💰 Inside the Windsurf–Google deal fallout

Weeks after it emerged that Google paid $2.4B to license Windsurf’s tech and hire its CEO plus 40 key staff, more details reveal why the deal stirred controversy in Silicon Valley.

🖱 Half of Google’s payment ($1.2B) went to investors, including Greenoaks, Kleiner Perkins, and General Catalyst — Greenoaks turned $65M into ~$500M.

🖱 The other half was compensation for the 40 hires, with a large share going to co-founders Varun Mohan and Douglas Chen.

🖱 ~200 remaining employees saw no payout despite hopes from an earlier $3B OpenAI acquisition attempt.

🖱 Investors and founders left Windsurf with $100M+ in capital, but opinions differ on whether it could’ve been used to pay all employees without sinking the company.

🖱 Some Google hires had stock grants revoked and vesting restarted, delaying full payouts by 4 years.

🖱 Vinod Khosla called the move “a bad example of founders leaving their teams behind.”

🖱 Eventually, Cognition acquired Windsurf’s remaining entity and staff for an estimated $250M, ensuring those employees got a financial benefit.

A lucrative win for VCs and founders — but a cautionary tale for startup teams betting on a big exit.

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🚀 What Startups Y Combinator Wants — Fall 2025

Y Combinator has updated its Requests for Startups, highlighting the areas it’s most eager to back. Almost all of them are now AI-focused. Here’s a condensed look at the fresh list.

🖱 Retraining Workers for the AI Economy – AI tools (possibly with AR/VR) for quickly training electricians, technicians, welders, and other skilled workers to meet infrastructure needs.

🖱 Video Generation as a Primitive – Building new applications and infrastructure for low-latency, unlimited AI-generated video as a core creative tool.
• The First 10-person, $100B Company – Leveraging AI agents to create ultra-efficient teams with unprecedented revenue per employee.

🖱 Infrastructure for Multi-Agent Systems – Developer tools for building, scaling, and maintaining distributed AI-agent architectures.

🖱 AI-Native Enterprise Software – Next-gen enterprise platforms deeply integrated with AI, replacing traditional “systems of record.”

🖱 LLMs Instead of Government Consulting – AI services that replace expensive government consulting contracts from firms like Deloitte and Accenture.

YC’s message is clear: if you’re building for AI-first markets with high leverage and big vision, they’re listening.

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👆 Round sizes for software startups over the past 12 months.

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🖥 Perplexity makes $34.5B bid to buy Chrome from Google

AI search startup Perplexity has made an unsolicited $34.5B cash offer to acquire Chrome, pledging to keep Chromium open source, invest $3B into it, and maintain Google as the default search engine.

🖱 Offer follows DOJ’s proposal that Google be forced to sell Chrome after monopoly ruling
🖱 Chrome holds ~68% global market share, making it the dominant browser
🖱 Perplexity’s bid exceeds its own $18B valuation and $1.5B total funding
🖱 DOJ could set divestment terms as early as this month, attracting multiple bidders

If approved, the move would give Perplexity one of the most valuable browser assets in the world - without touching its search defaults.

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🚀 Risk as the gateway to high returns

History shows that the most rewarding deals are rarely the safest ones. True success often comes from taking calculated risks in opportunities with strong growth potential. While most investors stick to the comfortable path, those willing to step into uncertainty often reap outsized rewards.

Examples:

🖱IPOs can be volatile, but some deliver rapid growth — Twilio’s stock more than doubled shortly after going public.

🖱 Cryptocurrencies are highly risky, yet early Bitcoin backers saw life-changing gains.

🖱 Venture capital comes with a high failure rate, but a winning startup can return multiples on the initial investment.

In investing, discomfort often signals the possibility of extraordinary upside.

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📊 Which VCs got in early on today’s $5B+ startups

Crunchbase ranked funds by how often they entered Series A or B rounds of companies now valued at $5B or more.

🖱 Accel leads with 12 Series A and 13 Series B bets

🖱 Index Ventures, IDG Capital, Lightspeed, and General Catalyst follow closely

🖱 Data excludes cases where the company was already a unicorn at its first round — rare, but common in AI

A clean snapshot of who’s spotting mega-winners before they blow up.

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📱 Apple is not having its BlackBerry moment

Business Insider claims Apple is missing the AI wave just like BlackBerry missed touchscreens. The comparison doesn’t hold up, BlackBerry lost the platform war, not the hardware war.

🖱 BlackBerry’s real killer was the iOS/Android app ecosystem - endless apps for users, endless users for devs.

🖱 Touchscreen vs. buttons was secondary. Big companies can change form factors — ecosystems are harder.

🖱 For Apple to be at risk, devs would need to skip mobile apps entirely and build straight for GPT or other AI-native platforms.

🖱 We’re far from that, and Apple could acquire an AI leader long before it becomes a threat.

Until AI platforms replace the App Store as the go-to launchpad, Apple’s not in danger of a BlackBerry-style collapse.

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🔎 Due Diligence hacks they don’t teach in VC handbooks

You can spin a perfect pitch deck with AI, but you can’t spin the energy of a team, the loyalty of employees, or the founder’s true mindset.

Early-stage due diligence is shifting away from just reading metrics and projections. The most revealing insights often come from creative, off-the-record moves that catch founders in real life, not in presentation mode.

Here’s how the savvier VCs do it 👇

🖱 Talk to ex-employees - the ghosts of startups past. Reach out on LinkedIn or via mutuals to ask why they left. Sometimes the tone says more than the words. Silence can be the loudest answer of all.

🖱 Chat with office neighbors. Other tenants notice patterns like when lights go off and laptops close. If that’s consistently 5 p.m., it raises questions about commitment and pace.

🖱 Probe by offering to buy shares from insiders. If early investors, founders, or key staff are quick to sell (even at a discount), it’s often a sign they’ve lost conviction in the company’s future.

🖱 Test loyalty by trying to poach a key hire. A friendly “job offer” via a portfolio company can reveal whether a star engineer is rooted in the mission or already halfway out the door.

🖱 Schedule a weekend meeting. Founders in the heat of building usually make it happen. A flat “no” without context might hint at a mismatch between words and hustle.

🖱 Cold-call customers, not the ones they hand-pick. Ask bluntly, “What would you change about the product?” The honest answers tell you the real product-market fit.

🖱 Audit personal social media. Instagram, X, or even TikTok can reveal more than polished LinkedIn profiles. Lavish trips during a cash crunch? Public industry rants? It’s all signal.

🖱 Work from their office for a day. The atmosphere doesn’t lie. Is there energy, urgency, and collaboration — or silence, clutter, and drift?

Spreadsheets show the story founders want to tell.
The vibe shows the story you actually need to know.

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📊 How co-founders split equity in startups

Only 1 in 10 startups with four founders split equity evenly. According to Carta, whether shares are split equally or not has no measurable impact on a startup’s success.

The time until hiring the first employee has also grown - now often reaching up to three years. And in recent years, the number of solo founders has been steadily rising.

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💉 Fountain Life raises $18M to expand AI-powered longevity centers

Founded by Dr. William Kapp with co-founders Tony Robbins and Peter Diamandis, Fountain Life focuses on early detection, optimization, and regenerative therapies to extend healthy lifespan.

🖱 Four centers already open, with Houston, LA, and Miami next
🖱 Memberships include full-body scans, 100+ biomarker blood tests, and AI health tracking via the Zori app
🖱 Pricing: $21.5K/year for full service, $10.5K/year for testing only
🖱 Series B led by EOS Ventures, bringing total funding to $108M
🖱 Cases include catching early kidney cancer and detecting a brain aneurysm before symptoms

Longevity medicine is still niche and pricey, but Fountain aims to scale access by training other clinics in its methods, betting that prevention-focused health tech will go mainstream.

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📄 LOI: the first step in sealing a deal

A Letter of Intent (LOI) is an informal document that often marks the official start of a transaction process. It’s not a binding contract, but it frames the key terms and sets the tone for negotiations.

🖱 Outlines valuation, structure, and main deadlines for the potential deal
🖱 May include exclusivity so talks happen only between the involved parties
🖱 Can detail due diligence obligations before signing a final agreement

For founders, every clause matters - unclear language can create unwanted commitments.

For investors, precision ensures there’s no room for misinterpretation.

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📈 Sub-$5M VC rounds are fading fast

A decade ago, over 70% of US VC deals were under $5M. Now it’s less than half that, with PitchBook data showing the decline accelerating since early 2024. Bigger funds and founder expectations are reshaping seed-stage investing.

🖱 Multi-stage funds are pushing up round sizes, crowding out smaller seed investors
🖱 Founders are drawn to big-brand firms, even if they get less hands-on support later
🖱 Some startups are asking for more capital early, pricing out boutique investors
🖱 AI hype and power-law thinking are fueling larger early rounds

If the trend continues, early-stage founders may find fewer small, founder-friendly checks and more pressure to grow fast under big-money expectations.

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📉 How Benchmark Capital is losing partners — and time

Benchmark Capital, the cult VC firm behind early bets on eBay, Uber, and Snapchat, built its brand on small teams, disciplined early-stage deals, and avoiding hype. But that same conservatism is now costing it top talent and market relevance.

🖱 Since March 2024, three younger partners have left - Miles Grimshaw (to Thrive Capital), Sarah Tavel (now venture partner), and Victor Lazarte (launched his own fund).

🖱 Departures stem partly from FOMO - the firm’s cautious approach blocked access to high-quality AI and frontier tech deals.

🖱 Missed opportunities include Stripe, Coinbase, OpenAI, and Anthropic, eroding connections with key market players.

🖱 Current leadership - Peter Fenton, Eric Vishria, and Chetan Puttagunta, has strong track records but faces skepticism over recent bets.

🖱 Benchmark’s understated investment in AI agent startup Manus drew criticism over perceived China ties.

Benchmark’s legacy was built on picking winners early and backing them hard. To stay relevant, it may need to evolve, attracting star partners who could run their own fund, but choose to play for the brand instead.

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🔎 How VCs run due diligence: 5 key stages

Before investing, venture funds run a deep dive into a startup across several dimensions to reduce risk and validate potential.

Here’s what they look at:

🖱 Team — Assessing the founders’ experience, past achievements, motivation, and ability to work together under pressure. A cohesive team with a clear understanding of the market is a major plus. Weak founder dynamics are one of the top reasons VCs walk away.

🖱 Market — Analyzing total addressable market (TAM), growth rate, competitive landscape, and key industry trends. Big and expanding markets increase the odds of a venture-scale return, while niche or shrinking markets are red flags unless the product has strong defensibility.

🖱 Product — Reviewing the stage of development, whether there’s real customer validation, and what technological or operational risks could block scaling. Pilots, paying customers, and clear user adoption metrics weigh heavily here.

🖱 Financials — Looking at revenue streams, burn rate, unit economics, and capital structure to gauge how sustainable and scalable the business is. Funds want to see enough runway and a clear path to future growth without constant emergency fundraising.

🖱 Legal — Checking intellectual property rights, ownership structure, existing contracts, and any litigation or compliance risks. This protects the investment and ensures the startup actually owns what it’s selling.

Strong performance in all five areas not only secures funding but also builds trust with investors and often speeds up the deal process.

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📊 Which top VCs hunt in packs — and which go solo

PitchBook ranked leading venture firms by how often they invest alongside other heavyweight funds.
At the top - those who almost always join deals with fellow giants.
At the bottom - the lone wolves.

🖱 “In the trend” startups often land investors from the first group.
🖱 Unusual or contrarian plays are more likely to attract the second.
🖱 Either way - landing any name from this list is already a strong signal.

A quick reminder that investor fit can be as important as the check size.

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💊 Eli Lilly bets $1.3B on AI-powered obesity drugs

Eli Lilly is partnering with Boston’s Superluminal Medicines in a $1.3 billion deal to develop oral treatments for obesity and other cardiometabolic diseases using AI.

🖱 Lilly gets exclusive rights to drugs discovered via Superluminal’s AI platform targeting GPCR proteins, a promising but underexplored pathway in obesity treatment.

🖱 The obesity drug market could reach $150B by the 2030s, and Lilly aims to maintain its lead after the success of its GLP-1 blockbusters like Zepbound.

🖱 Superluminal’s backers include RA Capital, Insight Partners, and NVIDIA’s venture arm; its in-house rare obesity drug is not part of this deal.

With obesity drugs becoming one of pharma’s biggest battlegrounds, Lilly is arming itself with AI to stay ahead.

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🦄 July’s new unicorns: 13 companies join the billion-dollar club

Thirteen startups crossed the $1B valuation mark last month, with AI still leading the charge but strong showings from e-commerce, healthcare, and more.

🖱 AI — Lovable (Sweden, vibe-coding), Fal (AI media creation), Reka AI (multimodal AI)
🖱 E-commerce — Etraveli (Sweden, flight booking), Ninja (Saudi Arabia, grocery delivery in MENA)
🖱 Data analytics — Anaconda (Python data analysis & project management)
🖱 Energy — CATL Intelligent (China, AI-powered battery design)
🖱 VR/AR — Xpanceo (UAE, smart contact lenses)
🖱 Healthcare — Ambience Healthcare (medical documentation assistant)
🖱 HR — LumApps (France, mobile workforce management)
🖱 Entertainment — Substack (subscription newsletters)
🖱 Telecom — Airalo (Singapore, travel eSIMs)
🖱 Transport — Rivian (EVs)

There were also five notable exits: IPOs from Figma, Geek+, and Accelerant, plus acquisitions of Windsurf by Cognition and Iodine Software by Waystar.

The mix shows AI’s continued dominance, but also that billion-dollar status is still achievable in more traditional sectors if the execution and timing are right.

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📊 Crypto Venture Weekly: August 11–15, 2025

$1.26B raised across 20 projects this week, led by Bullish’s $1.1B IPO. Alongside fundraising, $1.77B in digital asset treasury allocations made headlines, and Offchain Labs picked up ZeroDev to bolster smart account infra.

Here’s what the top 9 are building 👇

🖱 Bullish ($1.1B IPO, BlackRock, ARK Invest)
Centralized institutional crypto exchange and parent of CoinDesk, going public at a $5.41B valuation.

🖱 1Kosmos ($57M, Forgepoint, Oquirrh, NextEra)
Distributed identity cloud service storing encrypted data on a private blockchain.

🖱 Shrapnel ($19.5M, Gala Games, Polychain)
Free-to-play FPS with digital ownership, aiming to merge Web3 and gaming culture.

🖱 Transak ($16M, IDG, Tether, 1kx)
Payments infrastructure provider powering stablecoin and crypto on/off ramps.

🖱 USDai ($13M, Framework, Big Brain, Arbitrum Foundation)
Stablecoin backed by AI hardware collateral, designed to generate yield.

🖱 Mesh ($10M, Coinbase Ventures, PayPal Ventures, Bybit)
Payment network linking exchanges, wallets, and PSPs for seamless stablecoin conversions.

🖱 Mecka ($8M, Neo, Framework, Mechanism)
Decentralized data layer for AI-driven robotics and automation.

🖱 Hyperbeat ($5.2M, Electric, ether.fi, Coinbase Ventures)
Yield infra built on Hyperliquid, tapping into the exchange’s growing ecosystem.

🖱 HoneyCoin ($4.9M, Flourish, Stellar, Visa)
Stablecoin payment rails for emerging markets, starting with Africa.

Investor focus this week was split between exchange infra, stablecoin rails, and the crossover between AI and crypto.

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🎂 Steve Wozniak at 75: choosing joy over empires

Unlike many of his peers, Woz never chased wealth, power, or corporate dominance. On his 75th birthday, he reminded fans of the philosophy he set as a teenager: “Life was never about accomplishment, but about Happiness, which is Smiles minus Frowns.”

🖱 Gave away much of his Apple fortune, focusing instead on museums, arts, and education in San Jose
🖱 Designed the Apple II, a breakthrough that brought computing into homes and schools worldwide
🖱 Supported digital rights through the Electronic Frontier Foundation and children’s education projects
🖱 Remains active in tech forums and continues inventing, now working on space sustainability

Woz’s legacy isn’t just the machine that helped launch the PC era - it’s proof that true impact doesn’t require selling out.

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📈 Gemini files for IPO

The Winklevoss twins’ crypto exchange and custodian Gemini has filed to go public on Nasdaq under the ticker GEMI.

Founded in 2014, Gemini offers an exchange, USD-backed stablecoin, and a crypto rewards credit card.

🖱 2024 results: $142M revenue, $158.5M net loss
🖱 H1 2025: $67.9M revenue, $282.5M net loss
🖱 Joins Circle ($1.2B IPO in June) and Bullish ($1.1B IPO this month) in bringing major crypto firms to the market

With Trump’s administration easing regulations, the IPO window for crypto is reopening, but Gemini’s numbers show profitability will be the harder battle.

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🧪 US sees zero biopharma IPOs in Q2 — first since 2016

For the first time in nearly a decade, the US had no VC-backed biopharma IPOs in Q2 2025, according to PitchBook.

The freeze reflects weak post-IPO performance, a glut of biotech listings from 2020–21, and still-elevated interest rates.

🖱 Biopharma IPOs have underperformed for 18+ months, draining investor appetite
🖱 VC funding also fell — $5.4B across 198 deals, the lowest since 2020
🖱 Down rounds and valuation resets are becoming the norm in private markets
🖱 Regulatory noise around drug pricing adds to investor caution
🖱 Morningstar’s US Biotech index is down ~20% YoY, despite recent recovery

Investors expect a rebound by early 2026 as new AI-driven healthcare startups mature. But for now, liquidity is coming from M&A, not Wall Street.

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