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.

--

🛠️ 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://richwebster.notion.site/labjune

Instagram:   / richwebz 
Threads: https://threads.net/richwebz
Twitter:   / richwebz  
YouTube:  @richwebz

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

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

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

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

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

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

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

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

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