5 Years and 300 SaaStr Podcasts with Harry Stebbings. A Look Back.

SaaStr just crossed 300 (!) podcasts led by our good friend and family Harry Stebbings.  The first one launched on March 1, 2016 with Tiago Paiva, CEO of unicorn Talkdesk:

SaaStr Podcast #001: Tiago Paiva, Founder On How Talkdesk Reached $3m in Sales Without Spending $1 on Marketing

The whole team at SaaStr is blessed to work with Harry and I thought I’d share a few fun stories and learnings.  Harry originally had me on 20VC way back in 2015 here when I briefly worked at a Sand Hill venture capital firm.  I am not sure I had ever listened to a podcast back then, and didn’t really get why podcasting was having a renaissance.  I was more a blog/Quora kind of person back then.  But like everyone, Harry’s charisma and passion sucked me in, and I gladly agreed to join as Guest #50:

Boy look at us back then!  Harry with his Google glasses, me without a care in the world.

Harry and I kept in touch, but what I didn’t fully appreciate is that he already was deeply passionate about SaaS and was OG SaaStr.  A little later, he asked me if we’d like to have a SaaStr podcast.  I had exactly 1 team member at the time and didn’t totally get it, but after a little pushing (thank you, Harry) said sure let’s do it.  I had enjoyed working with him.

To kick it off, Harry flew out from London to the 2nd SaaStrAnnual.com in February 2016 and we gave him a podcast room and he interviewed dozens of SaaS leaders there, from Lew Cirne to Aaron Levie.  Unfortunately, the room at the Masonic in SF had acoustic issues and all the recordings were unusable!!  I would have been dejected, but Harry and I worked on a list of ringers to start over with, and we were off to the races.

The next year, Harry flew out again from London to attend the 3d SaaStrAnnual.com and we had “Drinks with Harry” at the Bill Graham.  Over 300+ folks signed up to meet Harry, and the hallways were overflowing with fans.  Somehow, we got the venue to serve Mojitos.  We did not tell them Harry wasn’t 21 🙂  SORRY.

Since then, I am super proud to have had a tiny side role in Harry’s growth over the past almost 5 years to VC partner and in many ways, a media mogul (really).

While 1000s of folks now consider Harry a friend — which truly is quite incredible — I consider him part of the family.

Thank you, Harry.  See you soon.

And catch up on some of our most popular podcasts here:

Published on January 18, 2020

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