How To Make Every Pitch End In A “YES”- The Art Of The Orbit Jump with Chelsea Riffe

Oct 16, 2025

58:24

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Is it just me, or are you also tired of getting cold pitches that make you want to hurl your phone across the room?

I sat down with Chelsea Riffe, podcast strategist extraordinaire and the human embodiment of "if you don't ask, the answer's always no." We're talking orbit jumping (borrowing someone else's audience), why your pitch probably sucks, and how to ask for literally anything without being half-assed about it.

If you've ever slid into someone's DMs with "I'd love to help" or "Let me know what you think" and wondered why you got no response, this episode is your intervention.

TOPICS & TANGENTS

— How to expand your world instead of staying in your echo chamber

— The anatomy of a perfect pitch

— The “charm and disarm” strategy

— Navy blue sheets = unacceptable living conditions

— Why "I'd love to help" makes me homicidal

— The worst pitches we've ever received

— My dating app line that worked every single time

POINT OF THE STORY

Don’t be afraid of pitching. The worst thing that can happen is hearing "no,” which is exactly what you'll get if you don't ask at all.

GIVEAWAY

Want a free one-on-one strategy session with me? Go to Spotify and comment on this podcast episode what you would love to pitch someone, and I’ll enter you to win!

Love you, mean it. 🖤

CHELSEA LINKS

— Follow Chelsea on Instagram and Threads

— Join her program Pitch Perfect (Code: SARABTL for $100 off in October, but if you listen to this after October and send her a good pitch on why she should honor the code, she might still accept it!)

— Subscribe to her podcasts The Art of the Ask and In My Non-Expert Opinion

— Check out her website

— Subscribe to her Substack

— Chelsea’s walkout song

BTL LINKS

— Use code "MILLIONAIRE" for $100 off my website copywriting course, Site Series Sprint.

— Join the Point of the Story community on Slack.

— Leave feedback or episode requests in our Suggestions Box.

— To stay up to date with all things Point of the Story, follow on Instagram and Substack.

— Follow me on Instagram, Threads, and Substack.

— Subscribe to my newsletters Tuesday Table of Contents for one marketing tip, once a week and Millionaire Moment for the insider tea on how I plan to make $1 mil in sales by my 31st birthday.

— Check out my website betweenthelinescopy.com.