Dave McClure of 500 Startups + Tiago Paiva of Talkdesk: “What It Takes to Win in SaaS”

Just before the holidays we had our second SaaStr CSS Speaker Series at the new SaaStr CoSelling Space.

SaaStr CSS Speaker Series w/ @JasonLK @davemcclure & @TTPaiva at the new SF @CoSellingSpace #saastr @saastr @500Startups @Talkdesk

This was a fun one with Dave McClure of 500 Startups and Tiago Paiva, CEO of Talkdesk. Dave has made over 1,400+ investments including Twilio, Sendgrid, and other leaders and Talkdesk is “in my top 5”.

You can catch the whole conversation above. I was the first “venture” investor in 2014 when Tiago was the only U.S. employee (of 6 total), but I had sort of half forgotten about the 3+ years before that — especially the first 2 as Tiago slugged through with zero revenue.

Talkdesk is a really fun story, from winning a Twilio hack-a-thon, to struggling and iterating to find product market-fit, to pre-nicorn rocketship.

All three of us have worked together for years, so you’ll find some good SaaS startup war stories in here from old friends.

And Tiago spends 60% of his time recruiting now. How about you?