20VC Newsletter - 19th October 2025
Venture Capital

20VC Newsletter - 19th October 2025

Harry Stebbings
Harry StebbingsOct 19, 2025

Summary

Here are the transcripts and top takeaways from 20VC episodes released this last week.

20VC Newsletter - 19th October 2025

20VC Newsletter · 19 October 2025 · Oct 19, 2025

SemiAnalysis & AlphaSense break down who’s building, buying, and bottlenecked in AI infrastructure

Monday’s episode with Mike Cannon‑Brookes, Co‑Founder & CEO of Atlassian

  • Full transcript (PDF, 199 KB)

    Download

My 6 takeaways

  1. The Secret to Co‑CEOship

    Find the sweet spot of shared responsibilities: Scott and I overlap by 60‑80 %. We interchange roles & functions over time. A clear understanding of roles plus a shared context is key.

  2. We Will Have More Devs and More Software in a World of AI

    Software will be cheaper to build and ideas will stay plentiful. More devs will be far more efficient, producing far more technology.

  3. Why None of the AI Startups Today Have a Moat and Why It Does Not Matter

    Everyone copies each other and switching costs are near zero. Future defensibility comes from value, data, and workflows. Incumbents and startups both have a good shot at winning.

  4. Does per‑Seat Pricing Die in a World of AI

    Two logical replacements emerge: per‑value delivered and consumption model. Customers dislike the consumption model and it’s hard to measure per‑value outcomes. Seat‑based pricing won’t die, but will likely mix with one of these two.

  5. The Single Greatest Threat to Atlassian Today?

    Our biggest threat is losing our creativity. We want to be a multi‑decade technology company, constantly reinventing ourselves rather than defending past wins.

  6. Fave Quote from Tobi @ Shopify

    “A founder’s job is to fight the entropy of ambition.”

    We cannot be complacent: fight for every customer and user. Stay hungry, act small – there is a long way to go.


The Trio Ep

Thursday’s episode with Rory O’Driscoll (GP @ Scale), Jason Lemkin (Founder @ SaaStr), and Roger Ehrenberg (Managing Partner @ Game Changers Ventures)

  • Full transcript (PDF, 240 KB)

    Download

My 4 takeaways

  1. Diversification in AI Investing Is the Same as Saying I Don’t Know

    Those who know the winners will concentrate capital. Those who don’t will diversify to bide time, which is better than sitting out entirely.

  2. Whenever a Tier One Firm Does an Investment in Your Company, Double Down With the Pro Rata

    If a reputable investor does a follow‑on at a high price, do everything to be in it. Don’t anchor to entry price; update for progress and external validation.

  3. The Most Valuable Venture Firms Are the Ones You Can Actually Sell

    Most venture firms are collections of individuals. If you remove the partners, there’s no residual value—no IP, moat, or brand. Institutionalizing a process‑driven platform (e.g., Industry Ventures) creates something acquirable.

  4. In AI, Your Downside Isn’t Valuation: It’s Founders Leaving

    One co‑founder of a $10 B AI startup left for a $3.5 B Meta package. No misconduct—just better personal economics. For early‑stage investors, founder loyalty—not terms—is the real risk.


20product Zach Lloyd @ Warp

Friday’s episode with Zach Lloyd, Founder & CEO of Warp

  • Full transcript (PDF, 224 KB)

    Download

Let us know what your big takeaways from this week’s shows were in the comments below!

Thank you for reading, and don’t miss the great guests we have next week:

  • Monday episode: Alex Bouaziz, Co‑Founder & CEO of Deel

  • Thursday episode: Jason Lemkin & Rory O’Driscoll

  • Friday episode: 20Growth

Thank you for reading 20VC.

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