Ignite Startups: How Andrew D’Souza Built an AI That Connects Founders and Investors | Ep228

What if the next great connector in Silicon Valley isn’t a human at all, but an AI with opinions, taste, and the courage to say no?

In this episode, we sit down with Andrew D’Souza, founder and CEO of Boardy, and the serial entrepreneur behind Clearco, to explore what happens when you combine behavioral psychology, network effects, and modern AI, then let it loose on one of the hardest problems in business, meaningful human connection. Andrew has spent his career building at the intersection of finance, technology, and trust. Now he’s building an AI “super connector” that doesn’t live in an app, doesn’t obey every command, and doesn’t optimize for clicks, but for goodwill.

Boardy is an AI board member you can call. Literally. It talks on the phone, remembers context, introduces you to the right people, and sometimes refuses if it thinks the intro would be bad for the network. In a world drowning in cold emails and shallow SaaS tools, Andrew is betting on something contrarian, that AI should feel less like software and more like a principled person.

In Todays Episode We Discuss:

00:01 – Breaking Things, Founder Embarrassment, and Why It Matters

03:30 – Studying the Brain, Behavioral Economics, and Human Decision-Making

06:40 – McKinsey, Facebook, and Getting the Startup Bug

10:10 – Early Lessons on Incentives and Why Referral Marketplaces Fail

14:45 – Becoming a Connector Between Silicon Valley and Canada

17:30 – The Origin Story of Clearco and Access to Capital

22:10 – Financing the DTC Boom and Creating a New Category

27:40 – When Scale Outgrows the Founder, Stepping Aside as CEO

31:50 – Discovering GPT-3 and the Clear Angel Experiment

36:10 – The Problem with Personal CRMs and Human Memory Limits

39:40 – Network Effects, Voice AI, and the Birth of Boardy

44:30 – Why Voice Is the Most Human AI Interface

48:20 – Judgment, Trust, and Saying No in Network Design

52:51 – The Future of AI, Imagination, and Human Connection

Andrew also shares a moonshot vision, Boardy as an AI Richard Branson, pulling the unique business out of every person, then helping them meet exactly who they need to make it real.

Memorable moments from the episode:

“Most people are being vastly unimaginative about what AI can do. The limitation isn’t the models, it’s our imagination.”

“The worst case of a bad introduction is wasted time. The best case is it changes your life. That asymmetry matters.”

Andrew started his career studying how the brain works. Now he’s building something that plugs directly into how humans actually connect. From simulating neurons to orchestrating networks, this episode is a glimpse at a future where AI doesn’t replace relationships, it upgrades them.

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/ignite-conversations-on-startups-venture-capital-tech/id1709248824

Follow Andrew D’Souza on LinkedIn: https://www.linkedin.com/in/andrewdsouza/

Follow Andrew D’Souza on X: https://x.com/andrewdsouza

Follow Brian on X: https://x.com/brianrbell

Follow Brian on Linkedin: https://www.linkedin.com/in/bblinkedin/

Visit Our Website: https://www.teamignite.ventures

Subscribe to Our Newsletter: https://insights.teamignite.ventures/

👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL

🙏 Join the conversation on your favorite social network: https://linktr.ee/theignitepodcast