Vibescaling Podcast This Week In GTM Episode #1 - 11/27/25
Timestamps:
(00:00) Why We Changed Our Name from T2D3 to VibeScaling
(12:00) Why Is Everyone Calling Sales "GTM" Now?
(17:00) Is Sales an Art or a Science?
(22:30) The Viral Giga Story: What to Look For Before Joining a Startup
(33:00) How to Evaluate Startup Equity (Shares Outstanding Explained)
(35:00) The AI Tools We're Actually Using Right Now
(44:00) "Choose Company Over Title" - Is This Advice Actually Useful?
(50:00) Easy Mode vs. Hard Mode: The Stripe 250M ARR Debate
(55:00) Nepotism in AI Hiring: Why Who You Know Still Matters
(57:00) Thanksgiving Food Power Rankings
Episode Description:
In the inaugural episode of "This Week in GTM," Chris and Cailen riff on the tweets they've been texting each other all week and share unfiltered takes on the state of early-stage sales.
Discussed in this episode:
- Why we rebranded from T2D3 to VibeScaling (and why the old name stopped making sense in AI)
- The "GTM" rebrand of sales: pretentious or practical?
- How to evaluate a startup before joining: the science of de-risking your next role
- Why you need to know shares outstanding before accepting an offer
- The AI tools we're actually using daily: Gemini, Clay, Nerve, Centralize, Gamma
- Maggie from OpenAI's viral advice and why we push back on "choose company over title"
- Easy mode vs. hard mode: why joining at $250M ARR is fundamentally different than $0-5M
- Why PLG sellers are "picking up money off the floor" and some admit their skills are atrophying
- The uncomfortable truth about nepotism in AI hiring
- Who you know still matters more than being qualified
Host Links:
Cailen DSa - LinkedIn - https://www.linkedin.com/in/cailen/
Chris Balestras - LinkedIn - https://www.linkedin.com/in/balestras/
About VibeScaling Podcast:
The VibeScaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, partner @ VibeScaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.
No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.
About VibeScaling:
VibeScaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.
Where to Find VibeScaling:
LinkedIn Company Page - / vibescaling
YouTube - / @vibescaling
Newsletter - GTMBA - https://gtmba.beehiiv.com/
Website - https://www.vibescaling.ai/