Harry

Podcast host and business intelligence analyst specializing in technology and venture capital.

Claims

As speaker

Mentioned in

Key positions and views

The current AI landscape is defined by rapid, 'leapfrogging' advancements between models, which makes the long-term durability of revenue for any single company more questionable than in past tech cycles.

Venture capital financing announcements often obscure the true economics of a deal through mechanisms like 'tranched rounds,' which give early investors much lower effective valuations than the publicly stated number.

The next generation of AI models, exemplified by Anthropic's unreleased 'Mythos,' possess dual-use capabilities like advanced hacking that are so powerful they warrant being withheld from public release for security reasons.

A specific 'death zone' exists for SaaS companies with Annual Contract Values (ACVs) between $5,000 and $25,000, a concept he attributes to Matt Plank of Rippling.

Large-scale 'circular deals,' where tech giants invest massive sums into their strategic partners and customers (e.g., NVIDIA investing in OpenAI), are becoming a defining trend in the AI ecosystem.

Podcast consensus on Harry

Points of consensus

▶Harry consistently focuses on the immense financial scale and rapid growth of leading AI companies like OpenAI and Anthropic, citing specific revenue figures, valuation multiples, and investment rounds across multiple episodes.

▶He frequently reports on the strategic moves and unreleased capabilities of major AI labs, particularly Anthropic's 'Mythos' model, which he discusses in detail across several podcasts, highlighting its power and the reasons for its withheld release.Apr 2026

▶Harry repeatedly analyzes the financial engineering and investment strategies within venture capital, discussing 'circular deals', 'tranched rounds', and the performance of specific funds like Lightspeed and Hummingbird.

▶Across different episodes, he highlights the strategic importance of key individuals and their predictions, such as Jonathan Ross's forecast for NVIDIA or Matt Plank's view on SaaS pricing.

Points of debate

▶Harry presents a conflicting view on market stability. He highlights massive growth predictions like NVIDIA reaching a $10 trillion valuation and SpaceX's historic IPO, while also noting that publicly traded software stocks are hitting new lows and that rapid AI advancements make revenue durability questionable.Apr 2026

▶He reports on both the immense financial success of AI companies (OpenAI's revenue growth, Anthropic's investor returns) and significant financial turmoil or strategic pivots elsewhere, such as SpaceX's reported $5 billion loss and Thoma Bravo shutting down its growth equity arm.Apr 2026

▶Harry's commentary on Meta is varied. He reports on the company potentially laying off 20% of its workforce while simultaneously noting it has surpassed Google as the world's largest advertising engine, presenting a picture of both contraction and market dominance.Apr 2026

▶He discusses OpenAI's strategic intent to move into the application layer by acquiring Windsurf, while also emphasizing the immense and growing revenue potential of its core offerings through advertising, suggesting a dual-pronged and potentially resource-intensive strategy.

Key themes

▶The AI Arms Race & Advanced Model CapabilitiesApr 2026

Harry frequently discusses the intense, 'leapfrogging' competition between major AI labs like OpenAI, Anthropic, and Google. He places special emphasis on the undisclosed and potentially dangerous capabilities of next-generation models, using Anthropic's 'Mythos' and its ability to find zero-day vulnerabilities as a prime example of this trend.

The focus on unreleased, powerful models suggests that the true value and risk in the AI sector lie in proprietary R&D that the public market cannot yet price, making insider information and leaks critical sources of intelligence.

▶Venture Capital Financial Engineering

A recurring theme is the sophisticated and sometimes misleading financial structures used in venture capital. Harry explains concepts like Sequoia's 'tranched rounds' to obscure entry valuations and the trend of 'circular deals,' where large corporations invest heavily in their own customers to fuel ecosystem growth.

Investors should be skeptical of headline valuation numbers and funding announcements, as the underlying economics for preferred investors can be substantially different and more complex than what is publicly reported.

▶Mega-Cap Financial Performance and StrategyApr 2026

Harry provides specific, data-driven insights into the financial performance of major tech companies. This includes OpenAI's explosive advertising revenue growth, SpaceX's nuanced $5 billion loss driven by an acquisition, Meta's simultaneous market dominance and workforce reduction, and Amazon's rapidly growing $20 billion Trainium chip business.

The analysis indicates a market bifurcation where companies with a clear AI or specialized hardware advantage are experiencing exponential growth, while even dominant legacy tech players face strategic pressures requiring significant operational adjustments.

▶The 2026 IPO Landscape

Harry makes specific, high-conviction predictions about which major tech companies will go public in the near future. He forecasts that Anthropic and SpaceX will IPO in 2026, with the latter being the largest in history, while asserting that other giants like Databricks, OpenAI, and Stripe will remain private.

His predictions suggest that the path to a successful IPO in the current climate requires either a monumental, culturally significant brand like SpaceX or a clear, defensible enterprise niche like Anthropic, while foundational infrastructure players like OpenAI may benefit more from staying private.

Source episodes

Sentiment over time

Not enough data for timeline

Changes over time

Recent Past (15 months prior)

Reports that OpenAI's valuation was $30 billion. He notes its current revenue is approximately half that figure, highlighting the company's extreme growth trajectory.

Present Day

Reports on several major events: Anthropic's accidental leak of the 'Mythos' model, SpaceX's leaked financials showing a $5B loss due to an acquisition, and OpenAI's ad pilot hitting a $100M run rate in six weeks.

2025

Predicts ElevenLabs will scale to $400 million in ARR. He also identifies a trend of 'circular deals' in the market, citing a hypothetical $100 billion NVIDIA investment into OpenAI as a key example.

2026

Forecasts that Anthropic and SpaceX will both IPO, with the SpaceX offering becoming the largest in history. Concurrently, he states OpenAI projects it will generate $2.5 billion in advertising revenue.

2027-2029

Relays OpenAI's forward guidance for its advertising business, projecting revenues to grow from $11 billion in 2027 to $25 billion in 2028, and reaching $53 billion in 2029.

Within 5 Years

Cites a prediction from Jonathan Ross of Grok that NVIDIA's valuation will 'unwaveringly' reach $10 trillion within this timeframe.

Suggested prompts

How does Harry's focus on 'circular deals' and 'tranched rounds' challenge conventional narratives about venture capital investment in the AI sector? &nearr;What are the potential market implications if Harry's reporting on Anthropic's Mythos model and its withheld release due to hacking capabilities is accurate? &nearr;Analyze the consistency of Harry's predictions. How do his bullish forecasts for specific companies like OpenAI and NVIDIA reconcile with his broader concerns about revenue durability in the AI space? &nearr;Based on Harry's claims, what are the key differences in the go-to-market and financing strategies between foundational model companies (OpenAI, Anthropic) and application-layer companies? &nearr;

Key concepts

Corporate Finance & Valuation 5 ep Anthropic 4 ep OpenAI 4 ep Venture Capital 4 ep AI Models 3 ep NVIDIA 2 ep SpaceX 2 ep Meta 2 ep IPOs 1 ep SaaS 1 ep

Notable quotes

“I have Matt Plank at Rippling on the show recently, and he said that five to 25K ACVs is where SaaS companies go to die.”

Harry · Julian Teixeira, CRO @ 1Password: How to Hire and Train Your First Sales Hires

“The amount of Sequoia rounds where it's like, oh, X raises money from Sequoia at 5 billion. Trust me, Sequoia got in at one, but they just club it together and then announce the sum and then the latest valuation. And it's just very misleading.”

Harry · OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN

“Jonathan Ross from Grok said on the show, they will unwaveringly get $10 trillion within a five-year timeline.”

Harry · Cerebras CEO, Andrew Feldman on Why Raise $1BN and Delay the IPO & Why NVIDIA’s Worried About Growth

“[0:00:05 -> 0:00:11] Anthropic unveils Mythos, but withholds it from public release because it's too good at hacking.”

Harry · SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race?

Report last updated: Apr 21, 2026

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