Pro Bono Clients & Messy Beginnings - Behind Grindstone #1 | 059
Sat Aug 23 2025
Episode 1 of "Behind Grindstone."
Dillan (CEO of Grindstone) and Colby (Head Coach of Grindstone) sit down and have their first-ever recorded debriefing of how they started the company. The goal is to track their journey, remember the hard times, and share all the mistakes and lessons as they try to scale Grindstone.
They discuss: the origin story of Grindstone, why accountability coaching works, starting with pro bono clients, learning to work as a team, celebrating small wins, handling problems as growth opportunities, why building a business is like eating glass, and much more.
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0:00 intro
2:24 why Dillan & Colby recorded this
4:27 defining a business through its problems
6:28 the idea for Grindstone
17:07 the power of accountability
19:40 benefits of having a team
21:40 getting your first clients (Alex Hormozi style)
32:18 first paid clients
39:26 entrepreneurship is “eating glass”
46:06 first $197 client moment
51:33 reflections and what’s next
More
Episode 1 of "Behind Grindstone." Dillan (CEO of Grindstone) and Colby (Head Coach of Grindstone) sit down and have their first-ever recorded debriefing of how they started the company. The goal is to track their journey, remember the hard times, and share all the mistakes and lessons as they try to scale Grindstone. They discuss: the origin story of Grindstone, why accountability coaching works, starting with pro bono clients, learning to work as a team, celebrating small wins, handling problems as growth opportunities, why building a business is like eating glass, and much more. ••• 0:00 intro 2:24 why Dillan & Colby recorded this 4:27 defining a business through its problems 6:28 the idea for Grindstone 17:07 the power of accountability 19:40 benefits of having a team 21:40 getting your first clients (Alex Hormozi style) 32:18 first paid clients 39:26 entrepreneurship is “eating glass” 46:06 first $197 client moment 51:33 reflections and what’s next