

The Rich Webster Show
Rich Webster
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
Topics I cover include: entrepreneurship, productivity, lifestyle design, social media, design, creativity, business
Episodes
Mentioned books

4 snips
Jan 5, 2026 • 24min
How to find clients who pay more money.
Discover why attracting better clients is less about lead generation and more about your inner readiness. Learn how self-esteem influences client relationships, with beliefs affecting your sales conversations. Embrace the idea of being trustworthy and practicing what you preach to enhance your business confidence. Rich emphasizes the importance of aligning your self-worth with pricing and skills. Ultimately, the key to charging more lies in building self-trust and fully believing in your value.

Sep 22, 2025 • 30min
I am shutting down How To Work Less (Q4 2025 update)
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/On October 1st, I'm shutting down the thing I'm arguably most known for: How To Work Less. Why? You'll have to watch.00:00 Intro00:55 Shutting down HTWL (Update 1)06:05 Starting a Substack (Update 2)10:21 Staying close to the work13:30 Alignment17:30 Mission and Business19:35 Ideal day22:10 From leverage to scale28:10 Final plug For HTWL---👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebzYouTube: @richwebz

8 snips
Sep 8, 2025 • 38min
How To Charge More (Without Working Harder)
Learn how to increase your fees without increasing your workload. Discover the secret to shifting focus from mere deliverables to impactful outcomes. Understand the power of positioning yourself as an expert to attract high-value clients. Networking plays a crucial role in client acquisition, so explore proactive strategies for expanding your reach. Finally, break through limiting beliefs that hold you back from maximizing your earnings. Change the way you think about business growth!

Aug 6, 2025 • 60min
10 Lessons From My Retreat For 6 Figure Solopreneurs
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/On August 1 & 2, I hosted a virtual retreat for my clients, all 6-7 figure creative entrepreneurs. No one paid less than $12k to be in the room.The good news? I’m going to give you the secrets for free.The theme of the event was Internal ←→ External. How to create external changes through internal work.I spoke myself and I invited a handful of speakers, including:- Steven Lawson, founder of Monk Manual (https://monkmanual.com/)- Jamie Brindle, influencer (500k followers) + agency owner (https://www.instagram.com/thejamiebrindle/)- Patrick McAndrew, entrepreneur + inner game expert (https://www.patrickmcandrew.co/)- Julien Wagemann, inner work guide for entrepreneurs (https://www.entrepreneurillumination.com/)I break down the 10 lessons my high-performing clients paid thousands to learn - and you're getting them for free.We explore the four fundamental problems entrepreneurs face, how to distinguish between maintenance and growth tasks, and why managing your inputs is crucial for quality outputs. I reveal why productivity systems eventually fail us, how to stop chasing happiness like a game of fetch, and the transformative shift from "having" goals to "being" goals.You'll learn why doing what works (and doubling down on it) is the simplest path to success, how entrepreneurship is actually accelerated self-development, and techniques to train your internal compass for better decision-making. Finally, we dive deep into healing the wounds that secretly sabotage your business success.👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

Jul 9, 2025 • 1h 3min
"Work-Life Balance" Is Killing Your Business - Live @ Creative Sovereignty Event (Part 1)
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/On May 18th, my good friend Zander Howard-Scott invited me to speak to a group of entrepreneurs at his Creative Sovereignty event in Montreal.Today, I’m excited to share the replay of one of two talks I gave at the event.In this talk, I cover:How “Work-Life Integration” leveled up my business (and life)Exactly how my $500k/year design business workedWhy I kept my recovery journey a secret for 14 yearsThe 4 things I needed to do to integrate my life and businessThe difference between using 0% and 1% of your brainThe 3 tools I use to maintain awareness in my businessThe whole event was incredible and I hope you enjoy the talk as much as I enjoyed giving it.Some context about the event & my buddy Zander:Zander (@zander_hs) is a pro musician and entrepreneur. His company, Creative Sovereignty, helps artists and creative professionals understand the value of their work and act accordingly.He also hosts a free Zoom call for artists and creative pros every Thursday at 12 pm EST inside his Skool community:👉 https://www.skool.com/creativesoverei...I’ll be sharing my second talk, “The Success Thermostat,” in the coming weeks.--👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

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)
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/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.👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

May 7, 2025 • 39min
Why You’re Stuck at the Same Income Level (The Success Thermostat)
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/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"👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

Apr 24, 2025 • 42min
$4 Million & Nothing To Show For It (How To Build Wealth As A Solopreneur)
💸 How To Charge More Free Workshop (January 21st): https://read.richwebster.co/htcm-workshop-1/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. 👤 inner entrepreneur (Substack)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/📬 Work Less Wednesday (Newsletter)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.https://read.richwebster.co/wlw🤝 Work With Me (Consulting)99% can ignore this. Work with 5 clients at a time. Expensive.https://read.richwebster.co/consultingwaitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.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.


