
The Rich Webster Show
On The Rich Webster Show, you'll get an unfiltered look behind the scenes at how I'm running my businesses, the frameworks I use to build them, and how you can design your own business to work less and earn more. Along the way, you'll learn the strategies, tools, and frameworks to create a one-person business that meets both your profit and lifestyle goals.
Topics I cover include: entrepreneurship, productivity, lifestyle design, social media, design, creativity, business
Latest episodes

11 snips
Jun 18, 2025 • 42min
Two Paths To $500k As A Solopreneur
Discover the hidden roadblocks that keep solopreneurs stuck at $100K. Explore the two paths to scale: leverage deep expertise in the expert business model or streamline operations using systems in the marketing model. Learn essential skills for each approach and how to attract clients effectively. Delve into real-life examples and uncover why generalist energy can be detrimental. Finally, hear about strategies that can elevate your solo business to new heights without the burden of a large team.

14 snips
Jun 4, 2025 • 45min
Why High Prices CREATE More Value (Art World Proof)
What does a dead shark in a glass tank have to teach you about pricing, branding, and human behavior?A lot, actually.In this episode, I break down seven unexpected business lessons from the strange, status-obsessed world of high-end contemporary art:Brand = Price. Why unknown artists starve while branded ones sell red splotches for millions. And how to use the same principle to raise your rates.High Price Creates Value. The shark wasn’t valuable so it was expensive. It became valuable because it was expensive. Yes, it’s weird. And yes, you can use this.Value by Association. How hanging your work next to someone prestigious (literally or metaphorically) triples its perceived worth. Most people never think to do this.The Agent Gap. If someone else sold your work, they’d charge more. So why aren’t you? Here’s how to become your own hype man - and get paid accordingly.Network is a Cheat Code. Contemporary art runs on relationships. So does business. Your next opportunity probably isn’t on your to-do list, it’s in your texts.Scarcity is a Power Tool. One-of-one art pieces command outrageous prices. Your time is just as limited. Are you pricing accordingly?People Who Pay, Pay Attention. When collectors gave their art away, it got shelved. When they sold it, it got hung on the wall. Same with your clients. Charging more = more buy-in.This episode isn’t really about art. It’s about leverage. And how to build a business that feels more like a masterpiece—and less like mass production.When you’re ready, here are 4 ways I can help you:🛠️ 6-Figure Solopreneur Systems (FREE COURSE)Steal the exact systems I use to run TWO multi-six-figure solo businesses in under 20 hours a week.https://startbuildingsystems.com/📬 Work Less Wednesday (NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k readers.https://www.worklesswednesday.com🏖 How To Work Less (PAID COURSE)From 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)https://www.learn.howtoworkless.com🧪 Work Closely With Me (MENTORSHIP)I advise and mentor 6-7 figure Creative Solopreneurs. If you want to work closely with me (i.e. we speak 1-2 times a week), watch this video, then let's talk:https://learn.howtoworkless.com/lab/Instagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

May 7, 2025 • 39min
Why You’re Stuck at the Same Income Level (The Success Thermostat)
We all have an 'inner thermostat' for the amount of money we feel that we “should” earn.- When we make less than that number, we scramble to earn more. - When we make more than that number, we self sabotage or take our foot off the gas.Many entrepreneurs get “stuck” at a certain income level for years as a result. After working with hundreds of entrepreneurs, I can confirm: It's an EXTREMELY common problem.So in this podcast, I reveal:Why entrepreneurs get stuck at the exact same income level for yearsWhy using fear as motivation leads to burnout (and what to do instead)Why your income ceiling isn't a business problem - it's an IDENTITY problemWhy your biggest fear isn't failure - it's actually success7 frameworks you can use to reset your internal "success thermostat"When you’re ready, here are 4 ways I can help you:🛠️ 6-Figure Solopreneur Systems (FREE COURSE)Steal the exact systems I use to run TWO multi-six-figure solo businesses in under 20 hours a week.https://startbuildingsystems.com/📬 Work Less Wednesday (NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k readers.https://www.worklesswednesday.com🏖 How To Work Less (PAID COURSE)From 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)https://www.learn.howtoworkless.com🧪 Work Closely With Me (MENTORSHIP)I advise and mentor 6-7 figure Creative Solopreneurs. If you want to work closely with me (i.e. we speak 1-2 times a week), watch this video, then let's talk:https://learn.howtoworkless.com/lab/Instagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

Apr 24, 2025 • 42min
$4 Million & Nothing To Show For It (How To Build Wealth As A Solopreneur)
I should be rich by now.That's a joke. But also kind of not.When I shut down my agency in 2023, I did a final breakdown of the business' finances. $4m+ earned over a decade. And nothing to show for it.This episode breaks down my story, what I learned, what I'm doing to build wealth now, and the 6 steps you can follow to build real wealth as a solopreneur. When you’re ready, here are 4 ways I can help you:🛠️ 6-Figure Solopreneur Systems (FREE COURSE)Steal the exact systems I use to run TWO multi-six-figure solo businesses in under 20 hours a week.https://startbuildingsystems.com/📬 Work Less Wednesday (NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k readers.https://www.worklesswednesday.com🏖 How To Work Less (PAID COURSE)From 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)https://www.learn.howtoworkless.com🧪 Work Closely With Me (MENTORSHIP)I advise and mentor 6-7 figure Creative Solopreneurs. If you want to work closely with me (i.e. we speak 1-2 times a week), watch this video, then let's talk:https://learn.howtoworkless.com/lab/Instagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

15 snips
Apr 14, 2025 • 1h 26min
38 Lessons From My Mastermind For 6 Figure Solopreneurs (March 2025)
Explore the secrets of successful solopreneurship with insights from a mastermind group. Learn about effective outreach strategies and practical scripts to attract new clients. Discover how to enhance sales calls and build trusting relationships that drive growth. Dive into luxury marketing techniques and the mindset shifts necessary for confidently raising prices. Uncover the importance of mastering content creation while avoiding distractions from shiny objects that derail progress. Focus on personalized approaches and leverage AI for greater productivity.

Mar 13, 2025 • 60min
10 Shifts To Go From $100k To $500k As A Solopreneur
A few weeks ago my client Seth asked me a great question: "What are the core principles I need to know to go $100k to $500k/yr?" This 60 minute podcast is my response.When you’re ready, here are 3 ways I can help you:📬 Work Less Wednesday (FREE)My weekly email. What I’m learning, doing, and thinking about. 30k readers.https://www.worklesswednesday.com🏖 How To Work LessFrom 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)https://www.learn.howtoworkless.com🧪 Work Closely With MeI advise and mentor 6-7 figure Creative Solopreneurs. If you want to work closely with me (i.e. we speak 1-2 times a week), watch this video, then let's talk:https://learn.howtoworkless.com/lab/Instagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

Feb 26, 2025 • 53min
Q&A: Outcomes Over Deliverables, Charging Your Worth, Saying No, Ignoring AI
Join Patrick McAndrew, a moderator at the Life's Work event who specializes in business strategy, as he chats with Rich Webster about vital entrepreneurial insights. They dive into the power of selling outcomes instead of mere deliverables and challenge the notion of 'charging what you're worth.' Discover the 'Line In The Sand' test for client selection and the intriguing dynamics of turning down big money. The discussion even tackles the cautious approach to AI in business. Prepare for enlightening strategies that could transform your professional journey!

8 snips
Dec 31, 2024 • 57min
10 Lessons I Learned About Entrepreneurship & Life In 2024
In this episode, I cover:- 10 lessons I learned about life and entrepreneurship in 2024- How sharing my addiction recovery story helped me align my life and business- The difference between “serving” and “servicing” clients- Why more entrepreneurs should be thinking about scaling with price- Why “Strategic Originality” is the only way to beat AI in 2025- How to create “Idea Space” in your life and business- Why entrepreneurs are not taking enough healthy risks (and taking too many stupid risks)- Why the biggest bottleneck to growth isn’t “more information” - it’s your internal issues and beliefs- Why you shouldn’t focus on “doing more” in 2025, you should focus on “doing different”Show Notes:- My Story: Addiction, Recovery, Alignment: https://youtu.be/ivE8j73SA2o?si=LE2liXejREZtlxFQ- Why Embracing Who You Are Is The Best Strategy: https://www.youtube.com/watch?v=sGIyIYtGl5s- 10X Is Easier Than 2X: https://www.amazon.com/10x-Easier-Than-World-Class-Entrepreneurs/dp/140196995XWhen you’re ready, here are 3 ways I can help you:📬 Work Less Wednesday (FREE)My weekly email. What I’m learning, doing, and thinking about. 30k readers.worklesswednesday.com🏖 How To Work LessFrom 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)learn.howtoworkless.com🧪 Work Closely With Me.If you’re an entrepreneur making 6-7 figures and want direct mentorship and consulting with me, let’s talk.calendly.com/richwebster/labInstagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

Jul 10, 2024 • 1h 17min
How I Made $454k In 7 Months: 7 Months In Kollege
FYI: There are some visuals to accompany this podcast. You can see the full video on YouTube. In this episode, I cover:- What I learned from joining a $30k mentorship program- What happened during my 5 hour marathon onboarding session- The 4 things I NEEDED to hear on my onboarding call- Why I shut down my agency doing $500k/year- How I picked up a new fuel and started sharing openly about who I am- How I launched a Minimum Viable Offer in under 30 days that made me a lot of money (and helped me discover my True Value)Learn more about Blake's business: https://www.kollege.comWhen you’re ready, here are 3 ways I can help you:📬 Work Less Wednesday (FREE)My weekly email. What I’m learning, doing, and thinking about. 30k readers.worklesswednesday.com🏖 How To Work LessFrom 2012-2023, I built a design agency that made me $500k/year, working 10 hours a week. HTWL teaches you how to do it. (350+ past students. 5 stars)learn.howtoworkless.com🧪 Work Closely With Me.If you’re an entrepreneur making 6-7 figures and want direct mentorship and consulting with me, let’s talk.calendly.com/richwebster/labInstagram: https://instagram.com/richwebzYouTube: https://www.youtube.com/@richwebzThreads: https://threads.net/richwebzTwitter: https://twitter.com/richwebz

8 snips
Jul 2, 2024 • 38min
Preparation, Ritual, and Abandonment: Life & Business In Flow
Discover the power of flow state for deep work and value creation. Learn from Trey Anastasio's pre-show routine. Explore the importance of Preparation, Ritual, and Abandonment. Avoid copying others' morning routines. Understand the consequences of not practicing abandonment. Dive into the significance of active listening in business interactions.