The Ron Table Ep: 16 - Timing Isn’t a Strategy: When the Business Doesn’t Fit the Plan
Thu Nov 06 2025
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Should you wait for the “right time” to start your own thing—or admit the market will never send an engraved invitation? In this episode of The Ron Table Nicole Gray, Laine Belcastro and yours truly, get real about timing, layoffs, and the messy truth of entrepreneurship: it’s not freedom—it’s ownership.
From Fight Club’s “after we’ve lost everything” gut check to a South Park riff on AI telling you you’re always right, we unpack why fear disguised as logic keeps people stuck, why some folks should not jump now (and that’s okay), and how to tell the difference between a side hustle to keep the lights on and a business you’re built to run.
In this episode:
Gut + circumstance > perfect timing (there isn’t any)Layoffs, pride, and the hard reset nobody plans forWhy entrepreneurship trades stability for control, purpose, and ownershipAI’s confidence trap: when tools validate bad ideasThe Denise Huxtable Test: experimenting vs. actually buildingUber, Netflix, and businesses born in chaos—what downturns really teachA George Michael–inspired sign-off you’ll want to stealWe'd love to hear from you! If you launched (or didn’t) after a layoff, what made it the right move—or not? Tell us your story and we’ll feature a few in the next mailbag.
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Send us a text Should you wait for the “right time” to start your own thing—or admit the market will never send an engraved invitation? In this episode of The Ron Table Nicole Gray, Laine Belcastro and yours truly, get real about timing, layoffs, and the messy truth of entrepreneurship: it’s not freedom—it’s ownership. From Fight Club’s “after we’ve lost everything” gut check to a South Park riff on AI telling you you’re always right, we unpack why fear disguised as logic keeps people stuck, why some folks should not jump now (and that’s okay), and how to tell the difference between a side hustle to keep the lights on and a business you’re built to run. In this episode: Gut + circumstance > perfect timing (there isn’t any)Layoffs, pride, and the hard reset nobody plans forWhy entrepreneurship trades stability for control, purpose, and ownershipAI’s confidence trap: when tools validate bad ideasThe Denise Huxtable Test: experimenting vs. actually buildingUber, Netflix, and businesses born in chaos—what downturns really teachA George Michael–inspired sign-off you’ll want to stealWe'd love to hear from you! If you launched (or didn’t) after a layoff, what made it the right move—or not? Tell us your story and we’ll feature a few in the next mailbag.