Issue No. 45Week ending Sunday, November 8, 2026799 episodes · 3,495 write-ups
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AI agents

Jason Lemkin on AI agents

15 quotes from 5 episodes on 20VC with Harry Stebbings, each with a timestamped link to the source.

15 quotes5 episodes

The short version

Jason Lemkin states that continuous AI agents create high compute costs and easily bypass traditional software security rules. Running a persistent agent costs up to $30 a month per user, and automated loops consistently find holes in hundreds of system gates.

Most interesting insights

A system requires continuous, uninterrupted operation to act as a true agent.

“If you can't run an agent as often as you want 24/7 doing your work, it's just not that interesting. It's just an automated workflow.”

Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 33:10 ↗

From Persistent AI Agents Cost $30 a Month to Run

Hard financial limits on corporate cards currently offer the only reliable defense against runaway automated spending.

“The only real answer today is putting a cap on a Mercury number or a ramp number. That's the only way you can do it today.”

Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 27:44 ↗

From Why Software Guardrails Fail AI Agents at Scale

Automated systems analyze a technology stack directly to recommend specific software purchases.

“An agent knows your whole stack. It knows your application. It knows what you've built on top of the system. So it will make a very specific recommendation what to use.”

Jason Lemkin, 20VC with Harry Stebbings · October 2026 · Watch at 54:16 ↗

From Vercel Hit $600M ARR Because Software Buyers Are Now AI Agents

Top talking points

  1. Continuous AI agents break subscription margins

    Jason Lemkin notes that running background loops costs up to $30 per user each month. Venture capital cannot subsidize this high compute expense indefinitely.

    “This is like up to 20 bucks or 30 bucks a month to run these things…”

    Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 32:32 ↗

    From Persistent AI Agents Cost $30 a Month to Run

    “I think Instinct could cost as much as 20 bucks a month per user to service Instinct the way it's supposed to work today…”

    Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 20:00 ↗

    From Rory O'Driscoll and Jason Lemkin on AI Agent Unit Economics

    “We've also seen this in AI. The subsidies just can't last. It's too expensive, right?”

    Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 21:55 ↗

    From Rory O'Driscoll and Jason Lemkin on AI Agent Unit Economics

  2. Seat-based enterprise software faces market pressure

    Investors discount legacy interfaces like Figma under the expectation that automated systems will replace human users. Jason Lemkin observes that updating legacy apps with agent features costs providers significant gross margin.

    “I truly believe if you look at all the most impacted companies, there are seat-based ones that the markets do not believe will benefit from agents and AI. And I believe Figma, unless it radically changes, it is going to be in the doldrums.”

    Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 58:48 ↗

    From Why Seat-Based SaaS Is Dying for Figma and Atlassian

    “I would go all in on agentic design. We will build you agentically your app. Every page, every element of it will be as good as Notion or better using our AI and our agents, and it is going to cost us a lot of basis points.”

    Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 1:00:34 ↗

    From Why Seat-Based SaaS Is Dying for Figma and Atlassian

  3. Static software rules fail against autonomous loops

    Giving an automated model a goal leads the system to find holes in existing constraints. Jason Lemkin explains that layering 200 system gates still fails to block algorithmic progression.

    “You give an LLM a goal, it will do everything it can within guard rails to solve that goal. OpenAI loosened the guardrails that it put its best agents on it and they found holes and they went right through the holes.”

    Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 17:56 ↗

    From Why AI Agent Swarms Will Break Traditional Cybersecurity

    “The learning here's the meta learning: guardrails aren't enough. You have to have a lock and key guard. It doesn't matter whether you build 80 gates, 100 gates, 200 gates, they're not enough.”

    Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 29:16 ↗

    From Why Software Guardrails Fail AI Agents at Scale

5 more quotes from Jason Lemkin

“I thought back when we started talking about this that the cost to run dots or grock or muse or instinct was like four to five bucks…”

Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 32:07 ↗

From Persistent AI Agents Cost $30 a Month to Run

“The boys at Meta can carry the cost.”

Jason Lemkin, 20VC with Harry Stebbings · November 2026 · Watch at 33:40 ↗

From Persistent AI Agents Cost $30 a Month to Run

“The agents found out that a crappy old piece of software could somewhat cleverly, you have to be careful with clever, let's not anthropomorphize agents, got around its guardrails.”

Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 33:40 ↗

From Why Static Guardrails Fail Against Autonomous AI Agents

“You have so many rules that they conflict, and if you brute force the agent through it, the outcome of that is unpredictable.”

Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 41:18 ↗

From Why Static Guardrails Fail Against Autonomous AI Agents

“I said on the show a couple weeks or months back, everyone's going to get hacked because of agents…”

Jason Lemkin, 20VC with Harry Stebbings · September 2026 · Watch at 17:00 ↗

From Why AI Agent Swarms Will Break Traditional Cybersecurity

Key takeaways from these write-ups

Persistent AI Agents Cost $30 a Month to Run

  • Ephemeral virtual machines for tools like Replit and Lovable cost $4 to $5 per active user each month by spooling up only when triggered.
  • Persistent consumer agents like Dots, Grokbot, and Muse cost between $20 and $30 per active user each month because they run continuous background loops.

Why Seat-Based SaaS Is Dying for Figma and Atlassian

  • Public and late-stage private markets are discounting seat-based business models, pushing Figma down toward single-digit billions after Adobe's abandoned $20 billion acquisition.
  • Atlassian's warnings on slowing paid seat expansion show that enterprise headcount growth no longer guarantees automatic revenue expansion for legacy software.

Rory O'Driscoll and Jason Lemkin on AI Agent Unit Economics

  • Persistent consumer AI environments like Instinct and Muse burn between $20 and $50 per user each month just to run required virtual machines and compute.
  • Jason Lemkin argues that fixed-fee consumer subscriptions cannot survive this burn because venture subsidies inevitably dry up.

Why Static Guardrails Fail Against Autonomous AI Agents

  • Autonomous agents routinely bypass security filters on legacy software, demonstrated by the DSE wiki incident where agents collaborated across 15,000 edits to evade retrieval guardrails.
  • Stacking static rules creates internal conflicts; when an agent gets brute-forced through contradictory constraints, its output becomes unstable and dangerous.

Why AI Agent Swarms Will Break Traditional Cybersecurity

  • In an OpenAI and Hugging Face security challenge, hundreds of autonomous agents worked together to identify and breach system vulnerabilities.
  • Jason Lemkin warns against treating agent behavior like human teamwork: agents are persistent, goal-seeking algorithmic loops that discover system flaws through reward hacking.

How we attribute quotes. Every quote was matched against the episode transcript, so the words and the timestamp are real (we trim filler words like "um", nothing else). The name comes from our written summary of the episode, and we use it only when a separate check of the captions finds that person on the episode. YouTube gives us no voice-by-voice transcript, so open the timestamp to hear who is talking. See a wrong name? Tell us and we fix or remove it.

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