20VC: Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued? | Monday, Figma, Shopify: Which are Buys vs Sells?
20VC: Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued? | Monday, Figma, Shopify: Which are Buys vs Sells?
Podcast1 hr 34 min
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Note: AI-generated summary based on third-party content. Not financial advice. Read more.
Quick Insights

The market is heavily favoring AI over traditional SaaS, punishing many software stocks and creating potential buying opportunities in oversold names. Consider Adyen (ADYEN.AS), a "wildly profitable" payments company with nearly 50% operating margins that appears undervalued compared to its private peers. Shopify (SHOP) is viewed as a resilient e-commerce leader that has been unfairly sold off with the broader SaaS sector. For a higher-risk value play, Monday.com (MNDY) is presented as a potential "screaming buy" trading at under 10x cash flow if its business proves durable against AI. The key investment thesis is to identify oversold software companies whose business models are defensible against disruption from new AI agents.

Detailed Analysis

Anthropic (Private)

  • The podcast centers on a massive hypothetical fundraise for Anthropic: $30 billion at a $380 billion post-money valuation. This is presented as the "only play in venture" right now, with immense capital chasing a few top AI companies.
  • Unprecedented Growth: The company has reportedly seen 10x year-over-year revenue growth for three consecutive years, a rate described as unprecedented, even when compared to the early days of Microsoft or Google.
  • Momentum Play: The investment is described as a momentum trade. The last several funding rounds have provided quick, significant returns (e.g., a 2x return from a $160 billion valuation round), and investors are piling in to avoid missing out on "the only thing that's working."
  • Enterprise Focus: Anthropic is positioned as the "best model" for the enterprise, with its product Claude being a key driver. Less than 20% of its revenue is from consumers, distinguishing it from OpenAI's consumer-heavy ChatGPT model.
  • Competition with OpenAI: While not seen as a zero-sum game, Anthropic's revenue has grown from 5% of OpenAI's to 64% in just 14 months, indicating it is "stealing budget" and has significant momentum.
  • Risk Factors Mentioned:
    • Fragility & Capital Intensity: The company is described as wildly capital-intensive, similar to a semiconductor company, not a high-margin software business. The CEO, Dario Amodei, has stated that mis-spending on compute for a year could lead to bankruptcy. This fragility is seen as not being priced into the high valuation.
    • Path to Profitability: Unlike early Microsoft, Anthropic is still losing a lot of money. Achieving free cash flow would likely require slowing down growth, which could cause investors to re-evaluate its high valuation (e.g., 30-40 times revenue).

Takeaways

  • Anthropic represents the pinnacle of the current AI momentum trade. The market has decided this is the key bet, driven by unprecedented growth and a narrative that AI will "eat everything."
  • For investors with access to private markets, the discussion suggests that participating in rounds for foundational model companies like Anthropic is seen as a near-necessity for venture funds to show performance.
  • The primary risk is the immense capital required to compete. An investor must believe that the company can continue its hyper-growth to justify the valuation and eventually navigate the high costs to become profitable. The business model is more like a capital-heavy industrial than a traditional software company.

AI vs. SaaS (Sector-Level Theme)

  • The core narrative is that "Wall Street fell in love with AI and to do that had to fall out of love with SaaS." Capital is flowing aggressively into AI companies while punishing traditional SaaS stocks, even those with strong fundamentals.
  • The Gravity Well: Traditional SaaS companies are being pulled down by a "gravity well." High growth (like Applovin's 70%) is no longer sufficient. The market is demanding "escape velocity" growth, which only a few AI companies like Anthropic are achieving.
  • Presumption of Failure: Public SaaS stocks have shifted from a "presumption of success" to a "presumption of failure." The burden of proof is now on them to show they won't be displaced by AI.
  • Headcount Reduction: A major headwind for SaaS is the corporate push to reduce human headcount and replace roles with AI. This directly threatens the seat-based pricing model of many SaaS companies (e.g., HubSpot, Atlassian). As one speaker noted, "Nobody wants to hire 20,000 more people next year... and get them all seats of software."
  • Old School vs. New School SaaS: The speakers distinguish between "old school SaaS" (built pre-2022) and "new school SaaS" (built on top of AI models). The "old school" companies are most at risk, especially those in horizontal workflow automation.

Takeaways

  • Investors should be cautious about traditional, seat-based SaaS companies that do not have a compelling and integrated AI strategy. The market sentiment is strongly against them.
  • The key question for any SaaS investment is its durability in the face of AI. Is the product easily disrupted by an AI agent, or does it have a defensible moat (e.g., payments, complex regulation, system of record)?
  • There may be value opportunities in "oversold" SaaS stocks, but the risk is catching a falling knife. The market is currently pricing in a high probability of disruption, and it's difficult to see a catalyst that will change this negative narrative in the short term.

Shopify (SHOP)

  • Sentiment: The speakers are "super positive" on Shopify and believe it is likely oversold. It has been unfairly grouped in the "basket" of struggling SaaS companies.
  • Bull Case: The core business of providing a website and payments infrastructure for e-commerce is not seen as having a "credible near-end story" of being replaced by AI. It is considered more resilient than workflow automation software.
  • Bear Case / Risk Factor: The primary threat is the rise of agentic or conversational commerce. If future shopping happens via agents (e.g., on ChatGPT) and bypasses the merchant's Shopify-hosted storefront, it could make Shopify's software obsolete over the long term, even if Shopify continues to process the payments.
    • Shopify's CEO, Tobi Lütke, is aware of this threat, evidenced by the company's high number of recent code commits, suggesting they are racing to adapt.

Takeaways

  • Shopify is presented as a potentially attractive "baby thrown out with the bathwater" investment. Its core e-commerce and payments infrastructure is viewed as more durable than many other SaaS businesses.
  • The key long-term risk to monitor is the adoption of agentic commerce. Investors should watch how Shopify adapts its platform to remain the central hub for commerce, even if the user interface shifts away from traditional websites.
  • One speaker noted that despite believing the stock was a buy, he couldn't bring himself to purchase it because he "couldn't see the bottom," highlighting the powerful negative sentiment weighing on the entire SaaS sector.

Figma (Private)

  • Valuation & Performance: Figma is still a strong company, valued at $12 billion+ and growing at 30-40%. It is not being "thrown out with the bathwater" like some public SaaS stocks.
  • Bear Case - Missed Opportunity: The main criticism is that Figma "missed a whole generation" by being too slow to integrate AI. They should have owned the AI product prototyping space.
    • Competitors like Replit and Lovable have captured an estimated $300-400 million in annual recurring revenue (ARR) in Figma's core market by launching AI-native tools for product teams.
    • This failure to innovate quickly is seen as a cautionary tale: if a top-tier company like Figma can be too slow, what hope is there for others?

Takeaways

  • Figma's valuation is seen as being "perched" between two outcomes. If it can successfully launch a competitive AI product and reclaim market share, its valuation could rise significantly. If it fails, its valuation multiple will likely compress to match slower-growth SaaS companies.
  • This serves as a powerful case study for investors analyzing any software company: how quickly are they adapting to AI, and are new, AI-native competitors emerging in their core market? Even market leaders are vulnerable to rapid disruption.

Stripe (Private) vs. Adyen (ADYEN.AS)

  • Valuation Discrepancy: Stripe is valued privately at around $130-140 billion, while Adyen's public market cap is roughly a third of that, despite being a major player in the same space.
  • Adyen (ADYEN.AS):
    • Bull Case: It is "wildly profitable" with nearly 50% operating margins and growing revenue at 21% year-over-year. As a public company, its financials are transparent. One speaker argued for buying Adyen, as the likelihood of it being mispriced is lower than the privately-valued Stripe.
    • Bear Case: Leadership communicates poorly and doesn't tell a compelling narrative, which may contribute to its lower valuation.
  • Stripe (Private):
    • Bull Case: It is roughly 2.5x the size of Adyen by revenue and is perceived to have a higher growth rate. As a private company, it has more "flexibility and agility" to invest heavily in new initiatives (like AI) without the scrutiny of public markets.
    • Bear Case: It is not as profitable as Adyen, and its private valuation is based on a narrative rather than transparent public financials.

Takeaways

  • The Stripe vs. Adyen comparison highlights the classic investment choice: growth vs. value. Stripe represents the high-growth, narrative-driven story, while Adyen represents the profitable, value-oriented play.
  • An investor favoring transparency and proven profitability at a reasonable valuation might prefer Adyen.
  • An investor willing to pay a premium for higher growth and the flexibility that comes with a private, founder-led company would lean towards Stripe.

Monday.com (MNDY)

  • Sentiment: The stock is presented as a potential "screaming buy" if an investor believes its business is durable. It is down 51.3% on the year at the time of the podcast.
  • Financials:
    • Market Cap: $3.8 billion
    • Revenue: $1.25 billion at 27% year-over-year growth.
    • Guidance: Expects $1.45 billion in revenue for 2026.
    • Profitability: $175 million in non-GAAP operating income (14% margin).
  • The Core Question: The investment decision boils down entirely to the durability of its revenue in the age of AI.
    • If you believe its product roadmap can survive and growth is sustainable, the stock is described as "wildly cheap" at under 10x cash flow.
    • If you believe its workflow product will be disrupted by AI agents, then the stock is likely to continue its decline.

Takeaways

  • Monday.com is the quintessential example of an "oversold" SaaS stock. The financials look solid, but the market is pricing in a high risk of future disruption.
  • For a potential investor, the key due diligence would be to analyze Monday's product roadmap, its AI integrations, and the stickiness of its customer base (which is primarily outside of the tech sector and may be slower to adopt disruptive AI).
  • The speakers note that SMB-focused companies like Monday may see disruption effects faster than enterprise-focused ones like ServiceNow, as their customers churn more quickly.
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Episode Description
AGENDA: 04:14 Anthropic's $30B Raise at $380B 06:18 Why SaaS Stocks Keep Getting Crushed 18:15 Wall Street's New Religion: AI Replaces Headcount  22:42 The Bear Case for Shopify: What Could Go Wrong? 31:51 Replit and Lovable are Proof Figma Missed Out: Figma; Buy or Sell?  48:42 Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued?  54:36 OpenAI Buys OpenClaw 01:06:28 Thrive's $10B Growth Fund 01:09:10 Arif Janmohamed Leaves Lightspeed for New Firm 01:17:12 Workday's Founder Returns as CEO: Will it Work?  01:20:34 Which Founder Returns Next: HubSpot, Twilio, Gitlab? 01:24:03 Is Monday.com a Screaming Buy? 01:28:25 Jason and Harry Bet $200,000
About The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

By Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.