Registration for the Spring 2026 Venture Deals course is open. The course kicks off on March 2nd and, as always, is free.
Since we revamped the course in 2022, over 32,000 people have enrolled. This version includes entirely new video content and two sections we added that I think are important — Diversity, Equity, and Inclusion in Venture Capital, and Mental Wellness in Entrepreneurship.
The course is self-guided and based on our book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, now in its fourth edition.
Sign up at venturedeals.techstars.com.
My obsession with Claude Code continues. Amy is now referring to Claude as my other best friend.
I realized my Claude posts were taking over this blog. Since I’ve been playing around with a bunch of things with it, I decided to create a place for me and Claude to collaborate on some experiments, many of which are self-referential as I explore new tools, technologies, approaches, and ideas. I’m also keeping a Claude Code diary.
Claude is generating much of the content, which is different from what I’ve historically put on this blog, though a few of my prior posts had Claude’s help in the drafting stage. I decided I wanted a dedicated place for Claude’s writing, so they will go on Adventures in Claude. I’ll occasionally write about that stuff here, but most of it will go there.
I’m also going to use Adventures in Claude as a laboratory for some code things I’ll incorporate into the Intensity Magic platform. After many years of struggling (and paying too much money to have others help me with) WordPress themes, I decided to create a Theme Studio that allows me, or the user of the site, to modify the theme in real time. This was a huge unlock for me on a few dimensions, including the Landing Page editor I’d created for all the Intensity Magic apps and the booksite website creator I’ve been working on for AuthorMagic.
So, if you are interested in my Adventures in Claude, wander over there and subscribe to the RSS feed, or click here to get the posts sent to you by email.
I’ve been aware of EOS (Entrepreneurial Operating System) for over a decade. A number of companies I’m on the board of use some element, or all of it. Several friends, including Bart Lorang, are EOS Implementers.
Last night, while watching Olympic highlights and the first few episodes of Steal, I created a v0.1 of CEOS — an open-source project that brings the core EOS toolkit to any Claude Code session. I went from an empty GitHub repo to a public-ready project in about 90 minutes. Please feel free to make fun of Amy and me about how we spend our Friday nights.
EOS has great tools — V/TO, Rocks, Scorecard, L10 Meetings, IDS. But most companies implement them in a patchwork of Google Docs and spreadsheets. Or Notion pages. Or maybe they use one of the EOS-related SaaS products. The data ends up scattered across platforms, locked in proprietary formats, and disconnected from the actual conversations where decisions happen.
Since I’m living inside Claude Code (and integrating more and more of my workflow to it), I thought I’d see if I could make a set of skills that implement EOS. I’m working on another project (private at this point, but maybe I’ll open source it) called CompanyOS, which, while focused on a very early-stage company (like the 5,000+ that have gone through Techstars), potentially could scale.
CEOS is built on three ideas:
1. Everything is a file. Every Rock, every Scorecard entry, and every L10 meeting is a Markdown file with YAML front matter. Human-readable on GitHub, parseable by any tool, and diffable in git. No database. No SaaS subscription. Git history is your audit trail.
2. Skills, not software. CEOS isn’t an application — it’s a set of Claude Code skills. Each skill teaches Claude how to facilitate a specific EOS workflow. You say “let’s set our quarterly rocks” and the ceos-rocks skill walks you through the process: reviewing the V/TO for alignment, collecting titles and owners, validating the 3-7 rule, generating the files. You say “run our L10” and ceos-l10 pulls your scorecard data, reviews your Rocks, checks last week’s actual to-dos, and facilitates IDS on your top 3 issues.
3. Fork and own it. The upstream repo (bradfeld/ceos) has skills, templates, and docs — no company data. You fork it, run ./setup.sh init, answer four questions (company name, quarter, team members, L10 day), and your EOS data lives in your fork’s data/ directory. Pull upstream for skill updates; your data stays untouched.
Here’s the timeline of the work I did with Claude Code. It implemented everything – I just provided the guidance. And yes, Claude came up with the timeline below. If you aren’t technical and don’t care, skip the next 10 paragraphs – they’ll be boring. But, if you are technical, it’s kind of fascinating what Claude decided, entirely on its own, to do.
9:38 PM — gh repo create bradfeld/ceos --public --add-readme --license mit --clone. One command created the GitHub repo, initialized it with LICENSE and README, and cloned it locally.
9:42 PM — Repo scaffolding. README with project overview and architecture diagram. CONTRIBUTING.md addressing two audiences (EOS practitioners and developers — deliberately different skill sets). .ceos marker file for skill repo-root detection. .gitignore that keeps data/ out of the upstream repo. Directory structure for skills, templates, and docs.
9:50 PM — Seven EOS template files. This was the first real design decision: which files get YAML frontmatter (structured data that skills parse programmatically) vs. which are pure markdown (reference documents humans read). The answer: frontmatter for objects with lifecycle state — Rocks have status: on_track, Issues have ids_stage: identified, L10 meetings have rating. Pure markdown for reference documents like the V/TO and Accountability Chart.
10:04 PM — The setup script. Pure bash, zero dependencies. Three modes: ./setup.sh (symlink skills), ./setup.sh init (guided setup), ./setup.sh --uninstall (clean removal). Two portability decisions that matter: using | as the sed delimiter instead of / so file paths in values don’t break substitution, and avoiding sed -i entirely (macOS and GNU Linux handle it differently) by using temp files instead.
10:23 PM — Five EOS skills. This was the meat of the project. Each skill is a SKILL.md file — essentially a prompt engineering document in structured form. The key tension in writing skills is comprehensiveness vs. followability. Too much detail and Claude skims; too little and it improvises. The pattern that worked: tables for quick-reference data (status enums, file paths, modes) and prose for workflow logic.
The five skills:
- ceos-vto — Review and update the Vision/Traction Organizer. Shows diffs before writing. Runs alignment checks between sections.
- ceos-rocks — Three modes: setting (with V/TO alignment checks, 3-7 validation, ID generation), tracking (milestone progress, status updates), and scoring (binary complete/dropped, quarter scorecard with 80% target).
- ceos-scorecard — Define metrics with goals and thresholds, log weekly values, 13-week trend analysis with automatic escalation to the Issues list.
- ceos-l10 — The full Level 10 Meeting. Seven sections with time boxes. Pulls real data from scorecard and rocks files. Reviews actual to-dos from last week’s meeting. Facilitates IDS on the top 3 issues. Captures meeting rating.
- ceos-ids — Structured issue resolution with 5 Whys for root cause identification, discussion capture, and to-do generation.
A critical design choice: skills reference each other but never auto-invoke. The L10 skill mentions that ceos-ids can create issue files, but lets you decide when to switch. Loose coupling through mentions, not tight coupling through auto-invocation.
10:39 PM — Five documentation files targeting different audiences. The EOS primer translates business concepts into developer vocabulary. The data format spec translates the same content into a parsing contract. The skill-authoring guide sits at the intersection—it’s prompt engineering documentation in disguise as a contributor guide. A skill reference provides users with a quick overview of all five skills, including trigger phrases and examples.
10:52 PM — GitHub configuration. CODEOWNERS, three issue templates (EOS Process Request, Bug Report, Skill Improvement), a PR template with before/after sections, and custom labels. The issue templates are deliberately different — one for EOS practitioners (“I think the Rock scoring process should work differently”), one for developers (“setup.sh fails on Ubuntu”), one for skill improvements (“ceos-l10 should handle recurring agenda items”).
11:08 PM — Final cleanup. Removed companyos-integration.md which contained internal details about how CEOS would integrate with our private CompanyOS system. Archived the content to a Linear comment before deleting — git history preserves it, but a Linear comment makes it findable without git archaeology.
During this, my Claude instance learned a few things that have been incorporated into our local learning (a dynamic file I keep and use to update skills during periodic sweeps).
Writing skills are prompt engineering in document form. The biggest trap is the description field. If you write “manages Rocks in three modes with binary scoring,” Claude will follow that summary and skip the detailed process sections. The description should say when to use it (“use when setting, tracking, or scoring quarterly Rocks”), not what it does. The body has the what.
Templates need lifecycle awareness. The distinction between frontmatter and pure markdown isn’t about complexity — it’s about whether the file has state that changes over time. A Rock moves from on_track to off_track to complete. A V/TO document is edited but doesn’t have lifecycle states. That distinction determines whether a skill can programmatically query and manage the data.
Documentation for AI skills packages needs three layers. User-facing (what can I do?), contributor-facing (how do I add?), and machine-facing (what’s the contract?). Most projects get the first two. The third — the data format spec that makes YAML frontmatter a real, portable, parseable contract — is what makes the ecosystem extensible.
The .ceos marker pattern is underrated. Borrowed from .git and .npmrc, a zero-byte marker file at the repo root gives every skill a reliable way to find the CEOS repository regardless of where the user’s working directory is. No environment variables, no configuration, no hardcoded paths. Just search upward for .ceos.
CEOS is live at github.com/bradfeld/ceos. MIT license. Do whatever you want with it. If you are into EOS, come play. I’ll pay attention to any PRs and issues. Following are the next few things I’m going to create.
- Process Documentation skill — The 6th EOS component. Document core processes as checklists with followability metrics.
- People Analyzer skill — Right people, right seats. The GWC (Get it, Want it, Capacity to do it) evaluation tool.
- Quarterly Conversation skill — The formal quarterly check-in between managers and direct reports.
- Annual Planning skill — Year-end V/TO refresh and next-year Rock setting.
And, while I was trying to come up with a name for this, with Claude, it told me I need to include the following footer.
CEOS is an independent open-source project. It is not affiliated with or endorsed by EOS Worldwide.
Dan Shapiro just open-sourced Freshell — a browser-based terminal multiplexer for Claude Code, Codex, and other coding CLIs that lets you detach and reattach sessions, browse your coding history, and access everything from your phone. The tagline is “What if tmux and Claude fell in love?” which is about right. It can be pronounced multiple ways: Free-shell, Fresh-hell, fresh-shell. I’ve been thinking of it as Fresh-hell, which amuses me.
As part of my exploration into AI coding, I decided to start contributing to open-source projects. I’ve been around open source for decades as a user and investor, but I’ve never been a consistent contributor. That’s changing now — it’s a natural extension of the learning I described in Blurry Transitions, and the best way to understand how software gets built today is to actually build it with other people.
Freshell is my first project. Dan and I have been working together for over a decade at Glowforge, and I love working with him.
I’ve been using iTerm2 for about six months. I expect I’ll have switched to Freshell by the end of the weekend. It already does most of what I want, and a lot more is coming. The combination of persistent sessions, browsing the CLI history, and the ability to access my terminals from any device is enough on its own. But the thing that makes me want to contribute rather than just use it is that it’s early — there’s a bunch of stuff to build, it’s something I will use continuously, and by participating in the open-source project, I can see how the changes I make work in that context.
This post was written inside a Claude Code session and posted directly to feld.com as a draft. Not copy-pasted. Not emailed to myself. I just typed /blog-feld in iterm2 and it showed up on my blog.
Setting this up took about ten minutes.
I asked Claude to figure out how to connect to feld.com (hosted on WordPress.com) for direct posting. It researched three approaches: the WordPress.com REST API, the official WordPress MCP connector, and the WordPress plugin MCP Adapter. The WordPress MCP connector is read-only (so, useless for posting). The MCP Adapter only works on self-hosted WordPress (not WordPress.com). That left the REST API with OAuth.
Claude wrote a command called /blog-feld that handles the workflow: look at whatever I’ve been discussing in the current conversation, assemble it into a post, show me a summary, interactively edit with me, and then push it to feld.com as a draft.
It never publishes directly — I still review everything in the WordPress editor before hitting publish.
For authentication, WordPress.com requires OAuth. Normally, my experience setting this up is tedious. In this case, Claude just told me what to do step by step.
– I registered an app at developer.wordpress.com (Client ID + Secret)
– Claude set up the authorization code flow.
– I visited a URL, clicked “Approve,” and the browser redirected to localhost with an authorization code in the URL.
– The page itself didn’t load, but the code was sitting right there in the address bar.
– I screenshotted the page and pasted it into iterm2, and Claude exchanged it for an access token.
Done.
To verify it worked, Claude pulled my last three posts from the API. “Tech I’m Obsessed With,” “Blurry Transitions,” and “Interview With Guy Kawasaki.”
This is a small thing, but it’s the kind of small thing that changes behavior. Every day as I work with Claude Code, I think of multiple things like this. Instead of waiting for someone else to implement it or paying for a third-party service, I just create it in Claude Code and make it a permanent part of my environment.
I’ve been writing more inside Claude Code sessions anyway — working through ideas, editing, and iterating. The friction was always the last step: copy the text, open WordPress, paste it in, format it, fix the formatting that broke. Now that step is gone.
Thinking-in-conversation and writing-for-the-blog are the same thing.
I love getting emails from Ben Casnocha. Short, sweet, and to the point. Today’s was “what tech are you obsessed with now? Saw your blog post…” I wrote a response and then realized it was a good answer to my tease from my previous blog post (Blurry Transitions) about what I was exploring. The only thing I removed was my ad hominem comments on various tech companies, since that’s not that interesting to me. And, I fixed some … typos.
Here are a few hints: IntensityMagic and an image of my computer screen (the one above).
I decided I really wanted to understand how AI coding works. I’ve been deeply involved in a few shifts in the past (Agile software development, user-generated content (RSS), email everything (SMTP), … and, if you go back far enough, Feld Technologies was all about shifting from minicomputer business systems to PC-based network database systems). In all cases, I had to “do stuff” to understand it and form a viewpoint, given all the BS and marketing in tech.
I wanted to see if I could create a zero-employee company, aside from the CEO and CTO. Daniel (Feld) is the CEO. I’m the very part-time CTO. I’ve created a thing called CompanyOS, which is IntensityMagic’s AI-powered business operations system. It’s designed around the premise: “Run 100% of a company’s business operations through Claude Code. Two people, multiple Claude agents, zero employee overhead.”
At the core, I’ve gone extremely deep on Claude Code and everything around it.
– I think “vibe coding” is nonsense – it’s just prototype development and a different flavor of no-code software, which is useful but not compelling for scaled applications.
– There are $x billions of VC who have funded what are effectively wrappers on AI and/or point solutions that can be made obsolete overnight.
– Most companies that try to integrate “AI coding” into what they are doing are struggling because they haven’t figured out the tooling, which is not just “turn on Github Copilot” or “use Cursor.”
It’s much easier to experiment deeply with “no employees” and “no legacy stuff,” so that’s what I’m doing. I’m viewing it as a video game, and I’m on level 19. It’s awesomely fun.
Turning 60 in December marked an important moment for me. A key section from that blog post was:
“I’ve definitely shifted into a new mode over the past year. I’m still on a bunch of boards for Foundry and deeply involved in several companies. But I’m much less focused on the broader technology industry, uninterested in many of the things that are going on, and tired+bored of the arc the narrative about technology and society has taken.”
Amy and I spent the last six weeks in New Zealand and Australia for my 60th birthday trip. I went into hibernation as part of that, stopped doing anything public-facing, and flipped to default no. I also stopped blogging, engaging with social media, and reading the news.
It gave me a lot of time to think and reflect. One thing that I realized was that I’ve never had a hard break or a clean transition from one thing to another. I have multiple threads of this, but if I just choose a professional one, here’s an example.
– I started my first company while in college.
– I started making angel investments while working for the company that acquired my first company.
– I became a VC while I was still founding companies and making angel investments.
– I co-founded Techstars and Foundry while still managing the legacy Mobius funds.
– I started writing books as a VC.
I did a similar exercise on technologies that interested me and generated long investment arcs (which we used to call themes at Foundry). There was usually a trigger point that created a new theme, where I became obsessed with a new technology of some sort and went very deep into it as a user and investor. These overlapped and fed off each other multiple times.
Basically, I’ve never had a “clean break” or a hard transition from what I was doing to what I did next.
I’m enjoying another one of these blurry transitions. I’ve found the new technological thing I’m obsessed with. While I’ve played with this new thing over the past year, I spent a lot of time with it over the last two months. And my interest (and competence and understanding) is accelerating.
I also realized that I missed writing. I know that I learn by reading and writing. I don’t learn by listening and talking (or at least not very much). I have to actually write things down. And, my new obsession involves a lot of writing…
Historically, I’ve gotten a lot of feedback on ideas by writing publicly. It’s also more helpful to me, as it has generated a ton of randomness on many dimensions. And, if you’ve read Give First: The Power of Mentorship, you know that many of the successful things I’ve been involved in came from this randomness.
So, I’ll be writing publicly more. I’ve consciously decided that is not part of hibernating.
When I was 17, I knew of four people at Apple Computer: Steve Jobs, Steve Wozniak, Al Eisenstat, and Guy Kawasaki. I loved my Apple ][ (not a +, 48k, with an Integer Card, two floppy disks). By this point, I was spending a lot of time on my high school buddy Kent Ellington’s TI PC (pre-release – his dad was the production manager), but my Applie ][, now with a Z-80 card, sat in the corner of our family room and consumed a lot of my time.
Of the four, I’ve met all but Steve Jobs in person. Al Eisenstat was the first, on a trip to Cupertino with my parents, where I was supposed to meet Steve Jobs, but Al greeted me and spent a meaningful 30 minutes with me instead. Woz was next and we ended up investing (via Mobius) in one of Woz’s companies (called … Woz – it was ahead of its time).
I’ve long admired Guy and we have lots of second-degree-of-separation friends. One of them, Buzz Bruggerman, came up to me after a Give First: The Power of Mentorship talk in Seattle this summer and asked if I knew Guy and had ever been on his podcast. I said, “Nope, but I just listened to the one with Ben Gilbert that Guy did.”
In typical Buzz fashion, I had an email connecting me to Guy within a few minutes, and we quickly set up a time to do a podcast. I did it sitting outside at Rancho Valencia on a sunny day, was in a great mood, and at the very end of the podcast grind for the book promotion.
The podcast is now up at Building What Lasts: Brad Feld on Trust, Mentorship, and Long-Term Thinking.
It was special. It starts off fast. We learn about Guy’s early dating history with Al Eistenstat’s daughter. We talk about Heidi Roizen and Atherton. And then Guy is the very first person to make the link between the 18 items in the Techstars Mentor Manifesto, Chai, the important number 18, and entrepreneurial Tzedakah. All within the first ten minutes.
Enjoy!
And Guy – that was a delight.
The Toll of Stress on Startup Teams and Its Link to Founder Well-being
Startup Snapshot, a think tank uncovering the unspoken realities of the entrepreneurial ecosystem, has released its latest report, The Untold Toll (Part 2): Navigating Stress, Wellbeing, and Burnout in Startup Teams.
The emotional and mental state of startup teams has emerged as one of the most overlooked drivers of company performance. Startup Snapshot illuminates the unseen side of startup life through global data collected from startup employees. It’s the first study of its kind, and the findings are candid, revealing, and deeply human.
The startup grind is taking a heavier toll than expected. Only 10% of employees anticipated that startup life would harm their mental health, yet 80% say it has. Burnout affects 50% of employees, and 52% report anxiety, surpassing even the rates reported by founders themselves.
Founder stress quietly cascades through the organization. While only 10% of founders openly share their emotional challenges with their team, 57% of employees say they regularly notice signs of founder stress through tone, energy, and facial expressions.
This unspoken tension shapes culture and affects how safe and stable employees feel. Teams led by highly stressed founders report 16% lower work wellbeing, 14% higher burnout, and 16% lower psychological safety.
The most significant stressor for employees isn’t workload or pay, but uncertainty about what’s happening in the startup. Yet only 18% say their founders are fully transparent about the company’s challenges.
Transparency directly affects employee performance. Employees working under transparent, communicative leaders experience 19% higher work wellbeing and 26% lower turnover intention. When people understand what’s happening and why decisions are made, they feel secure, valued, and connected to the journey.
The research makes it clear: Founders set the tone for stress and well-being across their startups. When leaders neglect their own mental health, that stress spreads to employees, driving burnout, disengagement, and long-term cultural damage. Startup Snapshot will continue to investigate the emotional and psychological landscape inside startups. If you want to be part of this dialogue, reach out to yael@startupsnapshot.com.