Dan and Ian discuss the importance of three key executive roles—CEO, COO, and CFO—within bootstrapped businesses, emphasizing the need for founders to embrace responsibilities beyond visionary tasks.
They share insights from this year’s DCBKK and a sneak peek into the upcoming DC Black event in New York.

(00:00:22) Welcome and Introduction
(00:01:03) The Three Hats of Bootstrapping
(00:09:51) Trends from DCBKK Event
(00:12:34) The Importance of Financial Planning
(00:19:30) LinkedIn as a Top Funnel Tool
(00:22:50) Reflections and Future Events

Useful links:
Access our free business resources
Connect with other entrepreneurs
Coaching for $250K+ founders
Community for 1M+ founders
Hire remote talent
Find a remote job

Past guests on TMBA include Cal Newport, David Heinemeier Hannson, Seth Godin, Ricardo Semler, Noah Kagan, Rob Walling, Jay Clouse, Einar Vollset, Sam Dogan, Gino Wickam, James Clear, Jodie Cook, Mark Webster, Steph Smith, Taylor Pearson, Tommy Griffith, Justin Tan, Matt Gartland, Travis Jamison, Ayman Al-Abdullah, Tynan, Lucy Bella Simkins, Brian Balfour, Nick Huber, Mike Michalowicz, Greg Crabtree, Jordan Gal

Additional episodes you might enjoy:

$30K a Month on Upwork in Less Than 2 Years

“You’re Gonna Mess It Up The Way Everybody Messes It Up”

“When is my LTV good enough?” + Founder Mode for Bootstrappers

$100K MRR in 12 Months… Can They Do It?

Life is Pain - The Babylonian Job (Worship, Part 3) - Episode 043