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
