Rich Webster

The Rich Webster Show

Business EN ↓ 41 episodes

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

Author

Rich Webster

Category

Business

Podcast website

howtoworkless.com

Latest episode

Apr 27, 2026

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Episodes

All The Details About How To Charge More! + Q&A 27.04.2026

📌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 th...

how to sell creativity (for a lot of money) 02.04.2026

🤝 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 fol...

How creative entrepreneurs close $100k+ clients (secret) 27.02.2026

🤝 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 fol...

How to find clients who pay more money. 05.01.2026

🤝 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 Branden The Ultimate Coach by Amy Hardison and Alan D. Thompson Why You're Stuck (Article): https://richwebz.substack.com/p/why-y... -- 📬 Work Less Wednesday (FREE NEWSLETTER) My weekly email....

I am shutting down How To Work Less (Q4 2025 update) 22.09.2025

🤝 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 Intro 00:55 Shutting down HTWL (Update 1) 06:05 Starting a Substack (Update 2) 10:21 Staying close to the work 13:30 Alignmen...

How To Charge More (Without Working Harder) 08.09.2025

🤝 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 anythi...

10 Lessons From My Retreat For 6 Figure Solopreneurs 06.08.2025

🤝 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 ←→ Extern...

"Work-Life Balance" Is Killing Your Business - Live @ Creative Sovereignty Event (Part 1) 09.07.2025

🤝 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 “Wor...

Two Paths To $500k As A Solopreneur 18.06.2025

🤝 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 Bus...

Why High Prices CREATE More Value (Art World Proof) 04.06.2025

🤝 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...

Why You’re Stuck at the Same Income Level (The Success Thermostat) 07.05.2025

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ 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 entrepreneu...

$4 Million & Nothing To Show For It (How To Build Wealth As A Solopreneur) 24.04.2025

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ 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, w...

38 Lessons From My Mastermind For 6 Figure Solopreneurs (March 2025) 14.04.2025

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ -- These are the 38 lessons that my mentorship clients learned in March 2025. If you want to be one of them, check out the 4th link below. -- 📬 Work Less Wednesday (FREE NEWSLETTER) My weekly email. What I’m learning, doing, and thinking about. 30k+ readers...

10 Shifts To Go From $100k To $500k As A Solopreneur 13.03.2025

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ -- 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. -- 📬 Work Less Wednesday (FREE NEWSLETTER) My weekly email. What I’m learning, doing,...

Q&A: Outcomes Over Deliverables, Charging Your Worth, Saying No, Ignoring AI 26.02.2025

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ Last month I spoke at an event called "Life's Work" in La Jolla, California, organized by my good friend ​Blake La Grange​. In the Q&A conversation, moderated by ​Patrick McAndrew​, we discussed: - Selling outcomes instead of deliverables - Why you shoul...

10 Lessons I Learned About Entrepreneurship & Life In 2024 31.12.2024

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ 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...

How I Made $454k In 7 Months: 7 Months In Kollege 10.07.2024

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ 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 NEE...

Preparation, Ritual, and Abandonment: Life & Business In Flow 02.07.2024

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: - How a true flow state creates more value and deeper work - What Trey Anastasio’s pre-show routine taught me about true flow - The 3 things that create the conditions for your best work to emerge: Preparation, Ritual, and Abandonme...

My Story: Addiction, Recovery, Alignment 26.06.2024

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: What I’ve been up to My addiction story How I got into recovery Why I’m sharing this now Work life integration Tapping into a new fuel The value is you What I’m doing next 📬 Work Less Wednesday (FREE NEWSLETTER) My weekly email. Wh...

Last Live Cohort of How To Work Less! + Q&A 04.01.2024

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ Everything you need to know about How To Work Less Cohort 6 , including who the program is for , what it includes , and what you can expect . Why this is the LAST TIME I’ll be teaching the curriculum live (very special!) The program structure and key dates ,...

2023 Year In Review 31.12.2023

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ Everything I accomplished in 2023 How much money I made How I grew my social media from 124k to 421k in 12 months Why I stopped newsletter ads, affiliate work, 1:1 coaching, and shut down my agency My top 5 books and my top tech of 2023 Show Notes: 2022 Year...

How To Charge More Money 18.12.2023

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: How to charge more money, doing exactly what you do now. How to use the “F-You” price to double your rates. Why getting more customers is a TERRIBLE way to scale your business. Why selling time punishes you for being good at your jo...

Nowhere Left To Run - Business Update 10.12.2023

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: What happens when you get to a point in your business when you know exactly what to do, and you just have to do it. How I set a date to shut down my design agency, and what it took to do it. How I launched a new brand new product an...

How To Scale Your Business Without Working More Hours 20.11.2023

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: How to break out of the “Time Bottleneck,” where you can’t work any less hours or make any more money. How to free up 10-15 hours a week, in 3 simple steps. How to make each hour of your time more valuable, using value pricing. The...

Planning The Rest of 2023 For My Business (Part 3) 12.11.2023

🤝 Work with Rich: https://richwebster.co/work 💸 How To Charge More Cohort 2 Waitlist (April): https://read.richwebster.co/htcm-c2-waitlist/ In this episode, I cover: My HUGE plans for the next 3 months in my business Why I paid $30,000 for a year of mentorship (and why its already paid for itself) 3 pieces of advice I’ve been telling my students, that I wasn’t taking myself Why I’m shutting down...

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