AI | and the word of the year is SLOP!! Merriam-Webster crowned “slop” as its Word of the Year, defining it as “low-quality digital content mass-produced by AI.” Ouch. Three years after ChatGPT kicked off the modern AI boom, slop is just about everywhere, and some enterprises are still struggling to turn AI into ROI. An MIT survey found that 95% of companies say they aren’t seeing meaningful returns on their AI investments. While many companies don’t feel they’re seeing ROI, another MIT study estimated that nearly 12% of jobs could already be automated with existing AI capabilities. Companies are increasingly citing AI as a reason to cut entry-level roles or conduct layoffs. That fear is now colliding with regulation. After a string of troubling mental-health incidents involving AI chatbots, dozens of state attorneys general sent a message to the major AI players demanding safeguards against “delusional” or psychologically harmful outputs. Their ask? Independent audits, incident reporting, and real oversight, even as a broader tug-of-war brews between state and federal regulators over who gets to set the rules. The era of awe is fading. The era of accountability is just getting started.

IPO WATCH | We’ve been saying the IPO iceberg melt is “coming soon” for years, but 2026 might finally be the year! SpaceX and Anthropic are topping many IPO watchlists as both look for fresh capital and a little competitive insulation. SpaceX, which reportedly raised money in July at a $400B valuation, has only widened its lead since, launching more payload into orbit than the rest of the world combined (yes, really). With reusable rockets getting cheaper and ambitions stretching from Starlink to Mars, a public debut would be less about validation and more about scale. Crypto exchange Kraken is another one to circle. After insisting in March 2025 that it was in “no rush” to go public, the company quietly and confidentially filed for an IPO in November, just one day after raising new funding at a $20B valuation. Motive, the fleet management and driver safety startup, has been laying the groundwork for its IPO, hiring JPMorgan Chase in August to lead an offering alongside Citi, Barclays, and Jefferies. And then there’s Discord: the gaming adjacent messaging app that walked away from a $10B Microsoft acquisition in 2021. According to the New York Times, Discord was back in early IPO talks as of March 2025, and while there hasn’t been much chatter since, 2026 could be their year 👀

VENTURE CAPITAL | Seed-stage venture is split into two different worlds, and everyone knows which one they want (or can afford) to live in.🌎 Carta’s State of Startup data shows the median seed valuation has crept up steadily over the past eight years, landing around $20M post-money in 2025. But zoom out to the top 5%, and it’s a different universe: seed valuations flirting with $100M, same stage, same label, wildly different expectations. This divergence explains a lot of today’s VC behavior. Fundraising is up again this year, roughly $110B in 2025, but the real momentum is happening earlier and looser, with pre-priced rounds now clearing $1B in deal volume per quarter. SAFEs have become the market’s favorite vehicle: fast, flexible, and just ambiguous enough to keep everyone optimistic. Pair that with valuation caps that stretch from “disciplined” to “vibes-based,” and you get a seed market where price discovery is more art than science. Layer in the social dynamics, and things get even spicier. As one viral VC Twitter thread put it: chasing hot logos may be bad for returns, but it’s often a good fit for fundraising. The Nash equilibrium? Everyone defects, bids up the same deals, and hopes access beats alpha. The alternative, a disciplined portfolio of weird, overlooked companies, might actually perform better, but it requires patience, conviction, and an LP that doesn’t just want the big-name brands. In 2025, seed investing wasn’t just about picking companies. It was about deciding which game you were playing.

INSIDER TRADING | Bet on anything: TV, sports, elections. But what happens when the bettors are the ones holding the nonpublic information: employees, contractors, government officials, who know the outcome before the rest of us? In traditional markets, insider trading rules at least try to make that illegal; prediction markets don’t yet have rules. One Polymarket wallet, AlphaRaccoon, won on 22 out of 23 bets on Google’s 2025 Year in Search rankings, turning about $10,000 into roughly $1M. This week, a wallet quietly piled about $35,000 into Maduro/Venezuela attack markets hours before any public news, then sat on approximately $400,000 in profit once news broke and the internet caught up. There’s been an influx of these types of accounts on Polymarket, with new wallets dropping five-figure first entries, hyper-focused on a single market. Prediction markets are supposed to be truth machines, with prices as probabilities, refined by people with skin in the game. But when insiders can repeatedly monetize information only they have, everyone else is just providing them exit liquidity. Polymarket has gone from a CFTC enforcement action and a forced wind-down to an $8B valuation in three years, which feels exactly like the trajectory you’d expect from a founder who was emailing regulators about prediction markets as a kid. 📈

INSTACART ECONOMICS | Many Instacart shoppers think they’re just ordering milk and eggs, but not all products are priced equally… This month, Consumer Reports conducted a study where 39 volunteers ordered the same 20-item grocery basket from a Safeway in Seattle and took screenshots of their totals. The result: five different prices for the same food. Identical carts ranged from $114.34 to $123.93, a nearly $10 swing, and only 8% of shoppers landed the cheapest option. Same groceries, same store, same day… very different outcomes. 🛒 After acquiring AI pricing startup Eversight in 2022, Instacart began offering retailers software designed to “optimize” prices by dynamically adjusting what different customers see. The company says the tech can boost grocery sales by 1–3% and increase incremental margins by 2–5%. Translation: a few extra dollars here and there, multiplied across millions of carts, adds up fast. For shoppers, though, it raises an uncomfortable question: when you check out on Instacart, are you getting the price or just your price? A week after the Consumer Reports study was published, Instacart just hit the kill switch on its AI pricing experiments, after publishing a handful of blog posts and “fact sheets” about its pricing practices. It's immediately discontinuing its Eversight technology that allowed retailers to run dynamic pricing tests.

Chicago-based startups closed a handful of rounds this month

Vyriad closed a $25M Series B based in Rochester, MN

Champ closed a $55M Series C led by Point 72

Ypsilanti, Michigan-based LuxWall raised a $77M Series C with participation from Kholsa Ventures

Alphyn Biologics, based in Cincinnati, wrapped a $25M Series B

Med-device company RoddyMedical closed a $5M Series A

Iowa-based Mach raised a $7M Seed Round

Fargo-based DetectAuto closed a $2.9M Seed Round

Unemployment in Missouri stayed steady this month at 4.1%, and the National Average did as well at 4.3% ✅

The Midwest Consumer Price Index stayed steady this month at around 3.0%, while the national rate is up 3% on the year ✅

Liquid Future 🔮

In 2026, AI will move from hype to pragmatism 🧠

The earnest, ambitious kid's guide to investors 📚

The New Rules for Platform Dominance 📝

From oil & gas spreadsheets to a soda giant to a $2B exit [38 min]

Uncapped #37 with Saam Motamedi from Greylock Partners [50 min]

Making complex ideas accessible on Think Fast Talk Smart [14 min]

Gearing up for a jam-packed 2026 full of events, dinners, and summits hosted by Redbud (stay tuned)

If Morning Brew’s CEO Alex Lieberman was planning a 12-month, weekly entrepreneurship class, here's how it'd go...

Actually good fundraising advice straight from a founder

The only market sizing guide founders will ever need

What to include in a data room 🗄

Early Stage Financial Template 💰

Need some examples? Check out these 50 pitch deck examples from successful fintech startups

➡️ +200 Non-VC Funding Sources for SaaS Founders

Thinking of raising some capital? Here’s the Due Diligence Checklist every founder should see 👀

YC's essential startup advice

Brian Chesky on when to hire 🧍🏼‍♀️

Metrics 101: What VCs look at while evaluating startups

Get started to build an outbound sales motion with these 130 SaaS Cold Email Templates

🤖 Why code is no longer a moat

A list of low/no code tools to get your company off the ground 🚀

Marc Andreessen on how to hire the best people

The complete guide on How to Interview and Hire ML/AI Engineers (one of our favorite reads on hiring out there)

One of the largest VC lists with over 18k investors 🫰

Founder who 120 VCs—he closed $2.7M in 5 weeks with demand for $5M+. Here's his step-by-step guide to close a round. 💰

📊 All-In-One Startup Metrics Guide - What to track, when and why

Resource page for founders we made here 📒