2025-12-27 08:55:17
Boxing Day Link Blog!
The Rumor Mill and the Propaganda Machine [Renée DiResta/Agents of Influence] – I never pass up an IRL opportunity with Renee, and we grabbed coffee this past summer after finding ourselves in the same city during family travel. Goodness she is smart and strong I thought leaving the conversation. In this post Renee puts context around the X mob that named and harassed a Brown college student they suspected of being the mass murderer, in which he was not at all implicated.
I’m not on social media much and heard about this incident only because horrifically some powerful folks in the tech community participated (most later deleting their posts). My first reaction was that this was closer to yelling fire in a crowded theater than freedom of speech. Renée discusses how reality has splintered and why consequences have decreased as well. She also touches an interesting third rail:
It’s my controversial opinion that defamation lawsuits should be far, far easier for private individuals who get screwed like this. I just don’t think the law has caught up to the infrastructure. Yes, defamation lawsuits are imperfect, slow, and expensive, and can be frivolously abused. But influencers who falsely accuse a private person of mass murder for clout and profit should face consequences. The legal system is one of the few mechanisms available to impose costs and deter this kind of behavior. The harm is real. Treating human beings as content is depraved. Defamation has always been outside the bounds of free speech, and our marketplace of ideas would benefit from less of it.
Year 5/6 Startup Learnings [Celine Halioua/CEO of Loyal] – Always love builders who periodically take a step back to share. In this case, Celine’s annual Learnings posts. The fifth of these posts includes several notes to chew on. My favorite is “You don’t know someone until they make a mistake.”
Self-driving cars are an unambiguous social good [Mathew Ingram/The Torment Nexus] – 2025 seemed like a big tipping point for Waymo going mainstream and the narrative of an autonomous future shifting another standard deviation in the positive direction. Heck yeah! Mathew writes a great roundup of the benefits here. Of course I agree! I was at Google during their earliest years of work in this space, enthusiastically reading whatever I could about the team’s findings! Then we invested in Cruise’s seed round and got to see another approach starting to work. In 2017 I worried that our measure of ‘safety’ for autonomy would be illogical and emotional. In 2023 I talked about how these might be the most inspirational use of technology in physical spaces that we’ve seen in years. And in 2024, I urged regulators to let more people die to move this space forward.
Dashboards or Pipes? [Gokul Rajaram/via LinkedIn] – Gokul was our colleague at Google back in the day, and in this specific context, our co-investor in Graphite, which was acquired by Cursor earlier this month. The outcome made Gokul recall, and resurface, some advice he’d given the Graphite cofounders about his theory on Dashboards or Pipes. Short post for you to read but the tldr is Dashboard products are used directly and regularly by end users as their primary interface for accomplishing tasks while Pipes products are used in the background, and you need to figure out strategically what you are.
Episode #60: 2025 in Review [The Learning Corner podcast/Precursor Ventures] – For me podcasts are usually escapism – NBA, history, some pop culture, maybe some 1980s pro wrestling. I very rarely listen to tech or tech-adjacent discussion but this pod has always been one that makes it into my queue. They take ~three articles that their firm discussed internally that week and share their thoughts. It also helps that I often agree emphatically with Charles Hudson (we’ve known one another for a very long time) and find that co-host Mia Farnham adds much to the mix. The one I’m sharing here had their first guests – Me! and Peter Walker from Carta.
AND OMG, adding this link I see that I spoke for 43% of the pod. Sorry, not sorry!
Enjoy!
I always love sharing something that delights me. My favorite purchase of 2025 might just be these microwavable bowls that are excellent for instant oatmeal.
2025-12-22 04:48:10
Org charts are more like funhouse mirrors than many people realize, providing a view of the truth but with multiple distortions. If you assume that all leadership is hierarchical, or everyone with the same title has the same influence, or that the number of people you manage is directly correlated with your importance, well, the way it works in Boardrooms, corporate offices, and hallways after hours can be dramatically different. During my days at Google there were multiple examples of “Eric, Larry and Sergey” whisperers who could help bless or kill a project without having a SVP title. There were senior engineers scattered about without any teams but who could look at your proposal and tell you whether the architecture would work or not. And there were culture carriers who served as weathervanes for morale, as well as being weather makers themselves.
These lessons never left me – I experienced them positively and sometimes less productively as a product exec there. Working with startups today via our venture firm Homebrew, they inform the guidance provided to the founders as they build and scale their own companies. And equally I try to remind people within those teams, especially the ones that are so impatient to get to a certain title or headcount responsibility that they can be their own worst enemies making career decisions, that Span of Influence is Not Limited to Span of Control. Don’t run to a worse startup just because you can get a VP role there, or OTOH stay somewhere uninteresting out of concern you’ll have to ‘take a step backwards’ [title/managerial-wise] applying for other positions. Again referencing my Google years, there were a ton of early business and operations team members who despite their seniority, came on in IC or lower-titled management roles after understanding the opportunity. You know what happened? They succeeded wildly and got promoted quickly as we scaled, ultimately with a much more satisfying career arc, and definitely more lucrative, than if they had said, nah, that’s beneath me.
As an aside, Mayor Lurie here in San Francisco has been an excellent positive version of this during his first year on the job compared to what I was experiencing on the ground prior. The Mayor’s office does have structural challenges given the Board of Supervisors governance responsibilities and all the various Commissions. GrowSF has written why this is a negative for our city, especially in light of the work to be done in public safety, housing development, and rezoning. Despite that reality, Lurie seems to be an energetic and present problem-solver, giving off vibes of accountability and effort, even if the solutions aren’t fully under his office’s authority. We’ll see if this hopefully can be precursor to collective action and sustainable progress.
2025-12-20 02:54:22
Some of you should skip this post. It falls into the ‘VC reminiscing about time with a startup after a successful outcome was announced,’ specifically software quality startup Graphite being acquired by code generation startup Cursor. Don’t get me wrong – it’s definitely better written and less aggrandizing than the most traditional versions (you’re not going to hear how ‘we’ built this company together), but still, it’s in this category of essays. I just don’t want anyone to be surprised – like when there’s a cute guinea pig on IG and you forget for a minute that they’re really just rats with a blowout.
With that warning done, yes, we led the seed round for Graphite in early 2020. I met Tomas first via a mutual, and then all five of us (me, Satya and the three Graphite cofounders) all did some quick conversations in various combinations. Satya’s feedback to me was memorable – something along the lines of ‘please get them a termsheet before other people realize how smart they are.’ And we did. It was a wonderful almost six years together and I know the relationships are going to outlast the transaction. I learned a ton from them about building in the developer ecosystem and from my fellow Board members, Peter Levine at a16z and Christine Esserman at Accel. While there were lots of microlessons, three particular memories are most personally indelible and I’d say if any one of these hadn’t happened the company would not have become what it did.
Took the Punches and Iterated to Durable PMF
Graphite started out as Screenplay. And while ‘code quality’ was always a true north mission statement for them – the reason the company was founded – it took some reps to find the best product manifestation of this goal. These weren’t pivots, but they did require first principles thinking, some intuition, and the confidence to leave something good behind in the search for great. In particular, before what we know today as Graphite was launched they had a mobile QA and release management tool deployed with customers. Given the frothy funding market at the time and the quality of this team they absolutely could have ‘forced’ this version of the company to a Series A. That is, an adequate set of performance curves, a bigger story, and pedigreed cofounders would be enough for a next funding round, and then with that capital they could hopefully figure it out from there. But Greg, Merrill and Tomas knew this wasn’t the way the best version of Graphite was going to be constructed. So they shut down that effort and repurposed some of the code – and a lot of the scars – into a new direction.
As mentioned earlier, going into the seed funding we had ZERO questions about the cofounders intelligence, ceiling, or relationship with one another. We did spend time – with them directly and via backchannels – to see if they could take a punch. If their first idea didn’t work would they be so shell-shocked as to run back to a BigCompany with their tails between their legs? Would the threat of failure be motivating or send them into denial? Would they have enough of a framework or guts to look at something as say ‘this can be ok, but we can do better?’ They did.
We still stress that seed is not a funding round, but a phase. And that most importantly it’s a time for experimentation and learning, not just brute-forcing an up and to the right curve. Or even worse, mindlessly doing what you put in a pitch deck just because that’s what you thought a year ago. The combination of bigger rounds and new/nervous VCs often asks founders to speedrun this process, but the best companies operate at the intersection of urgency and patience. Graphite threaded this needle.
Started During COVID and Back to IRL Quickly
Our conversations with Graphite started right before COVID 2020 lockdowns. It was a very weird time. I had at least met Tomas IRL but otherwise things became Zoom relationships quite quickly. As three close friends the cofounders were able to spend time together in NYC and began to assemble a small team virtually but not remotely, but still there was eagerness to get back to IRL ASAP. And they did as soon as it was advisable.
During this period I got to meet – mostly over Zoom, or in person outdoors – about the first ~20 hires they made. Often as part of the ‘close’ process once an offer had been made but sometimes earlier. It felt really wonderful to be included in this manner – the Graphite team appreciated the help (it was at their request) but more importantly it let me get a feel for the company as it started to grow. So many other startups at that time were sort of black boxes. Who knew where people were with their fake zoom backgrounds? Were people really committed to the cause or just working a few hours a day while trading NFTs and ICOs? This wasn’t the case with Graphite. Getting back IRL was about knitting a culture early and building the trust to do the aforementioned iteration. Put together everyone’s ideas and opinions together.
Were there some candidates who decided to not interview at Graphite because they preferred a remote lifestyle? Sure. But there were equal numbers who actually were leaving their jobs because their current employer was staying URL first. Remember, this was a young tech-focused startup in NYC – working from home with your two roommates and a small apartment is not glamorous. Having the social and physical separation to walk, bike or take the subway a few stops to an office was actually a feature, not a bug, for many. Graphite stayed true to who they wanted to be and ripped off the ‘what should we do’ bandaid early. It paid off – I don’t believe they would have been nearly as successful if they had stayed remote.
Three Founders Went the Distance Together
Point blank: By Year Six it’s unusual to see three technical cofounders all remain vital to the company. In my experience one of two situations tend to occur – they realize the CEO isn’t scaling and try to make that change or the two non-CEO cofounders overlap too much in engineering/don’t scale as leaders. There are versions of this which are polite and productive and versions of this which are toxic and disruptive. But it happens a lot. Obviously it didn’t here. But why?
Merrill wanted to be a great CEO not just a great cofounder. From early on he had the self-awareness that this would take work. And that the role would sometimes put him in disagreement with his cofounders on strategic decisions. He simultaneously embraced the responsibility while also prioritizing the effort to ensure the three of them were always communicating well, trusting each other, and putting Graphite ahead of any one of their feelings or ego.
Greg and Tomas were two sides of the same coin. They both cared deeply about Graphite being a place where engineers could make a difference. To oversimplify, Greg thought about this from a collective and structural perspective (what does the Engineering Org look like, what’s appropriate documentation and processes for our scale and culture, when do we need Engineering Management) and Tomas biased towards the individual (how could any one engineering hire make a difference, how could he look a potential team member in the eyes and sincerely say Graphite would be somewhere that they could have a great idea, build it, and ship it without five levels of approvals and a chilling effect of low risk tolerance), This is of course an abstraction – but they scaled beautifully. Tomas could work on experiments, Growth projects, lead Product within the technical and cross-functional org, while Greg had a natural role as CTO.
Of course I lived on the cap table, not the org chart, so my observations here are incomplete and reflect an outsider’s perspective, but I have such tremendous respect and admiration, not just for what they built, but how they built it. And that’s what we strive for at Homebrew. The intersection of joyful work with great teams and financial outcomes which make the work possible ongoing.
Onward!!!
2025-12-16 08:27:33
So much to read but only 408 hours left in the year… gulp
Elon Musk Has His Vision. Waymo Chief Tekedra Mawakana Says She’s Got a Better One [Noah Shachtman/Vanity Fair] – Waymo is magical. Reading this profile made me realize how little we hear from their executives versus how much we hear from that other guy. They’ve done over 14 million trips in 2025 alone and are a great example of technology changing the everyday physical world. We’re lucky here in SF – may your city get Waymo next!
Want This Hearing Aid? Well Who Do You Know? [Steven Levy/Wired] – Limited in release and $6,800 to start for an AI-enabled hearing aid. But (a) it’s apparently awesome and (b) this is how you move down the cost curve over time and (c) hearing aids in general are expensive [and not always covered by insurance unfortunately]. The company is named Fortell if you want to learn more.
MCPs: Value Creation, Capture, and Destruction—Lessons from the API Era [Leonis/The Thesis] – Pretty interesting take on where value will accrue once MCPs are mature in the AI stack, using lessons from the proliferations of APIs earlier.
“That era taught us something fundamental: once the connection layer is standardized, value doesn’t live there. It moves upstream to infrastructure providers who power the system, and downstream to vertical specialists who solve hard, domain-specific problems. The middle layer that acts as the glue gets squeezed. The same will happen with MCPs. Standardization creates new opportunities, but it also kills entire categories of shallow integration businesses. Some will mistake protocol adoption for defensibility. They’ll be wrong.”
Everyone is Gambling and No One is Happy [Kyla Scanlon/Kyla’s Newsletter] – Kyla riffs off of a study that pins twentysomething’s dissatisfaction to economic insecurity (one of many that arrive at the same conclusion). Alongside this – or maybe because of this – trust between groups is eroding, AI anxiety is increasing, and degen/YOLO/gambling activities are surging (especially among young men).
Reflections from Our 2025 AGM – $1T Private Companies, AI Fundraising, and Outbound Sourcing [Charles Hudson/Venture Reflections] – Charles runs a venture firm called Precursor and always brings his truth to these discussions. I attended this one and he definitely pulled out the meatiest topics to share here. It’s always interesting to see where he’s continued to evolve his understanding year over year. The $1 Trillion Dollar Private Company is one such area.
One Thing I’ve Currently Using Blackbird, this new local restaurant/bar app which is some combination of loyalty program, crypto payments, etc – it’s curious and I’m trying to make sense of it all. You get free somethings for trying it too. Here you go:
Download Blackbird and earn 2,000 $FLY when you check in for the first time. That’s $20.00 toward any meal!
Use my code bb-o9edk2 https://app.blackbird.xyz/r/bb-o9edk2
2025-12-11 11:24:03
So much to read but only 504 hours left in the year… gulp
How I Screwed Up Sales Hiring [Pete Warden/MoonshineAI] – Stop me if you heard this one before – the incredible technologist CEO/founder didn’t get sales motion/hiring right first time he tried. It’s a cliche but still very much real. We’re friends of, and small investors in, Pete’s company – I read his post-mortem eagerly because he’s a gem of a human, super smart, and dogged in getting MoonshineAI to where he wants it to be (moonshine is a speechAI model that runs locally).
Poems Can Trick AI Into Helping You Make a Nuclear Weapon [Matthew Gault/Wired] – Oh this is fantastic. Writing in poetic structure can make it easier to jailbreak some LLMs into giving forbidden answers. Adversarial poetry!
Lessons for New Leaders [Molly Graham/Glue Club] – So many good bits here. “Every time I’ve stepped into a new leadership role, I’ve made the same mistake: I’ve gone too slowly.” A bunch of advice and learnings for your first 30-60 days in a new org/role.
Startup Operating Principles [Sam Gerstenzang/Sam’s Newsletter] – Sam currently runs Boulton & Watt, described as the world’s slowest startup incubator!!! He previously did a bunch of stuff at Google, Stripe and another startup he cofounded. This SOP post is a follow-up to one he wrote about Stripe’s Operating Principles.
How to Fix a Typewriter and Your Life [Kurt Streeter/New York Times] – Prepare to cry. This is beautiful. When serendipity and intentionality collide, what do you do? Here our protagonist makes a decision which changes two lives. Please just read it.
Ciao for now!
I’m grooving on Blackbird, this new local restaurant/bar app which is some combination of loyalty program, crypto payments, etc – it’s curious and I’m trying to make sense of it all. You get free somethings for trying it too. Here you go:
Download Blackbird and earn 2,000 $FLY when you check in for the first time. That’s $20.00 toward any meal!
Use my code bb-o9edk2 https:/
2025-12-09 03:45:01
Prioritize ownership over valuation on any given deal, but price drives your portfolio construction. This was basically how we managed Homebrew during its first decade, when we were investing out of three institutional funds, all sub $100m. The guiding principle changed in 2022 given our evergreen personal capital model (as I detailed in Why I No Longer Care About Startup Valuation When I Invest (Except for These Four Reasons)), but it served us well when we were deploying in a more typical lifecycle.
Our strategy for Funds I, II, and III were basically to lead/co-lead seed rounds with a 10-15% ownership target. Our third fund averaged 11.6% but it was really more bimodal – a bunch of 8-12% combined with a roughly equal number of 15% – across 31 startups. The concentration of dollars (expressed in ownership) was primarily about being able to also focus our time working with the portfolio and keeping our funds modestly sized where $1b outcomes could make a real difference to returns.
So our thinking was basically something like this in Fund III [2018-2021, $90m, 31 companies]:
Did we ever say ‘no’ to an investment opportunity based on pricing? Sure, but it was more often a function of the overall round size becoming too big for us to write a lead check, rather than the difference between, say, $1.5m and $1.8m to get 15% ownership.
Much like the Mike Tyson quote “everyone has a plan until they get punched in the mouth,” every firm has a model that then gets hit by reality (aka The Market). You can decide what you put in a spreadsheet cell a year ago is gospel, or you can use it as a guidebook, and behave more dynamically given what occurs over your deployment period. But if you make every investment decision without some framework to understand what it means for the fund itself, you might find the whole becomes less than the sum of its parts.
Footnote: One of the fun parts in backing new venture firms via Screendoor, is talking with them about portfolio construction and seeing the different strategies/playbooks they implement to win.