101 Sketches To Start Meaningful Conversations with Carl Richards
Release Date: 10/14/2025
Five Questions To Ask About the Future of Your Business
Mission Driven Business
Ten years into building a business, the questions you ask yourself need to change. In this episode, Brian Thompson wraps up the BTF tenth anniversary series by looking forward, sharing five questions every entrepreneur should ask about the future of their business, and the power of writing a letter to your future self. This is not a strategic planning session. There are no revenue projections or growth targets. It is an honest and personal reflection on what intentional entrepreneurship looks like when survival is no longer the primary question. In this episode you will learn: ...
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What I Believed About Business in 2016 and What I Know Now
Mission Driven Business
Ten years of entrepreneurship changes the way you think about almost everything. In this episode, Brian Thompson shares ten belief shifts that shaped his journey from 2016 to 2026, and what they might mean for wherever you are in building your own business. Brian introduces two versions of himself: 2016 Brian, the guy who just walked away from a comfortable legal career with a vision and a lot of assumptions, and 2026 Brian, someone who has spent a decade building a business, serving clients, making mistakes, and learning along the way. The result is an honest and personal reflection on what...
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A Decade in Business: Lessons, Gratitude, and What Comes Next
Mission Driven Business
Ten years ago, Brian Thompson walked out of his law firm for the last time with a vision, a lot of fear, and no guaranteed paycheck. In this episode, he reflects on a decade of entrepreneurship, the lessons that shaped him, the people who made it possible, and what the next ten years of mission-driven financial planning looks like. This is not a strategy episode. It is a personal and heartfelt thank you to everyone who has been part of the BTF journey, and a reminder that meaningful businesses are not built overnight. They are built one conversation, one client, one courageous decision, and...
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How to Review Your Business Finances Mid-Year
Mission Driven Business
The halfway point of the year is one of the best moments to review your business finances, and most entrepreneurs let it pass without taking action. In this episode, Brian Thompson shares the CASH framework, a simple mid-year review you can complete in under an hour, that helps you understand where your business stands and make better decisions for the second half of the year. Brian gets honest about his own relationship with numbers and why most entrepreneurs avoid their finances, not because the news is bad, but because looking feels uncomfortable. This episode is a practical and...
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How to Make Better Business Decisions Using a Simple Framework
Mission Driven Business
Most entrepreneurs treat business problems as money problems. In this episode, Brian Thompson makes the case that they are almost always alignment problems, and that better decision-making starts not with tactics, but with mission, vision, and values. Brian shares the alignment framework he uses with entrepreneurs across industries to help them make decisions with more clarity, confidence, and purpose. If you have ever felt like your business decisions are harder than they should be, this episode will help you understand why, and what to do about it. In this episode you will learn: Why...
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Why Better Systems Won't Fix Entrepreneurial Burnout
Mission Driven Business
Refining workflows and checklists cannot solve every foundational business hurdle. In this episode, Brian Thompson explores why a focus on optimization often leads to the avoidance of deeper personal and operational challenges, and what actually builds true resilience over the long term. Brian opens up about navigating a profound capacity problem during a period of intense personal transition and business growth. If you have ever felt exhausted despite having a perfectly organized schedule, this episode explains why the solution often requires subtraction. In this episode you will...
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Choosing the Right Business Structure for a Mission-Driven Business
Mission Driven Business
Choosing the right business structure is one of the most important decisions a mission-driven business owner will make, and taxes are only part of the story. In this episode, Brian Thompson walks through every major business structure available to entrepreneurs, viewed through the lens of ownership, profit sharing, decision making, and mission protection. Whether you are just starting out, growing your team, or thinking about the best way to share profits, this episode will help you ask better questions and make a more informed decision about the structure that fits the business you are...
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People Before Profit: The Co-op Business Model
Mission Driven Business
Most entrepreneurs have never seriously considered the cooperative business model, even though some of the most recognizable brands in the world are co-ops. In this episode, Brian Thompson sits down with D.G. Safeer Hopton, entrepreneur, healer, and author of Creating a Co-op Village, to explore cooperative economics and what it could mean for mission-driven business owners. Safeer has spent decades building co-ops, studying cooperative economics, and helping communities create prosperity through shared ownership. This conversation is a practical and eye-opening introduction to a business...
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Why Revenue Growth Isn't Making You Feel Safer
Mission Driven Business
More revenue does not automatically create financial security. In this episode, Brian Thompson explores why so many entrepreneurs still feel anxious even when business is going well, and what actually builds business stability over the long term. Brian gets honest about the gap between revenue growth and emotional security, drawing from his own experience and years of working with entrepreneurs at every stage of business. If you have ever hit a goal and still felt like everything could fall apart, this episode will help you understand why, and what to do about it. In this episode you...
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The Cost of Hiding Who You Are in Your Business
Mission Driven Business
Let's explore the real emotional and strategic cost of hiding parts of yourself as an entrepreneur, and why building a business rooted in authenticity creates stronger alignment, better marketing, and a more sustainable path forward. Brian gets personal about his own journey navigating visibility as a Black, gay entrepreneur and financial planner, and what he has learned about the difference between protecting yourself and slowly erasing yourself. If you have ever felt exhausted by performing a version of yourself you thought people expected, this episode is for you. In this episode you...
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
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Carl’s newest book: “Your Money: Reimagining Wealth in Simple Sketches”
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Bulk order “Your Money: Reimagining Wealth in Simple Sketches” and save an additional 5% by using the code YourMoney5 at checkout
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Carl’s other books: The Behavior Gap and The One-Page Financial Plan
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Carl’s podcast: Behavior Gap Radio
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The Society of Advice online community of financial planners
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Carl’s New York Times column
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Follow Carl Richards Online: Website, Instagram, X, LinkedIn
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Brian Thompson Financial: Website, Newsletter, Podcast
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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.