/
© 2026 RiffOn. All rights reserved.
  1. The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
  2. 20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back
20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Oct 9, 2025

Analyzing OpenAI's power plays with AMD/NVIDIA, the broken venture math of AI deals, VC kingmaking, and the challenging exit landscape.

Increased LP Secondary Sales Are a Healthy Correction to Venture's Illiquidity Problem

With fund lifecycles stretching well beyond the traditional 10 years, LPs are increasingly seeking liquidity through secondary sales. This trend isn't just a sign of pressure but a necessary market evolution to manage illiquid, long-duration assets.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

The AI Industry Is Recreating the 1990s Wintel Monopoly with OpenAI and NVIDIA

The current AI landscape mirrors the historic Windows-Intel duopoly. OpenAI is the new Microsoft, controlling the user-facing software layer, while NVIDIA acts as the new Intel, dominating essential chip infrastructure. This parallel suggests a long-term power concentration is forming.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

OpenAI's User Base Gives It More Power Than Chip Giant AMD

Despite losing money, OpenAI leveraged its massive user base to secure warrants for 10% of AMD. This contrasts with NVIDIA, who received equity in OpenAI, showcasing how user control dictates power in strategic partnerships, even with hardware giants.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Hyper-Growth AI Companies Defy Tradition by Maintaining Flat Revenue Multiples

In the current AI boom, companies are raising subsequent funding rounds at the same high revenue multiples as previous ones, months apart. This is because growth rates aren't decelerating as expected, challenging the wisdom that valuation multiples must compress as revenue scales.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

A Hired CEO Can Scale a Company, But Can't Find Product-Market Fit

Bringing in a professional CEO to replace a founder can succeed only if the company has already achieved product-market fit. If PMF is still elusive, hiring an operator to find it is a fatal mistake. The unique, entrepreneurial act of discovering PMF belongs to the founder.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Private Equity Buyers Have Gone Quiet, Removing a Key Exit Path for SaaS Companies

A significant shift has occurred: private equity firms are no longer actively pursuing acquisitions of solid SaaS companies that fall short of IPO scale. This disappearance of a reliable exit path forces VCs and founders to find new strategies for liquidity and growth.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

OpenAI's App Store Risks Becoming Underutilized Like Slack's Integrations

The initial app integrations for ChatGPT lack a compelling "magic moment" and feel similar to Slack's app ecosystem, where connectors exist but are rarely used for complex tasks. This raises questions about whether users will meaningfully engage with another app marketplace.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Re-Incentivize Stalled Founders with "Equity for Growth" Grants for a Second Act

When a growth company stalls below IPO threshold and PE buyers are absent, the crucial move is to reignite the founder's motivation. An "Equity for Growth" (EFG) grant, tied to future performance, gives vested founders a new reason to pursue a second, multi-year act.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Capital Is a Persistent Moat in AI, Making Bootstrapped Competitors Obsolete

Unlike traditional SaaS where a bootstrapped company could eventually catch up to funded rivals, the AI landscape is different. The high, ongoing cost of talent and compute means an early capital advantage becomes a permanent, widening moat, making it nearly impossible for capital-light players to compete.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Venture Capital Is the Most Forgiving Asset Class for Overpaying on Price

Unlike Private Equity or public markets, venture is maximally forgiving of high entry valuations. The potential for exponential growth (high variance) means a breakout success can still generate massive returns, even if the initial price was wrong, explaining the industry's tolerance for seemingly irrational valuations.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Mega-Rounds for Proven Founders Compress Venture Risk, Justifying Extreme Valuations

Deals like Naveen Rao's $1B raise at a $5B pre-money valuation seem to break venture math. However, investors justify this by stipulating that proven founders in hard infrastructure markets compress key risks, making market size, not execution, the primary remaining question.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago

Unprofitable Companies Can Bestow Market Cap on Suppliers Via User Control

Even while losing significant money, a company's massive user base can be its core asset. This leverage allows it to influence the market cap of its suppliers simply by choosing them, demonstrating that user aggregation is more powerful than immediate profitability in today's market.

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back thumbnail

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 months ago