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Inbox Insiders #39 - Second Chances

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The Laidback Business Bulletin

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Inbox Insider #39 - October 26th, 2025

Welcome to Issue #39 of "Inbox Insiders": Your Email List-Building Backstage Pass

In this issue:

  1. By the Numbers: What worked and what didn't
  2. Deep Dive: Second Chances
  3. Up Next: What I'm working on this week

Welcome to Issue #39

"Inbox Insider" is my Sunday newsletter sharing the behind-the-scenes of what I'm doing to grow my email list to 100,000.

I share what works, what doesn't, and how I'm growing.

Thanks for reading.

Let's dive in:


By The Numbers:

My Email List

  • Total Subscribers: 14,476 (last week: 14,484)
  • Added last week (net): 40
  • 5* Subscribers (engaged in the last 30 days): 9,679 (last week: 9,747)

My Ad Account - Lead Magnets:

  • Ad Spend: $385 (last week: $385)
  • Gross Leads from FB: 205 (last week: 238)
  • Cost per lead: $1.87 (last week: $1.62)

Instagram (@emailschool): Started Feb 1st

  • Total Subscribers: 543 (+3 this week)

Email School (Email-Focused Membership):

  1. Paying Members: 244 (-0 from last week)
  2. Monthly Recurring Revenue: $4,921 (-$0/mo from last week)

Other Audiences:


Deep Dive: Second Chances.

How It Started

2 years ago, I had my first leveraged win. More on that later.

I spent all of 2023 (my first year back in Entrepreneur Land) doing VIP Days.

I was a mercenary.

A sword for hire.

Book me for a day and I'll make your marketing problems go away.

In January, it was $1,500 a day.

By March, $2,500.

My sweet spot was $3,000 for a day, and I could book as many as I had available.

This meant it was easy to hit $10K or $20K months, working 5-7 days per month.

But...

It wasn't scalable.

Even worse, it was pretty boring.

The "Anne" Model

The first VIP Day I booked in January 2023 was for a woman named Anne.

We were in a Mastermind together, and she needed help with her email welcome series.

As part of her VIP Day intake, I asked her how her business worked.

It was so simple, I thought I was missing something.

First, she sold a $10 "coaching week" on how to do a specific task.

Then, she sold a $2K cohort.

And finally, a $99/mo membership when the cohort was done.

The results?

She did like $80K+ in January of that year.

By May, she crossed the half-a-million mark and went to Europe.

It was such a simple model, I just had to try it.

List Building Breakthrough

For my Coaching Week, I chose my favorite party trick: automating your list-building with Ads.

I charged $20, and 100 people signed up.

Then, I sold a $997 cohort, and 30 people bought it.

When the cohort wrapped, I offered a $99/mo membership.

22 of the 30 stayed in the membership.

In January 2024, I cloned the promo.

I literally did it the exact same way, and the results were even better.

120 people bought the Ads Coaching Week.

31 bought the $997 offer.

It was like a $30k money-printing machine.

It was time to celebrate.

Globe Trotting in 2024

After the September 2023 promo, we booked a trip to Italy for April 2024 with my parents.

After the January 2024 success, I thought it would be nice to do something for my parents for their birthdays.

So I planned a guided fly-fishing trip in June with my Dad.

And an October trip to Napa with my Mom.

The fly-fishing trip happened.

But Napa was postponed because my Dad got sick 4 days before we were to leave.

A 2nd Attempt

Once my Dad got better earlier this year, I rebooked the Napa trip.

Same dates.

Same hotel.

Same itinerary.

It was a trip we won't soon forget.

I don't know why things happen the way they do.

I don't know why I landed and lost that dream job over 6 months.

I don't know why my dad had health issues (he's better now).

I do know, however, that I'm grateful for 2nd chances.

At business...

At life...

At Napa...

Thanks for reading,

~ Cody

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The Laidback Business Bulletin

Want a daily dose of digital marketing motivation? Join over 13,037 subscribers here 👇