Help Wanted

Jason reaches into the mailbag and selects two questions. One from someone about just starting out, one from someone figuring out what comes next.

When the check comes at the end of a business dinner, who should pay? The bigger company? Does that even matter? These are the questions on our Executive Producer Morgan's mind after an awkward fumble at the end of a business dinner with a big tab. Jason gives a framework you can use to assess when you should throw your card down, and what to say if you can't.

When we want someone to trust us, the instinct is to present ourselves as the perfect fit. But what if that's actually the thing that's making people skeptical? Jason shares the time-tested but counterintuitive tactic he uses in his own business.

The boom of online courses, coaching and consulting has opened up a new revenue stream for anyone with a teachable skill. This is all fun and games, until you get to the little detail of pricing. How do you set a price on… yourself? That’s the question that made listener Kelsey call the Help Line. To give her the cheat code on pricing strategy, Nicole and Jason phone a friend who knows the course landscape inside and out: Matt Gartland, CEO at Smart Passive Income Media. For more Matt, check out all things SPI: https://www.smartpassiveincome.com/ Originally aired in 2024

You’re ready to move on from something— but you’re struggling to leave. You keep asking yourself, “Is this worth staying for?” Today, Jason will help you answer that question. And he starts with his own version of this problem. Are you ready to meet Drunk Party Jason?

Do you have a sneaking suspicion your coworker is mad at you? At best, this feeling can darken your day. At worst, this feeling can turn your workplace into a toxic environment. Jason and Nicole tell you how to handle this hunch, using a very personal example: a time Nicole thought Jason hated her! Originally aired in 2024

Someone upset you and you wanna respond immediately. But Jason's learned that your short-term impulses rarely serve your long-term needs. Today he shares a framework that's helped him navigate moments of stress more effectively and shows you why the most satisfying response is rarely the smartest one.

What happens when you hire someone, and they charge way more than you expected? That happened to our caller, Kassi Underwood, whose babysitter handed her a steep bill. (So steep, a screenshot of it went viral on LinkedIn!) Jason and Nicole give advice on how to course-correct, and how to prevent making this big mistake in the first place. Originally aired in 2024

We’ve all held back from asking for what we wanted and ended up feeling hurt. But what you might not realize is that it's also hurting your potential partnerships.  To ask Jason and Nicole for help on the show, just fill out this form!

Nicole recently almost did a deal with one of her friends... until that friend pulled out of the deal. Now, Nicole has an emotional email sitting in her drafts: should she send it? Today, Jason shares the thought exercise he applies before sending any email he's not sure about.