Andrew D'Souza is the founder and CEO of Boardy AI, an AI "super connector" that helps founders, investors, and operators make high-value introductions through voice conversations. Previously, Andrew co-founded and scaled Clearco (formerly ClearBank) from a YC Fellowship company to over $100M in revenue and 600 employees across 11 countries before stepping down as CEO to pursue AI innovation.

What you'll learn:

How Andrew pivoted Clearco through three different markets before finding product-market fit with e-commerce financing
Why customers who "want to be found" create fundamentally easier go-to-market strategies
The psychology behind why financial incentives destroy natural networking behaviors and trust
How the best companies now generate inbound investor demand instead of running traditional fundraising processes
Why Andrew learned to trust founder intuition even when he couldn't articulate it to stakeholders
The technical and business model evolution from merchant cash advances to AI-powered networking
How Boardy uses voice AI to create more human-like relationship building at scale
Strategic insights on building in regulated industries like financial services
The transition from scaling a fintech business to creating AI characters with their own objectives
Why VCs don't actually remember your previous pitches and how to leverage that reality

In this episode, we cover:

(00:00) Introduction and Andrew's journey from Waterloo to YC

(02:32) Clearco's evolution from Uber driver financing to e-commerce

(04:27) The pivotal board meeting and Series A pivot decision

(05:25) Finding product-market fit with customers who "want to be found"

(09:35) Scaling Clearco to $100M+ revenue and 600 employees

(11:08) The COVID boom and building Clear Angel with GPT-3

(13:31) Andrew's decision to step down as CEO

(15:58) Introduction to Boardy AI and the AI super connector concept

(18:43) Live demonstration of Boardy's voice capabilities

(26:33) Business model and the "economy of Boardy" vision

(29:09) Why financial incentives destroy network effects

(33:36) Fundraising evolution from process-driven to inbound demand

(37:13) The reality of investor relationships and memory

(43:00) Rapid fire: biggest mistakes, inspiration, and founder psychology

(47:29) The creative expression of building AI characters

Space security, Italian disco and the Bayeux Tapestry

Monocle on Saturday

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