20VC Newsletter - 22nd March 2026
Here are the transcripts and top takeaways from 20VC episodes released this last week.
Monday’s episode with Gokul Rajaram, Founding Partner @ Marathon:
Download the full transcript:
Gokul’s 8 Defensible Moats you Need for Your Company to be Successful in a World of AI:
1. Data (Proprietary and inaccessible)
2. Workflow (Deeply embedded operations)
3. Regulatory (Licenses and contracts)
4. Distribution (Exclusive proprietary channels)
5. Ecosystem (Third-party platform reliance)
6. Network (Marketplace liquidity density)
7. Physical (Infrastructure and atoms)
8. Scale (Low cost through volume)
Thursday’s episode with Rory O’Driscoll, GP @ Scale, Jason Lemkin, Founder @ SaaStr:
Download the full transcript:
My 6 key takeaways:
The One Question to Determine if You Want to Hire Someone in the World of AI
The definitive test in 2026 for any candidate is: “What commercial AI tool have you brought into your organization this month?”. There is no longer an excuse in any role—sales, marketing, or engineering—to not have introduced at least one tool per month. You want hires who are at the bleeding edge, capable of explaining exactly why they picked a tool and how it is functioning.
You Have to Hire Agentic Deployment Expert.
Prompt engineering is a dead role; companies now require Agentic Deployment Experts (ADEs). An ADE is someone who identifies, deploys, and trains agentic products to replace brute-force human tasks. In 2026, winning with AI agents does not require technical skills, but rather the ability to deploy and iterate on software effectively.
Congratulations Anduril, You Are Now a New Prime!
The $20 billion Army contract marks Anduril’s transition into a “prime supplier,” consolidating over 120 separate procurement actions into one enterprise deal. Their Lattice software connectivity system is becoming the default for making disparate hardware systems talk to each other autonomously. In modern conflict, systems must connect in real-time because there are only milliseconds to respond to threats.
Uber Would Be Worth $1TN Today if Travis Was Still CEO
While Uber is a successful $160B company, its valuation could be $1T today if Travis Kalanick had remained CEO. His hyper-aggressiveness, which led to his earlier downfall, is perfectly suited for the current era. By dominating food delivery and pushing autonomy five years earlier, the company could have reached a trillion-dollar scale.
Why You Need Three Big Winners to Make Seed Fund Math Work
Seed funds now require three massive winners per fund to make the power law math successful. Because seed entry points have been productized at $60M+ post-money, a manager needs 30% of their investments to be true winners to return 5x. With higher concentration risk and dilution, outcomes must be significantly larger than $1B to justify the math.
The Adobe Risk: When Workflows Change, Moats Evaporate
Adobe faces significant disruption because AI is reinventing the fundamental way creators work. While “sticky” software like Intuit remains durable for fixed requirements like taxes, AI allows a total shift in creative workflows that bypasses traditional pixel-by-pixel editing. The CEO stepping down without a successor suggests a lack of confidence during this difficult transition.
Friday’s episode with Shaunt Voskanian, CRO @ Figma:
Download the full transcript:
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: Matthew Steckman, President & CBO @ Anduril
Thursday episode: Jason Lemkin & Rory O’Driscoll
Friday episode: Andrew Dudum, Founder & CEO @ hims
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This was very insightful talk!