
Welcome to another issue of Retire & RISE.
Where we turn complicated online marketing into warm human connection, share simple how-tos for beginners, and celebrate late-blooming digital creators who refuse to fade quietly into retirement! ☕✨
Know someone who just joined an email list and immediately regretted it? Forward this email to them!
In today’s issue:
● Why most welcome emails push readers away
● The simple 4-email structure that feels like a handshake
● How “trust first” turned my whole business around
I currently send the Retire & RISE Newsletter twice a week (Tuesday and Saturday). Some readers have ask for more frequent issues. Your opinion matters to me.

Write a Welcome Email That Feels Like a Handshake
💡 A thought-shifting opener
If your welcome email feels like a sales pitch, you’ve already lost them.
If it feels like a handshake, you’ve already won.
Most retirees (and honestly, most humans) don’t want another marketer in their inbox.
They want a guide.
A friend.
Someone who talks to them like a real person — not a funnel.
And that all starts with the very first email you send.

📖 A story
Not that long ago, when I first dipped my toes into online business, I treated welcome emails like a chance to “impress.”
I would cram in everything - my story, my program, my links, my perfect elevator pitch.
By the time someone reached the bottom (if they went that far) of the email, they were probably sweating and confused.
It tanked my engagement.
Nobody replied.
Nobody clicked.
And the only thing I “welcomed” people into was ghosting me.
Then came a lesson I picked up inside OLSP, one that completely reframed my approach:
“A welcome series isn’t where you sell. It’s where you build comfort.”
At first, I resisted it.
I thought, “But I need them to know everything upfront!”
Later, AI Scale Stack reinforced that same principle with even more clarity:
Trust before tactics. Connection before conversion.
When I finally applied it, everything shifted.
I started earning consistently.
I built an audience that actually replied.
And my emails began to feel like conversations with real people, not lectures from a podium.
If you have ever felt pressured or overwhelmed by someone online… that’s exactly what we’re avoiding here.

.
⚙️ Tactical Application: The 4-Email Handshake Series
Keep this simple, friendly, and human.
Think: two neighbors chatting on the porch, not a CEO blasting announcements.
Email 1 - The Warm Welcome
The goal: comfort, not conversion.
What to include:
● A genuine “I’m glad you’re here”
● One sentence about what they can expect
● A quick question that invites a reply (“What’s one thing you want to learn?”)
● A familiar signature, for example: “See you at the bank.”
Why it works:
It tells the reader you see them, not their wallet.
Email 2 - Introduce the Program or Product They Signed Up For
The goal: clarity and reassurance.
What to include:
● A simple explanation of the resource they came for
● How to use it
● What outcome it helps them achieve
● Any shortcuts to make it easier
Why it works:
It eliminates overwhelm, the #1 reason beginners quit.
Email 3 - Introduce Yourself (The Human Behind the Emails)
The goal: connection, not credentials.
What to include:
● A bite-sized version of your story
● Why you do this
● A real moment of honesty (a struggle or lesson learned)
● A gentle invitation: “What’s your story?”
Why it works:
People don’t follow experts.
People follow people.
Email 4 - Explain What’s Next
The goal: orientation + gentle forward motion.
What to include:
● What they’ll receive next
● How often you email
● The next micro-action (“Watch for tomorrow’s quick tip”)
● A standing invitation to ask questions
Why it works:
Anxiety disappears when expectations are clear.
Golden Rule of Every Email
Invite them to reply.
It doesn’t matter if they never do, what matters is that they feel like they can.

Crash Expert: “This Looks Like 1929” → 70,000 Hedging Here
Mark Spitznagel, who made $1B in a single day during the 2015 flash crash, warns markets are mimicking 1929. Yeah, just another oracle spouting gloom and doom, right?
Vanguard and Goldman Sachs forecast just 5% and 3% annual S&P returns respectively for the next decade (2024-2034).
Bonds? Not much better.
Enough warning signals—what’s something investors can actually do to diversify this week?
Almost no one knows this, but postwar and contemporary art appreciated 11.2% annually with near-zero correlation to equities from 1995–2024, according to Masterworks Data.
And sure… billionaires like Bezos and Gates can make headlines at auction, but what about the rest of us?
Masterworks makes it possible to invest in legendary artworks by Banksy, Basquiat, Picasso, and more – without spending millions.
23 exits. Net annualized returns like 17.6%, 17.8%, and 21.5%. $1.2 billion invested.
Shares in new offerings can sell quickly but…
*Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.

🧭 Intelligent Elevation
Frank, when someone joins your list, they’re not judging your technical skills.
They’re judging whether they can trust you.
A good welcome series says:
“You’re safe here. I won’t overwhelm you. We’ll take this one step at a time.”
People don’t unsubscribe from warmth.
They unsubscribe from pressure, confusion, and noise.

💬 Closing Insight
Your welcome series isn’t a sales funnel.
It’s the first friendship you build in your business.
Get that right… and everything else gets easier.
🔁 Quote to close
“People don’t care how much you know until they know how much you care.”
See you at the bank. 💰
Bob
Missed a previous issue? You can catch up any time at https://retireandrise.beehiiv.com.
Each newsletter is archived there for easy reading and sharing.
I also have reviews to profitable products there as well.
Check it out.

🏦 See You at the Bank Picks
💬 Real tools. Real results. No hype.
These are the exact programs and tools I personally use that keep producing real commissions - month after month.
I’m not chasing the latest “shiny object” anymore, just sticking with what works for everyday people who want honest online income.
💵 My Go-To Income Builders
1️⃣ OLSP System - My $7 starter turned into over $3,500 (and counting).
2️⃣ AI Cash Machines - A simple AI setup for daily commissions.
3️⃣ GotBackup - A legit data-protection service that pays monthly.
4️⃣ LeadsLeap - A must have for every internet marketer.
If you decide to try one of these, let me know if I can help and how it goes.
Your story might become the next See You at the Bank success I share here.

🏷 Hashtags
#EmailMarketingTips #RetireeSideHustle #AIForBeginners #WelcomeSequence #OnlineIncome50Plus #TrustFirst #WarmMarketing #BeginnerFriendlyAI #AffiliateMarketingForRetirees


