Resend strategy nuances and timing

If you have ever thought about quitting your agency job to start your own consultancy, Jessica Best has the blueprint on how to actually make it work. She joins Jay Schwedelson to break down why betting on yourself is less scary than staying in a job that drives you crazy. They also get into a heated debate over email marketing hot takes, including why resending to non-openers might be a waste of time and why most A/B tests fail to prove anything useful.

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Connect with Jessica on LinkedIn or visit her website at Jessica.Best

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Best Moments:

(02:00) Why getting mad at your current situation is the best fuel for starting a business

(04:23) The terrifying reality of keeping your sales pipeline full when you work for yourself

(06:30) Jessica argues that resending emails to non-openers is actually a bad strategy

(08:00) Jay reveals his aggressive subject line trick for getting people to open the second time

(10:00) Why testing every single email you send is a terrible idea that drives you crazy

(14:00) The myth of the perfect day and time to send an email campaign

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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out April 21, 2026). All net proceeds are donated to The V Foundation for Cancer Research—let’s kick cancer’s butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206