2026-02-14 23:07:28
President’s Weekend link blog.
VCs Break Taboo by Backing Both Anthropic, OpenAI in AI Battle [Rebecca Torrence and Natasha Mascarenhas/Bloomberg] – VC conflicts. More and more like hedge funds holding stocks in competitors. Less like OG VC.
For the longest time it was “no conflicts.”
Then became “well, this is our core fund and that other investment is in our growth fund.”
Then it evolved to, “it’s ok because two different GPs [within the fund] are making the investment”
Now it’s just straight up YOLO.
AI, Democracy, and the Responsibility of Leadership [Bijan Sabet] – Bijan is a former VC [Spark cofounder] who then served as our Ambassador to the Czech Republic during the Biden administration. He continues to do good work on educational boards, Human Rights Watch, and others. I always appreciate his writing, and here he calls on our industry to be mindful.
“Technology is not destiny. It is a tool. Its impact depends on who builds it, who benefits from it, and the values that guide its use.” Followed by five principles in AI development.
the dream is materializing [Jackie Luo/the dream machine] – Jackie writes about her own experiences with AI and LLMs, moving from her professional realizations to training her own model based. I don’t want to excerpt it because it’s beautiful and interesting as a whole piece. Read it.
No Coding Before 10am [Michael Bloch/In The Trenches] – Entrepreneur turned investor, Michael here covers how he’s seen one portfolio company transform its engineering practices around AI-aided development.
“Their playbook is not “use AI to code faster.” It’s a full inversion. Agents, not engineers, now do the work. Engineers make sure the agents can do the work well.”
The post’s title comes from this rule: No coding before 10am. Hands off keyboards. First hour or two every morning is for talking, aligning, and drafting prompts together. Once the team is aligned on what to build and how to set agents up, then you can code and let agents start working.
Craigslist Founder Signs Giving Pledge and Narrows Focus [Ben Gose/Chronicle of Philanthropy] – Craig Newmark is a wonderful mensch when it comes to philanthropy. Seems like a good dude who just wants a better world. Here he reconciles some of the limits of how philanthropy can/can’t help journalism.
“Craig Newmark made his fortune by starting Craigslist, the online classified site where people can buy or sell just about anything. But when it comes to his philanthropy, Newmark is taking a more focused approach. After some hard-earned lessons from gifts that didn’t pan out, Newmark is concentrating on his top two priorities – cybersecurity and helping military families and veterans.”
Enjoy your weekends!
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2026-02-10 23:33:36
I think Peter Kafka originally intro’ed me to Jason Del Rey, bunch of NY/NJ guys hanging out. I’m thankful for that connection because Jason and I have spent a lot of time in the years since talking about tech, family, and basketball. So felt appropriate in the months since he went Indie with The Aisle, covering the intersection of AI, tech and Future of Commerce, to turn the questions back on him. Here are Five Questions with Jason:
Hunter Walk: Of course I’m a Day One subscriber to “The Aisle,” your new media publication focused on the emerging intersection of AI + Commerce. I’m assuming your decision here was largely ‘running to something’ (wanting to take the swing at building your own thing, focused on the people and stories you think are most interesting and building an audience) but one can’t also ignore the fact that ‘traditional business media’ has been forced into a scarcity, rather than abundance, reality. So I guess what I’m asking is how much of taking this step now was “What does Jason want to do in 2026” vs creating a different model for the next decade where you control your own destiny?
Jason Del Rey: First, much love for your early support. I embrace the challenge and reality that I’m going to have to earn the trust and following of the vast majority of The Aisle subscribers, but I’m grateful that hundreds of folks subscribed on Day 1 based on what I’ve already proven in my career.
I’d say the answer to your question is….Yes? But seriously, there are personal, professional, and industry reasons for me making the leap.
On one hand, I’ve wanted to shoot my own shot for several years now, and this felt like the right time because of my expertise covering e-commerce and the fact that I believe we’re on the cusp of the biggest disruption in this space since at least the launch of Amazon Prime 20 years ago. I know employees and execs working in retail, e-commerce, and even those building new commerce features at AI startups and labs, are searching for signals amid all the AI noise, and I’m intent on building The Aisle into one of those signals .
As you know, I also lost my parents at relatively young ages, and had a close friend (and one of my biggest supporters) die suddenly in his mid-40s this summer. I’m in my 40s now too and thought if not now, when?
But yes, to state the obvious, this is the least “safe” the “mainstream” media industry has felt in my career so of course that played some role in the timing too. But not as much as the others.
HW: From the folks who’ve gone Indie before you, who do you particularly admire and what is The Aisle borrowing/evolving from them?
JDR: Man, this is a long list and I’m hoping to borrow a little inspiration from all of them. And I’m sadly sure I’ll leave some folks out.
I think because of my coverage area, I of course admire this generation’s indie tech reporting OGs: Casey Newton, Alex Kantrowitz, and Eric Newcomer. Among many other things, I admire Casey for his prolificness, Alex for his hustle, and Eric for taking an early, big swing at building a standout events business.
Beyond them, I’m loving what I’m seeing in the early days from the other two Alexes, Konrad and Heath, and admire their multi-media approach mixing newsletter, pods, and live events. I’ll follow their lead in this regard over time, but wanted to feel like I had the core product, the newsletter, in a great place first.
I’m also a Feed Me reader, and appreciate the consistency of Emily Sundberg’s voice, and how many industries her scoops span. Her Guest Lectures are brilliant too.
Oliver Darcy has also been an absolute killer building out Status, which is unflinching in a way I hope to emulate.
And in the sports world, a former lawyer-turned-special needs teacher-turned-indie sports content creator named Jonathan Macri has worked harder than anyone I follow to build a niche multi-platform media giant in Knicks Film School.
Beyond journalism/writing, I’ve loved following the trajectory of the basketball trainer Chris Brickley, who worked his way up from being a little-known Knicks assistant trainer into the go-to trainer for the biggest basketball stars from across the world–and a business in and of himself.
HW: I interviewed you in 2017 and asked about the potential conflict in covering founders and executives critically but still needing them to show up at paid conferences. Your response included “Most smart people in the industry realize and respect that, and will sit down with me onstage whether they view my coverage as “positive” or “negative,” so long as they believe it’s well-researched and fair.” Soooooo, do you think this is true given the vibe shift over the last eight years and more reporting being labeled a ‘hit piece’ or overly negative/cynical by powerful people?
JDR: It’s definitely harder now than it was then but I still believe there are enough level-headed folks who want deep, fair reporting whether it aligns with their world view or challenges it. You’d also maybe be surprised how many X thinkbois hate on the media publicly but don’t behave the same in private, and love being asked to speak on a podcast or a stage.
HW: In that same interview, we also discussed potential tension between covering ‘newsie’ things, even if it’s less unique or important, vs longer researched pieces. Maybe let’s call it snacks or meals – seems like we’re largely in a snacking economy now? At the time you said “The never-ending battle I have with myself is how to best balance the newsier items with the big, step-back impact pieces. It’s not a science and, when in doubt, I ask one of my editors.” Would you still characterize this as a ‘never-ending battle?’ And without an editor, how do you anticipate keeping the balance for The Aisle.
JDR: First, I should be clear that I’ve had some help behind the scenes on the editing front. But, yes, I’d say this is now an everyday battle for me as I’m just ramping up The Aisle, and still sorting out my cadence for short news-related analysis in addition to my guaranteed weekly pieces. That said, I think when you have a direct connection to a subscriber or member like I and many other independents do with a newsletter, you have earned some level of trust to deliver what you think is best. Thus far, most of my newsletters have run around 1200-1800 words and the open rates (60%+) and feedback tell me readers can handle more than a snack when called for.
HW: Looking back over the last few years, what’s a person, company or trend that you were sure was going to be really important and ended up being less impactful? On the other hands, what’s something that you largely ignored but then became too big to not cover (or maybe you just got religion late)?
JDR: I’m going to go back to 2015 when I wrote this in-depth profile of a shopping app called Wish. To those not familiar, it was kinda like Temu before Temu, but minus some of the supply chain advantages that Temu innately has from essentially, if not technically, being based in China. Wish was successful in many ways–it IPO’d and I think had a market cap of $15 billion or $20 billion at one point. But it ended up basically collapsing and selling its assets for less than $200 million a few years later.
I was skeptical of it in some ways—the product quality was so bad in some areas that I imagined customer churn would end up being a big issue––but I still thought it would have sustained success over a longer period of time.
On the flip side, I didn’t pay as much attention in 2023 to ChatGPT as I maybe should have. I was focused on my book launch for the first half of that year and really didn’t dive in until I started working at Fortune in early 2024. But I hope I’ve made up for that mistake x10 with my usage and reporting since then.
Thanks Jason – you bring authenticity and heart to this beat, along with great writing. Everyone should go try out The Aisle!
Tip: I’m using Junova to track purchased airline tickets I’ve taking and auto-reclaim credit if the price drops. It was started by a friend and so far has recouped $1500+ of American and United credits for me. Their business model is: service is no cost, but if they successfully get you credit, they charge 20% of the value to your credit card. If you use this referral link, your first $25 of fees (ie $125 of flight credit) is free. Let me know how it works for you!
2026-01-27 11:15:36
I see more of you speaking out today, and it’s not about which way you vote. It’s actually also not about border safety, or antitrust policy, or whether over the last decade your party moved away from you or towards you. It’s about our rights and drawing boundaries and what America you want to give to your children.
Peter Kafka [reporter, friend, New Yorker, dad, human being] writes his own call to action today. It’s behind a paywall but he said he doesn’t mind me quoting from it, given the circumstances.
“To be clear, I’m not asking you to launch an ad campaign, or order up some performative Instagram posts, or any other kind of corporate theatre.
Just say the thing you believe is right: It’s wrong for masked federal agents to kill protesters in the streets, and that you condemn it.
…
That’s because your silence tells everyone who is appalled by Pretti’s death that they shouldn’t speak up, either. That gives the federal government the tacit permission to carry on.
So say you’re against that. Now. Before it stops shocking you.”
Thank you Peter, and thank you all of the people I see using their voices too,
2026-01-23 04:27:48
Our wives are friends. That’s the true answer how GitHub cofounder Tom Preston-Werner and I reconnected over dinner a few months back. But when he shared news of evolving his angel investing into a firm called PWV, I knew we’d have a lot more to chat about. And I’d have at least Five Questions for him….
Hunter Walk: We’re both Gen X, which Google’s AI snippet notes was the ‘first generation to grow up with personal computers and MTV.” I know the former played a role in your life obviously, but what about the latter? Did you watch much MTV growing up? Generally a music fan?
Tom Preston-Werner: I was never as much of a music fan as many of my friends growing up, though I did listen to a certain MC Hammer cassette tape so many times that I wore it out. I guess I enjoyed music, but was never particularly introspective about it. I liked Paula Abdul and Vanilla Ice when they came on the radio, and got roped into buying tons of CDs through BMG’s shady “8 CDs for a penny” promotions. Stuff like Kansas, Stone Temple Pilots, and the Jurassic Park soundtrack. Maybe I was more into music than I remember! But it was never part of my identity. At least until I discovered Pink Floyd in high school.
I did watch a bit of MTV, but I liked the TV shows and commercials better than the music videos. I savored every moment of every Æon Flux episode I managed to stumble upon. That show is deeply seated in my core memory and probably explains some random pathology embedded in my limbic system. I couldn’t believe the weird self-promotional shorts and interstitials they aired. They did stuff on MTV that no other channel would touch, and I loved that. It expanded my perception of what you could do (or were allowed to do) with the medium of television. That same spirit of breaking the rules and expanding what’s possible is exactly what draws me to founders today.
HW: You recently blogged about evolving your angel investing strategy into a proper venture fund (PWV). Your ‘true north’ is to be “the venture firm we wish we’d had early in our startup journeys.” What was your relationship with VC firms like during the GitHub growth?
TPW: For the first four years of GitHub, I actually had a bit of an antagonistic approach to the VC world. We were fully bootstrapped during those years and ran the company entirely off income from GitHub customers. As such, we never approached VCs and didn’t spend much time thinking about them. We took it as a point of pride that we didn’t need to play the VC game to succeed. We made our own rules and were the masters of our own destiny, thank you very much!
The first VC that I recall ever reaching out to us was Mike Maples, Jr. He had put together some crazy algorithm (remember, this is 2008-ish) where he had an associate collecting data about the startup ecosystem and ingested it into his proprietary system and out would pop promising founders. That’s how he said he found us and we chatted with him a bit, but had no interest in taking VC money. I still think it’s cool he put that together way back then.
Even as a VC now, I think if you can bootstrap your company, go for it! When you have to rely on your customers to fund your company, you get very good at focusing on what matters, delivering value to people. This probably requires finding product market fit very early, but if you can do it, it’s a powerful way to control your destiny. At GitHub, we eventually did raise money, but we were able to do it on our own terms (literally). We wanted to go faster and our thin buffer in the bank was limiting our ability to hire rapidly to meet the opportunity in the enterprise. Partnering with Andreessen Horowitz for our $100M series A allowed us to grow faster and access advice around becoming more sophisticated when it came to finance and sales.
A simpler version of my ‘true north’ is that I want to help founders succeed. Not just because I want to plug a big number into a financial spreadsheet down the road, but because I really BELIEVE in founders and meeting them where they are. I want to dig into the technical details and ideate on the product. I want to help them make the thousand small decisions that prepare them for smooth sailing later on. I want to discuss branding and hiring and how to build an exciting, sustainable culture. I want to feel less like a VC and more like a mentor and champion.
HW: Raising a fund is one task – often easier than actually running and deploying it! Has anything changed about why/how you invest when it switches over from your own angel dollars to a proper fund structure (which includes outside capital)?
TPW: Angel investing is great, and I love doing it. But it means almost always being a small player on a big cap table. When David, DT, and I joined forces in 2022 to start the Preston-Werner Ventures Rolling Fund (a quarterly venture vehicle administered on AngelList) we brought in some outside LPs and drastically enhanced our evaluation and diligence process. We started writing a few bigger checks, and in doing so, found that many of our portfolio companies reached out to us when they were ready to raise their next round, asking if we could lead. But with a small fund, we had to say no. And that felt like a big lost opportunity to be more involved and help these founders even more.
By raising PWV Fund I, we’re putting together a vehicle that extends our experience in funding a broad range of startups, and adds on the ability to double down on our most promising companies. We’ll more often be able to lead rounds and set terms. It’s really about leverage and opportunity. In addition, we’re selecting LPs that want to join our community and help out. When we can leverage the networks of a broader group of investors, we can really move the needle.
Some things won’t change. For me this is much more than a financial game. I want to fund founders that want to create a better future for PEOPLE. Which means we spend a lot of time thinking about the ethical ramifications of each investment and how the technologies they enable will impact people’s lives in a few years, should they succeed. In speaking with LPs, we look for like-minded people that also want more than just a financial win. As a capital allocator, what we really are is a TIME allocator. And there is nothing more sacred to me than ensuring that the people I influence are working on meaningful, human-centered, value-creating technologies.
HW: SF is in a doomloop. SF is back. Rinse and repeat for those of us who have been here a while. Certainly a special place, but also a city with challenges. If a founder asks you whether they should base their company here versus somewhere else, what’s your advice to them? When you invest do you care about company location?
TPW: The Bay Area is awesome for startups. Everything here is optimized for founders working on big ideas. VC money is headquartered here. Legal folks know how to manage cap tables and stock grants. Banks understand that startups are different from brick and mortar establishments. If you’re building a startup in SF, you won’t be alone. There’s an AI event practically every night. Stop by a random cafe for a flat white and you’ll hear a founder pitching their idea to an investor or candidate. If you can find a way to live in the Bay Area, it will absolutely accelerate your timeline and create opportunities you won’t have elsewhere.
That said, there are downsides. You will spend a lot of money to be here. SF salaries are often four times what you might pay for similar talent in Germany or the UK. That means your runway is accordingly shorter. So you have to raise more money, which means more dilution. Maybe the upsides make all of this a moot point, but maybe they don’t and that extra year of runway could allow you to find success. One thing is clear, though. If you are building in SF, you better burn twice as bright, because you might just be burning half as long.
At PWV, we’re happy to invest in companies outside the Bay Area, because there is talent everywhere, and good ideas don’t care about geographic boundaries. But if you do start your venture somewhere else, you need to deliberately make up for the downsides. It means you need to make relationships with VCs and others in SF so we can help you get hooked into the right services. If you’re outside the USA, it’s especially important to have partners (VC or otherwise) in the USA to help you incorporate in a way that makes future funding rounds easy for US investors and smooth for US customers to pay you. We do all these things, and it allows us to help founders wherever they may be on the planet.
HW: Who is a person in tech – dead or alive – that you think deserves more recognition than they receive for their impact upon our industry?
TPW: My answer is not a single person, it’s a KIND of person. It’s every person that has ever contributed to an open source project because they believe that when we work together and share our best accomplishments, we raise the bar for what we can do as an industry.
Untold thousands of developers have spent time writing and giving away code, fixing bugs in critical open source infrastructure, and fielding support requests from users, all without being paid or recognized as the heroes they are.
You will know the names of very few of these people, yet their code makes our modern world of technology possible. Nearly every device you use, from your car to your phone to your watch, and certainly any software product you build and deploy will run and rely on open source libraries. A single line of code written by an open source contributor could run trillions of times a year on various computers around the world, all without that developer ever earning a dollar for it.
And that’s ok. It speaks to the belief so many of us have in the idea of giving back. Giving back to the community that helped us achieve what we have by standing on the shoulders of open source giants. But it also means we should think about and be thankful to open source authors. It means that when we submit an issue on an open source project, we should start with a big “thank you” and end with the best damn issue report the maintainers have ever seen. We owe them that. In fact, we owe them the very success of our industry.
Thanks TPW! Hope we’ll have lots of founders to back together! – HW
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2026-01-19 22:39:37
Digging in the crates at home I found this from Karen Kavett (who is now doing puzzle videos but at the time was more DIY stuff). It’s a fantastic snapshot of an era, I’m guessing 2010/11/12? I wonder what it would look like today now that everyone realizes that YouTube is for, well, anything and everything!
Junova tracks your flights and requests credit for you when prices decrease. Friend started this as a ‘lifestyle business’ – i’m giving it a whirl. It’s free – just take a percentage of the refund. Sign up and get $25 credit to start.
2026-01-18 08:47:01
I like words. Here are thousands of them.
The Boss Who Gave His Employees a $240 Million Gift [Gregory Zuckerman/Wall Street Journal] – Family owned business in Louisiana sells for $1.7 billion and the owners negotiated that 15% would go to 540 full time employees. Employee ownership is such a given in our industry but doesn’t extend to most jobs. Tech comps also tend to distort our perspective of outcomes since power laws can result in millions and millions, but for most people a six digit bonus is meaningful and life changing.
Sequencing vs. Equal Odds [Michael Dempsey/Compound] – I usually only understand 75% of what Michael writes, but this one resonated soundly enough to share! He outlines a theory around two types of companies/R&D: those which require sequencing through the idea maze and those which are better suited towards parallel experiments because you don’t know which is going to work best. There are successful outcomes available to either, but require very different skillsets and strategies. To be between the two is death.
Pre, Mid, Post-Training Way of Life [Tina He/Fakepixels] – Another banger from one of my favorite writers/chroniclers of the community right now. Here she applies (extends?) LLM metaphors into life and everyday language. Three different mindsets out and about in the world; the trio in the title. “Token by token, brick by brick, we train ourselves either toward a larger freedom or toward a more elegant cage. And the difference is rarely intellect. It is what we are willing to protect as sacred.”
Soft Serve Superpower [Dave Margulius/Electrified] – Dave’s an ex-operator (cofounder of Quizlet), who now works on climate issues. Soft Serve Superpower reminds me of Noah Smith’s Electric Tech Stack thesis, but tells the story via a surprising vessel: the American ice cream truck. And connects it to the front lines of Ukraine’s war with Russia.
What We’ve Learned About AI Readiness in Real Estate Today [Brad Hargreaves, Jonathan Gheller/Thesis Driven] – Sorry it’s behind a paywall but I wanted to at least put it down here because its main point is something I agree with pretty strongly for almost every business vertical today: namely that AI rollouts in industry are increasingly gated by security, governance and observability/reliability, not skepticism of the technology’s ability to create value. It’s why I’m bullish on AI but believe we’re going to be looking at 3-5 years of ‘rollout’ in many industries, with early adopters or AI-native players getting a headstart.
Enjoy!
Junova tracks your flights and requests credit for you when prices decrease. Friend started this as a ‘lifestyle business’ – i’m giving it a whirl. It’s free – just take a percentage of the refund. Sign up and get $25 credit to start.