Two Paths To $500k As A Solopreneur

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Jun 18, 2025

Discover the hidden roadblocks that keep solopreneurs stuck at $100K. Explore the two paths to scale: leverage deep expertise in the expert business model or streamline operations using systems in the marketing model. Learn essential skills for each approach and how to attract clients effectively. Delve into real-life examples and uncover why generalist energy can be detrimental. Finally, hear about strategies that can elevate your solo business to new heights without the burden of a large team.

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INSIGHT

The $100K Solopreneur Wall

Most solopreneurs get stuck around $100K because they model their business like a job, doing both fulfillment and marketing at a high level.
This causes maxed out time and earnings, requiring choosing a new path to break past this barrier.

ADVICE

Scale By Increasing Price

For solopreneurs who hate marketing but excel at their craft, scale by increasing prices and deepening expertise.
Focus on fewer clients who pay more instead of many low-paying ones.

ADVICE

Be The Expert, Master Sales

Transition from being an order taker to an expert by diagnosing client problems and suggesting solutions.
Master sales and value-based pricing, linking your work to tangible business outcomes, to justify higher prices.

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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:

🏖 How To Work Less (CLOSES FOR GOOD OCT. 1)
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. (400+ past students. 5 stars)
https://www.learn.howtoworkless.com

📬 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)
Launching October 6. Insights on life/business from: $5m selling design + consulting, 400k followers online & 14 years of recovery from addiction.
https://richwebz.substack.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/

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