The AI Superconnector Transforming The Future Of Networking With Andrew D’Souza (Founder & CEO, Boardy)

Sep 26, 2025

Andrew D'Souza, Founder and CEO of Boardy AI, dives into transforming networking with voice-driven high-trust introductions. He shares how Clearco’s pivot to e-commerce financing led to rapid growth and illustrates the psychology behind networking and financial incentives. Discover how Boardy uses AI for richer relationship building, the importance of allowing mutual willingness in introductions, and why savvy founders leverage inbound demand to attract investors. D'Souza also reveals lessons learned from trusting intuition and his vision for the future of AI in networking.

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ANECDOTE

Three Pivots Before Product-Market Fit

Andrew describes Clearco pivoting from Uber driver advances to Airbnb host financing and then to e-commerce financing.
The e-commerce pivot is where the business truly scaled and found product-market fit.

INSIGHT

Find Customers Who Want To Be Found

Product-market fit came from selling to customers who 'want to be found' because they actively seek capital and solutions.
That made go-to-market and sales far easier than with shy or hard-to-reach customers.

ANECDOTE

COVID Growth And An Early AI Experiment

During COVID Clearco scaled to 11 countries, 600 employees and over $100M in revenue while e-commerce demand surged.
Andrew used early access to GPT-3 to build Clear Angel coaching for startups, sparking his AI interest.

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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