It all started in August of 2020.
A quick coffee chat, founder to founder, with Kyle Racki
I had admired Proposify from a distance. The way they had grown the company. The way he shared his lessons online.
The conversation was easy.
There was clear mutual respect.
Big talk, not small talk, happened quickly.
A confident humility to the interaction.
There was a natural curiosity.
We shared a few emails and met twice more for lunch over the next 18 months.
At that third meeting, Kyle mentioned we should do a podcast featuring these conversations. The back and forth, the lessons learned, and most importantly, the respectful but important disagreements.
There are many ways to get to 9.
I give credit to Kyle for the smooth part of the dialogue. He has a natural way of calming the waters without diluting the lesson or taking away from the productive conflict. That’s why he is a great leader.
On New Year’s eve, I sent Kyle a quick text and said, let’s do that podcast. We set a time every Friday am to meet and record.
The result is the Racki & Symes Podcast.
I hope you enjoy it. It is a free flowing conversation on leadership, scale, and the evolution of an organization.
March 29, 2022