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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We spend so much time stressing about pitch decks…the formatting, the stats, and the perfect slide order. But honestly, that's not what trips most founders up.
The real issue is way simpler: a lot of us just aren't telling investors what they actually need to hear. Not because our ideas are bad, but because the way we explain them ends up hiding the good stuff.
Last week I listened to sixteen founder pitches in a row. Different industries, different personalities, and different business models.
And while every single one had real potential, almost all of them shared the same 5 blind spots.
What stood out wasn't the mistakes themselves, but how shockingly easy they are to fix. The founders who nailed just a few simple things immediately came across clearer, more confident, and honestly… way more fun to listen to.
The difference between a forgettable pitch and a memorable one usually isn't a full overhaul. It's tiny tweaks, and once those clicks happen, the whole pitch lands differently.
In this episode, I go through the 5 common mistakes I see in founder pitches, and why correcting them will get (and keep) the attention of investors.
Topics Covered;
Why most founders bury the most important part of the pitch
How jargon kills investor confidence, even when the idea is great.
The "single-takeaway rule" that instantly makes your deck clearer and more persuasive
What investors actually want to know about your funding ask
Invisible deal-breakers: lack of passion, weak projection, and low energy
How to present traction even when you don't have revenue yet
How to communicate a credible 18-month plan investors can believe in
Verbal, visual, and emotional signals that matter far more than data points
About Your Host
Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!
Connect:
Website: https://seedmoneypodcast.com/
Instagram: https://www.instagram.com/jaylasiciliano/
Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/
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