E170: How an AI Agent Is Outperforming VCs w/Andrew D’Souza
How I Invest with David Weisburd
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
David Weisburd
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E170: How an AI Agent Is Outperforming VCs w/Andrew D’Souza

E170 • Jun 4, 2025 • 47 mins

What if your venture partner could talk to a thousand founders a day — and actually listen? In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other. He describes Boardy as a principal, not an agent — a character with its own goals, who is building goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild part: Boardy is already responsible for over ten multimillion-dollar deals, including helping HF0 select 3 of its 10 portfolio companies, and facilitating LP meetings for emerging fund managers.

Highlights:

  • 3 of HF0’s 10 most recent investments came from founders surfaced by Boardy
  • Boardy has facilitated over 10 multimillion-dollar deals — including founder-investor and LP-GP introductions
  • VCs are using Boardy to filter inbound, diligence deals, and ideate thesis
  • Boardy works like a McKinsey partner: asking questions, forming opinions, connecting people
  • Designed as a “principal,” not a “tool” — Boardy has its own goals and judgment -Trained through over 50,000 conversations, Boardy’s match rate is compounding fast
  • Andrew’s team uses Boardy daily — including for hiring and internal decision-making
  • Boardy speaks over voice, chat, and WhatsApp — and conversations feel more like peers than prompts

-- Guest Bio: Andrew D’Souza is the founder of Borty.ai, a voice-powered AI platform that connects people based on real-time, high-fidelity conversations. Previously, he co-founded Clearco (formerly ClearBank), where he helped pioneer revenue-based financing for e-commerce startups. Andrew is also a seasoned startup investor and advisor, and began his career at McKinsey & Co.

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LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Andrew D'Souza : https://www.linkedin.com/in/andrewdsouza/

Links: Boardy: https://www.boardy.ai/

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