Andrew D’Souza, ex-co-founder of Clearco and now Boardy.ai, explains how he went from building a billion-dollar FinTech company to creating an AI “super-connector” that changes how founders meet investors.
Andrew breaks down why warm intros no longer work, how Boardy.ai sparked investor interest before he was even fundraising, and why real-time AI conversations may become the future of dealmaking.
He also shares ideas on founder psychology, network effects, and the next chapter of AI-driven relationship building.
What You’ll Learn in This Episode
How Andrew D’Souza raised $8M using an AI agent (Bordy.ai)
Why the “warm intro” is dead — and what replaces it
How Clearco scaled to a $2.5B unicorn
Why investors chase the same 50 deals (and what founders should do instead)
A breakdown of what’s actually broken in fundraising today
The mechanics of AI-driven dealflow, investor matching, and credibility building
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Here's what you're in for:
00:00 Introduction and Guest Welcome
00:16 Using AI to Raise Funds
01:11 The Evolution of Fundraising
05:02 Clear Co: Building a FinTech Unicorn
08:56 Transitioning from Clearco to AI
18:37 The Birth of Boardy
25:45 The Initial Growth Strategy
26:23 Defining Bordy's Vision and Purpose
27:23 Building a Horizontal AI Platform
27:55 Achieving Network Effects and User Success Stories
28:57 Experimenting with Investor-Founders Matching
30:12 The Importance of Trust in Business Introductions
31:41 Boardy's Unique Onboarding Process
36:23 Future Plans: Monetization and Expansion
47:54 The Role of AI in Human Relationships
53:17 How to Connect with Andrew
ABOUT Andrew D’Souza
Andrew D’Souza is a veteran founder and tech operator best known for co-founding and leading Clearco, the company that transformed non-dilutive capital and funded 10,000+ startups with over $2.5B deployed. With a background in Systems Design Engineering from the University of Waterloo, Andrew now invests, advises, and serves as a visiting partner at HF0, helping high-potential founders scale faster and build category-defining companies.
You can reach out to Andrew through:
Linkedin: https://ca.linkedin.com/in/andrewdsouza
Instagram:https://www.instagram.com/andrewdsouza/
Website:https://www.boardy.ai/
ABOUT JASON KIRBY
Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A.
He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+
You can reach out to Jason through:
Email: jason@thunder.vc
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT $100M EXITS
My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it.
For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast.
Be sure to subscribe and let me know who you want me to interview next.