[Editor's note: This piece, based on my PandoMonthly interview with Ben Lerer, originally ran on Startups.co as part of an editorial collaboration with Pando aimed at sharing founders' struggles, challenges, and origin stories with millions of founders across America.]

It's hard to decide who has changed the most in the last 12 years: Thrillist or its co-founder and CEO Ben Lerer.

Back in 2004, Thrillist was frequently described as the male equivalent of DailyCandy, a female oriented email newsletter that sold for $125 million only to be killed by Comcast. To be clear, that is still one of the largest content exits in the Web era, and it inspired plenty of envy at the time. Many expected Thrillist to be flip-bait as well.

Fast forward to today and Thrillist has raised more venture capital than that DailyCandy acquisition– much of it during a $100 million mega round announced last year. That deal rolled up Thrillist and three other media platforms into one company called Group Nine, and Discovery invested the cash. Lerer is the CEO of it all...