Building a Business at 50+ Without Quitting My Day Job: Week 3 Results

I’m embarrassed.

I haven't generated a single dollar yet.

It’s frustrating, and I'm starting to worry that I might not reach my goal of $500 in 30 days and let you down (the danger of building a business at 50 in public).

But I know that stewing on these thoughts too much only leads to anxiety. SO, I'm going to just focus on the work. I need to keep pushing forward and continue honing my skills.

I know that once I find the right combination of strategies and techniques, things will start to progress faster.

And it’s not all bad. I had some wins this week. And I have some pretty cool tips for you this week (like how to build your own AI assistant).

Let’s dig in…

Newsletter Business Week 2 Results

Current Stats/Results 📊

• Income: Still at $0 (keeping it real here - BUT a pending affiliate commission of $19.50 so that’s something)

• Leads: 4

• Meetings: 4 solid conversations

• Email List: 2 new signups in 24 hours (from the new lead magnet)

• Partnership Opportunities: 3

Weekly Wins 🎯

• Finished my first newsletter buildout for Dustin at Social Media Bites (free project to get my feet wet)

• Created a new lead magnet that's already getting traction

• Had three high-quality conversations with good people who could eventually become clients or business partners (Construction Manager, Technical Writer, and PR professional)

Those conversations might not have turned into immediate sales, but they're giving me invaluable insights into what people actually need (more on that in a minute).

Plus, I am building some goodwill while meeting some quality people who - even if we don’t work together anytime soon, I think they trust me enough to know they can reach out any time or maybe even refer someone they know who could use my help.

So, If you're also in the "building something new" phase, these early metrics might not look impressive, but they're the foundations we build on. Trust me on this.

What I Worked On This Week

• The Newsletter Buildout Project: Finally wrapped up that first buildout I mentioned. Man, documenting the process while you're doing it is harder than it sounds, but now I know exactly how long these take and what to charge going forward. (File that under "lessons learned the hard way")

• The Pivot (Again): So here's a funny story - I was all in on this welcome email series thing until I realized something pretty obvious during those calls: most people I'm talking to don't even have a newsletter yet. DOH! So, I shifted gears and created a newsletter "getting started" guide instead. Sometimes, the obvious answer is staring you right in the face.

• Social Media Series: Finally got that 7-14 day social series done (it's been haunting my to-do list forever). With AI tools, it actually came together pretty quickly once I finally sat down to do it. Now I can schedule posts in advance instead of scrambling every morning at 8 AM trying to figure out what to post on LinkedIn.

• Working with a Redefining Retirement Reader: This is exciting - I started working with one of you (hey Chris!) on adding to his offensive portfolio. He had some reservations about marketing, but we got into this whole discussion about being storytellers and toolmakers. I think it helped. I talk about this more in my article here → “Retirement Planning: Why Gen Xer’s Must Understand Marketing.”

What I Learned

Let's get real honest for a minute - my sales skills are WAY rustier than I thought. And yeah, sometimes late at night, when I'm staring at $0 revenue and looking like a fool in front of my newsletter readers (that’s you), the anxiety creeps in about hitting those goals I set.

But here's what I'm learning (besides the fact that I need to brush up on my sales game):

1. The Basics Matter More Than Ever: I was trying to sell people on welcome sequences when some hadn't even started their newsletter yet. Classic case of running before walking. It's like when I tried to learn Van Halen's "Eruption" before I could even play basic chords. (Spoiler: It didn't go well)

2. Video Is Your Friend: I started sending personal video messages on LinkedIn chat instead of just texting… game changer. Every single Zoom call I got this week came from someone who received a video message with my shiny face in it. There's something about seeing a real person (a receding hairline and all) that cuts through all the LinkedIn spam noise. I just use my phone, nothing fancy. "Hey [Name], Corey here! Just wanted to show you I'm a real person..."

3. The "Help First" Approach: You know what's funny? Once I know about someone's business, my brain won't shut up about ideas for them. So, I've been sending follow-up thoughts and suggestions to everyone I talk to, even if they're not ready to buy. It feels right, and I have a feeling it'll pay off in the long run.

What's Working Now

• LinkedIn engagement (4 leads and 3 Zoom calls came from)

• Personalized video messages in LinkedIn chat (huge difference in response rates)

• The documentation process makes content creation faster and easier.

• Helping first, selling second approach

Next Week's Focus

Here's where I'm putting my energy:

1. LinkedIn Momentum: Not changing what's working. Keeping up the daily posts and engagement. (If it ain't broke...)

2. B2B Expansion (Maybe?): My discussion with the technical writers has me mulling over the idea of expanding into the manufacturing/industrial/engineering space. I've got experience there from my Google Ads business and mechanical drafting days, and I know from working with clients that these businesses need email marketing help more than they realize.

3. Process Documentation: I am going to keep building out my "standard operating procedures" because every time I document something, it makes the next project faster and smoother.

4. Finish My Newsletter Start Guide Email Series: I built the guide, whipped up a landing and created a welcome message that delivers the guide. BUT I haven’t had the chance to create the series yet. Need to get this done ASAP because the guide talks about how important a welcome series is, and here I am with only one welcome message. 🤦 

💡 Tool of the Week: Loom

Sometimes, the simplest tools make the biggest difference. In addition to my phone, I’ve been using Loom for back-and-forth LinkedIn video messages:

• Link: Loom
  Cost: Free plan is perfect for starting

• Setup time: 5 minutes max

• Let's you record quick videos - screen capture or webcam - right from your browser

• Gives you a simple link to share

• Tracks if people watched (super helpful for follow-up)

I’ve been using it for years for all kinds of stuff, like showing clients instructions, walkthroughs, and monthly reports.

🤖 AI Tip of the Week: Custom ChatGPT Projects

Think of ChatGPT Projects like training your own AI helper who actually understands your work. It's like having a smart assistant who knows your communication style and can help you work faster.

Here's a real-world example:

Say you're a project manager. Create a "Management Assistant" project by uploading:

• Past team updates

• Project reports

• Meeting notes

• Company processes

• Writing example

Now when you ask it to "draft a status update for the marketing project," it uses your actual terminology and writing style instead of generic AI responses.

Some other real-world uses I've seen:

• Teachers creating lesson plan assistants

• Sales pros building proposal writers

• HR folks making job description helpers

• Small business owners creating customer service assistants

Here's how to create your first project (takes about 15-20 minutes):

1. Open ChatGPT (Plus subscription)

2. Click "New Project"

3. Name it (like "Work Assistant")

4. Upload 2-3 relevant documents

5. Add simple instructions:

   1. "You are an expert [ASSISTANTS ROLE]. Help me [DESCRIBE TASK]."

How I used it this past week: When building that newsletter for Dustin, I uploaded his content and brand info. The AI then helped me:

• Draft welcome emails that sounded like him

• Build customer personas of his ideal customers

• Generate content ideas aligned with his brand

• Spot inconsistencies in messaging

• More

Pro tip: Start small with just a few key documents. You can always add more later.

Question for you: Want me to show you how to create your own custom assistant? I’m thinking about giving a class on how to set them up. If I get enough of you, I’ll set it up. Just reply with "AI CLASS" if you’d take the class.

Your Action Steps

1. Create your first ChatGPT Project:

   • Start with just 2-3 work documents you use regularly

   • Use it to draft one email or report you normally write

   • See how much time it saves you

2. Try the video message approach on LinkedIn:

   • Download Loom (free version)

   • Send a quick 30-second intro to someone you want to connect with

   • Keep it casual - just be yourself

   • (Quick tip: Nobody likes perfect videos anyway. Just hit record and say hi)

3. Start documenting one regular process:

   • Pick something you do at least weekly

   • Write down the basic steps

   • You'll thank yourself later (trust me on this one)

You don't have to do all of these. Pick ONE that feels most doable and start there. Sometimes, the smallest steps lead to the biggest changes.

Music Therapy

No sales, feeling embarrassed.

15-20 years ago, I might’ve given up and went on a bender

But I know now that that’s not going to get me anywhere except really depressed and full of regret.

So, in the words of the late great Tom Petty (and at the risk of sounding a tad cheesy)…

“I Won’t Back Down”

And what a great album “Full Moon Fever” that song was on.

Have a good one,

Corey

P.S. Do you have experience in manufacturing or B2B? Hit reply - I'd love to pick your brain on potential opportunities.