Would You Trust AI To Help Raise Your Round?
Brash chatbot Boardy promised to help 100 startup founders fundraise by year's end. Upstarts has the story on what happened next.
My first interview of 2026 is with a chatbot with an Australian accent and a box for a head called Boardy.
Boardy bills itself as an “AI superconnector,” helping founders to meet peers, venture capitalists, or prospective customers and hires. Upstarts onboarded last month as part of one of our most popular stories of 2025, our deep dive into how VC firms are using internal AI tools to compete.
Why talk to Boardy? If you believe the account shared by founder and CEO Andrew D’Souza on social media, the AI-powered chatbot had “decided to raise a fund” to invest in some of the deals happening through its connections, quickly wracking up $300 million in capital interest.
Boardy’s boasts should be taken with a healthy dose of salt. While its team has claimed this will be the first AI to write investment checks directly into startups, such hype posts come appended with lengthy disclaimers clarifying that a human, D’Souza, has final say on all deals.
When D’Souza says Boardy raised its own $8 million seed round from Creandum, or decided to make investments, that’s also pushing a narrative that ignores a bunch of humans in the loop. (One example: Boardy’s fund will split carry with human power users who serve as scouts.)
“We’re not trying to disrupt venture capital,” D’Souza clarifies to Upstarts in December. “It’s more like Boardy is an angel investor who sees a lot of deal flow, and shares that deal flow with the network, and tries to participate in the ones that will have him.”
Aside from all those efforts happening within VC firms themselves – and readers pointed out many more to us than could appear in our story – Boardy isn’t the only automated VC matchmaker to emerge recently.
Investor Jason Lemkin vibe-coded SaaStr AI tools that have already analyzed nearly 3,000 pitch decks and made more than 800 intros for founders to VCs. (We got Lemkin’s take on all this below.) Just yesterday, another investor, Incisive Ventures founder Martin Tobias, posted a similar vibe-coded matching tool called Investor Match.
But Boardy is supposed to have an advantage over such self-serve tools because of its 30-minute onboarding calls with founders and deeper context about what investor signups and founders want in a match. And in late October, Boardy and D’Souza had thrown down a gauntlet: Boardy would help 100+ founders raise a funding round by the end of the year.
So we made a note at Upstarts to check in with Boardy first thing on Monday, January 5: did the AI tool pull it off?
Happy 2026, Upstarts readers! We’re excited to bring you more bangers and more fun in our startups news coverage this year. To read this story and more, enjoy 10% off monthly and annual subscriptions for a limited time.
