What building actually looks like from the inside, and why the public version of it is usually wrong.
Essays, talks, and podcast appearances.
Everything
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.HackerNoon 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.HackerNoon Oct2025 "The Dangers of Over-Confidence" at Berkeley Haas My biggest mistake wasn’t failing.chapin.blog 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.HackerNoon 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.HackerNoon Jun2025 The New Tools Rewriting the Web Publishing now means building a publishing system, not just writing the thing.HackerNoon May2025 "Founder-Friendly Really Means Isolation" at ACFE Exploring how “founder-friendly” partners, isolation, and a lack of organizational controls can set the stage for disaster - and what we can all do to prevent it.chapin.blog 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.HackerNoon 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.HackerNoon 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.HackerNoon Feb2025 "Hubris and Ethical Fading" at Yale School of Management How far would you go to close the deal?chapin.blog 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.HackerNoon 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.HackerNoon 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.HackerNoon Dec2024 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.chapin.blog Oct2024 "Afraid to Fail" at Drexel's Close School of Entrepreneurship Rather than acknowledging reality, I attempted to fake it ‘til you make it.chapin.blog Oct2024 AI Discoverability for Small Business The concrete steps that get a small business found on ChatGPT, Perplexity, Siri, and Alexa.HackerNoon Jan2024 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.chapin.blog Dec2023 AI That Helps Us Be More Human With Each Other ReadWrite 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.HackerNoon 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.Observer 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.Entrepreneur
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