I had my friend Villi Itchev on ‘Panic With Friends‘ last week to talk software enterprise investing, but the conversation covered a lot of ground beyond that.

Villi is a geek and an ex investment banker with the amazing ability to explain big investment themes in ways people can easily understand.

My favorite thought from Villi in this podcast is in regards to market cap and size….’every success story is bigger than anyone can imagine in the long run‘.

Today Villi is a Managing Director and Partner at Two Sigma Ventures.

From 2009 to 2013 Villi was part of the Corporate Development team at Salesforce and led their biggest ever acquisition (at the time) of Exact Target ($2.5 billion).

We talk about his venture investment in Gitlab (founded in 2011) which is a remote only company and now the largest remote work software company with over 1,200 employees. In 2014, remote work was THE big hurdle for writing a venture check. Today Villi sees remote work as a massive 20 year trend.

We also talk about Amazon, Shopify and as we both love riding bikes – Peloton.

You can listen to the podcast here on Spotify.

You can follow Villi on Twitter here.