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Explore every episode of the podcast The Rich Webster Show

Dive into the complete episode list for The Rich Webster Show. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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TitlePub. DateDuration
Why High Prices CREATE More Value (Art World Proof)04 Jun 202500:44:44

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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. Scarcity is a Power Tool.
    One-of-one art pieces command outrageous prices. Your time is just as limited. Are you pricing accordingly?
  7. 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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

Why You’re Stuck at the Same Income Level (The Success Thermostat)07 May 202500:38:59

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 years
  • Why 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 problem
  • Why your biggest fear isn't failure - it's actually success
  • 7 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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

Last Live Cohort of How To Work Less! + Q&A04 Jan 202400:32:46

📌 How To Work Less Cohort 6 is OPEN for enrollment until Sunday, January 7th at 11:59pm EST learn.howtoworkless.com 📌

In this episode, I cover:

  • 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, 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 Work Less.

📌 How To Work Less Cohort 5 is OPEN for enrollment until Sunday, January 7th at 11:59pm EST learn.howtoworkless.com 📌

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

2023 Year In Review31 Dec 202301:02:09

📌 How To Work Less Cohort 6 is OPEN for enrollment until Sunday, January 7th at 11:59pm EST learn.howtoworkless.com 📌

In this episode, I cover:

  • 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:

Top Books 2023:

10X Is Easier Than 2X – Dr. Ben Hardy & Dan Sullivan

Buy Back Your Time – Dan Martell

The Creative Act: A Way Of Being – Rick Rubin

No Boundary – Ken Wilbur

Implementing Value Pricing – Ron Baker

Fav fiction read: The 4 Body Problem Trilogy.

Favorite Tech 2023:

Lumosity: https://howtoworkless.com/wlw-98/

Loom: https://www.loom.com/

Circle: https://circle.so/

Skool: https://skool.com/

Notion: https://affiliate.notion.so/richwebz

MailTrack: https://howtoworkless.com/wlw-105/

ARC: https://howtoworkless.com/wlw-67/

Bartender for Mac: https://howtoworkless.com/wlw-67/

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

How To Charge More Money18 Dec 202300:50:54

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 job.
  • How to get better at talking about money.
  • The one question to ask yourself to know if you’re charging enough.

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Nowhere Left To Run - Business Update10 Dec 202300:45:27

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 and made $200k in 30 days.
  • Why people get totally wrong about charging high prices.
  • How to provide the most value to your clients, with the least amount of work.

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

How To Scale Your Business Without Working More Hours20 Nov 202300:44:59

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 two steps to get leverage in your business, so you can work less and earn more.

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Resources Mentioned:

  • How To Work Less Cohort 6 Early Enrollment: learn.howtoworkless.com
  • Implementing Value Pricing by Ron Baker
  • 3 Phases of Solopreneurship: Podcast Episode 13
  • 80/20 Delegation System: Podcast Episode 11
  • 7 Systems I’m Using In My Business: Podcast Episode 6

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Planning The Rest of 2023 For My Business (Part 3)12 Nov 202300:42:54

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 my agency in 2024
  • Some big changes coming to How To Work Less next year
  • And the NEW program that I’m testing with a select group of HTWL grads this week

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Planning The Rest Of 2023 For My Business (Part 2)29 Oct 202300:55:55

In this episode, I discuss:

  • What I discovered in the second week of planning for my business
  • The areas of my business where I am not taking my own advice (and what I’m doing about it!)
  • Why structuring your year in Sprints is the cure for Shiny Object Syndrome
  • The big bottleneck I’ve hit with How To Work Less (and how I’m thinking about solving it)
  • The conversations I had with my Personal Board of Directors this week (including course experts, automation masters, and 7 figure business owners)
  • How I’m going 10X in my business in 2024

Show Notes

Tommy Mallen: https://tommymallen.com/

Course Creator Lab (Julia Saxena): https://coursecreatorlab.co/

Matt Brown (Email Deliverability): matt@mattbrowncopy.com

Daniel Bustamante’s Email List: https://funnelbreakdowns.com/

Alex Oumn’s Notion & Legal Templates: https://www.zenmondays.com/

10X Is Easier Than 2X: https://www.amazon.com/10x-Easier-Than-World-Class-Entrepreneurs/dp/140196995X

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Planning The Rest Of 2023 For My Business (Part 1)22 Oct 202300:54:15

In this episode, I discuss:

  • How I plan my year in 3 sections using my “Sprint” Method (and how you can apply it to your business)
  • How much I’ve earned from January - October from my education business
  • The insights I learned from my 80/20 Analysis of my business
  • Why I’m stopping newsletter sponsorships, affiliate marketing, most coaching, and most brand deals, and what I’m doubling down on instead
  • How I’m planning to spend money to free up my time before the end of 2023

Show Notes:

Instagram Post on 80/20 Exercise & Runway Calculation: https://www.instagram.com/p/CwVgqXVvI-_/?img_index=1

Ep. 10 - Diversification Is A Distraction: https://therichwebstershow.transistor.fm/episodes/diversification-is-a-distraction

Ep. 6 - 7 Systems I’m Using In My Business: https://therichwebstershow.transistor.fm/episodes/7-systems-i-m-using-in-my-businesses

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

8 Secrets Big Content Creators Don’t Want You To Know08 Oct 202300:36:47

In this episode, I reveal:

  • 8 huge secrets big content creators don’t want you to know
  • Why many huge creators make very little money from content creation
  • The main difference between someone with 2k and 200k followers (it’s not the content)
  • What your favorite creator did when they started to give them an unfair advantage
  • Why creators I’m talking to are obsessed with owning their audience
  • How you can use these secrets to grow your audience online

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

The 3 Phases Of Solopreneurship (Say Yes, Say No, Buy Back Your Time)01 Oct 202300:34:22

In this episode, I cover:

  • My brand new “3 Phases of Solopreneurship” framework
  • The 3 most powerful resources you have as a solopreneur: your money, your time, your mind
  • 4 things you must do if you’re just getting started (and have more free time than money)
  • The two massive mistakes people make when they get a little bit of money.
  • How to buy back your time so you actually have more freedom (instead of just more work).

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Resources Mentioned

Episode on Maintenance vs. Growth Tasks: Ep. 7 - 7 Systems I’m Using In My Businesses

Ramit Article: https://www.iwillteachyoutoberich.com/how-to-use-money-to-buy-back-your-time/

Buy Back Your Time - By Dan Martell

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

$4 Million & Nothing To Show For It (How To Build Wealth As A Solopreneur)24 Apr 202500:41:58

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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

I Learned The Hard Way: Don’t Build Your House On Borrowed Land24 Sep 202300:34:24

In this episode, I cover:

  • How I (stupidly) built a product on someone else’s (digital) land and got hit with a $500k bill
  • 5 short cautionary tales of businesses affected by platform risk (and what happens)
  • Why diversification (usually) isn’t the solution to platform risk
  • 3 things you can do right now to avoid platform risk in 2023

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Steal My 80/20 Delegation System To Work 1 Day A Week17 Sep 202300:23:57

In this episode, I cover:

  • ⚖️ How to use my 80/20 Delegation system to 5x your income or work 1 day a week
  • 🧱 What to do when you hit the “One-Person Wall” and can’t make any progress in your business
  • 👥 How to know EXACTLY which work you should do, and which work your should delegate
  • 📊 Why the “Value 20” is the secret to successful delegation
  • 💸 How I used 80/20 Delegation to hit $500k/year in my agency last year

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Diversification Is A Distraction10 Sep 202300:36:24

In this episode, I cover:

  • Why you don’t need multiple streams of income, especially if you haven’t reached 6-figures.
  • Why most people think more revenue streams = more money and less risk (and why they’re wrong).
  • Why you should drop your 10+ projects and focus on 1-2 things that really move the needle.
  • Three questions I ask myself regularly to avoid this in my business.

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

6 Reasons Why Working More Is Hurting Your Business03 Sep 202300:51:00

📌 How To Work Less Cohort 5 is OPEN for enrollment until Sunday, September 3rd at 11:59pm EST learn.howtoworkless.com 📌

In this episode, I cover:

  • Why prioritization is the number one skill you must master as an entrepreneur
  • The most powerful time-management tactic I know of (and why we are hard-wired to be terrible at it)
  • 5 ways I’ve set up my workspace to be designed for focus and deep work
  • The 3 delegation mistakes I see all entrepreneurs make
  • Why the design of your business matters more than anything else when it comes to creating a lifestyle business
  • The answer to this quote - “The more you _______, the less effective and productive you become over both the short and long term.” Business Roundtable Report 1980

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

📌 How To Work Less Cohort 5 is OPEN for enrollment until Sunday, September 3rd at 11:59pm EST learn.howtoworkless.com 📌

All The Details About How To Work Less! + Q&A27 Aug 202300:45:39

📌 How To Work Less Cohort 5 is OPEN for enrollment until Sunday, September 3rd at 11:59pm EST learn.howtoworkless.com 📌

In this episode, I cover:

  • Everything you need to know about How To Work Less Cohort 5, 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.
  • Why How To Work Less is really 3 cohorts for the price of 1!
  • 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 receive about How To Work Less.

📌 How To Work Less Cohort 5 is OPEN for enrollment until Sunday, September 3rd at 11:59pm EST learn.howtoworkless.com 📌

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Revealed: How To Start Working With High Ticket Clients20 Aug 202300:45:49

In this episode, I cover:

  • The secret language high-ticket clients use to communicate (so you don’t embarrass yourself).
  • The real truth behind why some people can get big clients and others can’t.
  • My 6 rules if you want to start working with high-ticket clients.
  • The 4 things that motivate expensive clients to buy (now!)
  • The number one way people irreversibly screw up a client relationship within 24 hours of signing a contract.
  • Why it’s easier to sell a client worth $5 million than a client with $10k of credit card debt.

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

7 Systems I’m Using In My Businesses13 Aug 202300:47:17

In this episode, I cover:

  • 🛠️ The 7 systems I’m using in my businesses to work less and earn more
  • 📸 The content system that creates 7 posts a week on autopilot
  • 🛍️ How I automate getting clients for my agency and course
  • 📰 The newsletter system that takes me 1 hour and 53 minutes per week to write
  • 🔄 My design agency’s fulfillment system (SOPs + Templates + Tools)
  • 💬 How I use systems to handle thousands of DMs a month

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

How To Design Yourself Out Of Your Business06 Aug 202300:49:56

In this episode, I cover:

  • 🏋️‍♀️ How to stop doing all the work yourself and start working ON your business.
  • 💼 How to create a machine that doesn't rely on your time.
  • 📝 How to design yourself out of your business, using 3 phases to achieve freedom and flexibility.
  • 🔍 Phase 1 - Get clarity: figure out how you spend your time, how much your time is worth, and what actually makes you money
  • 📝 Phase 2 - Prepare your business: Figure out your runway and remove things that aren’t profitable
  • 🛠️ Phase 3 - Design yourself out: Build systems, delegate, and do leveraged tasks

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Lessons From $10,000 Of Coaching With Chris Do (Part 2)30 Jul 202300:50:41

In this episode, I cover:

  • Insights from 6 coaching sessions with Chris Do
  • Chris’ 9 steps to build a personal brand
  • How I grew from 0-100k followers in 18 months
  • The biggest mistake people make when they try to sell a course
  • My original (bad) idea for “How To Work Less”
  • The productivity tool Chris gave me that has saved my team 10,000+ DMs

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Lessons From $10,000 Of Coaching With Chris Do (Part 1)23 Jul 202300:50:10

In this episode, I cover:

  • The story behind how I hired Chris Do to coach me
  • The hidden value of coaching most people don’t realize
  • My 3 recommendations everyone should do when hiring a coach
  • The 3 questions I had for Chris Do in our first session
  • The #1 thing I was doing wrong with my high ticket clients
  • Chris’ advice for scaling an agency and managing a team

If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!

Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter

Find Me On Social

Instagram: https://instagram.com/richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

38 Lessons From My Mastermind For 6 Figure Solopreneurs (March 2025)14 Apr 202501:25:34

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.


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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

20+ Things I Don't Do As A $500k Solopreneur16 Jul 202301:03:27

In this episode, I cover:
- Why saying “No” is the most productive thing you can do
- All the things I don’t do in my design agency
- All the things I don’t do on social media
- 4 recent things I stopped doing
- How to apply this stuff to your life


If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!


Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter


Find Me On Social

Instagram: https://instagram.com/richwebz
Threads: https://threads.net/richwebz
Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

What's Going On Now & What's Up Next?06 Jul 202300:54:36

Welcome to the first episode of The Rich Webster Show! 

In this episode, I cover:
- Why I created this podcast (not what you think)
- Background on my businesses (for those who don't know me)
- What’s going on now in July 2023 (what I'm up to)
- My thoughts on the Threads launch (and what you should do)


If you enjoyed this episode, please subscribe and leave a rating and review. It makes a huge difference!


Work With Me

How To Work Less (My Signature Course): https://learn.howtoworkless.com

6-Figure Solopreneur Systems (FREE Course): https://startbuildingsystems.com

Work Less Wednesday (My Weekly Newsletter): https://howtoworkless.com/newsletter


Find Me On Social

Instagram: https://instagram.com/richwebz
Threads: https://threads.net/richwebz
Twitter: https://twitter.com/richwebz

YouTube: https://www.youtube.com/@richwebz

10 Shifts To Go From $100k To $500k As A Solopreneur13 Mar 202500:59:56

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 Less​
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​
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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

Q&A: Outcomes Over Deliverables, Charging Your Worth, Saying No, Ignoring AI26 Feb 202500:52:37

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 shouldn't "charge what you're worth"
- The "Line In The Sand" test for picking clients
- Why everyone's a gangster until they have to turn down $10k
- Good pain vs. bad pain in business
- How to use my "Agent Rule" to charge more money
- Why full price or free is still the best policy
- Why I didn't touch AI until 2025


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 Less​
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​
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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

10 Lessons I Learned About Entrepreneurship & Life In 202431 Dec 202400:57:23

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/140196995X

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.
worklesswednesday.com


🏖 How To Work Less
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)
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/lab


Instagram: https://instagram.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

How I Made $454k In 7 Months: 7 Months In Kollege10 Jul 202401:16:30

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.com

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.
worklesswednesday.com


🏖 How To Work Less
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)
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/lab


Instagram: https://instagram.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

Preparation, Ritual, and Abandonment: Life & Business In Flow02 Jul 202400:38:19

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 Abandonment
- Preparation for sales calls, public speaking, and content creation
- My current morning routine/ritual and why you shouldn’t copy someone else’s morning routine
- What happens if you don’t practice abandonment (it’s bad)


Show Notes:
- How Does Trey Anastasio Prepare For A Show? https://www.youtube.com/watch?v=5kKe9...
- Trey’s Full Pre-Show Ritual: https://jambands.com/news/2018/12/18/...
- The Creative Act by Rick Rubin: https://www.amazon.com/Creative-Act-W...
- Unreasonable Hospitality by Will Guidara: https://www.amazon.com/Unreasonable-H...

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.
worklesswednesday.com


🏖 How To Work Less
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)
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/lab


Instagram: https://instagram.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

My Story: Addiction, Recovery, Alignment26 Jun 202400:31:21

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

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.
worklesswednesday.com


🏖 How To Work Less
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)
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/lab


Instagram: https://instagram.com/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

Two Paths To $500k As A Solopreneur18 Jun 202500:42:17

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 are
  • Exactly how each makes money
  • What skills you would need to implement them
  • How you get clients with each model
  • What real life examples of these businesses look like

You’ll learn:

  • The hidden bottleneck keeping you stuck at $100K
  • The difference between scaling with price vs scaling with systems
  • The 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 heavier
  • The model that took me to $500K+ with zero team

If you're a freelancer, consultant, or creator trying to break past six figures without building a massive business, this one’s for you.

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 (FREE 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 for your biz. (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/richwebz

YouTube: https://www.youtube.com/@richwebz

Threads: https://threads.net/richwebz

Twitter: https://twitter.com/richwebz

© My Podcast Data