Brad Feld

Month: May 2023

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.