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OpenAI $830B vs Anthropic $380B: The Future of Private Market Pricing with Tyson Hendricksen | E24

February 24, 2026

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  • OpenAI is reportedly close to finalizing a massive $100 billion funding round at an $830 billion valuation, dwarfing previous private rounds, while competitor Anthropic is valued at $380 billion. 
  • Stripe is maintaining high private market valuations ($140B tender offer) and actively creating employee liquidity through secondary tenders, suggesting a potential long-term private existence. 
  • The Supreme Court struck down Trump's emergency tariffs in a 6-3 decision based on the major questions doctrine, though the split ruling suggests future tariff challenges are likely using different statutory authorities. 
  • The secondary market is expanding due to companies staying private longer, increasing demand for employee liquidity, and longer timeframes to IPO (11-15 years). 
  • OpenAI's projected cash burn of $100 billion over the next few years rivals or exceeds historical corporate spending like Meta's VR/AR initiative and the Apollo missions, raising questions about sustainability. 
  • The Valuation Corner segment ultimately favored Anthropic over OpenAI as the better bet due to its trajectory of gaining enterprise LLM market share, recent funding led by purely financially motivated investors, and lower projected cash burn. 

Segments

Initial Market News Recap
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(00:00:53)
  • Key Takeaway: The private market is seeing unprecedented funding rounds, particularly in AI.
  • Summary: The episode opens by highlighting OpenAI’s rumored $100 billion raise at an $830 billion valuation and Anthropic’s $380 billion valuation. Stripe’s employee tender offer reached $140 billion, and Databricks was valued at $134 billion following a funding round. Harvey AI also jumped to an $11 billion valuation.
OpenAI vs. Anthropic Valuation
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(00:03:12)
  • Key Takeaway: Anthropic might be the better bet on a valuation basis due to OpenAI’s higher valuation despite OpenAI leading in fundraising dollars.
  • Summary: OpenAI leads in total fundraising dollars, having broken the Saudi Aramco IPO record, but Anthropic is gaining ground in the B2B segment. The speaker argues that Anthropic at $380B might be a better bet than OpenAI at $830B, suggesting OpenAI has lost some B2B market share.
Stripe’s Private Market Strategy
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(00:04:02)
  • Key Takeaway: Stripe’s successful management of employee liquidity via tender offers at rising valuations suggests they may never need to go public.
  • Summary: Stripe’s $140 billion employee tender offer continues to maintain or increase prior valuations, allowing them to create liquidity without a primary raise. Companies like Stripe can sustain private status indefinitely if they consistently provide liquidity and manage valuation resets carefully, unlike many other private firms.
Databricks Valuation Context
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(00:06:38)
  • Key Takeaway: Databricks’ $134 billion private valuation implies a 25x ARR multiple, significantly higher than public comparable Snowflake’s valuation.
  • Summary: Databricks completed a funding round at $134 billion, supported by 65% year-over-year growth, exceeding $5 billion in revenue. This private valuation is substantially higher than Snowflake’s public market valuation, suggesting they benefit from staying private until public SaaS multiples potentially align.
Harvey AI Valuation Surge
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(00:08:39)
  • Key Takeaway: Harvey AI’s rapid valuation increase to $11 billion, just months after an $8 billion round, reflects investor confidence in AI disruption within the legal sector.
  • Summary: Harvey AI raised $200 million at an $11 billion valuation, marking a $3 billion jump from its previous round. This valuation is over 50x ARR, driven by the perceived threat AI poses to established public legal tech companies like CS Disco.
SCOTUS Tariff Ruling Analysis
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(00:11:07)
  • Key Takeaway: The Supreme Court struck down emergency tariffs using the major questions doctrine, but the narrow 6-3 split suggests future presidential tariffs may be attempted under different statutory authorities.
  • Summary: The 6-3 decision, supported by three conservatives (Roberts, Gorsuch, Barrett) on major questions doctrine grounds, invalidated the IEPA tariffs. The split indicates that Trump may attempt to reapply tariffs using other trade authorities, like Section 122 of the Trade Act of 1974, which limits tariffs to 15% for 150 days.
Introduction to Tyson Hendricksen
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(00:22:30)
  • Key Takeaway: Tyson Hendricksen’s background includes Olympic training, stand-up comedy, and social impact work in Uganda before founding Notice.co to address private market pricing transparency.
  • Summary: Hendricksen spent five years in Uganda farming pineapples and trading peanuts after initial social impact ideas failed to scale permanently. He entered the secondary market by helping a friend with Palantir liquidity issues, realizing the market’s fragmentation and lack of pricing data. Notice.co was founded to aggregate data from independent brokers to create transparent pricing.
Notice.co Business Model
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(00:28:29)
  • Key Takeaway: Notice.co prioritizes being a data-first, open public utility, contrasting with competitors who focus on institutional marketplace volume.
  • Summary: Notice.co focuses on product and transparency, publishing real-time pricing data publicly, which attracts 150,000 to 300,000 monthly users. Because Notice is not a broker-dealer, brokers willingly share data, allowing Notice to rank them based on trade volume and recency, fostering a content flywheel.
Private Market Index Performance
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(00:33:47)
  • Key Takeaway: The Notice.co 50 index (weighted private market benchmark) significantly outperformed the public QQQ index during 2021 and has recently separated again, indicating private market divergence.
  • Summary: The weighted private index shows a massive gap over the public index in 2021, with the private market bottoming around mid-2023 before taking off again, coinciding with the AI surge. The platform tracks about 1,200 companies in real-time out of 8,000 in its database.
Market Concentration and Discounts
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(00:44:48)
  • Key Takeaway: Market concentration is heavily focused on the top 20-30 AI names, leading to better potential discounts for buyers in the next 200-300 companies outside that visible tier.
  • Summary: The market is currently focused almost exclusively on AI names, sucking liquidity away from other sectors. Companies ranked 300+ that still show strong growth (e.g., 40-50% fintech growth) are seeing better discounts because there is no demand for them, unlike the premium paid for top-tier names.
Secondary Market Liquidity Dynamics
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(00:49:00)
  • Key Takeaway: Large primary funding rounds often inject significant capital into the secondary market via SPVs, creating expensive, primary-like access for retail investors, often without the seller retaining long-term interest.
  • Summary: Primary rounds are sometimes syndicated excessively into the secondary market, leading to secondary prices jumping 30% over the primary price within 30 days. Investors in these structures often pay high upfront fees (5-10% carry) but receive primary protections like liquidation preference, unlike true secondary buyers.
Secondary Market Liquidity Drivers
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(00:53:04)
  • Key Takeaway: Lack of options for smaller transactions ($5M-$10M) creates significant discounts for buyers.
  • Summary: Smaller private asset transactions often result in bargains or structured deals advantageous to the buyer due to limited market activity for sellers. Companies staying private longer increases demand for employee liquidity programs to aid retention. The secondary market is expanding across all paths, driven significantly by employee liquidity needs and fund managers seeking exits.
Private vs. Public Market Lifecycles
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(00:54:48)
  • Key Takeaway: The AI trend suggests companies will stay private longer, despite public markets being receptive to initial AI listings.
  • Summary: The median time for companies to IPO is stretching to 11-15 years, and the AI trend may extend this further. Public markets demand fundamentals, whereas private markets allow companies to ‘pretend the price is unchanged’ during downturns. Storytelling can temporarily inflate public market valuations beyond current fundamentals, as seen with Tesla.
Transparency in Private Market Pricing
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(00:57:34)
  • Key Takeaway: Transparent pricing services prevent employees from exercising options on worthless stock from 2021 zombie companies.
  • Summary: Providing pricing data has helped employees avoid spending significant personal savings to buy stock in companies that are essentially defunct. Issuers initially resisted pricing transparency, fearing negative perception, but some CFOs later engaged to dispute or confirm valuations using their own data. Private markets lack the frequent pricing, trading volume, and quarterly reporting that define public market fundamental analysis.
Prediction Markets as Data Sourcing
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(01:00:45)
  • Key Takeaway: Prediction markets could efficiently source otherwise confidential information, raising questions about confidentiality breaches.
  • Summary: Information can be sourced from prediction markets if the user base is large enough, potentially revealing insights about private companies. If employees use confidential information in these markets, it constitutes a confidentiality breach, even if not technically insider trading for a private entity. Order books often leak information before funding rounds, suggesting prediction markets could be a more efficient mechanism for this information flow.
Valuation Corner: OpenAI vs Anthropic
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(01:03:32)
  • Key Takeaway: OpenAI’s massive projected cash burn ($100B) is historically unprecedented, contrasting with Anthropic’s more financially conservative trajectory.
  • Summary: OpenAI is finalizing an $830B valuation round, having nearly tripled its valuation in one year, but faces concerns over its projected spending. Anthropic leads in business customers and shows stronger revenue growth, with its latest funding led by purely financial investors, unlike OpenAI’s recent rounds dominated by strategic investors like Amazon and NVIDIA. Anthropic’s enterprise LLM market share has grown from 12% to 40% in two years, while OpenAI’s has declined from 50% to 27%.
Final Verdict and Sam Altman
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(01:14:33)
  • Key Takeaway: Despite Sam Altman’s fundraising prowess, Anthropic is favored based on fundamentals, investment composition, and positive revenue trajectory.
  • Summary: Both hosts lean toward Anthropic as the better bet due to its positive revenue trajectory and investment composition featuring recent, purely financially motivated backers. Sam Altman is acknowledged as a master of fundraising and political theater, capable of pulling rabbits out of his hat. Dario Amedai (Anthropic) is characterized as focusing more on substance and execution rather than sizzle.