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!

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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

Junova tracks your flights and requests credit for you when prices decrease. A 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.

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.

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!

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I got to know Alex Heath during an earlier incarnation – maybe his Business Insider days? But always knew his entrepreneurial streak would lead him to do his own thing at some point, and now he has! Sources.news is his tech publication, covering “what’s next for AI and the tech industry.” Worth subscribing! I wanted to know more about this transition so here’s Five Questions with Alex.

Hunter Walk: You recently started Sources, which you describe as covering “what’s next for AI and the tech industry, featuring original reporting and unique access to the companies at the forefront of the AI race.” Why is this a beat you thought best done indie as opposed to inside an existing entity? Or was the motivation something different?

Alex Heath: I went indie for two simple reasons: it’s something I’ve been wanting to do for a few years, and everyone I know who has done it is glad they did. AI is the biggest story in tech ever (and maybe the world?), and it’s an area I’ve been steadily increasing my focus on over the last few years. It’s not so much that I thought the beat was best done on my own, but it is freeing to cover these crazy times in a way that is totally authentic to my interests and style.

With the podcast, Ellis Hamburger and I want ACCESS to feel more like your favorite tech interview/talk show. We sometimes talk about ‘Smartless for tech,’ but we are only a few months in and still figuring out the vibe. We’re not dumbing down topics for a mass audience, but we always want it to feel entertaining. I see ACCESS as part of the same cinematic universe as Sources, but it’s where I get to be less of the ‘reporter’ and just hang out more.

HW: From the folks who’ve gone Indie before you, who do you particularly admire and what is Sources borrowing/evolving from them?

AH: Our mutual friend Casey Newton has been a huge inspiration and has pushed me to do this for a long time. I really admire how Emily Sunderberg is 100% herself and such a natural at taking advantage everything that makes the Substack ecosystem unique. Stylistically, I’m probably closest to Matt Beloni. If I could build something half as relevant to the tech industry as what he has built for Hollywood, I’ll consider Sources to be a success.

HW: When a source shares news with you, how do you decipher what their motivation might be, and how does your estimation of their trustworthiness factor into how you use that information?

AH: It’s pretty easy to tell this upfront. Usually, people share information they shouldn’t because they feel slighted, want to force change, or just like to gossip. Often, I find that the people on the other side of leaks discount the prevalence of that third reason. Motivation doesn’t really impact trustworthiness if I’m getting verifiable facts (internal docs, chat logs, etc.), but I always try to corroborate and assume the worst intentions from the start when engaging with a new source. There’s probably nothing that bothers me more than getting something wrong.

HW: An aspiring new grad tech reporter asks you for one piece of career advice – what would you tell them?

AH: Do your damndest to become a world top-three expert in a specific, valuable niche of tech reporting. I spent about a decade trying to be the best social media reporter in the world, and not to toot my own horn, but as far as I can tell, I have more scoops under my belt on Meta and the other key social media companies than anyone else. For awhile, I knew Facebook’s org chart better than a lot of people I talked to who worked there. That’s the kind of obessive detail you have to be willing to drill into as a baby reporter. 

Right now, if I were a new to this, I would try to become the single greatest OpenAI or Anthropic reporter in the world and manically cover the ins and outs of those two companies. If you start breaking news there and can be consistent, your career will be set.

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 hand, what’s something that you largely ignored but then became too big to not cover (or maybe you just got religion late)?

AH: While it’s more relevant now, I certainly thought augmented reality glasses would be a bigger deal than they are today. I covered AR and VR a lot over the last decade based on the investments and hopes the leading players in the space were projecting. It’s taken a lot longer to hit as a category than everyone thought, though I do think this will be an interesting year with new Meta glasses, the return of Google Glass, and Snap’s consumer Specs glasses coming out. AI is also making the form factor more compelling, which dovetails nicely with my past and current reporting focus. 

I deeply regret not paying more attention to AI as a field before the release of ChatGPT. Like everyone, I’m certainly paying attention now!

Thanks Alex! Folks should check out Sources!!!

New Year’s Links

Backchanneling is Becoming a Crutch [Cristina Cordova/Linear] – I love a good backchannel reference but it takes skill and knowing what you’re trying to accomplish in order to get the most from this activity. Here Cristina points out how you can make mistakes using this tactic – especially in exec hiring. “If you want executives who can actually move a company, you have to do the harder work yourself: understand the role, accept the tradeoffs, and talk to the person before letting someone else’s context make the call.”

How the Hell Are You Supposed to Have a Career in Tech in 2026? [Anil Dash] – I do sometimes wonder if I was 20 years younger how I’d be approaching my career right now Would AI be exciting or freak me out as an existential risk? Would the culture of tech be as attractive as it once was now that it’s powerful, not the underdog? Would I find my tribe?

Strange Math [Ashritha Karuturi/Ambrook] – Ambrook makes financial software for farmers and is a company we’ve backed since their first fundraise. The team is so smart, so intentional, so iterative in their willingness to learn and adapt. Here they write about tactics for building a culture of radical honesty.

How Kraft Heinz Lost Its Lock on Mac and Cheese—and American Shoppers [Jesse Newman/WSJ] – They’ve given up mindshare and shelf space to new competitors.

The 9s of AI Reliability [Kushal Chakrabarti/Obviously Wrong] – Opendoor’s former Chief Research Officer, and a AI/ML advisor to startups, takes on the question of ‘how reliable does AI need to be to be of value’ and notes the answer is quite different depending on the use case and situation.

Two Things to Sign Up for in January 2026

1. Founders Card: If you travel a lot for business, it’s worth it alone for the discounts on hotels, airfare, etc. Generally a perks-based membership club. I’m usually dubious of these but have done this for several years and always renew.
2. Blackbird.xyz: Local app [SF, LA, NYC, Denver] – get $20 for free on first ‘check in’ – coffee, bars, restaurants. I’m a former 4SQ/Swarm users and trying to figure out if this is interesting or not. But in the meantime, you’ll at least get some venture capital subsidy 😉

Most Silicon Valley folks expect some degree of ‘tech talk’ when returning home for the holidays. Sometimes it’s in the form of IT support. Or nephews excited about the latest degen trends. The Uncle who is very excited to share he cut the cord on cable this summer and went all in on YouTube TV. But last week there was a single topic of conversation: are we in an AI Bubble? I expected this from portions of family tree, but it came from, well, everyone. My mother-in-law wanted to know if she could visit a Data Center with her friends. Basically my holiday table was no different than a San Francisco Blue Bottle.

Despite the Bubble question being topic du jour back home as well, I was kinda unprepared for how to summarize my current feelings. Largely because regardless of the outcome, our industry is incentivized heavily to play the game right now. And while I don’t mind shrugging and saying ‘I can argue both sides’ over cocktails at The Battery, my relatives demand more specific responses!

So here’s my 100 Hours to Go in 2025 summary. There’s not one type of bubble to assess, but instead four.

Technology Bubble -> NO. You can be a believer in Artificial Intelligence without having to assume it can achieve AGI or Superintelligence. And that’s where I am. The opportunity and promise of the technologies currently being built is as impactful as every other phase change I’ve lived through: personal computer, Internet/WWW, cloud computing, and the smartphone. I’m incredibly excited about both edges of applications – the mundane and the advanced – while thinking the middle is going to be harder to solve. What I mean by this is, lots of small productivity gains doing basic repetitive tasks and hyper-compression of complex simulations and analysis, but workflows that require multiple points of offline interactions or situational judgment or five 9s accuracy, are still elusive. That’s fine! The small stuff actually adds up to a TON of productivity gains. And the large stuff (drug discovery!) is hugely impactful.

Investment Bubble -> Likely YES. By this I mean, will the total amount of capital being deployed into the AI space provide in aggregate its expected returns (whereas the Valuation question below is the price of each asset). Here I tend to buy more of the ‘telecom buildout’ bubble thesis – that it’s not clear the starry-eyed modeling for $2 trillion more of data center capacity and so on is going to have the IRR that’s modeled today – the same can be same for chips that could lose value faster, and so on. But that these assets will still be *productive* assets over an extended period of time, not nothingburgers. So capital markets, circular business development deals, and the like are supporting an over-investment, that will decrease overall returns of much of the category, but that the yields will still be positive overall (yes, some players will go to zero).

Valuation Bubble -> Absolutely YES, in the private markets. I can’t even really bring myself to write much here. Read Pace Capital’s Chris Paik’s “Paying $3 for a Dollar: The Rational Irrationality of Venture Capital.”

Revenue Bubble -> NO. If you read my Technology Bubble paragraph above then this shouldn’t be a surprise. We could stop new model development and current model improvement RIGHT NOW and I believe it would still take 3-5 years for society to understand how to adopt all the use cases the current stack supports. Because it’s not just the input/output part, it’s also the changing of processes, strategies, and organizations to realized all the benefit of these tools. There are various reports which say “AI Revenue Must Grow XXX% YoY” to fulfill current expectations, and folks often repeat these numbers with skepticism. I’m on the bull side here – the pie is going to grow much larger over time. This isn’t just about company pilots and consumer experimentation (although there will be many shifts in where the revenue goes over the years), this is evergreen.

So I guess I’m generally bullish on the technology and business, and believe there’s a bit of a mania right now in the funding, which might help society overall but is a crazy time to live through.

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.

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.