Monday’s episode – Everett Randle, GP @ Benchmark

My 5 takeaways

1. Why the Mega Funds are Focused on Capital Velocity

   The North Star for General Catalyst & Lightspeed is investment velocity. When writing $ bn checks, the main product is speed. Profit will largely come from the large stakes (e.g., in Databricks), not from early‑stage Series A deals.

2. Why We Need a New Taxonomy for AI

   AI‑app companies differ from traditional SaaS. High usage translates into significant AI inference costs in COGS, so gross‑margin and revenue multiples are less useful. We should discuss gross‑profit multiples and absolute gross‑profit dollars per customer.

3. Is It Incongruous to Say: “We Want to Be the Best Partner to Founders and Still Fire Founders?”

   Context matters. The norm of pushing founders out has shifted since 2000. If a founder breaks the law or crosses ethical lines, board members must intervene.

4. OpenAI at $500 bn or Anthropic at $360 bn

   ChatGPT’s growth trajectory seems hard to disrupt, but competition will arise in coding. OpenAI’s Codex is strong; Anthropic still leads in B2B. Personally, I’d prefer OpenAI at $500 bn over Anthropic at $350 bn.

5. Biggest Investing Lesson from Mary Meeker

   Mary is the most quantitative investor I’ve known. She maps historical sequential numbers and projects forward, visualizing a company’s 8‑10‑year horizon. Use numbers to drive the narrative of an investment.

---

Thursday’s episode – Rory O’Driscoll (GP @ Scale) & Jason Lemkin (Founder @ SaaStr)

My 6 takeaways

1. Palantir Will Have a Correction

   Trading at >120× revenue with 60 % growth last quarter, Palantir is likely to face a significant correction within the next two years. Monetizing that insight is the challenge.

2. What Rory Finds Most Stressful Right Now

   The pace of evolution is extremely fast; knowledge from six months ago may already be obsolete.

3. What Seed Investors Should Bet on When “Copy‑Paste” Is No Longer Viable

   Bet on the best founders. Early‑month hype is less defensible; sustained innovation and top‑tier founders remain the key.

4. Increasing Fund Diversification and Doing More Checks

   Longer exit timelines and higher risk call for broader diversification: smaller checks, more deals, and larger funds to maintain ownership percentages.

5. One of the Biggest Mistakes Founders Make When Raising

   Sending detailed data to only one or two investors unintentionally starts a fundraising process. If those investors pass, the founder has already experienced a failed round before the official launch.

6. What Everyone Gets Wrong About Running a Fundraising Process

   Classic advice: build a massive data room. Better approach: investors often want to commit before any data room exists; they may only need a concise diligence file.

---

Friday’s episode – Carl Rivera, Chief Design Officer @ Shopify

(No specific takeaways were listed in the newsletter.)

---

Looking ahead – upcoming guests

• Monday: Andrew Ng, Managing General Partner @ AI Fund

• Thursday: Jason Lemkin, Rory O’Driscoll, and Tomasz Tunguz

• Friday: William Shu, Founder & CEO @ Deliveroo

---

Thank you for reading 20VC.