Ask Us ANYTHING!! 💀 Stop Throwing MONEY at Bad Offers & DATING Advice??? | Ep. 493

There is something oddly relatable about getting dating advice from a guy who hasn't opened a dating app in over two decades. Jay Schwedelson tackles two very different kinds of questions this episode - one sharp and practical about why your "great" offer is probably not great, and one completely unhinged series of dating questions submitted by listeners who really should know better than to ask him.

ㅤ

Best Moments:

(01:45) Jay drops the cold truth: if you think your offer is great but results say otherwise, the offer just isn't great

(02:58) The 100% Rule - the single question you should always ask before trying to save a failing campaign

(04:18) Why throwing more money at a bad offer is a trap, and what to do instead

(06:15) Venmo requesting someone after a bad date - Jay's take is exactly what you'd expect

(07:45) Why going on vacation too early in a relationship is a recipe for disaster (he learned this the hard way)

(08:45) The real reason you need to Google someone before a first date, according to Netflix true crime

ㅤ

MASSIVE thank you to our Sponsor, CallRail!

CallRail is the AI-powered lead intelligence platform that helps marketers prove exactly what’s driving results. With CallRail, you can connect every call, text, chat, and form submission directly to the campaign that generated it so you finally know what’s working and where to double down.

Plus, with built-in AI conversation intelligence, CallRail analyzes your customer conversations, captures leads 24/7, and gives you deeper insights into what your prospects actually care about.

If you’re tired of guessing about your marketing ROI and want real data behind your campaigns, CallRail has you covered.

Start a Free Trial Here: https://www.callrail.com/dothis

ㅤ

Partner with Jay! https://www.jayschwedelson.com/contact

ㅤ

Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out June 9, 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

ㅤ

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/