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
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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.
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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/
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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
How I Invest with David Weisburd 
