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The Mission Driven Business Podcast Episode 101: 101 Sketches To Start Meaningful Conversations with Carl Richards

Mission Driven Business

Release Date: 10/14/2025

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Brian Thompson chats with Carl Richards — Certified Financial Planner™, creator of The New York Times “Sketch Guy” column, and bestselling author of “The Behavior Gap” and “The One-Page Financial Plan.” Carl’s simple Sharpie sketches have transformed how millions of people think and talk about money. In his latest book, “Your Money: Reimagining Wealth in Simple Sketches”, he shares 101 drawings and essays designed to spark deeper conversations about money, values, and what matters most.

In this conversation, Brian and Carl dive into the emotional side of money and debate whether money actually can buy happiness.

Episode Highlights

A good sketch can start a conversation.

Carl said the impetus behind his new book is simple: we’re not talking about money in the right way. Instead of focusing on financial “noise” like markets and TV pundits, he wanted to give people tools to have conversations that align money with their values.

“Really good financial decisions happen when we make a little bit of meaning out of money,” Carl said. “We’re getting clear about our purpose.”

Money = feelings.

Carl’s first sketch in the book, and arguably the most powerful, is simply, “Money = Feelings.” He emphasized that money evokes an emotional response, whether that’s anxiety, freedom, or joy.

“We’re not talking about spreadsheets and calculators,” Carl said.

Order can be powerful.

Bringing order to chaos can provide a sense of control when life feels overwhelming. Whether it’s finally sorting through a pile of unopened mail or cleaning the garage, creating a sense of order can help ease anxiety and overwhelm.

“There are so many global things going on that are out of our control,” Carl said. “If you feel nervous or scared, go clean the garage, do the dishes, do something that gives you a sense of control and order.”

Money can buy happiness — if you spend it right.

Can money buy happiness? Carl believes the answer is yes — if you know how to spend it. Money spent on meaningful experiences with loved ones or exerting more freedom over your time is money well spent.

“Nobody wants more money,” he said. “They want what they think money will give them, and if you don’t do the work to figure out the difference, then more money won’t buy you happiness.”

Resources + Links

About Brian and the Mission Driven Business Podcast

Brian Thompson, JD/CFP, is a tax attorney and Certified Financial Planner® who specializes in providing comprehensive financial planning to LGBTQ+ entrepreneurs who run mission-driven businesses. The Mission Driven Business podcast was born out of his passion for helping social entrepreneurs create businesses with purpose and profit.

On the podcast, Brian talks with diverse entrepreneurs and the people who support them. Listeners hear stories of experiences, strength, and hope and get practical advice to help them build businesses that might just change the world, too.