PIN

A newsletter for communities, investors, angels, and founders

Author

Power in Numbers
August 15, 2025

Welcome to PIN’d - our weekly newsletter where we pin (lol, bear with us) the most important tech/startup news of the week for aspiring angels, vc’s, startup investors, founders, etc. Expect a new weekly roundup from us every Friday morning!

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📰 This week’s best news

StubHub has resumed its plan to go public, aiming to start its IPO roadshow after Labor Day and debut later in September. The company paused the process in April due to market volatility from new tariffs. In Q1, revenue rose 10% to $397.6 million, but net loss widened to $35.9 million. StubHub, valued at $16.5 billion before the pause, faces strong competition from Ticketmaster, Vivid Seats, and SeatGeek.

Forbes just dropped their new list for 2025. To qualify, startups must be venture-backed, based in the U.S. and (currently) worth less than $1 billion. Unsurprisingly, artificial intelligence dominates this year—20 of the 25 companies are AI-focused, with applications in military, accounting and health tech.

Bullish surges 83% in trading debut after $1.1 billion IPO

Bullish (BLSH) made a strong public market debut Wednesday, with shares surging 83% to close at $68 on the New York Stock Exchange following the cryptocurrency exchange's $1.1 billion initial public offering. The stock opened at $90 before settling at $68 by market close, giving the Peter Thiel-backed company a market valuation of $9.9 billion.

OpenAI is restoring older models like GPT-4o after backlash over its GPT-5 rollout, which removed the option to choose between models. CEO Sam Altman announced the reversal on X, along with higher usage limits for paying subscribers. The change comes after widespread subscription cancellations and petitions from users whose workflows were disrupted.

41% of all VC dollars deployed this year have gone to just 10 startups

So far in 2025, $81.3 billion (41% of all US VC funding) has flowed to just 10 companies, eight of them in AI. OpenAI alone raised $40 billion, the largest single venture round ever, with xAI and Anthropic following. The concentration of capital is fueling huge competition among investors and raising concerns about reduced diversification.

GitHub CEO Thomas Dohmke is stepping down after nearly four years to start a new venture, and Microsoft will not replace him. Instead, GitHub’s leadership will report directly to Microsoft’s CoreAI team, led by Jay Parikh. The move further integrates GitHub into Microsoft’s AI strategy, ending its run under a single dedicated CEO. Dohmke will stay through the end of 2025 to oversee the transition.

AI and AR startup Squint has raised a $40 million Series B led by The Westly Group and TCV, with Sequoia Capital and Menlo Ventures also participating. Founded in 2021, Squint digitizes veteran factory know-how to boost efficiency and safety. Its platform is already used by companies like PepsiCo, Michelin, and Ford across hundreds of factories. The funding comes as manufacturers look to reshore production and modernize amid geopolitical and technological shifts.

AI search engine Perplexity has made a $34.5 billion cash offer to buy Chrome from Google, promising to keep Chromium open source and invest $3 billion in it. The bid follows a Department of Justice push for Google to sell Chrome after being found guilty of monopolistic practices. Perplexity has raised about $1.5 billion to date and launched its own browser, Comet, last month.

💰 Funding announcement highlights

Confido, a New York-based AI financial operating system for consumer brands, raised $15 million in Series A funding. Footwork led the round, with Watchfire Ventures, Barrel Ventures, Liquid 2, Boulder Food Groups, and Y Combinator also joining.

Casap, a San Francisco-based developer of automation technology for dispute and fraud cases, raised $25 million in Series A funding. The deal was led by Emergence Capital with Lightspeed Venture Partners, Primary Venture Partners, SoF also contributing.

Profound, a one-year startup that develops AI-powered tools that track and improve how brands appear in AI-generated search results, raised a $35 million Series B. Sequoia Capital was the main investor, with Kleiner Perkins, Khosla Ventures, Saga VC, and South Park Commons also participating.

Novig, a New York startup that operates a commission-free, peer-to-peer sports prediction market where users trade directly with each other on game outcomes, raised an $18 million Series A round. Forerunner Ventures led the deal, with Y Combinator, NFX, Perceptive Ventures, and Gaingels also investing.

Evertune, a startup developing AI marketing software that helps brands improve visibility and performance in AI-powered search results, raised a $15 million Series A round. The deal was led by Felicis Ventures.

📚 Interesting reads of the week

AI is creating new billionaires at a record pace

The artificial intelligence boom is minting billionaires faster than any wave in history. Fundraising surges for companies like Anthropic, OpenAI, Safe Superintelligence and Anysphere have driven valuations to unprecedented levels, creating vast private fortunes. There are now 498 AI unicorns worth $2.7 trillion, many founded in just the past two years. While most wealth is still illiquid, secondary sales, acquisitions and eventual IPOs are set to reshape the billionaire landscape.

$13 trillion is stuck in U.S. venture capital and private equity, choking the country’s startup engine. Since 1999, regulatory changes have halved public companies, making IPOs rare and trapping value in private firms. Without liquidity, VC returns collapse, capital dries up, and startup incentives vanish.

The sunk cost fallacy is when we keep investing time, money, or effort into something just because we’ve already put so much in, even if quitting would be wiser. The trap comes from focusing on past investment instead of future benefit, causing wasted resources and missed opportunities. To avoid it, ask if you’d start again today, focus on next steps, and get comfortable walking away.

True contrarianism isn’t about being difficult for its own sake, it’s about having conviction and being right. This article explores three “layers of dependencies” that can hold people back, starting with the need for others’ approval and culminating in focusing only on essential partners and allies. The path to meaningful deviance requires rejecting mimicry, anchoring actions to beliefs, and pursuing change grounded in first principles.

Figma’s IPO soared 250% on its first day, sparking claims it left over $3 billion “on the table.” OnlyCFO argues that most of that figure ignores key factors like secondary sales, a tiny effective float, and IPO-driven demand. While the stock was underpriced at $33, the post-IPO surge was likely amplified by the mechanics of the process, not just mispricing.

💪Tech mafia of the week

Highlights:

💰 Most money raised: Curve

🤑 Total money raised by the Checkout.com Mafia: $408.6 million

Weekly Tech Mafia Leaderboard

The Checkout.com alumni has built some amazing companies. This tech mafia group takes the 98th spot on our leaderboard, with 17 companies founded and $408.6 million raised.

PS: Are you a Checkout.com alum interested in getting your community together to invest in the community (and earn carry/other benefits along the way)? Or are you a member of another community that you think would make for an amazing startup investment community?

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🫶 We’re Here for the Drama

📌 PIN tweet of the week

💼 Who’s hiring in VC?

Looking to get into VC? Below are this week’s curated VC job openings.

Antler is looking for a VC Principal.

Impact Capital Managers is looking for a VC Manager.

Voy Ventures is looking for a VC Analyst.

Ajinomoto Group Ventures is looking for a VC Associate.

IMEC is looking for a VC Manager.

📌 Introducing PinPoint - Get paid to refer your friends to great jobs

Want to earn thousands of dollars for referring candidates to top companies? Sign up to PinPoint.

📠 Fun fact of the week

The first video ever uploaded to YouTube was called "Me at the Zoo," uploaded in 2005 by one of the platform’s co-founders.