New @Sugar_Capital office! The Presidio is such a privilege to work in, so beautiful. 💙

What SEO shenanigans does @SubstackInc play so the platform's version of my posts show up and the ones from my custom domain do not?.

10/ AI will not fix the business model. But the right business model, enabled by AI, might finally fix fashion discovery. Full analysis of why AI shopping platforms face the same old problems (and what might actually work):.

9/ But here's the opportunity. The AI advances are real. The technology finally works. The entrepreneurs who build around structural realities rather than against them will create something genuinely transformative.

8/ The brutal truth: The tech industry has spent over a decade and billions trying to disrupt fashion discovery. The incumbents have only grown stronger. Amazon dominates retail. Google controls search. Social platforms own discovery.

7/ The customer experience is still broken. Find three pieces for an outfit across different brands = three separate checkouts, three shipping fees, three return policies. When something goes wrong, customer service becomes finger-pointing between platform and retailers.

6/ Then there's the attribution nightmare. Browser extensions hijack commissions. Cross-device shopping breaks tracking. And now AI itself creates new attribution challenges. They do the work. The giants get paid.

5/ Meanwhile, the retailers that discovery platforms depend on for inventory are also their direct competitors for keywords and advertising. Nordstrom and Zara bid against Daydream for the same Google search terms. The retailers' CAC will always be lower.

4/ Here's the structural problem: When OpenAI adds shopping to ChatGPT, it's not creating a new destination. It's embedding commerce into existing behavior. Discovery startups must convince users to develop new habits while tech giants embed shopping into existing flows.

3/ The real issue was never technology. Polyvore had elegant visual discovery. ShopStyle offered comprehensive search. Lyst, Wanelo, Fancy, Pose, Spring, and about fifty others you've probably forgotten all had powerful capabilities. None became billion-dollar businesses.

2/ As CEO of POPSUGAR (which owned ShopStyle), I watched fashion discovery platforms struggle with the same fundamental problems for over a decade. Better algorithms, same broken math.

1/ The AI shopping boom is here. ChatGPT can shop for you. Google's virtual try-on is uncannily good. Daydream raised $50M. OneOff and Alta are building AI styling platforms. The technology is genuinely impressive. But I've seen this movie before. 🧵.

Q3 starts today.

8/.Read more: The Paper Tigers of Venture Capital.

7/.Smart founders reverse-DD: . "Do they honor commitments when shit gets real?". Answers spread fast.

6/.Standard excuses from the messenger: . "Partners had concerns" ."Macro uncertainty" ."Being disciplined". Translation: "Our word means nothing.".

5/.These VCs dress it up as "fiduciary duty to our LPs.". They've just marked themselves forever. Founders remember.

4/.Often it's the lapdog junior VC who delivers the bad news. Convenient scapegoat for a firm-wide decision. Cowardice dressed as delegation.

3/.Tier 1 firm just cut friend's Series A by 30%. Six weeks post-signature. Zero business changes. No backbone.

2/."Retrading" is Venture speak for lying. Sign. Stall. Cut valuation. Blame "macro.". It's theft.