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The Rich Webster Show

The Rich Webster Show

By: Rich Webster
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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© Work Less LLC Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • I am shutting down How To Work Less (Q4 2025 update)
    Sep 22 2025

    🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)
    🤝 Work with me: https://learn.howtoworkless.com/lab/

    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
    ---

    🏖 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/

    Social Links:
    Twitter: https://www.twitter.com/richwebz
    Instagram: https://www.instagram.com/richwebz
    YouTube: @richwebz

    Show More Show Less
    30 mins
  • How To Charge More (Without Working Harder)
    Sep 8 2025

    🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)
    🤝 Work with me: https://learn.howtoworkless.com/lab/

    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


    🏖 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/

    Social Links:
    Twitter: https://www.twitter.com/richwebz
    Instagram: https://www.instagram.com/richwebz/
    YouTube: https://www.youtube.com/@richwebz

    Show More Show Less
    38 mins
  • 10 Lessons From My Retreat For 6 Figure Solopreneurs
    Aug 6 2025

    🏖 Get How To Work Less for $500! https://learn.howtoworkless.com/ (Doors close for good Oct. 1st)
    🤝 Work with me: https://learn.howtoworkless.com/lab/

    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.

    🏖 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/

    Social Links:
    Twitter: https://www.twitter.com/richwebz
    Instagram: https://www.instagram.com/richwebz/
    YouTube: https://www.youtube.com/@richwebz

    Show More Show Less
    1 hr
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