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Hunter Walk
Self-Aware Self-Promotion
- Posts
- 1,765 from 16 Jun 2005 to 12 Oct 2026
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- weekly (49 in the last year)
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Latest
October 2026
- Why There Will Be More Pro Rata Conflicts
- Mercury’s CEO on their Principles of Writing (and AI Usage)
September 2026
- I used to respond to every cold email but now AI slop is killing my inbox
- AI: “It’s very difficult to have a sober conversation about this when there’s so much money at stake”
August 2026
- Does Your Startup Have an AI Writing Policy Yet? Here’s One from Clay.
- AI is Changing South Korea Even Faster Than it’s Changing the US; Why 🥀 Is The Fastest-Rising Emoji; How Robots Might Save Cherry Blossom Season; +++ [link blog]
- Why “Grab Any Seat on the Rocketship” is a bad career strategy; this VC thinks people are right to hate today’s capitalism; look for founders who play RTS games; and a Chrome extension which blocks slop ecom brands ++ [link blog]
July 2026
- Airlines Are Using AI to Maximize Prices – Here’s How You Fight Back
- Startup Kool-Aid; Why You’re Making Enough Money but Still Anxious; $100 Million in Odyssey Popcorn Buckets; the World’s Best Fake $50 Bill, +++ [link post]
- I’ve Changed My Mind. Early Stage Venture Funds of $100 Million or Less Should Hold Almost No Reserves for Follow-On.
- Three Words That It’s Time For Us To Leave Behind: Non-Technical, Unicorn, and Oversubscribed.
- Product Market Fit is Hard to Find, but False PMF is Even More Painful
June 2026
- Celebrate People like Om Malik and Susan Wojcicki When They’re Alive. That’s the Best Chance We Have To Make Tech Good Again.
- Let’s Learn Together: Financial Tools Startup Ambrook Spent Six Weeks Helping Their Entire Team Adopt AI. And Now They’ve Open Sourced the Materials
- 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.
May 2026
April 2026
- 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.
March 2026
- 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]
February 2026
- 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
January 2026
- “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]
December 2025
- 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.
November 2025
- 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.
October 2025
- 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)
September 2025
- 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
August 2025
- 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]
July 2025
June 2025
April 2025
- Praise Our Lord For Secondary Markets, Because Selling Shares Is Now an Essential Part of (Seed) Venture Capital
- “I think CEOs that are interested in a future acquisition need to be building relationships or at least awareness with potential buyers at least 2-3 years in advance, especially with strategics. If you’re not on the list, it’s rare for a deal to happen.” Joe Hyrkin on Selling Issuu to Bending Spoons
- Anonymous AI Engineer Funding SF Events, How Startup Decision Making is Like an Outdoor Survival Trip, the Guy Who Reports on Hacks Gets Pwned Himself, and +++ [link blog]
March 2025
- The Right Amount of Fraud in Seed Stages Startups is Greater than 0% But It Shouldn’t Be Pardoned
- “I consider my writing a success if I’m able to produce words I can both stand behind/formally weave into my worldview.” Five Questions with Moth Fund’s Molly Mielke
- Men Spend More Time with TV than with People, Founder Gives Away Half His Wealth to Progressive Causes, a VC Thinks the LLMs are Going to Try and Eat SaaS, & the AI Prompts That Saved a Life [link blog]
- How a Venture Fund (Ours!) Actually Works With Their LPAC
- When Software Eats the World, Vulnerable Populations – Like Kids – Can Get Exposed to Venture Risk Without Knowing It
- After Investing $100 Million Into New VC Firms, Here’s What I Look For: Traditional But Better, or Different & Excellent.
February 2025
- Exceptional Startups Are Needles in a Haystack. So the Best VCs Build Needle Magnets.
- Simple Advice for Junior Folks in Venture Capital: Don’t Be a Generalist. Do One Thing Really Well for your GP and One Thing Really Well for Founders.
- “You have to assume every company will have access to the same LLMs and voices. The challenge, then, is to build a company that thrives despite this reality” Five Questions with RegalAI’s Alex Levin on Building In a Fast Moving Industry and More
- “I wanted to do the deal but couldn’t get it through my partnership” is always such weaksauce
- Nine Signs Your Startup Is Going to Fail; Planning Your Annual Family Summit; SNL Performers Cracking Themselves Up; and +++ [link blog]
- Don’t Take It Personally. Take It Professionally.
- I never want founders to QUIT, but sometimes they should STOP
January 2025
- Scarcity During Experimentation, Abundance During Scaling [mini post]
- Profitability Can Be a False Goal If You’re Playing Defense to Get There
December 2024
- If You Don’t Like Sales, Don’t Start a Company
- 10 Tips for a Great Career, Will AI Help Us Talk to Animals, an Economic Fairness Metric to Rival GDP and +++ [link blog]
- What to do about sports gambling addiction in America [mini post]
- Self-Driving Cars are (a) magical, (b) ready, and (c) should be allowed to kill people [mini post]
- A VC Firm Can Be Either a Partnership or a Collection of Partners [mini post]
- VCs Leave Their Funds and Their Portfolio Companies Often Suffer [mini post]
- “Look, like, i don’t know if this company is going to be around in three to six months. But what i can tell you is it’s going to be the most memorable three to six months of your life”: Sequoia’s Roelof Botha with YouTube’s Steve Chen
November 2024
- Duct Taping Your Org Chart, How to Use ‘Code-Yellows’ at Your Startup, Do AI Meeting Assistants Make You More Present, and MORE+++ [link blog]
- “I think viewing your board as an audience to be ‘sold’ to instead of a partner in your journey will orient your board to be less trusting and collaborative.” Five Questions with Nilam Ganenthiran, Former President of Instacart
- Winning at Seed Investing Isn’t Just About When to Buy, but Increasingly Also When to Sell
October 2024
- “I actually thought I’d stay at Flexport my entire career.” Ben Braverman’s Path Into, and Out of, His Dream Job and Then Founding Saga, a New Venture Firm
- My Goal is to NEVER be on the VC Midas List
- “Sanzo is at its best when we serve as a bridge across cultures for both AAPI and non-AAPI.” CEO Sandro Roco on building a beverage startup, what to avoid in influencer deals, & protecting the brand.
- Are Bookstores a Waste of Space, Can Scientists Change the Weather, Future of AI Agents, and Curing Loneliness Is Tough [link blog]
- I Once Feared Professional Irrelevance. Now I Embrace It.
September 2024
- “One Thing You Wish People Better Understood About Venture Capital” – Part V, featuring Ethan Kurzweil, Lily Lyman, Ashley Mayer, and Leshika Samarasinghe.
- “One Thing You Wish People Better Understood About Venture Capital” – Part IV, featuring Diana Kimball Berlin, Jake Gibson, Jesse Middleton, Adam Nelson and Nikhil Basu Trivedi.
- “One Thing You Wish People Better Understood About Venture Capital” – Part III, featuring Maya Bakhai, Paris Heymann, Nakul Mandan, Eric Tarczynski, and ANONYMOUS.
- “One Thing You Wish People Better Understood About Venture Capital” – Part II, featuring Victor Echevarria, Chris Neumann, Micah Rosenbloom, Alexa von Tobel and Roseanne Wincek.
- “One Thing You Wish People Better Understood About Venture Capital” – Part I, featuring Andre Charoo, Bill Clerico, Ryan Hoover, Amy Saper, and Dan Teran.
- 30 Years Ago I Said ‘No’ to Working for Phil Donahue, and ‘Yes’ to Conan O’Brien. No Regrets, But Only Now Do I Understand How Amazing Donahue Was.
August 2024
- “I will say that a lot of tension arose from Googler’s expectations that the company’s culture had to be exactly the same as what it was when the company was one fifth the size” Former GOOG & MSFT executive (and multiple time founder) Javier Soltero on Career Advice, Big Company Culture, and Startup
- A Hollywood Director on Whether AI Will Replace Him, What It Takes to Raise a Series B in 2024, Don’t Hire an Executive If They’ve Never at a Job for at Least Five Years, and +++ [link blog]
- Email Introductions 101. And Why a Strong Cold Email Always Beats a Weak Warm One.
- What Do VC Returns Actually Look Like? Here’s a Screenshot from my AngelList account
- The Best of the New VCs Will Outperform Most of the Legacy Ones. That’s Why We Created Screendoor to Back Them.
- Thank You Susan
- Why Company Communication Breaks at 50 People; a VC Notices What Happens When a Startup is Down to their Final $250k; You Are Almost Certainly Mispricing Your Product; and MOOOORE
July 2024
- Building Your First Exec Team; Avoiding Micromanagement; Skilled Immigration Should Be Prioritized; Spielberg is a Genius; and More [link blog]
- Traits a VC Looks For In Founders, Are Plants Actually Intelligent?, How Duolingo Streaks Work, and +++ [link blog]
June 2024
- The Future of Fashion Commerce Is a Designer’s AI Bot Saying You Look Great and Your Personal AI Bot Sifting Through the Bullshit
- A Guide to VC “Congrats” Tweets, From 🤑 to 😐
- An Operating Manual for Cofounders, Why It’s Silly to Say Your Funding Round was “Oversubscribed,” Space Weather Forecaster is a real job, and more… [link blog]
May 2024
- Backing New VC Firms With Screendoor: Welcoming OGs from First Round Capital, Pear VC, Reach Capital, and Refactor to the Cause
- Textio’s Founder Kieran Snyder on the Two Advantages Startups Have in AI (While Remaining Skeptical Of The Funding Gold Rush)
- The Airline Chatbot Lied and a Passenger Sued, Why You Shouldn’t Care About Your VC Being ‘Founder Friendly,’ and Will AI Slop Kill the Internet? [link blog]
- Are Startup Stock Options Like ‘Lottery Tickets?’ A CEO and Former Employee Discuss. And My POV.
- He Sold His Startup for $130 Million, Here’s What He Learned, and Questions to Ask When Considering Whether a New Job is a ‘Fit’ for You, Plus Other Great Reads [link blog]
April 2024
March 2024
- When to Tip $$, Andrew Huberman-ization of America, Jelly Roll Owns 100% of His Masters, and More [Link Blog]
- Seven ‘Pivots’ Later, Warmly Finally Found Its Stride. CEO Max Greenwald Covers What He Wishes He Knew At The Beginning, and More…
February 2024
- Every time OpenAI cuts a check for training data, an unlaunched competitive startup dies. Without a ‘safe harbor,’ AI will be ruled by incumbents.
- The Introvert Economy, the Case for Longer Founder Vesting Cycles, What Happens When Your Product Goes Viral on TikTok, and More [link blog]
- Incentives in Venture Capital, Why You Should Avoid Your Competitors’ Investors, China’s Malaise, and More [link blog]
- The Fonz on Leadership Lessons He Learned From Happy Days
January 2024
- VCs Are Leaving Their Firms But It’s The Founders They Backed Who Often Get Hurt
- “It takes a year to find great executives so you must always look down the field.” Proof’s Pat Kinsel on why he believes a VCs most critical task is to make sure the WRONG person doesn’t get hired into a startup.
- 2024’s First Link Blog Post (Because Happy Birthday Matt Mullenweg)
December 2023
November 2023
October 2023
September 2023
- How You Actually Feel Selling Your Company, Is It Worth Tolerating a Toxic Employee, & TechCrunch’s Former Editor in Chief Reflects on His Decade at the Helm [linkblog]
- Startups Fail All The Time, But Many Could Fail Better By Thinking Beyond the VCs and Founders
- Venture Capitalists Will Overpay For Seed Rounds But For Reasons You Likely Haven’t Considered
- Why VC Isn’t Right for Most Startups, The Place Where Taylor Swift, Gwar & Cypress Hill are Equals, and Parrothead Memories (RIP Jimmy)
- The Only Thing Which Has Failed About The ‘Creator Economy’ Thus Far Is Venture Capital’s Attempts to Get Their Piece. Why There’s Never Been a Better Time to Be a Creator.
- A Technical Cofounder Tells You How To Find Your Technical Cofounder, Where The Stuff We Return to Amazon Goes, a Benchmark VC on Rethinking Your AI Startup, and More….
August 2023
- And let’s be clear: The term “culture and employee engagement” doesn’t mean “Happy Hours” and “Pizza Parties:” Navigating Market Downturns and Other Startup Advice with Melanie Naranjo, Head of People at SaaS Startup Ethena
- The Best View of “What’s San Francisco Like Right Now?” Is Understanding This Simple Framework
- Why Starting Your Investor Updates With “Cash on Hand” Information is a Major Red Flag Right Now. It’s Maybe the Only Thing Worse Than Not Sending Updates at All.
- Lightspeed VC Michael Mignano on Why Apple’s Threats Influenced His Decision to Sell Anchor to Spotify, Why No FOMO in Venture is Good (AI Aside), & What NYC Founders Need to Realize
- I Like You But You’re Not Yet My Friend. What Do We Call Each Other? A Struggle to Replace “Acquaintance” With Something Better.
- US VCs Need to Lobby For High Skilled Immigration Reform (and Sacrifice Preferential Tax Treatment If Needed)
- Why We’re Heading Into the “Perfect Storm” of Startup Closures.
- Sold at the Peak: Congrats to Founders of Honey, Mirror, Frame.io and Others. You Timed It Perfectly.
- VC Optimism Returning But More Pain Ahead In Their Portfolios
- “Winners Take None:” Coworking, Self Storage, Scooters Have Burned Billions of Investor Dollars and Maybe Were Never ‘Tech Companies’
- Link Blog: Run Away When a VC Wants to ‘Preempt Your Next Round,’ How Barbie Got Made, Air Jordan Fraud, and More
- Great Time to Start a Company, Tough Time to Be Running One
July 2023
- Threads Gives You The Chance To Rebuild Your Follow Graph. Here’s All the Reasons You’ll Mess It Up.
- July 4th Linkblog: Don’t Fake FOMO When Fundraising, 50 Cent on Success, Miss Texas on Reproductive Rights, +++
Every year
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