AI in Logistics, Taxes, and Voice Tech
AI isn’t just generating text—it’s moving freight, automating taxes, and making software engineering faster than ever.
Hello!
Welcome back to Why Join.
Still helping a few great companies hire:
Enterprise AEs (3-5 years at a top B2B software company) – SF/NYC.
BDR/SDRs (1-3 years in SaaS or sharp new grads from top schools with competitive backgrounds). Scrappy, startup-minded, cold-calling experience preferred – SF/NYC.
If that’s you (or someone you know), hit reply—I read every email.
Now, onto this week’s edition.
Sponsored by Wispr Flow
Stop Typing. Start Flowing.
Wispr Flow for Windows & Mac is here—your voice-first dictation tool that’s 3× faster than typing and gets smarter with every word you say.
Why Flow?
Learns as you go—adapts to your vocabulary and edits
Blazing-fast recognition—keeps up with your thoughts
Works everywhere—MS Word, Slack, Teams, WhatsApp, emails, even code editors
Supports 100+ languages, including UK English & Hinglish
Now with Team Plans—equip your entire startup and reclaim hours of wasted typing.
Want to sponsor a future edition? Let’s talk.
This Week in Startups
🇺🇸 Graphite
Funding — Series B, $52M; Investors — Accel (lead), Menlo Ventures (Anthology Fund), Anthropic, Shopify Ventures, Figma Ventures, a16z, The General Partnership.
TL;DR: AI-powered code collaboration and review
AI coding tools are taking over, with developers adopting them at record speed. Y Combinator says a quarter of its latest batch has 95% of their code written by AI. But writing code is one thing—reviewing it is another.
Graphite focuses on AI-powered code review, helping developers catch errors, suggest fixes, and streamline collaboration. Unlike generic AI assistants, Graphite is built for large engineering teams, allowing them to define custom patterns and filter sensitive data to ensure security.
Now, it’s spinning out Diamond, an AI tool that automatically catches bugs before they hit production. Graphite has seen 20x revenue growth in 2024 and now serves 500+ companies.
Hiring: Software Engineer, Product Marketing Lead, Founding Account Executive - New York
🇺🇸 Town
Funding — Seed, $18M; Investors — First Round Capital (lead), Conviction, Alt Capital, Defy, Depth, Mischief, WndrCo.
TL;DR: Small business tax automation
Big corporations have tax teams. Small businesses? They’re stuck with overwhelmed accountants or DIY tax software. The result? Higher costs, missed deductions, and last-minute stress.
Town acts as a full-service tax department for small businesses—without the overhead. Its AI-powered platform automates tax prep, identifies savings, and connects directly to financial systems. Plus, dedicated advisors provide real support, not just tax filing.
Hiring: Designer, Front-End Engineer, AI Product Engineer - San Francisco
🇺🇸 Augment
Funding — Seed, $25M; Investor — 8VC.
TL;DR: AI-powered logistics assistant that takes the grunt work out of freight
The $900B freight industry still runs on emails and phone calls—hundreds of them, every day. Brokers, shippers, and carriers are drowning in back-and-forth just to book and track shipments. Augie, Augment’s AI assistant, handles it all. It emails, calls, negotiates rates, and manages workflows so teams can focus on the deals that matter.
Harish Abbott (ex-Shopify, sold Deliverr for $2.1B) is behind this one. Early customers already move $20B+ in freight, including Arrive Logistics and NFI.
Hiring: Customer Success Representative - Chicago; Product Marketing Manager - Remote; Business Operations and Strategy Associate - Chicago; Software Engineer - San Francisco
🇺🇸 Cartesia
Funding — Series A, $64M; Investors — Kleiner Perkins (lead), Index Ventures, Lightspeed, A, Factory, Greycroft, Dell Technologies Capital, Samsung Ventures.
TL;DR: AI-generated voices that don’t sound AI-generated
AI voices have improved, but most still sound... off. They’re either high-quality but slow, or real-time but robotic. Cartesia says it can do both.
Its new Sonic 2.0 model generates speech in 90ms (40ms in turbo mode) while maintaining high fidelity. 10,000+ customers already use it across media, gaming, and customer support.
The secret? State space models (SSMs)—an alternative to transformers that processes speech continuously in real time, cutting latency and costs while improving naturalness and scalability.
Hiring: Intern (Software Engineer), PhD Research Intern (Spring/Summer 2025), Chief of Staff, Business Operations, Content Marketing Manager, Founding Product Marketer, Founding Sales, Software Engineer, Designer - San Francisco
Top News
X Raises Nearly $1B, Holds $44B Valuation: Elon Musk’s X just raised close to $1 billion, keeping its valuation in line with the $44 billion he paid in 2022. Musk himself pitched in, and part of the cash might go toward debt. Investors like Darsana Capital and 1789 Capital joined the round—both longtime Musk backers. Meanwhile, X’s ad business is recovering, though Fidelity still values its stake 68% lower than before. Musk’s other ventures are soaring (SpaceX at $350B, xAI eyeing $75B), but Tesla’s down 40% this year, feeling the heat from China’s BYD.
Cognition AI Scores $4B Valuation: Cognition AI just pulled in hundreds of millions, doubling its valuation to nearly $4 billion. The round, led by 8VC, also included Founders Fund and Khosla Ventures—showing VCs are still betting big on AI, especially in coding. Cognition’s star product, Devin, is pitched as “the world’s first AI software engineer.” With rivals like Anysphere chasing a $10B valuation and StackBlitz raising at $700M, the AI coding space is on fire.
Google Snaps Up Wiz for $32B—Its Biggest Deal Yet: Google is making its biggest acquisition ever, buying cybersecurity firm Wiz for $32 billion in cash. The deal, set to close next year pending regulatory approval, will fold Wiz into Google Cloud, boosting its security offerings as it battles Microsoft and Amazon. Wiz, founded in 2020, previously walked away from a $23B bid, betting on an IPO instead. Regulatory scrutiny looms, with antitrust watchdogs keeping a close eye on Big Tech. But for now, Google’s cloud play just got a serious security upgrade. The biggest winners? Wiz’s investors—Sequoia, a16z, Index Ventures, and Greenoaks.
Rippling vs. Deel: HR tech rivals Rippling and Deel are locked in a lawsuit straight out of Hollywood. Rippling accuses Deel of corporate espionage, claiming an insider fed Deel confidential data—including sales pipelines and pricing—for months. The kicker? When confronted, the alleged mole locked himself in a bathroom before fleeing. Deel denies any wrongdoing and is firing back with counterclaims, calling Rippling’s accusations “sensationalized.” But this isn’t their first clash—Rippling previously restricted ex-employees from selling vested equity if they joined competitors like Deel. Meanwhile, Deel has faced separate legal scrutiny over alleged sanctions violations. With Rippling valued at $13.5B and Deel at $12B, this battle isn’t just about lawsuits—it’s about who dominates the HR tech market.
Klarna’s IPO: Swedish buy-now-pay-later giant Klarna has filed to go public on the NYSE under the ticker "KLAR", reporting $2.8B in revenue and a $21M profit in 2024. Once valued at $46B, Klarna is now eyeing an IPO valuation between $15B and $20B. Adding fuel to its debut, Klarna just secured an exclusive BNPL deal with Walmart—bad news for rival Affirm. The fintech sector has been stuck in a deep freeze. In 2021, fintech IPOs raked in $222.7B in VC exit value. Over the last three years? Just $28.7B. Klarna’s public debut is a major test case—if it thrives, others may follow. If it stumbles, the drought continues.
Billionaires wanted it, but 66,930 everyday investors got it first.
When incredibly valuable assets come up for sale, it's typically the wealthiest people that end up taking home an amazing investment. But not always…
One platform is taking on the billionaires at their own game, buying up and securitizing some of the most prized blue-chip artworks for its investors.
It's called Masterworks. Their nearly $1 billion collection includes works by greats like Banksy, Picasso, and Basquiat. When Masterworks sells a painting – like the 23 it's already sold – investors reap their portion of the net proceeds.
In just the last few years, Masterworks investors have realized net annualized returns like +17.6%, +17.8%, and +21.5% (from 3 illustrative sales held longer than one year).
Now, you can skip the waitlist with OUR EXCLUSIVE LINK.1
Who's Hiring
FUSE Ventures: Analyst/Associate - Seattle/Bellevue
Quona Capital: Asia Investment Associate - India
MongoDB Ventures: Analyst - San Francisco/New York
Distributed Ventures: Associate - Chicago
Nauta: Investment Analyst Intern - Barcelona
Chalk: Sales Development Representative, Account Executive, Software Engineer - San Francisco/New York
Modal: Account Executive, Member of Technical Staff - Product (Frontend) - New York
Norm AI: Full-Stack Engineer, Legal Implementation Associate, Legal Engineer - Senior Analyst - New York
Decagon: Head of Sales Development, Brand Designer, Software Engineer, Product Designer, Product Manager, Business Recruiter - San Francisco
Encord: US Founding Engineer - San Francisco; Business Development Representative - London/San Francisco; Growth Associate - San Francisco; Paid Media Specialist - London; Chief of Staff - London; Founders Associate - London
Tabs: Software Engineer, Partnerships Manager, Applied AI Engineer - New York
Tomo Mortgage: Business Development Representative - New York
That’s it for today.
See you Saturday—Chief
See important Reg A disclosures at masterworks.com/cd.