EP 141: Making Clients Comfortable With Uncomfortable Subjects With Financial Behaviorist Jacquette Timmons

The Nitty Gritty

  • How Jacquette uses different themes every month to inform the activities and questions she poses during her monthly dinner series, The Comfort Circle™
  • Why Jacquette increased the event pricing from $75 to $150 per person and what went into the decision to host the dinner in the same restaurant month after month
  • How the dinner series works into her larger business model — and why she’ll be offering self-hosted dinners as well as firm-hosted ones
  • What’s the future of The Comfort Circle™? Jacquette says that it might include retreats

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Financial behaviorist Jacquette Timmons helps people talk about uncomfortable things. One of the ways she does that is through The Comfort Circle™, an intimate gathering where she walks her guests through curated topics about money and life over a three-course meal.

In this episode of What Works, Jacquette shares her perspective on discomfort and why it’s crucial to success, how she uses different topics to curate The Comfort Circle™ experience, and where this in-person event fits into her business model.

If you’re a coach or consultant and you’re looking for new ways to approach your business model, this episode is for you. And even if you aren’t, Jacquette’s stories and experience provide insights into pricing a service and leaning into discomfort: two essential skills that every entrepreneur needs.

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Why an in-person dinner on money and life?

“My clients can talk about sex with their friends. But they can’t talk about money because there isn’t an environment where people feel that they can be vulnerable.” — Jacquette Timmons

It was obvious to Jacquette: people need safe spaces to have difficult conversations. Initially, Jacquette considered a traveling conference that would pop-up in several U.S. cities. But she realized that it required too many resources.

Instead, she decided to think smaller and more intimate… and that’s where the idea for The Comfort Circle™ came. The dinner series, which started in January 2017 in New York, provided a space for real talk around money and fit within her business vision while suiting Jacquette’s natural inclination to connect in person. “I know live events are powerful,” she says. “I know I show up powerfully and I connect well with people that way.”

Jacquette consistently hosts The Comfort Circle in the same restaurant for a small group. She says the max is twelve guests because her intent was always to keep the dinners intimate.

How The Comfort Circle™ fits into her larger business model

“The dinner is a lead generation vehicle. It’s an opportunity to get to know me and my approach. Some of them convert into coaching clients. Not every dinner results in immediate conversion or a conversion to a four figure coaching engagement but that does happen.” — Jacquette Timmons

Jacquette uses the monthly dinner series as a way to connect with potential clients — both personal and corporate. “I already do financial workshops for corporations,” she explains, “but there are times when they don’t want to do the same old thing. This is a way of doing something different.”

Different indeed! For example, a law firm hired her to host a customized dinner for 40 people. And instead of charging the typical $150/per person, the firm paid her as a speaker. “I now think of this as there’s a self-hosted version of the dinners and there’s the firm-hosted dinners, which I’m hoping will gain some traction,” Jacquette adds.

Besides strategically using the dinners as a lead generation experience, they also inform her content strategy. Because every dinner has a theme, Jacquette uses that as her marketing focus. For example, she’ll make an announcement for an upcoming dinner in her email, blog posts, and social media focusing on that same theme.

Hear more from Jacquette Timmons on how she uses The Comfort Circle™ as a lead generation strategy and what the future looks like for these intimate dining experiences.

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