Writing
Everything I've written.
48 articles on business, investing, leadership and legacy.
- 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 LivingLeadership & Legacy · AI is changing every job title, including the CEO's.
- Sep 23, 2026Why I Own Tankers and Oil Companies Right NowInvesting · I now own Scorpio Tankers, Chevron and other energy companies, not SaaS.
- Sep 1, 2026Why I Stepped Away for Seven Years, and Why I'm BackLeadership & Legacy · I stepped away from public life in 2018 after twenty years of the grind, but I kept working with founders the…
- Aug 29, 2026Founder Mode vs. Founder DriftLeadership & Legacy · 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 & Legacy · 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 ClearlyLeadership & Legacy · 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 PeopleLeadership & Legacy · One founder sent 100,000 AI-written emails in thirty days and got a flagged domain and a handful of MQLs.
- Jul 1, 2026Your Best Experiences Are on the Other Side of FearLeadership & Legacy · We reached a lighthouse where only one person could go up at a time.
- Jun 18, 2026Fix the Problem Behind Your Other ProblemsLeadership & Legacy · 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 GrowerBusiness · Most companies are still buying players who look the part instead of buying wins.
- 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 DownLeadership & Legacy · We paid engineers like professional athletes because engineering was the bottleneck.
- Apr 16, 2026Legacy SaaS Is Worth Its DataInvesting · 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 SaaSInvesting · Most of my net worth sits in tech, so I want the SaaS party to continue.
- Mar 2, 2026The End of Management as CoordinationLeadership & Legacy · 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 CompaniesInvesting · Not all of the record-breaking ARR of the last two years is recurring.
- Feb 4, 2026How Chasing Approval Quietly Runs Your CompanyLeadership & Legacy · 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 UnpluggingLeadership & Legacy · On my first trip to Miraval, my phone went into a little cotton bag.
- Dec 30, 2025What I Learned in 2025 and What I Expect in 2026Leadership & Legacy · 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 12, 2025We Think About the Next Hour While Some Families Plan 100 YearsLeadership & Legacy · I visited a friend's ranch.
- Sep 30, 2025The Power Dynamics Behind Partnership LanguageLeadership & Legacy · “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 & Legacy · At 19 I was the night manager of Womack's Gym in Keller, Texas.
- 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 CompanyBusiness · 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?Business · 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 MarketLeadership & Legacy · 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 · The fight over offices and remote work is really a fight about measuring output.
- Feb 21, 2021Why Not Everyone Can Be a CEOLeadership & Legacy · People who say they want to be a CEO rarely become one, and the people who do almost never set out for the…
- Jul 30, 2020Why I Quit LinkedIn and Deleted a Decade of AudienceLeadership & Legacy · I deleted a decade of audience on purpose.
- Jul 28, 2020Why I Sold My Slack Stock After It Attacked MicrosoftBusiness · I sold my Slack stock after its full-page ad aimed at Microsoft.
- Jun 23, 2020How I Have Vulnerable Conversations at WorkLeadership & Legacy · 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 & Legacy · There's no required degree for law school, and that taught me the real lesson: learning isn't a set path.
- Apr 26, 2019Preparing for Slack's IPO as an Early InvestorUpdates · I was an early investor in Slack.
- Dec 3, 2018Why Entrepreneurs Struggle with EmpathyLeadership & Legacy · Founders who live in the future often miss the people in front of them.
- Oct 15, 2011What 100,000 Customer Complaints Taught Me About GrowthBusiness · I have read more than 100,000 customer complaints through a complaints site I founded.
- Oct 25, 2010Unlearn Your MBALeadership & Legacy · Written in 2010 on DHH's argument that planning is guessing and constraints are what actually drive good work.
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