Writing
Everything I've written.
84 articles on business, investing, leadership and life.
- Oct 23, 2026How to Spot Aphorism Slop in AI WritingLeadership · AI adds quotable lines that sound wise and carry no facts.
- Oct 23, 2026Why California's Poor Will Pay the Billionaire TaxInvesting · California's billionaire tax sounds like a bill for a few hundred people.
- Oct 23, 2026Own Assets or Be Left BehindInvesting · Elon Musk's $1 billion Skydance investment is the latest example of owners putting their ownership to work.
- Oct 23, 2026How Leaders Can Use AI to Recover From Hard WeeksLife · Most leaders use AI for work.
- Oct 23, 2026Why Forward-Deployed Engineers Are the FutureBusiness · Forward-deployed engineers sit between businesses that need help adopting AI and people who need new skills.
- Oct 21, 2026Trump's Data Center Dividend Shows AI Has to Give BackBusiness · President Trump says data centers should make their own electricity and pay the communities around them a…
- Oct 21, 2026How Lifestyle Inflation Eats Every RaiseLife · Employers and the government call about 3.6% a cost of living raise.
- Oct 21, 2026Everyone's Job Is Changing at OnceLeadership · From the PE firm to the intern to the high school student, every role is changing at the same time.
- Oct 20, 2026How to Spot a Bubble, According to Ray DalioInvesting · Bubbles take years to form and years to burst.
- Oct 20, 2026Why the Energy Trade Can Work for YearsBusiness · The war has gone on long enough to change the floor.
- Oct 20, 2026Where Software Engineers Will Work NextBusiness · Software vendors need fewer engineers.
- Oct 20, 2026Why ARR Is Over in the Age of AIBusiness · Companies spend on AI in bursts, a heavy build followed by light upkeep.
- Oct 19, 2026Why Elon Musk and Anthropic Are Giving Away SharesInvesting · AI is making the people who own it richer, fast, while people with only a paycheck fall behind.
- Oct 19, 2026What Berkshire's Bending Spoons Bet Says About SoftwareInvesting · Bending Spoons buys software brands cheaply and runs them for profit, and the market values it at about four…
- Oct 19, 2026We Need a New Model for EmploymentBusiness · The 40-hour week was built for factories.
- Oct 18, 2026What Andrew Ross Sorkin's 1929 Teaches AI InvestorsInvesting · Good leaders in 1929 propped up a market they had doubts about, and they weren't villains.
- Oct 17, 2026What Elon Musk’s Net Worth Teaches About OwnershipInvesting · You can start owning businesses without founding one or buying a whole share.
- Oct 17, 2026Is AI Propping Up the US Economy?Investing · Business owners using AI well are running with far fewer people.
- Oct 15, 2026Amazon's Bee Means Leaders Are Always on the RecordLeadership · Recording devices are going mainstream.
- Oct 15, 2026beehiiv CEO Tyler Denk Is Right About Vibe-CodingBusiness · AI makes the first version of almost any product cheap.
- Oct 14, 2026Bending Spoons Shows SaaS Doesn't Need 5,000 EngineersBusiness · Bending Spoons runs Evernote, Vimeo, AOL and now Airtable with small teams and AI.
- Oct 14, 2026How to Use AI Skills to Become Better at Your JobLeadership · Skills may be the most underused part of AI.
- Oct 13, 2026Americans Are Wealthier Than Ever and Giving Less of ItLeadership · Household wealth has roughly doubled, and giving has shrunk as a share of it.
- Oct 13, 2026We Forget Jeff Bezos Was Once a Broke EntrepreneurBusiness · We see Jeff Bezos the billionaire and forget the founder who started Amazon in a garage.
- Oct 13, 2026Kroger Is Cutting 3,000 Corporate Jobs to Run LeanerBusiness · AI lets leaders do more with less work, so companies need fewer layers between a decision and the customer.
- Oct 12, 2026What Happened to My SEO When I Left WordPress for LovableBusiness · The real numbers from moving my sites off WordPress and WP Engine, a side-by-side comparison, and the…
- Oct 11, 2026Why Even Dividend Stocks Aren't Safe AnymoreInvesting · A steady payout doesn't protect a business from fast change.
- Oct 10, 2026How to Plan Five Years Out When AI Changes FastLeadership · You can't forecast five years out anymore.
- Oct 9, 2026Welcome to the Integration WarsBusiness · The open web ran on two assumptions: users are human, and platforms are hard to build.
- Oct 8, 2026Where I'd Put Money Instead of the Anthropic IPOInvesting · Where I'd put money instead as AI models get cheaper, and why I think the IPO lands after the November…
- Oct 7, 2026What Are My Stock Options Worth?Investing · Your stock options are only worth something if the company is.
- Oct 6, 2026Tesla Is Having Its iPhone MomentInvesting · I think Tesla has passed its tipping point.
- Oct 3, 2026Recurring Revenue Is About to Get a Lot Less RecurringBusiness · Recurring revenue works because people sign up on impulse and cancel on procrastination.
- Sep 30, 2026Your Identity Was Never What You Do for a LivingLife · Your title is what you do, and AI will change it.
- Sep 27, 2026Why Your Voice Is Replacing the KeyboardBusiness · I now write articles by talking.
- Sep 23, 2026Why I Own Tankers and Oil Companies Right NowInvesting · Software can be rebuilt cheaply now.
- Sep 1, 2026Why I Stepped Away for Seven Years, and Why I'm BackLife · There are more people building companies than ever, and they need more support to match.
- Aug 29, 2026Founder Mode vs. Founder DriftLeadership · Founder mode is a founder staying in the details of the company that made them a founder.
- Aug 19, 2026AI Watermarking Is a Pattern I've Watched for Twenty YearsBusiness · AI watermarking is the fourth version of a pattern I have watched for twenty years: cheap content floods a…
- Aug 8, 2026The Best Companies Run Two LoopsLeadership · For the next few years, the winning company runs two loops: a tight builder loop where agents compress what…
- Aug 1, 2026The Hour in New York That Helped Me Think ClearlyLife · Some of my best thinking happens when I step away from work.
- Jul 22, 2026AI-Native Companies Move Faster in Every DepartmentBusiness · Every department in your company is a deployment pipeline, and almost none of them measure lead time.
- Jul 15, 2026Why Human Marketing Wins When Bots Outnumber PeopleBusiness · One founder sent 100,000 AI-written emails in thirty days and got a flagged domain and a handful of MQLs.
- Jul 8, 2026When Social Media Helps Leaders, and When It Quietly HurtsLife · The best way to know whether social media is helping you is to step away for a while and notice how you feel.
- Jul 1, 2026Your Best Experiences Are on the Other Side of FearLife · Only one person could climb the lighthouse at a time.
- Jun 18, 2026Fix the Problem Behind Your Other ProblemsLeadership · A full calendar feels like progress and usually is not.
- Jun 2, 2026Where Anthropic's Biggest Users Do Their WorkBusiness · Ahead of the Anthropic IPO I went looking at where coding work actually runs.
- May 23, 2026Is Every Hire a Builder or a Grower?Business · Most companies are still buying players who look the part instead of buying wins.
- May 14, 2026How to Build Generational Wealth That Outlives YouLife · Wealth lasts across generations when a family plans for the money and the people together, often with a…
- May 6, 2026What the AI-Native Executive Team Looks LikeBusiness · The AI-native exec team is not a bigger boat.
- Apr 29, 2026Hire for the Problem Slowing Your Company DownBusiness · We paid engineers like professional athletes because engineering was the bottleneck.
- Apr 16, 2026Legacy SaaS Is Worth Its DataBusiness · Your customers can now rebuild your interface in a month, and some of them will.
- Apr 8, 2026AI Only Picks One WinnerInvesting · AI does not hand you ten results to compare.
- Mar 24, 2026Per-Seat Software Is the Last Castle of SaaSBusiness · Most of my net worth sits in tech, so I want the SaaS party to continue.
- Mar 2, 2026The End of Management as CoordinationLeadership · The gap between a high performer and an average one went from ten times to something closer to a hundred.
- Feb 15, 2026The Rise of Hollow ARR in AI CompaniesBusiness · Not all of the record-breaking ARR of the last two years is recurring.
- Feb 4, 2026How Chasing Approval Quietly Runs Your CompanyLeadership · If you learned to read rooms to stay safe as a kid, that radar made you a fast operator and it will also…
- Jan 21, 2026What My First Trip to Miraval Taught Me About UnpluggingLife · What I learned about unplugging and being present, and simple ways to do it without a week away.
- Dec 30, 2025What I Learned in 2025 and What I Expect in 2026Life · The year I noticed the digital world and the real world are moving in opposite directions.
- Dec 2, 2025What Private Equity Spreadsheets Leave OutInvesting · Private equity is not inherently evil, it is inherently numerical, and once numbers dominate the worldview…
- Nov 19, 2025Most of What We Eat Is Acidic. So Is Most of Modern Life.Life · Balance in the body and the mind is the whole idea.
- Nov 12, 2025We Think About the Next Hour While Some Families Plan 100 YearsLife · I visited a friend's ranch.
- Sep 30, 2025The Power Dynamics Behind Partnership LanguageLeadership · “We're all in this together” is partnership language laid over control reality, and everyone in the room can…
- Aug 27, 2025What Managing a Gym at 19 Taught Me About LeadershipLeadership · My first leadership job was running a gym at night.
- Aug 3, 2025AI Is Ending the Entry-Level JobBusiness · AI is taking the bottom rungs of the org chart, and scale no longer means hiring.
- Jul 9, 2025How to Find What Is Capping Your Company's GrowthBusiness · Growth usually stalls at one main constraint.
- Jun 17, 2025Headless CRMs Train Customers to Stop Logging InBusiness · When you invite customers to plug an LLM straight into your CRM, you train them to stop logging in.
- Apr 16, 2025What You Actually Take Home When You Sell Your CompanyInvesting · The sale price is not what you take home.
- Mar 12, 2025Should You Raise Money or Bootstrap?Business · Raise when speed decides who wins your market and you can use the money to grow faster than you otherwise…
- Jan 22, 2025What Is My Company Worth?Investing · A private company is worth what a specific buyer will pay on a specific day, so any honest valuation is a…
- Nov 20, 2024Should You Start a Company or Stay an EmployeeBusiness · Start a company if you can live with years of uncertainty, you're drawn to one specific problem, and you'd…
- Sep 18, 2024How to Find Your Ideal Customer Before You ScaleBusiness · Your ideal customer is the narrowest group that feels the problem most, can buy without a committee, and…
- Jun 12, 2024How to Tell if Your Startup Idea Is Any GoodBusiness · A good idea is a painful, frequent problem that a specific group already spends money or time trying to…
- Sep 26, 2022The Great Reset in the Post-Pandemic Labor MarketBusiness · Written in 2022, after a lunch with an HR leader in the middle of a second round of layoffs.
- Sep 2, 2021Remote Work Exposed the Illusion of Measuring OutputBusiness · Many companies measured presence because it was easy.
- Feb 21, 2021Why Not Everyone Can Be a CEOLeadership · Chasing the title is the surest way to miss it.
- Jul 30, 2020Why I Quit LinkedIn and Deleted a Decade of AudienceLife · I deleted a decade of audience on purpose.
- Jul 28, 2020Why I Sold My Slack Stock After It Attacked MicrosoftInvesting · I sold my Slack stock after its full-page ad aimed at Microsoft.
- Jun 23, 2020How I Have Vulnerable Conversations at WorkLeadership · When the line between home and work disappeared in 2020, so did the illusion that people leave their lives at…
- Dec 21, 2019What Law School Taught Me About How to LearnLeadership · You decide what you need to know and go get it.
- Apr 26, 2019Preparing for Slack's IPO as an Early InvestorUpdates · What a public filing tells an early investor: how far a company has spread, how enterprises adopt it, and…
- Dec 3, 2018Why Entrepreneurs Struggle with EmpathyLeadership · Vision pulls founders into the future.
- Oct 15, 2011What 100,000 Customer Complaints Taught Me About GrowthBusiness · Companies grow, outsource support and stop listening.
- Oct 25, 2010Unlearn Your MBALeadership · Written in 2010 on DHH's argument that planning is guessing and constraints are what actually drive good work.
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