. I’d never heard of it, or of the Tulsa race massacre before.

It’s 2020, so I went looking around on the Internet. The more I read, the more upset I became. Amy and I then watched the first few episodes of The Watchman, and I suddenly had a desire to get a full picture of what happened.

I do this by reading a book. I’m not a history buff, so I don’t spend a lot of time going deep on a particular historical event. Most of the surface level history I know comes from high school in Dallas (where, of course, we began with Texas history), a lifetime of museums, occasional TV documentaries, Wikipedia, or conversations. And books.

When I’m interested in something, I read a book on it. Since I’m reading one book on racial injustice each weekend this summer (and, given the pile of books I’ve accumulated, I expect I’ll continue into the fall), I decided to make my Saturday book Tulsa 1921: Reporting a Massacre.

I chose it carefully after reading the backgrounds of a few other books. I was looking for a reporting of the event, which I expected would be challenging given both the time frame (99 years ago) along with what I expected to be a lot of historical bias. I chose this book because the author, Randy Krehbiel, has been a reporter for the Tulsa World (Tulsa’s daily newspaper since 1905) for over 40 years and a Tulsa native. I figured, if anyone, he’d be able to mine the history from a reporter’s perspective, while balancing the topophilia he had for Tulsa, against the backdrop of a horrific event in the city’s history. Finally, Karlos K Hill, the Department Chair, African and African American Studies at the University of Oklahoma, wrote the foreword and endorsed the book, giving it more credibility in my eyes.

I lost myself in Tulsa in 1921 yesterday afternoon and into the evening. The Tulsa race massacre was an injustice on multiple levels. It included the willful destruction of what at the time was one of the most successful Black communities in America. In addition to the 24-hour destruction of the Black community by a variety of White Tulsans in pogram-like fashion, the ensuing several years of efforts to relocate the community, rather than allow the Black property-owning residents to rebuild, was deeply disturbing. Alongside this was a continual denial of any sort of meaningful redress or compensation by the White leadership of Tulsa.

During this period, the KKK had a new resurgence, which reinforced many aspects of systemic racism, both related to this period in Tulsa, as well as across the entire United States. Black leaders, with a few White allies, fought for justice for the residents, victims, and families of Greenwood. They also fought against the corruption, blame-shifting, and systemic racism that existed at the time in Tulsa. The Black Tulsans of Greenwood eventually prevailed and rebuilt their community.

Krehbiel handled this story exceptionally well. There are many ambiguities and unknowns. Rather than rendering an opinion, he tried to acknowledge the biases, the potential perspectives, and citied whatever he could find in history. Rather than tell the reader what to think, he painted a full story, incorporating many voices from different frames of reference, and allowed the reader to form a view and decide when the record was ambiguous, what had happened.

While an emotionally challenging book to read, I ended my day Saturday with another layer of understanding of how systemic racism is and has worked, for many years, in the U.S.