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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 for
• Why entrepreneurship trades stability for control, purpose, and ownership
• AI’s confidence trap: when tools validate bad ideas
• The Denise Huxtable Test: experimenting vs. actually building
• Uber, Netflix, and businesses born in chaos—what downturns really teach
• A George Michael–inspired sign-off you’ll want to steal

We'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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When did “thought leadership” turn into a high-school popularity contest with ring lights? In this episode of The Ron Table, I sit down with co-hosts Nicole Gray and Laine Belcastro to separate real thought leadership (insight that changes how you think) from the algorithm-friendly soundbites that rack up likes but say nothing.

We talk authenticity over aesthetics, stories over quotes-on-Canva, and why “leadership that fits on a coffee mug” is…well…merch. Expect movie references (Mean Girls, Anchorman, Coming to America, Ghost), a Yankees sidebar, and a hilarious dryer-string near-death experience. More importantly, expect a candid framework for what useful leadership content looks like in 2025—and how to spot the difference between a true perspective and a discount-code pitch.

You’ll hear about:

• Thought leadership vs. influencer content (and why both exist for different jobs)
• How “algorithm-first” posting is insulting your audience’s intelligence
• The difference between motivation, information, and transformation
• Platform fit: where short clips belong and where deeper ideas should live
• A simple test: “Does this reframe my thinking—or just juice my dopamine?”

Question for you: Are you actually learning—or just liking? Tell us what you want more of in future episodes: real playbooks, case studies, frameworks, or quick hits.

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Unlimited Vacation: Perk or PR?
This week on The Ron Table, Laine Belcastro, Nicole Gray and I pull apart the shiny wrapper on “unlimited vacation.” We compare corporate policies (a.k.a. take time off at your own risk) with entrepreneurial “freedom” (answering client emails from a roller coaster). We talk culture vs. policy, permission vs. discipline, and why so many teams still guilt people for stepping away.

Along the way: the real reason unlimited PTO became a thing (follow the money), how good managers actually signal “go take Friday,” and why for business owners the work doesn’t disappear—it waits.

Hit play, then tell us: which is harder—asking your boss for time off, or asking yourself to stop working?