In this episode of Smart Leaders Sell, Jessica addresses what happens when the strategy isn’t working, when to stick, and when to twist. She describes her experiences with her cool grandma, who taught her how to play cards like a hustler.

She goes on to explain the game of 21, the rules, the probability, the chance. Jess compares it to business as she continues to inject actionable strategies, quotes and explanations into the metaphor.

She talks about planning, and choosing proper launch and sales strategies for your business. Why they are important, and what can be derived from them. Jess also gets into market research, and validating ideas before launching them, and why these things are such a good idea.

She talks about selling at scale, and getting enough eyes on your offers in order to meet your desired outcome. She also delves into communication of value, and the difference between features and benefits.


“It’s a game of probability and chance”

“Failure to plan equals plan to fail”

“We get very stuck in the minutia of how we’re going to sell”

“If there’s no pain, then it’s going to be really really difficult to sell it”

“If people are purchasing, you are doing the right things”

“Are you clearly communicating the transformation?”

“Ultimately we can only control the effort that we put in”

“People want you to be very confident in your side of the bargain”