Ditching Hourly

Pranav Kale returns for another reverse interview — this time grilling Jonathan about his personal productivity and time management system.Jonathan walks through the system he's refined over two decades and used with his private coaching students: from consolidating all your to-dos in one place, to creating SOPs for recurring tasks, to the "event loop" that drives his day. The core idea: when you have the right things on your list and the right things in your calendar, you can just do whatever you feel like — and your business still moves forward.Topics covered include why your calendar is not a to-do list, how procrastination is actually a useful signal, the "love-hate list" for designing your ideal workday, why batching doesn't work for everyone, and the Segovia principle — why one focused hour beats five mediocre ones.This one's especially relevant for soloists who've tried rigid productivity systems and found they don't stick.Chapters00:00 Introduction01:00 The Three Buckets Every Soloist Needs06:16 Get All Your To-Dos in One Place09:14 SOPs and Checklists: Stop Winging It18:23 The Feast-Famine Trigger20:16 Why Your Calendar Is Not a To-Do List25:40 The Event Loop30:20 Procrastination Is a Signal37:37 When You Hate Part of a Task, Cut It42:06 The Love-Hate List49:15 Batching vs. Gardening Your Business56:22 How the System Came Together59:00 The Segovia Principle67:05 Adapting This to Your Personality70:41 Pranav's TakeawaysPranav Kale helps soloists find their one big idea through his Big Idea Sprint. Learn more at pranavkale.com. ----Do you have questions about how to improve your business? Things like:Value pricing your work instead of billing for your time?Positioning yourself as the go-to person in your space?Productizing your services so you never have to have another awkward sales call or spend hours writing another custom proposal?Book a one-on-one coaching call with me and get answers to these questions and others in the time it takes to get ready for work in the morning.Best of all, you're covered by my 100% satisfaction guarantee. If at the end of the call, you don't feel like it was worth it, just say the word, and I'll refund your purchase in full.To book your one-on-one coaching call, go to: https://jonathanstark.com/callI hope to see you there!

Joe Pine, management adviser and bestselling author known for The Experience Economy, explains his new Transformation Economy. He outlines how businesses guide identity-change, four aspiration types, and techniques to reveal a client’s future self. He also covers pricing by outcome, guarantees that align risk, and models for sustaining long-term change.

Jason Staats, accounting firm owner turned creator and community builder who teaches automation and no-code for firms. He discusses shifting from firm work to video and newsletter content, growing a large paid community, crafting attraction offers, and balancing distribution, staffing, and sponsorships. Short, practical conversations on visibility and building retention-driven communities.

Ben Kettle, a UK town planner focused on rural projects, explains his switch from hourly billing to fixed-fee and risk-based pricing. He outlines a three-tier pricing approach with shared-risk and success-fee options. Short stories cover client reactions, implementation, and how outcome-focused fees changed his workflow and client relationships.

Zach Stevens, co-founder of Conversion Factory and builder of a subscription marketing agency for software, shares an update on year three. He talks scaling a subscription model, hiring distributed designers, and systems for async client work. Short takes on onboarding, capacity per teammate, and where AI helps vs where human design still rules.

Charles Miller, founder of Platoon, joins to unpack the concept of 'good' taste and how it evolves over time. He shares insights on taste as an informed opinion shaped through experience, drawing parallels with music and design. The discussion delves into navigating client relationships when their taste isn’t developed, emphasizing the importance of guiding clients through strategic choices rather than surface demands. Miller also explores the balance between personal taste and commercial needs, illustrating how everyone can articulate their preferences.

Alex M H Smith, a savvy business strategist and author of No Bullshit Strategy, joins to unravel the elusive concept of value. He distinguishes between measurable utility and emotional value, urging businesses to create novel offerings. Alex shares insights on market research limitations and the need for unique positioning. He emphasizes focusing on solving expensive problems rather than generic benefits, and discusses the importance of specialization while cautioning against over-niching. This conversation is a treasure trove for anyone looking to elevate their business strategy!

Dr. J.J. Peterson, a Professor-in-residence at StoryBrand and founder of Conscious Brand Agency, explores the delicate balance between empathy and authority in business. He shares insights on the 'Badass Softie' concept, urging sensitive professionals to embrace both softness and strength. J.J. discusses the importance of defining one's unique guide style and overcoming imposter syndrome. Plus, he provides a compelling take on leveraging AI for content generation, emphasizing the need for human perspective in storytelling.

Shachar Meir, a former data leader at PayPal and Meta, shares his journey from corporate management to solo consulting. He discusses the factors that motivated his transition, including career stagnation and personal loss. Shachar reveals practical steps for landing initial clients, the emotional challenges of solopreneurship, and the importance of networking. He highlights how leveraging LinkedIn and content creation has helped grow his business. Finally, he offers valuable advice on managing finances and building a supportive network.

(NOTE: this ep was recorded in October 2025, but I didn't get around to publishing it until March 2026. It was WILD listening to the AI portions of the conversation five months later - post OpenClaw.)Old friend and self-described “workaholic” developer Tim Dietrich joined me on Ditching Hourly to share his journey from FileMaker freelancer to the undisputed SuiteQL expert in the NetSuite ecosystem — a niche so specific that the platform itself became his marketing engine.We also dig into what happens when AI comes for your platform and how to think about the next wave.Chapters(00:00) - Introduction (00:53) - Tim's Background (03:02) - Early Career and FileMaker Days (06:08) - Transition to NetSuite (16:02) - SuiteQL and SQL Integration (21:00) - Positioning as SuiteQL Expert (30:03) - Managing Demand and Consulting Opportunities (34:39) - Current Client Work and Scaling Back (36:01) - The Rise of AI in NetSuite (50:27) - Comparing to Other Waves and Platforms (01:05:37) - Exploring Monetization Strategies (01:22:31) - Future Trends and Opportunities ----Do you have questions about how to improve your business? Things like:Value pricing your work instead of billing for your time?Positioning yourself as the go-to person in your space?Productizing your services so you never have to have another awkward sales call or spend hours writing another custom proposal?Book a one-on-one coaching call with me and get answers to these questions and others in the time it takes to get ready for work in the morning.Best of all, you're covered by my 100% satisfaction guarantee. If at the end of the call, you don't feel like it was worth it, just say the word, and I'll refund your purchase in full.To book your one-on-one coaching call, go to: https://jonathanstark.com/callI hope to see you there!