HeyJaredBreakout
Breakout is a private podcast where I think out loud about business, life, and everything in between.It’s a space for nuance, honesty, and real conversation — not content calendars or copy-and-paste strategies.
- Indexed episodes, last 90 days
- 7
- Latest publication
- Sep 8, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 11, 2026
Latest episodes
I thought I already unlearned this (opens the original)
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The short version: Sometimes the should doesn’t look like a should. Sometimes it looks like growth, certainty, better positioning, or the version of business everyone else seems to be doing. What this is: A solo riff from the middle of the fog clearing. I’m talking about what happened after I launched Move It Out, made the hard call to let go of a misaligned client, and found myself trying to force my business into a version that looked good on paper but didn’t actually feel like me. This one is
The thing you keep not doing (opens the original)
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The short version: You already know what to do. That’s exactly why the one thing you still haven’t done can fuck with your head so much. What this is: A solo riff on what’s usually happening underneath the business project you keep saying you’ll get to “next month” and why another strategy, template, AI chat, or prettier plan probably isn’t the missing piece. In this episode: – Why one unfinished project can somehow start feeling more convincing than the entire pile of evidence that you know how
The Least Interesting Thing About Me with Karrie Lemansky - 2 of 2 (opens the original)
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Quick Take: Karrie and I keep going: what unmasking actually costs, ending a 20-year friendship I didn't see coming, and the difference between a coach and a business friend, and why you need both. What's Inside: – Why "ADHD is the least interesting thing about me" isn't erasure, it's the compliment – Regression after diagnosis: when things that used to be easy suddenly feel impossible because the mask is gone – Proof of concept versus external validation, and why needing proof is smart business
Give Me the Roadmap, But Don't Tell Me What to Do with Karrie Lemansky 1 of 2 (opens the original)
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Quick Take: Karrie Lemansky and I get into why "just do it" makes us both feral, why seventeen dead offers weren't a waste of time, and the real reason "imposter syndrome" was never the right name for what either of us was dealing with. What's Inside: – How Karrie and I actually met (the Anti Framework Playbook, a five-day thing, me being "a nosy little fucker") – Why "why can't you just do this" might be the phrase we hate most, and what it gets wrong about how our brains work – The self-trust
ai as an accessibility tool with Claire Paniccia - 3 of 3 (opens the original)
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The short version: "I would have made absolutely no money this year if I hadn't been able to rely on Claude to help me write emails." What this is: The last one with Claire Paniccia (3 of 3) — the accessibility stack behind her summit, and the honest version of the AI conversation: what it's for, what it's not, and why the guilt so many of us carry about using it doesn't hold up. What we get into: – The accessibility build behind the Neurodiverse Entrepreneur Summit: 12-hour buy timers, closed c
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