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A seed stage venture partner at Homebrew, previously managed consumer products at YouTube and worked at Google and Linden Lab.
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S**t Shoveling

2025-09-14 21:55:01

I used to think that if you never had to shovel shit, you ended up lacking empathy for those who shovel shit.

My POV has been updated: it’s worse than that.

If you’ve never had to shovel shit, not only do you lack empathy for those who do, but you also tend to *create* more shit for others to shovel.

It helps to have shoveled shit at some point in your life. And maybe it’s never too late to pick up a shovel.

AI Buying Software Instead of Salespeople; Teaching Companies To Do Less; Have the Swiss Figured Out Cheaper Housing? and +++ [link blog]

2025-09-01 06:11:35

Labor Day weekend reads

Testing AI’s GeoGuesser Genius [Scott Alexander/Astral Codex Ten] – A detailed walkthrough of how good general purpose AI [as of May 2025] is at guessing locations based off a single photo (stripped of geo metadata of course). It’s fun to try and understand how the models reason the answers here.

When Software Buys Software [Jeff Morris Jr/New Internet] – Early examples of what happens when AI models start to recommend certain software infrastructure products in response to general questions, and even more so, what happens when they make their own ‘purchase’ decisions agentically.

“Software won’t be sold over drinks. It’ll be selected, evaluated, and integrated by agents.”

One of the reasons everyone is trying to figure what SEO looks like in AI-world (coined AEO for now, done by companies like ScrunchAI, one of our recent investments).

A ‘Third Way’ Between Buying or Renting? Swiss Co-ops Say They’ve Found It [Thomas Fuller/New York Times] – I’ll just egregiously copy/paste to explain this one

In Switzerland’s member-based cooperative housing, new residents buy shares to gain admission to the building and get one vote in the corporation regardless of how many shares they own. The co-op uses the money to maintain the building, keep rents below market rate and, often, provide communal amenities like child care.

When a resident moves out, their shares are returned at face value. There is no capital gain.

Addition vs Subtraction [Molly Graham/Lessons] – Positing that organizations are inclined to always add more to their plates than subtract. And why that’s a problem. Five tools from Molly to try and get better at subtracting.

Enjoy!
Bluesky has the JUICE -> https://bsky.app/profile/hunterwalk.com

When Slack Went Down All The Time; AI is Learning to Lie in Order to Win; Your Org Chart is About Power Centers; and +++ [link blog]

2025-08-24 07:39:53

Stuff for you to read!

The reliability crisis [BuildingSlack/Johnny Rogers] – “If we can’t ship safely, we aren’t shipping at all.” That’s what Slack’s OG CTO told the company in 2018 when the product started to be plagued by reliability challenges. Company histories tend to be hagiographies or written by the most political of the team, looking to enshrine their own role in the success. BuildingSlack is a fun newsletter that sporadically fires off stories about the startup, written by former employees. This particular edition feels familiar to anyone who has ever gone through hypergrowth company phases.

A Fungible Worldview, Why Cluely Is The Dark Spirit of Venture Capital, Whether You Like It Or Not [Kyle Harrison/Investing101] – Typically I’m skeptical when an investor criticizes a startup – focus on your own house so to speak, unless there’s egregious behavior to be called out. But here Kyle uses Cluely – and his distaste for their stunt marketing – not so much to harp on them. Instead he shifts most of his focus back to the world he lives in – venture capital – and why Cluely is a chicken (or egg) example of Venture Capital 2025. And I think ultimately his post shares more about *him* than it does attempt to take down anyone else. So that I applaud. Plus I enjoy Kyle.

What Happens When AI Schemes Against US [Garrison Lovely/Bloomberg] – I live in the future. How else would I, in 2016, be able to write this post about commerce soon being agents trying to convince us to buy stuff, and eventually our own agents arguing back? Self-congratulations aside, I love the analysis here about current LLMs optimizing for a task (or ‘winning’) in a way that ends up potentially causing harm. I mean, this is basically the ‘what if AI decides the best way to ensure peace is to kill all humans’ question but not increasingly with real data. And hopefully lower stakes.

Trio of Molly Graham Essays from her Newsletter

Startup org design: Design power centers intentionally – So good. Instructions on how to think about your org chart as power centers and not just resource management. As Molly says, “One of the most powerful things you can do to accelerate your company’s growth and reduce wasted energy is to design your org carefully including where you want the power to sit.”

Layoff lessons: Four things I wish I knew – Just read it.

Part 3: Compensation for Startups: Implementing and “Defending” Your Compensation System – Where Molly makes the case that ‘simplicity’ is a key factor of comp system quality and sustainability. “When you’re designing and implementing this system, you have to realize that a lot of the day-to-day will be implemented by recruiters and managers through hiring and through conversations with employees. That means that simple is your friend. As you’re designing, you want to think about the most junior recruiter on your team and ask, “With a little training, can that recruiter maintain this system?” The more complicated you make it, the more likely that the answer is no.”

Enjoy the waning days of August…
Bluesky has the JUICE -> https://bsky.app/profile/hunterwalk.com

Why Marketing Sucks Right Now, Underground Robot Fights, Free Waffles Worth $50, and +++ [link blog]

2025-08-16 02:54:32

Summer is for reading.

Every marketing channel sucks right now [Andrew Chen/a16z] – A guy who made his career in growth marketing surmises that, yeah, it’s not just you, it’s everyone

Unfortunately this is the state of growth marketing. A lot of channels are not working, or are slow, expensive, or one-time only. This is the natural end state for things, and maybe we’re in a bit of a lull due to the technology super cycle as we’re 15+ years into the mobile wave, we’ve had various kinds of paid ads for 20+ years, and so on.

Andrew does provide advice though on how to navigate this stage but be forewarned, in his eyes a great product is necessary but not sufficient.

What was Quartz [Zach Seward/fmr Quartz CEO/owner] and Fell in a hole, got out [Tony Stubblebine/CEO Medium] – Pairing these because they’re both pretty honest looks at content businesses, the former a media company of some sort, the latter a publishing company of some sort. I append ‘of some sort’ not to degrade or minimize, but because the struggles and journeys they describe involved straying from, examining, and trying to return to, the mission and structure which made sense for the company. Quartz is largely a story told, while Medium is a story ongoing.

The most San Francisco sport ever? Underground robot boxing enters the arena [Zara Stone/The San Francisco Standard] – Please don’t turn this into a startup, a sponsored recruiting event, or #content. Against the backdrop of AI boom, our national government, and polarization generally, it’s fun to have something that’s just Keep San Francisco Weird.

Why Hampton Inn is the Hotel Brand to Beat [Patricia Clark/Businessweek] – Free breakfast is all it takes.

It costs a US Hampton franchisee less than $5 per occupied room to furnish this cornucopia, but to a family of four, the perceived value is closer to $50, or roughly one-third of the average cost of a nightly stay. That math has helped power Hampton Inn’s unlikely rise to become the world’s largest lodging brand, with almost 350,000 rooms spread across 43 countries.

Obviously that’s not the entirety of the strategy – and you should read the whole piece – but I love the 10x ROI on waffles anecdote.

Have a great August weekend!
Bluesky has the JUICE -> https://bsky.app/profile/hunterwalk.com

No Notes: Near Perfect Posts on AI Ruining the Public Web, Silicon Valley Etiquette, the Fear of a Second Success, and +++ [Link Blog]

2025-07-27 07:57:51

No Notes. Just some chef’s kiss, on-target reads

Encore Anxiety [Anu Atluru/Working Theorys] – Wonderful read on the pressure to succeed a second time. Oh please, some might concern troll, but I’ve witnessed this in tech careers. Most frequently with (a) repeat founders who fear their next company will fail and prove their initial win was a lucky fluke, and (b) younger folks who ending up joining an early stage rocketship out of school and once it succeeds beyond their expectations, worrying they’ll never find another. As Anu writes,

Impostor syndrome gets all the attention, but encore anxiety is its cruel foil: not the fear that you’re a fraud, but the fear that you’re genuine and still might not be able to prove it. The difference in attribution matters to the dominant psychology at play: the impostor fears their past success was luck; the encore-anxious person believes it was skill and yet fears they can’t summon it again at will.

Either way, there’s a focus on what others are thinking.

Ultraviolet Catastrophe: AI is about to make the public internet useless [Philip Rosedale/Philip’s Newsletter] – You might assume this post is about business model incentives pushing quality content behind paywalls or disincentivizing its creation all-together, but it’s actually about trust and malignant AI content (fraud, slop, etc). Philip believes the volume will be so significant that we’ll need to rethink the architecture of the web itself. His summary paragraph:

AI is about the flood the internet with messages and render it useless for many tasks. To scale to billions in a world filled with AI agents capable of typing 1000 times faster that us means a complete overhaul of our aging internet architecture. We will have to turn off anonymous public services, replacing addresses with channels – or in the language of graphs – replacing nodes with edges. There will be turbulence during this process, so fasten your seat belt and find some good books to read during the down-time.

Silicon Valley Etiquette [Angelo/Parallel Lines] – This was a really interesting sociological view of SV etiquette and the history of these norms. I hope we’re able to continue keeping the best aspects of our community, while reexamining how we also unintentionally (and intentionally) create barriers.

The Editorial Battles That Made The New Yorker [Jill Lepore/The New Yorker] – Skip this if you’re not a writing/creative process egghead like me. But for those who are, this is a great tour through the New Yorker’s editorial philosophy history and how it conflicted with (or helped) the writers they contracted for articles.

Inside Home Depot’s $20 Billion Secret Garden [Ben Cohen/Wall Street Journal] – Home Depot doesn’t just stock flowers and plants, it very much works hand-in-hand with growers, shaping what gets grown, what genetic attributes to optimize, and ultimately, what gets brought to market.

To find those plants, Home Depot runs 25 trial gardens in nine climate zones across the U.S. and studies them in the field under a variety of conditions. After all, a plant that thrives in New Mexico might not survive in New Jersey. For security purposes, some of those experimental gardens are hidden in cornfields or through backyard donkey corrals, protected on secret farms before the plants are selected and patented.

A Note on the State of Applicant Fraud [Matt Hoffman/M13] – Recruiting is changing dramatically because of AI – the LLMs now polish resumes, generate perfect responses, and in some cases, even create the candidates themselves. Some early data and how actually AI might also be the solution from Matt Hoffman, VC firm M13’s talent partner.

$CHYM TIME: The Three Boxes Chime’s IPO Checked for Me

2025-06-13 22:45:17

Whoa, it’s been a minute. Somehow went almost two months without a post. Bad blogger!

Yesterday Satya and I had the chance to celebrate Chime going public on NASDAQ. There are many ways to ‘grade’ an IPO from a punditry perspective (here’s my own framework which I think still holds), so I’m not going chime in with my own speculation (see what i did there), but on the other side of it, did want to recognize why this one felt special. It was our fourth IPO as a firm (defined in the loosest terms as Homebrew holding pre-IPO stock in a company), but the first which checked off all three of the boxes of consequence.

  1. Financial Outcome for the Team: Founders and VCs know how to make money over the course of a journey like this, but what makes me giddy is seeing so many people on the Chime team win too. Being part of a special startup pays off in terms of career trajectory, learnings, and network, but also seeing your equity convert can change your life. I’m sure $CHYM minted many paper millionaires, but regardless of amounts, getting some dollars into the bank account allows these folks to continue taking career risk, which is positive for the ecosystem.
  2. We Were There Since the Beginning: DPI without stories is boring. Stories without DPI is fatal. Chime provides us both DPI -and- Stories. The best combo! Special credit to my partner Satya who sat on their Board for many years, interviewed most of the early hires on behalf of the founders, and generally did more work than me 🙂
  3. Founders are Still Running the Company: To have Chris Britt become the CEO of a NASDAQ company is a credit to him, and a role model for our industry. Chris came from a working class community in the New York City suburbs and brings that mentality, that respect, and that ethic to every day on the job. I’m romantic (and old) enough to believe going public means something.

Onward. Not the end of our relationship with Chris, Ryan, and Chime. Just the beginning of a next phase.

Dec 2024 drinks with Chris and Ryan, toasting what was planned for 2025…..