If AI is about to transform tax filing, why do 55% of Americans still trust a human to do it for them?

In this episode, host Reggie Young sits down with Gavin Nachbar, founder of Column Tax and Chief Product Officer at Aiwyn, to unpack what it really takes to build in one of fintech’s most complex and overlooked spaces: tax filing.

Gavin shares how Column Tax built the first modern embedded tax engine in the US, what AI is about to change for the 55% who still rely on a human preparer, and why he’s genuinely bullish — not worried — about the road ahead. They also dig into his lessons on entering a regulated space as an outsider, the unique challenges of a seasonal product, and the hard-won takeaways from going through an acquisition.