E170: How an AI Agent Is Outperforming VCs w/Andrew D’Souza

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.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected: X / Twitter: David Weisburd: @dweisburd

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

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

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:21) Bordy's role and application in venture space and team hiring (3:45) Bordy's experience with HF Zero accelerator and deal facilitation (8:00) Confidence in Bordy's model and matchmaking judgment (15:27)Improving fund performance and early use cases (19:12)Boardy's intelligence growth and internal company use (23:26)AI's impact on business operations and data analysis (25:02)Boardy's scalability and role in asset management (28:25)Boardy's creation, use cases, and product road map (33:39)Future integration of AI and humans in society (37:33)Boardy's market focus and compounding skills (41:28)Hiring at Boardy Inc. using Bordie (44:44)Closing remarks and contact information (46:35)Closing remarks