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...
Jul 09, 2025•1 hr 3 min•Ep. 34
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...
Jun 18, 2025•42 min•Ep. 33
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: 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. High Price Creates Value. The shark wasn’t valuable so it was expensive. It became valuable becaus...
Jun 04, 2025•45 min•Ep. 32
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 incom...
May 07, 2025•39 min•Ep. 31
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 ...
Apr 24, 2025•42 min•Ep. 30
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.workle...
Apr 14, 2025•1 hr 26 min•Ep. 29
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 ...
Mar 13, 2025•1 hr•Ep. 28
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 ...
Feb 26, 2025•53 min•Ep. 27
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 ...
Dec 31, 2024•57 min•Ep. 26
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 hel...
Jul 10, 2024•1 hr 17 min•Ep. 25
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: - Ho...
Jul 02, 2024•38 min•Ep. 24
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 ...
Jun 26, 2024•31 min•Ep. 23
📌 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 ...
Jan 04, 2024•33 min•Ep. 22
📌 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: 2022 Year In Review: https://howtoworkless.com/wlw-63/ IG Reach Drop (2022): https://howtoworkless.com/wl...
Dec 31, 2023•1 hr 2 min•Ep. 21
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...
Dec 18, 2023•51 min•Ep. 20
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 ma...
Dec 10, 2023•45 min•Ep. 19
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 Enro...
Nov 20, 2023•45 min•Ep. 18
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 ...
Nov 12, 2023•43 min•Ep. 17
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...
Oct 29, 2023•56 min•Ep. 16
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...
Oct 22, 2023•54 min•Ep. 15
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 l...
Oct 08, 2023•37 min•Ep. 14
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...
Oct 01, 2023•34 min•Ep. 13
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://l...
Sep 24, 2023•34 min•Ep. 12
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 ma...
Sep 17, 2023•24 min•Ep. 11
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 Wo...
Sep 10, 2023•36 min•Ep. 10
📌 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 tha...
Sep 03, 2023•51 min•Ep. 9
📌 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 pr...
Aug 27, 2023•46 min•Ep. 8
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 ...
Aug 20, 2023•46 min•Ep. 7
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....
Aug 13, 2023•47 min•Ep. 6
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 🛠️ Phas...
Aug 06, 2023•50 min•Ep. 5
