Jason Stoffer was still early in his career at venture capital firm Maveron in 2012 when he declined an opportunity to invest in Remitly, then a fledgling Seattle startup with ambitions to challenge Western Union by bringing a tech mindset to the business of international money transfers.

He was impressed by Remitly co-founders Matt Oppenheimer and Josh Hug but knew they faced a huge challenge in getting the state-by-state regulatory approval required to make monetary remittances to what was then their initial international market, the Philippines.

"It felt like the end vision was powerful — if they can get there," Stoffer recalled. "But two guys in a room in Seattle saying they were going to navigate an incredibly complex regulatory environment and figure out how to market in a country a continent away, it felt like too big a hill to climb. And they proved me wrong."

Ten years later, Remitly is poised to go public in an initial public offering that values the company at $6.5 billion, as we reported this week.

Stoffer, whose successful exits as an investor include Flywire, Course Hero, General Assembly and Zulily, analyzed Remitly's financials recently on his new blog, Ringing the Bell, displaying an admirable humility in his assessment of a company that could have been part of the Maveron portfolio.

He joins my colleague John Cook and me on the GeekWire Podcast to talk more about Remitly, lessons learned, the current market for tech investing, and his approach to reading S-1 regulatory filings.

In the final segment, we discuss Amazon CEO Andy Jassy's first television appearance since assuming the top role from founder Jeff Bezos. Stoffer is an investor in Cap Hill Brands, an aggregator of third-party Amazon sellers.

Audio editing and production by Curt Milton; Theme music by Daniel L.K. Caldwell.

See omnystudio.com/listener for privacy information.