What starts as "I need to practice presenting" can turn into a personal brand that opens doors. Ann Marie Chrudimsky, Enterprise Account Executive at Box, joins John and Nate to share how her Blue Microphone interview series evolved from Instagram book reviews to interviewing executives at her company's annual conference.

The conversation explores why some of the best side projects start with skill-building rather than ambition, how to navigate organizational politics when you want to create content, and why writing and project management are becoming more valuable as AI floods inboxes with generic messages. Ann Marie also breaks down the reality of enterprise sales cycles, navigating increasingly complex procurement processes, and how relationship-building remains the differentiator when everyone else is automating.

Plus: How AI may solve a decades old OCR challenge, why tech barriers stop more projects than fear does, the strategic advantage of starting with low-stakes personal content, and proof that John was once good at talking to customers.

Topics covered:

• Building skills through low-stakes practice
• Creating content that serves your development (not just your company)
• Navigating organizational support for personal brand initiatives
• Enterprise sales in an era of security scrutiny
• Why human touch matters more as automation increases

Lessons learned: Dead mice at school require parental conversations, 5.5 million devices still run Windows XP, and Best Buy now helps your grandma stay at home longer.

Find Ann Marie and the Blue Microphone series on LinkedIn: https://www.linkedin.com/in/annmariechrudimsky/

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod