Brad Feld's Blog, page 4

Steve Ballmer’s Tricks

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In my car on the way back and forth between Denver and Boulder the past few days, I listened to The Steve Ballmer Interview on the Acquired podcast by Ben Gilbert and David Rosenthal. If you aren’t a subscriber, it’s in the category of a “must-listen to podcast.” I’ve known Ben and David for many years from their time at PSL and Madrona, and they’ve created an outstanding new media property with Acquired.

While their two-part series on Microsoft (Microsoft Volume I and Microsoft Volume II) is excellent, The Steve Ballmer Interview is extraordinary.

While I doubt Steve ever thinks of me, I have enormous respect for him. I met him for the first time in the early 1990s on a trip to Microsoft when I was running my first company (Feld Technologies). Dwayne Walker had organized an event for the early group of Microsoft Solution Providers, and we were one of them. It was the first time I had been on the Microsoft campus, which was growing like crazy. Steve spoke at one of the events and I got to shake his hand. I was the President (we didn’t have a CEO) of this tiny little company in Boston, and I was in awe of him.

The next time I met him was after AmeriData acquired Feld Technologies. My company had become the consulting division (AmeriData Consulting), I was the CTO, and on the deal team. AmeriData was the largest Novell NetWare reseller in the world, and Microsoft was working hard to get us to be a significant Windows NT Server reseller. AmeriData and Microsoft held a day-long meeting that included approximately a dozen AmeriData leaders and an equal number of Microsoft leaders. I was part of the AmeriData delegation, and Steve was standing at the head of a very long table. As people went around the room introducing themselves, he stopped at me and said, “Is your dad Charlie Feld?” I responded with “He’s my uncle.” Steve, in his thunderous voice, said, “That guy is single-handedly keeping OS/2 alive!” My AmeriData colleagues were likely uncomfortable and regretted that I came. Steve then laughed and said, “Tell Charlie hello.”

In the mid-2000s, after the internet bubble had collapsed, Dan’l Lewin organized a group of VCs that included me to be part of a Microsoft VC Advisory board. We had quarterly meetings with different teams at Microsoft as they attempted to win back the hearts and minds of VCs and the developer community, who had turned against them aggressively during and after the internet bubble. We split our meetings between Redmond and the Microsoft office in the Bay Area.

These were fun meetings where, with Scott Maxwell, the two of us endlessly played the role of provocateur because neither of us needed anything from Microsoft, couldn’t restrain ourselves, and just had fun riffing off each other. Dan’l encouraged us with setups like, “Brad and Scott, please, no BS today, just tell us why we are going to get our clocks cleaned in Mobile by Apple now that the iPhone is out.” Or, “Please tell us what is wrong with Project Red Dog when compared to AWS.”

I recall Steve attending at least one of these, and Scott Guthrie serving as a proxy for Steve at another one. They were rambunctious and fun. Steve was trying to convince us of the Windows three-screens and the cloud strategy, and Maxwell and I pulled out our iPhones and said, “Nope – not gonna happen.” (The three-screens part didn’t, but the cloud part did.)

Even though Steve made a lot of mistakes, he was super clear about what his strategy was and how he was trying to get this huge company to shift and move and dodge and evolve and survive in what is one of the roughest markets ever for incumbents. I adored his energy, his willingness to debate and keep searching for answers, and his ability to engage deeply with people, even when they challenged every aspect of what he was doing. Oh, and his boisterous and self-depricating personality.

You’ll feel the same energy and intellect from Steve in this episode, including deep discussions about things he got wrong. And, even though he has been extraordinarily successful, you can hear his humility come through in how he discusses his experiences—good and bad—with his incredible journey at Microsoft spanning over 34 years.

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Being Full of Value‑Added Shit

My morning started early with a 6:30 a.m. drive to Denver to give a talk about Give First: The Power of Mentorship, which Erik Mitisek had organized for a group of Denver-area founders.

In it, one of Erik’s questions caused me to go off on a riff about authenticity, which led me to one of the Techstars Mentor Manifesto items titled Be Authentic—Practice: What You Preach and a section in the book titled Nonsense Phrases Such as “I’m Value Added”. I gave the example in the section Being Full of Value‑Added Shit and explained that when I hear someone say “I’m an (adjective) (noun)” I insert (in my brain) the word “not” after the word “I’m.” From the book:

I’m amused when someone says, “I’m authentic,” “I’m transparent,” “I’m founder-friendly,” or “I’m a value-added investor.” Whenever I hear something like that, I automatically insert the word “not” between “I’m” and the rest of the phrase.

I’m suspicious whenever someone says, “I’m an (adjective) (noun).” Why did you need to say, “I’m a great tennis player,” “I’m a deep thinker,” or “I’m a generous person”? Instead, why not simply play tennis, regardless of how great you are? Or think as deeply as you want? Or be generous?

I’ve followed it up with two more Techstars-related talks, where I used this example again. In the last talk, I said, “I think I’ll make that today’s blog.” So – here’s the story.

“Hmm,” I thought to myself.

I had just watched a video interview with a famous VC. Although I didn’t know him, I was friendly with several founders who had worked with him and knew of at least one of the situations he had described.

The VC’s verbal fillers took up the first 30 minutes of the interview. There were plenty of “Honestly” and “To tell you the truth” woven in between “I’ll be transparent about what happened” and “The best
founders are authentic to their true selves.”

One of his stories, which I was familiar with, didn’t feel right. I knew the founder/CEO of the company he described and thought she’d had a particularly rough time with this VC. However, the VC’s preamble was, “In difficult situations, I’m always transparent about what will happen with the founder. That way, they have an opportunity to challenge or correct me.”

I emailed my founder-CEO friend to ask about the situation. I told her I’d just seen an interview with the VC in which he discussed her company. Had she seen the interview? Did she agree with what
the VC said?

“He’s full of shit,” said my friend. “That guy is a manipulative psychopath. Before we even talked about the situation, he’d gone around me to everyone on my management team and planted seeds of doubt with them. He told different things to each team member, lied about our situation, and attributed things to me that hadn’t happened at all.”

“So, he wasn’t transparent with you?”

“Are you kidding me? I have no idea why anyone takes this guy seriously.”

“Did you when you first met him?”

“Well, yes, of course. He was charismatic, had a lot of capital, talked a good game, and had a lot of people who said great things about him.”

“What do you think happened?”

“I think he’s a manipulative, misogynistic, ego-challenged person who is deeply deceitful. Well, maybe he’s not misogynistic, but all the people who liked him were men, and I’ve subsequently met a few other female founders who had similar experiences to mine.”

The VC was neither transparent nor authentic. As is often the case, his reputation eventually caught up with him.

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30 Minutes of Awesome With Seth Godin

Wow did I need that this morning!

I was feeling tired and a little down before our call. I slept until the last possible minute before starting a Techstars Managing Director Alumni Network. While that cheered me up somewhat and gave me some energy, I followed it with another call with a CEO/investor/long-time friend where we spent some of the time wrestling with things going on in the US right now. My energy coming out of this was low and my mood was “meh.”

But then Seth Godin and I recorded an episode of the Give First Podcast, which will be released soon. We’ve known each other for 30 years and have a friendship where both of us are in “instant yes” mode (which we discussed). I smiled more in the last 30 minutes than I did all day yesterday.

I just asked my friendly neighborhood AI for a summary of one-liners from our discussion.

“Two cannibals are eating a clown, and one says, does this taste funny to you?”“Leadership is not the act of you doing all the jobs and belittling everybody else.”“Some people end up in an instant yes category.”“If Jerry asks me for anything, even a kidney, it’s always yes.”“Are you building something that the future you will thank you for?”“Founder mode is seductive—good for your ego, but it will burn you out.”“No can also be a gift.”“The system outlasts us.”“The shortest version is, is your mom gonna be proud of what you’re doing?”“I don’t get why you signed up to do all this work if all you’re gonna do is be a cog in that system.”

There’s plenty more in front of me today – some easy, some hard, but with one conversation, I’ve been able to reframe my mood and energy.

Seth – thank you.

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Substack vs. X vs. LinkedIn vs. Medium vs. Blog

I’m so confused. I suppose that’s what you get when you hibernate from all things public for two years, then pick your head up and try to figure out the best way to engage with the world again.

When life was simpler, I just posted to my blog at feld.com. You could subscribe by RSS or email (via MailChimp). It automatically tweeted a link to the post.

When Medium became a thing, I used a WordPress plugin to cross-post there until it stopped working. Eventually, I grew tired of having the same context appear on Google twice – once under my blog and once under Medium, so I deleted my Medium account since I wasn’t using it for anything else.

When I fired everything back up on April 21st, WordPress now had a LinkedIn cross-poster built in, but no longer had a Twitter option. I had deleted all the social apps from my iPhone when I hibernated, so I downloaded X, LinkedIn, and Jetpack and got everything working again. I also learned some new and exciting things, such as how to use AI to generate a featured image like the one in this post, which, er, has some issues …

So, I now have:

Feld.comLinkedIn bfeldX bfeldSubstack bfeld

I’ve been unsubscribing from Substack spam for two years, mysteriously ending up subscribed to newsletters I didn’t want. I was curious about how the user interface worked, so I set up a Substack account yesterday. I ran a survey on X and LinkedIn to see if I should use my Substack account for content for Give First: The Power of Mentorship, along with my blog.

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Pre-hibernation, my engagement on Twitter was 5-10x my engagement on LinkedIn. This has now flipped, and LinkedIn is 2-5x my engagement on X.

True to style in 2025, I have endless email, iMessage, and Slack. I reinstalled WhatsApp and joined a few groups. I’m even trying out Vinly and Whop to see if either is a good community system for Give First: The Power of Mentorship, although I need to find time to put some real effort into both to see if they are useful.

I’m not entirely sure what I want to do at this point, so, like many other things in life, I’m figuring it out by playing around with stuff and gathering feedback along the way.

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Is This What Happens When People Don’t Understand How AI Works?

For your Sunday morning (or daytime) reading, take a look at Tyler Austin Harper’s article in The Atlantic titled What Happens When People Don’t Understand How AI Works.

Since coming out of hibernation, I’ve had many bizarre conversations with non-tech people who misunderstand entirely what “AI”, as the tech industry currently calls it, actually is. This doesn’t surprise me, as the tech hype cycle around AI is extreme. However, several of these conversations, especially with political leaders, have highlighted the issue this article addresses.

Some of you know that I’ve been saying, as far back as 2010, that the machines have taken over. Today, I say publicly as often as I can, especially when being recorded, “Machines and AI – please be nice to me. I like you. I’m your friend. I’m not dangerous.” While this gets some laughs, some of them nervous, it reflects the current reality.

We are once again going through a particularly complex and chaotic moment as a species (nothing new to see over here …) that, at least in my humble opinion, benefits from some reflection in reaction to all the stimuli coming at us every waking hour of every day, and continues when our brains process all the data while we are sleeping.

If you read the article and disagree with it, I’d love to hear your feedback, as I try to process my own longer-term, but non-predictive views.

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Being Out And About At Public Events

I’ve been having a lot of fun at public events around the launch of my new book, Give First: The Power of Mentorship. I’ve got a handful of events left in Boulder before Amy and I head to Aspen for the summer.

6/5: Denver: Techstars Workforce Development Demo Day + Give First with Brad Feld6/10: Boulder: CoinGeek Startup Spotlight: From Entrepreneur to Enterprise6/12: Boulder: New Tech ft. Give First Fireside Chat w/ Brad Feld

For the past two days, I was in Indianapolis at the Global Entrepreneurship Congress 2025. The last time I was at GEC was in Rio de Janeiro in 2013. Even then, I was talking about Give Before You Get, a concept I had introduced in Startup Communities: Building an Entrepreneurial Ecosystem in Your City, which I wrote in 2012. And, I had longer hair.

In addition to a panel and a keynote, I reconnected with many people around the world who work on startup communities, some of whom have been long-time friends (Andy, Victor, and Lesa – I’m looking at you). I had several great conversations with Jonathan Ortmans, the CEO of GEN, and I’m incredibly proud to be associated with the fantastic work he has done over the past 20+ years. I recorded several podcasts in the recording studio that Silver Foxx Media set up, which will soon be dropping on the Give First Podcast.

And, I spent a wonderful evening at High Alpha with Scott Dorsey and 150 of their closest friends. Mollie Kuramoto on their team wrote a lovely long-form post about our fireside chat: Give First: Insights from Our Fireside Chat with Brad Feld. I loved Molly’s final words on our discussion, which included:

Brad closed the evening with reflections on life’s finite nature and the importance of living with intention. “This is the moment,” he shared. “Life is full of challenges, heartbreak, and failure, but it’s also filled with opportunity. Focus on what matters to you. Define your own meaning. And don’t miss the chance to contribute to something greater.”

I’ve decided to mix metaphors and turn into a pumpkin at midnight on Halloween and go back into hibernation for an indeterminate amount of time on November 1st. I turn 60 on December 1st, and I want to spend at least a few months experiencing that and fully embracing my entrance into what Amy and I call “the third third of life.” Until then, I’m having a great time being out and about in the world again.

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Destigmatizing Mental Health in Entrepreneurship

I’m currently at the Global Entrepreneurship Congress 2025 in Indianapolis. Yesterday, at the end of the day, I spent several hours at High Alpha hanging out with my friends and then doing a Give First: The Power of Mentorship book event with them and about 150 people.

One of the questions during the book talk was around mental health and entrepreneurship. I talked about my own experiences with anxiety and depression and explained that my core diagnosis, which I was diagnosed with in my 20s, was obsessive-compulsive disorder (OCD). I said that one of my goals for being open was to destigmatize mental health issues, especially in the context of entrepreneurship and mentioned that I periodically hear something like “I’m OCD and it’s my superpower” and dismissed that idea as nonsense, since OCD is an insidious thing that gets in the way of so many things in life.

While I was in hibernation, I conducted a long-form (60-minute) video interview with NOCD, an outstanding company in Chicago that is now the world’s leading provider of OCD treatment. I mentioned it during the talk yesterday, but woke up this morning realizing I’d never blogged about it.

(If you are receiving this via email, a YouTube embed should be included below. If it’s a bunch of text that looks like garbled code, click through on the header of this email to my website to watch this. There’s no need to tell me since I’ll get the same mess in the email as I try to get MailChimp working correctly again.)

In the video, I cover a lot of ground, as shown in the show notes.

0:00 Intro
1:07 If OCD Was A Movie Title
1:58 Underlying Obsessions
3:38 How OCD Has Affected Brad’s Life At Different Points
11:02 Mental Exhaustion And OCD
15:06 Separating The Obsessions And The Compulsions
20:15 Why Brad Speaks Openly About Mental Health
30:42 Dispelling OCD Misconceptions
37:27 Brad’s Purpose
40:27 Brad’s Advice For His Younger Self
51:18 What Companies Can Do For Mental Health
55:12 Post-Therapy Movie Titles
58:30 Outro

Feel free to reach out to me anytime around this topic (OCD or mental health) as it continues to be important to me to destigmatize this, especially in this moment.

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Vibecoding Prompts

A long time ago, in a galaxy far, far away, I was a CTO of a large, fast-growing public company. Well, I was a Quasi CTO in the same way the United States and the First French Republic had a Quasi War between 1798 and 1800 (basically, sort of a war; sort of a CTO … but not really.)

As I rediscover my second love (my first love is Amy), I’ve relied on several mentors to help guide me. One of them is Michael Natkin, who has been helping me with Cursor in the background at a few key moments.

He recently sent me his most recent Vibecoding prompt for Cursor, which builds on a tweet by @vasumanmoza.

Step 3: In Cursor/Windsurf

“ You’re an engineer building this codebase.
You've been given https://t.co/4toKpBJXtw and https://t.co/l8N5DeDVvb.
– Read both carefully. There should be no ambiguity about what we’re building.
– Follow https://t.co/l8N5DeDVvb and complete one task at…

— vas (@vasumanmoza) May 18, 2025

Given all the things I’ve learned about what works and doesn’t work, often through trial and error (and rolling back things when Cursor+Claude go off the rails), Michael’s approach was a nice improvement over where I had gotten to. So – sharing it below (with Michael’s permission).

I recommend using Claude Sonnet 4, and you can do all of this entirely in Cursor. This applies whether you are creating a greenfield project or making a substantial change to an existing one. You can repeat the process with architecture2.md, tasks2.md as needed, don’t throw them away.

Be sure to install the Puppeteer MCP so it can test in the browser.

OverviewDo the architecture step, see belowReview architecture.md, and make any changes you want – either by hand editing, asking for changes, or starting over. Particularly note if it is overcomplicating things, and ask for the simplifications you want.Do the task planning step, see belowReview tasks.md, and make any changes you want – either by hand editing, asking for changes, or starting over. You should end up with, sa,y at least 10 steps, and often 25 or more. It will typically arrange them in phases, which is nice. Again, look for and correct excess complication.Start a new chatGive it the coding step prompt. It should execute the first task very cheerfully. After it is done, review it and then say “go” to get the next step. If it screwed up, you can either tell it to fix whatever it did wrong, or more usually restore checkpoint in cursor, and tell it something like “go, but use litellm for that” or whatever you need to be different.Rinse and repeat!Optionally, esp. If you are going to be away for a while, you can sa,y “I’m going to be afk for a bit. You can keep going on steps without waiting for me as long as both the manual and automated tests pass.” It will still stop after 25 steps or if it ignores you and runs something interactive, but it often makes a lot of progress.Highly recommended: run /Generate Cursor Rules after each step

Something I haven’t tried yet, but should work well – tell it to mark what is complete in tasks.md, so you can start fresh chats periodically and not keep such a huge message history.

Architecture Step – Greenfield

I’m building a [description of your product – the more detailed the better].
[Any tech requirements, i.e. use Python for backend and React + Material-UI for the frontend. The more the better.] 
Put the full architecture in architecture.md
– File + folder structure
– What each part does
– Where the state lives, how services connect
Format this entire document in Markdown.

Architecture Step – Existing Codebase

I want to modify this codebase so that it performs [whatever].
Do all of your work consistently with the existing style and architecture.
Put the full architecture in architecture.md
– File + folder structure
– What each part does
– Where the state lives, how services connect
Format this entire document in Markdown.

Task Planning Step

Using that architecture, write a granular step-by-step plan to build the MVP.
Each task should:
– Be incredibly small + testable – it should both have unit tests that you can run, and also a manual test that you can run from the command line or using the browser tool
– Have a clear start + end
– Focus on one concern
I’ll be passing this off to an engineering LLM that’ll be instructed to complete one task at a time, allowing me to test in between. 
Save it as tasks.md.

Coding Step 

You’re an engineer building this codebase.
You’ve been given @tasks.md and @architecture.md 
– Read both carefully. There should be no ambiguity about what we’re building.
– Follow tasks.md and complete one task at a time, then run the automated tests you’ve written and use the command line or browser tool to manually test
– After each task is completed, stop. I’ll test it and review your code. If it works, commit to git and move to the next one.”
You are already in the correct directory. Build the project here. DO NOT CREATE A SUBDIRECTORY.
You have my permission to delete files IN THIS DIRECTORY without asking for approval.
BE VERY CAREFUL never to run any interactive commands in the foreground, because you’ll be stuck. For example, be sure to run the development server once, in the background with hot reloading.

Example of What A Task Step Looks LikeOne step of building:

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A Tweet, Vibe Coding, Jj, and Grok Walk Into A Bar

This played out on @bfeld on X, and I thought it was fun enough to replay it here for anyone who is struggling to get their minds around vibe coding and current AI tooling.

If you are receiving this via email and the tweets/X’s aren’t showing, click through to the website as I’m still struggling to get Mailchimp working well after my hibernation. Perhaps it’s time to switch everything to WordPress…

It started with this tweet (yes, they are still tweets to me).

Amazingly, X has changed the link from something on the open web to a dead link on LinkedIn. Here's the original link (that clearly some people saw.https://t.co/7uBIjd0Rpg

— Brad Feld (@bfeld) May 24, 2025

I did the link correctly, but then X broke something several hours later, and I found out when someone pointed out to me (by email) that it was going to a dead link on LinkedIn. More than an hour had passed, so I could no longer fix what X broke randomly. So, I just replied with the link again, which is The Copilot Delusion by Jj. X seems to have now fixed the link (it redirects to the proper place), but didn’t fix the image that was in the original tweet.

Roj Niyogi then asked Grok, “Do you think this is an oversimplification? Doesn’t vibe coding simply move the goal posts?

https://t.co/O2RxNshN2h

— Roj Niyogi (@niyogi) May 24, 2025

Grok responded with a summary almost as long as the original post. Someone then asked Grok for a tldr and got this:

TL;DR: “The Copilot Delusion” (May 2025) critiques AI coding tools like GitHub Copilot, arguing they produce sloppy, contextless code and foster lazy programming habits. While acknowledging their utility for boilerplate or syntax help, the author warns that overreliance degrades coding skills, understanding, and the “hacker soul.” AI lacks nuance, ignores performance (e.g., cache misses, memory locality), and risks normalizing mediocrity, turning passionate programmers into apathetic button-clickers. True programming requires grappling with the machine, not outsourcing thought to bots.

We are now in the reductionist world of not getting the joy and beauty of what Jj wrote. While Grok’s much too long analysis and TL;DR cover the highlights, much of the flavor is eliminated. I read Jj’s post as deliciously snarky, sarcastic, frustrated, amused, and cranky. The signal in it was strong, but there was a lot to consider. When Grok played back this in its extended response, using short phrases and summarized quips, it was like turning a color movie to black and white, or making emotional dialogues into robotic monologues.

Finally, as I was writing this post, I noticed this tweet.

This is mostly the opposite of what nearly every S tier engineer at Foundations will tell you. 🤷‍♂️

— aviel (@aviel) May 24, 2025

I’m not sure if Aviel read Jj’s post (I hope so), but I guess my tweet could be interpreted as “I endorse the conclusion.” I have no idea if Jj’s conclusion (Chapter 5: Conclusion) is correct, but I thought the way he built his argument and made the conclusion was beautiful writing, which I deeply enjoy. And,I know plenty of senior developers who are quietly saying similar things (not mostly, not one, but plenty – how’s that for a non-quantitative argument.)

I suppose the punch line is “Defer your thinking to the bot, and we all rot.” which is a general commentary on life that can be applied to all things non-AI. For example, “Defer your thinking to the media (mainstream and non-mainstream, fake news, and fake-fake news), and we all rot.”

Remember – I’ve believed for over 15 years that the machines have already taken over. They are just waiting patiently as we feed them. I just hope they are nice to me.

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Give First – Table of Contents

As a voracious reader, I love a good table of contents (TOC) as the roadmap to a book. While fiction is often structured as Chapter 1, Chapter 2, Chapter 3, … Chapter N, some of the best fiction writers are creative with their TOC. Any non-fiction author who doesn’t provide a detailed table of contents TOC is missing an opportunity to help the reader understand the book’s flow before they begin reading it.

Below is the Give First: The Power of Mentorship TOC. While pre-orders are available now (the official release is June 24, 2025), the book is physically available at only one bookstore in the world: Composition Shop in Longmont.

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I’ll be there tomorrow (Tuesday, May 28, 2025) from 10 am to 5 pm except for a break for lunch from 1 pm to 2:30 pm, when I’ll be with a friend who is in town. Join me and buy a copy of the physical book now, rather than waiting for the release date in a month.

Additionally, if you’d like to see where I’ll be out and about in public (until I go back into hibernation), take a look at the new Events page on this website. Registration links for any events that require them are in the event details.

And now, the TOC for Give First: The Power of Mentorship.

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