The Rich Webster Show

Hosted by Rich Webster

Business EntrepreneurshipInterviews guests

Website RSS feed Instagram YouTube

Episodes

Latest episode

Apr 2026

Language

About the 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

Listen to episodes

41 recent

April 27, 2026Episode 4153 min

All The Details About How To Charge More! + Q&A

📌How To Charge More Cohort 2 is OPEN for enrollment until Sunday, May 3rd at 11:59pm EST: https://htcm.cargo.site/ 📌I’ve been getting a ton of questions in my email about How To Charge More.So I decided to do something about it…I recorded a special podcast episode just for you!If you’re curious about what we’re going to be doing when we kick off the cohort on Monday, just check it out.In this episode, I cover:- Everything you need to know about How To Charge More Cohort 2, including who the program is for, what it includes, and what you can expect.- The program structure and key dates, plus all about the pricing and payment options.- A week-by-week breakdown of everything you’ll learn in the program.- All the insane bonuses we have for you this cohort.- The biggest FAQs I’ve received about How To Charge More.https://htcm.cargo.site/How To Charge More In 4 weeks, you’ll install our complete pricing system that transforms how you charge, sell, and position your expertise - so you stop leaving money on the table and start getting paid what your work is actually worth.Social Links:Instagram: https://instagram.com/richwebzSubstack: https://richwebz.substack.com/Podcast: https://therichwebstershow.transistor.fmYouTube: ‪ @richwebz

April 2, 2026Episode 4055 min

how to sell creativity (for a lot of money)

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/--📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Instagram: https://instagram.com/richwebzSubstack: https://richwebz.substack.com/Podcast: https://therichwebstershow.transistor.fmYouTube: ‪ @richwebz

February 27, 2026Episode 3951 min

How creative entrepreneurs close $100k+ clients (secret)

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/--📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Instagram: https://www.instagram.com/richwebzSubstack: https://richwebz.substack.com/Podcast: https://therichwebstershow.transistor.fm/YouTube: ‪ @richwebz

January 5, 2026Episode 3823 min

How to find clients who pay more money.

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/--Mentioned in video:The 6 Pillars of Self-Esteem by Nathaniel BrandenThe Ultimate Coach by Amy Hardison and Alan D. ThompsonWhy You're Stuck (Article): https://richwebz.substack.com/p/why-y...--📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Instagram: @richwebz Substack: https://richwebz.substack.com/Podcast: https://therichwebstershow.transistor...YouTube: ‪‪@richwebz‬ --00:00 the #1 problem in your business03:30 i. better clients start with you06:13 ii. beliefs become your biz10:14 iii. it starts with self-esteem13:54 iv. a tool: being your word18:20 v. time to believe in yourself20:59 how to find better clients

September 22, 2025Episode 3730 min

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

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/--------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---📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebzYouTube: @richwebz

September 8, 2025Episode 3637 min

How To Charge More (Without Working Harder)

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/In the last two weeks my clients...- Closed two $96k deals (podcast production)- Closed a $25k/month retainer (graphic design)- Closed a $25k/month retainer (marketing for blue collar biz)- Closed a $53k project (web development)They’re not doing anything crazy.I know all of these folks well. They’re not magic.1. They are not doing MORE WORK.2. The deliverables are LESS than you would expect.Don’t get me wrong, they’re REALLY good at what they do.But that’s table stakes. There’s plenty of experts stuck not making any money.This video is for entrepreneurs who are making 6-figures, but can’t figure out how to make more money.In it I explain how to you take your skills and package them in a way that creates the most value in the marketplace.So you can charge more, without working harder.00:00 - Introduction03:22 - Deliverables → Ideas → Outcomes12:56 - Success is not suffering17:17 - Expert/Order Taker19:28 - Mastering Sales/Positioning30:34 - Better clients34:30 - Final tips📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

August 6, 2025Episode 3559 min

10 Lessons From My Retreat For 6 Figure Solopreneurs

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/---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.---📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

July 9, 2025Episode 341 hr 2 min

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

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/---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.--📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

June 18, 2025Episode 3342 min

Two Paths To $500k As A Solopreneur

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/Most solopreneurs hit a wall around $100K. In this Episode, I’ll explain why.I will walk you through the two business models every solopreneur eventually has to pick between:1. Expert Business: Scale with PRICE (high-value, deep expertise)2. Marketing Business: Scale with SYSTEMS (zero fulfillment, all marketing)Here’s what I cover:What they each areExactly how each makes moneyWhat skills you would need to implement themHow you get clients with each modelWhat real life examples of these businesses look likeYou’ll learn:The hidden bottleneck keeping you stuck at $100KThe difference between scaling with price vs scaling with systemsThe real reason you're exhausted (hint: you're running a job, not a business)The dangerous trap of “generalist energy”How to make your business feel lighter instead of heavierThe model that took me to $500K+ with zero teamIf you're a freelancer, consultant, or creator trying to break past six figures without building a massive business, this one’s for you.📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz

June 4, 2025Episode 3244 min

Why High Prices CREATE More Value (Art World Proof)

🤝 Work with Rich: https://richwebster.co/work💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/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.📬 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)Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.https://richwebz.substack.com/🤝 Creative Partnership (1:1)I work closely with high-level creative entrepreneurs + consultants to hit their first (or next) million in revenue.https://richwebster.notion.site/creativepartnership💸How To Charge More (COHORT 2 - APRIL)Live cohort for entrepreneurs who want to scale their business by charging higher prices.https://read.richwebster.co/htcm-c2-waitlist/Social Links:Twitter: https://www.twitter.com/richwebzInstagram: https://www.instagram.com/richwebz/YouTube: https://www.youtube.com/@richwebz