How to Build a Career When the Rules Keep Changing w/ Taylor Desseyn & Jason Torres

How to Build a Career When the Rules Keep Changing w/ Taylor Desseyn & Jason Torres

Author: Skill Issue Studios November 13, 2025 Duration: 44:38

Recorded live at All Things Open, Robbie talks with Taylor Desseyn and Jason Torres about the future of tech careers, AI’s impact on hiring, and why relationships still matter more than résumés. They share insights from years in recruiting and community building, stressing that genuine connection—not cold applications—opens doors in today’s market.

In this episode:

  • (00:00) - Intro
  • (01:48) - A toast to Busch Light
  • (05:46) - Meet Taylor and Jason
  • (08:14) - Is now a good time to get into tech?
  • (13:12) - How AI is reshaping the tech job market
  • (16:07) - Standing out in a crowded industry
  • (20:36) - Can open source help you get hired?
  • (23:48) - Will Shane Beamer head to Virginia Tech?
  • (25:13) - Do pro athletes really make too much money?
  • (26:47) - Should politicians be paid like CEOs?
  • (30:43) - What it means to be an authentic creator
  • (34:07) - How Torc is chasing greatness
  • (38:01) - Is AI killing organic content growth?
  • (39:26) - Parenting, perspective, and balance
  • (42:20) - Where to connect with Taylor and Jason online

Links

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Connect with Jason

Connect with the hosts

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There's a certain alchemy that happens when you combine deep technical expertise with the warmth of a good conversation, and that's exactly what you'll find in Whiskey Web and Whatnot. Hosts Robbie Wagner, Charles William Carpenter III, and Adam Argyle bring decades of collective experience to the table, but they leave the lecture format at the door. Instead, each episode feels like pulling up a chair with colleagues who are just as passionate about the craft of building for the web as they are about the nuanced flavors in a glass of whiskey. The discussion naturally flows between the concrete details of modern development-like navigating JavaScript frameworks, CSS architecture, or the practical realities of agentic AI and new coding tools-and the broader, human aspects of a software engineering career. This podcast from Skill Issue Studios is built on the idea that the tools and the people who use them are equally important. You'll come for insightful, grounded advice on developer productivity and emerging technologies, but you'll stay for the genuine camaraderie and the occasional spirited debate about which whiskey bottle truly earns a spot on the shelf. It’s a refreshing blend of substance and personality, making complex topics accessible and reminding everyone that there's always a story behind the code.
Author: Language: English Episodes: 100

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