Ever wonder if your newsletter should be the product…or just promote the product?

I’ve been treating mine more like a magazine than a sales tool — and it’s cost me. So I sat down with Dylan Bridger, who helps course creators and coaches turn their newsletters into profit machines.

We talk about:

• The difference between a “magazine” newsletter and a “sales team” newsletter
• How to actually warm up your audience so they buy when you make an offer

But we also get into the impact becoming a new dad had on Dylan’s workflows, and a short-lived side project that taught him big lessons fast.

This conversation helped me clear up a ton of issues with my own newsletter, and I think it’ll do the same for you.

Seeking clarity in your business systems? Take the Business Overwhelm Diagnostic.

Dylan Bridger is an email marketing expert who helps coaches and course creators increase their conversions while building stronger relationships with their lists. A full-time marketing consultant since 2021, more than 7,000 entrepreneurs follow his insights across newsletter and social media. When he's not working, you can find Dylan writing songs, goofing around with his daughter, or enjoying a nice cup of coffee.

Links

• Dylan Bridger
• Dylan on LinkedIn
• Dylan on Twitter/X
• Dead-Eyed Portraits: The Real Risk of AI Headshots
• Nathan Barry
• Kit (formerly ConvertKit)
• Ken McCarthy – Jazz on the Tube
• Beehiiv

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

Read to build your perfect site? Check out StellarSites.

When I was a kid, I said things like, “I won’t forget,” or “When I’m a dad, I won’t get mad.” Or…”I’m bored.”

But as you get older, and life puts you in various, unforeseen situations, it’s easy to get blindsided and react in a way you hoped you wouldn’t.

I think about this a lot when I consider what’s changed between turn 20 and turn 40. And there’s a common theme that has cropped up: pruning.

Letting go of what doesn’t work. Of where you used to spend your energy. About making more space in your life for the things that matter.

And I thought that there was no better person to bring on to talk about this than my friend, fellow freelancer, and fellow father, Austin L. Church. He’s a deep thinker, committed family man, and wants to help people.

Looking to prune what’s stealing your energy? Take the Business Overwhelm Diagnostic.

Top Takeaways

• Fluff vs. value in business books — many books stretch one idea into 300 pages, but the best insights are usually old, durable ideas worth revisiting.
• Growth by subtraction — focus and pruning beat doing “all the things.” Fractured attention leads to mediocre results.
• Attention as water — what you focus on grows. Stop “watering” indignation and instead nurture gratitude, creativity, and presence.
• Values over virality — not all success is worth emulating. If someone’s optimizing for attention or wealth at all costs, that doesn’t mean you should.
• Parenting parallels — kids remember how you respond more than what you say. Choosing patience, presence, and love shapes both them and you.
• “These are the good old days” — a simple mindset shift that makes it easier to stay present with family and avoid regrets later.

Links

• Austin’s post on pruning
• Austin L. Church — Freelance Cake
• Austin’s Book: Free Money
• Buy Back Your Time — Dan Martell
• Good Strategy Bad Strategy — Richard Rumelt
• Essentialism — Greg McKeown
• Dieter Rams — Principles Of Good Design

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

Read to build your perfect site? Check out StellarSites.

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