On startup culture.
Posts, talks, and podcast appearances related to startup failure, founder psychology, ethics, go-to-market, and getting found in the age of AI. I’m always eager to share what I’m learning and un-learning along the way.
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Coming October 2026 Stanford Technology Ventures ProgramPatterns of Startup Failure
Coming October 2026 Berkeley Haas, with Erica BaileyPatterns of Startup Failure Talk: “The Dangers of Over-Confidence” Berkeley Haas, with Don A. MoorePatterns of Startup Failure
Talk: “Hilariously Early” New York UniversityStandalone
Talk: “Hubris and Ethical Fading” Yale School of ManagementPatterns of Startup Failure Sep2026 The SEO Abilities of MediaWiki and the .Wiki TLD Fourteen MediaWiki sites, measured for most of a year.AI May2026 Research: Programmatic and News Aggregators Are Cooked, Social Is a Discoverability Terror Five months of running AI-generated local news sites and paid placements to see what the gatekeepers would let through. They held. Social is the harder fight.AI Nov2025 Crowdfunding Your Startup Is Making a Big Comeback With venture money chasing AI, founders are going back to raising from the people who already believe them.Go-To-Market Aug2025 Wikipedia Rules Everything Around Me Wikipedia is the backbone the models were trained on, which quietly makes it the arbiter of your digital reputation.AI Aug2025 Who Should Handle Your Digital ID? We are running the largest identity verification experiment in history and almost nobody is asking who ends up holding the data.Crypto Jun2025 The Difference Between Early-Stage Theater and Traction When progress slows, appearances become the product. What looks like momentum and what actually is are not the same thing.Failure Jun2025 You Are Not Your Startup, Your Startup is Not You The overlap between founder and company fuels conviction early and destroys objectivity later. Feedback starts to feel like attack.Failure 
Talk: “When ‘Founder-Friendly’ Turns Into Isolation” ACFEPatterns of Startup Failure Jun2025 The New Tools Rewriting the Web Publishing now means building a publishing system, not just writing the thing.AI May2025 The Modern Job Hunt: AI Interviewing AI Both sides of hiring are automating at once, and the ethics have not caught up to either of them.AI Apr2025 If Your Products Aren't AI-Searchable, You're Already Losing What it actually takes to show up inside ChatGPT's shopping answers, on the page and off it.AI Mar2025 The Rise (and Real Value) of #PrisonTok The case for what specialized TikTok communities are worth, against a discourse that treats the whole platform as one thing.Media Feb2025 Sam Mangel to Sam Bankman-Fried: Acceptance Is the Path Forward SBF's mitigation strategy gives away that he still does not believe he did anything wrong. I have some experience with what that costs.Failure Jan2025 Livestream Shopping: Ready to Explode in 2025 TikTok made livestream shopping work by pairing real-time interaction with community trust. American brands are late to it.Media Jan2025 Ladies Is Apes, Too: It's Not Just Men Thriving in Bro Trading Culture What started as a rallying point for young finance bros quietly became something much broader, and much less male.Media 
ShowUp, When Business Gets Messy Stories like the FedEx CEO who gambled the company's last $5k to keep the company afloat fuel an unhealthy appetite for risk that has become core to the entrepreneurial ecosystem.Failure 
Talk: “Afraid to Fail” Drexel’s Close School of EntrepreneurshipPatterns of Startup Failure Oct2024 AI Discoverability for Small Business The concrete steps that get a small business found on ChatGPT, Perplexity, Siri, and Alexa.AI 
Nightmare Success, From Peak to Valley Brent Cassity's Nightmare Success podcast was the perfect place to share my startup failure story in podcast form for the first time.Failure Dec2023 AI That Helps Us Be More Human With Each Other AI Mar2017 Your Bank Tried to Kill My Company There are countless ways for a startup to die. Nobody warns you that your own bank is one of them.Failure Jan2017 Unicorn Delusion: The Dark Side of Seeking a Billion-Dollar Valuation The link between chasing a billion-dollar valuation and the depression that tends to arrive with it.Failure Oct2016 3 Ways to Make Sure Your Online Ads Aren't a Turnoff Placement does more damage than creative. Start with where the ad sits, not what it says.Go-To-Market Nothing in that category yet.
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