Brad Feld

Feld Thoughts

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Soundarya kept me updated, and I got the unpublished manuscript for Unshacked five months later.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


Alan Arkin is one of my favorite actors. I just saw a note that he passed away yesterday.

I expect I’ll look like him when I lose my hair since he looks like my dad. And every time I see Alan Arkin, I think of my dad.

If you see me driving my Jeep around Boulder, I just gave you a hint about what my license plate (ARGOFY) means.

Rest in peace, Edwin Hoover.


The Venture Deals course is free and starts on June 20, 2023.

This is the fourth time we are running the new version of the course (v2!) that was co-created with Techstars and Kauffman Fellows.

If interested, sign up now. I hope to see you in one of the AMAs we will host for anyone who takes the course.


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.


I got an email from Matt Blumberg this morning with the above image that said,

“We have been blogging for 19 years. I can remember sitting together above Super Liquor futzing with Typepad like it was yesterday.”

“Super Liquor” is Superior Liquor in Superior, Colorado, which was on the first floor of the building off of Hwy 36, which was my office at the time. There was also a pizza restaurant on the first floor.

I asked Matt if we started on the same day because I couldn’t remember. He said,

“Literally the same day.  We sat at a desk right outside your office in Superior, pulled up our laptops, and taught ourselves Typepad together and created our templates.  Fred had already been blogging for about 6 months, and we had dinner the night before (can’t remember where, think The Med) and decided we would give it a try.  We couldn’t find other good examples of VC or CEO blogs. “

I went and looked at some of those first few posts. Matt’s was You’re Only a First Time CEO Once. Mine included To Blog or Not to Blog (which called out a handful of VC bloggers who started before me), Blog tools – Newsgator and Moveable Poster, TDC (Thinly Disguised Contempt), and my first book review: Free Prize Inside the Radioactive Boy Scout Rate Hikes.

My favorite of those was TDC (Thinly Disguised Contempt).

As was the tradition at the time when new bloggers appeared on the scene, Fred Wilson wrote nice posts linking to each of us. His welcome to Matt was Welcome to the Blog World Matt, and his welcome to me was This Is Going To Be Interesting.

This post wouldn’t be complete without my hat tip to Fred, who, in my view, is the OG VC blogger. His first post was creatively (well – not really) titled MY First Post.

19 years is a long time to do anything. It’s close to my board service record, which ironically was on Matt’s company Return Path with Fred. The ending of Fred’s first post resonates with me today as it did 19 years ago.

“I have no idea if i’ll write a lot in my blog or rarely. I hope its a lot, because i have a lot to say. But we’ll see about that.”


Startup Snapshot, a data-sharing platform for the entrepreneurial ecosystem, recently released its latest report, The Untold Toll: The Impact of stress on the well-being of startup founders and CEOs.

Clearly, the emotional state of founders and entrepreneurs in any period, especially now in this economic environment, is a critical driver of success. Yet the emotional, cognitive, and physical toll that founding and leading a startup takes is dangerously overlooked and rarely spoken about. 

Startup Snapshot is illuminating the current state of the startup mindset through global data collected from hundreds of founders in startups of all sizes, in all verticals. It’s the largest study of its kind. And it is honest and gritty, with no punches pulled.

  • The startup grind takes a major toll on a founder’s mental health. 72% of founders reported that the entrepreneurial journey affected their mental health, 37% suffered from anxiety, and 36% from burnout.
  • Founders are known for their innovative spirit, but in terms of therapy, they are stuck in the past. Only 23% of founders report going to a psychologist or coach.
  • 50% of founders report a negative stigma around professional mental health support. Surprisingly, the stigma is higher for younger founders, with 59% of founders under 35 reporting a negative stigma, compared to only 47% of founders over 35. 
  • Founders mask the stress, and it catches up to them. 81% of founders reported they do not openly share their stress, fears, and challenges, worried that vulnerability could affect their reputation or chances of success. 
  • Venture capitalists need serious self-reflection as their portfolio companies don’t turn to them for support. Only 10% of founders reported that they talk to their investors about their stressors, worried that transparency could affect their chances of securing additional funding. 

Startup Snapshot is continuing to research founder mental health, if you want to take part in normalizing the dialogue around this important topic, reach out to yael@ybenjamin.com.


I’m not a sports fan, but wow, this is good.

Thanks, Dave Mayer, for sending this to me.

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.


After my post about the Founder Mental Health Pledge, I received a note from Kari Palazzari, the Executive Director of Studio Arts Boulder, a local nonprofit that manages a community pottery studio. She lamented that very few members of the Boulder startup community seem to take advantage of their programs.

She said, “Studio Arts Boulder would love to help support the Founder Mental Health Pledge.”

A couple of my local colleagues have taken classes at the pottery studio, and they speak avidly about the impact of working with clay. It helped them be less stressed and more focused, which makes a big difference when tackling a startup’s unique problems. Kari said, “People come out of the studio less twitchy, for sure.”

There’s a lot of data about the impact of the arts. Making art, in particular, helps combat anxiety and depression. It improves cognitive function by making our brains more resilient and flexible, which means we become more creative problem-solvers all around. 

We can tackle the mental health challenges within our industry in many ways, and I encourage more of us to try art. Start small with a date night – offered by Studio Arts Boulder every Saturday. Or better yet, schedule a private program for your team at your office or in the pottery studio.

And if clay isn’t your jam, early next year, Studio Arts Boulder is opening a new facility that will include woodworking, blacksmithing, printmaking, and glass art studios. How cool is that?