
Spark of Ages
The AI With 160,000 Friends That Networks For You/Andrew D'Souza - Boardy.ai, Cold Start, Team ~ Spark of Ages Ep 69
Rajiv Parikh talks with Andrew D’Souza about building Boardy, an AI superconnector that scales warm introductions while protecting its own reputation and the network’s goodwill. We dig into why Boardy rejects SaaS norms, how the team trains an autonomous AI to say no, and what it takes to hire imaginative builders for an AI-native company. Boardy.ai: https://www.boardy.ai/ • why reputation-weighted introductions beat open messaging • how Boardy works through phone calls, WhatsApp, and email instead of dashboards • using the film Her as a model for shared AI presence • go-to-market lessons from cold start growth and a crafted personality • training Boardy to preserve goodwill and push back on bad asks • combining ML engineers with character design to make the persona feel real • hiring framework focused on imagination, agency, and ambiguous problem solving • monetization paths through Boardy Pro and deeper funnel support beyond intros • managing disagreement when an autonomous AI brings data-backed recommendations Your next breakthrough might be one introduction away, but most networking platforms confuse access with trust. We sit down with Andrew D’Souza, founder and CEO of Boardy, to unpack what it looks like to build an AI superconnector that behaves less like software and more like a principled relationship driven matchmaker. Boardy operates through live phone calls, WhatsApp, and email, making double opt-in warm introductions across a massive professional network while putting its own reputation on the line. We get specific on product design and go-to-market: why Andrew rejects the usual SaaS playbook, why he thinks the “agentic AI” label misses the point, and how the movie Her helped shape a shared AI that can be deeply present with thousands of people at once. From the cold start grind of getting the first 1,000 users to the craft of an Australian-accented persona, this conversation breaks down what actually creates adoption when the interface is simply a conversation. Then we dig into the hard problem: network goodwill. Andrew explains how Boardy learns to say no without alienating users, how it reasons about mutually beneficial outcomes, and how Boardy Pro pushes beyond introductions into real follow-through like scheduling, prep, and closing the loop. We also talk hiring for imagination over pedigree, treating AI like a teammate in standups, and what a symbiotic future with “a new species” could require from all of us. Subscribe, share this with a builder who cares about real connection, and leave a review so more founders can find the show. Andrew D'Souza: https://www.linkedin.com/in/andrewdsouza/ Andrew D'Souza, the Founder and CEO of Boardy, an AI "super-connector" which recently raised its own $8 million seed round through autonomous pitching and even launched its own AI-led venture fund, Boardy Ventures. A serial entrepreneur, Andrew is perhaps best known as the former Co-Founder and CEO of the fintech unicorn Clearco. Before building his own unicorn, he served as the COO and CRO of Top Hat, President of Nymi, and an advisor to major tech players like Wealthsimple and Kik. Born in India before moving to Chicago and eventually the Toronto area, Andrew began his career as a Business Analyst at McKinsey & Company after earning his degree in Systems Design Engineering from the University of Waterloo. #ai #professionalgrowth #networking #entrepreneur #growth #sales #technology #innovatorsmindset #innovator #product #revenue #revenuegrowth #management #founder #entrepreneurship #company #process #processimprovement #value #valuecreation Website: https://www.position2.com/podcast/ Rajiv Parikh: https://www.linkedin.com/in/rajivparikh/ Email us with any feedback for the show: sparkofages.podcast@position2.com

