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🕶️ OpenAI’s $1 power play

🕶️ OpenAI’s $1 power play

Selling shares, selling software—just don’t make it look desperate.

Paula Echeverria
August 07, 2025

Sponsored by

Startups want exits. VCs want liquidity. The market says: not today.

In this edition, we look at the quiet boom in secondary sales (and the awkward politics behind them), OpenAI’s shockingly cheap bid to win over the U.S. government, and the startup that told its engineers to work weekends… or walk.

Also inside: new funding rounds, data leaks, TikTok-driven glasses hacks, and the kind of leadership advice that actually holds up.

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Ten bullets of updates

🫀 CEO shares a simple courage formula: vulnerability plus integrity. Says tough feedback gets easier when you lead with honesty, not perfection.
🎵 ElevenLabs launches an AI music generator trained on licensed data, claiming it’s safe for commercial use: no copyright headaches, just royalty-free beats.
💘 Tinder tests a major redesign with new dating modes and college-only features, aiming to boost engagement and win back younger users.
💻 AI coding startup Codeium tells employees to work weekends or take a buyout, sparking fresh debate over hustle culture in high-growth tech.
👩‍💼 Linda Yaccarino lands a new CEO role just days after leaving X, marking a swift rebound from one of tech’s most scrutinized executive exits..
🌱 A founder says giving back, not chasing growth, became the unexpected engine behind her startup’s success, fueling purpose, resilience, and stronger business outcomes.
🇨🇳 Two arrested for smuggling high-performance AI chips to China; denials of kill switch plans followed.
👓️ TikTok drives users to supercharge sales of “ghost dot” stickers hiding the smart glasses’ recording LED.
⚖️ OpenAI faces a lawsuit over scraping NYT content; user chat data might be under the microscope.
⚠️ A “Tea for men” rival app is leaking user data, including selfies and driver’s licenses; raising serious questions about privacy in niche social platforms.

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🪙 The Unspoken Rules of Selling Out

Photo by Charles Forerunner on Unsplash

With exits still few and far between, early-stage investors and founders are quietly turning to the secondary market to get some cash back. But these deals come with baggage. Selling—even a small slice—can trigger board pushback, founder resentment, or send the wrong message to the market.

There’s a delicate etiquette at play. Investors who try to sell too much, too soon risk looking like they’ve lost faith. Founders hoping for a bit of liquidity often get blocked by their own boards. And employees? They’re usually not even invited to the conversation.

Still, secondaries are booming. The market hit $60B last quarter, and everyone from pre-seed angels to seasoned VCs is trying to navigate these deals without burning bridges. In today’s startup world, getting paid shouldn’t feel like a betrayal; but often, it still does.

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How Much Equity Are Founders Keeping

How much should you actually own of your startup? Most founders shed more equity than they realize by the time they hit Seed or Series A — and it could cost them millions down the line. In this video, we break down founder equity benchmarks, cap table traps, and why owning 5% of a unicorn might still beat 50% of a “meh” business.

🕶️ More videos here 🕶️

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Big investors are buying this “unlisted” stock

When the founder who sold his last company to Zillow for $120M starts a new venture, people notice. That’s why the same VCs who backed Uber, Venmo, and eBay also invested in Pacaso.

Disrupting the real estate industry once again, Pacaso’s streamlined platform offers co-ownership of premier properties, revamping the $1.3T vacation home market.

And it works. By handing keys to 2,000+ happy homeowners, Pacaso has already made $110M+ in gross profits in their operating history.

Now, after 41% YoY gross profit growth last year alone, they recently reserved the Nasdaq ticker PCSO.

Invest for $2.90/Share

_{Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at}_{invest.pacaso.com}_{. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.}

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These companies just raised money

📇 Clay confirms $100M raise at a $3.1B valuation, as its AI-powered relationship management platform gains traction with execs and investor teams.
💳 AI-powered fintech Alaan raises $48M in one of MENA’s largest Series A rounds, fueling its push to modernize corporate spending across the region.
🌐 Tavily raises $25M to help AI agents browse the web in real time, aiming to make autonomous tools smarter, faster, and actually useful.
💸 Lava raises $5.8M to build digital wallets for the “agent-native” economy, betting big on a future where AI agents handle your transactions.

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Turn AI Into Your Income Stream

The AI economy is booming, and smart entrepreneurs are already profiting. Subscribe to Mindstream and get instant access to 200+ proven strategies to monetize AI tools like ChatGPT, Midjourney, and more. From content creation to automation services, discover actionable ways to build your AI-powered income. No coding required, just practical strategies that work.

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🏛️ OpenAI’s $1 Power Move

OpenAI is basically giving ChatGPT Enterprise away to the U.S. government; just $1 per agency for a year. The move, part of a new deal with the GSA, is a clear play to beat Anthropic and Google in the race to power federal workflows with AI.

It’s a clever wedge: all three companies just got listed as approved AI vendors, but only OpenAI is throwing out a price tag this aggressive. That $1 deal also includes 60 days of unlimited access to advanced models and custom onboarding. If you're wondering who’s going to own the government AI stack in a few years, this might be your answer.

The timing tracks with Trump’s new AI agenda, which bans “woke” algorithms from government contracts and encourages faster adoption of AI in federal agencies. So while OpenAI courts public-sector dominance, it also has to play nice with an administration that wants to shape how the tech behaves.