Software missed a lot
Retail deductions. Construction payroll. Brand design.
Hello hello!
Welcome to another edition of Why Join.
Software ate the world. Everyone knows that line. What people missed is the footnote: it ate the parts of the world that were already legible. The parts that could be modeled, digitized, put in a database.
Everything else stayed analog. Not because it was unimportant. Because it was too messy, too contextual, too dependent on judgment calls made by humans who’d seen a thousand similar situations. You couldn’t write rules for it so you just hired people to do it.
That’s the actual unlock with AI. Not that it’s smarter. That it can operate in mess. In ambiguity. In the parts of the economy that software couldn’t touch.
That is an absolutely enormous amount of the economy.
Let’s get into it.
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Who Just Raised 💰
🇺🇸 Moda
💵 Raised: $7.5M seed, led by General Catalyst. Pear VC, Jeffrey Katzenberg’s WndrCo, and execs from Dropbox, Stripe, Segment, Google, and Scale AI also in.
One-liner: AI design agent that actually learns your brand and produces fully editable work.
Why it’s a fave: AI image generators made it easy to create visuals, but the outputs are generic, can’t be edited, and have zero brand awareness. As AI-generated content floods every channel, looking on-brand is becoming the clearest way to stand out. And the most important materials in a company (the pitch deck that closes a round, the sales collateral that wins a deal) still require taste.
Moda gives every company an AI agent that learns their visual language. It indexes your website, Google Drive, past decks, existing assets, and builds an understanding of your brand that gets sharper with every design you create. The output is fully editable on a layered canvas, not a static image. Presentations, social posts, reports, ads. It understands layout, typography, color. Imports and exports from Google Slides and PowerPoint so there’s no workflow disruption.
Founding team is stacked. CEO Anvisha Pai co-founded Dover (AI recruiting, $23M raised from YC, Founders Fund, Tiger Global). COO Ravi Parikh co-founded Heap ($960M valuation, acquired by Contentsquare) and Airplane (acquired by Airtable). CTO John Holliman was employee #1 at Dover.
Hiring: Chief of Staff, Founding AI/ML Engineer, Founding Engineer, Software Engineer - New Grad - NYC
🇺🇸 Glimpse
💵 Raised: $35M Series A, led by a16z. 8VC and YC also in. $52M raised to date.
One-liner: AI agents that recover money retailers wrongly deducted from brands.
Why it’s a fave: Here’s how retail works: a brand ships product to a retailer, sends an invoice, retailer pays. Except retailers routinely pay less than what’s billed and attach a reason (damaged goods, short shipment, whatever). Some deductions are legit. A lot aren’t. A brand might ship inventory perfectly and still get charged for a short shipment. If nobody catches it, that’s just... lost revenue. Quietly, over and over.
The process to actually dispute these is brutal. Teams log into multiple retailer portals, pull scattered documents, review line items, reconcile against internal records, manage disputes end to end. It’s fragmented, unstructured data across siloed systems and teams. Most brands either eat the losses or throw bodies at the problem.
Glimpse’s AI agents log into retailer portals, centralize all the documents, classify each deduction, validate it against internal data (supply chain records, promotion calendars), then automatically file disputes, follow through, apply recovered cash, and sync everything back to the brand’s ERP. Humans stay in the loop for quality assurance and following up on resolution. The system gets smarter with every deduction it processes, building a compounding data advantage across the network.
Hiring: Sales Development Representative, Head of Operations, Growth Marketing Manager, Software Engineer, Customer Success Manager - NYC
🇺🇸 Trayd
💵 Raised: $10M Series A, led by White Star Capital. YC, Suffolk Technologies, and RXR Realty also in. Total funding now $17M.
One-liner: Back-office operating system for specialty trade contractors in construction.
Why it’s a fave: Specialty trade contractors (electricians, plumbers, ironworkers, concrete crews) outnumber general contractors, but almost all construction tech has been built for GCs. The trades get stuck with ADP, Paychex, or Excel. And construction payroll is uniquely painful. A single worker might earn four different pay rates in one day depending on the trade task, project scope, and jurisdiction. Union rules, prevailing wage requirements, multistate taxes. Payroll admins are literally receiving paper timesheets, hand-calculating variable rates, then double-entering numbers into a generic payroll system and again into accounting software. What takes 14 hours of manual work, Trayd does in under 30 minutes.
Hiring: Product Operations Associate, Senior Software Engineer, Business Development Representative - Sales, Sales Account Executive, Senior Implementations Analyst, Enterprise - New York
Open Tabs (stuff we’re reading) 📖
Nvidia-backed Reflection AI raising $2.5B at $25B valuation: The “DeepSeek of the West” is building open-source US AI models to counter Chinese offerings. Nvidia invested ~$800M in a previous round and has been introducing Reflection to potential customers, including foreign governments building sovereign AI infrastructure. JPMorgan in talks to participate through its new $10B Security and Resiliency Initiative. Already cut a deal with South Korea’s Shinsegae Group to build Korean-language models. Part of Nvidia’s new Nemotron Coalition alongside Cursor and Thinking Machines Lab. CEO Misha Laskin, ex-DeepMind: “Open models are Trojan horses for the infrastructure they bring with them.” Investors include Sequoia, Lightspeed, CRV, and 1789 Capital (where Donald Trump Jr. is a partner).
Physical Intelligence raising $1B at $11B valuation: The two-year-old robotics startup founded by ex-DeepMind researchers is in talks to double its valuation in four months. Founders Fund and Lightspeed set to participate. The company builds AI models for robots, has deployed on robotic arms for tasks like folding clothes, making coffee, assembling boxes. Already raised $1B+ from Bezos, CapitalG, Thrive, Lux. Robotics AI is hot right now: Skild AI at $14B, Figure AI at $39B, and Big Tech (DeepMind, Apple, Meta) all piling in.
ChatGPT ads hit $100M annualized revenue in 6 weeks: And that’s from less than 20% of eligible users actually seeing ads. 600+ advertisers on the platform now. Self-serve access launching in April. OpenAI hired former Meta ad exec Dave Dugan to run sales. Expanding to Canada, Australia, NZ soon. This is key to the IPO story: execs told investors they expect $17B+ from ChatGPT consumers in 2026. (Early pilot had rough CTR numbers, nearly 7x below Google benchmarks, but scale is clearly there.)
And then there were none at xAI: Musk’s last remaining cofounder, Ross Nordeen, is out. That’s all 11 original cofounders gone in under three years. Eight left since January alone, most after the SpaceX merger. Musk has cut teams working on Grok Imagine and Macrohard (its AI agent project), gone through multiple reorgs, and admitted publicly that “xAI was not built right first time around.” The company’s valued at ~$250B but still trails OpenAI and Anthropic on scale. They’ve hired a few senior Cursor engineers but the talent bleed is hard to spin.
Mistral secures $830M in debt financing for Paris data center: On top of the €1.2B Sweden investment from February, Mistral is now building a Paris-area data center powered by 13,800 Nvidia GB300 GPUs (44 MW capacity). Backed by seven banks including BNP Paribas and HSBC. Aiming for 200 MW across Europe by end of 2027. For context: Mistral has raised $2.9B total. OpenAI has raised $180B, Anthropic $59B.
NYSE owner drops another $600M into Polymarket: ICE (parent of NYSE) added $600M on top of the $1B it invested in October, bringing total commitment to nearly $2B. Polymarket also acquired a licensed exchange and clearinghouse this year and partnered with Palantir to build a trading surveillance system. Meanwhile rival Kalshi raised $1B+ at a $22B valuation and is pulling ~$1.5B in annual revenue. The prediction market space is getting real, fast, even as lawmakers question whether these platforms are vulnerable to manipulation.
Claude’s consumer growth is skyrocketing: Analysis by Indagari of billions of credit card transactions from ~28M US consumers (conducted for TechCrunch) shows Claude gaining paid subs in record numbers. New subscriber growth spiked between the late January DoD feud coverage and Amodei’s public statement in February. Anthropic says paid subs have more than doubled this year. The Super Bowl ads mocking ChatGPT’s decision to run ads helped too. Claude Code, Cowork, and the new Computer Use feature (lets Claude navigate your computer independently) are all driving upgrades. ChatGPT still way bigger overall, but OpenAI’s uninstalls spiked after the Pentagon deal while Claude hit #1 on the App Store.
Image Credits: TechCrunch Waymo hits 500K paid rides per week: 10x growth in under two years (50K/week in May 2024). Now in 10 US cities, added seven Sun Belt markets in the past year alone. Fleet is still ~3,000 vehicles, meaning they’re squeezing way more utilization out of each car. Still tiny vs Uber (13.5B trips in 2025) but the lead over every other robotaxi company keeps growing. Tesla launched paid rides in Austin in January but still lacks permits for California. 6th gen system coming on the Zeekr Ojai minivan and Hyundai Ioniq 5.
Image Credits: TechCrunch OpenAI kills Sora, $1B Disney deal dies with it: OpenAI scrapped its video gen app and the three-year Disney partnership collapsed with it. Disney had pledged $1B in equity plus licensing of 200+ characters from Disney, Pixar, Marvel, Star Wars. No money ever changed hands. Sora was eating compute without the revenue to justify it, downloads cratered from 6.1M in November to 1.1M in March, and it was losing to Google, Kling, and others. Apps chief Fidji Simo told staff to drop “side quests” and focus on coding and enterprise. OpenAI also deprioritized the “adult mode” sexting feature. The pivot is clear: all in on competing with Anthropic on coding and enterprise.
Who’s Hiring 💼
Oximy: GTM Intern (Founder’s Office), Content Intern (Product + Founder Content), Founding Full Stack Engineer - San Francisco; Remote
Bastion: Account Executive, Senior Software Engineer - NYC
Truewind: Accounting Agents Solutions, Growth Business Development Representative (BDR) - San Francisco; Remote
Mirai: Machine Learning Engineer - Model Optimization, Inference Engineer - Remote; San Francisco; Europe
Clasp: Data Engineer, Full Stack Engineer, B2B Demand Generation Lead, Executive Partner to the COO - Boston, MA/ Recruitment Marketing Manager, Manager, Student Engagement - Remote
Eragon: Applied AI Intern, AI Product Manager, Applied Research Engineer - San Francisco
Mutable Tactics: ML Engineer (perception & state estimation), Robotics Engineer (planning & behaviour) - London
Notch: Product Marketing, Demand Generation & ABM Lead - New York/ Product Designer - Ramat Gan, Israel
Chexy: Marketing & Events Intern - Summer 2026, Customer Success Manager, Full Stack Engineer, Chief of Staff - Toronto
Ambrook: Software Engineer, AI, Content Marketing Lead - New York; Denver; San Francisco; Remote/ Founding Operations Associate - New York
Top Tier Capital Partners: Investment Senior Analyst or Associate - London
Alumni Ventures: Platform Operations Analyst Internship - New York/ Nurture Marketing Intern - Manchester, NH
a16z: Partner 6, Executive Assistant, Crypto - New York
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See you Wednesday, Ryan
Sponsorships: We are now accepting sponsors for Q2 ‘26. If you are interested in reaching my audience of founders, investors, and tech executives, send me an email at chief@whyjoin.xyz.