Episode 36: From scaling Carta to $300M ARR to showing you how the rich stay tax-free and build generational wealth.

Alessandro Chesser helped build Carta from zero to $300M+ ARR as their first sales hire—before walking away to start Dynasty, they make billionaire-level wealth tools accessible to everyone. In this episode, we dig into the playbook behind Carta’s early sales engine, the contrarian pivot to B2C, the growth loops powering Dynasty, and why Alessandro believes most Americans are getting screwed by the current wealth system. If you’re a founder or GTM operator, this one’s packed with battle-tested lessons, failures, and play-by-play stories.

Key Discussion Points:

🔥 What's the secret to selling a product that doesn't exist yet?

🤝 How to build a sales team that can sell the future, not just the present

🚀 The importance of prototyping and iterating quickly to meet customer needs

📈 Why most founders get sales wrong and how to avoid common pitfalls

💡 The surprising way to get customers to commit to a product that's still in development

📊 How to measure the success of a sales approach that's focused on the future

🚫 The biggest mistake founders make when trying to scale their sales team

Timecodes:

0:00 - Introduction

2:00 - 0 to $300M: Inside Carta’s Sales Machine

7:19 - Building relationships with early adopters and positioning them as design partners

14:06 - Building trust and promoting from within in a team

29:05 - Understanding dynasty trusts and their benefits

36:54 - Leveraging AI for SaaS scaling and customer support

44:29 - Cold email marketing strategies and organic content creation

47:00 - Closing remarks

Important links:

Dynasty: https://www.getdynasty.com

Struggling to come up with ideas to write on social - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com