Joe Casabona

Creator Wizard

I help creators pitch and secure brand deals.

Sponsorship Coach

Good House Media, LLC

I am a podcast systems coach who helps busy solopreneurs and small business owners take back their time. I do that by help them create systems for automation and delegation — that way you have more freedom to do what you want to do — whether it's grow your business, spend time with your family, or just relax.

You'll save over 12 hours per week, and trade-in that stress and overwhelm for freedom.

Podcast Systems Coach

Streamlined Solopreneur

What if you could save 12+ hours per week in your business? Being a solopreneur sometimes focuses too much on the “solo” part: doing all the jobs, figuring things out yourself, and spending too much time in your business. But we didn’t start our own solo business to spend all of our time at our desk.

Podcast Host

RSS.com 

I help keep podcasters informed of how to best launch, grow, and monetize their podcasts, while also teaching them how to leverage the fantastic features and tools available through RSS.com.

Content Creator / Evangelist

LinkedIn

I help site creators develop WordPress websites through online courses.

Course Instructor for LinkedIn Learning

University of Scranton

Teach courses in Computer Literacy, E-Commerce, and Programming in PHP.

Develop lesson plans that educate students on current computer trends and history of computing, what programming is, and how to develop function, database driven web applications.

Part Time Faculty

Develop and support a wide range of applications written in PHP, ASP, Java, PL/SQL, and on platforms such as Luminis and Cascade CMS. 

Modernize and update web applications to use recent and best practices. 

Work with the Marketing Department on web-based projects, including converting Scranton.edu to be fully responsive. 

Introduced and now support WordPress based projects on campus

System Integrator/Web Developer

Crowd Favorite

Develop custom WordPress websites using all sorts of cool techniques! I specialize in Responsive Development.

Team Lead

Manifest Development

Develop modern, clean, useable websites and web applications for a wide range of clients and businesses, primarily using WordPress.

Work directly with clients to elicit requirements, develop, and test web-based software systems.

Advise clients on new, emerging, and important technologies including Mobile, Responsive Web Design, and Security.

Freelance Web Developer

I help busy solopreneurs leverage and grow their podcasts through process improvements and automation.

Podcast Producer and Coach

At Podcast Liftoff, I help podcasters of any size make money by helping them put the right systems in place for consistency, efficiency, and sponsorship outreach. That way they can transform their podcast from a hobby to a revenue-generating machine.

We're giving up too much to AI. 

Giving up personal growth, critical thinking, and professional help in the name of efficiency reminds me of another trend from the early 2000s. 

Giving up privacy in the name of security. 

You end up not having either, and only one party benefits. 

(hint: it's not us)

I've been thinking a lot about this lately. 

Meta's AI guidance on what they think is acceptable for children. 

Truly heartbreaking stories about teenagers losing everything because of what ChatGPT has told them. 

Technology should help us be better humans. Not catapult is into isolation. 

If you run a business, you should be suspicious. 

If you have kids, you're probably terrified. I know I am.

I don't have much of a solution besides this: 

As yourself this question, and be completely honest: 

"Is AI (or any automation) helping me show up better for the people I serve, or just letting me half-ass my work?"

Helping solopreneurs use tech to build better human interactions, not replace them. Learn why, and how I get here, in About ↓

I hate social media. 

I don't have any social apps on my phone. I'm not continuously logged-in to any of them. 

I feel like it's a time suck, and a terrible distraction. 

But some would say it's undeniable that you need it to grow your business, your podcast, your newsletter. 

On top of that, I get a TON of questions on how to build automations and systems around this specifically, and my answer has always been ¯\_(ツ)_/¯

That's why I joined Chenell Basilio's 30 Days of Growth: Social Challenge. 

To see if I can grow my newsletter, as well as build some automations to help me hate it less. 

Part of me hopes it doesn't work so that I'm proven right. 

But Chenell's usually right about these things, and I'm a, "strong opinions, loosely held," kinda guy. 

Have any good tips for me? Leave a comment and let me know! 

--- 
Hey I'm Joe Casabona. 

⏳ I talk a lot about automations and systems. 
I help solopreneurs use tech to build better human interactions (not replace them). 

⚙️ I also have a newsletter where I teach and build automations. Join using the blue link under my name.

👇 Steal this for your email replies this week:

Hey [NAME],

Thanks for emailing me sometime between June and Today. 

It's the first day of school so I'm finally able to catch up my email inbox. I'll be sending you a proper response very soon. 

Joe

When is switching a tool worth it? 

This is the face of a dude who switches tools too much, so I know a thing or two. 

Over the summer, I switched from Dropbox to Google Drive because they told me the plan I'd been using for my business for a decade suddenly wasn't for business anymore. 

I switched from Bonjoro to Senja recently because it cut *several* steps out of my workflow. 

And now I'm considering moving from Cal(dot com) BACK to Calendly. 

Why? 

Some time between when I signed up and a month ago, they turned reminder email editing off for the free plan. 

I get that I'm using a free tool — the only paid options are for teams and enterprises. 

But the problem is I made edits to those emails, and now I can't change them at all. 

So...is it worth me moving from Cal back to Calendly? Let's weigh the pros and cons: 

Pros of switching
✅ I can edit these emails that I need to edit
✅ Switching on the surface (moving calendars) is easy enough from a feature point of view
✅ Paid plans are generally more stable than free software. I mean...I don't have much room to complain for something I'm not paying for, right? 

Cons of switching
❌ The time it takes to migrate my calendars over
❌ The time it takes to update and test my automations
❌ Increasing my costs from $0 to $120
❌ The time it takes for me to make sure all of my Cal links are removed and replaced with Calendly. 

Luckily for that last one, I use redirects (something a guy who switches too much learned to do). 

So...when should you switch tools? 

1. When the pain of using the current tool outweighs the effort to switch
2. When the new tools has a feature you absolutely need
3. When the level of effort to switch is near zero. 

Based on that criteria, I'm not switching. The effort is too high, and I suspect support will be able to help me. 

Worst case, I upgrade to Teams for one month to make the changes to the emails, and then immediately downgrade. 

What about you? When do you know it's time to switch tools?

It hurt…kind of a lot. 

The first time I put my CGM in my arm, there was a sharp pain. 

I have Type 2 Diabetes and my doctor recommended a Continuous Glucose Monitor so I could learn how different food affects my blood sugar. 

“I guess that makes sense,” I thought. It’s a needle going into my arm. 

But then it continued to hurt. Every time I moved my arm, pretty much. 

“Well it’s probably sore.”

But the readings were also kind of weird. Sometimes vastly different than a finger stick. 

After 2 days of pain, I went to the Diabetics Subreddit. I mean, tons of people wear these. They can’t possibly be in near constant pain.

I learned from the more experienced: turns out the needle probably bent going in. 

So I replaced it and you know what?

I didn’t even feel it going in. 
It didn’t hurt when I moved my arm. 
And the readings were accurate. 

When you do something for the first time, it’s can be tough to know if you’re doing it the right way. 

But you probably have a gut feeling. 

When that happens, you should try something different. Ask questions. Experiment. Consult people with experience. 

You’ll probably find a much better, less painful experience. 

--- 
Hey I'm Joe Casabona. 

⏳ I talk a lot about automations and systems. 
I help solopreneurs use tech to build better human interactions (not replace them). 

⚙️ I also have a newsletter where I teach and build automations. Join using the blue link under my name.

Students today don’t need more handouts.

They need high-impact, flexible content… in formats they already use.

That's why Margaret J. Cunningham (a school district Work Based Learning Coordinator) came to me with a brilliant idea: Launch a podcast to give students AND parents ongoing access to career advice, guest speakers, and program info.

But she had one big question: 

How do I actually make this work… without driving myself crazy?

Here's how we applied the GAPS Framework to make it happen without adding a ton more to her plate (or her budget): 

1. Gear: Start with a sub-$100 mic like the Samsung Q2U or ATR2100. Beginner-friendly, portable, and plugs straight into a laptop. No overbuying needed 

2. Automations: Use Riverside for remote interviews. Edit right in the platform by cutting text from the transcript and using their magic editing tools. Then use RSS.com (which has special pricing for educators) to make sure it gets everywhere, including YouTube. 

3. Playbooks: We walked through her basic workflow right on the call, so she has a clear path from record to publish, without having figure it out on her own. She also got a follow-up document and the recording to serve as her manual. 

4. Support: We discussed ways where she can get help from students in the school to help her with editing, graphics, and more — giving them a work-based learning experience! 

Now she’s setting things up to launch smart, stay consistent — and elevate her students’ experience beyond that 8:30 to 2:40 school slot.

You don’t need fancy video, editors, or strong social. You just need a simple, repeatable system that serves your audience where they are.

Here's what she had to say after the call!

Every business is a content business now — whether they know it or not.

Nathan Barry said it recently, and he's right...content is the key to communicating your value, building community, and helping people actually understand your product.

The truth is, a lot of companies aren't good at content. They either don't produce enough, or they don't speak to their customers in the right way.

That’s where we have the advantage.

If you know how to explain software in a technical-but-human way…
If you can create content that actually helps people…
If you’re the kind of person who can be a strong community builder…

You're sitting on a high-demand skillset.

Right now, I feel really lucky to have a job where I get to use that skill to help balance everything else I have going on.

Because the value is there. And it’s real.

Listen to the full episode  of Streamlined Solopreneur with 🎙 Matt Medeiros wherever you listen to podcasts

This is snake oil. 

Forget that 92% is very likely a made up number chosen because it's big and specific, and therefore memorable. 

Imagine telling people that *last month* you changed your entire business operation to implicitly trust the information AI is giving you. 

And then making important decisions based on it. 

And then presenting this as if it's absolutely the way to run your business.

The magical weight loss drug. 
The elixir to reverse balding. 
The new passive income.

It's selling people something they want to believe. 

We're going to see a lot more posts like this. 

When the AI bubble bursts, we're going to see those same people with posts that start: "I bet everything on AI. I was wrong. Here's why 👇" 

You should experiment with AI, sure.

But unless you're already hugely successful, you're going to need to give more than 8%.

📘 Bestselling Author (Buy Back Your Time) 🚀 Building AI startups @Martell Ventures ⚙️ 3x Software Exits • $100M+ HoldCo 💬 DM "COACH" if you're looking to scale

6 weeks ago I told my team that AI needs to do 92% of their work or they'll get left behind.

Here’s how we're doing it (and why):

Step 1: Get ChatGPT Plus/Pro


Step 2: Create your master prompt

• Tell AI: "I'm [your role] at [company type]. Create a master prompt for me. Ask me every question you need to give me the most context possible."
• Spend 30-45 minutes answering everything it asks
• Save the output as a PDF
• Upload this to every new chat so AI knows your full context


Step 3: Build system prompts
Master prompts tell AI who you are. System prompts tell AI HOW to work.

Here's the process:
• Ask AI to create any output (email, ad, report)
• Keep refining until it's perfect (3-6 iterations)
• Then ask: "Write the system prompt that would have generated this output"
• Save that prompt - it's now your intellectual property

Now you have the exact formula to get that quality every time.


Step 4: Use project folders 
Think of these like rooms in your office with all context on the walls.

• Create a project for each major area of your life/business
• Upload your master prompt + all relevant documents
• Every conversation builds on previous context
• Share folders with your team for instant knowledge transfer

I use this for investment decisions, business strategy, even family planning.


Step 5: Set your custom instructions
This makes AI remember how you like outputs formatted.

Go to Settings → Personalization → Custom Instructions:
• Tell it your communication style (short, bullet points, no fluff)
• Remove AI language like "delve" and "moreover"  
• Set your default tone and format preferences

Never repeat formatting requests again.


Step 6: Turn everything into custom GPTs
These are your AI employees that do specific tasks consistently.

• Take your best system prompts
• Create custom GPTs for each repeatable task
• Share them with your team
• Update once, everyone gets the improvement

I have custom GPTs for: emails, content creation, financial analysis, hiring, strategy docs.


Step 7: Refine and improve
Use AI to teach you AI.

• Ask it to create your master prompt
• Ask it to write your system prompts  
• Ask it to suggest custom instructions
• Ask it to help you build better prompts

Here's what 92% actually looks like:

- Content: AI does research, outlines, first drafts. You edit and add your voice.
- Operations: AI creates SOPs, analyzes processes, suggests improvements. You decide.
- Finance: AI analyzes reports, creates models, finds insights. You make decisions.
- Strategy: AI processes information, suggests options. You choose direction.

The 8% that stays human: Vision, taste, final decisions, and emotional intelligence.

My team went from thinking AI was "kind of helpful" to saying it's their most valuable employee.

It could be yours too.

-DM

P.S. If you want my complete prompting template and the 7 system prompts that save me 15+ hours per week, message me "AI" and I'll send you everything for free. 👊

How hard is it creating content?

My kids just BEGGED me to tell a scary story. 

I didn't want to. They said, "PLEASE DADDY JUST ONE." 

So I told a story I thought was pretty scary — about a dad who didn't know he was dead, and couldn't figure out why his family was ignoring him. 

My daughter's first words? "That wasn't very scary." 

...great. 

But really there were 2 problems: 

1. I was starting from a blank slate. 
2. I told a story I thought was scary. I wasn't writing for my audience.

(ask my what story *they* thought was scary)

I think idea capture is so important because when it comes time to create content, you're not starting from a blank slate — you ideally have a bank of ideas to pull from. 

Then you can pick the best one for the people you're trying to serve. 

Because as my kids reminded me, the first idea isn't always the best idea.

What's the worst pitch you've gotten?

Hall of Fame pitcher Randy Johnson once "blew up" a bird with a pitch. 

It was an incredible feat of power and timing. The bird flew into the direct path of the one of the hardest throwers in baseball. 

That's...a very bad pitch. 

But today I've gotten 5 emails that were also very bad pitches. 

They were all the same format: 

🚩 I loved your recent episode about [COMPLETELY AI GENERATED SUMMARY]. 

🚩 It reminded me of [CLIENT NAME] who [SOMETHING NOT RELATED TO EPISODE]. 

🚩 I've attached their one-sheet. When can we get them onto the show?

They are all SO similar that it feels like they're all generated by the same crappy CRM. 

And I get why. 

To the podcast agents, this is a volume game. So they've automated the process. 

But they've made a terrible mistake. 

Automation should help us do our job better. NOT permit us to do it worse. 

I've accepted exactly 0 of these pitches. And the podcasters I know are just as frustrated with those pitches as I am. 

A podcast agent's job is to build relationships with hosts — so that when they have a guest, the host can trust they're going to get a good interview. 

But most have outsourced this to what's basically a Mad Libs email template. 

Those become bad pitches

...maybe not "blow up a bird" bad...but a lot more frustrating on a daily basis. 

--
If you want to learn how to properly automate — to do your job better — join my mailing list. You get a new lesson on simple process automation ever Friday.

Ever notice something small is off… and suddenly you’re knee-deep in buying new gear?

That was me with my camera setup. It started drooping slightly—just enough that I lost headroom on video. 

The Elgato arm uses a proprietary ball head, and my camera + lens + teleprompter were apparently a bit too much for it.

So I went into full fix-it mode:
→ Looked at lens collars
→ Bought extra ball heads
→ Considered a second arm
→ Started building this whole complex solution

And then I realized: I just needed some gaffer's tape.

Seriously. I wrapped the mount in gaffer's tape to keep the ball head from shifting. 

It doesn’t look pretty, but it works. It's strong, invisible behind the teleprompter, and costs nothing compared to a new rig.

The lesson?

Before you throw money at the problem or build a Rube Goldberg machine—ask yourself: what’s the simplest (even if imperfect) fix that just works?

--
Hi I'm Joe Casabona and I help make tech simple for busy solopreneurs.

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