The only podcast you have to listen to every week. No politics. Just tech. - Anthropic's Superbowl Ad: Who Won - Who Lost - Harvey Raises $200M at $11BN Valuation - Sierra Hits $150M in ARR: Is Customer Support Too Crowded Spotify 👉 Youtube 👉 Apple Podcasts 👉 My 6 takeaways with @jasonlk, @rodriscoll, and @mcannonbrookes 👇 Timestamps: 00:00 Intro 01:06 Anthropic Predicts $149B in ARR in 2029 11:33 Mike’s Thoughts on SaaS Today 26:26 Harvey Raises $200M at an $11BN Valuation 45:56 Is Customer Support a Terrible or Terrific Investment Category? 01:00:58 Anthropic's Super Bowl Ad: Who Won & Lost 01:15:58 Do CEOs Have to Work Harder Today Than Ever

1. Anthropic’s SuperBowl Ad Analysed Consumer is Anthropic’s weakest sector. They could have targeted the Super Bowl ad for engineers. But they went for a cheap dig & advertised their worst product.

2. The AI Budget Revenue Stack & Why It's Not a Zero-Sum Game AI revenue can be the same dollar showing up in multiple layers. When a customer pays Atlassian, they pay AWS first, then AWS pays Anthropic. Big headline numbers hide how much is shared across the stack.

3. The Idea That SaaS is Dead as a Category is BS SaaS is not dead; it is alive and kicking. Not all companies will make it in the next 5-10 years, but there will be companies that will continue to prosper. It’s the history of the tech industry.

4. We Have to Give Up on TAM We have to let the revenue numbers show us the path to TAM. Harvey went from $200M to $600M ARR. They showed us the money to TAM.

5. Why Customer Support Is a Trojan Horse When the customer support agent becomes the main agent you’re working with, it understands the context of your business. You can start using it for sales help or research. It becomes a trojan horse to do everything else.

6. You Can't Get Fired for Buying the Winner No one is trying to be contrarian anymore; they are all piling on winners. You can’t get fired for putting money with a 1x preference. It’s the VC equivalent of “You can’t get fired for buying IBM”