Hunter Walk
Tips on Asking for Advice; Foreign Spies All Over Florida; Feeling Like You Don’t Have Enough Money Drives You Nuts; How to Use AI (and when not to) in Your Hiring; +++ [link blog]
Technical Interviews Are Dead – What Comes Next?, The Cosmetics You Buy Online Are Fake (and Unsafe), If You Can’t Get a Job Right Now It’s Your Fault, and +++ [link blog]
SAFE Adjusted TVPI: How Early Stage VCs Should Communicate SAFE Note Markups to their LPs
Some investors shape markets, while others are shaped by them
With all the AI money sloshing around Skin in the Game isn’t enough anymore. I’m looking for Heart in the Game too.
When Your VC Quits, Is The Founder Screwed?, Dads Are Doing More Dadding Than Ever, VC Who Founded Multibillion Firm Thinks Employees Need More Equity, AI for Old People +++ [link post]
At AI Dinners, You Can Leave Before Dessert. And Other Rules for IRL IS BACK Networking
Why I Hope I’m Wrong When I Pass on Investing in a Startup
“Having said that, it’s not a company that I’d start today. My bar for working on meaningful problems has gone up since I was 24” – Dan Teran, on evolving from a founder to an investor, and building what matters to him.
Don’t Worry 26, 34, 41 Year Old Friend In Tech. You’re Not ‘Too Old.’
Before You Automate It, Ask Whether You Should Even Be Doing It in the First Place
Opting Out of the Unicorn Race; The Code Doesn’t Love You Back – former Meta/Google Exec on How Engineering is Changing; A Case Against Big Companies (Why People Are Gonna Get Laid Off); and More+++ [link blog]
“If they raise VC, they usually get stuck and it’s a bad outcome for an otherwise good company.” Brad Hargreaves on which proptech companies should seek (or avoid) venture dollars. And more, from the founder of General Assembly, Common, and now, Thesis Driven.
“My one big tip for any of these business side roles is you still need to get close to the product. Nothing bothers me more than people that work at companies and never use their own products.” Zapier’s Corp Dev Lead Austin Johnsen on how AI is changing his job and building his own tools with Claude.
Can You Be Part of the System Without Also Being Part of the Problem? Yes but…
“Vast wealth of tech billionaires has made many of them unconcerned with the little people’s lives — and deeply unpatriotic.” Is Paul Krugman correct?
The AI Vampire; Startup Tolan Changes How It Hires Engineers in an AI World; Do You Back Into Parking Spots?; Social Engineer Hacks Against AI Agents; and More++ [link blog]
No Coding Before 10am; VCs Are Investing in Competing Companies – DGAF About Conflicts; “Technology is Not Destiny” – Principles for AI’s Future; and +++ [link blog]
“You’d also maybe be surprised how many X thinkbois hate on the media publicly but don’t behave the same in private” – reporter Jason Del Rey on going Indie with The Aisle, who inspires him, and why he failed to pay enough attention the the ChatGPT launch
“So say you’re against that. Now. Before it stops shocking you.”
GitHub Cofounder on Becoming a VC: “For me this is much more than a financial game. I want to fund founders that want to create a better future for PEOPLE.” Five Questions With Tom Preston-Werner.
So You Want To Watch YouTube
The LLM Way of Life; Boss Gives $240 Million to Workers; Connecting Ice Cream Trucks to Ukraine’s War; and +++ [link blog]
“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!” More Truths and Advice from Sources Founder reporter Alex Health
How Reliable Does AI Actually Need to Be?; Building a Career in Tech These Days is Hard; Backchannel References Are Lazy; Mac & Cheese is Changing; and More+++ [link blog]
My Mother-in-Law Wanted to Visit a Data Center. This Holiday, “Are we in an AI bubble?” Went Mainstream.
Should It Be Easier To Sue Influencers for Defamation?; 2025 Was the Year Self-Driving Car Optimism Went Mainstream; a Startup CEO’s Annual Learnings Post; a Podcast Where I Spoke for 43% of the Time; and +++ [link blog]
Org Charts Are Funhouse Mirrors Because Span of Influence is Not Limited to Span of Control
Graphite Gets Bought By Cursor: Three Reflections from Six Years of Work [PMF didn’t happen right away; working IRL mattered; three founders, three distinct roles]
Waymo’s CEO Isn’t Like Elon At All; Venture Capital Might Soon Depend on $1 Trillion Startups; Everyone is Gambling and No One is Happy; Are MCPs Just APIs 2.0? and more++++ [link blog]
Technical CEO Described How He Screwed Up Sales; Startup Operating Principles from an Ex-Stripe Founder; Most Leaders Move Too Slowly; and MORE [link blog]
Does valuation or ownership matter more to a seed VC? Yes.
Bodegas Aren’t Going Anywhere; Degen Economics is Hollowing Out Society; the New Electric Tech Stack; and more++ [link blog]
Vice Signaling is Poisoning Tech; Playing Entrepreneur on ‘Hard Mode’ is Worth Doing; OpenAI Won’t Build Every Dev Tool; and more++ [link blog]
“I tend to manage via a mix of advice and opportunity” – what I told a young product manager 15 years ago. And how it applies to startups today.
Smart AI Guidelines for Students: It’s Not All or Nothing
Why I No Longer Care About Startup Valuation When I Invest (Except for These Four Reasons)
When is Institutional Capital Right for a New VC Firm? And Two Myths About The Downsides of Taking LP Money.
It might not be true, but it is real. AI, SF and our culture.
Headcount isn’t a KPI, but talent density should be
Tech Reporter Alex Konrad on Going Independent with Upstarts, What Drives Subscribers (vs Just Views) and How He Uses AI in His Content Creation
S**t Shoveling
AI Buying Software Instead of Salespeople; Teaching Companies To Do Less; Have the Swiss Figured Out Cheaper Housing? and +++ [link blog]
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]
Why Marketing Sucks Right Now, Underground Robot Fights, Free Waffles Worth $50, and +++ [link blog]
No Notes: Near Perfect Posts on AI Ruining the Public Web, Silicon Valley Etiquette, the Fear of a Second Success, and +++ [Link Blog]
$CHYM TIME: The Three Boxes Chime’s IPO Checked for Me