Notes on Startups and Startup Culture.
Building, fundraising, go-to-market, AI, and the human stuff that comes with trying to make something work. Some of it I learned by getting it right. Some of it I learned the expensive way.
More on booking a speaking engagement.
Everything
Talk: “Hilariously Early”New York UniversityStandaloneSep2026The SEO Abilities of MediaWiki and the .Wiki TLDFourteen MediaWiki sites, measured for most of a year.AIMay2026Research: Programmatic and News Aggregators Are Cooked, Social Is a Discoverability TerrorFive 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.AINov2025Crowdfunding Your Startup Is Making a Big ComebackWith venture money chasing AI, founders are going back to raising from the people who already believe them.Go-To-MarketAug2025Wikipedia Rules Everything Around MeWikipedia is the backbone the models were trained on, which quietly makes it the arbiter of your digital reputation.AIAug2025Who 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.CryptoJun2025Rentaba, "Credit Where Rent Is Due"Rentaba is reworking the tenant-landlord relationship by bridging the rental market and modern financial technology.MemoJun2025NextPick, Fixing College Athletic RecruitingNextPick offers the college athletic recruiting process a modern three-sided marketplace that connects parents of athletes, vetted recruiting agents, and college coaches.MemoJun2025The Difference Between Early-Stage Theater and TractionWhen progress slows, appearances become the product. What looks like momentum and what actually is are not the same thing.FailureJun2025You Are Not Your Startup, Your Startup is Not YouThe overlap between founder and company fuels conviction early and destroys objectivity later. Feedback starts to feel like attack.FailureJun2025The New Tools Rewriting the WebPublishing now means building a publishing system, not just writing the thing.AIMay2025The Modern Job Hunt: AI Interviewing AIBoth sides of hiring are automating at once, and the ethics have not caught up to either of them.AIApr2025If Your Products Aren't AI-Searchable, You're Already LosingWhat it actually takes to show up inside ChatGPT's shopping answers, on the page and off it.AIMar2025The Rise (and Real Value) of #PrisonTokThe case for what specialized TikTok communities are worth, against a discourse that treats the whole platform as one thing.MediaFeb2025Sam Mangel to Sam Bankman-Fried: Acceptance Is the Path ForwardSBF's mitigation strategy gives away that he still does not believe he did anything wrong. I have some experience with what that costs.FailureJan2025Livestream Shopping: Ready to Explode in 2025TikTok made livestream shopping work by pairing real-time interaction with community trust. American brands are late to it.MediaJan2025Ladies Is Apes, Too: It's Not Just Men Thriving in Bro Trading CultureWhat started as a rallying point for young finance bros quietly became something much broader, and much less male.Media
ShowUp, When Business Gets MessyStories 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.FailureOct2024AI Discoverability for Small BusinessThe concrete steps that get a small business found on ChatGPT, Perplexity, Siri, and Alexa.AI
Nightmare Success, From Peak to ValleyBrent Cassity's Nightmare Success podcast was the perfect place to share my startup failure story in podcast form for the first time.FailureDec2023AI That Helps Us Be More Human With Each OtherAIMar2017Your Bank Tried to Kill My CompanyThere are countless ways for a startup to die. Nobody warns you that your own bank is one of them.FailureJan2017Unicorn Delusion: The Dark Side of Seeking a Billion-Dollar ValuationThe link between chasing a billion-dollar valuation and the depression that tends to arrive with it.FailureOct20163 Ways to Make Sure Your Online Ads Aren't a TurnoffPlacement 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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