The Rich Webster Show

Rich Webster
undefined
Sep 22, 2025 • 30min

I am shutting down How To Work Less (Q4 2025 update)

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/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---🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/Social Links:Twitter:  https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebzYouTube:  @richwebz 
undefined
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!
undefined
Aug 6, 2025 • 60min

10 Lessons From My Retreat For 6 Figure Solopreneurs

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/ 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.🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/ Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz
undefined
Jul 9, 2025 • 1h 3min

"Work-Life Balance" Is Killing Your Business - Live @ Creative Sovereignty Event (Part 1)

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/ 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.--🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/ Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz
undefined
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.
undefined
14 snips
Jun 4, 2025 • 45min

Why High Prices CREATE More Value (Art World Proof)

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/ 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:🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/ Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz
undefined
May 7, 2025 • 39min

Why You’re Stuck at the Same Income Level (The Success Thermostat)

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/ 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:🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/ Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz
undefined
Apr 24, 2025 • 42min

$4 Million & Nothing To Show For It (How To Build Wealth As A Solopreneur)

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/ 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:🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/ Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz
undefined
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.
undefined
Mar 13, 2025 • 60min

10 Shifts To Go From $100k To $500k As A Solopreneur

🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)🤝 Work with me: https://learn.howtoworkless.com/lab/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 4 ways I can help you:🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)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 for your biz. (400+ past students. 5 stars)https://www.learn.howtoworkless.com📬 Work Less Wednesday (FREE NEWSLETTER)My weekly email. What I’m learning, doing, and thinking about. 30k+ readers.http://read.richwebster.co/wlw📰 inner entrepreneur (SUBSTACK)Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.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/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app