Episode 500 of the show came out on Monday. Here’s I I put it together using Google NotebookLM

Nine years. 500 episodes. And one big question I've asked since the beginning. Do you have any trade secrets for us?

When I started this show (back when it was How I Built It), I was a newly married web developer with a side hustle and a curiosity for how others built their businesses. Ten years and three kids later, I’ve realized the mission has always been the same — helping solopreneurs build a business that supports their life, not consumes it.

In this special milestone episode, I’m sharing the story behind the show’s evolution, the real “trade secret” I’ve learned from hundreds of conversations, and how the GAPS Framework — Gear, Automation, Playbooks, and Support — is guiding my next experiment.

Want my systems delivered directly to your inbox for free? Join my mailing list at https://casabona.org/streamlined

Show Notes

• Ecamm Live
• Stream Deck
• Tella
• Gling.ai
• Riverside
• Everything on my Desk
• Zapier
• Castmagic
• YouTube
• LinkedIn
• Growth in Reverse Pro

💬 Send me your thoughts: streamlinedfeedback.com

Read to build your perfect site? Check out StellarSites.

Am I overthinking how to approach episode 500? Plus, I got an android phone.

Send feedback to https://streamlined feedback.com

We turned productivity into a fantasy draft! 🏆

Four small business owners battle it out, picking the apps and tools we cannot live without — with some surprise steals, hot takes, and even a bonus round for our favorite analog gear.

Looking for new ways to save time, systemize your business, and actually enjoy the tools you use? This draft is packed with ideas you’ll want to steal.

Draft Order:

1. Mike Schmitz
2. Layla Pomper
3. Cat Mulvihill
4. Joe Casabona

Wondering how you can manage your time to find the perfect balance? Take the Business Overwhelm Diagnostic.

Show Notes

• Mike Schmitz | Episode 422
• Layla Pomper | Episode 495
• Cat Mulvihill | Episode 305
• Obsidian
• Circle
• Kit (ConvertKit)
• ClickUp
• Raycast
• Canva
• Missive
• Zapier
• SmartSuite
• Kajabi
• Notion
• Sunsama
• Zoom
• Apple Text Replacement
• SavvyCal
• Stream Deck
• SaneBox
• Ecamm Live
• Todoist
• Google Drive
• Personal Retreat Planner (Mike’s custom tool)
• Rocketbook
• Field Notes
• Opus Clip
• Tella
• Gather
• Vimeo

What do you think? Send your feedback to streamlinedfeedback.com

I just wrapped up a Social Growth for my friend Chenell’s community where I posted on LinkedIn for 40 days.

Here’s what I learned and what’s next.

Send your feedback at https://streamlinedfeedback.com

Can you really delegate out when you are your business? Don’t people hire you to work with…well, you?

That’s the question Justin Moore and I wrestle with. We talk about the challenge of running personality-driven businesses, why it’s so hard to step away, and how to build a company that serves your life instead of consuming it.

Justin shares how he’s built a coaching business with a team he trusts, why impact is his North Star, and the mindset shift that helped him let go of control.

We also get real about balancing work with family time, the guilt that comes with stepping away, and why building a lifestyle business is just as valid as chasing a big exit.

Things get real – it’s something all business owners need to think about.

Wondering how you can step away from your business? Take the Business Overwhelm Diagnostic.

Top Takeaways

• Use a North Star mission (like impact) to guide decisions about hiring, delegating, and growth.
• Letting go of control is a mindset shift—delegating doesn’t dilute your business, it expands your reach.
• A lifestyle business is not a failure; you don’t have to build for an exit if you love the work.
• Balancing work and family isn’t about hacks—it’s about daily choices to be present in the moment.

Show Notes

• Sponsor Magnet Podcast (hosted by Justin and me)
• Sponsor Magnet (Book)
• Creator Wizard
• Key Person of Influence (Book by Daniel Priestley)
• Write Useful Books (by Rob Fitzpatrick)
• One to Many: The Secret to Webinar Success (by Jason Fladlien)
• CEX (Creator Economy Expo)
• Lulu (Publishing)

What do you think? Send your feedback to streamlinedfeedback.com

It seems like every day there’s a new tool designed to help us be more productive. They promise to help us to more, faster, better, with fewer resources. And it’s easy to get shiny object syndrome. So how do you know when it’s time to switch, or when it’s a waste of time and energy?

Luckily, as a chronic tool switcher, I’ve thought a lot about this very problem. And I have a framework to help you decide.

We’ll go through the 4 questions you should ask yourself when evaluating whether or not to switch. Then we’ll apply these tests to case studies so you can see how they work with actual examples.

Wondering if you should switch? Go to https://shouldyouswitch.com to apply this framework!

What do you think? How do you decide when to switch tools? Let me know at https://streamlinedfeedback.com

• (00:00) - The Rapid Evolution of AI Tools
• (01:26) - Framework for Tool Switching
• (06:39) - Case Study: Dropbox to Google Drive
• (11:22) - Case Study: Cal.com to Calendly
• (13:30) - Case Study: Switching from Arc
• (18:30) - Final Thoughts on Tool Switching

I’m considering a membership again, but this one is different! I’m going to do a paid newsletter, powered by Memberful and Kit.