The Rich Webster Show

🤝 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 Alignment
17:30 Mission and Business
19:35 Ideal day
22:10 From leverage to scale
28:10 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/richwebz
Instagram: https://www.instagram.com/richwebz
YouTube:  @richwebz 

🤝 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 - Introduction
03:22 - Deliverables → Ideas → Outcomes
12:56 - Success is not suffering
17:17 - Expert/Order Taker
19:28 - Mastering Sales/Positioning
30:34 - Better clients
34:30 - 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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 worked
• Why I kept my recovery journey a secret for 14 years
• The 4 things I needed to do to integrate my life and business
• The difference between using 0% and 1% of your brain
• The 3 tools I use to maintain awareness in my business

The 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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 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.

📬 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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:

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.

📬 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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 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"

--

📬 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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, what I'm doing to build wealth now, and the 6 steps you can follow to build real wealth as a solopreneur. 

📬 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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.
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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz

🤝 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, 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/richwebz
Instagram: https://www.instagram.com/richwebz/
YouTube: https://www.youtube.com/@richwebz