101 Sketches To Start Meaningful Conversations with Carl Richards
Release Date: 10/14/2025
Why You're Feeling Stuck: The Hidden Cost of Clutter in Your Business
Mission Driven Business
Clutter has a way of building quietly, and before long it starts affecting more than just how your desk looks. In this episode, Brian Thompson takes an honest look at how small pockets of disorganization pile up during busy seasons and what they actually cost you, not just in time, but in decision-making, financial clarity, and the ability to move your business forward. Coming off tax season, Brian gets personal about his own clutter habits and offers a simple, practical approach to clearing the backlog without overhauling everything at once. Clutter Is About Avoidance, Not Organization...
info_outline
Why You'll Never Find Balance in Your Business
Mission Driven Business
Balance is one of the most talked about goals in entrepreneurship, and one of the most elusive. In this episode, Brian Thompson gets honest about why balance isn't something you achieve once and move on from, and why chasing that perfect equilibrium might be the wrong goal entirely. Coming off a particularly intense tax season, Brian shares what his own body was telling him, and what it made him realize about the way entrepreneurs expect themselves to show up all year long. What Does Business Balance Actually Look Like? This year's tax season hit differently for Brian. For the first...
info_outline
How to Bet on Yourself and Build a Business Around Freedom
Mission Driven Business
Building a business around freedom is more than a financial decision, it's a deeply personal one. In this episode, Brian Thompson sits down with Kyra Mitchell Lewis, a brand strategist, marketer, podcast host, and founder of and , to talk about what it truly means to bet on yourself. Kyra shares how more than 20 years in corporate marketing led her to a pivotal moment of liberation, how she built a thriving consulting business in under a year, and why keeping an open mind has been one of her greatest entrepreneurial assets. A Business Built Around Purpose Kyra defines a mission-driven...
info_outline
How to Prepare for Next Year's Taxes Without the Stress
Mission Driven Business
Tax season doesn't have to be a scramble, but for most business owners, it is. In this episode, Brian Thompson offers a simple, practical system for taking the stress and surprise out of taxes by shifting from a once-a-year reaction to a year-round strategy. If last episode left you wondering whether you missed something, this one is your action plan. Start With a Mindset Shift Before getting into tactics, Brian makes an important reframe: taxes are not a once-a-year event. They are a year-round strategy. This matters especially for mission-driven business owners who are growing...
info_outline
How to Optimize Your Tax Return for More Business Tax Savings
Mission Driven Business
In this episode, Brian Thompson discusses key insights from the recent tax season, highlighting trends, surprises, and strategic opportunities for business owners to optimize their tax planning and financial health. Your tax return is not something to file and forget. If you pay attention, your tax return gives you a roadmap for what to do better this coming year. Brian also gives real-life examples of two clients that stood out this tax season. Understanding Unexpected Tax Outcomes One of the most significant stress points during tax season is the unexpected tax outcome. Many business...
info_outline
S-Corps Explained: Tax Savings, Trade-Offs, and What No One Tells You
Mission Driven Business
The S-Corp question is one of the most common Brian hears from entrepreneurs, but the answer is almost never as simple as the internet makes it sound. In this episode, Brian Thompson breaks down what an S-Corp actually is, how the potential tax savings work, and the real-world trade-offs that often get left out of the conversation. Whether you're considering the election for the first time or revisiting the decision, this episode gives you the context you need to make an informed choice. What is an S-Corp? First, an important clarification: an S-Corporation is not a business structure,...
info_outline
Budgeting Series #3: A Guide to Building Your Financial Strategy
Mission Driven Business
Awareness and acceptance lay the groundwork, but nothing changes until you take action. In this final episode of the budgeting series, Brian Thompson brings the framework full circle by focusing on what to actually do with your numbers. Because understanding your finances and accepting where you are is only powerful if it leads somewhere. This episode is about making intentional, strategic decisions that move your mission-driven business forward. Start With Vision, Not Spreadsheets Before diving into tactics, Brian starts with something that might surprise you in a budgeting...
info_outline
Building a Profitable Practice with Authenticity and Heart
Mission Driven Business
Rooted in identity, community, and purpose is what it truly means to build a business with heart. Brian Thompson sits down with Kala Lacy, an EMDR-trained yoga psychotherapist and founder of , a holistic wellness practice centered on Black and queer people of color. Kala shares how she turned her own healing journey into a thriving private practice, why niching down with radical specificity was the key to her success, and what inspired her newest venture: , a mentorship community for Black, queer, and trans clinicians building aligned private practices. A Business With Heart Kala...
info_outline
Budgeting Series #2: A Guide to Money Mindset Shifts
Mission Driven Business
Money isn't just math and for most entrepreneurs, it never has been. In this episode, Brian Thompson continues the budgeting series with part two: acceptance. Building on , Brian explores the emotional side of budgeting and why looking at your numbers without shame or judgment is just as important as looking at them at all. Why Financial Acceptance Is the Missing Piece Once you have your numbers, you're naturally going to have feelings about them. Money is tied to your upbringing, your fears, your identity, and your sense of security. Brian sees it constantly in his client work: people...
info_outline
Budgeting Series #1: A Guide to Financial Awareness
Mission Driven Business
Budgeting doesn't have to be intimidating, but it does have to be intentional. In this episode, Brian Thompson kicks off a brand new solo series on budgeting for entrepreneurs, approaching the topic through three lenses: awareness, acceptance, and action. The episode is the first and most foundational step: Awareness. Whether you're a new business owner or a seasoned mission-driven entrepreneur, understanding where your money is actually going is the starting point for everything else. Why Financial Awareness Comes First Every January, Brian's inbox fills up with clients asking to...
info_outlineBrian 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
-
Carl’s newest book: “Your Money: Reimagining Wealth in Simple Sketches”
-
Bulk order “Your Money: Reimagining Wealth in Simple Sketches” and save an additional 5% by using the code YourMoney5 at checkout
-
Carl’s other books: The Behavior Gap and The One-Page Financial Plan
-
Carl’s podcast: Behavior Gap Radio
-
The Society of Advice online community of financial planners
-
Carl’s New York Times column
-
Follow Carl Richards Online: Website, Instagram, X, LinkedIn
-
Brian Thompson Financial: Website, Newsletter, Podcast
-
Follow Brian Thompson Online: Instagram, Facebook, LinkedIn, X, Forbes
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.